Organic electroluminescent element and electronic device
Patent Information
- Application Number
- CN202180005612.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2020-02-14
- Filing Date
- 2021-02-10
- Publication Date
- 2026-10-16
- Estimated Expiration
- 2041-02-10
AI Technical Summary
[0056] According to one aspect of the present invention, an organic electroluminescent element with improved performance can be provided. Furthermore, according to another aspect of the present invention, an organic electroluminescent element with improved luminous efficiency and longer lifetime can be provided. Additionally, according to another aspect of the present invention, an electronic device incorporating the organic electroluminescent element can be provided.
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Figure CN114450817B_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 (see, for example, Patent Documents 1-6). For instance, Patent Documents 6 and 7 investigated the stacking of multiple light-emitting layers. Furthermore, Patent Document 8 describes a phenomenon where singlet excitons are generated through the collisional fusion of two triplet excitons to improve the performance of organic EL devices (hereinafter sometimes referred to as Triplet-Triplet Fusion = TTF phenomenon). Examples of the performance characteristics of organic EL devices include, for instance, brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime.
[0004] Existing technical documents
[0005] Patent documents
[0006] Patent Document 1: Japanese Patent Application Publication No. 2013-157552
[0007] Patent Document 2: International Publication No. 2004 / 018587
[0008] Patent Document 3: International Publication No. 2005 / 115950
[0009] Patent Document 4: International Publication No. 2011 / 077691
[0010] Patent Document 5: Japanese Patent Application Publication No. 2018-125504
[0011] Patent Document 6: U.S. Patent Application Publication No. 2019 / 280209
[0012] Patent Document 7: Japanese Patent Application Publication No. 2007-294261
[0013] Patent Document 8: International Publication No. 2010 / 134350 Summary of the Invention
[0014] The problem the invention aims to solve
[0015] For example, Patent Document 7 describes an organic EL element in which red phenanthroline (BCP), a phenanthroline compound with a phenanthroline skeleton, is deposited on the light-emitting layer to form an electron transport layer, and then BCP and Cs (cesium) are co-deposited to form an electron injection layer, and aluminum is further deposited to form a cathode.
[0016] If phenanthroline compounds are used in the intermediate layer between the light-emitting units of a tandem organic EL element with multiple light-emitting units, there is a tendency for the element lifespan to decrease.
[0017] One object of the present invention is to provide an organic electroluminescent element with improved performance. Another object of the present invention is to provide an organic electroluminescent element with improved luminous efficiency and longer lifetime, and an electronic device incorporating the organic electroluminescent element.
[0018] means for solving problems
[0019] According to one aspect of the present invention, an organic electroluminescent element is provided, the organic electroluminescent element having
[0020] anode,
[0021] cathode,
[0022] Two or more light-emitting units disposed between the anode and the cathode, and
[0023] The first cathode-side organic layer disposed between the anode and the cathode,
[0024] At least one of the above two or more light-emitting units is a stacked light-emitting unit.
[0025] The first cathode-side organic layer is disposed on the cathode side of at least one of the aforementioned stacked light-emitting units.
[0026] The aforementioned first cathode-side organic layer contains phenanthroline compounds with a phenanthroline skeleton.
[0027] The aforementioned stacked light-emitting unit includes a first light-emitting layer and a second light-emitting layer.
[0028] The aforementioned first light-emitting layer contains a first host material.
[0029] The aforementioned second light-emitting layer contains a second host material.
[0030] The first main material mentioned above is different from the second main material mentioned above.
[0031] The aforementioned first luminescent layer contains at least a first luminescent compound exhibiting luminescence with a maximum peak wavelength of less than 500 nm.
[0032] The aforementioned second luminescent layer contains at least a second luminescent compound exhibiting luminescence with a maximum peak wavelength below 500 nm.
[0033] The first luminescent compound described above may be the same as or different from the second luminescent compound described above.
[0034] 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 3).
[0035] T1(H1)>T1(H2)...(Mathematical Expression 3)
[0036] According to one aspect of the present invention, an organic electroluminescent element is provided, the organic electroluminescent element having
[0037] anode,
[0038] cathode,
[0039] Two or more light-emitting units disposed between the anode and the cathode, and
[0040] The first cathode-side organic layer disposed between the anode and the cathode,
[0041] At least one of the above two or more light-emitting units is a stacked light-emitting unit.
[0042] The first cathode-side organic layer is disposed on the cathode side of at least one of the aforementioned stacked light-emitting units.
[0043] The aforementioned first cathode-side organic layer contains phenanthroline compounds with a phenanthroline skeleton.
[0044] The aforementioned stacked light-emitting unit includes a first light-emitting layer and a second light-emitting layer.
[0045] The aforementioned first light-emitting layer contains a first host material.
[0046] The aforementioned second light-emitting layer contains a second host material.
[0047] The aforementioned first host material has a structure in its molecule that meets either condition (i) or condition (ii).
[0048] The second main material mentioned above is an anthracene derivative.
[0049] The first main material mentioned above is different from the second main material mentioned above.
[0050] The aforementioned first luminescent layer contains at least a first luminescent compound exhibiting luminescence with a maximum peak wavelength of less than 500 nm.
[0051] The aforementioned second luminescent layer contains at least a second luminescent compound exhibiting luminescence with a maximum peak wavelength below 500 nm.
[0052] The first luminescent compound described above may be the same as or different from the second luminescent compound described above.
[0053] Condition (i) has a biphenyl structure in which a first benzene ring and a second benzene ring are connected by a single bond, wherein the first benzene ring and the second benzene ring in the biphenyl structure are further connected by crosslinking in at least one part other than the single bond.
[0054] Condition (ii) has a linkage structure comprising a benzene ring and a naphthalene ring linked by a single bond, wherein the benzene ring and the naphthalene ring in the linkage structure are each further independently fused with a single ring or a fused ring, or are not fused, and 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.
[0055] According to one aspect of the present invention, an electronic device incorporating the organic electroluminescent element described above is provided.
[0056] According to one aspect of the present invention, an organic electroluminescent element with improved performance can be provided. Furthermore, according to another aspect of the present invention, an organic electroluminescent element with improved luminous efficiency and longer lifetime can be provided. Additionally, according to another aspect of the present invention, an electronic device incorporating the organic electroluminescent element can be provided. Attached Figure Description
[0057] 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. Detailed Implementation
[0058] [definition]
[0059] In this specification, a hydrogen atom means an isotope containing different numbers of neutrons, namely protium, deuterium, and tritium.
[0060] 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.
[0061] 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.
[0062] 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.
[0063] 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.
[0064] 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.
[0065] 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.
[0066] In this specification, "unsubstituted ZZ group" means "substituted or unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".
[0067] 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 substituted with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.
[0068] 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.
[0069] Substituents described in this specification
[0070] The substituents described in this specification are explained below.
[0071] 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.
[0072] 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.
[0073] 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.
[0074] 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.
[0075] 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.
[0076] 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.
[0077] 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.
[0078] 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.
[0079] 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.
[0080] • "Substituted or unsubstituted aryl groups"
[0081] 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.
[0082] "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.
[0083] • Unsubstituted aryl groups (specific example group G1A):
[0084] phenyl,
[0085] p-phenyl,
[0086] metaphenyl,
[0087] o-phenyl,
[0088] p-terphenyl-4-yl,
[0089] p-terphenyl-3-yl,
[0090] p-terphenyl-2-yl,
[0091] m-terphenyl-4-yl,
[0092] m-terphenyl-3-yl,
[0093] m-terphenyl-2-yl,
[0094] o-terphenyl-4-yl
[0095] o-terphenyl-3-yl
[0096] o-terphenyl-2-yl,
[0097] 1-Naphthyl,
[0098] 2-Naphthyl,
[0099] anthracene,
[0100] Benzanthracene,
[0101] Fiki,
[0102] Benzphenanthrene,
[0103] Finadenyl,
[0104] Pyrene
[0105] base,
[0106] benzo[a] base,
[0107] Tri-phenylene,
[0108] Benzotrimethylene
[0109] phenoxytetraphenyl,
[0110] Pentaphenyl,
[0111] Fluorine
[0112] 9,9'-spirobisfluorene,
[0113] benzo[f]fluorenyl,
[0114] Dibenzofluorene,
[0115] Fluoranthene group,
[0116] Benzofluoranthyl,
[0117] 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.
[0118]
Chemical Formula 1
[0119]
[0120]
Chemical Formula 2
[0121]
[0122] • Substituted aryl groups (specific example group G1B):
[0123] o-Tolyl,
[0124] m-Tolyl,
[0125] p-Tolyl,
[0126] p-Xylyl,
[0127] m-Xylyl,
[0128] o-xylyl,
[0129] p-isopropylphenyl,
[0130] m-Isopropylphenyl,
[0131] o-isopropylphenyl,
[0132] p-tert-butylphenyl,
[0133] m-tert-butylphenyl,
[0134] o-tert-butylphenyl,
[0135] 3,4,5-Trimethylphenyl,
[0136] 9,9-Dimethylfluorenyl,
[0137] 9,9-Diphenylfluorenyl,
[0138] 9,9-bis(4-methylphenyl)fluorenyl,
[0139] 9,9-Bis(4-isopropylphenyl)fluorenyl,
[0140] 9,9-Bis(4-tert-butylphenyl)fluorenyl,
[0141] cyanophenyl,
[0142] Triphenylsilylphenyl
[0143] Trimethylsilylphenyl
[0144] Phenylacetyl,
[0145] 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.
[0146] • "Substituted or unsubstituted heterocyclic groups"
[0147] 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.
[0148] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.
[0149] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.
[0150] 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".
[0151] "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.
[0152] 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).
[0153] 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).
[0154] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):
[0155] pyrrole,
[0156] Imidazole group,
[0157] Pyrazolyl,
[0158] Triazole group,
[0159] Tetrazolyl,
[0160] Oxazolyl,
[0161] Isoxazolyl,
[0162] Oxadiazole group,
[0163] Thiazole group,
[0164] Isothiazolyl,
[0165] Thiadiazole group,
[0166] pyridyl,
[0167] pyridazinyl,
[0168] Pyrimidinyl,
[0169] Pyrazinyl,
[0170] Triazine group
[0171] Indole,
[0172] Isoindolyl,
[0173] Indazine group
[0174] Quinazine-based
[0175] Quinoline,
[0176] Isoquinoline,
[0177] Crenoline group
[0178] Phthaloazine
[0179] Quinazolinyl,
[0180] Quinoxaloyl,
[0181] Benzimidazole group,
[0182] Indazole group,
[0183] phenanthroline,
[0184] phenanthridine,
[0185] acridine group,
[0186] Phenazine group,
[0187] Carbazolyl,
[0188] Benzocarbazolyl,
[0189] Morpholinyl
[0190] phenoxazine group,
[0191] phenothiazine group,
[0192] Azacarbazolyl and diazacarbazolyl.
[0193] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2):
[0194] furanyl,
[0195] Oxazolyl,
[0196] Isoxazolyl,
[0197] Oxadiazole group,
[0198] Xuton base,
[0199] Benzofuranyl,
[0200] Isobenzofuranyl,
[0201] Dibenzofuranyl,
[0202] Naphthobenzofuranyl,
[0203] Benzoxazolyl,
[0204] Benzisoxazole group,
[0205] phenoxazine group,
[0206] Morpholinyl
[0207] Dinaphthylfuranyl,
[0208] Azadibenzofuranyl,
[0209] diazadibenzofuranyl,
[0210] Azanaphthobenzofuranyl and diazanaphthobenzofuranyl.
[0211] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3):
[0212] Thiophene group
[0213] Thiazole group,
[0214] Isothiazolyl,
[0215] Thiadiazole group,
[0216] benzothienyl
[0217] isobenzothienyl
[0218] dibenzothienyl
[0219] Naphthobenzothienyl
[0220] Benzothiazolyl,
[0221] Benzisothiazolyl,
[0222] phenothiazine group,
[0223] dinaphthothienyl
[0224] azadibenzothienyl
[0225] diazadibenzothienyl
[0226] Azanaphthobenzothienyl and diazanaphthobenzothienyl.
[0227] • 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):
[0228]
Chemical Formula 3
[0229]
[0230] [Chemical Formula 4]
[0231]
[0232] 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.
[0233] 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.
[0234] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):
[0235] (9-phenyl)carbazole group,
[0236] (9-Biphenyl)carbazole,
[0237] (9-Phenyl)phenylcarbazolyl,
[0238] (9-Naphthyl)carbazole,
[0239] Diphenylcarbazole-9-yl,
[0240] Phenylexacarbazole-9-yl,
[0241] Methylbenzimidazole,
[0242] Ethylbenzimidazole,
[0243] Phenylacetyl,
[0244] Biphenyltriazine,
[0245] diphenyltriazine group,
[0246] Phenylacetinyl and biphenylquinazolinyl.
[0247] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):
[0248] Phenyl dibenzofuranyl,
[0249] Methyldibenzofuranyl,
[0250] The monovalent residues of tert-butyldibenzofuranyl and spiro[9H-xanton-9,9'-[9H]fluorene].
[0251] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):
[0252] Phenyl dibenzothiophene,
[0253] Methyldibenzothiophene,
[0254] The monovalent residues of tert-butyldibenzothiophene and spiro[9H-thiophene-9,9'-[9H]fluorene].
[0255] • 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):
[0256] 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.
[0257] • "Substituted or unsubstituted alkyl groups"
[0258] 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.
[0259] "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.
[0260] • Unsubstituted alkyl groups (specific example group G3A):
[0261] methyl,
[0262] Ethyl,
[0263] n-propyl,
[0264] Isopropyl,
[0265] n-Butyl,
[0266] Isobutyl,
[0267] Sec-butyl and tert-butyl.
[0268] • Substituted alkyl groups (specific example group G3B):
[0269] Heptafluoropropyl (including isomers),
[0270] Pentafluoroethyl,
[0271] 2,2,2-Trifluoroethyl and trifluoromethyl.
[0272] • "Substituted or unsubstituted alkenyl groups"
[0273] 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.
[0274] "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 which the hydrogen atoms of the alkenyl group itself in the "substituted alkenyl" group of specific example group G4B have been further substituted with a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted alkenyl" group of specific example group G4B have been further substituted with a substituent.
[0275] • Unsubstituted alkenyl groups (specific example group G4A):
[0276] vinyl,
[0277] Allyl
[0278] 1-Butenyl,
[0279] 2-Butenyl and 3-Butenyl.
[0280] • Substituted alkenyl groups (specific example group G4B):
[0281] 1,3-Butadienyl,
[0282] 1-Methylvinyl
[0283] 1-Methylallyl,
[0284] 1,1-Dimethylallyl,
[0285] 2-Methylallyl and 1,2-dimethylallyl.
[0286] • "Substituted or unsubstituted alkynyl groups"
[0287] 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".
[0288] "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.
[0289] • Unsubstituted alkynyl group (specific example group G5A): ethynyl group.
[0290] • "Substituted or unsubstituted cycloalkyl groups"
[0291] 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.
[0292] "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.
[0293] • Unsubstituted cycloalkyl groups (specific example group G6A):
[0294] Cyclopropyl
[0295] Cyclobutyl,
[0296] Cyclopentyl,
[0297] Cyclohexyl,
[0298] 1-Adamantyl,
[0299] 2-Adamantyl,
[0300] 1-norborneol and 2-norborneol.
[0301] • Substituted cycloalkyl group (specific example group G6B): 4-methylcyclohexyl.
[0302] ·"-Si(R 901 (R) 902 (R)903 The group shown in the figure”
[0303] 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:
[0304] -Si(G1)(G1)(G1),
[0305] -Si(G1)(G2)(G2)
[0306] -Si(G1)(G1)(G2),
[0307] -Si(G2)(G2)(G2),
[0308] -Si(G3)(G3)(G3) and -Si(G6)(G6)(G6). Here,
[0309] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.
[0310] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
[0311] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.
[0312] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.
[0313] In -Si(G1)(G1)(G1), multiple G1s may be the same or different from each other.
[0314] In -Si(G1)(G2)(G2), multiple G2s may be the same or different from each other.
[0315] In -Si(G1)(G1)(G2), multiple G1s may be the same or different from each other.
[0316] In -Si(G2)(G2)(G2), multiple G2s may be the same or different from each other.
[0317] In -Si(G3)(G3)(G3), multiple G3s may be the same or different from each other.
[0318] In -Si(G6)(G6)(G6), multiple G6s may be the same or different from each other.
[0319] ·“-O-(R 904 The group shown in the figure”
[0320] As described in this specification, -O-(R)904 Specific examples of the group shown (specific example group G8) can be given as follows:
[0321] -O(G1)
[0322] -O(G2),
[0323] -O(G3) and -O(G6).
[0324] Here,
[0325] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.
[0326] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
[0327] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.
[0328] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.
[0329] ·“-S-(R 905 The group shown in the figure”
[0330] As described in this specification, -S-(R) 905 Specific examples of the group shown (specific example group G9) can be given as follows:
[0331] -S(G1),
[0332] -S(G2),
[0333] -S(G3) and -S(G6).
[0334] Here,
[0335] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.
[0336] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
[0337] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.
[0338] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.
[0339] ·"-N(R 906 (R) 907 The group shown in the figure”
[0340] As described in this specification, -N(R) 906 (R) 907Specific examples of the group shown (specific example group G10) can be given as follows:
[0341] -N(G1)(G1),
[0342] -N(G2)(G2),
[0343] -N(G1)(G2),
[0344] -N(G3)(G3) and -N(G6)(G6).
[0345] Here,
[0346] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.
[0347] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
[0348] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.
[0349] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.
[0350] In -N(G1)(G1), multiple G1s may be the same or different from each other.
[0351] In -N(G2)(G2), multiple G2 values may be the same or different from each other.
[0352] In -N(G3)(G3), multiple G3s may be the same or different from each other.
[0353] In -N(G6)(G6), multiple G6 values may be the same or different from each other.
[0354] • "Halogen atom"
[0355] Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.
[0356] • "Substituted or unsubstituted fluoroalkyl groups"
[0357] 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.
[0358] • "Substituted or unsubstituted haloalkyl groups"
[0359] 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.
[0360] • "Substituted or unsubstituted alkoxy groups"
[0361] 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.
[0362] • "Substituted or unsubstituted alkylthio groups"
[0363] 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.
[0364] • "Substituted or unsubstituted aryloxy groups"
[0365] 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.
[0366] • "Substituted or unsubstituted arylthio groups"
[0367] 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.
[0368] • "Substituted or unsubstituted trialkylsilyl groups"
[0369] 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.
[0370] • "Substituted or unsubstituted aralkyl groups"
[0371] 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.
[0372] 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.
[0373] 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.
[0374] 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.
[0375] In this specification, the carbazoyl group, unless otherwise specified herein, specifically refers to any one of the following groups.
[0376] [Chemical Formula 5]
[0377]
[0378] In this specification, (9-phenyl)carbazolyl refers specifically to any one of the following groups unless otherwise specified herein.
[0379]
Chemical Formula 6
[0380]
[0381] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.
[0382] In this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any one of the following groups unless otherwise stated in this specification.
[0383] [Chemical Formula 7]
[0384]
[0385] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.
[0386] 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.
[0387] • "Substituted or unsubstituted aryl groups"
[0388] 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.
[0389] • "Substituted or unsubstituted divalent heterocyclic groups"
[0390] 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.
[0391] • "Substituted or unsubstituted alkylene compounds"
[0392] 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.
[0393] 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).
[0394] [Chemical Formula 8]
[0395]
[0396] [Chemical Formula 9]
[0397]
[0398] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.
[0399] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.
[0400]
Chemical Formula 10
[0401]
[0402] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.
[0403] Formulas Q9 and Q 10 They can form rings by bonding with each other via single bonds.
[0404] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.
[0405]
Chemical Formula 11
[0406]
[0407] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.
[0408] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.
[0409] 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).
[0410]
Chemical Formula 12
[0411]
[0412]
Chemical Formula 13
[0413]
[0414]
Chemical Formula 14
[0415]
[0416] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.
[0417]
Chemical Formula 15
[0418]
[0419] [Chemical Formula 16]
[0420]
[0421]
Chemical Formula 17
[0422]
[0423] [Chemical Formula 18]
[0424]
[0425] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.
[0426] The above is an explanation of "substituents described in this specification".
[0427] • "Cases where bonds form rings"
[0428] 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".
[0429] 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.
[0430] [Chemical Formula 19]
[0431]
[0432] 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, R930 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.
[0433] 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).
[0434]
Chemical Formula 20
[0435]
[0436] 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 923 When 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 .
[0437]
Chemical Formula 21
[0438]
[0439] 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 occurs, forming a fused ring. If 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. If the ring Q of the above general formula (TMEP-104) is... A If it is a naphthalene ring, then ring Q A It is a fused ring.
[0440] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.
[0441] 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.
[0442] 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.
[0443] 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.
[0444] "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 R921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 When the bonded anthracene skeleton carbon atoms and 4 carbon atoms form a monocyclic unsaturated ring, R 921 With R 922 The resulting ring is a benzene ring.
[0445] 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.
[0446] 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.
[0447] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".
[0448] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".
[0449] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.
[0450] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.
[0451] 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.
[0452] 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.
[0453] 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.
[0454] 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").
[0455] Substituents when described as "substituted or unsubstituted"
[0456] 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...
[0457] Unsubstituted alkyl groups having 1 to 50 carbon atoms
[0458] Unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0459] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms
[0460] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0461] -Si(R 901 (R) 902 (R) 903 ),
[0462] -O-(R 904 ),
[0463] -S-(R 905 ),
[0464] -N(R 906 (R) 907 ),
[0465] Halogen atom, cyano group, nitro group,
[0466] Groups in the group consisting of unsubstituted aryl groups with 6 to 50 carbon atoms and unsubstituted heterocyclic groups with 5 to 50 atoms.
[0467] Here, R 901 ~R 907 Each independently
[0468] hydrogen atom,
[0469] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0470] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0471] 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.
[0472] 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.
[0473] 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.
[0474] 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.
[0475] 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.
[0476] 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.
[0477] 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.
[0478] In R 907 If there are two or more instances, the two or more R907s are either the same or different from each other.
[0479] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.
[0480] Alkyl groups with 1 to 50 carbon atoms
[0481] Groups in the group consisting of aryl groups with 6 to 50 carbon atoms and heterocyclic groups with 5 to 50 atoms.
[0482] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.
[0483] Alkyl groups having 1 to 18 carbon atoms
[0484] Groups in the group consisting of aryl groups with 6 to 18 carbon atoms and heterocyclic groups with 5 to 18 atoms.
[0485] Specific examples of each of the optional substituents are those described in the section "Substituents as described in this specification" above.
[0486] 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.
[0487] 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.
[0488] 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.
[0489] [First Embodiment] (Organic Electroluminescent Element)
[0490] The organic electroluminescent element involved in this embodiment has the basic structure shown below.
[0491] (Basic Components)
[0492] The organic electroluminescent element according to this embodiment has an anode, a cathode, two or more light-emitting units disposed between the anode and the cathode, and a first cathode-side organic layer disposed between the anode and the cathode. At least one of the two or more light-emitting units is a stacked light-emitting unit. The first cathode-side organic layer is disposed on the cathode side of the at least one of the stacked light-emitting units. The first cathode-side organic layer contains a phenanthroline compound having a phenanthroline skeleton. The stacked light-emitting unit includes a first light-emitting layer and a second light-emitting layer. The first light-emitting layer contains a first host material, and the second light-emitting layer contains 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 first luminescent compound that emits light with a maximum peak wavelength of 500 nm or less, and the second light-emitting layer contains at least a second luminescent compound that emits light with a maximum peak wavelength of 500 nm or less. The first luminescent compound and the second luminescent compound may be the same as or different from each other.
[0493] In addition to the basic structure described above, the organic EL element involved in this embodiment also includes at least one of the following elements (1) and (2).
[0494] (Element 1)
[0495] In element 1, 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 3).
[0496] T1(H1)>T1(H2)...(Mathematical Expression 3)
[0497] (Element 2)
[0498] In element 2, the first host material has a structure under condition (i) or condition (ii) in the molecule, wherein the first benzene ring and the second benzene ring in the biphenyl structure are further connected by crosslinking in at least one part other than the single bond, and the second host material is an anthracene derivative.
[0499] Condition (i) has a biphenyl structure in which a first benzene ring and a second benzene ring are connected by a single bond, wherein the first benzene ring and the second benzene ring in the biphenyl structure are further connected by crosslinking in at least one part other than the single bond.
[0500] Condition (ii) has a linkage structure comprising a benzene ring and a naphthalene ring linked by a single bond, wherein the benzene ring and the naphthalene ring in the linkage structure are each further independently fused with a single ring or a fused ring, or are not fused, and 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.
[0501] Hereinafter, the organic EL element involved in this embodiment, which includes the basic structure described above and at least one of (element 1) and (element 2), will be described.
[0502] In this specification, an organic electroluminescent element having two or more light-emitting units disposed between the anode and the cathode is referred to as a series-type organic electroluminescent element (series-type organic EL element).
[0503] According to this embodiment, an organic electroluminescent element with improved luminous efficiency can be provided.
[0504] Previously, triplet-triple annihilation (sometimes called TTA) was known as a technique for improving the luminous efficiency of organic electroluminescent devices. TTA is the mechanism by which triplet excitons collide with each other to generate singlet excitons. It should be noted that the TTA mechanism is sometimes also referred to as the TTF mechanism, as described in Patent Document 8.
[0505] 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%.
[0506] 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.
[0507] 3 A*+ 3 A*→(4 / 9) 1 A+(1 / 9) 1 A*+(13 / 9) 3 A*
[0508] 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 originating from TTF in the total luminescence intensity (TTF ratio) 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%.
[0509] According to the organic electroluminescent element of this embodiment, it is believed that for triplet excitons generated by the recombination of holes and electrons in the first light-emitting layer of the stacked light-emitting unit, even if there are excess charge carriers at the interface between the first light-emitting layer and the directly connected 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 the recombination region is 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 the recombination region is 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.
[0510] The organic electroluminescent element according to this embodiment includes a stacked light-emitting unit comprising 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 3).
[0511] By employing stacked luminescent units comprising a first luminescent layer and a second luminescent layer, as per the relationship satisfying the aforementioned mathematical formula (Formula 3), 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.
[0512] Thus, the stacked light-emitting unit in 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 and mainly exhibits 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 triplet energy difference, thereby improving the luminous efficiency.
[0513] Phenanthroline compounds with a phenanthroline backbone are suitable for use as electron transport materials in so-called tandem organic EL devices with multiple light-emitting units because they readily generate charges. However, phenanthroline compounds have low tolerance to holes. If holes migrate from the light-emitting layer to the organic layer containing the phenanthroline compound (such as the electron transport layer), the phenanthroline compound tends to degrade, leading to a decrease in device lifetime.
[0514] In the organic EL element of this embodiment, a first cathode-side organic layer containing a phenanthroline compound is disposed on the cathode side of a stacked light-emitting unit comprising a first light-emitting layer and a second light-emitting layer. This stacked light-emitting unit has a first light-emitting layer that primarily generates triplet excitons and a second light-emitting layer that effectively utilizes triplet excitons migrating from the first light-emitting layer and primarily embodies the TTF mechanism as distinct regions. Therefore, the easily degraded first cathode-side organic layer containing a phenanthroline compound can be separated from the first light-emitting layer (composite layer), suppressing the amount of holes migrating from the stacked light-emitting unit to the first cathode-side organic layer, thus extending the lifetime of the organic EL element.
[0515] The first cathode-side organic layer is an organic layer disposed on the cathode side of at least one stacked light-emitting unit. The first cathode-side organic layer is sometimes referred to as the intermediate layer.
[0516] The intermediate layer is also commonly referred to as the intermediate electrode, intermediate conductive layer, charge generation layer, electron extraction layer, connection layer, connector layer, or intermediate insulating layer.
[0517] An intermediate layer supplies electrons to layers located further anode than the intermediate layer and holes to layers located further cathode than the intermediate layer. The intermediate layer can be formed from known materials. An intermediate layer can consist of one layer or two or more layers. Sometimes, a unit consisting of two or more intermediate layers is called an intermediate unit. The compositions of the multiple intermediate layers contained in an intermediate unit may be the same or different.
[0518] In addition, the multiple layers containing the light-emitting layer disposed between the intermediate layer or intermediate unit and the anode or cathode are sometimes referred to as light-emitting units. Examples of organic EL elements having multiple light-emitting units include the following (TND1) to (TND4) configurations.
[0519] (TND1) Anode / First Light-Emitting Unit / Intermediate Layer / Second Light-Emitting Unit / Cathode
[0520] (TND2) Anode / First Light-Emitting Unit / Intermediate Unit / Second Light-Emitting Unit / Cathode
[0521] (TND3) Anode / First Light-Emitting Unit / First Intermediate Layer / Second Light-Emitting Unit / Second Intermediate Layer / Third Light-Emitting Unit / Cathode
[0522] (TND4) Anode / First Light-Emitting Unit / First Intermediate Unit / Second Light-Emitting Unit / Second Intermediate Unit / Third Light-Emitting Unit / Cathode
[0523] In the organic EL element of this embodiment, the number of light-emitting units and intermediate layers (or intermediate units) is not limited to the examples (TND1) to (TND4) shown here.
[0524] In the above-described element configurations (TND1) to (TND4), it is also preferable that the first cathode-side organic layer is included as at least one intermediate layer, or as an intermediate layer within at least one intermediate unit.
[0525] The first light-emitting layer and the second light-emitting layer are preferably included in at least one of the first light-emitting unit, the second light-emitting unit, and the third light-emitting unit.
[0526] The first and second light-emitting layers are preferably included in all the light-emitting units of the organic EL element.
[0527] In the above-described element configurations (TND1) to (TND4), the light-emitting unit disposed on the anode side of the intermediate layer that serves as the first cathode-side organic layer, or the light-emitting unit disposed on the anode side of the intermediate unit containing the first cathode-side organic layer, is preferably the stacked light-emitting unit according to this embodiment.
[0528] In addition to the first and second light-emitting layers, the stacked light-emitting unit of the organic EL element 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.
[0529] In the organic EL element of this embodiment, the organic layer of the stacked light-emitting unit may consist only of a first light-emitting layer and a second light-emitting layer, or may also have at least one layer selected from, for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer, and an electron blocking layer.
[0530] The region disposed on the anode side of the light-emitting layer in a light-emitting unit is sometimes called the hole transport region. The hole transport region can be a single layer or multiple layers. In addition to the hole transport layer, other layers that constitute the hole transport region include, for example, the hole injection layer and the electron blocking layer.
[0531] The region disposed on the cathode side of the light-emitting layer of a light-emitting unit is sometimes called the electron transport region. The electron transport region can be a single layer or multiple layers. In addition to the electron transport layer, other layers that constitute the electron transport region include, for example, an electron injection layer and a hole blocking layer.
[0532] The organic EL element involved in this embodiment may have a light-emitting unit having at least one light-emitting layer as a light-emitting unit other than the stacked light-emitting unit. In addition to the light-emitting layer, the light-emitting unit other than the stacked light-emitting unit may also have at least one layer selected from the group consisting of hole injection layer, hole transport layer, electron injection layer, electron transport layer, hole blocking layer and electron blocking layer as an organic layer.
[0533] In the organic EL element according to this embodiment, the two or more light-emitting units preferably include stacked light-emitting units and at least one phosphorescent light-emitting unit different from the stacked light-emitting units. Preferably, the phosphorescent light-emitting unit contains a phosphorescent compound that exhibits phosphorescence. The phosphorescent compound is preferably a metal complex. The metal complex used as the phosphorescent compound is preferably an iridium complex, a copper complex, a platinum complex, an osmium complex, or a gold complex.
[0534] The phosphorescent unit preferably has at least one phosphorescent layer containing a phosphorescent compound. The phosphorescent unit may have two or more phosphorescent layers. When the phosphorescent unit has two or more phosphorescent layers, the phosphorescent layers may be directly connected to each other or not connected.
[0535] Furthermore, the phosphorescent emitting unit preferably comprises a green phosphorescent layer containing a phosphorescent compound with green luminescence and a red phosphorescent layer containing a phosphorescent compound with red luminescence. In this specification, green luminescence refers to luminescence with a maximum peak wavelength of 500 nm or more and 550 nm or less. In this specification, red luminescence refers to luminescence with a maximum peak wavelength of 600 nm or more and 640 nm or less.
[0536] In this embodiment, the organic EL element having a phosphorescent light-emitting unit is preferably provided, and preferably has two or more stacked light-emitting units. Furthermore, the organic EL element in this embodiment is preferably provided with one stacked light-emitting unit and one phosphorescent light-emitting unit.
[0537] Furthermore, the organic EL element involved in this embodiment preferably does not contain a phosphorescent light-emitting unit.
[0538] Figure 1 In this embodiment, as an example of an organic EL element, the general structure of organic EL element 1 is shown. Organic EL element 1 is a series-connected organic EL element. Organic EL element 1 includes a substrate 2, a cathode 4, an anode 3, an intermediate unit 20 contained between the cathode 4 and the anode 3, a first light-emitting unit 11 contained between the intermediate unit 20 and the anode 3, and a second light-emitting unit 12 contained between the intermediate unit 20 and the cathode 4.
[0539] In the organic EL element 1, the first light-emitting unit 11 and the second light-emitting unit 12 are connected in series via the intermediate unit 20.
[0540] The organic EL element 1 has a first light-emitting unit 11 and a second light-emitting unit 12 as two light-emitting units. Both the first light-emitting unit 11 and the second light-emitting unit 12 in the organic EL element 1 are stacked light-emitting units according to this embodiment. Sometimes the first light-emitting unit 11 is referred to as a first stacked light-emitting unit. Sometimes the second light-emitting unit 12 is referred to as a second stacked light-emitting unit.
[0541] The first light-emitting unit 11 is constructed by stacking hole injection layer 113, hole transport layer 114, first light-emitting layer 111, second light-emitting layer 112 and electron transport layer 115 in sequence from the anode 3 side.
[0542] The second light-emitting unit 12 is constructed by stacking hole transport layer 123, first light-emitting layer 121, second light-emitting layer 122, electron transport layer 124 and electron injection layer 125 in sequence from the anode 3 side.
[0543] The intermediate unit 20 is constructed by sequentially stacking a first cathode-side organic layer 21 (sometimes referred to as the first N layer) and a first P layer 22, starting from the anode 3 side.
[0544] This invention is not limited to Figure 1 The diagram illustrates the structure of an organic EL element. Another example of an organic EL element configuration is one in which a second light-emitting layer and a first light-emitting layer are stacked sequentially from the anode side in the light-emitting unit. Furthermore, the number of light-emitting units and intermediate units is not limited. Figure 1 The organic EL element shown is configured as follows. Alternatively, a scheme in which a first cathode-side organic layer, which is not an intermediate layer, is disposed between the first light-emitting unit and the second light-emitting unit.
[0545] The organic EL element involved in this embodiment can be a bottom-emitting organic EL element. Alternatively, the organic EL element involved in this embodiment can also be a top-emitting organic EL element.
[0546] In addition, as an organic EL element having multiple light-emitting units, including stacked light-emitting units and phosphorescent light-emitting units, examples of such element configurations as (TND5) to (TND8) can be given.
[0547] (TND5) Anode / First Light-Emitting Unit (Stacked Light-Emitting Unit) / Intermediate Layer / Second Light-Emitting Unit (Phosphorescent Light-Emitting Unit) / Cathode
[0548] (TND6) Anode / First Light-Emitting Unit (Stacked Light-Emitting Unit) / Intermediate Unit / Second Light-Emitting Unit (Phosphorescent Light-Emitting Unit) / Cathode
[0549] (TND7) Anode / First Light-Emitting Unit (Stacked Light-Emitting Unit) / First Intermediate Layer / Second Light-Emitting Unit (Phosphorescent Light-Emitting Unit) / Second Intermediate Layer / Third Light-Emitting Unit (Stacked Light-Emitting Unit) / Cathode
[0550] (TND8) Anode / First Light-Emitting Unit (Stacked Light-Emitting Unit) / First Intermediate Unit / Second Light-Emitting Unit (Phosphorescent Light-Emitting Unit) / Second Intermediate Unit / Third Light-Emitting Unit (Stacked Light-Emitting Unit) / Cathode
[0551] The number of light-emitting units and intermediate layers (or intermediate units) is not limited to the examples shown in (TND5) to (TND8). Furthermore, the arrangement order of the stacked light-emitting units and phosphorescent light-emitting units is not limited to the examples shown in (TND5) to (TND8).
[0552] (Organic layer on the first cathode side)
[0553] The organic layer on the first cathode side contains phenanthroline compounds with a phenanthroline skeleton.
[0554] The organic layer on the first cathode side preferably contains phenanthroline compounds and electron-donating materials.
[0555] The electron-donating material is preferably selected from at least one of the group consisting of elemental metals, metal compounds, and metal complexes that have electron-donating properties. Specifically, the electron-donating material is preferably selected from at least one of the group consisting of alkali metals, alkali metal compounds, organometallic complexes containing alkali metals, alkaline earth metals, alkaline earth metal compounds, organometallic complexes containing alkaline earth metals, rare earth metals, rare earth metal compounds, and organometallic complexes containing rare earth metals. More preferably, it is selected from at least one of the group consisting of elemental alkali metals, alkaline earth metals, rare earth metals, rare earth metal compounds, and rare earth metal complexes. For example, the organic layer on the first cathode side also preferably contains a phenanthroline compound and a metal selected from at least one of the group consisting of Li, Yb, and Cs.
[0556] (Intermediate Unit)
[0557] The organic EL element according to this embodiment may include intermediate units between the light-emitting units. The intermediate unit includes multiple organic layers. The first cathode-side organic layer may be an organic layer constituting the intermediate unit.
[0558] In the organic EL element involved in this embodiment, it is also preferable to arrange an intermediate unit on the cathode side of at least one stacked light-emitting unit, the intermediate unit comprising a first cathode-side organic layer.
[0559] The intermediate unit preferably comprises at least one N-layer and at least one P-layer. The N-layer is configured to be closer to the anode side than the P-layer. In the organic EL element according to this embodiment, the intermediate unit preferably comprises a first cathode-side organic layer as the N-layer. The intermediate unit may also have a first N-layer configured on the anode side and a second N-layer configured closer to the cathode side than the first N-layer as multiple N-layers. The first cathode-side organic layer can be either the first N-layer or the second N-layer. If the second N-layer is the first cathode-side organic layer, it is easy to separate the first cathode-side organic layer from the first light-emitting layer.
[0560] The N-layer preferably comprises π-electron-deficient compounds and electron-donating materials. Examples of π-electron-deficient compounds include compounds capable of coordinating with metal atoms. Examples of π-electron-deficient compounds include phenanthrene-coral compounds, benzimidazole compounds, azazine compounds, and hydroxyquinoline.
[0561] The P-layer is a layer containing acceptor material. The P-layer can also be a layer doped with acceptor material (P-doped layer). The acceptor material can also be appropriately selected from the "materials with high hole injection activity" exemplified in the section on hole injection layers.
[0562] In the organic EL element involved in this embodiment, it can also be configured such that a second cathode-side organic layer is disposed between the first light-emitting layer and the first cathode-side organic layer.
[0563] For example, in the organic EL element according to this embodiment, a second light-emitting layer, a first light-emitting layer, a second cathode-side organic layer, and a first cathode-side organic layer may be sequentially provided from the anode side. As described above, when the second light-emitting layer and the first light-emitting layer are sequentially provided from the anode side, the first light-emitting layer and the first cathode-side organic layer can be separated by the second cathode-side organic layer.
[0564] Alternatively, for example, in the organic EL element according to this embodiment, a first light-emitting layer, a second light-emitting layer, a second cathode-side organic layer, and a first cathode-side organic layer may be provided sequentially from the anode side. It should be noted that when the first light-emitting layer and the second light-emitting layer are provided sequentially from the anode side, the first light-emitting layer and the first cathode-side organic layer containing the phenanthroline compound can be separated even without the second cathode-side organic layer.
[0565] In the organic EL element involved in this embodiment, the organic layer on the second cathode side preferably does not contain phenanthroline compounds having a phenanthroline skeleton.
[0566] The second cathode-side organic layer can be an N-layer that is different from the first cathode-side organic layer in the intermediate unit. For example, the second cathode-side organic layer can be a first N-layer while the first cathode-side organic layer can be a second N-layer.
[0567] In addition, the organic layer on the second cathode side can be an electron transport layer or a hole blocking layer in the light-emitting unit.
[0568] In the organic EL element of this embodiment, it is preferable that the first light-emitting layer and the first cathode-side organic layer are spaced at least 30 nm apart. It is believed that by spaced at least 30 nm apart between the first cathode-side organic layer and the first light-emitting layer, the amount of holes moving from the stacked light-emitting units to the first cathode-side organic layer can be easily suppressed, thus facilitating a longer lifetime for the organic EL element.
[0569] In the organic EL element involved in this embodiment, at least one light-emitting unit may be disposed between the organic layer on the first cathode side and the cathode.
[0570] In the organic EL element of this embodiment, a first cathode-side organic layer containing a phenanthroline compound can be disposed between a stacked light-emitting unit and another light-emitting unit different from the stacked light-emitting unit.
[0571] When an organic layer containing phenanthrene-line compounds is positioned in a location where it can easily receive electron injection from the cathode (e.g., in direct contact with the cathode or electron injection layer), the degradation caused by the injection of holes moving from the light-emitting layer is mitigated because the organic layer containing phenanthrene-line compounds can easily receive electron injection.
[0572] On the other hand, when organic layers containing phenanthroline compounds are arranged between light-emitting units and cannot obtain cathode (metal electrode)-based activity and are not easily injected with electrons, the phenanthroline compounds are prone to deterioration due to holes.
[0573] In the organic EL element of this embodiment, it is believed that even if the first cathode-side organic layer containing phenanthrene compounds is arranged between light-emitting units and does not easily accept electron injection, since the stacked light-emitting units are arranged on the anode side of the first cathode-side organic layer, the amount of holes moving from the stacked light-emitting units to the first cathode-side organic layer is suppressed, thus extending the lifetime of the organic EL element.
[0574] In the organic EL element of this embodiment, the organic layer containing phenanthroline compound may or may not be disposed in the light-emitting unit that is closest to the cathode side among the two or more light-emitting units.
[0575] (Light-emitting unit)
[0576] The organic EL element involved in this embodiment includes two or more light-emitting units. Each light-emitting unit includes a light-emitting layer. The organic EL element involved in this embodiment includes at least one stacked light-emitting unit, which, as described above, includes a first light-emitting layer and a second light-emitting layer.
[0577] The organic EL element involved in this embodiment may contain two or more stacked light-emitting units. Other light-emitting units that are not stacked light-emitting units may contain a single light-emitting layer or multiple light-emitting layers.
[0578] In the organic EL element according to this embodiment, it is also preferable that the second light-emitting layer of the stacked light-emitting unit is disposed between the first light-emitting layer and the first cathode-side organic layer. Since the second light-emitting layer is disposed between the first light-emitting layer, which is a composite layer, and the first cathode-side organic layer containing a phenanthroline compound, even if no other organic layer is disposed between the first light-emitting layer and the first cathode-side organic layer, the first light-emitting layer and the first cathode-side organic layer can be separated by the second light-emitting layer.
[0579] In the organic EL element involved in this embodiment, it is also preferable that the first light-emitting layer of the stacked light-emitting unit is disposed between the second light-emitting layer and the first cathode-side organic layer.
[0580] The organic EL element according to this embodiment may have a first light-emitting layer and a second light-emitting layer in sequence from the anode side, or it may have a second light-emitting layer and a first light-emitting layer in sequence from the anode side. In the case where the order of the first light-emitting layer and the second light-emitting layer is either one, by selecting a combination of materials that satisfy the relationship of the above mathematical formula (mathematical formula 3), it is also possible to expect the effect of the light-emitting layer being a stacked structure.
[0581] In the organic EL element according to this embodiment, when the stacking order of the first light-emitting layer and the second light-emitting layer is from the anode side to the second light-emitting layer, the hole mobility μh(H1) of the first host material and the hole mobility μh(H2) of the second host material preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 31). By satisfying the relationship of the first host material and the second host material as described in the following mathematical formula (Mathematical Formula 31), the degradation of the phenanthrene-roline compound can be further suppressed.
[0582] μh(H1)>μh(H2)...(Mathematical Equation 31)
[0583] In the organic EL element according to this embodiment, when the stacking order of the first light-emitting layer and the second light-emitting layer is from the anode side to the second light-emitting layer, the hole mobility μh(H1), electron mobility μe(H1), hole mobility μh(H2), and electron mobility μe(H2) of the first host material preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 32). By satisfying the relationship of the first host material and the second host material according to the following mathematical formula (Mathematical Formula 32), the degradation of the phenanthrene compound can be further suppressed.
[0584] (μe(H1) / μh(H1))<(μe(H2) / μh(H2))...(Mathematical Equation 32)
[0585] In the organic EL element according to this embodiment, when the stacking order of the first light-emitting layer and the second light-emitting layer is from the anode side to the second light-emitting layer, the electron mobility μe(H1) of the first host material and the electron mobility μe(H2) of the second host material preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 33). By satisfying the relationship of the first host material and the second host material as described in the following mathematical formula (Mathematical Formula 33), the recombination ability of holes and electrons in the first light-emitting layer is improved.
[0586] μe(H1)<μe(H2)...(Mathematical Equation 33)
[0587] Electron mobility can be measured by impedance measurement using a mobility evaluation element manufactured according to the steps below. The mobility evaluation element is manufactured, for example, according to the steps below.
[0588] On a glass substrate with an aluminum electrode (anode), a compound Target, which is the object of electron mobility measurement, is deposited by vapor deposition in a manner covering the aluminum electrode to form a measurement object layer. An electron transport layer is formed by vapor deposition of compound ET-A on the measurement object layer. An electron injection layer is formed by vapor deposition of LiF on the electron transport layer. A metallic cathode is formed by vapor deposition of metallic aluminum (Al) on the electron injection layer.
[0589] The components used for the above mobility evaluation are simplified as shown below.
[0590] glass / Al(50) / Target(200) / ET-A(10) / LiF(1) / Al(50)
[0591] It should be noted that the numbers in parentheses represent the film thickness (nm).
[0592]
Chemical Formula 22
[0593]
[0594] An electron mobility evaluation element is placed in an impedance measuring device for impedance measurement. The impedance measurement is performed by scanning the measurement frequency from 1 Hz to 1 MHz. At this time, a DC voltage V is applied to the element simultaneously with an AC amplitude of 0.1 V. The modulus M is calculated based on the measured impedance Z using the following formula (C1).
[0595] Formula (C1): M=jωZ
[0596] In the above calculation formula (C1), j is its imaginary unit with a square of -1, and ω is the angular frequency [rad / s].
[0597] In a Bode plot where the imaginary part of the modulus M is set as the vertical axis and the frequency [Hz] is set as the horizontal axis, the electrical time constant τ of the mobility evaluation element is calculated using the following formula (C2) based on the frequency fmax representing the peak.
[0598] Formula (C2): τ=1 / (2πfinax)
[0599] In the above calculation formula (C2), π is the symbol for the value of pi.
[0600] The electron mobility μe is calculated using the above τ according to the following formula (C3-1).
[0601] Calculation formula (C3-1): μe=d 2 / (Vτ)
[0602] In the above calculation formula (C3-1), d is the total thickness of the organic thin film constituting the element. In the case of an element used for evaluating electron mobility, d = 210 [nm].
[0603] Hole mobility can be measured by impedance measurement using a mobility evaluation element manufactured according to the steps below. The mobility evaluation element is manufactured, for example, according to the steps below.
[0604] A hole injection layer is formed by vapor deposition of compound HA-2 on a glass substrate with an ITO transparent electrode (anode) to cover the transparent electrode. A hole transport layer is formed by vapor deposition of compound HT-A on the hole injection layer. Then, a test layer is formed by vapor deposition of compound Target, which is the target for hole mobility measurement. Finally, a metal cathode is formed by vapor deposition of metallic aluminum (Al) on the test layer.
[0605] The components used for the above mobility evaluation are simplified as shown below.
[0606] ITO(130) / HA-2(5) / HT-A(10) / Target(200) / Al(80)
[0607] It should be noted that the numbers in parentheses represent the film thickness (nm).
[0608]
Chemical Formula 23
[0609]
[0610] An element for evaluating hole mobility was placed in an impedance measuring device, and impedance measurements were performed. The impedance measurement was conducted by scanning from 1 Hz to 1 MHz. At this time, a DC voltage V was applied to the element simultaneously with an AC amplitude of 0.1 V. Based on the measured impedance Z, the modulus M was calculated using the aforementioned formula (C1).
[0611] In a Bode plot where the imaginary part of the modulus M is set as the vertical axis and the frequency [Hz] is set as the horizontal axis, the electrical time constant τ of the mobility evaluation element is calculated using the above formula (C2) based on the frequency finax representing the peak.
[0612] Using τ obtained from the above formula (C2), the hole mobility μh is calculated according to the relationship of the following formula (C3-2).
[0613] Calculation formula (C3-2): μh=d 2 / (Vτ)
[0614] In the above calculation formula (C3-2), d is the total thickness of the organic thin film constituting the element. In the case of the element constituting the hole mobility evaluation, d = 215 [nm].
[0615] The electron mobility and hole mobility in this specification are the square root of the electric field strength E. 1 / 2 =500[V 1 / 2 / cm 1 / 2 The value at time []. The square root of the electric field strength E 1 / 2 It can be calculated from the following formula (C4).
[0616] Calculation formula (C4): E 1 / 2 =V 1 / 2 / d 1 / 2
[0617] The impedance measurement described above uses Solartron's Model 1260 as the impedance measuring device. For higher accuracy, Solartron's Model 1296 dielectric constant measuring interface can also be used.
[0618] 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).
[0619] T1(H1)-T1(H2)>0.03eV...(Mathematical Formula 5)
[0620] (First light-emitting layer)
[0621] 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.
[0622] The first luminescent layer comprises at least a first luminescent compound exhibiting luminescence with a maximum peak wavelength of 500 nm or less. The first luminescent compound is preferably a fluorescent luminescent compound exhibiting fluorescence with a maximum peak wavelength of 500 nm or less.
[0623] In the organic EL element involved in this embodiment, the first luminescent compound is preferably a compound that does not contain an azazine ring structure in its molecule.
[0624] In the organic EL element involved in this embodiment, the first luminescent compound is preferably not a boron-containing complex, and more preferably not a complex.
[0625] 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 also preferably does not contain boron-containing complexes.
[0626] In the organic EL element involved in this embodiment, the first light-emitting layer preferably does not contain phosphorescent materials (dopant materials).
[0627] 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.
[0628] In the emission spectrum of the first luminescent compound, when the peak with the highest emission intensity is taken as the maximum peak and the height of the 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.
[0629] Furthermore, the number of peaks in the emission spectrum of the first luminescent compound is preferably less than three.
[0630] 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.
[0631] The maximum peak wavelength of light emitted by the light-emitting layer when the element is driven can be determined using the method described below.
[0632] • The maximum peak wavelength λp of light emitted from the light-emitting layer when the element is driven.
[0633] For the maximum peak wavelength λp1 of the light emitted from the first emissive layer during device driving, the second emissive layer is made of the same material as the first 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 spectroradiometer CS-2000 (manufactured by Konica Minolta Co., Ltd.). 2 The spectroscopic emission spectrum at that time was obtained. The maximum peak wavelength λp1 (unit: nm) was calculated based on the obtained spectroscopic emission spectrum.
[0634] 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. A spectroradiometer CS-2000 (manufactured by Konica Minolta Co., Ltd.) was used to measure the applied voltage to the device, resulting in a current density of 10 mA / cm² for the organic EL device. 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.
[0635] 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 luminescent compound preferably satisfy the following mathematical formula (Mathematical Formula 20).
[0636] S1(H1)>S1(D1)...(Mathematical Expression 20)
[0637] The singlet energy S1 refers to the energy difference between the lowest excited singlet state and the ground state.
[0638] The first host material and the first luminescent compound satisfy the relationship of mathematical formula (Mathematical Formula 20), thereby making it easier for singlet excitons generated on the first host material to undergo energy transfer from the first host material to the first luminescent compound, which contributes to the fluorescence of the first luminescent compound.
[0639] 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 luminescent compound preferably satisfy the following mathematical formula (mathematical formula 20A).
[0640] T1(D1)>T1(H1)...(Mathematical expression 20A)
[0641] The first host material and the first luminescent compound satisfy a mathematical formula (Formula 20A), so that the triplet excitons generated in the first luminescent layer do not move in the first luminescent compound with higher triplet energy but in the first host material, and thus can easily move to the second luminescent layer.
[0642] The organic EL element involved in this embodiment preferably satisfies the following mathematical formula (mathematical formula 20B).
[0643] T1(D1)>T1(H1)>T1(H2)...(Mathematical expression 20B)
[0644] In the organic EL element according to this embodiment, the content of the first luminescent compound in the first luminescent layer is preferably more than 1.1% by mass. That is, the content of the first luminescent compound in the first luminescent layer is preferably more than 1.1% by mass of the total mass of the first luminescent layer, more preferably 1.2% by mass or more of the total mass of the first luminescent layer, and even more preferably 1.5% by mass or more of the total mass of the first luminescent layer.
[0645] In the first luminescent layer, the content of the first luminescent compound is preferably 10% or less of the total mass of the first luminescent layer, more preferably 7% or less of the total mass of the first luminescent layer, and even more preferably 5% or less of the total mass of the first luminescent layer.
[0646] 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.
[0647] 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.
[0648] Wherein, when the first light-emitting layer contains a first host material and a first luminescent compound, the upper limit of the total content of the first host material and the first luminescent compound is 100% by mass.
[0649] It should be noted that this embodiment does not exclude the inclusion of materials other than the first host material and the first luminescent compound in the first luminescent layer.
[0650] In the first luminescent layer, the first host material may contain only one type or two or more types. In the first luminescent layer, the first luminescent compound may contain only one type or two or more types.
[0651] In the organic EL device according to this embodiment, the thickness of the first light-emitting layer is preferably 3 nm or more, and more preferably 5 nm or more. If the thickness of the first light-emitting layer is 3 nm or more, it is sufficient to induce recombination of holes and electrons in the first light-emitting layer.
[0652] In the organic EL device of this embodiment, the thickness of the first light-emitting layer is preferably 15 nm or less, more preferably 10 nm or less. If the thickness of the first light-emitting layer is 15 nm or less, it is thin enough to allow triplet excitons to migrate to the second light-emitting layer.
[0653] In the organic EL element involved in this embodiment, the thickness of the first light-emitting layer is more preferably 3 nm or more and 15 nm or less.
[0654] (Second light-emitting layer)
[0655] The second light-emitting layer contains a second host material. The second host material is a compound different from the first host material contained in the first light-emitting layer.
[0656] The second luminescent layer comprises at least a second luminescent compound exhibiting luminescence with a maximum peak wavelength of less than 500 nm. The second luminescent compound is preferably a fluorescent luminescent compound exhibiting fluorescence with a maximum peak wavelength of less than 500 nm.
[0657] The method for determining the maximum peak wavelength of the compound is as described above.
[0658] In the organic EL element involved in this embodiment, the second light-emitting layer preferably emits light with a maximum peak wavelength of less than 500 nm when the element is driven.
[0659] In the organic EL element involved in this embodiment, the full width at half maximum (FWHM) of the maximum peak of the second luminescent compound is preferably 1 nm or more and 20 nm or less.
[0660] In the organic EL element involved in this embodiment, the Stokes shift of the second luminescent compound is preferably greater than 7 nm.
[0661] If the Stokes shift of the second luminescent compound exceeds 7 nm, it is easy to prevent the decrease in luminescence efficiency due to self-absorption.
[0662] Self-absorption refers to the phenomenon where a compound absorbs the light it emits, leading to a decrease in luminescence efficiency. Since significant self-absorption has been observed in compounds with small Stokes shifts (i.e., large overlap between absorption and fluorescence spectra), compounds with large Stokes shifts (small overlap between absorption and fluorescence spectra) are preferred for suppressing self-absorption. Stokes shifts can be determined using the methods described below.
[0663] The compounds to be measured were 2.0 × 10⁻⁶. -5The sample for assay is prepared by dissolving it in toluene at a concentration of mol / L. The sample, added to a quartz cuvette, is irradiated with continuous light in the ultraviolet-visible region at room temperature (300 K), and the absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength) is measured. Absorption spectroscopy can be performed using a spectrophotometer, such as the Hitachi High-Tech U-3900 / 3900H spectrophotometer. Additionally, the compound to be measured is precipitated at 4.9 × 10⁻⁶ mol / L. - 6 The sample for assay is prepared by dissolving it in toluene at a concentration of mol / L. The sample, added to a quartz cuvette, is irradiated with excitation light at room temperature (300K), and the fluorescence spectrum (vertical axis: fluorescence intensity, horizontal axis: wavelength) is measured. Fluorescence spectroscopy can be performed using a spectrophotometer, such as the Hitachi Advanced Scientific & Technical Co., Ltd. F-7000 spectrophotometer.
[0664] Based on these absorption and fluorescence spectra, the difference between the absorption maximum wavelength and the fluorescence maximum wavelength is calculated, and the Stokes shift (SS) is determined. The unit of the Stokes shift SS is nm.
[0665] In the organic EL element of this embodiment, the triplet energy T1(D2) of the second luminescent compound and the triplet energy T1(H2) of the second host material preferably satisfy the following mathematical formula (Mathematical Formula 3A).
[0666] T1(D2)>T1(H2)...(Mathematical expression 3A)
[0667] In the organic EL element according to this embodiment, the second luminescent compound and the second host material satisfy the relationship described above (Mathematical Formula 3A). Therefore, when triplet excitons generated in the first luminescent layer move towards the second luminescent layer, they undergo energy transfer towards the molecules of the second host material instead of towards the second luminescent compound, which has a higher triplet energy. Furthermore, triplet excitons generated by the recombination of holes and electrons on the second host material do not move towards the second luminescent compound, which has a higher triplet energy. Triplett excitons generated by recombination on the molecules of the second luminescent compound rapidly undergo energy transfer towards the molecules of the second host material.
[0668] Instead of moving to the second luminescent compound, triplet excitons in the second host material effectively collide with each other on the second host material via the TTF phenomenon, thereby generating singlet excitons.
[0669] In the organic EL element of this embodiment, the singlet energy S1(H2) of the second host material and the singlet energy S1(D2) of the second luminescent compound preferably satisfy the following mathematical formula (Mathematical Formula 4).
[0670] S1(H2)>S1(D2)...(Mathematical Expression 4)
[0671] In the organic EL element of this embodiment, the second luminescent compound and the second host material satisfy the above mathematical formula (Mathematical Formula 4). Since the singlet energy of the second luminescent compound is lower than that of the second host material, the singlet excitons generated by the TTF phenomenon carry out energy transfer from the second host material to the second luminescent compound, which helps the second luminescent compound to emit fluorescence.
[0672] In the organic EL element involved in this embodiment, the second luminescent compound is preferably a compound whose molecule does not contain an azazine ring structure.
[0673] In the organic EL element involved in this embodiment, the second luminescent compound is preferably not a boron-containing complex, and more preferably not a complex.
[0674] In the organic EL element according to this embodiment, the second light-emitting layer preferably does not contain metal complexes. Furthermore, in the organic EL element according to this embodiment, the second light-emitting layer also preferably does not contain boron-containing complexes.
[0675] In the organic EL element involved in this embodiment, the second light-emitting layer preferably does not contain phosphorescent materials (dopant materials).
[0676] 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.
[0677] In the organic EL element according to this embodiment, the content of the second luminescent compound in the second luminescent layer is preferably more than 1.1% by mass. That is, the content of the second luminescent compound in the second luminescent layer is preferably greater than 1.1% by mass of the total mass of the second luminescent layer, more preferably 1.2% by mass or more of the total mass of the second luminescent layer, and even more preferably 1.5% by mass or more of the total mass of the second luminescent layer.
[0678] In the second luminescent layer, the content of the second luminescent compound is preferably 10% or less of the total mass of the second luminescent layer, more preferably 7% or less of the total mass of the second luminescent layer, and even more preferably 5% or less of the total mass of the second luminescent layer.
[0679] In the second light-emitting layer, the content of the second compound, which is the second main material, is preferably 60% or more of the total mass of the second light-emitting layer, more preferably 70% or more of the total mass of the second light-emitting layer, even more preferably 80% or more of the total mass of the second light-emitting layer, even more preferably 90% or more of the total mass of the second light-emitting layer, and even more preferably 95% or more of the total mass of the second light-emitting layer.
[0680] In the second light-emitting layer, the content of the second host material is preferably less than 99% by mass of the total mass of the second light-emitting layer.
[0681] When the second luminescent layer contains a second host material and a second luminescent compound, the upper limit of the total content of the second host material and the second luminescent compound is 100% by mass.
[0682] It should be noted that this embodiment does not exclude the inclusion of materials other than the second host material and the second luminescent compound in the second luminescent layer.
[0683] In the second luminescent layer, the second host material may contain only one type or more types. Similarly, the second luminescent compound in the second luminescent layer may contain only one type or more types.
[0684] In the organic EL element according to this embodiment, the thickness of the second light-emitting layer is preferably 5 nm or more, and more preferably 15 nm or more. If the thickness of the second light-emitting layer is 5 nm or more, it is easy to suppress the return of triplet excitons that have migrated from the first light-emitting layer to the second light-emitting layer to the first light-emitting layer. In addition, if the thickness of the second light-emitting layer is 5 nm or more, it is possible to sufficiently separate the triplet excitons from the recombination portion in the first light-emitting layer.
[0685] In the organic EL element of this embodiment, the thickness of the second light-emitting layer is preferably 25 nm or less, more preferably 20 nm or less. If the thickness of the second light-emitting layer is 25 nm or less, the density of triplet excitons in the second light-emitting layer can be increased, thereby making it easier to induce the TTF phenomenon.
[0686] In the organic EL element involved in this embodiment, the thickness of the second light-emitting layer is preferably 5 nm or more and 25 nm or less.
[0687] In the organic EL element of this embodiment, the triplet energy T1(DX) of the first luminescent compound or the second luminescent compound, 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 10).
[0688] 2.6eV>T1(DX)>T1(H1)>T1(H2)...(Mathematical Equation 10)
[0689] The triplet energy T1(D1) of the first luminescent compound preferably satisfies the following mathematical formula (Formula 10A).
[0690] 2.6eV>T1(D1)>T1(H1)>T1(H2)...(Mathematical expression 10A)
[0691] The triplet energy T1(D2) of the second luminescent compound preferably satisfies the following mathematical formula (Formula 10B).
[0692] 2.6eV>T1(D2)>T1(H1)>T1(H2)...(Mathematical formula 10B)
[0693] In the organic EL element of this embodiment, the triplet energy T1(DX) of the first luminescent compound or the second luminescent compound and the triplet energy T1(H1) of the first host material preferably satisfy the following mathematical formula (Mathematical Formula 11).
[0694] 0 eV < T1(DX) - T1(H1) < 0.6 eV... (Mathematical Equation 11)
[0695] The triplet energy T1(D1) of the first luminescent compound preferably satisfies the following mathematical formula (Formula 11A).
[0696] 0 eV < T1(D1) - T1(H1) < 0.6 eV... (Mathematical formula 11A)
[0697] The triplet energy T1(D2) of the second luminescent compound preferably satisfies the following mathematical formula (Formula 11B).
[0698] 0 eV < T1(D2) - T1(H2) < 0.8 eV... (Mathematical expression 11B)
[0699] In the organic EL element of this embodiment, the triplet energy T1(H1) of the first host material preferably satisfies the following mathematical formula (Mathematical Formula 12).
[0700] T1(H1)>2.0eV...(Mathematical Equation 12)
[0701] In the organic EL element of this embodiment, the triplet energy T1(H1) of the first host material preferably satisfies the following mathematical formula (mathematical formula 12A) and preferably satisfies the following mathematical formula (mathematical formula 12B).
[0702] T1(H1)>2.10eV...(Mathematical expression 12A)
[0703] T1(H1)>2.15eV...(Mathematical expression 12B)
[0704] In the organic EL element according to this embodiment, the triplet energy T1(H1) of the first host material satisfies the relationship of the above-described mathematical formula (Formula 12A) or the above-described mathematical formula (Formula 12B). As a result, triplet excitons generated in the first emissive layer easily migrate to the second emissive layer, and their reverse migration from the second emissive layer to the first emissive layer is easily suppressed. Consequently, singlet excitons are efficiently generated in the second emissive layer, improving luminescence efficiency.
[0705] In the organic EL element of this embodiment, the triplet energy T1(H1) of the first host material preferably satisfies the following mathematical formula (mathematical formula 12C) and preferably satisfies the following mathematical formula (mathematical formula 12D).
[0706] 2.08 eV > T1(H1) > 1.87 eV... (Mathematical formula 12C)
[0707] 2.05 eV > T1(H1) > 1.90 eV... (Mathematical formula 12D)
[0708] In the organic EL element involved in this embodiment, the triplet exciton generated in the first light-emitting layer has a smaller energy because the triplet energy T1(H1) of the first host material satisfies the relationship of the above mathematical formula (mathematical formula 12C) or the above mathematical formula (mathematical formula 12D), and the long lifetime of the organic EL element can be expected.
[0709] In the organic EL element of this embodiment, the triplet energy T1(D1) of the first luminescent compound preferably satisfies the following mathematical formula (mathematical formula 14A) and preferably satisfies the following mathematical formula (mathematical formula 14B).
[0710] 2.60 eV > T1(D1)...(Mathematical expression 14A)
[0711] 2.50 eV > T1(D1)...(Mathematical expression 14B)
[0712] The first light-emitting layer contains a first light-emitting compound that satisfies the relationship described above (Formula 14A) or (Formula 14B), thereby extending the lifetime of the organic EL element.
[0713] In the organic EL element of this embodiment, the triplet energy T1(D2) of the second luminescent compound preferably satisfies the following mathematical formula (mathematical formula 14C) and preferably satisfies the following mathematical formula (mathematical formula 14D).
[0714] 2.60 eV > T1(D2)...(Mathematical expression 14C)
[0715] 2.50 eV > T1(D2)...(Mathematical expression 14D)
[0716] By having a second light-emitting layer containing compounds that satisfy the above mathematical formula (Formula 14C) or (Formula 14D), the organic EL element has a longer lifetime.
[0717] In the organic EL element of this embodiment, the triplet energy T1(H2) of the second host material preferably satisfies the following mathematical formula (Mathematical Formula 13).
[0718] T1(H2)≥1.9eV...(Mathematical Equation 13)
[0719] (Third luminescent layer)
[0720] The organic EL element involved in this embodiment may further include a third light-emitting layer.
[0721] The third luminescent layer preferably comprises a third host material, the first host material is different from the second host material and the third host material, the third luminescent layer comprises at least a third luminescent compound that exhibits luminescence with a maximum peak wavelength of less than 500 nm, the first luminescent compound is the same as or different from the second luminescent compound and the third luminescent compound, and the triplet energy T1(H1) of the first host material and the triplet energy T1(H3) of the third host material satisfy the following mathematical formula (Mathematical Formula 1A).
[0722] T1(H1)>T1(H3)...(Mathematical Expression 1A)
[0723] In the case where the organic EL element of this embodiment includes a third light-emitting layer, the triplet energy T1(H2) of the second host material and the triplet energy T1(H3) of the third host material preferably satisfy the following mathematical formula (Mathematical Formula 1B).
[0724] T1(H2)>T1(H3)...(Mathematical Expression 1B)
[0725] In the organic EL element involved in this embodiment, it is preferable that the first light-emitting layer and the second light-emitting layer are directly connected.
[0726] In this specification, the layer structure in which "the first light-emitting layer and the second light-emitting layer are directly connected" may also include any of the following schemes (LS1), (LS2) and (LS3).
[0727] (LS1) A scheme in which a region is formed where the first host material and the second host material coexist during the vapor deposition process of the compound involved in the first light-emitting layer and the vapor deposition process of the compound involved in the second light-emitting layer, and the region exists at the interface between the first light-emitting layer and the second light-emitting layer.
[0728] (LS2) In the case where the first light-emitting layer and the second light-emitting layer contain luminescent compounds, a region in which the first host material, the second host material and the luminescent compound coexist is generated during the vapor deposition process of the compound involved in the first light-emitting layer and the vapor deposition process of the compound involved in the second light-emitting layer, and the region exists at the interface between the first light-emitting layer and the second light-emitting layer.
[0729] (LS3) In the case where the first light-emitting layer and the second light-emitting layer contain a luminescent compound, a region formed by the luminescent compound, a region formed by the first host material, or a region formed by the second host material is generated during the vapor deposition process of the compound involved in the first light-emitting layer and the vapor deposition process of the compound involved in the second light-emitting layer, and the region exists at the interface between the first light-emitting layer and the second light-emitting layer.
[0730] In this embodiment, when the organic EL element includes a third light-emitting layer, it is preferable that the first light-emitting layer and the second light-emitting layer are directly connected, and the second light-emitting layer and the third light-emitting layer are directly connected.
[0731] In this specification, the layer structure in which "the second light-emitting layer is directly connected to the third light-emitting layer" may also include any of the following schemes (LS4), (LS5) and (LS6).
[0732] (LS4) A scheme in which a region is formed where the second host material and the third host material coexist during the vapor deposition process of the compound involved in the second light-emitting layer and the vapor deposition process of the compound involved in the third light-emitting layer, and the region exists at the interface between the second light-emitting layer and the third light-emitting layer.
[0733] (LS5) In the case where the second and third light-emitting layers contain luminescent compounds, a region in which the second host material, the third host material, and the luminescent compound coexist during the vapor deposition process of the compound involved in the second light-emitting layer and the vapor deposition process of the compound involved in the third light-emitting layer is generated, and this region exists at the interface between the second and third light-emitting layers.
[0734] (LS6) In the case where the second and third light-emitting layers contain luminescent compounds, a region formed by the luminescent compound, a region formed by the second host material, or a region formed by the third host material is generated during the vapor deposition process of the compound involved in the second light-emitting layer and the vapor deposition process of the compound involved in the third light-emitting layer, and the region exists at the interface between the second and third light-emitting layers.
[0735] For example, in the organic EL element according to this embodiment, the first light-emitting layer containing the first compound shown in the above general formula (1) as the first host material and the second light-emitting layer containing the second compound shown in the above general formula (2) as the second host material can be directly connected. By stacking the first light-emitting layer and the second light-emitting layer in this way, the generated singlet and triplet excitons can also be effectively utilized, resulting in an improvement in the luminous efficiency of the organic EL element.
[0736] (Layer that does not contain luminescent compounds)
[0737] In addition, the stacked light-emitting unit of the organic EL element according to this embodiment preferably also has a layer (sometimes called a spacer layer) disposed between the organic layers and not containing light-emitting compounds.
[0738] In this embodiment, when the stacked light-emitting unit of the organic EL element has a layer (interlayer) that does not contain a light-emitting compound, it is preferable that the layer (interlayer) that does not contain a light-emitting compound is disposed between the first light-emitting layer and the second light-emitting layer.
[0739] The interlayer preferably does not contain metal atoms.
[0740] The interlayer contains organic materials. Preferably, the organic materials contained in the interlayer are not luminescent compounds.
[0741] Examples of organic materials that can be included in the interlayer include: 1) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives; 2) carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or... 3) Aromatic amine compounds such as derivatives, fused aromatic compounds, triarylamine derivatives, or fused polycyclic aromatic amine derivatives.
[0742] The organic material contained in the interlayer can be one of the first host material contained in the first light-emitting layer and the second host material contained in the second light-emitting layer, or both of these host materials.
[0743] When the interlayer contains multiple organic materials, the content of each organic material is preferably 10% or more of the total mass of the interlayer.
[0744] In the interlayer, the content of the aforementioned organic material is preferably 60% or more of the total mass of the interlayer, more preferably 70% or more of the total mass of the interlayer, even more preferably 80% or more of the total mass of the interlayer, even more preferably 90% or more of the total mass of the interlayer, and even more preferably 95% or more of the total mass of the interlayer.
[0745] The interlayer may contain only one type of organic material or more than two types.
[0746] When the interlayer contains two or more organic materials, the maximum total content of the two or more organic materials is 100% by mass.
[0747] It should be noted that this embodiment does not exclude the inclusion of materials other than the organic materials mentioned above in the interlayer.
[0748] The interlayer can be a single layer or two or more layers stacked together.
[0749] There are no particular restrictions on the thickness of the interlayer, but it is preferred that each layer is 3nm or more and 15nm or less, and more preferably 5nm or more and 10nm or less.
[0750] In both the first and second compounds, groups described as "substituted or unsubstituted" are preferably "unsubstituted".
[0751] In this specification, "main 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.
[0752] (Phenanthroline compounds)
[0753] The phenanthrene-rhein compound is preferably a compound having at least one group represented by the following general formula (21) and represented by the following general formula (20).
[0754] [Chemical Formula 24]
[0755]
[0756] (In the above general formula (20),
[0757] X 21 ~X 28 Each independently consists of a nitrogen atom and CR. 21 Or carbon atoms bonded to the groups shown in the above general formula (21),
[0758] X 21 ~X 28 At least one of them is a carbon atom bonded to the group shown in the above general formula (21).
[0759] When there are multiple groups represented by the above general formula (21), the multiple groups represented by the above general formula (21) may be the same as or different from each other.
[0760] Multiple R 21 One or more of the groups consisting of two or more adjacent elements.
[0761] They bond together to form substituted or unsubstituted monocyclic rings.
[0762] They bond together to form substituted or unsubstituted fused rings, or
[0763] They do not bond with each other.
[0764] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 21 Each independently
[0765] hydrogen atom,
[0766] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0767] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[0768] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[0769] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[0770] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0771] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[0772] -O-(R 904 The groups shown in the figure,
[0773] -S-(R 905 The groups shown in the figure,
[0774] -N(R 906 (R) 907 The groups shown in the figure,
[0775] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[0776] -C(=O)R 931 The groups shown
[0777] -COOR 932 The groups shown
[0778] -S(=O)2R 933 The groups shown
[0779] -B(R 934 (R) 935 The groups shown in the figure,
[0780] -P(=O)(R 936 (R) 937 The groups shown in the figure,
[0781] Halogen atoms,
[0782] cyano,
[0783] Nitro,
[0784] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0785] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[0786] (In the above general formula (21),
[0787] Ar2 is
[0788] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0789] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0790] p is 1, 2, 3, 4 or 5.
[0791] When there are two or more Ar2 atoms, the two or more Ar2 atoms are either the same or different from each other.
[0792] L2 is a single bond or a linking group.
[0793] L2, as a linking group, is
[0794] Substituted or unsubstituted linear, branched, or cyclic polyvalent aliphatic hydrocarbon groups with 1 to 50 carbon atoms.
[0795] Substituted or unsubstituted polyvalent aromatic hydrocarbon groups with 6 to 50 carbon atoms,
[0796] Substituted or unsubstituted polyvalent heterocyclic groups with 5 to 50 cyclic atoms, or
[0797] A multivalent, multi-linked group formed by bonding two or three groups selected from the above-mentioned polyvalent aromatic hydrocarbon cyclic groups and polyvalent heterocyclic groups.
[0798] The aromatic hydrocarbon cyclic groups and heterocyclic groups constituting the aforementioned multiple linking groups may be the same or different from each other; adjacent groups may be bonded to each other to form a ring, or they may not be bonded to each other.
[0799] Ar2 may bond with L2, which acts as a linking group, to form a ring, or they may not bond with each other.
[0800] L2, acting as a linking group, is adjacent to the carbon atom bonded to L2. 21 ~X 28 any one of the carbon atoms or CR 21 R 21 They may bond together to form a ring, or they may not bond together.
[0801] In the above general formula (21), * indicates the bonding position with the ring shown in the above general formula (20).
[0802] (In the above phenanthroline compounds, R) 901 R 902 R 903 R 904 R 905 R 906 R 907 R 931 R 932 R 933 R 934 R 935 R 936 and R 937 Each independently
[0803] hydrogen atom,
[0804] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[0805] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[0806] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[0807] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[0808] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[0809] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[0810] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[0811] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[0812] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.
[0813] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[0814] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.
[0815] In R 931 In the case of multiple Rs, multiple Rs 931 They are the same or different.
[0816] In R 932 In the case of multiple Rs, multiple Rs 932 They are the same or different.
[0817] In R 933 In the case of multiple Rs, multiple Rs 933 They are the same or different.
[0818] In R 934 In the case of multiple Rs, multiple Rs 934 They are the same or different.
[0819] In R 935 In the case of multiple Rs, multiple Rs 935 They are the same or different.
[0820] In R 936 In the case of multiple Rs, multiple Rs 936 They are the same or different.
[0821] In R 937 In the case of multiple Rs, multiple Rs 937 (They may be the same or different.)
[0822] In this specification, -O-(R 904 The group shown in R 904 In the case of hydrogen atoms, it is a hydroxyl group.
[0823] In this specification, -S-(R 905 The group shown in R 905In the case of hydrogen atoms, it is a thiol group.
[0824] In this specification, -S(=O)2R 933 The groups shown are in R 933 In the case of a substituent, it is a substituted sulfonyl group.
[0825] In this specification, -B(R) 934 (R) 935 The group shown in R 934 and R 935 In the case of a substituent, it is a substituted methylborane.
[0826] In this specification, -P(=O)(R 936 (R) 937 The group shown in R 936 and R 937 In the case of substituents, for the substitution of phosphine oxide group, in R 936 and R 937 In the case of an aryl group, it is an arylphosphoyl group.
[0827] Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted linear, branched, or cyclic polyvalent aliphatic hydrocarbon group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[0828] Unless otherwise stated in this specification, the number of carbon atoms in the ring of the "unsubstituted polyvalent aromatic hydrocarbon group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.
[0829] Unless otherwise stated in this specification, the number of cyclic atoms in the "unsubstituted polyvalent heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.
[0830] The heterocyclic group with 5 to 50 cyclic atoms in Ar2 of the above general formula (21) preferably includes substituted or unsubstituted groups derived from the ring structure shown in the above general formula (20).
[0831] X of the above general formula (20) is also preferred. 21 and X 28 The carbon atom is bonded to the group shown in the above general formula (21).
[0832] X of the above general formula (20) is also preferred. 21 and X 28 One of them is a carbon atom bonded to the group shown in the above general formula (21), X 21 and X 28 The other one is a carbon atom bonded to a hydrogen atom.
[0833] X in the above general formula (20) 21 ~X 28 Each is independently preferred to be CR 21 Or carbon atoms bonded to the groups shown in the above general formula (21).
[0834] X of the above general formula (20) is preferred. 21 ~X 28 Except for the carbon atoms bonded to the groups shown in the above general formula (21), all other carbon atoms are CR. 21 That is, the compound represented by the above general formula (20) is preferably a 1,10-phenanthroline derivative.
[0835] It is also preferred that Ar2 in the above general formula (21) is a substituted or unsubstituted fused aromatic hydrocarbon group with 8 to 20 carbon atoms.
[0836] The fused aromatic hydrocarbon group having 8 to 20 carbon atoms is preferably selected from naphthalene, anthracene, benzo[e]acenaphthene, acethracene, benzo[e]anthracene, triphenylene, pyrene, etc. A group derived from any of the aromatic hydrocarbons in the group consisting of tetraphenyl, fluorene, phenanthrene, fluoranthene, and benzofluoranthene.
[0837] Ar2 in the above general formula (21) is preferably substituted or unsubstituted anthracene group.
[0838] Ar2 in the above general formula (21) is preferably a heterocyclic group with 5 to 40 cyclic carbons, either substituted or unsubstituted.
[0839] Ar2 in the above general formula (21) is preferably a substituted or unsubstituted group derived from the ring structure shown in the above general formula (20).
[0840] Ar2 in the above general formula (21) is also preferably the group shown in the following general formula (23).
[0841] [Chemical Formula 25]
[0842]
[0843] (In the above general formula (23),
[0844] X 21 ~X 28 Each independently consists of a nitrogen atom and CR. 21 , and the group or L shown in the above general formula (21) 22 or L 23 Bonded carbon atoms,
[0845] L 21 As a linking group, L is used as a linking group. 21The trivalent aliphatic hydrocarbon group consisting of substituted or unsubstituted carbon atoms in the form of straight chains, branches, or rings with 1 to 50 carbon atoms; a trivalent aromatic hydrocarbon group consisting of substituted or unsubstituted cyclic carbon atoms with 6 to 50 carbon atoms; or a trivalent heterocyclic group consisting of substituted or unsubstituted cyclic carbon atoms with 5 to 50 carbon atoms.
[0846] L 22 and L 23 Each can be an independent single bond or a linking group, with L acting as a linking group. 22 and L 23 Each group can be independently a substituted or unsubstituted linear, branched, or cyclic divalent aliphatic hydrocarbon group with 1 to 50 carbon atoms; a substituted or unsubstituted cyclic aryl group with 6 to 50 carbon atoms; or a substituted or unsubstituted cyclic heterocyclic group with 5 to 50 carbon atoms.
[0847] In the general formula of phenanthrene compounds,
[0848] In X 21 In the case of multiple X, multiple X 21 They are the same or different.
[0849] In X 22 In the case of multiple X, multiple X 22 They are the same or different.
[0850] In X 23 In the case of multiple X, multiple X 23 They are the same or different.
[0851] In X 24 In the case of multiple X, multiple X 24 They are the same or different.
[0852] In X 25 In the case of multiple X, multiple X 25 They are the same or different.
[0853] In X 26 In the case of multiple X, multiple X 26 They are the same or different.
[0854] In X 27 In the case of multiple X, multiple X 27 They are the same or different.
[0855] In X 28 In the case of multiple X, multiple X 28 They are the same or different.
[0856] X in the above general formula (23) 21 ~X 28 Each is independently preferred to have nitrogen atoms and CR21 Or with L 22 or L 23 The bonded carbon atoms are more preferably CR 21 Or with L 22 or L 23 Bonded carbon atoms.
[0857] The phenanthrene-rhein compounds are also preferably those represented by the following general formula (24).
[0858]
Chemical Formula 26
[0859]
[0860] (In the above general formula (24),
[0861] Multiple R 21 Each independently relates to R in the above general formula (20) 21 Same meaning
[0862] Multiple R 22 Each independently relates to R in the above general formula (20) 21 Same meaning
[0863] L2 has the same meaning as L2 in the above general formula (21).
[0864] p is 1, 2, 3, 4 or 5.
[0865] Multiple R 22 (A carbon atom from position 1 to position 10 of the anthracene ring that is bonded to L2.)
[0866] The phenanthrene-rhein compounds are also preferably those represented by the following general formula (24A).
[0867] [Chemical Formula 27]
[0868]
[0869] (In the above general formula (24A),
[0870] Multiple R 21 Each independently relates to R in the above general formula (20) 21 Same meaning
[0871] Multiple R 22 Each independently relates to R in the above general formula (20) 21 Same meaning
[0872] L2 has the same meaning as L2 in the above general formula (21).
[0873] The phenanthrene-rhein compounds are also preferably those represented by the following general formula (24B).
[0874] [Chemical Formula 28]
[0875]
[0876] (In the above general formula (24B),
[0877] Multiple R 21 Each independently relates to R in the above general formula (20) 21 Same meaning
[0878] Multiple R 22 Each independently relates to R in the above general formula (20) 21 Same meaning
[0879] L2 has the same meaning as L2 in the above general formula (21).
[0880] The phenanthrene-rhein compounds are also preferably those represented by the following general formula (25).
[0881] [Chemical Formula 29]
[0882]
[0883] (In the above general formula (25),
[0884] Multiple R 21 Each independently relates to R in the above general formula (20) 21 Same meaning
[0885] Multiple R 22 Each independently relates to R in the above general formula (20) 21 Same meaning
[0886] L2 has the same meaning as L2 in the above general formula (21).
[0887] p is 1, 2, 3, 4 or 5.
[0888] Multiple R 22 (A carbon atom from position 2 to position 9 of the phenanthroline ring that is bonded to L2.)
[0889] The phenanthrene-rhein compounds are also preferably those represented by the following general formula (25A).
[0890]
Chemical Formula 30
[0891]
[0892] (In the above general formula (25A),
[0893] Multiple R 21 Each independently relates to R in the above general formula (20)21 Same meaning
[0894] Multiple R 22 Each independently relates to R in the above general formula (20) 21 Same meaning
[0895] L2 has the same meaning as L2 in the above general formula (21).
[0896] L2 in the above general formulas (24), (24A), (24B), (25) and (25A) is preferably a single bond, a substituted or unsubstituted aryl group with 6 to 50 cyclic carbon atoms, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 cyclic atoms.
[0897] The phenanthrene-rhein compounds are also preferably those represented by the following general formula (25B).
[0898]
Chemical Formula 31
[0899]
[0900] (In the above general formula (25B),
[0901] Multiple R 21 Each independently relates to R in the above general formula (20) 21 Same meaning
[0902] Multiple R 22 Each independently relates to R in the above general formula (20) 21 Same meaning
[0903] L3 is a linking group; L3 as a linking group is
[0904] Substituted or unsubstituted linear, branched, or cyclic polyvalent aliphatic hydrocarbon groups with 1 to 50 carbon atoms.
[0905] Substituted or unsubstituted polyvalent amino groups
[0906] Substituted or unsubstituted cyclic groups of polyvalent aromatic hydrocarbons with 6 to 50 carbon atoms,
[0907] Substituted or unsubstituted polyvalent heterocyclic groups with 5 to 50 cyclic atoms, or
[0908] A multivalent, multi-linked group formed by bonding two or three groups selected from the above-mentioned polyvalent aromatic hydrocarbon cyclic groups and polyvalent heterocyclic groups.
[0909] The aromatic hydrocarbon cyclic group and the heterocyclic group constituting L3, which are multiple linking groups, may be the same as or different from each other. Adjacent groups may be bonded to each other to form a ring or may not be bonded to each other.
[0910] p is 1, 2, 3, 4 or 5.
[0911] Multiple R 22 (A carbon atom from position 1 to position 10 of the phenanthrene ring that is bonded to the L3 group.)
[0912] The phenanthrene-rhein compounds are also preferably those represented by the following general formula (25C).
[0913]
Chemical Formula 32
[0914]
[0915] (In the above general formula (25C),
[0916] Multiple R 21 Each independently relates to R in the above general formula (20) 21 Same meaning
[0917] R 221 ~R 230 Among them, one is a single bond bonded to L3, and the other is an R bond bonded to L3. 221 ~R 230 Each independently relates to R in the above general formula (20) 21 Same meaning
[0918] L3 is a linking group, and the meaning of L3 as a linking group is the same as that of L3 as a linking group in the above general formula (25B).
[0919] p is 1, 2, 3, 4, or 5.
[0920] Phenanthroline compounds are also preferably compounds represented by the following general formula (25D).
[0921]
Chemical Formula 33
[0922]
[0923] (In the above general formula (25D),
[0924] Multiple R 21 Each independently relates to R in the above general formula (20) 21 Same meaning
[0925] R 221 ~R 232 Among them, one is a single bond bonded to L3, and the other is an R bond bonded to L3. 221 ~R 232 Each independently relates to R in the above general formula (20) 21 Same meaning
[0926] L3 is a linking group, and the meaning of L3 as a linking group is the same as that of L3 as a linking group in the above general formula (25B).
[0927] p is 1, 2, 3, 4, or 5.
[0928] The phenanthrene-rhein compounds are also preferably those represented by the following general formula (25E).
[0929] [Chemical Formula 34]
[0930]
[0931] (In the above general formula (25E),
[0932] Multiple R 21 Each independently relates to R in the above general formula (20) 21 Same meaning
[0933] R 221 ~R 230 Among them, one is a single bond bonded to L3, and the other is an R bond bonded to L3. 221 ~R 230 Each independently relates to R in the above general formula (20) 21 Same meaning
[0934] L3 is a linking group, and the meaning of L3 as a linking group is the same as that of L3 as a linking group in the above general formula (25B).
[0935] p is 1, 2, 3, 4, or 5.
[0936] L3 in the above general formulas (25B), (25C), (25D) and (25E) is preferably a substituted or unsubstituted aryl group with 6 to 50 cyclic carbon atoms, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 cyclic atoms.
[0937] (Method for manufacturing phenanthrene-coral compounds)
[0938] Phenanthroline compounds can be manufactured using known methods. Alternatively, they can be manufactured by analogy with known alternative reactions and starting materials corresponding to the target substance.
[0939] (Specific examples of phenanthrene-coral compounds)
[0940] Specific examples of phenanthrene-rhein compounds include the following compounds. However, the present invention is not limited to these specific examples of phenanthrene-rhein compounds.
[0941]
Chemical Formula 35
[0942]
[0943]
Chemical Formula 36
[0944]
[0945]
Chemical Formula 37
[0946]
[0947] [Chemical Formula 38]
[0948]
[0949] [Chemical Formula 39]
[0950]
[0951]
Chemical Formula 40
[0952]
[0953]
Chemical Formula 41
[0954]
[0955]
Chemical Formula 42
[0956]
[0957]
Chemical Formula 43
[0958]
[0959]
Chemical Formula 44
[0960]
[0961] [Chemical Formula 45]
[0962]
[0963]
Chemical Formula 46
[0964]
[0965] [Chemical Formula 47]
[0966]
[0967] [Chemical Formula 48]
[0968]
[0969] [Chemical Formula 49]
[0970]
[0971] [Chemical Formula 50]
[0972]
[0973]
Chemical Formula 51
[0974]
[0975]
Chemical Formula 52
[0976]
[0977]
Chemical Formula 53
[0978]
[0979] (First main material, second main material, and third main material)
[0980] In the organic EL element according to this embodiment, the first host material, the second host material, and the third host material can be, for example, the first compound shown in general formula (1), general formula (1X), general formula (12X), general formula (13X), general formula (14X), general formula (15X), or general formula (16X) and the second compound shown in general formula (2). Alternatively, the first compound can be used as both the first host material and the second host material. In this case, the compound shown in general formula (1), or general formula (1X), general formula (12X), general formula (13X), general formula (14X), general formula (15X), or general formula (16X) used as the second host material is sometimes referred to as the second compound for convenience.
[0981] (First main material)
[0982] In the organic EL element involved in this embodiment, the first host material is also preferably in the molecule having the structure described in condition (ii), that is, a linking structure comprising a benzene ring and a naphthalene ring connected by a single bond, wherein the benzene ring and the naphthalene ring in the linking structure are each further independently fused with a single ring or a fused ring, or not fused, and the benzene ring and the naphthalene ring in the linking structure are further linked by crosslinking at least one part other than the single bond.
[0983] By having such a cross-linked connection structure in the first host material, it is expected that the color degradation of organic EL elements can be suppressed.
[0984] The first host material at this point only needs to have a linkage structure (sometimes called a benzene-naphthalene linkage structure) consisting of a benzene ring and a naphthalene ring linked by a single bond, as shown in formula (X1) or formula (X2), as the smallest unit in the molecule. Alternatively, a single ring or a fused ring may be further fused onto the benzene ring, or a single ring or a fused ring may be further fused onto the naphthalene ring. For example, for the first host material, since one of the naphthalene rings in the linkage structure (sometimes called a naphthalene-naphthalene linkage structure) consisting of a naphthalene ring and a naphthalene ring linked by a single bond, as shown in formula (X3), formula (X4), or formula (X5), contains a benzene ring, it also constitutes a molecule containing a benzene-naphthalene linkage structure.
[0985] [Chemical Formula 54]
[0986]
[0987] In the organic EL element of this embodiment, the crosslinking preferably includes double bonds. That is, it is also preferable to have a structure in which the benzene ring and the naphthalene ring are further connected by a crosslinking structure including double bonds in the portions other than single bonds.
[0988] If the benzene ring and naphthalene ring in the benzene-naphthalene linkage structure are further linked by crosslinking at least one part other than the single bond, then, for example, in the case of the above formula (X1), the linkage structure (fused ring) shown in the following formula (X11) is formed, and in the case of the above formula (X3), the linkage structure (fused ring) shown in the following formula (X31) is formed.
[0989] If the benzene ring and naphthalene ring in the benzene-naphthalene linkage structure are further linked by crosslinking including double bonds in the part other than single bonds, then, for example, in the case of the above formula (X1), it becomes the linkage structure (fused ring) shown in the following formula (X12); in the case of the above formula (X2), it becomes the linkage structure (fused ring) shown in the following formula (X21), formula (X22) or formula (X23); in the case of the above formula (X4), it becomes the linkage structure (fused ring) shown in the following formula (X41); and in the case of the above formula (X5), it becomes the linkage structure (fused ring) shown in the following formula (X51).
[0990] If the benzene ring and naphthalene ring in the benzene-naphthalene linkage structure are further linked in at least one part other than the single bond by crosslinking containing heteroatoms (e.g., oxygen atoms), then, for example, in the case of the above formula (X1), the linkage structure (fused ring) shown in the following formula (X13) is formed.
[0991]
Chemical Formula 55
[0992]
[0993] In the organic EL element involved in this embodiment, the first host material is preferably the structure of the above condition (i), that is, a biphenyl structure in which a first benzene ring and a second benzene ring are connected by a single bond in the molecule, and the first benzene ring and the second benzene ring in the biphenyl structure are further connected by crosslinking in at least one part other than the single bond.
[0994] In the organic EL element of this embodiment, the first host material preferably has the structure described in condition (i) in its molecule, wherein the first benzene ring and the second benzene ring in the biphenyl structure are further connected by crosslinking in one part other than the single bond. By having such a crosslinked biphenyl structure in the first host material, it is expected that color degradation of the organic EL element can be suppressed.
[0995] In the organic EL element involved in this embodiment, it is also preferred that the first host material has the structure of the above-described condition (i) in the molecule, and the first benzene ring and the second benzene ring in the biphenyl structure are further connected in two parts other than the above-described single bond through the above-described crosslinking.
[0996] In the organic EL element involved in this embodiment, the first host material is preferably also having the structure of the above-described condition (i) in the molecule, and the crosslinking includes double bonds.
[0997] In the organic EL element involved in this embodiment, the first host material is preferably structured in the molecule under the above condition (i), and the crosslinking does not include double bonds.
[0998] In the organic EL element of this embodiment, it is also preferable that the first host material has the structure described in condition (i) in the molecule, wherein the first benzene ring and the second benzene ring in the biphenyl structure are further connected in two parts other than the single bond by the crosslinking described above, and the crosslinking does not include double bonds. By having such a crosslinked biphenyl structure in the first host material, it is expected that the color deterioration of the organic EL element can be suppressed.
[0999] For example, if the first benzene ring and the second benzene ring in the biphenyl structure shown in the following formula (BP1) are further connected by crosslinking in at least one part other than the single bond, the biphenyl structure forms a connected structure (fused ring) such as the following formulas (BP11) to (BP15).
[1000] [Chemical Formula 56]
[1001]
[1002] The above formula (BP11) is a structure in which one part other than the single bond is connected by crosslinking without double bonds.
[1003] The above formula (BP12) is a structure in which one part other than the single bond is connected by cross-linking containing double bonds.
[1004] The above formula (BP13) is a structure in which two parts other than the single bond are connected by cross-linking without double bonds.
[1005] The above formula (BP14) is a structure in which one of the two parts other than the single bond is connected by a crosslinking link that does not contain a double bond, and the other part of the two parts other than the single bond is connected by a crosslinking link that contains a double bond.
[1006] The above formula (BP15) is a structure in which two parts other than the single bond are connected by cross-linking containing double bonds.
[1007] (First compound)
[1008] In the organic EL element involved in this embodiment, the first host material is preferably a first compound having at least one group represented by the following general formula (11) and represented by the following general formula (1).
[1009] [Chemical Formula 57]
[1010]
[1011] (In the above general formula (1),
[1012] R 101 ~R 110 Each independently
[1013] hydrogen atom,
[1014] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1015] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1016] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1017] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1018] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1019] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1020] -O-(R 904 The groups shown in the figure,
[1021] -S-(R 905 The groups shown in the figure,
[1022] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1023] -C(=O)R 801 The groups shown
[1024] -COOR 802 The groups shown
[1025] Halogen atoms,
[1026] cyano,
[1027] Nitro,
[1028] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1029] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1030] The groups represented by the above general formula (11),
[1031] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11) above.
[1032] 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.
[1033] L 101 for
[1034] single bond,
[1035] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1036] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1037] Ar 101 for
[1038] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1039] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1040] mx is 0, 1, 2, 3, 4, or 5.
[1041] 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.
[1042] In Ar 101In cases where there are two or more Ar, two or more Ar 101 They are the same or different.
[1043] In the above general formula (11), * indicates the bonding position with the pyrene ring in the above general formula (1).
[1044] (In the first 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
[1045] hydrogen atom,
[1046] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1047] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1048] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1049] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1050] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[1051] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[1052] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[1053] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[1054] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.
[1055] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[1056] In R 907In the case of multiple Rs, multiple Rs 907 They are the same or different.
[1057] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[1058] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)
[1059] In the organic EL element of this embodiment, the group represented by the above general formula (11) is preferably the group represented by the following general formula (111).
[1060] [Chemical Formula 58]
[1061]
[1062] (In the above general formula (111),
[1063] X1 is CR 123 R 124 oxygen atom, sulfur atom or NR 125 ,
[1064] L 111 and L 112 Each independently
[1065] single bond,
[1066] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1067] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1068] ma is 0, 1, 2, 3 or 4.
[1069] mb can be 0, 1, 2, 3, or 4.
[1070] ma+mb is 0, 1, 2, 3 or 4.
[1071] Ar 101 Ar in the above general formula (11) 101 Same meaning
[1072] R 121 R 122 R 123 R 124 and R 125 Each independently
[1073] hydrogen atom,
[1074] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1075] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1076] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1077] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1078] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1079] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1080] -O-(R 904 The groups shown in the figure,
[1081] -S-(R 905 The groups shown in the figure,
[1082] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1083] -C(=O)R 801 The groups shown
[1084] -COOR 802 The groups shown
[1085] Halogen atoms,
[1086] cyano,
[1087] Nitro,
[1088] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1089] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1090] mc is 3.
[1091] 3 Rs 121 They are the same or different.
[1092] md is 3
[1093] 3 Rs 122 (They may be the same or different.)
[1094] 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 121Bonded 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.
[1095] [Chemical Formula 59]
[1096]
[1097] 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).
[1098] [Chemical Formula 60]
[1099]
[1100] (In the above general formula (111b),
[1101] X1, L 111 L 112 ma, mb, Ar 101 R 121 R 122 R 123 R 124 and 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
[1102] Multiple R 121 They are the same or different.
[1103] Multiple R 122 (They may be the same or different.)
[1104] 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).
[1105] In the organic EL element involved in this embodiment, the preferred one is...
[1106] ma is 0, 1, or 2.
[1107] mb can be 0, 1, or 2.
[1108] In the organic EL element involved in this embodiment, the preferred one is...
[1109] ma is 0 or 1.
[1110] mb is 0 or 1.
[1111] 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.
[1112] In the organic EL element involved in this embodiment,
[1113] Ar 101 Preferred
[1114] Substituted or unsubstituted phenyl
[1115] Substituted or unsubstituted naphthyl groups
[1116] Substituted or unsubstituted biphenyl,
[1117] Substituted or unsubstituted triphenyl,
[1118] Substituted or unsubstituted pyrene group
[1119] Replaced or unreplaced foie gras, or
[1120] Substituted or unsubstituted fluorene group.
[1121] In the organic EL element involved in this embodiment,
[1122] Ar is also preferred 101 It is a group represented by the following general formula (12), general formula (13) or general formula (14).
[1123]
Chemical Formula 61
[1124]
[1125] (In the above general formulas (12), (13) and (14),
[1126] R 111 ~R 120 Each independently
[1127] hydrogen atom,
[1128] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1129] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1130] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1131] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1132] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1133] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1134] -O-(R 904 The groups shown in the figure,
[1135] -S-(R 905 The groups shown in the figure,
[1136] -N(R 906 (R) 907 The groups shown in the figure,
[1137] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1138] -C(=O)R 124 The groups shown
[1139] -COOR 125 The groups shown
[1140] Halogen atoms,
[1141] cyano,
[1142] Nitro,
[1143] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1144] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1145] In the above general formulas (12), (13), and (14), * indicates the same as L in the above general formula (11). 101 The bonding position, or the L in the above general formula (111) or general formula (111b) 112 (The bonding location.)
[1146] In the organic EL element involved in this embodiment, the first compound is preferably represented by the following general formula (101).
[1147]
Chemical Formula 62
[1148]
[1149] (In the above general formula (101),
[1150] R 101 ~R 120 Each independently
[1151] hydrogen atom,
[1152] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1153] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1154] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1155] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1156] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1157] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1158] -O-(R 904 The groups shown in the figure,
[1159] -S-(R 905 The groups shown in the figure,
[1160] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1161] -C(=O)R 801 The groups shown
[1162] -COOR 802 The groups shown
[1163] Halogen atoms,
[1164] cyano,
[1165] Nitro,
[1166] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1167] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1168] 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,
[1169] L101 for
[1170] single bond,
[1171] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1172] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1173] mx is 0, 1, 2, 3, 4, or 5.
[1174] 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.)
[1175] Of the first compound represented by the above general formula (101), the preferred one is...
[1176] R 101 ~R 110 and R 111 ~R 120 Each independently
[1177] hydrogen atom,
[1178] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1179] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1180] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1181] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1182] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1183] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1184] -O-(R 904 The groups shown in the figure,
[1185] -S-(R 905 The groups shown in the figure,
[1186] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1187] -C(=O)R 801 The groups shown
[1188] -COOR 802 The groups shown
[1189] Halogen atoms,
[1190] cyano,
[1191] Nitro,
[1192] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1193] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1194] 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,
[1195] L 101 for
[1196] single bond,
[1197] Substituted or unsubstituted arylene groups with 6 to 24 carbon atoms, or
[1198] Divalent heterocyclic groups with 5–24 cyclic atoms, substituted or unsubstituted.
[1199] mx is 1, 2, 3, 4, or 5.
[1200] 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.
[1201] In the organic EL element of this embodiment, the first compound is preferably represented by the following general formulas (1010), (1011), (1012), (1013), (1014), or (1015).
[1202]
Chemical Formula 63
[1203]
[1204]
Chemical Formula 64
[1205]
[1206]
Chemical Formula 65
[1207]
[1208]
Chemical Formula 66
[1209]
[1210] [Chemical Formula 67]
[1211]
[1212]
Chemical Formula 68
[1213]
[1214] (In the above general formulas (1010) to (1015),
[1215] R 101 ~R 120 Each independently
[1216] hydrogen atom,
[1217] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1218] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1219] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1220] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1221] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1222] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1223] -O-(R 904 The groups shown in the figure,
[1224] -S-(R 905 The groups shown in the figure,
[1225] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1226] -C(=O)R 801 The groups shown
[1227] -COOR 802 The groups shown
[1228] Halogen atoms,
[1229] cyano,
[1230] Nitro,
[1231] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1232] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1233] L 101 for
[1234] single bond,
[1235] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1236] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1237] mx is 0, 1, 2, 3, 4, or 5.
[1238] 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.)
[1239] It should be noted that the compound represented by the above general formula (1010) is equivalent to R. 103 Indicates with L 101 The bonding position, R 120 Indicates with L 101 Compounds at the bonding positions.
[1240] It should be noted that the compound represented by the above general formula (1011) is equivalent to R. 103 Indicates with L 101 The bonding position, R 111 Indicates with L 101 Compounds at the bonding positions.
[1241] It should be noted that the compound represented by the above general formula (1012) is equivalent to R. 103 Indicates with L 101 The bonding position, R 118 Indicates with L 101 Compounds at the bonding positions.
[1242] It should be noted that the compound represented by the above general formula (1013) is equivalent to R. 102 Indicates with L 101 The bonding position, R 111 Indicates with L 101 Compounds at the bonding positions.
[1243] It should be noted that the compound represented by the above general formula (1014) is equivalent to R. 102 Indicates with L 101 The bonding position, R 118 Indicates with L 101 Compounds at the bonding positions.
[1244] It should be noted that the compound represented by the above general formula (1015) is equivalent to R. 105 Indicates with L 101 The bonding position, R 118 Indicates with L 101 Compounds at the bonding positions.
[1245] In the organic EL element involved in this embodiment, the first compound is preferably represented by the above general formula (1010).
[1246] In the organic EL element involved in this embodiment, it is not related to L 101 The bonding position of R 101 ~R 110 Each independently preferred
[1247] hydrogen atom,
[1248] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1249] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1250] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1251] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1252] In the organic EL element involved in this embodiment, it is not related to L 101 The bonding position of R 101 ~R 110 Each independently preferred
[1253] hydrogen atom,
[1254] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[1255] Cycloalkyl groups, substituted or unsubstituted, having 3 to 50 carbon atoms.
[1256] In the organic EL element involved in this embodiment, it is not related to L 101 The bonding position of R 101 ~R 110 Hydrogen atoms are preferred.
[1257] In the organic EL element involved in this embodiment, it is not related to L 101 The bonding position of R 111 ~R 120 Each independently preferred
[1258] hydrogen atom,
[1259] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1260] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1261] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1262] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1263] In the organic EL element involved in this embodiment, it is not related to L 101 The bonding position of R 111 ~R 120 Each independently preferred
[1264] hydrogen atom,
[1265] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[1266] Cycloalkyl groups, substituted or unsubstituted, having 3 to 50 carbon atoms.
[1267] In the organic EL element involved in this embodiment, it is not related to L 101 The bonding position of R 111 ~R 120 Hydrogen atoms are preferred.
[1268] In the organic EL element involved in this embodiment,
[1269] Preferred L 101 for
[1270] single key, or
[1271] A substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.
[1272] In the organic EL element involved in this embodiment, L is also preferred. 101 for
[1273] single bond,
[1274] Substituted or unsubstituted arylene groups with 6 to 18 carbon atoms, or
[1275] A divalent heterocyclic group with 5 to 18 cyclic atoms, substituted or unsubstituted.
[1276] In the organic EL element involved in this embodiment, L is also preferred. 101 for
[1277] single key, or
[1278] A substituted or unsubstituted aryl group with 6 to 18 carbon atoms in a cyclic ring.
[1279] In the organic EL element involved in this embodiment, L is also preferred. 101for
[1280] A substituted or unsubstituted aryl group with 6 to 18 carbon atoms in a cyclic ring.
[1281] In the organic EL element involved in this embodiment, L is also preferred. 101 for
[1282] single bond,
[1283] Substituted or unsubstituted arylene groups with 6 to 13 carbon atoms, or
[1284] A divalent heterocyclic group with 5 to 13 cyclic atoms, substituted or unsubstituted.
[1285] In the organic EL element involved in this embodiment, L is also preferred. 101 for
[1286] single key, or
[1287] A substituted or unsubstituted aryl group with 6 to 13 carbon atoms in a cyclic ring.
[1288] In the organic EL element involved in this embodiment, L is also preferred. 101 for
[1289] A substituted or unsubstituted aryl group with 6 to 13 carbon atoms in a cyclic ring.
[1290] In the organic EL element involved in this embodiment, mx is preferably 1, 2 or 3.
[1291] In the organic EL element involved in this embodiment, mx is preferably 1 or 2.
[1292] In the organic EL element involved in this embodiment, mx is preferably 1, 2, or 3.
[1293] L 101 for
[1294] Substituted or unsubstituted arylene groups with 6 to 18 carbon atoms, or
[1295] A divalent heterocyclic group with 5 to 18 cyclic atoms, substituted or unsubstituted.
[1296] In the organic EL element involved in this embodiment, mx is preferably 1 or 2.
[1297] L 101 for
[1298] Substituted or unsubstituted arylene groups with 6 to 18 carbon atoms, or
[1299] A divalent heterocyclic group with 5 to 18 cyclic atoms, substituted or unsubstituted.
[1300] In the organic EL element involved in this embodiment, mx is preferably 1 or 2.
[1301] L 101 It is a substituted or unsubstituted aryl group with 6 to 18 carbon atoms in a cyclic structure.
[1302] In the organic EL element involved in this embodiment, the first compound is preferably represented by the following general formula (102).
[1303]
Chemical Formula 69
[1304]
[1305] (In the above general formula (102),
[1306] R 101 ~R 120 Each independently relates to R in the above general formula (101). 101 ~R 120 Same meaning
[1307] 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,
[1308] X1 is CR 123 R 124 oxygen atom, sulfur atom or NR 125 ,
[1309] L 111 and L 112 Each independently
[1310] single bond,
[1311] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1312] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1313] ma is 0, 1, 2, 3 or 4.
[1314] mb can be 0, 1, 2, 3, or 4.
[1315] ma+mb is 0, 1, 2, 3 or 4.
[1316] R 121 R 122 R 123 R 124 and R 125Each independently
[1317] hydrogen atom,
[1318] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1319] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1320] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1321] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1322] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1323] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1324] -O-(R 904 The groups shown in the figure,
[1325] -S-(R 905 The groups shown in the figure,
[1326] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1327] -C(=O)R 801 The groups shown
[1328] -COOR 802 The groups shown
[1329] Halogen atoms,
[1330] cyano,
[1331] Nitro,
[1332] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1333] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1334] mc is 3.
[1335] 3 Rs 121 They are the same or different.
[1336] md is 3
[1337] 3 Rs 122 (They may be the same or different.)
[1338] Of the compounds represented by the above general formula (102), the preferred one is...
[1339] ma is 0, 1, or 2.
[1340] mb can be 0, 1, or 2.
[1341] Of the compounds represented by the above general formula (102), the preferred one is...
[1342] ma is 0 or 1.
[1343] mb is 0 or 1.
[1344] In the compounds represented by the above general formula (102), L is preferred. 111 and L 112 Each independently
[1345] single bond,
[1346] Substituted or unsubstituted arylene groups with 6 to 24 carbon atoms, or
[1347] A divalent heterocyclic group with 5 to 24 cyclic atoms, substituted or unsubstituted.
[1348] In the compounds represented by the above general formula (102),
[1349] ma is 1, 2, or 3.
[1350] mb is 1, 2 or 3,
[1351] ma+mb is 2, 3, or 4.
[1352] Of the compounds represented by the above general formula (102), the preferred one is...
[1353] ma is 1 or 2.
[1354] mb is 1 or 2.
[1355] Of the compounds represented by the above general formula (102), the preferred one is...
[1356] ma is 1.
[1357] mb is 1.
[1358] In the organic EL element involved in this embodiment, it is not related to L 111 The bonding position of R 101 ~R 110 Each independently preferred
[1359] hydrogen atom,
[1360] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1361] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1362] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1363] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1364] In the organic EL element involved in this embodiment, it is not related to L 111 The bonding position of R 101 ~R 110 Each independently preferred
[1365] hydrogen atom,
[1366] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[1367] Cycloalkyl groups, substituted or unsubstituted, having 3 to 50 carbon atoms.
[1368] In the organic EL element involved in this embodiment, it is not related to L 111 The bonding position of R 101 ~R 110 Hydrogen atoms are preferred.
[1369] In the organic EL element involved in this embodiment, it is not related to L 112 The bonding position of R 111 ~R 120 Each independently preferred
[1370] hydrogen atom,
[1371] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1372] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1373] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1374] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1375] In the organic EL element involved in this embodiment, it is not related to L 112 The bonding position of R 111 ~R 120 Each independently preferred
[1376] hydrogen atom,
[1377] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[1378] Cycloalkyl groups, substituted or unsubstituted, having 3 to 50 carbon atoms.
[1379] In the organic EL element involved in this embodiment, it is not related to L 112 The bonding position of R111 ~R 120 Hydrogen atoms are preferred.
[1380] In the organic EL element involved in this embodiment,
[1381] Preferred R 101 ~R 110 Two or more of them are groups represented by the general formula (11) above.
[1382] In the organic EL element involved in this embodiment, it is preferred that,
[1383] R 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.
[1384] In the organic EL element involved in this embodiment, it is preferred that,
[1385] Ar 101 It is neither a substituted nor an unsubstituted pyrene group.
[1386] L 101 It is neither a replaced nor unreplaced pyrene group.
[1387] 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.
[1388] In the organic EL element involved in this embodiment,
[1389] R is not a group represented by the general formula (11) above. 101 ~R 110 Each independently preferred
[1390] hydrogen atom,
[1391] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1392] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1393] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1394] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1395] In the organic EL element involved in this embodiment,
[1396] R is not a group represented by the general formula (11) above.101 ~R 110 Each independently preferred
[1397] hydrogen atom,
[1398] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[1399] Cycloalkyl groups, substituted or unsubstituted, having 3 to 50 carbon atoms.
[1400] 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.
[1401] In both the first compound and the second compound, the groups described as "substituted or unsubstituted" are preferably "unsubstituted".
[1402] In the organic EL element involved in this embodiment,
[1403] For example, R in the first compound represented by the above general formula (1) 101 To R 110 Two of them are groups represented by general formula (11).
[1404] In the organic EL element involved in this embodiment,
[1405] For example, R in the first compound represented by the above general formula (1) 101 To R 110 Three of them are groups represented by general formula (11).
[1406] In the organic EL element involved in this embodiment,
[1407] For example, R in the first compound represented by the above general formula (1) 101 To R 110 Four of them are groups represented by general formula (11).
[1408] In the organic EL element involved in this embodiment,
[1409] For example, R in the first compound represented by the above general formula (1) 101 To R 110 One of them is a group represented by general formula (11), and mx is 1 or more.
[1410] In the organic EL element involved in this embodiment,
[1411] For example, R in the first compound represented by the above general formula (1) 101 To R 110One of them is a group represented by general formula (11), mx is 0, Ar 101 Aryl groups, whether substituted or unsubstituted.
[1412] In the organic EL element involved in this embodiment,
[1413] For example, R in the first compound represented by the above general formula (1) 101 To R 110 One of them is a group represented by general formula (11), mx is 0, Ar 101 A substituted or unsubstituted heterocyclic group containing a nitrogen atom.
[1414] In the organic EL element involved in this embodiment,
[1415] For example, R in the first compound represented by the above general formula (1) 101 To R 110 One of them is a group represented by general formula (11), mx is 0, Ar 101 A substituted or unsubstituted heterocyclic group containing a sulfur atom.
[1416] In the organic EL element involved in this embodiment,
[1417] For example, R in the first compound represented by the above general formula (1) 101 To R 110 One of them is a group represented by general formula (11), mx is 0, Ar 101 For substituted or unsubstituted furanyl groups,
[1418] Oxazolyl,
[1419] Isoxazolyl,
[1420] Oxadiazole group,
[1421] Xuton base,
[1422] Benzofuranyl,
[1423] Isobenzofuranyl,
[1424] Dibenzofuranyl,
[1425] Benzoxazolyl,
[1426] Benzisoxazole group,
[1427] phenoxazine group,
[1428] Morpholinyl
[1429] Dinaphthylfuranyl,
[1430] Azadibenzofuranyl,
[1431] diazadibenzofuranyl,
[1432] Azanaphthobenzofuranyl and diazanaphthobenzofuranyl.
[1433] In the organic EL element involved in this embodiment,
[1434] For example, R in the first compound represented by the above general formula (1) 101 To R 110 One of them is a group represented by general formula (11), mx is 0, Ar 101 To select unsubstituted furanyl groups,
[1435] Oxazolyl,
[1436] Isoxazolyl,
[1437] Oxadiazole group,
[1438] Xuton base,
[1439] Benzofuranyl,
[1440] Isobenzofuranyl,
[1441] Dibenzofuranyl,
[1442] Benzoxazolyl,
[1443] Benzisoxazole group,
[1444] phenoxazine group,
[1445] Morpholinyl
[1446] Dinaphthylfuranyl,
[1447] Azadibenzofuranyl,
[1448] diazadibenzofuranyl,
[1449] At least one group from the group consisting of azinaphthobenzofuranyl and diazinaphthobenzofuranyl.
[1450] In the organic EL element involved in this embodiment, for example, R in the first compound represented by the above general formula (1) 101 To R 110 One of them is a group represented by general formula (11), mx is 0, Ar 101 It is a substituted or unsubstituted dibenzofuranyl group.
[1451] In the organic EL element involved in this embodiment, for example, R in the first compound represented by the above general formula (1) 101 To R 110One of them is a group represented by general formula (11), mx is 0, Ar 101 It is an unsubstituted dibenzofuranyl group.
[1452] In the organic EL element involved in this embodiment, for example, mx in the first compound shown in the above general formula (101) is 2 or more.
[1453] In the organic EL element involved in this embodiment, for example, mx in the first compound represented by the above general formula (101) is 1 or more, L 101 It is an arylene group with 6 to 24 carbon atoms or a divalent heterocyclic group with 5 to 24 atoms.
[1454] In the organic EL element involved in this embodiment, for example, mx in the first compound represented by the above general formula (101) is 1 or more, L 101 It is an arylene group with 6 to 18 carbon atoms in the ring, or a divalent heterocyclic group with 5 to 18 carbon atoms in the ring.
[1455] Compounds represented by general formula (1X)
[1456] In the organic EL element involved in this embodiment, the first compound is preferably a compound represented by the following general formula (1X).
[1457] [Chemical Formula 70]
[1458]
[1459] (In the above general formula (1X),
[1460] R 101 ~R 112 Each independently
[1461] hydrogen atom,
[1462] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1463] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1464] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1465] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1466] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1467] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1468] -O-(R904 The groups shown in the figure,
[1469] -S-(R 905 The groups shown in the figure,
[1470] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1471] -C(=O)R 801 The groups shown
[1472] -COOR 802 The groups shown
[1473] Halogen atoms,
[1474] cyano,
[1475] Nitro,
[1476] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1477] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1478] The groups represented by the above general formula (11X),
[1479] Among them, R 101 ~R 112 At least one of them is a group represented by the general formula (11X) above.
[1480] When multiple groups represented by the above general formula (11X) are present, the multiple groups represented by the above general formula (11X) may be the same as or different from each other.
[1481] L 101 for
[1482] single bond,
[1483] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1484] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1485] Ar 101 for
[1486] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1487] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1488] mx is 1, 2, 3, 4, or 5.
[1489] 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.
[1490] In Ar 101 In cases where there are two or more Ar, two or more Ar 101 They are the same or different.
[1491] In the above general formula (11X), * indicates the bonding position with the benzo[a]anthracene ring in the above general formula (1X).
[1492] In the organic EL element of this embodiment, the group represented by the above general formula (11X) is preferably the group represented by the following general formula (111X).
[1493]
Chemical Formula 71
[1494]
[1495] (In the above general formula (111X),
[1496] X1 is CR 143 R 144 oxygen atom, sulfur atom or NR 145 ,
[1497] L 111 and L 112 Each independently
[1498] single bond,
[1499] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1500] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1501] ma is 1, 2, 3, or 4.
[1502] mb is 1, 2, 3, or 4.
[1503] ma+mb is 2, 3, or 4.
[1504] Ar 101 Ar in the above general formula (11) 101 Same meaning
[1505] R 141 R 142 R 143 R 144 and R 145 Each independently
[1506] hydrogen atom,
[1507] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1508] Substituted or unsubstituted alkyl halides with 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] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1513] -O-(R 904 The groups shown in the figure,
[1514] -S-(R 905 The groups shown in the figure,
[1515] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1516] -C(=O)R 801 The groups shown
[1517] -COOR 802 The groups shown
[1518] Halogen atoms,
[1519] cyano,
[1520] Nitro,
[1521] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1522] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1523] mc is 3.
[1524] 3 Rs 141 They are the same or different.
[1525] md is 3
[1526] 3 Rs 142 (They may be the same or different.)
[1527] In the group represented by the above general formula (111X), at positions *1 to *8 of the carbon atoms in the ring structure represented by the following general formula (111aX), L 111 Bonded to any of the positions from *1 to *4, R 141 Bonded to the remaining 3 positions from *1 to *4, L 112Bonded to any position from *5 to *8, R 142 It is bonded to the other 3 positions from *5 to *8.
[1528]
Chemical Formula 72
[1529]
[1530] For example, in the groups represented by the above general formula (111X), in L 111 The positions of the carbon atoms *2 bonded to the ring structure shown in the above general formula (111aX), L 112 When the carbon atom of *7 in the ring structure shown in the above general formula (111aX) is bonded, the group shown in the above general formula (111X) is represented by the following general formula (111bX).
[1531]
Chemical Formula 73
[1532]
[1533] (In the above general formula (111bX),
[1534] X1, L 111 L 112 ma, mb, Ar 101 R 141 R 142 R 143 R 144 and R 145 Each independently relates to X1 and L in the above general formula (111X). 111 L 112 ma, mb, Ar 101 R 141 R 142 R 143 R 144 and R 145 Same meaning
[1535] Multiple R 141 They are the same or different.
[1536] Multiple R 142 (They may be the same or different.)
[1537] In the organic EL element of this embodiment, the group represented by the above general formula (111X) is preferably the group represented by the above general formula (111bX).
[1538] In the compounds represented by the above general formula (1X), preferably, ma is 1 or 2 and mb is 1 or 2.
[1539] In the compounds represented by the above general formula (1X), preferably, ma is 1 and mb is 1.
[1540] In the compounds represented by the above general formula (1X), Ar 101 Preferably, it is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[1541] Of the compounds represented by the above general formula (1X), Ar is preferred. 101 for
[1542] Substituted or unsubstituted phenyl
[1543] Substituted or unsubstituted naphthyl groups
[1544] Substituted or unsubstituted biphenyl,
[1545] Substituted or unsubstituted triphenyl,
[1546] Substituted or unsubstituted benzo[a]anthracene,
[1547] Substituted or unsubstituted pyrene group
[1548] Replaced or unreplaced foie gras, or
[1549] Substituted or unsubstituted fluorene group.
[1550] The compound represented by the above general formula (1X) is also preferably represented by the following general formula (101X).
[1551] [Chemical Formula 74]
[1552]
[1553] (In the above general formula (101X),
[1554] R 111 and R 112 One of them represents L 101 The bonding position, R 133 and R 134 One of them represents L 101 The bonding position,
[1555] R 101 ~R 110 R 121 ~R 130 Not related to L 101 The bonding position of R 111 or R 112 and not related to L 101 The bonding position of R 133 or R 134 Each independently
[1556] hydrogen atom,
[1557] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1558] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1559] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1560] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1561] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1562] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1563] -O-(R 904 The groups shown in the figure,
[1564] -S-(R 905 The groups shown in the figure,
[1565] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1566] -C(=O)R 801 The groups shown
[1567] -COOR 802 The groups shown
[1568] Halogen atoms,
[1569] cyano,
[1570] Nitro,
[1571] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1572] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1573] L 101 for
[1574] single bond,
[1575] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1576] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1577] mx is 1, 2, 3, 4, or 5.
[1578] In L 101In cases where there are two or more L's, there are two or more L's. 101 (They may be the same or different.)
[1579] In the compounds represented by the above general formula (1X), L 101 Preferably, it is a single bond, or a cyclic aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[1580] The compound represented by the above general formula (1X) is also preferably represented by the following general formula (102X).
[1581] [Chemical Formula 75]
[1582]
[1583] (In the above general formula (102X),
[1584] R 111 and R 112 One of them represents L 111 The bonding position, R 133 and R 134 One of them represents L 112 The bonding position,
[1585] R 101 ~R 110 R 121 ~R 130 Not related to L 111 The bonding position of R 111 or R 112 And not related to L 112 The bonding position of R 133 or R 134 Each independently
[1586] hydrogen atom,
[1587] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1588] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1589] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1590] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1591] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1592] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1593] -O-(R904 The groups shown in the figure,
[1594] -S-(R 905 The groups shown in the figure,
[1595] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1596] -C(=O)R 801 The groups shown
[1597] -COOR 802 The groups shown
[1598] Halogen atoms,
[1599] cyano,
[1600] Nitro,
[1601] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1602] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1603] X1 is CR 143 R 144 oxygen atom, sulfur atom or NR 145 ,
[1604] L 111 and L 112 Each independently
[1605] single bond,
[1606] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1607] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1608] ma is 1, 2, 3, or 4.
[1609] mb is 1, 2, 3, or 4.
[1610] ma+mb is 2, 3, 4 or 5.
[1611] R 141 R 142 R 143 R 144 and R 145 Each independently
[1612] hydrogen atom,
[1613] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1614] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1615] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1616] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1617] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1618] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1619] -O-(R 904 The groups shown in the figure,
[1620] -S-(R 905 The groups shown in the figure,
[1621] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1622] -C(=O)R 801 The groups shown
[1623] -COOR 802 The groups shown
[1624] Halogen atoms,
[1625] cyano,
[1626] Nitro,
[1627] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1628] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1629] mc is 3.
[1630] 3 Rs 141 They are the same or different.
[1631] md is 3
[1632] 3 Rs 142 (They may be the same or different.)
[1633] In the compounds represented by the above general formula (1X), it is preferred that ma in the above general formula (102X) is 1 or 2, and mb is 1 or 2.
[1634] In the compounds represented by the above general formula (1X), it is preferred that ma is 1 and mb is 1 in the above general formula (102X).
[1635] In the compounds represented by the above general formula (1X), the groups represented by the above general formula (11X) are also preferably groups represented by the following general formula (11AX) or groups represented by the following general formula (11BX).
[1636] [Chemical Formula 76]
[1637]
[1638] (In the above general formula (11AX) and the above general formula (11BX),
[1639] R 121 ~R 131 Each independently
[1640] hydrogen atom,
[1641] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1642] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1643] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1644] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1645] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1646] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1647] -O-(R 904 The groups shown in the figure,
[1648] -S-(R 905 The groups shown in the figure,
[1649] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1650] -C(=O)R 801 The groups shown
[1651] -COOR 802 The groups shown
[1652] Halogen atoms,
[1653] cyano,
[1654] Nitro,
[1655] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1656] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1657] When multiple groups represented by the above general formula (11AX) are present, the multiple groups represented by the above general formula (11AX) may be the same as or different from each other.
[1658] When multiple groups represented by the above general formula (11BX) are present, the multiple groups represented by the above general formula (11BX) may be the same as or different from each other.
[1659] L 131 and L 132 Each independently
[1660] single bond,
[1661] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1662] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1663] In the above general formulas (11AX) and (11BX), * denotes the bonding positions with the benzo[a]anthracene ring in general formula (1X).
[1664] The compound represented by the above general formula (1X) is also preferably represented by the following general formula (103X).
[1665]
Chemical Formula 77
[1666]
[1667] (In the above general formula (103X),
[1668] R 101 ~R 110 and R 112 Each of them corresponds to R in the above general formula (1X) 101 ~R 110 and R 112 Same meaning
[1669] R 121 ~R 131 L 131 and L 132 Each of them corresponds to R in the above general formula (11BX) 121 ~R 131 L 131 and L 132 The meaning is the same.
[1670] In the compounds represented by the above general formula (1X), L 131 It is also preferred to use substituted or unsubstituted aryl groups with 6 to 50 cyclic carbons.
[1671] In the compounds represented by the above general formula (1X), L 132 It is also preferred to use substituted or unsubstituted aryl groups with 6 to 50 cyclic carbons.
[1672] In the compounds represented by the above general formula (1X), R is also preferred. 101 ~R 112 Two or more of them are groups represented by the general formula (11) above.
[1673] In the compounds represented by the above general formula (1X), R is preferred. 101 ~R 112 Two or more of them are groups represented by the general formula (11X) above, and Ar in general formula (11X) 101 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[1674] Among the compounds represented by the above general formula (1X), it is also preferred
[1675] Ar 101 Not substituted or unsubstituted benzo[a]anthracene,
[1676] L 101 Not substituted or unsubstituted benzo[a]anthracene,
[1677] R, as a group not represented by the above general formula (11X) 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is not a substituted or unsubstituted benzo[a]anthyl group.
[1678] In the compounds represented by the above general formula (1X), it is preferable that the R group is not represented by the group represented by the above general formula (11X). 101 ~R 112 Each independently
[1679] hydrogen atom,
[1680] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1681] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1682] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1683] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[1684] In the compounds represented by the above general formula (1X), the R group is not the group represented by the above general formula (11X). 101 ~R 112 Preferred
[1685] hydrogen atom,
[1686] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[1687] Cycloalkyl groups, substituted or unsubstituted, having 3 to 50 carbon atoms.
[1688] In the compounds represented by the above general formula (1X), the R group is not the group represented by the above general formula (11X). 101 ~R 112 Hydrogen atoms are preferred.
[1689] Compounds represented by general formula (12X)
[1690] In the organic EL element involved in this embodiment, the first compound is preferably a compound represented by the following general formula (12X).
[1691] [Chemical Formula 78]
[1692]
[1693] (In the above general formula (12X),
[1694] R 1201 ~R 1210 One or more of the groups consisting of two or more adjacent elements.
[1695] They bond together to form substituted or unsubstituted monocyclic rings, or
[1696] They bond together to form substituted or unsubstituted fused rings.
[1697] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 1201 ~R 1210 Each independently
[1698] hydrogen atom,
[1699] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1700] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1701] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1702] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1703] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1704] -Si(R 901 (R) 902 (R)903 The groups shown in the figure,
[1705] -O-(R 904 The groups shown in the figure,
[1706] -S-(R 905 The groups shown in the figure,
[1707] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1708] -C(=O)R 801 The groups shown
[1709] -COOR 802 The groups shown
[1710] Halogen atoms,
[1711] cyano,
[1712] Nitro,
[1713] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1714] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1715] The groups represented by the above general formula (121),
[1716] Wherein, the substituent when the aforementioned substituted or unsubstituted monocyclic ring has a substituent, the substituent when the aforementioned 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) above.
[1717] When there are multiple groups represented by the above general formula (121), the multiple groups represented by the above general formula (121) may be the same as or different from each other.
[1718] L 1201 for
[1719] single bond,
[1720] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1721] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1722] Ar 1201 for
[1723] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1724] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1725] mx2 is 0, 1, 2, 3, 4, or 5.
[1726] 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.
[1727] In Ar 1201 In cases where there are two or more Ar, two or more Ar 1201 They are the same or different.
[1728] In the above general formula (121), * indicates the bonding position with the ring shown in the above general formula (12X).
[1729] In the above general formula (12X), R 1201 ~R 1210 The group consisting of two adjacent elements in R refers to... 1201 With R 1202 group, R 1202 With R 1203 group, R 1203 With R 1204 group, R 1204 With R 1205 group, R 1205 With R 1206 group, R 1207 With R 1208 group, R 1208 With R 1209 The group, and R 1209 With R 1210 The group.
[1730] Compounds represented by general formula (13X)
[1731] In the organic EL element involved in this embodiment, the first compound is preferably a compound represented by the following general formula (13X).
[1732] [Chemical Formula 79]
[1733]
[1734] (In the above general formula (13X),
[1735] R 1301 ~R 1310 Each independently
[1736] hydrogen atom,
[1737] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1738] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1739] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1740] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1741] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1742] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1743] -O-(R 904 The groups shown in the figure,
[1744] -S-(R 905 The groups shown in the figure,
[1745] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1746] -C(=O)R 801 The groups shown
[1747] -COOR 802 The groups shown
[1748] Halogen atoms,
[1749] cyano,
[1750] Nitro,
[1751] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1752] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1753] The groups represented by the above general formula (131),
[1754] Among them, R 1301 ~R 1310 At least one of them is a group represented by the general formula (131) above.
[1755] When there are multiple groups represented by the above general formula (131), the multiple groups represented by the above general formula (131) may be the same as or different from each other.
[1756] L 1301 for
[1757] single bond,
[1758] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1759] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1760] Ar 1301 for
[1761] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1762] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1763] mx3 can be 0, 1, 2, 3, 4, or 5.
[1764] 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.
[1765] In Ar 1301 In cases where there are two or more Ar, two or more Ar 1301 They are the same or different.
[1766] In the above general formula (131), * indicates the bonding position with the fluoranthene ring in the above general formula (13X).
[1767] In the organic EL element involved in this embodiment, the R group is not the group shown in the above general formula (131). 1301 ~R 1310 In this context, groups consisting of two or more adjacent elements are not bonded to each other. In the general formula (13X) above, a group consisting of two adjacent elements refers to R... 1301 With R 1302 group, R 1302 With R 1303 group, R 1303 With R 1304 group, R 1304 With R 1305 group, R 1305 With R 1306 group, R 1307 With R 1308 group, R 1308 With R 1309 The group, and R 1309 With R 1310 The group.
[1768] Compounds represented by general formula (14X)
[1769] In the organic EL element involved in this embodiment, the first compound is preferably a compound represented by the following general formula (14X).
[1770] [Chemical Formula 80]
[1771]
[1772] (In the above general formula (14X),
[1773] R 1401 ~R 1410 Each independently
[1774] hydrogen atom,
[1775] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1776] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1777] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1778] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1779] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1780] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1781] -O-(R 904 The groups shown in the figure,
[1782] -S-(R 905 The groups shown in the figure,
[1783] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1784] -C(=O)R 801 The groups shown
[1785] -COOR 802 The groups shown
[1786] Halogen atoms,
[1787] cyano,
[1788] Nitro,
[1789] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1790] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1791] The groups represented by the above general formula (141),
[1792] Among them, R 1401 ~R 1410 At least one of them is a group represented by the general formula (141) above.
[1793] When there are multiple groups represented by the above general formula (141), the multiple groups represented by the above general formula (141) may be the same as or different from each other.
[1794] L 1401 for
[1795] single bond,
[1796] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1797] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1798] Ar 1401 for
[1799] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1800] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1801] mx4 can be 0, 1, 2, 3, 4, or 5.
[1802] 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.
[1803] In Ar 1401 In cases where there are two or more Ar, two or more Ar 1401 They are the same or different.
[1804] In the above general formula (141), * indicates the bonding position with the ring shown in the above general formula (14X).
[1805] Compounds represented by general formula (15X)
[1806] In the organic EL element involved in this embodiment, the first compound is preferably a compound represented by the following general formula (15X).
[1807]
Chemical Formula 81
[1808]
[1809] (In the above general formula (15X),
[1810] R 1501 ~R 1514 Each independently
[1811] hydrogen atom,
[1812] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1813] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1814] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1815] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1816] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1817] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1818] -O-(R 904 The groups shown in the figure,
[1819] -S-(R 905 The groups shown in the figure,
[1820] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1821] -C(=O)R 801 The groups shown
[1822] -COOR 802 The groups shown
[1823] Halogen atoms,
[1824] cyano,
[1825] Nitro,
[1826] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1827] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1828] The groups represented by the above general formula (151),
[1829] Among them, R 1501 ~R 1514 At least one of them is a group represented by the general formula (151) above.
[1830] When there are multiple groups represented by the above general formula (151), the multiple groups represented by the above general formula (151) may be the same as or different from each other.
[1831] L 15 01 is
[1832] single bond,
[1833] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1834] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1835] Ar 1501 for
[1836] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1837] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1838] mx5 can be 0, 1, 2, 3, 4, or 5.
[1839] 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.
[1840] In Ar 1501 In cases where there are two or more Ar, two or more Ar 1501 They are the same or different.
[1841] In the above general formula (151), * indicates the bonding position with the ring shown in the above general formula (15X).
[1842] Compounds represented by general formula (16X)
[1843] In the organic EL element involved in this embodiment, the first compound is preferably a compound represented by the following general formula (16X).
[1844]
Chemical Formula 82
[1845]
[1846] (In the above general formula (16X),
[1847] R 1601 ~R 1614 Each independently
[1848] hydrogen atom,
[1849] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[1850] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[1851] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[1852] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[1853] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[1854] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[1855] -O-(R 904 The groups shown in the figure,
[1856] -S-(R 905 The groups shown in the figure,
[1857] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[1858] -C(=O)R 801 The groups shown
[1859] -COOR 802 The groups shown
[1860] Halogen atoms,
[1861] cyano,
[1862] Nitro,
[1863] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[1864] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[1865] The groups represented by the above general formula (161),
[1866] Among them, R 1601 ~R 1614 At least one of them is a group represented by the general formula (161) above.
[1867] When there are multiple groups represented by the above general formula (161), the multiple groups represented by the above general formula (161) may be the same as or different from each other.
[1868] L 1601 for
[1869] single bond,
[1870] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[1871] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1872] Ar 1601 for
[1873] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[1874] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[1875] mx6 can be 0, 1, 2, 3, 4, or 5.
[1876] 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.
[1877] In Ar 1601 In cases where there are two or more Ar, two or more Ar 1601 They are the same or different.
[1878] In the above general formula (161), * indicates the bonding position with the ring shown in the above general formula (16X).
[1879] In both the first and second compounds, groups described as "substituted or unsubstituted" are preferably "unsubstituted".
[1880] (Method for manufacturing the first compound)
[1881] 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.
[1882] (Specific examples of the first compound)
[1883] 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.
[1884] In this specification, in specific examples of compounds, D represents a deuterium atom, Me represents a methyl group, and tBu represents a tert-butyl group.
[1885]
Chemical Formula 83
[1886]
[1887]
Chemical Formula 84
[1888]
[1889]
Chemical Formula 85
[1890]
[1891]
Chemical Formula 86
[1892]
[1893] [Chemical Formula 87]
[1894]
[1895]
Chemical Formula 88
[1896]
[1897]
Chemical Formula 89
[1898]
[1899] [Chemical Formula 90]
[1900]
[1901]
Chemical Formula 91
[1902]
[1903]
Chemical Formula 92
[1904]
[1905] [Chemical Formula 93]
[1906]
[1907] [Chemical Formula 94]
[1908]
[1909] [Chemical Formula 95]
[1910]
[1911] [Chemical Formula 96]
[1912]
[1913] [Chemical Formula 97]
[1914]
[1915]
Chemical Formula 98
[1916]
[1917]
Chemical Formula 99
[1918]
[1919]
Chemical Formula 100
[1920]
[1921]
Chemical Formula 101
[1922]
[1923]
Chemical Formula 102
[1924]
[1925]
Chemical Formula 103
[1926]
[1927] [Chemical Formula 104]
[1928]
[1929] [Chemical Formula 105]
[1930]
[1931] [Chemical Formula 106]
[1932]
[1933] [Chemical Formula 107]
[1934]
[1935] [Chemical Formula 108]
[1936]
[1937] [Chemical Formula 109]
[1938]
[1939]
Chemical Formula 110
[1940]
[1941]
Chemical Formula 111
[1942]
[1943]
Chemical Formula 112
[1944]
[1945]
Chemical Formula 113
[1946]
[1947]
Chemical Formula 114
[1948]
[1949]
Chemical Formula 115
[1950]
[1951]
Chemical Formula 116
[1952]
[1953]
Chemical Formula 117
[1954]
[1955]
Chemical Formula 118
[1956]
[1957]
Chemical Formula 119
[1958]
[1959]
Chemical Formula 120
[1960]
[1961]
Chemical Formula 121
[1962]
[1963]
Chemical Formula 122
[1964]
[1965]
Chemical Formula 123
[1966]
[1967] [Chemical Formula 124]
[1968]
[1969] [Chemical Formula 125]
[1970]
[1971] [Chemical Formula 126]
[1972]
[1973] [Chemical Formula 127]
[1974]
[1975] [Chemical Formula 128]
[1976]
[1977] [Chemical Formula 129]
[1978]
[1979]
Chemical Formula 130
[1980]
[1981]
Chemical Formula 131
[1982]
[1983]
Chemical Formula 132
[1984]
[1985]
Chemical Formula 133
[1986]
[1987] [Chemical Formula 134]
[1988]
[1989] [Chemical Formula 135]
[1990]
[1991]
Chemical Formula 136
[1992]
[1993]
Chemical Formula 137
[1994]
[1995] [Chemical Formula 138]
[1996]
[1997]
Chemical Formula 139
[1998]
[1999] [Chemical Formula 140]
[2000]
[2001]
Chemical Formula 141
[2002]
[2003] [Chemical Formula 142]
[2004]
[2005] [Chemical Formula 143]
[2006]
[2007] [Chemical Formula 144]
[2008]
[2009] [Chemical Formula 145]
[2010]
[2011] [Chemical Formula 146]
[2012]
[2013] [Chemical Formula 147]
[2014]
[2015] [Chemical Formula 148]
[2016]
[2017] [Chemical Formula 149]
[2018]
[2019] [Chemical Formula 150]
[2020]
[2021]
Chemical Formula 151
[2022]
[2023]
Chemical Formula 152
[2024]
[2025]
Chemical Formula 153
[2026]
[2027]
Chemical Formula 154
[2028]
[2029]
Chemical Formula 155
[2030]
[2031] [Chemical Formula 156]
[2032]
[2033] [Chemical Formula 157]
[2034]
[2035]
Chemical Formula 158
[2036]
[2037] [Chemical Formula 159]
[2038]
[2039] [Chemical Formula 160]
[2040]
[2041]
Chemical Formula 161
[2042]
[2043]
Chemical Formula 162
[2044]
[2045] [Chemical Formula 163]
[2046]
[2047] [Chemical Formula 164]
[2048]
[2049] [Chemical Formula 165]
[2050]
[2051]
Chemical Formula 166
[2052]
[2053] [Chemical Formula 167]
[2054]
[2055] [Chemical Formula 168]
[2056]
[2057] [Chemical Formula 169]
[2058]
[2059] [Chemical Formula 170]
[2060]
[2061]
Chemical Formula 171
[2062]
[2063] [Chemical Formula 172]
[2064]
[2065]
Chemical Formula 173
[2066]
[2067] [Chemical Formula 174]
[2068]
[2069] (Second main material)
[2070] In the organic EL element involved in this embodiment, the second host material is preferably an anthracene derivative.
[2071] In the organic EL element involved in this embodiment, the second host material is preferably the second compound shown in the following general formula (2).
[2072] [Chemical Formula 175]
[2073]
[2074] (In the above general formula (2),
[2075] R 201 ~R 208 Each independently
[2076] hydrogen atom,
[2077] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2078] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[2079] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2080] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2081] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2082] -Si(R 901 (R) 902 (R)903 The groups shown in the figure,
[2083] -O-(R 904 The groups shown in the figure,
[2084] -S-(R 905 The groups shown in the figure,
[2085] -N(R 906 (R) 907 The groups shown in the figure,
[2086] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[2087] -C(=O)R 801 The groups shown
[2088] -COOR 802 The groups shown
[2089] Halogen atoms,
[2090] cyano,
[2091] Nitro,
[2092] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2093] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2094] L 201 and L 202 Each independently
[2095] single bond,
[2096] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[2097] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2098] Ar 201 and Ar 202 Each independently
[2099] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2100] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2101] (In the second compound involved in this embodiment, R) 901 R 902 R 903 R 904 R 905 R 906 R907 R 801 and R 802 Each independently
[2102] hydrogen atom,
[2103] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2104] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2105] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2106] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2107] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[2108] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.
[2109] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[2110] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[2111] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.
[2112] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[2113] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.
[2114] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[2115] In R 802 In the case of multiple Rs, multiple Rs 802 (They may be the same or different.)
[2116] In the organic EL element involved in this embodiment, it is preferred that,
[2117] R 201 ~R 208 Each independently
[2118] hydrogen atom,
[2119] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2120] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms
[2121] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2122] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2123] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2124] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2125] -O-(R 904 The groups shown in the figure,
[2126] -S-(R 905 The groups shown in the figure,
[2127] -N(R 906 (R) 907 The groups shown in the figure,
[2128] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms
[2129] -C(=O)R 801 The groups shown
[2130] -COOR 802 The groups shown
[2131] Halogen atoms,
[2132] cyano, or
[2133] Nitro,
[2134] L 201 and L 202 Each independently
[2135] single bond,
[2136] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or
[2137] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2138] Ar 201 and Ar 202 Each independently
[2139] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2140] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[2141] In the organic EL element involved in this embodiment, the preferred one is...
[2142] L 201 and L 202 Each independently
[2143] single key, or
[2144] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms in a cyclic structure.
[2145] Ar 201 and Ar 202 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.
[2146] In the organic EL element involved in this embodiment,
[2147] Ar 201 and Ar 202 Each independently preferred
[2148] phenyl,
[2149] Naphthyl,
[2150] Fiki,
[2151] Biphenyl
[2152] Triphenyl
[2153] Diphenylfluorenyl,
[2154] Dimethylfluorenyl,
[2155] benzodiphenylfluorenyl,
[2156] benzodimethylfluorenyl,
[2157] Dibenzofuranyl,
[2158] Dibenzothiophene group,
[2159] Naphthobenzofuranyl, or
[2160] Naphthobenzothiophene group.
[2161] 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), or (209).
[2162] [Chemical Formula 176]
[2163]
[2164] [Chemical Formula 177]
[2165]
[2166] [Chemical Formula 178]
[2167]
[2168] [Chemical Formula 179]
[2169]
[2170] [Chemical Formula 180]
[2171]
[2172]
Chemical Formula 181
[2173]
[2174] [Chemical Formula 182]
[2175]
[2176]
Chemical Formula 183
[2177]
[2178] [Chemical Formula 184]
[2179]
[2180] (In the above general formulas (201) to (209),
[2181] L 201 and Ar 201 L in the above general formula (2) 201 and Ar 201 Same meaning
[2182] R 201 ~R 208 Each independently relates to R in the above general formula (2) 201~R 208 The meaning is the same.
[2183] 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).
[2184] [Chemical Formula 185]
[2185]
[2186] [Chemical Formula 186]
[2187]
[2188] [Chemical Formula 187]
[2189]
[2190]
Chemical Formula 188
[2191]
[2192] [Chemical Formula 189]
[2193]
[2194] [Chemical Formula 190]
[2195]
[2196]
Chemical Formula 191
[2197]
[2198] [Chemical Formula 192]
[2199]
[2200]
Chemical Formula 193
[2201]
[2202] (In the above general formulas (221), (222), (223), (224), (225), (226), (227), (228), and (229),
[2203] 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
[2204] L 201 and Ar 201 Each of the above general formulas (2) with L 201 and Ar 201 Same meaning
[2205] L 203 L in the above general formula (2) 201 Same meaning
[2206] L 203 With L 201 They are the same or different.
[2207] Ar 203 Ar in the above general formula (2) 201 Same meaning
[2208] Ar 203 with Ar 201 (They may be the same or different.)
[2209] 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).
[2210] [Chemical Formula 194]
[2211]
[2212] [Chemical Formula 195]
[2213]
[2214] [Chemical Formula 196]
[2215]
[2216] [Chemical Formula 197]
[2217]
[2218] [Chemical Formula 198]
[2219]
[2220]
Chemical Formula 199
[2221]
[2222] [Chemical Formula 200]
[2223]
[2224]
Chemical Formula 201
[2225]
[2226]
Chemical Formula 202
[2227]
[2228] (In the above general formulas (241), (242), (243), (244), (245), (246), (247), (248), and (249),
[2229] 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
[2230] L 201 and Ar 201 Each of the above general formulas (2) with L 201 and Ar 201 Same meaning
[2231] L 203 L in the above general formula (2) 201 Same meaning
[2232] L 203 With L 201 They are the same or different.
[2233] Ar 203 Ar in the above general formula (2) 201 Same meaning
[2234] Ar 203 with Ar 201 (They may be the same or different.)
[2235] In the second compound represented by the above general formula (2), the R group is not the group represented by the above general formula (21). 201 ~R 208 Each independently preferred
[2236] hydrogen atom,
[2237] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2238] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or
[2239] -Si(R 901 (R) 902 (R) 903 The group shown is ).
[2240] Preferred L 101 for
[2241] single key, or
[2242] Unsubstituted arylene groups with 6 to 22 carbon atoms in the cyclic group,
[2243] Ar101 is an aryl group with 6 to 22 carbon atoms, either substituted or unsubstituted.
[2244] In the organic EL element involved in this embodiment, in the second compound shown by the above general formula (2), R, as a substituent of the anthracene skeleton, 201 ~R 208 From the perspective of preventing the suppression of intermolecular interactions and inhibiting the decrease in electron mobility, hydrogen atoms are preferred, but R 201 ~R 208 It can also be an aryl group with 6 to 50 cyclic carbon atoms, substituted or unsubstituted, or a heterocyclic group with 5 to 50 cyclic atoms.
[2245] In R 201 ~R 208 When the substituents are sterically hindered, such as alkyl and cycloalkyl groups, intermolecular interactions are suppressed, resulting in a decrease in electron mobility relative to the first host material. This may prevent the μe(H1) < μe(H2) relationship described in the aforementioned mathematical formula (Formula 33) from being satisfied. When the second compound is used in the second luminescent layer, by satisfying the μe(H1) < μe(H2) relationship, it is expected that the decrease in the recombination ability of holes and electrons in the first luminescent layer and the decrease in luminous efficiency can be suppressed. It should be noted that as substituents, alkyl halogens, alkenyl groups, alkynyl groups, and -Si(R) are suitable choices. 901 (R) 902 (R) 903 The group shown is -O-(R) 904 The group shown is -S-(R) 905 The group shown is -N(R) 906 (R) 907 The groups shown are aralkyl groups, -C(=O)R 801 The indicated group, -COOR 802The groups, halogen atoms, cyano groups, and nitro groups shown may form high steric hindrance, while alkyl and cycloalkyl groups may form even higher steric hindrance.
[2246] In the second compound represented by the above general formula (2), R, as a substituent of the anthracene skeleton, 201 ~R 208 Preferably, the substituent is not a highly sterically hindered substituent; preferably, it is not alkyl or cycloalkyl; more preferably, it is not alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, or -Si(R) 901 (R) 902 (R) 903 The group shown is -O-(R) 904 The group shown is -S-(R) 905 The group shown is -N(R) 906 (R) 907 The groups shown are aralkyl groups, -C(=O)R 801 The indicated group, -COOR 802 The groups shown include halogen atoms, cyano groups, and nitro groups.
[2247] In the organic EL element involved in this embodiment,
[2248] In the second compound represented by the above general formula (2), R 201 ~R 208 Each independently preferred
[2249] hydrogen atom,
[2250] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2251] Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or
[2252] -Si(R 901 (R) 902 (R) 903 The group shown is ).
[2253] In the organic EL element of this embodiment, in the second compound represented by the above general formula (2), R 201 ~R 208 Hydrogen atoms are preferred.
[2254] In the second compound, R 201 ~R 208 When the expression "substituted or unsubstituted" is used, the substituents preferably do not include the substituents that may lead to high steric hindrance, especially substituted or unsubstituted alkyl groups and substituted or unsubstituted cycloalkyl groups. R 201 ~R 208When the substituent is described as "substituted or unsubstituted", it prevents the intermolecular interactions caused by the presence of highly sterically hindered substituents such as alkyl and cycloalkyl groups from being suppressed by not containing substituted or unsubstituted alkyl groups or substituted or unsubstituted cycloalkyl groups. This prevents the decrease in electron mobility. In addition, when such a second compound is used in the second light-emitting layer, it can suppress the decrease in the recombination ability of holes and electrons in the first light-emitting layer and the decrease in luminous efficiency.
[2255] Further preferred is that R, as a substituent of the anthracene skeleton, 201 ~R 208 It is not a sterically hindered substituent, but rather R as a substituent. 201 ~R 208 It is unsubstituted. Additionally, R, as a substituent in the anthracene skeleton... 201 ~R 208 In the case that it is not a highly sterically hindered substituent, R is a substituent with low steric hindrance. 201 ~R 208 In the case of top-bonded substituents, these substituents are preferably not sterically hindered substituents, and R as a substituent... 201 ~R 208 The substituent bonded above is preferably not alkyl or cycloalkyl, more preferably not alkyl, cycloalkyl, haloalkyl, alkenyl, ynyl, or -Si(R) 901 (R) 902 (R) 903 The group shown is -O-(R) 904 The group shown is -S-(R) 905 The group shown is -N(R) 906 (R) 907 The groups shown are aralkyl groups, -C(=O)R 801 The indicated group, -COOR 802 The groups shown include halogen atoms, cyano groups, and nitro groups.
[2256] In the second compound described above, the groups described as "substituted or unsubstituted" are preferably "unsubstituted".
[2257] In the organic EL element involved in this embodiment, for example, Ar in the second compound shown in the above general formula (2) 201 It is a substituted or unsubstituted dibenzofuranyl group.
[2258] In the organic EL element involved in this embodiment, for example, Ar in the second compound shown in the above general formula (2) 201 It is an unsubstituted dibenzofuranyl group.
[2259] In the organic EL element involved in this embodiment, for example, the second compound shown in the above general formula (2) has at least one hydrogen, of which at least one is deuterium.
[2260] In the organic EL element involved in this embodiment, for example, L in the second compound shown in the above general formula (2) 201 The range is from TEMP-63 to TEMP-68.
[2261]
Chemical Formula 203
[2262]
[2263] In the organic EL element involved in this embodiment, for example, Ar in the second compound shown in the above general formula (2) 201 To select freely substituted or unsubstituted anthracene groups,
[2264] Benzanthracene,
[2265] Fiki,
[2266] Benzphenanthrene,
[2267] Finadenyl,
[2268] Pyrene
[2269] base,
[2270] benzo[a] base,
[2271] Tri-phenylene,
[2272] Benzotrimethylene
[2273] phenoxytetraphenyl,
[2274] Pentaphenyl,
[2275] Fluoranthene group,
[2276] At least one group from the group consisting of benzo[anthracene] and peryl.
[2277] In the organic EL element involved in this embodiment, for example, Ar in the second compound shown in the above general formula (2) 201 The fluorene group can be substituted or unsubstituted.
[2278] In the organic EL element involved in this embodiment, for example, Ar in the second compound shown in the above general formula (2) 201 For substituted or unsubstituted thallium groups.
[2279] In the organic EL element involved in this embodiment, for example, Ar in the second compound shown in the above general formula (2)201 It is benzoxanthryl.
[2280] (Method for manufacturing the second compound)
[2281] 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.
[2282] (Specific example of the second compound)
[2283] 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.
[2284]
Chemical Formula 204
[2285]
[2286]
Chemical Formula 205
[2287]
[2288]
Chemical Formula 206
[2289]
[2290] [Chemical Formula 207]
[2291]
[2292] [Chemical Formula 208]
[2293]
[2294]
Chemical Formula 209
[2295]
[2296]
Chemical Formula 210
[2297]
[2298]
Chemical Formula 211
[2299]
[2300]
Chemical Formula 212
[2301]
[2302]
Chemical Formula 213
[2303]
[2304]
Chemical Formula 214
[2305]
[2306]
Chemical Formula 215
[2307]
[2308]
Chemical Formula 216
[2309]
[2310]
Chemical Formula 217
[2311]
[2312]
Chemical Formula 218
[2313]
[2314]
Chemical Formula 219
[2315]
[2316]
Chemical Formula 220
[2317]
[2318]
Chemical Formula 221
[2319]
[2320]
Chemical Formula 222
[2321]
[2322]
Chemical Formula 223
[2323]
[2324] [Chemical Formula 224]
[2325]
[2326] [Chemical Formula 225]
[2327]
[2328]
Chemical Formula 226
[2329]
[2330] [Chemical Formula 227]
[2331]
[2332] [Chemical Formula 228]
[2333]
[2334] [Chemical Formula 229]
[2335]
[2336]
Chemical Formula 230
[2337]
[2338]
Chemical Formula 231
[2339]
[2340]
Chemical Formula 232
[2341]
[2342]
Chemical Formula 233
[2343]
[2344]
Chemical Formula 234
[2345]
[2346] [Chemical Formula 235]
[2347]
[2348] [Chemical Formula 236]
[2349]
[2350] [Chemical Formula 237]
[2351]
[2352] [Chemical Formula 238]
[2353]
[2354] [Chemical Formula 239]
[2355]
[2356] [Chemical Formula 240]
[2357]
[2358]
Chemical Formula 241
[2359]
[2360]
Chemical Formula 242
[2361]
[2362] [Chemical Formula 243]
[2363]
[2364] [Chemical Formula 244]
[2365]
[2366] [Chemical Formula 245]
[2367]
[2368] [Chemical Formula 246]
[2369]
[2370] (First luminescent compound, second luminescent compound, and third luminescent compound)
[2371] In the organic EL element according to this embodiment, the first luminescent compound, the second luminescent compound, and the third luminescent compound can be exemplified by the following third compound and the following fourth compound. The third compound and the fourth compound are each independently selected from the group consisting of the compound shown in the following general formula (3), the compound shown in the following general formula (4), the compound shown in the following general formula (5), the compound shown in the following general formula (6), the compound shown in the following general formula (7), the compound shown in the following general formula (8), the compound shown in the following general formula (9), and the compound shown in the following general formula (10).
[2372] (The compound represented by general formula (3))
[2373] The compounds represented by general formula (3) will be described.
[2374] [Chemical Formula 247]
[2375]
[2376] (In the above general formula (3),
[2377] R 301 ~R 310 One or more of the groups consisting of two or more adjacent elements.
[2378] They bond together to form substituted or unsubstituted monocyclic rings.
[2379] They bond together to form substituted or unsubstituted fused rings, or
[2380] They do not bond with each other.
[2381] R 301 ~R 310 At least one of them is a monovalent group represented by the following general formula (31),
[2382] R that 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 (31) 301 ~R 310 Each independently
[2383] hydrogen atom,
[2384] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2385] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2386] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2387] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2388] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2389] -O-(R 904 The groups shown in the figure,
[2390] -S-(R 905 The groups shown in the figure,
[2391] -N(R 906 (R) 907 The groups shown in the figure,
[2392] Halogen atoms,
[2393] cyano,
[2394] Nitro,
[2395] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2396] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2397] [Chemical Formula 248]
[2398]
[2399] In the above general formula (31),
[2400] Ar 301 and Ar 302 Each independently
[2401] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2402] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2403] L 301 ~L 303 Each independently
[2404] single bond,
[2405] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or
[2406] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.
[2407] * indicates the bonding position in the pyrene ring in the above general formula (3).
[2408] In the third and fourth compounds, R 901 R 902 R 903 R 904 R 905 R 906 and R 907 Each independently
[2409] hydrogen atom,
[2410] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2411] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2412] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2413] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2414] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[2415] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[2416] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.
[2417] In R 902 In the case of multiple Rs, multiple Rs902 They are the same or different.
[2418] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.
[2419] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.
[2420] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.
[2421] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.
[2422] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.
[2423] In the above general formula (3), R is preferred. 301 ~R 310 Two of them are groups represented by the general formula (31) above.
[2424] In one embodiment, the compound represented by the above general formula (3) is the compound represented by the following general formula (33).
[2425] [Chemical Formula 249]
[2426]
[2427] (In the above general formula (33),
[2428] R 311 ~R 318 Each independently interacts with the R group in the above general formula (3) that is not a monovalent group represented by the above general formula (31). 301 ~R 310 Same meaning
[2429] L 311 ~L 316 Each independently
[2430] single bond,
[2431] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or
[2432] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.
[2433] Ar312 Ar 313 Ar 315 and Ar 316 Each independently
[2434] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2435] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2436] In the above general formula (31), L 301 Preferably a single bond, L 302 and L 303 Single bonds are preferred.
[2437] In one embodiment, the compound represented by the above general formula (3) is represented by the following general formula (34) or general formula (35).
[2438] [Chemical Formula 250]
[2439]
[2440] (In the above general formula (34),
[2441] R 311 ~R 318 Each independently interacts with the R group in the above general formula (3) that is not a monovalent group represented by the above general formula (31). 301 ~R 310 Same meaning
[2442] L 312 L 313 L 315 and L 316 Each independently relates to L in the above general formula (33) 312 L 313 L 315 and L 316 Same meaning
[2443] Ar 312 Ar 313 Ar 315 and Ar 316 Each independently relates to Ar in the above general formula (33) 312 Ar 313 Ar 315 and Ar 316 The meaning is the same.
[2444]
Chemical Formula 251
[2445]
[2446] (In the above general formula (35),
[2447] R 311 ~R 318 Each independently interacts with the R group in the above general formula (3) that is not a monovalent group represented by the above general formula (31). 301 ~R 310 Same meaning
[2448] Ar 312 Ar 313 Ar 315 and Ar 316 Each independently relates to Ar in the above general formula (33) 312 Ar 313 Ar 315 and Ar 316 The meaning is the same.
[2449] In the above general formula (31), Ar is preferred. 301 and Ar 302 At least one of them is a group represented by the following general formula (36).
[2450] In the above general formulas (33) to (35), Ar is preferred. 312 and Ar 313 At least one of them is a group represented by the following general formula (36).
[2451] In the above general formulas (33) to (35), Ar is preferred. 315 and Ar 316 At least one of them is a group represented by the following general formula (36).
[2452]
Chemical Formula 252
[2453]
[2454] (In the above general formula (36),
[2455] X3 represents an oxygen atom or a sulfur atom.
[2456] R 321 ~R 327 One or more of the groups consisting of two or more adjacent elements.
[2457] They bond together to form substituted or unsubstituted monocyclic rings.
[2458] They bond together to form substituted or unsubstituted fused rings, or
[2459] They do not bond with each other.
[2460] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 321 ~R 327Each independently constitutes a hydrogen atom,
[2461] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2462] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2463] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2464] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2465] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2466] -O-(R 904 The groups shown in the figure,
[2467] -S-(R 905 The groups shown in the figure,
[2468] -N(R 906 (R) 907 The groups shown in the figure,
[2469] Halogen atoms,
[2470] cyano,
[2471] Nitro,
[2472] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2473] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2474] * indicates that L 302 L 303 L 312 L 313 L 315 or L 316 (The bonding location.)
[2475] X3 is preferably an oxygen atom.
[2476] Preferred R 321 ~R 327 At least one of them is
[2477] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2478] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2479] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2480] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2481] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2482] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[2483] In the above general formula (31), Ar is preferred. 301 For the group represented by the above general formula (36), Ar 302 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[2484] In the above general formulas (33) to (35), Ar is preferred. 312 For the group represented by the above general formula (36), Ar 313 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[2485] In the above general formulas (33) to (35), Ar is preferred. 315 For the group represented by the above general formula (36), Ar 316 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.
[2486] In one embodiment, the compound represented by the above general formula (3) is represented by the following general formula (37).
[2487] [Chemical Formula 253]
[2488]
[2489] (In the above general formula (37),
[2490] R 311 ~R 318 Each independently interacts with the R group in the above general formula (3) that is not a monovalent group represented by the above general formula (31). 301 ~R 310 Same meaning
[2491] R 321 ~R 327 One or more of the groups consisting of two or more adjacent elements.
[2492] They bond together to form substituted or unsubstituted monocyclic rings.
[2493] They bond together to form substituted or unsubstituted fused rings, or
[2494] They do not bond with each other.
[2495] R 341 ~R 347One or more of the groups consisting of two or more adjacent elements.
[2496] They bond together to form substituted or unsubstituted monocyclic rings.
[2497] They bond together to form substituted or unsubstituted fused rings, or
[2498] They do not bond with each other.
[2499] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 321 ~R 327 and R 341 ~R 347 Each independently
[2500] hydrogen atom,
[2501] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2502] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2503] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2504] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2505] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2506] -O-(R 904 The groups shown in the figure,
[2507] -S-(R 905 The groups shown in the figure,
[2508] -N(R 906 (R) 907 The groups shown in the figure,
[2509] Halogen atoms,
[2510] cyano,
[2511] Nitro,
[2512] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2513] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2514] R 331 ~R 335 and R 351 ~R 355 Each independently
[2515] hydrogen atom,
[2516] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2517] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2518] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2519] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2520] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2521] -O-(R 904 The groups shown in the figure,
[2522] -S-(R 905 The groups shown in the figure,
[2523] -N(R 906 (R) 907 The groups shown in the figure,
[2524] Halogen atom, cyano group, nitro group,
[2525] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2526] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2527] As a compound represented by the above general formula (3), the following compounds can be cited as specific examples.
[2528] [Chemical Formula 254]
[2529]
[2530] [Chemical Formula 255]
[2531]
[2532] [Chemical Formula 256]
[2533]
[2534] [Chemical Formula 257]
[2535]
[2536] [Chemical Formula 258]
[2537]
[2538] (The compound represented by general formula (4))
[2539] The compounds represented by general formula (4) will be described.
[2540] [Chemical Formula 259]
[2541]
[2542] (In the above general formula (4),
[2543] Z can be independently represented by CRa or nitrogen atoms.
[2544] Rings A1 and A2 are each independent of each other.
[2545] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or
[2546] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2547] When there are multiple Ra, one or more groups consisting of two or more adjacent Ra are selected.
[2548] They bond together to form substituted or unsubstituted monocyclic rings.
[2549] They bond together to form substituted or unsubstituted fused rings, or
[2550] They do not bond with each other.
[2551] n21 and n22 are each independently 0, 1, 2, 3 or 4.
[2552] When there are multiple Rb, one or more groups consisting of two or more adjacent Rb are considered.
[2553] They bond together to form substituted or unsubstituted monocyclic rings.
[2554] They bond together to form substituted or unsubstituted fused rings, or
[2555] They do not bond with each other.
[2556] When there are multiple Rc, one or more groups are formed by two or more adjacent Rc.
[2557] They bond together to form substituted or unsubstituted monocyclic rings.
[2558] They bond together to form substituted or unsubstituted fused rings, or
[2559] They do not bond with each other.
[2560] Ra, Rb, and Rc, which do not form the aforementioned single rings and do not form the aforementioned fused rings, are each independently...
[2561] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2562] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2563] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2564] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2565] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2566] -O-(R 904 The groups shown in the figure,
[2567] -S-(R 905 The groups shown in the figure,
[2568] -N(R 906 (R) 907 The groups shown in the figure,
[2569] Halogen atoms,
[2570] cyano,
[2571] Nitro,
[2572] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2573] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2574] 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.
[2575] 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.
[2576] 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.
[2577] The "heterocyclic" rings A1 and A2 have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "heterocyclic group".
[2578] 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.
[2579] 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.
[2580] 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.
[2581] 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.
[2582] 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).
[2583] [Chemical Formula 260]
[2584] *-L 401 -Ar 401 (4a)
[2585] (In the above general formula (4a),
[2586] L 401 for
[2587] single bond,
[2588] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or
[2589] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.
[2590] Ar 401 for
[2591] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[2592] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[2593] The group represented by the following general formula (4b).
[2594]
Chemical Formula 261
[2595]
[2596] (In the above general formula (4b),
[2597] L 402 and L403 Each independently
[2598] single bond,
[2599] Substituted or unsubstituted arylene groups with 6 to 30 carbon atoms, or
[2600] Divalent heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted.
[2601] Ar 402 and Ar 403 The group formed
[2602] They bond together to form substituted or unsubstituted monocyclic rings.
[2603] They bond together to form substituted or unsubstituted fused rings, or
[2604] They do not bond with each other.
[2605] Ar does not form the aforementioned single ring and does not form the aforementioned fused ring 402 and A r 4 03 Each independently
[2606] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2607] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2608] In one embodiment, the compound represented by the above general formula (4) is represented by the following general formula (42).
[2609]
Chemical Formula 262
[2610]
[2611] (In the above general formula (42),
[2612] R 401 ~R 411 One or more of the groups consisting of two or more adjacent elements.
[2613] They bond together to form substituted or unsubstituted monocyclic rings.
[2614] They bond together to form substituted or unsubstituted fused rings, or
[2615] They do not bond with each other.
[2616] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 401 ~R 411 Each independently
[2617] hydrogen atom,
[2618] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2619] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2620] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2621] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2622] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2623] -O-(R 904 The groups shown in the figure,
[2624] -S-(R 905 The groups shown in the figure,
[2625] -N(R 906 (R) 907 The groups shown in the figure,
[2626] Halogen atoms,
[2627] cyano,
[2628] Nitro,
[2629] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2630] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2631] 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).
[2632] R 404 and R 411 Preferably, it is a group represented by the above general formula (4a).
[2633] 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.
[2634] 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.
[2635] [Chemical Formula 263]
[2636]
[2637] 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,
[2638] 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,
[2639] R 421 ~R 427 One or more of the groups consisting of two or more adjacent elements.
[2640] They bond together to form substituted or unsubstituted monocyclic rings.
[2641] They bond together to form substituted or unsubstituted fused rings, or
[2642] They do not bond with each other.
[2643] R 431 ~R 438 One or more of the groups consisting of two or more adjacent elements.
[2644] They bond together to form substituted or unsubstituted monocyclic rings.
[2645] They bond together to form substituted or unsubstituted fused rings, or
[2646] They do not bond with each other.
[2647] 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
[2648] hydrogen atom,
[2649] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2650] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2651] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2652] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2653] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2654] -O-(R 904 The groups shown in the figure,
[2655] -S-(R 905 The groups shown in the figure,
[2656] -N(R 906 (R) 907 The groups shown in the figure,
[2657] Halogen atoms,
[2658] cyano,
[2659] Nitro,
[2660] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2661] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2662] 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).
[2663] [Chemical Formula 264]
[2664]
[2665] [Chemical Formula 265]
[2666]
[2667]
Chemical Formula 266
[2668]
[2669] (In the above general formulas (41-3), (41-4), and (41-5),
[2670] Ring A1 is defined in the same way as in general formula (4) above.
[2671] R 421 ~R 427 Each independently relates to R in the above general formula (4-1) 421 ~R 427 Same meaning
[2672] R440 ~R 448 Each independently relates to R in the above general formula (42) 401 ~R 411 They have the same meaning.
[2673] 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...
[2674] Substituted or unsubstituted naphthalene ring, or
[2675] Substituted or unsubstituted fluorene ring.
[2676] 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...
[2677] Substituted or unsubstituted dibenzofuran rings,
[2678] Substituted or unsubstituted carbazole ring, or
[2679] Substituted or unsubstituted dibenzothiophene ring.
[2680] 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).
[2681] [Chemical Formula 267]
[2682]
[2683] [Chemical Formula 268]
[2684]
[2685] [Chemical Formula 269]
[2686]
[2687] [Chemical Formula 270]
[2688]
[2689]
Chemical Formula 271
[2690]
[2691] (In the above general formulas (461), (462), (463), (464), (465), (466), and (467),
[2692] R 421 ~R427 Each independently relates to R in the above general formula (4-1) 421 ~R 427 Same meaning
[2693] R 431 ~R 438 Each independently relates to R in the above general formula (4-2) 431 ~R 438 Same meaning
[2694] 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
[2695] X4 represents an oxygen atom, NR 801 or C(R) 802 (R) 803 ),
[2696] R 801 R 802 and R 803 Each independently
[2697] hydrogen atom,
[2698] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2699] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2700] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2701] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2702] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[2703] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[2704] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[2705] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
[2706] In R 803 In the case of multiple Rs, multiple Rs 803 (They may be the same or different.)
[2707] 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.
[2708] (The compound represented by general formula (45))
[2709] The compounds represented by general formula (45) will be described.
[2710]
Chemical Formula 272
[2711]
[2712] (In the above general formula (45),
[2713] 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.
[2714] in,
[2715] R 461 With R 462 The groups formed and R 462 With R 463 The groups do not simultaneously form a ring;
[2716] R 464 With R 465 The groups formed and R 465 With R 466 The groups do not simultaneously form a ring;
[2717] R 465 With R466 The groups formed and R 466 With R 467 The groups do not simultaneously form a ring;
[2718] R 468 With R 469 The groups formed and R 469 With R 470 The groups do not simultaneously form a ring; and
[2719] R 469 With R 470 The groups formed and R 470 With R 471 The groups formed do not simultaneously form a ring.
[2720] R 461 ~R 471 Two or more rings are formed that are identical or different from each other.
[2721] R that does not form the aforementioned single ring and does not form the aforementioned fused ring 461 ~R 471 Each independently
[2722] hydrogen atom,
[2723] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2724] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2725] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2726] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2727] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2728] -O-(R 904 The groups shown in the figure,
[2729] -S-(R 905 ), -N(R 906 (R) 907 The groups shown in the figure,
[2730] Halogen atoms,
[2731] cyano,
[2732] Nitro,
[2733] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2734] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)
[2735] 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.
[2736] 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).
[2737] 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).
[2738] [Chemical Formula 273]
[2739]
[2740] (In the above general formulas (451) to (457),
[2741] *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,
[2742] 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.
[2743] X 45 For C(R) 4512 (R) 4513 ), NR 4514 oxygen or sulfur atoms
[2744] R 4501 ~R 4506 and R4512 ~R 4513 One or more of the groups consisting of two or more adjacent elements.
[2745] They bond together to form substituted or unsubstituted monocyclic rings.
[2746] They bond together to form substituted or unsubstituted fused rings, or
[2747] They do not bond with each other.
[2748] 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.
[2749] [Chemical Formula 274]
[2750]
[2751] (In the above general formulas (458) to (460),
[2752] *1 and *2, and *3 and *4 respectively represent R n and R n+1 The two cyclic carbon atoms bonded above,
[2753] 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.
[2754] X 45 For C(R) 4512 (R) 4513 ), NR 4514 oxygen or sulfur atoms
[2755] R 4512 ~R 4513 and R 4515 ~R 4525 One or more of the groups consisting of two or more adjacent elements.
[2756] They bond together to form substituted or unsubstituted monocyclic rings.
[2757] They bond together to form substituted or unsubstituted fused rings, or
[2758] They do not bond with each other.
[2759] 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.
[2760] 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.
[2761] (i) In the above general formula (45), R n With R n+1 When the formed ring structure has substituents, the substituents,
[2762] (ii) R in the above general formula (45) that does not form a ring structure 461 ~R 471 as well as
[2763] (iii) R in equations (451) to (460) 4501 ~R 4514 R 4515 ~R 4525 Each is preferred to be independent of the other.
[2764] hydrogen atom,
[2765] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2766] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2767] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2768] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2769] -N(R 906 (R) 907 The groups shown in the figure,
[2770] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[2771] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or
[2772] Any group in the group consisting of the groups represented by the following general formulas (461) to (464).
[2773] [Chemical Formula 275]
[2774]
[2775] (In the above general formulas (461) to (464),
[2776] R d Each independently
[2777] hydrogen atom,
[2778] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2779] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2780] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2781] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2782] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2783] -O-(R 904 The groups shown in the figure,
[2784] -S-(R 905 The groups shown in the figure,
[2785] -N(R 906 (R) 907 The groups shown in the figure,
[2786] Halogen atoms,
[2787] cyano,
[2788] Nitro,
[2789] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2790] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2791] X 46 For C(R) 801 (R) 802 ), NR 803 oxygen or sulfur atoms
[2792] R 801 R 802 and R 803 Each independently
[2793] hydrogen atom,
[2794] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2795] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2796] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2797] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2798] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[2799] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[2800] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[2801] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
[2802] In R 803 In the case of multiple Rs, multiple Rs 803 They are the same or different.
[2803] p1 is 5.
[2804] p2 is 4.
[2805] p3 is 3.
[2806] p4 is 7.
[2807] In the above general formulas (461) to (464), each * independently represents a bonding position with the ring structure.
[2808] In the third and fourth compounds, R 901 ~R 907 Same as the definition above.
[2809] 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).
[2810] [Chemical Formula 276]
[2811]
[2812] [Chemical Formula 277]
[2813]
[2814] (In the above general formulas (45-1) to (45-6),
[2815] Each of the rings d to i is independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.
[2816] R 461 ~R 471 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.
[2817] 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).
[2818] [Chemical Formula 278]
[2819]
[2820] [Chemical Formula 279]
[2821]
[2822] (In the above general formulas (45-7) to (45-12),
[2823] Rings d to f, k, and j are each independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.
[2824] R 461 ~R 471 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.
[2825] 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).
[2826] [Chemical Formula 280]
[2827]
[2828]
Chemical Formula 281
[2829]
[2830]
Chemical Formula 282
[2831]
[2832] (In the above general formulas (45-13) to (45-21),
[2833] Each of the rings d to k is independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.
[2834] R 461 ~R 471 Each independently relates to R in the above general formula (45) 461 ~R 471 The meaning is the same.
[2835] Substituents that further have substituents, such as those found in the above-mentioned ring g or ring h, can be used as examples.
[2836] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2837] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms
[2838] The groups represented by the above general formula (461),
[2839] The groups represented by the above general formula (463), or
[2840] The group represented by the above general formula (464).
[2841] 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).
[2842] [Chemical Formula 283]
[2843]
[2844] (In the above general formulas (45-22) to (45-25),
[2845] X 46 and X 47 Each independently is C(R) 801 (R) 802 ), NR 803 oxygen or sulfur atoms
[2846] 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.
[2847] R 801 R 802 and R 803 Each independently
[2848] hydrogen atom,
[2849] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2850] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2851] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2852] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2853] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[2854] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[2855] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[2856] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
[2857] In R 803 In the case of multiple Rs, multiple Rs 803 (They may be the same or different.)
[2858] In one embodiment, the compound represented by the above general formula (45) is represented by the following general formulas (45-26).
[2859] [Chemical Formula 284]
[2860]
[2861] (In the above general formula (45-26),
[2862] X 46 For C(R) 801 (R) 802 ), NR 803 oxygen or sulfur atoms
[2863] 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.
[2864] R 801 R 802 and R803 Each independently
[2865] hydrogen atom,
[2866] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2867] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2868] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2869] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.
[2870] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or
[2871] Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms.
[2872] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.
[2873] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.
[2874] In R 803 In the case of multiple Rs, multiple Rs 803 (They may be the same or different.)
[2875] 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.
[2876] [Chemical Formula 285]
[2877]
[2878] [Chemical Formula 286]
[2879]
[2880] [Chemical Formula 287]
[2881]
[2882] [Chemical Formula 288]
[2883]
[2884] [Chemical Formula 289]
[2885]
[2886] [Chemical Formula 290]
[2887]
[2888]
Chemical Formula 291
[2889]
[2890]
Chemical Formula 292
[2891]
[2892] [Chemical Formula 293]
[2893]
[2894] [Chemical Formula 294]
[2895]
[2896] (The compound represented by general formula (5))
[2897] 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.
[2898] [Chemical Formula 295]
[2899]
[2900] (In the above general formula (5),
[2901] R 501 ~R 507 and R 511 ~R 517 One or more of the groups consisting of two or more adjacent elements.
[2902] They bond together to form substituted or unsubstituted monocyclic rings.
[2903] They bond together to form substituted or unsubstituted fused rings, or
[2904] They do not bond with each other.
[2905] 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
[2906] hydrogen atom,
[2907] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2908] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2909] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2910] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2911] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2912] -O-(R 904 The groups shown in the figure,
[2913] -S-(R 905 The groups shown in the figure,
[2914] -N(R 906 (R) 907 The groups shown in the figure,
[2915] Halogen atoms,
[2916] cyano,
[2917] Nitro,
[2918] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or
[2919] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.
[2920] R 521 and R 522 Each independently
[2921] hydrogen atom,
[2922] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms
[2923] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms
[2924] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms
[2925] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms
[2926] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,
[2927] -O-(R 904 The groups shown in the figure,
[2928] -S-(R905 The groups shown in the figure,
[2929] -N(R 906 (R) 907 The groups shown in the figure, [29...
Claims
1. An organic electroluminescent element having anode, cathode, Two or more light-emitting units disposed between the anode and the cathode, and A first cathode-side organic layer disposed between the anode and the cathode, At least one of the two or more light-emitting units is a stacked light-emitting unit. A first cathode-side organic layer is disposed on the cathode side of at least one of the stacked light-emitting units. The first cathode-side organic layer contains a phenanthroline compound with a phenanthroline skeleton. The stacked light-emitting unit includes a first light-emitting layer and a second light-emitting layer. The first light-emitting layer contains a first host material and a first luminescent compound that exhibits luminescence with a maximum peak wavelength below 500 nm. The second light-emitting layer contains a second host material and a second luminescent compound that exhibits luminescence with a maximum peak wavelength below 500 nm. The first main material and the second main material are different from each other. The first luminescent compound and the second luminescent compound may be 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 expression (Mathematical Expression 3). T1(H1)>T1(H2) …(Mathematical expression 3).
2. The organic electroluminescent element according to claim 1, wherein, The first host material has a structure in its molecule that meets either condition (i) or condition (ii). The second main material is an anthracene derivative. Condition (i): A biphenyl structure having a first benzene ring and a second benzene ring connected by a single bond, wherein at least one portion of the first benzene ring and the second benzene ring in the biphenyl structure other than the single bond is further connected by crosslinking. Condition (ii): having a linkage structure comprising a benzene ring and a naphthalene ring linked by a single bond, wherein the benzene ring and the naphthalene ring in the linkage structure are each further independently fused with a single ring or a fused ring, or not fused, and 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.
3. The organic electroluminescent element according to claim 2, wherein, The first host material has the structure of condition (i) in its molecules. 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.
4. The organic electroluminescent element according to claim 2, wherein, The first host material has the structure of condition (i) in its molecules. The first benzene ring and the second benzene ring in the biphenyl structure are further connected by crosslinking in two parts other than the single bond.
5. The organic electroluminescent element according to claim 2, wherein, The crosslinking involves double bonds.
6. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first host material is a first compound having at least one group represented by the following general formula (11) and 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), * indicates the bonding position with the pyrene ring in the general formula (1). 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.
7. The organic electroluminescent element according to claim 6, wherein, The first compound is represented by the following general formula (101), In the general formula (101), R 101 ~R 120 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, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. 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, 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. 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.
8. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first main material is a first compound represented by the following general formula (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), * 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), * 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), * 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), * 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), * 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), * 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.
9. The organic electroluminescent element according to claim 2, wherein, The first host material has the structure of condition (i) in its molecules. The first benzene ring and the second benzene ring in the biphenyl structure are further connected by crosslinking in two parts other than the single bond. The crosslinking does not include double bonds.
10. The organic electroluminescent element according to claim 2, wherein, The first host material has the structure of condition (ii) in the molecule.
11. The organic electroluminescent element according to claim 10, wherein, The crosslinking involves double bonds.
12. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The second main material is the second 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, 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.
13. The organic electroluminescent element according to claim 12, wherein, Ar 201 and Ar 202 Each independently Phenyl, Naphthyl, Fiki, Biphenyl Triphenyl Diphenylfluorenyl, Dimethylfluorenyl, benzodiphenylfluorenyl, benzodimethylfluorenyl, Dibenzofuranyl, Dibenzothiophene group, Naphthobenzofuranyl, or Naphthobenzothiophene group.
14. The organic electroluminescent element according to claim 12, wherein, The second compound represented by general formula (2) is a compound represented by the following general formulas (201), (202), (203), (204), (205), (206), (207), (208), or (209). In the general formulas (201) to (209), L 201 and Ar 201 L in the general formula (2) 201 and Ar 201 Same meaning R 201 ~R 208 Each independently relates to R in the general formula (2). 201 ~R 208 They have the same meaning.
15. The organic electroluminescent element according to claim 6, wherein, Groups described as "substituted or unsubstituted" are all "unsubstituted" groups.
16. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The phenanthroline compound is a compound having at least one group represented by the following general formula (21) and represented by the following general formula (20). In the general formula (20), X 21 ~X 28 Each independently consists of a nitrogen atom and CR. 21 Or carbon atoms bonded to the groups represented by the general formula (21), X 21 ~X 28 At least one of them is a carbon atom bonded to the group represented by the general formula (21). When there are multiple groups represented by the general formula (21), the multiple groups represented by the general formula (21) may be the same as or different from each other. Multiple R 21 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. 21 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 931 The groups shown -COOR 932 The groups shown -S(=O)2R 933 The groups shown -B(R 934 (R) 935 The groups shown in the figure, -P(=O)(R 936 (R) 937 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 (21), Ar2 is Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. p is 1, 2, 3, 4 or 5. When there are two or more Ar2 atoms, the two or more Ar2 atoms are either the same or different from each other. L2 is a single bond or a linking group. L2, as a linking group, is Substituted or unsubstituted linear, branched, or cyclic polyvalent aliphatic hydrocarbon groups with 1 to 50 carbon atoms. Substituted or unsubstituted cyclic groups of polyvalent aromatic hydrocarbons with 6 to 50 carbon atoms, Substituted or unsubstituted polyvalent heterocyclic groups with 5 to 50 cyclic atoms, or A multivalent, multi-linked group formed by bonding two or three groups selected from the polyvalent aromatic hydrocarbon cyclic group and the polyvalent heterocyclic group. The aromatic hydrocarbon cyclic group and the heterocyclic group constituting L2, which are the multiple linking groups, may be the same or different from each other. Adjacent groups may be bonded to each other to form a ring or may not be bonded to each other. Ar2 may bond with L2, which acts as a linking group, to form a ring, or they may not bond with each other. As a linking group, L2 is adjacent to the carbon atom bonded to L2. 21 ~X 28 any one of the carbon atoms or CR 21 R 21 They may bond together to form a ring, or they may not bond together. In the general formula (21), * indicates the bonding position with the ring shown in the general formula (20). In the phenanthroline compound, R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 931 R 932 R 933 R 934 R 935 R 936 and R 937 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 931 In the case of multiple Rs, multiple Rs 931 They are the same or different. In R 932 In the case of multiple Rs, multiple Rs 932 They are the same or different. In R 933 In the case of multiple Rs, multiple Rs 933 They are the same or different. In R 934 In the case of multiple Rs, multiple Rs 934 They are the same or different. In R 935 In the case of multiple Rs, multiple Rs 935 They are the same or different. In R 936 In the case of multiple Rs, multiple Rs 936 They are the same or different. In R 937 In the case of multiple Rs, multiple Rs 937 They are the same or different.
17. The organic electroluminescent element according to claim 16, wherein, Ar2 in the general formula (21) is a heterocyclic group with 5 to 40 cyclic carbons, either substituted or unsubstituted.
18. The organic electroluminescent element according to claim 16, wherein, As a heterocyclic group with 5 to 50 cyclic atoms in Ar2 of the general formula (21), it includes substituted or unsubstituted groups derived from the ring structure shown in the general formula (20).
19. The organic electroluminescent element according to claim 16, wherein, Ar2 in the general formula (21) is a substituted or unsubstituted fused aromatic hydrocarbon group with 8 to 20 carbon atoms.
20. The organic electroluminescent element according to claim 19, wherein, The fused aromatic hydrocarbon group with 8 to 20 carbon atoms is a group derived from any aromatic hydrocarbon selected from the group consisting of naphthalene, anthracene, benzo[e]acenaphthene, acethracene, benzo[e]anthracene, triphenylene, pyrene, β-triphenylene, fluorene, phenanthrene, fluoranthene and benzo[e]fluoranthene.
21. The organic electroluminescent element according to claim 19, wherein, Ar2 in the general formula (21) is a substituted or unsubstituted anthracene group.
22. The organic electroluminescent element according to claim 16, wherein, X of the general formula (20) 21 and X 28 The carbon atom is bonded to the group represented by the general formula (21).
23. The organic electroluminescent element according to claim 16, wherein, X of the general formula (20) 21 and X 28 One of them is a carbon atom bonded to the group represented by the general formula (21), X 21 and X 28 The other one is a carbon atom bonded to a hydrogen atom.
24. The organic electroluminescent element according to claim 16, wherein, X of the general formula (20) 21 ~X 28 Except for the carbon atoms bonded to the groups represented by the general formula (21), all other carbon atoms are CR. 21 .
25. The organic electroluminescent element according to claim 16, wherein, The phenanthroline compound is a compound represented by the following general formula (24). In the general formula (24), Multiple R 21 Each independently relates to R in the general formula (20) 21 Same meaning Multiple R 22 Each independently relates to R in the general formula (20) 21 Same meaning L2 has the same meaning as L2 in the general formula (21). p is 1, 2, 3, 4 or 5. Multiple R 22 The carbon atom from position 1 to position 10 of the anthracene ring is bonded to L2.
26. The organic electroluminescent element according to claim 25, wherein, The phenanthroline compound is a compound represented by the following general formula (24A) or general formula (24B). In the general formula (24A), Multiple R 21 Each independently relates to R in the general formula (20) 21 Same meaning Multiple R 22 Each independently relates to R in the general formula (20) 21 Same meaning L2 has the same meaning as L2 in the general formula (21). In the general formula (24B), Multiple R 21 Each independently relates to R in the general formula (20) 21 Same meaning Multiple R 22 Each independently relates to R in the general formula (20) 21 Same meaning L2 has the same meaning as L2 in the general formula (21).
27. The organic electroluminescent element according to claim 16, wherein, The phenanthroline compound is a compound represented by the following general formula (25). In the general formula (25), Multiple R 21 Each independently relates to R in the general formula (20) 21 Same meaning Multiple R 22 Each independently relates to R in the general formula (20) 21 Same meaning L2 has the same meaning as L2 in the general formula (21). p is 1, 2, 3, 4 or 5. Multiple R 22 The carbon atom from position 2 to position 9 of the phenanthroline ring that is bonded to L2.
28. The organic electroluminescent element according to claim 16, wherein, The phenanthroline compound is a compound represented by the following general formula (25A). In the general formula (25A), Multiple R 21 Each independently relates to R in the general formula (20) 21 Same meaning Multiple R 22 Each independently relates to R in the general formula (20) 21 Same meaning L2 has the same meaning as L2 in the general formula (21).
29. The organic electroluminescent element according to any one of claims 25 to 28, wherein, The L2 in the general formulas (24), (24A), (24B), (25) or (25A) is a single bond, a substituted or unsubstituted aryl group with 6 to 50 cyclic carbon atoms, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 cyclic atoms.
30. The organic electroluminescent element according to claim 16, wherein, The phenanthroline compound is a compound represented by the following general formula (25B), (25C), (25D), or (25E). In the general formula (25B), Multiple R 21 Each independently relates to R in the general formula (20) 21 Same meaning Multiple R 22 Each independently relates to R in the general formula (20) 21 Same meaning L3 is a linking group; L3 as a linking group is Substituted or unsubstituted linear, branched, or cyclic polyvalent aliphatic hydrocarbon groups with 1 to 50 carbon atoms. Substituted or unsubstituted polyvalent amino groups Substituted or unsubstituted cyclic groups of polyvalent aromatic hydrocarbons with 6 to 50 carbon atoms, Substituted or unsubstituted polyvalent heterocyclic groups with 5 to 50 cyclic atoms, or A multivalent, multi-linked group formed by bonding two or three groups selected from the polyvalent aromatic hydrocarbon cyclic group and the polyvalent heterocyclic group. The aromatic hydrocarbon cyclic group and the heterocyclic group constituting L3, which are the multiple linking groups, may be the same or different from each other. Adjacent groups may be bonded to each other to form a ring or may not be bonded to each other. p is 1, 2, 3, 4 or 5. Multiple R 22 The carbon atom from position 1 to position 10 of the phenanthrene ring is bonded to L3. In the general formula (25C), Multiple R 21 Each independently relates to R in the general formula (20) 21 Same meaning R 221 ~R 230 Among them, one is a single bond bonded to L3, and the other is an R bond bonded to L3. 221 ~R 230 Each independently relates to R in the general formula (20) 21 Same meaning L3 is a linking group, and the meaning of L3 as a linking group is the same as that of L3 as a linking group in the general formula (25B). p is 1, 2, 3, 4 or 5. In the general formula (25D), Multiple R 21 Each independently relates to R in the general formula (20) 21 Same meaning R 221 ~R 232 Among them, one is a single bond bonded to L3, and the other is an R bond bonded to L3. 221 ~R 232 Each independently relates to R in the general formula (20) 21 Same meaning L3 is a linking group, and the meaning of L3 as a linking group is the same as that of L3 as a linking group in the general formula (25B). p is 1, 2, 3, 4 or 5. In the general formula (25E), Multiple R 21 Each independently relates to R in the general formula (20) 21 Same meaning R 221 ~R 230 Among them, one is a single bond bonded to L3, and the other is an R bond bonded to L3. 221 ~R 230 Each independently relates to R in the general formula (20) 21 Same meaning L3 is a linking group, and the meaning of L3 as a linking group is the same as that of L3 as a linking group in the general formula (25B). p can be 1, 2, 3, 4 or 5.
31. The organic electroluminescent element according to claim 30, wherein, The L3 in the general formula (25B), (25C), (25D) or (25E) is a substituted or unsubstituted aryl group with 6 to 50 cyclic carbon atoms, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 cyclic atoms.
32. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The second light-emitting layer of the stacked light-emitting unit is disposed between the first light-emitting layer and the first cathode-side organic layer.
33. The organic electroluminescent element according to claim 32, wherein, A second cathode-side organic layer is disposed between the second light-emitting layer and the first cathode-side organic layer.
34. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first light-emitting layer of the stacked light-emitting unit is disposed between the second light-emitting layer and the first cathode-side organic layer.
35. The organic electroluminescent element according to claim 34, wherein, A second cathode-side organic layer is disposed between the first light-emitting layer and the first cathode-side organic layer.
36. The organic electroluminescent element according to claim 33 or 35, wherein, The second cathode-side organic layer does not contain phenanthroline compounds with a phenanthroline skeleton.
37. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first light-emitting layer is spaced at least 30 nm apart from the first cathode-side organic layer.
38. The organic electroluminescent element according to claim 1, wherein, 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 5). T1(H1)-T1(H2)>0.03eV …(Mathematical formula 5).
39. The organic electroluminescent element according to claim 1, wherein, The first luminescent compound is a fluorescent compound that exhibits fluorescence emission with a maximum peak wavelength of less than 500 nm.
40. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first luminescent compound is a compound whose molecule does not contain an azazine ring structure.
41. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first light-emitting layer does not contain metal complexes.
42. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first light-emitting layer does not contain boron-containing complexes.
43. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first light-emitting layer does not contain phosphorescent materials.
44. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first luminescent layer does not contain heavy metal complexes or phosphorescent rare earth metal complexes.
45. The organic electroluminescent element according to claim 1, wherein, The singlet state energy S1(H1) of the first host material and the singlet state energy S1(D1) of the first luminescent compound satisfy the following mathematical expression (Mathematical Expression 20). S1(H1)>S1(D1) …(Mathematical formula 20).
46. The organic electroluminescent element according to claim 1, wherein, The triplet energy T1(H1) of the first host material and the triplet energy T1(D1) of the first luminescent compound satisfy the following mathematical expression (Mathematical Expression 20A). T1(D1)>T1(H1) …(Mathematical expression 20A).
47. The organic electroluminescent element according to claim 1, wherein, The second luminescent compound is a fluorescent compound that exhibits fluorescence emission with a maximum peak wavelength below 500 nm.
48. The organic electroluminescent element according to claim 1, wherein, The triplet energy T1(D2) of the second luminescent compound and the triplet energy T1(H2) of the second host material satisfy the following mathematical expression (Mathematical Expression 3A). T1(D2)>T1(H2) …(Mathematical expression 3A).
49. The organic electroluminescent element according to claim 1, wherein, The singlet state energy S1(H2) of the second host material and the singlet state energy S1(D2) of the second luminescent compound satisfy the following mathematical expression (Mathematical Expression 4). S1(H2)>S1(D2) …(Mathematical formula 4).
50. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The second light-emitting layer does not contain phosphorescent materials.
51. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The second luminescent layer does not contain heavy metal complexes or phosphorescent rare earth metal complexes.
52. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first luminescent compound and the second luminescent compound are each independently one or more compounds selected from the group consisting of compounds represented by general formula (3), general formula (4), general formula (5), general formula (6), general formula (7), general formula (8), general formula (9), and general formula (10). In the general formula (3), R 301 ~R 310 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 301 ~R 310 At least one of them is a monovalent group represented by the following general formula (31), R that does not form the monocyclic ring, does not form the fused ring, and is not a monovalent group represented by the following general formula (31) 301 ~R 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 (31), Ar 301 and Ar 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. L 301 ~L 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. * indicates the bonding position in the pyrene ring in the general formula (3). 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 between 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 R, 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 in the group is bonded to each other to form a divalent group as shown in the following general formula (82). R 805 With R 806 R 806 With R 807 and R 807 With R 808 At least one group in the group is bonded to each other to form a divalent group as shown in the following general formula (83). 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 represents an oxygen atom, a sulfur atom, or NR. 809 , 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 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), * indicates the bonding position with the ring structure shown in general formula (8), the group shown in general formula (82), or the group shown in 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 are bonded to the structure shown in the following general formula (92). 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 asterisks in the general formula (10b) are 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 first luminescent compound and the second luminescent 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.
53. The organic electroluminescent element according to claim 6, wherein, When expressed as "substituted or unsubstituted", the substituent is Unsubstituted alkyl groups having 1 to 50 carbon atoms Unsubstituted aryl groups with 6 to 50 carbon atoms, or Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms.
54. The organic electroluminescent element according to claim 6, wherein, When expressed as "substituted or unsubstituted", the substituent is Unsubstituted alkyl groups having 1 to 18 carbon atoms Unsubstituted aryl groups with 6 to 18 carbon atoms, or Unsubstituted heterocyclic groups with 5 to 18 cyclic atoms.
55. The organic electroluminescent element according to claim 1, wherein, The first luminescent compound is a compound that exhibits luminescence with a maximum peak wavelength of 430 nm or higher and 480 nm or lower.
56. The organic electroluminescent element according to claim 1, wherein, The second luminescent compound is a compound that exhibits luminescence with a maximum peak wavelength of 430 nm or higher and 480 nm or lower.
57. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The two or more light-emitting units include the stacked light-emitting units and at least one phosphorescent light-emitting unit that is different from the stacked light-emitting units. The phosphorescent unit contains a phosphorescent compound that exhibits phosphorescence.
58. The organic electroluminescent element according to claim 57, wherein, The phosphorescent compound is an iridium complex, a copper complex, a platinum complex, an osmium complex, or a gold complex.
59. The organic electroluminescent element according to claim 57, wherein, The phosphorescent unit has at least one phosphorescent layer containing the phosphorescent compound.
60. The organic electroluminescent element according to claim 59, wherein, The phosphorescent unit has two or more phosphorescent layers.
61. The organic electroluminescent element according to claim 60, wherein, The phosphorescent light-emitting layers are in direct contact with each other.
62. The organic electroluminescent element according to claim 60, wherein, The phosphorescent light-emitting layers are not in direct contact with each other.
63. The organic electroluminescent element according to claim 60, wherein, The phosphorescent unit has a green phosphorescent layer containing a phosphorescent compound with green luminescence and a red phosphorescent layer containing a phosphorescent compound with red luminescence.
64. The organic electroluminescent element according to claim 63, wherein, Green light emission refers to light emission with a maximum peak wavelength in the emission spectrum between 500 nm and 550 nm, while red light emission refers to light emission with a maximum peak wavelength in the emission spectrum between 600 nm and 640 nm.
65. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The two or more light-emitting units do not include phosphorescent units containing phosphorescent compounds that exhibit phosphorescent emission.
66. The organic electroluminescent element according to claim 1, wherein, The two or more light-emitting units contain intermediate units between them. The intermediate unit includes the first cathode-side organic layer.
67. The organic electroluminescent element according to claim 1, wherein, An intermediate unit is disposed on the cathode side of at least one of the stacked light-emitting units. The intermediate unit includes the first cathode-side organic layer.
68. The organic electroluminescent element according to claim 66 or 67, wherein, The intermediate unit comprises at least one N layer and at least one P layer. The N layer is configured to be closer to the anode side than the P layer. The intermediate unit includes the first cathode-side organic layer as the N layer.
69. The organic electroluminescent element according to claim 68, wherein, The intermediate unit has a first N layer disposed on the anode side and a second N layer disposed further on the cathode side than the first N layer as a plurality of N layers.
70. The organic electroluminescent element according to claim 69, wherein, The second N layer is the organic layer on the first cathode side.
71. The organic electroluminescent element according to claim 68, wherein, The N-layer comprises π-electron-deficient compounds and electron-donating materials. The π-electron-deficient compound is a compound that can coordinate with metal atoms.
72. The organic electroluminescent element according to claim 71, wherein, The π-electron-deficient compounds are selected from phenanthroline compounds, benzimidazole compounds, azazine compounds, and hydroxyquinoline.
73. The organic electroluminescent element according to claim 68, wherein, The P layer is a layer containing the acceptor material.
74. The organic electroluminescent element according to claim 73, wherein, The acceptor material is selected from 4,4',4''-Tris(N,N-diphenylamino)triphenylamine, 4,4',4''-Tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine, 4,4'-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl, 4,4'-Bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl, 1,3,5-Tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene, 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole, 3,6-Bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole, 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole, and Dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarboxylonitrile.
75. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The organic layer containing phenanthrene compounds is disposed in the two or more light-emitting units, and is disposed further away from the cathode side of the light-emitting unit closest to the cathode side.
76. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The organic layer containing phenanthrene compounds is not disposed among the two or more light-emitting units, but is disposed further away from the cathode side of the light-emitting unit closest to the cathode side.
77. The organic electroluminescent element according to any one of claims 1 to 5, wherein, It contains two or more of the aforementioned stacked light-emitting units.
78. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The first cathode-side organic layer is disposed between the stacked light-emitting unit and another light-emitting unit that is different from the stacked light-emitting unit.
79. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The hole mobility μh(H1) of the first host material and the hole mobility μh(H2) of the second host material satisfy the following mathematical expression (Mathematical Expression 31). μh(H1)>μh(H2) …(Mathematical formula 31).
80. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The hole mobility μh(H1), electron mobility μe(H1), hole mobility μh(H2), and electron mobility μe(H2) of the first host material satisfy the following mathematical expression (Mathematical Expression 32). (μe(H1) / μh(H1))<(μe(H2) / μh(H2)) …(Mathematical formula 32).
81. The organic electroluminescent element according to any one of claims 1 to 5, wherein, The electron mobility μe(H1) of the first host material and the electron mobility μe(H2) of the second host material satisfy the following mathematical expression (Mathematical Expression 33). μe(H1)<μe(H2) …(Mathematical formula 33).
82. The organic electroluminescent element according to any one of claims 1 to 5, wherein, It has a color conversion section disposed on the light extraction side of the organic electroluminescent element.
83. The organic electroluminescent element according to claim 1, wherein, The phenanthroline compound is selected from the following compounds: ET9, ET10, and ET11. The first host material is a compound selected from the following compounds: BH1, BH1-2, BH1-3, and BH1-4. The second host material is a compound selected from the following compounds: BH2-8, BH2-19, and BH2-30. 。 84. The organic electroluminescent element according to claim 1, 38, 46 or 48, 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. Conversion formula (F1): T1 = 1239.85 / λ edge , It should be noted that the unit of T1 is eV, and λ edge The unit is nm.
85. The organic electroluminescent element according to claim 45 or 49, 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. For the downward-pointing tangent on the longer wavelength side of the absorption spectrum, the wavelength value λedge at the intersection of the tangent and the horizontal axis was substituted into the conversion formula (F2) shown later to calculate the singlet energy S1. In this formula, the vertical axis of the absorption spectrum represents the absorption intensity, and the horizontal axis represents the wavelength. Conversion formula (F2): S1 = 1239.85 / λedge, It should be noted that the unit of S1 is eV, and the unit of λedge is nm.
86. The organic electroluminescent element according to claim 1, 39, 47, 55, 56 or 64, wherein, The maximum peak wavelength of a compound refers to the wavelength of the compound prepared as the test target, measured at 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 300K. The peak wavelength of the emission spectrum in which the emission intensity reaches its maximum was determined. The vertical axis of the emission spectrum represents the emission intensity, and the horizontal axis represents the wavelength.
87. The organic electroluminescent element according to any one of claims 1 to 5, used in a display for a television, personal computer, tablet computer or mobile device.
88. An electronic device comprising an organic electroluminescent element according to any one of claims 1 to 86.
89. The electronic device of claim 88, wherein it is a display for a television, personal computer, tablet computer or mobile device.
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