Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device

Abstract

Provided are a compound represented by the following formula (1), an organic electroluminescent element comprising the compound, and an electronic device comprising the organic electroluminescent element. The symbols in formula (1) are the same as those defined in the specification.

Description

Technical Field

[0001] This invention relates to compounds, materials for organic electroluminescent elements, organic electroluminescent elements, and electronic devices comprising the organic electroluminescent elements. Background Art

[0002] Generally, organic electroluminescent devices (hereinafter sometimes referred to as "organic EL devices") consist of an anode, a cathode, and an organic layer sandwiched between the anode and cathode. When a voltage is applied between the two electrodes, electrons are injected into the luminescent region from the cathode side, and holes are injected into the luminescent region from the anode side. The injected electrons and holes recombine in the luminescent region to generate an excited state, which emits light when it returns to the ground state. Therefore, the development of materials that efficiently transport electrons or holes to the luminescent region and facilitate electron-hole recombination to efficiently generate excitons, as well as finding suitable combinations of these materials, are crucial for obtaining high-performance organic EL devices.

[0003] Patent documents 1-4 disclose compounds used as materials for organic electroluminescent elements.

[0004] Existing technical documents

[0005] Patent Literature

[0006] Patent Document 1: International Publication No. 2022 / 009999

[0007] Patent Document 2: International Publication No. 2019 / 185061

[0008] Patent Document 3: Chinese Patent Publication No. 112430225

[0009] Patent Document 4: Chinese Patent Publication No. 108689972 Summary of the Invention

[0010] Problems to be solved by the invention

[0011] In the past, many compounds for organic EL devices have been reported, but there is still a need to further improve the performance of organic EL devices.

[0012] The present invention was made to solve the above-mentioned problems, and its object is to provide a compound that further improves the performance of an organic EL element, an organic EL element whose performance is further improved by including a specific compound, and an electronic device including such an organic EL element.

[0013] means for solving problems

[0014] The inventors have conducted repeated and in-depth studies on the performance of organic EL elements containing compounds described in Patent Documents 1 to 4, and have found that the performance of organic EL elements containing compounds represented by the following formula (1) is further improved.

[0015] In one embodiment, the present invention provides a compound represented by the following formula (1).

[0016] [Chemical Formula 1]

[0017]

[0018] (In formula (1),)

[0019] N ＊ The central nitrogen atom.

[0020] R 1 ~R 4 Each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted cyclic aryl group having 6 to 12 carbon atoms.

[0021] Selected from R 1 ~R 4 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0022] L 1 ~L 4 Each is independently a single bond, an unsubstituted aryl group with 6 to 30 carbon atoms in the cyclic ring, or an unsubstituted divalent heterocyclic group with 5 to 30 carbon atoms in the cyclic ring.

[0023] Ar 1 and Ar 2 Each of the following groups is independently an aryl group consisting of a six-membered ring with 6 to 30 carbon atoms, a heterocyclic group consisting of 5 to 30 carbon atoms, or a group represented by formula (a) below.

[0024]

Chemical Formula 2

[0025]

[0026] (in formula (a),

[0027] *1 is related to L 1 or L 2 The bonding positions.

[0028] R a and R b Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic group having 5 to 30 heterocyclic atoms.

[0029] Ra and R b They can bond with each other to form substituted or unsubstituted rings, or they can not bond with each other and therefore not form rings.

[0030] Selected from R 21 ~R 28 One of them is a single bond bonded to *2, not the R of the single bond bonded to *2. 21 ~R 28 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 cyclic atoms.

[0031] Selected from R that is not one of the above single bonds 21 ~R 28 Two adjacent benzene rings can bond together to form one or more unsubstituted benzene rings, or they can not bond together and thus not form a ring.

[0032] Among them, in R a and R b When they bond together with the carbon atom at position 9 of the fluorene framework to form a substituted or unsubstituted spirofluorene ring, selected from R 22 ~R 27 One of them is a single bond that bonds with *2.

[0033] In L 1 ~L 4 All are single bonds, Ar 1 and Ar 2 The group is shown in formula (a) and R 22 or R 27 In the case of a single bond bonded to *2, selected from 2 R a and 2 R b At least one of the atoms is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms in a cyclic structure.

[0034] Ar 3 It is the group represented by the following formula (x).

[0035]

Chemical Formula 3

[0036]

[0037] (in formula (x),

[0038] *3 is related to L 4 The bonding positions.

[0039] R 31 ~R 38 R 41 ~R 44 and R 51~R 58 Each of the following groups is independently composed of a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group with 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 50 carbon atoms, or a -Si(R group). 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 group shown in the figure, substituted or unsubstituted aryl group with 6 to 50 carbon atoms, or substituted or unsubstituted heterocyclic group with 5 to 50 cyclic atoms,

[0040] R 901 ~R 907 Each of the following groups is independently composed of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0041] In R 901 In the case of two or more R, two or more R 901 They are the same or different.

[0042] In R 902 In the case of two or more R, two or more R 902 They are the same or different.

[0043] In R 903 In the case of two or more R, two or more R 903 They are the same or different.

[0044] In R 904 In the case of two or more R, two or more R 904 They are the same or different.

[0045] In R 905 In the case of two or more R, two or more R 905 They are the same or different.

[0046] In R 906 In the case of two or more R, two or more R 906 They are the same or different.

[0047] In R 907 In the case of two or more R, two or more R 907 They are the same or different.

[0048] m is 0 or 1, and n is 0 or 1.

[0049] When m and n are 0, R 31 and R 32 R 32 and R 33 or R 33 and R 34 One of them is a single bond bonded to *a, and the other is a single bond bonded to *b.

[0050] R selected from single bonds that are not bonded to *a and *b 31 ~R 38 and R 41 ~R 44 One of them is a single bond that bonds with *4.

[0051] When m is 1 and n is 0, R 31 and R 32 R 32 and R 33 or R 33 and R 34 One of them is a single bond bonded to *a, and the other is a single bond bonded to *b.

[0052] R 35 and R 36 R 36 and R 37 or R 37 and R 38 One of them is a single bond that bonds with *c, and the other is a single bond that bonds with *d.

[0053] R selected from single bonds that are not bonded to *a and *b 31 ~R 34 R is not a single bond that bonds with *c and *d. 35 ~R 38 R 41 ~R 44 and R 51 ~R 54 One of them is a single bond that bonds with *4.

[0054] When m is 0 and n is 1, R 31 and R 32 R 32 and R 33 or R 33 and R 34 One of them is a single bond bonded to *a, and the other is a single bond bonded to *b.

[0055] R 35 and R 36 R36 and R 37 or R 37 and R 38 One of them is a single bond that bonds with *e, and the other is a single bond that bonds with *f.

[0056] R selected from single bonds that are not bonded to *a and *b 31 ~R 34 R is not a single bond that bonds with *e and *f. 35 ~R 38 R 41 ~R 44 and R 55 ~R 58 One of them is a single bond that bonds with *4.

[0057] When m is 1 and n is 1, R 31 and R 32 R 32 and R 33 or R 33 and R 34 One of them is a single bond bonded to *a, and the other is a single bond bonded to *b.

[0058] R 35 and R 36 R 36 and R 37 and R 37 and R 38 In any of these three groups, one bond is a single bond bonded to *c, and the other is a single bond bonded to *d.

[0059] R 35 and R 36 R 36 and R 37 or R 37 and R 38 In the remaining two groups, one of them is a single bond bonded to *e, and the other is a single bond bonded to *f.

[0060] R selected from single bonds that are not bonded to *a and *b 31 ~R 34 R is not a single bond that bonds with *c to *f. 35 ~R 38 R 41 ~R 44 and R 51 ~R 58 One of them is a single bond that bonds with *4.

[0061] Among them, in L 3 and L 4 For single bonds, m and n are 0, R33 For a single bond bonded to *a and R 34 For a single bond or R bond that bonds with *b 34 For a single bond bonded to *a and R 33 In the case of a single bond bonded to *b, selected from R 31 R 32 R 35 ~R 37 and R 41 ~R 44 One of them is a single bond that bonds with *4.

[0062] In L 3 and L 4 For single bonds, m and n are 0, R 31 For a single bond bonded to *a and R 32 In the case of a single bond bonded to *b, selected from R 33 ~R 38 and R 42 ~R 44 One of them is a single bond that bonds with *4.

[0063] In L 3 and L 4 For single bonds, m and n are 0, R 32 For a single bond bonded to *a and R 31 In the case of a single bond bonded to *b, selected from R 33 ~R 38 and R 41 ~R 43 One of them is a single bond that bonds with *4.

[0064] X 1 It consists of oxygen or sulfur atoms.

[0065] In another embodiment, the present invention provides a material for an organic EL element comprising the compound shown in formula (1) above.

[0066] In another embodiment, the present invention provides an organic electroluminescent element comprising a cathode, an anode, and an organic layer located between the cathode and the anode, the organic layer comprising a light-emitting layer, at least one layer of the organic layer containing a compound represented by formula (1) above.

[0067] In another embodiment, the present invention provides an electronic device comprising the aforementioned organic electroluminescent element.

[0068] The effects of the invention

[0069] Organic EL elements containing the compound shown in formula (1) above exhibit improved element performance. Attached Figure Description

[0070] Figure 1 This is a schematic diagram illustrating an example of the layer configuration of an organic EL element according to one aspect of the present invention.

[0071] Figure 2 This is a schematic diagram illustrating another example of the layer configuration of an organic EL element according to one aspect of the present invention.

[0072] Figure 3 This is a schematic diagram illustrating yet another example of the layer configuration of an organic EL element according to one aspect of the present invention. Detailed Implementation

[0073] [definition]

[0074] In this specification, a hydrogen atom means an isotope containing different numbers of neutrons, namely protium, deuterium, and tritium.

[0075] 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.

[0076] 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.

[0077] 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.

[0078] In this specification, the number of cyclic atoms refers to the number of atoms constituting the ring itself in compounds with a cyclic structure (e.g., monocyclic, fused-ring, and ring assemblies). Atoms that do not constitute the ring (e.g., hydrogen atoms ending 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.

[0079] 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.

[0080] 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.

[0081] In this specification, "unsubstituted ZZ group" means "substituted or unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".

[0082] 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.

[0083] 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.

[0084] Substituents described in this specification

[0085] The substituents described in this specification are explained below.

[0086] 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.

[0087] 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.

[0088] 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.

[0089] 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.

[0090] 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.

[0091] 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.

[0092] 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.

[0093] 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.

[0094] 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.

[0095] • "Substituted or unsubstituted aryl groups"

[0096] 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.

[0097] "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.

[0098] • Unsubstituted aryl groups (specific example group G1A):

[0099] phenyl,

[0100] p-phenyl,

[0101] metaphenyl,

[0102] o-phenyl,

[0103] p-terphenyl-4-yl,

[0104] p-terphenyl-3-yl,

[0105] p-terphenyl-2-yl,

[0106] m-terphenyl-4-yl,

[0107] m-terphenyl-3-yl,

[0108] m-terphenyl-2-yl,

[0109] o-terphenyl-4-yl

[0110] o-terphenyl-3-yl

[0111] o-terphenyl-2-yl,

[0112] 1-Naphthyl,

[0113] 2-Naphthyl,

[0114] anthracene,

[0115] Benzanthracene,

[0116] Fiki,

[0117] Benzphenanthrene,

[0118] Finadenyl,

[0119] Pyrene

[0120] base,

[0121] benzo[a] base,

[0122] Tri-phenylene,

[0123] Benzotrimethylene

[0124] phenylene,

[0125] Pentaphenyl,

[0126] Fluorine

[0127] 9,9'-spirobisfluorene,

[0128] benzo[f]fluorenyl,

[0129] Dibenzofluorene,

[0130] Fluoranthene base,

[0131] Benzofluoranthyl,

[0132] Peripheral, and

[0133] The monovalent aryl group is derived by removing one hydrogen atom from the ring structure shown in the following general formulas (TEMP-1) to (TEMP-15).

[0134] [Chemical Formula 4]

[0135]

[0136] [Chemical Formula 5]

[0137]

[0138] • Substituted aryl groups (specific example group G1B): o-tolyl,

[0139] m-Tolyl,

[0140] p-Tolyl,

[0141] p-Xylyl,

[0142] m-Xylyl,

[0143] o-xylyl,

[0144] p-isopropylphenyl,

[0145] m-Isopropylphenyl,

[0146] o-isopropylphenyl,

[0147] p-tert-butylphenyl,

[0148] m-tert-butylphenyl,

[0149] o-tert-butylphenyl,

[0150] 3,4,5-Trimethylphenyl,

[0151] 9,9-Dimethylfluorenyl,

[0152] 9,9-Diphenylfluorenyl

[0153] 9,9-bis(4-methylphenyl)fluorenyl,

[0154] 9,9-Bis(4-isopropylphenyl)fluorenyl,

[0155] 9,9-Bis(4-tert-butylphenyl)fluorenyl,

[0156] cyanophenyl,

[0157] Triphenylsilylphenyl

[0158] Trimethylsilylphenyl

[0159] Phenynaphthyl,

[0160] Naphthylphenyl and

[0161] A group derived from the ring structure shown in the above general formulas (TEMP-1) to (TEMP-15) by substitution of one or more hydrogen atoms of a monovalent group with a substituent.

[0162] • "Substituted or unsubstituted heterocyclic groups"

[0163] The term "heterocyclic group" as used in this specification refers to a cyclic group whose cyclic atom comprises at least one heteroatom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.

[0164] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.

[0165] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0166] 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".

[0167] "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.

[0168] 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).

[0169] 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).

[0170] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):

[0171] pyrrole,

[0172] Imidazole group,

[0173] Pyrazolyl,

[0174] Triazole group,

[0175] Tetrazolyl,

[0176] Oxazolyl,

[0177] Isoxazolyl,

[0178] Oxadiazole group,

[0179] Thiazole group,

[0180] Isothiazolyl,

[0181] Thiadiazole group,

[0182] pyridyl,

[0183] pyridazinyl,

[0184] Pyrimidine group,

[0185] Pyrazinyl,

[0186] Triazine group

[0187] Indole,

[0188] Isoindolyl,

[0189] Indazine-based

[0190] Quinazine-based

[0191] Quinoline,

[0192] Isoquinoline,

[0193] Crenoline group

[0194] Phthaloazine

[0195] Quinazolinyl,

[0196] Quinoxaloyl,

[0197] Benzimidazole group,

[0198] Indazole group,

[0199] phenanthroline,

[0200] phenanthridine,

[0201] acridine group,

[0202] Phenazine group,

[0203] Carbazolyl,

[0204] Benzocarbazolyl,

[0205] Morpholinyl,

[0206] phenoxazine group,

[0207] phenothiazine group,

[0208] Azacarbazolyl and diazacarbazolyl.

[0209] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2):

[0210] furanyl,

[0211] Oxazolyl,

[0212] Isoxazolyl,

[0213] Oxadiazole group,

[0214] Xuton base,

[0215] Benzofuranyl,

[0216] Isobenzofuranyl,

[0217] Dibenzofuranyl,

[0218] Naphthobenzofuranyl,

[0219] Benzoxazolyl,

[0220] Benzisoxazole group,

[0221] phenoxazine group,

[0222] Morpholinyl,

[0223] Dinaphthylfuranyl,

[0224] Azadibenzofuranyl,

[0225] diazadibenzofuranyl,

[0226] Azanaphthalenebenzofuranyl, and

[0227] Diazanaphthenebenzofuranyl.

[0228] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3):

[0229] Thiophene group

[0230] Thiazole group,

[0231] Isothiazolyl,

[0232] Thiadiazole group,

[0233] benzothienyl

[0234] isobenzothienyl

[0235] dibenzothienyl

[0236] Naphthobenzothienyl

[0237] Benzothiazolyl,

[0238] Benzisothiazolyl,

[0239] phenothiazine group,

[0240] dinaphthothienyl

[0241] azadibenzothienyl

[0242] diazadibenzothienyl

[0243] Azanaphthobenzothienyl, and

[0244] diazanaphthobenzothienyl.

[0245] • 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):

[0246]

Chemical Formula 6

[0247]

[0248] [Chemical Formula 7]

[0249]

[0250] 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.

[0251] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y AWhen 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.

[0252] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):

[0253] (9-phenyl)carbazole group,

[0254] (9-Biphenyl)carbazolyl,

[0255] (9-Phenyl)phenylcarbazolyl,

[0256] (9-Naphthyl)carbazole,

[0257] Diphenylcarbazole-9-yl,

[0258] Phenylexacarbazole-9-yl,

[0259] Methylbenzimidazole,

[0260] Ethylbenzimidazole,

[0261] Phenylacetyl,

[0262] Biphenyltriazine

[0263] diphenyltriazine group,

[0264] phenylquinazolinyl, and

[0265] Biphenylquinazolinyl.

[0266] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):

[0267] Phenyl dibenzofuranyl,

[0268] Methyldibenzofuranyl,

[0269] tert-butyldibenzofuranyl, and

[0270] The monovalent residue of [9H-xanton-9,9'-[9H]fluorene].

[0271] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):

[0272] Phenyl dibenzothiophene,

[0273] Methyldibenzothiophene,

[0274] tert-butyldibenzothiophene, and

[0275] The monovalent residue of [9H-thiophene-9,9'-[9H]fluorene].

[0276] • 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):

[0277] The aforementioned "one or more hydrogen atoms in a monovalent heterocyclic group" refers to hydrogen atoms bonded to the cyclic carbon atoms of the monovalent heterocyclic group, X A and Y A The hydrogen atom bonded to the nitrogen atom when at least one of them is NH and X A and Y A One of them is one or more hydrogen atoms in the methylene group when CH2 is present.

[0278] • "Substituted or unsubstituted alkyl groups"

[0279] 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.

[0280] "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.

[0281] • Unsubstituted alkyl groups (specific example group G3A):

[0282] methyl,

[0283] Ethyl,

[0284] n-propyl,

[0285] Isopropyl,

[0286] n-Butyl,

[0287] Isobutyl,

[0288] sec-butyl, and

[0289] tert-butyl.

[0290] • Substituted alkyl groups (specific example group G3B):

[0291] Heptafluoropropyl (including isomers),

[0292] Pentafluoroethyl,

[0293] 2,2,2-trifluoroethyl, and

[0294] Trifluoromethyl

[0295] • "Substituted or unsubstituted alkenyl groups"

[0296] 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.

[0297] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" group have been substituted with a substituent. Specific examples of "substituted alkenyl" include the "unsubstituted alkenyl" group (specific example group G4A) having a substituent and examples of substituted alkenyl groups (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples; the "substituted alkenyl" described in this specification also includes groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the alkenyl itself have been further substituted with a substituent, and groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the substituent have been further substituted with a substituent.

[0298] • Unsubstituted alkenyl groups (specific example group G4A):

[0299] vinyl,

[0300] Allyl

[0301] 1-Butenyl,

[0302] 2-Butenyl, and

[0303] 3-Butenyl.

[0304] • Substituted alkenyl groups (specific example group G4B):

[0305] 1,3-Butadienyl,

[0306] 1-Methylvinyl

[0307] 1-Methylallyl,

[0308] 1,1-Dimethylallyl,

[0309] 2-Methylallyl, and

[0310] 1,2-Dimethylallyl.

[0311] • "Substituted or unsubstituted alkynyl groups"

[0312] 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".

[0313] "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.

[0314] • Unsubstituted alkynyl group (specific example group G5A):

[0315] Acetylene group.

[0316] • "Substituted or unsubstituted cycloalkyl groups"

[0317] 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.

[0318] "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.

[0319] • Unsubstituted cycloalkyl groups (specific example group G6A):

[0320] Cyclopropyl

[0321] Cyclobutyl,

[0322] Cyclopentyl,

[0323] Cyclohexyl,

[0324] 1-Adamantyl,

[0325] 2-Adamantyl,

[0326] 1-norborneol, and

[0327] 2-norborneol.

[0328] • Substituted cycloalkyl groups (specific example group G6B):

[0329] 4-Methylcyclohexyl.

[0330] ·"-Si(R 901 )(R 902 )(R 903 The group shown in the figure”

[0331] 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:

[0332] -Si(G1)(G1)(G1),

[0333] -Si(G1)(G2)(G2)

[0334] -Si(G1)(G1)(G2),

[0335] -Si(G2)(G2)(G2),

[0336] -Si(G3)(G3)(G3), and

[0337] -Si(G6)(G6)(G6). Here,

[0338] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0339] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0340] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0341] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0342] In -Si(G1)(G1)(G1), multiple G1s may be the same or different from each other.

[0343] In -Si(G1)(G2)(G2), multiple G2s may be the same or different from each other.

[0344] In -Si(G1)(G1)(G2), multiple G1s may be the same or different from each other.

[0345] In -Si(G2)(G2)(G2), multiple G2s may be the same or different from each other.

[0346] In -Si(G3)(G3)(G3), multiple G3s may be the same or different from each other.

[0347] In -Si(G6)(G6)(G6), multiple G6s may be the same or different from each other.

[0348] ·“-O-(R 904 The group shown in the figure”

[0349] As described in this specification, -O-(R) 904 Specific examples of the group shown in the figure (specific example group G8) can be given as follows:

[0350] -O(G1)

[0351] -O(G2),

[0352] -O(G3) and

[0353] -O(G6).

[0354] Here,

[0355] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0356] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0357] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0358] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0359] ·“-S-(R 905 The group shown in the figure”

[0360] As described in this specification, -S-(R) 905 Specific examples of the group shown in the figure (specific example group G9) can be given as follows:

[0361] -S(G1)

[0362] -S(G2),

[0363] -S(G3) and

[0364] -S(G6).

[0365] Here,

[0366] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0367] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0368] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0369] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0370] ·"-N(R 906 )(R 907 The group shown in the figure”

[0371] As described in this specification, -N(R) 906 )(R 907 Specific examples of the group shown (specific example group G10) can be given as follows:

[0372] -N(G1)(G1),

[0373] -N(G2)(G2),

[0374] -N(G1)(G2),

[0375] -N(G3)(G3) and

[0376] -N(G6)(G6).

[0377] Here,

[0378] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0379] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0380] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0381] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0382] In -N(G1)(G1), multiple G1s may be the same or different from each other.

[0383] In -N(G2)(G2), multiple G2 values ​​may be the same or different from each other.

[0384] In -N(G3)(G3), multiple G3s may be the same or different from each other.

[0385] In -N(G6)(G6), multiple G6 values ​​may be the same or different from each other.

[0386] • "Halogen atom"

[0387] Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0388] • "Substituted or unsubstituted fluoroalkyl groups"

[0389] 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.

[0390] • "Substituted or unsubstituted haloalkyl groups"

[0391] 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.

[0392] • "Substituted or unsubstituted alkoxy groups"

[0393] 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.

[0394] • "Substituted or unsubstituted alkylthio groups"

[0395] 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.

[0396] • "Substituted or unsubstituted aryloxy groups"

[0397] 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.

[0398] • "Substituted or unsubstituted arylthio groups"

[0399] 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.

[0400] • "Substituted or unsubstituted trialkylsilyl groups"

[0401] 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.

[0402] • "Substituted or unsubstituted aralkyl groups"

[0403] 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.

[0404] 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.

[0405] 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.

[0406] 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.

[0407] In this specification, the carbazoyl group, unless otherwise specified herein, specifically refers to any one of the following groups.

[0408] [Chemical Formula 8]

[0409]

[0410] In this specification, (9-phenyl)carbazolyl refers specifically to any one of the following groups unless otherwise stated herein.

[0411] [Chemical Formula 9]

[0412]

[0413] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.

[0414] In this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any one of the following groups unless otherwise stated in this specification.

[0415]

Chemical Formula 10

[0416]

[0417] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

[0418] 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.

[0419] • "Substituted or unsubstituted aryl groups"

[0420] 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.

[0421] • "Substituted or unsubstituted divalent heterocyclic groups"

[0422] 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.

[0423] • "Substituted or unsubstituted alkylene compounds"

[0424] 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.

[0425] 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).

[0426]

Chemical Formula 11

[0427]

[0428]

Chemical Formula 12

[0429]

[0430] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0431] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0432]

Chemical Formula 13

[0433]

[0434] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0435] Formulas Q9 and Q 10 They can form rings by bonding with each other via single bonds.

[0436] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.

[0437]

Chemical Formula 14

[0438]

[0439] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0440] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.

[0441] 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).

[0442]

Chemical Formula 15

[0443]

[0444] [Chemical Formula 16]

[0445]

[0446]

Chemical Formula 17

[0447]

[0448] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0449] [Chemical Formula 18]

[0450]

[0451] [Chemical Formula 19]

[0452]

[0453]

Chemical Formula 20

[0454]

[0455]

Chemical Formula 21

[0456]

[0457] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0458] The above is an explanation of "substituents described in this specification".

[0459] • "Cases where bonds form rings"

[0460] 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".

[0461] The following description addresses the cases described in this specification as "forming a substituted or unsubstituted monocyclic ring by bonding one or more groups of two or more adjacent elements together" and "forming a substituted or unsubstituted fused ring by bonding one or more groups of two or more adjacent elements together" (hereinafter, these cases are sometimes collectively referred to as "forming a ring by bonding"). The case of anthracene compounds represented by the following general formula (TEMP-103) with an anthracene ring as the parent skeleton will be used as an example.

[0462]

Chemical Formula 22

[0463]

[0464] For example, in the case of 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 that form a group refers to R. 921 With R 922 group, R 922 With R 923 group, R 923 With R 924 group, R 924 With R 930 group, R 930 With R 925 group, R 925 With R 926 group, R 926 With R 927 group, R 927 With R 928 group, R 928 With R 929 The group, and R 929 With R 921 The group.

[0465] The phrase "one or more groups" refers to the fact that two or more groups consisting of two or more adjacent elements can simultaneously form a loop. For example, in R... 921 With R 922 They bond together to form a ring QA 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).

[0466]

Chemical Formula 23

[0467]

[0468] The formation of rings from "groups consisting of two or more adjacent elements" includes not only the case of bonds formed by groups consisting of "two" adjacent elements, as in the previous example, but also the case of bonds formed by groups consisting of "three or more" adjacent elements. For example, this 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 .

[0469] [Chemical Formula 24]

[0470]

[0471] In the formed "single ring" or "fused ring", the ring itself can be either a saturated or unsaturated ring. Even when a "single ring" or "fused ring" is formed from "one of two adjacent groups", it can still be either a saturated or 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 CFusing together forms a fused ring. The ring Q of the above general formula (TEMP-104) A If it is a benzene ring, then ring Q A It is a single ring. The ring Q of the above general formula (TEMP-104) A If it is a naphthalene ring, then ring Q A It is a fused ring.

[0472] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.

[0473] 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.

[0474] 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.

[0475] 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.

[0476] "Ring formation" refers to the formation of a ring solely by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton forming a ring with one or more other optional elements. For example, R shown in the above general formula (TEMP-104) 921 With R 922 The ring Q formed by mutual bonding A It refers to R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 The carbon atoms of the bonded anthracene framework form rings with one or more optional elements. As a specific example, in the case of R... 921 With R 922 Forming ring Q A In the case of R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 When the bonded anthracene skeleton carbon atoms and 4 carbon atoms form a monocyclic unsaturated ring, R 921 With R 922 The resulting ring is a benzene ring.

[0477] 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.

[0478] 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.

[0479] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".

[0480] Unless otherwise stated in this specification, the term "saturated ring" is preferred over "unsaturated ring".

[0481] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.

[0482] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.

[0483] In the case of "one or more groups consisting of two or more adjacent atoms" or "forming a substituted or unsubstituted monocyclic ring by mutual bonding" or "forming a substituted or unsubstituted fused ring by mutual bonding", unless otherwise stated in this specification, it is preferred that one or more groups consisting of two or more adjacent atoms form an "unsaturated ring" formed by mutual bonding of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0484] 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.

[0485] 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.

[0486] The above explains the cases of "a single ring formed by bonding one or more groups of two or more adjacent elements together, whether substituted or unsubstituted" and "a fused ring formed by bonding one or more groups of two or more adjacent elements together, whether substituted or unsubstituted" ("the case of forming a ring by bonding").

[0487] Substituents when described as "substituted or unsubstituted"

[0488] 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 unsubstituted alkyl groups having 1 to 50 carbon atoms.

[0489] Unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0490] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms

[0491] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0492] -Si(R 901 )(R 902 )(R 903 ),

[0493] -O-(R 904 ),

[0494] -S-(R 905 ),

[0495] -N(R 906 )(R 907 ),

[0496] Halogen atom, cyano group, nitro group,

[0497] Unsubstituted aryl groups with 6 to 50 carbon atoms and

[0498] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms

[0499] Groups, etc., in the composition group

[0500] Here, R 901 ~R 907 Each independently

[0501] hydrogen atom,

[0502] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0503] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0504] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0505] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0506] 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.

[0507] In R 902In cases where there are two or more R's, there are two or more R's. 902 They are the same or different.

[0508] 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.

[0509] 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.

[0510] 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.

[0511] 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.

[0512] In R 907 In cases where there are two or more R's, there are two or more R's. 907 They are the same or different.

[0513] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0514] Alkyl groups with 1 to 50 carbon atoms

[0515] Aryl groups with 6 to 50 carbon atoms and

[0516] Heterocyclic groups with 5 to 50 cyclic atoms

[0517] The groups that make up the group.

[0518] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0519] Alkyl groups having 1 to 18 carbon atoms

[0520] aryl groups with 6 to 18 carbon atoms and

[0521] Heterocyclic groups with 5 to 18 cyclic atoms

[0522] The groups that make up the group.

[0523] Specific examples of the substituents mentioned above are those described in the section "Substituents as set forth in this specification".

[0524] 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.

[0525] 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.

[0526] In this specification, the numerical range represented by "AA~BB" refers to the range included by taking the value AA, which is written before "AA~BB", as the lower limit and the value BB, which is written after "AA~BB", as the upper limit.

[0527] The compounds of the present invention will be described below.

[0528] The compounds of the present invention are represented by the above formula (1). Hereinafter, the symbols in formula (1) and the various formulas included in formula (1) will be explained. Unless otherwise specified, the same symbols have the same meaning.

[0529] The compounds of the present invention represented by formula (1) and the formulas contained in formula (1) described later are called "inventive compounds".

[0530] [Chemical Formula 25]

[0531]

[0532] N ＊ The central nitrogen atom.

[0533] R 1 ~R 4 Each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted cyclic aryl group having 6 to 12 carbon atoms.

[0534] Selected from R 1 ~R 4 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0535] The above R 1 ~R 4 The unsubstituted alkyl group having 1 to 6 carbon atoms is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, or hexyl, preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, more preferably methyl or tert-butyl.

[0536] The above R 1~R 4 The unsubstituted aryl group having 6 to 12 carbon atoms is, for example, phenyl, biphenyl, biphenylenyl or naphthyl, preferably phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, or 1-naphthyl or 2-naphthyl, more preferably phenyl.

[0537] R 1 ~R 4 All are hydrogen atoms.

[0538] L 1 ~L 4 Each is independently a single bond, an unsubstituted cyclic carbon group with 6 to 30, preferably 6 to 25, more preferably 6 to 12 aryl groups, or an unsubstituted cyclic atom group with 5 to 30, preferably 5 to 18, more preferably 5 to 13 divalent heterocyclic groups.

[0539] L 1 ~L 4 Each is preferably a single bond or an unsubstituted aryl group with 6 to 30 carbon atoms in the cyclic group.

[0540] In one aspect of the invention, L 3 Single bonds are preferred.

[0541] In another aspect of the invention, L 4 Single bonds are preferred.

[0542] The above L 1 ~L 4 The unsubstituted aryl group with 6 to 30 carbon atoms refers to a divalent group obtained by removing one hydrogen atom from an unsubstituted aryl group with 6 to 30 carbon atoms. Examples of unsubstituted aryl groups with 6 to 30 carbon atoms include phenyl, biphenyl, terphenyl, biphenylenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, phenatenyl, styrene, pentylene, pyrene, etc. Benzyl, benzo[ The compound is phenyl, fluorenyl, fluoranyl, perylene, or triphenylene, preferably phenyl, biphenyl, terphenyl, or naphthyl, more preferably phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, 2-o-terphenyl, 3-o-terphenyl or 4-o-terphenyl, 2-m-terphenyl, 3-m-terphenyl or 4-m-terphenyl, 2-p-terphenyl, 3-p-terphenyl or 4-p-terphenyl, or 1-naphthyl or 2-naphthyl, further preferably phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, or 1-naphthyl or 2-naphthyl, and particularly preferably phenyl.

[0543] The above L 1 ~L 4The term "unsubstituted divalent heterocyclic group with 5 to 30 unsubstituted cyclic atoms" refers to a divalent group obtained by removing one hydrogen atom from an unsubstituted heterocyclic group.

[0544] The above L 1 ~L 4 The unsubstituted aromatic heterocyclic groups representing 5 to 30 cyclic atoms are, for example, pyrrolyl, furanyl, thiophene, pyridyl, imidazopyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiazolyl, triazolyl, tetrazolyl, indoleyl, isoindoleyl, indazinyl, quinazinyl, quinolinyl, isoquinolinyl, terpineyl, phthalazinyl, quinazolinyl, quinoxolinyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, indoleyl, benzoisoxazolyl, benzoisothiazolyl, phenanthridine, acridineyl, phenanthrolinyl, phenazinyl, phenthiazolyl, phenoxazinyl, xanthonyl, benzofuranyl, isobenzene The preferred compounds are benzofuranyl, naphthobenzofuranyl, dibenzofuranyl, benzothienyl, isobenzothienyl, naphthobenzothienyl, dibenzothienyl, or carbazoleyl, preferably benzofuranyl, isobenzofuranyl, naphthobenzofuranyl, dibenzofuranyl, benzothienyl, isobenzothienyl, naphthobenzothienyl, dibenzothienyl, or carbazoleyl (9-carbazoleyl, 1-carbazoleyl, 2-carbazoleyl, 3-carbazoleyl, or 4-carbazoleyl).

[0545] Ar 1 and Ar 2 Each of the following groups is independently an aryl group consisting of only a six-membered ring with 6 to 30, preferably 6 to 25, more preferably 6 to 12, substituted or unsubstituted cyclic carbons; a heterocyclic group with 5 to 30, preferably 5 to 18, more preferably 5 to 13, substituted or unsubstituted cyclic atoms; or a group represented by formula (a) below.

[0546]

Chemical Formula 26

[0547]

[0548] In equation (a), *1 represents the relationship between L and L. 1 or L 2 The bonding positions.

[0549] R a and R bEach of the following groups is independently a hydrogen atom, an alkyl group with 1 to 30 substituted or unsubstituted carbon atoms, preferably 1 to 18, more preferably 1 to 6, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, preferably 6 to 25, more preferably 6 to 12, or a heterocyclic group with 5 to 30 substituted or unsubstituted cyclic atoms, preferably 5 to 18, more preferably 5 to 13.

[0550] R a and R b They can bond with each other to form substituted or unsubstituted rings, or they can not bond with each other and therefore not form rings.

[0551] R a and R b Each is preferably an alkyl group with 1 to 30 carbon atoms, either substituted or unsubstituted, or an aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0552] The above R a and R b The unsubstituted alkyl group having 1 to 30 carbon atoms is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, or dodecyl, preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, or pentyl, more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, and even more preferably methyl or tert-butyl.

[0553] The above R a and R b Details of unsubstituted aryl groups with 6 to 30 carbon atoms and their application to L 1 ~L 4 The records are the same.

[0554] The above R a and R b Details of unsubstituted heterocyclic groups with 5–30 cyclic atoms are shown in relation to L. 1 ~L 4 The records are the same.

[0555] By R a and R b The unsubstituted monocyclic rings formed are, for example, benzene rings, cyclopentane rings, and cyclohexane rings.

[0556] By R a and R b The unsubstituted fused rings formed are, for example, naphthalene rings and anthracene rings.

[0557] Additionally, in R a and R b When they bond together to form unsubstituted monocyclic rings or unsubstituted fused rings, Ra and R b These groups can form spirocyclic rings by combining with the fluorene skeleton to which they are bonded. The aforementioned spirocyclic rings are hydrocarbon rings or heterocyclic rings, selected from monocyclic, fused, bicyclic bridged, and tricyclic bridged rings. Examples of substituted or unsubstituted spirocyclic rings are shown below, but are not limited to these. * indicates the bonding position with the benzene ring of the fluorene skeleton.

[0558] [Chemical Formula 27]

[0559]

[0560] Selected from R 21 ~R 28 One of them is a single bond bonded to *2, not the R of the single bond bonded to *2. 21 ~R 28 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 cyclic atoms.

[0561] Selected from R that is not one of the above single bonds 21 ~R 28 Two adjacent benzene rings can bond together to form one or more unsubstituted benzene rings, or they can not bond together and thus not form a ring.

[0562] The above is not a single bond R that is bonded to *2. 21 ~R 28 Details of the unsubstituted alkyl groups having 1 to 6 carbon atoms are shown in relation to R. 1 ~R 4 The records are the same.

[0563] The above is not a single bond R that is bonded to *2. 21 ~R 28 Details of the unsubstituted aryl groups with 6 to 12 carbon atoms, except for the number of carbon atoms in the ring, are the same as those for L. 1 ~L 4 The records are the same.

[0564] The above is not a single bond R that is bonded to *2. 21 ~R 28 Details of the unsubstituted heterocyclic groups with 5 to 13 cyclic atoms are shown, except that the number of cyclic atoms is 5 to 13, and are consistent with those for L 1 ~L 4 The records are the same.

[0565] In R a and R b When they bond together with the carbon atom at position 9 of the fluorene framework to form a substituted or unsubstituted spirofluorene ring, selected from R 22 ~R27 One of them is a single bond that bonds with *2.

[0566] In L 1 ~L 4 All are single bonds, Ar 1 and Ar 2 The group is shown in formula (a) and R 22 or R 27 In the case of a single bond bonded to *2, selected from 2 R a and 2 R b At least one of them is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms in a cyclic structure.

[0567] R is not a single bond that bonds with *2. 21 ~R 28 Both can be hydrogen atoms.

[0568] Ar 1 and Ar 2 Details of unsubstituted aryl groups consisting of only a six-membered ring with 6 to 30 carbon atoms are provided, except that they are aryl groups consisting only of a six-membered ring and are the same as those for L. 1 ~L 4 The records are the same.

[0569] Ar 1 and Ar 2 Details of unsubstituted heterocyclic groups with 5–30 cyclic atoms are shown in relation to L. 1 ~L 4 The records are the same.

[0570] Ar 1 and Ar 2 Each is preferably an aryl group containing only a six-membered ring with 6 to 30 cyclic carbons, either substituted or unsubstituted, or a heterocyclic group containing 5 to 30 cyclic atoms, and more preferably an aryl group containing only a six-membered ring with 6 to 30 cyclic carbons, either substituted or unsubstituted.

[0571] Ar 1 and Ar 2 Each group is preferably represented by any one of the following formulas (1a) to (1e), and more preferably by any one of the following formulas (1a), (1b) and (1d).

[0572] [Chemical Formula 28]

[0573]

[0574] In equation (1a),

[0575] *21 is related to L 1 or L 2 The bonding positions.

[0576] R 101 ~R 110 Each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted cyclic aryl group having 6 to 12 carbon atoms. Among them, R is selected from... 101 ~R 105 One of them is a single bond bonded to *22, selected from R 106 ~R 110 One of them is a single bond that bonds with *23.

[0577] Selected from R that is not one of the above single bonds 101 ~R 105 Two adjacent elements in the loop are not bonded to each other and therefore do not form a loop.

[0578] Selected from R that is not one of the above single bonds 106 ~R 110 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0579] The above R 101 ~R 110 Details of the unsubstituted alkyl groups having 1 to 6 carbon atoms are shown in relation to R. 1 ~R 4 The records are the same.

[0580] The above R 101 ~R 110 Details of the unsubstituted aryl groups with 6 to 12 carbon atoms, except for the number of carbon atoms in the ring, are the same as those for L. 1 ~L 4 The records are the same.

[0581] R is a single bond that is neither bonded to *22 nor bonded to *23. 101 ~R 110 All are hydrogen atoms.

[0582] k is either 0 or 1, 1 is either 0 or 1

[0583] k+l is an integer from 0 to 2.

[0584] In one embodiment of the invention, k is 0 and 1 is 0. In this case, *23 represents *21, and equation (1a) is represented by the following equation.

[0585] [Chemical Formula 29]

[0586]

[0587] In another embodiment of the invention, k is 1 and l is 0. In this case, *23 represents *22, and equation (1a) is represented by the following equation.

[0588]

Chemical Formula 30

[0589]

[0590] In another embodiment of the invention, k is 0 and 1 is 1. In this case, *22 represents *21, and equation (1a) is represented by the following equation.

[0591]

Chemical Formula 31

[0592]

[0593] In another embodiment of the invention, k is 1 and 1 is 1. In this case, equation (1a) is represented by the following equation.

[0594]

Chemical Formula 32

[0595]

[0596] In one embodiment of the present invention, k+1 is preferably 1.

[0597] R 111 ~R 115 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms, or a substituted or unsubstituted cyclic group having 5 to 13 heterocyclic atoms.

[0598] Selected from R 111 ~R 115 Two adjacent benzene rings can bond together to form one or more unsubstituted benzene rings, or they can not bond together and thus not form a ring.

[0599] The above R 111 ~R 115 Details of the unsubstituted alkyl groups having 1 to 6 carbon atoms are shown in relation to R. 1 ~R 4 The records are the same.

[0600] The above R 111 ~R 115 Details of the unsubstituted aryl groups with 6 to 12 carbon atoms, except for the number of carbon atoms in the ring, are the same as those for L. 1 ~L 4 The records are the same.

[0601] The above R 111 ~R 115 Details of the unsubstituted heterocyclic groups with 5 to 13 cyclic atoms are shown, except that the number of cyclic atoms is 5 to 13, and are consistent with those for L 1 ~L 4 The records are the same.

[0602] R111 ~R 115 All are hydrogen atoms.

[0603] The group represented by formula (1a) is preferably represented by the following formula. In the following formula, R is omitted for simplification.

[0604]

Chemical Formula 33

[0605]

[0606] Equation (1b) is represented by the following equation.

[0607]

Chemical Formula 34

[0608]

[0609] In equation (1b),

[0610] *24 is related to L 1 or L 2 The bonding positions.

[0611] R 121 ~R 128 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms.

[0612] Among them, selected from R 121 ~R 128 One of them is a single bond bonded to *25, selected from R that is not one of the aforementioned single bonds. 121 ~R 128 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0613] The above R 121 ~R 128 Details of the unsubstituted alkyl groups having 1 to 6 carbon atoms are shown in relation to R. 1 ~R 4 The records are the same.

[0614] The above R 121 ~R 128 Details of the unsubstituted aryl groups with 6 to 12 carbon atoms, except for the number of carbon atoms in the ring, are the same as those for L. 1 ~L 4 The records are the same.

[0615] In one embodiment of the invention, R is preferred. 121 In another scheme, R is preferred as the single bond that bonds with *25. 122 This is a single bond that bonds with *25.

[0616] R is not a single bond that bonds with *25 121 ~R128 All are hydrogen atoms.

[0617] Equation (1c) is represented by the following equation.

[0618]

Chemical Formula 35

[0619]

[0620] In equation (1c),

[0621] *26 is related to L 1 or L 2 The bonding positions.

[0622] R 131 ~R 140 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms.

[0623] Among them, selected from R 131 ~R 140 One of them is a single bond bonded to *27, selected from R that is not one of the aforementioned single bonds. 131 ~R 140 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0624] The above R 131 ~R 140 Details of the unsubstituted alkyl groups having 1 to 6 carbon atoms are shown in relation to R. 1 ~R 4 The records are the same.

[0625] The above R 131 ~R 140 Details of the unsubstituted aryl groups with 6 to 12 carbon atoms, except for the number of carbon atoms in the ring, are the same as those for L. 1 ~L 4 The records are the same.

[0626] Preferred selection from R 131 R 132 and R 140 One of them is a single bond bonded to *27. In one embodiment of the invention, R 131 For a single bond that bonds with *27, in another scheme, R 132 For a single bond that bonds with *27, in another scheme, R 140 It is a single bond that bonds with *27.

[0627] R is not a single bond that bonds with *27 131 ~R 140 All are hydrogen atoms.

[0628] Equation (1d) is represented by the following equation.

[0629]

Chemical Formula 36

[0630]

[0631] In equation (1d),

[0632] *26 is related to L 1 or L 2 The bonding positions.

[0633] X 2 It is an oxygen atom, a sulfur atom, or NR. A .

[0634] X 2 Preferably oxygen atoms or NR A .

[0635] R A It is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms.

[0636] The above R A Details of the unsubstituted alkyl groups having 1 to 6 carbon atoms are shown in relation to R. 1 ~R 4 The records are the same.

[0637] The above R A Details of the unsubstituted aryl groups with 6 to 12 carbon atoms, except for the number of carbon atoms in the ring, are the same as those for L. 1 ~L 4 The records are the same.

[0638] R 141 ~R 148 Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 cyclic atoms. The group selected from the above R groups... 141 ~R 148 and R A One of them is a single bond that bonds with *29.

[0639] Selected from R that is not one of the above single bonds 141 ~R 148 At least one pair of adjacent 2 atoms in the benzene ring can bond to each other to form one or more unsubstituted benzene rings, or they can not bond to each other and thus not form a ring.

[0640] The above R 141 ~R 148 Details of the unsubstituted alkyl groups having 1 to 6 carbon atoms are shown in relation to R. 1 ~R4 The records are the same.

[0641] The above R 141 ~R 148 Details of the unsubstituted aryl groups with 6 to 12 carbon atoms, except for the number of carbon atoms in the ring, are the same as those for L. 1 ~L 4 The records are the same.

[0642] The above R 141 ~R 148 Details of the unsubstituted heterocyclic groups with 5 to 13 cyclic atoms are shown, except that the number of cyclic atoms is 5 to 13, and are consistent with those for L 1 ~L 4 The records are the same.

[0643] R is not a single bond that bonds with *29 141 ~R 148 and R A All are hydrogen atoms.

[0644] In X 2 In the case of oxygen or sulfur atoms, it is preferably selected from R 141 ~R 144 One of them is a single bond that bonds with *29.

[0645] In X 2 NR A In the case of R, it is preferred to select 141 ~R 144 and R A One of them is a single bond that bonds with *29.

[0646] R A It is particularly preferred to have a single bond, an unsubstituted phenyl or naphthyl group bonded to *29.

[0647] Equation (1e) is represented by the following equation.

[0648]

Chemical Formula 37

[0649]

[0650] In equation (1e),

[0651] *30 is related to L 1 or L 2 The bonding positions.

[0652] R 151 ~R 155 Each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted phenyl group.

[0653] Among them, selected from R 151 ~R155 One of them is a single bond bonded to *31, selected from R 151 ~R 155 The other one is a single bond that bonds with *32.

[0654] R selected from a single bond that is neither bonded to *31 nor to *32 151 ~R 155 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0655] The above R 151 ~R 155 Details of the unsubstituted alkyl groups having 1 to 6 carbon atoms are shown in relation to R. 1 ~R 4 The records are the same.

[0656] R is neither a single bond bonded to *31 nor a single bond bonded to *32. 151 ~R 155 All are hydrogen atoms.

[0657] R 161 ~R 165 and R 171 ~R 175 Each is independently a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0658] Among them, selected from R 161 ~R 165 At least one pair of adjacent benzene rings can bond together to form one or more unsubstituted benzene rings, or they can not bond together and therefore not form a ring.

[0659] Selected from R 171 ~R 175 At least one pair of adjacent 2 atoms in the benzene ring can bond to each other to form one or more unsubstituted benzene rings, or they can not bond to each other and thus not form a ring.

[0660] The above R 161 ~R 165 and R 171 ~R 175 Details of the unsubstituted alkyl groups having 1 to 6 carbon atoms are shown in relation to R. 1 ~R 4 The records are the same.

[0661] R 161 ~R 165 and R 171 ~R 175 All are hydrogen atoms.

[0662] Formula (1e) includes the groups shown in the following formulas (1e-1) to (1e-5), preferably formulas (1e-1), (1e-2) or (1e-4).

[0663] [Chemical Formula 38]

[0664]

[0665] Ar 3 It is the group represented by the following formula (x).

[0666] [Chemical Formula 39]

[0667]

[0668] In equation (x),

[0669] *3 is related to L 4 The bonding positions.

[0670] R 31 ~R 38 R 41 ~R 44 and R 51 ~R 58 Each of the following groups is independently composed of a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group with 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group with 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 50 carbon atoms, or a -Si(R group). 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 group shown in the figure, substituted or unsubstituted aryl group with 6 to 50 carbon atoms, or substituted or unsubstituted heterocyclic group with 5 to 50 cyclic atoms,

[0671] R 901 ~R 907 Each of the following groups is independently composed of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms.

[0672] In R 901 In the case of two or more R, two or more R 901 They are the same or different.

[0673] In R 902In the case of two or more R, two or more R 902 They are the same or different.

[0674] In R 903 In the case of two or more R, two or more R 903 They are the same or different.

[0675] In R 904 In the case of two or more R, two or more R 904 They are the same or different.

[0676] In R 905 In the case of two or more R, two or more R 905 They are the same or different.

[0677] In R 906 In the case of two or more R, two or more R 906 They are the same or different.

[0678] In R 907 In the case of two or more R, two or more R 907 They are the same or different.

[0679] R 31 ~R 38 R 41 ~R 44 and R 51 ~R 58 Each of the following is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 cyclic carbon atoms; more preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms; even more preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 cyclic carbon atoms; and even more preferably a hydrogen atom.

[0680] The above R 31 ~R 38 R 41 ~R 44 and R 51 ~R 58 The details of the halogen atom are the same as those described in the section on "Substituents as described in this specification", and are preferably fluorine atoms.

[0681] The above R 31 ~R 38 R 41 ~R 44 and R 51 ~R 58The details of the substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms are the same as those described in the section on "Substituents described in this specification".

[0682] The above R 31 ~R 38 R 41 ~R 44 and R 51 ~R 58 The unsubstituted alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, more preferably methyl, ethyl, isopropyl, or tert-butyl, and even more preferably methyl or tert-butyl.

[0683] The above R 31 ~R 38 R 41 ~R 44 and R 51 ~R 58 The details of the substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms are the same as those described in the section on "Substituents described in this specification".

[0684] The above R 31 ~R 38 R 41 ~R 44 and R 51 ~R 58 The details of the substituted or unsubstituted cycloalkyne groups with 2 to 50 carbon atoms are the same as those described in the section on "Substituents described in this specification".

[0685] The above R 31 ~R 38 R 41 ~R 44 and R 51 ~R 58 The details of the substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms are the same as those described in the section on "Substituents described in this specification".

[0686] The above R 31 ~R 38 R 41 ~R 44 and R 51 ~R 58 The unsubstituted cycloalkyl group indicated above is preferably cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, or 2-norbornyl, more preferably cyclopentyl or cyclohexyl.

[0687] The above R 31 ~R 38 R 41 ~R 44and R 51 ~R 58 -Si(R) represents 901 )(R 902 )(R 903 ), the above-mentioned -O-(R 904 The group shown is -S-(R) 905 The groups shown are -N(R) 906 )(R 907 The details of the groups shown are the same as those described in "Substituents as described in this specification".

[0688] The above R 31 ~R 38 R 41 ~R 44 and R 51 ~R 58 The details of the substituted or unsubstituted aryl groups with 6 to 50 carbon atoms are the same as those described in "Substituents Described in this Specification".

[0689] The above R 1 ~R 8 and R 11 ~R 18 The unsubstituted aryl group is preferably phenyl, biphenyl, naphthyl, or phenanthrene, more preferably phenyl, biphenyl, or naphthyl, and even more preferably phenyl.

[0690] The above R 31 ~R 38 R 41 ~R 44 and R 51 ~R 58 The details of the substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms are the same as those described in "Substituents Described in this Specification".

[0691] The above R 31 ~R 38 R 41 ~R 44 and R 51 ~R 58 The unsubstituted heterocyclic group is preferably dibenzofuranyl or dibenzothiophenyl.

[0692] m is 0 or 1, and n is 0 or 1.

[0693] When m and n are 0, R 31 and R 32 R 32 and R 33 or R 33 and R 34 One of them is a single bond bonded to *a, and the other is a single bond bonded to *b.

[0694] R selected from single bonds that are not bonded to *a and *b 31 ~R 38 and R 41 ~R 44 One of them is a single bond that bonds with *4.

[0695] When m is 1 and n is 0, R 31 and R 32 R 32 and R 33 or R 33 and R 34 One of them is a single bond bonded to *a, and the other is a single bond bonded to *b.

[0696] R 35 and R 36 R 36 and R 37 or R 37 and R 38 One of them is a single bond that bonds with *c, and the other is a single bond that bonds with *d.

[0697] R selected from single bonds that are not bonded to *a and *b 31 ~R 34 R is not a single bond that bonds with *c and *d. 35 ~R 38 R 41 ~R 44 and R 51 ~R 54 One of them is a single bond that bonds with *4.

[0698] When m is 0 and n is 1, R 31 and R 32 R 32 and R 33 or R 33 and R 34 One of them is a single bond bonded to *a, and the other is a single bond bonded to *b.

[0699] R 35 and R 36 R 36 and R 37 or R 37 and R 38 One of them is a single bond that bonds with *e, and the other is a single bond that bonds with *f.

[0700] R selected from single bonds that are not bonded to *a and *b 31 ~R 34 R is not a single bond that bonds with *e and *f. 35 ~R38 R 41 ~R 44 and R 55 ~R 58 One of them is a single bond that bonds with *4.

[0701] When m is 1 and n is 1, R 31 and R 32 R 32 and R 33 or R 33 and R 34 One of them is a single bond bonded to *a, and the other is a single bond bonded to *b.

[0702] R 35 and R 36 R 36 and R 37 and R 37 and R 38 In any of these three groups, one bond is a single bond bonded to *c, and the other is a single bond bonded to *d.

[0703] R 35 and R 36 R 36 and R 37 or R 37 and R 38 In the remaining two groups, one of them is a single bond bonded to *e, and the other is a single bond bonded to *f.

[0704] R selected from single bonds that are not bonded to *a and *b 31 ~R 34 R is not a single bond that bonds with *c to *f. 35 ~R 38 R 41 ~R 44 and R 51 ~R 58 One of them is a single bond that bonds with *4.

[0705] Among them, in L 3 and L 4 For single bonds, m and n are 0, R 33 For a single bond bonded to *a and R 34 For a single bond or R bond that bonds with *b 34 For a single bond bonded to *a and R 33 In the case of a single bond bonded to *b, selected from R 31 R 32 R 35 ~R 37 and R 41 ~R 44One of them is a single bond that bonds with *4.

[0706] In L 3 and L 4 For single bonds, m and n are 0, R 31 For a single bond bonded to *a and R 32 In the case of a single bond bonded to *b, selected from R 33 ~R 38 and R 42 ~R 44 One of them is a single bond that bonds with *4.

[0707] In L 3 and L 4 For single bonds, m and n are 0, R 32 For a single bond bonded to *a and R 31 In the case of a single bond bonded to *b, selected from R 33 ~R 38 and R 41 ~R 43 One of them is a single bond that bonds with *4.

[0708] In one embodiment of the present invention, m is preferably 0.

[0709] In another aspect of the invention, n is preferably 0.

[0710] In another embodiment of the invention, it is preferred that m is 0 and n is 0.

[0711] When m is 0 and n is 1, R is preferably selected from single bonds that are not bonded to *a and *b. 31 ~R 33 and R 36 ~R 38 One of them is a single bond bonded to *4, more preferably selected from R bonds that are not bonded to *a and *b. 31 and R 32 and R 37 and R 38 One of them is a single bond bonded to *4, and R is further preferred to be a single bond that is not bonded to *a and *b. 32 or R 37 It is a single bond that bonds with *4.

[0712] X 1 It consists of oxygen or sulfur atoms.

[0713] X 1 Oxygen atoms are preferred.

[0714] As described above, the term "hydrogen atom" as used in this specification includes protium, deuterium, and tritium atoms. Therefore, the inventive compounds may contain naturally occurring deuterium atoms.

[0715] Alternatively, deuterium atoms can be intentionally introduced into compound (1) by using a portion or all of the raw material compound as a deuterated compound. Therefore, in one aspect of the present invention, compound (1) contains at least one deuterium atom. That is, the inventive compound can be a compound represented by formula (1), in which at least one of the hydrogen atoms contained is a deuterium atom.

[0716] At least one hydrogen atom selected from the hydrogen atoms listed below may be a deuterium atom. It should be noted that "substituted or unsubstituted", number of carbon atoms and number of atoms are omitted below.

[0717] R in equation (1) 1 ~R 4 The hydrogen atom is represented;

[0718] In equation (1) R 1 ~R 4 When the group is alkyl or aryl, these groups have hydrogen atoms;

[0719] In equation (1) L 1 ~L 4 In the case of arylene or divalent heterocyclic groups, these groups have hydrogen atoms;

[0720] In equation (1) Ar 1 and Ar 2 In the case where these groups consist only of aryl or heterocyclic groups containing a six-membered ring, the hydrogen atoms present in these groups are:

[0721] R in equation (a) a and R b The hydrogen atom is represented;

[0722] In equation (a) R a and R b When these groups are alkyl, aryl, or heterocyclic, they contain hydrogen atoms;

[0723] In equation (a), the R bond is not a single bond bonded to *2. 21 ~R 28 The hydrogen atom is represented;

[0724] In equation (a), the R bond is not a single bond bonded to *2. 21 ~R 28 When these groups are alkyl, aryl, or heterocyclic, they contain hydrogen atoms;

[0725] The R in equation (x) is not a single bond bonded to *a~*f. 31 ~R 38 R 41 ~R 44 and R51 ~R 58 The hydrogen atom is represented;

[0726] In equation (x), R is not a single bond bonded to *a~*f. 31 ~R 38 R 41 ~R 44 and R 51 ~R 58 Alkyl, alkenyl, ynyl, cycloalkyl, -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 In the case of groups, aryl or heterocyclic groups, these groups have hydrogen atoms.

[0727] The deuteration rate of the inventive compound depends on the deuteration rate of the raw material compound used. Even when using a raw material with a specified deuteration rate, it may contain a certain proportion of protium isotopes from natural sources. Therefore, the deuteration rate schemes of the inventive compounds shown below, relative to the proportions obtained by simply counting the number of deuterium atoms represented by the chemical formula, include the ratio of trace amounts of naturally sourced isotopes.

[0728] The deuteration rate of the inventive compound is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, even more preferably 10% or more, and even more preferably 50% or more.

[0729] The inventive compound can be a mixture comprising a deuterated compound and an undeuterated compound, or a mixture of two or more compounds with different deuteration rates. The deuteration rate of such a mixture is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, even more preferably 10% or more, even more preferably 50% or more, and less than 100%.

[0730] Furthermore, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, and even more preferably 10% or more and 100% or less.

[0731] When the "substituted or unsubstituted XX group" included in the definitions of the above formulas refers to a substituted XX group, the details of the substituent are the same as those described in "substituents expressed as 'substituted or unsubstituted'", preferably an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 cyclic carbon atoms, or an aromatic heterocyclic group having 5 to 13 cyclic atoms, more preferably an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 12 cyclic carbon atoms. The details of each group are as described above.

[0732] The inventive compound can be readily manufactured by those skilled in the art with reference to the following synthetic examples and known synthetic methods.

[0733] The following examples of the inventive compounds are shown, but are not limited to the exemplified compounds below.

[0734] In the specific examples below, D represents a deuterium atom.

[0735]

Chemical Formula 40

[0736]

[0737]

Chemical Formula 41

[0738]

[0739]

Chemical Formula 42

[0740]

[0741]

Chemical Formula 43

[0742]

[0743]

Chemical Formula 44

[0744]

[0745] [Chemical Formula 45]

[0746]

[0747]

Chemical Formula 46

[0748]

[0749] [Chemical Formula 47]

[0750]

[0751] [Chemical Formula 48]

[0752]

[0753] [Chemical Formula 49]

[0754]

[0755] [Chemical Formula 50]

[0756]

[0757]

Chemical Formula 51

[0758]

[0759]

Chemical Formula 52

[0760]

[0761]

Chemical Formula 53

[0762]

[0763] [Chemical Formula 54]

[0764]

[0765]

Chemical Formula 55

[0766]

[0767] [Chemical Formula 56]

[0768]

[0769] [Chemical Formula 57]

[0770]

[0771] [Chemical Formula 58]

[0772]

[0773] [Chemical Formula 59]

[0774]

[0775] [Chemical Formula 60]

[0776]

[0777]

Chemical Formula 61

[0778]

[0779]

Chemical Formula 62

[0780]

[0781]

Chemical Formula 63

[0782]

[0783]

Chemical Formula 64

[0784]

[0785]

Chemical Formula 65

[0786]

[0787]

Chemical Formula 66

[0788]

[0789] [Chemical Formula 67]

[0790]

[0791]

Chemical Formula 68

[0792]

[0793]

Chemical Formula 69

[0794]

[0795] [Chemical Formula 70]

[0796]

[0797]

Chemical Formula 71

[0798]

[0799]

Chemical Formula 72

[0800]

[0801]

Chemical Formula 73

[0802]

[0803] [Chemical Formula 74]

[0804]

[0805] [Chemical Formula 75]

[0806]

[0807] [Chemical Formula 76]

[0808]

[0809]

Chemical Formula 77

[0810]

[0811] [Chemical Formula 78]

[0812]

[0813] [Chemical Formula 79]

[0814]

[0815] [Chemical Formula 80]

[0816]

[0817]

Chemical Formula 81

[0818]

[0819]

Chemical Formula 82

[0820]

[0821]

Chemical Formula 83

[0822]

[0823]

Chemical Formula 84

[0824]

[0825]

Chemical Formula 85

[0826]

[0827]

Chemical Formula 86

[0828]

[0829]

Chemical Formula 87

[0830]

[0831]

Chemical Formula 88

[0832]

[0833]

Chemical Formula 89

[0834]

[0835] [Chemical Formula 90]

[0836]

[0837]

Chemical Formula 91

[0838]

[0839]

Chemical Formula 92

[0840]

[0841] [Chemical Formula 93]

[0842]

[0843] [Chemical Formula 94]

[0844]

[0845] [Chemical Formula 95]

[0846]

[0847] [Chemical Formula 96]

[0848]

[0849] [Chemical Formula 97]

[0850]

[0851]

Chemical Formula 98

[0852]

[0853]

Chemical Formula 99

[0854]

[0855]

Chemical Formula 100

[0856]

[0857]

Chemical Formula 101

[0858]

[0859]

Chemical Formula 102

[0860]

[0861]

Chemical Formula 103

[0862]

[0863] [Chemical Formula 104]

[0864]

[0865] [Chemical Formula 105]

[0866]

[0867] [Chemical Formula 106]

[0868]

[0869] [Chemical Formula 107]

[0870]

[0871] [Chemical Formula 108]

[0872]

[0873] [Chemical Formula 109]

[0874]

[0875]

Chemical Formula 110

[0876]

[0877]

Chemical Formula 111

[0878]

[0879]

Chemical Formula 112

[0880]

[0881]

Chemical Formula 113

[0882]

[0883]

Chemical Formula 114

[0884]

[0885]

Chemical Formula 115

[0886]

[0887]

Chemical Formula 116

[0888]

[0889]

Chemical Formula 117

[0890]

[0891]

Chemical Formula 118

[0892]

[0893]

Chemical Formula 119

[0894]

[0895]

Chemical Formula 120

[0896]

[0897]

Chemical Formula 121

[0898]

[0899]

Chemical Formula 122

[0900]

[0901]

Chemical Formula 123

[0902]

[0903] [Chemical Formula 124]

[0904]

[0905] [Chemical Formula 125]

[0906]

[0907] [Chemical Formula 126]

[0908]

[0909] [Chemical Formula 127]

[0910]

[0911] [Chemical Formula 128]

[0912]

[0913] [Chemical Formula 129]

[0914]

[0915]

Chemical Formula 130

[0916]

[0917]

Chemical Formula 131

[0918]

[0919]

Chemical Formula 132

[0920]

[0921]

Chemical Formula 133

[0922]

[0923]

Chemical Formula 134

[0924]

[0925] [Chemical Formula 135]

[0926]

[0927]

Chemical Formula 136

[0928]

[0929]

Chemical Formula 137

[0930]

[0931]

Chemical Formula 138

[0932]

[0933]

Chemical Formula 139

[0934]

[0935] [Chemical Formula 140]

[0936]

[0937]

Chemical Formula 141

[0938]

[0939] [Chemical Formula 142]

[0940]

[0941] [Chemical Formula 143]

[0942]

[0943] [Chemical Formula 144]

[0944]

[0945] [Chemical Formula 145]

[0946]

[0947] [Chemical Formula 146]

[0948]

[0949] [Chemical Formula 147]

[0950]

[0951] [Chemical Formula 148]

[0952]

[0953] [Chemical Formula 149]

[0954]

[0955] [Chemical Formula 150]

[0956]

[0957]

Chemical Formula 151

[0958]

[0959]

Chemical Formula 152

[0960]

[0961] [Chemical Formula 1.53]

[0962]

[0963]

Chemical Formula 154

[0964]

[0965]

Chemical Formula 155

[0966]

[0967] [Chemical Formula 156]

[0968]

[0969] [Chemical Formula 157]

[0970]

[0971] [Chemical Formula 158]

[0972]

[0973] [Chemical Formula 159]

[0974]

[0975] [Chemical Formula 160]

[0976]

[0977]

Chemical Formula 161

[0978]

[0979] [Chemical Formula 162]

[0980]

[0981] [Chemical Formula 163]

[0982]

[0983] [Chemical Formula 164]

[0984]

[0985] [Chemical Formula 165]

[0986]

[0987]

Chemical Formula 166

[0988]

[0989] [Chemical Formula 167]

[0990]

[0991] [Chemical Formula 168]

[0992]

[0993] [Chemical Formula 169]

[0994]

[0995] [Chemical Formula 170]

[0996]

[0997]

Chemical Formula 171

[0998]

[0999] [Chemical Formula 172]

[1000]

[1001]

Chemical Formula 173

[1002]

[1003] [Chemical Formula 174]

[1004]

[1005] [Chemical Formula 175]

[1006]

[1007] [Chemical Formula 176]

[1008]

[1009]

Chemical Formula 177

[1010]

[1011] [Chemical Formula 178]

[1012]

[1013] [Chemical Formula 179]

[1014]

[1015] [Chemical Formula 180]

[1016]

[1017]

Chemical Formula 181

[1018]

[1019]

Chemical Formula 182

[1020]

[1021] [Chemical Formula 183]

[1022]

[1023] [Chemical Formula 184]

[1024]

[1025] [Chemical Formula 185]

[1026]

[1027] [Chemical Formula 186]

[1028]

[1029] [Chemical Formula 187]

[1030]

[1031]

Chemical Formula 188

[1032]

[1033]

Chemical Formula 189

[1034]

[1035] [Chemical Formula 190]

[1036]

[1037]

Chemical Formula 191

[1038]

[1039] [Chemical Formula 192]

[1040]

[1041] [Chemical Formula 193]

[1042]

[1043] [Chemical Formula 194]

[1044]

[1045] [Chemical Formula 195]

[1046]

[1047] [Chemical Formula 196]

[1048]

[1049] [Chemical Formula 197]

[1050]

[1051] [Chemical Formula 198]

[1052]

[1053]

Chemical Formula 199

[1054]

[1055] [Chemical Formula 200]

[1056]

[1057]

Chemical Formula 201

[1058]

[1059]

Chemical Formula 202

[1060]

[1061]

Chemical Formula 203

[1062]

[1063]

Chemical Formula 204

[1064]

[1065]

Chemical Formula 205

[1066]

[1067]

Chemical Formula 206

[1068]

[1069] [Chemical Formula 207]

[1070]

[1071] [Chemical Formula 208]

[1072]

[1073]

Chemical Formula 209

[1074]

[1075]

Chemical Formula 210

[1076]

[1077]

Chemical Formula 211

[1078]

[1079]

Chemical Formula 212

[1080]

[1081]

Chemical Formula 213

[1082]

[1083]

Chemical Formula 214

[1084]

[1085]

Chemical Formula 215

[1086]

[1087]

Chemical Formula 216

[1088]

[1089]

Chemical Formula 217

[1090]

[1091]

Chemical Formula 218

[1092]

[1093]

Chemical Formula 219

[1094]

[1095]

Chemical Formula 220

[1096]

[1097]

Chemical Formula 221

[1098]

[1099]

Chemical Formula 222

[1100]

[1101]

Chemical Formula 223

[1102]

[1103] [Chemical Formula 224]

[1104]

[1105] [Chemical Formula 225]

[1106]

[1107]

Chemical Formula 226

[1108]

[1109] [Chemical Formula 227]

[1110]

[1111] [Chemical Formula 228]

[1112]

[1113] [Chemical Formula 229]

[1114]

[1115]

Chemical Formula 230

[1116]

[1117]

Chemical Formula 231

[1118]

[1119]

Chemical Formula 232

[1120]

[1121]

Chemical Formula 233

[1122]

[1123]

Chemical Formula 234

[1124]

[1125] [Chemical Formula 235]

[1126]

[1127]

Chemical Formula 236

[1128]

[1129] [Chemical Formula 237]

[1130]

[1131] [Chemical Formula 238]

[1132]

[1133] [Chemical Formula 239]

[1134]

[1135] [Chemical Formula 240]

[1136]

[1137]

Chemical Formula 241

[1138]

[1139]

Chemical Formula 242

[1140]

[1141] [Chemical Formula 243]

[1142]

[1143] [Chemical Formula 244]

[1144]

[1145] [Chemical Formula 245]

[1146]

[1147] [Chemical Formula 246]

[1148]

[1149] [Chemical Formula 247]

[1150]

[1151] [Chemical Formula 248]

[1152]

[1153] [Chemical Formula 249]

[1154]

[1155] [Chemical Formula 250]

[1156]

[1157]

Chemical Formula 251

[1158]

[1159]

Chemical Formula 252

[1160]

[1161] [Chemical Formula 253]

[1162]

[1163] [Chemical Formula 254]

[1164]

[1165] [Chemical Formula 255]

[1166]

[1167] [Chemical Formula 256]

[1168]

[1169] [Chemical Formula 257]

[1170]

[1171] [Chemical Formula 258]

[1172]

[1173] [Chemical Formula 259]

[1174]

[1175] [Chemical Formula 260]

[1176]

[1177]

Chemical Formula 261

[1178]

[1179]

Chemical Formula 262

[1180]

[1181] [Chemical Formula 263]

[1182]

[1183] [Chemical Formula 264]

[1184]

[1185] [Chemical Formula 265]

[1186]

[1187]

Chemical Formula 266

[1188]

[1189] [Chemical Formula 267]

[1190]

[1191] [Chemical Formula 268]

[1192]

[1193] [Chemical Formula 269]

[1194]

[1195] [Chemical Formula 270]

[1196]

[1197]

Chemical Formula 271

[1198]

[1199]

Chemical Formula 272

[1200]

[1201] [Chemical Formula 273]

[1202]

[1203] [Chemical Formula 274]

[1204]

[1205] [Chemical Formula 275]

[1206]

[1207] [Chemical Formula 276]

[1208]

[1209] [Chemical Formula 277]

[1210]

[1211] [Chemical Formula 278]

[1212]

[1213] [Chemical Formula 279]

[1214]

[1215] [Chemical Formula 280]

[1216]

[1217]

Chemical Formula 281

[1218]

[1219]

Chemical Formula 282

[1220]

[1221] [Chemical Formula 283]

[1222]

[1223] [Chemical Formula 284]

[1224]

[1225] [Chemical Formula 285]

[1226]

[1227] [Chemical Formula 286]

[1228]

[1229] [Chemical Formula 287]

[1230]

[1231] [Chemical Formula 288]

[1232]

[1233] [Chemical Formula 289]

[1234]

[1235] [Chemical Formula 290]

[1236]

[1237]

Chemical Formula 291

[1238]

[1239]

Chemical Formula 292

[1240]

[1241] [Chemical Formula 293]

[1242]

[1243] [Chemical Formula 294]

[1244]

[1245] [Chemical Formula 295]

[1246]

[1247] [Chemical Formula 296]

[1248]

[1249] [Chemical Formula 297]

[1250]

[1251] [Chemical Formula 298]

[1252]

[1253] [Chemical Formula 299]

[1254]

[1255]

Chemical Formula 300

[1256]

[1257]

Chemical Formula 301

[1258]

[1259]

Chemical Formula 302

[1260]

[1261]

Chemical Formula 303

[1262]

[1263] Chemical formula 304

[1264]

[1265]

Chemical Formula 305

[1266]

[1267]

Chemical Formula 306

[1268]

[1269]

Chemical Formula 307

[1270]

[1271] [Chemical Formula 308]

[1272]

[1273]

Chemical Formula 309

[1274]

[1275]

Chemical Formula 310

[1276]

[1277]

Chemical Formula 311

[1278]

[1279]

Chemical Formula 312

[1280]

[1281]

Chemical Formula 313

[1282]

[1283]

Chemical Formula 314

[1284]

[1285]

Chemical Formula 315

[1286]

[1287]

Chemical Formula 316

[1288]

[1289]

Chemical Formula 317

[1290]

[1291]

Chemical Formula 318

[1292]

[1293]

Chemical Formula 319

[1294]

[1295]

Chemical Formula 320

[1296]

[1297]

Chemical Formula 321

[1298]

[1299]

Chemical Formula 322

[1300]

[1301]

Chemical Formula 323

[1302]

[1303] [Chemical Formula 324]

[1304]

[1305] [Chemical Formula 325]

[1306]

[1307]

Chemical Formula 326

[1308]

[1309] [Chemical Formula 327]

[1310]

[1311] [Chemical Formula 328]

[1312]

[1313]

Chemical Formula 329

[1314]

[1315]

Chemical Formula 330

[1316]

[1317]

Chemical Formula 331

[1318]

[1319]

Chemical Formula 332

[1320]

[1321]

Chemical Formula 333

[1322]

[1323]

Chemical Formula 334

[1324]

[1325]

Chemical Formula 335

[1326]

[1327]

Chemical Formula 336

[1328]

[1329]

Chemical Formula 337

[1330]

[1331]

Chemical Formula 338

[1332]

[1333] [Chemical Formula 339]

[1334]

[1335] [Chemical Formula 340]

[1336]

[1337]

Chemical Formula 341

[1338]

[1339]

Chemical Formula 342

[1340]

[1341]

Chemical Formula 343

[1342]

[1343]

Chemical Formula 344

[1344]

[1345] [Chemical Formula 345]

[1346]

[1347] [Chemical Formula 346]

[1348]

[1349] [Chemical Formula 347]

[1350]

[1351] [Chemical Formula 348]

[1352]

[1353] [Chemical Formula 349]

[1354]

[1355] [Chemical Formula 350]

[1356]

[1357]

Chemical Formula 351

[1358]

[1359]

Chemical Formula 352

[1360]

[1361]

Chemical Formula 353

[1362]

[1363] [Chemical Formula 354]

[1364]

[1365]

Chemical Formula 355

[1366]

[1367] [Chemical Formula 356]

[1368]

[1369] [Chemical Formula 357]

[1370]

[1371] Materials for organic EL components

[1372] The organic EL element material of the present invention comprises the inventive compound. The content of the inventive compound in the organic EL element material is 1% by mass or more (including 100%), preferably 10% by mass or more (including 100%), more preferably 50% by mass or more (including 100%), further preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). The organic EL element material of the present invention is useful for the manufacture of organic EL elements.

[1373] Organic EL components

[1374] The organic EL element of the present invention includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer includes a light-emitting layer, and at least one layer of the organic layer includes the inventive compound.

[1375] Examples of organic layers comprising the inventive compound include hole transport regions (hole injection layers, hole transport layers, electron blocking layers, exciton blocking layers, etc.) disposed between the anode and the light-emitting layer, light-emitting layers, spacer layers, and electron transport regions (electron injection layers, electron transport layers, hole blocking layers, etc.) disposed between the cathode and the light-emitting layer, and are not limited thereto. The inventive compound is preferably used as a material for the hole transport region or light-emitting layer of a fluorescent or phosphorescent EL element, more preferably as a material for the hole transport region, even more preferably as a material for the hole injection layer, hole transport layer, electron blocking layer, or exciton blocking layer, and particularly preferably as a material for the hole injection layer or hole transport layer.

[1376] The organic EL element of the present invention can be a monochromatic light-emitting element of the fluorescent or phosphorescent type, or a white light-emitting element of the fluorescent / phosphorescent hybrid type. It can be a simple type with a single light-emitting unit, or a series type with multiple light-emitting units. Preferably, it is a fluorescent light-emitting element. Here, "light-emitting unit" refers to the smallest unit that contains an organic layer, wherein at least one layer is a light-emitting layer, and the injected holes and electrons emit light by recombination.

[1377] For example, the following are typical component configurations for a simple organic EL element.

[1378] (1) Anode / Light-emitting unit / Cathode

[1379] Alternatively, the aforementioned light-emitting unit can also be a multilayer type with multiple phosphorescent and fluorescent light-emitting layers. In this case, spacer layers can be provided between the light-emitting layers to prevent excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer. The following shows a typical layer configuration of a simplified light-emitting unit. The layers in parentheses are optional.

[1380] (a)(hole injection layer / )hole transport layer / fluorescent layer / electron transport layer( / electron injection layer)

[1381] (b) (Hole injection layer / ) Hole transport layer / First fluorescent layer / Second fluorescent layer / Electron transport layer ( / Electron injection layer)

[1382] (c)(Hole injection layer / )Hole transport layer / phosphorescent layer / spacer layer / fluorescent layer / electron transport layer( / electron injection layer)

[1383] (d)(Hole injection layer / )Hole transport layer / First phosphorescent layer / Second phosphorescent layer / Spacer layer / Fluorescent layer / Electron transport layer( / Electron injection layer)

[1384] (e)(hole injection layer / )hole transport layer / phosphorescent layer / spacer layer / first fluorescent layer / second fluorescent layer / electron transport layer( / electron injection layer)

[1385] (f)(hole injection layer / )hole transport layer / electron blocking layer / fluorescent layer / electron transport layer( / electron injection layer)

[1386] (g)(hole injection layer / )hole transport layer / exciton blocking layer / fluorescent layer / electron transport layer( / electron injection layer)

[1387] (h)(Hole Injection Layer / )First Hole Transport Layer / Second Hole Transport Layer / Fluorescent Layer / Electron Transport Layer( / Electron Injection Layer)

[1388] (i)(hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent layer / first electron transport layer / second electron transport layer( / electron injection layer)

[1389] (j)(hole injection layer / )hole transport layer / fluorescent layer / hole blocking layer / electron transport layer( / electron injection layer)

[1390] (k)(hole injection layer / )hole transport layer / fluorescent layer / exciton blocking layer / electron transport layer( / electron injection layer)

[1391] (1)(Hole injection layer / )First hole transport layer / Second hole transport layer / First fluorescent emissive layer / Second fluorescent emissive layer / First electron transport layer / Second electron transport layer( / electron injection layer)

[1392] (m)(hole injection layer / ) 1st hole transport layer / 2nd hole transport layer / 3rd hole transport layer / 1st fluorescent emissive layer / 2nd fluorescent emissive layer / 1st electron transport layer / 2nd electron transport layer ( / electron injection layer)

[1393] (n)(hole injection layer / ) 1st hole transport layer / 2nd hole transport layer / 3rd hole transport layer / fluorescent emission layer / 1st electron transport layer / 2nd electron transport layer ( / electron injection layer)

[1394] Each of the aforementioned phosphorescent or fluorescent emitting layers can be configured to display a different emitting color. Specifically, in the aforementioned emitting unit (f), a layer configuration such as (hole injection layer / ) hole transport layer / first phosphorescent emitting layer (red emitting light) / second phosphorescent emitting layer (green emitting light) / spacer layer / fluorescent emitting layer (blue emitting light) / electron transport layer can be used.

[1395] It should be noted that electron blocking layers can be appropriately placed between each light-emitting layer and the hole transport layer or spacer layer. Similarly, hole blocking layers can be appropriately placed between each light-emitting layer and the electron transport layer. By placing electron blocking layers and hole blocking layers, electrons or holes can be confined within the light-emitting layer, thereby increasing the recombination probability of charges in the light-emitting layer and thus improving luminous efficiency.

[1396] The following are typical component configurations for tandem organic EL elements.

[1397] (2) Anode / First Light-Emitting Unit / Intermediate Layer / Second Light-Emitting Unit / Cathode

[1398] Here, the first light-emitting unit and the second light-emitting unit described above can be selected independently from the light-emitting units described above.

[1399] The aforementioned intermediate layer is also commonly referred to as an intermediate electrode, intermediate conductive layer, charge generation layer, electron extraction layer, connecting layer, or intermediate insulating layer, and can be constructed using known materials that supply electrons to the first light-emitting unit and holes to the second light-emitting unit.

[1400] Figure 1 This is a schematic diagram illustrating an example of the structure of the organic EL element of the present invention. The organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10 disposed between the anode 3 and the cathode 4. The light-emitting unit 10 has a light-emitting layer 5. A hole transport region 6 (hole injection layer, hole transport layer, etc.) is provided between the light-emitting layer 5 and the anode 3, and an electron transport region 7 (electron injection layer, electron transport layer, etc.) is provided between the light-emitting layer 5 and the cathode 4. In addition, an electron blocking layer (not shown) can be provided on the anode 3 side of the light-emitting layer 5, and a hole blocking layer (not shown) can be provided on the cathode 4 side of the light-emitting layer 5. As a result, electrons and holes can be confined in the light-emitting layer 5, thereby further improving the exciton generation efficiency in the light-emitting layer 5.

[1401] Figure 2 This is a schematic diagram illustrating another configuration of the organic EL element of the present invention. The organic EL element 11 includes a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 20 disposed between the anode 3 and the cathode 4. The light-emitting unit 20 has a light-emitting layer 5. The hole transport region disposed between the anode 3 and the light-emitting layer 5 is formed by a hole injection layer 6a, a first hole transport layer 6b, and a second hole transport layer 6c. In addition, the electron transport region disposed between the light-emitting layer 5 and the cathode 4 is formed by a first electron transport layer 7a and a second electron transport layer 7b.

[1402] Figure 3This is a schematic diagram illustrating another configuration of the organic EL element of the present invention. The organic EL element 12 includes a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 30 disposed between the anode 3 and the cathode 4. The light-emitting unit 30 has a light-emitting layer 5. The hole transport region disposed between the anode 3 and the light-emitting layer 5 is formed by a hole injection layer 6a, a first hole transport layer 6b, a second hole transport layer 6c, and a third hole transport layer 6d. Furthermore, the electron transport region disposed between the light-emitting layer 5 and the cathode 4 is formed by a first electron transport layer 7a and a second electron transport layer 7b.

[1403] It should be noted that in this invention, the host material combined with the fluorescent dopant material (fluorescent emitting material) is called the fluorescent host material, and the host material combined with the phosphorescent dopant material is called the phosphorescent host material. The distinction between fluorescent and phosphorescent hosts is not solely based on molecular structure. That is, a phosphorescent host material refers to the material that forms a phosphorescent emitting layer containing phosphorescent dopant, and does not mean that it cannot be used as a material to form a fluorescent emitting layer. The same applies to fluorescent hosts.

[1404] substrate

[1405] The substrate serves as a support for the organic EL element. Examples of substrates include sheets made of glass, quartz, or plastic. Flexible substrates can also be used. Examples of flexible substrates include plastic substrates formed from polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Inorganic vapor-deposited films can also be used.

[1406] anode

[1407] The anode formed on the substrate is preferably a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically 4.0 eV or higher). Examples of such anodes include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the aforementioned metals (e.g., titanium nitride).

[1408] These materials are typically formed into films using sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1–10 wt% zinc oxide relative to indium oxide, and indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5–5 wt% tungsten oxide and 0.1–1 wt% zinc oxide relative to indium oxide. Alternatively, they can be fabricated using vacuum evaporation, coating, inkjet printing, spin coating, and other methods.

[1409] Hole transport region

[1410] As described above, the organic layer may include a hole transport region located between the anode and the light-emitting layer. The hole transport region is composed of a hole injection layer, a hole transport layer, an electron blocking layer, etc. Preferably, the hole transport region contains the inventive compound. Preferably, at least one of the layers constituting the hole transport layer contains the inventive compound, and more preferably, the hole transport layer contains the inventive compound.

[1411] The hole injection layer formed adjacent to the anode is formed using a material that is easy to inject holes into regardless of the work function of the anode. Therefore, materials commonly used as electrode materials (e.g., metals, alloys, conductive compounds and mixtures thereof, elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[1412] Elements belonging to Group 1 or Group 2 of the periodic table that have low work functions can also be used, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them. It should be noted that when using alkali metals, alkaline earth metals, and alloys containing them to form the anode, vacuum evaporation or sputtering methods can be used. Furthermore, when using silver paste, coating or inkjet printing methods can be used.

[1413] Hole injection layer

[1414] A hole injection layer is a layer containing a material with high hole injection properties (hole injection material), which is formed between the anode and the light-emitting layer, or between the hole transport layer and the anode in the presence of a hole transport layer.

[1415] Other than the inventive compound, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc., can be used as hole-injecting materials.

[1416] Examples of hole injection layer materials include 4,4',4'-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4'-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), and 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (DNT), all of which are low-molecular-weight organic compounds. Aromatic amine compounds such as PD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1).

[1417] Polymers (oligomers, dendritic polymers, polymers, etc.) can also be used. Examples include: poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVT PA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (PTPDMA), and poly[N,N'bis(4-butylphenyl)-N,N'bis(phenyl)benzidine] (Poly-TPD). Additionally, polymers containing acids, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[1418] In addition, acceptor materials such as hexaazabenzophenanthrene (HAT) compounds represented by the following formula (K) are also preferred.

[1419] [Chemical Formula 358]

[1420]

[1421] (In the above formula, R) 221 ~R 226 Each can independently represent a cyano group, -CONH2, a carboxyl group, or -COOR. 227 (R 227 (Refers to alkyl groups having 1 to 20 carbon atoms or cycloalkyl groups having 3 to 20 carbon atoms). Additionally, it is selected from R... 221 With R 222 R223 With R 224 and R 225 With R 226 Two adjacent groups can bond with each other to form a group represented by -CO-O-CO-.

[1422] As R 227 Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, and cyclohexyl.

[1423] Hole transport layer

[1424] A hole transport layer is a layer containing a material with high hole transportability (hole transport material) formed between the anode and the light-emitting layer, or between the hole injection layer and the light-emitting layer in the presence of a hole injection layer. The inventive compound can be used alone or in combination with the compounds described below for use in the hole transport layer.

[1425] The hole transport layer can be a single-layer structure or a multi-layer structure containing two or more layers. For example, the hole transport layer can be a two-layer structure comprising a first hole transport layer (anode side) and a second hole transport layer (cathode side). That is, the aforementioned hole transport region can include a first hole transport layer on the anode side and a second hole transport layer on the cathode side. Alternatively, the hole transport layer can be a three-layer structure comprising a first hole transport layer, a second hole transport layer, and a third hole transport layer sequentially from the anode side. That is, a third hole transport layer can be disposed between the second hole transport layer and the light-emitting layer.

[1426] In one embodiment of the present invention, the hole transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, or the hole transport layer closest to the cathode in the multilayer structure, such as the second hole transport layer of the two-layer structure or the third hole transport layer of the three-layer structure, is preferably adjacent to the light-emitting layer. In another embodiment of the present invention, an electron blocking layer, as described later, is sandwiched between the hole transport layer and the light-emitting layer of the single-layer structure, or between the hole transport layer closest to the light-emitting layer and the light-emitting layer in the multilayer structure.

[1427] In the case where the hole transport layer has a two-layer structure, at least one of the first hole transport layer and the second hole transport layer contains the inventive compound. That is, the inventive compound is contained only in the first hole transport layer, or only in the second hole transport layer, or in both the first and second hole transport layers. In one aspect of the invention, it is preferable that the inventive compound is contained in the second hole transport layer. That is, preferably, the inventive compound is contained only in the second hole transport layer, or the inventive compound is contained in both the first and second hole transport layers.

[1428] In the case where the hole transport layer has a three-layer structure, at least one of the first to third hole transport layers contains the inventive compound. That is, the inventive compound is contained in only one layer selected from the first to third hole transport layers (containing only the first hole transport layer, only the second hole transport layer, or only the third hole transport layer), only two layers selected from the first to third hole transport layers (containing only the first and second hole transport layers, only the first and third hole transport layers, or only the second and third hole transport layers), or all layers of the first to third hole transport layers.

[1429] In one aspect of the invention, the inventive compound is preferably contained in the third hole transport layer. That is, preferably, the inventive compound is contained only in the third hole transport layer, or the inventive compound is contained in the third hole transport layer and selected from one or both of the first hole transport layer and the second hole transport layer.

[1430] In one aspect of the present invention, the inventive compound contained in each of the aforementioned hole transport layers is preferably a protium-based compound from a manufacturing cost perspective. The aforementioned protium-based compound refers to an inventive compound in which all hydrogen atoms are protium atoms.

[1431] Therefore, the present invention includes an organic EL element comprising an inventive compound that substantially contains only protium, either of the first hole transport layer and the second hole transport layer or both of these (in the case of a two-layer structure), and an organic EL element comprising at least one of the first to third hole transport layers comprising an inventive compound that substantially contains only protium. "Inventive compound that substantially contains only protium" means that, relative to the total amount of the inventive compound, the proportion of protium is 90 mol% or more, preferably 95 mol% or more, more preferably 99 mol% or more (each comprising 100%).

[1432] Other hole transport layer materials besides the inventive compound can be, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc.

[1433] Examples of aromatic amine compounds include: 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BAFLP), and 4,4'-bis[N-(9,9-dimethyl]... [fluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The above compounds have 10 -6 cm 2 Hole mobility above / Vs.

[1434] Examples of carbazole derivatives include 4,4'-bis(9-carbazolyl)biphenyl (CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (PCzPA).

[1435] Examples of anthracene derivatives include 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (abbreviated as t-BuDNA), 9,10-bis(2-naphthyl)anthracene (abbreviated as DNA), and 9,10-diphenylanthracene (abbreviated as DPAnnth).

[1436] Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used.

[1437] Among them, any compound whose hole transport capability is higher than its electron transport capability can use compounds other than those mentioned above.

[1438] In the organic EL element having a hole transport layer with a two-layer structure of the present invention, it is preferred that the first hole transport layer contains one or more compounds as shown in formula (11) or formula (12).

[1439] In the organic EL element having a three-layer hole transport layer of the present invention, it is preferred that one or both of the first hole transport layer and the second hole transport layer contain one or more compounds represented by the following formula (11) or (12).

[1440] In the organic EL element of the present invention having an n-layer structure (n being an integer of 4 or more) of hole transport layers, it is preferred that at least one of the first hole transport layer to the (n-1)th hole transport layer contains one or more compounds as shown in formula (11) or formula (12).

[1441] [Chemical Formula 359]

[1442]

[1443] In equations (11) and (12) above,

[1444] L A1 、L B1 、L C1 、L A2 、L B2 、L C2 and L D2 Each is independently a single bond, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in the cyclic ring, or a divalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms.

[1445] k is 1, 2, 3, or 4.

[1446] When k is 1, L E2 It is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in the cyclic ring, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 carbon atoms in the cyclic ring.

[1447] When k is 2, 3, or 4, there are 2, 3, or 4 L E2 They are the same or different.

[1448] When k is 2, 3, or 4, multiple L E2 They may bond together to form substituted or unsubstituted monocyclic rings, substituted or unsubstituted fused rings, or they may not bond together.

[1449] L does not form the aforementioned single ring and does not form the aforementioned fused ring E2 It is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in the cyclic ring, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 carbon atoms in the cyclic ring.

[1450] A 1 、B 1 、C 1 A 2 、B 2 、C 2 and D 2 Each is independently a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group with 5 to 50 cyclic atoms, or a -Si(R') group. 901 )(R'902 )(R' 903 ),

[1451] R' 901 、R' 902 and R' 903 Each is independently a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic formation.

[1452] In R' 901 In the case of multiple R's, multiple R's 901 They are the same or different.

[1453] In R' 902 In the case of multiple R's, multiple R's 902 They are the same or different.

[1454] In R' 903 In the case of multiple R's, multiple R's 903 They are the same or different.

[1455] In formulas (11) and (12), A1, B1, C1, A2, B2, C2, and D2 are preferably each independently selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, and substituted or unsubstituted carbazoyl.

[1456] Furthermore, more preferably, at least one of A1, B1 and C1 in formula (11) and at least one of A2, B2, C2 and D2 in formula (12) are substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or substituted or unsubstituted carbazoyl.

[1457] The fluorene groups in A1, B1, C1, A2, B2, C2, and D2 may have a substituent at the 9-position, such as 9,9-dimethylfluorene or 9,9-diphenylfluorene. Alternatively, the substituents at the 9-position may form a ring with each other, for example, a fluorene skeleton or a thallium skeleton.

[1458] L A1 、L B1 、L C1 、L A2 、L B2 、L C2 and L D2 Preferably, each arylene group is a single bond, substituted or unsubstituted, and has 6 to 12 carbon atoms in the cyclic group.

[1459] As specific examples of the compounds shown in formulas (11) and (12), the following compounds can be cited.

[1460]

Chemical Formula 360

[1461]

[1462] dopant material of the light-emitting layer

[1463] The luminescent layer is a layer containing a highly luminescent material (dopant material), and various materials can be used. For example, fluorescent luminescent materials and phosphorescent luminescent materials can be used as dopant materials. Fluorescent luminescent materials are compounds that emit light using a singlet excited state, while phosphorescent luminescent materials are compounds that emit light using a triplet excited state.

[1464] In one embodiment of the organic EL element involved in this invention, the light-emitting layer is a single layer.

[1465] In another embodiment of the organic EL element involved in this invention, the light-emitting layer comprises a first light-emitting layer and a second light-emitting layer.

[1466] As blue fluorescent luminescent materials that can be used in the luminescent layer, pyrene derivatives, styrene amine derivatives, etc., can be used. Derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. Specifically, examples include N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviated as YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthrayl)triphenylamine (abbreviated as YGAPA), and 4-(10-phenyl-9-anthrayl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCPAPA), etc.

[1467] As green fluorescent materials that can be used in the luminescent layer, aromatic amine derivatives can be used. Specifically, examples include N-(9,10-diphenyl-2-anthrayl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthrayl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCABPhA), and N-(9,10-diphenyl-2-anthrayl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPA). PA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthrayl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviated as: 2YGABPhA), N,N,9-triphenylanthracene-9-amine (abbreviated as: DPhAPhA), etc.

[1468] As red-based fluorescent materials that can be used in the luminescent layer, tetraphenyl derivatives, diamine derivatives, etc., can be used. Specifically, examples include N,N,N',N'-tetra(4-methylphenyl)tetraphenyl-5,11-diamine (abbreviated as p-mPhTD) and 7,14-diphenyl-N,N,N',N'-tetra(4-methylphenyl)acenaphthene[1,2-a]fluoranthene-3,10-diamine (abbreviated as p-mPhAFD).

[1469] In one embodiment of the present invention, the light-emitting layer preferably comprises a fluorescent light-emitting material (fluorescent dopant material).

[1470] As blue phosphorescent materials that can be used in the luminescent layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes can be used. Specifically, examples include bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)tetra(1-pyrazolyl)borate (abbreviated as Fir6), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (abbreviated as Firpic), bis[2-(3',5'-bistrifluoromethylphenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (abbreviated as Ir(CF3ppy)2(pic)), and bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)acetylacetone (abbreviated as FIracac).

[1471] As a green phosphorescent material that can be used in the light-emitting layer, iridium complexes can be used. Examples include tris(2-phenylpyridine-N,C2')iridium(III) (abbreviated as Ir(ppy)3), bis(2-phenylpyridine-N,C2')iridium(III)acetylacetonate (abbreviated as Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazole)iridium(III)acetylacetonate (abbreviated as Ir(pbi)2(acac)), and bis(benzo[h]quinoline)iridium(III)acetylacetonate (abbreviated as Ir(bzq)2(acac)).

[1472] As red phosphorescent materials that can be used in the luminescent layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes can be used. Specifically, organometallic complexes such as bis[2-(2'-benzo[4,5-α]thienyl)pyridine-N,C3']iridium(III)acetylacetonate (abbreviated as: Ir(btp)2(acac)), bis(1-phenylisoquinoline-N,C2')iridium(III)acetylacetonate (abbreviated as: Ir(piq)2(acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviated as: Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as: PtOEP) can be used.

[1473] In addition, rare earth metal complexes such as tri(acetylacetonyl)(monophenanthrene)terbium(III) (abbreviated as Tb(acac)3(Phen)), tri(1,3-diphenyl-1,3-propanedione)(monophenanthrene)eupium(III) (abbreviated as Eu(DBM)3(Phen)), and tri[1-(2-thiophenecarboxyl)-3,3,3-trifluoroacetone](monophenanthrene)eupium(III) (abbreviated as Eu(TTA)3(Phen)) can be used as phosphorescent materials because their luminescence originates from the luminescence of rare earth metal ions (electronic transitions between different multiplicity levels).

[1474] The main material of the light-emitting layer

[1475] The light-emitting layer can be configured by dispersing the aforementioned dopant material within other materials (the host material). Preferably, a material with a lower unoccupied orbital level (LUMO level) higher than the dopant material and a higher occupied orbital level (HOMO level) lower than the dopant material is used.

[1476] As the main material, for example, using

[1477] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes;

[1478] (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives;

[1479] (3) Carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or Derivatives and other fused aromatic compounds,

[1480] (4) Aromatic amine compounds such as triarylamine derivatives or fused polycyclic aromatic amine derivatives.

[1481] For example, metal complexes such as tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-hydroxyquinoline)aluminum(III) (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium(II) (abbreviated as BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO), and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ) can be used;

[1482] Heterocyclic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-biphenyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviated as TAZ), 2,2',2'-(1,3,5-phenyltriyl)tris(1-phenyl-1H-benzimidazole) (abbreviated as TPBI), phenanthroline (abbreviated as BPhen), and copper bath (abbreviated as BCP);

[1483] 9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (abbreviated as CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (abbreviated as DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviated as DPPA), 9,10-bis(2-naphthyl)anthracene (abbreviated as DNA), 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (abbreviated as DNA) t-BuDNA), 9,9'-Bantane (BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (DPNS2), 3,3',3'-(benzene-1,3,5-triyl)tripyrene (TPB3), 9,10-diphenylanthracene (DPAnth), 6,12-dimethoxy-5,11-diphenyl Equally fused aromatic compounds; and

[1484] N,N-Diphenyl-9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole-3-amine (abbreviation: CzAlPA), 4-(10-phenyl-9-anthrayl)triphenylamine (abbreviation: DPhPA), N,9-Diphenyl-N-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), N,9-Diphenyl-N-{4-[4-(10-phenyl-9-anthrayl)phenyl]phenyl)-9H-carbazole-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthrayl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), 4, Aromatic amine compounds such as 4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as DFLDPBi), and 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB) can be used as the main material.

[1485] In particular, in the case of blue fluorescent elements, the following anthracene compounds are preferred as the main material.

[1486]

Chemical Formula 361

[1487]

[1488]

Chemical Formula 362

[1489]

[1490]

Chemical Formula 363

[1491]

[1492] In one embodiment of the organic EL element of the present invention, when the light-emitting layer comprises a first light-emitting layer and a second light-emitting layer, at least one of the components constituting the first light-emitting layer is different from the component constituting the second light-emitting layer. For example, embodiments such as: the dopant material contained in the first light-emitting layer is different from the dopant material contained in the second light-emitting layer, and the host material contained in the first light-emitting layer is different from the host material contained in the second light-emitting layer.

[1493] In the organic EL element of the present invention, the light-emitting layer may contain a luminescent compound exhibiting fluorescence with a main peak wavelength of less than 500 nm (hereinafter sometimes referred to simply as "fluorescent compound").

[1494] The method for determining the peak wavelength of the main peak of the compound is as follows. A 5 μmol / L toluene solution of the compound to be measured is prepared and added to a quartz cuvette. The emission spectrum of the sample is measured at room temperature (300 K) (vertical axis is set as emission intensity, and horizontal axis is set as wavelength). The emission spectrum can be measured using a spectrophotometer (device name: F-7000) manufactured by Hitachi Advanced Scientific Corporation. It should be noted that the emission spectroscopy measuring device is not limited to the device used here.

[1495] In the emission spectrum, the peak wavelength at which the emission intensity reaches its maximum is taken as the main peak wavelength. It should be noted that, in this specification, the main peak wavelength is sometimes referred to as the fluorescence emission main peak wavelength (FL-peak).

[1496] The fluorescent compound can be either the dopant material or the host material.

[1497] When the light-emitting layer is a single layer, either the dopant material or the host material may be the aforementioned fluorescent luminescent compound, or both may be the aforementioned fluorescent luminescent compound.

[1498] Furthermore, when the light-emitting layer comprises a first light-emitting layer (anode side) and a second light-emitting layer (cathode side), only one of the first and second light-emitting layers may contain the aforementioned fluorescent luminescent compound, or both light-emitting layers may contain the aforementioned fluorescent luminescent compound. When the first light-emitting layer contains the aforementioned fluorescent luminescent compound, only one of the dopant material and the host material contained in the first light-emitting layer may be the aforementioned fluorescent luminescent compound, or both may be the aforementioned fluorescent luminescent compound. Similarly, when the second light-emitting layer contains the aforementioned fluorescent luminescent compound, only one of the dopant material and the host material contained in the second light-emitting layer may be the aforementioned fluorescent luminescent compound, or both may be the aforementioned fluorescent luminescent compound.

[1499] Electron transport layer

[1500] An electron transport layer is a layer containing a material with high electron transport properties (electron transport material), which is formed between the light-emitting layer and the cathode, or between the electron injection layer and the light-emitting layer in the presence of an electron injection layer.

[1501] The electron transport layer can be a single-layer structure or a multi-layer structure containing two or more layers. For example, the electron transport layer can be a two-layer structure containing a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one aspect of the invention, the electron transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, or the electron transport layer closest to the anode in the multi-layer structure, such as the first electron transport layer in the two-layer structure, is preferably adjacent to the light-emitting layer. In another aspect of the invention, a hole-blocking layer, as described later, may be sandwiched between the electron transport layer and the light-emitting layer in the single-layer structure, or between the electron transport layer closest to the light-emitting layer in the multi-layer structure.

[1502] For example, an electron transport layer can be used

[1503] (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes;

[1504] (2) Imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives, and other heteroaromatic compounds.

[1505] (3) Polymer compounds.

[1506] Examples of metal complexes include: tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-hydroxyquinoline)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (abbreviated as BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO), and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ).

[1507] Examples of heteroaromatic compounds include: 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviated as p-EtTAZ), phenanthroline (abbreviated as BPhen), copper hydroxide (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)zirconia (abbreviated as BzOs).

[1508] Examples of high molecular weight compounds include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy).

[1509] The above material has 10 -6 cm 2 Materials with electron mobility greater than / Vs. It should be noted that any material whose electron transport capability is higher than its hole transport capability can be used for the electron transport layer.

[1510] Electron injection layer

[1511] The electron injection layer is a layer containing a material with high electron injection capability. The electron injection layer can use alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), rare earth metals such as europium (Eu) and ytterbium (Yb), and compounds containing these metals. Examples of such compounds include alkali metal oxides, alkali metal halides, organic complexes containing alkali metals, alkaline earth metal oxides, alkaline earth metal halides, organic complexes containing alkaline earth metals, rare earth metal oxides, rare earth metal halides, and organic complexes containing rare earth metals. Furthermore, multiple such compounds can be used in combination.

[1512] Alternatively, substances containing alkali metals, alkaline earth metals, or compounds thereof in the electron-transporting material can be used; specifically, substances containing magnesium (Mg) in Alq can also be used. It should be noted that in this case, electron injection from the cathode can be performed more efficiently.

[1513] Alternatively, the electron injection layer can be a composite material formed by mixing an organic compound and an electron donor. Such a composite material exhibits excellent electron injection and electron transport properties because the organic compound accepts electrons from the electron donor. In this case, the organic compound is preferably a material with excellent electron transport properties; specifically, materials constituting the electron transport layer, such as those described above (metal complexes, heteroaromatic compounds, etc.), can be used. The electron donor can be any material that exhibits electron-donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Additionally, alkali metal oxides and alkaline earth metal oxides are preferred, such as lithium oxides, calcium oxides, and barium oxides. Furthermore, Lewis bases such as magnesium oxide can also be used. Additionally, organic compounds such as tetrathiofulvalene (TTF) can also be used.

[1514] cathode

[1515] The cathode preferably uses metals, alloys, conductive compounds, and mixtures thereof with low work functions (specifically below 3.8 eV). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr) and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb) and alloys containing them.

[1516] It should be noted that when using alkali metals, alkaline earth metals, or alloys containing them to form the cathode, vacuum evaporation or sputtering methods can be used. Additionally, when using silver paste, coating or inkjet printing methods can be used.

[1517] It should be noted that by setting an electron injection layer, a wide variety of conductive materials, such as Al, Ag, ITO, graphene, and indium tin oxide containing silicon or silicon oxide, can be used to form cathodes regardless of the work function. These conductive materials can be deposited using methods such as sputtering, inkjet printing, and spin coating.

[1518] Insulation layer

[1519] Organic EL elements are prone to pixel defects due to leakage and short circuits because an electric field is applied to the ultrathin film. To prevent this, an insulating layer formed by an insulating thin film can be inserted between a pair of electrodes.

[1520] Examples of materials that can be used as insulating layers include alumina, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. It should be noted that mixtures or laminates of these materials can also be used.

[1521] Spacer layer

[1522] In the case of a stacked fluorescent and phosphorescent layer, the spacer layer refers to a layer disposed between the fluorescent and phosphorescent layers to prevent excitons generated in the phosphorescent layer from diffusing to the fluorescent layer or to adjust carrier balance. Alternatively, the spacer layer may be disposed between multiple phosphorescent layers.

[1523] Since the spacer layer is disposed between the light-emitting layers, it is preferably made of a material that has both electron transport and hole transport properties. Furthermore, to prevent the diffusion of triplet energy within adjacent phosphorescent light-emitting layers, the triplet energy is preferably 2.6 eV or higher. Materials similar to those used for the hole transport layer can be used as examples of materials for the spacer layer.

[1524] Barrier layer

[1525] Electron blocking layers, hole blocking layers, exciton blocking layers, and other blocking layers can also be placed adjacent to the light-emitting layer. An electron blocking layer prevents electrons from leaking from the light-emitting layer to the hole transport layer, while a hole blocking layer prevents holes from leaking from the light-emitting layer to the electron transport layer. An exciton blocking layer prevents excitons generated in the light-emitting layer from diffusing to surrounding layers, thus confining the excitons within the light-emitting layer.

[1526] The layers of the aforementioned organic EL element can be formed using conventional vapor deposition or coating methods. For example, they can be formed using vapor deposition methods such as vacuum vapor deposition or molecular beam vapor deposition (MBE), or using known coating methods based on solutions of the compound forming the layer, such as dip coating, spin coating, casting, rod coating, and roll coating.

[1527] There are no particular limitations on the thickness of the above-mentioned layers. Generally speaking, if the film thickness is too thin, it is easy to generate defects such as pinholes. Conversely, if it is too thick, a high driving voltage is required and the efficiency will be reduced. Therefore, it is usually 5nm to 10μm, and more preferably 10nm to 0.2μm.

[1528] In the organic EL element of the present invention having a hole transport layer with a 2-layer or 3-layer structure, the combined thickness of the first hole transport layer and the second hole transport layer is preferably 30 nm or more and 150 nm or less, more preferably 40 nm or more and 130 nm or less.

[1529] In addition, in one aspect of the present invention, the thickness of the second hole transport layer in the 2-layer or 3-layer structure is preferably 5 nm or more, more preferably 20 nm or more, further preferably 25 nm or more, particularly preferably 35 nm or more, and preferably 100 nm or less.

[1530] In another aspect of the present invention, the thickness of the hole transport layer adjacent to the light-emitting layer is preferably 5 nm or more, more preferably 20 nm or more, even more preferably 25 nm or more, particularly preferably 30 nm or more, and preferably 100 nm or less.

[1531] Furthermore, in the organic EL element of the present invention having a hole transport layer with a 2-layer or 3-layer structure, the ratio of the thickness D2 of the second hole transport layer to the thickness D1 of the first hole transport layer is preferably 0.3 < D2 / D1 < 4.0, more preferably 0.5 < D2 / D1 < 3.5, and even more preferably 0.75 < D2 / D1 < 3.0.

[1532] As a preferred embodiment of the organic EL element of the present invention, examples include:

[1533] (1) Organic EL element with a hole transport layer with a two-layer structure

[1534] • A first embodiment in which the second hole transport layer contains the inventive compound and the first hole transport layer does not contain the inventive compound;

[1535] Both the first hole transport layer and the second hole transport layer contain the second embodiment of the inventive compound;

[1536] • A third embodiment in which the first hole transport layer contains the inventive compound and the second hole transport layer does not contain the inventive compound;

[1537] (2) Organic EL element with a hole transport layer with a 3-layer structure

[1538] • A fourth embodiment in which the first hole transport layer contains the inventive compound, and the second and third hole transport layers do not contain the inventive compound;

[1539] • A fifth embodiment in which the second hole transport layer contains the inventive compound, and the first and third hole transport layers do not contain the inventive compound;

[1540] • A sixth embodiment in which the third hole transport layer contains the inventive compound, and the first and second hole transport layers do not contain the inventive compound;

[1541] • A seventh embodiment in which the first and second hole transport layers contain the inventive compound, and the third hole transport layer does not contain the inventive compound;

[1542] • An eighth embodiment in which the first and third hole transport layers contain the inventive compound, and the second hole transport layer does not contain the inventive compound;

[1543] • A tenth embodiment in which the second and third hole transport layers contain the inventive compound, and the first hole transport layer does not contain the inventive compound;

[1544] • The first to third hole transport layers all contain the tenth embodiment of the inventive compound; etc.

[1545] electronic devices

[1546] One embodiment of the present invention relates to an organic EL element that can be used in electronic devices such as display devices and light-emitting devices. Examples of display devices include display components such as organic EL flat panel modules, televisions, mobile phones, tablet computers, or personal computers. Examples of light-emitting devices include lighting fixtures or vehicle lights.

[1547] The aforementioned organic EL elements can be used in display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, as well as electronic devices such as lighting and vehicle lamps.

[1548] Example

[1549] The present invention will be further described in detail below using examples, but the present invention is not limited to the following examples.

[1550] The inventive compound used in the manufacture of the organic EL element (I) in Example 1

[1551]

Chemical Formula 364

[1552]

[1553] The comparative compound used in the manufacture of the organic EL element (I) of Comparative Example 1

[1554]

Chemical Formula 365

[1555]

[1556] Other compounds used in the manufacture of the organic EL element (I) of Example 1 and Comparative Example 1

[1557]

Chemical Formula 366

[1558]

[1559] Fabrication of organic EL elements (I)

[1560] <Example 1>

[1561] A 25mm × 75mm × 1.1mm glass substrate (manufactured by Geomatec Corporation) with an ITO transparent electrode (anode) was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was set to 130nm.

[1562] The cleaned glass substrate with the ITO transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, compound HT-1 and compound HA were co-deposited on the side where the transparent electrode was formed to cover the transparent electrode, thus forming a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-1 to compound HA (HT-1:HA) was 97:3.

[1563] Next, compound HT-1 was deposited on the hole injection layer to form the first hole transport layer with a thickness of 40 nm.

[1564] Next, compound Inv-1 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 5 nm.

[1565] Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited on the second hole transport layer to form a first emitting layer with a thickness of 10 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 99:1.

[1566] Next, compound BH-2 (the host material) and compound BD-1 (the dopant material) were co-deposited on the first luminescent layer to form a second luminescent layer with a thickness of 10 nm. The mass ratio of compound BH-2 to compound BD-1 (BH-2:BD-1) was 99:1.

[1567] Next, compound ET-1 was deposited on the luminescent layer to form a first electron transport layer with a thickness of 5 nm.

[1568] Next, a second electron transport layer with a thickness of 25 nm was formed by co-evaporating compounds ET-2 and Liq onto the first electron transport layer. The mass ratio of compounds ET-2 to Liq (ET-2:Liq) was 50:50.

[1569] Next, Yb was deposited on the second electron transport layer to form an electron injection electrode with a film thickness of 1 nm.

[1570] Then, metallic Al was deposited on the electron-injecting electrode to form a metal cathode with a film thickness of 50 nm.

[1571] The following shows the layer configuration of the organic EL element (I) of Example 1 thus obtained.

[1572] ITO(130) / HT-1:HA=97:3(10) / HT-1(40) / Inv-1(5) / BH-1:BD-1=99:1(1 0) / BH-2:BD-1=99:1(10) / ET-1(5) / ET-2:Liq=50:50(25) / Yb(1) / Al(50)

[1573] In the above layer composition, the numbers in parentheses are film thicknesses (nm), and the ratios are mass ratios.

[1574] <Comparative Example 1>

[1575] Instead of the inventive compound Inv-1, comparative compound Ref-1 was used, and each organic EL element (I) was fabricated in the same manner as in Example 1.

[1576] Evaluation of organic EL elements (I)

[1577] (1) 95% lifespan (LT95)

[1578] For the obtained organic EL element (I), at a current density of 50 mA / cm², 2 A DC constant current drive was used to measure the time it took for the brightness to decrease to 95% of the initial brightness, which was taken as the 95% lifetime (LT95).

[1579] The results are shown in Table 1.

[1580]

Table 1

[1581] Table 1

[1582]

[1583] The results in Table 1 clearly show that compound Inv-1 provides a longer-lived organic EL element compared to the comparative compound Ref-1.

[1584] The inventive compounds used in the manufacture of the organic EL element (II) in Examples 2-11

[1585]

Chemical Formula 367

[1586]

[1587] The comparative compound [Chemical Formula 368] used in the manufacture of the organic EL element (II) of Comparative Example 2

[1588]

[1589] Other compounds used in the manufacture of the organic EL element (II) of Examples 2-11 and Comparative Example 2

[1590]

Chemical Formula 369

[1591]

[1592] Fabrication of Organic EL Components (II)

[1593] <Example 2>

[1594] A 25mm × 75mm × 1.1mm glass substrate (manufactured by Geomatec Corporation) with an ITO transparent electrode (anode) was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was set to 130nm.

[1595] The cleaned glass substrate with the ITO transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, compound HT-2 and compound HA were co-deposited on the side where the transparent electrode was formed to cover the transparent electrode, thus forming a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-2 to compound HA (HT-2:HA) was 97:3.

[1596] Next, compound HT-2 was deposited on the hole injection layer to form the first hole transport layer with a thickness of 85 nm.

[1597] Next, compound Inv-4 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 5 nm.

[1598] Next, compound BH-3 (host material) and compound BD-2 (dopant material) were co-deposited on the second hole transport layer to form a first emitting layer with a thickness of 20 nm. The mass ratio of compound BH-3 to compound BD-2 (BH-3:BD-2) was 99:1.

[1599] Next, compound ET-3 was deposited on the luminescent layer to form a first electron transport layer with a thickness of 5 nm.

[1600] Next, a second electron transport layer with a thickness of 31 nm was formed by co-evaporating compounds ET-4 and Liq onto the first electron transport layer. The mass ratio of compounds ET-4 to Liq (ET-4:Liq) was 50:50.

[1601] Next, Liq was deposited on the second electron transport layer to form an electron injection electrode with a film thickness of 1 nm.

[1602] Then, metallic Al was deposited on the electron-injecting electrode to form a metal cathode with a film thickness of 80 nm.

[1603] The following shows the layer configuration of the organic EL element (II) of Example 2 thus obtained.

[1604] ITO(130) / HT-2:HA=97:3(10) / HT-2(85) / Inv-4(5) / BH-3:BD-2=99:1(20) / ET-3(5) / ET-4:Liq=50:50(31) / Liq(1) / Al(80)

[1605] In the above layer composition, the numbers in parentheses are film thicknesses (nm), and the ratios are mass ratios.

[1606] <Examples 3-11 and Comparative Example 2>

[1607] The organic EL element (II) was prepared in the same manner as in Example 2, except that the compound listed in Table 2 was used instead of compound Inv-2.

[1608] Evaluation of Organic EL Element (II)

[1609] The 95% lifetime (LT95) of the obtained organic EL element (II) was determined using the same method as that used for evaluating the organic EL element (I). The results are shown in Table 2.

[1610]

Table 2

[1611] Table 2

[1612]

[1613] The results in Table 2 clearly show that compounds Inv-4 to 12 and 20 provide organic EL elements with longer lifespans compared to the comparative compound Ref-2.

[1614] The inventive compounds used in the manufacture of the organic EL element (III) in Examples 12-18

[1615] [Chemical Formula 370]

[1616]

[1617] The comparative compound used in the manufacture of the organic EL element (III) of Comparative Example 3

[1618]

Chemical Formula 371

[1619]

[1620] Other compounds used in the manufacture of the organic EL element (III) of Examples 12-18 and Comparative Example 3

[1621]

Chemical Formula 372

[1622]

[1623] Fabrication of Organic EL Components (III)

[1624] <Example 12>

[1625] A 25mm × 75mm × 1.1mm glass substrate (manufactured by Geomatec Corporation) with an ITO transparent electrode (anode) was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was set to 130nm.

[1626] The cleaned glass substrate with the ITO transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, compound HT-3 and compound HA were co-deposited on the side where the transparent electrode was formed to cover the transparent electrode, thus forming a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-3 to compound HA (HT-3:HA) was 97:3.

[1627] Next, compound HT-3 was deposited on the hole injection layer to form the first hole transport layer with a thickness of 80 nm.

[1628] Next, compound Inv-13 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 7.5 nm.

[1629] Next, a 20 nm thick BH (host material):BD-3 (dopant material) film was formed on the second hole transport layer. This BH:BD-3 film functions as the emissive layer. The BH [compounds BH-4 and BH-5 (both host materials)] contained in the emissive layer are in a mass ratio of 3:2, and the concentration of BD-3 is 2% by mass relative to the entire emissive layer.

[1630] Next, compound ET-5 was deposited on the luminescent layer to form a first electron transport layer with a thickness of 5 nm.

[1631] Next, a second electron transport layer with a thickness of 25 nm was formed by co-evaporating compounds ET-6 and Liq onto the first electron transport layer. The mass ratio of compounds ET-6 to Liq (ET-6:Liq) was 67:33.

[1632] Next, Yb was deposited on the second electron transport layer to form an electron injection electrode with a film thickness of 1 nm.

[1633] Then, metallic Al was deposited on the electron-injecting electrode to form a metal cathode with a film thickness of 80 nm.

[1634] The following shows the layer configuration of the organic EL element (III) of Example 12 thus obtained.

[1635] ITO(130) / HT-3:HA=97:3(10) / HT-3(80) / Inv-13(7.5) / BH-4:BH-5 ∶BD-3=60∶40∶2(20) / ET-5(5) / ET-6∶Liq=67∶33(25) / Yb(1) / Al(80)

[1636] In the above layer composition, the numbers in parentheses are film thicknesses (nm), and the ratios are mass ratios.

[1637] <Examples 13-18 and Comparative Example 3>

[1638] Organic EL elements (III) were prepared in the same manner as in Example 12, except that the compounds listed in Table 3 were used instead of compound Inv-13.

[1639] Evaluation of Organic EL Element (III)

[1640] The 95% lifetime (LT95) of the obtained organic EL element (III) was determined using the same method as that used for evaluating the organic EL element (I). The results are shown in Table 3.

[1641] Table 3

[1642] Table 3

[1643]

[1644] The results in Table 3 clearly show that compounds Inv-13 to 19 provide organic EL elements with longer lifespans compared to the comparative compound Ref-3.

[1645] The inventive compound synthesized in the synthetic example

[1646]

Chemical Formula 373

[1647]

[1648] [Chemical Formula 374]

[1649]

[1650] Intermediate Synthesis Example 1: Synthesis of Benzo[b]naphtho[2,1-d]furan-4-yl Trifluoromethanesulfonate [Chemical Formula 375]

[1651]

[1652] Under an argon atmosphere, a mixture of 10.0 g (57.4 mmol) of 5-methoxy-1-naphthol, 50.2 g (287 mmol) of 1-bromo-2-fluorobenzene, 28.1 g (86.0 mmol) of cesium carbonate, and 287 mL of N-methyl-2-pyrrolidone was stirred at 145 °C for 12 hours. The reaction mixture was cooled to room temperature, water was added, and extraction was performed using toluene, followed by concentration under reduced pressure. The residue was purified by silica gel column chromatography to yield 14.7 g of 1-(2-bromophenoxy)-5-methoxynaphthalene as a colorless liquid. The yield was 78%.

[1653] Under an argon atmosphere, a mixture of 14.7 g (44.8 mmol) of 1-(2-bromophenoxy)-5-methoxynaphthalene, 1.83 g (2.24 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, 21.9 g (67.2 mmol) of cesium carbonate, and 224 mL of N-methyl-2-pyrrolidone was stirred at 130 °C for 5 hours. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with toluene and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 8.0 g of 4-methoxybenzo[b]naphtho[2,1-d]furan as a white solid. The yield was 72%.

[1654] Under an argon atmosphere, a mixture of 2.48 g (10.0 mmol) of the obtained 4-methoxybenzo[b]naphtho[2,1-d]furan and 100 mL of dichloromethane was cooled to 0 °C, and 20 mL of a 1.0 mol / L boron tribromide dichloromethane solution was added. The mixture was stirred at room temperature for 5 hours. The reaction solution was cooled to -78 °C, water was added, and extraction was performed using dichloromethane, followed by concentration under reduced pressure. The residue was purified by silica gel column chromatography to give 2.13 g of benzo[b]naphtho[2,1-d]furan-4-ol as a white solid. The yield was 91%.

[1655] Under an argon atmosphere, a mixture of 1.17 g (5.0 mmol) of the obtained benzo[b]naphtho[2,1-d]furan-4-ol, 0.061 g (0.50 mmol) of N,N-dimethyl-4-aminopyridine, 10.0 mL (125 mmol) of pyridine, 1.01 mL (6.00 mmol) of trifluoromethanesulfonic anhydride, and 25 mL of dichloromethane was stirred at 0 °C for 5 hours. Water was added, and the mixture was extracted with dichloromethane and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 1.48 g of benzo[b]naphtho[2,1-d]furan-4-yl trifluoromethanesulfonic acid as a white solid. The yield was 81%.

[1656] Example 2 of intermediate synthesis: Synthesis of intermediate A-1

[1657] [Chemical Formula 376]

[1658]

[1659] Under an argon atmosphere, a mixture of 6.66 g (22.4 mmol) of 5-bromobenzo[b]naphtho[2,1-d]furan (starting material 1), 5.21 g (23.8 mmol) of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborhexacyclopentane-2-yl)aniline (starting material 2), 0.205 g (0.224 mmol) of tris(dibenzylacetone)dipalladium(0), 0.427 g (0.897 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos), 33.6 mL (67.2 mmol) of 2M potassium phosphate aqueous solution, and 149 mL of 1,4-dioxane was stirred at 110 °C for 7 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 6.01 g of intermediate A-1 as a white solid. The yield was 87%.

[1660] Synthesis Examples 3 and 4 of Intermediates: Synthesis of Intermediates A-2 and A-3

[1661] In intermediate synthesis example 2, starting materials 1 and 2 were used as the substances listed in Table 4, and the same operation was performed to obtain intermediates A-2 and A-3. The yields of intermediates A-2 and A-3 are shown in Table 4.

[1662] Table 4

[1663] Table 4

[1664]

[1665] Example 5 of intermediate synthesis: Synthesis of intermediate B-1

[1666]

Chemical Formula 377

[1667]

[1668] Under an argon atmosphere, a mixture of 11.0 g (30.0 mmol) of 5-bromobenzo[b]naphtho[2,1-d]furan (starting material 1), 5.16 g (33.0 mmol) of 2-chlorophenylboronic acid (starting material 2), 1.04 g (0.90 mmol) of tetrakis(triphenylphosphine)palladium(0), 37.5 mL (75.0 mmol) of 2M sodium carbonate aqueous solution, and 100 mL of DME was refluxed to boiling point for 5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 8.15 g of intermediate B-1 as a white solid. The yield was 83%.

[1669] Synthesis Examples of Intermediates 6-9: Synthesis of Intermediates B-2 to B-5

[1670] In intermediate synthesis example 5, starting materials 1 and 2 were used as the substances listed in Table 5, and the same operation was performed to obtain intermediates B-2 to B-5. The yields of intermediates B-2 to B-5 are shown in Table 5.

[1671] Table 5

[1672] Table 5

[1673]

[1674] Example 10: Synthesis of intermediate C-1

[1675] [Chemical Formula 378]

[1676]

[1677] Under an argon atmosphere, a mixture of 21.5 g (69.5 mmol) of intermediate A-3 (starting material 1), 16.2 g (69.5 mmol) of 4-bromobiphenyl (starting material 2), 1.27 g (1.39 mmol) of tris(dibenzylacetone)dipalladium(0), 1.73 g (2.78 mmol) of BINAP, 7.35 g (76.0 mmol) of sodium tert-butoxide, and 460 mL of toluene was refluxed at boiling point for 7 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to give 26.2 g of intermediate C-1 as a white solid. The yield was 82%.

[1678] Examples of intermediate synthesis 11-14: Synthesis of intermediates C-2 to C-5

[1679] In intermediate synthesis example 10, starting materials 1 and 2 were used as the substances listed in Table 6, and the same operation was performed to obtain intermediates C-2 to C-5. The yields of intermediates C-2 to C-5 are shown in Table 5.

[1680] Table 6

[1681] Table 6

[1682]

[1683] Synthesis Example 1-1: Synthesis of the inventive compound Inv-1

[1684] [Chemical Formula 379]

[1685]

[1686] Under an argon atmosphere, a mixture of 3.09 g (10.0 mmol) of intermediate A-1 (intermediate 1), 4.90 g (21.0 mmol) of 4-bromobiphenyl (intermediate 2), 0.366 g (0.400 mmol) of tris(dibenzylacetone)dipalladium(0), 0.464 g (1.60 mmol) of tri-tert-butylphosphonium tetrafluoroborate, 2.69 g (28.0 mmol) of sodium tert-butoxide, and 100 mL of toluene was refluxed at boiling point for 7 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica gel column chromatography and recrystallization to give 3.87 g of a white solid. The yield was 63%.

[1687] The obtained substance was identified by mass spectrometry as compound Inv-1, with a molecular weight of 613.76 and an m / e ratio of 614.

[1688] Synthetic Examples 1-2 and 1-3: Synthesis of the inventive compounds Inv-2 and Inv-3

[1689] In Synthesis Example 1-1, intermediates 1 and 2 were used as the substances listed in Table 7, and the same operation was performed otherwise to obtain the inventive compounds Inv-2 and Inv-12. The yields of the inventive compounds Inv-2 and Inv-12 are shown in Table 7.

[1690]

Table 7

[1691] Table 7

[1692]

[1693] Synthesis Example 2-1: Synthesis of the inventive compound Inv-3

[1694] [Chemical Formula 380]

[1695]

[1696] Under an argon atmosphere, a mixture of 3.45 g (10.5 mmol) of intermediate B-1 (intermediate 1), 3.21 g (21.0 mmol) of N-[1,1'-biphenyl]-4-yl[1,1'-biphenyl]-4-amine (intermediate 2), 0.366 g (0.400 mmol) of tris(dibenzylacetone)dipalladium(0), 0.328 g (0.800 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos), 4.2 mL of sodium tert-amyloxide (40% toluene solution), and 67 mL of toluene was refluxed at boiling point for 7 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica gel column chromatography and recrystallization to give 4.16 g of a white solid. The yield was 68%.

[1697] The obtained substance was identified by mass spectrometry as compound Inv-3, with a molecular weight of 613.76 and an m / e ratio of 614.

[1698] Synthetic Examples 2-2 to 2-17: Synthesis of Inventive Compounds Inv-4 to Inv-11 and Inv-13 to Inv-20

[1699] In Synthesis Example 2-1, intermediates 1 and 2 were used as substances listed in Tables 8-10, and the same operation was performed otherwise to obtain the inventive compounds Inv-4-Inv-11 and Inv-13-Inv-20. The yields of the inventive compounds Inv-4-Inv-11 and Inv-13-Inv-20 are shown in Tables 8-10.

[1700]

Table 8

[1701] Table 8

[1702]

[1703]

Table 9

[1704] Table 9

[1705]

[1706] Table 10

[1707] Table 0

[1708]

[1709] Explanation of symbols

[1710] 1, 11, 12 Organic EL elements

[1711] 2 substrate

[1712] 3 Anode

[1713] 4 Cathode

[1714] 5. Light-emitting layer

[1715] 5a First luminescent layer

[1716] 5b Second luminescent layer

[1717] 6. Hole transport region (hole transport layer)

[1718] 6a Hole injection layer

[1719] 6b Hole Transport Layer 1

[1720] 6c Hole transport layer 2

[1721] 6d Third Hole Transport Layer

[1722] 7. Electron transport region (electron transport layer)

[1723] 7a First electron transport layer

[1724] 7b Second electron transport layer

[1725] 10, 20, 30 light-emitting units

Claims

1. The compound represented by the following formula (1), wherein, In equation (1), N ＊ The central nitrogen atom, R 1 ~R 4 It is a hydrogen atom. L 1 and L 2 Each is independently a single bond or an unsubstituted aryl group with 6 to 12 carbon atoms in a cyclic ring. L 3 and L 4 It is a single key. Ar 1 and Ar 2 Each of the groups is independently represented by any one of the following formulas (1a), (1b), and (1d). In equation (1a), *21 is related to L 1 or L 2 The bonding position, R 101 ~R 105 and R 106 ~R 110 Each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted cyclic aryl group having 6 to 12 carbon atoms, wherein the atom is selected from R. 101 ~R 105 One of them is a single bond bonded to *22, selected from R 106 ~R 110 One of them is a single bond that bonds with *23. Selected from R which is not the single bond described 101 ~R 105 Two adjacent elements in the loop are not bonded to each other and therefore do not form a loop. Selected from R which is not the single bond described 106 ~R 110 Two adjacent elements in the loop are not bonded to each other and therefore do not form a loop. k is 0 or 1, l is 0 or 1 k + l is an integer from 1 to 2. R 111 ~R 115 Each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 carbon atoms in a cyclic structure. Selected from R 111 ~R 115 Two adjacent elements in the loop are not bonded to each other and therefore do not form a loop. In equation (1b), *24 is related to L 1 or L 2 The bonding position, R 121 ~R 128 Each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted cyclic aryl group having 6 to 12 carbon atoms. Among them, selected from R 121 ~R 128 One of them is a single bond bonded to *25, selected from R that is not the single bond mentioned above. 121 ~R 128 Two adjacent elements in the loop are not bonded to each other and therefore do not form a loop. In equation (1d), *28 is related to L 1 or L 2 The bonding position, X 2 For oxygen atoms, sulfur atoms, or NR A , R A It is an unsubstituted alkyl group having 1 to 6 carbon atoms or an unsubstituted aryl group having 6 to 12 carbon atoms in a cyclic structure. R 141 ~R 148 Each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted cyclic aryl group having 6 to 12 carbon atoms, wherein the atom is selected from the R group. 141 ~R 148 and R A One of them is a single bond that bonds with *29. Selected from R which is not the single bond described 141 ~R 148 The two adjacent groups in it do not bond to each other and therefore do not form a ring. Ar 3 The group represented by the following formula (x) In equation (x), *3 is related to L 4 The bonding position, R 31 R 32 R 36 ~R 38 and R 41 ~R 44 Each is independently a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms. m is 0, n is 0 R 33 and R 34 One of them is a single bond bonded to *a, and the other is a single bond bonded to *b. R 35 For a single bond that bonds with *4, X 1 It consists of oxygen or sulfur atoms.

2. The compound according to claim 1, wherein, X 1 It is an oxygen atom.

3. The compound according to claim 1 or 2, wherein, It contains at least one deuterium atom.

4. A material for an organic electroluminescent element comprising the compound of claim 1 or 2.

5. A hole transport layer material comprising the compound of claim 1 or 2.

6. An organic electroluminescent element having a cathode, an anode, and an organic layer located between the cathode and the anode, the organic layer comprising a light-emitting layer, at least one layer of the organic layer comprising the compound of claim 1 or 2.

7. The organic electroluminescent element according to claim 6, wherein, The organic layer includes a hole transport region located between the anode and the light-emitting layer, and the hole transport region contains the compound.

8. The organic electroluminescent element according to claim 7, wherein, The hole transport region includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side, wherein one of the first hole transport layer and the second hole transport layer contains the compound or both of them contain the compound.

9. The organic electroluminescent element according to claim 8, wherein, The light-emitting layer is directly connected to the second hole transport layer.

10. The organic electroluminescent element according to claim 8, wherein, The combined thickness of the first hole transport layer and the second hole transport layer is greater than 30 nm and less than 150 nm.

11. The organic electroluminescent element according to claim 6, wherein, The light-emitting layer is a single layer.

12. The organic electroluminescent element according to claim 6, wherein, The luminescent layer contains a luminescent compound that exhibits fluorescence with a main peak wavelength below 500 nm.

13. The organic electroluminescent element according to claim 6, wherein, The light-emitting layer contains fluorescent dopant material.

14. An electronic device comprising an organic electroluminescent element according to any one of claims 6 to 13.

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