Compounds, materials for organic electroluminescent elements, organic electroluminescent elements, and electronic devices.

Abstract

The present invention provides compounds that further improve the performance of organic EL elements, organic electroluminescent elements with improved element performance, and electronic devices containing such organic electroluminescent elements. [Solution] A compound represented by the following formula (1) is provided. JPEG2026144795000120.jpg66129

Description

[Technical Field]

[0001] The present invention relates to compounds, materials for organic electroluminescent elements, organic electroluminescent elements, and electronic devices including said organic electroluminescent elements. [Background technology]

[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 light-emitting region from the cathode side and holes from the anode side. The injected electrons and holes recombine in the light-emitting region to generate an excited state, and light is emitted when the excited state returns to the ground state. Therefore, the development of materials that efficiently transport electrons or holes to the light-emitting region and facilitate the recombination of electrons and holes is important for obtaining high-performance organic EL devices.

[0003] Patent documents 1 to 4 disclose compounds used as materials for organic electroluminescent devices (hereinafter sometimes referred to as "materials for organic EL devices"). [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Chinese Patent Application Publication No. 116813658 Specification [Patent Document 2] International Publication No. 2014 / 015935 [Patent Document 3] Chinese Patent Application Publication No. 117362185 Specification [Patent Document 4] U.S. Patent Application Publication No. 2023 / 0142412 [Overview of the project] [Problems that the invention aims to solve]

[0005] Conventionally, many compounds for organic EL devices have been reported, but compounds that can further improve the performance of organic EL devices are still in demand.

[0006] The present invention has been made to solve the above problems, and an object of the present invention is to provide a compound that further improves the performance of organic EL devices, an organic EL device with improved device performance, and an electronic device including such an organic EL device.

Means for Solving the Problems

[0007] The present inventors have conducted intensive studies on the performance of organic EL devices containing the compounds described in Patent Documents 1 to 4, and as a result, have found that the performance of an organic EL device containing a compound represented by the following formula (1) is further improved.

[0008] In one aspect, the present invention provides a compound represented by the following formula (1).

Chem

[0009] In another embodiment, the present invention provides a material for an organic EL device comprising a compound represented by formula (1).

[0010] In yet another embodiment, the present invention provides an organic electroluminescent element having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer contains the compound.

[0011] In yet another embodiment, the present invention provides an electronic device comprising the organic electroluminescent element. [Effects of the Invention]

[0012] Organic EL elements containing the compound represented by formula (1) exhibit improved element performance. [Brief explanation of the drawing]

[0013] [Figure 1] This is a schematic diagram showing an example of the layer configuration of an organic EL element according to one aspect of the present invention. [Figure 2] This is a schematic diagram showing another example of the layer configuration of an organic EL element according to one aspect of the present invention. [Figure 3] This is a schematic diagram showing another example of the layer configuration of an organic EL element according to one aspect of the present invention. [Modes for carrying out the invention]

[0014] [Definition] In this specification, the term "hydrogen atom" includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0015] In this specification, in chemical structural formulas, any bondable positions where symbols such as "R" or "D" representing a deuterium atom are not explicitly indicated shall be assumed to be bonded to hydrogen atoms, i.e., light hydrogen atoms, deuterium atoms, or tritium atoms.

[0016] In this specification, the ring-forming carbon number refers to the number of carbon atoms among the atoms constituting the ring itself in a compound with a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, fused ring compounds, crosslinked compounds, carbocyclic compounds, and heterocyclic compounds). If the ring is substituted by a substituent, the carbon atoms in the substituent are not included in the ring-forming carbon number. The same applies to the "ring-forming carbon number" described below unless otherwise specified. For example, a benzene ring has 6 ring-forming carbon atoms, a naphthalene ring has 10 ring-forming carbon atoms, a pyridine ring has 5 ring-forming carbon atoms, and a furan ring has 4 ring-forming carbon atoms. Also, for example, the ring-forming carbon number of a 9,9-diphenylfluorenyl group is 13, and the ring-forming carbon number of a 9,9'-spirobifluorenyl group is 25. Furthermore, when a benzene ring is substituted with an alkyl group, for example, the number of carbon atoms in that alkyl group is not included in the number of ring-forming carbon atoms of the benzene ring. Therefore, the number of ring-forming carbon atoms in a benzene ring substituted with an alkyl group is 6. Similarly, when a naphthalene ring is substituted with an alkyl group, for example, the number of carbon atoms in that alkyl group is not included in the number of ring-forming carbon atoms of the naphthalene ring. Therefore, the number of ring-forming carbon atoms in a naphthalene ring substituted with an alkyl group is 10.

[0017] In this specification, the number of ring-forming atoms refers to the number of atoms that constitute the ring itself in compounds with a ring-bonded structure (e.g., monocyclic compounds, fused rings, and ring aggregates) (e.g., monocyclic compounds, fused ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of ring-forming atoms) and atoms included in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. The same applies to "number of ring-forming atoms" as described below unless otherwise specified. For example, the number of ring-forming atoms in a pyridine ring is 6, the number of ring-forming atoms in a quinazoline ring is 10, and the number of ring-forming atoms in a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring, or the number of atoms constituting substituents, are not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms in a pyridine ring to which hydrogen atoms or substituents are bonded is 6. Furthermore, for example, hydrogen atoms bonded to the carbon atom of the quinazoline ring, or atoms constituting substituents, are not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring-forming atoms of a quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

[0018] In this specification, the expression "substituted or unsubstituted ZZ group having XX to YY carbon atoms" means that "XX to YY carbon atoms" represents the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of substituents when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0019] In this specification, the expression "ZZ group with substituted or unsubstituted atoms of XX to YY" means that "atom count XX to YY" represents the number of atoms when the ZZ group is unsubstituted, and does not include the number of substituent atoms when it is substituted. Here, "YY" is greater than "XX", where "XX" is an integer of 1 or more, and "YY" is an integer of 2 or more.

[0020] In this specification, an unsubstituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is "unsubstituted ZZ group," and a substituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is "substituted ZZ group." In this specification, "unsubstituted" in the context of a "substituted or unsubstituted ZZ group" means that the hydrogen atoms in the ZZ group are not replaced by substituents. The hydrogen atoms in an "unsubstituted ZZ group" are light hydrogen atoms, deuterium atoms, or tritium atoms. Furthermore, in this specification, "substituted" in the context of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. Similarly, "substituted" in the context of "BB group substituted with AA group" means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0021] "Substituents as described herein" The substituents described herein will be explained below.

[0022] The number of ring-forming carbon atoms in the "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring-forming atoms in the "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkyl group" as described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkenyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkynyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted cycloalkyl groups" described herein is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted arylene group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring-forming atoms in the "unsubstituted divalent heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkylene group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein.

[0023] • "substituted or unsubstituted aryl groups" Specific examples of "substituted or unsubstituted aryl groups" as described herein (Specific Examples Group G1) include the following unsubstituted aryl groups (Specific Examples Group G1A) and substituted aryl groups (Specific Examples Group G1B), etc. (Here, "unsubstituted aryl group" refers to the case where "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and "substituted aryl group" refers to the case where "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" simply includes both "unsubstituted aryl groups" and "substituted aryl groups." A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced by substituents. Examples of "substituted aryl groups" include the groups in which one or more hydrogen atoms of an "unsubstituted aryl group" in specific example group G1A below are replaced by substituents, and the examples of substituted aryl groups in specific example group G1B below. Note that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl groups" described herein also include groups in which the hydrogen atoms bonded to the carbon atom of the aryl group itself in the "substituted aryl group" in specific example group G1B below are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted aryl group" in specific example group G1B below are further replaced by substituents.

[0024] • Unsubstituted aryl groups (specific examples group G1A): Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-Naphthyl group, 2-Naphthyl group, anthryl group, Benzoantryl group, Phenanthryl group, Benzophenanthryl group, Phenalenyl group, Pyrenyl group, Chrysenyl group, Benzocrisenyl group, Triphenylenyl group, benzotriphenylenyl group, Tetraceryl group, Pentacenyl group, Fluorenyl group, 9,9'-Spirobifluorenyl group, Benzofluorenyl group, Dibenzofluorenyl group, Fluoranthenyl group, Benzofluoranthenyl group, Perilenyl group, and A monovalent aryl group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0025] [ka]

[0026] [ka]

[0027] • Substitutive aryl groups (Specific examples group G1B): o-Tryl group, m-tolyl group, p-tril group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, Meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, Cyanophenyl group, Triphenylsilylphenyl group, Trimethylsilylphenyl group, Phenylnaphthyl group, Naphthylphenyl group, and A group obtained by replacing one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the general formulas (TEMP-1) to (TEMP-15) above with substituents.

[0028] • "Substitutable or unsubstituted heterocyclic groups" The “heterocyclic group” as described herein is a cyclic group containing at least one heteroatom in its ring-forming atoms. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron. The term "heterocyclic group" as used herein refers to either a monocyclic group or a fused ring group. The term "heterocyclic group" as used herein refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples of "substituted or unsubstituted heterocyclic groups" as described herein (Specific Examples Group G2) include the following unsubstituted heterocyclic groups (Specific Examples Group G2A) and substituted heterocyclic groups (Specific Examples 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" simply includes both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups." A "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of "substituted heterocyclic groups" include the groups in specific example group G2A below in which hydrogen atoms of an "unsubstituted heterocyclic group" are replaced, and the examples of substituted heterocyclic groups in specific example group G2B below. Note that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic groups" described herein also include groups in which hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself are further replaced by substituents, and groups in which hydrogen atoms of substituents are further replaced by substituents.

[0029] The specific examples group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0030] Specific examples group G2B includes, for example, substituted heterocyclic groups containing a nitrogen atom (Specific Examples Group G2B1), substituted heterocyclic groups containing an oxygen atom (Specific Examples Group G2B2), substituted heterocyclic groups containing a sulfur atom (Specific Examples Group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (Specific Examples Group G2B4).

[0031] • Unsubstituted heterocyclic groups containing a nitrogen atom (specific examples group G2A1): Pyrrolyl group, imidazolyl group, Pyrazolyl group, Triazolyl group, Tetrazolyl group, Oxazolyl group, isoxazolyl group, Oxadiazolyl group, Thiazolyl group, isothiazolyl group, Thiadianzolyl group, Pyridyl group, Pyridazinyl group, Pyrimidinyl group, pyrazinyl group, Triazinyl group, Indolyl group, isoindolyl group, indolidinyl group, Quinolidinyl group, quinolyl group, Isoquinolyl group, cinnolyl group, Phthalazinyl group, Quinazolinyl group, Quinoxalinyl group, Benzimidazolyl group, Indazolyl group, Phenanthrolinyl group, Phenantridinyl group, Acridinyl group, Phenazinyl group, Carbazolyl group, Benzocarbazolyl group, Morpholino group, Phenoxadinyl group, Phenothiazinyl group, Azacarbazolyl group and diazacarbazolyl group.

[0032] • Unsubstituted heterocyclic groups containing an oxygen atom (specific examples group G2A2): Frill group, Oxazolyl group, isoxazolyl group, Oxadiazolyl group, xanthenyl group, Benzofuranyl group, Isobenzofuranyl group, Dibenzofuranyl group, Naphthobenzofuranyl group, Benzoxazolyl group, Benzoisoxazolyl group, Phenoxadinyl group, Morpholino group, Dinaphthofuranyl group, Azadibenzofuranyl group, Diazadibenzofuranyl group, Azanaftobenzofuranyl group, and Diazanaphthobenzofuranyl group.

[0033] • Unsubstituted heterocyclic groups containing a sulfur atom (specific examples group G2A3): Thienyl group, Thiazolyl group, isothiazolyl group, Thiadianzolyl group, Benzothiophenyl group (benzothienyl group), Isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), Naphthobenzothiophenyl group (naphthobenzothienyl group), Benzothiazolyl group, Benzoisothiazolyl group, Phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), azadibenzothiophenyl group (azadibenzothienyl group), Diazadibenzothiophenyl group (diazadibenzothienyl group), Azanaphtobenzothiophenyl group (azanaphthobenzothienyl group), and Diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0034] • Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (Specific examples group G2A4):

[0035] [ka]

[0036] [ka]

[0037] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each of these is independently an oxygen atom, a sulfur atom, NH, or CH2. However, X A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH. In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A If at least one of the members is NH or CH2, the monovalent heterocyclic groups derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) include monovalent groups obtained by removing one hydrogen atom from these NH or CH2 members.

[0038] • Heterocyclic groups with substitutions containing a nitrogen atom (Specific examples group G2B1): (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazole-9-yl group, Phenylcarbazole-9-yl group, Methyl benzimidazolyl group, Ethyl benzimidazolyl group, Phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, Phenylquinazolinyl group, and Biphenylylquinazolinyl group.

[0039] • Heterocyclic groups with substitutions containing an oxygen atom (Specific examples group G2B2): Phenyldibenzofuranyl group, Methyldibenzofuranyl group, t-butyldibenzofuranyl group, and A monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0040] • Heterocyclic groups with substitutions containing a sulfur atom (specific examples group G2B3): Phenyldibenzothiophenyl group, Methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and A monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0041] • Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific examples group G2B4):

[0042] The aforementioned "one or more hydrogen atoms of a monovalent heterocyclic group" means one or more hydrogen atoms selected from the hydrogen atoms bonded to the ring-forming carbon atoms of the monovalent heterocyclic group, the hydrogen atoms bonded to the nitrogen atom when at least one of XA and YA is NH, and the hydrogen atoms of the methylene group when one of XA and YA is CH2.

[0043] • "Substituted or unsubstituted alkyl groups" Specific examples of "substituted or unsubstituted alkyl groups" as described herein (Specific Examples Group G3) include the following unsubstituted alkyl groups (Specific Examples Group G3A) and substituted alkyl groups (Specific Examples Group G3B). (Here, "unsubstituted alkyl group" refers to the case where "substituted or unsubstituted alkyl group" is "unsubstituted alkyl group," and "substituted alkyl group" refers to the case where "substituted or unsubstituted alkyl group" is "substituted alkyl group.") Hereafter, "alkyl group" simply refers to both "unsubstituted alkyl groups" and "substituted alkyl groups." A "substituted alkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced by substituents. Specific examples of "substituted alkyl groups" include the groups in which one or more hydrogen atoms in the "unsubstituted alkyl groups" (specific example group G3A) below are replaced by substituents, and examples of substituted alkyl groups (specific example group G3B). In this specification, the alkyl group in "unsubstituted alkyl group" refers to a linear alkyl group. Therefore, "unsubstituted alkyl groups" include both linear "unsubstituted alkyl groups" and branched "unsubstituted alkyl groups". The examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed here are merely examples, and the "substituted alkyl groups" described herein also include groups in which the hydrogen atoms of the alkyl group itself in the "substituted alkyl groups" of specific example group G3B are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted alkyl groups" of specific example group G3B are further replaced by substituents.

[0044] • Unsubstituted alkyl groups (specific examples group G3A): Methyl group, Ethyl group, n-propyl group, Isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group.

[0045] • Substituting alkyl groups (specific examples group G3B): Heptafluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.

[0046] • "Substituted or unsubstituted alkenyl groups" Specific examples of "substituted or unsubstituted alkenyl groups" as described herein (Specific Examples Group G4) include the following unsubstituted alkenyl groups (Specific Examples Group G4A) and substituted alkenyl groups (Specific Examples Group G4B), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply includes both "unsubstituted alkenyl groups" and "substituted alkenyl groups." A "substituted alkenyl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted alkenyl group" are replaced by substituents. Specific examples of "substituted alkenyl groups" include groups in which the "unsubstituted alkenyl group" (Specific Example Group G4A) has substituents, and examples of substituted alkenyl groups (Specific Example Group G4B). Note that the examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl groups" described herein also include groups in which the hydrogen atoms of the alkenyl group itself in the "substituted alkenyl group" of Specific Example Group G4B are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted alkenyl group" of Specific Example Group G4B are further replaced by substituents.

[0047] • Unsubstituted alkenyl groups (specific examples group G4A): vinyl group, allyl group, 1-Butenyl group, 2-butenyl group, and 3-Butenyl group.

[0048] • Substitutive alkenyl groups (specific examples group G4B): 1,3-butanedienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.

[0049] • "Substituted or unsubstituted alkynyl groups" Specific examples of "substituted or unsubstituted alkynyl groups" as described herein (Specific Examples Group G5) include the following unsubstituted alkynyl groups (Specific Examples Group G5A), etc. (Here, "unsubstituted alkynyl group" refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group.") Hereafter, when simply referred to as "alkynyl group," it includes both "unsubstituted alkynyl groups" and "substituted alkynyl groups." A "substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced by substituents. Specific examples of "substituted alkynyl groups" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl group" (specific example group G5A) are replaced by substituents.

[0050] • Unsubstituted alkynyl groups (specific examples group G5A): Ethynyl group

[0051] • "Substituted or unsubstituted cycloalkyl groups" Specific examples of "substituted or unsubstituted cycloalkyl groups" as described herein (Specific Examples Group G6) include the following unsubstituted cycloalkyl groups (Specific Examples Group G6A) and substituted cycloalkyl groups (Specific Examples Group G6B), etc. (Here, "unsubstituted cycloalkyl group" refers to the case where "substituted or unsubstituted cycloalkyl group" is "unsubstituted cycloalkyl group," and "substituted cycloalkyl group" refers to the case where "substituted or unsubstituted cycloalkyl group" is "substituted cycloalkyl group.") In this specification, the term "cycloalkyl group" simply includes both "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups." A "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced by a substituent. Specific examples of "substituted cycloalkyl groups" include the groups in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" (specific example group G6A) are replaced by a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed here are merely examples, and the "substituted cycloalkyl groups" described herein also include groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself are replaced by a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted cycloalkyl group" of specific example group G6B are further replaced by a substituent.

[0052] • Unsubstituted cycloalkyl groups (specific examples group G6A): Cyclopropyl group, Cyclobutyl group, Cyclopentyl group, Cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.

[0053] • Substituting cycloalkyl groups (specific examples group G6B): 4-methylcyclohexyl group.

[0054] · "-Si(R 901 )(R 902 )(R 903 ) a base represented by -Si(R 901 )(R 902 )(R 903 ) Examples of the base represented by (Example Group G7) are: -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) Here are some examples. G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6. In -Si(G1)(G1)(G1), the multiple G1s are either identical or different from one another. In -Si(G1)(G2)(G2), the multiple G2s are either identical or different from one another. In -Si(G1)(G1)(G2), the multiple G1s are either identical or different from one another. In -Si(G2)(G2)(G2), the multiple G2s are either identical or different from one another. In -Si(G3)(G3)(G3), the multiple G3s are either identical or different from one another. In -Si(G6)(G6)(G6), the multiple G6s are either identical or different from one another.

[0055] ·「-O-(R 904 ) a base represented by The following information pertains to the -O-(R 904 ) Examples of the base represented by (Example Group G8) are: -O(G1), -O(G2), -O(G3), and -O(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6.

[0056] · "-S-(R 905 ) a base represented by The following information pertains to the -S-(R 905 ) Examples of the base represented by (example group G9) are: -S(G1), -S(G2), -S(G3), and -S(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6.

[0057] · "-N(R 906 )(R 907 ) a base represented by -N(R) as described in this specification 906 )(R 907 ) Examples of the base represented by (Example Group G10) are: -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6. In -N(G1)(G1), multiple G1s are either identical or different from one another. In -N(G2)(G2), multiple G2s are either identical or different from one another. In -N(G3)(G3), multiple G3s are either identical or different from one another. In -N(G6)(G6), multiple G6s are either identical or different from one another.

[0058] • "Halogen atom" Specific examples of "halogen atoms" as described herein (Specific Examples Group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0059] • "Substituted or unsubstituted fluoroalkyl groups" The terms "substituted or unsubstituted fluoroalkyl groups" as used herein refer to groups in which at least one hydrogen atom bonded to the carbon atoms constituting the alkyl group is replaced by a fluorine atom, and also include groups in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group are replaced by fluorine atoms (perfluoro groups). The number of carbon atoms in an "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. A "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced by substituents. The terms "substituted fluoroalkyl groups" as used herein also include groups in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent are further replaced by substituents. Specific examples of "unsubstituted fluoroalkyl groups" include the example of a group in which one or more hydrogen atoms in the aforementioned "alkyl group" (specific example group G3) are replaced by fluorine atoms.

[0060] • "Substituted or unsubstituted haloalkyl groups" The terms "substituted or unsubstituted haloalkyl groups" as used herein refer to groups in which at least one hydrogen atom bonded to the carbon atoms constituting the alkyl group is replaced by a halogen atom, and also include groups in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group are replaced by halogen atoms. The number of carbon atoms in an "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. A "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of a "haloalkyl group" are replaced by substituents. The terms "substituted haloalkyl groups" as used herein also include groups in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent are further replaced by substituents. Specific examples of "unsubstituted haloalkyl groups" include groups in which one or more hydrogen atoms of the aforementioned "alkyl group" (specific example group G3) are replaced by halogen atoms. Haloalkyl groups are sometimes referred to as alkyl halogens.

[0061] • "Substituted or unsubstituted alkoxy groups" A specific example of a "substituted or unsubstituted alkoxy group" as described herein is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. The number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein.

[0062] • "substituted or unsubstituted alkylthio groups" As a specific example of the "substituted or unsubstituted alkylthio group" described in the present specification, it is a group represented by -S(G3), wherein G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. Unless otherwise specified separately in the present specification, the number of carbon atoms of an "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, more preferably 1 to 18.

[0063] • "Substituted or unsubstituted aryloxy group" As a specific example of the "substituted or unsubstituted aryloxy group" described in the present specification, it is a group represented by -O(G1), wherein G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. Unless otherwise specified separately in the present specification, the number of ring-forming carbon atoms of an "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, more preferably 6 to 18.

[0064] • "Substituted or unsubstituted arylthio group" As a specific example of the "substituted or unsubstituted arylthio group" described in the present specification, it is a group represented by -S(G1), wherein G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. Unless otherwise specified separately in the present specification, the number of ring-forming carbon atoms of an "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, more preferably 6 to 18.

[0065] • "Substituted or unsubstituted trialkylsilyl group" As a specific example of the "trialkylsilyl group" described in the present specification, it is a group represented by -Si(G3)(G3)(G3), wherein G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The plurality of G3 in -Si(G3)(G3)(G3) are the same as or different from each other. Unless otherwise specified separately in the present specification, the number of carbon atoms of each alkyl group in the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, more preferably 1 to 6.

[0066] • "Substituted or unsubstituted aralkyl group" As specific examples of the "substituted or unsubstituted aralkyl group" described in the present specification, the group is represented by -(G3)-(G1), wherein G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3, and G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. Accordingly, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" serving as a substituent, and is one embodiment of a "substituted alkyl group". An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and unless otherwise specified separately in the present specification, the carbon number of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, more preferably 7 to 18. Specific examples of the "substituted or unsubstituted aralkyl group" include a benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.

[0067] Unless otherwise specified separately in the present specification, the substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group, pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, 9,9'-spirobifluorenyl group, 9,9-dimethylfluorenyl group, and 9,9-diphenylfluorenyl group.

[0068] Unless otherwise specified herein, the substituted or unsubstituted heterocyclic groups are preferably pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, benzimidazolyl, phenanthrolinyl, carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, or 9-carbazolyl), benzocarbazolyl, azacarbazolyl, diazacarbazolyl, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, aza These include dibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazole-1-yl group, (9-phenyl)carbazole-2-yl group, (9-phenyl)carbazole-3-yl group, or (9-phenyl)carbazole-4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazole-9-yl group, phenylcarbazole-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group, etc.

[0069] In this specification, unless otherwise specified, the carbazolyl group is specifically one of the following groups:

[0070] [ka]

[0071] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically one of the following groups:

[0072] [ka]

[0073] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bond position.

[0074] In this specification, unless otherwise specified, the dibenzofuranyl group and the dibenzothiophenyl group specifically refer to any of the following groups:

[0075] [ka]

[0076] In the general formulas (TEMP-34) to (TEMP-41) above, * represents a bond position.

[0077] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t-butyl groups.

[0078] • "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described herein is a divalent group derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described above. Specific examples of the "substituted or unsubstituted arylene group" (Specific Examples Group G12) include the divalent group derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described in Specific Examples Group G1.

[0079] • "Substitutable or unsubstituted divalent heterocyclic groups" Unless otherwise specified, the “substituted or unsubstituted divalent heterocyclic groups” described herein refer to divalent groups derived by removing one hydrogen atom from the heterocycle of the “substituted or unsubstituted heterocyclic groups” described above. Specific examples of “substituted or unsubstituted divalent heterocyclic groups” (Specific Examples Group G13) include the divalent groups derived by removing one hydrogen atom from the heterocycle of the “substituted or unsubstituted heterocyclic groups” described in Specific Examples Group G2.

[0080] • "substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in the present specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above "substituted or unsubstituted alkyl group". Specific examples of "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3, and the like.

[0081] Unless otherwise specified in the present specification, the substituted or unsubstituted arylene group described in the present specification is preferably any group of the following general formulas (TEMP-42) to (TEMP-68).

[0082]

Chemical Formula

[0083]

Chemical Formula

[0084] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent. In the above general formulas (TEMP-42) to (TEMP-52), * represents a bonding position.

[0085]

Chemical Formula

[0086] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent. Formula Q9 and Q 10 may be bonded to each other via a single bond to form a ring. In the general formulas (TEMP-53) to (TEMP-62) above, * represents a bond position.

[0087] [ka]

[0088] In the general formulas (TEMP-63) to (TEMP-68) above, Q1 to Q8 are each independently a hydrogen atom or a substituent. In the general formulas (TEMP-63) to (TEMP-68) above, * represents a bond position.

[0089] Unless otherwise specified herein, the substituted or unsubstituted divalent heterocyclic groups described herein are preferably any of the following general formulas (TEMP-69) to (TEMP-102).

[0090] [ka]

[0091] [ka]

[0092] [ka]

[0093] In the general formulas (TEMP-69) to (TEMP-82) above, Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0094] [ka]

[0095] [ka]

[0096] [ka]

[0097] [ka]

[0098] In the general formulas (TEMP-83) to (TEMP-102) above, Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0099] The above is a description of the substituents described herein.

[0100] • "When they combine to form a ring" In this specification, the phrase "one or more pairs of adjacent elements join together to form a substituted or unsubstituted monoring, join together to form a substituted or unsubstituted fused ring, or do not join together" means the case where "one or more pairs of adjacent elements join together to form a substituted or unsubstituted monoring," the case where "one or more pairs of adjacent elements join together to form a substituted or unsubstituted fused ring," and the case where "one or more pairs of adjacent elements do not join together." In this specification, the cases in which "one or more pairs of adjacent elements bond to each other to form a substituted or unsubstituted monoring" and "one or more pairs of adjacent elements bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "cases where elements bond to form a ring") will be explained below. An example will be given of an anthracene compound represented by the following general formula (TEMP-103), whose parent skeleton is an anthracene ring.

[0101] [ka]

[0102] For example, R921 ~R 930 In the case where "one or more pairs of adjacent groups are joined together to form a ring," the pairs of adjacent groups that make up one set are R 921 and R 922 The pair, R 922 and R 923 The pair, R 923 and R 924 The pair, R 924 and R 930 The pair, R 930 and R 925 The pair, R 925 and R 926 The pair, R 926 and R 927 The pair, R 927 and R 928 The pair, R 928 and R 929 The pair with, and R 929 and R 921 They are a pair.

[0103] The phrase "one or more pairs" above means that two or more pairs of adjacent pairs may simultaneously form a ring. For example, R 921 and R 922 and are joined to form a ring Q A Forms R 925 and R 926 and are joined to form a ring Q B If the above general formula (TEMP-103) is formed, the anthracene compound represented by the above general formula (TEMP-104) is represented by the following general formula (TEMP-104).

[0104] [ka]

[0105] The case where "two or more adjacent elements form a ring" includes not only cases where two adjacent elements are joined, as in the example above, but also cases where three or more adjacent elements are joined. For example, R 921 and R 922 and are joined to form a ring Q A Forms R 922 and R923 and are bonded to each other to form ring Q C , and a group consisting of three mutually adjacent R 921 , R 922 and R 923 are bonded to each other to form a ring that is fused to the anthracene parent skeleton; in this case, the anthracene compound represented by the 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 share R 922 .

[0106]

Chemical Formula

[0107] The "monocycle" or "fused ring" formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even in a case where "one set of two adjacent groups" forms a "monocycle" or a "fused ring", the "monocycle" or "fused ring" may form a saturated ring or an unsaturated ring. For example, ring Q formed in the general formula (TEMP-104) A and ring Q B are each a "monocycle" or a "fused ring". Further, ring Q formed in the general formula (TEMP-105) A and ring Q C are "fused rings". Ring Q A and ring Q C in the general formula (TEMP-105) form a fused ring by fusing ring Q A and ring Q C to each other. If ring Q A in the general formula (TEMP-104) is a benzene ring, ring Q A is a monocycle. If ring Q A in the general formula (TEMP-104) is a naphthalene ring, ring Q A is a fused ring.

[0108] An "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocycle. A "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocycle. Specific examples of aromatic hydrocarbon rings include structures in which the groups listed as examples in specific example group G1 are terminated by hydrogen atoms. A concrete example of an aromatic heterocycle is the structure in which the aromatic heterocycle group listed as a concrete example in concrete example group G2 is terminated by a hydrogen atom. Specific examples of aliphatic hydrocarbon rings include structures in which the groups listed as examples in example group G6 are terminated by hydrogen atoms. "To form a ring" means to form a ring with only multiple atoms of the parent skeleton, or with multiple atoms of the parent skeleton and one or more additional arbitrary elements. For example, as shown in the general formula (TEMP-104), 921 and R 922 A ring Q is formed when these two elements are bonded together. A R 921 The carbon atoms of the anthracene skeleton to which R is bonded, 922 It refers to a ring formed by the carbon atoms of the anthracene skeleton to which the R atoms are bonded, and one or more arbitrary elements. A specific example is R 921 and R 922 And the environment Q A When forming R 921 The carbon atoms of the anthracene skeleton to which R is bonded, 922 When the carbon atoms of the anthracene skeleton bonded to the four carbon atoms form a monocyclic unsaturated ring, R 921 and R 922 The ring formed by these two is a benzene ring.

[0109] Here, "any element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur, unless otherwise specified herein. In any element (for example, carbon or nitrogen), bonds that do not form a ring may be terminated by a hydrogen atom or the like, or substituted by "any substituent" as described later. If any element other than carbon is included, the formed ring is a heterocycle. The "one or more arbitrary elements" constituting the monoring or fused ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5, unless otherwise specified herein. Unless otherwise specified herein, the preferred form is a monoring or a fused ring. Unless otherwise specified herein, the "unsaturated ring" is preferred over the "saturated ring". Unless otherwise specified herein, “monocyclic” is preferably a benzene ring. Unless otherwise specified herein, the “unsaturated ring” is preferably a benzene ring. When "one or more sets of two or more adjacent elements" "bond to each other to form a substituted or unsubstituted monoring" or "bond to each other to form a substituted or unsubstituted fused ring", unless otherwise specified herein, preferably, one or more sets of two or more adjacent elements bond to each other to form a substituted or unsubstituted "unsaturated ring" consisting of multiple atoms of the parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur elements, ranging from one to fifteen.

[0110] When the above-mentioned "monocyclic ring" or "fused ring" has substituents, the substituents are, for example, "any substituents" as described later. Specific examples of substituents when the above-mentioned "monocyclic ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described herein" above. When the above-mentioned "saturated ring" or "unsaturated ring" has substituents, the substituents are, for example, "any substituents" as described later. Specific examples of substituents when the above-mentioned "mono-ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described herein" above. The above explains the cases in which "one or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring" and "one or more pairs of adjacent elements combine to form a substituted or unsubstituted fused ring" ("the case of combining to form a ring").

[0111] • Substituents in the phrase "substituted or unsubstituted" In one embodiment described herein, the substituent referred to as "substituted or unsubstituted" (which may be referred to herein as "any substituent") is, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms. Unsubstituted alkenyl groups with 2 to 50 carbon atoms, Unsubstituted alkynyl groups with 2 to 50 carbon atoms, Unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, Unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, and Unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms It is a base selected from the group consisting of, Here, R 901 ~R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If there are two or more of them, then there are two or more R 901 They are either identical or different from each other. R 902 If there are two or more of them, then there are two or more R 902 They are either identical or different from each other. R 903If there are two or more of them, then there are two or more R 903 They are either identical or different from each other. R 904 If there are two or more of them, then there are two or more R 904 They are either identical or different from each other. R 905 If there are two or more of them, then there are two or more R 905 They are either identical or different from each other. R 906 If there are two or more of them, then there are two or more R 906 They are either identical or different from each other. R 907 If there are two or more of them, then there are two or more R 907 They are either identical or different from one another.

[0112] In one embodiment, the substituent in the case of "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 50 carbon atoms, A ring-forming aryl group with 6 to 50 carbon atoms, and Heterocyclic groups with 5 to 50 ring-forming atoms It is a group selected from the group consisting of the following.

[0113] In one embodiment, the substituent in the case of "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 18 carbon atoms, Ring-forming aryl groups with 6 to 18 carbon atoms, and Heterocyclic groups with 5 to 18 ring-forming atoms It is a group selected from the group consisting of the following.

[0114] Specific examples of each of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents as described herein" above.

[0115] Unless otherwise specified herein, adjacent substituents may form a "saturated ring" or an "unsaturated ring," preferably 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, and more preferably a benzene ring. Unless otherwise specified herein, any substituent may have further substituents, such as those described above.

[0116] In this specification, a numerical range expressed using "AA~BB" means a range that includes the numerical value AA, which is listed before "AA~BB", as the lower limit, and the numerical value BB, which is listed after "AA~BB", as the upper limit.

[0117] The compounds of the present invention will be described below. The compound of the present invention is represented by the following formula (1). However, hereinafter, the compound of the present invention represented by the formula included in formula (1) may simply be referred to as the “inventive compound.” [ka]

[0118] The following explains the symbols in equation (1). Note that the same symbol has the same meaning.

[0119] In formula (1), N * It is the central nitrogen atom.

[0120] R 1 ~R 8 Each of these is independently either a hydrogen atom or an unsubstituted phenyl group. R is not a single bond. 1 ~R 8 Two adjacent elements selected from these elements may bond to each other to form one or more substituted or unsubstituted benzene rings, or they may not bond to each other and therefore not form benzene rings. However, R 1and R 4 One of the options selected is a single bond that connects to *a.

[0121] R a and R b Each of these is independently a hydrogen atom or a substituent, and the substituent is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms that forms a ring. R a and R b They do not bond with each other and do not form a ring.

[0122] R a and R b Examples of the unsubstituted C1-C20 alkyl group represented by include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, amyl group, isoamyl group, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, and 3-methylpentyl group. Among these, preferably is a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, or t-butyl group, more preferably a methyl group, ethyl group, isopropyl group, or t-butyl group, and even more preferably a methyl group or t-butyl group.

[0123] R a and R bIn the unsubstituted ring-forming aryl group having 6 to 18 carbon atoms represented by , examples of the aryl group include phenyl, biphenylyl, terphenyl, naphthyl, anthryl, phenanthryl, phenalenyl, pentaphenyl, pyrenyl, chrysenyl, fluorenyl, and triphenylenyl groups. Among these, phenyl, biphenylyl, naphthyl, phenanthryl, anthryl, fluorenyl, or triphenylenyl groups are preferred.

[0124] R a and R b In one embodiment, it is particularly preferable that each of them is an independently unsubstituted methyl group.

[0125] L 4 These are single-bonded or unsubstituted ring-forming arylene groups with 6 to 18 carbon atoms. L 4 In one embodiment, it is preferable that it be a single bond.

[0126] L 4 In the unsubstituted ring-forming arylene group having 6 to 18 carbon atoms represented by , the arylene group is preferably a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, or a phenanthrylene group.

[0127] L 4 The phenylene group represented by is an o-phenylene group, an m-phenylene group, or a p-phenylene group. L 4 In one embodiment, this is preferably a substituted or unsubstituted o-phenylene group, or a substituted or unsubstituted p-phenylene group. L 4 The naphthylene group represented by is preferably a 1,3-naphthylene group, a 1,4-naphthylene group, a 2,4-naphthylene group, or a 1,8-naphthylene group.

[0128] Ar is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms forming a ring. However, when Ar is represented by a substituted or unsubstituted fluorenyl group, the adjacent substituents at positions 9,9 on the fluorenyl group are not bonded to each other and do not form a ring.

[0129] In the unsubstituted ring-forming aryl group having 6 to 30 carbon atoms represented by Ar, the aryl group is, for example, a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, anthryl group, a benzoantryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a picenyl group, a pentaphenyl group, a pyrenyl group, a crisenyl group, a benzocrisenyl group, a fluorenyl group, a fluoranteyl group, a fluoranthenyl group, a perilenyl group, or a triphenylenyl group. Preferably, it is a phenyl group, a biphenylyl group, a terphenylyl group, or a naphthyl group; more preferably, it is a phenyl group, a 2-, 3-, or 4-biphenylyl group, a 2-, 3-, or 4-o-terphenylyl group, a 2-, 3-, or 4-m-terphenylyl group, a 2-, 3-, or 4-p-terphenylyl group, or a 1- or 2-naphthyl group; and even more preferably, it is a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group.

[0130] In one embodiment, Ar is preferably a substituted or unsubstituted ring-forming aryl group having 6 to 14 carbon atoms.

[0131] In the unsubstituted ring-forming aryl group having 6 to 14 carbon atoms represented by Ar, the aryl group is, for example, a phenyl group, a biphenylyl group, a naphthyl group, anthryl group, a phenanthryl group, a phenalenyl group, or a fluorenyl group, preferably a phenyl group, a biphenylyl group, or a naphthyl group, and more preferably a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group.

[0132] L 1 、 L 2 and L 3 Each of these is independently a single-bonded, substituted, or unsubstituted ring-forming arylene group with 6 to 18 carbon atoms.

[0133] L 1 、 L 2 and L 3 In the unsubstituted ring-forming arylene group having 6 to 18 carbon atoms represented by , the arylene group is preferably a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, or a phenanthrylene group.

[0134] L 1 In one embodiment, it is preferable that it be a single bond. L 1 and L 2 In one embodiment, it is preferable that each of these is an unsubstituted phenylene group, independently of the others. L 3 In one embodiment, it is preferable that it is an unsubstituted phenylene group.

[0135] L 1 The phenylene group represented by is an o-phenylene group, an m-phenylene group, or a p-phenylene group. L 1 In one embodiment, this is preferably a substituted or unsubstituted o-phenylene group, or a substituted or unsubstituted p-phenylene group. L 1 The naphthylene group represented by is preferably a 1,4-naphthylene group, a 2,6-naphthylene group, a 2,7-naphthylene group, or a 1,8-naphthylene group.

[0136] L 2 The phenylene group represented by is an o-phenylene group, an m-phenylene group, or a p-phenylene group.

[0137] L 3 The phenylene group represented by is an o-phenylene group, an m-phenylene group, or a p-phenylene group.

[0138] R 11 ~R 25 Each of these is independently a hydrogen atom or a substituted or unsubstituted ring-forming aryl group having 6 to 18 carbon atoms.

[0139] R 11 ~R 25 In the unsubstituted ring-forming aryl group having 6 to 18 carbon atoms represented by , examples of the aryl group include phenyl, biphenylyl, terphenyl, naphthyl, anthryl, phenanthryl, phenalenyl, pentaphenyl, pyrenyl, chrysenyl, fluorenyl, and triphenylenyl groups. Among these, phenyl, biphenylyl, naphthyl, phenanthryl, anthryl, fluorenyl, or triphenylenyl groups are preferred.

[0140] R 11 ~R 15 Two adjacent elements are selected from R 16 ~R 20 Two adjacent elements are selected from, or R 21 ~R 25 Two adjacent groups selected from the group may bond to each other to form one or more substituted or unsubstituted benzene rings, or they may not bond to each other and therefore not form benzene rings. For example, the multiple substituted or unsubstituted benzene rings can be naphthyl groups, phenanthryl groups, and the like.

[0141] Formula (1) is preferably represented by the following formula (1-a) or formula (1-b). [ka] (In the formula, N * , R a , R b , R 1 ~R 8 , R 11 ~R 25 , L 1 ~L 4 A, B, C, and Ar are defined in equation (1).

[0142] In one embodiment, formula (1) is preferably represented by formula (1-a).

[0143] Formula (1) is preferably represented by the following formula (1-a-1) or formula (1-a-2). [ka] (In the formula, N * , R a , R b , R 1 ~R 8 , R 11 ~R 25 , L 1 ~L 4 A, B, C, and Ar are defined in equation (1), and R 31 ~R 35 Each of these is independently a hydrogen atom or a substituent, and the substituent is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms that forms a ring.

[0144] R 31 ~R 35 Details of substituted or unsubstituted C1-C20 alkyl groups represented by and preferred examples thereof are as follows: a and R b As described above. R 31 ~R 35 Details of substituted or unsubstituted ring-forming aryl groups with 6 to 18 carbon atoms represented by and preferred examples thereof are as follows: a and R b As described above.

[0145] Two adjacent rings selected from benzene ring A, benzene ring B, and benzene ring C do not crosslink with each other.

[0146] The substituents referred to as "substituted or unsubstituted" are unsubstituted C1-C20 alkyl groups, unsubstituted ring-forming C3-C20 cycloalkyl groups, unsubstituted ring-forming C6-C18 aryl groups, or unsubstituted ring-forming C5-C13 heterocyclic groups.

[0147] Examples of unsubstituted alkyl groups having 1 to 20 carbon atoms as substituents in the case of "substituted or unsubstituted" include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, amyl group, isoamyl group, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, and 3-methylpentyl group. Among these, preferably is a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, or t-butyl group, more preferably a methyl group, ethyl group, isopropyl group, or t-butyl group, and even more preferably a methyl group or t-butyl group.

[0148] When referring to "substituted or unsubstituted," unsubstituted ring-forming cycloalkyl groups having 3 to 20 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl groups. Of these, cyclopropyl, cyclobutyl, cyclohexyl, 1-adamantyl, or 1-norbornyl groups are preferred, and cyclohexyl or 1-adamantyl groups are more preferred.

[0149] Examples of unsubstituted ring-forming aryl groups with 6 to 18 carbon atoms, as substituents in the case of "substituted or unsubstituted," include phenyl, biphenylyl, terphenyl, naphthyl, anthryl, phenanthryl, phenalenyl, pentaphenyl, pyrenyl, chrysenyl, fluorenyl, and triphenylenyl groups. Among these, phenyl, biphenylyl, naphthyl, phenanthryl, anthryl, fluorenyl, or triphenylenyl groups are preferred.

[0150] Examples of unsubstituted heterocyclic groups with 5 to 13 ring-forming atoms as substituents in the case of "substituted or unsubstituted" include pyridyl, pyrimidinyl, triazinyl, quinolyl, carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, or 9-carbazolyl), dibenzofuranyl, or dibenzothiophenyl. Among these, carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, or 9-carbazolyl), dibenzofuranyl, or dibenzothiophenyl.

[0151] However, in the case of Ar, if the substituent referred to as "substituted or unsubstituted" is an unsubstituted C1-C20 alkyl group, then two adjacent unsubstituted C1-C20 alkyl groups do not bond to each other and therefore do not form a ring.

[0152] In one embodiment of the present invention, (A-1)R 1 ~R 4 All of them may be hydrogen atoms, (A-2)R 5 ~R 8 All of them may be hydrogen atoms, (A-3)R 11 ~R 15 All of them may be hydrogen atoms, (A-4)R 16 ~R 20 All of them may be hydrogen atoms, (A-5)R 21 ~R 25 All of them may be hydrogen atoms, (A-6)R 31 ~R 35 All of them may be hydrogen atoms. The inventive compound may simultaneously satisfy all of the above conditions (A-1) to (A-6), or it may satisfy some of the above conditions (A-1) to (A-6).

[0153] As stated above, the term "hydrogen atom" as used herein includes light hydrogen atoms, deuterium atoms, and tritium atoms. Therefore, the inventive compound may contain naturally occurring deuterium atoms. Furthermore, deuterium atoms may be intentionally introduced into the inventive compound by using a deuterized compound as part or all of the raw material compound. Accordingly, in one embodiment of the present invention, it is preferable that the inventive compound contains at least one deuterium atom. That is, the inventive compound may be a compound represented by formula (1) in which at least one of the hydrogen atoms contained in the compound is a deuterium atom.

[0154] The deuterated ratio of the inventive compound depends on the deuterated ratio of the raw material compound used. Even when using raw materials with a predetermined deuterated ratio, a certain proportion of naturally occurring light hydrogen isotopes may be present. Therefore, the forms of deuterated ratio of the inventive compound shown below include a ratio that takes into account trace amounts of naturally occurring isotopes, in addition to the ratio obtained by simply counting the number of deuterium atoms represented by the chemical formula. The deuteration rate of the inventive compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, and even more preferably 20% or more. Furthermore, the deuteration rate may be 1-100%, 3-80%, 5-60%, 10-50%, or 20-30%.

[0155] The inventive compound may be a mixture containing a deuterated compound and an undeuterated compound, or a mixture of two or more compounds having different deuterated rates. The deuterated rate of such a mixture is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, and even more preferably 20% or more. Furthermore, the deuterated rate may be 1-100%, 3-80%, 5-60%, 10-50%, or 20-30%.

[0156] In one embodiment of the present invention, (B-1)R1 ~R 4 The hydrogen atoms may all be deuterium atoms. (B-2)R 5 ~R 8 The hydrogen atoms may all be deuterium atoms. (B-3)R 11 ~R 15 The hydrogen atoms may all be deuterium atoms. (B-4)R 16 ~R 20 The hydrogen atoms may all be deuterium atoms. (B-5)R 21 ~R 25 The hydrogen atoms may all be deuterium atoms. (B-6)R 31 ~R 35 It is also possible that all of the hydrogen atoms are deuterium atoms. (B-7) The unsubstituted aryl group represented by Ar may have all its hydrogen atoms be deuterium atoms. (B-8)L 1 The unsubstituted arylene group represented by may have all its hydrogen atoms be deuterium atoms. (B-9)L 2 The unsubstituted arylene group represented by may have all its hydrogen atoms be deuterium atoms. (B-10)L 3 The unsubstituted arylene group represented by may have all its hydrogen atoms be deuterium atoms. (B-11)L 4 The unsubstituted arylene group represented by may have all its hydrogen atoms be deuterium atoms. Depending on their composition, the inventive compounds may simultaneously satisfy two or more of the above conditions (B-1) to (B-11).

[0157] In one embodiment of the present invention, (C-1)L 1 , L 2 , L 3 and L 4 If all of these are unsubstituted phenylene groups, each of these unsubstituted phenylene groups may independently contain at least one deuterium atom. (C-2)L 1 , L 2 , L 3 and L 4 If all of these are unsubstituted phenylene groups, then all of the hydrogen atoms in one of these unsubstituted phenylene groups may be deuterium atoms. (C-3)L 1 , L 2 , L 3 and L 4 If all of these are unsubstituted phenylene groups, then all of the hydrogen atoms in these unsubstituted phenylene groups may be deuterium atoms, and (C-4)L 1 If it is an unsubstituted phenylene group, all of the hydrogen atoms in the unsubstituted phenylene group may be deuterium atoms. (C-5)L 2 If it is an unsubstituted phenylene group, all of the hydrogen atoms in the unsubstituted phenylene group may be deuterium atoms. (C-6)L 3 If it is an unsubstituted phenylene group, all of the hydrogen atoms in the unsubstituted phenylene group may be deuterium atoms. (C-7)L 4 If the group is an unsubstituted phenylene group, all of the hydrogen atoms in the unsubstituted phenylene group may be deuterium atoms.

[0158] Except in special cases, the details of substituents (any substituents) in the case of "substituted or unsubstituted" included in the definition of each of the above formulas are as described in the section "Substituents in the case of "substituted or unsubstituted"".

[0159] Those skilled in the art can easily produce the inventive compound by referring to the following synthesis examples and known synthesis methods.

[0160] The following are specific examples of the inventive compounds, but the invention is not limited to these example compounds. In addition to the compounds listed below as example compounds, the inventive compounds also include compounds in which some hydrogen atoms are not deuterated due to the synthesis technique. In the specific examples below, D represents a deuterium atom.

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[0231] Materials for organic EL devices A material for organic EL devices according to one aspect of the present invention contains the inventive compound. The content of the inventive compound in the material for organic EL devices 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%), even more preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). A material for organic EL devices according to one aspect of the present invention is useful for the manufacture of organic EL devices. In one embodiment of the present invention, it is preferable that the inventive compound is a hole transport layer material.

[0232] A material for an organic electroluminescent device according to one aspect of the present invention is a hole transport layer material. The content of the inventive compound in the material for organic electroluminescent elements is preferably 1% by mass or more (including 100%), more preferably 10% by mass or more (including 100%), even more preferably 50% by mass or more (including 100%), even more preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%).

[0233] Organic EL element An organic EL element according to one aspect of the present invention has 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 contains the inventive compound. Examples of organic layers containing the inventive compound include, but are not limited to, hole transport bands (hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer, etc.) provided between the anode and the light-emitting layer, light-emitting layer, space layer, electron transport bands (electron injection layer, electron transport layer, hole blocking layer, etc.) provided between the cathode and the light-emitting layer. The inventive compound is preferably used as a material for the hole transport band or light-emitting layer of a fluorescent or phosphorescent EL element, more preferably as a material for the hole transport band, 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.

[0234] An organic EL element according to one aspect of the present invention may be a monochromatic light-emitting element of the fluorescent or phosphorescent type, or a white light-emitting element of the fluorescent / phosphorescent hybrid type, and may be a simple type having a single light-emitting unit, or a tandem type having multiple light-emitting units, with a fluorescent light-emitting element being preferred. Here, "light-emitting unit" refers to the smallest unit that includes an organic layer, consists of one or more layers made up of the organic layer, and at least one layer selected from the group consisting of the single layer and the multiple layers is a light-emitting layer, and emits light when injected holes and electrons recombine.

[0235] For example, the following are typical device configurations for simple organic EL elements. (1) Anode / Light-emitting unit / Cathode Furthermore, the above-mentioned light-emitting unit may be a multilayer type having multiple phosphorescent and fluorescent light-emitting layers. In this case, a space layer may be provided between each light-emitting layer to prevent excitons generated in the phosphorescent layer from diffusing into the fluorescent light-emitting layer. A typical layer configuration of a simple light-emitting unit is shown below. The layers in parentheses are arbitrary. (a) (Hole injection layer / ) Hole transport layer / Fluorescence layer / Electron transport layer ( / Electron injection layer) (b) (Hole injection layer / ) Hole transport layer / First fluorescence emission layer / Second fluorescence emission layer / Electron transport layer ( / Electron injection layer) (c) (Hole injection layer / ) Hole transport layer / Phosphorescent layer / Space layer / Fluorescent layer / Electron transport layer ( / Electron injection layer) (d) (Hole injection layer / ) Hole transport layer / First phosphorescent layer / Second phosphorescent layer / Space layer / Fluorescent layer / Electron transport layer ( / Electron injection layer) (e) (Hole injection layer / ) Hole transport layer / Phosphorescent layer / Space layer / First fluorescence layer / Second fluorescence layer / Electron transport layer ( / Electron injection layer) (f) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Fluorescence layer / Electron transport layer ( / Electron injection layer) (g) (Hole injection layer / ) Hole transport layer / Exciton blocking layer / Fluorescence layer / Electron transport layer ( / Electron injection layer) (h)(Hole injection layer / )First hole transport layer / Second hole transport layer / Fluorescence-emitting layer / Electron transport layer( / Electron injection layer) (h1)(Hole injection layer / )First hole transport layer / Second hole transport layer / Third hole transport layer / Fluorescence-emitting layer / Electron transport layer( / Electron injection layer). (i) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Fluorescence layer / First electron transport layer / Second electron transport layer ( / Electron injection layer) (i1)(Hole injection layer / )First hole transport layer / Second hole transport layer / Third hole transport layer / Fluorescence-emitting layer / First electron transport layer / Second electron transport layer( / Electron injection layer) (j)(Hole injection layer / )Hole transport layer / Fluorescence layer / Hole blocking layer / Electron transport layer( / Electron injection layer) (k)(hole injection layer / )hole transport layer / fluorescence layer / exciton blocking layer / electron transport layer( / electron injection layer)

[0236] Each of the phosphorescent or fluorescent layers described above may exhibit a different emission color from one another. Specifically, in the light-emitting unit (d) described above, examples of layer configurations include (hole injection layer / )hole transport layer / first phosphorescent layer (red emission) / second phosphorescent layer (green emission) / space layer / fluorescent layer (blue emission) / electron transport layer. Furthermore, an electron blocking layer may be provided between each light-emitting layer and the hole transport layer or space layer as appropriate. A hole blocking layer may also be provided between each light-emitting layer and the electron transport layer as appropriate. By providing electron blocking layers or hole blocking layers, electrons or holes can be confined within the light-emitting layer, increasing the probability of charge recombination in the light-emitting layer and improving the luminescence efficiency.

[0237] Typical device configurations for tandem organic EL elements include the following: (2) Anode / First light-emitting unit / Intermediate layer / Second light-emitting unit / Cathode Here, the first light-emitting unit and the second light-emitting unit can, for example, be independently selected from the light-emitting units described above. The above-mentioned intermediate layer is generally also called an intermediate electrode, intermediate conductive layer, charge generation layer, electron extraction layer, connecting layer, or intermediate insulating layer, and a known material configuration can be used to supply electrons to the first light-emitting unit and holes to the second light-emitting unit. Furthermore, if the hole transport layer is a multilayer structure containing two or more hole transport layers, the hole transport layers adjacent to the light-emitting layer in the multilayer structure, for example, the second hole transport layer in the two-layer structure or the third hole transport layer in the three-layer structure, may function as electron blocking layers. In other words, if the hole transport layer is a multilayer structure containing two or more hole transport layers, the hole transport layers adjacent to the light-emitting layer in the multilayer structure can also be used as electron blocking layers.

[0238] Figure 1 is a schematic diagram showing an example of the configuration of an organic EL element according to one aspect of the present invention. The organic EL element 1 shown in Figure 1 has 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. There is a hole transport band 6 (hole injection layer, hole transport layer, etc.) between the light-emitting layer 5 and the anode 3, and an electron transport band 7 (electron injection layer, electron transport layer, etc.) between the light-emitting layer 5 and the cathode 4. In addition, an electron blocking layer (not shown) may be provided on the anode 3 side of the light-emitting layer 5, and a hole blocking layer (not shown) may be provided on the cathode 4 side of the light-emitting layer 5. This can confine electrons and holes in the light-emitting layer 5 and further increase the exciton generation efficiency in the light-emitting layer 5.

[0239] Figure 2 is a schematic diagram showing another configuration of an organic EL element according to one aspect of the present invention. The organic EL element 11 shown in Figure 2 has 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 band disposed between the anode 3 and the light-emitting layer 5 is formed from a hole injection layer 6a, a first hole transport layer 6b, and a second hole transport layer 6c. The electron transport band disposed between the light-emitting layer 5 and the cathode 4 is formed from a first electron transport layer 7a and a second electron transport layer 7b.

[0240] Figure 3 is a schematic diagram showing yet another configuration of an organic EL element according to one aspect 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 band disposed between the anode 3 and the light-emitting layer 5 is formed from a hole injection layer 6a, a first hole transport layer 6b, a second hole transport layer 6c, and a third hole transport layer 6d. The electron transport band disposed between the light-emitting layer 5 and the cathode 4 is formed from a first electron transport layer 7a and a second electron transport layer 7b.

[0241] In Figures 1 to 3, the light-emitting layer 5 includes at least one light-emitting layer. The light-emitting layer 5 may be a single layer or may include multiple layers (for example, multiple light-emitting layers, multiple light-emitting layers and a space layer). In one embodiment, it is preferable that it is laminated with multiple layers.

[0242] In this invention, a host combined with a fluorescent dopant material (fluorescent material) is referred to as a fluorescent host, and a host combined with a phosphorescent dopant material is referred to as a phosphorescent host. Fluorescent hosts and phosphorescent hosts are not distinguished solely by their molecular structure. That is, a phosphorescent host refers to a material that forms a phosphorescent layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material for forming a fluorescent layer. The same applies to fluorescent hosts.

[0243] substrate The substrate is used as a support for the organic EL element. Examples of substrates include glass, quartz, and plastic plates. Flexible substrates may also be used. Examples of flexible substrates include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Inorganic vapor-deposited films can also be used.

[0244] anode For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or more). Specifically, examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium oxide containing tungsten oxide and zinc oxide, graphene, etc. 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 above metals (e.g., titanium nitride).

[0245] These materials are typically deposited by 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, while 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. Other methods such as vacuum deposition, coating, inkjet printing, and spin coating may also be used.

[0246] Hole transport band As described above, the organic layer may include a hole transport band between the anode and the light-emitting layer. The hole transport band is composed of a hole injection layer, a hole transport layer, an electron blocking layer, etc. It is preferable that the hole transport band contains the inventive compound. It is preferable that at least one layer selected from the group consisting of these layers constituting the hole transport band (hole injection layer, hole transport layer, electron blocking layer, etc.) contains the inventive compound, and it is particularly preferable that the hole transport layer contains the inventive compound.

[0247] The hole injection layer formed in contact with the anode is formed using a material that facilitates hole injection regardless of the anode's work function; therefore, materials commonly used as electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, elements belonging to Group 1 or Group 2 of the periodic table) can be used. Materials with low work functions, such as elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these, can also be used. When forming an anode using alkali metals, alkaline earth metals, or alloys containing these, vacuum deposition or sputtering methods can be used. Furthermore, when using silver paste or similar materials, coating methods or inkjet methods can be employed.

[0248] Hole injection layer The hole injection layer is a layer containing a material with high hole injection potential (hole injection material), and is formed between the anode and the light-emitting layer, or, if present, between the hole transport layer and the anode.

[0249] Other hole-injectable materials besides the inventive compound include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, and the like.

[0250] These are low-molecular-weight organic compounds: 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), and 1,3,5-tris[N-(4-di Aromatic amine compounds such as phenylaminophenyl)-N-phenylamino]benzene (abbreviated as DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviated as PCzPCN1) can also be used as hole implantation layer materials.

[0251] Polymeric compounds (oligomers, dendrimers, polymers, etc.) can also be used. Examples of polymeric compounds include poly(N-vinylcarbazole) (abbreviated as PVK), poly(4-vinyltriphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD). In addition, polymeric compounds to which acids such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can be added can also be used.

[0252] Furthermore, it is also preferable to use an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K).

[0253] [ka]

[0254] (In the above formula, R 221 ~R 226 These are, independently, a cyano group, -CONH2, a carboxyl group, or -COOR. 227 (R 227 (represents an alkyl group with 1 to 20 carbon atoms or a cycloalkyl group with 3 to 20 carbon atoms). Also, R 221 and R 222 , R 223 and R 224 , and R 225 and R 226 Two adjacent elements selected from the group may bond to each other to form a group represented by -CO-O-CO-. R 227 Examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, cyclopentyl group, and cyclohexyl group.

[0255] In one embodiment of the organic EL element according to the present invention, the hole transport band includes a hole injection layer between the anode and the first hole transport layer on the anode side, the hole injection layer includes a first organic material and a second organic material, the first organic material and the second organic material are different from each other, and the content of the second organic material in the hole injection layer is 0.01% by mass or more and less than 50% by mass, preferably 0.05% by mass or more and 30% by mass or less, more preferably 0.10% by mass or more and 10% by mass or less, even more preferably 0.50% by mass or more and 5% by mass or less, and particularly preferably 1.0% by mass or more and 3% by mass or less.

[0256] Examples of the first organic material include the inventive compound or the aforementioned hole-injectable materials other than the inventive compound.

[0257] In one embodiment of the organic EL element of this embodiment, the second organic material is a compound comprising at least one of a first ring structure represented by the following general formula (P11) and a second ring structure represented by the following general formula (P12).

[0258] [ka]

[0259] (The first ring structure represented by the general formula (P11) is condensed in the molecule of the second organic material with at least one of the ring structures of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted heterocycle having 5 to 50 ring-forming atoms.) = Z 10 The structure represented by the following general formulas is (11a), (11b), (11c), (11d), (11e), (11f), (11g), (11h), (11i), (11j), (11k), or (11m).

[0260] [ka]

[0261] [ka]

[0262] (In the above general formulas (11a), (11b), (11c), (11d), (11e), (11f), (11g), (11h), (11i), (11j), (11k), or (11m), R 11 ~R 14 R 1101 ~R 1110 Each of them operates independently. hydrogen atom, halogen atom, Hydroxyl group, Cyano group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R 906 )(R 907 ) a base represented by A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted. (In the above general formula (P12), Z1 to Z5 are each independent of each other.) Nitrogen atom, R 15 A carbon atom that bonds with it, or A carbon atom that bonds with other atoms in the molecule of the second organic material, Of Z1 to Z5, at least one is a carbon atom that bonds with other atoms in the molecule of the second organic material. R 15 teeth, hydrogen atom, halogen atom, Cyano group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, -Si(R 901 )(R 902 )(R 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R 906)(R 907 ) a base represented by Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, Carboxy group, Substituted or unsubstituted ester groups, Substituted or unsubstituted carbamoyl groups, Nitro group, and Selected from the group consisting of substituted or unsubstituted siloxanil groups, R 15 If multiple R 15 They are either identical or different. (In the second organic material, R 901 ~R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If there are multiple R 901 They are either identical or different from each other. R 902 If there are multiple R 902 They are either identical or different from each other. R 903 If there are multiple R 903 They are either identical or different from each other. R 904 If there are multiple R 904 They are either identical or different from each other. R 905 If there are multiple R 905 They are either identical or different from each other. R 906 If there are multiple R 906 They are either identical or different from each other. R907 If there are multiple R 907 They are either identical or different to one another.

[0263] In this specification, an ester group is at least one group selected from the group consisting of alkyl ester groups and aryl ester groups. In this specification, alkyl ester groups are, for example, -C(=O)OR E It is represented as R E For example, this is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 10 carbon atoms). In this specification, the aryl ester group is, for example, -C(=O)OR Ar It is represented as R Ar These are, for example, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms forming a ring.

[0264] In this specification, the siloxanyl group is a silicon compound group via an ether bond, such as a trimethylsiloxanyl group.

[0265] In this specification, the carbamoyl group is represented by -CONH2. In this specification, substituted carbamoyl groups include, for example, -CONH-Ar C , or -CONH-R C It is represented as Ar C This is, for example, at least one group selected from the group consisting of substituted or unsubstituted aryl groups with 6 to 50 (preferably 6 to 10) ring-forming carbon atoms and heterocyclic groups with 5 to 50 (preferably 5 to 14) ring-forming atoms. C This may be a group formed by bonding a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms with a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. R C For example, this is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 6 carbon atoms). In the second organic material described above, it is preferable that any group described as "substituted or unsubstituted" is an "unsubstituted" group.

[0266] Examples of the second organic material include the following compounds. However, the present invention is not limited to these specific examples of the second organic material.

[0267] [ka] [ka]

[0268] Hole transport layer The hole transport layer is a layer containing a material with high hole transport properties (hole transport material), and is formed between the anode and the light-emitting layer, or, if present, between the hole injection layer and the light-emitting layer. The inventive compound may be used alone or in combination with the following compounds in the hole transport layer.

[0269] The hole transport layer may be a single-layer structure or a multilayer structure containing two or more layers. For example, the hole transport layer may be a two-layer structure containing a first hole transport layer (anode side) and a second hole transport layer (cathode side). In other words, the hole transport band may include the first hole transport layer on the anode side and the second hole transport layer on the cathode side. Alternatively, the hole transport layer may be a three-layer structure containing a first hole transport layer, a second hole transport layer, and a third hole transport layer in order from the anode side. In other words, the third hole transport layer may be placed between the second hole transport layer and the light-emitting layer. In one embodiment of the present invention, the hole transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, and the hole transport layer closest to the cathode in the multilayer structure, for example, the second hole transport layer in the two-layer structure or the third hole transport layer in the three-layer structure, is preferably adjacent to the light-emitting layer. In particular, it is preferable that the light-emitting layer and the second hole transport layer are in direct contact. In another embodiment of the present invention, an electron blocking layer, etc., described later, may be interposed between the hole transport layer of the single-layer structure and the light-emitting layer, or between the hole transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer. Furthermore, as described above, if the hole transport layer is a multilayer structure containing two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer in the multilayer structure can also be used as an electron blocking layer. In one embodiment of the organic electroluminescent element according to the present invention, one or both of the first hole transport layer and the second hole transport layer contain the compound. Specifically, in the two-layer hole transport layer, the inventive compound may be contained in one of the first hole transport layer and the second hole transport layer, or in both. In another embodiment, at least one selected from the group consisting of the first to third hole transport layers contains the inventive compound. Specifically, in the three-layer hole transport layer, the inventive compound may be contained in only one of the first to third hole transport layers, in only two of them, or in all of them.

[0270] In one embodiment of the present invention, it is preferable that the inventive compound is contained in the second hole transport layer, and more specifically, it is preferable that the inventive compound is contained only in the second hole transport layer, or that the inventive compound is contained in both the first hole transport layer and the second hole transport layer.

[0271] Other hole transport layer materials besides the inventive compound can be used, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, and the like. Examples of aromatic amine compounds include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as BAFLP), and 4,4'-bis[N-(9,9-dimethylfluoren-2-yl Examples include )-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'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The above compounds are 10 -6 cm 2 It has a hole mobility of / Vs or greater.

[0272] Examples of carbazole derivatives include 4,4'-di(9-carbazolyl)biphenyl (abbreviated as CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviated as CzPA), and 9-phenyl-3-[4-(10-phenyl-9-antryl)phenyl]-9H-carbazole (abbreviated as PCzPA). Examples of anthracene derivatives include 2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviated as t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviated as DNA), and 9,10-diphenylanthracene (abbreviated as DPAnth). High molecular weight compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used. However, any compound other than those mentioned above may be used if it has higher hole transport properties than electron transport properties.

[0273] In one embodiment of the organic EL element according to the present invention, the first hole transport layer contains a compound represented by the following formula (21) or formula (22).

[0274] [ka] [In formulas (21) and (22) above, L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 Each of these is independently an arylene group with 6 to 50 ring-forming carbon atoms, either single-bonded, substituted, or unsubstituted, or a divalent heterocyclic group with 5 to 50 ring-forming atoms, k is 1, 2, 3, or 4. If k is 1, L E2 This is a substituted or unsubstituted arylene group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 ring-forming atoms. If k is 2, 3, or 4, multiple L E2 They are either identical or different from each other. If k is 2, 3, or 4, multiple L E2 They either bond to each other to form a substituted or unsubstituted monoring, or bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other. L that does not form the aforementioned monoring and does not form the aforementioned condensed ring E2 This is a substituted or unsubstituted arylene group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 ring-forming atoms. A 1 B 1 , C 1 , A 2 B 2 , C 2 , and D 2 These are, independently, substituted or unsubstituted aryl groups with 6 to 50 ring-forming carbon atoms, substituted or unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms, or -Si(R' 901 )(R'902 )(R' 903 ) and R' 901 , R' 902 and R' 903 These are, independently, substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms. R' 901 If multiple R's exist, 901 They are either identical or different from each other. R' 902 If multiple R's exist, 902 They are either identical or different from each other. R' 903 If multiple R's exist, 903 They are either identical or different from one another.

[0275] The first hole transport layer may contain one compound represented by formula (21) and formula (22), or it may contain multiple compounds represented by formula (21) and formula (22).

[0276] In formulas (21) and (22), A1, B1, C1, A2, B2, C2, and D2 are preferably each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibensofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group. Furthermore, more preferably, in formula (21), at least one selected from the group consisting of A1, B1, and C1, and in formula (22), at least one selected from the group consisting of A2, B2, C2, and D2, is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibensofuranil group, or a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0277] The fluorenyl groups that A1, B1, C1, A2, B2, C2, and D2 can take may have substituents at the 9-position, for example, a 9,9-dimethylfluorenyl group or a 9,9-diphenylfluorenyl group. Furthermore, the substituents at the 9-position may form a ring, for example, a fluorene skeleton or a xanthene skeleton.

[0278] L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 Preferably, each is independently a single-bonded, substituted, or unsubstituted ring-forming arylene group having 6 to 12 carbon atoms.

[0279] Specific examples of compounds represented by formulas (21) and (22) include the following compounds.

[0280] [ka]

[0281] Dopant material for the light-emitting layer The light-emitting layer is a layer containing a highly luminescent material (dopant material), and various materials can be used. For example, fluorescent materials and phosphorescent materials can be used as dopant materials. Fluorescent materials are compounds that emit light from a singlet excited state, and phosphorescent materials are compounds that emit light from a triplet excited state. In one embodiment of the organic EL element according to the present invention, the light-emitting layer is preferably a single layer. Furthermore, in one embodiment of the organic EL element according to the present invention, it is preferable that the light-emitting layer is stacked in multiple layers.

[0282] Examples of blue fluorescent materials that can be used in the light-emitting layer include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluorantene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, azavorin derivatives, and arylborane derivatives. 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-anthryl)triphenylamine (abbreviated as YGAPA), and 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCBAPA).

[0283] Aromatic amine derivatives can be used as green fluorescent luminescent materials that can be used in the light-emitting layer. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[ Examples include 9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), and N,N,9-triphenylanthracene-9-amine (abbreviation: DPhAPhA).

[0284] As red fluorescent materials that can be used in the light-emitting layer, tetracene derivatives and diamine derivatives can be used. Specifically, examples include N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviated as p-mPhTD) and 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluorantene-3,10-diamine (abbreviated as p-mPhAFD).

[0285] In one embodiment of the present invention, it is preferable that the light-emitting layer includes a fluorescent light-emitting material (fluorescent dopant material).

[0286] Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used as blue phosphorescent materials that can be used in the light-emitting layer. Specifically, examples include bis[2-(4',6'-difluorophenyl)pyridinate-N,C2']iridium(III)tetrakis(1-pyrazolyl)borate (abbreviated as FIr6), bis[2-(4',6'-difluorophenyl)pyridinate-N,C2']iridium(III) picolinate (abbreviated as FIrpic), bis[2-(3',5'bistrifluoromethylphenyl)pyridinate-N,C2']iridium(III) picolinate (abbreviated as Ir(CF3ppy)2(pic)), and bis[2-(4',6'-difluorophenyl)pyridinate-N,C2']iridium(III) acetylacetonate (abbreviated as FIracac).

[0287] Iridium complexes and the like are used as green phosphorescent materials that can be used in the light-emitting layer. Examples include tris(2-phenylpyridinato-N,C2')iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazolato)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), and bis(benzo[h]quinolinate)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)).

[0288] Metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used as red phosphorescent materials that can be used in the light-emitting layer. Specifically, examples include organometallic complexes such as bis[2-(2'-benzo[4,5-α]thienyl)pyridinate-N,C3']iridium(III) acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinolinate-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP).

[0289] Furthermore, rare earth metal complexes such as tris(acetylacetonate)(monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: Eu(DBM)3(Phen)), and tris[1-(2-tenoyl)-3,3,3-trifluoroacetonate](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3(Phen)) can be used as phosphorescent materials because the emission is due to electron transitions between different multiplicities from rare earth metal ions.

[0290] In one embodiment of the present invention, it is preferable that the light-emitting layer includes a phosphorescent material (phosphor dopant material).

[0291] Host material for the light-emitting layer The light-emitting layer may be configured by dispersing the dopant material described above in another material (host material). It is preferable to use a material that has a lower least unoccupied orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) than the dopant material.

[0292] For example, host materials include (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes, (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives, (3) Condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives, (4) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives are used.

[0293] In one embodiment of the present invention, the light-emitting layer preferably contains an anthracene derivative, and it is preferable that at least one hydrogen atom present on the benzene ring of the anthracene derivative is deuterated. Specific examples of anthracene derivatives will be discussed later.

[0294] For example, metal complexes such as tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ); Heterocyclic compounds such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), vasophenanthroline (abbreviation: BPhen), and vasocuproin (abbreviation: BCP); 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviated as CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviated as DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviated as DPPA), 9,10-di(2-naphthyl)anthracene (abbreviated as DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviated as t-Bu DNA), 9,9'-biantryl (abbreviated as BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviated as DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviated as DPNS2), 3,3',3''-(benzene-1,3,5-triyl)tripylene (abbreviated as TPB3), 9,10-diphenylanthracene (abbreviated as DPAnth), 6,12-dimethoxy-5,11-diphenylchrysene, and other condensed aromatic compounds; and N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H Aromatic amine compounds such as -carbazole-3-amine (abbreviated as 2PCAPA), 4,4'-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-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as DFLDPBi), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB) can be used. Multiple types of host materials may be used.

[0295] In particular, for blue fluorescent elements, it is preferable to use the following anthracene derivatives as the host material.

[0296] [ka]

[0297] [ka]

[0298] [ka]

[0299] [ka]

[0300] In one embodiment of the organic EL element according to the present invention, it is preferable that the light-emitting layer is stacked in a plurality of layers. When the light-emitting layer stacked in a plurality of layers is composed of, for example, 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 components constituting the second light-emitting layer. For example, this includes embodiments in which the dopant material contained in the first light-emitting layer is different from the dopant material contained in the second light-emitting layer, or embodiments in which the host material contained in the first light-emitting layer is different from the host material contained in the second light-emitting layer.

[0301] In the organic EL element according to this embodiment, the light-emitting layer may contain a light-emitting compound that exhibits fluorescence emission with a main peak wavelength of 500 nm or less.

[0302] The method for measuring the main peak wavelength of a compound is as follows: Prepare a 5 μmol / L toluene solution of the compound to be measured, place it in a quartz cell, and measure the emission spectrum of the sample at room temperature (300 K) (vertical axis: emission intensity, horizontal axis: wavelength). The emission spectrum can be measured using a spectrofluorometer (instrument name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is defined as the principal peak wavelength. In this specification, the principal peak wavelength may be referred to as the fluorescence emission principal peak wavelength (FL-peak).

[0303] The luminescent compound exhibiting fluorescence emission with a main peak wavelength of 500 nm or less may be the dopant material or the host material.

[0304] When the light-emitting layer is a single layer, either only one of the dopant material or the host material may be a light-emitting compound that exhibits fluorescence emission with a main peak wavelength of 500 nm or less, or both materials may be light-emitting compounds that exhibit fluorescence emission with a main peak wavelength of 500 nm or less. Furthermore, if the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, only one of the first or second light-emitting layer may contain a luminescent compound exhibiting fluorescence emission with a main peak wavelength of 500 nm or less, or both light-emitting layers may contain a luminescent compound exhibiting fluorescence emission with a main peak wavelength of 500 nm or less. Also, if the first light-emitting layer contains a luminescent compound exhibiting fluorescence emission with a main peak wavelength of 500 nm or less, only one of the dopant material and host material contained in the first light-emitting layer may contain a luminescent compound exhibiting fluorescence emission with a main peak wavelength of 500 nm or less, or both materials may contain a luminescent compound exhibiting fluorescence emission with a main peak wavelength of 500 nm or less. Furthermore, if the second light-emitting layer contains a luminescent compound exhibiting fluorescence emission with a main peak wavelength of 500 nm or less, only one of the dopant material and host material contained in the second light-emitting layer may contain a luminescent compound exhibiting fluorescence emission with a main peak wavelength of 500 nm or less, or both materials may contain a luminescent compound exhibiting fluorescence emission with a main peak wavelength of 500 nm or less.

[0305] electron transport layer The electron transport layer is a layer containing a material with high electron transport properties (electron transport material), and is formed between the light-emitting layer and the cathode, or, if present, between the electron injection layer and the light-emitting layer. The electron transport layer may be a single layer or a multilayer structure containing two or more layers. For example, the electron transport layer may be a two-layer structure containing a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one embodiment of the present invention, it is preferable that the electron transport layer of the single layer structure is adjacent to the light-emitting layer, and it is also preferable that the electron transport layer closest to the anode in the multilayer structure, for example, the first electron transport layer of the two-layer structure, is adjacent to the light-emitting layer. In another embodiment of the present invention, a hole blocking layer, etc., described later may be interposed between the electron transport layer of the single layer structure and the light-emitting layer, or between the electron transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer.

[0306] The electron transport layer includes, for example, (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, (2) Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, (3) Polymer compounds can be used.

[0307] Examples of metal complexes include tris(8-quinolinolato)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviated as BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviated as BAlq), bis(8-quinolinolato)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviated as ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviated as ZnBTZ), and (8-quinolinolato)lithium (abbreviated as Liq).

[0308] Examples of heteroaromatic compounds include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), vasophenanthroline (abbreviated as BPhen), vasocuproin (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviated as BzOs).

[0309] Examples of polymer 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).

[0310] The above materials are 10 -6 cm 2 The material has an electron mobility of / Vs or higher. However, any material with higher electron transport properties than hole transport properties may be used for the electron transport layer. Furthermore, the electron transport layer may be a single layer or a stack of two or more layers, each containing the above material. When the electron transport layer has a two-layer structure, the anode-side layer is referred to as the first electron transport layer, and the cathode-side layer as the second electron transport layer.

[0311] electron injection layer The electron injection layer is a layer containing a material with high electron injection potential. The electron injection layer can contain 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, alkali metal-containing organic complexes such as (8-quinolinolato)lithium (abbreviated as Liq), alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, rare earth metal halides, and rare earth metal-containing organic complexes. Multiple of these compounds can also be used in mixture form. In addition, materials containing alkali metals, alkaline earth metals, or compounds thereof in an electron-transporting material, specifically those containing magnesium (Mg) in Alq, may also be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, a composite material formed by mixing an organic compound with an electron donor may be used in the electron injection layer. 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, and specifically, for example, the materials that constitute the electron transport layer 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. Alkali metal oxides and alkaline earth metal oxides are also preferred, such as lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (abbreviated as TTF) can also be used.

[0312] cathode For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof with a small work function (specifically, 3.8 eV or less). 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 these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these. Furthermore, when forming a cathode using alkali metals, alkaline earth metals, or alloys containing these, vacuum deposition or sputtering methods can be used. Additionally, when using silver paste or similar materials, coating or inkjet methods can be employed. Furthermore, by providing an electron injection layer, cathodes can be formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium tin oxide containing silicon oxide, regardless of the magnitude of the work function. These conductive materials can be deposited using methods such as sputtering, inkjet printing, or spin coating.

[0313] insulating layer Organic EL elements are prone to pixel defects due to leakage and short circuits because an electric field is applied to an ultrathin film. To prevent this, an insulating layer consisting of an insulating thin film layer may be inserted between a pair of electrodes. Examples of materials used for the insulating layer include aluminum oxide, 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. Mixtures or laminates of these materials may also be used.

[0314] Space layer The space layer described above is, for example, a layer provided between a fluorescent emission layer and a phosphorescent emission layer when stacking them, to prevent excitons generated in the phosphorescent emission layer from diffusing into the fluorescent emission layer, or to adjust the carrier balance. Furthermore, a space layer can also be provided between multiple phosphorescent emission layers. Since the space layer is provided between the light-emitting layers, it is preferable that the material possesses both electron-transporting and hole-transporting properties. Furthermore, in order to prevent the diffusion of triplet energy within the adjacent phosphorescent light-emitting layer, it is preferable that the triplet energy be 2.6 eV or higher. Examples of materials used for the space layer include those used for the hole-transporting layer described above.

[0315] blocking layer A blocking layer such as an electron blocking layer, a hole blocking layer, or an exciton blocking layer may be provided adjacent to the light-emitting layer. The electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer, and the hole blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron transport layer. The exciton blocking layer prevents excitons generated in the light-emitting layer from diffusing into surrounding layers and has a function of confining excitons within the light-emitting layer.

[0316] Each layer of the organic EL element can be formed by conventionally known methods such as a vapor deposition method, a coating method, or the like. For example, the layers can be formed by known methods including vapor deposition methods such as a vacuum vapor deposition method and a molecular beam epitaxy (MBE) method, or coating methods using a solution of a compound for forming the layer, such as a dipping method, a spin coating method, a casting method, a bar coating method, and a roll coating method.

[0317] The film thickness of each layer is not particularly limited. In general, if the film thickness is too thin, defects such as pinholes tend to occur, while if the film thickness is too thick, a high driving voltage is required resulting in poor efficiency. Therefore, the film thickness is usually 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm.

[0318] In one embodiment of the organic EL element of the present invention, the sum of the thickness of the first hole transport layer and the thickness of the second hole transport layer is not less than 30 nm and not more than 150 nm. In this case, it is preferably not less than 40 nm and not more than 130 nm. Further, in one embodiment of the organic EL element of the present invention, the thickness of the second hole transport layer is not less than 20 nm. It is preferably not less than 25 nm, more preferably not less than 35 nm, and preferably not more than 100 nm. Further, in one embodiment of the organic EL element of the present invention, the thickness of the hole transport layer adjacent to the light-emitting layer is not less than 20 nm. It is preferably not less than 25 nm, more preferably not less than 30 nm, and preferably not more than 100 nm. Further, in one embodiment of the organic EL element of the present invention, the film thickness D1 of the first hole transport layer and the film thickness D2 of the second hole transport layer satisfy the relationship of 0.3 < D2 / D1 < 4.0. They preferably satisfy the relationship of 0.5 < D2 / D1 < 3.5, and more preferably satisfy the relationship of 0.75 < D2 / D1 < 3.0.

[0319] Examples of embodiments of the organic EL element of the present invention include, An organic EL element having the above-described two-layer hole transport layer, • A first embodiment in which the second hole transport layer contains the compound of the present invention, and the first hole transport layer does not contain the compound of the present invention; • A second embodiment in which both the first hole transport layer and the second hole transport layer contain the compound of the present invention; • A third embodiment in which the first hole transport layer contains the compound of the present invention, and the second hole transport layer does not contain the compound of the present invention; An organic EL element having the above-described three-layer hole transport layer, • A fourth embodiment in which the first hole transport layer contains the compound of the present invention, and the second and third hole transport layers do not contain the compound of the present invention; • A fifth embodiment in which the second hole transport layer contains the compound of the present invention, and the first and third hole transport layers do not contain the compound of the present invention; • A sixth embodiment in which the third hole transport layer contains the compound of the present invention, and the first and second hole transport layers do not contain the compound of the present invention; • A seventh embodiment in which the first and second hole transport layers contain the compound of the present invention, and the third hole transport layer does not contain the compound of the present invention; • An eighth embodiment in which the first and third hole transport layers contain the compound of the present invention, and the second hole transport layer does not contain the compound of the present invention; • A tenth embodiment in which the second and third hole transport layers contain the compound of the present invention, and the first hole transport layer does not contain the compound of the present invention; Examples include a tenth embodiment in which all of the first to third hole transport layers contain the compound of the present invention; and so on.

[0320] electronic equipment In one embodiment of the present invention, it is preferable that the electronic device includes an organic electroluminescent element. The aforementioned organic EL element can be used in display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and electronic devices such as lighting and vehicle light fixtures. [Examples]

[0321] The present invention will be described in more detail below using examples, but the present invention is not limited to the following examples.

[0322] The inventive compound used in the manufacture of the organic EL elements in Examples 1 and 2 [ka]

[0323] Comparative compounds used in the manufacture of organic EL elements in Comparative Examples 1 and 2 [ka]

[0324] Other compounds used in the production of organic EL elements in Examples 1-2 and Comparative Examples 1-2 [ka]

[0325] Fabrication of organic EL elements Example 1 A glass substrate with a 25mm x 75mm x 1.1mm ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was set to 130 nm. The glass substrate with the ITO transparent electrode, after cleaning, was mounted in the substrate holder of the vacuum deposition apparatus. First, compound HT-1 and compound HA were co-deposited onto the surface on which the transparent electrode was formed, covering the transparent electrode, to form 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. Next, compound HT-1 was deposited onto the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, compound HT-2 (compound 1) was deposited onto this first hole transport layer to form a second hole transport layer with a thickness of 10 nm. Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited onto this second hole transport layer to form a light-emitting layer with a thickness of 25 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 96:4. Next, compound ET-1 was deposited onto this light-emitting layer to form a first electron transport layer with a thickness of 5 nm. Next, compound ET-2 and Liq were co-deposited onto this first electron transport layer to form a second electron transport layer with a thickness of 20 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50. Next, LiF was deposited onto this second electron transport layer to form an electron injection electrode with a thickness of 1 nm. Then, metallic aluminum was deposited onto this electron-injection electrode to form a metallic cathode with a thickness of 50 nm. The layer configuration of the organic EL element of Example 1 obtained in this way is shown below. ITO (130) / HT-1:HA=97:3 (10) / HT-1 (80) / HT-2(Compound 1) (10) / BH-1:BD-1=96:4 (25) / ET-1 (5) / ET-2:Liq=50:50 (20) / LiF (1) / Al (50) In the above layer configuration, the numbers in parentheses represent the film thickness (nm), and the ratios represent the mass ratios.

[0326] Example 2 An organic EL device was fabricated in the same manner as in Example 1, except that compound 2 was used instead of compound 1.

[0327] Comparative Example 1 An organic EL device was fabricated in the same manner as in Example 1, except that comparative compound 1 was used instead of compound 1.

[0328] Comparative Example 2 An organic EL device was fabricated in the same manner as in Example 1, except that comparative compound 2 was used instead of compound 1.

[0329] Evaluation of organic EL elements Measurement of element lifespan (LT95) The resulting organic EL element was subjected to a current density of 50 mA / cm². 2 The device was driven by DC current, and the time (h) until the brightness decreased to 95% of the initial brightness was measured. This was defined as the 95% lifetime (LT95). Table 1 shows the relative values ​​(%) to the 95% lifetime (LT95) of Comparative Example 1, which is set to 100.

[0330] [Table 1]

[0331] As is clear from the results in Table 1, monoamines that satisfy the provisions of the present invention (compound 1 and compound 2) provide an organic EL device with significantly improved device lifetime compared to monoamines that do not satisfy the provisions of the present invention (comparative compound 1 and comparative compound 2).

[0332] The inventive compound synthesized in the synthesis example. [ka]

[0333] <Synthesis of Compounds> Intermediate synthesis example 1: Synthesis of intermediate A

[0334] [ka]

[0335] Under an argon atmosphere, a mixture of B-[4-(triphenylsilyl)phenyl]boronic acid (3.80 g, 10 mmol), 4-bromoaniline (1.72 g, 10 mmol), tetrakis(triphenylphosphine)palladium (0) (0.231 g, 0.2 mmol), sodium carbonate (3.18 g, 30 mmol), dioxane (40 mL), and water (10 mL) was placed in a flask and heated under reflux and stirred for 8 hours. After stirring, the mixture was cooled to room temperature (25°C), and toluene was added to separate the aqueous layer from the organic layer. The solvent of the resulting organic layer was removed by distillation, and the resulting residue was purified by silica gel column chromatography and recrystallization to obtain intermediate A, a white solid (2.7 g). The yield was 63%.

[0336] Intermediate synthesis example 2: Synthesis of intermediate B

[0337] [ka]

[0338] Under an argon atmosphere, a mixture of intermediate A (4'-(triphenylsilyl)-[1,1'-biphenyl]-4-amine (2.18 g, 5 mmol), 1-chloro-9,9-dimethyl-9H-fluorene (1.14 g, 5 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.092 g, 0.1 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.191 g, 0.4 mmol), sodium tert-butoxide (0.961 g, 10 mmol), and toluene (25 mL) was placed in a flask and heated under reflux and stirred for 8 hours. After stirring, the mixture was cooled to room temperature (25 °C), the solvent was removed by distillation, and the resulting residue was purified by silica gel column chromatography and recrystallization to obtain intermediate B as a white solid (1.4 g). The yield was 45%.

[0339] Synthesis Example 1: Synthesis of Compound 1

[0340] [ka]

[0341] Under an argon atmosphere, a mixture of intermediate B, 9,9-dimethyl-N-(4'-(triphenylsilyl)-[1,1'-biphenyl]-4-yl)-9H-fluoren-1-amine (3.10 g, 5 mmol), 4-bromo-1,1'-biphenyl (1.16 g, 5 mmol), tris(dibenzylideneacetone)dipalladium(0) (0).092 g, 0.1 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.191 g, 0.4 mmol), sodium tert-butoxide (0.961 g, 10 mmol), and toluene (25 mL) was placed in a flask and heated under reflux and stirred for 8 hours. After stirring, the mixture was cooled to room temperature (25°C), the solvent was removed by distillation, and the resulting residue was purified by silica gel column chromatography and recrystallization to obtain 2.4 g of a white solid. The yield was 62%. The obtained substance was identified as compound 1 by mass spectrometry, with a molecular weight of 772.08 and a m / e ratio of 773.

[0342] Synthesis Example 2: Synthesis of Compound 2 Compound 2 was synthesized using the same procedure as for compound 1, except that the compounds shown in Table 2 below were used as intermediates A and B. Compounds 1 and 2, along with intermediates A and B and their yields, are shown in Table 2.

[0343] [Table 2] [Explanation of symbols]

[0344] 1, 11, 12 Organic EL elements 2 circuit boards 3 Anode 4 cathode 5. Emitting layer 6. Hole transport zone (hole transport layer) 6a Hole injection layer 6b First Hole Transport Layer 6c Second Hole Transport Layer 6d Third Hole Transport Layer 7. Electron transport band (electron transport layer) 7a First electron transport layer 7b Second electron transport layer 10, 20, 30 Light-emitting units

Claims

1. A compound represented by the following formula (1). 【Chemistry 1】 [In formula (1), N ＊ It is the central nitrogen atom. R １ ~R ８ Each of these is independently either a hydrogen atom or an unsubstituted phenyl group. R is not a single bond. １ ~R ８ Two adjacent elements selected from these elements may bond to each other to form one or more substituted or unsubstituted benzene rings, or they may not bond to each other and therefore not form benzene rings. However, R １ and R ４ One of the options selected is a single bond that connects to *a. R ａ and R ｂ each independently represent a hydrogen atom or a substituent, and said substituent is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms. R ａ and R ｂ They do not bond with each other and do not form a ring. L ４ These are single-bonded or unsubstituted ring-forming arylene groups with 6 to 18 carbon atoms. Ar is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms forming a ring. However, when Ar is represented by a substituted or unsubstituted fluorenyl group, the adjacent substituents at positions 9,9 on the fluorenyl group are not bonded to each other and do not form a ring. L １ 、 L ２ and L ３ Each of these is independently a single-bonded, substituted, or unsubstituted ring-forming arylene group with 6 to 18 carbon atoms. R １１ ~R ２５ Each of these is independently a hydrogen atom or a substituted or unsubstituted ring-forming aryl group having 6 to 18 carbon atoms. R １１ ~R １５ Two adjacent elements are selected from R １６ ~R ２０ Two adjacent elements are selected from, or R ２１ ~R ２５ Two adjacent elements selected from these elements may bond to each other to form one or more substituted or unsubstituted benzene rings, or they may not bond to each other and therefore not form benzene rings. Two adjacent rings selected from benzene ring A, benzene ring B, and benzene ring C do not crosslink with each other. The substituents referred to as "substituted or unsubstituted" are unsubstituted C1-C20 alkyl groups, unsubstituted C3-C20 cycloalkyl groups, unsubstituted C6-C18 aryl groups, or unsubstituted C5-C13 heterocyclic groups. However, in the case of Ar, if the substituent referred to as "substituted or unsubstituted" is an unsubstituted C1-C20 alkyl group, two adjacent unsubstituted C1-C20 alkyl groups do not bond to each other and therefore do not form a ring.

2. R ａ and R ｂ The compound according to claim 1, wherein each of them is independently an unsubstituted methyl group.

3. The compound according to claim 1, wherein formula (1) is represented by the following formula (1-a) or formula (1-b). 【Chemistry 2】 (In the formula, N * , R ａ , R ｂ , R １ ~R ８ , R １１ ~R ２５ , L １ ~L ４ A, B, C, and Ar are defined in equation (1).

4. L １ The compound according to any one of claims 1 to 3, wherein is an unsubstituted phenylene group.

5. L ２ The compound according to any one of claims 1 to 4, wherein is an unsubstituted phenylene group.

6. L ３ The compound according to any one of claims 1 to 5, wherein is an unsubstituted phenylene group.

7. L １ The compound according to any one of claims 1 to 3, wherein the bond is a single bond.

8. L ４ The compound according to any one of claims 1 to 7, wherein the bond is a single bond.

9. The compound according to claim 3, wherein formula (1) is represented by formula (1-a).

10. The compound according to any one of claims 1 and 3 to 8, wherein formula (1) is represented by the following formula (1-a-1) or formula (1-a-2). 【Transformation 3】 (In the formula, N * , R ａ , R ｂ , R １ ~R ８ , R １１ ~R ２５ , L １ ~L ４ A, B, C, and Ar are defined in formula (1), and R ３１ ~R ３５ Each of these is independently a hydrogen atom or a substituent, and the substituent is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 18 carbon atoms.

11. The compound according to any one of claims 1 to 10, wherein Ar is a substituted or unsubstituted aryl group having 6 to 14 ring-forming carbon atoms.

12. The compound according to any one of claims 1 to 11, wherein the compound represented by formula (1) contains at least one deuterium atom.

13. A material for an organic electroluminescent device comprising the compound described in any one of claims 1 to 12.

14. An organic electroluminescent element having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer contains a compound according to any one of claims 1 to 12.

15. The organic electroluminescent element according to claim 14, wherein the organic layer includes a hole transport band between the anode and the light-emitting layer, and the hole transport band includes the compound.

16. The organic electroluminescent element according to claim 15, wherein the hole transport band includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side, and one or both of the first hole transport layer and the second hole transport layer contain the compound.

17. The organic electroluminescent element according to any one of claims 14 to 16, wherein the light-emitting layer comprises a fluorescent dopant material.

18. The organic electroluminescent element according to any one of claims 14 to 16, wherein the light-emitting layer comprises a phosphorescent dopant material.

19. An electronic device comprising an organic electroluminescent element according to any one of claims 14 to 18.

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