Organic electroluminescent elements and electronic devices
By using compounds with specific structures as the host material and electron transport layer in organic electroluminescent elements, the problems of insufficient luminous efficiency and lifetime have been solved, achieving a high-efficiency and long-life luminous effect.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2020-11-06
- Publication Date
- 2026-04-03
AI Technical Summary
Existing organic electroluminescent devices have shortcomings in terms of luminous efficiency and lifespan, making it difficult to achieve efficient and long-lasting luminous effects.
By using compounds with specific structures as the main materials for the first and second light-emitting layers, and setting a first electron transport layer between the light-emitting layer and the cathode, a specific triplet energy relationship is satisfied, thereby improving luminous efficiency and lifetime.
Organic electroluminescent elements with high luminous efficiency and long lifespan have been developed, improving the performance of electronic devices.
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Figure CN114467188B_ABST
Abstract
Description
Technical Field
[0001] This invention relates to organic electroluminescent elements and electronic devices. Background Technology
[0002] Organic electroluminescent devices (hereinafter sometimes referred to as "organic EL devices") are used in full-color displays for mobile phones, televisions, and other applications. When a voltage is applied to an organic EL device, holes are injected from the anode into the emitting layer, and electrons are injected from the cathode into the emitting layer. Then, in the emitting layer, the injected holes recombine with the electrons to form excitons. At this point, according to the statistical rules of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons at a rate of 75%.
[0003] To improve the performance of organic EL devices, various studies have been conducted on compounds used in organic EL devices. Performance characteristics of organic EL devices include, for example, brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime.
[0004] For example, Patent Document 1 describes an organic electroluminescent element having a light-emitting layer on the anode side containing a pyrene derivative and a light-emitting layer on the cathode side containing an anthracene derivative.
[0005] For example, Patent Document 2 describes an organic electroluminescent element having a light-emitting layer containing an anthracene derivative as the host material and a pyrene derivative as a dopant material.
[0006] For example, Patent Document 3 describes an organic electroluminescent element having an anode-side light-emitting layer containing a pyrene derivative as the main material and a cathode-side light-emitting layer containing an anthracene derivative as the main material.
[0007] Existing technical documents
[0008] Patent documents
[0009] Patent Document 1: Japanese Patent Application Publication No. 2007-294261
[0010] Patent Document 2: Japanese Patent Application Publication No. 2013-157552
[0011] Patent Document 3: Japanese Patent Application Publication No. 2019-161218 Summary of the Invention
[0012] The problem the invention aims to solve
[0013] The object of the present invention is to provide an organic electroluminescent element that emits light with high luminous efficiency and long lifetime, and an electronic device equipped with the organic electroluminescent element.
[0014] means for solving problems
[0015] According to one aspect of the present invention, an organic electroluminescent element is provided, which has an anode, a cathode, a first light-emitting layer and a second light-emitting layer disposed between the anode and the cathode and directly connected to each other, and a first electron transport layer disposed between the first light-emitting layer and the second light-emitting layer and the cathode, wherein the first light-emitting layer contains a first compound of the following general formula (1) as a first host material, the first compound having at least one group of the following general formula (11), the second light-emitting layer contains a second compound of the following general formula (2) as a second host material, and the first electron transport layer contains a third compound of the following general formula (3).
[0016]
Chemical Formula 1
[0017]
[0018] (In the above general formula (1),
[0019] R 101 ~R 110 Each independently
[0020] hydrogen atom,
[0021] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0022] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0023] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0024] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0025] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0026] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0027] -O-(R 904 The groups shown in the figure,
[0028] -S-(R 905 The groups shown in the figure,
[0029] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0030] -C(=O)R 801 The groups shown
[0031] -COOR802 The groups shown
[0032] Halogen atoms,
[0033] cyano,
[0034] Nitro,
[0035] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[0036] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[0037] The groups represented by the above general formula (11),
[0038] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11) above.
[0039] When there are multiple groups represented by the above general formula (11), the multiple groups represented by the above general formula (11) may be the same as or different from each other.
[0040] L 101 for
[0041] single bond,
[0042] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[0043] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0044] Ar 101 for
[0045] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0046] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0047] mx is 0, 1, 2, 3, 4, or 5.
[0048] In L 101 In cases where there are two or more L's, there are two or more L's. 101 They are the same or different.
[0049] In Ar 101 In cases where there are two or more Ar, two or more Ar 101 They are the same or different.
[0050] In the above general formula (11), * indicates the bonding position with the pyrene ring in the above general formula (1).
[0051]
Chemical Formula 2
[0052]
[0053] (In the above general formula (2),
[0054] R 201 ~R 208 Each independently
[0055] hydrogen atom,
[0056] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0057] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0058] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0059] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0060] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0061] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0062] -O-(R 904 The groups shown in the figure,
[0063] -S-(R 905 The groups shown in the figure,
[0064] -N(R 906 (R) 907 The groups shown in the figure,
[0065] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0066] -C(=O)R 801 The groups shown
[0067] -COOR 802 The groups shown
[0068] Halogen atoms,
[0069] cyano,
[0070] Nitro,
[0071] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0072] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0073] L201 and L 202 Each independently
[0074] single bond,
[0075] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[0076] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0077] Ar 201 and Ar 202 Each independently
[0078] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0079] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[0080]
Chemical Formula 3
[0081]
[0082] (In the above general formula (3),
[0083] A is
[0084] Substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, or
[0085] Heterocyclic groups with 5 to 13 cyclic atoms, substituted or unsubstituted.
[0086] B is
[0087] Substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, or
[0088] Heterocyclic groups with 5 to 13 cyclic atoms, substituted or unsubstituted.
[0089] L is
[0090] single bond,
[0091] Substituted or unsubstituted cyclic aromatic hydrocarbons with 6–18 carbon atoms (n+1) cyclic groups
[0092] Substituted or unsubstituted heterocyclic groups with 5 to 13 cyclic atoms (n+1) valence, or
[0093] A (n+1) valence group having a structure consisting of two or three distinct groups bonded together from a substituted or unsubstituted aromatic hydrocarbon cyclic group having 6 to 18 carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 13 cyclic atoms.
[0094] C is
[0095] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0096] Heterocyclic groups with 5 to 60 cyclic atoms, substituted or unsubstituted.
[0097] n is 1, 2, or 3.
[0098] When n is 2 or higher, L is not a single bond.
[0099] When n is 2 or more, multiple Cs may be identical or different.
[0100] (In the first compound represented by the above general formula (1) and the second compound represented by the above general formula (2), R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently
[0101] hydrogen atom,
[0102] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0103] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0104] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0105] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0106] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[0107] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[0108] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[0109] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[0110] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.
[0111] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[0112] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.
[0113] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[0114] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)
[0115] According to one aspect of the present invention, an organic electroluminescent element is provided, comprising an anode, a cathode, a first light-emitting layer and a second light-emitting layer disposed between the anode and the cathode and directly connected to each other, and a first electron transport layer disposed between the directly connected first and second light-emitting layers and the cathode. The first light-emitting layer contains a first compound as a first host material, and the second light-emitting layer contains a second compound as a second host material. The first host material and the second host material are different from each other. The first light-emitting layer contains at least a compound that emits light with a maximum peak wavelength of 500 nm or less, and the second light-emitting layer contains at least a compound that emits light with a maximum peak wavelength of 500 nm or less. The compound that emits light with a maximum peak wavelength of 500 nm or less in the first light-emitting layer is the same as or different from the compound that emits light with a maximum peak wavelength of 500 nm or less in the second light-emitting layer. The triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the following mathematical formula (Mathematical Formula 1A). The first electron transport layer contains a third compound as shown in the above general formula (3).
[0116] T1(H1)>T1(H2)...(Mathematical Expression 1A)
[0117] According to one aspect of the present invention, an electronic device incorporating the organic electroluminescent element described above is provided.
[0118] According to one aspect of the present invention, an organic electroluminescent element that emits light with high luminous efficiency and long lifetime can be provided. Furthermore, according to another aspect of the present invention, an electronic device incorporating the organic electroluminescent element can be provided. Attached Figure Description
[0119] Figure 1 This is a diagram illustrating the general configuration of an example of an organic electroluminescent element according to one embodiment of the present invention.
[0120] Figure 2 This is a diagram illustrating the general configuration of an example of an organic electroluminescent element according to one embodiment of the present invention.
[0121] Figure 3 This is a diagram illustrating the general configuration of an example of an organic electroluminescent element according to one embodiment of the present invention.
[0122] Figure 4 This is a diagram illustrating the general configuration of an example of an organic electroluminescent element according to one embodiment of the present invention. Detailed Implementation
[0123] [definition]
[0124] In this specification, a hydrogen atom means an isotope containing different numbers of neutrons, namely protium, deuterium, and tritium.
[0125] In this specification, the chemical structural formula does not explicitly show that the bonding positions of symbols such as "R" and "D" representing deuterium atoms are set to be bonded to hydrogen atoms, i.e., protium atoms, deuterium atoms, or tritium atoms.
[0126] In this specification, the number of carbon atoms forming a ring refers to the number of carbon atoms in the ring itself of a compound whose atoms are bonded in a ring (e.g., monocyclic compounds, fused-ring compounds, bridged-ring compounds, carbocyclic compounds, and heterocyclic compounds). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of carbon atoms forming the ring. The term "number of carbon atoms forming a ring" is used as described below unless otherwise specified. For example, the number of carbon atoms forming a ring is 6 for a benzene ring, 10 for a naphthalene ring, 5 for a pyridine ring, and 4 for a furan ring. Additionally, for example, the number of carbon atoms forming a ring is 13 for 9,9-diphenylfluoreneyl and 25 for 9,9'-spirobifluoreneyl.
[0127] Furthermore, when a benzene ring is substituted with an alkyl group, the carbon number of the alkyl group is not included in the number of carbon atoms in the ring-forming process of the benzene ring. Therefore, the number of carbon atoms in the cyclic benzene ring substituted with an alkyl group is 6. Similarly, when a naphthalene ring is substituted with an alkyl group, the carbon number of the alkyl group is not included in the number of carbon atoms in the ring-forming process of the naphthalene ring. Therefore, the number of carbon atoms in the cyclic naphthalene ring substituted with an alkyl group is 10.
[0128] In this specification, the number of cyclic atoms refers to the number of atoms constituting the ring itself in compounds (e.g., monocyclic compounds, fused-ring compounds, bridged-ring compounds, carbocyclic compounds, and heterocyclic compounds) where atoms are bonded in a ring structure (e.g., monocyclic, fused-ring, and aggregated-ring). Atoms that do not constitute a ring (e.g., hydrogen atoms that end the bonds of the ring-forming atoms) and atoms contained in substituents when the ring is substituted are not included in the number of cyclic atoms. The term "number of cyclic atoms" as used below is the same unless otherwise stated. For example, the number of cyclic atoms in a pyridine ring is 6, in a quinazoline ring it is 10, and in a furan ring it is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or atoms constituting substituents are not included in the number of cyclic atoms in pyridine. Therefore, the number of cyclic atoms in a pyridine ring bonded with hydrogen atoms or substituents is 6. Furthermore, hydrogen atoms bonded to the carbon atoms of the quinazoline ring, or atoms constituting substituents, are not included in the number of cyclic atoms of the quinazoline ring. Therefore, the number of cyclic atoms in a quinazoline ring with bonded hydrogen atoms or substituents is 10.
[0129] In this specification, the phrase "ZZ group with substituted or unsubstituted carbon numbers of XX to YY" indicates the number of carbons when the ZZ group is unsubstituted; the number of carbons in substituents is not included. Here, "YY" is greater than "XX," where "XX" refers to an integer greater than 1, and "YY" refers to an integer greater than 2.
[0130] In this specification, the phrase "ZZ group with substituted or unsubstituted atoms of XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, excluding the number of atoms of substituents when substitution has occurred. Here, "YY" is greater than "XX", where "XX" is an integer greater than or equal to 1, and "YY" is an integer greater than or equal to 2.
[0131] In this specification, "unsubstituted ZZ group" means "substituted or unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".
[0132] In this specification, "unsubstituted" when referred to as "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group has not been replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.
[0133] Furthermore, in this specification, "substitution" when expressed as "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group have been replaced by a substituent. Similarly, "substitution" when expressed as "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group have been replaced by an AA group.
[0134] Substituents described in this specification
[0135] The substituents described in this specification are explained below.
[0136] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.
[0137] Unless otherwise stated in this specification, the number of cyclic atoms in the "unsubstituted heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.
[0138] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[0139] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkenyl group" is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
[0140] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkynyl group" is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
[0141] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted cycloalkyl group" is 3 to 50, preferably 3 to 20, and more preferably 3 to 6.
[0142] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.
[0143] Unless otherwise stated in this specification, the number of cyclic atoms in the "unsubstituted divalent heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.
[0144] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkylene group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[0145] • "Substituted or unsubstituted aryl groups"
[0146] Specific examples of "substituted or unsubstituted aryl" as described in this specification (specific example group G1) include unsubstituted aryl (specific example group G1A) and substituted aryl (specific example group G1B), etc. (Here, unsubstituted aryl refers to the case where "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl refers to the case where "substituted or unsubstituted aryl" is "substituted aryl".) In this specification, when referred to only as "aryl", both "unsubstituted aryl" and "substituted aryl" are included.
[0147] "Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" group have been substituted with a substituent. Examples of "substituted aryl" include the group in Specific Example Group G1A below in which one or more hydrogen atoms of an "unsubstituted aryl" group have been substituted with a substituent, and the substituted aryl group in Specific Example Group G1B below. It should be noted that the examples of "unsubstituted aryl" and "substituted aryl" listed here are only examples. The "substituted aryl" described in this specification also includes the group in Specific Example Group G1B below in which hydrogen atoms bonded to the carbon atom of the aryl group itself have been further substituted with a substituent, and the group in Specific Example Group G1B below in which hydrogen atoms of the substituent have been further substituted with a substituent.
[0148] • Unsubstituted aryl groups (specific example group G1A):
[0149] phenyl,
[0150] p-phenyl,
[0151] metaphenyl,
[0152] o-phenyl,
[0153] p-terphenyl-4-yl,
[0154] p-terphenyl-3-yl,
[0155] p-terphenyl-2-yl,
[0156] m-terphenyl-4-yl,
[0157] m-terphenyl-3-yl,
[0158] m-terphenyl-2-yl,
[0159] o-terphenyl-4-yl
[0160] o-terphenyl-3-yl
[0161] o-terphenyl-2-yl,
[0162] 1-Naphthyl,
[0163] 2-Naphthyl,
[0164] anthracene,
[0165] Benzanthracene,
[0166] Fiki,
[0167] Benzphenanthrene,
[0168] Finadenyl,
[0169] Pyrene
[0170] base,
[0171] benzo[a] base,
[0172] Tri-phenylene,
[0173] Benzotrimethylene
[0174] phenylene,
[0175] Pentaphenyl,
[0176] Fluorine
[0177] 9,9'-spirobisfluorene,
[0178] benzo[f]fluorenyl,
[0179] Dibenzofluorene,
[0180] Fluoranthene group,
[0181] Benzofluoranthyl,
[0182] Perylene group, and monovalent aryl group derived from the ring structure shown in the following general formulas (TEMP-1) to (TEMP-15) by removing one hydrogen atom.
[0183] [Chemical Formula 4]
[0184]
[0185] [Chemical Formula 5]
[0186]
[0187] • Substituted aryl groups (specific example group G1B):
[0188] o-Tolyl,
[0189] m-Tolyl,
[0190] p-Tolyl,
[0191] p-Xylyl,
[0192] m-Xylyl,
[0193] o-xylyl,
[0194] p-isopropylphenyl,
[0195] m-Isopropylphenyl,
[0196] o-isopropylphenyl,
[0197] p-tert-butylphenyl,
[0198] m-tert-butylphenyl,
[0199] o-tert-butylphenyl,
[0200] 3,4,5-Trimethylphenyl,
[0201] 9,9-Dimethylfluorenyl,
[0202] 9,9-Diphenylfluorenyl,
[0203] 9,9-bis(4-methylphenyl)fluorenyl,
[0204] 9,9-Bis(4-isopropylphenyl)fluorenyl,
[0205] 9,9-Bis(4-tert-butylphenyl)fluorenyl,
[0206] cyanophenyl,
[0207] Triphenylsilylphenyl
[0208] Trimethylsilylphenyl
[0209] Phenynaphthyl,
[0210] Naphthylphenyl, and groups in which one or more hydrogen atoms of a monovalent group derived from the ring structures shown in the above general formulas (TEMP-1) to (TEMP-15) have been replaced by substituents.
[0211] • "Substituted or unsubstituted heterocyclic groups"
[0212] The term "heterocyclic group" as used in this specification refers to a cyclic group whose cyclic atoms contain at least one heteroatom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.
[0213] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.
[0214] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.
[0215] Specific examples of "substituted or unsubstituted heterocyclic groups" described in this specification (specific example group G2) include unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B), etc. (Here, unsubstituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group", and substituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group".) In this specification, the term "heterocyclic group" includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".
[0216] "Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" have been substituted with a substituent. Specific examples of "substituted heterocyclic groups" include the group in example group G2A below where the hydrogen atoms of the "unsubstituted heterocyclic group" have been substituted, and the example of a substituted heterocyclic group in example group G2B below. It should be noted that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are only examples. The "substituted heterocyclic groups" described in this specification also include the group in example group G2B where the hydrogen atoms bonded to the cyclic atoms of the heterocyclic group itself have been further substituted with a substituent, and the group in example group G2B where the hydrogen atoms of the substituent have been further substituted with a substituent.
[0217] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1), unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2), unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3), and monovalent heterocyclic groups derived from the ring structures shown in the following general formulas (TEMP-16) to (TEMP-33) by removing one hydrogen atom (specific example group G2A4).
[0218] Specific example group G2B includes, for example, the following: a nitrogen-containing substituted heterocyclic group (specific example group G2B1), an oxygen-containing substituted heterocyclic group (specific example group G2B2), a sulfur-containing substituted heterocyclic group (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) have been substituted with a substituent (specific example group G2B4).
[0219] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):
[0220] pyrrole,
[0221] Imidazole group,
[0222] Pyrazolyl,
[0223] Triazole group,
[0224] Tetrazolyl,
[0225] Oxazolyl,
[0226] Isoxazolyl,
[0227] Oxadiazole group,
[0228] Thiazole group,
[0229] Isothiazolyl,
[0230] Thiadiazole group,
[0231] pyridyl,
[0232] pyridazinyl,
[0233] Pyrimidinyl,
[0234] Pyrazinyl,
[0235] Triazine group
[0236] Indole,
[0237] Isoindolyl,
[0238] Indazine-based
[0239] Quinazine-based
[0240] Quinoline,
[0241] Isoquinoline,
[0242] Crenoline group
[0243] Phthaloazine
[0244] Quinazolinyl,
[0245] Quinoxaloyl,
[0246] Benzimidazole group,
[0247] Indazole group,
[0248] phenanthroline,
[0249] phenanthridine,
[0250] acridine group,
[0251] Phenazine group,
[0252] Carbazole group,
[0253] Benzocarbazolyl,
[0254] Morpholinyl,
[0255] phenoxazine group,
[0256] phenothiazine group,
[0257] Azacarbazolyl and diazacarbazolyl.
[0258] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2):
[0259] furanyl,
[0260] Oxazolyl,
[0261] Isoxazolyl,
[0262] Oxadiazole group,
[0263] Xuton base,
[0264] Benzofuranyl,
[0265] Isobenzofuranyl,
[0266] Dibenzofuranyl,
[0267] Naphthobenzofuranyl,
[0268] Benzoxazolyl,
[0269] Benzisoxazole group,
[0270] phenoxazine group,
[0271] Morpholinyl,
[0272] Dinaphthylfuranyl,
[0273] Azadibenzofuranyl,
[0274] diazadibenzofuranyl,
[0275] Azanaphthobenzofuranyl and diazanaphthobenzofuranyl.
[0276] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3):
[0277] Thiophene group
[0278] Thiazole group,
[0279] Isothiazolyl,
[0280] Thiadiazole group,
[0281] benzothienyl
[0282] isobenzothienyl
[0283] dibenzothienyl
[0284] Naphthobenzothienyl
[0285] Benzothiazolyl,
[0286] Benzisothiazolyl,
[0287] phenothiazine group,
[0288] dinaphthothienyl
[0289] azadibenzothienyl
[0290] diazadibenzothienyl
[0291] Azanaphthobenzothienyl and diazanaphthobenzothienyl.
[0292] • The monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures shown in the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):
[0293]
Chemical Formula 6
[0294]
[0295] [Chemical Formula 7]
[0296]
[0297] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each can be independently composed of an oxygen atom, a sulfur atom, NH, or CH2. Among them, X... A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH.
[0298] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A When at least one of them is NH or CH2, the monovalent heterocyclic group derived from the ring structure shown in the above general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.
[0299] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):
[0300] (9-phenyl)carbazole group,
[0301] (9-Biphenyl)carbazole,
[0302] (9-Phenyl)phenylcarbazoyl,
[0303] (9-Naphthyl)carbazole,
[0304] Diphenylcarbazole-9-yl,
[0305] Phenylexacarbazole-9-yl,
[0306] Methylbenzimidazole,
[0307] Ethylbenzimidazole,
[0308] Phenylacetyl,
[0309] Biphenyltriazine,
[0310] diphenyltriazine group,
[0311] Phenylacetinyl and biphenylquinazolinyl.
[0312] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):
[0313] Phenyl dibenzofuranyl,
[0314] Methyldibenzofuranyl,
[0315] The monovalent residues of tert-butyldibenzofuranyl and spiro[9H-xanton-9,9'-[9H]fluorene].
[0316] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):
[0317] Phenyl dibenzothiophene,
[0318] Methyldibenzothiophene,
[0319] The monovalent residues of tert-butyldibenzothiophene and spiro[9H-thiophene-9,9'-[9H]fluorene].
[0320] • Groups derived from the ring structures shown in the above general formulas (TEMP-16) to (TEMP-33) in which one or more hydrogen atoms of a monovalent heterocyclic group have been substituted with substituents (specific example group G2B4):
[0321] The aforementioned "one or more hydrogen atoms of a monovalent heterocyclic group" refers to one or more hydrogen atoms selected from the following: hydrogen atoms bonded to the cyclic carbon atom of the monovalent heterocyclic group, hydrogen atoms bonded to the nitrogen atom when at least one of XA and YA is NH, and hydrogen atoms of the methylene group when one of XA and YA is CH2.
[0322] • "Substituted or unsubstituted alkyl groups"
[0323] As specific examples of "substituted or unsubstituted alkyl" described in this specification (specific example group G3), the following unsubstituted alkyl (specific example group G3A) and substituted alkyl (specific example group G3B) can be cited. (Here, unsubstituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when referred to as "alkyl", both "unsubstituted alkyl" and "substituted alkyl" are included.
[0324] "Substituted alkyl" refers to a group in which one or more hydrogen atoms of an "unsubstituted alkyl" have been substituted with a substituent. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms of an "unsubstituted alkyl" (specific example group G3A) have been substituted with a substituent, and examples of substituted alkyl (specific example group G3B). In this specification, "unsubstituted alkyl" refers to a chain-like alkyl group. Therefore, "unsubstituted alkyl" includes both straight-chain and branched-chain unsubstituted alkyl groups. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples; the "substituted alkyl" described in this specification also includes groups in which the hydrogen atoms of the alkyl group in specific example group G3B have been further substituted with a substituent, and groups in which the hydrogen atoms of the substituents in specific example group G3B have been further substituted with a substituent.
[0325] • Unsubstituted alkyl groups (specific example group G3A):
[0326] methyl,
[0327] Ethyl,
[0328] n-propyl,
[0329] Isopropyl,
[0330] n-Butyl,
[0331] Isobutyl,
[0332] Sec-butyl and tert-butyl.
[0333] • Substituted alkyl groups (specific example group G3B):
[0334] Heptafluoropropyl (including isomers),
[0335] Pentafluoroethyl,
[0336] 2,2,2-trifluoroethyl, and
[0337] Trifluoromethyl
[0338] • "Substituted or unsubstituted alkenyl groups"
[0339] Specific examples of "substituted or unsubstituted alkenyl groups" (specific example group G4) described in this specification include unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "substituted alkenyl group".) In this specification, when simply referred to as "alkenyl group", both "unsubstituted alkenyl group" and "substituted alkenyl group" are included.
[0340] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" group have been substituted with a substituent. Specific examples of "substituted alkenyl" include the "unsubstituted alkenyl" group (specific example group G4A) having a substituent and examples of substituted alkenyl groups (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples; the "substituted alkenyl" described in this specification also includes groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the alkenyl itself have been further substituted with a substituent, and groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the substituent have been further substituted with a substituent.
[0341] • Unsubstituted alkenyl groups (specific example group G4A):
[0342] vinyl,
[0343] Allyl
[0344] 1-Butenyl,
[0345] 2-Butenyl, and
[0346] 3-Butenyl.
[0347] • Substituted alkenyl groups (specific example group G4B):
[0348] 1,3-Butadienyl,
[0349] 1-Methylvinyl
[0350] 1-Methylallyl,
[0351] 1,1-Dimethylallyl,
[0352] 2-Methylallyl, and
[0353] 1,2-Dimethylallyl.
[0354] • "Substituted or unsubstituted alkynyl groups"
[0355] As specific examples of "substituted or unsubstituted alkynyl groups" described in this specification (specific example group G5), the following unsubstituted alkynyl groups (specific example group G5A) can be cited. (Here, unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group".) The following description of "alkynyl group" includes both "unsubstituted alkynyl group" and "substituted alkynyl group".
[0356] "Substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" have been replaced by a substituent. Specific examples of "substituted alkynyl group" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl group" (specific example group G5A) have been replaced by a substituent.
[0357] • Unsubstituted alkynyl group (specific example group G5A):
[0358] Acetylene
[0359] • "Substituted or unsubstituted cycloalkyl groups"
[0360] Specific examples of "substituted or unsubstituted cycloalkyl" described in this specification (specific example group G6) include unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B), etc. (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl".) In this specification, when referred to only as "cycloalkyl", both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.
[0361] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group have been substituted with a substituent. Specific examples of "substituted cycloalkyl" include the group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group (specific example group G6A) have been substituted with a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples. The "substituted cycloalkyl" described in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl" group of specific example group G6B have been substituted with a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted cycloalkyl" group of specific example group G6B have been further substituted with a substituent.
[0362] • Unsubstituted cycloalkyl groups (specific example group G6A):
[0363] Cyclopropyl,
[0364] Cyclobutyl,
[0365] Cyclopentyl,
[0366] Cyclohexyl,
[0367] 1-Adamantyl,
[0368] 2-Adamantyl,
[0369] 1-norborneol and 2-norborneol.
[0370] • Substituted cycloalkyl group (specific example group G6B): 4-methylcyclohexyl.
[0371] ·"-Si(R 901 (R) 902 (R) 903 The group shown in the figure”
[0372] As described in this specification, -Si(R) 901 (R) 902 (R) 903 Specific examples of the group shown in the figure (specific example group G7) can be given as follows:
[0373] -Si(G1)(G1)(G1),
[0374] -Si(G1)(G2)(G2)
[0375] -Si(G1)(G1)(G2),
[0376] -Si(G2)(G2)(G2),
[0377] -Si(G3)(G3)(G3) and -Si(G6)(G6)(G6). Here,
[0378] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.
[0379] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
[0380] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.
[0381] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.
[0382] In -Si(G1)(G1)(G1), multiple G1s may be the same or different from each other.
[0383] In -Si(G1)(G2)(G2), multiple G2s may be the same or different from each other.
[0384] In -Si(G1)(G1)(G2), multiple G1s may be the same or different from each other.
[0385] In -Si(G2)(G2)(G2), multiple G2s may be the same or different from each other.
[0386] In -Si(G3)(G3)(G3), multiple G3s may be the same or different from each other.
[0387] In -Si(G6)(G6)(G6), multiple G6s may be the same or different from each other.
[0388] ·“-O-(R 904 The group shown in the figure”
[0389] As described in this specification, -O-(R) 904 Specific examples of the group shown in the figure (specific example group G8) can be given as follows:
[0390] -O(G1)
[0391] -O(G2),
[0392] -O(G3) and
[0393] -O(G6).
[0394] Here,
[0395] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.
[0396] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
[0397] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.
[0398] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.
[0399] ·“-S-(R 905 The group shown in the figure”
[0400] As described in this specification, -S-(R) 905 Specific examples of the group shown in the figure (specific example group G9) can be given as follows:
[0401] -S(G1)
[0402] -S(G2),
[0403] -S(G3) and -S(G6).
[0404] Here,
[0405] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.
[0406] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
[0407] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.
[0408] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.
[0409] ·"-N(R 906 (R) 907 The group shown in the figure”
[0410] As described in this specification, -N(R) 906 (R) 907 Specific examples of the group shown (specific example group G10) can be given as follows:
[0411] -N(G1)(G1),
[0412] -N(G2)(G2),
[0413] -N(G1)(G2),
[0414] -N(G3)(G3) and -N(G6)(G6).
[0415] Here,
[0416] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.
[0417] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
[0418] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.
[0419] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.
[0420] In -N(G1)(G1), multiple G1s may be the same or different from each other.
[0421] In -N(G2)(G2), multiple G2 values may be the same or different from each other.
[0422] In -N(G3)(G3), multiple G3s may be the same or different from each other.
[0423] In -N(G6)(G6), multiple G6 values may be the same or different from each other.
[0424] • "Halogen atom"
[0425] Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.
[0426] • "Substituted or unsubstituted fluoroalkyl groups"
[0427] The term "substituted or unsubstituted fluoroalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group has been replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group have been replaced by fluorine atoms (perfluorinated groups). Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted fluoroalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted fluoroalkyl" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl" group have been replaced by a substituent. It should be noted that the term "substituted fluoroalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in a "substituted fluoroalkyl" group have been further replaced by a substituent, and groups in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl" group have been further replaced by a substituent. As a specific example of "unsubstituted fluoroalkyl", examples can be given of groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (specific example group G3) have been replaced by fluorine atoms.
[0428] • "Substituted or unsubstituted haloalkyl groups"
[0429] The term "substituted or unsubstituted haloalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group has been replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group have been replaced by halogen atoms. Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted haloalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted haloalkyl" refers to a group in which one or more hydrogen atoms of a "haloalkyl" group have been replaced by a substituent. It should be noted that "substituted haloalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in a "substituted haloalkyl" group have been further replaced by a substituent, and groups in which one or more hydrogen atoms of a substituent in a "substituted haloalkyl" group have been further replaced by a substituent. As a specific example of "unsubstituted haloalkyl", examples can be given of groups in which one or more hydrogen atoms of the above-mentioned "alkyl" (specific example group G3) have been substituted with halogen atoms. Haloalkyl is sometimes called haloalkyl.
[0430] • "Substituted or unsubstituted alkoxy groups"
[0431] As a specific example of "substituted or unsubstituted alkoxy group" as described in this specification, it is the group indicated by -O (G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
[0432] • "Substituted or unsubstituted alkylthio groups"
[0433] As a specific example of "substituted or unsubstituted alkylthio group" as described in this specification, it is the group indicated by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
[0434] • "Substituted or unsubstituted aryloxy groups"
[0435] As a specific example of "substituted or unsubstituted aryloxy group" as described in this specification, it is the group indicated by -O (G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of carbon atoms in the ring of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
[0436] • "Substituted or unsubstituted arylthio groups"
[0437] As a specific example of "substituted or unsubstituted arylthio group" as described in this specification, it is the group indicated by -S(G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of carbon atoms in the ring of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
[0438] • "Substituted or unsubstituted trialkylsilyl groups"
[0439] As a specific example of "trialkylsilyl" as described in this specification, it is the group represented by -Si(G3)(G3)(G3), where G3 refers to the "substituted or unsubstituted alkyl" described in the specific example group G3. The plurality of G3s in -Si(G3)(G3)(G3) may be identical or different from each other. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the "trialkylsilyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[0440] • "Substituted or unsubstituted aralkyl groups"
[0441] As a specific example of "substituted or unsubstituted aralkyl" as described in this specification, it is the group shown as -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl" described in specific example group G3, and G1 is the "substituted or unsubstituted aryl" described in specific example group G1. Therefore, "aralkyl" is a group in which the hydrogen atom of "alkyl" is replaced by "aryl" as a substituent, and is one embodiment of "substituted alkyl". "Unsubstituted aralkyl" is an "unsubstituted alkyl" that is substituted with "unsubstituted aryl", and the number of carbon atoms of "unsubstituted aralkyl" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.
[0442] Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl.
[0443] Unless otherwise specified in this specification, the substituted or unsubstituted aryl groups described herein are preferably phenyl, p-phenyl, meta-phenyl, o-phenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthraceneyl, phenanthryl, pyreneyl, etc. It includes methyl, triphenyl, fluorenyl, 9,9'-spirobisfluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl, etc.
[0444] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic groups described herein are preferably pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinel, carbazole (1-carbazole, 2-carbazole, 3-carbazole, 4-carbazole or 9-carbazole), benzocarbazole, azacarbazole, diazacarbazole, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophene, and naphtho-benzofuranyl. Benzothiophene, azadibenzothiophene, diazadibenzothiophene, (9-phenyl)carbazoyl ((9-phenyl)carbazo-1-yl, (9-phenyl)carbazo-2-yl, (9-phenyl)carbazo-3-yl, or (9-phenyl)carbazo-4-yl), (9-biphenyl)carbazoyl, (9-phenyl)phenylcarbazoyl, diphenylcarbazo-9-yl, phenylcarbazo-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl, and phenyldibenzothiophene, etc.
[0445] In this specification, the carbazoyl group, unless otherwise specified herein, specifically refers to any one of the following groups.
[0446] [Chemical Formula 8]
[0447]
[0448] In this specification, (9-phenyl)carbazolyl refers specifically to any one of the following groups unless otherwise specified herein.
[0449] [Chemical Formula 9]
[0450]
[0451] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.
[0452] In this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any one of the following groups unless otherwise stated in this specification.
[0453]
Chemical Formula 10
[0454]
[0455] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.
[0456] Unless otherwise specified in this specification, the substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and tert-butyl.
[0457] • "Substituted or unsubstituted aryl groups"
[0458] Unless otherwise stated, the "substituted or unsubstituted aryl group" described in this specification refers to a divalent group derived from the "substituted or unsubstituted aryl group" by removing one hydrogen atom from the aryl ring. Specific examples of "substituted or unsubstituted aryl group" (specific example group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in specific example group G1 by removing one hydrogen atom from the aryl ring.
[0459] • "Substituted or unsubstituted divalent heterocyclic groups"
[0460] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification refers to a divalent group derived from the aforementioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom from the heterocycle. Specific examples of "substituted or unsubstituted divalent heterocyclic groups" (specific example group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in specific example group G2 by removing one hydrogen atom from the heterocycle.
[0461] • "Substituted or unsubstituted alkylene compounds"
[0462] Unless otherwise stated, "substituted or unsubstituted alkylene" as described in this specification refers to a divalent group derived from the aforementioned "substituted or unsubstituted alkyl" by removing one hydrogen atom from the alkyl chain. Specific examples of "substituted or unsubstituted alkylene" (Specific Example Group G14) include divalent groups derived from the "substituted or unsubstituted alkyl" described in Specific Example Group G3 by removing one hydrogen atom from the alkyl chain.
[0463] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described herein is preferably any one of the groups in the following general formulas (TEMP-42) to (TEMP-68).
[0464]
Chemical Formula 11
[0465]
[0466]
Chemical Formula 12
[0467]
[0468] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.
[0469] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.
[0470]
Chemical Formula 13
[0471]
[0472] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.
[0473] Formulas Q9 and Q 10 They can form rings by bonding with each other via single bonds.
[0474] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.
[0475]
Chemical Formula 14
[0476]
[0477] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.
[0478] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.
[0479] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described herein is preferably any group of the following general formulas (TEMP-69) to (TEMP-102).
[0480]
Chemical Formula 15
[0481]
[0482] [Chemical Formula 16]
[0483]
[0484]
Chemical Formula 17
[0485]
[0486] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.
[0487] [Chemical Formula 18]
[0488]
[0489] [Chemical Formula 19]
[0490]
[0491]
Chemical Formula 20
[0492]
[0493]
Chemical Formula 21
[0494]
[0495] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.
[0496] The above is an explanation of "substituents described in this specification".
[0497] • "Cases where bonds form rings"
[0498] In this specification, the description of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring, or bonded together to form a substituted or unsubstituted fused ring, or not bonded together" refers to the cases of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring", "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted fused ring", and "one or more groups of two or more adjacent elements not bonded together".
[0499] The following description addresses the cases where "one or more groups of two or more adjacent rings are bonded together to form a substituted or unsubstituted monocyclic ring" and "one or more groups of two or more adjacent rings are bonded together to form a substituted or unsubstituted fused ring" (hereinafter, these cases are sometimes collectively referred to as "the case of forming a ring by bonding"). The case of anthracene compounds with the following general formula (TEMP-103) whose parent skeleton is anthracene ring will be used as an example.
[0500]
Chemical Formula 22
[0501]
[0502] For example, in R 921 ~R 930 In the case of "one or more groups of two or more adjacent elements bonded together to form a loop", the group consisting of two adjacent elements as a group refers to R. 921 With R 922 group, R 922 With R 923 group, R 923 With R 924 group, R 924 With R 930 group, R 930 With R 925 group, R 925 With R 926 group, R 926 With R 927 group, R 927 With R 928 group, R 928 With R 929 The group, and R 929 With R 921 The group.
[0503] The phrase "one or more groups" refers to the fact that two or more of the aforementioned adjacent groups can simultaneously form a loop. For example, in R... 921 With R 922 They bond together to form a ring Q A Moreover, R 925 With R 926 They bond together to form a ring Q B In this case, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).
[0504]
Chemical Formula 23
[0505]
[0506] The formation of rings from "groups of two or more adjacent elements" includes not only the case of bonds formed by groups of "two" adjacent elements, as in the previous example, but also the case of bonds formed by groups of "three or more" adjacent elements. For example, it refers to R... 921 With R 922 They bond together to form a ring Q A And R 922 With R 923 They bond together to form a ring Q C , consisting of 3 adjacent (R) 921 R 922 and R 923When the groups of components Q bond together to form a ring and fuse to the anthracene matrix, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q... A and ring Q C There are a total of R 922 .
[0507]
Chemical Formula 24
[0508]
[0509] In the formed "single ring" or "fused ring," the structure of the ring alone can be either a saturated ring or an unsaturated ring. Even when "one of the groups of two adjacent rings" forms a "single ring" or "fused ring," that "single ring" or "fused ring" can form either a saturated ring or an unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104) A and ring Q B Each is either a "single ring" or a "fused ring". Additionally, the ring Q formed in the above general formula (TEMP-105) A and Q ring C It is a "fused ring". The ring Q of the above general formula (TEMP-105) A With ring Q C Through ring Q A With ring Q C Fusing together forms a fused ring. The ring Q of the above general formula (TMEP-104) A If it is a benzene ring, then ring Q A It is a single ring. The ring Q in the above general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a fused ring.
[0510] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.
[0511] As a specific example of an aromatic hydrocarbon ring, the structure formed by the hydrogen atom-terminated group in specific example group G1 can be cited.
[0512] As a specific example of an aromatic heterocycle, one can cite the structure formed by end-capping an aromatic heterocycle group with hydrogen atoms in specific example group G2.
[0513] As a specific example of an aliphatic hydrocarbon ring, the structure formed by the hydrogen atom-terminated group in specific example group G6 can be cited.
[0514] "Ring formation" refers to the formation of a ring solely by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton forming a ring with one or more other optional elements. For example, R shown in the above general formula (TEMP-104) 921 With R 922 The ring Q formed by mutual bonding A It refers to R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 The carbon atoms of the bonded anthracene framework form rings with one or more optional elements. As a specific example, in the case of R... 921 With R 922 Forming ring Q A In the case of R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 When the bonded anthracene skeleton carbon atoms and four carbon atoms form a monocyclic unsaturated ring, R 921 With R 922 The resulting ring is a benzene ring.
[0515] Here, "optional element" is preferably selected from at least one element chosen from the group consisting of carbon, nitrogen, oxygen, and sulfur, unless otherwise specified in this specification. In the case of optional elements (e.g., carbon or nitrogen), non-ring bonds can be capped by hydrogen atoms or replaced by "optional substituents" described later. When optional elements other than carbon are included, the resulting ring is a heterocycle.
[0516] Unless otherwise specified in this specification, the "one or more optional elements" constituting a monocyclic or fused ring are preferably two or more and 15 or less, more preferably three or more and 12 or less, and even more preferably three or more and 5 or less.
[0517] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".
[0518] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".
[0519] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.
[0520] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.
[0521] In the case of "one or more groups of two or more adjacent atoms forming a substituted or unsubstituted monocyclic ring" or "a substituted or unsubstituted fused ring formed by mutual bonding", unless otherwise stated in this specification, it is preferred that one or more groups of two or more adjacent atoms form an unsaturated ring formed by mutual bonding of a plurality of atoms of a parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur.
[0522] When the aforementioned "monocyclic" or "fused-ring" rings have substituents, the substituents are, for example, the "optional substituents" described later. Specific examples of substituents when the aforementioned "monocyclic" or "fused-ring" rings have substituents are the substituents described in the section "Substituents Represented in This Specification" above.
[0523] When the aforementioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of substituents when the aforementioned "monocyclic" or "fused ring" has a substituent are the substituents described in the section "Substituents Represented in This Specification" above.
[0524] The above explains the cases of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring" and "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted fused ring" ("the case of bonding to form a ring").
[0525] Substituents when described as "substituted or unsubstituted"
[0526] In one embodiment of this specification, the substituents described above as "substituted or unsubstituted" (sometimes referred to as "optional substituents" in this specification) are, for example, selected from...
[0527] Unsubstituted alkyl groups having 1 to 50 carbon atoms
[0528] Unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0529] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms
[0530] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0531] -Si(R 901 (R) 902 (R) 903 ),
[0532] -O-(R 904 ),
[0533] -S-(R905 ),
[0534] -N(R 906 (R) 907 ),
[0535] Halogen atom, cyano group, nitro group,
[0536] Groups in the group consisting of unsubstituted aryl groups with 6 to 50 carbon atoms in the ring and unsubstituted heterocyclic groups with 5 to 50 carbon atoms in the ring, etc.
[0537] Here, R 901 ~R 907 Each independently
[0538] hydrogen atom,
[0539] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0540] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0541] A substituted or unsubstituted aryl group with 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms.
[0542] In R 901 In cases where there are two or more R's, there are two or more R's. 901 They are the same or different.
[0543] In R 902 In cases where there are two or more R's, there are two or more R's. 902 They are the same or different.
[0544] In R 903 In cases where there are two or more R's, there are two or more R's. 903 They are the same or different.
[0545] In R 904 In cases where there are two or more R's, there are two or more R's. 904 They are the same or different.
[0546] In R 905 In cases where there are two or more R's, there are two or more R's. 905 They are the same or different.
[0547] In R 906 In cases where there are two or more R's, there are two or more R's. 906 They are the same or different.
[0548] In R 907 In cases where there are two or more R's, there are two or more R's. 907 They are the same or different.
[0549] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.
[0550] Alkyl groups with 1 to 50 carbon atoms
[0551] Groups in the group consisting of aryl groups with 6 to 50 carbon atoms and heterocyclic groups with 5 to 50 atoms.
[0552] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.
[0553] Alkyl groups having 1 to 18 carbon atoms
[0554] Groups in the group consisting of aryl groups with 6 to 18 carbon atoms and heterocyclic groups with 5 to 18 atoms.
[0555] Specific examples of the substituents mentioned above are those described in the section "Substituents as set forth in this specification".
[0556] Unless otherwise stated in this specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring" with each other, preferably forming a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably forming a benzene ring.
[0557] Unless otherwise stated in this specification, optional substituents may also have other substituents. Any further substituents that may be present as optional substituents are the same as those described above.
[0558] In this specification, the numerical range referred to as "AA~BB" refers to the range included by taking the value AA recorded before "AA~BB" as the lower limit and the value BB recorded after "AA~BB" as the upper limit.
[0559] [First Implementation Method]
[0560] (Organic electroluminescent device)
[0561] The organic EL element according to this embodiment includes an anode, a cathode, a first light-emitting layer and a second light-emitting layer disposed between the anode and the cathode and directly connected to each other, and a first electron transport layer disposed between the directly connected first and second light-emitting layers and the cathode. The first light-emitting layer contains a first compound of the following general formula (1) as a first host material, and the first compound has at least one group of the following general formula (11). The second light-emitting layer contains a second compound of the following general formula (2) as a second host material. The first electron transport layer contains a third compound of the following general formula (3).
[0562] In this specification, "body material" refers, for example, to a material having a content of "50% by mass or more of the layer". Therefore, for example, the content of the first compound shown in the following general formula (1) in the first light-emitting layer is 50% by mass or more of the total mass of the first light-emitting layer. The content of the second compound shown in the following general formula (2) in the second light-emitting layer is, for example, 50% by mass or more of the total mass of the second light-emitting layer. Furthermore, for example, the content of "body material" can be 60% by mass or more of the layer, 70% by mass or more of the layer, 80% by mass or more of the layer, 90% by mass or more of the layer, or 95% by mass or more of the layer.
[0563] In the organic EL element of this embodiment, it is also preferable that the first light-emitting layer is disposed between the anode and the second light-emitting layer.
[0564] In the organic EL element of this embodiment, it is also preferable that the second light-emitting layer is disposed between the anode and the first light-emitting layer.
[0565] In addition to the first light-emitting layer, the second light-emitting layer, and the first electron transport layer, the organic EL device according to this embodiment may have one or more organic layers. Examples of organic layers include at least one layer selected from hole injection layer, hole transport layer, light-emitting layer, electron injection layer, electron transport layer, hole blocking layer, and electron blocking layer.
[0566] In the organic EL element of this embodiment, the organic layer may consist only of a first light-emitting layer, a second light-emitting layer, and a first electron transport layer. For example, it may further have at least one layer selected from hole injection layer, hole transport layer, electron injection layer, electron transport layer, hole blocking layer, and electron blocking layer.
[0567] (Electron transport layer)
[0568] The organic EL element involved in this embodiment preferably has at least one of a second electron transport layer and a third electron transport layer, in addition to the first electron transport layer.
[0569] The second electron transport layer is preferably disposed between the first electron transport layer and the cathode.
[0570] The third electron transport layer is preferably disposed between the first electron transport layer and the light-emitting layer.
[0571] In the case of an organic EL device according to this embodiment that includes multiple electron transport layers, the electron transport layer disposed on the light-emitting layer side within these electron transport layers is sometimes referred to as a hole blocking layer.
[0572] In the organic EL element of this embodiment, it is also preferable that the first electron transport layer is directly connected to the light-emitting layer disposed on the cathode side of the first light-emitting layer and the second light-emitting layer.
[0573] In the organic EL element of this embodiment, it is also preferable to further have a second electron transport layer disposed between the first electron transport layer and the cathode.
[0574] In the organic EL element of this embodiment, it is also preferable that the first electron transport layer is directly connected to the light-emitting layer disposed on the cathode side of the first light-emitting layer and the second light-emitting layer, and that a second electron transport layer is disposed between the first electron transport layer and the cathode.
[0575] In the organic EL element of this embodiment, the second electron transport layer preferably contains a fourth compound represented by the following general formula (3). It should be noted that the third compound contained in the first electron transport layer and the fourth compound contained in the second electron transport layer have different structures.
[0576] In the organic EL element involved in this embodiment, it is preferable that the first electron transport layer and the second electron transport layer are directly connected.
[0577] In the organic EL element of this embodiment, it is also preferable that a third electron transport layer is provided between the first and second light-emitting layers that are directly connected to each other and the first electron transport layer.
[0578] In the organic EL element of this embodiment, the third electron transport layer preferably contains the fifth compound shown in the following general formula (3). It should be noted that the third compound contained in the first electron transport layer and the fifth compound contained in the third electron transport layer have different structures.
[0579] In the organic EL element involved in this embodiment, it is preferable that the first electron transport layer and the third electron transport layer are directly connected.
[0580] In the organic EL element of this embodiment, it is preferable that the third electron transport layer is directly connected to the light-emitting layer disposed on the cathode side of the first light-emitting layer and the second light-emitting layer.
[0581] (Hole transport layer)
[0582] In the organic EL element of this embodiment, a hole transport layer is preferably provided between the anode and the light-emitting layer.
[0583] (The general structure of an organic EL device)
[0584] Figure 1 This illustrates the general configuration of an example of an organic EL element involved in this embodiment.
[0585] The organic EL element 1 includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is constructed by stacking a hole injection layer 6, a hole transport layer 7, a first light-emitting layer 51, a second light-emitting layer 52, a first electron transport layer 81, a second electron transport layer 82, and an electron injection layer 9 in sequence from the anode 3 side.
[0586] Figure 2 This illustrates the general configuration of an example of an organic EL element involved in this embodiment.
[0587] The organic EL element 1A includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10A disposed between the anode 3 and the cathode 4. The organic layer 10A is constructed by stacking a hole injection layer 6, a hole transport layer 7, a first light-emitting layer 51, a second light-emitting layer 52, a third electron transport layer 83, a first electron transport layer 81, and an electron injection layer 9 in sequence from the anode 3 side.
[0588] Figure 3 This illustrates the general configuration of an example of an organic EL element involved in this embodiment.
[0589] The organic EL element 1B includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10B disposed between the anode 3 and the cathode 4. The organic layer 10B is constructed by stacking a hole injection layer 6, a hole transport layer 7, a second light-emitting layer 52, a first light-emitting layer 51, a first electron transport layer 81, a second electron transport layer 82, and an electron injection layer 9 in sequence from the anode 3 side.
[0590] Figure 4 This illustrates the general configuration of an example of an organic EL element involved in this embodiment.
[0591] The organic EL element 1C includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10C disposed between the anode 3 and the cathode 4. The organic layer 10C is constructed by stacking a hole injection layer 6, a hole transport layer 7, a second light-emitting layer 52, a first light-emitting layer 51, a third electron transport layer 83, a first electron transport layer 81, and an electron injection layer 9 in sequence from the anode 3 side.
[0592] (First light-emitting layer)
[0593] The first light-emitting layer is directly connected to the second light-emitting layer. The first light-emitting layer contains a first compound represented by the following general formula (1) as a first host material. The first compound has at least one group represented by the following general formula (11).
[0594] The first luminescent layer preferably contains a compound that exhibits luminescence with a peak wavelength of 430 nm or higher and 480 nm or lower.
[0595] The first luminescent layer preferably also contains a seventh compound with fluorescent properties.
[0596] The seventh compound is preferably a compound that exhibits luminescence with a maximum peak wavelength of 430 nm or more and 480 nm or less.
[0597] In the organic EL element of this embodiment, when the first light-emitting layer comprises a first compound and a seventh compound, the first compound is preferably a host material (sometimes also called a matrix material), and the seventh compound is preferably a dopant material (sometimes also called a guest material, emitter, or light-emitting material).
[0598] The first luminescent layer preferably does not contain phosphorescent materials as dopants.
[0599] Furthermore, the first light-emitting layer preferably does not contain heavy metal complexes or phosphorescent rare-earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.
[0600] In addition, the first light-emitting layer preferably does not contain metal complexes.
[0601] ·First compound
[0602] The first compound is a compound represented by the following general formula (1). The first compound has at least one group represented by the following general formula (11).
[0603] [Chemical Formula 25]
[0604]
[0605] In the above general formula (1),
[0606] R 101 ~R 110 Each independently
[0607] hydrogen atom,
[0608] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0609] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0610] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0611] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0612] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0613] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0614] -O-(R 904 The groups shown in the figure,
[0615] -S-(R 905 The groups shown in the figure,
[0616] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0617] -C(=O)R 801 The groups shown
[0618] -COOR 802 The groups shown
[0619] Halogen atoms,
[0620] cyano,
[0621] Nitro,
[0622] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[0623] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[0624] The groups represented by the above general formula (11),
[0625] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11) above.
[0626] When there are multiple groups represented by the above general formula (11), the multiple groups represented by the above general formula (11) may be the same as or different from each other.
[0627] L 101 for
[0628] single bond,
[0629] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[0630] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0631] Ar 101 for
[0632] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0633] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0634] mx is 0, 1, 2, 3, 4, or 5.
[0635] In L 101 In cases where there are two or more L's, there are two or more L's. 101 They are the same or different.
[0636] In Ar 101 In cases where there are two or more Ar, two or more Ar 101 They are the same or different.
[0637] In the above general formula (11), * indicates the bonding position with the pyrene ring in the above general formula (1).
[0638] In the first compound represented by the above general formula (1), R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently
[0639] hydrogen atom,
[0640] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0641] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0642] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0643] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0644] In R 901In the case of multiple Rs, multiple Rs 901 They are the same or different.
[0645] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[0646] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[0647] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[0648] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.
[0649] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[0650] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.
[0651] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[0652] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
[0653] The group represented by the above general formula (11) is preferably the group represented by the following general formula (111).
[0654]
Chemical Formula 26
[0655]
[0656] (In the above general formula (111),
[0657] X1 is CR 123 R 124 oxygen atom, sulfur atom or NR 125 ,
[0658] L 111 and L 112 Each independently
[0659] single bond,
[0660] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[0661] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0662] ma can be 0, 1, 2, 3, or 4.
[0663] mb can be 0, 1, 2, 3, or 4.
[0664] ma+mb is 0, 1, 2, 3 or 4.
[0665] Ar 101 Ar in the above general formula (11) 101 Same meaning
[0666] R 121 R 122 R 123 R 124 and R 125 Each independently
[0667] hydrogen atom,
[0668] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0669] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0670] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0671] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0672] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0673] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0674] -O-(R 904 The groups shown in the figure,
[0675] -S-(R 905 The groups shown in the figure,
[0676] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0677] -C(=O)R 801 The groups shown
[0678] -COOR 802 The groups shown
[0679] Halogen atoms,
[0680] cyano,
[0681] Nitro,
[0682] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0683] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0684] mc is 3.
[0685] 3 Rs 121 They are the same or different.
[0686] md is 3
[0687] 3 Rs 122 (They may be the same or different.)
[0688] In the group represented by the above general formula (111), at positions *1 to *8 of the carbon atoms in the ring structure represented by the following general formula (111a), L 111 Bonded to any position from *1 to *4, R 121 Bonded to the remaining 3 positions in *1 to *4, L 112 Bonded to any position from *5 to *8, R 122 It is bonded to the other 3 positions in *5 to *8.
[0689] [Chemical Formula 27]
[0690]
[0691] For example, in the groups shown in the above general formula (111), in L 111 The position of the carbon atom *2 bonded to the ring structure shown in the above general formula (111a), L 112 When the carbon atom of *7 in the ring structure shown in the above general formula (111a) is bonded, the group shown in the above general formula (111) is represented by the following general formula (111b).
[0692] [Chemical Formula 28]
[0693]
[0694] (In the above general formula (111b),
[0695] X1, L 111 L 112 ma, mb, Ar 101 R 121 R 122 R 123 R 124and R 125 Each independently relates to X1 and L in the above general formula (111). 111 L 112 ma, mb, Ar 101 R 121 R 122 R 123 R 124 and R 125 Same meaning
[0696] Multiple R 121 They are the same or different.
[0697] Multiple R 122 (They may be the same or different.)
[0698] In the organic EL element of this embodiment, the group represented by the above general formula (111) is preferably the group represented by the above general formula (111b).
[0699] In the organic EL element involved in this embodiment, it is preferred that ma is 0, 1 or 2, and mb is 0, 1 or 2.
[0700] In the organic EL element involved in this embodiment, it is preferred that ma is 0 or 1 and mb is 0 or 1.
[0701] In the group represented by the above general formula (111), when ma is 0 and mb is 1, the group represented by the above general formula (111) is represented by the following general formula (111c).
[0702] [Chemical Formula 29]
[0703]
[0704] (In the above general formula (111c), X1, L 112 ,mc,md,Ar 101 R 121 and R 122 Each independently relates to X1 and L in the above general formula (111). 112 ,mc,md,Ar 101 R 121 and R 122 The meaning is the same.
[0705] In the organic EL element involved in this embodiment, Ar is preferred. 101 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[0706] In the organic EL element involved in this embodiment, Ar is preferred. 101It can be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted pyrene, a substituted or unsubstituted phenanthryl, or a substituted or unsubstituted fluorene.
[0707] In the organic EL element involved in this embodiment, Ar is also preferred. 101 It is a group represented by the following general formula (12), general formula (13) or general formula (14).
[0708]
Chemical Formula 30
[0709]
[0710] (In the above general formulas (12), (13) and (14),
[0711] R 111 ~R 120 Each independently
[0712] hydrogen atom,
[0713] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0714] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0715] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0716] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0717] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0718] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0719] -O-(R 904 The groups shown in the figure,
[0720] -S-(R 905 The groups shown in the figure,
[0721] -N(R 906 (R) 907 The groups shown in the figure,
[0722] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0723] -C(=O)R 124 The groups shown
[0724] -COOR 125 The groups shown
[0725] Halogen atoms,
[0726] cyano,
[0727] Nitro,
[0728] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0729] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0730] In the above general formulas (12), (13), and (14), * indicates the same as L in the above general formula (11). 101 The bonding position and the L in the above general formula (111) 112 The bonding position, or the L in the above general formula (111b) 112 (The bonding location.)
[0731] R in the above general formulas (12), (13) and (14) is also preferred. 124 and R 125 Each independently of the aforementioned R 801 and R 802 They have the same meaning.
[0732] The first compound is preferably represented by the following general formula (101).
[0733]
Chemical Formula 31
[0734]
[0735] (In the above general formula (101),
[0736] R 101 ~R 120 Each independently
[0737] hydrogen atom,
[0738] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0739] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0740] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0741] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0742] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0743] -Si(R 901 (R) 902 (R) 903The groups shown in the figure,
[0744] -O-(R 904 The groups shown in the figure,
[0745] -S-(R 905 The groups shown in the figure,
[0746] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0747] -C(=O)R 801 The groups shown
[0748] -COOR 802 The groups shown
[0749] Halogen atoms,
[0750] cyano,
[0751] Nitro,
[0752] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0753] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0754] Among them, R 101 ~R 110 One of them represents L 101 The bonding position, R 111 ~R 120 One of them represents L 101 The bonding position,
[0755] L 101 for
[0756] single bond,
[0757] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[0758] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0759] mx is 0, 1, 2, 3, 4, or 5.
[0760] In L 101 In cases where there are two or more L's, there are two or more L's. 101 (They may be the same or different.)
[0761] In the above general formula (101), R 103 To be with L 101 The bonding position, R 120 To be with L 101In the case of the bonding positions, the compound represented by the above general formula (101) is represented by the following general formula (101A).
[0762]
Chemical Formula 32
[0763]
[0764] (In the above general formula (101A), R) 101 R 102 R 104 ~R 119 L 101 And mx are respectively related to R in the above general formula (101) 101 R 102 R 104 ~R 119 L 101 (Same meaning as mx)
[0765] In the organic EL element involved in this embodiment, L is preferred. 101 It is a single bond, or a cyclic aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[0766] In the organic EL element involved in this embodiment, the first compound is preferably represented by the following general formula (102).
[0767]
Chemical Formula 33
[0768]
[0769] (In the above general formula (102),
[0770] R 101 ~R 120 Each independently relates to R in the above general formula (101). 101 ~R 120 Same meaning
[0771] Among them, R 101 ~R 110 One of them represents L 111 The bonding position, R 111 ~R 120 One of them represents L 112 The bonding position,
[0772] X1 is CR 123 R 124 oxygen atom, sulfur atom or NR 125 ,
[0773] L 111 and L 112 Each independently
[0774] single bond,
[0775] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[0776] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0777] ma can be 0, 1, 2, 3, or 4.
[0778] mb can be 0, 1, 2, 3, or 4.
[0779] ma+mb is 0, 1, 2, 3 or 4.
[0780] R 121 R 122 R 123 R 124 and R 125 Each independently
[0781] hydrogen atom,
[0782] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0783] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0784] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0785] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0786] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0787] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0788] -O-(R 904 The groups shown in the figure,
[0789] -S-(R 905 The groups shown in the figure,
[0790] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0791] -C(=O)R 801 The groups shown
[0792] -COOR 802 The groups shown
[0793] Halogen atoms,
[0794] cyano,
[0795] Nitro,
[0796] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0797] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0798] mc is 3.
[0799] 3 Rs 121 They are the same or different.
[0800] md is 3
[0801] 3 Rs 122 (They may be the same or different.)
[0802] In the compounds represented by the above general formula (102), preferably, ma is 0, 1 or 2, and mb is 0, 1 or 2.
[0803] In the compounds represented by the above general formula (102), preferably, ma is 0 or 1 and mb is 0 or 1.
[0804] In the organic EL element involved in this embodiment, R is preferred. 101 ~R 110 Two or more of them are groups represented by the general formula (11) above.
[0805] In the organic EL element involved in this embodiment, R is preferred. 101 ~R 110 Two or more of them are groups represented by the general formula (11) above and Ar 101 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[0806] In the organic EL element involved in this embodiment, the preferred one is...
[0807] Ar 101 It is neither a substituted nor an unsubstituted pyrene group.
[0808] L 101 It is neither a replaced nor unreplaced pyrene group.
[0809] R, which is not a group represented by the above general formula (11) 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted pyrene group.
[0810] In the organic EL element involved in this embodiment, the preferred one is...
[0811] R is not a group represented by the general formula (11) above. 101 ~R 110 Each independently
[0812] hydrogen atom,
[0813] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0814] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0815] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0816] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[0817] In the organic EL element involved in this embodiment, the preferred one is...
[0818] R is not a group represented by the general formula (11) above. 101 ~R 110 Each independently
[0819] hydrogen atom,
[0820] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[0821] Cycloalkyl groups, substituted or unsubstituted, having 3 to 50 carbon atoms.
[0822] In the organic EL element involved in this embodiment, the R group is not the group shown in the above general formula (11). 101 ~R 110 Hydrogen atoms are preferred.
[0823] In the organic EL element involved in this embodiment, X1 is preferably CR. 123 R 124 For example, when X1 is CR 123 R 124 In the case of the above general formula (111), the group represented by the above general formula (111d) is represented by the following general formula (111d).
[0824]
Chemical Formula 34
[0825]
[0826] (In the above general formula (111d), L) 111 L 112 ma, mb, ma+mb, Ar 101 R 121 R 122 R 123 R 124 R 125 , mc and md are defined in the same way as in the general formula (111) above.
[0827] In the organic EL element involved in this embodiment, R 123 With R 124 Ideally, they should not be bonded to each other.
[0828] In the organic EL element involved in this embodiment, L is preferred. 111 and L 112 At least one of them is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in the cyclic ring, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 carbon atoms in the cyclic ring.
[0829] In the first compound, groups described as "substituted or unsubstituted" are preferably "unsubstituted".
[0830] (Method for manufacturing the first compound)
[0831] The first compound can be manufactured using known methods. Alternatively, the first compound can also be manufactured by using known alternative reactions and starting materials corresponding to the target substance, following the known methods.
[0832] (Specific examples of the first compound)
[0833] Specific examples of the first compound include the following compounds. However, the present invention is not limited to these specific examples of the first compound.
[0834]
Chemical Formula 35
[0835]
[0836]
Chemical Formula 36
[0837]
[0838]
Chemical Formula 37
[0839]
[0840] [Chemical Formula 38]
[0841]
[0842] [Chemical Formula 39]
[0843]
[0844]
Chemical Formula 40
[0845]
[0846]
Chemical Formula 41
[0847]
[0848]
Chemical Formula 42
[0849]
[0850]
Chemical Formula 43
[0851]
[0852]
Chemical Formula 44
[0853]
[0854] [Chemical Formula 45]
[0855]
[0856]
Chemical Formula 46
[0857]
[0858] [Chemical Formula 47]
[0859]
[0860] [Chemical Formula 48]
[0861]
[0862] [Chemical Formula 49]
[0863]
[0864] [Chemical Formula 50]
[0865]
[0866]
Chemical Formula 51
[0867]
[0868]
Chemical Formula 52
[0869]
[0870]
Chemical Formula 53
[0871]
[0872] [Chemical Formula 54]
[0873]
[0874]
Chemical Formula 55
[0875]
[0876] [Chemical Formula 56]
[0877]
[0878] [Chemical Formula 57]
[0879]
[0880] [Chemical Formula 58]
[0881]
[0882] (Second light-emitting layer)
[0883] The second light-emitting layer is directly connected to the first light-emitting layer. The second light-emitting layer contains a second compound as a second host material, as shown in the following general formula (2).
[0884] The second luminescent layer preferably contains a compound that exhibits luminescence with a maximum peak wavelength of 430 nm or higher and 480 nm or lower.
[0885] The second luminescent layer preferably also contains a sixth compound with fluorescent properties.
[0886] The sixth compound is preferably a compound that exhibits luminescence with a maximum peak wavelength of 430 nm or more and 480 nm or less.
[0887] In the organic EL element of this embodiment, when the second light-emitting layer comprises a second compound and a sixth compound, the second compound is preferably a host material (sometimes also called a matrix material), and the sixth compound is preferably a dopant material (sometimes also called a guest material, emitter, or light-emitting material).
[0888] The second light-emitting layer preferably does not contain phosphorescent materials as dopants.
[0889] Furthermore, the second luminescent layer preferably does not contain heavy metal complexes or phosphorescent rare-earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.
[0890] In addition, the second light-emitting layer preferably does not contain metal complexes.
[0891] ·Second compound
[0892] The second compound represented by general formula (2) involved in this embodiment will be described.
[0893] [Chemical Formula 59]
[0894]
[0895] (In the above general formula (2),
[0896] R 201 ~R 208 Each independently
[0897] hydrogen atom,
[0898] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0899] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0900] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0901] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0902] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0903] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0904] -O-(R 904 The groups shown in the figure,
[0905] -S-(R 905 The groups shown in the figure,
[0906] -N(R 906 (R) 907 The groups shown in the figure,
[0907] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0908] -C(=O)R 801 The groups shown
[0909] -COOR 802 The groups shown
[0910] Halogen atoms,
[0911] cyano,
[0912] Nitro,
[0913] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0914] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0915] L 201 and L 202 Each independently
[0916] single bond,
[0917] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[0918] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0919] Ar 201 and Ar 202 Each independently
[0920] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0921] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[0922] (In the second compound involved in this embodiment, R) 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently
[0923] hydrogen atom,
[0924] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0925] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0926] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0927] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0928] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[0929] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[0930] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[0931] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[0932] In R 905In the case of multiple Rs, multiple Rs 905 They are the same or different.
[0933] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[0934] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.
[0935] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[0936] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)
[0937] In the organic EL element involved in this embodiment, R is preferred. 201 ~R 208 Each independently
[0938] hydrogen atom,
[0939] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0940] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0941] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0942] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0943] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0944] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0945] -O-(R 904 The groups shown in the figure,
[0946] -S-(R 905 The groups shown in the figure,
[0947] -N(R 906 (R) 907 The groups shown in the figure,
[0948] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0949] -C(=O)R801 The groups shown
[0950] -COOR 802 The groups shown
[0951] Halogen atoms,
[0952] cyano, or
[0953] Nitro,
[0954] L 201 and L 202 Each independently
[0955] single bond,
[0956] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[0957] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0958] Ar 201 and Ar 202 Each independently
[0959] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0960] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[0961] In the organic EL element involved in this embodiment, L is preferred. 201 and L 202 Each is an arylene group, independently of a single bond, or substituted or unsubstituted, forming a cyclic group with 6 to 50 carbon atoms. 201 and Ar 202 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.
[0962] In the organic EL element involved in this embodiment, Ar 201 and Ar 202 Each of the following is preferably phenyl, naphthyl, phenanthryl, biphenyl, terphenyl, diphenylfluorenyl, dimethylfluorenyl, benzodiphenylfluorenyl, benzodimethylfluorenyl, dibenzofuranyl, dibenzothiophene, naphthobenzofuranyl, or naphthobenzothiophene.
[0963] In the organic EL element of this embodiment, the second compound represented by the above general formula (2) is preferably a compound represented by the following general formulas (201), (202), (203), (204), (205), (206), (207), (208), (209), or (210).
[0964] [Chemical Formula 60]
[0965]
[0966]
Chemical Formula 61
[0967]
[0968]
Chemical Formula 62
[0969]
[0970]
Chemical Formula 63
[0971]
[0972]
Chemical Formula 64
[0973]
[0974]
Chemical Formula 65
[0975]
[0976]
Chemical Formula 66
[0977]
[0978] [Chemical Formula 67]
[0979]
[0980]
Chemical Formula 68
[0981]
[0982]
Chemical Formula 69
[0983]
[0984] In the above general formulas (201) to (210),
[0985] L 201 and Ar 201 L in the above general formula (2) 201 and Ar 201 Same meaning
[0986] R 201 ~R 208 Each independently relates to R in the above general formula (2) 201 ~R 208 The meaning is the same.
[0987] The second compound represented by the above general formula (2) is also preferably a compound represented by the following general formulas (221), (222), (223), (224), (225), (226), (227), (228) or (229).
[0988] [Chemical Formula 70]
[0989]
[0990]
Chemical Formula 71
[0991]
[0992]
Chemical Formula 72
[0993]
[0994]
Chemical Formula 73
[0995]
[0996] [Chemical Formula 74]
[0997]
[0998] [Chemical Formula 75]
[0999]
[1000] [Chemical Formula 76]
[1001]
[1002]
Chemical Formula 77
[1003]
[1004] [Chemical Formula 78]
[1005]
[1006] (In the above general formulas (221), (222), (223), (224), (225), (226), (227), (228), and (229),
[1007] R 201 and R 203 ~R 208 Each independently relates to R in the above general formula (2) 201 and R 203 ~R 208 Same meaning
[1008] L 201 and Ar 201 Each of the above general formulas (2) with L 201 and Ar 201 Same meaning
[1009] L 203 L in the above general formula (2) 201 Same meaning
[1010] L 203 With L 201 They are the same or different.
[1011] Ar 203 Ar in the above general formula (2) 201 Same meaning
[1012] Ar 203 with Ar 201 (They may be the same or different.)
[1013] The second compound represented by the above general formula (2) is also preferably a compound represented by the following general formulas (241), (242), (243), (244), (245), (246), (247), (248) or (249).
[1014] [Chemical Formula 79]
[1015]
[1016] [Chemical Formula 80]
[1017]
[1018]
Chemical Formula 81
[1019]
[1020]
Chemical Formula 82
[1021]
[1022]
Chemical Formula 83
[1023]
[1024]
Chemical Formula 84
[1025]
[1026]
Chemical Formula 85
[1027]
[1028]
Chemical Formula 86
[1029]
[1030] [Chemical Formula 87]
[1031]
[1032] (In the above general formulas (241), (242), (243), (244), (245), (246), (247), (248), and (249),
[1033] R 201 R 202 and R 204 ~R 208 Each independently relates to R in the above general formula (2) 201 R 202 and R 204 ~R 208 Same meaning
[1034] L 201 and Ar 201 Each of the above general formulas (2) with L 201 and Ar 201 Same meaning
[1035] L 203 L in the above general formula (2) 201 Same meaning
[1036] L 203 With L 201 They are the same or different.
[1037] Ar 203 Ar in the above general formula (2) 201 Same meaning
[1038] Ar 203 with Ar 201 (They may be the same or different.)
[1039] In the second compound represented by the above general formula (2), it is preferable that the R group is not represented by the group represented by the above general formula (21). 201 ~R 208 Each independently
[1040] hydrogen atom,
[1041] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1042] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or
[1043] -Si(R 901 (R) 902 (R) 903 The group shown is ).
[1044] Preferred L 101 for
[1045] single key, or
[1046] Unsubstituted arylene groups with 6 to 22 carbon atoms in the cyclic group,
[1047] Ar 101 It is an aryl group with 6 to 22 carbon atoms, either substituted or unsubstituted.
[1048] In the organic EL element involved in this embodiment, the preferred one is...
[1049] In the second compound represented by the above general formula (2), R 201 ~R 208 Each independently
[1050] hydrogen atom,
[1051] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1052] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or
[1053] -Si(R 901 (R) 902 (R) 903 The group shown is ).
[1054] In the organic EL element involved in this embodiment,
[1055] In the second compound represented by the above general formula (2), R 201 ~R 208 Hydrogen atoms are preferred.
[1056] In the second compound described above, the groups described as "substituted or unsubstituted" are preferably "unsubstituted".
[1057] (Method for manufacturing the second compound)
[1058] The second compound can be manufactured using known methods. Alternatively, the second compound can also be manufactured by using known alternative reactions and starting materials corresponding to the target substance, following the known methods.
[1059] (Specific example of the second compound)
[1060] Specific examples of the second compound include the following compounds. However, the present invention is not limited to these specific examples of the second compound.
[1061]
Chemical Formula 88
[1062]
[1063]
Chemical Formula 89
[1064]
[1065] [Chemical Formula 90]
[1066]
[1067]
Chemical Formula 91
[1068]
[1069]
Chemical Formula 92
[1070]
[1071] [Chemical Formula 93]
[1072]
[1073] [Chemical Formula 94]
[1074]
[1075] [Chemical Formula 95]
[1076]
[1077]
Chemical Formula 96
[1078]
[1079] [Chemical Formula 97]
[1080]
[1081]
Chemical Formula 98
[1082]
[1083]
Chemical Formula 99
[1084]
[1085]
Chemical Formula 100
[1086]
[1087]
Chemical Formula 101
[1088]
[1089]
Chemical Formula 102
[1090]
[1091]
Chemical Formula 103
[1092]
[1093] [Chemical Formula 104]
[1094]
[1095] [Chemical Formula 105]
[1096]
[1097] [Chemical Formula 106]
[1098]
[1099] [Chemical Formula 107]
[1100]
[1101] [Chemical Formula 108]
[1102]
[1103] [Chemical Formula 109]
[1104]
[1105]
Chemical Formula 110
[1106]
[1107]
Chemical Formula 111
[1108]
[1109]
Chemical Formula 112
[1110]
[1111] Compounds 6 and 7
[1112] The sixth and seventh compounds are each independently selected from one or more compounds shown in the following general formula (3A), the following general formula (4), the following general formula (5), the following general formula (6), the following general formula (7), the following general formula (8), the following general formula (9), and the following general formula (10).
[1113] (The compound represented by general formula (3A))
[1114] The compounds represented by general formula (3A) will be described.
[1115]
Chemical Formula 113
[1116]
[1117] (In the above general formula (3A),
[1118] Ra 301 Ra 302 Ra 303 Ra 304 Ra 305 Ra 306 Ra 307 Ra 308 Ra 309 and Ra 310 One or more of the groups consisting of two or more adjacent elements.
[1119] They bond together to form substituted or unsubstituted monocyclic rings.
[1120] They bond together to form substituted or unsubstituted fused rings, or
[1121] They do not bond with each other.
[1122] Ra 301 ~Ra 310 At least one of them is a monovalent group represented by the following general formula (31A),
[1123] Ra does not form the above-mentioned monocyclic ring, does not form the above-mentioned fused ring, and is not a monovalent group represented by the following general formula (31A). 301 ~Ra 310 Each independently
[1124] hydrogen atom,
[1125] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1126] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1127] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1128] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1129] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1130] -O-(R 904 The groups shown in the figure,
[1131] -S-(R 905 The groups shown in the figure,
[1132] -N(R 906 (R) 907 The groups shown in the figure,
[1133] Halogen atoms,
[1134] cyano,
[1135] Nitro,
[1136] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1137] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1138]
Chemical Formula 114
[1139]
[1140] (In the above general formula (31A),
[1141] Ara 301 and Ara 302 Each independently
[1142] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1143] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1144] La 301 La 302 and La 303 Each independently
[1145] single bond,
[1146] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or
[1147] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.
[1148] * indicates the bonding position in the pyrene ring in the above general formula (3A).
[1149] In compounds six and seven, R 901 R 902 R 903 R 904 R 905 R 906 and R 907 Each independently
[1150] hydrogen atom,
[1151] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1152] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1153] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1154] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1155] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[1156] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[1157] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[1158] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[1159] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[1160] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[1161] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.
[1162] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[1163] In R 907 In the case of multiple Rs, multiple Rs 907They are the same or different.
[1164] In the above general formula (3A), Ra is preferred. 301 ~Ra 310 Two of them are groups represented by the general formula (31A) above.
[1165] In one embodiment, the compound represented by the above general formula (3A) is the compound represented by the following general formula (33A).
[1166]
Chemical Formula 115
[1167]
[1168] (In the above general formula (33A),
[1169] Ra 311 Ra 312 Ra 313 Ra 314 Ra 315 Ra 316 Ra 317 and Ra 318 Each independently interacts with Ra in the above general formula (3A) that is not a monovalent group represented by the above general formula (31A). 301 ~Ra 310 Same meaning
[1170] La 311 La 312 La 313 La 314 La 315 and La 316 Each independently
[1171] single bond,
[1172] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or
[1173] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.
[1174] Ara 312 Ara 313 Ara 315 and Ara 316 Each independently
[1175] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1176] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1177] In the above general formula (31A), La 301Preferred to be a single bond, La 302 and La 303 Single bonds are preferred.
[1178] In one embodiment, the compound represented by the above general formula (3A) is represented by the following general formula (34A) or general formula (35A).
[1179]
Chemical Formula 116
[1180]
[1181] (In the above general formula (34A),
[1182] Ra 311 ~Ra 318 Each independently interacts with Ra in the above general formula (3A) that is not a monovalent group represented by the above general formula (31A). 301 ~Ra 310 Same meaning
[1183] La 312 La 313 La 315 and La 316 Each independently relates to La in the above general formula (33A) 312 La 313 La 315 and La 316 Same meaning
[1184] Ara 312 Ara 313 Ara 315 and Ara 316 Each independently relates to Ara in the above general formula (33A). 312 Ara 313 Ara 315 and Ara 316 The meaning is the same.
[1185]
Chemical Formula 117
[1186]
[1187] (In the above general formula (35A),
[1188] Ra 311 ~Ra 318 Each independently interacts with Ra in the above general formula (3A) that is not a monovalent group represented by the above general formula (31A). 301 ~Ra 310 Same meaning
[1189] Ara 312 Ara313 Ara 315 and Ara 316 Each independently relates to Ara in the above general formula (33A). 312 Ara 313 、ATa 315 and Ara 316 The meaning is the same.
[1190] In the above general formula (31A), Ara is preferred. 301 and Ara 302 At least one of them is a group represented by the following general formula (36A).
[1191] In the above general formulas (33A) to (35A), Ara is preferred. 312 and Ara 313 At least one of them is a group represented by the following general formula (36A).
[1192] In the above general formulas (33A) to (35A), Ara is preferred. 315 and Ara 316 At least one of them is a group represented by the following general formula (36A).
[1193]
Chemical Formula 118
[1194]
[1195] (In the above general formula (36A),
[1196] Xa3 represents an oxygen atom or a sulfur atom.
[1197] Ra 321 ~Ra 327 One or more of the groups consisting of two or more adjacent elements.
[1198] They bond together to form substituted or unsubstituted monocyclic rings.
[1199] They bond together to form substituted or unsubstituted fused rings, or
[1200] They do not bond with each other.
[1201] Ra does not form the aforementioned single ring and does not form the aforementioned fused ring 321 Ra 322 Ra 323 Ra 324 Ra 325 Ra 326 and Ra 327 Each independently
[1202] hydrogen atom,
[1203] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1204] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1205] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1206] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1207] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1208] -O-(R 904 The groups shown in the figure,
[1209] -S-(R 905 The groups shown in the figure,
[1210] -N(R 906 (R) 907 The groups shown in the figure,
[1211] Halogen atoms,
[1212] cyano,
[1213] Nitro,
[1214] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1215] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1216] * indicates that it is related to La 302 La 303 La 312 La 313 La 315 Or La 316 (The bonding location.)
[1217] Xa3 is preferably composed of oxygen atoms.
[1218] Preferred Ra 321 ~Ra 327 At least one of them is
[1219] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1220] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1221] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1222] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1223] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1224] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1225] In the above general formula (31A), Ara is preferred. 301 For the group represented by the above general formula (36A), Ara 302 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[1226] In the above general formulas (33A) to (35A), Ara is preferred. 312 For the group represented by the above general formula (36A), Ara 313 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[1227] In the above general formulas (33A) to (35A), Ara is preferred. 315 For the group represented by the above general formula (36A), Ara 316 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[1228] In one embodiment, the compound represented by the above general formula (3A) is represented by the following general formula (37A).
[1229]
Chemical Formula 119
[1230]
[1231] (In the above general formula (37A),
[1232] Ra 311 ~Ra 318 Each independently interacts with Ra in the above general formula (3A) that is not a monovalent group represented by the above general formula (31A). 301 ~Ra 310 Same meaning
[1233] Ra 321 ~Ra 327 One or more of the groups consisting of two or more adjacent elements.
[1234] They bond together to form substituted or unsubstituted monocyclic rings.
[1235] They bond together to form substituted or unsubstituted fused rings, or
[1236] They do not bond with each other.
[1237] Ra 341 ~Ra 347One or more of the groups consisting of two or more adjacent elements.
[1238] They bond together to form substituted or unsubstituted monocyclic rings.
[1239] They bond together to form substituted or unsubstituted fused rings, or
[1240] They do not bond with each other.
[1241] Ra does not form the aforementioned single ring and does not form the aforementioned fused ring 321 ~Ra 327 and Ra 341 ~Ra 347 Each independently
[1242] hydrogen atom,
[1243] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1244] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1245] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1246] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1247] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1248] -O-(R 904 The groups shown in the figure,
[1249] -S-(R 905 The groups shown in the figure,
[1250] -N(R 906 (R) 907 The groups shown in the figure,
[1251] Halogen atoms,
[1252] cyano,
[1253] Nitro,
[1254] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1255] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1256] Ra 331 ~Ra 335 and Ra 351 ~Ra 355 Each independently
[1257] hydrogen atom,
[1258] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1259] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1260] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1261] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1262] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1263] -O-(R 904 The groups shown in the figure,
[1264] -S-(R 905 The groups shown in the figure,
[1265] -N(R 906 (R) 907 The groups shown in the figure,
[1266] Halogen atom, cyano group, nitro group,
[1267] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1268] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1269] (Specific examples of compounds represented by general formula (3A))
[1270] As a compound represented by the above general formula (3A), for example, the following compounds can be cited as specific examples.
[1271]
Chemical Formula 120
[1272]
[1273]
Chemical Formula 121
[1274]
[1275]
Chemical Formula 122
[1276]
[1277]
Chemical Formula 123
[1278]
[1279] [Chemical Formula 124]
[1280]
[1281] (The compound represented by general formula (4))
[1282] The compounds represented by general formula (4) will be described.
[1283] [Chemical Formula 125]
[1284]
[1285] (In the above general formula (4),
[1286] Z can be independently represented by CRa or nitrogen atoms.
[1287] Rings A1 and A2 are each independent of each other.
[1288] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or
[1289] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1290] When there are multiple Ra, one or more groups consisting of two or more adjacent Ra are selected.
[1291] They bond together to form substituted or unsubstituted monocyclic rings.
[1292] They bond together to form substituted or unsubstituted fused rings, or
[1293] They do not bond with each other.
[1294] n21 and n22 are each independently 0, 1, 2, 3 or 4.
[1295] When there are multiple Rb, one or more groups consisting of two or more adjacent Rb are considered.
[1296] They bond together to form substituted or unsubstituted monocyclic rings.
[1297] They bond together to form substituted or unsubstituted fused rings, or
[1298] They do not bond with each other.
[1299] When there are multiple Rc, one or more groups are formed by two or more adjacent Rc.
[1300] They bond together to form substituted or unsubstituted monocyclic rings.
[1301] They bond together to form substituted or unsubstituted fused rings, or
[1302] They do not bond with each other.
[1303] Ra, Rb, and Rc, which do not form the aforementioned single rings and do not form the aforementioned fused rings, are each independently...
[1304] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1305] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1306] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1307] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1308] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1309] -O-(R 904 The groups shown in the figure,
[1310] -S-(R 905 The groups shown in the figure,
[1311] -N(R 906 (R) 907 The groups shown in the figure,
[1312] Halogen atoms,
[1313] cyano,
[1314] Nitro,
[1315] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1316] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1317] The "aromatic hydrocarbon rings" of the A1 and A2 rings have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "aryl" group.
[1318] The "aromatic hydrocarbon rings" of A1 and A2 rings contain two carbon atoms on the fused 2-ring structure in the center of the above general formula (4) as cyclic atoms.
[1319] As a specific example of "a cyclic aromatic hydrocarbon ring with 6 to 50 carbon atoms, whether substituted or unsubstituted", compounds formed by introducing hydrogen atoms into the "aryl" group described in Specific Example Group G1 can be cited.
[1320] The "heterocyclic" rings A1 and A2 have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "heterocyclic group".
[1321] The "heterocyclic" rings A1 and A2 contain two carbon atoms from the fused 2-ring structure in the center of the above general formula (4) as cyclic atoms.
[1322] As a specific example of "a heterocycle with 5 to 50 cyclic atoms, whether substituted or unsubstituted", one can cite compounds formed by introducing hydrogen atoms into the "heterocyclic group" described in Specific Example Group G2.
[1323] Rb is bonded to any of the carbon atoms that form an aromatic hydrocarbon ring as an A1 ring, or to any of the atoms that form a heterocycle as an A1 ring.
[1324] Rc is bonded to any one of the carbon atoms that form an aromatic hydrocarbon ring as an A2 ring, or to any one of the atoms that form a heterocycle as an A2 ring.
[1325] Among Ra, Rb and Rc, at least one is preferably a group represented by the following general formula (4a), and more preferably at least two are groups represented by the following general formula (4a).
[1326] [Chemical Formula 126]
[1327] *-L 401 -Ar 401 (4a)
[1328] (In the above general formula (4a),
[1329] L 401 for
[1330] single bond,
[1331] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or
[1332] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.
[1333] Ar 401 for
[1334] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1335] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1336] The group represented by the following general formula (4b).
[1337] [Chemical Formula 127]
[1338]
[1339] (In the above general formula (4b),
[1340] L 402and L 403 Each independently
[1341] single bond,
[1342] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or
[1343] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.
[1344] Ar 402 and Ar 403 The group formed
[1345] They bond together to form substituted or unsubstituted monocyclic rings.
[1346] They bond together to form substituted or unsubstituted fused rings, or
[1347] They do not bond with each other.
[1348] Ar does not form the aforementioned single ring and does not form the aforementioned fused ring 402 and Ar 403 Each independently
[1349] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1350] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1351] In one embodiment, the compound represented by the above general formula (4) is represented by the following general formula (42).
[1352] [Chemical Formula 128]
[1353]
[1354] (In the above general formula (42),
[1355] R 401 ~R 411 One or more of the groups consisting of two or more adjacent elements.
[1356] They bond together to form substituted or unsubstituted monocyclic rings.
[1357] They bond together to form substituted or unsubstituted fused rings, or
[1358] They do not bond with each other.
[1359] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 401 ~R 411 Each independently
[1360] hydrogen atom,
[1361] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1362] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1363] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1364] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1365] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1366] -O-(R 904 The groups shown in the figure,
[1367] -S-(R 905 The groups shown in the figure,
[1368] -N(R 906 (R) 907 The groups shown in the figure,
[1369] Halogen atoms,
[1370] cyano,
[1371] Nitro,
[1372] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1373] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1374] R 401 ~R 411 Preferably, at least one of them is a group represented by the above general formula (4a), and more preferably at least two of them are groups represented by the above general formula (4a).
[1375] R 404 and R 411 Preferably, it is a group represented by the above general formula (4a).
[1376] In one embodiment, the compound represented by the above general formula (4) is a compound formed by bonding the structure represented by the following general formula (4-1) or general formula (4-2) onto the A1 ring.
[1377] Additionally, in one embodiment, the compound represented by the above general formula (42) is in R 404 ~R 407 Compounds formed by bonding the following general formula (4-1) or general formula (4-2) to the bonded ring.
[1378] [Chemical Formula 129]
[1379]
[1380] In the above general formula (4-1), each of the two * is independently bonded to the cyclic carbon atom of the aromatic hydrocarbon ring or the cyclic atom of the heterocycle in the above general formula (4), or to the R in the above general formula (42). 404 ~R 407 Any one of the bonds in,
[1381] The three asterisks in the above general formula (4-2) are each independently bonded to the cyclic carbon atom of the aromatic hydrocarbon ring or the cyclic atom of the heterocycle in the above general formula (4), or to the R in the above general formula (42). 404 ~R 407 Any one of the bonds in,
[1382] R 421 ~R 427 One or more of the groups consisting of two or more adjacent elements.
[1383] They bond together to form substituted or unsubstituted monocyclic rings.
[1384] They bond together to form substituted or unsubstituted fused rings, or
[1385] They do not bond with each other.
[1386] R 431 ~R 438 One or more of the groups consisting of two or more adjacent elements.
[1387] They bond together to form substituted or unsubstituted monocyclic rings.
[1388] They bond together to form substituted or unsubstituted fused rings, or
[1389] They do not bond with each other.
[1390] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 421 ~R 427 and R 431 ~R 438 Each independently
[1391] hydrogen atom,
[1392] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1393] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1394] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1395] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1396] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1397] -O-(R 904 The groups shown in the figure,
[1398] -S-(R 905 The groups shown in the figure,
[1399] -N(R 906 (R) 907 The groups shown in the figure,
[1400] Halogen atoms,
[1401] cyano,
[1402] Nitro,
[1403] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1404] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1405] In one embodiment, the compound represented by the above general formula (4) is a compound represented by the following general formula (41-3), general formula (41-4) or general formula (41-5).
[1406]
Chemical Formula 130
[1407]
[1408]
Chemical Formula 131
[1409]
[1410]
Chemical Formula 132
[1411]
[1412] (In the above general formulas (41-3), (41-4), and (41-5),
[1413] Ring A1 is defined in the same way as in general formula (4) above.
[1414] R 421 ~R 427 Each independently relates to R in the above general formula (4-1) 421 ~R 427 Same meaning
[1415] R440 ~R 448 Each independently relates to R in the above general formula (42) 401 ~R 411 The meaning is the same.
[1416] In one embodiment, the aromatic hydrocarbon ring of the above general formula (41-5) with 6 to 50 carbon atoms, either substituted or unsubstituted for the A1 ring, is...
[1417] Substituted or unsubstituted naphthalene ring, or
[1418] Substituted or unsubstituted fluorene ring.
[1419] In one embodiment, the heterocycle of the above general formula (41-5), which has 5 to 50 cyclic atoms and is either substituted or unsubstituted for the A1 ring, is...
[1420] Substituted or unsubstituted dibenzofuran rings,
[1421] Substituted or unsubstituted carbazole ring, or
[1422] Substituted or unsubstituted dibenzothiophene ring.
[1423] In one embodiment, the compound represented by the above general formula (4) or the above general formula (42) is selected from the group consisting of the compounds represented by the following general formulas (461) to (467).
[1424]
Chemical Formula 133
[1425]
[1426] [Chemical Formula 134]
[1427]
[1428] [Chemical Formula 135]
[1429]
[1430]
Chemical Formula 136
[1431]
[1432]
Chemical Formula 137
[1433]
[1434] (In the above general formulas (461), (462), (463), (464), (465), (466), and (467),
[1435] R 421 ~R427 Each independently relates to R in the above general formula (4-1) 421 ~R 427 Same meaning
[1436] R 431 ~R 438 Each independently relates to R in the above general formula (4-2) 431 ~R 438 Same meaning
[1437] R 440 ~R 448 and R 451 ~R 454 Each independently relates to R in the above general formula (42) 401 ~R 411 Same meaning
[1438] X4 represents an oxygen atom, NR 801 or C(R) 802 (R) 803 ),
[1439] R 801 R 802 and R 803 Each independently
[1440] hydrogen atom,
[1441] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1442] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1443] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1444] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1445] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[1446] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[1447] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[1448] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
[1449] In R 803 In the case of multiple Rs, multiple Rs 803 (They may be the same or different.)
[1450] In one embodiment, for the compound represented by the above general formula (42), R 401 ~R 411 The compounds in this embodiment are described in detail as compounds represented by the following general formula (45), in which two or more adjacent groups are bonded to each other to form substituted or unsubstituted monocyclic rings or substituted or unsubstituted fused rings.
[1451] (The compound represented by general formula (45))
[1452] The compounds represented by general formula (45) will be described.
[1453] [Chemical Formula 138]
[1454]
[1455] (In the above general formula (45),
[1456] Choose freely R 461 With R 462 The group formed, R 462 With R 463 The group formed, R 464 With R 465 The group formed, R 465 With R 466 The group formed, R 466 With R 467 The group formed, R 468 With R 469 The group formed, R 469 With R 470 The groups formed, and R 470 With R 471 Within a larger group, two or more groups are bonded together to form substituted or unsubstituted monocyclic rings or substituted or unsubstituted fused rings.
[1457] in,
[1458] R 461 With R 462 The groups formed and R 462 With R 463 The groups do not simultaneously form a ring;
[1459] R 464 With R 465 The groups formed and R 465 With R 466 The groups do not simultaneously form a ring;
[1460] R 465 With R466 The groups formed and R 466 With R 467 The groups do not simultaneously form a ring;
[1461] R 468 With R 469 The groups formed and R 469 With R 470 The groups do not simultaneously form a ring; and
[1462] R 469 With R 470 The groups formed and R 470 With R 471 The groups formed do not simultaneously form a ring.
[1463] R 461 ~R 471 Two or more rings are formed that are identical or different from each other.
[1464] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 461 ~R 471 Each independently
[1465] hydrogen atom,
[1466] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1467] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1468] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1469] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1470] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1471] -O-(R 904 The groups shown in the figure,
[1472] -S-(R 905 ), -N(R 906 (R) 907 The groups shown in the figure,
[1473] Halogen atoms,
[1474] cyano,
[1475] Nitro,
[1476] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1477] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1478] In the above general formula (45), R n With R n+1 (n represents an integer selected from 461, 462, 464-466 and 468-470) mutually bonded with R n and R n+1 The two bonded cyclic carbon atoms together form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring. The ring is preferably composed of atoms selected from carbon, oxygen, sulfur and nitrogen, and the number of atoms in the ring is preferably 3 to 7, more preferably 5 or 6.
[1479] The compound represented by the above general formula (45) may have, for example, two, three, or four ring structures. Two or more ring structures may each reside on the same benzene ring in the parent skeleton of the above general formula (45), or they may reside on different benzene rings. For example, in the case of three ring structures, one ring structure may reside on each of the three benzene rings in the above general formula (45).
[1480] Examples of the ring structures in the compounds represented by the general formula (45) above include those represented by the general formulas (451) to (460).
[1481]
Chemical Formula 139
[1482]
[1483] (In the above general formulas (451) to (457),
[1484] *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14 represent R respectively. n and R n+1 The two cyclic carbon atoms bonded above,
[1485] R n The bonded cyclic carbon atoms can be any one of the two cyclic carbon atoms represented by *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14.
[1486] X 45 For C(R) 4512 (R) 4513 ), NR 4514 oxygen or sulfur atoms
[1487] R 4501 ~R 4506 and R4512 ~R 4513 One or more of the groups consisting of two or more adjacent elements.
[1488] They bond together to form substituted or unsubstituted monocyclic rings.
[1489] They bond together to form substituted or unsubstituted fused rings, or
[1490] They do not bond with each other.
[1491] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 4501 ~R 4514 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.
[1492] [Chemical Formula 140]
[1493]
[1494] (In the above general formulas (458) to (460),
[1495] *1 and *2, and *3 and *4 respectively represent R n and R n+1 The two cyclic carbon atoms bonded above,
[1496] R n The bonded cyclic carbon atoms can be any one of the two cyclic carbon atoms represented by *1 and *2 or *3 and *4.
[1497] X 45 For C(R) 4512 (R) 4513 ), NR 4514 oxygen or sulfur atoms
[1498] R 4512 ~R 4513 and R 4515 ~R 4525 One or more of the groups consisting of two or more adjacent elements.
[1499] They bond together to form substituted or unsubstituted monocyclic rings.
[1500] They bond together to form substituted or unsubstituted fused rings, or
[1501] They do not bond with each other.
[1502] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 4512 ~R 4513 R 4515 ~R 4521 and R4522 ~R 4525 and R 4514 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.
[1503] In the above general formula (45), R is preferred. 462 R 464 R 465 R 470 and R 471 At least one of them (preferably R) 462 R 465 and R 470 At least one of them, further preferred R 462 () are groups that do not form ring structures.
[1504] (i) In the above general formula (45), R n With R n+1 When the formed ring structure has substituents, the substituents,
[1505] (ii) R in the above general formula (45) that does not form a ring structure 461 ~R 471 as well as
[1506] (iii) R in equations (451) to (460) 4501 ~R 4514 R 4515 ~R 4525 Each is preferred to be independent of the other.
[1507] hydrogen atom,
[1508] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1509] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1510] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1511] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1512] -N(R 906 (R) 907 The groups shown in the figure,
[1513] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1514] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1515] Any group in the group consisting of the groups represented by the following general formulas (461) to (464).
[1516]
Chemical Formula 141
[1517]
[1518] (In the above general formulas (461) to (464),
[1519] R d Each independently
[1520] hydrogen atom,
[1521] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1522] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1523] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1524] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1525] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1526] -O-(R 904 The groups shown in the figure,
[1527] -S-(R 905 The groups shown in the figure,
[1528] -N(R 906 (R) 907 The groups shown in the figure,
[1529] Halogen atoms,
[1530] cyano,
[1531] Nitro,
[1532] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1533] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1534] X 46 For C(R) 801 (R) 802 ), NR 803 oxygen or sulfur atoms
[1535] R 801 R 802 and R 803 Each independently
[1536] hydrogen atom,
[1537] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1538] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1539] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1540] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1541] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[1542] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[1543] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[1544] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
[1545] In R 803 In the case of multiple Rs, multiple Rs 803 They are the same or different.
[1546] p1 is 5.
[1547] p2 is 4.
[1548] p3 is 3.
[1549] p4 is 7.
[1550] In the above general formulas (461) to (464), each * independently represents a bonding position with the ring structure.
[1551] In compounds six and seven, R 901 ~R 907 Same as the definition above.
[1552] In one embodiment, the compound represented by the above general formula (45) is represented by any one of the following general formulas (45-1) to (45-6).
[1553] [Chemical Formula 142]
[1554]
[1555] [Chemical Formula 143]
[1556]
[1557] (In the above general formulas (45-1) to (45-6),
[1558] Each of the rings d to i is independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.
[1559] R 461 ~R 471 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.
[1560] In one embodiment, the compound represented by the above general formula (45) is represented by any one of the following general formulas (45-7) to (45-12).
[1561] [Chemical Formula 144]
[1562]
[1563] [Chemical Formula 145]
[1564]
[1565] (In the above general formulas (45-7) to (45-12),
[1566] Rings d to f, k, and j are each independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.
[1567] R 461 ~R 471 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.
[1568] In one embodiment, the compound represented by the above general formula (45) is represented by any one of the following general formulas (45-13) to (45-21).
[1569] [Chemical Formula 146]
[1570]
[1571] [Chemical Formula 147]
[1572]
[1573] [Chemical Formula 148]
[1574]
[1575] (In the above general formulas (45-13) to (45-21),
[1576] Each of the rings d to k is independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.
[1577] R 461 ~R 471 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.
[1578] Substituents that further have substituents, such as those found in the above-mentioned ring g or ring h, can be exemplified by...
[1579] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1580] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1581] The groups represented by the above general formula (461),
[1582] The groups represented by the above general formula (463), or
[1583] The group represented by the above general formula (464).
[1584] In one embodiment, the compound represented by the above general formula (45) is represented by any one of the following general formulas (45-22) to (45-25).
[1585] [Chemical Formula 149]
[1586]
[1587] (In the above general formulas (45-22) to (45-25),
[1588] X 46 and X 47 Each independently is C(R) 801 (R) 802 ), NR 803 oxygen or sulfur atoms
[1589] R 461 ~R 471 and R 481 ~R 488 Each independently relates to R in the above general formula (45) 461 ~R 471 They have the same meaning.
[1590] R 801 R 802 and R 803 Each independently
[1591] hydrogen atom,
[1592] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1593] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1594] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1595] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1596] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[1597] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[1598] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[1599] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
[1600] In R 803 In the case of multiple Rs, multiple Rs 803 (They may be the same or different.)
[1601] In one embodiment, the compound represented by the above general formula (45) is represented by the following general formulas (45-26).
[1602] [Chemical Formula 150]
[1603]
[1604] (In the above general formula (45-26),
[1605] X 46 For C(R) 801 (R) 802 ), NR 803 oxygen or sulfur atoms
[1606] R 463 R 464 R 467 R 468 R 471 and R 481 ~R 492 Each independently relates to R in the above general formula (45) 461 ~R 471 They have the same meaning.
[1607] R 801 R 802 and R803 Each independently
[1608] hydrogen atom,
[1609] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1610] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1611] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1612] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1613] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[1614] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[1615] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[1616] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
[1617] In R 803 In the case of multiple Rs, multiple Rs 803 (They may be the same or different.)
[1618] (Specific examples of compounds represented by general formula (4))
[1619] As a compound represented by the above general formula (4), the following compounds can be cited as specific examples. In the following specific examples, Ph represents a phenyl group and D represents a deuterium atom.
[1620]
Chemical Formula 151
[1621]
[1622]
Chemical Formula 152
[1623]
[1624]
Chemical Formula 153
[1625]
[1626] [Chemical Formula 154]
[1627]
[1628]
Chemical Formula 155
[1629]
[1630] [Chemical Formula 156]
[1631]
[1632] [Chemical Formula 157]
[1633]
[1634] [Chemical Formula 158]
[1635]
[1636] [Chemical Formula 159]
[1637]
[1638] [Chemical Formula 160]
[1639]
[1640] (The compound represented by general formula (5))
[1641] The compounds represented by general formula (5) will be described. The compounds represented by general formula (5) are the compounds corresponding to the compounds represented by general formula (41-3) above.
[1642]
Chemical Formula 161
[1643]
[1644] (In the above general formula (5),
[1645] R 501 ~R 507 and R 511 ~R 517 One or more of the groups consisting of two or more adjacent elements.
[1646] They bond together to form substituted or unsubstituted monocyclic rings.
[1647] They bond together to form substituted or unsubstituted fused rings, or
[1648] They do not bond with each other.
[1649] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 501 ~R 507 and R 511 ~R 517 Each independently
[1650] hydrogen atom,
[1651] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1652] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1653] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1654] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1655] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1656] -O-(R 904 The groups shown in the figure,
[1657] -S-(R 905 The groups shown in the figure,
[1658] -N(R 906 (R) 907 The groups shown in the figure,
[1659] Halogen atoms,
[1660] cyano,
[1661] Nitro,
[1662] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1663] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1664] R 521 and R 522 Each independently
[1665] hydrogen atom,
[1666] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1667] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1668] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1669] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1670] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1671] -O-(R904 The groups shown in the figure,
[1672] -S-(R 905 The groups shown in the figure,
[1673] -N(R 906 (R) 907 The groups shown in the figure,
[1674] Halogen atoms,
[1675] cyano,
[1676] Nitro,
[1677] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1678] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1679] “R 501 ~R 507 and R 511 ~R 517 "One of the groups consisting of two or more adjacent elements" is, for example, R. 501 With R 502 The group formed, R 502 With R 503 The group formed, R 503 With R 504 The group formed, R 505 With R 506 The group formed, R 506 With R 507 The group formed, R 501 With R 502 With R 503 The groups and combinations formed by them.
[1680] In one implementation, R 501 ~R 507 and R 511 ~R 517 At least one, preferably two, of them are -N(R) 906 (R) 907 The group shown is ).
[1681] In one implementation, R 501 ~R 507 and R 511 ~R 517 Each independently
[1682] hydrogen atom,
[1683] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1684] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1685] In one embodiment, the compound represented by the above general formula (5) is the compound represented by the following general formula (52).
[1686] [Chemical Formula 162]
[1687]
[1688] (In the above general formula (52),
[1689] R 531 ~R 534 and R 541 ~R 544 One or more of the groups consisting of two or more adjacent elements.
[1690] They bond together to form substituted or unsubstituted monocyclic rings.
[1691] They bond together to form substituted or unsubstituted fused rings, or
[1692] They do not bond with each other.
[1693] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 531 ~R 534 R 541 ~R 544 and R 551 and R 552 Each independently
[1694] hydrogen atom,
[1695] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1696] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1697] R 561 ~R 564 Each independently
[1698] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1699] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1700] In one embodiment, the compound represented by the above general formula (5) is the compound represented by the following general formula (53).
[1701] [Chemical Formula 163]
[1702]
[1703] (In the above general formula (53), R) 551 R 552 and R 561 ~R 564 Each independently relates to R in the above general formula (52) 551 R 552 and R 561 ~R 564 The meaning is the same.
[1704] In one implementation, R in the above general formulas (52) and (53) 561 ~R 564 Each is independently a substituted or unsubstituted aryl group (preferably phenyl) with 6 to 50 carbon atoms in a cyclic structure.
[1705] In one implementation, R in the above general formula (5) 521 and R 522 R in the above general formulas (52) and (53) 551 and R 552 It is a hydrogen atom.
[1706] In one embodiment, the substituents expressed as "substituted or unsubstituted" in the above general formulas (5), (52), and (53) are...
[1707] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1708] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1709] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1710] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1711] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1712] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1713] (Specific examples of compounds represented by general formula (5))
[1714] As a compound represented by the above general formula (5), the following compounds can be cited as specific examples.
[1715] [Chemical Formula 164]
[1716]
[1717] [Chemical Formula 165]
[1718]
[1719]
Chemical Formula 166
[1720]
[1721] [Chemical Formula 167]
[1722]
[1723] [Chemical Formula 168]
[1724]
[1725] [Chemical Formula 169]
[1726]
[1727] [Chemical Formula 170]
[1728]
[1729]
Chemical Formula 171
[1730]
[1731] [Chemical Formula 172]
[1732]
[1733]
Chemical Formula 173
[1734]
[1735] [Chemical Formula 174]
[1736]
[1737] [Chemical Formula 175]
[1738]
[1739] [Chemical Formula 176]
[1740]
[1741]
Chemical Formula 177
[1742]
[1743] [Chemical Formula 178]
[1744]
[1745] [Chemical Formula 179]
[1746]
[1747] [Chemical Formula 180]
[1748]
[1749] (The compound represented by general formula (6))
[1750] The compounds represented by general formula (6) will be described.
[1751]
Chemical Formula 181
[1752]
[1753] (In the above general formula (6),
[1754] Rings a, b, and c are each independently...
[1755] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or
[1756] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1757] R 601 and R 602 Each ring independently bonds to the aforementioned a-ring, b-ring, or c-ring to form a substituted or unsubstituted heterocycle, or not to form a substituted or unsubstituted heterocycle.
[1758] R does not form the aforementioned substituted or unsubstituted heterocycles 601 and R 602 Each independently
[1759] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1760] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1761] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1762] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1763] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1764] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1765] Rings a, b, and c are rings fused with the central fused 2-ring structure of the above general formula (6) consisting of boron atoms and two nitrogen atoms (substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 cyclic carbon atoms, or substituted or unsubstituted heterocycles with 5 to 50 cyclic atoms).
[1766] The "aromatic hydrocarbon rings" of rings a, b, and c have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "aryl" group.
[1767] The "aromatic hydrocarbon ring" of ring a contains three carbon atoms on the fused 2-ring structure in the center of the above general formula (6) as cyclic atoms.
[1768] The "aromatic hydrocarbon rings" of rings b and c contain two carbon atoms on the fused 2-ring structure in the center of the above general formula (6) as cyclic atoms.
[1769] As a specific example of "a cyclic aromatic hydrocarbon ring with 6 to 50 carbon atoms, whether substituted or unsubstituted", compounds formed by introducing hydrogen atoms into the "aryl" group described in Specific Example Group G1 can be cited.
[1770] The "heterocyclic" rings a, b, and c have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "heterocyclic groups".
[1771] The "heterocyclic ring" of ring a includes three carbon atoms in the fused 2-ring structure at the center of the above general formula (6) as cyclic atoms. The "heterocyclic rings" of rings b and c include two carbon atoms in the fused 2-ring structure at the center of the above general formula (6) as cyclic atoms. As a specific example of "heterocyclic rings with 5 to 50 substituted or unsubstituted cyclic atoms", compounds formed by introducing hydrogen atoms into the "heterocyclic group" described in specific example group G2 can be cited.
[1772] R 601 and R 602 Each ring can independently bond with ring a, ring b, or ring c to form substituted or unsubstituted heterocycles. In this case, the heterocycle contains the nitrogen atom in the fused 2-ring structure at the center of the general formula (6). The heterocycle may also contain heteroatoms other than the nitrogen atom. R 601 and R 602 Specifically, bonding with ring a, ring b, or ring c refers to the bonding between atoms constituting ring a, ring b, or ring c and atoms constituting ring R. 601 and R 602 The atoms are bonded together. For example, it could also be R. 601 fused with α ring to form R 601 A nitrogen-containing heterocycle in which two rings (or three or more rings) are fused with the a ring. Specific examples of such nitrogen-containing heterocycles include compounds corresponding to the heterocyclic groups in Specific Example Group G2 that contain nitrogen and are fused with two or more rings.
[1773] R 601 Cases involving b-ring bonding, R 602 The case of α-ring bonding and R 602 The situation regarding bonding with the c-ring is the same as described above.
[1774] In one embodiment, ring a, ring b, and ring c in the above general formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring with 6 to 50 carbon atoms.
[1775] In one embodiment, ring a, ring b, and ring c in the above general formula (6) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.
[1776] In one implementation, R in the above general formula (6) 601 and R 602 Each independently
[1777] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1778] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1779] Preferably, it is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[1780] In one embodiment, the compound represented by the above general formula (6) is the compound represented by the following general formula (62).
[1781] [Chemical Formula 182]
[1782]
[1783] (In the above general formula (62),
[1784] R 601A With selection from R 611 and R 621 One or more of them are bonded together to form a substituted or unsubstituted heterocycle, or they do not form a substituted or unsubstituted heterocycle.
[1785] R 602A With selection from R 613 and R 614 One or more of them are bonded together to form a substituted or unsubstituted heterocycle, or they do not form a substituted or unsubstituted heterocycle.
[1786] R does not form the aforementioned substituted or unsubstituted heterocycles 601A and R 602A Each independently
[1787] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1788] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1789] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1790] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1791] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1792] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1793] R 611 ~R 621 One or more of the groups consisting of two or more adjacent elements.
[1794] They bond together to form substituted or unsubstituted monocyclic rings.
[1795] They bond together to form substituted or unsubstituted fused rings, or
[1796] They do not bond with each other.
[1797] R does not form the aforementioned substituted or unsubstituted heterocycles, does not form the aforementioned monocyclic rings, and does not form the aforementioned fused rings. 611 ~R 621 Each independently
[1798] hydrogen atom,
[1799] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1800] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1801] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1802] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1803] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1804] -O-(R 904 The groups shown in the figure,
[1805] -S-(R 905 The groups shown in the figure,
[1806] -N(R 906 (R) 907 The groups shown in the figure,
[1807] Halogen atoms,
[1808] cyano,
[1809] Nitro,
[1810] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1811] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1812] R in the above general formula (62) 601A and R 602A R, respectively, is the same as the general formula (6) above. 601 and R 602 The corresponding functional group.
[1813] For example, R 601A With R 611 These are nitrogen-containing heterocycles that are bonded together to form a fused two-ring (or three-ring or more) fused ring, comprising the rings containing the rings and a benzene ring corresponding to the α-ring. Specific examples of such nitrogen-containing heterocycles include compounds corresponding to the nitrogen-containing fused heterocyclic groups in Specific Example Group G2. R 601A With R 621 Bonding situation, R 602A With R 613 Bonding conditions and R 602A With R 614 The bonding situation is the same as above.
[1814] R 611 ~R 621 One or more of the two or more adjacent groups can
[1815] They bond together to form substituted or unsubstituted monocyclic rings, or
[1816] They bond together to form substituted or unsubstituted fused rings.
[1817] For example, R 611 With R 612 The bonds can be combined to form structures consisting of six-membered rings such as benzene rings, indole rings, pyrrole rings, benzofuran rings, or benzothiophene rings. The resulting fused rings can be naphthalene rings, carbazole rings, indole rings, dibenzofuran rings, or dibenzothiophene rings.
[1818] In one implementation, R does not participate in forming the ring. 611 ~R 621 Each independently
[1819] hydrogen atom,
[1820] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1821] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1822] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1823] In one implementation, R does not participate in forming the ring. 611~R 621 Each independently
[1824] hydrogen atom,
[1825] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1826] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1827] In one implementation, R does not participate in forming the ring. 611 ~R 621 Each independently
[1828] hydrogen atom, or
[1829] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted.
[1830] In one implementation, R does not participate in forming the ring. 611 ~R 621 Each independently
[1831] hydrogen atom, or
[1832] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1833] R 611 ~R 621 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[1834] In one embodiment, the compound represented by the above general formula (62) is the compound represented by the following general formula (63).
[1835] [Chemical Formula 183]
[1836]
[1837] (In the above general formula (63),
[1838] R 631 With R 646 Bonding to form substituted or unsubstituted heterocycles, or not forming substituted or unsubstituted heterocycles.
[1839] R 633 With R 647 Bonding to form substituted or unsubstituted heterocycles, or not forming substituted or unsubstituted heterocycles.
[1840] R 634 With R 651 Bonding to form substituted or unsubstituted heterocycles, or not forming substituted or unsubstituted heterocycles.
[1841] R 641 With R642 Bonding to form substituted or unsubstituted heterocycles, or not forming substituted or unsubstituted heterocycles.
[1842] R 631 ~R 651 One or more of the groups consisting of two or more adjacent elements.
[1843] They bond together to form substituted or unsubstituted monocyclic rings.
[1844] They bond together to form substituted or unsubstituted fused rings, or
[1845] They do not bond with each other.
[1846] R does not form the aforementioned substituted or unsubstituted heterocycles, does not form the aforementioned monocyclic rings, and does not form the aforementioned fused rings. 631 ~R 651 Each independently
[1847] hydrogen atom,
[1848] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1849] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1850] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1851] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1852] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1853] -O-(R 904 The groups shown in the figure,
[1854] -S-(R 905 The groups shown in the figure,
[1855] -N(R 906 (R) 907 The groups shown in the figure,
[1856] Halogen atoms,
[1857] cyano,
[1858] Nitro,
[1859] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1860] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[1861] R631 Can be used with R 646 Bonding forms substituted or unsubstituted heterocycles. For example, R can be... 631 With R 646 Bonding to form fused R 646 The bonded benzene ring, or a nitrogen-containing heterocycle consisting of three or more rings fused together with a nitrogen-containing ring and a benzene ring corresponding to the a ring. Specific examples of such nitrogen-containing heterocycles include compounds corresponding to the nitrogen-containing heterocyclic groups fused together in Specific Example Group G2. R 633 With R 647 Bonding situation, R 634 With R 651 Bonding conditions and R 641 With R 642 The bonding situation is the same as above.
[1862] In one implementation, R does not participate in forming the ring. 631 ~R 651 Each independently
[1863] hydrogen atom,
[1864] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1865] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1866] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1867] In one implementation, R does not participate in forming the ring. 631 ~R 651 Each independently
[1868] hydrogen atom,
[1869] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1870] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1871] In one implementation, R does not participate in forming the ring. 631 ~R 651 Each independently
[1872] hydrogen atom, or
[1873] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted.
[1874] In one implementation, R does not participate in forming the ring. 631 ~R 651 Each independently
[1875] hydrogen atom, or
[1876] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
[1877] R 631 ~R 651 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[1878] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63A).
[1879] [Chemical Formula 184]
[1880]
[1881] (In the above general formula (63A),
[1882] R 661 for
[1883] hydrogen atom,
[1884] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1885] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1886] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1887] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or
[1888] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[1889] R 662 ~R 665 Each independently
[1890] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1891] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1892] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1893] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or
[1894] (Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure.)
[1895] In one implementation, R 661 ~R 665 Each independently
[1896] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[1897] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.
[1898] In one implementation, R 661 ~R 665 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[1899] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63B).
[1900] [Chemical Formula 185]
[1901]
[1902] (In the above general formula (63B),
[1903] R 671 and R 672 Each independently
[1904] hydrogen atom,
[1905] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1906] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1907] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1908] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1909] -N(R 906 (R) 907 The group shown in the figure, or
[1910] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[1911] R 673 ~R 675 Each independently
[1912] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1913] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1914] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1915] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1916] -N(R 906 (R) 907 The group shown in the figure, or
[1917] (Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure.)
[1918] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63B').
[1919] [Chemical Formula 186]
[1920]
[1921] (In the above general formula (63B'), R) 672 ~R 675 Each independently relates to R in the above general formula (63B) 672 ~R 675 The meaning is the same.
[1922] In one implementation, R 671 ~R 675 At least one of them is
[1923] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1924] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1925] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1926] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1927] -N(R 906 (R) 907 The group shown in the figure, or
[1928] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.
[1929] In one implementation method
[1930] R 672 for
[1931] hydrogen atom,
[1932] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1933] -N(R 906 (R) 907 The group shown in the figure, or
[1934] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[1935] R 671 and R 673 ~R 675 Each independently
[1936] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1937] -N(R 906 (R) 907 The group shown in the figure, or
[1938] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.
[1939] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63C).
[1940] [Chemical Formula 187]
[1941]
[1942] (In the above general formula (63C),
[1943] R 681 and R 682 Each independently
[1944] hydrogen atom,
[1945] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1946] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1947] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1948] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or
[1949] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.
[1950] R 683 ~R 686 Each independently
[1951] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1952] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1953] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1954] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or
[1955] (Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic structure.)
[1956] In one embodiment, the compound represented by the above general formula (63) is the compound represented by the following general formula (63C').
[1957]
Chemical Formula 188
[1958]
[1959] (In the above general formula (63C'), R) 683 ~R 686 Each independently relates to R in the above general formula (63C). 683 ~R 686 The meaning is the same.
[1960] In one implementation, R 681 ~R 686 Each independently
[1961] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[1962] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.
[1963] In one implementation, R 681 ~R 686 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.
[1964] For the compound shown in the general formula (6) above, the a ring, b ring and c ring can first be connected by a linking group (containing NR). 601 Groups and containing NR 602 The intermediate is produced by bonding the boron rings (a, b, and c) with a linking group (a group containing boron atoms). The final product is then produced by bonding the a, b, and c rings together with a linking group (a group containing boron atoms). Amination reactions such as the Buchwald-Hartwig reaction can be used in the first reaction. The tandem hetero Friedel-Crafts reaction can be used in the second reaction.
[1965] (Specific examples of compounds represented by general formula (6))
[1966] Although specific examples of compounds represented by the above general formula (6) are described below, these are merely examples, and the compounds represented by the above general formula (6) are not limited to the specific examples described below.
[1967] [Chemical Formula 189]
[1968]
[1969] [Chemical Formula 190]
[1970]
[1971]
Chemical Formula 191
[1972]
[1973] [Chemical Formula 192]
[1974]
[1975] [Chemical Formula 193]
[1976]
[1977] [Chemical Formula 194]
[1978]
[1979] [Chemical Formula 195]
[1980]
[1981] [Chemical Formula 196]
[1982]
[1983] [Chemical Formula 197]
[1984]
[1985] [Chemical Formula 198]
[1986]
[1987]
Chemical Formula 199
[1988]
[1989] [Chemical Formula 200]
[1990]
[1991] (The compound represented by general formula (7))
[1992] The compounds represented by general formula (7) will be described.
[1993]
Chemical Formula 201
[1994]
[1995]
Chemical Formula 202
[1996]
[1997] (In the above general formula (7),
[1998] The r-ring is a ring shown in the above general formula (72) or general formula (73) that is fused at any position of adjacent rings.
[1999] The q-ring and s-ring are each independently rings fused at any position of adjacent rings as shown in the above general formula (74).
[2000] The p-ring and t-ring are each independently structures shown in the above general formula (75) or general formula (76) that are fused at any position of adjacent rings.
[2001] X7 represents an oxygen atom, a sulfur atom, or NR. 702 .
[2002] In R 701 In the case of multiple occurrences, multiple adjacent R 701
[2003] They bond together to form substituted or unsubstituted monocyclic rings.
[2004] They bond together to form substituted or unsubstituted fused rings, or
[2005] They do not bond with each other.
[2006] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 701 and R 702 Each independently
[2007] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2008] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2009] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2010] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2011] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2012] -O-(R 904 The groups shown in the figure,
[2013] -S-(R 905 The groups shown in the figure,
[2014] -N(R 906 (R) 907 The groups shown in the figure,
[2015] Halogen atoms,
[2016] cyano,
[2017] Nitro,
[2018] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2019] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2020] Ar 701 and Ar 702 Each independently
[2021] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2022] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2023] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2024] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2025] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2026] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2027] L 701 for
[2028] Substituted or unsubstituted alkylene groups having 1 to 50 carbon atoms
[2029] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2030] Substituted or unsubstituted ynylene groups with 2 to 50 carbon atoms
[2031] Substituted or unsubstituted cycloalkylene groups with 3 to 50 carbon atoms
[2032] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[2033] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2034] m1 is 0, 1, or 2.
[2035] m2 can be 0, 1, 2, 3, or 4.
[2036] m3 can be independently 0, 1, 2 or 3.
[2037] Each m4 is independently 0, 1, 2, 3, 4, or 5.
[2038] In R 701 In the case of multiple Rs, multiple Rs 701 They are the same or different.
[2039] When multiple X7s exist, they may be identical or different from each other.
[2040] In R 702 In the case of multiple Rs, multiple Rs 702 They are the same or different.
[2041] In Ar 701 In the case of multiple instances, multiple Ar 701 They are the same or different.
[2042] In Ar 702 In the case of multiple instances, multiple Ar 702 They are the same or different.
[2043] In L 701 In the case of multiple Ls, multiple Ls 701 (They may be the same or different.)
[2044] In the above general formula (7), each of the p-ring, q-ring, r-ring, s-ring, and t-ring is fused with its adjacent ring by two carbon atoms. The position and direction of fusion are not limited, and fusion can occur at any position and in any direction.
[2045] In one embodiment, in the above general formula (72) or general formula (73) which is an r-ring, m1 = 0 or m2 = 0.
[2046] In one embodiment, the compound represented by the above general formula (7) is represented by any one of the following general formulas (71-1) to (71-6).
[2047]
Chemical Formula 203
[2048]
[2049]
Chemical Formula 204
[2050]
[2051]
Chemical Formula 205
[2052]
[2053]
Chemical Formula 206
[2054]
[2055] [Chemical Formula 207]
[2056]
[2057] [Chemical Formula 208]
[2058]
[2059] (In the above general formulas (71-1) to (71-6), R) 701 X7, Ar 701 Ar 702 L 701 m1 and m3 are respectively related to R in the above general formula (7). 701 X7, Ar 701 Ar 702 L 701 (m1 and m3 have the same meaning.)
[2060] In one embodiment, the compound represented by the above general formula (7) is represented by any one of the following general formulas (71-11) to (71-13).
[2061]
Chemical Formula 209
[2062]
[2063]
Chemical Formula 210
[2064]
[2065]
Chemical Formula 211
[2066]
[2067] (In the above general formulas (71-11) to (71-13), R) 701 X7, Ar 701 Ar 702 L 701 m1, m3 and m4 are respectively related to R in the above general formula (7) 701 X7, Ar 701 Ar 702 L 701 m1, m3, and m4 have the same meaning.
[2068] In one embodiment, the compound represented by the above general formula (7) is represented by any one of the following general formulas (71-21) to (71-25).
[2069]
Chemical Formula 212
[2070]
[2071]
Chemical Formula 213
[2072]
[2073]
Chemical Formula 214
[2074]
[2075]
Chemical Formula 215
[2076]
[2077]
Chemical Formula 216
[2078]
[2079] (In the above general formulas (71-21) to (71-25), R) 701 X7, Ar 701 Ar 702 L 701 m1 and m4 are respectively related to R in the above general formula (7). 701 X7, Ar 701 Ar 702 L 701 (m1 and m4 have the same meaning.)
[2080] In one embodiment, the compound represented by the above general formula (7) is represented by any one of the following general formulas (71-31) to (71-33).
[2081]
Chemical Formula 217
[2082]
[2083]
Chemical Formula 218
[2084]
[2085]
Chemical Formula 219
[2086]
[2087] (In the above general formulas (71-31) to (71-33), R) 701 X7, Ar 701 Ar 702 L 701 m2 to m4 are respectively related to R in the above general formula (7). 701 X7, Ar 701 Ar 702 L 701 (m2 to m4 have the same meaning.)
[2088] In one implementation, Ar 701 and Ar 702 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.
[2089] In one implementation, Ar 701 and Ar 702 One of them is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic ring, Ar 701 and Ar 702 The other one is a heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[2090] (Specific examples of compounds represented by general formula (7))
[2091] As a compound represented by the above general formula (7), the following compounds can be cited as specific examples.
[2092]
Chemical Formula 220
[2093]
[2094]
Chemical Formula 221
[2095]
[2096]
Chemical Formula 222
[2097]
[2098]
Chemical Formula 223
[2099]
[2100] [Chemical Formula 224]
[2101]
[2102] [Chemical Formula 225]
[2103]
[2104] (The compound represented by general formula (8))
[2105] The compounds represented by general formula (8) will be described.
[2106]
Chemical Formula 226
[2107]
[2108] (In the above general formula (8),
[2109] R 801 With R 802 R 802 With R 803 and R 803 With R 804At least one group of the groups are bonded to each other to form the divalent groups shown in the general formula (82) below, or they are not bonded to each other.
[2110] R 805 With R 806 R 806 With R 807 and R 807 With R 808 At least one group of the radicals may bond to each other to form a divalent group as shown in the general formula (83) below, or they may not bond to each other.
[2111] [Chemical Formula 227]
[2112]
[2113] (R that does not form the divalent group shown in the above general formula (82)) 801 ~R 804 and R 811 ~R 814 At least one of them is a monovalent group represented by the following general formula (84),
[2114] R that does not form the divalent group shown in the above general formula (83) 805 ~R 808 and R 821 ~R 824 At least one of them is a monovalent group represented by the following general formula (84),
[2115] X8 is CR 81 R 82 oxygen atom, sulfur atom or NR 809 ,
[2116] R 81 and R 82 The group formed
[2117] They bond together to form substituted or unsubstituted monocyclic rings.
[2118] They bond together to form substituted or unsubstituted fused rings, or
[2119] They do not bond with each other.
[2120] R that does not form the divalent groups shown in general formulas (82) and (83) above and is not the monovalent group shown in general formula (84) above. 801 ~R 808 R that is not a monovalent group as shown in the above general formula (84) 811 ~R 814 and R 821 ~R 824 R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings.81 and R 82 and R 809 Each independently
[2121] hydrogen atom,
[2122] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2123] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2124] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2125] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2126] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2127] -O-(R 904 The groups shown in the figure,
[2128] -S-(R 905 The groups shown in the figure,
[2129] -N(R 906 (R) 907 The groups shown in the figure,
[2130] Halogen atoms,
[2131] cyano,
[2132] Nitro,
[2133] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2134] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2135] [Chemical Formula 228]
[2136]
[2137] (In the above general formula (84),
[2138] Ar 801 and Ar 802 Each independently
[2139] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2140] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2141] L 801 ~L803 Each independently
[2142] single bond,
[2143] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms
[2144] Substituted or unsubstituted divalent heterocyclic groups with 5 to 30 cyclic atoms, or
[2145] A divalent linker is formed by bonding 2 to 4 groups from the group consisting of a substituted or unsubstituted aryl group with 6 to 30 carbon atoms and a substituted or unsubstituted divalent heterocyclic group with 5 to 30 carbon atoms.
[2146] In the above general formula (84), * indicates the bonding position with the ring structure shown in general formula (8), or the group shown in general formula (82) or general formula (83).
[2147] R is also preferred 801 With R 802 R 802 With R 803 and R 803 With R 804 At least one pair of mutual bonds and R 805 With R 806 R 806 With R 807 and R 807 With R 808 They do not bond with each other.
[2148] R is also preferred 801 With R 802 R 802 With R 803 and R 803 With R 804 Non-bonded and R 805 With R 806 R 806 With R 807 and R 807 With R 808 At least one pair of bonds exists between them.
[2149] R is also preferred 801 With R 802 R 802 With R 803 and R 803 With R 804 At least one group in R is bonded to each other to form a divalent group as shown in the following general formula (82), and R 805 With R 806 R 806 With R 807 and R 807 With R808 At least one group of the groups are bonded together to form a divalent group as shown in the following general formula (83).
[2150] In the above general formula (8), the positions of the divalent groups shown in general formula (82) and general formula (83) are not particularly limited, and can be formed in R 801 ~R 808 The group can be formed at any of the possible positions.
[2151] In one embodiment, the compound represented by the above general formula (8) is represented by any one of the following general formulas (81A-1) to (81A-3).
[2152] [Chemical Formula 229]
[2153]
[2154]
Chemical Formula 230
[2155]
[2156] (In the above general formulas (81A-1) to (81A-3),
[2157] X8 has the same meaning as X8 in the above general formula (8).
[2158] In the above general formula (81A-1), R 803 R 804 and R 811 ~R 814 At least one of them is a monovalent group represented by the above general formula (84).
[2159] In the above general formula (81A-2), R 801 R 804 and R 811 ~R 814 At least one of them is a monovalent group represented by the above general formula (84).
[2160] In the above general formula (81A-3), R 801 R 802 and R 811 ~R 814 At least one of them is a monovalent group represented by the above general formula (84).
[2161] In the above general formulas (81A-1) to (81A-3), R 805 ~R 808 At least one of them is a monovalent group represented by the above general formula (84).
[2162] R is not a monovalent group as shown in the above general formula (84) 801~R 808 and R 811 ~R 814 Each independently
[2163] hydrogen atom,
[2164] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2165] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2166] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2167] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2168] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2169] -O-(R 904 The groups shown in the figure,
[2170] -S-(R 905 The groups shown in the figure,
[2171] -N(R 906 (R) 907 The groups shown in the figure,
[2172] Halogen atoms,
[2173] cyano,
[2174] Nitro,
[2175] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2176] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2177] In one embodiment, the compound represented by the above general formula (8) is represented by any one of the following general formulas (81-1) to (81-6).
[2178]
Chemical Formula 231
[2179]
[2180]
Chemical Formula 232
[2181]
[2182]
Chemical Formula 233
[2183]
[2184] (In the above general formulas (81-1) to (81-6),
[2185] X8 has the same meaning as X8 in the above general formula (8).
[2186] R 801 ~R 824 At least two of them are monovalent groups as shown in the above general formula (84).
[2187] R is not a monovalent group as shown in the above general formula (84) 801 ~R 824 Each independently
[2188] hydrogen atom,
[2189] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2190] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2191] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2192] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2193] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2194] -O-(R 904 The groups shown in the figure,
[2195] -S-(R 905 The groups shown in the figure,
[2196] -N(R 906 (R) 907 The groups shown in the figure,
[2197] Halogen atoms,
[2198] cyano,
[2199] Nitro,
[2200] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2201] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2202] In one embodiment, the compound represented by the above general formula (8) is represented by any one of the following general formulas (81-7) to (81-18).
[2203]
Chemical Formula 234
[2204]
[2205] [Chemical Formula 235]
[2206]
[2207]
Chemical Formula 236
[2208]
[2209] [Chemical Formula 237]
[2210]
[2211] [Chemical Formula 238]
[2212]
[2213] [Chemical Formula 239]
[2214]
[2215] (In the above general formulas (81-7) to (81-18),
[2216] X8 has the same meaning as X8 in the above general formula (8).
[2217] * represents a single bond bonded to the monovalent group shown in the above general formula (84).
[2218] R 801 ~R 824 Each independently relates to the R group in the above general formulas (81-1) to (81-6) that is not the monovalent group shown in the above general formula (84). 801 ~R 824 The meaning is the same.
[2219] R that does not form the divalent groups shown in general formulas (82) and (83) above and is not the monovalent group shown in general formula (84) above. 801 ~R 808 And R groups that are not monovalent groups represented by the above general formula (84) 811 ~R 814 and R 821 ~R 824 Preferred to be independent
[2220] hydrogen atom,
[2221] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2222] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2223] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2224] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2225] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2226] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[2227] The monovalent group represented by the above general formula (84) is preferably represented by the following general formula (85) or general formula (86).
[2228] [Chemical Formula 240]
[2229]
[2230] (In the above general formula (85),
[2231] R 831 ~R 840 Each independently
[2232] hydrogen atom,
[2233] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2234] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2235] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2236] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2237] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2238] -O-(R 904 The groups shown in the figure,
[2239] -S-(R 905 The groups shown in the figure,
[2240] -N(R 906 (R) 907 The groups shown in the figure,
[2241] Halogen atoms,
[2242] cyano,
[2243] Nitro,
[2244] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2245] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2246] The asterisk (*) in the above general formula (85) has the same meaning as the asterisk (*) in the above general formula (84).
[2247]
Chemical Formula 241
[2248]
[2249] (In the above general formula (86),
[2250] Ar 801 L 801 and L 803 Ar in the above general formula (84) 801 L 801 and L 803 Same meaning
[2251] HAr 801 The structure is shown in the following general formula (87).
[2252]
Chemical Formula 242
[2253]
[2254] (In the above general formula (87),
[2255] X 81 It consists of oxygen or sulfur atoms.
[2256] R 841 ~R 848 Any one of them is related to L 803 Bonded single bonds,
[2257] R is not a single-key letter. 841 ~R 848 Each independently
[2258] hydrogen atom,
[2259] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2260] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2261] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2262] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2263] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2264] -O-(R 904 The groups shown in the figure,
[2265] -S-(R 905 The groups shown in the figure,
[2266] -N(R 906 (R) 907 The groups shown in the figure,
[2267] Halogen atoms,
[2268] cyano,
[2269] Nitro,
[2270] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2271] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2272] (Specific examples of compounds represented by general formula (8))
[2273] As a compound represented by the above general formula (8), the compounds disclosed in International Publication No. 2014 / 104144 and, for example, the compounds shown below can be cited as specific examples.
[2274] [Chemical Formula 243]
[2275]
[2276] [Chemical Formula 244]
[2277]
[2278] [Chemical Formula 245]
[2279]
[2280] [Chemical Formula 246]
[2281]
[2282] [Chemical Formula 247]
[2283]
[2284] [Chemical Formula 248]
[2285]
[2286] [Chemical Formula 249]
[2287]
[2288] (The compound represented by general formula (9))
[2289] The compounds represented by general formula (9) will be described.
[2290] [Chemical Formula 250]
[2291]
[2292] (In the above general formula (9),
[2293] A 91 Ring and A 92 Each ring is independent of the others.
[2294] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or
[2295] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2296] Selected from A 91 Ring and A 92 One or more rings in the ring and
[2297] The bonding of the structure shown in the following general formula (92) is as follows.
[2298]
Chemical Formula 251
[2299]
[2300] (In the above general formula (92),
[2301] A 93 Ring for
[2302] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or
[2303] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2304] X9 is NR 93 C(R) 94 (R) 95 ), Si(R) 96 (R) 97 ), Ge(R) 98 (R) 99 ), oxygen atoms, sulfur atoms or selenium atoms,
[2305] R 91 and R 92
[2306] They bond together to form substituted or unsubstituted monocyclic rings.
[2307] They bond together to form substituted or unsubstituted fused rings, or
[2308] They do not bond with each other.
[2309] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 91 and R 92 and R 93 ~R 99 Each independently
[2310] hydrogen atom,
[2311] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2312] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2313] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2314] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2315] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2316] -O-(R 904 The groups shown in the figure,
[2317] -S-(R 905 The groups shown in the figure,
[2318] -N(R 906 (R) 907 The groups shown in the figure,
[2319] Halogen atoms,
[2320] cyano,
[2321] Nitro,
[2322] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2323] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2324] Selected from A 91 Ring and A 92 One or more rings in the ring are bonded to the structure shown in the above general formula (92). That is, in one embodiment, A 91 The cyclic carbon atom of the aforementioned aromatic hydrocarbon ring or the cyclic atom of the aforementioned heterocycle is bonded to the structure shown in the aforementioned general formula (92). Additionally, in one embodiment, A 92The cyclic carbon atom of the above-mentioned aromatic hydrocarbon ring or the cyclic atom of the above-mentioned heterocycle is bonded to the structure shown in the above-mentioned general formula (92).
[2325] In one embodiment, the group represented by the following general formula (93) is bonded to A 91 Ring and A 92 One or both of them in the ring.
[2326]
Chemical Formula 252
[2327]
[2328] (In the above general formula (93),
[2329] Ar 91 and Ar 92 Each independently
[2330] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2331] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2332] L 91 ~L 93 Each independently
[2333] single bond,
[2334] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms
[2335] Substituted or unsubstituted divalent heterocyclic groups with 5 to 30 cyclic atoms, or
[2336] A divalent linking group is formed by bonding 2 to 4 groups from the group consisting of a substituted or unsubstituted aryl group with 6 to 30 carbon atoms and a substituted or unsubstituted divalent heterocyclic group with 5 to 30 carbon atoms.
[2337] In the above general formula (93), * indicates that it is related to A. 91 Ring and A 92 The bonding position of any element in the ring.
[2338] In one implementation, besides A 91 Outside the ring, there is A. 92 The cyclic carbon atom of the aforementioned aromatic hydrocarbon ring or the cyclic atom of the aforementioned heterocycle is bonded to the structure shown in the aforementioned general formula (92). In this case, the structures shown in the aforementioned general formula (92) may be the same as or different from each other.
[2339] In one implementation, R 91 and R 92 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.
[2340] In one implementation, R 91 and R 92 They bond together to form a fluorene structure.
[2341] In one implementation, ring A 91 And Ring A 92 Each is an aromatic hydrocarbon ring, either substituted or unsubstituted, having 6 to 50 carbon atoms, such as a substituted or unsubstituted benzene ring.
[2342] In one implementation, ring A 93 A cyclic aromatic hydrocarbon ring with 6 to 50 carbon atoms, either substituted or unsubstituted, such as a substituted or unsubstituted benzene ring.
[2343] In one implementation, X9 is an oxygen atom or a sulfur atom.
[2344] (Specific examples of compounds represented by general formula (9))
[2345] As a compound represented by the above general formula (9), the following compounds can be cited as specific examples.
[2346] [Chemical Formula 253]
[2347]
[2348] [Chemical Formula 254]
[2349]
[2350] [Chemical Formula 255]
[2351]
[2352] [Chemical Formula 256]
[2353]
[2354] (The compound represented by general formula (10))
[2355] The compounds represented by general formula (10) will be described.
[2356] [Chemical Formula 257]
[2357]
[2358] [Chemical Formula 258]
[2359]
[2360] (In the above general formula (10),
[2361] Ax1 ring is a ring as shown in the above general formula (10a) that is fused at any position of adjacent rings.
[2362] Ax2 ring is a ring as shown in the above general formula (10b) that is fused at any position between adjacent rings.
[2363] The two asterisks in the above general formula (10b) are bonded to any position of the Ax3 ring.
[2364] X A and X B Each independently is C(R) 1003 (R) 1004 ), Si(R) 1005 (R) 1006 ), oxygen atom or sulfur atom,
[2365] Ax3 ring is
[2366] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or
[2367] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2368] Ar 1001 for
[2369] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2370] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2371] R 1001 ~R 1006 Each independently
[2372] hydrogen atom,
[2373] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2374] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2375] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2376] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2377] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2378] -O-(R 904 The groups shown in the figure,
[2379] -S-(R 905 The groups shown in the figure,
[2380] -N(R 906 (R) 907 The groups shown in the figure,
[2381] Halogen atoms,
[2382] cyano,
[2383] Nitro,
[2384] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2385] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2386] mx1 is 3, mx2 is 2.
[2387] Multiple R 1001 They are the same or different.
[2388] Multiple R 1002 They are the same or different.
[2389] ax is 0, 1, or 2.
[2390] When ax is 0 or 1, the structures within the parentheses shown in "3-ax" are either the same or different.
[2391] When ax = 2, multiple Ar 1001 (They may be the same or different.)
[2392] In one implementation, Ar 1001 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[2393] In one embodiment, the Ax3 ring is a substituted or unsubstituted aromatic hydrocarbon ring with 6 to 50 carbon atoms, such as a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.
[2394] In one implementation, R 1003 and R 1004 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[2395] In one implementation, ax is 1.
[2396] (Specific examples of compounds represented by general formula (10))
[2397] As a compound represented by the above general formula (10), the following compounds can be cited as specific examples.
[2398] [Chemical Formula 259]
[2399]
[2400] In one embodiment, the light-emitting layer contains, as the sixth and seventh compounds, one or more compounds selected from the compounds shown in the above general formula (4), the compounds shown in the above general formula (5), the compounds shown in the above general formula (7), the compounds shown in the above general formula (8), the compounds shown in the above general formula (9), and the compounds shown in the following general formula (63a).
[2401] [Chemical Formula 260]
[2402]
[2403] (In the above general formula (63a),
[2404] R 631 With R 646 They may bond to form substituted or unsubstituted heterocycles, or they may not form substituted or unsubstituted heterocycles.
[2405] R 633 With R 647 They may bond to form substituted or unsubstituted heterocycles, or they may not form substituted or unsubstituted heterocycles.
[2406] R 634 With R 651 They may bond to form substituted or unsubstituted heterocycles, or they may not form substituted or unsubstituted heterocycles.
[2407] R 641 With R 642 They may bond to form substituted or unsubstituted heterocycles, or they may not form substituted or unsubstituted heterocycles.
[2408] R 631 ~R 651 Two or more adjacent groups
[2409] They bond together to form substituted or unsubstituted monocyclic rings.
[2410] They bond together to form substituted or unsubstituted fused rings, or
[2411] They do not bond with each other.
[2412] R does not form the aforementioned substituted or unsubstituted heterocycles, does not form the aforementioned monocyclic rings, and does not form the aforementioned fused rings. 631 ~R 651 Each independently
[2413] hydrogen atom,
[2414] Halogen atoms,
[2415] cyano,
[2416] Nitro,
[2417] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2418] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2419] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2420] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2421] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2422] -O-(R 904 The groups shown in the figure,
[2423] -S-(R 905 The groups shown in the figure,
[2424] -N(R 906 (R) 907 The groups shown in the figure,
[2425] A substituted or unsubstituted aryl group with 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 cyclic atoms.
[2426] Among them, R does not form the aforementioned substituted or unsubstituted heterocycles, does not form the aforementioned monocyclic rings, and does not form the aforementioned fused rings. 631 ~R 651 At least one of them is
[2427] Halogen atoms,
[2428] cyano,
[2429] Nitro,
[2430] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2431] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2432] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2433] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2434] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2435] -O-(R904 The groups shown in the figure,
[2436] -S-(R 905 The groups shown in the figure,
[2437] -N(R 906 (R) 907 The groups shown in the figure,
[2438] Halogen atoms,
[2439] cyano,
[2440] Nitro,
[2441] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2442] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2443] In one embodiment, the compound represented by the above general formula (4) is a compound represented by the above general formula (41-3), general formula (41-4) or general formula (41-5), wherein the A1 ring in the above general formula (41-5) is a fused aromatic hydrocarbon ring with 10 to 50 cyclic carbon atoms, substituted or unsubstituted, or a fused heterocycle with 8 to 50 cyclic atoms, substituted or unsubstituted.
[2444] In one embodiment, the substituted or unsubstituted fused aromatic hydrocarbon rings with 10 to 50 carbon atoms in the above general formulas (41-3), (41-4), and (41-5) are...
[2445] Substituted or unsubstituted naphthalene ring,
[2446] Substituted or unsubstituted anthracene rings, or
[2447] Substituted or unsubstituted fluorene ring,
[2448] The above-mentioned fused heterocycles with 8 to 50 cyclic atoms, whether substituted or unsubstituted, are
[2449] Substituted or unsubstituted dibenzofuran rings,
[2450] Substituted or unsubstituted carbazole ring, or
[2451] Substituted or unsubstituted dibenzothiophene ring.
[2452] In one embodiment, the substituted or unsubstituted fused aromatic hydrocarbon ring with 10 to 50 carbon atoms in the above general formulas (41-3), (41-4), or (41-5) is...
[2453] Substituted or unsubstituted naphthalene ring, or
[2454] Substituted or unsubstituted fluorene ring,
[2455] The above-mentioned fused heterocycles with 8 to 50 cyclic atoms, whether substituted or unsubstituted, are
[2456] Substituted or unsubstituted dibenzofuran rings,
[2457] Substituted or unsubstituted carbazole ring, or
[2458] Substituted or unsubstituted dibenzothiophene ring.
[2459] In one embodiment, the compound represented by the above general formula (4) is selected from...
[2460] The compounds represented by the following general formula (461),
[2461] The compounds represented by the following general formula (462),
[2462] The compounds represented by the following general formula (463),
[2463] The compounds represented by the following general formula (464),
[2464] The compounds represented by the following general formula (465),
[2465] The compounds represented by the following general formula (466), and
[2466] The group consisting of compounds represented by the following general formula (467).
[2467]
Chemical Formula 261
[2468]
[2469]
Chemical Formula 262
[2470]
[2471] [Chemical Formula 263]
[2472]
[2473] [Chemical Formula 264]
[2474]
[2475] [Chemical Formula 265]
[2476]
[2477] (In the above general formulas (461) to (467),
[2478] R 421 ~R 427 R431 ~R 436 R 440 ~R 448 and R 451 ~R 454 One or more of the groups consisting of two or more adjacent elements.
[2479] They bond together to form substituted or unsubstituted monocyclic rings.
[2480] They bond together to form substituted or unsubstituted fused rings, or
[2481] They do not bond with each other.
[2482] R 437 R 438 and R that does not form the aforementioned single ring and does not form the aforementioned fused ring. 421 ~R 427 R 431 ~R 436 R 440 ~R 448 and R 451 ~R 454 Each independently
[2483] hydrogen atom,
[2484] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2485] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2486] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2487] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2488] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2489] -O-(R 904 The groups shown in the figure,
[2490] -S-(R 905 The groups shown in the figure,
[2491] -N(R 906 (R) 907 The groups shown in the figure,
[2492] Halogen atoms,
[2493] cyano,
[2494] Nitro,
[2495] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2496] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2497] X4 represents an oxygen atom, NR 801 or C(R) 802 (R) 803 ),
[2498] R 801 R 802 and R 803 Each independently
[2499] hydrogen atom,
[2500] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2501] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2502] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2503] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2504] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[2505] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[2506] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[2507] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
[2508] In R 803 In the case of multiple Rs, multiple Rs 803 (They may be the same or different.)
[2509] In one implementation, R 421 ~R 427 and R 440 ~R 448 Each independently
[2510] hydrogen atom,
[2511] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2512] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[2513] In one implementation, R 421 ~R 427 and R 440 ~R 447 Each independently chooses freedom
[2514] hydrogen atom,
[2515] Substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, and
[2516] The group consisting of substituted or unsubstituted heterocyclic groups with 5 to 18 cyclic atoms.
[2517] In one embodiment, the compound represented by the above general formula (41-3) is the compound represented by the following general formula (41-3-1).
[2518]
Chemical Formula 266
[2519]
[2520] (In the above general formula (41-3-1), R) 423 R 425 R 426 R 442 R 444 and R 445 Each independently relates to R in the above general formula (41-3). 423 R 425 R 426 R 442 R 444 and R 445 The meaning is the same.
[2521] In one embodiment, the compound represented by the above general formula (41-3) is the compound represented by the following general formula (41-3-2).
[2522] [Chemical Formula 267]
[2523]
[2524] (In the above general formula (41-3-2), R) 421 ~R 427 and R 440 ~R 448 Each independently relates to R in the above general formula (41-3). 421 ~R 427 and R 440 ~R 448 Same meaning
[2525] Among them, R 421 ~R 427 and R 440~R 446 At least one of them is -N(R) 906 (R) 907 The group shown in the diagram.
[2526] In one embodiment, R in the above formula (41-3-2) 421 ~R 427 and R 440 ~R 446 Any two of them are -N(R) 906 (R) 907 The group shown is ).
[2527] In one embodiment, the compound represented by formula (41-3-2) above is the compound represented by formula (41-3-3) below.
[2528] [Chemical Formula 268]
[2529]
[2530] (In the above general formula (41-3-3), R) 421 ~R 424 R 440 ~R 443 R 447 and R 448 Each independently relates to R in the above general formula (41-3). 421 ~R 424 R 440 ~R 443 R 447 and R 448 Same meaning
[2531] R A R B R C and R D Each independently
[2532] Substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, or
[2533] (Substituted or unsubstituted heterocyclic groups with 5 to 18 cyclic atoms)
[2534] In one embodiment, the compound represented by formula (41-3-3) above is the compound represented by formula (41-3-4) below.
[2535] [Chemical Formula 269]
[2536]
[2537] (In the above general formula (41-3-4), R) 447 R 448R A R B R C and R D Each independently relates to R in the above equation (41-3-3) 447 R 448 R A R B R C and R D The meaning is the same.
[2538] In one implementation, R A R B R C and R D Each is an aryl group, either substituted or unsubstituted, with 6 to 18 carbon atoms.
[2539] In one implementation, R A R B R C and R D Each can be a substituted or unsubstituted phenyl group.
[2540] In one implementation, R 447 and R 448 It is a hydrogen atom.
[2541] In one embodiment, the substituents expressed as "substituted or unsubstituted" in the above formulas are:
[2542] Unsubstituted alkyl groups having 1 to 50 carbon atoms
[2543] Unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2544] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms
[2545] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2546] -Si(R 901a (R) 902a (R) 903a ),
[2547] -O-(R 904a ),
[2548] -S-(R 905a ),
[2549] -N(R 906a (R) 907a ),
[2550] Halogen atoms,
[2551] cyano,
[2552] Nitro,
[2553] Unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2554] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms
[2555] R 901a ~R 907a Each independently
[2556] hydrogen atom,
[2557] Unsubstituted alkyl groups having 1 to 50 carbon atoms
[2558] Unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2559] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms
[2560] In R 901a In cases where there are two or more R's, there are two or more R's. 901a They are the same or different.
[2561] In R 902a In cases where there are two or more R's, there are two or more R's. 902a They are the same or different.
[2562] In R 903a In cases where there are two or more R's, there are two or more R's. 903a They are the same or different.
[2563] In R 904a In cases where there are two or more R's, there are two or more R's. 904a They are the same or different.
[2564] In R 905a In cases where there are two or more R's, there are two or more R's. 905a They are the same or different.
[2565] In R 906a In cases where there are two or more R's, there are two or more R's. 906a They are the same or different.
[2566] In R 907a In cases where there are two or more R's, there are two or more R's. 907a They are the same or different.
[2567] In one embodiment, the substituents expressed as "substituted or unsubstituted" in the above formulas are:
[2568] Unsubstituted alkyl groups having 1 to 50 carbon atoms
[2569] Unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2570] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms.
[2571] In one embodiment, the substituents expressed as "substituted or unsubstituted" in the above formulas are:
[2572] Unsubstituted alkyl groups having 1 to 18 carbon atoms
[2573] Unsubstituted aryl groups with 6 to 18 carbon atoms, or
[2574] Unsubstituted heterocyclic groups with 5 to 18 cyclic atoms.
[2575] In the sixth and seventh compounds, the groups described as "substituted or unsubstituted" are preferably "unsubstituted".
[2576] In the organic EL element involved in this embodiment, the sixth compound is preferably a compound that exhibits light emission with a main peak wavelength of 430 nm or more and 480 nm or less.
[2577] In the organic EL element involved in this embodiment, the seventh compound is preferably a compound that emits light with a main peak wavelength of 430 nm or more and 480 nm or less.
[2578] The method for determining the maximum peak wavelength of a compound is shown below. Ten samples of the compound to be measured were prepared. -6 mol / L or higher and 10 -5 A toluene solution with a concentration of less than mol / L was added to a quartz cuvette, and the emission spectrum of the sample was measured at room temperature (300K) (vertical axis is set as emission intensity, and horizontal axis is set as wavelength). The emission spectrum can be measured using a spectrophotometer (device name: F-7000) manufactured by Hitachi Advanced Scientific Corporation. It should be noted that the emission spectrum measurement device is not limited to the device used here.
[2579] In the emission spectrum, the peak wavelength of the emission spectrum with the highest emission intensity is taken as the maximum emission peak wavelength. It should be noted that, in this specification, the maximum peak wavelength of fluorescence emission is sometimes referred to as the maximum fluorescence emission peak wavelength (FL-peak).
[2580] In the organic EL element of this embodiment, when the first light-emitting layer includes a first compound and a seventh compound, the singlet energy S1(H1) of the first compound and the singlet energy S1(D7) of the seventh compound preferably satisfy the following mathematical formula (Mathematical Formula 1).
[2581] S1(H1)>S1(D7)...(Mathematical Formula 1)
[2582] In the organic EL element of this embodiment, when the second light-emitting layer contains a second compound and a sixth compound, the singlet energy S1(H2) of the second compound and the singlet energy S1(D6) of the sixth compound preferably satisfy the following mathematical formula (Mathematical Formula 2).
[2583] S1(H2)>S1(D6)...(Mathematical Expression 2)
[2584] (Singlet energy S1)
[2585] The following methods can be cited as methods for determining the singlet energy S1 using a solution (sometimes called the solution method).
[2586] 10 compounds prepared as the test targets -5 mol / L or higher and 10 -4 A toluene solution with a concentration of less than mol / L was added to a quartz cuvette, and the absorption spectrum of the sample was measured at room temperature (300K) (the vertical axis is set as absorption intensity, and the horizontal axis is set as wavelength). For the downward tangent on the longer wavelength side of the absorption spectrum, the wavelength value λedge [nm] at the intersection of the tangent and the horizontal axis was substituted into the conversion formula (F2) shown later to calculate the singlet energy.
[2587] Conversion formula (F2): S1[eV]=1239.85 / λedge
[2588] As an absorption spectroscopy measuring device, examples include, but are not limited to, the Hitachi spectrophotometer (device name: U3310).
[2589] The tangent for the downward sag on the longer wavelength side of the absorption spectrum is derived as follows. Consider the tangent at various points on the spectral curve as the longest wavelength maximum is moved along the longer wavelength direction. This tangent exhibits a repeated pattern of decreasing and then increasing slope as the curve declines (i.e., as the value on the vertical axis decreases). The tangent drawn at the point where the slope is minimized on the longest wavelength side (excluding cases where absorbance is below 0.1) is taken as the tangent for the downward sag on the longer wavelength side of the absorption spectrum.
[2590] It should be noted that the maximum absorbance values below 0.2 are not included in the maximum values on the longest wavelength side mentioned above.
[2591] (Thickness of the light-emitting layer)
[2592] In this embodiment, the film thickness of the first and second light-emitting layers of the organic EL element is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less. If the film thickness of the first and second light-emitting layers is 5 nm or more, it is easier to form the light-emitting layers and adjust the chromaticity. If the film thickness of the first and second light-emitting layers is 50 nm or less, it is easier to suppress the rise in driving voltage.
[2593] (The content of compounds in the luminescent layer)
[2594] When the first light-emitting layer contains the first compound and the seventh compound, the contents of the first compound and the seventh compound in the first light-emitting layer are preferably within the following ranges, for example.
[2595] The content of the first compound is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less.
[2596] The content of the seventh compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less.
[2597] The maximum combined content of the first compound and the seventh compound in the first luminescent layer is 100% by mass.
[2598] It should be noted that this embodiment does not exclude the inclusion of materials other than the first compound and the seventh compound in the first light-emitting layer.
[2599] In the first luminescent layer, the first compound may contain only one type or two or more types. In the first luminescent layer, the seventh compound may contain only one type or two or more types.
[2600] When the second light-emitting layer contains the second compound and the sixth compound, the content of the second compound and the sixth compound in the second light-emitting layer is preferably within the following ranges, for example.
[2601] The content of the second compound is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less.
[2602] The content of the sixth compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less.
[2603] The maximum combined content of the second and sixth compounds in the second luminescent layer is 100% by mass.
[2604] It should be noted that this embodiment does not exclude the inclusion of materials other than the second compound and the sixth compound in the second light-emitting layer.
[2605] In the second luminescent layer, the second compound may contain only one type or more types. In the second luminescent layer, the sixth compound may contain only one type or more types.
[2606] (First electron transport layer)
[2607] In the organic EL element involved in this embodiment, the first electron transport layer comprises a third compound represented by the following general formula (3).
[2608] In the organic EL element involved in this embodiment, the first electron transport layer preferably contains only the third compound.
[2609] (Third compound)
[2610] The third compound represented by general formula (3) will be explained. It should be noted that the fourth compound contained in the second electron transport layer and the fifth compound contained in the third electron transport layer are sometimes represented by the following general formula (3).
[2611] [Chemical Formula 270]
[2612]
[2613] (In the above general formula (3),
[2614] A is
[2615] Substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, or
[2616] Heterocyclic groups with 5 to 13 cyclic atoms, substituted or unsubstituted.
[2617] B is
[2618] Substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, or
[2619] Heterocyclic groups with 5 to 13 cyclic atoms, substituted or unsubstituted.
[2620] L is
[2621] single bond,
[2622] Substituted or unsubstituted cyclic aromatic hydrocarbons with 6–18 carbon atoms (n+1) cyclic groups
[2623] Substituted or unsubstituted heterocyclic groups with 5 to 13 cyclic atoms (n+1) valence, or
[2624] A (n+1) valence group having a structure consisting of two or three distinct groups bonded together from a substituted or unsubstituted aromatic hydrocarbon cyclic group having 6 to 18 carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 13 cyclic atoms.
[2625] C is
[2626] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2627] Heterocyclic groups with 5 to 60 cyclic atoms, substituted or unsubstituted.
[2628] n is 1, 2, or 3.
[2629] When n is 2 or higher, L is not a single bond.
[2630] When n is 2 or more, multiple Cs may be identical or different.
[2631] In the organic EL element involved in this embodiment,
[2632] The third compound is preferably a compound represented by the following general formula (31) or general formula (310).
[2633]
Chemical Formula 271
[2634]
[2635] In the above general formula (31),
[2636] A, B, and C are defined in the same way as in the general formula (3) above.
[2637] R 31 ~R 34 One or more of the groups consisting of two or more adjacent elements.
[2638] They bond together to form substituted or unsubstituted monocyclic rings.
[2639] They bond together to form substituted or unsubstituted fused rings, or
[2640] They do not bond with each other.
[2641] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 31 ~R 34 Each independently
[2642] hydrogen atom,
[2643] cyano,
[2644] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2645] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2646] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2647] -O-(R 904 The groups shown in the figure,
[2648] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2649] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2650]
Chemical Formula 272
[2651]
[2652] (In the above general formula (310),
[2653] A and B are defined in the same way as in the general formula (3) above.
[2654] X 30 For CR 51 R 52 NR 53 oxygen or sulfur atoms
[2655] In X 30 For CR 51 R 52 In the case of R 51 and R 52 Groups
[2656] They bond together to form substituted or unsubstituted monocyclic rings.
[2657] They bond together to form substituted or unsubstituted fused rings, or
[2658] They do not bond with each other.
[2659] R 300 ~R 304 One or more of the groups consisting of two or more adjacent elements.
[2660] They bond together to form substituted or unsubstituted monocyclic rings.
[2661] They bond together to form substituted or unsubstituted fused rings, or
[2662] They do not bond with each other.
[2663] R 53 R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 51 R 52 R 300 ~R 304 Each independently
[2664] hydrogen atom,
[2665] cyano,
[2666] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2667] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2668] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2669] -O-(R 904 The groups shown in the figure,
[2670] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2671] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2672] na is 3, 3 R 300 (They may be the same or different.)
[2673] (In the third compound mentioned above, R) 901 R 902 R 903 and R 904 Each independently
[2674] hydrogen atom,
[2675] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2676] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2677] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2678] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2679] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[2680] In R 902 In the case of multiple Rs, multiple Rs902 They are the same or different.
[2681] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[2682] In R 904 In the case of multiple Rs, multiple Rs 904 (They may be the same or different.)
[2683] In the organic EL element of this embodiment, the third compound is preferably a compound represented by the following general formula (32), general formula (33), general formula (34) or general formula (35).
[2684] [Chemical Formula 273]
[2685]
[2686] [Chemical Formula 274]
[2687]
[2688] (In the above general formulas (32) to (35),
[2689] A and B are defined in the same way as in the general formula (3) above.
[2690] X 30 For CR 51 R 52 NR 53 oxygen or sulfur atoms
[2691] In X 30 For CR 51 R 52 In the case of R 51 and R 52 Groups
[2692] They bond together to form substituted or unsubstituted monocyclic rings.
[2693] They bond together to form substituted or unsubstituted fused rings, or
[2694] They do not bond with each other.
[2695] R 301 ~R 308 One or more of the groups consisting of two or more adjacent elements.
[2696] They bond together to form substituted or unsubstituted monocyclic rings.
[2697] They bond together to form substituted or unsubstituted fused rings, or
[2698] They do not bond with each other.
[2699] R 53 R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 51 R 52 R 301 ~R 308 Each independently
[2700] hydrogen atom,
[2701] cyano,
[2702] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2703] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2704] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2705] -O-(R 904 The groups shown in the figure,
[2706] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2707] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2708] In the organic EL element involved in this embodiment, the third compound is preferably a compound represented by the above general formula (32).
[2709] In the organic EL element involved in this embodiment, the third compound is preferably a compound represented by the following general formula (36).
[2710] [Chemical Formula 275]
[2711]
[2712] (In the above general formula (36),
[2713] A, B, and C are defined in the same way as in the general formula (3) above.
[2714] R 32 ~R 39 One or more of the groups consisting of two or more adjacent elements.
[2715] They bond together to form substituted or unsubstituted monocyclic rings.
[2716] They bond together to form substituted or unsubstituted fused rings, or
[2717] They do not bond with each other.
[2718] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 32 ~R 39 Each independently
[2719] hydrogen atom,
[2720] cyano,
[2721] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2722] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2723] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2724] -O-(R 904 The groups shown in the figure,
[2725] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2726] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2727] In the third compound mentioned above, R 901 R 902 R 903 and R 904 Each independently
[2728] hydrogen atom,
[2729] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2730] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2731] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2732] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2733] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[2734] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[2735] In R 903In the case of multiple Rs, multiple Rs 903 They are the same or different.
[2736] In R 904 In the case of multiple Rs, multiple Rs 904 (They may be the same or different.)
[2737] In the third compound of the organic EL element involved in this embodiment, C is preferably a heterocyclic group with 13 to 35 cyclic atoms, either substituted or unsubstituted.
[2738] In the third compound of the organic EL element involved in this embodiment, C is preferably an aryl group with 14 to 24 cyclic carbons, either substituted or unsubstituted.
[2739] In the organic EL element involved in this embodiment, the third compound is preferably a compound represented by the following general formula (37).
[2740] [Chemical Formula 276]
[2741]
[2742] (In the above general formula (37),
[2743] A, B, and L are defined in the same way as in the general formula (3) above.
[2744] Cz is a group represented by the following general formula (Cz1), (Cz2) or (Cz3).
[2745] n is 1, 2, or 3.
[2746] When n is 2 or 3, multiple Cz may be identical or different.
[2747] [Chemical Formula 277]
[2748]
[2749] [Chemical Formula 278]
[2750]
[2751] [Chemical Formula 279]
[2752]
[2753] In the above general formulas (Cz1), (Cz2), and (Cz3),
[2754] R 311 ~R 318 One or more of the groups consisting of two or more adjacent elements.
[2755] They bond together to form substituted or unsubstituted monocyclic rings.
[2756] They bond together to form substituted or unsubstituted fused rings, or
[2757] They do not bond with each other.
[2758] R 320 ~R 324 One or more of the groups consisting of two or more adjacent elements.
[2759] They bond together to form substituted or unsubstituted monocyclic rings.
[2760] They bond together to form substituted or unsubstituted fused rings, or
[2761] They do not bond with each other.
[2762] R 330 ~R 334 One or more groups consisting of two or more adjacent elements in Rx.
[2763] They bond together to form substituted or unsubstituted monocyclic rings.
[2764] They bond together to form substituted or unsubstituted fused rings, or
[2765] They do not bond with each other.
[2766] R 340 ~R 344 One or more of the groups consisting of two or more adjacent elements.
[2767] They bond together to form substituted or unsubstituted monocyclic rings.
[2768] They bond together to form substituted or unsubstituted fused rings, or
[2769] They do not bond with each other.
[2770] R 351 ~R 358 One or more of the groups consisting of two or more adjacent elements.
[2771] They bond together to form substituted or unsubstituted monocyclic rings.
[2772] They bond together to form substituted or unsubstituted fused rings, or
[2773] They do not bond with each other.
[2774] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 311 ~R 318 R 320 ~R 324 R330 ~R 334 R X R 340 ~R 344 and R 351 ~R 358 Each independently
[2775] hydrogen atom,
[2776] cyano,
[2777] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2778] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2779] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2780] -O-(R 904 The groups shown in the figure,
[2781] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2782] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2783] n1, n2, and n3 are all 3.
[2784] 3 Rs 320 They are the same or different.
[2785] 3 Rs 330 They are the same or different.
[2786] 3 Rs 340 They are the same or different.
[2787] In the above general formulas (Cz1), (Cz2), and (Cz3), the * is bonded to L.
[2788] In the third compound mentioned above, R 901 R 902 R 903 and R 904 Each independently
[2789] hydrogen atom,
[2790] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2791] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2792] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2793] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2794] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[2795] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[2796] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[2797] In R 904 In the case of multiple Rs, multiple Rs 904 (They may be the same or different.)
[2798] In the organic EL element involved in this embodiment, the compound represented by the above general formula (3) is preferably the compound represented by the following general formula (38).
[2799] [Chemical Formula 280]
[2800]
[2801] (In the above general formula (38),
[2802] A and B are defined in the same way as in the general formula (3) above.
[2803] La for
[2804] single bond,
[2805] Substituted or unsubstituted cyclic groups of divalent aromatic hydrocarbons with 6 to 18 carbon atoms, or
[2806] Divalent heterocyclic groups with 5 to 13 cyclic atoms, substituted or unsubstituted.
[2807] Ac is a group represented by any of the following general formulas (Ac1), (Ac2), and (Ac3).
[2808]
Chemical Formula 281
[2809]
[2810] (In the above general formula (Ac1),
[2811] X 31 ~X 36 Each independently
[2812] nitrogen atoms,
[2813] Carbon atoms bonded to La, or
[2814] Carbon atoms bonded to Ry
[2815] X 31 ~X 36 One or more of them are nitrogen atoms.
[2816] X 31 ~X 36 One of them is a carbon atom bonded to La.
[2817] Ry is
[2818] hydrogen atom,
[2819] cyano,
[2820] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2821] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2822] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2823] -O-(R 904 The groups shown in the figure,
[2824] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2825] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2826] When multiple Ry exist, they may be identical or different from each other.
[2827] (In the above general formula (Ac2),
[2828] X 21 ~X 28 Each independently
[2829] nitrogen atoms,
[2830] Carbon atoms bonded to La, or
[2831] Carbon atoms bonded to Rz
[2832] X 21 ~X 28 One or more of them are nitrogen atoms.
[2833] X 21 ~X 28One of them is a carbon atom bonded to La.
[2834] When there are multiple Rz, one or more groups consisting of two or more adjacent Rz are considered.
[2835] They bond together to form substituted or unsubstituted monocyclic rings.
[2836] They bond together to form substituted or unsubstituted fused rings, or
[2837] They do not bond with each other.
[2838] Rz for each of the following not forming a monocyclic ring with or without the aforementioned substitution or unsubstituent form, and for each of the following not forming a fused ring with or without the aforementioned substitution or unsubstituent form, is independently [value missing].
[2839] hydrogen atom,
[2840] cyano,
[2841] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2842] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2843] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2844] -O-(R 904 The groups shown in the figure,
[2845] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2846] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2847] (In the above general formula (Ac3),
[2848] n4 is 1, 2, 3, 4, 5, 6, 7, 8, or 9.
[2849] D is
[2850] Aryl groups with 6 to 18 carbon atoms forming a ring with n4 cyano groups, or
[2851] Heterocyclic groups with 5 to 13 cyclic atoms and n4 cyano groups
[2852] Wherein, D has substituents other than cyano, or does not have substituents other than cyano.
[2853] In the above general formula (Ac3), the * is bonded to La.
[2854] In the third compound mentioned above, R 901R 902 R 903 and R 904 Each independently
[2855] hydrogen atom,
[2856] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2857] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2858] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2859] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2860] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[2861] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[2862] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[2863] In R 904 In the case of multiple Rs, multiple Rs 904 (They may be the same or different.)
[2864] In the organic EL element of this embodiment, the compound represented by the above general formula (38) is preferably the compound represented by the following general formula (381).
[2865]
Chemical Formula 282
[2866]
[2867] (In the above general formula (381),
[2868] A, B, and Ac are defined in the same way as in the general formula (38) above.
[2869] R 381 ~R 384 One or more of the groups consisting of two or more adjacent elements.
[2870] They bond together to form substituted or unsubstituted monocyclic rings.
[2871] They bond together to form substituted or unsubstituted fused rings, or
[2872] They do not bond with each other.
[2873] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 381 ~R 384 Each independently
[2874] hydrogen atom,
[2875] cyano,
[2876] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2877] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2878] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2879] -O-(R 904 The groups shown in the figure,
[2880] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2881] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2882] R 901 ~R 904 Same as the definition in general formula (38) above.
[2883] In the organic EL element of this embodiment, the compound represented by the above general formula (38) is preferably the compound represented by the following general formula (382).
[2884] [Chemical Formula 283]
[2885]
[2886] (In the above general formula (382),
[2887] A, B, and Ac are defined in the same way as in the general formula (38) above.
[2888] R 383 for
[2889] hydrogen atom,
[2890] cyano,
[2891] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2892] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2893] -Si(R901 (R) 902 (R) 903 The groups shown in the figure,
[2894] -O-(R 904 The groups shown in the figure,
[2895] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2896] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2897] R 901 ~R 904 Same as the definition in general formula (38) above.
[2898] In the organic EL element involved in this embodiment, L is preferably a single bond, or a substituted or unsubstituted cyclic aromatic hydrocarbon cyclogroup with 6 to 12 carbon atoms in the (n+1) valence.
[2899] In the organic EL element involved in this embodiment, L or La is preferably a single bond.
[2900] In the organic EL element involved in this embodiment, L or La is preferably an aromatic hydrocarbon cyclogroup represented by the following general formula (L1) or (L2).
[2901] [Chemical Formula 284]
[2902]
[2903] (In the above general formulas (L1) and (L2),
[2904] One of the two asterisks is bonded to the triazine ring shown in the above general formula (3).
[2905] The other of the two * is bonded to (C)n, (Cz)n, or Ac.
[2906] When n is 1, there is 1 * that is bonded to (C)n or (Cz)n.
[2907] When n is 2, there are 2 * that are bonded to (C)n or (Cz)n.
[2908] When n is 3, there are 3 * that are bonded to (C)n or (Cz)n.
[2909] In the organic EL element involved in this embodiment, A is preferably an aryl group with 6 to 12 cyclic carbons, either substituted or unsubstituted.
[2910] In the third compound of the organic EL element involved in this embodiment, A is preferably...
[2911] Substituted or unsubstituted phenyl
[2912] Substituted or unsubstituted biphenyl, or
[2913] Substituted or unsubstituted naphthyl groups.
[2914] In the third compound of the organic EL element involved in this embodiment, A is preferably...
[2915] phenyl,
[2916] biphenyl, or
[2917] Naphthyl group.
[2918] In the third compound of the organic EL element involved in this embodiment, B is preferably an aryl group with 6 to 12 cyclic carbons, either substituted or unsubstituted.
[2919] In the third compound of the organic EL element involved in this embodiment, B is preferably...
[2920] Substituted or unsubstituted phenyl
[2921] Substituted or unsubstituted biphenyl, or
[2922] Substituted or unsubstituted naphthyl groups.
[2923] In the third compound of the organic EL element involved in this embodiment, A and B are each preferably independently preferred.
[2924] Substituted or unsubstituted phenyl
[2925] Substituted or unsubstituted biphenyl, or
[2926] Substituted or unsubstituted naphthyl groups.
[2927] In the third compound, groups described as "substituted or unsubstituted" are preferably "unsubstituted".
[2928] (Method for manufacturing the third compound)
[2929] The third compound can be manufactured using known methods. Alternatively, the third compound can also be manufactured by using known alternative reactions and starting materials corresponding to the target substance, following the known methods.
[2930] (Specific examples of the third compound)
[2931] Specific examples of third compounds include the following compounds. However, the present invention is not limited to these specific examples of third compounds.
[2932] [Chemical Formula 285]
[2933]
[2934] [Chemical Formula 286]
[2935]
[2936] [Chemical Formula 287]
[2937]
[2938] [Chemical Formula 288]
[2939]
[2940] [Chemical Formula 289]
[2941]
[2942] [Chemical Formula 290]
[2943]
[2944]
Chemical Formula 291
[2945]
[2946]
Chemical Formula 292
[2947]
[2948] [Chemical Formula 293]
[2949]
[2950] [Chemical Formula 294]
[2951]
[2952] [Chemical Formula 295]
[2953]
[2954] [Chemical Formula 296]
[2955]
[2956] [Chemical Formula 297]
[2957]
[2958] [Chemical Formula 298]
[2959]
[2960] [Chemical Formula 299]
[2961]
[2962]
Chemical Formula 300
[2963]
[2964]
Chemical Formula 301
[2965]
[2966]
Chemical Formula 302
[2967]
[2968]
Chemical Formula 303
[2969]
[2970] Chemical formula 304
[2971]
[2972]
Chemical Formula 305
[2973]
[2974] The configuration of the organic EL element involved in this embodiment will be further explained. Hereinafter, the description of symbols will sometimes be omitted.
[2975] (Substrate)
[2976] The substrate is used as a support for the organic electroluminescent (EL) element. Examples of substrates that can be used include glass, quartz, and plastic. Flexible substrates can also be used. A flexible substrate is a substrate that can be bent (flexible). Examples of flexible substrates include plastic substrates. Materials used to form the plastic substrate include, for example, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Inorganic vapor-deposited films can also be used.
[2977] (anode)
[2978] The anode formed on the substrate is preferably a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically 4.0 eV or higher). Examples of such anodes include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metallic materials (e.g., titanium nitride).
[2979] These materials are typically formed by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1% to 10% zinc oxide relative to indium oxide. Alternatively, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5% to 5% tungsten oxide and 0.1% to 1% zinc oxide relative to indium oxide. Furthermore, these materials can also be fabricated using vacuum evaporation, coating, inkjet printing, spin coating, and other similar methods.
[2980] In the EL layer formed on the anode, the hole injection layer formed with the anode in contact with the ground is formed using a composite material that is easy to inject holes with, which is independent of the work function of the anode. Therefore, materials that can be used as electrode materials (such as metals, alloys, conductive compounds and mixtures thereof, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.
[2981] Elements belonging to Group 1 or Group 2 of the periodic table that have low work functions can also be used, namely alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them. It should be noted that when using alkali metals, alkaline earth metals, and their alloys to form the anode, vacuum evaporation or sputtering methods can be used. Furthermore, when using silver paste, coating or inkjet printing methods can be used.
[2982] (cathode)
[2983] The cathode preferably uses metals, alloys, conductive compounds, and mixtures thereof with low work functions (specifically, below 3.8 eV). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them.
[2984] It should be noted that when using alkali metals, alkaline earth metals, or alloys containing them to form the cathode, vacuum evaporation or sputtering methods can be used. Additionally, when using silver paste, coating or inkjet printing methods can be used.
[2985] It should be noted that by setting an electron injection layer, a wide variety of conductive materials, such as Al, Ag, ITO, graphene, and indium tin oxide containing silicon or silicon oxide, can be used to form cathodes regardless of the work function. These conductive materials can be deposited using methods such as sputtering, inkjet printing, and spin coating.
[2986] (hole injection layer)
[2987] A hole injection layer is a layer containing a material with high hole injection capability. Materials with high hole injection capability can include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.
[2988] In addition, other substances with high hole-injection potential include 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (DNTPD), and 1,3,5-tris[N-(4-diphenylamino)- ...]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]-[N-(4-diphenylamino]- Aromatic amine compounds such as phenyl(N-phenylamino)benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile (HAT-CN).
[2989] In addition, high-molecular-weight compounds (oligomers, dendritic polymers, polymers, etc.) can also be used as substances with high hole injection capabilities. Examples include poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (Poly-TPD). Furthermore, acid-containing polymers such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can also be used.
[2990] (Hole transport layer)
[2991] The hole transport layer is a layer containing substances with high hole transport capacity. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used in the hole transport layer. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BAFLP), and 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N Aromatic amine compounds such as 4,4',4'-tris(N,N-diphenylamino)triphenylamine (DFLDPBi), 4,4',4'-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), and 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (BSPB) are mentioned. -6 cm 2 Substances with a hole mobility of / (V·s) or higher.
[2992] Carbazole derivatives such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (PCzPA), as well as anthracene derivatives such as t-BuDNA, DNA, and DPAnth, can also be used in the hole transport layer. Polymers such as poly(N-vinylcarbazole) (PVK) and poly(4-vinyltriphenylamine) (PVTPA) can also be used.
[2993] It should be noted that any substance whose hole transport capacity is higher than that of an electron can also use these other substances. It should also be noted that the layer containing the substance with high hole transport capacity can be not only a single layer, but also a stack of two or more layers formed by the aforementioned substances.
[2994] The organic EL element according to this embodiment also preferably has a hole transport layer disposed between the anode and the first and second light-emitting layers that are directly connected to each other, and preferably the hole transport layer contains a compound represented by the following general formula (C1) or (D1).
[2995]
Chemical Formula 306
[2996]
[2997] (In the above general formula (C1),
[2998] L A LB and L C Each independently
[2999] single bond,
[3000] Substituted or unsubstituted arylene groups with 6 to 18 carbon atoms, or
[3001] Divalent heterocyclic groups with 5 to 13 cyclic atoms, substituted or unsubstituted.
[3002] A A B B and C C Each independently
[3003] Substituted or unsubstituted aryl groups with 6 to 30 carbon atoms
[3004] Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms, or
[3005] -Si(R' 901 )(R' 902 )(R' 903 The group shown is ).
[3006] R' 901 ~R' 903 Each is independently a substituted or unsubstituted aryl group with 6 to 30 carbon atoms in a cyclic formation.
[3007] In R' 901 In the case of multiple R's, there are multiple R's. 901 They are the same or different.
[3008] In R' 902 In the case of multiple R's, there are multiple R's. 902 They are the same or different.
[3009] In R' 903 In the case of multiple R's, there are multiple R's. 903 (They may be the same or different.)
[3010]
Chemical Formula 307
[3011]
[3012] (In the above general formula (D1),
[3013] A 41 and A 42 Each independently
[3014] Substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or
[3015] Heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.
[3016] L 41 and L 42 Each independently
[3017] single bond,
[3018] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or
[3019] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.
[3020] Ra 410 ~Ra 414 One or more of the groups consisting of two or more adjacent elements.
[3021] They bond together to form substituted or unsubstituted monocyclic rings.
[3022] They bond together to form substituted or unsubstituted fused rings, or
[3023] They do not bond with each other.
[3024] Ra 420 ~Ra 424 One or more of the groups consisting of two or more adjacent elements.
[3025] They bond together to form substituted or unsubstituted monocyclic rings.
[3026] They bond together to form substituted or unsubstituted fused rings, or
[3027] They do not bond with each other.
[3028] Ra does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 410 ~Ra 414 and Ra 420 ~Ra 424 Each independently
[3029] hydrogen atom,
[3030] cyano,
[3031] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3032] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[3033] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[3034] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[3035] -Si(R 901 (R) 902(R) 903 The groups shown in the figure,
[3036] -O-(R 904 The groups shown in the figure,
[3037] Halogen atoms,
[3038] Nitro,
[3039] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3040] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[3041] m1 and m2 are both 3.
[3042] 3 Ra 410 They are the same or different.
[3043] 3 Ra 420 They are the same or different.
[3044] In the compounds represented by the above general formula (D1), R 901 R 902 R 903 and R 904 Each independently
[3045] hydrogen atom,
[3046] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[3047] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[3048] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[3049] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[3050] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[3051] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[3052] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[3053] In R 904 In the case of multiple Rs, multiple Rs 904 (They may be the same or different.)
[3054] In the organic EL element of this embodiment, the hole transport layer preferably contains a compound represented by the general formula (C1).
[3055] In the compounds represented by the above general formula (C1), the groups described as "substituted or unsubstituted" are preferably "unsubstituted".
[3056] (Electron transport layer)
[3057] The organic EL element involved in this embodiment may further include an additional electron transport layer (e.g., a second electron transport layer and a third electron transport layer) between the first light-emitting layer, the second light-emitting layer and the cathode.
[3058] The electron transport layer is a layer containing substances with high electron transport capacity. The electron transport layer can utilize 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) high molecular weight compounds. Specifically, as low molecular weight organic compounds, metal complexes such as Alq, tris(4-methyl-8-hydroxyquinoline)aluminum (Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to metal complexes, heteroaromatic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviated as p-EtTAZ), phenanthroline (abbreviated as BPhen), copper hydroxide (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)zirconia (abbreviated as BzOs) can also be used. In this embodiment, a benzimidazole compound, for example, can be used in the additional electron transport layer. The substances described herein mainly have 10 -6 cm 2 Substances with an electron mobility of / (V·s) or higher. It should be noted that any substance with electron transport capacity higher than hole transport capacity can also be used as an electron transport layer, regardless of the specific substance mentioned above.
[3059] In addition, polymeric compounds can also be used in the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy) can be used.
[3060] (Electron injection layer)
[3061] The electron injection layer is a layer containing a material with high electron-injection properties. Alkali metals, alkaline earth metals, or their compounds, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx), can be used in the electron injection layer. Alternatively, materials containing alkali metals, alkaline earth metals, or their compounds can be used; specifically, materials containing magnesium (Mg) in Alq can be used. It should be noted that electron injection from the cathode can be performed more efficiently in this case.
[3062] Alternatively, a composite material consisting of an organic compound and an electron donor can be used in the electron injection layer. Such a composite material exhibits excellent electron injection and electron transport properties because it generates electrons within the organic compound through the electron donor. In this case, the organic compound is preferably a material with excellent electron transport properties; specifically, substances constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) described above can be used. The electron donor can be any substance that exhibits electron-donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Additionally, alkali metal oxides and alkaline earth metal oxides are preferred, such as lithium oxides, calcium oxides, and barium oxides. Furthermore, Lewis bases such as magnesium oxide can also be used. Additionally, organic compounds such as tetrathiofulvalene (TTF) can also be used.
[3063] In the organic EL element described in this embodiment, the substituents, when expressed as "substituted or unsubstituted," are preferably selected from...
[3064] Alkyl groups having 1 to 18 carbon atoms
[3065] aryl groups with 6 to 18 carbon atoms, and
[3066] At least one group from the group consisting of heterocyclic groups with 5 to 18 cyclic atoms.
[3067] In the organic EL element involved in this embodiment, the substituent, when described as "substituted or unsubstituted", is preferably an alkyl group having 1 to 5 carbon atoms.
[3068] (Layer Formation Method)
[3069] The method for forming each layer of the organic EL element in this embodiment is not limited except as specifically mentioned above. Known methods such as vacuum evaporation, sputtering, plasma deposition, ion plating, spin coating, dip coating, flow coating, and inkjet coating can be used.
[3070] (film thickness)
[3071] The thickness of each organic layer in the organic EL element of this embodiment is not limited except as specifically mentioned above. Generally speaking, if the film thickness is too thin, defects such as pinholes are easily generated, while if the film thickness is too thick, a high applied voltage is required, which degrades the efficiency. Therefore, the film thickness of each organic layer in an organic EL element is usually preferably in the range of a few nm to 1 μm.
[3072] (Emitting wavelength of organic EL devices)
[3073] The organic electroluminescent element involved in this embodiment preferably emits light with a maximum peak wavelength of 430 nm or more and 480 nm or less when the element is driven.
[3074] The maximum peak wavelength of light emitted by the organic EL element during element driving was determined as follows. A voltage was applied to the organic EL element such that the current density was 10 mA / cm². 2 The spectrophotometer emission spectrum was measured using a CS-2000 spectrophotometer (manufactured by Konica Minolta). The peak wavelength of the emission spectrum at which the luminous intensity reaches its maximum was determined and taken as the maximum peak wavelength (unit: nm).
[3075] According to this embodiment, an organic electroluminescent element that emits light with high luminous efficiency and long lifetime can be provided.
[3076] [Second Implementation]
[3077] (Organic electroluminescent device)
[3078] The structure of the organic EL element according to the second embodiment will be described.
[3079] The organic EL element according to the second embodiment differs from the organic EL element according to the first embodiment in that it involves the first and second light-emitting layers, but is otherwise the same as the organic EL element according to the first embodiment. Therefore, in the description of the second embodiment, the same symbols, names, etc., are used for the same constituent elements as in the first embodiment, and the description is omitted or simplified. In addition, in the second embodiment, for element structures, materials, and compounds not specifically mentioned, the same element structures, materials, and compounds as those described in the first embodiment can be used.
[3080] The organic EL element according to this embodiment has an anode, a cathode, a first light-emitting layer and a second light-emitting layer disposed between the anode and the cathode and directly connected to each other, and a first electron transport layer disposed between the directly connected first and second light-emitting layers and the cathode. The first light-emitting layer contains a first compound as a first host material, and the second light-emitting layer contains a second compound as a second host material. The first host material and the second host material are different from each other. The first light-emitting layer contains at least a compound that emits light with a maximum peak wavelength of 500 nm or less, and the second light-emitting layer contains at least a compound that emits light with a maximum peak wavelength of 500 nm or less. The compounds that emit light with a maximum peak wavelength of 500 nm or less in the first light-emitting layer and the compounds that emit light with a maximum peak wavelength of 500 nm or less in the second light-emitting layer are the same as or different from each other. The triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the following mathematical formula (Mathematical Formula 1A). The first electron transport layer contains a third compound.
[3081] T1(H1)>T1(H2)...(Mathematical expression 1A))
[3082] The third compound contained in the first electron transport layer of the organic EL element involved in this embodiment is the same compound as the third compound described in the first embodiment.
[3083] Previously, triplet-triplet annihilation (sometimes called TTA) was a known technique for improving the luminous efficiency of organic electroluminescent devices. TTA is a mechanism in which triplet excitons collide with each other to generate singlet excitons. It should be noted that the TTA mechanism is sometimes also called the TTF mechanism. TTF is short for Triplet-Triplet Fusion.
[3084] The TTF phenomenon is explained. Holes injected from the anode recombine with electrons injected from the cathode within the emissive layer to generate excitons. Their spin states, as previously known, are 25% singlet excitons and 75% triplet excitons. In previously known fluorescent elements, 25% of the singlet excitons relax to the ground state and emit light, while the remaining 75% of the triplet excitons do not emit light but recover to the ground state through thermal deactivation. Therefore, the theoretical limit of the internal quantum efficiency of previous fluorescent elements was claimed to be 25%.
[3085] On the other hand, the behavior of triplet excitons generated within organic matter has been theoretically studied. According to SMBachilo et al. (J. Phys. Chem. A, 104, 7711 (2000)), if we assume that excitons of higher orders, such as quintet, immediately revert to the triplet state, then in triplet excitons (hereinafter referred to as...) 3 A * As the density of ) gradually increases, triplet excitons collide with each other, resulting in the reaction shown in the following equation. Here, 1 A represents the ground state. 1 A * This represents the lowest excited singlet exciton.
[3086] 3 A*+ 3 A*→(4 / 9) 1 A+(1 / 9) 1 A*+(13 / 9) 3 A*
[3087] That is, to become 5 3 A * →4 1 A+1A * It is predicted that of the initially generated 75% of triplet excitons, 1 / 5, or 20%, will transform into singlet excitons. Therefore, the singlet excitons contributing in the form of light become 40%, which is the initial 25% plus 75% × (1 / 5) = 15%. At this point, the proportion of light emitted from the TTF (TTF ratio) in the total luminescence intensity becomes 15 / 40, or 37.5%. Furthermore, if the initially generated 75% of triplet excitons collide with each other to generate singlet excitons (two triplet excitons generate one singlet exciton), a very high internal quantum efficiency of 62.5% can be obtained, which is the initial 25% of singlet excitons plus 75% × (1 / 2) = 37.5%. At this point, the TTF ratio is 37.5 / 62.5 = 60%.
[3088] According to the organic electroluminescent device of this embodiment, it is believed that for triplet excitons generated in the first light-emitting layer through recombination of holes and electrons, even if there are excess charge carriers at the interface between the first light-emitting layer and the directly adjacent organic layer, the triplet excitons at the interface between the first light-emitting layer and the organic layer are not easily quenched. For example, if recombination regions are locally present at the interface between the first light-emitting layer and the hole transport layer or the electron blocking layer, quenching due to excess electrons can be considered. On the other hand, if recombination regions are locally present at the interface between the first light-emitting layer and the electron transport layer or the hole blocking layer, quenching due to excess holes can be considered.
[3089] The organic electroluminescent element according to this embodiment has at least two light-emitting layers (i.e., a first light-emitting layer and a second light-emitting layer) that satisfy a specified relationship. The triplet energy T1(H1) of the first host material in the first light-emitting layer and the triplet energy T1(H2) of the second host material in the second light-emitting layer satisfy the relationship of the above mathematical formula (mathematical formula 1A).
[3090] By having a first luminescent layer and a second luminescent layer as described in the mathematical formula (Formula 1A), triplet excitons generated in the first luminescent layer are not quenched by excess carriers and migrate to the second luminescent layer. Furthermore, reverse migration from the second luminescent layer to the first luminescent layer is suppressed. As a result, the second luminescent layer exhibits a TTF mechanism, efficiently generating singlet excitons and improving luminescence efficiency.
[3091] Thus, the organic electroluminescent element has a first light-emitting layer that mainly generates triplet excitons and a second light-emitting layer that effectively utilizes the triplet excitons that move from the first light-emitting layer to mainly exhibit the TTF mechanism as different regions. As the second host material in the second light-emitting layer, a compound with a smaller triplet energy than the first host material in the first light-emitting layer is used to set the difference in triplet energy, thereby improving the luminous efficiency.
[3092] In the organic EL element of this embodiment, the triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material preferably satisfy the following mathematical formula (Mathematical Formula 5).
[3093] T1(H1)-T1(H2)>0.03eV...(Mathematical Formula 5)
[3094] (Emitting wavelength of organic EL devices)
[3095] The organic electroluminescent element involved in this embodiment preferably emits light with a maximum peak wavelength of less than 500 nm when the element is driven.
[3096] The organic electroluminescent element involved in this embodiment is more preferably emitted when the element is driven, with a maximum peak wavelength of 430 nm or more and 480 nm or less.
[3097] The maximum peak wavelength of light emitted by an organic EL element during element driving can be determined using the method described above.
[3098] (First light-emitting layer)
[3099] The first light-emitting layer contains a first host material. The first host material is a compound different from the second host material contained in the second light-emitting layer.
[3100] The first luminescent layer contains at least a compound exhibiting emission with a maximum peak wavelength of 500 nm or less. This "compound exhibiting emission with a maximum peak wavelength of 500 nm or less" can be a first host material or a compound different from the first host material. Preferably, the compound exhibiting emission with a maximum peak wavelength of 500 nm or less contained in the first luminescent layer is a fluorescent luminescent compound exhibiting a maximum peak wavelength of 500 nm or less.
[3101] In this embodiment, the compound exhibiting emission with a maximum peak wavelength of 500 nm or less is preferably a compound exhibiting fluorescence emission with a maximum peak wavelength of 500 nm or less.
[3102] In the organic EL element involved in this embodiment, it is preferred that the first light-emitting layer further includes a first dopant material, which is a fluorescent luminescent compound.
[3103] In the organic EL element involved in this embodiment, the first dopant material is preferably a compound that does not contain an azazine ring structure in its molecule.
[3104] In the organic EL element involved in this embodiment, the first dopant material is preferably not a boron-containing complex, and more preferably not a complex.
[3105] In the organic EL element according to this embodiment, the first light-emitting layer preferably does not contain metal complexes. Furthermore, in the organic EL element according to this embodiment, the first light-emitting layer preferably also does not contain boron-containing complexes.
[3106] In the organic EL element involved in this embodiment, the first light-emitting layer preferably does not contain phosphorescent materials (dopant materials).
[3107] Furthermore, the aforementioned first luminescent layer preferably does not contain heavy metal complexes or phosphorescent rare-earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.
[3108] In the organic EL element of this embodiment, the first dopant material is preferably a compound that emits light with a maximum peak wavelength of 500 nm or less, and more preferably a compound that emits fluorescence with a maximum peak wavelength of 500 nm or less. The method for determining the maximum peak wavelength of the compound is as described above.
[3109] In the emission spectrum of the first dopant material described above, when the peak with the highest emission intensity is taken as the maximum peak and the height of this maximum peak is set to 1, the heights of other peaks appearing in the emission spectrum are preferably less than 0.6. It should be noted that the peaks in the emission spectrum are set to maximum values.
[3110] Furthermore, in the emission spectrum of the first dopant material described above, the number of peaks is preferably less than three.
[3111] In the organic EL element involved in this embodiment, the first light-emitting layer preferably emits light with a maximum peak wavelength of less than 500 nm when the element is driven.
[3112] The maximum peak wavelength of the light emitted by the light-emitting layer when the element is driven can be determined using the method described below.
[3113] • The maximum peak wavelength λp of light emitted from the light-emitting layer when the element is driven
[3114] To determine the maximum peak wavelength λp1 of the light emitted from the first emitting layer during device driving, the second emitting layer was fabricated using the same material as the first emitting layer. The organic EL device was then measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta Co., Ltd.) to measure the applied voltage to the device, resulting in a current density of 10 mA / cm². 2 The spectroscopic emission spectrum at that time was obtained. The maximum peak wavelength λp1 (in nm) was calculated based on the obtained spectroscopic emission spectrum.
[3115] For the maximum peak wavelength λp2 of the light emitted from the second emissive layer during device driving, the first emissive layer is made of the same material as the second emissive layer to fabricate the organic EL device. The current density of the organic EL device reaches 10 mA / cm² when a voltage is applied to the device, measured using a CS-2000 spectroradiometer (manufactured by Konica Minolta Co., Ltd.). 2 The spectroscopic emission spectrum at that time was obtained. The maximum peak wavelength λp2 (unit: nm) was calculated based on the obtained spectroscopic emission spectrum.
[3116] In the organic EL element of this embodiment, the singlet energy S1(H1) of the first host material and the singlet energy S1(D1) of the first dopant material preferably satisfy the following mathematical formula (mathematical formula 20).
[3117] S1(H1)>S1(D1)...(Mathematical Expression 20)
[3118] The singlet energy S1 refers to the energy difference between the lowest excited singlet state and the ground state.
[3119] The first host material and the first dopant material satisfy the relationship described in the above mathematical formula (Formula 20). As a result, the singlet excitons generated on the first host material are more likely to undergo energy transfer from the first host material to the first dopant material, which helps the first dopant material to exhibit fluorescence luminescence.
[3120] In the organic EL element of this embodiment, the triplet energy T1(H1) of the first host material and the triplet energy T1(D1) of the first dopant material preferably satisfy the following mathematical formula (mathematical formula 2A).
[3121] T1(D1)>T1(H1)...(Mathematical expression 2A)
[3122] The first host material and the first dopant material satisfy the above mathematical formula (Mathematical Formula 2A). The triplet excitons generated in the first light-emitting layer are more likely to move to the second light-emitting layer because they do not move in the first dopant material with higher triplet energy but in the first host material.
[3123] The organic EL element involved in this embodiment preferably satisfies the following mathematical formula (Mathematical Formula 2B).
[3124] T1(D1)>T1(H1)>T1(H2)...(Mathematical expression 2B)
[3125] (Triplet energy T1)
[3126] The following methods can be cited as methods for determining the triplet energy T1.
[3127] The compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to achieve a concentration of 10. -5 mol / L or higher and 10 -4 The solution with a concentration below mol / L was added to a quartz cuvette as the test sample. For this test sample, the phosphorescence spectrum was measured at a low temperature (77 K) (the vertical axis was set to phosphorescence intensity, and the horizontal axis to wavelength). The wavelength value λ at the intersection of the tangent line and the horizontal axis was used to determine the rising tangent line on the shorter wavelength side of the phosphorescence spectrum.edge [nm], the energy calculated according to the following conversion formula (F1) is taken as the triplet energy T1.
[3128] Conversion formula (F1): T1[eV]=1239.85 / λ edge
[3129] The tangent for the rise on the short-wavelength side of the phosphorescence spectrum is derived as follows. Consider the tangent at each point on the spectral curve, moving from the short-wavelength side of the phosphorescence spectrum up to the shortest wavelength maximum among the spectral maxima, towards the long-wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope reaches its maximum (i.e., the tangent at the inflection point) is taken as the tangent for the rise on the short-wavelength side of the phosphorescence spectrum.
[3130] It should be noted that the maximum point of peak intensity with less than 15% of the maximum peak intensity of the spectrum is not included in the maximum value on the shortest wavelength side mentioned above. The tangent line drawn at the point where the slope value is the maximum value closest to the maximum value on the shortest wavelength side is taken as the tangent line for the rise on the short wavelength side of the phosphorescence spectrum.
[3131] Phosphorescence can be measured using the main body of the F-4500 spectrophotometer manufactured by Hitachi High Tech Co., Ltd. It should be noted that the measuring apparatus is not limited to this; a cooling device, a cryogenic container, an excitation source, and a light-receiving device can be combined for measurement.
[3132] In the organic EL element involved in this embodiment, the electron mobility μH1 of the first host material and the electron mobility μH2 of the second host material preferably satisfy the following mathematical formula (Mathematical Formula 6).
[3133] μH2>μH1...(Mathematical Equation 6)
[3134] The first host material and the second host material satisfy the relationship of the above mathematical formula (Mathematical Formula 6), thereby improving the recombination ability of holes and electrons in the first light-emitting layer.
[3135] Electron mobility can be determined using impedance spectroscopy using the following methods.
[3136] A measurement layer with a thickness of 100 nm to 200 nm is held between an anode and a cathode, and a small AC voltage of less than 100 mV is applied simultaneously with a bias DC voltage. The AC current flowing under these conditions is measured (absolute value and phase). This measurement is performed while changing the frequency of the AC voltage, and the complex impedance (Z) is calculated from the current and voltage values. The frequency dependence of the imaginary part (ImM) of the modulus M = iωZ (i: imaginary unit, ω: angular frequency) is then determined, and the reciprocal of the frequency ω at which ImM reaches its maximum value is defined as the response time of electrons conducted within the measurement layer. Then, the electron mobility is calculated using the following formula.
[3137] Electron mobility = (film thickness of the measured object layer) 2 / (Response Time·Voltage)
[3138] In the organic EL element according to this embodiment, the first dopant material is preferably present in the first light-emitting layer at a content of more than 1.1% by mass. That is, the first light-emitting layer preferably has a content of the first dopant material exceeding 1.1% by mass of the total mass of the first light-emitting layer, more preferably 1.2% by mass or more of the total mass of the first light-emitting layer, and even more preferably 1.5% by mass or more of the total mass of the first light-emitting layer.
[3139] Preferably, the content of the first dopant material in the first light-emitting layer is 10% or less of the total mass of the first light-emitting layer, more preferably 7% or less of the total mass of the first light-emitting layer, and even more preferably 5% or less of the total mass of the first light-emitting layer.
[3140] In the organic EL element of this embodiment, the content of the first compound, which is the first host material, in the first light-emitting layer is preferably 60% or more of the total mass of the first light-emitting layer, more preferably 70% or more of the total mass of the first light-emitting layer, even more preferably 80% or more of the total mass of the first light-emitting layer, even more preferably 90% or more of the total mass of the first light-emitting layer, and even more preferably 95% or more of the total mass of the first light-emitting layer.
[3141] In the first light-emitting layer, the content of the first host material is preferably 99% or less of the total mass of the first light-emitting layer.
[3142] Wherein, when the first light-emitting layer contains a first host material and a ...
Claims
1. An organic electroluminescent element having anode, cathode, A first light-emitting layer and a second light-emitting layer disposed between the anode and the cathode and directly connected to each other, and A first electron transport layer is disposed between the first and second light-emitting layers, which are directly connected to each other, and the cathode. The first light-emitting layer contains a first compound as the first host material. The second light-emitting layer contains a second compound as a second host material. The first main material and the second main material are different from each other. The first light-emitting layer contains at least a compound that exhibits luminescence with a maximum peak wavelength below 500 nm. The second luminescent layer contains at least a compound that exhibits luminescence with a maximum peak wavelength below 500 nm. The first light-emitting layer contains a luminescent compound with a maximum peak wavelength of less than 500 nm, which may be the same as or different from the luminescent compound with a maximum peak wavelength of less than 500 nm contained in the second light-emitting layer. The triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the following mathematical expression (Mathematical Expression 1A). The first electron transport layer contains a third compound represented by the following general formula (3). T1(H1)>T1(H2) …(Mathematical Expression 1A) In the general formula (3), A is Substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, or Heterocyclic groups with 5 to 13 cyclic atoms, substituted or unsubstituted. B is Substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, or Heterocyclic groups with 5 to 13 cyclic atoms, substituted or unsubstituted. L is single bond, Substituted or unsubstituted cyclic aromatic hydrocarbons with 6–18 carbon atoms (n+1) cyclic groups Substituted or unsubstituted (n+1) valent heterocyclic groups with 5 to 13 cyclic atoms, or A (n+1) valence group having a structure consisting of two or three distinct groups bonded together from a substituted or unsubstituted aromatic hydrocarbon cyclic group having 6 to 18 carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 13 cyclic atoms. C is Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 60 cyclic atoms, substituted or unsubstituted. n is 1, 2, or 3. When n is 2 or higher, L is not a single bond. When n is 2 or more, multiple Cs can be the same or different.
2. The organic electroluminescent element according to claim 1, wherein, The triplet energy T1(H1) of the first host material satisfies the following mathematical expression (Mathematical Expression 12A): T1(H1)>2.10eV …(Mathematical formula 12A).
3. The organic electroluminescent element according to claim 1, wherein, The triplet energy T1(H1) of the first host material satisfies the following mathematical expression (Mathematical Expression 12C). 2.08eV>T1(H1)>1.87eV …(Mathematical formula 12C).
4. The organic electroluminescent element according to claim 1, wherein, The triplet energy T1(F1) of the luminescent compound containing the first luminescent layer, whose maximum peak wavelength is below 500 nm, satisfies the following mathematical formula (Formula 14A). 2.60eV>T1(F1) …(Mathematical formula 14A).
5. The organic electroluminescent element according to claim 1, wherein, The triplet energy T1(F2) of the luminescent compound containing the second luminescent layer, whose maximum peak wavelength is below 500 nm, satisfies the following mathematical expression (Formula 14C). 2.60eV>T1(F2) …(Mathematical formula 14C).
6. The organic electroluminescent element according to claim 1, wherein, The triplet energy T1(H2) of the second host material satisfies the following mathematical expression (Mathematical Expression 13): T1(H2)≥1.9eV …(Mathematical formula 13).
7. The organic electroluminescent element according to claim 1, wherein, The first host material has a molecule containing a benzene ring and a naphthalene ring linked by a single bond. In the connecting structure, the benzene ring and the naphthalene ring are each independently further fused with monocyclic or fused rings, or are not fused. The benzene ring and the naphthalene ring in the linkage structure are further linked by crosslinking at least one portion other than the single bond.
8. The organic electroluminescent element according to claim 7, wherein, The crosslinking involves double bonds.
9. The organic electroluminescent element according to claim 1, wherein, The first host material has a biphenyl structure in its molecule, in which a first benzene ring and a second benzene ring are connected by a single bond. The first benzene ring and the second benzene ring in the biphenyl structure are further connected by crosslinking at least one portion other than the single bond.
10. The organic electroluminescent element according to claim 9, wherein, The first benzene ring and the second benzene ring in the biphenyl structure are further connected by crosslinking in a portion other than the single bond.
11. The organic electroluminescent element according to claim 9, wherein, The crosslinking involves double bonds.
12. The organic electroluminescent element according to claim 10, wherein, The first benzene ring and the second benzene ring in the biphenyl structure are further connected through crosslinking in two parts other than the single bond. The crosslinking does not include double bonds.
13. The organic electroluminescent element according to claim 1, wherein, The first compound is a compound represented by the following general formula (1). In the general formula (1), R 101 ~R 110 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or The group represented by the general formula (11), Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11). When there are multiple groups represented by the general formula (11), the multiple groups represented by the general formula (11) may be the same as or different from each other. L 101 for single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 101 for Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. mx is 0, 1, 2, 3, 4, or 5. In L 101 In cases where there are two or more L's, there are two or more L's. 101 They are the same or different. In Ar 101 In cases where there are two or more Ar, two or more Ar 101 They are the same or different. In the general formula (11) This indicates the bonding position with the pyrene ring in the general formula (1). In the first compound represented by general formula (1), R 901 R 902 R 903 R 904 R 905 R 801 and R 802 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different. In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different. In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different. In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different. In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different. In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different. In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
14. The organic electroluminescent element according to claim 1, wherein, The first compound is a compound represented by the following general formulas (1X), (12X), (13X), (14X), (15X), or (16X). In the general formula (1X), R 101 ~R 112 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or The group represented by the general formula (11X), Among them, R 101 ~R 112 At least one of them is a group represented by the general formula (11X). When multiple groups represented by the general formula (11X) are present, the multiple groups represented by the general formula (11X) may be the same as or different from each other. L 101 for single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 101 for Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. mx is 1, 2, 3, 4, or 5. In L 101 In cases where there are two or more L's, there are two or more L's. 101 They are the same or different. In Ar 101 In cases where there are two or more Ar, two or more Ar 101 They are the same or different. In the general formula (11X) This indicates the bonding position with the benzo[a]anthracene ring in the general formula (1X). In the general formula (12X), R 1201 ~R 1210 One or more of the groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings, or They bond together to form substituted or unsubstituted fused rings. R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 1201 ~R 1210 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or The group represented by the general formula (121), Wherein, the substituent when the substituted or unsubstituted monocyclic ring has a substituent, the substituent when the substituted or unsubstituted fused ring has a substituent, and R 1201 ~R 1210 At least one of them is a group represented by the general formula (121). When multiple groups represented by the general formula (121) are present, the multiple groups represented by the general formula (121) may be the same as or different from each other. L 1201 for single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 1201 for Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. mx2 is 0, 1, 2, 3, 4, or 5. In L 1201 In cases where there are two or more L's, there are two or more L's. 1201 They are the same or different. In Ar 1201 In cases where there are two or more Ar, two or more Ar 1201 They are the same or different. In the general formula (121) This indicates the bonding position with the ring shown in the general formula (12X). In the general formula (13X), R 1301 ~R 1310 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or The group represented by the general formula (131), Among them, R 1301 ~R 1310 At least one of them is a group represented by the general formula (131). When multiple groups represented by the general formula (131) are present, the multiple groups represented by the general formula (131) may be the same as or different from each other. L 1301 for single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 1301 for Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. mx3 can be 0, 1, 2, 3, 4, or 5. In L 1301 In cases where there are two or more L's, there are two or more L's. 1301 They are the same or different. In Ar 1301 In cases where there are two or more Ar, two or more Ar 1301 They are the same or different. In the general formula (131) This indicates the bonding position with the fluoranthene ring in the general formula (13X). In the general formula (14X), R 1401 ~R 1410 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or The group represented by the general formula (141), Among them, R 1401 ~R 1410 At least one of them is a group represented by the general formula (141). When multiple groups represented by the general formula (141) are present, the multiple groups represented by the general formula (141) may be the same as or different from each other. L 1401 for single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 1401 for Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. mx4 can be 0, 1, 2, 3, 4, or 5. In L 1401 In cases where there are two or more L's, there are two or more L's. 1401 They are the same or different. In Ar 1401 In cases where there are two or more Ar, two or more Ar 1401 They are the same or different. In the general formula (141) This indicates the bonding position with the ring shown in the general formula (14X). In the general formula (15X), R 1501 ~R 1514 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or The group represented by the general formula (151), Among them, R 1501 ~R 1514 At least one of them is a group represented by the general formula (151). When multiple groups represented by the general formula (151) are present, the multiple groups represented by the general formula (151) may be the same as or different from each other. L 1501 for single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 1501 for Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. mx5 can be 0, 1, 2, 3, 4, or 5. In L 1501 In cases where there are two or more L's, there are two or more L's. 1501 They are the same or different. In Ar 1501 In cases where there are two or more Ar, two or more Ar 1501 They are the same or different. In the general formula (151) This indicates the bonding position with the ring shown in the general formula (15X). In the general formula (16X), R 1601 ~R 1614 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or The group represented by the general formula (161), Among them, R 1601 ~R 1614 At least one of them is a group represented by the general formula (161). When multiple groups represented by the general formula (161) are present, the multiple groups represented by the general formula (161) may be the same as or different from each other. L 1601 for single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 1601 for Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. mx6 can be 0, 1, 2, 3, 4, or 5. In L 1601 In cases where there are two or more L's, there are two or more L's. 1601 They are the same or different. In Ar 1601 In cases where there are two or more Ar, two or more Ar 1601 They are the same or different. In the general formula (161) This indicates the bonding position with the ring shown in the general formula (16X). In the first compound, R 901 R 902 R 903 R 904 R 905 R 801 and R 802 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different. In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different. In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different. In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different. In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different. In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different. In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
15. The organic electroluminescent element according to claim 1, wherein, The second compound is a compound represented by the following general formula (2). In the general formula (2), R 201 ~R 208 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. L 201 and L 202 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 201 and Ar 202 Each independently Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the second compound represented by general formula (2), R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different. In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different. In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different. In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different. In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different. In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different. In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different. In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different. In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
16. The organic electroluminescent element according to claim 1, wherein, The first luminescent layer contains a compound that exhibits fluorescence with a maximum peak wavelength of less than 500 nm.
17. The organic electroluminescent element according to claim 1, wherein, The first light-emitting layer contains a compound that emits light with a maximum peak wavelength below 500 nm, which is the first dopant material.
18. The organic electroluminescent element according to claim 17, wherein, The first dopant material is a compound whose molecule does not contain an azazine ring structure.
19. The organic electroluminescent element according to claim 17, wherein, The first dopant material is not a boron-containing complex.
20. The organic electroluminescent element according to claim 17, wherein, The first dopant material is not a complex.
21. The organic electroluminescent element according to claim 17, wherein, The singlet state energy S1(H1) of the first host material and the singlet state energy S1(D1) of the first dopant material satisfy the following mathematical expression (Mathematical Expression 20). S1(H1)>S1(D1) …(Mathematical formula 20).
22. The organic electroluminescent element according to claim 17, wherein, The triplet energy T1(H1) of the first host material and the triplet energy T1(D1) of the first dopant material satisfy the following mathematical expression (Mathematical Expression 2A). T1(D1)>T1(H1) …(Mathematical expression 2A).
23. The organic electroluminescent element according to claim 1, wherein, The second luminescent layer contains a compound that exhibits fluorescence with a maximum peak wavelength of less than 500 nm.
24. The organic electroluminescent element according to claim 1, wherein, The second light-emitting layer contains a compound that emits light with a maximum peak wavelength below 500 nm, which is a second dopant material.
25. The organic electroluminescent element according to claim 24, wherein, The second dopant material is a compound whose molecule does not contain an azazine ring structure.
26. The organic electroluminescent element according to claim 24, wherein, The second dopant material is not a boron-containing complex.
27. The organic electroluminescent element according to claim 24, wherein, The second dopant material is not a complex.
28. The organic electroluminescent element according to claim 24, wherein, The singlet state energy S1(H2) of the second host material and the singlet state energy S1(D2) of the second dopant material satisfy the following mathematical expression (Mathematical Expression 4). S1(H2)>S1(D2) …(Mathematical formula 4).
29. The organic electroluminescent element according to claim 24, wherein, The triplet energy T1(D2) of the second dopant material and the triplet energy T1(H2) of the second host material satisfy the following mathematical expression (Mathematical Expression 3). T1(D2)>T1(H2) …(Mathematical expression 3).
30. The organic electroluminescent element according to claim 13 or 14, wherein, L 101 for single key, or A substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.
31. The organic electroluminescent element according to any one of claims 1 to 29, wherein, The third compound is a compound represented by the following general formula (31) or general formula (310). In the general formula (31), A, B, and C are defined in the same way as in general formula (3). R 31 ~R 34 One or more of the groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 34 Each independently hydrogen atom, cyano, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the general formula (310), A and B are defined in the general formula (3). X 30 For CR 51 R 52 NR 53 oxygen or sulfur atoms In X 30 For CR 51 R 52 In the case of R 51 and R 52 Groups They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R 300 ~R 304 One or more of the groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R 53 R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 51 R 52 R 300 ~R 304 Each independently hydrogen atom, cyano, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. na is 3, 3 R 300 They are the same or different. In the third compound, R 901 R 902 R 903 and R 904 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different. In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different. In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different. In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
32. The organic electroluminescent element according to claim 31, wherein, The third compound is a compound represented by the following general formula (32). In the general formula (32), A and B are defined in the general formula (3). X 30 For CR 51 R 52 NR 53 oxygen or sulfur atoms In X 30 For CR 51 R 52 In the case of R 51 and R 52 Groups They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R 301 ~R 304 and R 306 ~R 308 One or more of the groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R 53 R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 51 R 52 R 301 ~R 304 and R 306 ~R 308 Each independently hydrogen atom, cyano, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or A heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.
33. The organic electroluminescent element according to claim 31, wherein, The third compound is a compound represented by the following general formula (33), the following general formula (34), or the following general formula (35). In the general formulas (33) to (35), A and B are defined in the general formula (3). X 30 For CR 51 R 52 NR 53 oxygen or sulfur atoms In X 30 For CR 51 R 52 In the case of R 51 and R 52 Groups They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R 301 ~R 308 One or more of the groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R 53 R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 51 R 52 R 301 ~R 308 Each independently hydrogen atom, cyano, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or A heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.
34. The organic electroluminescent element according to any one of claims 1 to 29, wherein, The third compound is a compound represented by the following general formula (36). In the general formula (36), A, B, and C are defined in the same way as in general formula (3). R 32 ~R 39 One or more of the groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 32 ~R 39 Each independently hydrogen atom, cyano, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the third compound, R 901 R 902 R 903 and R 904 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different. In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different. In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different. In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
35. The organic electroluminescent element according to any one of claims 1 to 29, wherein, C is a heterocyclic group with 13 to 35 cyclic atoms, either substituted or unsubstituted.
36. The organic electroluminescent element according to any one of claims 1 to 29, wherein, C is an aryl group with 14 to 24 cyclic carbons, either substituted or unsubstituted.
37. The organic electroluminescent element according to any one of claims 1 to 29, wherein, The third compound is a compound represented by the following general formula (37). In the general formula (37), A, B, and L are defined in the same way as in general formula (3). Cz is a group represented by the following general formula (Cz1), (Cz2) or (Cz3). n is 1, 2, or 3. When n is 2 or 3, multiple Cz may be identical or different. In the general formulas (Cz1), (Cz2), and (Cz3), R 311 ~R 318 One or more of the groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R 320 ~R 324 One or more of the groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R 330 ~R 334 One or more groups consisting of two or more adjacent elements in Rx. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R 340 ~R 344 One or more of the groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R 351 ~R 358 One or more of the groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 311 ~R 318 R 320 ~R 324 R 330 ~R 334 R X R 340 ~R 344 and R 351 ~R 358 Each independently hydrogen atom, cyano, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. n1, n2, and n3 are all 3. 3 Rs 320 They are the same or different. 3 Rs 330 They are the same or different. 3 Rs 340 They are the same or different. The general formulas (Cz1), (Cz2), and (Cz3) Bonded to L, In the third compound, R 901 R 902 R 903 and R 904 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different. In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different. In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different. In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
38. The organic electroluminescent element according to any one of claims 1 to 29, wherein, The compound represented by general formula (3) is the compound represented by the following general formula (38). In the general formula (38), A and B are defined in the general formula (3). La for single bond, Substituted or unsubstituted cyclic groups of divalent aromatic hydrocarbons with 6 to 18 carbon atoms, or Divalent heterocyclic groups with 5 to 13 cyclic atoms, substituted or unsubstituted. Ac is a group represented by any of the following general formulas (Ac1), (Ac2), and (Ac3). In the general formula (Ac1), X 31 ~X 36 Each independently nitrogen atoms, Carbon atoms bonded to La, or Carbon atoms bonded to Ry X 31 ~X 36 One or more of them are nitrogen atoms. X 31 ~X 36 One of them is a carbon atom bonded to La. Ry is hydrogen atom, cyano, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. When multiple Ry exist, they may be identical or different from each other. In the general formula (Ac2), X 21 ~X 28 Each independently nitrogen atoms, Carbon atoms bonded to La, or Carbon atoms bonded to Rz X 21 ~X 28 One or more of them are nitrogen atoms. X 21 ~X 28 One of them is a carbon atom bonded to La. When there are multiple Rz, one or more groups consisting of two or more adjacent Rz are considered. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. The Rz values that do not form the substituted or unsubstituted monocyclic rings and the substituted or unsubstituted fused rings are each independently [value missing]. hydrogen atom, cyano, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the general formula (Ac3), n4 is 1, 2, 3, 4, 5, 6, 7, 8, or 9. D is Aryl groups with 6 to 18 carbon atoms forming a ring with n4 cyano groups, or Heterocyclic groups with 5 to 13 cyclic atoms and n4 cyano groups Wherein, D has substituents other than cyano, or does not have substituents other than cyano. In the general formula (Ac3) Bonded to La, In the third compound, R 901 R 902 R 903 and R 904 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different. In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different. In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different. In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
39. The organic electroluminescent element according to claim 38, wherein, The compound represented by general formula (38) is the compound represented by the following general formula (381). In the general formula (381), A, B, and Ac are defined in the general formula (38). R 381 ~R 384 One or more of the groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 381 ~R 384 Each independently hydrogen atom, cyano, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. R 901 ~R 904 Same as the definition in general formula (38).
40. The organic electroluminescent element according to claim 38, wherein, The compound represented by general formula (38) is the compound represented by the following general formula (382). In the general formula (382), A, B, and Ac are defined in the general formula (38). R 383 for hydrogen atom, cyano, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. R 901 ~R 904 Same as the definition in general formula (38).
41. The organic electroluminescent element according to any one of claims 1 to 29, wherein, L is single key, or A cyclic group of (n+1) valent aromatic hydrocarbons with 6 to 12 carbon atoms, substituted or unsubstituted.
42. The organic electroluminescent element according to any one of claims 1 to 29, wherein, L stands for a single bond.
43. The organic electroluminescent element according to claim 38, wherein, La represents a single bond.
44. The organic electroluminescent element according to any one of claims 1 to 29, wherein, L is an aromatic hydrocarbon cyclic group represented by the following general formula (L1) or (L2). In the general formulas (L1) and (L2), 2 One of them is bonded to the triazine ring shown in general formula (3), 2 The other one of them is bonded to (C)n. When n is 1, the bonded to (C)n There is 1. When n is 2, the bonded to (C)n There are 2. When n is 3, the bonded to (C)n There are 3.
45. The organic electroluminescent element according to claim 38, wherein, La is an aromatic hydrocarbon cyclic group represented by the following general formula (L1) or (L2). In the general formulas (L1) and (L2), 2 One of them is bonded to the triazine ring shown in general formula (3), 2 The other one of them is bonded to Ac.
46. The organic electroluminescent element according to any one of claims 1 to 29, wherein, A is an aryl group with 6 to 12 carbon atoms, either substituted or unsubstituted.
47. The organic electroluminescent element according to any one of claims 1 to 29, wherein, A is Substituted or unsubstituted phenyl Substituted or unsubstituted biphenyl, or Substituted or unsubstituted naphthyl groups.
48. The organic electroluminescent element according to any one of claims 1 to 29, wherein, B is an aryl group with 6 to 12 carbon atoms, either substituted or unsubstituted.
49. The organic electroluminescent element according to any one of claims 1 to 29, wherein, B is Substituted or unsubstituted phenyl Substituted or unsubstituted biphenyl, or Substituted or unsubstituted naphthyl groups.
50. The organic electroluminescent element according to any one of claims 1 to 29, wherein, A and B are each independently Substituted or unsubstituted phenyl Substituted or unsubstituted biphenyl, or Substituted or unsubstituted naphthyl groups.
51. The organic electroluminescent element according to any one of claims 1 to 29, wherein, The first electron transport layer contains only the third compound.
52. The organic electroluminescent element according to any one of claims 1 to 29, wherein, The first electron transport layer is directly connected to the light-emitting layer disposed on the cathode side of the first light-emitting layer and the second light-emitting layer.
53. The organic electroluminescent element according to any one of claims 1 to 29, wherein, A third electron transport layer is also provided between the first electron transport layer and the first and second light-emitting layers, specifically the light-emitting layer disposed on the cathode side.
54. The organic electroluminescent element according to claim 53, wherein, The third electron transport layer contains a fifth compound represented by the following general formula (3). It should be noted that the third compound contained in the first electron transport layer and the fifth compound contained in the third electron transport layer have different structures.
55. The organic electroluminescent element according to claim 53, wherein, The first electron transport layer is directly connected to the third electron transport layer.
56. The organic electroluminescent element according to claim 53, wherein, The third electron transport layer is directly connected to the light-emitting layer disposed on the cathode side of the first light-emitting layer and the second light-emitting layer.
57. The organic electroluminescent element according to any one of claims 1 to 29, wherein, It also has a second electron transport layer disposed between the first electron transport layer and the cathode.
58. The organic electroluminescent element according to claim 57, wherein, The second electron transport layer contains the fourth compound represented by the general formula (3). It should be noted that the third compound contained in the first electron transport layer and the fourth compound contained in the second electron transport layer have different structures.
59. The organic electroluminescent element according to claim 57, wherein, The first electron transport layer is directly connected to the second electron transport layer.
60. The organic electroluminescent element according to any one of claims 1 to 29, wherein, The first light-emitting layer is disposed between the anode and the second light-emitting layer.
61. The organic electroluminescent element according to any one of claims 1 to 29, wherein, The second light-emitting layer is disposed between the anode and the first light-emitting layer.
62. The organic electroluminescent element according to any one of claims 1 to 29, wherein, It also has a hole transport layer disposed between the anode and the first and second light-emitting layers that are directly in contact with each other. The hole transport layer contains compounds represented by the following general formula (C1) or (D1). In the general formula (C1), L A L B and L C Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 18 carbon atoms, or Divalent heterocyclic groups with 5 to 13 cyclic atoms, substituted or unsubstituted. A A B B and C C Each independently Substituted or unsubstituted aryl groups with 6 to 30 carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms, or -Si(R' 901 )(R' 902 )(R' 903 The group shown in the figure, R' 901 ~R' 903 Each is independently a substituted or unsubstituted aryl group with 6 to 30 carbon atoms in a cyclic formation. In R' 901 In the case of multiple R's, there are multiple R's. 901 They are the same or different. In R' 902 In the case of multiple R's, there are multiple R's. 902 They are the same or different. In R' 903 In the case of multiple R's, there are multiple R's. 903 They are the same or different. In the general formula (D1), A 41 and A 42 Each independently Substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or Heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted. L 41 and L 42 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted. Ra 410 ~Ra 414 One or more of the groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. Ra 420 ~Ra 424 One or more of the groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. Ra does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 410 ~Ra 414 and Ra 420 ~Ra 424 Each independently hydrogen atom, cyano, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, Halogen atoms, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. m1 and m2 are both 3. 3 Ra 410 They are the same or different. 3 Ra 420 They are the same or different. In the compounds represented by the general formula (D1), R 901 R 902 R 903 and R 904 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different. In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different. In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different. In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
63. The organic electroluminescent element according to claim 62, wherein, The hole transport layer contains a compound represented by the general formula (C1).
64. The organic electroluminescent element according to any one of claims 1 to 29, wherein, The organic electroluminescent element emits light with a maximum peak wavelength of 430 nm or higher and 480 nm or lower when the element is driven.
65. The organic electroluminescent element according to claim 1, wherein, The second light-emitting layer also contains a sixth fluorescent compound. The sixth compound is a compound that exhibits luminescence with a maximum peak wavelength of 430 nm or higher and 480 nm or lower.
66. The organic electroluminescent element according to claim 65, wherein, The content of the second compound is 80% by mass or more and 99% by mass or less. The content of the sixth compound is more than 1% by mass and less than 10% by mass.
67. The organic electroluminescent element according to any one of claims 1 to 29, wherein, The second light-emitting layer does not contain phosphorescent materials.
68. The organic electroluminescent element according to any one of claims 1 to 29, wherein, The second luminescent layer does not contain heavy metal complexes or phosphorescent rare earth metal complexes.
69. The organic electroluminescent element according to any one of claims 1 to 29, wherein, The second light-emitting layer does not contain metal complexes.
70. The organic electroluminescent element according to any one of claims 1 to 29, wherein, The second light-emitting layer does not contain boron-containing complexes.
71. The organic electroluminescent element according to claim 1, wherein, The first light-emitting layer also contains a seventh fluorescent compound. The seventh compound is a compound that exhibits luminescence with a maximum peak wavelength of 430 nm or higher and 480 nm or lower.
72. The organic electroluminescent element according to claim 71, wherein, The content of the first compound is 80% by mass or more and 99% by mass or less. The content of the seventh compound is more than 1% by mass and less than 10% by mass.
73. The organic electroluminescent element according to any one of claims 1 to 29, wherein, The first light-emitting layer does not contain phosphorescent materials.
74. The organic electroluminescent element according to any one of claims 1 to 29, wherein, The first luminescent layer does not contain heavy metal complexes or phosphorescent rare earth metal complexes.
75. The organic electroluminescent element according to any one of claims 1 to 29, wherein, The first light-emitting layer does not contain metal complexes.
76. The organic electroluminescent element according to any one of claims 1 to 29, wherein, The first light-emitting layer does not contain boron-containing complexes.
77. The organic electroluminescent element according to claim 65 or 71, wherein, In the presence of a sixth compound or a seventh compound, each of the sixth compound or the seventh compound is independently selected. The compounds represented by the following general formula (3A), The compounds represented by the following general formula (4), The compounds represented by the following general formula (5), The compounds represented by the following general formula (6), The compounds represented by the following general formula (7), The compounds represented by the following general formula (8), The compounds represented by the following general formula (9) and One or more compounds in the group consisting of compounds represented by the general formula (10) below, In the general formula (3A), Ra 301 Ra 302 Ra 303 Ra 304 Ra 305 Ra 306 Ra 307 Ra 308 Ra 309 and Ra 310 One or more of the groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. Ra 301 ~Ra 310 At least one of them is a monovalent group represented by the following general formula (31A), Ra does not form the monocyclic ring, does not form the fused ring, and is not a monovalent group represented by the following general formula (31A). 301 ~Ra 310 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the general formula (31A), Ara 301 and Ara 302 Each independently Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. La 301 La 302 and La 303 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted. This indicates the bonding position in the pyrene ring of the general formula (3A). In the general formula (4), Z can be independently represented by CRa or nitrogen atoms. Rings A1 and A2 are each independent of each other. Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted. When there are multiple Ra, one or more groups consisting of two or more adjacent Ra are selected. They bond together to form substituted or unsubstituted monocyclic rings, or They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. n21 and n22 are each independently 0, 1, 2, 3 or 4. When there are multiple Rb, one or more groups consisting of two or more adjacent Rb are considered. They bond together to form substituted or unsubstituted monocyclic rings, or They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. When there are multiple Rc, one or more groups are formed by two or more adjacent Rc. They bond together to form substituted or unsubstituted monocyclic rings, or They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. Ra, Rb, and Rc, which do not form the single ring and do not form the fused ring, are each independently [value missing]. Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Rb is bonded to any one of the carbon atoms that form the aromatic hydrocarbon ring as the Al ring, or to any one of the atoms that form the heterocycle as the Al ring. Rc is bonded to any one of the carbon atoms that form the aromatic hydrocarbon ring as the A2 ring, or to any one of the atoms that form the heterocycle as the A2 ring. In the general formula (5), R 501 ~R 507 and R 511 ~R 517 One or more of the groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings, or They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R that does not form the single ring and does not form the fused ring 501 ~R 507 and R 511 ~R 517 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. R 521 and R 522 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the general formula (6), Rings a, b, and c are each independently... Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted. R 601 and R 602 Each ring independently bonds to ring a, ring b, or ring c to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R does not form the substituted or unsubstituted heterocycles. 601 and R 602 Each independently Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the general formula (7), The r-ring is a ring represented by the general formula (72) or general formula (73) that is fused at any position of adjacent rings. The q-ring and s-ring are each independently rings fused at any position of adjacent rings as shown in the general formula (74). The p-ring and t-ring are each independently structures shown in general formula (75) or general formula (76) that are fused at any position of adjacent rings. X7 represents an oxygen atom, a sulfur atom, or NR. 702 , In R 701 In the case of multiple occurrences, multiple adjacent R 701 They bond together to form substituted or unsubstituted monocyclic rings, or They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R that does not form the single ring and does not form the fused ring 701 and R 702 Each independently Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 701 and Ar 702 Each independently Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. L 701 for Substituted or unsubstituted alkylene groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted ynylene groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkylene groups with 3 to 50 carbon atoms Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. m1 is 0, 1, or 2. m2 can be 0, 1, 2, 3, or 4. m3 can be independently 0, 1, 2 or 3. Each m4 is independently 0, 1, 2, 3, 4, or 5. In R 701 In the case of multiple Rs, multiple Rs 701 They are the same or different. When multiple X7s exist, these X7s may be identical or different from each other. In R 702 In the case of multiple Rs, multiple Rs 702 They are the same or different. In Ar 701 In the case of multiple instances, multiple Ar 701 They are the same or different. In Ar 702 In the case of multiple instances, multiple Ar 702 They are the same or different. In L 701 In the case of multiple Ls, multiple Ls 701 They are the same or different. In the general formula (8), R 801 With R 802 R 802 With R 803 and R 803 With R 804 At least one group of the groups are bonded to each other to form the divalent groups shown in the following general formula (82), or they are not bonded to each other. R 805 With R 806 R 806 With R 807 and R 807 With R 808 At least one group of the groups are bonded to each other to form the divalent group shown in the following general formula (83), or they are not bonded to each other. R that does not form the divalent group shown in the general formula (82) 801 ~R 804 and R 811 ~R 814 At least one of them is a monovalent group represented by the following general formula (84), R that does not form the divalent group shown in the general formula (83) 805 ~R 808 and R 821 ~R 824 At least one of them is a monovalent group represented by the following general formula (84), X8 is CR 81 R 82 oxygen atom, sulfur atom or NR 809 , R 81 and R 82 The group formed They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R that does not form the divalent groups shown in general formulas (82) and (83) and is not the monovalent group shown in general formula (84) 801 ~R 808 R is not a monovalent group represented by the general formula (84). 811 ~R 814 and R 821 ~R 824 R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 81 and R 82 and R 809 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the general formula (84), Ar 801 and Ar 802 Each independently Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. L 801 ~L 803 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms Substituted or unsubstituted divalent heterocyclic groups with 5 to 30 cyclic atoms, or A divalent linker is formed by bonding 2 to 4 groups from the group consisting of a substituted or unsubstituted aryl group with 6 to 30 carbon atoms and a substituted or unsubstituted divalent heterocyclic group with 5 to 30 carbon atoms. In the general formula (84) This indicates the bonding position with the ring structure shown in general formula (8), or the group shown in general formula (82) or general formula (83). In the general formula (9), A 91 Ring and A 92 Each ring is independent of the others. Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted. Selected from A 91 Ring and A 92 One or more rings in the ring have the structure shown in the following general formula (92) bonding, In the general formula (92), A 93 Ring for Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted. X9 is NR 93 C(R) 94 (R) 95 ), Si(R) 96 (R) 97 ), Ge(R) 98 (R) 99 ), oxygen atoms, sulfur atoms or selenium atoms, R 91 and R 92 for They bond together to form substituted or unsubstituted monocyclic rings, or They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R that does not form the single ring and does not form the fused ring 91 and R 92 and R 93 ~R 99 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In the general formula (10), Ax1 ring is a ring of the general formula (10a) that is fused at any position between adjacent rings. Ax2 ring is a ring of the general formula (10b) that is fused at any position between adjacent rings. The two in the general formula (10b) Bonded to any position on the Ax3 ring, X A and X B Each independently is C(R) 1003 (R) 1004 ), Si(R) 1005 (R) 1006 ), oxygen atom or sulfur atom, Ax3 ring is Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted. Ar 1001 for Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. R 1001 ~R 1006 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. mx1 is 3, mx2 is 2. Multiple R 1001 They are the same or different. Multiple R 1002 They are the same or different. ax is 0, 1, or 2. When ax is 0 or 1, the structures within the parentheses shown in "3-ax" are either identical or different. When ax = 2, multiple Ar 1001 They are the same or different. In the sixth or seventh compound, R 901 R 902 R 903 R 904 R 905 R 906 and R 907 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different. In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different. In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different. In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different. In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different. In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different. In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.
78. The organic electroluminescent element according to claim 77, wherein, In the sixth and seventh compounds, the groups described as "substituted or unsubstituted" are all "unsubstituted" groups.
79. The organic electroluminescent element according to any one of claims 1 to 29, wherein, When expressed as "substituted or unsubstituted", the substituents are free to be selected. Alkyl groups having 1 to 18 carbon atoms aryl groups with 6 to 18 carbon atoms, and At least one group from the group consisting of heterocyclic groups with 5 to 18 cyclic atoms.
80. The organic electroluminescent element according to any one of claims 1 to 29, wherein, When expressed as "substituted or unsubstituted", the substituent is an alkyl group having 1 to 5 carbon atoms.
81. The organic electroluminescent element according to any one of claims 1 to 29, wherein, In the first compound, the second compound, and the third compound, all groups described as "substituted or unsubstituted" are "unsubstituted" groups.
82. The organic electroluminescent element according to claim 1, wherein, The first compound is selected from the following compounds: BH1, BH3, BH1-1, BH1-2, BH1-3, BH1-4, and BH1-5. The second compound is selected from the following compounds: BH2, BH4, BH2-1, and BH2-2. The third compound is selected from compounds ET1-ET12 and ET14-ET20. 。 83. The organic electroluminescent element according to claim 1, 65, or 71, wherein, The maximum peak wavelength of a compound refers to the wavelength at which the compound prepared for the assay reaches its maximum value within 1000 nm. -6 mol / L or higher and 10 - 5 A toluene solution with a concentration of less than mol / L was added to a quartz cuvette as a sample. The emission spectrum of the sample was measured at room temperature (300K). The peak wavelength of the emission spectrum with the highest emission intensity was determined. The vertical axis represents the emission intensity and the horizontal axis represents the wavelength.
84. The organic electroluminescent element according to claim 1, 22, or 29, wherein, The compound to be measured for the triplet energy T1 was dissolved in EPA with a volume ratio of diethyl ether:isopentane:ethanol = 5:5:2 to achieve 10 -5 mol / L or higher and 10 -4 A solution with a concentration below mol / L was obtained and added to a quartz cuvette as the test sample. The phosphorescence spectrum of this test sample was measured at 77 K. The wavelength λ at the intersection of the rising tangent on the short wavelength side of the phosphorescence spectrum was determined. edge The energy calculated according to the following conversion formula (F1) is taken as the triplet energy T1, where the vertical axis of the phosphorescence spectrum is the phosphorescence intensity and the horizontal axis is the wavelength, λ. edge The unit is nm, and the unit of T1 is eV. Conversion formula (F1): T1 = 1239.85 / λ edge .
85. The organic electroluminescent element according to claim 21 or 28, wherein, 10 compounds prepared for determination of singlet energy S1 -5 mol / L or higher and 10 -4 A toluene solution with a concentration below mol / L was added to a quartz cuvette as a sample. The absorption spectrum of the sample was measured at 300 K. A downward-sloping tangent was drawn on the longer wavelength side of the absorption spectrum. The wavelength value λedge at the intersection of this tangent and the horizontal axis was substituted into the conversion formula (F2) shown later to calculate the singlet energy S1. Here, the vertical axis of the absorption spectrum represents the absorption intensity, and the horizontal axis represents the wavelength. The unit of λedge is nm, and the unit of S1 is eV. Conversion formula (F2): S1 = 1239.85 / λedge.
86. An electronic device comprising an organic electroluminescent element according to any one of claims 1 to 85.
Citation Information
Patent Citations
Organic electroluminescent element
JP2007294261A
Organic light emitting element
JP2013157552A
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JP2019161218A
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JP2009016693A
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