Compound, Material for Organic Electroluminescence Element, Organic Electroluminescence Element, and Electronic Device

Abstract

Provided is a compound represented by formula (1).

Description

Technical Field

[0001] The present invention relates to a novel compound, a material for an organic electroluminescence device, an organic electroluminescence device, and an electronic device.

Background Art

[0002] When a voltage is applied to an organic electroluminescence device (hereinafter also referred to as an organic EL device), holes are injected from the anode and electrons are injected from the cathode into the light-emitting layer, respectively. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons.

[0003] The performance of conventional organic EL devices has not yet been sufficient. Although the improvement of materials used in organic EL devices has been gradually advanced to enhance the device performance, further high performance is required.

Summary of the Invention

[0004] An object of the present invention is to provide a high-performance organic EL device and a compound capable of realizing the organic EL device.

[0005] As a result of intensive studies to achieve the above object, the present inventors have found that a compound having a specific structure contributes to the high performance of an organic EL device, and completed the present invention.

[0006] According to the present invention, the following compounds and the like are provided. 1. A compound represented by the following formula (1).

Chemical Formula

[0007] According to the present invention, a high-performance organic EL element and a compound capable of realizing the organic EL element can be provided.

Brief Description of the Drawings

[0008]

Figure 1

Embodiments for Carrying Out the Invention

[0009] [Definitions] In the present specification, the hydrogen atom includes isotopes having different numbers of neutrons, that is, protium, deuterium, and tritium.

[0010] In the present specification, in a chemical structural formula, at a bondable position where symbols such as "R" and "D" representing a deuterium atom are not explicitly shown, a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded.

[0011] In the present specification, the number of ring-forming carbon atoms represents the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded cyclically (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted by a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbon atoms. The "number of ring-forming carbon atoms" described below shall be the same 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 number of ring-forming carbon atoms of a 9,9-diphenylfluorenyl group is 13, and the number of ring-forming carbon atoms of a 9,9'-spirobifluorenyl group is 25. In addition, when, for example, an alkyl group is substituted as a substituent on a benzene ring, the number of carbon atoms of the 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 of the benzene ring substituted with an alkyl group is 6. Further, when, for example, an alkyl group is substituted as a substituent on a naphthalene ring, the number of carbon atoms of the 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 of the naphthalene ring substituted with an alkyl group is 10.

[0012] In this specification, the number of ring-forming atoms refers to the number of atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic ring, a condensed ring, and a ring assembly) (for example, a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, and a heterocyclic compound). Atoms that do not constitute the ring (for example, hydrogen atoms that terminate the bonds of the atoms constituting the ring) or atoms included in the substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms. The same shall apply to the "number of ring-forming atoms" described below unless otherwise specified. For example, the number of ring-forming atoms of a pyridine ring is 6, the number of ring-forming atoms of a quinazoline ring is 10, and the number of ring-forming atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or the number of atoms constituting a substituent is not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms of the pyridine ring to which a hydrogen atom or a substituent is bonded is 6. Further, for example, with respect to a hydrogen atom bonded to a carbon atom of a quinazoline ring or an atom constituting a substituent, it is not included in the number of quinazoline ring-forming atoms. Therefore, the number of ring-forming atoms of the quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

[0013] In this specification, in the expression "substituted or unsubstituted ZZ group having XX to YY carbon atoms", "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 the substituent 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.

[0014] In this specification, in the expression "ZZ group having XX to YY carbon atoms, which may be substituted or unsubstituted", "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 the substituent 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.

[0015] In this specification, an unsubstituted ZZ group represents the case where the "ZZ group which may be substituted or unsubstituted" is an "unsubstituted ZZ group", and a substituted ZZ group represents the case where the "ZZ group which may be substituted or unsubstituted" is a "substituted ZZ group". In this specification, "unsubstituted" in the case of "ZZ group which may be substituted or unsubstituted" means that the hydrogen atom in the ZZ group is not replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom. Also, in this specification, "substituted" in the case of "ZZ group which may be substituted or unsubstituted" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. Similarly, "substituted" in the case of "BB group substituted with AA group" means that one or more hydrogen atoms in the BB group are replaced by the AA group.

[0016] "Substituents described in this specification" Hereinafter, the substituents described in this specification will be described.

[0017] Unless otherwise specified in this specification, the number of ring-forming carbon atoms of the "unsubstituted aryl group" described in this specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18. Unless otherwise specified in this specification, the number of ring-forming atoms of the "unsubstituted heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18. Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkyl group" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6. Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted alkenyl group" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6. Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted alkynyl group" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6. Unless otherwise specified herein, the number of ring-forming carbon atoms in the "unsubstituted cycloalkyl group" described in this specification is 3 to 50, preferably 3 to 20, more preferably 3 to 6. Unless otherwise specified herein, the number of ring-forming carbon atoms in the "unsubstituted arylene group" described in this specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18. Unless otherwise specified herein, the number of ring-forming atoms in the "unsubstituted divalent heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18. Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted alkylene group" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6.

[0018] · "Substituted or unsubstituted aryl group" Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B), etc. (Here, the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is the "unsubstituted aryl group", and the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is the "substituted aryl group"). In this specification, when simply referring to the "aryl group", it includes both the "unsubstituted aryl group" and the "substituted aryl group". "Aryl group of substitution" means a group in which one or more hydrogen atoms of "unsubstituted aryl group" are replaced by substituents. Examples of "aryl group of substitution" include, for example, a group in which one or more hydrogen atoms of the "unsubstituted aryl group" in the following specific example group G1A are replaced by substituents, and examples of the aryl group of substitution in the following specific example group G1B. In addition, the examples of the "unsubstituted aryl group" and the examples of the "aryl group of substitution" listed here are only examples, and the "aryl group of substitution" described in this specification includes a group in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "aryl group of substitution" in the following specific example group G1B is further replaced by a substituent, and a group in which a hydrogen atom of the substituent in the "aryl group of substitution" in the following specific example group G1B is further replaced by a substituent.

[0019] · Unsubstituted aryl group (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, Benzoanthryl group, Phenanthryl group, Benzophenanthryl group, Phenalenyl group, Pyrenyl group, Chrysenyl group, Benzochrysenyl group, Triphenylenyl group, Benzotriphenylenyl group, Tetrasenyl group, Pentasenyl group, Fluorenyl group, 9,9'-Spirobifluorenyl group, Benzofluorenyl group, Dibenzofluorenyl group, Fluoranthenyl group, Benzofluoranhenyl group, Perylenyl group, and A monovalent aryl group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-1) to (TEMP-15).

[0020]

Chemical formula

[0021]

Chemical formula

[0022] ·Substituted aryl group (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-t-Butylphenyl group, Meta-t-Butylphenyl group, Ortho-t-Butylphenyl group, 3,4,5-Trimethylphenyl group, 9,9-Dimethylfluorenyl group, 9,9-Diphenylfluorenyl group 9,9-Bis(4-methylphenyl)fluorenyl group, 9,9-Bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, cyanophenyl group, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl group, and a group in which one or more hydrogen atoms of a monovalent group derived from the ring structures represented by the general formulas (TEMP-1) to (TEMP-15) are replaced with substituents.

[0023] · "substituted or unsubstituted heterocyclic group" The "heterocyclic group" described in this specification is a cyclic group containing at least one heteroatom in the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom. The "heterocyclic group" described in this specification is a monocyclic group or a condensed-ring group. The "heterocyclic group" described in this specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic groups (specific example group G2A), substituted heterocyclic groups (specific example group G2B), and the like. (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when simply referring to a "heterocyclic group", it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group". The "substituted heterocyclic group" means a group in which one or more hydrogen atoms of the "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of the "substituted heterocyclic group" include groups in which the hydrogen atoms of the "unsubstituted heterocyclic group" in the following specific example group G2A are replaced, and examples of the substituted heterocyclic group in the following specific example group G2B, etc. It should be noted that the examples of the "unsubstituted heterocyclic group" and the "substituted heterocyclic group" listed here are only examples, and the "substituted heterocyclic group" described in this specification includes groups in which the hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents.

[0024] The specific example 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 structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0025] The specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of the monovalent heterocyclic groups derived from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific example group G2B4).

[0026] ·Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1): Pyrrolyl group, Imidazolyl group, Pyrazolyl group, Triazolyl group, Tetrazolyl group, Oxazolyl group, Isoxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolizinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, an indazolyl group, a phenanthrolinyl group, a phenanthridinyl group, an acridinyl group, a phenazinyl group, a carbazolyl group, a benzocarbazolyl group, a morpholino group, a phenoxazinyl group, a phenothiazinyl group, an azacarbazolyl group and a diazacarbazolyl group.

[0027] · an unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): a furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a xanthenyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a benzoxazolyl group, a benzoisoxazolyl group, a phenoxazinyl group, a morpholino group, a dinaphthofuranyl group, Azadibenzofuranyl group, Diazaazadibenzofuranyl group, Azananofuranyl group, and Diazaazananofuranyl group.

[0028] · Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3): Thienyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl group, Benzothiophenyl group (benzothienyl group), Isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), Naphthobenzothiophenyl group (naphthobenzothienyl group), Benzothiazolyl group, Benzisothiazolyl group, Phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), Diazaazadibenzothiophenyl group (diazaazadibenzothienyl group), Azananobenzothiophenyl group (azananobenzothienyl group), and Diazaazananobenzothiophenyl group (diazaazananobenzothienyl group).

[0029] · Monovalent heterocyclic group 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]

Chemical formula

[0031]

Chemical formula

[0032] In the general formulas (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2. However, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH. In the general formulas (TEMP-16) to (TEMP-33), when at least one of X A and Y A is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0033] · Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): (9-Phenyl)carbazolyl group, (9-Biphenylyl)carbazolyl group, (9-Phenyl)phenylcarbazolyl group, (9-Naphthyl)carbazolyl group, Diphenylcarbazol-9-yl group, Phenylcarbazol-9-yl group, Methylbenzimidazolyl group, Ethylbenzimidazolyl group, Phenyltriazinyl group, Biphenylyltriazinyl group, Diphenyltriazinyl group, Phenylquinazolinyl group, and Biphenylylquinazolinyl group.

[0034] · Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): Phenyldibenzofuranyl group, Methyldibenzofuranyl group, t-Butyldibenzofuranyl group, and Monovalent residue of spiro[9H-xanthene-9,9’-[9H]fluorene].

[0035] · Substituted heterocyclic groups containing sulfur atoms (specific example group G2B3): Phenyldibenzothiophenyl group, Methyldibenzothiophenyl group, t-Butyldibenzothiophenyl group, and The monovalent residue of spiro[9H-thioxanthene-9,9’-[9H]fluorene].

[0036] · A group in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structures represented by the general formulas (TEMP-16) to (TEMP-33) are replaced with substituents (specific example group G2B4):

[0037] The above-mentioned "one or more hydrogen atoms of the monovalent heterocyclic group" means one or more hydrogen atoms selected from the hydrogen atoms bonded to the ring-forming carbon atoms of the monovalent heterocyclic group, the hydrogen atoms bonded to the nitrogen atom when at least one of XA and YA is NH, and the hydrogen atoms of the methylene group when one of XA and YA is CH2.

[0038] · "Substituted or unsubstituted alkyl group" Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B). (Here, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group", and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group".) Hereinafter, when simply referred to as "alkyl group", it includes both "unsubstituted alkyl group" and "substituted alkyl group". "Substituted alkyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced by substituents. Specific examples of the "substituted alkyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl group" (specific example group G3A) are replaced by substituents, and examples of the substituted alkyl group (specific example group G3B). In this specification, the alkyl group in the "unsubstituted alkyl group" means a chain alkyl group. Therefore, the "unsubstituted alkyl group" includes a linear "unsubstituted alkyl group" and a branched "unsubstituted alkyl group". Note that the examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" listed here are only examples, and the "substituted alkyl group" described in this specification includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" of specific example group G3B is further replaced by a substituent, and a group in which a hydrogen atom of the substituent in the "substituted alkyl group" of specific example group G3B is further replaced by a substituent.

[0039] · Unsubstituted alkyl group (specific example group G3A): Methyl group, Ethyl group, n-Propyl group, Isopropyl group, n-Butyl group, Isobutyl group, s-Butyl group, and t-Butyl group.

[0040] · Substituted alkyl group (specific example group G3B): Heptafluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-Trifluoroethyl group, and Trifluoromethyl group.

[0041] · "Substituted or unsubstituted alkenyl group" Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described in this specification include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group", and the "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group".) In this specification, when simply referring to an "alkenyl group", it includes both "unsubstituted alkenyl groups" and "substituted alkenyl groups". The "substituted alkenyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkenyl group" are replaced by substituents. Specific examples of the "substituted alkenyl group" include groups in which the following "unsubstituted alkenyl groups" (specific example group G4A) have substituents, and examples of substituted alkenyl groups (specific example group G4B), etc. It should be noted that the examples of the "unsubstituted alkenyl group" and the "substituted alkenyl group" listed here are only examples, and the "substituted alkenyl group" described in this specification includes 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 substituents in the "substituted alkenyl group" of specific example group G4B are further replaced by substituents.

[0042] · Unsubstituted alkenyl groups (specific example group G4A): Vinyl group, Allyl group, 1-Butenyl group, 2-Butenyl group, and 3-Butenyl group.

[0043] · Substituted alkenyl groups (specific example group G4B): 1,3-Butadienyl group, 1-Methylvinyl group, 1-Methylallyl group, 1,1-Dimethylallyl group, 2-Methylallyl group, and 1,2-Dimethylallyl group.

[0044] · "Substituted or unsubstituted alkynyl group" Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl groups (specific example group G5A), etc. (Here, the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group"). Hereinafter, when simply referred to as "alkynyl group", it includes both "unsubstituted alkynyl group" and "substituted alkynyl group". "Substituted alkynyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" are replaced by substituents. Specific examples of the "substituted alkynyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl groups" (specific example group G5A) are replaced by substituents, etc.

[0045] · Unsubstituted alkynyl group (specific example group G5A): Ethynyl group

[0046] · "Substituted or unsubstituted cycloalkyl group" Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described in this specification include the following unsubstituted cycloalkyl groups (specific example group G6A) and substituted cycloalkyl groups (specific example group G6B), etc. (Here, the unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group", and the substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group"). In this specification, when simply referred to as "cycloalkyl group", it includes both "unsubstituted cycloalkyl group" and "substituted cycloalkyl group". "Substituted cycloalkyl group" means a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced by substituents. Specific examples of the "substituted cycloalkyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl group" (specific example group G6A) are replaced by substituents, and examples of the substituted cycloalkyl group (specific example group G6B). It should be noted that the examples of the "unsubstituted cycloalkyl group" and the "substituted cycloalkyl group" listed here are only examples. The "substituted cycloalkyl group" described in this specification includes groups in which one or more hydrogen atoms bonded to the carbon atoms of the cycloalkyl group itself in the "substituted cycloalkyl group" of specific example group G6B are replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted cycloalkyl group" of specific example group G6B are further replaced by substituents.

[0047] · Unsubstituted cycloalkyl group (specific example group G6A): Cyclopropyl group, Cyclobutyl group, Cyclopentyl group, Cyclohexyl group, 1-Adamantyl group, 2-Adamantyl group, 1-Norbornyl group, and 2-Norbornyl group.

[0048] · Substituted cycloalkyl group (specific example group G6B): 4-Methylcyclohexyl group.

[0049] · Group represented by "-Si(R 901 )(R 902 )(R 903 )" Specific examples (specific example group G7) of the group represented by -Si(R 901 )(R 902 )(R 903 ) described in this specification include -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) are mentioned. Here, G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in specific example group G6. The plurality of G1 in -Si(G1)(G1)(G1) are the same as or different from each other. The plurality of G2 in -Si(G1)(G2)(G2) are the same as or different from each other. The plurality of G1 in -Si(G1)(G1)(G2) are the same as or different from each other. The plurality of G2 in -Si(G2)(G2)(G2) are the same as or different from each other. The plurality of G3 in -Si(G3)(G3)(G3) are the same as or different from each other. The plurality of G6 in -Si(G6)(G6)(G6) are the same as or different from each other.

[0050] · "Group represented by -O-(R 904 )" Specific examples (specific example group G8) of the group represented by -O-(R 904 ) described in this specification include -O(G1), -O(G2), -O(G3), and -O(G6) are mentioned. Here, G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.

[0051] · The group represented by "-S-(R 905 )" Specific examples (specific example group G9) of the group represented by -S-(R 905 ) described in this specification include -S(G1), -S(G2), -S(G3), and -S(G6) may be mentioned. Here, G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2. G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.

[0052] · The group represented by "-N(R 906 )(R 907 )" Specific examples (specific example group G10) of the group represented by -N(R 906 )(R 907 ) described in this specification include -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) may be mentioned. Here, G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2. G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in the specific example group G6. - The plurality of G1s in -N(G1)(G1) are the same as or different from each other. - The plurality of G2s in -N(G2)(G2) are the same as or different from each other. - The plurality of G3s in -N(G3)(G3) are the same as or different from each other. - The plurality of G6s in -N(G6)(G6) are the same as or different from each other.

[0053] · "Halogen atom" Specific examples (specific example group G11) of the "halogen atom" described in this specification include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.

[0054] · "Substituted or unsubstituted fluoroalkyl group" The "substituted or unsubstituted fluoroalkyl group" described in this specification means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced by fluorine atoms (perfluoro group). The carbon number of the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. The "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms of the "fluoroalkyl group" are replaced by substituents. In addition, the "substituted fluoroalkyl group" described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the "substituted fluoroalkyl group" are further replaced by substituents, and a group in which one or more hydrogen atoms of the substituents in the "substituted fluoroalkyl group" are further replaced by substituents. Specific examples of the "unsubstituted fluoroalkyl group" include examples of groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced by fluorine atoms.

[0055] · "Substituted or unsubstituted haloalkyl group" As used herein, the "substituted or unsubstituted haloalkyl group" means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced by halogen atoms. Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted haloalkyl group" means a group in which one or more hydrogen atoms in the "haloalkyl group" are replaced by substituents. It should be noted that the "substituted haloalkyl group" described herein also includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the "substituted haloalkyl group" are further replaced by substituents, and a group in which one or more hydrogen atoms of the substituents in the "substituted haloalkyl group" are further replaced by substituents. Specific examples of the "unsubstituted haloalkyl group" include examples of groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced by halogen atoms. The haloalkyl group may sometimes be referred to as a halogenated alkyl group.

[0056] · "Substituted or unsubstituted alkoxy group" Specific examples of the "substituted or unsubstituted alkoxy group" described herein are groups represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0057] · "Substituted or unsubstituted alkylthio group" Specific examples of the "substituted or unsubstituted alkylthio group" described in this specification are groups represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3. The carbon number of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0058] · "Substituted or unsubstituted aryloxy group" Specific examples of the "substituted or unsubstituted aryloxy group" described in this specification are groups represented by -O(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 aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0059] · "Substituted or unsubstituted arylthio group" Specific examples of the "substituted or unsubstituted arylthio group" described in this specification are groups 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 in this specification.

[0060] · "Substituted or unsubstituted trialkylsilyl group" Specific examples of the "trialkylsilyl group" described in this specification are groups represented by -Si(G3)(G3)(G3), where G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3. The plurality of G3 in -Si(G3)(G3)(G3) are the same as or different from each other. The carbon number of each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.

[0061] · "Substituted or unsubstituted aralkyl group" Specific examples of the "substituted or unsubstituted aralkyl group" described in this specification include a 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, the "aralkyl group" is a group in which a hydrogen atom of the "alkyl group" is replaced with an "aryl group" as a substituent, and is one aspect of the "substituted alkyl group". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the number of carbon atoms of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification. Specific examples of the "substituted or unsubstituted aralkyl group" 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, etc.

[0062] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described in this specification is preferably phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group, pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, 9,9'-spirobifluorenyl group, 9,9-dimethylfluorenyl group, and 9,9-diphenylfluorenyl group, etc.

[0063] The substituted or unsubstituted heterocyclic group described in this specification is preferably a pyridyl group, pyrimidinyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, benzimidazolyl group, phenanthrolinyl group, carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group, dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazol-4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group, etc., unless otherwise described in this specification.

[0064] In this specification, unless otherwise described in this specification, the carbazolyl group is specifically any of the following groups.

[0065]

Chemical formula

[0066] In this specification, unless otherwise described in this specification, the (9-phenyl)carbazolyl group is specifically any of the following groups.

[0067]

Chemical formula

[0068] In the general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding site.

[0069] In this specification, unless otherwise specified herein, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups.

[0070]

Chemical formula

[0071] In the general formulas (TEMP-34) to (TEMP-41), * represents a bonding site.

[0072] Unless otherwise specified herein, the substituted or unsubstituted alkyl group described in this specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, etc.

[0073] · "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above "substituted or unsubstituted aryl group". Specific examples (specific example group G12) of the "substituted or unsubstituted arylene group" include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1, etc.

[0074] · "Substituted or unsubstituted divalent heterocyclic group" Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom on the heterocyclic ring from the above "substituted or unsubstituted heterocyclic group". Specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group" include divalent groups derived by removing one hydrogen atom on the heterocyclic ring from the "substituted or unsubstituted heterocyclic group" described in specific example group G2, etc.

[0075] · "Substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group". Specific examples (specific example group G14) of the "substituted or unsubstituted alkylene group" include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3, etc.

[0076] Unless otherwise specified in this specification, the substituted or unsubstituted arylene group described in this specification is preferably a group of any of the following general formulas (TEMP-42) to (TEMP-68).

[0077]

Chemical formula

[0078]

Chemical formula

[0079] In the general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent. In the general formulas (TEMP-42) to (TEMP-52), * represents a bonding site.

[0080]

Chemical formula

[0081] In the general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent. Formula Q9 and Q 10 may be bonded to each other via a single bond to form a ring. In the general formulas (TEMP-53) to (TEMP-62), * represents a bonding site.

[0082]

Chem.

[0083] In the general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent. In the general formulas (TEMP-63) to (TEMP-68), * represents a bonding site.

[0084] Unless otherwise specified herein, the substituted or unsubstituted divalent heterocyclic group described herein is preferably a group of any of the following general formulas (TEMP-69) to (TEMP-102).

[0085]

Chem.

[0086]

Chem.

[0087]

Chem.

[0088] In the general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0089]

Chem.

[0090]

Chem.

[0091] [Chemistry]

[0092] [Chemistry]

[0093] In the general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0094] The above is the description of "the substituents described in this specification".

[0095] · "When bonding to form a ring" In this specification, the case of "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted monocyclic ring, or bond to each other to form a substituted or unsubstituted condensed ring, or do not bond to each other" means the case where "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted monocyclic ring", the case where "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted condensed ring", and the case where "one or more sets of two or more adjacent ones do not bond to each other". Regarding the case in this specification where "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted condensed ring" (hereinafter, these cases may be collectively referred to as "the case of bonding to form a ring"), the following will be described. Taking the case of an anthracene compound represented by the following general formula (TEMP-103) whose mother skeleton is an anthracene ring as an example.

[0096] [Chemistry]

[0097] For example, R921 ~R 930 In the case of "one or more sets consisting of two or more adjacent ones are combined with each other to form a ring", the set consisting of two adjacent ones that forms one set is R 921 and R 922 and the set of R 922 and R 923 and the set of R 923 and R 924 and the set of R 924 and R 930 and the set of R 930 and R 925 and the set of R 925 and R 926 and the set of R 926 and R 927 and the set of R 927 and R 928 and the set of R 928 and R 929 and the set of, and R 929 and R 921 and the set of.

[0098] The above "one or more sets" means that two or more sets consisting of two or more adjacent ones may form a ring at the same time. For example, R 921 and R 922 are combined with each other to form ring Q A , and at the same time R 925 and R 926 are combined with each other to form ring Q B is formed, then the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0099]

Chemical formula

[0100] The case where a "set consisting of two or more adjacent ones" forms a ring includes not only the case where a set consisting of "two" adjacent ones is combined as in the above example, but also the case where a set consisting of "three or more" adjacent ones is combined. For example, R 921 and R 922 are combined with each other to form ring Q A , and R 922 and R923 are bonded to each other to form ring Q C to form, and a group consisting of three adjacent ones (R 921 , R 922 and R 923 ) are bonded to each other to form a ring and are condensed to the anthracene backbone. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C share R 922 .

[0101] [Chemical formula]

[0102] The "monocyclic ring" or "condensed ring" formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when "a set of two adjacent ones" forms a "monocyclic ring" or "condensed ring", the "monocyclic ring" or "condensed ring" can form a saturated ring or an unsaturated ring. For example, ring Q A and ring Q B formed in the general formula (TEMP-104) are each a "monocyclic ring" or "condensed ring", respectively. Also, ring Q A and ring Q C formed in the general formula (TEMP-105) are "condensed rings". Ring Q A and ring Q C in the general formula (TEMP-105) are a condensed ring formed by the condensation of ring Q A and ring Q C . If ring Q A in the general formula (TMEP-104) is a benzene ring, ring Q A is a monocyclic ring. If ring Q A in the general formula (TMEP-104) is a naphthalene ring, ring Q A is a condensed ring.

[0103] The "unsaturated ring" includes aromatic hydrocarbon rings, aromatic heterocyclic rings, aliphatic hydrocarbon rings having unsaturated bonds, i.e., double bonds and / or triple bonds in the ring structure (e.g., cyclohexene, cyclohexadiene, etc.), and non-aromatic heterocyclic rings having unsaturated bonds (e.g., dihydropyran, imidazoline, pyrazoline, quinolizine, indoline, isoindoline, etc.). The "saturated ring" includes an aliphatic hydrocarbon ring having no unsaturated bond or a non-aromatic heterocyclic ring having no unsaturated bond. Specific examples of the aromatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G1 are terminated by hydrogen atoms. Specific examples of the aromatic heterocyclic ring include structures in which the aromatic heterocyclic ring groups exemplified as specific examples in Specific Example Group G2 are terminated by hydrogen atoms. Specific examples of the aliphatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G6 are terminated by hydrogen atoms. "Forming a ring" means forming a ring with only a plurality of atoms of the mother skeleton or a plurality of atoms of the mother skeleton and one or more arbitrary atoms. For example, in the general formula (TEMP-104), the ring Q formed by bonding R 921 and R 922 to each other means a ring formed by a carbon atom of the anthracene skeleton to which R A is bonded, a carbon atom of the anthracene skeleton to which R 921 is bonded, and one or more arbitrary atoms. As a specific example, when forming the ring Q 922 with R 921 and R 922 , when a single-ring unsaturated ring is formed by a carbon atom of the anthracene skeleton to which R A is bonded, a carbon atom of the anthracene skeleton to which R 921 is bonded, and four carbon atoms, the ring formed by R 922 and R 921 and R 922 is a benzene ring.

[0104] Here, "any atom" is preferably at least one atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, unless otherwise described in this specification. In any atom (for example, in the case of a carbon atom or a nitrogen atom), a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described later. When any atom other than a carbon atom is included, the formed ring is a heterocyclic ring. The "one or more arbitrary atoms" constituting a monocyclic or condensed ring are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and still more preferably 3 or more and 5 or less, unless otherwise described in this specification. Unless otherwise described in this specification, among the "monocyclic ring" and the "condensed ring", the "monocyclic ring" is preferred. Unless otherwise described in this specification, among the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred. Unless otherwise described in this specification, the "monocyclic ring" is preferably a benzene ring. Unless otherwise described in this specification, the "unsaturated ring" is preferably a benzene ring. When "one or more sets of two or more adjacent ones" are "bonded to each other to form a substituted or unsubstituted monocyclic ring" or "bonded to each other to form a substituted or unsubstituted condensed ring", unless otherwise described in this specification, preferably, one or more sets of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted "unsaturated ring" composed of a plurality of atoms of the parent skeleton and at least one atom selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0105] The substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent is, for example, the "arbitrary substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the section of the "substituents described in this specification" mentioned above. When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "arbitrary substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the section of "substituents described in this specification" mentioned above. The above is the explanation for the case where "one or more of the sets consisting of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more of the sets consisting of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted condensed ring" (the case of "bonding to form a ring").

[0106] · Substituent in the case of "substituted or unsubstituted" In one embodiment of this specification, the substituent in the case of "substituted or unsubstituted" (which may be referred to as "arbitrary substituent" in this specification) is, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms and groups selected from the group consisting of, etc., Here, R 901 ~R 907 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, an aryl group having 6 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, or a heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted. R 901 When two or more Rs are present, the two or more Rs 901 may be the same as or different from each other, R 902 When two or more Rs are present, the two or more Rs 902 may be the same as or different from each other, R 903 When two or more Rs are present, the two or more Rs 903 may be the same as or different from each other, R 904 When two or more Rs are present, the two or more Rs 904 may be the same as or different from each other, R 905 When two or more Rs are present, the two or more Rs 905 may be the same as or different from each other, R 906 When two or more Rs are present, the two or more Rs 906 may be the same as or different from each other, R 907 When two or more Rs are present, the two or more Rs 907 may be the same as or different from each other.

[0107] In one embodiment, the substituent in the case of "substituted or unsubstituted" is an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring-forming carbon atoms, and a heterocyclic group having 5 to 50 ring-forming atoms selected from the group consisting of.

[0108] In one embodiment, the substituent in the case of "substituted or unsubstituted" is an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring-forming carbon atoms, and a heterocyclic group having 5 to 18 ring-forming atoms a group selected from the group consisting of

[0109] Specific examples of each of the above-mentioned optional substituents are the specific examples of the substituents described in the section of "Substituents Described in the Present Specification" described above.

[0110] Unless otherwise specified in the present specification, any adjacent substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, and more preferably a benzene ring. Unless otherwise specified in the present specification, any substituent may further have a substituent. The substituents further possessed by any substituent are the same as the above-mentioned any substituents.

[0111] In the present specification, a numerical range represented by "AA to BB" means a range including the numerical value AA described before "AA to BB" as the lower limit value and the numerical value BB described after "AA to BB" as the upper limit value.

[0112] [Novel compound] The compound according to one aspect of the present invention is represented by the following formula (1). [Chemical formula] [In formula (1), X1 and X2 are each independently N or CH, and one of X1 and X2 is N. Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring-forming atoms which may be substituted or unsubstituted. L1 to L3 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or It is a divalent heterocyclic group having 5 to 50 ring-forming atoms, which may or may not be substituted. n1 is an integer from 0 to 4. When n1 is 0, (L1) n1 is a single bond. When there are a plurality of L1, each of the plurality of L1 may be the same or different. n2 is an integer from 0 to 4. When n2 is 0, (L2) n2 is a single bond. When there are a plurality of L2, each of the plurality of L2 may be the same or different. n3 is an integer from 0 to 4. When n3 is 0, (L3) n3 is a single bond. When there are a plurality of L3, each of the plurality of L3 may be the same or different. R 11 ~R 19 are each independently a hydrogen atom or a substituent R. R 11 ~R 19 Two or more adjacent groups among them do not bond to each other. R 21 and R 22 bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring. R 21 and R 22 that do not form the substituted or unsubstituted saturated or unsaturated ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms. The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R904 ) -S-(R 905 ) -N(R 906 )(R 907 ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms selected from the group consisting of. R 901 ~R 907 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 monovalent heterocyclic group having 5 to 50 ring-forming atoms. R 901 ~R 907 When two or more R 901 ~R 907 are present, each of the two or more R ~R

[0113] In formula (1), either one of X1 and X2 is N and the other is CH. That is, when X1 is N, X2 is CH. When X2 is N, X1 is CH.

[0114] In formula (1), when a plurality of L1 are present (when n1 is 2 or more), Ar1 is bonded to the L1 farthest from the nitrogen-containing six-membered ring containing X1 and X2. Similarly, when a plurality of L2 are present (when n2 is 2 or more), Ar2 is bonded to the L2 farthest from the nitrogen-containing six-membered ring containing X1 and X2. Similarly, when a plurality of L3 are present (when n3 is 2 or more), the benzofluorene skeleton is bonded to the L3 farthest from the nitrogen-containing six-membered ring containing X1 and X2. For example, when n1 is 2, n2 is 3, and n3 is 2, the compound represented by formula (1) has the following structure. The "nitrogen-containing six-membered ring containing X1 and X2" is shown as ring α. [Chemical formula]

[0115] In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (11). [Chemical formula] [In formula (11), X1, X2, Ar1, Ar2, L1, L2, n1, n2, R 11 ~R 19 , R 21 , and R 22 are as defined in the formula (1).]

[0116] In one embodiment, R 21 and R 22 in formula (11) do not form a substituted or unsubstituted saturated or unsaturated ring.

[0117] In one embodiment, R 21 and R 22 in formula (11) are a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms.

[0118] In one embodiment, R 21 and R 22 in formula (11) are methyl groups.

[0119] In one embodiment, X1 in formula (11) is N and X2 is CH.

[0120] In one embodiment, the compound represented by the formula (11) is a compound represented by any one of the following formulas (111) to (113). [Chemical formula] [Chemical] [In formula (111), L1, L2, n1, n2, and R 11 ~R 19 are as defined in the above formula (1). R 111 ~R 120 are each independently a hydrogen atom or a substituent R. Two or more adjacent groups among R 111 ~R 120 do not bond to each other. [In formula (112), L1, L2, n1, n2, and R 11 ~R 19 are as defined in the above formula (1). Y1 is N(R 129 ), C(R 130a )(R 130b ), O, or S. R 121 ~R 129 One of them represents a bond to L2. R that does not represent a bond to L2 121 ~R 129 are each independently a hydrogen atom or a substituent R. Two or more adjacent groups among R that do not represent a bond to L2 121 ~R 129 do not bond to each other. R 130a and R 130b either bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring. R that does not form the substituted or unsubstituted saturated or unsaturated ring 130a and R 130b are each independently a hydrogen atom or a substituent R. R 131 ~R 135 are each independently a hydrogen atom or a substituent R. Two or more adjacent groups among R 131 ~R 135 do not bond to each other. [In formula (113), L1, L2, n1, n2, and R11 ~R 19 is as defined in the above formula (1). R 141 ~R 150 Any one of them represents a bond with L2. R that does not represent a bond with L2 141 ~R 150 are each independently a hydrogen atom or a substituent R. R that does not represent a bond with L2 141 ~R 150 A group consisting of two or more adjacent ones among them do not bond to each other. R 151 ~R 155 are each independently a hydrogen atom or a substituent R. R 151 ~R 155 A group consisting of two or more adjacent ones among them do not bond to each other. The substituent R is as defined in the above formula (1).]

[0121] In one embodiment, R in formula (112) 123 represents a bond with L2. R 123 When represents a bond with L2, the compound represented by formula (112) has the following structure.

Chemical formula

[0122] In one embodiment, Y1 is O.

[0123] In one embodiment, R in formula (113) 141 R 143 or R 149 represents a bond with L2.

[0124] In one embodiment, X1 in formula (11) is CH and X2 is N.

[0125] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (21).

Chemical formula

[0126] In one embodiment, R 21 and R 22 in formula (21) do not form a substituted or unsubstituted saturated or unsaturated ring.

[0127] In one embodiment, R 21 and R 22 in formula (21) are substituted or unsubstituted alkyl groups having 1 to 5 carbon atoms.

[0128] In one embodiment, R 21 and R 22 in formula (21) are methyl groups.

[0129] In one embodiment, L 21 in formula (21) is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms.

[0130] In one embodiment, L 21 in formula (21) is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

[0131] In one embodiment, X1 in formula (21) is N and X2 is CH.

[0132] In one embodiment, the compound represented by the formula (21) is a compound represented by the following formula (211) or formula (212). [Chemical formula] [In formula (211), Ar1, Ar2, L1, L2, n1, n2, and R 11 ~R 19 are as defined in the formula (1). R 211 ~R 214 are each independently a hydrogen atom or a substituent R. Two or more adjacent groups among R 211 ~R 214 do not bond to each other. In formula (212), Ar1, Ar2, L1, L2, n1, n2, and R 11 ~R 19 are as defined in the formula (1). R 221 ~R 226 are each independently a hydrogen atom or a substituent R. Two or more adjacent groups among R 221 ~R 226 do not bond to each other. The substituent R is as defined in the formula (1).]

[0133] In one embodiment, X1 in formula (21) is CH and X2 is N.

[0134] In one embodiment, the compound represented by the formula (21) is a compound represented by the following formula (221) or formula (222). [Chemical formula] [In formula (221), Ar1, Ar2, L1, L2, n1, n2, and R 11 ~R 19 are as defined in the formula (1). R 211 ~R 214is, independently of each other, a hydrogen atom or a substituent R. R 211 ~R 214 Two or more adjacent groups among them do not bond to each other. In formula (222), Ar1, Ar2, L1, L2, n1, n2, and R 11 ~R 19 are as defined in the above formula (1). R 221 ~R 226 is, independently of each other, a hydrogen atom or a substituent R. R 221 ~R 226 Two or more adjacent groups among them do not bond to each other. The substituent R is as defined in the above formula (1).

[0135] In one embodiment, Ar1 and Ar2 in formula (21) are, independently of each other, a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 18 ring-forming atoms.

[0136] In one embodiment, Ar1 and Ar2 in formula (21) are, independently of each other, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0137] In one embodiment, L1 and L2 in formula (1) are, independently of each other, a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

[0138] In one embodiment, R 11 ~R 19 is a hydrogen atom.

[0139] In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (1), and the substituent R are groups selected from the group consisting of an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring-forming carbon atoms, and a monovalent heterocyclic group having 5 to 50 ring-forming atoms.

[0140] In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (1), and the substituent R are groups selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring-forming carbon atoms, and a monovalent heterocyclic group having 5 to 18 ring-forming atoms.

[0141] In one embodiment, the compound represented by formula (1) has at least one deuterium atom in the molecule as a hydrogen atom.

[0142] As used herein, "having a deuterium atom as a hydrogen atom" means that the ratio of the deuterium atom to the total of the light hydrogen atom and the deuterium atom in the hydrogen atom is higher than the natural abundance ratio. That the ratio of the deuterium atom to the total of the light hydrogen atom and the deuterium atom is higher than the natural abundance ratio can be confirmed by a nuclear magnetic resonance apparatus.

[0143] In one embodiment, the compound represented by formula (1) does not have a deuterium atom in the molecule as a hydrogen atom.

[0144] As used herein, "not having a deuterium atom as a hydrogen atom" means that in all hydrogen atoms in the molecule, the ratio of the deuterium atom to the total of the light hydrogen atom and the deuterium atom is equal to or less than the natural abundance ratio. In other words, a compound represented by formula (1) that does not have a deuterium atom in the molecule as a hydrogen atom may contain the deuterium atom at a ratio equal to or less than the natural abundance ratio. The abundance of the light hydrogen atom can be confirmed by a nuclear magnetic resonance apparatus.

[0145] In one embodiment, Ar1 in formula (1) has at least one deuterium atom as a hydrogen atom. In one embodiment, Ar2 in formula (1) has at least one deuterium atom as a hydrogen atom. In one embodiment, L3 in formula (1) has at least one deuterium atom as a hydrogen atom. In one embodiment, the hydrogen atom R in formula (1) 11 ~R19 , R 21 , and R 22 , and the substituent R which is R 11 ~R 19 , R 21 , and R 22 At least one of the hydrogen atoms possessed by is a deuterium atom.

[0146] In one embodiment, L in formula (1) 23 does not have a deuterium atom as a hydrogen atom.

[0147] In one embodiment, in formula (1) The hydrogen atom which is R 11 ~R 19 , and The substituent R which is R 11 ~R 19 The hydrogen atoms possessed by are protium atoms. In one embodiment, R in formula (1) 21 and R 22 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and the R 21 and R 22 The hydrogen atoms possessed by are protium atoms.

[0148] The compound represented by formula (1) can be synthesized by following the examples and using known alternative reactions and raw materials according to the target product.

[0149] Specific examples of the compound represented by formula (1) are described below, but these are merely illustrative, and the compound represented by formula (1) is not limited to the following specific examples.

[0150]

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[0151] [Materials for Organic Electroluminescent Devices] The compound according to one aspect of the present invention is useful as a material for an organic EL device, for example, as a material used in the electron transport band of an organic EL device.

[0152] [Organic EL Device] An organic EL device according to one aspect of the present invention will be described. The organic EL device according to one aspect of the present invention has a cathode, an anode, and one or more organic layers disposed between the cathode and the anode, and at least one of the organic layers contains a compound according to one aspect of the present invention (the compound represented by formula (1)).

[0153] In one embodiment, an organic EL element according to one aspect of the present invention includes an anode, a light-emitting layer, an electron transport region, and a cathode in this order, and the electron transport region includes a compound according to one aspect of the present invention (a compound represented by formula (1)).

[0154] In one embodiment, the electron transport region has, in this order from the light-emitting layer side, a first layer (also referred to as a "first electron transport layer" or a "hole blocking layer") and a second layer (also referred to as a "second electron transport layer"), and the first layer contains a compound represented by formula (1). As the second layer in this case, for example, the configuration of the electron transport layer described later can be applied.

[0155] As a typical element configuration of the organic EL element, a structure in which the following structures are laminated on a substrate is exemplified. (1) Anode / Light-emitting layer / Electron transport region / Cathode (2) Anode / Hole transport region / Light-emitting layer / Electron transport region / Cathode ( " / " indicates that each layer is laminated adjacent to each other. ) The electron transport region generally consists of one or more layers selected from an electron injection layer and an electron transport layer. The hole transport region generally consists of one or more layers selected from a hole injection layer and a hole transport layer.

[0156] The schematic configuration of the organic EL element according to one aspect of the present invention will be described with reference to FIG. 1. An organic EL element 1 according to one aspect of the present invention has a substrate 2, an anode 3, a light-emitting layer 5, a cathode 10, a hole transport region 4 between the anode 3 and the light-emitting layer 5, and an electron transport region 6 between the light-emitting layer 5 and the cathode 10.

[0157] Hereinafter, members that can be used in the organic EL element according to one aspect of the present invention, and materials other than the above compounds that constitute each layer will be described.

[0158] (Substrate) The substrate is used as a support for the light-emitting element. As the substrate, for example, glass, quartz, plastic, etc. can be used. Also, a flexible substrate may be used. A flexible substrate is a substrate that can be bent (flexible), and examples thereof include plastic substrates made of polycarbonate and polyvinyl chloride.

[0159] (Anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, and mixtures thereof having a large work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene, etc. can be mentioned. In addition, gold (Au), platinum (Pt), or nitrides of metal materials (for example, titanium nitride), etc. can be mentioned.

[0160] (Hole injection layer) The hole injection layer is a layer containing a substance with high hole injection properties. As substances with high hole injection properties, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compounds, or polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used.

[0161] (Hole transport layer) The hole transport layer is a layer containing a substance with high hole transport properties. For the hole transport layer, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. However, as long as it is a substance with higher hole transport properties than electrons, other substances may be used. In addition, the layer containing a substance with high hole transport properties may be not only a single layer but also a laminate of two or more layers made of the above substances.

[0162] (Guest (dopant) material of the light-emitting layer) The light-emitting layer is a layer containing a highly luminescent substance, and various materials can be used. For example, as the highly luminescent substance, a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used. A fluorescent compound is a compound that can emit light from the singlet excited state, and a phosphorescent compound is a compound that can emit light from the triplet excited state. As a blue fluorescent light-emitting material that can be used in the light-emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. can be used. As a green fluorescent light-emitting material that can be used in the light-emitting layer, aromatic amine derivatives, etc. can be used. As a red fluorescent light-emitting material that can be used in the light-emitting layer, tetracene derivatives, diamine derivatives, etc. can be used. As a blue phosphorescent light-emitting material that can be used in the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used. As a green phosphorescent light-emitting material that can be used in the light-emitting layer, iridium complexes, etc. are used. As a red phosphorescent light-emitting material that can be used in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used.

[0163] (Host material of the light-emitting layer) The light-emitting layer may have a structure in which the above-mentioned highly luminescent substance (guest material) is dispersed in another substance (host material). As the substance for dispersing the highly luminescent substance, various substances can be used, and it is preferable to use a substance having a higher lowest unoccupied molecular orbital level (LUMO level) and a lower highest occupied molecular orbital level (HOMO level) than the highly luminescent substance. As substances (host materials) for dispersing highly luminescent substances, 1) metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes, 2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives, 3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives, 4) aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives are used.

[0164] (Electron transport layer) The electron transport layer is a layer containing a substance with high electron transport properties. For the electron transport layer, 1) metal complexes such as aluminum complexes, beryllium complexes, zinc complexes, etc., 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives, etc., 3) polymer compounds can be used. In one aspect of the present invention, the electron transport layer may or may not contain the above other substances in addition to the compound (the compound represented by formula (1)) according to one aspect of the present invention.

[0165] (Electron injection layer) The electron injection layer is a layer containing a substance with high electron injection properties. For the electron injection layer, metal complex compounds such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), 8-hydroxyquinolinolato-lithium (Liq), etc., alkali metals, alkaline earth metals, or their compounds such as lithium oxide (LiO x ) can be used.

[0166] (Cathode) For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture 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, that is, 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 (for example, MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these. The cathode is usually formed by a vacuum evaporation method or a sputtering method. When using a silver paste or the like, a coating method such as a coating method or an inkjet method can be used.

[0167] When an electron injection layer is provided, regardless of the work function, the cathode can be formed using various conductive materials such as aluminum, silver, ITO, graphene, indium tin oxide containing silicon or silicon oxide, etc.

[0168] In the organic EL element according to one aspect of the present invention, the film thickness of each layer is not particularly limited, but generally, in order to suppress defects such as pinholes, keep the applied voltage low, and improve the light emission efficiency, a range of usually several nm to 1 μm is preferable.

[0169] In the organic EL element according to one aspect of the present invention, the formation method of each layer is not particularly limited. A formation method by a conventionally known vacuum evaporation method, spin coating method, etc. can be used. Each layer such as the light emitting layer can be formed by a known method by a coating method such as a vacuum evaporation method, a molecular beam epitaxy method (MBE method), or a dipping method, spin coating method, casting method, bar coating method, roll coating method, etc. of a solution dissolved in a solvent.

[0170] [Electronic device] An electronic device according to one aspect of the present invention is characterized by including an organic EL element according to one aspect of the present invention. Specific examples of electronic devices include display components such as organic EL panel modules, display devices such as televisions, mobile phones, or personal computers, and light-emitting devices such as lighting or vehicle lamps.

Example

[0171] <Compound> The compound represented by formula (1) used in the production of the organic EL element of the example is shown below.

Chemical formula

Chemical formula

[0172] The compound used in the production of the organic EL element of the comparative example is shown below.

Chemical formula

[0173] Other compounds used in the production of the organic EL elements of the examples and comparative examples are shown below.

Chemical formula

Chemical formula

[0174] Example 1 <Fabrication of organic EL element> The organic EL element was fabricated as follows. A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) having a size of 25 mm × 75 mm × 1.1 mm thick was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV-ozone cleaned for 30 minutes. The film thickness of ITO was 130 nm. The glass substrate with a transparent electrode after cleaning was mounted on the substrate holder of a vacuum evaporation apparatus. First, compound HTL-1 and HI-1 were co-evaporated so that the ratio of compound HI-1 was 3% by mass to cover the transparent electrode on the surface where the transparent electrode was formed, and a hole injection layer with a film thickness of 10 nm was formed. Compound HTL-1 was evaporated on the hole injection layer to form a first hole transport layer with a film thickness of 80 nm. Compound EBL-1 was evaporated on the first hole transport layer to form a second hole transport layer with a film thickness of 5 nm. Compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated on the second hole transport layer so that the ratio of compound BD-1 was 1% by mass, and a light-emitting layer with a film thickness of 20 nm was formed. Compound ET-1 was evaporated on the light-emitting layer to form a first electron transport layer (hole barrier layer) with a film thickness of 5 nm. Compound ETL-1 and Liq were co-evaporated on the first electron transport layer so that the ratio of Liq was 50% by mass to form a second electron transport layer with a film thickness of 25 nm. Metal Yb was evaporated on the second electron transport layer to form an electron injection layer with a film thickness of 1 nm. Metal Al was evaporated on the electron injection layer to form a cathode with a film thickness of 80 nm.

[0175] The device structure of the organic EL device of Example 1 is schematically shown as follows. ITO(130) / HTL-1:HI-1(10:3%) / HTL-1(80) / EBL-1(5) / BH-1:BD-1(20:1%) / ET-1(5) / ETL-1:Liq(25:50%) / Yb(1) / Al(80) The numbers in parentheses represent the film thickness (unit: nm). Also, the numbers shown as percentages in parentheses indicate the ratio (% by mass) of the latter compound in the layer.

[0176] <Evaluation of Organic EL Device> The following evaluations were performed on the fabricated organic EL device. The results are shown in Table 1. · External quantum efficiency (EQE) When the current density is 10 mA / cm 2A voltage was applied to the organic EL element so as to obtain the EL emission spectrum, which was measured with a spectro-radiometer CS-2000 (manufactured by Konica Minolta Inc.). The EQE (%) was calculated from the obtained spectro-radiance spectrum. In Table 1, the EQE ratio (%) indicates the relative value when Comparative Example 1 described later is taken as 100.

[0177] Examples 2 to 18, Comparative Example 1 An organic EL element was fabricated and evaluated in the same manner as in Example 1, except that the compound described in Table 1 was used instead of ET-1. The results are shown in Table 1.

[0178]

Table 1

[0179] Example 19 <Fabrication of Organic EL Element> An organic EL element was fabricated as follows. A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) having a size of 25 mm × 75 mm × 1.1 mm thick was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The film thickness of ITO was 130 nm. The cleaned glass substrate with the transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, Compound HTL-2 and HI-1 were co-evaporated on the surface where the transparent electrode was formed so that the ratio of Compound HI-1 was 3% by mass to form a hole injection layer with a film thickness of 10 nm. Compound HTL-2 was evaporated on the hole injection layer to form a first hole transport layer with a film thickness of 80 nm. Compound EBL-1 was evaporated on the first hole transport layer to form a second hole transport layer with a film thickness of 5 nm. Compound BH-1 (host material) and Compound BD-1 (dopant material) were co-evaporated on the second hole transport layer so that the ratio of Compound BD-1 was 1% by mass to form a light-emitting layer with a film thickness of 20 nm. Compound ET-6 was evaporated on the light-emitting layer to form a first electron transport layer (hole barrier layer) with a film thickness of 5 nm. On the first electron transport layer, compound ETL-1 and Liq were co-evaporated such that the ratio of Liq was 50% by mass to form a second electron transport layer with a film thickness of 25 nm. On the second electron transport layer, metal Yb was evaporated to form an electron injection layer with a film thickness of 1 nm. On the electron injection layer, metal Al was evaporated to form a cathode with a film thickness of 80 nm.

[0180] When the device structure of the organic EL device of Example 19 is schematically shown, it is as follows. ITO(130) / HTL-2:HI-1(10:3%) / HTL-2(80) / EBL-1(5) / BH-1:BD-1(20:1%) / ET-6(5) / ETL-1:Liq(25:50%) / Yb(1) / Al(80) The numbers in parentheses represent the film thickness (unit: nm). Also, the numbers shown as percentages in parentheses indicate the ratio (% by mass) of the latter compound in the layer.

[0181] <Evaluation of Organic EL Device> The fabricated organic EL device was evaluated in the same manner as in Example 1. The results are shown in Table 2. In Table 2, the EQE ratio indicates the relative value when Comparative Example 2 described later is taken as 100.

[0182] Examples 20 to 21, Comparative Example 2 An organic EL device was fabricated and evaluated in the same manner as in Example 19, except that the compounds described in Table 2 were used instead of ET-6. The results are shown in Table 2.

[0183]

Table 2

[0184] Example 22 <Fabrication of Organic EL Device> An organic EL device was fabricated as follows. A glass substrate (manufactured by Geomatic Co., Ltd.) with a 25 mm × 75 mm × 1.1 mm thick ITO transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The film thickness of ITO was 130 nm. The glass substrate with the transparent electrode after cleaning was mounted on the substrate holder of a vacuum evaporation apparatus. First, compounds HTL-1 and HI-1 were co-evaporated so that the ratio of compound HI-1 was 3% by mass to cover the transparent electrode on the surface where the transparent electrode was formed, and a hole injection layer with a film thickness of 10 nm was formed. Compound HTL-3 was evaporated on the hole injection layer to form a first hole transport layer with a film thickness of 80 nm. Compound EBL-1 was evaporated on the first hole transport layer to form a second hole transport layer with a film thickness of 5 nm. Compounds BH-2 (host material) and BD-1 (dopant material) were co-evaporated on the second hole transport layer so that the ratio of compound BD-1 was 1% by mass, and a light-emitting layer with a film thickness of 20 nm was formed. Compound ET-4 was evaporated on the light-emitting layer to form a first electron transport layer (hole barrier layer) with a film thickness of 5 nm. Compounds ETL-1 and Liq were co-evaporated on the first electron transport layer so that the ratio of Liq was 50% by mass to form a second electron transport layer with a film thickness of 25 nm. Metal Yb was evaporated on the second electron transport layer to form an electron injection layer with a film thickness of 1 nm. Metal Al was evaporated on the electron injection layer to form a cathode with a film thickness of 80 nm.

[0185] The device structure of the organic EL device of Example 22 is schematically shown as follows. ITO(130) / HTL-1:HI-1(10:3%) / HTL-3(80) / EBL-1(5) / BH-2:BD-1(20:1%) / ET-4(5) / ETL-1:Liq(25:50%) / Yb(1) / Al(80) The numbers in parentheses represent the film thickness (unit: nm). Also, the numbers shown as percentages in parentheses indicate the ratio (% by mass) of the latter compound in the layer.

[0186] <Evaluation of Organic EL Element> The following evaluations were performed on the fabricated organic EL elements. The results are shown in Table 3. · Element lifetime At room temperature, a voltage was applied to the organic EL element so that the current density became 50 mA / cm 2 and the time (LT95 (unit: h)) until the luminance reached 95% of the initial luminance was measured. The LT95 ratio (%) indicates the relative value when Comparative Example 3 described later is set to 100.

[0187] Comparative Example 3 An organic EL element was fabricated and evaluated in the same manner as in Example 22, except that the compound described in Table 3 was used instead of ET-4. The results are shown in Table 3.

[0188]

Table 3

[0189] <Synthesis of Compound> (Synthesis Example 1) Synthesis of ET-1 ET-1 was synthesized according to the following synthetic route.

Chemical Formula

[0190] (Synthesis Example 2) Synthesis of ET-2 ET-2 was synthesized according to the following synthetic route.

Chemical formula

[0191] (Synthesis Example 3) Synthesis of ET-3 ET-3 was synthesized according to the following synthetic route.

Chemical formula

[0192] (Synthesis Example 4) Synthesis of ET-4 ET-4 was synthesized according to the following synthetic route. [Chemical formula] 4,6-Dichloro-2-phenylpyrimidine (17.84 g), 2-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (14.68 g), and PdCl2(dppf)CH2Cl2 (1.30 g) were placed in a flask. After replacing the atmosphere in the flask with argon gas, toluene (317 mL), DME (79 mL), and 2 M aqueous sodium carbonate solution (59.5 mL) were added, and the mixture was heated and stirred under reflux conditions for 6.5 hours. After cooling the reaction solution, filtration was performed through silica gel. The crude product obtained by distilling off the solvent was purified by silica gel chromatography and washed with hexane to obtain 4-chloro-6-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-2-phenylpyrimidine as a white solid (13.37 g, yield 76%). [Chemical formula] 4-Chloro-6-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-2-phenylpyrimidine (4.30 g), 2-(4-(dibenzo[b,d]furan-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.23 g), and (Amphos)2PdCl2 (0.28 g) were placed in a flask. After replacing the atmosphere in the flask with argon gas, 1,4-dioxane (99 mL) and 2M aqueous sodium carbonate solution (12.4 mL) were added, and the mixture was heated and stirred under reflux conditions for 4 hours. After cooling the reaction solution, MeOH was added, and the precipitated solid was collected by filtration. The obtained crude product was purified by silica gel chromatography and washed with hexane to obtain ET-4 as a white solid (4.90 g, yield 77%). As a result of mass spectrum analysis, m / e = 641 for a molecular weight of 640.79, and this white solid was identified as the target product.

[0193] (Synthesis Example 5) Synthesis of ET-5 ET-5 was synthesized according to the following synthetic route.

Chemical formula

[0194] (Synthesis Example 6) Synthesis of ET-6 ET-6 was synthesized according to the following synthetic route.

Chemical formula

[0195] (Synthesis Example 7) Synthesis of ET-7 ET-7 was synthesized according to the following synthetic route.

Chemical formula

[0196] (Synthesis Example 8) Synthesis of ET-8 ET-8 was synthesized according to the following synthetic route. [Chemical formula] 4-([1,1'-Biphenyl]-4-yl)-6-(4-bromophenyl)-2-phenylpyrimidine (5.00 g), 2-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.79 g), Pd2(dba)3 (0.20 g), and SPhos (0.35 g) were placed in a flask. After replacing the atmosphere in the flask with argon gas, 1,4-dioxane (108 mL) and 2M aqueous sodium carbonate solution (13.5 mL) were added, and the mixture was heated and stirred under reflux conditions for 7 hours. The reaction solution was filtered through silica gel, and the crude product obtained by distilling off the solvent was purified by silica gel chromatography and washed with hexane to obtain ET-8 as a white solid (5.78 g, yield 85%). As a result of mass spectrum analysis, m / e = 627 for a molecular weight of 626.80, and this white solid was identified as the target product.

[0197] (Synthesis Example 9) Synthesis of ET-9 ET-9 was synthesized according to the following synthetic route.

Chemical Structure

[0198] (Synthesis Example 10) Synthesis of ET-10 ET-10 was synthesized according to the following synthetic route.

Chemical Structure

[0199] (Synthesis Example 11) Synthesis of ET-11 ET-11 was synthesized according to the following synthetic route. [Chemical formula] 4-Chloro-6-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-2-phenylpyrimidine (4.33 g), (3-(naphthalen-1-yl)phenyl)boronic acid (2.60 g), and (Amphos)2PdCl2 (0.28 g) were placed in a flask, replaced with argon gas, and then 1,4-dioxane (67 mL) and 2 M aqueous sodium carbonate solution (12.5 mL) were added. The mixture was heated and stirred under reflux conditions for 7 hours. After cooling the reaction solution, water and dichloromethane were added for liquid separation, and the organic phase was extracted. The crude product obtained by distilling off the solvent was purified by silica gel chromatography to obtain ET-11 as a pale yellow solid (4.14 g, yield 69%). As a result of mass spectrum analysis, m / e = 601 for a molecular weight of 600.76, and it was identified as the target product.

[0200] (Synthesis Example 12) Synthesis of ET-12 ET-12 was synthesized according to the following synthetic route.

Chemical formula

[0201] (Synthesis Example 13) Synthesis of ET-13 ET-13 was synthesized according to the following synthetic route.

Chemical formula

[0202] (Synthesis Example 14) Synthesis of ET-14 ET-14 was synthesized according to the following synthetic route.

Chemical formula

[0203] (Synthesis Example 15) Synthesis of ET-15 ET-15 was synthesized according to the following synthetic route.

Chemical formula

[0204] (Synthesis Example 16) Synthesis of ET-16 ET-16 was synthesized according to the following synthetic route. [Chemical formula] 4-Chloro-6-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-2-phenylpyrimidine (4.33 g), dibenzo[b,d]furan-2-ylboronic acid (2.22 g), and (Amphos)2PdCl2 (0.28 g) were placed in a flask, and after purging with argon gas, 1,4-dioxane (67 mL) and 2M aqueous sodium carbonate solution (12.5 mL) were added, and the mixture was heated and stirred under reflux conditions for 7 hours. After cooling the reaction solution, water was added and the precipitated solid was collected by filtration. The obtained crude product was purified by silica gel chromatography to obtain ET-16 as a white solid (3.62 g, yield 64%). As a result of mass spectrum analysis, m / e = 565 for a molecular weight of 564.68, and it was identified as the target product.

[0205] (Synthesis Example 17) Synthesis of ET-17 ET-17 was synthesized according to the following synthetic route. [Chemical formula] 4-Chloro-6-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-2-phenylpyrimidine (4.33 g), dibenzo[b,d]thiophen-2-ylboronic acid (2.40 g), and (Amphos)2PdCl2 (0.28 g) were placed in a flask, and after purging with argon gas, 1,4-dioxane (67 mL) and 2M aqueous sodium carbonate solution (12.5 mL) were added, and the mixture was heated and stirred under reflux conditions for 7 hours. After cooling the reaction solution, water was added, and the precipitated solid was collected by filtration. The obtained crude product was purified by silica gel chromatography and recrystallized using xylene to obtain ET-17 as a white solid (4.13 g, yield 71%). As a result of mass spectrum analysis, m / e = 581 for a molecular weight of 580.74, and it was identified as the target product.

[0206] (Synthesis Example 18) Synthesis of ET-18 ET-18 was synthesized according to the following synthetic route. [Chemical formula] 4-Chloro-2,6-bis(phenyl-2,3,4,5,6-d5)pyrimidine (3.50 g), 2-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.15 g), and (Amphos)2PdCl2 (0.22 g) were placed in a flask, and after purging with argon gas, 1,4-dioxane (126 mL) and 2M aqueous sodium carbonate solution (15.8 mL) were added, and the mixture was heated and stirred under reflux conditions for 7 hours. After cooling the reaction solution, dichloromethane was added, and the resulting solution was filtered through silica gel. The solvent was distilled off, and the obtained crude product was purified by silica gel chromatography and washed with hexane to obtain ET-18 as a white solid (5.03 g, yield 82%). As a result of mass spectrum analysis, m / e = 484 for a molecular weight of 483.66, and it was identified as the target product.

[0207] (Synthesis Example 19) Synthesis of ET-19 ET-19 was synthesized according to the following synthetic route.

Chemical Structure

[0208] Although several embodiments and / or examples of the present invention have been described in detail above, those skilled in the art can easily make many changes to these exemplary embodiments and / or examples without substantially departing from the novel teachings and effects of the present invention. Therefore, many of these changes are included within the scope of the present invention. All of the documents described in this specification and the content of the application that is the basis of the priority under the Paris Convention of this application are incorporated by reference.

Claims

1. A material compound for an electron transport band represented by the following formula (21). 【Chemical 165】 [In formula (21), X1 is N, and X2 is CH. Ar １ and Ar ２ are each independently, an unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 18 ring-forming atoms. (L1)n1 and (L2)n2 are each independently, a single bond, an unsubstituted phenylene group, or an unsubstituted naphthylene group. R １１ ~R １９ are each independently a hydrogen atom. R ２１ and R ２２ do not combine with each other to form a substituted or unsubstituted saturated or unsaturated ring. R ２１ and R ２２ are each independently, an unsubstituted methyl group, or an unsubstituted phenyl group. (L ２１ ) ｎ２１ is, an unsubstituted naphthylene group. ]

2. The material compound for an electron transport band according to claim 1, wherein R ２１ and R ２２ are methyl groups.

3. The material compound for an electron transport band according to claim 1, wherein the compound represented by the formula (21) is a compound represented by the following formula (212). 【Chemical 166】 [In formula (212), Ar １ 、Ar ２ 、L １ , L ２ , n1, n2, and R １１ ~R １９ are as defined in the above formula (21). R ２２１ ~R ２２６ are hydrogen atoms. ]

4. Ar １ and Ar ２ are each independently an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, an unsubstituted fluorenyl group, an unsubstituted phenanthryl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothiophenyl group The material compound for an electron transport band according to claim 1.

5. Ar １ and Ar ２ are each independently an unsubstituted phenyl group, or an unsubstituted naphthyl group. The material compound for an electron transport band according to claim 1.

6. The material compound for an electron transport band according to claim 1, which is selected from the group consisting of the following compounds. 【Chemical formula 136】

7. An organic electroluminescence device including an anode, a light-emitting layer, an electron transport band, and a cathode in this order, wherein the electron transport band contains the material compound for an electron transport band according to claim 1.

8. The electron transport band has a first layer and a second layer in this order from the light-emitting layer side, The organic electroluminescence device according to claim 7, wherein the first layer contains the material compound for an electron transport band.

9. An electronic device comprising the organic electroluminescence element according to claim 7 or 8.

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