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

Abstract

The present invention provides compounds that further improve the performance of organic EL elements, materials for organic electroluminescent elements that further improve the performance of organic EL elements, organic electroluminescent elements with improved element performance, and electronic devices containing such organic electroluminescent elements. [Solution] Compound represented by the following formula (1): [Case 1] JPEG2026144985000137.jpg2570 (Each symbol in the formula is as defined in the specification.) A material for an organic electroluminescent element comprising the compound, an organic electroluminescent element comprising the compound, and an electronic device comprising 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, the development of materials that efficiently transport electrons or holes to the light-emitting region and facilitate the recombination of electrons and holes is important for obtaining high-performance organic EL devices.

[0003] Patent documents 1 and 2 disclose compounds used as materials for organic electroluminescent devices (hereinafter sometimes referred to as "materials for organic EL devices"). [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] International Publication No. 2014 / 088047 [Patent Document 2] Japanese Patent Publication No. 2016-207885 [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. An object of the present invention is to provide a compound that further improves the performance of organic EL elements, a material for organic electroluminescence elements that further improves the performance of organic EL elements, an organic EL element with further improved element performance, and an electronic device including such an organic EL element. [Means for Solving the Problems]

[0007] The present inventors have conducted intensive studies on the performance of organic EL elements containing the compounds described in Patent Documents 1 to 2, and as a result, have found that the performance of an organic EL element containing a compound represented by the following formula (1) is further improved.

[0008] In one aspect, the present invention provides a compound represented by the following formula (1). [Chemical Formula] In formula (1), N * is a central nitrogen atom. R 1 and R 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, or -Si(R 901 ')(R 902 ')(R 903 '). R 901 ' to R 903 ' are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms. When two or more R 901 ' to R 903 ' are present, the two or more R 901 ' to R 903 ' may be the same or different. R 3 to R 5Each of these is independently a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heteroaryl group. 3 ~R 5 However, if each is independently a substituted or unsubstituted ring-forming aryl group with 6 to 30 carbon atoms, then R 3 ~R 5 In the case of substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms represented by R, the substituents "substituted or unsubstituted" do not include amino groups. 4 is a substituted or unsubstituted ring-forming aryl group with 6 to 30 carbon atoms, and R 3 and R 5 If R is a substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, 3 and R 5 At least one of these is a substituted or unsubstituted alkyl group having 2 to 30 carbon atoms. R 3 ~R 5 Two adjacent elements selected from the set may join together to form a ring, or they may not join together to form a ring. L 1 and L 2 Each of these is independently an arylene group with 6 to 18 ring-forming carbon atoms, either single-bonded, substituted, or unsubstituted, or a heteroarylene group with 5 to 18 ring-forming atoms, either substituted or unsubstituted. R 1 and R 2 However, if each is independently a substituted or unsubstituted aryl group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group with 5 to 30 ring-forming atoms, then R 1 and R 2 The "number of ring-forming carbon atoms" in substituted or unsubstituted aryl groups with 6 to 30 ring-forming carbon atoms, R 1 and R 2 The "number of ring-forming atoms" in heteroaryl groups with substituted or unsubstituted ring-forming atoms numbering from 5 to 30, L 1 and L 2The "number of ring-forming carbon atoms" in the substituted or unsubstituted arylene group with 6 to 18 ring-forming carbon atoms, and L 1 and L 2 In heteroarylene groups with substituted or unsubstituted ring-forming atoms numbering from 5 to 18, the total number of "ring-forming atoms" is 17 or more. R 1 , R 2 , L 1 , and L 2 Two adjacent elements selected from this list do not join to each other and do not form a ring. R 3 ~R 5 One is selected from and R 1 , R 2 , L 1 , and L 2 The adjacent element chosen from among them may be joined to form a ring, or it may not be joined to form a ring.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[0024] ·Unsubstituted aryl groups (Specific example group G1A): phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, benzanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, chrysenyl group, benzochrysenyl group, triphenylenyl group, benzotriphenylenyl group, tetracenyl group, pentacenyl group, fluorenyl group, 9,9'-spirobifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, fluoranthenyl group, benzofluoranthenyl group, perylenyl 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]

Chemical formula

[0026] [Chem.]]

[0027] • Substituted aryl groups (Specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-tert-butylphenyl group, meta-tert-butylphenyl group, ortho-tert-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-tert-butylphenyl)fluorenyl group, cyanophenyl group, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl group, and groups in which one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the general formula (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0028] • "Substituted or unsubstituted heterocyclic group" 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 is either a monocyclic group or a fused ring group. The term "heterocyclic group" as used herein refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples of "substituted or unsubstituted heterocyclic groups" as described herein (Specific Examples Group G2) include the following unsubstituted heterocyclic groups (Specific Examples Group G2A) and substituted heterocyclic groups (Specific Examples Group G2B), etc. (Here, "unsubstituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group," and "substituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group.") In this specification, the term "heterocyclic group" simply includes both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups." A "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of "substituted heterocyclic groups" include the groups in specific example group G2A below in which hydrogen atoms of an "unsubstituted heterocyclic group" are replaced, and the examples of substituted heterocyclic groups in specific example group G2B below. Note that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic groups" described herein also include groups in which hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself are further replaced by substituents, and groups in which hydrogen atoms of substituents are further replaced by substituents.

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

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

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

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

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

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

[0035] [ka]

[0036] [ka]

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

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

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

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

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

[0042] The aforementioned "one or more hydrogen atoms of a monovalent heterocyclic group" refers to hydrogen atoms bonded to the ring-forming carbon atoms of the monovalent heterocyclic group, X A and Y A A hydrogen atom bonded to a nitrogen atom when at least one of them is NH, and X A and Y AThis refers to one or more hydrogen atoms selected from the hydrogen atoms of the methylene group when one of the atoms 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 ) represented by the base -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 ) represented by the base The following information pertains to the -O-(R904 ) 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 ) represented by the base 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 ) represented by the base -N(R) as described in this specification 906 )(R 907 ) Examples of the base represented by (Example Group G10) are: -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6. In -N(G1)(G1), multiple G1s are either identical or different from one another. In -N(G2)(G2), multiple G2s are either identical or different from one another. In -N(G3)(G3), multiple G3s are either identical or different from one another. In -N(G6)(G6), multiple G6s are either identical or different from one another.

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

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

[0060] • "Substituted or unsubstituted haloalkyl groups" The terms "substituted or unsubstituted haloalkyl groups" as used herein refer to groups in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group is replaced by a halogen atom, and also include groups in which all hydrogen atoms bonded to a carbon atom 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. The terms "substituted haloalkyl group" refer to groups 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 a carbon atom 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 are specifically 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 where "one or more sets of two or more adjacent groups are bonded to each other to form a ring", the set of two adjacent groups forming one set refers to R 921 and R 922 , the set of R 922 and R 923 , the set of R 923 and R 924 , the set of R 924 and R 930 , the set of R 930 and R 925 , the set of R 925 and R 926 , the set of R 926 and R 927 , the set of R 927 and R 928 , the set of R 928 and R 929 , and the set of R 929 and R 921 .

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

[0104]

Chemical Formula

[0105] The case where "a set of two or more adjacent groups" forms a ring includes not only the case where a set of two adjacent groups is bonded as in the above example, but also the case where a set of three or more adjacent groups is bonded. For example, R 921 and R 922 are bonded to each other to form ring Q A , and R 922 and R923 and are joined to form a ring Q C It forms three adjacent (R 921 , R 922 and R 923 This refers to the case where a set consisting of ) is bonded to each other to form a ring and condenses onto the anthracene matrix skeleton, in which case the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C is, R 922 Share.

[0106] [ka]

[0107] The formed "mono-ring" or "condensed-ring" may be saturated or unsaturated, as a structure of the formed ring alone. Even when "a pair of adjacent rings" forms a "mono-ring" or "condensed-ring," the "mono-ring" or "condensed-ring" can form a saturated or unsaturated ring. For example, ring Q formed in the general formula (TEMP-104) A and ring Q B These are, respectively, a "single ring" or a "condensed ring". Also, ring Q formed in the general formula (TEMP-105) is A , and ring Q C This is a "condensed ring". The ring Q of the general formula (TEMP-105) A and Q C This refers to the Q environment. A and Q C The ring Q of the general formula (TEMP-104) is formed by the condensation of the two rings. A If it is a benzene ring, then ring Q A It is a single ring. The ring Q of the general formula (TEMP-104) A If it is a naphthalene ring, then ring Q A It 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 is, 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, an unsubstituted alkyl group having 1 to 50 carbon atoms. Unsubstituted alkenyl groups with 2 to 50 carbon atoms, Unsubstituted alkynyl groups with 2 to 50 carbon atoms, Unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, Unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, and Unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms It is a base selected from the group consisting of, Here, R 901 ~R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If there are two or more of them, then there are two or more R 901 They are either identical or different from each other. R 902 If there are two or more of them, then there are two or more R 902 They are either identical or different from each other. R 903If there are two or more of them, then there are two or more R 903 They are either identical or different from each other. R 904 If there are two or more of them, then there are two or more R 904 They are either identical or different from each other. R 905 If there are two or more of them, then there are two or more R 905 They are either identical or different from each other. R 906 If there are two or more of them, then there are two or more R 906 They are either identical or different from each other. R 907 If there are two or more of them, then there are two or more R 907 They are either identical or different from one another.

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

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

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

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

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

[0117] The compounds of the present invention will be described below. The compounds of the present invention are represented by the following formula (1). However, hereafter, the compounds of the present invention included in formula (1) and the formulas (1-AA), (1-AB), (1-AD), (1-BD), and (1-DD) described later may simply be referred to as the "inventive compounds."

[0118] [ka]

[0119] The following explains the symbols in equation (1).

[0120] In formula (1), N * It is the central nitrogen atom.

[0121] In formula (1), R 1 and R 2 These are, independently, substituted or unsubstituted aryl groups with 6 to 30 ring-forming carbon atoms, substituted or unsubstituted heteroaryl groups with 5 to 30 ring-forming atoms, or -Si(R 901 ')(R 902 ')(R 903') is preferably 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, more preferably a group represented by formula (2A), (2B), (2C), (2D), or (2E) described later, and particularly preferably a group represented by formula (2A), (2B), or (2D) described later.

[0122] -Si(R 901 ')(R 902 ')(R 903 ') in R 901 '~R 903 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heteroaryl group, preferably a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C50 aryl group, more preferably a substituted or unsubstituted C1-C50 alkyl group, or a substituted or unsubstituted ring-forming C6-C50 aryl group. R 901 '~R 903 If there are two or more ', then there are two or more R 901 '~R 903 The symbols ' may be the same or different.'

[0123] -Si(R 901 ')(R 902 ')(R 903 ') in R 901 '~R 903 The number of carbon atoms in the substituted or unsubstituted alkyl group represented by ' is not particularly limited as long as it is between 1 and 50, but is preferably between 1 and 30, more preferably between 1 and 15, and most preferably between 1 and 5. -Si(R 901 ')(R 902 ')(R 903 ') in R 901 '~R 903In the substituted or unsubstituted C1-C50 alkyl group represented by ', there are no particular restrictions on the unsubstituted C1-C50 alkyl group, and examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, etc. Among these, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, and pentyl group are preferred, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group are more preferred, and methyl group and t-butyl group are particularly preferred.

[0124] -Si(R 901 ')(R 902 ')(R 903 ') in R 901 '~R 903 The number of ring-forming carbon atoms in the substituted or unsubstituted cycloalkyl group represented by ' is not particularly limited as long as it is between 3 and 50, but is preferably 1 to 30, more preferably 1 to 15, and most preferably 1 to 10. -Si(R 901 ')(R 902 ')(R 903 ') in R 901 '~R 903 In the substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms represented by ', there are no particular restrictions on the unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, and examples include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group. Among these, cyclopropyl group, cyclobutyl group, cyclohexyl group, 1-adamantyl group, and 1-norbornyl group are preferred, and cyclohexyl group and 1-adamantyl group are more preferred.

[0125] -Si(R 901 ')(R 902 ')(R 903 ') in R901 '~R 903 The number of ring-forming carbon atoms in the substituted or unsubstituted aryl group represented by ' is not particularly limited as long as it is between 6 and 50, but is preferably between 6 and 30, more preferably between 6 and 18, and particularly preferably between 6 and 12. -Si(R 901 ')(R 902 ')(R 903 ') in R 901 '~R 903 In the substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms represented by ', there are no particular restrictions on the unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and examples include phenyl group, biphenylyl group, terphenylyl group, biphenylenyl group, naphthyl group, anthryl group, benzoanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, picenyl group, pentaphenyl group, pyrenyl group, crisenyl group, benzocrisenyl group, fluorenyl group, fluoranteyl group, perilenyl group, triphenylenyl group, etc. Among these, phenyl group, biphenylyl group, and naphthyl group are preferred.

[0126] -Si(R 901 ')(R 902 ')(R 903 ') in R 901 '~R 903 The number of ring-forming atoms of the substituted or unsubstituted heteroaryl group represented by ' is not particularly limited as long as it is between 5 and 50, but is preferably between 5 and 30, more preferably between 5 and 18, and particularly preferably between 5 and 13. -Si(R 901 ')(R 902 ')(R 903 ') in R 901 '~R 903In the heteroaryl group having 5 to 50 substituted or unsubstituted ring-forming atoms represented by ', there are no particular restrictions on the unsubstituted heteroaryl group having 5 to 50 ring-forming atoms, and examples include 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, indolidinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, futa Examples include radinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, benzoisoxazolyl group, benzoisothiazolyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group (benzothienyl group, hereafter the same), isobenzothiophenyl group (isobenzothienyl group, hereafter the same), dibenzothiophenyl group (dibenzothienyl group, hereafter the same), carbazolyl group, phenanthridinel group, acridinyl group, phenanthrolinyl group, phenazinyl group, phenothiazinyl group, phenoxazinyl group, xanthenyl group, etc. Among these, furyl group, thienyl group, pyridyl group, pyrimidinyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, benzimidazolyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group, isobenzothiophenyl group, dibenzothiophenyl group, and carbazolyl group are preferred, and benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group, isobenzothiophenyl group, dibenzothiophenyl group, and carbazolyl group (9-carbazolyl group, 1-, 2-, 3- or 4-carbazolyl group) are more preferred.

[0127] Below, R 1 and R 2 The equations (2A), (2B), (2C), (2D), and (2E) that can be represented by this expression, as well as the symbols in each equation, are explained below.

[0128] [ka]

[0129] In equation (2A), *21 is L 1 or L 2 This represents a connection to something.

[0130] 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 101 ~R 105 and R that is not a single bond 106 ~R 110 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C3-C15 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heteroaryl group.

[0131] R is not a single bond 101 ~R 105 and R that is not a single bond 106 ~R 110 In the substituted or unsubstituted C1-C10 alkyl group represented by , there are no particular restrictions on the unsubstituted C1-C10 alkyl group, and examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, etc. Among these, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, and hexyl group are preferred, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group are more preferred, methyl group and t-butyl group are even more preferred, and t-butyl group is particularly preferred.

[0132] R is not a single bond101 ~R 105 and R that is not a single bond 106 ~R 110 In the substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 15 carbon atoms represented by , there are no particular restrictions on the unsubstituted ring-forming cycloalkyl groups having 3 to 15 carbon atoms, and examples include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group. Among these, cyclopropyl group, cyclobutyl group, cyclohexyl group, 1-adamantyl group, and 1-norbornyl group are preferred.

[0133] R is not a single bond 101 ~R 105 and R that is not a single bond 106 ~R 110 In the substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms represented by , there are no particular restrictions on the unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, and examples include phenyl group, biphenyl group, naphthyl group, etc. Among these, phenyl group, 2-, 3-, or 4-biphenylyl group, or 1- or 2-naphthyl group are preferred, phenyl group or 1- or 2-naphthyl group are more preferred, and phenyl group is particularly preferred.

[0134] R is not a single bond 101 ~R 105 and R that is not a single bond 106 ~R 110In the heteroaryl groups represented by , which are substituted or unsubstituted and have 5 to 13 ring-forming atoms, there are no particular restrictions on the unsubstituted heteroaryl groups having 5 to 13 ring-forming atoms, and examples include 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, and indolidinyl group. Examples include the group, quinolidinyl group, quinolyl group, isoquinolyl group, sinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, benzoisoxazolyl group, benzoisothiazolyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group (benzothienyl group, hereafter the same), isobenzothiophenyl group (isobenzothienyl group, hereafter the same), dibenzothiophenyl group (dibenzothienyl group, hereafter the same), carbazolyl group, etc. Among these, furyl group, thienyl group, pyridyl group, pyrimidinyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, benzimidazolyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group, isobenzothiophenyl group, dibenzothiophenyl group, and carbazolyl group are preferred, and benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group, isobenzothiophenyl group, dibenzothiophenyl group, and carbazolyl group (9-carbazolyl group, 1-, 2-, 3- or 4-carbazolyl group) are more preferred. R is not a single bond 101 ~R 105 and R that is not a single bond 106 ~R 110In the substituted or unsubstituted heteroaryl groups having 5 to 13 ring-forming atoms represented by , there are no particular restrictions on the substituted heteroaryl groups having 5 to 13 ring-forming atoms, and examples include 9-phenylcarbazolyl group, 9-biphenylylcarbazolyl group, 9-phenylphenylcarbazolyl group, 9-naphthylcarbazolyl group, phenyldibenzofuranyl group, phenyldibenzothiophenyl group (phenyldibenzothienyl group), etc. If substituted or unsubstituted heteroaryl groups having 5 to 13 ring-forming atoms exist, isomer groups are included.

[0135] In equation (2A), R is not a single bond. 101 ~R 105 Two adjacent elements selected from this list do not join to each other and do not form a ring. In equation (2A), R is not a single bond. 106 ~R 110 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0136] 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 C3-C15 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heteroaryl group. In formula (2A), R 111 ~R 115 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0137] R 111 ~R 115 Details of the substituted or unsubstituted C1-C10 alkyl groups represented by and preferred examples thereof are as follows: 101 ~R 105 As described above. R 111 ~R 115 Details of the substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 15 carbon atoms represented by and preferred examples thereof are as follows: 101 ~R 105As described above. R 111 ~R 115 Details of the substituted or unsubstituted ring-forming aryl groups with 6 to 12 carbon atoms represented by and preferred examples thereof are as follows: 101 ~R 105 As described above. R 111 ~R 115 Details of the aryl group of a heteroaryl group with 5 to 13 substituted or unsubstituted ring-forming atoms represented by R, and preferred examples thereof, are as follows: 101 ~R 105 As described above.

[0138] In equation (2A), j is 0, 1, or 2, and k is 0 or 1, except when j is 2 and k is 0. When j=0 and k=0, *23 represents *21. When j=0 and k=1, *22 represents *21. When j=1 and k=0, *23 represents *22.

[0139] In one embodiment of the present invention, j is 0 and k is 0. In this case, *23 represents *21, and equation (2A) is expressed by the following equation.

[0140] [ka]

[0141] In another embodiment of the present invention, j is 0 and k is 1. In this case, *22 represents *21, and equation (2A) is expressed as follows.

[0142] [ka]

[0143] In another embodiment of the present invention, j is 1 and k is 0. In this case, *23 represents *22, and equation (2A) is expressed as follows.

[0144] [ka]

[0145] In another embodiment of the present invention, j is 1 and k is 1. In this case, formula (2A) is expressed as follows:

[0146] [ka]

[0147] In another embodiment of the present invention, j is 2 and k is 1. In this case, formula (2A) is expressed as follows:

[0148] [ka]

[0149] The group represented by formula (2A) is preferably represented by the following formula. In the following formula, R is omitted for simplification.

[0150] [ka]

[0151] *R that is not a single bond attached to 22 101 ~R 105 *23 is not a single bond R 106 ~R 110 , and R 111 ~R 115 It is also possible that all of them are hydrogen atoms.

[0152] [ka]

[0153] In equation (2B), *24 is L 1 or L 2 This represents a connection to [something].

[0154] In formula (2B), R 121 ~R128 One of the options selected is a single bond that connects to *25.

[0155] In equation (2B), R is not a single bond. 121 ~R 128 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C3-C15 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heteroaryl group. In equation (2B), R is not a single bond. 121 ~R 128 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0156] R 121 ~R 128 Details of substituted or unsubstituted C1-C10 alkyl groups represented by and preferred examples thereof are as follows: 101 ~R 105 As described above. R 121 ~R 128 Details and preferred examples of substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 15 carbon atoms represented by R 101 ~R 105 As described above. R 121 ~R 128 Details of substituted or unsubstituted ring-forming aryl groups with 6 to 12 carbon atoms represented by and preferred examples thereof are as follows: 101 ~R 105 As described above. R 121 ~R 128 Details of the aryl group of a heteroaryl group with 5 to 13 substituted or unsubstituted ring-forming atoms represented by and preferred examples thereof are as follows: 101 ~R 105 As described above.

[0157] One aspect of the present invention is not particularly limited, but preferably R 121 , R 124 , R 125, and R 128 One of the options selected is a single bond that connects to *25.

[0158] *R is not a single bond that forms 25 bonds. 121 ~R 128 It is also possible that all of them are hydrogen atoms.

[0159] [ka]

[0160] In equation (2C), *26 is L 1 or L 2 This represents a connection to [something].

[0161] 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 131 ~R 140 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C3-C15 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heteroaryl group. R is not a single bond 131 ~R 140 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0162] R 131 ~R 140 Details of substituted or unsubstituted C1-C10 alkyl groups represented by and preferred examples thereof are as follows: 101 ~R 105 As described above. R 131 ~R 140 Details and preferred examples of substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 15 carbon atoms represented by R 101 ~R 105 As described above. R 131 ~R140 Details of substituted or unsubstituted ring-forming aryl groups with 6 to 12 carbon atoms represented by and preferred examples thereof are as follows: 101 ~R 105 As described above. R 131 ~R 140 Details of the aryl group of a heteroaryl group with 5 to 13 substituted or unsubstituted ring-forming atoms represented by R, and preferred examples thereof, are as follows: 101 ~R 105 As described above.

[0163] One aspect of the present invention is not particularly limited, but preferably R 137 and R 138 One of the selected is a single bond that connects to *27, more preferably R 137 This is a single bond that connects to *27.

[0164] *27 bonds are not single bonds R 131 ~R 140 However, they could all be hydrogen atoms.

[0165] [ka]

[0166] In equation (2D), *28 is L 1 or L 2 This represents a connection to [something].

[0167] In formula (2D), X 1 It consists of an oxygen atom, a sulfur atom, and -CR a R b , or -NR c Among these, -CR a R b , -NR c It is preferable.

[0168] In equation (2D), *29 is R 141 ~R 148 , R 200 ~R 203 , R a , R b, or R c It joins to one of the following.

[0169] In equation (2D), *29 is R a , R b , and R c When combining with any of the following, R a , R b , and R c One of these is either a single bond attached to *29 or a divalent group attached to *29. R a , R b , or R c There are no particular restrictions on the divalent group that can be formed, and examples include an unsubstituted phenylene group, an unsubstituted biphenylene group, and an unsubstituted naphthylene group. Among these, an unsubstituted phenylene group is preferred, and an unsubstituted m-phenylene group and an unsubstituted p-phenylene group are more preferred.

[0170] In equation (2D), p is either 0 or 1. p is 0, X 1 However, oxygen atoms, sulfur atoms, -CR a R b , or -NR c When R a , R b , R c , and R 141 ~R 148 One of the options selected is a single bond that connects to *29. p is 1, X 1 ga-CR a R b or -NR c When R 145 and R 146 , R 146 and R 147 , or R 147 and R 148 One of the R atoms is a single bond that connects to *e, and the other is a single bond that connects to *f, and is not a single bond that connects to *e or *f. 145 ~R 148 , R 141 ~R 144 , R 200 ~R 203 , R a , Rb , and R c One of the options selected is a single bond that connects to *29. p is 1, X 1 When is an oxygen atom or a sulfur atom, R 145 and R 146 , R 146 and R 147 , or R 147 and R 148 One of the R atoms is a single bond that connects to *e, and the other is a single bond that connects to *f, and is not a single bond that connects to *e or *f. 145 ~R 148 , R 141 ~R 144 , and R 200 ~R 203 One of the options selected is a single bond that connects to *29.

[0171] In equation (2D), R 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 C3-C15 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heteroaryl group. R 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 list do not join to each other and do not form a ring.

[0172] R is not a single bond 141 ~R 148 and R that is not a single bond 200 ~R 203 Details of substituted or unsubstituted C1-C10 alkyl groups represented by and preferred examples thereof are as follows: 101 ~R 105 As described above. R is not a single bond 141 ~R 148 and R that is not a single bond 200 ~R203 Details and preferred examples of substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 15 carbon atoms represented by R 101 ~R 105 As described above. R is not a single bond 141 ~R 148 and R that is not a single bond 200 ~R 203 Details of substituted or unsubstituted ring-forming aryl groups with 6 to 12 carbon atoms represented by and preferred examples thereof are as follows: 101 ~R 105 As described above. R is not a single bond 141 ~R 148 and R that is not a single bond 200 ~R 203 Details of the substituted or unsubstituted ring-forming heteroaryl groups with 5 to 13 carbon atoms represented by and preferred examples thereof are as follows: 101 ~R 105 As described above.

[0173] In formula (2D), R is not a single bond but a divalent group. a , R b , and R c Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C5 alkyl group, or a substituted or unsubstituted ring-forming C6-C12 aryl group. R is not a single bond and is not a divalent group. a , R b , and R c Two adjacent elements selected from the set may join together to form a ring, or they may not join together to form a ring.

[0174] R is not a single bond and is not a divalent group. a , R b , and R cIn the substituted or unsubstituted C1-C5 alkyl group represented by , there are no particular restrictions on the unsubstituted C1-C5 alkyl group, and examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, etc. Among these, the methyl group and t-butyl group are preferred, and the t-butyl group is particularly preferred. R is not a single bond and is not a divalent group. a , R b , and R c Details of substituted or unsubstituted ring-forming aryl groups with 6 to 12 carbon atoms represented by and preferred examples thereof are as follows: 101 ~R 105 As described above.

[0175] R is not a single bond 141 ~R 148 , not a single bond R 200 ~R 203 R is not a single bond and is not a divalent group. a and R b , and also, R c These may all be hydrogen atoms.

[0176] [ka]

[0177] In equation (2E), *30 is L 1 or L 2 This represents a connection to [something].

[0178] 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 from these is a single bond that connects to *32.

[0179] In equation (2E), R is not a single bond. 151 ~R 155Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C3-C15 cycloalkyl group, or an unsubstituted phenyl group. In equation (2E), R is not a single bond. 151 ~R 155 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0180] In formula (2E), R 161 ~R 165 and R 171 ~R 175 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted ring-forming C3-C15 cycloalkyl group. In equation (2E), R is not a hydrogen atom. 161 ~R 165 At least one adjacent pair selected from the set 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. In equation (2E), R is not a hydrogen atom. 171 ~R 175 At least one adjacent pair selected from the set 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 a ring.

[0181] R 151 ~R 155 , R 161 ~R 165 , and R 171 ~R 175 Details of substituted or unsubstituted C1-C10 alkyl groups represented by and preferred examples thereof are as follows: 101 ~R 105 As described above. R 151 ~R 155 , R 161 ~R 165 , and R 171 ~R 175 Details and preferred examples of substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 15 carbon atoms represented by R 101 ~R105 As described above.

[0182] In one embodiment of the present invention, R 161 ~R 165 Two adjacent elements selected from are bonded to each other to form one or more unsubstituted benzene rings. In another embodiment of the present invention, R 161 ~R 165 Two adjacent elements selected from the set do not bond to each other and therefore do not form a ring structure. In one embodiment of the present invention, R 171 ~R 175 Two adjacent elements selected from are bonded to each other to form one or more unsubstituted benzene rings. In another embodiment of the present invention, R 171 ~R 175 Two adjacent elements selected from the set do not bond to each other and therefore do not form a ring structure.

[0183] R is not a single bond 151 ~R 155 These may all be hydrogen atoms, R 161 ~R 165 R may be all hydrogen atoms, 171 ~R 175 All of them may be hydrogen atoms.

[0184] In formula (1), R 3 ~R 5 There are no particular restrictions as long as each is independently a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heteroaryl group, but preferably R 3 ~R 5 At least one of the selected groups is a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, more preferably a substituted or unsubstituted ring-forming aryl group having 6 to 18 carbon atoms, even more preferably a substituted or unsubstituted phenyl group, and particularly preferably an unsubstituted phenyl group.

[0185] R 3 ~R 5 The number of carbon atoms in the substituted or unsubstituted alkyl group represented by is not particularly limited as long as it is between 1 and 30, but is preferably between 1 and 15, and more preferably between 1 and 5. R 3 ~R 5 In the substituted or unsubstituted C1-C30 alkyl group represented by , there are no particular restrictions on the unsubstituted C1-C30 alkyl group, and examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, etc. Among these, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, and pentyl group are preferred, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group are more preferred, and methyl group and t-butyl group are particularly preferred.

[0186] R 3 ~R 5 The number of ring-forming carbon atoms in the substituted or unsubstituted cycloalkyl group represented by is not particularly limited as long as it is between 3 and 20, but is preferably between 3 and 15, and more preferably between 3 and 10. R 3 ~R 5 In the substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 20 carbon atoms represented by , there are no particular restrictions on the unsubstituted ring-forming cycloalkyl groups having 3 to 20 carbon atoms, and examples include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group. Among these, cyclopropyl group, cyclobutyl group, cyclohexyl group, 1-adamantyl group, and 1-norbornyl group are preferred, and cyclohexyl group and 1-adamantyl group are more preferred.

[0187] R 3 ~R 5Details of substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms represented by and preferred examples thereof are as follows: 901 '~R 903 As stated in the document regarding '. R 3 ~R 5 Details and preferred examples of substituted or unsubstituted heteroaryl groups having 5 to 30 ring-forming atoms represented by R 901 '~R 903 As stated in the document regarding '.

[0188] In formula (1), R 3 ~R 5 However, if each is independently a substituted or unsubstituted ring-forming aryl group with 6 to 30 carbon atoms, then R 3 ~R 5 In the context of substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms, the substituents referred to as "substituted or unsubstituted" do not include amino groups.

[0189] In formula (1), R 4 is a substituted or unsubstituted ring-forming aryl group with 6 to 30 carbon atoms, and R 3 and R 5 If R is a substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, 3 and R 5 At least one of these is a substituted or unsubstituted alkyl group having 2 to 30 carbon atoms.

[0190] In formula (1), R 3 ~R 5 Two adjacent elements selected from the set may join together to form a ring, or they may not join together to form a ring. Of these, it is preferable that they do not join together to form a ring.

[0191] In formula (1), L 1 and L 2There are no particular restrictions as long as each is independently a single-bonded, substituted, or unsubstituted arylene group having 6 to 18 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 18 ring-forming atoms. Preferably, each is a single-bonded, substituted, or unsubstituted arylene group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 13 ring-forming atoms. More preferably, each is a single-bonded, substituted, or unsubstituted arylene group having 6 to 12 ring-forming carbon atoms, and particularly preferably, a single-bonded, substituted, or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0192] L 1 and L 2 In the substituted or unsubstituted ring-forming arylene group having 6 to 18 carbon atoms represented by , there are no particular restrictions on the unsubstituted ring-forming arylene group having 6 to 18 carbon atoms, and examples include phenylene group, biphenylene group, terphenylene group, naphthylene group, anthreene group, benzoantrylene group, phenanthrylene group, benzophenanthrylene group, phenalenylene group, picenylene group, pentaphenylene group, pyrenylene group, chrysenylene group, benzochrysenylene group, triphenylenylene group, etc.

[0193] L 1 and L 2In the substituted or unsubstituted heteroarylene group having 5 to 18 ring-forming atoms represented by , there are no particular restrictions on the unsubstituted heteroarylene group having 5 to 18 ring-forming atoms, for example, pyrrolylene group, flirene group, thienylene group, pyridylene group, imidazopyridylene group, pyridadinylene group, pyrimidinylene group, pyradinylene group, triazinylene group, imidazolyylene group, oxazolylene group, thiazolyylene group, pyrazolylene group, isoxazolylene group, isothiazolyylene group, oxadiazolyylene group, thiadiazolyylene group, triazolylene group, tetrazolyylene group, indolylene group, isoindolylene group, ben Examples include zofuranylene group, isobenzofuranylene group, benzothiophenylene group, isobenzothiophenylene group, indolidinelen group, quinolidinylene group, quinolylene group, isoquinolylene group, synnoylene group, phthalazinelen group, quinazolinylene group, quinoxalinylene group, benzimidazoylene group, benzoxazolylene group, benzthiazoylene group, indazoylene group, benzisoxazolylene group, benzisothiazoylene group, phenanthridinelen group, acridinylene group, phenanthrolinylene group, phenadinylene group, phenothiazinylene group, phenoxadinylene group, xanthenylene group, and the like.

[0194] In formula (1), R 1 and R 2 However, if each is independently a substituted or unsubstituted aryl group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group with 5 to 30 ring-forming atoms, then R 1 and R 2 The "number of ring-forming carbon atoms" in substituted or unsubstituted aryl groups with 6 to 30 ring-forming carbon atoms, R 1 and R 2 The "number of ring-forming atoms" in heteroaryl groups with substituted or unsubstituted ring-forming atoms numbering from 5 to 30, L 1 and L 2 The "number of ring-forming carbon atoms" in the substituted or unsubstituted arylene group with 6 to 18 ring-forming carbon atoms, and L 1 and L 2The total number of "ring-forming atoms" in the substituted or unsubstituted heteroarylene groups with 5 to 18 ring-forming atoms represented by is 17 or more, preferably 20 or more, more preferably 22 or more, and particularly preferably 24 or more.

[0195] In formula (1), R 1 , R 2 , L 1 , and L 2 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0196] In formula (1), R 3 ~R 5 One is selected from and R 1 , R 2 , L 1 , and L 2 The adjacent element selected from the group may or may not join to form a ring. Of these, it is preferable that the elements not join to form a ring.

[0197] In formula (1), R 1 and R 2 There are no particular restrictions, but as mentioned above, it is preferable that each be independently represented by formula (2A), (2B), or (2D). R 1 and R 2 One embodiment is not particularly limited, but is preferably represented by the following formulas (1-AA), (1-AB), (1-AD), (1-BD), or (1-DD), and more preferably R 1 and R 2 These are expressed independently by equation (2A) or (2B), and R 1 and R 2 At least one of them is equation (2A) (i.e., it is expressed by the following equations (1-AA) or (1-AB)).

[0198] [ka]

[0199] In formula (1-AA), N * , R 3 ~R 5 , R 101 ~R 115 , j, k, *22, *23, L 1 , and L 2 This is defined in equations (1) and (2A) above. Note that R 101 ~R 115 If there are two or more instances of j, k, *22 and *23, then there are two or more instances of R. 101 ~R 115 j, k, *22, and *23 may be the same or different.

[0200] [ka]

[0201] In formula (1-AB), N * , R 3 ~R 5 , R 101 ~R 115 , R 121 ~R 128 ,j,k,*22,*23,*25,L 1 , and L 2 This is as defined in equations (1), (2A), and (2B) above.

[0202] [ka]

[0203] In formula (1-AD), N * , R 3 ~R 5 , R 101 ~R 115 , R 141 ~R 148 , R 200 ~R 203 , X 1 , j, k, p, *22, *23, *29, *e, *f, L 1 , and L 2 This is as defined in equations (1), (2A), and (2D) above.

[0204] [ka]

[0205] In formula (1-BD), N * , R 3 ~R 5 , R 121 ~R 128 , R 141 ~R 148 , R 200 ~R 203 , X 1 , p, *25, *29, *e, *f, L 1 , and L 2 This is as defined in equations (1), (2B), and (2D) above.

[0206] [ka]

[0207] In formula (1-DD), N * , R 3 ~R 5 , R 141 ~R 148 , R 200 ~R 203 , X 1 , p, *29, *e, *f, L 1 , and L 2 This is defined in equations (1) and (2D) above. Note that R 141 ~R 148 , R 200 ~R 203 , X 1 If there are two or more of , p, *29, *e, and *f, then there are two or more R 141 ~R 148 , R 200 ~R 203 , X 1 p, *29, *e, and *f may be the same or different.

[0208] The 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 the section "Substituents in the case of 'substituted or unsubstituted'," except in special cases. The substituents in the definitions of the above formulas, when referred to as "substituted or unsubstituted," are not particularly limited, but are preferably unsubstituted C1-C20 alkyl groups, unsubstituted C3-C20 cycloalkyl groups, unsubstituted C6-C18 aryl groups, or unsubstituted C5-C18 heteroaryl groups; more preferably unsubstituted C1-C15 alkyl groups, unsubstituted C3-C15 cycloalkyl groups, unsubstituted C6-C12 aryl groups, or unsubstituted C5-C13 heteroaryl groups; and particularly preferably unsubstituted C1-C5 alkyl groups, unsubstituted C3-C10 cycloalkyl groups, unsubstituted C6-C10 aryl groups, or unsubstituted C5-C10 heteroaryl groups.

[0209] The unsubstituted C1-C20 alkyl group used as a substituent in the definition of each of the above formulas, in the case of "substituted or unsubstituted," is not particularly limited. Examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, etc. Among these, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, and pentyl group are preferred, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group are more preferred, and methyl group and t-butyl group are particularly preferred.

[0210] The unsubstituted ring-forming cycloalkyl groups having 3 to 20 carbon atoms, as substituents in the definitions of the above formulas, are not particularly limited. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl groups. Among these, cyclopropyl, cyclobutyl, cyclohexyl, 1-adamantyl, and 1-norbornyl groups are preferred, and cyclohexyl and 1-adamantyl groups are more preferred.

[0211] The unsubstituted ring-forming aryl group having 6 to 18 carbon atoms, as a substituent in the definition of each of the above formulas, is not particularly limited. Examples include phenyl, biphenylyl, terphenylyl, biphenylenyl, naphthyl, anthryl, benzoantryl, phenanthryl, benzophenanthryl, phenalenyl, picenyl, pentaphenyl, pyrenyl, crisenyl, benzocrisenyl, fluorenyl, fluorantenyl, perilenyl, and triphenylenyl groups. Among these, phenyl, biphenylyl, and naphthyl groups are preferred.

[0212] In the definitions of the above formulas, there are no particular restrictions on the unsubstituted heteroaryl groups with 5 to 18 ring-forming atoms as substituents in the case of "substituted or unsubstituted". Examples include 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, indolidinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, futa Examples include radinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, benzoisoxazolyl group, benzoisothiazolyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group (benzothienyl group, hereafter the same), isobenzothiophenyl group (isobenzothienyl group, hereafter the same), dibenzothiophenyl group (dibenzothienyl group, hereafter the same), carbazolyl group, phenanthridinel group, acridinyl group, phenanthrolinyl group, phenazinyl group, phenothiazinyl group, phenoxazinyl group, xanthenyl group, etc. Among these, furyl group, thienyl group, pyridyl group, pyrimidinyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, benzimidazolyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group, isobenzothiophenyl group, dibenzothiophenyl group, and carbazolyl group are preferred, and benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group, isobenzothiophenyl group, dibenzothiophenyl group, and carbazolyl group (9-carbazolyl group, 1-, 2-, 3- or 4-carbazolyl group) are more preferred.

[0213] As stated above, the term "hydrogen atom" as used herein includes light hydrogen atoms, deuterium atoms, and tritium atoms. Therefore, the inventive compound may contain naturally occurring deuterium atoms. Furthermore, deuterium atoms may be intentionally introduced into the inventive compound by using a deuterized compound as part or all of the raw material compound. Accordingly, in one embodiment of the present invention, the inventive compound may contain at least one deuterium atom in its molecule. That is, the inventive compound may be a compound represented by formula (1) in which at least one of the hydrogen atoms contained in the compound is a deuterium atom.

[0214] In one embodiment of the present invention, L 1 , and L 2 If all of these are unsubstituted phenylene groups, each of these unsubstituted phenylene groups may independently contain at least one deuterium atom. In one embodiment of the present invention, L 1 , and L 2 If all of these are unsubstituted phenylene groups, then all of the hydrogen atoms in one of these unsubstituted phenylene groups may be deuterium atoms. In one embodiment of the present invention, L 1 , and L 2 If all of these are unsubstituted phenylene groups, then all of the hydrogen atoms contained in these unsubstituted phenylene groups may be deuterium atoms.

[0215] The deuterated ratio of the inventive compound depends on the deuterated ratio of the raw material compound used. Even when using raw materials with a predetermined deuterated ratio, a certain proportion of naturally occurring light hydrogen isotopes may be present. Therefore, the forms of deuterated ratio of the inventive compound shown below include a ratio that takes into account trace amounts of naturally occurring isotopes, in addition to the ratio obtained by simply counting the number of deuterium atoms represented by the chemical formula. The deuterated rate of the inventive compound is not particularly limited, but is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, and particularly preferably 20% or more. Furthermore, the deuterated rate may be 1-100%, 2-90%, 3-80%, 5-60%, 10-50%, or 20-30%.

[0216] The inventive compound may be a mixture containing a deuterated compound and an undeuterated compound, or a mixture of two or more compounds having different deuterated rates. The deuterated rate of such a mixture is not particularly limited, but is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, and particularly preferably 20% or more. Furthermore, the deuterated rate may be 1-100%, 3-80%, 5-60%, 10-50%, or 20-30%.

[0217] Those skilled in the art can easily produce the inventive compound by referring to the following synthesis examples and known synthesis methods.

[0218] The following are specific examples of the inventive compounds, but the invention is not limited to these example compounds. In addition to the compounds listed below as example compounds, the inventive compounds also include compounds in which some hydrogen atoms are not deuterated due to the synthesis technique. In the specific examples below, D represents a deuterium atom.

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[0288] Materials for organic EL devices A material for organic EL devices according to one aspect of the present invention contains the inventive compound. The content of the inventive compound in the material for organic EL devices is 1% by mass or more (including 100%), and is not particularly limited, but is preferably 10% by mass or more (including 100%), more preferably 50% by mass or more (including 100%), even more preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). A material for organic EL devices according to one aspect of the present invention is useful for the manufacture of organic EL devices. In one embodiment of the present invention, it is preferable that the inventive compound is a hole transport layer material.

[0289] A material for an organic electroluminescent device according to one aspect of the present invention is a hole transport layer material. There are no particular restrictions on the content of the inventive compound in the material for organic electroluminescent elements, but it 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%).

[0290] Organic EL element An organic EL element according to one aspect of the present invention has an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer includes a light-emitting layer, and at least one layer of the organic layer contains the inventive compound. Examples of organic layers containing the inventive compound include, but are not limited to, hole transport bands (hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer, etc.) provided between the anode and the light-emitting layer, light-emitting layer, space layer, electron transport bands (electron injection layer, electron transport layer, hole blocking layer, etc.) provided between the cathode and the light-emitting layer. The inventive compound is not particularly limited, but 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, a material for the hole transport layer, a material for the electron blocking layer, a material for the exciton blocking layer, and especially preferably as a material for the hole injection layer or a material for the hole transport layer.

[0291] 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, a white light-emitting element of the fluorescent / phosphorescent hybrid type, a simple type having a single light-emitting unit, or a tandem type having multiple light-emitting units. Among these, a fluorescent light-emitting element is preferred. Here, "light-emitting unit" refers to the smallest unit that includes an organic layer, consists of one or more layers made up of the organic layer, and at least one layer selected from the group consisting of the single layer and the multiple layers is a light-emitting layer, and emits light when injected holes and electrons recombine.

[0292] For example, the following are typical device configurations for simple organic EL elements. (1) Anode / Light-emitting unit / Cathode Furthermore, the above-mentioned light-emitting unit may be a multilayer type having multiple phosphorescent and fluorescent light-emitting layers. In this case, a space layer may be provided between each light-emitting layer to prevent excitons generated in the phosphorescent layer from diffusing into the fluorescent light-emitting layer. A typical layer configuration of a simple light-emitting unit is shown below. The layers in parentheses are arbitrary. (a) (Hole injection layer / ) Hole transport layer / Fluorescence layer / Electron transport layer ( / Electron injection layer) (b) (Hole injection layer / ) Hole transport layer / First fluorescence emission layer / Second fluorescence emission layer / Electron transport layer ( / Electron injection layer) (c) (Hole injection layer / ) Hole transport layer / Phosphorescent layer / Space layer / Fluorescent layer / Electron transport layer ( / Electron injection layer) (d) (Hole injection layer / ) Hole transport layer / First phosphorescent layer / Second phosphorescent layer / Space layer / Fluorescent layer / Electron transport layer ( / Electron injection layer) (e) (Hole injection layer / ) Hole transport layer / Phosphorescent layer / Space layer / First fluorescence layer / Second fluorescence layer / Electron transport layer ( / Electron injection layer) (f) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Fluorescence layer / Electron transport layer ( / Electron injection layer) (g) (Hole injection layer / ) Hole transport layer / Exciton blocking layer / Fluorescence layer / Electron transport layer ( / Electron injection layer) (h)(Hole injection layer / )First hole transport layer / Second hole transport layer / Fluorescence-emitting layer / Electron transport layer( / Electron injection layer) (h1)(Hole injection layer / )First hole transport layer / Second hole transport layer / Third hole transport layer / Fluorescence-emitting layer / Electron transport layer( / Electron injection layer) (i) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Fluorescence layer / First electron transport layer / Second electron transport layer ( / Electron injection layer) (i1)(Hole injection layer / )First hole transport layer / Second hole transport layer / Third hole transport layer / Fluorescence-emitting layer / First electron transport layer / Second electron transport layer( / Electron injection layer) (j)(Hole injection layer / )Hole transport layer / Fluorescence layer / Hole blocking layer / Electron transport layer( / Electron injection layer) (k)(hole injection layer / )hole transport layer / fluorescence layer / exciton blocking layer / electron transport layer( / electron injection layer)

[0293] 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.

[0294] 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, there are no particular restrictions on the first and second light-emitting units; for example, they can be independently selected from the above-mentioned light-emitting units. The above-mentioned intermediate layer is generally also called an intermediate electrode, intermediate conductive layer, charge generation layer, electron extraction layer, connecting layer, or intermediate insulating layer, and a known material configuration can be used to supply electrons to the first light-emitting unit and holes to the second light-emitting unit. Furthermore, if the hole transport layer is a multilayer structure containing two or more hole transport layers, the hole transport layers adjacent to the light-emitting layer in the multilayer structure, for example, the second hole transport layer in the two-layer structure or the third hole transport layer in the three-layer structure, may function as electron blocking layers. In other words, if the hole transport layer is a multilayer structure containing two or more hole transport layers, the hole transport layers adjacent to the light-emitting layer in the multilayer structure can also be used as electron blocking layers.

[0295] Figure 1 is a schematic diagram showing an example of the configuration of an organic EL element according to one aspect of the present invention. The organic EL element 1 shown in Figure 1 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10 disposed between the anode 3 and the cathode 4. The light-emitting unit 10 has a light-emitting layer 5. There is a hole transport band 6 (hole injection layer, hole transport layer, etc.) between the light-emitting layer 5 and the anode 3, and an electron transport band 7 (electron injection layer, electron transport layer, etc.) between the light-emitting layer 5 and the cathode 4. In addition, an electron blocking layer (not shown) may be provided on the anode 3 side of the light-emitting layer 5, and a hole blocking layer (not shown) may be provided on the cathode 4 side of the light-emitting layer 5. This can confine electrons and holes in the light-emitting layer 5 and further increase the exciton generation efficiency in the light-emitting layer 5.

[0296] Figure 2 is a schematic diagram showing another configuration of an organic EL element according to one aspect of the present invention. The organic EL element 11 shown in Figure 2 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 20 disposed between the anode 3 and the cathode 4. The light-emitting unit 20 has a light-emitting layer 5. The hole transport band disposed between the anode 3 and the light-emitting layer 5 is formed from a hole injection layer 6a, a first hole transport layer 6b, and a second hole transport layer 6c. The electron transport band disposed between the light-emitting layer 5 and the cathode 4 is formed from a first electron transport layer 7a and a second electron transport layer 7b.

[0297] Figure 3 is a schematic diagram showing yet another configuration of an organic EL element according to one aspect of the present invention. The organic EL element 12 includes a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 30 disposed between the anode 3 and the cathode 4. The light-emitting unit 30 has a light-emitting layer 5. The hole transport band disposed between the anode 3 and the light-emitting layer 5 is formed from a hole injection layer 6a, a first hole transport layer 6b, a second hole transport layer 6c, and a third hole transport layer 6d. The electron transport band disposed between the light-emitting layer 5 and the cathode 4 is formed from a first electron transport layer 7a and a second electron transport layer 7b.

[0298] In Figures 1 to 3, the light-emitting layer 5 includes at least one light-emitting layer. The light-emitting layer 5 may be a single layer or may include multiple layers (for example, multiple light-emitting layers, multiple light-emitting layers and a space layer). In one embodiment, it is preferable that it is laminated with multiple layers.

[0299] 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 (phosphorescent 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.

[0300] substrate The substrate is used as a support for the organic EL element. There are no particular restrictions on the substrate; for example, plates made of glass, quartz, or plastic can be used. A flexible substrate may also be used. There are no particular restrictions on the flexible substrate; for example, plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride can be used. An inorganic vapor-deposited film can also be used.

[0301] anode There are no particular restrictions on the anode formed on the substrate, but preferably, a metal, alloy, electrically conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or more) is used. 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), and nitrides of the above metals (e.g., titanium nitride).

[0302] 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.

[0303] Hole transport band As described above, the organic layer may include a hole transport band between the anode and the light-emitting layer. The hole transport band is composed of a hole injection layer, a hole transport layer, an electron blocking layer, etc. It is preferable that the hole transport band contains the inventive compound. It is preferable that at least one layer selected from the group consisting of these layers constituting the hole transport band (hole injection layer, hole transport layer, electron blocking layer, etc.) contains the inventive compound, and it is particularly preferable that the hole transport layer contains the inventive compound.

[0304] 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, can also be used, including 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); and rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these. When forming the anode using alkali metals, alkaline earth metals, and alloys containing them, vacuum deposition or sputtering methods can be used. Furthermore, when using silver paste or the like, coating or inkjet methods can be used.

[0305] 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.

[0306] Other hole-injectable materials besides the inventive compound are not particularly limited and include, for example, 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.

[0307] 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.

[0308] 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 have been added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[0309] Furthermore, it is also preferable to use an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K).

[0310] [ka]

[0311] (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 together to form a group represented by -CO-O-CO-. R 227 There are no particular restrictions on the group, but examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, cyclopentyl group, cyclohexyl group, etc.

[0312] In one embodiment of the organic EL element according to the present invention, the hole transport band includes a hole injection layer between the anode and the first hole transport layer on the anode side, and the hole injection layer includes a first organic material and a second organic material, wherein the first organic material and the second organic material are different from each other. The content of the second organic material in the hole injection layer is not particularly limited, but is preferably 0.01% by mass or more and less than 50% by mass, more preferably 0.05 to 30% by mass, even more preferably 0.10 to 10% by mass, even more preferably 0.50 to 5% by mass, and particularly preferably 1.0% to 3% by mass.

[0313] Examples of the first organic material include the inventive compound or the aforementioned hole-injectable materials other than the inventive compound.

[0314] In one embodiment of the organic EL element of this embodiment, the second organic material is not particularly limited and is, for example, a compound containing at least one of a first ring structure represented by the following general formula (P11) and a second ring structure represented by the following general formula (P12).

[0315] [ka]

[0316] (The first ring structure represented by the general formula (P11) is condensed in the molecule of the second organic material with at least one of the ring structures of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted heterocycle having 5 to 50 ring-forming atoms.) = Z 10 The structure represented by the following general formulas is (11a), (11b), (11c), (11d), (11e), (11f), (11g), (11h), (11i), (11j), (11k), or (11m).

[0317] [ka]

[0318] [ka]

[0319] (In the above general formulas (11a), (11b), (11c), (11d), (11e), (11f), (11g), (11h), (11i), (11j), (11k), or (11m), R 11 ~R 14 R 1101 ~R 1110 Each of them operates independently. hydrogen atom, halogen atom, Hydroxyl group, Cyano group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted. (In the above general formula (P12), Z1 to Z5 are each independent of each other.) Nitrogen atom, R 15 A carbon atom that bonds with it, or A carbon atom that bonds with other atoms in the molecule of the second organic material, Of Z1 to Z5, at least one is a carbon atom that bonds with other atoms in the molecule of the second organic material. R 15 teeth, hydrogen atom, halogen atom, Cyano group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, Carboxy group, Substituted or unsubstituted ester groups, Substituted or unsubstituted carbamoyl groups, Nitro group, and Selected from the group consisting of substituted or unsubstituted siloxanil groups, R 15 If multiple R 15 They are either identical or different. (In the second organic material, R 901 ~R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, 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 906They are either identical or different from each other. R 907 If there are multiple R 907 They are either identical or different to one another.

[0320] In this specification, an ester group is at least one group selected from the group consisting of alkyl ester groups and aryl ester groups. The alkyl ester group used herein is not particularly limited, for example, -C(=O)OR E It is represented as R E There are no particular restrictions on the type of alkyl group, but examples include substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms (preferably 1 to 10 carbon atoms). The aryl ester group used herein is not particularly limited, for example, -C(=O)OR Ar It is represented as R Ar There are no particular restrictions on the type of ring-forming group; for example, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms can be used.

[0321] In this specification, the siloxanyl group is a silicon compound group via an ether bond. There are no particular limitations on the siloxanyl group, and examples include the trimethylsiloxanyl group.

[0322] In this specification, the carbamoyl group is represented by -CONH2. The substituted carbamoyl group in this specification is not particularly limited, for example, -CONH-Ar C -CONH-R C It is represented by, for example, Ar C There are no particular restrictions on these, but examples include substituted or unsubstituted aryl groups with 6 to 50 (preferably 6 to 10) ring-forming carbon atoms, and heterocyclic groups with 5 to 50 (preferably 5 to 14) ring-forming atoms. Also, Ar C This may be a group formed by bonding a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms to a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. R CThere are no particular restrictions on the type of alkyl group, but examples include substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms (preferably 1 to 6 carbon atoms). In the second organic material described above, it is preferable that any group described as "substituted or unsubstituted" is an "unsubstituted" group.

[0323] The second organic material is not particularly limited, and examples include the following compounds. However, the present invention is not limited to these specific examples of the second organic material.

[0324] [ka] [ka]

[0325] 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.

[0326] The hole transport layer may be a single-layer structure or a multilayer structure containing two or more layers. For example, the hole transport layer may be a two-layer structure containing a first hole transport layer (anode side) and a second hole transport layer (cathode side). In other words, the hole transport band may include the first hole transport layer on the anode side and the second hole transport layer on the cathode side. Alternatively, the hole transport layer may be a three-layer structure containing a first hole transport layer, a second hole transport layer, and a third hole transport layer in order from the anode side. In other words, the third hole transport layer may be placed between the second hole transport layer and the light-emitting layer. In one embodiment of the present invention, the hole transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, and the hole transport layer closest to the cathode in the multilayer structure, for example, the second hole transport layer in the two-layer structure or the third hole transport layer in the three-layer structure, is preferably adjacent to the light-emitting layer. In particular, it is preferable that the light-emitting layer and the second hole transport layer are in direct contact. In another embodiment of the present invention, an electron blocking layer, etc., described later, may be interposed between the hole transport layer of the single-layer structure and the light-emitting layer, or between the hole transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer. Furthermore, as described above, if the hole transport layer is a multilayer structure containing two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer in the multilayer structure can also be used as an electron blocking layer. In one embodiment of the organic electroluminescent element according to the present invention, one or both of the first hole transport layer and the second hole transport layer contain the 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 selected from the group consisting of the first to third hole transport layers contains the inventive compound. Specifically, in the three-layer hole transport layer, the inventive compound may be contained in only one of the first to third hole transport layers, in only two of them, or in all of them.

[0327] 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.

[0328] There are no particular limitations on hole transport layer materials other than the inventive compound, and examples include aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. There are no particular restrictions on the aromatic amine compounds, for example, 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), 4,4'-bis[N-(9,9-dimethylfluoren] Examples include -2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-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.

[0329] There are no particular restrictions on the carbazole derivatives, and examples 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). There are no particular restrictions on the anthracene derivatives, and examples 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.

[0330] In one embodiment of the organic EL element according to the present invention, the first hole transport layer contains a compound represented by the following formula (21) or formula (22).

[0331] [ka] [In formulas (21) and (22) above, L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 Each of these is independently an arylene group with 6 to 50 ring-forming carbon atoms, either single-bonded, substituted, or unsubstituted, or a divalent heterocyclic group with 5 to 50 ring-forming atoms, k is 1, 2, 3, or 4. If k is 1, L E2 This is a substituted or unsubstituted arylene group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 ring-forming atoms. If k is 2, 3, or 4, multiple L E2 They are either identical or different from each other. If k is 2, 3, or 4, multiple L E2 They may bond to each other to form substituted or unsubstituted monorings, or bond to each other to form substituted or unsubstituted fused rings, or not bond to each other. L that does not form the aforementioned monoring and does not form the aforementioned condensed ring E2 This is a substituted or unsubstituted arylene group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 ring-forming atoms. A 1 B 1 , C 1 , A 2 B 2 , C 2 , and D 2 These are, independently, substituted or unsubstituted aryl groups with 6 to 50 ring-forming carbon atoms, substituted or unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms, or -Si(R' 901 )(R'902 )(R' 903 ) and R' 901 , R' 902 and R' 903 These are, independently, substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms. R' 901 If multiple R's exist, 901 They are either identical or different from each other. R' 902 If multiple R's exist, 902 They are either identical or different from each other. R' 903 If multiple R's exist, 903 They are either identical or different from one another.

[0332] 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).

[0333] In equations (21) and (22), A 1 B 1 , C 1 , A 2 B 2 , C 2 , and D 2 There are no particular restrictions on these groups, but preferably they are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibensofuranil group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group. Furthermore, more preferably, in formula (21), A 1 B 1 and C 1 At least one selected from the group consisting of and in equation (22), A 2 B 2 , C 2 and D 2At least one selected from the group consisting of 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, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0334] A 1 B 1 , C 1 , A 2 B 2 , C 2 , and D 2 The fluorenyl group that can be formed may have a substituent at the 9-position, for example, a 9,9-dimethylfluorenyl group or a 9,9-diphenylfluorenyl group. Alternatively, the substituents at the 9-position may form a ring, for example, a fluorene skeleton or a xanthene skeleton.

[0335] L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 There are no particular restrictions, but preferably, each is independently a single-bonded, substituted, or unsubstituted ring-forming arylene group having 6 to 12 carbon atoms.

[0336] Specific examples of compounds represented by formulas (21) and (22) include the following compounds.

[0337] [ka]

[0338] 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 preferably includes a fluorescent light-emitting material. Furthermore, in one embodiment of the organic EL element according to the present invention, the light-emitting layer preferably includes a phosphorescent material. Furthermore, in one embodiment of the organic EL element according to the present invention, it is preferable that the light-emitting layer is a single layer. Furthermore, in one embodiment of the organic EL element according to the present invention, it is preferable that the light-emitting layer is stacked in multiple layers.

[0339] There are no particular limitations on the blue fluorescent material that can be used in the light-emitting layer. Examples include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluorantene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, azavorin derivatives, and arylborane derivatives. Specifically, examples include N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviated as YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviated as YGAPA), and 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCBAPA).

[0340] There are no particular restrictions on the green fluorescent material that can be used in the light-emitting layer, and examples include aromatic amine derivatives. Specifically, these include 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).

[0341] There are no particular restrictions on the red fluorescent material that can be used in the light-emitting layer, and examples include tetracene derivatives and diamine derivatives. Specifically, examples include N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD) and 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluorantene-3,10-diamine (abbreviation: p-mPhAFD).

[0342] In one embodiment of the present invention, it is preferable that the light-emitting layer includes a fluorescent light-emitting material (fluorescent dopant material).

[0343] There are no particular restrictions on the blue phosphorescent materials that can be used in the light-emitting layer. Examples include iridium complexes, osmium complexes, platinum complexes, and other metal complexes. 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).

[0344] There are no particular restrictions on the green phosphorescent material that can be used in the light-emitting layer; for example, iridium complexes can be used. 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)).

[0345] There are no particular limitations on the red phosphorescent material that can be used in the light-emitting layer. Examples include metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes. 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).

[0346] 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.

[0347] 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.

[0348] There are no particular restrictions on the host material; for example, (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 and condensed polycyclic aromatic amine derivatives; and so on.

[0349] In one embodiment of the present invention, the light-emitting layer preferably contains an anthracene derivative, and it is preferable that at least one hydrogen atom present on the benzene ring of the anthracene derivative is deuterated. Specific examples of anthracene derivatives will be discussed later.

[0350] Specific examples of anthracene derivatives include metal complexes such as tris(8-quinolinolato)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (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); 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- Examples include aromatic amine compounds such as 9H-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). Multiple types of host materials may be used.

[0351] In particular, for blue fluorescent elements, it is preferable to use the following anthracene derivatives as the host material.

[0352] [ka]

[0353] [ka]

[0354] [ka]

[0355] [ka]

[0356] In one embodiment of the organic EL element according to the present invention, it is preferable that the light-emitting layer is stacked in a plurality of layers. When the light-emitting layer stacked in a plurality of layers is composed of, for example, a first light-emitting layer and a second light-emitting layer, at least one of the components constituting the first light-emitting layer is different from the components constituting the second light-emitting layer. For example, this includes embodiments in which the dopant material contained in the first light-emitting layer is different from the dopant material contained in the second light-emitting layer, or embodiments in which the host material contained in the first light-emitting layer is different from the host material contained in the second light-emitting layer.

[0357] In the organic EL element according to this embodiment, the light-emitting layer may include a layer containing a light-emitting compound that exhibits fluorescence emission with a main peak wavelength of 500 nm or less.

[0358] 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).

[0359] 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.

[0360] 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.

[0361] electron transport layer The electron transport layer is a layer containing a material with high electron transport properties (electron transport material), and is formed between the light-emitting layer and the cathode, or, if present, between the electron injection layer and the light-emitting layer. The electron transport layer may be a single layer or a multilayer structure containing two or more layers. For example, the electron transport layer may be a two-layer structure containing a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one embodiment of the present invention, it is preferable that the electron transport layer of the single layer structure is adjacent to the light-emitting layer, and it is also preferable that the electron transport layer closest to the anode in the multilayer structure, for example, the first electron transport layer of the two-layer structure described above, is adjacent to the light-emitting layer. In another embodiment of the present invention, a hole blocking layer or the like, described later, may be interposed between the electron transport layer of the single layer structure and the light-emitting layer, or between the electron transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer.

[0362] There are no particular restrictions on the electron transport layer; for example, (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; (2) Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; (3) Polymer compounds; etc.

[0363] There are no particular restrictions on the metal complexes, and examples include tris(8-quinolinolato)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviated as BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviated as BAlq), bis(8-quinolinolato)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviated as ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviated as ZnBTZ), and (8-quinolinolato)lithium (abbreviated as Liq).

[0364] There are no particular restrictions on the heteroaromatic compounds, for example, 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-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)- Examples include 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).

[0365] There are no particular restrictions on the polymer compounds used; for example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy), etc.

[0366] The above materials are 10 -6 cm 2 The material has an electron mobility of / Vs or higher. However, any material with higher electron transport properties than hole transport properties may be used for the electron transport layer. Furthermore, the electron transport layer may be a single layer or a stack of two or more layers, each containing the above material. When the electron transport layer has a two-layer structure, the anode-side layer is referred to as the first electron transport layer, and the cathode-side layer as the second electron transport layer.

[0367] 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); or compounds containing these metals. Such compounds are not particularly limited and include, for example, alkali metal oxides; alkali metal halides; alkali metal-containing organic complexes such as (8-quinolinolato)lithium (abbreviated as Liq); alkaline earth metal oxides; alkaline earth metal halides; alkaline earth metal-containing organic complexes; rare earth metal oxides; rare earth metal halides; and rare earth metal-containing organic complexes. Multiple compounds can also 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 and 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, there are no particular restrictions on the organic compound, but preferably it is a material that is excellent at transporting the received electrons. Specifically, for example, the materials that constitute the electron transport layer described above (metal complexes, heteroaromatic compounds, etc.) can be used. As the electron donor, any material that exhibits electron-donating properties to the organic compound is acceptable. There are no particular restrictions on the electron donor, but preferably alkali metals, alkaline earth metals, rare earth metals, and more preferably alkali metal oxides and alkaline earth metal oxides. There are no particular restrictions on the alkali metals, alkaline earth metals, and rare earth metals, and examples include lithium, cesium, magnesium, calcium, erbium, and ytterbium. There are no particular restrictions on the alkali metal oxides and alkaline earth metal oxides, and examples include lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviated as TTF) can also be used.

[0368] cathode There are no particular restrictions on the cathode, but it is preferable to use metals, alloys, electrically conductive compounds, or 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, i.e., 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; and so on. 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.

[0369] 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. There are no particular restrictions on the materials used for the insulating layer. Examples 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.

[0370] 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.

[0371] blocking layer Blocking layers such as electron blocking layers, hole blocking layers, and exciton blocking layers may be provided adjacent to the light-emitting layer. An electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer, and a hole blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron transport layer. An exciton blocking layer has the function of preventing excitons generated in the light-emitting layer from diffusing into surrounding layers and confining the excitons within the light-emitting layer.

[0372] Each layer of the organic EL element can be formed by conventionally known deposition methods, coating methods, etc. There are no particular limitations on the deposition method; for example, known methods such as vacuum deposition and molecular beam deposition (MBE) can be used. There are no particular limitations on the coating method; for example, known methods such as dipping, spin coating, casting, bar coating, and roll coating can be used, using a solution of the compound that forms the layer.

[0373] There are no particular restrictions on the thickness of each layer, but generally, if the thickness is too thin, defects such as pinholes are likely to occur, and if it is too thick, a high driving voltage is required and efficiency will be reduced. Therefore, the thickness is preferably 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm.

[0374] In one embodiment of the organic EL element of the present invention, the sum of the thickness of the first hole transport layer and the thickness of the second hole transport layer is 30 nm or more and 150 nm or less, preferably 40 nm or more and 130 nm or less. Furthermore, in one embodiment of the organic EL element of the present invention, the thickness of the second hole transport layer is 20 nm or more, preferably 25 nm or more, more preferably 35 nm or more, and preferably 100 nm or less. Furthermore, in one embodiment of the organic EL element of the present invention, the hole transport layer adjacent to the light-emitting layer is 20 nm or larger, preferably 25 nm or larger, more preferably 30 nm or larger, and preferably 100 nm or smaller. Furthermore, in one aspect of the organic EL element of the present invention, the film thickness D1 of the first hole transport layer and the film thickness D2 of the second hole transport layer satisfy the relationship 0.3<D2 / D1<4.0, preferably satisfy the relationship 0.5<D2 / D1<3.5, and more preferably satisfy the relationship 0.75<D2 / D1<3.0.

[0375] Examples of embodiments of the organic EL element of the present invention include: an organic EL element having the above two-layer hole transport layer structure, wherein: • a first embodiment, wherein 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, wherein both the first hole transport layer and the second hole transport layer contain the compound of the present invention; • a third embodiment, wherein 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 three-layer hole transport layer structure, wherein: • a fourth embodiment, wherein 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, wherein 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, wherein 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, wherein 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, wherein 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, wherein 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; • a tenth embodiment, wherein all of the first to third hole transport layers contain the compound of the present invention; and the like.

[0376] Electronic Device The aforementioned organic EL element can be used in display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and electronic devices such as lighting and vehicle light fixtures. In one aspect of the present invention, the electronic device preferably includes the organic electroluminescent element described above. [Examples]

[0377] The present invention will be described in more detail below using examples, but the present invention is not limited to the following examples.

[0378] Inventive compounds used in the manufacture of organic EL elements in Examples 1-8 [ka] [ka]

[0379] Comparative compounds used in the manufacture of organic EL elements in Comparative Examples 1 and 2 [ka]

[0380] Other compounds used in the production of organic EL elements in Examples 1-8 and Comparative Examples 1-2 [ka] [ka]

[0381] Fabrication of organic EL elements Example 1 A glass substrate with a 25mm x 75mm x 1.1mm ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was set to 130 nm. The glass substrate with the 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 form a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-1 to compound HA (HT-1:HA) was 97:3. Next, compound HT-1 was deposited onto the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, compound HT-2 (compound Inv-1) was deposited onto this first hole transport layer to form a second hole transport layer with a thickness of 10 nm. Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited onto this second hole transport layer to form a light-emitting layer with a thickness of 25 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 96:4. Next, compound ET-1 was deposited onto this light-emitting layer to form a first electron transport layer with a thickness of 5 nm. Next, compound ET-2 and Liq were co-deposited onto this first electron transport layer to form a second electron transport layer with a thickness of 20 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50. Next, LiF was deposited onto this second electron transport layer to form an electron injection electrode with a thickness of 1 nm. Then, metallic aluminum was deposited onto this electron-injection electrode to form a metallic cathode with a thickness of 50 nm. The layer configuration of the organic EL element of Example 1 obtained in this way is shown below. ITO(130) / HT-1:HA=97:3(10) / HT-1(80) / HT-2(10) / BH-1:BD-1=96:4(25) / ET-1(5) / ET-2:Liq=50:50(20) / LiF(1) / Al(50) In the above layer configuration, the numbers in parentheses represent the film thickness (nm), and the ratios represent the mass ratios.

[0382] Examples 2-8 and Comparative Examples 1-2 Organic EL devices for Examples 2-8 and Comparative Examples 1-2 were fabricated in the same manner as in Example 1, except that the compounds shown in Table 1 (second hole transport layer materials) were used instead of compound Inv-1.

[0383] Evaluation of organic EL elements Measurement of element lifespan (LT95) The resulting organic EL element was subjected to a current density of 50 mA / cm². 2 The device was driven by DC current, and the time (h) until the brightness decreased to 95% of the initial brightness was measured. This was defined as the 95% lifetime (LT95). Table 1 shows the relative values ​​(%) of the 95% life (LT95) of Examples 1-8 and Comparative Example 2, with the 95% life (LT95) of Comparative Example 1 set to 100.

[0384] [Table 1]

[0385] As is clear from the results in Table 1, compounds that satisfy the provisions of the present invention (compounds Inv-1 to Inv-8) provide organic EL devices with significantly improved device lifetimes compared to compounds that do not satisfy the provisions of the present invention (compounds Ref-1 and Ref-2).

[0386] The inventive compound synthesized in the synthesis example. [ka] [ka] Synthesis Example 1: Synthesis of Compound Inv-1 [ka]

[0387] Under an argon atmosphere, intermediate 1 (3.21 g, 10 mmol) and tetrahydrofuran (50 mL) were placed in a flask and cooled to -30°C while stirring. Then, a hexane solution of n-butyllithium (1.6 M, 6.25 mL, 10 mmol) was slowly added dropwise, and after the addition was complete, the mixture was stirred at -30°C for 5 minutes. Next, a tetrahydrofuran solution of intermediate 2 (1.0 M, 10 mL, 10 mmol) was slowly added dropwise, and the mixture was stirred for 6 hours while raising the temperature to room temperature. After that, the solvent was removed by distillation, and the resulting residue was purified by sublimation to obtain 2.0 g of compound Inv-1 as a white solid (yield 35%). Mass spectrometry analysis confirmed that the obtained substance was compound Inv-1, with a molecular weight of 579.82 and an m / z of 580.

[0388] Synthesis examples 2 to 8: Compound Inv-2 to Compound Inv-8 Compounds Inv-2 to Inv-8 were synthesized in the same manner as in Synthesis Example 1, except that intermediates 1 and 2 in Synthesis Example 1 were replaced with the compounds shown in Table 2 below.

[0389] [Table 2] [Explanation of Symbols]

[0390] 1, 11, 12 Organic EL elements 2 circuit boards 3 Anode 4 cathode 5. Emitting layer 6. Hole transport zone (hole transport layer) 6a Hole injection layer 6b First Hole Transport Layer 6c Second Hole Transport Layer 6d Third Hole Transport Layer 7. Electron transport band (electron transport layer) 7a First electron transport layer 7b Second electron transport layer 10, 20, 30 Light-emitting units

Claims

1. A compound represented by the following formula (1). 【Chemistry 1】 [In formula (1), N ＊ It is the central nitrogen atom. R １ and R ２ are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, or -Si(R ９０１ ')(R ９０２ ')(R ９０３ '). R ９０１ ' to R ９０３ ' are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms. When two or more of R ９０１ ' to R ９０３ ' exist, the two or more R ９０１ ' to R ９０３ ' may be the same or different. R ３ ~R ５ Each of these is independently a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heteroaryl group. ３ ~R ５ However, if each is independently a substituted or unsubstituted ring-forming aryl group with 6 to 30 carbon atoms, then R ３ ~R ５ In the case of substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms represented by R, the substituents "substituted or unsubstituted" do not include amino groups. ４ is a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, and R ３ and R ５ If R is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, ３ and R ５ At least one of these is a substituted or unsubstituted alkyl group having 2 to 30 carbon atoms. R ３ ~R ５ Two adjacent elements selected from the set may join together to form a ring, or they may not join together to form a ring. L １ and L ２ Each of these is independently an arylene group having 6 to 18 ring-forming carbon atoms, either single-bonded, substituted, or unsubstituted, or a heteroarylene group having 5 to 18 ring-forming atoms, either substituted or unsubstituted. R １ and R ２ However, if each is independently a substituted or unsubstituted aryl group with 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroaryl group with 5 to 30 ring-forming atoms, then R １ and R ２ The "number of ring-forming carbon atoms" in substituted or unsubstituted aryl groups with 6 to 30 ring-forming carbon atoms, R １ and R ２ The "number of ring-forming atoms" in heteroaryl groups with 5 to 30 substituted or unsubstituted ring-forming atoms, L １ and L ２ The "number of ring-forming carbon atoms" in the substituted or unsubstituted ring-forming arylene group with 6 to 18 carbon atoms, and L １ and L ２ In heteroarylene groups with substituted or unsubstituted ring-forming atoms numbering from 5 to 18, the total number of "ring-forming atoms" is 17 or more. R １ , R ２ , L １ , and L ２ Two adjacent elements selected from this set do not join with each other and do not form a ring. R ３ ~R ５ One will be selected from and R １ , R ２ , L １ , and L ２ The adjacent element selected from these elements may or may not join to form a ring.

2. R ３ ~R ５ The compound according to claim 1, wherein at least one selected from is a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.

3. R ３ ~R ５ The compound according to claim 1 or 2, wherein each is independently a substituted or unsubstituted ring-forming aryl group having 6 to 18 carbon atoms.

4. R ３ ~R ５ The compound according to any one of claims 1 to 3, wherein each is independently a substituted or unsubstituted phenyl group.

5. R １ and R ２ The compound according to any one of claims 1 to 4, wherein each 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.

6. R １ and R ２ The compound according to claim 5, wherein each of these is independently represented by the following formulas (2A), (2B), (2C), (2D), or (2E). 【Chemistry 2】 [In formula (2A), *21 is L １ or L ２ This represents a connection to [something]. 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 that 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, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C3-C15 cycloalkyl 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 １０１ ~R １０５ Two adjacent elements selected from this set do not join with each other and do not form a ring. R that 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 C3-C15 cycloalkyl 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. j is 0, 1, or 2, and k is 0 or 1, except when j is 2 and k is 0. When j=0 and k=0, *23 represents *21. When j=0 and k=1, *22 represents *21. When j=1 and k=0, *23 represents *22. 【Transformation 3】 [In formula (2B), *24 is L １ or L ２ This represents a connection to [something]. R １２１ ~R １２８ One of the options selected is a single bond that connects to *25. R that is not a single bond １２１ ~R １２８ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C3-C15 cycloalkyl 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 １２１ ~R １２８ Two adjacent elements selected from this set do not join with each other and do not form a ring. 【Chemistry 4】 [In formula (2C), *26 is L １ or L ２ This represents a connection to something. R １３１ ~R １４０ One of the options selected is a single bond that connects to *27. R that is not a single bond １３１ ~R １４０ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C3-C15 cycloalkyl 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 the aforementioned single bond １３１ to R １４０ any two adjacent groups selected from among the above do not bond to each other and do not form a ring.]] 【Transformation 5】 [In formula (2D), *28 is L １ or L ２ This represents a connection to something. X １ represents an oxygen atom, a sulfur atom, -CR ａ R ｂ , or -NR ｃ . *29 is R １４１ ~R １４８ , R ２００ ~R ２０３ , R ａ , R ｂ , or R ｃ It joins to one of the following. *29 is R ａ , R ｂ , and R ｃ When combining with any of the following, R ａ , R ｂ , and R ｃ One of these is either a single bond attached to *29 or a divalent group attached to *29. p is either 0 or 1. p is 0, X １ However, oxygen atom, sulfur atom, -CR ａ R ｂ , or -NR ｃ At that time, R ａ , R ｂ , R ｃ , and R １４１ ~R １４８ One of the options selected is a single bond that connects to *29. p is 1, X １ ga-CR ａ R ｂ or -NR ｃ At that time, R １４５ and R １４６ , R １４６ and R １４７ , or R １４７ and R １４８ One of the Rs is a single bond that connects to *e, and the other is a single bond that connects to *f, and is not a single bond that connects to *e or *f. １４５ ~R １４８ , R １４１ ~R １４４ , R ２００ ~R ２０３ , R ａ , R ｂ , and R ｃ One of the options selected is a single bond that connects to *29. p is 1, X １ When is an oxygen atom or a sulfur atom, R １４５ and R １４６ , R １４６ and R １４７ , or R １４７ and R １４８ One of the Rs is a single bond that connects to *e, and the other is a single bond that connects to *f, and is not a single bond that connects to *e or *f. １４５ ~R １４８ , R １４１ ~R １４４ , and R ２００ ~R ２０３ One of the options selected is a single bond that connects to *29. R that is not a single bond １４１ ~R １４８ , R which 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 C3-C15 cycloalkyl 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 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 is not a single bond as described above, nor is it a divalent group as described above. ａ , R ｂ , and R ｃ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C5 alkyl group, or a substituted or unsubstituted ring-forming C6-C12 aryl group. R is not a single bond as described above, nor is it a divalent group as described above. ａ , R ｂ , and R ｃ Two adjacent elements selected from this set may join together to form a ring, or they may not join together to form a ring. 【Transformation 6】 [In formula (2E), *30 is L １ or L ２ This represents a connection to something. 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 that is not a single bond １５１ ~R １５５ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C3-C15 cycloalkyl group, or an unsubstituted phenyl group. R that 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, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted ring-forming C3-C15 cycloalkyl group. R is not a hydrogen atom １６１ ~R １６５ At least one adjacent pair selected from the set 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 the set 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 a ring.

7. R １ and R ２ The compound according to claim 6, wherein each is independently represented by formula (2A), (2B), or (2D).

8. R １ and R ２ These are each independently represented by the above formula (2A) or (2B), R １ and R ２ The compound according to claim 6 or 7, wherein at least one of the is formula (2A).

9. The compound according to any one of claims 1 to 8, wherein the substituent in the case of "substituted or unsubstituted" is an unsubstituted C1 to C20 alkyl group, an unsubstituted ring-forming C3 to C20 cycloalkyl group, an unsubstituted ring-forming C6 to C18 aryl group, or an unsubstituted ring-forming C5 to C18 heteroaryl group.

10. A compound according to any one of claims 1 to 9, comprising at least one deuterium atom in the molecule.

11. A material for an organic electroluminescent device comprising the compound described in any one of claims 1 to 10.

12. An organic electroluminescent element having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer contains a compound according to any one of claims 1 to 10.

13. The organic electroluminescent element according to claim 12, wherein the organic layer includes a hole transport band between the anode and the light-emitting layer, and the hole transport band includes the compound.

14. 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 13, wherein one or both of the first hole transport layer and the second hole transport layer contain the compound.

15. The organic electroluminescent element according to any one of claims 12 to 14, wherein the light-emitting layer includes a fluorescent light-emitting material.

16. The organic electroluminescent element according to any one of claims 12 to 14, wherein the light-emitting layer includes a phosphorescent material.

17. An electronic device comprising an organic electroluminescent element according to any one of claims 12 to 16.

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