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

Abstract

Provided are a compound represented by formula (1A) or formula (1B) (the symbols in the formulas are as defined in the specification), a material for an organic electroluminescent element that contains the compound, an organic electroluminescent element that contains the compound, and an electronic device that contains such an organic electroluminescent element.

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, developing 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 3 disclose compounds to be used as materials for organic electroluminescent devices. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] U.S. Patent No. 7598667 [Patent Document 2] Chinese Patent Application Publication No. 114133333 Specification [Patent Document 3] U.S. Patent Application Publication No. 2022 / 0059771 [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] While many compounds for organic EL devices have been reported to date, there is still a need for compounds that can further improve the performance of organic EL devices.

[0006] The present invention has been made to solve the above problems, and an object thereof is to provide a compound for further improving the performance of an organic EL element, a material for an organic electroluminescence element, an organic EL element having further improved element performance, and an electronic device including such an organic EL element.

Means for Solving the Problems

[0007] As a result of intensive studies on the performance of an organic EL element containing a novel compound, the present inventors have found that the performance of an organic EL element containing a compound represented by the following formula (1A) or formula (1B) is further improved.

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

Chemical formula

Chemical formula

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

[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 consists of one or more layers including a light-emitting layer, and at least one layer selected from the group consisting of one and more layers constituting the organic layer contains a compound represented by formula (1A) or formula (1B).

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

[0012] Organic EL elements containing the compound represented by formula (1A) or formula (1B) 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 yet 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 an 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 are described below. Unless otherwise specified, each substituent described herein is defined as follows:

[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, m-terphenyl-3'-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 "heterocyclic group" as described herein may be 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) 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 -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), the 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" A specific example of the "substituted or unsubstituted alkylthio group" described herein is the group represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. The number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein.

[0063] • "Substituted or unsubstituted aryloxy groups" A specific example of a "substituted or unsubstituted aryloxy group" as described herein is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.

[0064] • "Substituted or unsubstituted arylthio groups" A specific example of the "substituted or unsubstituted arylthio group" described herein is the group represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.

[0065] • "Substituted or unsubstituted trialkylsilyl groups" A specific example of the "trialkylsilyl group" described herein is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) are either identical or different from one another. Unless otherwise specified herein, the number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0066] • "Substituted or unsubstituted aralkyl groups" Specific examples of the "substituted or unsubstituted aralkyl group" described herein include the group represented by -(G3)-(G1), where 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. Therefore, an "aralkyl group" is a group in which the hydrogen atom of an "alkyl group" is replaced by an "aryl group" as a substituent, and is one form of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" in which an "unsubstituted aryl group" is substituted, and the number of carbon atoms in the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified herein. Specific examples of "substituted or unsubstituted aralkyl groups" include 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 herein, the substituted or unsubstituted aryl groups are preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, pyrenyl, chrysenyl, triphenylenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl.

[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 groups" Unless otherwise specified, the "substituted or unsubstituted alkylene groups" described herein are divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl groups" described above. Specific examples of "substituted or unsubstituted alkylene groups" (Specific Examples Group G14) include the divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl groups" described in Specific Examples Group G3.

[0081] Unless otherwise specified herein, the substituted or unsubstituted arylene groups are preferably any of the following general formulas (TEMP-42) to (TEMP-68).

[0082] [ka]

[0083] [ka]

[0084] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each of these is independently either a hydrogen atom or a substituent. In the general formulas (TEMP-42) to (TEMP-52) above, * represents a bond position.

[0085] [ka]

[0086] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each of these is independently either a hydrogen atom or a substituent. Equations Q9 and Q 10 These elements may be bonded to each other via single bonds 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 of "one or more of the pairs consisting of two or more adjacent ones are bonded to each other to form a ring", the pair consisting of two adjacent ones that forms one pair is R 921 and R 922 and the pair of R 922 and R 923 and the pair of R 923 [[ID=X]]and R 924 and the pair of R 924 and R 930 and the pair of R 930 and R 925 and the pair of R 925 and R 926 and the pair of R<000l078>and R 927 and the pair of R 927 and R 928 and the pair of R 928 and R 929 and the pair of, and R 929 and R 921 and the pair of.

[0103] The above "one or more" means that two or more of the pairs consisting of two or more adjacent ones may form a ring simultaneously. For example, R 921 and R 922 are bonded to each other to form ring Q A , and at the same time R 925 and R 926 are bonded to each other to form ring Q B is formed, then the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0104]

Chemical formula

[0105] The case where a "pair consisting of two or more adjacent ones" forms a ring includes not only the case where a pair consisting of "two" adjacent ones is bonded as in the above example, but also the case where a pair consisting of "three or more" adjacent ones is bonded. For example, R 921 [[ID=7X]]and R 922 are bonded to each other to form ring Q A , and R 922 and R923 are combined with each other to form ring Q C to form, and a group consisting of three adjacent ones (R 921 , R 922 and R 923 ) are combined with each other to form a ring and condensed to the anthracene backbone, which means that 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 "monocyclic ring" or "condensed ring" formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when "one pair consisting of two adjacent ones" forms a "monocyclic ring" or "condensed ring", the "monocyclic ring" or "condensed ring" can form a saturated ring or an unsaturated ring. For example, in the general formula (TEMP-104), ring Q A and ring Q B are each a "monocyclic ring" or "condensed ring". Also, in the general formula (TEMP-105), ring Q A , and ring Q C are "condensed rings". Ring Q A and ring Q C in the general formula (TEMP-105) are a condensed ring formed by the condensation of ring Q A and ring Q C . If ring Q A in the general formula (TMEP-104) is a benzene ring, ring Q A is a monocyclic ring. If ring Q A in the general formula (TMEP-104) is a naphthalene ring, ring Q A is a condensed 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 with a hydrogen atom or the like, or substituted with "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, Unsubstituted alkyl groups with 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, It is a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 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. A compound according to one aspect of the present invention is represented by the following formula (1A) or formula (1B). However, the compounds of the present invention represented by formula (1A) and each formula included in formula (1A) described later may be simply referred to as "compound (1A)", "inventive compound (1A)", or "first inventive compound". Furthermore, the compounds of the present invention represented by formula (1B) and each formula included in formula (1B) described later may be simply referred to as "compound (1B)", "inventive compound (1B)", or "second inventive compound". In addition, the above first and second inventive compounds may be collectively referred to as "inventive compound". [ka] [ka]

[0118] The following explains the symbols in formula (1A) and the formula (1A) described later, as well as the symbols in formula (1B) and the formula (1B) described later. Note that the same symbols have the same meaning. In this specification, as shown below, the substructure that binds to *a in formula (1A) may be referred to as "substructure A". Also, the substructure that binds to *a in formula (1B) may be referred to as "substructure B". [ka]

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

[0120] In formula (1A), Z 1 ~Z 4 One of the selected is a single bond that joins *a, preferably Z 1 or Z 3 This is a single bond that connects to *a. In other words, the substructure A in the above formula (1A) is represented by the following formulas (1x-1), (1x-2), (1x-3), or (1x-4), and is preferably represented by the following formulas (1x-1) or (1x-3). When substructure A is represented by the following formula (1x-1), compound (1A) is represented by the formula (1A-1) described later. When substructure A is represented by the following formula (1x-3), compound (1A) is represented by the formula (1A-2) described later. [ka]

[0121] In equations (1x-1) to (1x-4), *x indicates the bonding position to *a. 1 ~Z 4 Details and other symbols are explained below.

[0122] The above Z is not a single bond. 1 ~Z 4 , and R 5 ~R 12Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heteroaryl group (aromatic heterocyclic group), preferably independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, or a ring-forming C6-C12 aryl group, and more preferably a hydrogen atom. The above Z is not a single bond. 1 ~Z 4 , and R 5 ~R 12 All of them may be hydrogen atoms. The above Z is not a single bond. 1 ~Z 4 , and R 5 ~R 12 They do not bond to each other to form a ring.

[0123] The above-mentioned substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, preferably 1 to 6 carbon atoms, include, for example, unsubstituted alkyl groups. These are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, or dodecyl groups; Preferably, the group is a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, or pentyl group; More preferably, the group is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group; More preferably, the group is a methyl group, an ethyl group, an isopropyl group, or a t-butyl group; A methyl group is particularly preferred.

[0124] The above-mentioned substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms, preferably 6 to 18, more preferably 6 to 12 carbon atoms, include, for example, The group is a phenyl group, biphenyl group, terphenyl group, naphthyl group, anthryl group, benzoantryl group, phenanthryl group, benzophenanthryl group, pyrenyl group, crisenyl group, benzocrisenyl group, fluorenyl group, fluoranteyl group, perilenyl group, or triphenylenyl group; Preferably, it is a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group; More preferably, 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; More preferably, the group is a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group; Particularly preferred is a phenyl group.

[0125] The above-mentioned substituted or unsubstituted heteroaryl groups having 5 to 30, preferably 5 to 20, and more preferably 5 to 13 ring-forming atoms are, for example, Pyrrolyl group, furyl group, thienyl group, pyridyl group, imidazopyridyl group, pyridadinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyrazolyl group, isoxazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, indolyl group, isoindolyl group, indollidinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, benzoisothia The group is a zolyl group, phenanthridine group, acridinyl group, phenanthrolinyl group, phenazinyl group, phenothiazinyl group, phenoxazinyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, naphthobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group (benzothienyl group, the same applies hereinafter), isobenzothiophenyl group (isobenzothienyl group, the same applies hereinafter), naphthobenzothiophenyl group (naphthobenzothienyl group, the same applies hereinafter), dibenzothiophenyl group (dibenzothienyl group, the same applies hereinafter), or a carbazolyl group (including a 9-carbazolyl group or a 1-, 2-, 3- or 4-carbazolyl group; the same applies hereinafter); Preferably, the group is a benzofuranyl group, an isobenzofuranyl group, a naphthobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, a naphthobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group. More preferably, it is a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.

[0126] In formula (1A), R 1 ~R 4 These are, independently, light hydrogen atoms.

[0127] In formula (1A), L 1 ~L 3Each of these is independently a substituted or unsubstituted ring-forming arylene group having 6 to 12 carbon atoms, preferably a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group, more preferably a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, and even more preferably a substituted or unsubstituted phenylene group.

[0128] The phenylene group is an o-phenylene group, an m-phenylene group, or a p-phenylene group, with a p-phenylene group being preferred. The above biphenylene group is a 4,2'-biphenylene group, a 4,3'-biphenylene group, a 4,4'-biphenylene group, a 3,2'-biphenylene group, a 3,3'-biphenylene group, or a 2,2'-biphenylene group, preferably a 4,2'-biphenylene group, a 4,3'-biphenylene group, a 4,4'-biphenylene group, or a 3,3'-biphenylene group, and more preferably a 4,4'-biphenylene group. The naphthylene group described above is preferably a 1,4-naphthylene group, a 2,6-naphthylene group, a 1,5-naphthylene group, or a 1,8-naphthylene group.

[0129] L is an arylene group 1 ~L 3 Each substituent is independently selected from unsubstituted C1-C6 alkyl groups and ring-forming C6-C12 aryl groups, and the substituents do not bond to each other or form a ring. Details of the above substituents, which are unsubstituted alkyl groups having 1 to 6 carbon atoms, and details of the above substituents, which are unsubstituted ring-forming aryl groups having 6 to 12 carbon atoms, are as follows: Z is not a single bond in formula (1A). 1 ~Z 4 , and R 5 ~R 12 As described above.

[0130] In equation (1A), n1 is either 0 or 1. When n1 is 0, Z 1 ~Z 4 One of the selected elements is the central nitrogen atom N *Combine.

[0131] In equation (1A), n² is either 0 or 1. When n2 is 0, Ar 1 The central nitrogen atom N * Combine.

[0132] In equation (1A), n3 is either 0 or 1. When n3 is 0, Ar 2 The central nitrogen atom N * Combine.

[0133] In one embodiment, n1, n2, and n3 are all 0; in another embodiment, n1, n2, and n3 are all 1; in yet another embodiment, n1 and n2 are 0 and n3 is 1; in yet another embodiment, n1 and n3 are 0 and n2 is 1; in yet another embodiment, n2 and n3 are 0 and n1 is 1; in yet another embodiment, n1 is 0, n2 and n3 are 1; in yet another embodiment, n2 is 0, n1 and n3 are 1; and in yet another embodiment, n3 is 0 and n1 and n2 are 1.

[0134] In equation (1A), L 1 and L 2 and L 3 If such a combination exists, the three may be identical, different from each other, or two of the three may be identical and the other one different. In equation (1A), L 1 and L 2 and L 3 Only two of these may exist (that is, two of n1, n2, and n3 may be 1 and the other one may be 0), and in this case, the two existing values ​​may be the same or they may be different. In equation (1A), L 1 and L 2 and L 3 Only one of these may exist (that is, two of n1, n2, and n3 may be 0 and the other one may be 1), L 1 ~L 3None of them must exist (i.e., n1, n2, and n3 may be 0). Preferably, the above "-(L 1 ) n1 -" and "-(L 2 ) n2 -" and "-(L 3 ) n3 The combination of "-" can be represented by one of the following combinations [k11] to [k18]. • [k11]: single bond / single bond / single bond • [k12]: single bond / single bond / phenylene • [k13]: single bond / phenylene / single bond • [k14]: Phenylene / single bond / single bond • [k15]: Single bond / phenylene / phenylene • [k16]: Phenylene / single bond / phenylene • [k17]: Phenylene / Phenylene / Single bond • [k18]: Phenylene / Phenylene / Phenylene

[0135] In formula (1A), Ar 1 and Ar 2 Each of these is independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, with substituted or unsubstituted aryl groups having 6 to 30 ring-forming carbon atoms being preferred. Ar 1 and Ar 2 Details of the substituted or unsubstituted aryl groups with 6 to 30 ring-forming carbon atoms represented by and the substituted or unsubstituted heteroaryl groups with 5 to 30 ring-forming atoms are shown in formula (1A) and the non-single bond Z. 1 ~Z 4 , and R 5 ~R 12 As described above.

[0136] (i)Ar 1 The group is represented by the following formula (2-1), and Ar 2 (ii)Ar 2The group is represented by the following formula (3-1), and Ar 1 (iii)Ar 1 The group is represented by the following formula (2-1), and Ar 2 The group may be represented by the following formula (3-1). [ka] [ka]

[0137] In equation (2-1), ** is L 2 This indicates the connection position to the destination.

[0138] In formula (2-1), X 1 This consists of an oxygen atom, a sulfur atom, and =NR 100 , or =CR A R B It is preferably an oxygen atom, or =CR A R B It is, and more preferably, an oxygen atom.

[0139] In formula (2-1), R 41 ~R 44 , R 100 , R A , and R B One of the options selected is either a single bond that joins *d, or R A and R B One of the selected groups is a divalent group that binds to *d. R is not a single bond as described above. 41 ~R 44 , and R 45 ~R 48Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heteroaryl group, preferably independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, or a ring-forming C6-C12 aryl group, and more preferably a hydrogen atom. R is not a single bond as described above. 41 ~R 44 , and R 45 ~R 48 All of them may be hydrogen atoms. R is not a single bond as described above. 41 ~R 44 Among them, a pair of adjacent bases, and R 45 ~R 48 Among these, adjacent pairs of groups may or may not bond to each other to form a ring.

[0140] R is not a single bond as described above. 41 ~R 44 , and R 45 ~R 48 Details of the substituted or unsubstituted C1-C6 alkyl groups, substituted or unsubstituted ring-forming C6-C12 aryl groups, and substituted or unsubstituted ring-forming C5-C13 heteroaryl groups represented by are shown in formula (1A) and the non-single bond Z. 1 ~Z 4 , and R 5 ~R 12 As described above.

[0141] R that is not a single bond as described above 100 Furthermore, R is not a single bond as described above, but a divalent group that is not bonded to *d as described above. A and R B Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heteroaryl group, preferably independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, and a ring-forming C6-C12 aryl group. R that is not a single bond as described above 100 Furthermore, R is not a single bond as described above, but a divalent group that is not bonded to *d as described above. A and R B It may also be a hydrogen atom. R 100 , R A , and R B Details of the substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted ring-forming C6-C30 aryl groups, and substituted or unsubstituted ring-forming C5-C30 heteroaryl groups represented by are shown in formula (1A) and the non-single bond Z. 1 ~Z 4 , and R 5 ~R 12 As described above.

[0142] R is not a single bond as described above, nor is it a divalent group that bonds to *d as described above. A and R B These elements may or may not combine to form a ring. R is not a single bond as described above, nor is it a divalent group that bonds to *d as described above. A and R B The rings formed by the bonding of these elements are substituted or unsubstituted spiro rings. These spiro rings are hydrocarbon rings or heterocycles, and can be selected from monocycles, fused rings, bridged bicyclo rings, or bridged tricyclo rings. Examples of substituted or unsubstituted spiro rings are shown below, but are not limited to these. * indicates the bond position of the fluorene skeleton to the benzene ring. [ka]

[0143] In one embodiment, equation (2-1) can be expressed as any of the following equations (1-a1) to (1-a5). [ka] [ka]

[0144] In equations (1-a1) to (1-a5), ** represents L 2 This indicates the connection position to the destination. R 41 ~R 48 , and *d are as defined in formula (1A) above. In formulas (1-a1) to (1-a5), R A1 ~R A3 , R A4 ~R A8 , R B1 ~R B3 , and R B4 ~R B8 It is a hydrogen atom.

[0145] R A and R B The divalent group bonded to *d above, represented by , is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring-forming atoms. R A and R B The alkylene group, arylene group, and heteroarylene group represented by the above are R A and R B The alkyl groups, aryl groups, and heteroaryl groups represented by the above-mentioned groups include divalent residues of each group as described, and the same applies to preferred groups.

[0146] In equation (3-1), *** is L 3 This indicates the connection position to the destination.

[0147] In formula (3-1), X 2 This consists of an oxygen atom, a sulfur atom, and =NR 101 , or =CR C R D It is preferably an oxygen atom, or =CR C R D It is, and more preferably, an oxygen atom.

[0148] In formula (3-1), R 21B ~R 24B , R 101 , R C, and R D One of the options is a single bond that joins *b2, or R C and R D One of the selected groups is a divalent group that binds to *b2. X 2 However, when it is an oxygen atom or a sulfur atom, R 21B ~R 24B One of the selected bonds is a single bond that connects to *b2, preferably R 21B , R 22B , and R 24B One of the selected is a single bond that connects to *b2, and more preferably R 21B and R 24B One of the selected bonds is a single bond that connects to *b2, and more preferably R 24B This is a single bond that connects to *b2. X 2 However, =NR 101 In that case, preferably R 21B ~R 23B , and R 101 One of the selected bonds is a single bond that connects to *b2, or more preferably R 23B or R 101 One of the options selected is a single bond that connects to *b2. X 2 However, =CR C R D In that case, preferably R 21B ~R 23B , R C , and R D One of the selected bonds is a single bond that connects to *b2, or R C and R D One of the selected groups is a divalent group that binds to *b2, more preferably R 23B , R C , or R D One of the selected bonds is a single bond that connects to *b2, or R C and R D One of the selected groups is a divalent group that binds to *b2. R is not a single bond as described above. 21B ~R 24B , and R 25B ~R 28BEach of these is independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heteroaryl group, preferably independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, or a ring-forming C6-C12 aryl group, and more preferably a hydrogen atom. R is not a single bond as described above. 21B ~R 24B , and R 25B ~R 28B All of them may be hydrogen atoms. R 21B ~R 28B Details of the substituted or unsubstituted C1-C6 alkyl groups, substituted or unsubstituted ring-forming C6-C12 aryl groups, and substituted or unsubstituted ring-forming C5-C13 heteroaryl groups represented by are shown in formula (1A) and the non-single bond Z. 1 ~Z 4 , and R 5 ~R 12 As described above.

[0149] In formula (3-1), R 21B ~R 24B If one of the selected options is a single bond that connects to *b2, then R is not the single bond mentioned above. 21B ~R 24B They do not bond to each other to form a ring, and R 25B ~R 28B These elements may or may not combine to form a ring.

[0150] R that is not a single bond as described above 101 Furthermore, R is not a single bond as described above, but a divalent group that is not bonded to *b2 as described above. C and R DEach of these is independently a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heteroaryl group, preferably independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, or a ring-forming C6-C12 aryl group, and more preferably a hydrogen atom. R that is not a single bond as described above 101 Furthermore, R is not a single bond as described above, but a divalent group that is not bonded to *b2 as described above. C and R D It may also be a hydrogen atom. R is not a single bond as described above, nor is it a divalent group that is bonded to *b2 as described above. C and R D These elements may or may not combine to form a ring. R 101 , R C , and R D Details of the substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted ring-forming C6-C30 aryl groups, and substituted or unsubstituted ring-forming C5-C30 heteroaryl groups represented by are shown in formula (1A) and the non-single bond Z. 1 ~Z 4 , and R 5 ~R 12 As described above.

[0151] R C and R D The divalent group bonded to *b2 as represented by the above is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring-forming atoms. R C and R D The alkylene group, arylene group, and heteroarylene group represented by the above are R A and R B The alkyl groups, aryl groups, and heteroaryl groups represented by the above-mentioned groups include divalent residues of each group as described, and the same applies to preferred groups.

[0152] In one aspect, Ar 1 and Ar 2 At least one of these can be expressed by one of the following equations (2A) to (2F). [ka]

[0153] In equation (2A), *21 is L 2 or L 3 This is the binding position to [the target].

[0154] In formula (2A), R 101 ~R 105 One of the selected options is a single bond that connects to *22, R 106 ~R 110 One of the options selected is a single bond that connects to *23. R is not a single bond as described above. 101 ~R 105 and R that is not a single bond 106 ~R 110 Each of these is independently a hydrogen atom, an unsubstituted C1-C10 alkyl group, or an unsubstituted ring-forming C6-C12 aryl group, preferably a hydrogen atom. R is not a single bond as described above. 101 ~R 105 and R that is not a single bond as described above 106 ~R 110 All of them may be hydrogen atoms. Details of the above substituted or unsubstituted C1-C10 alkyl groups are as follows: Except for having 1-10 carbon atoms, Z is not a single bond in formula (1A). 1 ~Z 4 , and R 5 ~R 12 As described above. Details of the above-mentioned substituted or unsubstituted ring-forming aryl groups with 6 to 12 carbon atoms can be found in formula (1A) Z. 1 ~Z 4 , and R 5 ~R 12 As described above. R is not a single bond as described above. 101 ~R105 Two adjacent elements selected from this list do not join to each other and do not form a ring. R is not a single bond as described above. 106 ~R 110 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0155] In formula (2A), R 111 ~R 115 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heteroaryl group, preferably independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, or a ring-forming C6-C12 aryl group, and more preferably a hydrogen atom. R 111 ~R 115 All of them may be hydrogen atoms. Details of the above substituted or unsubstituted C1-C10 alkyl groups are as follows: Except for having 1-10 carbon atoms, Z is not a single bond in formula (1A). 1 ~Z 4 , and R 5 ~R 12 As described above. Details of the above-mentioned substituted or unsubstituted ring-forming aryl groups with 6 to 12 carbon atoms, and details of the above-mentioned substituted or unsubstituted ring-forming heteroaryl groups with 5 to 13 carbon atoms, are shown in formula (1A) and Z, which is not a single bond. 1 ~Z 4 , and R 5 ~R 12 As described above. R 111 ~R 115 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0156] In equation (2A), m11 is 0, 1, or 2, and n11 is 0 or 1, except when m11 is 2 and n11 is 0. If m11=0 and n11=0, then *23 represents *21. When m11=0 and n11=1, *22 represents *21. When m11=1 and n11=0, *23 represents *22. Ar 1 When expressed by equation (2A), it is preferable that n2 is 0, and Ar 2 When expressed by equation (2A), it is preferable that n3 is 0. Also, Ar 1 and Ar 2 If at least one of the following is expressed by equation (2A), and m11 is 0 and n11 is 1, then R 106 ~R 110 It is preferable that this is a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms. Furthermore, Ar 1 and Ar 2 At least one of the following is expressed by equation (2A), and when m11 is 1 and n11 is 0, the R bond that is not a single bond to *22 is 101 ~R 105 It is preferable that this is a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.

[0157] The group represented by formula (2A) is preferably represented by the following formula. In the following formula, R is omitted for simplification. [ka]

[0158] [ka]

[0159] In equation (2B), *24 is L 2 or L 3 This is the binding position to [the target].

[0160] In formula (2B), R 121 ~R 128 One of the options selected is a single bond that connects to *25. R is not a single bond as described above. 121 ~R 128Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted ring-forming C6-C12 aryl group, preferably a hydrogen atom. R 121 ~R 125 All of them may be hydrogen atoms. Details of the above substituted or unsubstituted C1-C10 alkyl groups are as follows: Except for having 1-10 carbon atoms, Z is not a single bond in formula (1A). 1 ~Z 4 , and R 5 ~R 12 As described above. Details of the above-mentioned substituted or unsubstituted ring-forming aryl groups with 6 to 12 carbon atoms are shown in formula (1A), which is not a single bond. 1 ~Z 4 , and R 5 ~R 12 As described above. R is not a single bond as described above. 121 ~R 128 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0161] [ka]

[0162] In equation (2C), *26 is L 2 or L 3 This is the binding position to [the target].

[0163] In formula (2C), R 131 ~R 140 One of the options selected is a single bond that connects to *27. R is not a single bond as described above. 131 ~R 140 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted ring-forming C6-C12 aryl group, preferably a hydrogen atom. R is not a single bond as described above. 131 ~R 140 All of them may be hydrogen atoms. Details of the above substituted or unsubstituted C1-C10 alkyl groups are as follows: Except for having 1-10 carbon atoms, Z is not a single bond in formula (1A). 1 ~Z 4 , and R 5 ~R 12 As described above. Details of the above-mentioned substituted or unsubstituted ring-forming aryl groups with 6 to 12 carbon atoms are shown in formula (1A), which is not a single bond. 1 ~Z 4 , and R 5 ~R 12 As described above. R is not a single bond as described above. 131 ~R 140 Two adjacent elements selected from this list do not join to each other and do not form a ring. [ka]

[0164] In equation (2D), *28 is L 2 or L 3 This is the binding position to [the target].

[0165] In equation (2D), n12 is either 0 or 1. When n12 is 0, R 141 ~R 148 One of the options selected is a single bond that connects to *29. When n12 is 1, R 141 and R 142 , R 142 and R 143 , or R 143 and R 144 One of the R atoms is a single bond that connects to *h, and the other is a single bond that connects to *i, and is not a single bond that connects to both *h and *i. 141 ~R 144 , R 145 ~R 148 , and R 200 ~R 203 One of the options selected is a single bond that connects to *29.

[0166] In equation (2D), R is not a single bond as described above. 141~R 148 and R that is not a single bond as described above 200 ~R 203 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heteroaryl group, preferably independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, or a ring-forming C6-C12 aryl group, and more preferably a hydrogen atom. R is not a single bond as described above. 141 ~R 148 and R that is not a single bond as described above 200 ~R 203 All of them may be hydrogen atoms. Details of the above substituted or unsubstituted C1-C10 alkyl groups are as follows: Except for having 1-10 carbon atoms, Z is not a single bond in formula (1A). 1 ~Z 4 , and R 5 ~R 12 As described above. Details of the above-mentioned substituted or unsubstituted ring-forming aryl groups with 6 to 12 carbon atoms, and details of the above-mentioned substituted or unsubstituted ring-forming heteroaryl groups with 5 to 13 carbon atoms, are shown in formula (1A) and Z, which is not a single bond. 1 ~Z 4 , and R 5 ~R 12 As described above. R is not a single bond as described above. 141 ~R 148 and R that is not a single bond as described above 200 ~R 203 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0167] In formula (2D), R E and R FEach of these is independently a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heteroaryl group, preferably independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, and a ring-forming C6-C12 aryl group. The above R E and R F It may also be a hydrogen atom. Details of the above substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms are shown in formula (1A), which is not a single bond. 1 ~Z 4 , and R 5 ~R 12 As described above. Details of the above-mentioned substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms, and details of the above-mentioned substituted or unsubstituted ring-forming heteroaryl groups with 5 to 30 atoms, are shown in formula (1A) and Z, which is not a single bond. 1 ~Z 4 , and R 5 ~R 12 As described above. The above R E and R F These elements may or may not combine to form a ring.

[0168] [ka]

[0169] In equation (2E), *30 is L 2 or L 3 This is the binding position to [the target].

[0170] In formula (2E), R 151 ~R 155 One of the selected bonds is a single bond that connects to *31, R 151 ~R 155 The other one selected is a single bond that connects to *32. R is not a single bond as described above. 151 ~R 155Each of these is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group, preferably a hydrogen atom. R is not a single bond as described above. 151 ~R 155 All of them may be hydrogen atoms. Details of the above substituted or unsubstituted C1-C10 alkyl groups are as follows: Except for having 1-10 carbon atoms, Z is not a single bond in formula (1A). 1 ~Z 4 , and R 5 ~R 12 As described above. R is not a single bond as described above. 151 ~R 155 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0171] In formula (2E), R 161 ~R 165 and R 171 ~R 175 Each of these is independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms, preferably a hydrogen atom. R 161 ~R 165 and R 171 ~R 175 All of them may be hydrogen atoms. Details of the above substituted or unsubstituted C1-C10 alkyl groups are as follows: Except for having 1-10 carbon atoms, Z is not a single bond in formula (1A). 1 ~Z 4 , and R 5 ~R 12 As described above. R is not a hydrogen atom 161 ~R 165 At least one adjacent pair selected from may bond to each other to form one or more unsubstituted benzene rings, or they may not bond to each other to form a ring. R is not a hydrogen atom. 171 ~R 175At least one adjacent pair selected from may bond to each other to form one or more unsubstituted benzene rings, or they may not bond to each other and therefore not form rings.

[0172] Formula (2E) includes a group represented by the following formulas (2E-1) to (2E-5), with formulas (2E-1), (2E-2), or (2E-5) being preferred. [ka]

[0173] [ka]

[0174] In equation (2F), *32 is L 2 or L 3 This is the binding position to [the target].

[0175] In formula (2F), R 181 ~R 192 One of the options selected is a single bond that connects to *33. R is not a single bond as described above. 181 ~R 192 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted ring-forming C6-C12 aryl group, preferably a hydrogen atom. R is not a single bond as described above. 181 ~R 192 All of them may be hydrogen atoms. Details of the above substituted or unsubstituted C1-C10 alkyl groups are as follows: Except for having 1-10 carbon atoms, Z is not a single bond in formula (1A). 1 ~Z 4 , and R 5 ~R 12 As described above. Details of the above-mentioned substituted or unsubstituted ring-forming aryl groups with 6 to 12 carbon atoms are shown in formula (1A), which is not a single bond. 1 ~Z 4 , and R 5 ~R12 As described above. R is not a single bond as described above. 181 ~R 192 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0176] <Compound (1B)> In formula (1B), N * It is the central nitrogen atom.

[0177] In formula (1B), Z 5 ~Z 8 One of the selected is a single bond that joins *a, preferably Z 5 ~Z 6 One of the selected options is a single bond that connects to *a. In other words, the substructure B in the above formula (1B) can be represented by any of the following formulas (1y-1) to (1y-4), preferably by any of the following formulas (1y-1) to (1y-2). [ka]

[0178] In equations (1y-1) to (1y-4), *y indicates the bond position to *a. 5 ~Z 8 Details and other symbols are explained below.

[0179] The above Z is not a single bond. 5 ~Z 8 , and R 21 ~R 32 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heteroaryl group (aromatic heterocyclic group), preferably independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, or a ring-forming C6-C12 aryl group, and more preferably a hydrogen atom. The above Z is not a single bond. 5 ~Z 8 , and R21 ~R 32 All of them may be hydrogen atoms. The above Z is not a single bond. 5 ~Z 8 , and R 21 ~R 32 They do not bond to each other to form a ring. Z is not a single bond. 5 ~Z 8 , and R 21 ~R 32 Details of the substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted ring-forming C6-C30 aryl groups, and substituted or unsubstituted ring-forming C5-C30 heteroaryl groups represented by are shown in formula (1A) and the non-single bond Z. 1 ~Z 4 , and R 5 ~R 12 As described above.

[0180] In formula (1B), L 1 ~L 3 Ar 1 ~Ar 2 , and n1~n3 are equivalent to those defined in equation (1A).

[0181] In one preferred embodiment, the above compound (1A) is represented by the following formula (1A-1). [ka]

[0182] In formula (1A-1), R 1 ~ 12 , Z 2 ~Z 4 , N * Ar 1 ~Ar 2 , L 1 ~L 3 , and n1 to n3 are as defined in equation (1A) above.

[0183] In one embodiment, the above compound (1A) is represented by the following formula (1A-2). [ka]

[0184] In formula (1A-2), R 1 ~R 12 , Z 1 , Z 2 , Z 4 , N * Ar 1 ~Ar 2 , L 1 ~L 3 , and n1 to n3 are as defined in equation (1A) above.

[0185] In one embodiment, compound (1A) is represented by the above formula (1A), formula (1A-1), or formula (1A-2), and when n1 is 1, L 1 It is a phenylene group, and when n2 is 1, L 2 It is a phenylene group, and when n3 is 1, L 3 This is a phenylene group.

[0186] In one embodiment, the above compound (1A) is represented by any of the following formulas (1A-3) to (1A-9). [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0187] In formulas (1A-3) to (1A-9), R 1 ~R 12 , Z 1 ~Z 4 , N * , *a, Ar 1 ~Ar 2 , L 1 ~L 3 , and n1 to n3 are as defined in equation (1A) above.

[0188] In one embodiment, the above compound (1A) is represented by any of the following formulas (1A-10) to (1A-16). [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0189] In equations (1A-10), (1A-13), (1A-14), and (1A-16), R 51 ~R 55 Each of these is independently a hydrogen atom, an unsubstituted C1-C6 alkyl group, or an unsubstituted ring-forming C6-C12 aryl group. However, R 51 ~R 55One of the options is a single bond that joins *d. R is not a single bond that joins *d. 51 ~R 55 All of them may be hydrogen atoms. R that is not a single bond 51 ~R 55 Of these, one adjacent pair does not connect with each other and does not form a ring.

[0190] In equations (1A-11), (1A-13), (1A-15), and (1A-16), R 71 ~R 75 Each of these is independently a hydrogen atom, an unsubstituted C1-C6 alkyl group, or an unsubstituted ring-forming C6-C12 aryl group. However, R 71 ~R 75 One of the options is a single bond that connects to *f. R is not a single bond that connects to *f. 71 ~R 75 All of them may be hydrogen atoms. R that is not a single bond 71 ~R 75 Of these, one adjacent pair does not connect with each other and does not form a ring.

[0191] In equations (1A-12) and (1A-14) to (1A-16), R 81 ~R 85 Each of these is independently a hydrogen atom, an unsubstituted C1-C6 alkyl group, or an unsubstituted ring-forming C6-C12 aryl group. However, R 81 ~R 85 One of the options is a single bond that connects to *g. R is not a single bond that connects to *g. 81 ~R 85 All of them may be hydrogen atoms. R that is not a single bond 81 ~R 85 Of these, one adjacent pair does not connect with each other and does not form a ring.

[0192] R 51 ~R 55 , R 71 ~R 75 , and R 81 ~R 85Details of the unsubstituted C1-C6 alkyl group and the unsubstituted ring-forming C6-C12 aryl group represented by are shown in formula (1A) and Z, which is not a single bond. 1 ~Z 4 , and R 5 ~R 12 As described above.

[0193] In formulas (1A-10) to (1A-16), R 1 ~R 12 , Z 1 ~Z 4 , N * , *a, Ar 1 ~Ar 2 , L 1 ~L 3 , and n1 to n3 are as defined in equation (1A) above.

[0194] In one embodiment, the above compound (1B) is represented by the following formula (1B-1). [ka]

[0195] In formula (1B-1), R 21 ~R 32 , Z 6 ~Z 8 , N * Ar 1 ~Ar 2 , L 1 ~L 3 , and n1 to n3 are as defined in equation (1B) above.

[0196] In one embodiment, the above compound (1B) is represented by the following formula (1B-2). [ka]

[0197] In formula (1B-2), R 21 ~R 32 , Z 5 , Z 7 ~Z 8 , N *Ar 1 ~Ar 2 , L 1 ~L 3 , and n1 to n3 are as defined in equation (1B) above.

[0198] In one embodiment, it is expressed by any of the above formulas (1B), (1B-1), and (1B-2), and when n1 is 1, L 1 It is a phenylene group, and when n2 is 1, L 2 It is a phenylene group, and when n3 is 1, L 3 This is a phenylene group.

[0199] In one embodiment, the above compound (1B) is represented by any of the following formulas (1B-3) to (1B-9). [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0200] In formulas (1B-3) to (1B-9), R 21 ~R 32 , Z 5 ~Z 8 , N * Ar 1 ~Ar 2 , L1 ~L 3 , and n1 to n3 are as defined in equation (1B) above.

[0201] In one embodiment, the above compound (1B) is represented by any of the following formulas (1B-10) to (1B-16). [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0202] In formula (1B-10), formula (1B-13), formula (1B-14), and formula (1B-16), R 51 ~R 55 Each of these is independently a hydrogen atom, an unsubstituted C1-C6 alkyl group, or an unsubstituted ring-forming C6-C12 aryl group, preferably a hydrogen atom. However, R 51 ~R 55 One of the options is a single bond that joins *d. R is not a single bond that joins *d. 51 ~R 55 All of them may be hydrogen atoms. R is not a single bond as described above. 51 ~R 55 Of these, one adjacent pair does not connect with each other and does not form a ring.

[0203] In formula (1B-11), formula (1B-13), formula (1B-15), and formula (1B-16), R 71 ~R 75 Each of these is independently a hydrogen atom, an unsubstituted C1-C6 alkyl group, or an unsubstituted ring-forming C6-C12 aryl group, preferably a hydrogen atom. However, R 71 ~R 75 One of the options is a single bond that connects to *f. R is not a single bond that connects to *f. 71 ~R 75 All of them may be hydrogen atoms. R that is not a single bond 71 ~R 75 Of these, one adjacent pair does not connect with each other and does not form a ring.

[0204] In formula (1B-12) and formula (1B-14) to formula (1B-16), R 81 ~R 85 Each of these is independently a hydrogen atom, an unsubstituted C1-C6 alkyl group, or an unsubstituted ring-forming C6-C12 aryl group, preferably a hydrogen atom. However, R 81 ~R 85 One of the options is a single bond that connects to *g. R is not a single bond that connects to *g. 81 ~R 85 All of them may be hydrogen atoms. R that is not a single bond 81 ~R 85 Of these, one adjacent pair does not connect with each other and does not form a ring.

[0205] R 51 ~R 55 , R 71 ~R 75 , and R 81 ~R 85 Details of the unsubstituted C1-C6 alkyl group and the unsubstituted ring-forming C6-C12 aryl group represented by are shown in formula (1A) and Z, which is not a single bond. 1 ~Z 4 , and R 5 ~R 12 As described above.

[0206] In formulas (1B-10) to (1B-16), R 21 ~R 32 , Z 5 ~Z 8 , N * Ar 1 ~Ar 2 , L 1 ~L 3 , and n1 to n3 are as defined in equation (1B) above.

[0207] In one embodiment, the inventive compound is represented by any of the above formulas (1A) and (1A-1) to (1A-16), X 1 That is an oxygen atom.

[0208] In one embodiment, the inventive compound is represented by any of the above formulas (1B) and (1B-1) to (1B-16), X 2 This is an oxygen atom.

[0209] One aspect, the above is not a single bond Z 1 ~Z 4 , R 5 ~R 12 , Z which is not a single bond as described above 5 ~Z 8 , R 21 ~R 32 , R which is not a single bond as described above 41 ~R 44 , R 45 ~R 48 , R which is not a single bond as described above 100 R is not a divalent group that bonds to *d, rather than the single bond mentioned above. A and R B , R which is not a single bond as described above 21B ~R 24B , R 25B ~R 28B , R which is not a single bond as described above 101 R is not a divalent group that bonds to *b2, rather than the single bond mentioned above. C and R D , R 51 ~R 55 , R 71 ~R 75 , R 81~R 85 , R which is not a single bond as described above 101 ~R 105 , R which is not a single bond as described above 106 ~R 110 , R 111 ~R 115 , R which is not a single bond as described above 121 ~R 128 , R which is not a single bond as described above 131 ~R 140 , R which is not a single bond as described above 141 ~R 148 , R which is not a single bond as described above 200 ~R 203 , R E and R F , R which is not a single bond as described above 151 ~R 155 , R 161 ~R 165 , R 171 ~R 175 , and also R that is not a single bond as described above 181 ~R 192 All of them are hydrogen atoms.

[0210] In one embodiment, the compound represented by formula (1A) or formula (1B) contains at least one deuterium atom. The deuterium atoms contained in compound (1A) and compound (1B) will be explained in detail later.

[0211] In one embodiment of compound (1A) and compound (1B), at least one of the following (1) to (9) is a deuterium atom. (1)Z 1 ~Z 4 , R 5 ~R 12 , Z 5 ~Z 8 , R 21 ~R 32 , R 41 ~R 44 , R 45 ~R 48 , R 100 , R A and R B , R 21B ~R 24B , R 25B ~R 28B , R101 , R C and R D , R 51 ~R 55 , R 71 ~R 75 , R 81 ~R 85 , R 101 ~R 105 , R 106 ~R 110 , R 111 ~R 115 , R 121 ~R 128 , R 131 ~R 140 , R 141 ~R 148 , R 200 ~R 203 , R E and R F , R 151 ~R 155 , R 161 ~R 165 , R 171 ~R 175 , and R 181 ~R 192 The hydrogen atom represented by; (2)Z 1 ~Z 4 , R 5 ~R 12 , Z 5 ~Z 8 , R 21 ~R 32 , R 41 ~R 44 , R 45 ~R 48 , R 100 , R A and R B , R 21B ~R 24B , R 25B ~R 28B , R 101 , R C and R D , R 51 ~R 55 , R 71 ~R 75 , R 81 ~R 85 , R 101 ~R 105 , R 106 ~R 110, R 111 ~R 115 , R 121 ~R 128 , R 131 ~R 140 , R 141 ~R 148 , R 200 ~R 203 , R E and R F , R 151 ~R 155 , R 161 ~R 165 , R 171 ~R 175 , and, R 181 ~R 192 a hydrogen atom directly bonded to the alkyl group represented by; (3)Z 1 ~Z 4 , R 5 ~R 12 , Z 5 ~Z 8 , R 21 ~R 32 , R 41 ~R 44 , R 45 ~R 48 , R 100 , R A and R B , R 21B ~R 24B , R 25B ~R 28B , R 101 , R C and R D , R 51 ~R 55 , R 71 ~R 75 , R 81 ~R 85 , R 101 ~R 105 , R 106 ~R 110 , R 111 ~R 115 , R 121 ~R 128 , R 131 ~R 140 , R 141 ~R 148 , R 200 ~R 203 , R E and R F, and a hydrogen atom directly bonded to the aryl group represented by R 181 ~R 192 ; a hydrogen atom directly bonded to the aryl group represented by R (4)Z 1 ~Z 4 、R 5 ~R 12 、Z 5 ~Z 8 、R 21 ~R 32 、R 41 ~R 44 、R 45 ~R 48 、R 100 、R A and R B 、R 21B ~R 24B 、R 25B ~R 28B 、R 101 、R C and R D 、R 111 ~R 115 、R 141 ~R 148 、R 200 ~R 203 , and a hydrogen atom directly bonded to the heteroaryl group represented by R E and R F ; a hydrogen atom directly bonded to the heteroaryl group represented by R (5)Z 1 ~Z 4 、R 5 ~R 12 、Z 5 ~Z 8 、R 21 ~R 32 、R 41 ~R 44 、R 45 ~R 48 、R 100 、R A and R B 、R 21B ~R 24B 、R 25B ~R 28B 、R 101 、R C and R D 、R 51 ~R 55 、R 71 ~R 75 、R 81 ~R 85 、R 101 ~R105 , R 106 ~R 110 , R 111 ~R 115 , R 121 ~R 128 , R 131 ~R 140 , R 141 ~R 148 , R 200 ~R 203 , R E and R F , R 151 ~R 155 , R 161 ~R 165 , R 171 ~R 175 , and R 181 ~R 192 A hydrogen atom directly attached to a substituent of the alkyl group represented by ; (6)Z 1 ~Z 4 , R 5 ~R 12 , Z 5 ~Z 8 , R 21 ~R 32 , R 41 ~R 44 , R 45 ~R 48 , R 100 , R A and R B , R 21B ~R 24B , R 25B ~R 28B , R 101 , R C and R D , R 51 ~R 55 , R 71 ~R 75 , R 81 ~R 85 , R 101 ~R 105 , R 106 ~R 110 , R 111 ~R 115 , R 121 ~R 128 , R 131 ~R 140 , R 141 ~R 148 , R 200~R 203 , R E and R F , and R 181 ~R 192 The hydrogen atom directly attached to the substituent of the aryl group represented by ; (7)Z 1 ~Z 4 , R 5 ~R 12 , Z 5 ~Z 8 , R 21 ~R 32 , R 41 ~R 44 , R 45 ~R 48 , R 100 , R A and R B , R 21B ~R 24B , R 25B ~R 28B , R 101 , R C and R D , R 111 ~R 115 , R 141 ~R 148 , R 200 ~R 203 , and R E and R F The hydrogen atom directly attached to the substituent of the heteroaryl group represented by ; (8)L 1 ~L 3 The hydrogen atom directly attached to the arylene group represented by; and (9)L 1 ~L 3 The hydrogen atom directly attached to the substituent of the arylene group represented by .

[0212] As stated above, the term "hydrogen atom" as used herein includes light hydrogen atoms, deuterium atoms, and tritium atoms. The first or second inventive compound may also contain naturally occurring deuterium atoms. Furthermore, deuterium atoms may be intentionally introduced into the first or second inventive compound by using a deuterized compound as part or all of the raw material compound.

[0213] The deuterated ratio of the first or second 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 compounds 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 first or second 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 50% or more. The second inventive compound may be a deuterium compound in which all hydrogen atoms are deuterium atoms (i.e., the deuteration rate of the inventive compound is 100%).

[0214] The first or second 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, even more preferably 50% or more, and less than 100%. Furthermore, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the first inventive compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, and even more preferably 10% or more, and less than 100%. Furthermore, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the second inventive compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, and even more preferably 10% or more, and 100% or less.

[0215] Details of the substituents (any substituents) in the case of "substituted or unsubstituted" included in the definitions of each of the above formulas are as described in "Substituents in the case of 'substituted or unsubstituted'".

[0216] Those skilled in the art can easily produce the first or second inventive compound by referring to the synthesis examples and known synthesis methods described later.

[0217] Specific examples of the first or second inventive compounds are shown below, but the invention is not limited to these example compounds. In the specific examples below, D represents a deuterium atom.

[0218] [ka]

[0219] [ka]

[0220] [ka]

[0221] [ka]

[0222] [ka]

[0223] [ka]

[0224] [ka]

[0225] [ka]

[0226] [ka]

[0227]

change

[0228]

change

[0229]

change

[0230]

change

[0231]

change

[0232]

change

[0233]

change

[0234]

change

[0235]

change

[0236]

change

[0237]

change

[0238]

change

[0239]

change

[0240]

change

[0241]

change

[0242]

change

[0243]

change

[0244]

change

[0245]

change

[0246]

change

[0247]

change

[0248]

change

[0249]

change

[0250]

change

[0251]

change

[0252]

change

[0253]

change

[0254]

change

[0255]

change

[0256]

change

[0257]

change

[0258]

change

[0259]

change

[0260]

change

[0261]

change

[0262]

change

[0263]

change

[0264]

change

[0265]

change

[0266]

change

[0267]

change

[0268]

change

[0269]

change

[0270]

change

[0271]

change

[0272]

change

[0273]

change

[0274]

change

[0275]

change

[0276]

change

[0277]

change

[0278]

change

[0279]

change

[0280]

change

[0281]

change

[0282]

change

[0283]

change

[0284]

change

[0285]

change

[0286]

change

[0287]

change

[0288]

change

[0289]

change

[0290]

change

[0291]

change

[0292]

change

[0293]

change

[0294]

change

[0295]

change

[0296]

change

[0297]

change

[0298]

change

[0299]

change

[0300]

change

[0301]

change

[0302]

change

[0303]

change

[0304]

change

[0305]

change

[0306]

change

[0307]

change

[0308]

change

[0309]

change

[0310]

change

[0311]

change

[0312]

change

[0313]

change

[0314]

change

[0315]

change

[0316]

change

[0317]

change

[0318]

change

[0319]

change

[0320]

change

[0321]

change

[0322]

change

[0323]

change

[0324]

change

[0325]

change

[0326]

change

[0327]

change

[0328]

change

[0329]

change

[0330]

change

[0331]

change

[0332]

change

[0333]

change

[0334]

change

[0335]

change

[0336]

change

[0337]

change

[0338]

change

[0339]

change

[0340]

change

[0341]

change

[0342]

change

[0343]

change

[0344]

change

[0345]

change

[0346]

change

[0347]

change

[0348]

change

[0349]

change

[0350]

change

[0351]

change

[0352]

change

[0353]

change

[0354]

change

[0355]

change

[0356]

change

[0357]

change

[0358]

change

[0359]

change

[0360]

change

[0361]

change

[0362]

change

[0363]

change

[0364]

change

[0365]

change

[0366]

change

[0367]

change

[0368]

change

[0369]

change

[0370]

change

[0371]

change

[0372]

change

[0373]

change

[0374]

change

[0375]

change

[0376]

change

[0377]

change

[0378]

change

[0379]

change

[0380]

change

[0381]

change

[0382]

change

[0383]

change

[0384]

change

[0385]

change

[0386]

change

[0387]

change

[0388]

change

[0389]

change

[0390]

change

[0391]

change

[0392]

change

[0393]

change

[0394]

change

[0395]

change

[0396]

change

[0397]

change

[0398]

change

[0399]

change

[0400]

change

[0401]

change

[0402]

change

[0403]

change

[0404]

change

[0405]

change

[0406]

change

[0407]

change

[0408]

change

[0409]

change

[0410]

change

[0411]

change

[0412]

change

[0413]

change

[0414]

change

[0415]

change

[0416]

change

[0417]

change

[0418]

change

[0419]

change

[0420]

change

[0421]

change

[0422]

change

[0423]

change

[0424]

change

[0425]

change

[0426]

change

[0427]

change

[0428]

change

[0429]

change

[0430]

change

[0431]

change

[0432]

change

[0433]

change

[0434]

change

[0435]

change

[0436]

change

[0437]

change

[0438]

change

[0439]

change

[0440]

change

[0441]

change

[0442]

change

[0443]

change

[0444]

change

[0445]

change

[0446]

change

[0447]

change

[0448]

change

[0449]

change

[0450]

change

[0451]

change

[0452]

change

[0453]

change

[0454]

change

[0455]

change

[0456]

change

[0457]

change

[0458]

change

[0459]

change

[0460] [ka]

[0461] [ka]

[0462] [ka]

[0463] [ka]

[0464] [ka]

[0465] Materials for organic EL devices A material for an organic EL element according to one aspect of the present invention contains the first or second inventive compound. The content of the first or second inventive compound in the material for the organic EL element 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 an organic EL element according to one aspect of the present invention is useful for the manufacture of organic EL elements. In one embodiment of the present invention, it is preferable that the first or second inventive compound is a hole transport layer material.

[0466] In one embodiment of the present invention, when the first or second inventive compound contains at least one deuterium atom, the material for the organic EL element preferably further contains a light hydrogen compound of the first or second inventive compound. The light hydrogen compound is a compound in which all of the hydrogen atoms in the first or second inventive compound are light hydrogen atoms. The molar ratio of the first or second inventive compound to the light hydrogen form of the first or second inventive compound (inventive compound: light hydrogen form) is preferably 10:90 to 90:10, more preferably 20:80 to 80:20, even more preferably 30:70 to 70:30, and particularly preferably 40:60 to 60:40.

[0467] 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%).

[0468] Organic EL element An organic EL element according to one aspect of the present invention includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer consists of one or more layers including an emissive layer, and at least one layer selected from the group consisting of a single layer and a plurality of layers constituting 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.

[0469] 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, of which at least one layer is a light-emitting layer, and emits light when injected holes and electrons recombine.

[0470] 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) (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) (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)

[0471] 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.

[0472] 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.

[0473] 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 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 confines electrons and holes in the light-emitting layer 5, further increasing the exciton generation efficiency in the light-emitting layer 5.

[0474] 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 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.

[0475] Figure 3 is a schematic diagram showing another example of the configuration of the organic EL element of the present invention. The organic EL element 12 has 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. Furthermore, in one embodiment of the present invention, it is preferable that the hole transport layer (B) is an electron blocking layer. Therefore, in one embodiment of the present invention, for example, when describing the configuration of an organic EL element shown in the schematic diagram of Figure 3, it is more preferable that at least one layer selected from the first hole transport layer 6b and the second hole transport layer 6c is the hole transport layer (A), and the third hole transport layer 6d is the hole transport layer (B) and is an electron blocking layer. Furthermore, in one embodiment of the present invention, it is preferable that the hole transport layer (A) and the hole transport layer (B) are in direct contact. Therefore, in one embodiment of the present invention, for example, when describing the configuration of the organic EL element shown in the schematic diagram of Figure 3, it is more preferable that at least the second hole transport layer 6c is the hole transport layer (A), the third hole transport layer 6d is the hole transport layer (B), and is an electron blocking layer.

[0476] 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.

[0477] 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.

[0478] 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).

[0479] 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.

[0480] 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 of these layers constituting the hole transport layer contains the inventive compound, and it is more preferable that the hole transport layer contains the inventive compound.

[0481] Since 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, materials commonly used as electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, or 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, i.e., 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 the anode using alkali metals, alkaline earth metals, and alloys containing these, vacuum deposition or sputtering methods can be used. Furthermore, when using silver paste, coating methods or inkjet methods can be used.

[0482] 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.

[0483] 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.

[0484] 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.

[0485] 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.

[0486] Furthermore, it is also preferable to use an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K). [ka]

[0487] (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.

[0488] 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.

[0489] 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 in 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 another embodiment of the present invention, an electron blocking layer, etc., described later, may be interposed between the hole transport layer in 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. In one embodiment of the organic electroluminescent element according to the present invention, at least one of the first hole transport layer and the second hole transport layer contains the inventive 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 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. 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. In one embodiment of the present invention, the inventive compound contained in one or both of the first hole transport layer and the second hole transport layer, or the inventive compound contained in at least one or more of the first to third hole transport layers, is preferably a light hydrogen compound from the viewpoint of manufacturing cost. The above-mentioned light hydrogen compound refers to the inventive compound in which all of the hydrogen atoms are light hydrogen atoms. Accordingly, the present invention includes an organic EL element in which one or both of the first hole transport layer and the second hole transport layer, or at least one or more of the first to third hole transport layers, consist substantially of only light hydrogen, in the inventive compound. "Substantially consisting solely of light hydrogen" means that the content ratio of light hydrogen to the total amount of the inventive compound is 90 mol% or more, preferably 95 mol% or more, and more preferably 99 mol% or more (including 100%).

[0490] 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.

[0491] 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.

[0492] In one embodiment of the organic EL element according to the present invention, the first hole transport layer comprises a compound represented by the following formula (21) or formula (22). [ka] [In equations (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 above monoring and does not form the above condensed ring E2This 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. R 901 ~R 907 Each of them independently consists of a 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 having 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. R 907 If there are multiple R 907 They are either identical or different from one another.

[0493] 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).

[0494] In formulas (21) and (22), A1, B1, C1, A2, B2, C2, and D2 are preferably each independently selected from a substituted or unsubstituted phenylene 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 dibensofuranil group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group. Furthermore, more preferably, in formula (21), at least one of A1, B1, and C1, and in formula (22), at least one 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 dibensofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group or a substituted or unsubstituted carbazolyl group.

[0495] 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.

[0496] 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.

[0497] Specific examples of compounds represented by formulas (21) and (22) include the following compounds. [ka]

[0498] 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 a single layer. Furthermore, in another embodiment of the organic EL element according to the present invention, the light-emitting layer includes a first light-emitting layer and a second light-emitting layer.

[0499] 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, and triarylamine derivatives. Specifically, these 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).

[0500] 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).

[0501] 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).

[0502] In one embodiment of the present invention, it is preferable that the light-emitting layer includes a fluorescent light-emitting material (fluorescent dopant material).

[0503] 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).

[0504] 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)).

[0505] 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).

[0506] 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.

[0507] 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.

[0508] 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.

[0509] 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-9 Aromatic amine compounds such as H-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.

[0510] In particular, for blue fluorescent elements, it is preferable to use the following anthracene compounds as the host material.

[0511] [ka]

[0512] [ka]

[0513] [ka]

[0514] In one embodiment of the organic EL element according to the present invention, when the light-emitting layer includes 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.

[0515] 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.

[0516] 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).

[0517] 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.

[0518] 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.

[0519] 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 in 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 in 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 in 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.

[0520] For example, the electron transport layer includes: (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.

[0521] 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), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviated as ZnBTZ).

[0522] 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).

[0523] 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).

[0524] 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.

[0525] 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, 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. Furthermore, multiple compounds can be used in combination. 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.

[0526] 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.

[0527] 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.

[0528] 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.

[0529] blocking layer Blocking layers such as an electron blocking layer, a hole blocking layer, and 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 has a function of preventing excitons generated in the light-emitting layer from diffusing into the surrounding layers and confining the excitons within the light-emitting layer.

[0530] Each layer of the organic EL device can be formed by a conventionally known vapor deposition method, coating method, etc. For example, it can be formed by a vapor deposition method such as a vacuum vapor deposition method or a molecular beam epitaxy method (MBE method), or a known method such as a dipping method, a spin coating method, a casting method, a bar coating method, a roll coating method, etc. using a solution of a compound for forming the layer.

[0531] The film thickness of each layer is not particularly limited, but generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and conversely, if it is too thick, a high driving voltage is required and the efficiency deteriorates. Therefore, it is usually 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm.

[0532] In one aspect of the organic EL device 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 30 nm or more and 150 nm or less. In this case, preferably, it is 40 nm or more and 130 nm or less. Also, in one aspect of the organic EL device of the present invention, the thickness of the second hole transport layer is 20 nm or more. Preferably it is 25 nm or more, more preferably 35 nm or more, and also preferably 100 nm or less. Also, in one aspect of the organic EL device of the present invention, the hole transport layer adjacent to the light-emitting layer is 20 nm or more. Preferably it is 25 nm or more, more preferably 30 nm or more, and also preferably 100 nm or less. Also, in one aspect of the organic EL device 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. Preferably, it satisfies the relationship of 0.5 < D2 / D1 < 3.5, and more preferably satisfies the relationship of 0.75 < D2 / D1 < 3.0.

[0533] 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 ninth 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.

[0534] electronic equipment The above-mentioned organic EL elements can be used in display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and electronic devices such as lighting and vehicle light fixtures. [Examples]

[0535] The present invention will be described in more detail below using examples, but the present invention is not limited to the following.

[0536] <Compounds used in the manufacture of the organic EL elements in the examples> [ka] [ka]

[0537] <Comparative compound used in the manufacture of the organic EL element in the comparative example> [ka]

[0538] <Other compounds used in the manufacture of organic EL elements in the examples and comparative examples> [ka] [ka] [ka] [ka] [ka]

[0539] <Fabrication of Organic EL Devices> (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 cleaned ITO transparent electrode was mounted in the substrate holder of the vacuum deposition apparatus. First, compound Inv-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 Inv-1 to compound HA (Inv-1:HA) was 90:10. Next, compound Inv-1 was deposited onto the hole injection layer to form a first hole transport layer with a thickness of 70 nm. Next, compound HT-2 was deposited onto this first hole transport layer to form a second hole transport layer with a thickness of 7.5 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 first light-emitting layer with a thickness of 8.5 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 98.5:1.5. Next, compound BH-2 (host material) and compound BD-1 (dopant material) were co-deposited onto this first light-emitting layer to form a second light-emitting layer with a thickness of 8.5 nm. The mass ratio of compound BH-2 to compound BD-1 (BH-2:BD-1) was 98.5:1.5. Next, compound ET-1 was deposited on this second 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 30 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50. Next, Yb was deposited on this second electron transport layer to form an electron injection layer with a thickness of 1 nm. Next, metallic aluminum was deposited onto this electron injection layer to form a metallic cathode with a thickness of 80 nm. The layer configuration of the organic EL element of Example 1 obtained in this way is shown below. ITO(130) / Inv-1:HA=90:10(10) / Inv-1(70) / HT-2(7.5) / BH-1:BD-1=98.5:1.5( 8.5) / BH-2:BD-1=98.5:1.5(8.5) / ET-1(5) / ET-2:Liq=50:50(30) / Yb(1) / Al(80) In the above layer configuration, the numbers in parentheses represent the film thickness (nm), and the ratios represent the mass ratios.

[0540] (Example 2) An organic EL device was fabricated in the same manner as in Example 1, except that compound Inv-1 in the hole injection layer and the first hole transport layer was replaced with compound Inv-2.

[0541] (Comparative Example 1) An organic EL device was fabricated in the same manner as in Example 1, except that compound Inv-1 in the hole injection layer and the first hole transport layer was replaced with compound Ref-1.

[0542] (Evaluation of organic EL elements) The organic EL elements fabricated in Examples 1 and 2 and Comparative Example 1 had a current density of 10 mA / cm². 2 A voltage was applied to the organic EL element to evaluate its external quantum efficiency (EQE). The results are shown in Table 1.

[0543] [Table 1]

[0544] As is clear from the results in Table 1, the compounds that satisfy the provisions of the present invention (compound Inv-1 in Example 1 and compound Inv-2 in Example 2) show significantly improved EQE values ​​compared to the compound that does not satisfy the provisions of the present invention (compound Ref-1 in Comparative Example 1).

[0545] (Example 3) 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 cleaned ITO transparent electrode 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 create a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-1 to compound HA (HT-1:HA) was 95:5. Next, compound HT-1 was deposited onto the hole injection layer to form a first hole transport layer with a thickness of 30 nm. Next, compound Inv-1 was deposited onto this first hole transport layer to form a second hole transport layer with a thickness of 40 nm. Next, compound HT-3 was deposited onto this second hole transport layer to form a third hole transport layer with a thickness of 15 nm. Next, compound BH (host material) and compound BD (dopant material) were co-deposited onto this third hole transport layer to form a light-emitting layer with a thickness of 20 nm. The mass ratio of compound BH to compound BD (BH:BD) was 98:2. Next, compound ET-3 was deposited onto this light-emitting layer to form a first electron transport layer with a thickness of 10 nm. Next, compound ET-4 and Li 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-4 to Li (ET-4:Li) was 96:4. Next, metallic aluminum was deposited onto this second electron transport layer to form a metallic cathode with a thickness of 80 nm. The layer configuration of the organic EL element of Example 3 obtained in this way is shown below. ITO(130) / HT-1:HA=95:5(10) / HT-1(30) / Inv-1(40) / HT-3(15) / BH:BD=98:2(20) / ET-3(10) / ET-4:Li=96:4(20) / Al(80) In the above layer configuration, the numbers in parentheses represent the film thickness (nm), and the ratios represent the mass ratios.

[0546] (Example 4) An organic EL device was fabricated in the same manner as in Example 3, except that compound Inv-1 in the second hole transport layer material was replaced with compound Inv-2.

[0547] (Comparative Example 2) An organic EL device was fabricated in the same manner as in Example 3, except that compound Inv-1 in the second hole transport layer material was replaced with compound Ref-2.

[0548] (Evaluation of organic EL elements) The organic EL elements fabricated in Examples 3 and 4, and Comparative Example 2, had a current density of 10 mA / cm². 2 A voltage was applied to the organic EL element to evaluate its external quantum efficiency (EQE). The results are shown in Table 2.

[0549] [Table 2]

[0550] As is clear from the results in Table 2, compounds that satisfy the provisions of the present invention (compound Inv-1 in Example 3 and compound Inv-2 in Example 4) show significantly improved EQE values ​​compared to compounds that do not satisfy the provisions of the present invention (compound Ref-2 in Comparative Example 2).

[0551] (Example 5) 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 cleaned ITO transparent electrode was mounted in the substrate holder of the vacuum deposition apparatus. First, compound HT-4 and compound HA were co-deposited onto the surface on which the transparent electrode was formed, covering the transparent electrode and creating a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-4 to compound HA (HT-4:HA) was 95:5. Next, compound HT-4 was deposited onto the hole injection layer to form a first hole transport layer with a thickness of 30 nm. Next, compound Inv-3 was deposited onto this first hole transport layer to form a second hole transport layer with a thickness of 40 nm. Next, compound HT-3 was deposited onto this second hole transport layer to form a third hole transport layer with a thickness of 15 nm. Next, compound BH (host material) and compound BD (dopant material) were co-deposited onto this third hole transport layer to form a light-emitting layer with a thickness of 20 nm. The mass ratio of compound BH to compound BD (BH:BD) was 98:2. Next, compound ET-3 was deposited onto this light-emitting layer to form a first electron transport layer with a thickness of 10 nm. Next, compound ET-4 and Li 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-4 to Li (ET-4:Li) was 96:4. Next, metallic aluminum was deposited onto this second electron transport layer to form a metallic cathode with a thickness of 80 nm. The layer configuration of the organic EL element of Example 5 obtained in this way is shown below. ITO(130) / HT-4:HA=95:5(10) / HT-4(30) / Inv-3(40) / HT-3(15) / BH:BD=98:2(20) / ET-3(10) / ET-4:Li=96:4(20) / Al(80) In the above layer configuration, the numbers in parentheses represent the film thickness (nm), and the ratios represent the mass ratios.

[0552] (Example 6) An organic EL device was fabricated in the same manner as in Example 5, except that compound Inv-3 in the second hole transport layer material was replaced with compound Inv-4.

[0553] (Example 7) An organic EL device was fabricated in the same manner as in Example 5, except that compound Inv-3 in the second hole transport layer material was replaced with compound Inv-5.

[0554] (Comparative Example 3) An organic EL device was fabricated in the same manner as in Example 5, except that compound Inv-3 in the second hole transport layer material was replaced with compound Ref-2.

[0555] (Evaluation of organic EL elements) The organic EL elements fabricated in Examples 5, 6, and 7, and Comparative Example 3, had a current density of 10 mA / cm². 2A voltage was applied to the organic EL element to evaluate its external quantum efficiency (EQE). The results are shown in Table 3.

[0556] [Table 3]

[0557] As is clear from the results in Table 3, the compounds that satisfy the provisions of the present invention (Compound Inv-3 in Example 5, Compound Inv-4 in Example 6, and Compound Inv-5 in Example 7) show significantly improved EQE values ​​compared to the compounds that do not satisfy the provisions of the present invention (Compound Ref-2 in Comparative Example 3).

[0558] (Example 8) 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 cleaned ITO transparent electrode was mounted in the substrate holder of the vacuum deposition apparatus. First, compound HT-4 and compound HA were co-deposited onto the surface on which the transparent electrode was formed, covering the transparent electrode and creating a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-4 to compound HA (HT-4:HA) was 95:5. Next, compound HT-4 was deposited onto the hole injection layer to form a first hole transport layer with a thickness of 30 nm. Next, compound Inv-2 was deposited onto this first hole transport layer to form a second hole transport layer with a thickness of 40 nm. Next, compound HT-3 was deposited onto this second hole transport layer to form a third hole transport layer with a thickness of 15 nm. Next, compound BH (host material) and compound BD (dopant material) were co-deposited onto this third hole transport layer to form a light-emitting layer with a thickness of 20 nm. The mass ratio of compound BH to compound BD (BH:BD) was 98:2. Next, compound ET-3 was deposited onto this light-emitting layer to form a first electron transport layer with a thickness of 10 nm. Next, compound ET-5 and Li 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-5 to Li (ET-5:Li) was 96:4. Next, metallic aluminum was deposited onto this second electron transport layer to form a metallic cathode with a thickness of 80 nm. The layer configuration of the organic EL element of Example 8 obtained in this way is shown below. ITO(130) / HT-4:HA=95:5(10) / HT-4(30) / Inv-2(40) / HT-3(15) / BH:BD=98:2(20) / ET-3(10) / ET-5:Li=96:4(20) / Al(80) In the above layer configuration, the numbers in parentheses represent the film thickness (nm), and the ratios represent the mass ratios.

[0559] (Example 9) An organic EL device was fabricated in the same manner as in Example 8, except that compound Inv-2 in the second hole transport layer material was replaced with compound Inv-6.

[0560] (Example 10) An organic EL device was fabricated in the same manner as in Example 8, except that compound Inv-2 in the second hole transport layer material was replaced with compound Inv-7.

[0561] (Comparative Example 4) An organic EL device was fabricated in the same manner as in Example 8, except that compound Inv-2 in the second hole transport layer material was replaced with compound Ref-2.

[0562] (Evaluation of organic EL elements) The organic EL elements fabricated in Examples 8, 9, 10, and Comparative Example 4 had a current density of 10 mA / cm². 2 A voltage was applied to the organic EL element to evaluate its external quantum efficiency (EQE). The results are shown in Table 4.

[0563] [Table 4]

[0564] As is clear from the results in Table 4, the compounds that satisfy the provisions of the present invention (Compound Inv-2 in Example 8, Compound Inv-6 in Example 9, and Compound Inv-7 in Example 10) show significantly improved EQE values ​​compared to the compounds that do not satisfy the provisions of the present invention (Compound Ref-2 in Comparative Example 4).

[0565] Compounds synthesized in the synthesis example [ka] [ka]

[0566] <Synthesis of Compounds> (Intermediate synthesis example 1: Synthesis of intermediate 1) [ka]

[0567] Under an argon atmosphere, 11.2 mL of n-butyllithium (2.6 mol / L, hexane solution) was slowly added dropwise to 85 mL of tetrahydrofuran solution of 2-bromo-4,4'-di-tert-butyl-1,1'-biphenyl (9.65 g, 27.9 mmol) at -78°C, and the mixture was stirred. After 1 hour, 4-bromo-2,3-dihydro-1H-inden-1-one (5.36 g, 25.4 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature. After 3 hours, saturated aqueous solution of ammonium chloride and ethyl acetate were added, and the mixture was stirred. The aqueous layer was removed using a separatory funnel, and the resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain a pale yellow solid. The obtained solid was dissolved in xylene (48 mL), p-toluenesulfonic acid monohydrate (3.63 g, 19.1 mmol) was added, and the mixture was heated to 140°C and stirred for 3 hours. After cooling, water was added, and the aqueous layer was removed. The resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain intermediate 1, a white solid (4.32 g). The yield for the two steps was 37%.

[0568] (Intermediate synthesis example 2: Synthesis of intermediate 2) [ka]

[0569] Under an argon atmosphere, 20.0 mL of n-butyllithium (2.6 mol / L, hexane solution) was slowly added dropwise to a tetrahydrofuran solution (95 mL) of 2-bromo-4,4'-di-tert-butyl-1,1'-biphenyl (17.2 g, 49.7 mmol) at -78°C, and the mixture was stirred. After 1 hour, 6-bromo-2,3-dihydro-1H-inden-1-one (10.0 g, 47.4 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature. After 3 hours, saturated aqueous solution of ammonium chloride and ethyl acetate were added, and the mixture was stirred. The aqueous layer was removed using a separatory funnel, and the resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain a pale yellow solid. The obtained solid was dissolved in xylene (131 mL), p-toluenesulfonic acid monohydrate (9.93 g, 52.2 mmol) was added, and the mixture was heated to 140°C and stirred for 3 hours. After cooling, water was added, and the aqueous layer was removed. The resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain intermediate 2, a white solid (10.79 g). The yield for the two steps was 49%.

[0570] (Synthesis Example 1: Synthesis of Compound 1) [ka]

[0571] First, a mixture was prepared containing 4.590 g (10.0 mmol) of intermediate 1 (4'-bromo-2,7-di-tert-butyl-2',3'-dihydrospiro[fluorene-9,1'-indene]), 3.610 g (10.0 mmol) of intermediate 3 (N-([1,1'-biphenyl]-2-yl)-9,9-dimethyl-9H-fluorene-2-amine), 0.183 g (0.2 mmol) of tris(dibenzylideneacetone)dipalladium(0) as a catalyst, 0.232 g (0.8 mmol) of tri-tert-butylphosphonium tetrafluoroborate as a ligand, 1.350 g (14.0 mmol) of sodium-t-butoxide as a base, and 50 mL of xylene as a solvent. The above mixture was stirred at 110°C for 4 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain 4.07 g of a white solid. The yield was 55% by mass. Mass spectrometry revealed that the obtained compound was Inv-1, with a molecular weight of 740.05 and a m / e ratio of 740.

[0572] (Synthesis Example 2: Synthesis of Compound 2) The compound in the "Synthesis Example 2" column of Table 5 (compound Inv-2) was synthesized in the same manner as in Synthesis Example 1, except that intermediates A and B from the "Synthesis Example 2" column of Table 5 were used instead of intermediates 1 and 3 in Synthesis Example 1. The yield was 72% by mass, as shown in Table 5.

[0573] (Synthesis Example 3: Synthesis of Compound 3) The compound in the "Synthesis Example 3" column of Table 5 (compound Inv-3) was synthesized in the same manner as in Synthesis Example 1, except that intermediates A and B from the "Synthesis Example 3" column of Table 5 were used instead of intermediates 1 and 3 in Synthesis Example 1. The yield was 45% by mass, as shown in Table 5.

[0574] (Synthesis Example 4: Synthesis of Compound 4) The compound in the column for Synthesis Example 4 in Table 5 (compound Inv-4) was synthesized in the same manner as in Synthesis Example 1, except that intermediates A and B in the column for Synthesis Example 4 in Table 5 were used instead of intermediates 1 and 3 in Synthesis Example 1. The yield was 46% by mass, as shown in Table 5.

[0575] (Synthesis Example 5: Synthesis of Compound 5) The compound in the "Synthesis Example 5" column of Table 5 (compound Inv-5) was synthesized in the same manner as in Synthesis Example 1, except that intermediates A and B from the "Synthesis Example 5" column of Table 5 were used instead of intermediates 1 and 3 in Synthesis Example 1. The yield was 61% by mass, as shown in Table 5.

[0576] (Synthesis Example 6: Synthesis of Compound 6) The compound in the "Synthesis Example 6" column of Table 5 (compound Inv-6) was synthesized in the same manner as in Synthesis Example 1, except that intermediates A and B from the "Synthesis Example 6" column of Table 5 were used instead of intermediates 1 and 3 in Synthesis Example 1. The yield was 57% by mass, as shown in Table 5.

[0577] (Synthesis Example 7: Synthesis of Compound 7) The compound in the column for Synthesis Example 7 in Table 5 (compound Inv-7) was synthesized in the same manner as in Synthesis Example 1, except that intermediates A and B in the column for Synthesis Example 7 in Table 5 were used instead of intermediates 1 and 3 in Synthesis Example 1. The yield was 45% by mass, as shown in Table 5.

[0578] [Table 5] [Explanation of symbols]

[0579] 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 (1A). 【Chemistry 1】 [In formula (1A), N ＊ It is the central nitrogen atom. Z １ ~Z ４ One of the options selected is a single bond that connects to *a. R １ ~R ４ These are, independently, light hydrogen atoms. The non-single bonds Z1 to Z4 are, independently, a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted ring-forming C6 to C30 aryl group, or a substituted or unsubstituted ring-forming C5 to C30 heteroaryl group. R6 and R11 are each independently tert-butyl groups, and R5, R7-R10 and R12 are each independently hydrogen atoms. The Z that is not the single bond １ ~Z ４ , and R ５ ~R １２ do not combine with each other to form a ring. L １ These are substituted or unsubstituted ring-forming arylene groups with 6 to 12 carbon atoms. n1 is either 0 or 1. When n1 is 0, Z １ ~Z ４ One of the selected elements is the central nitrogen atom N ＊ Combine. L ２ These are substituted or unsubstituted ring-forming arylene groups with 6 to 12 carbon atoms. n2 is either 0 or 1. When n2 is 0, Ar １ The central nitrogen atom N ＊ Combine. L ３ These are substituted or unsubstituted ring-forming arylene groups with 6 to 12 carbon atoms. n3 is either 0 or 1. When n3 is 0, Ar ２ The central nitrogen atom N ＊ Combine. Ar １ and Ar ２ These are, independently, substituted or unsubstituted aryl groups having 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 30 ring-forming atoms.

2. (i) Ar １ The group is represented by the following formula (2-1), and Ar ２ Is it not the group represented by the following formula (3-1)? (ii)Ar ２ The group is represented by the following formula (3-1), and Ar １ Is it not a group represented by the following formula (2-1), or (iii)Ar １ The group is represented by the following formula (2-1), and Ar ２ The compound according to claim 1, wherein is a group represented by the following formula (3-1). 【Chemistry 2】 【Transformation 3】 In formula (2-1), ** is L ２ This indicates the connection position to the destination. X １ is an oxygen atom, a sulfur atom, =NR １００ , or =CR Ａ R Ｂ That is the case. R ４１ ~R ４４ , R １００ , R Ａ , and R Ｂ One of the selected options is either a single bond that joins *d, or R Ａ and R Ｂ One of the selected groups is a divalent group that binds to *d. R that is not a single bond ４１ ~R ４４ , and R ４５ ~R ４８ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heteroaryl group. R that is not a single bond ４１ ~R ４４ Among them, a pair of adjacent bases, and R ４５ ~R ４８ Among these, adjacent pairs of groups may or may not bond to each other to form a ring. The R that is not a single bond １００ This is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms. R is not a single bond as described above, nor is it a divalent group that bonds to *d. Ａ and R Ｂ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heteroaryl group, which may or may not bond to each other to form a ring. In formula (3-1), *** is L ３ This indicates the connection position to the destination. X ２ is an oxygen atom, a sulfur atom, =NR １０１ , or =CR Ｃ R Ｄ That is the case. R ２１Ｂ ~R ２４Ｂ , R １０１ , R Ｃ , and R Ｄ One of the options selected is either a single bond that connects to *b2, or R Ｃ and R Ｄ One of the selected groups is a divalent group that binds to *b2. R that is not a single bond ２１Ｂ ~R ２４Ｂ , and R ２５Ｂ ~R ２８Ｂ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heteroaryl group. R ２１Ｂ ~R ２４Ｂ If one of those selected is a single bond that connects to *b2, then R which is not the single bond ２１Ｂ ~R ２４Ｂ They do not bond to each other to form a ring, and R ２５Ｂ ~R ２８Ｂ These elements may or may not combine to form a ring. The R that is not a single bond １０１ This is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms. R is not a single bond as described above, nor is it a divalent group that is bonded to *b2. Ｃ and R Ｄ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heteroaryl group, which may or may not bond to each other to form a ring.

3. The compound according to claim 1, represented by the following formula (1A-1). 【Chemistry 4】 [In formula (1A-1), R １ ~R １２ Z ２ ~Z ４ , N ＊ Ar １ ~Ar ２ , L １ ~L ３ , and n1 to n3 are as defined in formula (1A) above.

4. The compound according to claim 1, represented by the following formula (1A-2). 【Transformation 5】 〔In formula (1A-2), R １ ~R １２ , Z １ , Z ２ , Z ４ , N ＊ , Ar １ ~Ar ２ , L １ ~L ３ , and n1 to n3 are as defined in the said formula (1A).〕

5. When represented by the formula (1A) and n1 is 1, L １ is a phenylene group, and when n2 is 1, L ２ is a phenylene group, and when n3 is 1, L ３ is a phenylene group, the compound according to claim 1.

6. Represented by the above formula (1A), Ar ２ The group is represented by the above formula (3-1), and X ２ ga = CR Ｃ R Ｄ The compound according to claim 2.

7. Represented by the above formula (1A), Ar １ The compound according to claim 1, wherein is a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.

8. The compound according to claim 1, represented by any of the following formulas (1A-3) to (1A-9). 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 [In formulas (1A-3) to (1A-9), R １ ~R １２ Z １ ~Z ４ , N ＊ , *a, Ar １ ~Ar ２ , L １ ~L ３ , and n1 to n3 are as defined in formula (1A) above.

9. The compound according to claim 1, represented by any of the following formulas (1A-10) to (1A-16). 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 [In formulas (1A-10), (1A-13), (1A-14), and (1A-16), R ５１ ~R ５５ Each of these is independently a hydrogen atom, an unsubstituted C1-C6 alkyl group, or an unsubstituted ring-forming C6-C12 aryl group. However, R ５１ ~R ５５ One of the options selected is a single bond that connects to *d. R that is not a single bond ５１ ~R ５５ Of these, one adjacent pair does not connect with each other and does not form a ring. In equations (1A-11), (1A-13), (1A-15), and (1A-16), R ７１ ~R ７５ Each of these is independently a hydrogen atom, an unsubstituted C1-C6 alkyl group, or an unsubstituted ring-forming C6-C12 aryl group. However, R ７１ ~R ７５ One of the options is a single bond that connects to *f. R that is not a single bond ７１ ~R ７５ Of these, one adjacent pair does not connect with each other and does not form a ring. In equation (1A-12) and equations (1A-14) to (1A-16), R ８１ ~R ８５ Each of these is independently a hydrogen atom, an unsubstituted C1-C6 alkyl group, or an unsubstituted ring-forming C6-C12 aryl group. However, R ８１ ~R ８５ One of the options is a single bond that connects to *g. R that is not a single bond ８１ ~R ８５ Of these, one adjacent pair does not connect with each other and does not form a ring. In formulas (1A-10) to (1A-16), R １ ~R １２ Z １ ~Z ４ , N ＊ , *a, Ar １ ~Ar ２ , L １ ~L ３ , and n1 to n3 are as defined in formula (1A) above.

10. Ar １ and Ar ２ The compound according to claim 7, wherein at least one of the following is represented by any of the formulas (2A) to (2F). 【Chemistry 20】 (In formula (2A), *21 is L ２ or L ３ This is the binding position to [the target]. ・R １０１ ~R １０５ One of the selected bonds is a single bond that connects to *22, R １０６ ~R １１０ One of the options selected is a single bond that connects to *23. - R which is not a single bond １０１ ~R １０５ and R that is not a single bond １０６ ~R １１０ Each of these is independently a hydrogen atom, an unsubstituted C1-C10 alkyl group, or an unsubstituted ring-forming C6-C12 aryl group. - R which is not a single bond １０１ ~R １０５ Two adjacent elements selected from this set do not join with each other and do not form a ring. - R which is not a single bond １０６ ~R １１０ Two adjacent elements selected from this set do not join with each other and do not form a ring. ・R １１１ ~R １１５ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heteroaryl group. ・R １１１ ~R １１５ Two adjacent elements selected from this set do not join with each other and do not form a ring. - m11 is 0, 1, or 2, and n11 is 0 or 1, except when m11 is 2 and n11 is 0. - If m11 = 0 and n11 = 0, then *23 represents *21. - When m11 = 0 and n11 = 1, *22 represents *21. (If m11 = 1 and n11 = 0, then *23 represents *22.) 【Chemistry 21】 (In formula (2B), *24 is L ２ or L ３ This is the binding position to [the target]. ・R １２１ ~R １２８ One of the options selected is a single bond that connects to *25. - R which is not a single bond １２１ ~R １２８ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted ring-forming C6-C12 aryl group. - R which is not a single bond １２１ ~R １２８ Two adjacent elements selected from this set do not join to each other and do not form a ring. 【Chemistry 22】 (In formula (2C), *26 is L ２ or L ３ This is the binding position to [the target]. ・R １３１ ~R １４０ One of the options selected is a single bond that connects to *27. - R which is not a single bond １３１ ~R １４０ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted ring-forming C6-C12 aryl group. - R which is not a single bond １３１ ~R １４０ Two adjacent elements selected from this set do not join to each other and do not form a ring. 【Chemistry 23】 (In formula (2D), *28 is L ２ or L ３ This is the binding position to [the target]. n12 is either 0 or 1. - When n12 is 0, R １４１ ~R １４８ One of the options selected is a single bond that connects to *29. When n12 is 1, R １４１ and R １４２ , R １４２ and R １４３ , or R １４３ and R １４４ One of the R components is a single bond that connects to *h, and the other is a single bond that connects to *i, and is not a single bond that connects to *h and *i. １４１ ~R １４４ , R １４５ ~R １４８ , and R ２００ ~R ２０３ One of the options selected is a single bond that connects to *29. - R which is not a single bond １４１ ~R １４８ and R that is not a single bond ２００ ~R ２０３ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heteroaryl group. - R which is not a single bond １４１ ~R １４８ and R that is not a single bond ２００ ~R ２０３ Two adjacent elements selected from this set do not join with each other and do not form a ring. ・R Ｅ and R Ｆ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heteroaryl group, which may or may not bond to each other to form a ring. 【Chemistry 24】 (In formula (2E), *30 is L ２ or L ３ This is the binding position to [the target]. ・R １５１ ~R １５５ One of the selected bonds is a single bond that connects to *31, R １５１ ~R １５５ The other one selected is a single bond that connects to *32. - R which is not a single bond １５１ ~R １５５ Each of these is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group. - R which is not a single bond １５１ ~R １５５ Two adjacent elements selected from this set do not join with each other and do not form a ring. ・R １６１ ~R １６５ and R １７１ ~R １７５ Each of these is independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms. R is not a hydrogen atom. １６１ ~R １６５ At least one adjacent pair selected from these may bond to each other to form one or more unsubstituted benzene rings, or they may not bond to each other to form a ring. R is not a hydrogen atom. １７１ ~R １７５ At least one adjacent pair selected from these may bond to each other to form one or more unsubstituted benzene rings, or they may not bond to each other and therefore not form rings. 【Chemistry 25】 (In formula (2F), *32 is L ２ or L ３ This is the binding position to [the target]. ・R １８１ ~R １９２ One of the options selected is a single bond that connects to *33. - Not the single bond mentioned above １８１ ~R １９２ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted ring-forming C6-C12 aryl group. - R which is not a single bond １８１ ~R １９２ Two adjacent elements selected from this set do not join to each other and do not form a ring.

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

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

13. The compound according to claim 1, wherein the compound represented by formula (1A) contains at least one deuterium atom.

14. The compound according to claim 1, which is any of the following compounds 1 to 7. 【Chemistry 26】

15. The compound according to claim 1, which is either compound 1 or 2 below. 【Chemistry 27】

16. A material for an organic electroluminescent device comprising the compound described in any one of claims 1 to 15.

17. The material for an organic electroluminescent device according to claim 16, wherein the compound according to any one of claims 1 to 15 is a hole transport layer material.

18. An organic electroluminescent element having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer consists of one or more layers including a light-emitting layer, and at least one layer selected from the group consisting of one and more layers constituting the organic layer contains the compound described in any one of claims 1 to 15.

19. The organic electroluminescent element according to claim 18, wherein the organic layer includes a hole transport band between the anode and the light-emitting layer, and the hole transport band includes a compound according to any one of claims 1 to 15.

20. The hole transport band includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side. The organic electroluminescent element according to claim 19, wherein at least one of the first hole transport layer and the second hole transport layer contains a compound according to any one of claims 1 to 15.

21. The organic electroluminescent element according to claim 20, wherein the second hole transport layer comprises a compound according to any one of claims 1 to 15.

22. The organic electroluminescent element according to claim 20, wherein the light-emitting layer and the second hole transport layer are in direct contact.

23. The organic electroluminescent element according to claim 20, wherein the sum of the thickness of the first hole transport layer and the thickness of the second hole transport layer is 30 nm or more and 150 nm or less.

24. The organic electroluminescent element according to claim 18, wherein the light-emitting layer includes a layer containing a light-emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less.

25. The organic electroluminescent element according to claim 18, wherein the light-emitting layer is a single layer.

26. An electronic device comprising the organic electroluminescent element described in claim 18.

Images