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

Abstract

Provided is a compound represented by formula (1). (The symbols in formula (1) are as defined in the specification.) Also provided are an organic electroluminescent element that contains the compound and an electronic device that includes the organic electroluminescent element.

Description

Technical Field

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

Background Art

[0002] Generally, an organic electroluminescence device (hereinafter sometimes referred to as an “organic EL device”) is composed of an anode, a cathode, and an organic layer sandwiched between the anode and the cathode. When a voltage is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side into the light-emitting region. The injected electrons and holes recombine in the light-emitting region to generate an excited state, and light is emitted when the excited state returns to the ground state. Therefore, it is important to find a combination of materials that efficiently transport electrons or holes to the light-emitting region, facilitate the recombination of electrons and holes, and efficiently generate excitons in order to obtain a high-performance organic EL device.

[0003] Patent Documents 1 to 13 disclose compounds used as materials for organic electroluminescence devices.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Patent Document 2

Patent Document 3

Patent Document 4

Patent Document 5

Patent Document 6

Patent Document 7

Patent Document 8

Patent Document 9

Patent Document 10

Patent Document 11

Patent Document 12

Patent Document 13

Summary of the Invention

Problems to be Solved by the Invention

[0005] Conventionally, many compounds for organic EL elements have been reported, but there is still a demand to further improve the performance of organic EL elements.

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

Means for Solving the Problems

[0007] As a result of intensive studies on the performance of organic EL elements containing the compounds described in Patent Documents 1 to 13, the present inventors have found that the performance of organic EL elements containing the compound represented by the following formula (1) is further improved.

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

Chemical Formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0009] In another aspect, the present invention provides a material for an organic EL element containing a compound represented by the above formula (1).

[0010] In still another aspect, the present invention provides an organic electroluminescence element including a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer contains a compound represented by the above formula (1).

[0011] In still another aspect, the present invention provides an electronic device including the above organic electroluminescence element.

Advantages of the Invention

[0012] An organic EL element containing a compound represented by the above formula (1) exhibits improved element performance.

Brief Description of the Drawings

[0013]

Figure 1

Figure 2

Figure 3

Modes for Carrying Out the Invention

[0014] [Definitions] In the present specification, the hydrogen atom includes isotopes having different numbers of neutrons, that is, protium, deuterium, and tritium.

[0015] In this specification, in a chemical structural formula, at a bondable position where symbols such as "R" or "D" representing a deuterium atom are not explicitly shown, it is assumed that a hydrogen atom, that is, a light hydrogen atom, a deuterium atom, or a tritium atom is bonded.

[0016] In this 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 in a ring (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 same shall apply to the "number of ring-forming carbon atoms" described below unless otherwise specified. For example, a benzene ring has 6 ring-forming carbon atoms, a naphthalene ring has 10 ring-forming carbon atoms, a pyridine ring has 5 ring-forming carbon atoms, and a furan ring has 4 ring-forming carbon atoms. Further, 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. Also, 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 a benzene ring substituted with an alkyl group is 6. Also, 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 a naphthalene ring substituted with an alkyl group is 10.

[0017] In this specification, the number of ring-forming atoms refers to the number of atoms that constitute the ring itself in a compound having a structure in which atoms are bonded in a ring (e.g., monocyclic, fused ring, and ring assembly) (e.g., monocyclic compound, fused ring compound, crosslinked compound, carbocyclic compound, and heterocyclic compound). Atoms that do not constitute the ring (e.g., hydrogen atoms that terminate the bonds of the atoms constituting the ring) and atoms contained in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. Unless otherwise specified, the "number of ring-forming atoms" described below shall be the same. For example, the number of ring-forming atoms in a pyridine ring is 6, the number of ring-forming atoms in a quinazoline ring is 10, and the number of ring-forming atoms in a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or the number of atoms constituting a substituent is not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms in a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. Also, for example, the number of hydrogen atoms bonded to a carbon atom of a quinazoline ring or the number of atoms constituting a substituent is not included in the number of quinazoline ring-forming atoms. Therefore, the number of ring-forming atoms in a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

[0018] 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 substituents when the ZZ group is substituted. Here, "YY" is greater than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0019] In this specification, in the expression "substituted or unsubstituted ZZ group having XX to YY atoms", "XX to YY atoms" represents the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of substituents when the ZZ group 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.

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

[0021] "Substituents described in this specification" Hereinafter, the substituents described in this specification will be described.

[0022] Unless otherwise specified in this specification, the number of ring-forming carbon atoms of an "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 an "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 an "unsubstituted alkyl group" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6. Unless otherwise specified in this specification, the number of carbon atoms of an "unsubstituted alkenyl group" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6. Unless otherwise specified in this specification, the number of carbon atoms of an "unsubstituted alkynyl group" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6. The number of ring-forming carbon atoms of the "unsubstituted cycloalkyl group" described in this specification is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified in this specification. The number of ring-forming carbon atoms of the "unsubstituted arylene 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 divalent 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 alkylene group" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified in this specification.

[0023] · "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". The "substituted aryl group" means a group in which one or more hydrogen atoms of the "unsubstituted aryl group" are replaced by substituents. Examples of the "substituted aryl group" 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 substituted aryl groups in the following specific example group G1B. It should be noted that the examples of the "unsubstituted aryl group" and the "substituted aryl group" listed here are only examples, and the "substituted aryl group" described in this specification includes a group in which the hydrogen atom bonded to the carbon atom of the aryl group itself in the "substituted aryl group" in the following specific example group G1B is further replaced by a substituent, and a group in which the hydrogen atom of the substituent in the "substituted aryl group" in the following specific example group G1B is further replaced by a substituent.

[0024] · Aryl group without substitution (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, Tetracenyl group, Pentacenyl group, Fluorenyl group, 9,9’ - Spirobifluorenyl group, Benzofluorenyl group, Dibenzofluorenyl group, Fluoranthenyl group, Benzofluoranthenyl group, Perylenyl group, and A monovalent aryl group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP - 1) to (TEMP - 15).

[0025]

Chemical formula

[0026]

Chem.

[0027] ·Aryl group for substitution (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.

[0028] ·"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 fused-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 the "heterocyclic group", it includes both the "unsubstituted heterocyclic group" and the "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 groups in the following specific example group G2B. 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 also 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.

[0029] 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).

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

[0031] · 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, Thiadiazolyl group, Pyridyl group, Pyridazinyl group, Pyrimidinyl group, Pyrazinyl group, Triazinyl group, Indolyl group, Isoindolyl group, Indolizinyl group, Quinolizinyl group, Quinolyl group, Isoquinolyl group, Cinnolyl group, Phthalazinyl group, Quinazolinyl group, Quinoxalinyl group, Benzimidazolyl group, Indazolyl group, Phenanthrolinyl group, Phenanthridinyl group, Acridinyl group, Phenazinyl group, Carbazolyl group, Benzocarbazolyl group, Morpholino group, a phenoxazinyl group, a phenothiazinyl group, an azacarbazolyl group, and a diazacarbazolyl group.

[0032] · 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, an azadibenzofuranyl group, a diazadibenzofuranyl group, an azanaphthobenzofuranyl group, and a diazanaphthobenzofuranyl group.

[0033] · an unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3): a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a benzothiophenyl group (benzothienyl group), an isobenzothiophenyl group (isobenzothienyl group), a dibenzothiophenyl group (dibenzothienyl group), a naphthobenzothiophenyl group (naphthobenzothienyl group), a benzothiazolyl group, a benzoisothiazolyl group, a phenothiazinyl group, a dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), Diazaazadibenzothiophenyl group (diazaazadibenzothienyl group), Azananofluorobenzothiophenyl group (azananofluorobenzothienyl group), and Diazaazananofluorobenzothiophenyl group (diazaazananofluorobenzothienyl group).

[0034] · A 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):

[0035]

Chemical formula

[0036]

Chemical formula

[0037] In the above 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 above 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 above general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0038] · A substituted heterocyclic group 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.

[0039] ·Substituted heterocyclic group 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].

[0040] ·Substituted heterocyclic group containing a sulfur atom (specific example group G2B3): Phenyldibenzothiophenyl group, Methyldibenzothiophenyl group, t-Butyldibenzothiophenyl group, and Monovalent residue of spiro[9H-thioxanthene-9,9’-[9H]fluorene].

[0041] ·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):

[0042] The "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 atoms when at least one of XA and YA is NH, and the hydrogen atoms of the methylene group when one of XA and YA is CH2.

[0043] · "Substituted or unsubstituted alkyl 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", both "unsubstituted alkyl group" and "substituted alkyl group" are included. "Substituted alkyl group" means a group in which one or more hydrogen atoms in the "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 groups" (specific example group G3A) are replaced by substituents, and examples of substituted alkyl groups (specific example group G3B), etc. 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.

[0044] · 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.

[0045] · Substituted alkyl group (specific example group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group, and trifluoromethyl group.

[0046] · "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). (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 an "unsubstituted alkenyl group" and a "substituted alkenyl group". 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). 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.

[0047] · Unsubstituted alkenyl group (specific example group G4A): vinyl group, allyl group, 1-butenyl group, 2-butenyl group, and 3-butenyl group.

[0048] · Substituted alkenyl group (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.

[0049] · "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 referring to an "alkynyl group", it includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group". The "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.

[0050] · Unsubstituted alkynyl group (specific example group G5A): Ethynyl group

[0051] · "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 referring to a "cycloalkyl group", it includes both an "unsubstituted cycloalkyl group" and a "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, and 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.

[0052] · 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.

[0053] · Substituted cycloalkyl group (specific example group G6B): 4-Methylcyclohexyl group.

[0054] · 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) may be 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 G1s in -Si(G1)(G1)(G1) are the same as or different from each other. The plurality of G2s in -Si(G1)(G2)(G2) are the same as or different from each other. The plurality of G1s in -Si(G1)(G1)(G2) are the same as or different from each other. The plurality of G2s in -Si(G2)(G2)(G2) are the same as or different from each other. The plurality of G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The plurality of G6s in -Si(G6)(G6)(G6) are the same as or different from each other.

[0055] · "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) may be 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.

[0056] · 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) are 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.

[0057] · 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) are 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. - In -N(G1)(G1), the plurality of G1s are the same as or different from each other. - In -N(G2)(G2), the plurality of G2s are the same as or different from each other. - In -N(G3)(G3), the plurality of G3s are the same as or different from each other. - In -N(G6)(G6), the plurality of G6s are the same as or different from each other.

[0058] · "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.

[0059] · "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). Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms in 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.

[0060] · "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, more preferably 1 to 18. The "substituted haloalkyl group" means a group in which one or more hydrogen atoms of the "haloalkyl group" are replaced by a substituent. In addition, the "substituted haloalkyl group" as described herein 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 a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted haloalkyl group" are further replaced by a substituent. 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 be referred to as a halogenated alkyl group.

[0061] · "Substituted or unsubstituted alkoxy group" Specific examples of the "substituted or unsubstituted alkoxy group" as 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, more preferably 1 to 18.

[0062] · "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 number of carbon atoms of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0063] · "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.

[0064] · "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.

[0065] · "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 number of carbon atoms 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.

[0066] · "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 by 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 by 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.

[0067] 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.

[0068] 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 phenyl dibenzothiophenyl group, etc., unless otherwise described in this specification.

[0069] In this specification, unless otherwise described in this specification, the carbazolyl group is specifically any of the following groups.

[0070]

Chemical formula

[0071] In this specification, unless otherwise described in this specification, the (9-phenyl)carbazolyl group is specifically any of the following groups.

[0072]

Chemical formula

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

[0074] In this specification, unless otherwise specified herein, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups.

[0075]

Chemical formula

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

[0077] 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.

[0078] · "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.

[0079] · "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.

[0080] · "A 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.

[0081] 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).

[0082]

Chemical formula

[0083]

Chemical formula

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

[0085]

Chemical formula

[0086] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent. The groups 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 the bonding position.

[0087]

Chemical formula

[0088] 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 the bonding position.

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

[0090]

Chemical formula

[0091]

Chemical formula

[0092]

Chemical formula

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

[0094]

Chemical formula

[0095]

Chemical formula

[0096] [Chemistry]

[0097] [Chemistry]

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

[0099] The above is the description of "the substituents described in this specification".

[0100] · "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 of "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted monocyclic ring", the case of "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 of "one or more sets of two or more adjacent ones do not bond to each other". 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" and the case of "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") will be described below. 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.

[0101] [Chemistry]

[0102] 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.

[0103] 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. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0104]

Chemical formula

[0105] The case where a "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, and R 922 and R923 are combined with each other to form ring Q C to form, and a group consisting of three (R 921 , R 922 and R 923 ) are combined with each other to form a ring and condense with 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 .

[0106]

Chemical formula

[0107] The "monocyclic ring" or "condensed ring" formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when "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 (TEMP-104) is a benzene ring, ring Q A is a monocyclic ring. If ring Q A in the general formula (TEMP-104) is a naphthalene ring, ring Q A is a condensed ring.

[0108] "Unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. "Saturated ring" means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. 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 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 elements. For example, in the general formula (TEMP-104), R 921 and R 922 are bonded to each other to form a ring Q A which means a ring formed by a carbon atom of the anthracene skeleton to which R 921 is bonded, a carbon atom of the anthracene skeleton to which R 922 is bonded, and one or more arbitrary elements. Specific examples include, when forming ring Q 921 with R 922 , when R A forms a monocyclic unsaturated ring with a carbon atom of the anthracene skeleton to which R 921 is bonded, a carbon atom of the anthracene skeleton to which R 922 is bonded, and four carbon atoms, the ring formed by R 921 and R 922 is a benzene ring.

[0109] Here, "arbitrary element" is preferably at least one element selected from the group consisting of a carbon element, a nitrogen element, an oxygen element, and a sulfur element, unless otherwise specified in this specification. In an arbitrary element (for example, in the case of a carbon element or a nitrogen element), 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 an arbitrary element other than the carbon element is included, the formed ring is a heterocyclic ring. Unless otherwise specified in this specification, the "one or more arbitrary elements" constituting the monocyclic or fused 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 specified in this specification, among the "monocyclic ring" and the "fused ring", the "monocyclic ring" is preferred. Unless otherwise specified in this specification, among the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred. Unless otherwise specified in this specification, the "monocyclic ring" is preferably a benzene ring. Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring. When "one or more sets of two or more adjacent groups" "are bonded to each other to form a substituted or unsubstituted monocyclic ring" or "are bonded to each other to form a substituted or unsubstituted fused ring", unless otherwise specified in this specification, preferably, one or more sets of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted "unsaturated ring" composed of a plurality of atoms of the main skeleton and at least one element selected from the group consisting of 1 to 15 carbon, nitrogen, oxygen, and sulfur elements.

[0110] When the above-mentioned "monocyclic ring" or "fused 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 "fused ring" has a substituent are the substituents described in the section of "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 "fused 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 sets of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more sets of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted fused ring" (the case of "bonding to form a ring").

[0111] · Substituents in the case of "substituted or unsubstituted" In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (which may be referred to as "any substituent" in the present 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 the like selected from the group consisting of, wherein R 901 to 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 heterocyclic group having 5 to 50 ring-forming atoms. When two or more R 901 are present, two or more R 901 are the same as or different from each other, When two or more R 902 are present, two or more R 902 are the same as or different from each other, R 903When there are two or more, two or more Rs 903 are either identical to each other or different, R 904 When there are two or more, two or more Rs 904 are either identical to each other or different, R 905 When there are two or more, two or more Rs 905 are either identical to each other or different, R 906 When there are two or more, two or more Rs 906 are either identical to each other or different, R 907 When there are two or more, two or more Rs 907 are either identical to each other or different.

[0112] 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 and is a group selected from the group consisting of.

[0113] 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 and is a group selected from the group consisting of.

[0114] Specific examples of each group of the above-mentioned arbitrary substituents are the specific examples of the substituents described in the section of "substituents described in this specification" described above.

[0115] Unless otherwise specified herein, 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 herein, any substituent may further have a substituent. The substituent that any substituent further has is the same as the above any substituent.

[0116] As used herein, the numerical range represented by "AA~BB" means a range including the numerical value AA described before "AA~BB" as the lower limit value and the numerical value BB described after "AA~BB" as the upper limit value.

[0117] Hereinafter, the compounds of the present invention will be described. The compound of the present invention is represented by the above formula (1). Hereinafter, the symbols in formula (1) and each of the following formulas included in formula (1) will be described. Unless otherwise specified, the same symbol has the same meaning. The compound of the present invention represented by formula (1) and the following formulas included in formula (1) may be referred to as an "inventive compound".

[0118]

Chemical formula

[0119] N * is the central nitrogen atom.

[0120] R a and R b One of them is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 10 carbon atoms, and still more preferably 1 to 6 carbon atoms, and the other is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, preferably 6 to 25 carbon atoms, more preferably 6 to 12 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms, preferably 5 to 18 ring-forming atoms, and more preferably 5 to 13 ring-forming atoms. However, Ra and R b may be combined with each other to form a substituted or unsubstituted ring.

[0121] In one embodiment of the present invention, R a and R b one of them is preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and the other is a substituted or aryl group having 6 to 30 ring-forming carbon atoms. R a and R b more preferably, one of them is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and the other is a substituted or unsubstituted phenyl group.

[0122] The unsubstituted alkyl group having 1 to 30 carbon atoms represented by the above R a and R b is, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, or a dodecyl group, preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, or a pentyl group, more preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group, and still more preferably a methyl group or a t-butyl group.

[0123] The above R a and R bThe unsubstituted aryl group having 6 to 30 ring-forming carbon atoms represented by, for example, a phenyl group, a biphenylyl group, a terphenylyl group, a biphenyleneyl group, a naphthyl group, an anthryl group, a benzoanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a picenyl group, a pentaphenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a fluorenyl group, a fluoranthenyl group, a perylenyl group, or a triphenylenylenyl group, preferably a phenyl group, a biphenylyl group, a terphenylyl group, or a naphthyl group, more preferably a phenyl group, a 2-, 3-, or 4-biphenylyl group, a 2-, 3-, or 4-o-terphenylyl group, a 2-, 3-, or 4-m-terphenylyl group, a 2-, 3-, or 4-p-terphenylyl group, or a 1- or 2-naphthyl group, still more preferably a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group, and particularly preferably a phenyl group.

[0124] Said R a and R bThe unsubstituted aromatic heterocyclic group having 5 to 30 ring-forming atoms represented thereby is, for example, a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, an imidazopyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, an isoxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a tetrazolyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolidinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, an indazolyl group, a benzoisoxazolyl group, a benzoisothiazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a phenothiazinyl group, a phenoxazinyl group, a xanthenyl group, a benzofuranyl group, an isobenzofuranyl group, a naphthobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group (benzothienyl group, the same applies hereinafter), an isobenzothiophenyl group (isobenzothienyl group, the same applies hereinafter), a naphthobenzothiophenyl group (naphthobenzothienyl group, the same applies hereinafter), a dibenzothiophenyl group (dibenzothienyl group, the same applies hereinafter), or a carbazolyl group, preferably a benzofuranyl group, an isobenzofuranyl group, a naphthobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, a naphthobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group (9-carbazolyl group, or 1-, 2-, 3- or 4-carbazolyl group).

[0125] Said R a and R b The unsubstituted monocyclic ring formed by is, for example, a benzene ring, a cyclopentane ring, or a cyclohexane ring. Said R a and R b The unsubstituted condensed ring formed by is, for example, a naphthalene ring or an anthracene ring. Also, when R a and R b are bonded to each other to form an unsubstituted monocyclic ring or an unsubstituted condensed ring, R aand R b may form a ring together with the fluorene skeleton to which they are attached, to form a spiro ring. The spiro ring is a hydrocarbon ring or a heterocyclic ring, and is selected from a monocyclic ring, a condensed ring, a bridged bicyclic ring, and a bridged tricyclic ring. Examples of the substituted or unsubstituted spiro ring are shown below, but are not limited thereto. * indicates the bonding position to the benzene ring of the fluorene skeleton.

[0126]

Chemical formula

[0127] In one aspect of the present invention, R a and R b are preferably not bonded to each other to form a substituted or unsubstituted ring.

[0128] R 2 、R 3 、R 6 and R 7 One selected from is a single bond bonded to *1, and R 1 、R 4 、R 5 、R 8 、and R 2 、R 3 、R 6 and R 7 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 10 carbon atoms, still more preferably 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 15 ring-forming carbon atoms, preferably 3 to 10 carbon atoms, more preferably 3 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms. R 1 、R 4 、R 5 、R 8 、and the R 2 、R 3 、R 6 and R 7Two adjacent ones selected from [the following] do not bond to each other and thus do not form a ring.

[0129] In one embodiment of the present invention, R 2 or R 7 is preferably a single bond that binds to *1.

[0130] The aforementioned R 1 , R 4 , R 5 , R 8 , and the R 2 , R 3 , R 6 and R 7 representing an unsubstituted alkyl group having 1 to 30 carbon atoms are as described for R a and R b .

[0131] The aforementioned R 1 , R 4 , R 5 , R 8 , and the R 2 , R 3 , R 6 and R 7 representing an unsubstituted cycloalkyl group having 3 to 15 ring-forming carbon atoms are, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, or a cyclooctyl group, preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group.

[0132] The aforementioned R 1 , R 4 , R 5 , R 8 , and the R 2 , R 3 , R 6 and R 7 representing an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms are as described for R a and R b , except that the number of ring-forming carbon atoms is 6 to 12.

[0133] Said R 1 , R 4 , R 5 , R 8 , and R which is not a single bond bonded to *1 2 , R 3 , R 6 and R 7 The details of the unsubstituted heterocyclic group having 5 to 13 ring-forming atoms represented by are the same as those described for R a and R b except that the number of ring-forming atoms is 5 to 13.

[0134] Said R 1 , R 4 , R 5 , R 8 , and R which is not a single bond bonded to *1 2 , R 3 , R 6 and R 7 may all be hydrogen atoms.

[0135] R 11 ~R 14 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 10 carbon atoms, still more preferably 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, preferably 6 to 12 carbon atoms. R 11 ~R 14 Two adjacent ones selected from do not bond to each other and thus do not form a ring.

[0136] Said R 11 ~R 14 The details of the unsubstituted alkyl group having 1 to 30 carbon atoms represented by are the same as those described for R a and R b are the same as those described.

[0137] Said R 11 ~R 14 The details of the unsubstituted aryl group having 6 to 18 ring-forming carbon atoms represented by are the same as those described for R a and R b except that the number of ring-forming carbon atoms is 6 to 18.

[0138] Said R 11 ~R 14 may all be hydrogen atoms.

[0139] L 1 ~L 4 are each independently a single bond or an arylene group having 6 to 30 ring-forming carbon atoms, preferably 6 to 25, more preferably 6 to 12.

[0140] In one embodiment of the present invention, L 1 and L 2 are each independently preferably a single bond or an arylene group having 6 to 12 ring-forming carbon atoms. L 1 may be a single bond, and L 2 may be a single bond.

[0141] In one embodiment of the present invention, L 3 is preferably a single bond. Also, in one embodiment of the present invention, L 4 is preferably a single bond. Also, in one embodiment of the present invention, L 3 and L 4 are preferably single bonds.

[0142] The unsubstituted arylene group having 6 to 30 ring-forming carbon atoms represented by said L 1 ~L 4 is a divalent group obtained by removing one hydrogen atom from an unsubstituted aryl group having 6 to 30 ring-forming carbon atoms. Details of the unsubstituted aryl group having 6 to 30 ring-forming carbon atoms are as described for R a and R b above.

[0143] Ar 1 and Ar 2 are groups represented by any of the following formulas (1a) to (1g).

[0144]

Chemical formula

[0145] In formula (1a), *21 is the bonding position to L 1 or L 2 and is the bonding position thereto. R 101 ~R 105 One selected from is a single bond connecting to *22, and R 106 ~R 110 One selected from is a single bond connecting to *23, and R 111 ~R 115 One selected from is a single bond connecting to *24. R other than the single bond 101 ~R 115 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms. R other than the single bond 101 ~R 105 Two adjacent ones selected from do not bond to each other and thus do not form a ring, R other than the single bond 106 ~R 110 Two adjacent ones selected from do not bond to each other and thus do not form a ring, R other than the single bond 111 ~R 115 Two adjacent ones selected from do not bond to each other and thus do not form a ring.

[0146] L 1 When is a single bond, *21 of the group represented by formula (1a) where Ar 1 is represents the bonding position to the central nitrogen atom N * and, L 2 When is a single bond, *21 of the group represented by formula (1a) where Ar 2 is represents the bonding position to the central nitrogen atom N * and.

[0147] R other than the single bond 101 ~R 115The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by are the same as those described for R except that the number of carbon atoms is 1 to 10. a and R b as described.

[0148] The above R 101 ~R 115 The details of the unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by are the same as those described for R and R except that the number of ring-forming carbon atoms is 6 to 12. a and R b as described.

[0149] All of R that is not a single bond bonded to *22 101 ~R 105 may all be hydrogen atoms, and all of R that is not a single bond bonded to *23 106 ~R 110 may all be hydrogen atoms, and all of R that is not a single bond bonded to *24 111 ~R 115 may all be hydrogen atoms.

[0150] m is 0 or 1, n is 0 or 1, and l is 0 or 1. When m is 0, n is 1, and l is 0 or 1, *22 represents the bonding position to L 1 or L 2 (*22 represents *21), when m is 0, n is 0, and l is 1, *23 represents the bonding position to L 1 or L 2 (*23 represents *21), when m is 0, n is 0, and l is 0, *24 represents the bonding position to L 1 or L 2 (*24 represents *21).

[0151] In one embodiment of the present invention, m is 0, n is 0, and l is 0. In this case, *24 represents *21, and the formula (1a) is represented by the following formula.

Chemical formula

[0152] In another aspect of the present invention, m is 1, n is 0, and l is 0. In this case, *24 represents *22, and formula (1a) is represented by the following formula.

Chemical formula

[0153] In yet another aspect of the present invention, m is 0, n is 1, and l is 0. In this case, *22 represents *21, *24 represents *23, and formula (1a) is represented by the following formula.

Chemical formula

[0154] In yet another aspect of the present invention, m is 0, n is 0, and l is 1. In this case, *23 represents *21, and formula (1a) is represented by the following formula.

Chemical formula

[0155] In yet another aspect of the present invention, m is 1, n is 1, and l is 0. In this case, *24 represents *23, and formula (1a) is represented by the following formula.

Chemical formula

[0156] In yet another aspect of the present invention, m is 1, n is 0, and l is 1. In this case, *23 represents *22, and formula (1a) is represented by the following formula.

Chemical formula

[0157] In yet another aspect of the present invention, m is 0, n is 1, and l is 1. In this case, *22 represents *21, and formula (1a) is represented by the following formula.

Chemical formula

[0158] In still another aspect of the present invention, m is 1, n is 1, and l is 1. In this case, formula (1a) is represented by the following formula.

Chemical formula

[0159] The group represented by the formula (1a) preferably satisfies at least one of the following (i) to (iii). (i) R 101 or R 105 is a single bond that binds to *22 (ii) R 106 or R 110 is a single bond that binds to *23 (iii) R 111 or R 115 is a single bond that binds to *24

[0160] R 116 ~R 120 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms. R 116 ~R 120 Two adjacent ones selected from these do not bond to each other and thus do not form a ring.

[0161] The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by the above R 116 ~R 120 are the same as those described for R a and R b except that the number of carbon atoms is 1 to 10.

[0162] The details of the unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by the above R 116 ~R 120 are the same as those described for R a and R b except that the number of ring-forming carbon atoms is 6 to 12.

[0163] Said R 116 ~R 120 The details of the unsubstituted aryl group having 5 to 13 ring-forming carbon atoms represented by are the same as those described for R a and R b as described.

[0164] Said R 116 ~R 120 may all be hydrogen atoms.

[0165] The group represented by formula (1a) is preferably represented by the following formula. In the following formula, R is omitted for simplicity.

Chemical formula

[0166] Formula (1b) is represented by the following formula.

[0167]

Chemical formula

[0168] In formula (1b), *25 is the bonding position to L 1 or L 2 One of them is a single bond that binds to R 121 ~R 128 selected from binds to *26. The R 121 ~R 128 that is not the single bond is each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10, preferably 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms. The R 121 ~R 128 selected from two adjacent ones do not bind to each other and thus do not form a ring. However, L 1 is a p-phenylene group, Ar 1When it is represented by the formula (1b), R in the group represented by the formula (1b) bonded to the p-phenylene group 121 , R 124 , R 125 , and R 128 selected from is a single bond bonded to *26, L 2 is a p-phenylene group, and when Ar 2 is represented by the formula (1b), R in the group represented by the formula (1b) bonded to the p-phenylene group 121 , R 124 , R 125 , and R 128 selected from is a single bond bonded to *26.

[0169] L 1 is a single bond, and *25 of the group represented by the formula (1b) where Ar 1 represents the bonding position to the central nitrogen atom N * , L 2 is a single bond, and *25 of the group represented by the formula (1b) where Ar 2 represents the bonding position to the central nitrogen atom N * .

[0170] The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by the said R 121 ~R 128 are the same as those described for R a and R b except that the number of carbon atoms is 1 to 10. The details of the unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by the said R 121 ~R 128 are the same as those described for R a and R b except that the number of ring-forming carbon atoms is 6 to 12.

[0171] In one aspect of the present invention, it is preferable that R 121 is a single bond bonded to *26, and in another aspect, it is preferable that R 122 is a single bond bonded to *26. R that is not a single bond bonded to *26121 ~R 128 All of them may be hydrogen atoms.

[0172] Formula (1c) is represented by the following formula.

[0173]

Chemical formula

[0174] In formula (1c), *27 is the bonding position to L 1 or L 2 is the bonding position to. R 131 ~R 140 One selected from is a single bond that binds to *28. R other than the single bond 131 ~R 140 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms. R other than the single bond 131 ~R 140 Two adjacent ones selected from do not bond to each other and thus do not form a ring.

[0175] L 1 When is a single bond, *27 of the group represented by formula (1c) where Ar 1 is the bonding position to the central nitrogen atom N * represents the bonding position to, L 2 When is a single bond, *27 of the group represented by formula (1c) where Ar 2 is the bonding position to the central nitrogen atom N * represents the bonding position to.

[0176] The above R 131 ~R 140 The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by are the same as those described for R a and R b as described above. The above R 131 ~R 140The details of the unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by are the same as those described for R except that the number of ring-forming carbon atoms is 6 to 12. a and R b are as described. In one aspect of the present invention, R 131 in another aspect, R 132 in yet another aspect, R 140 is preferably a single bond that binds to *28. R that is not a single bond binding to *28 131 ~R 140 may all be hydrogen atoms.

[0177] Formula (1d) is represented by the following formula.

[0178]

Chemical formula

[0179] In formula (1d), *29 is the bonding position to L 1 or L 2 is the bonding position to. R 141 ~R 152 One selected from is a single bond that binds to *30. R that is not the single bond 141 ~R 152 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms. R that is not the single bond 141 ~R 152 Two adjacent ones selected from do not bond to each other and thus do not form a ring structure.

[0180] L 1 When L is a single bond, *29 of the group represented by formula (1d) where Ar 1 is represents the bonding position to the central nitrogen atom N * to, L 2 When L is a single bond, Ar 2In formula (1d), *29 of the group represented by formula (1d) is the central nitrogen atom N * represents the bonding position to.

[0181] The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by the above R 141 ~R 152 are the same as those described for R a and R b except that the number of carbon atoms is 1 to 10. The details of the unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by the above R 141 ~R 152 are the same as those described for R a and R b except that the number of ring-forming carbon atoms is 6 to 12. All of R 141 ~R 152 that are not single bonds bonded to *30 may all be hydrogen atoms.

[0182] Formula (1e) is represented by the following formula.

[0183]

Chemical formula

[0184] In formula (1e), *31 is the bonding position to L 1 or L 2 is. One selected from R 161 ~R 165 is a single bond bonded to *32, and the other one selected from R 161 ~R 165 is a single bond bonded to *33. R 161 ~R 165 which is not a single bond bonded to *32 and not a single bond bonded to *33 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10, preferably 1 to 6 carbon atoms, or an unsubstituted phenyl group. R 161 ~R 165Two adjacent ones selected from [the following] do not bond to each other and thus do not form a ring.

[0185] L 1 When L is a single bond, *31 of the group represented by formula (1e) where Ar 1 is as defined below represents the bonding position to the central nitrogen atom N * and L 2 When L is a single bond, *31 of the group represented by formula (1e) where Ar 2 is as defined below represents the bonding position to the central nitrogen atom N * and

[0186] R which is not a single bond bonding to *32 and not a single bond bonding to *33 161 ~R 165 The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by [R] are the same as those described for R a and R b except that the number of carbon atoms is 1 to 10. The R 141 ~R 152 The details of the unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by [R] are the same as those described for R a and R b except that the number of ring-forming carbon atoms is 6 to 12. R which is not a single bond bonding to *32 and not a single bond bonding to *33 161 ~R 165 All of them may be hydrogen atoms.

[0187] R 171 ~R 175 and R 181 ~R 185 are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10, preferably 1 to 6 carbon atoms. R 171 ~R 175 Two adjacent ones selected from [the following] may bond to each other to form one or more unsubstituted benzene rings, or may not bond to each other and thus may not form a ring. R 181 ~R 185Two adjacent ones selected from the following may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and thus may not form a ring.

[0188] Said R 171 ~R 175 and R 181 ~R 185 The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by are the same as those described for R a and R b as described above. Said R 171 ~R 175 and R 181 ~R 185 All of may be hydrogen atoms.

[0189] Formula (1e) includes groups represented by the following formulas (1e-1) to (1e-5), and formula (1e-1), (1e-2) or (1e-4) is preferred.

[0190]

Chemical formula

[0191] Formula (1f) is represented by the following formula.

[0192]

Chemical formula

[0193] In formula (1f), *34 is the bonding position to L 1 or L 2 is the bonding position. X is an oxygen atom, a sulfur atom, or NR A is. X is preferably an oxygen atom or NR A is.

[0194] R 191 ~R 198 and R A One selected from is a single bond that binds to *35. The R that is not a single bond A is an unsubstituted or substituted alkyl group having 1 to 6 carbon atoms or an unsubstituted or substituted aryl group having 6 to 12 ring-forming carbon atoms.

[0195] L 1 When L is a single bond, *34 of the group represented by the formula (1f) where Ar 1 is as follows represents the bonding position to the central nitrogen atom N * and L 2 When L is a single bond, *34 of the group represented by the formula (1f) where Ar 2 is as follows represents the bonding position to the central nitrogen atom N * to it.

[0196] The above-mentioned R A The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by are, except that the number of carbon atoms is 1 to 6, as described for R a and R b as described above. The above-mentioned R A The details of the unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by are, except that the number of ring-forming carbon atoms is 6 to 12, as described for R a and R b as described above.

[0197] The R that is not a single bond 191 ~R 198 are each independently a hydrogen atom, an unsubstituted or substituted alkyl group having 1 to 6 carbon atoms, an unsubstituted or substituted aryl group having 6 to 12 ring-forming carbon atoms, or an unsubstituted or substituted heterocyclic group having 5 to 13 ring-forming atoms. The R that is not a single bond 191 ~R 198 Two adjacent ones selected from may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and thus may not form a ring.

[0198] The R that is not a single bond 191 ~R 198 The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by are, except that the number of carbon atoms is 1 to 6, as described for Ra and R b is as described with respect to R other than the single bond 191 ~R 198 The details of the unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by are, except that the number of ring-forming carbon atoms is 6 to 12, R a and R b is as described with respect to R other than the single bond 191 ~R 198 The details of the unsubstituted heterocyclic group having 5 to 13 ring-forming atoms represented by are, except that the number of ring-forming atoms is 5 to 13, R a and R b is as described with respect to

[0199] R other than the single bond bonded to *35 191 ~R 198 may all be hydrogen atoms.

[0200] When X is an oxygen atom or a sulfur atom, preferably one selected from R 191 ~R 194 is a single bond bonded to *35. When X is NR A preferably one selected from R 191 ~R 194 and R A is a single bond bonded to *35. R A is particularly preferably a single bond bonded to *35 or an unsubstituted phenyl group.

[0201] Formula (1g) is represented by the following formula.

[0202]

Chemical formula

[0203] In formula (1g), *36 is the bonding position to L 1 or L 2 R B 、R​C and R 201 ~R 208 One selected from them is a single bond that binds to *37. R other than the single bond B and R C are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms. R other than the single bond B and R C may be bonded to each other to form a substituted or unsubstituted ring.

[0204] L 1 When L is a single bond, *36 of the group represented by the formula (1g) where Ar 1 is the bonding position to the central nitrogen atom N * and represents L 2 When L is a single bond, *36 of the group represented by the formula (1g) where Ar 2 is the bonding position to the central nitrogen atom N * and represents.

[0205] In one aspect of the present invention, R B and R C are each independently preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a phenyl group.

[0206] R other than the single bond B and R C The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by are the same as those described for R a and R b except that the number of carbon atoms is 1 to 6. R other than the single bond B and R C The details of the unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by are the same as those described for R a and R b except that the number of ring-forming carbon atoms is 6 to 12. R other than the single bond B and RC The details of the unsubstituted heterocyclic group having 5 to 13 ring-forming atoms represented by are the same as those described for R except that the ring-forming atoms are 5 to 13. a and R b are as described. For the R that is not a single bond B and R C The details of the unsubstituted ring formed by their bonding to each other are the same as those described for R a and R b are as described.

[0207] For the R that is not a single bond 201 ~R 208 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms. However, two adjacent ones selected from the R that is not a single bond 201 ~R 208 do not bond to each other and thus do not form a ring.

[0208] For the R that is not a single bond 201 ~R 208 The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by are the same as those described for R except that the number of carbon atoms is 1 to 6. a and R b are as described. For the R that is not a single bond 201 ~R 208 The details of the unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by are the same as those described for R except that the number of ring-forming carbon atoms is 6 to 12. a and R b are as described. For the R that is not a single bond 201 ~R 208 The details of the unsubstituted heterocyclic group having 5 to 13 ring-forming atoms represented by are the same as those described for R except that the ring-forming atoms are 5 to 13. a and R b are as described.

[0209] In one aspect of the present invention, R 202 or R207 is preferably a single bond that binds to *37.

[0210] In one embodiment of the present invention, Ar 1 and Ar 2 at least one of is preferably a group represented by the formula (1a) or (1g).

[0211] In one embodiment of the present invention, Ar 1 or Ar 2 is a group represented by the formula (1a), and the group represented by the formula (1a) preferably satisfies at least one of the following (i) to (iii). (i) R 101 or R 105 is a single bond that binds to *22 (ii) R 106 or R 110 is a single bond that binds to *23 (iii) R 111 or R 115 is a single bond that binds to *24

[0212] In one embodiment of the present invention, Ar 1 or Ar 2 is a group represented by the formula (1g), and in the group represented by the formula (1g), R B and R C are each independently preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group.

[0213] In one embodiment of the present invention, Ar 1 or Ar 2 is a group represented by the formula (1g), and in the group represented by the formula (1g), R 202 or R 207 is preferably a single bond that binds to *37.

[0214] As described above, the "hydrogen atom" used in this specification includes a light hydrogen atom, a deuterium atom, and a tritium atom. Therefore, the inventive compound may contain deuterium atoms derived from nature. Alternatively, by using a deuterated compound for part or all of the starting compound, deuterium atoms may be intentionally introduced into compound (1). Therefore, in one embodiment of the present invention, compound (1) contains at least one deuterium atom. That is, the inventive compound may be a compound represented by formula (1), wherein at least one of the hydrogen atoms contained in the compound is a deuterium atom.

[0215] At least one hydrogen atom selected from the following hydrogen atoms may be a deuterium atom. In the following, "substituted or unsubstituted", the number of carbon atoms and the number of atoms are omitted. R in formula (1) a and R b When is an alkyl group, an aryl group, or a heterocyclic group, the hydrogen atoms they have; R in formula (1) 1 ~R 5 、R 8 、and the R that is not a single bond bonded to *1 6 and R 7 The hydrogen atoms represented by; R in formula (1) 1 ~R 5 、R 8 、and the R that is not a single bond bonded to *1 6 and R 7 When is an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group, the hydrogen atoms they have; R in formula (1) 11 ~R 14 The hydrogen atoms represented by; R in formula (1) 11 ~R 14 When is an alkyl group or an aryl group, the hydrogen atoms they have; L in formula (1) 1 ~L 4 When is an arylene group, the hydrogen atoms they have; R that is not a single bond bonded to *22 in formula (1a) 101 ~R 105 、R that is not a single bond bonded to *23 106 ~R 110 、R that is not a single bond bonded to *24 111 ~R115 The hydrogen atom represented by; R that is not a single bond bonded to *22 in formula (1a) 101 ~R 105 R that is not a single bond bonded to *23 106 ~R 110 R that is not a single bond bonded to *24 111 ~R 115 When these are an alkyl group or an aryl group, the hydrogen atoms they have; R in formula (1a) 116 ~R 120 The hydrogen atom represented by; R in formula (1a) 116 ~R 120 When these are an alkyl group, an aryl group, or a heterocyclic group, the hydrogen atoms they have; R that is not a single bond bonded to *26 in formula (1b) 121 ~R 128 The hydrogen atom represented by; R that is not a single bond bonded to *26 in formula (1b) 121 ~R 128 When these are an alkyl group or an aryl group, the hydrogen atoms they have; R that is not a single bond bonded to *28 in formula (1c) 131 ~R 140 The hydrogen atom represented by; R that is not a single bond bonded to *28 in formula (1c) 131 ~R 140 When these are an alkyl group or an aryl group, the hydrogen atoms they have; R that is not a single bond bonded to *30 in formula (1d) 141 ~R 152 The hydrogen atom represented by; R that is not a single bond bonded to *30 in formula (1d) 141 ~R 152 When these are an alkyl group or an aryl group, the hydrogen atoms they have; R that is not a single bond bonded to *32 in formula (1e) and not a single bond bonded to said *33 161 ~R 165 The hydrogen atom represented by; R that is not a single bond bonded to *32 in formula (1e) and not a single bond bonded to said *33 161 ~R165 When it is an alkyl group or a phenyl group, the hydrogen atoms they have; R in formula (1e) 171 ~R 175 and R 181 ~R 185 The hydrogen atoms represented; R in formula (1e) 171 ~R 175 and R 181 ~R 185 When it is an alkyl group, the hydrogen atoms they have; R other than a single bond bonded to *35 in formula (1f) A When it is an alkyl group or an aryl group, the hydrogen atoms they have; R other than a single bond bonded to *35 in formula (1f) 191 ~R 198 The hydrogen atoms represented; R other than a single bond bonded to *35 in formula (1f) 191 ~R 198 When it is an alkyl group, an aryl group, or a heterocyclic group, the hydrogen atoms they have; R in formula (1g) B and R C When it is an alkyl group, an aryl group, or a heterocyclic group, the hydrogen atoms they have; R other than a single bond bonded to *37 in formula (1g) 201 ~R 208 The hydrogen atoms represented; R other than a single bond bonded to *37 in formula (1g) 201 ~R 208 When it is an alkyl group, an aryl group, or a heterocyclic group, the hydrogen atoms they have.

[0216] The deuteration rate of the inventive compound depends on the deuteration rate of the starting compound used. Even if starting materials with a predetermined deuteration rate are used, light hydrogen isotopes may be contained at a certain ratio of natural origin. Therefore, the aspects of the deuteration rate of the inventive compound shown below include ratios considering trace amounts of isotopes of natural origin, relative to the ratio obtained by simply counting the number of deuterium atoms represented by the chemical formula. The deuteration rate of the inventive compound is preferably 1% or more, more preferably 3% or more, still more preferably 5% or more, even more preferably 10% or more, and even more preferably 50% or more.

[0217] The inventive compound may be a mixture containing a deuterated compound and a non-deuterated compound, or a mixture of two or more compounds having different deuteration rates. The deuteration rate of such a mixture is preferably 1% or more, more preferably 3% or more, still more preferably 5% or more, even more preferably 10% or more, even more preferably 50% or more, and less than 100%. Also, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the inventive compound is preferably 1% or more, more preferably 3% or more, still more preferably 5% or more, even more preferably 10% or more, and 100% or less.

[0218] When the "substituted or unsubstituted XX group" included in the definition of the above formulas is a substituted XX group, the details of the substituent are as described in "the substituent in the case of'substituted or unsubstituted'", and are preferably an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring-forming carbon atoms, or an aromatic heterocyclic group having 5 to 13 ring-forming atoms, and more preferably an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 12 ring-forming carbon atoms. The details of each group are as described above.

[0219] Those skilled in the art can easily manufacture the inventive compound with reference to the following synthesis examples and known synthesis methods.

[0220] Specific examples of the inventive compound are shown below, but the present invention is not limited to the following exemplified compounds. In the following specific examples, D represents a deuterium atom.

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[0352] Materials for organic EL devices The material for organic EL devices of the present invention contains an inventive compound. The content of the inventive compound in the material for organic EL devices is 1% by mass or more (including 100%), preferably 10% by mass or more (including 100%), more preferably 50% by mass or more (including 100%), still more preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). The material for organic EL devices of the present invention is useful for the production of organic EL devices.

[0353] Organic EL device The organic EL device of the present invention includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer includes a light-emitting layer, and at least one layer of the organic layer contains an inventive compound. Examples of the organic layer containing the inventive compound include a hole transport region (hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer, etc.) provided between the anode and the light-emitting layer, a light-emitting layer, a spacer layer, an electron transport region (electron injection layer, electron transport layer, hole blocking layer, etc.) provided between the cathode and the light-emitting layer, etc., but are not limited thereto. The inventive compound is preferably a material for the hole transport region or the light-emitting layer of a fluorescent or phosphorescent EL device, more preferably a material for the hole transport region, still more preferably a material for the hole injection layer, hole transport layer, electron blocking layer, or exciton blocking layer, and particularly preferably a material for the hole injection layer or hole transport layer.

[0354] The organic EL element of the present invention may be a fluorescent or phosphorescent single-color light-emitting element, a fluorescent / phosphorescent hybrid white light-emitting element, a simple type having a single light-emitting unit, or a tandem type having a plurality of light-emitting units. Among them, a fluorescent light-emitting element is preferably used. Here, the "light-emitting unit" refers to the minimum unit that includes an organic layer, at least one of which is a light-emitting layer, and emits light by the recombination of injected holes and electrons.

[0355] For example, as a typical element configuration of a simple type organic EL element, the following element configurations can be cited. (1) Anode / Light-emitting unit / Cathode In addition, the above light-emitting unit may be a multilayer type having a plurality of phosphorescent light-emitting layers or fluorescent light-emitting layers. In that case, for the purpose of preventing excitons generated in the phosphorescent light-emitting layer from diffusing into the fluorescent light-emitting layer, a space layer may be provided between each light-emitting layer. Representative layer configurations of a simple type light-emitting unit are shown below. The layers in parentheses are optional. (a) (Hole injection layer / ) Hole transport layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer) (b) (Hole injection layer / ) Hole transport layer / First fluorescent light-emitting layer / Second fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer) (c) (Hole injection layer / ) Hole transport layer / Phosphorescent light-emitting layer / Space layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer) (d) (Hole injection layer / ) Hole transport layer / First phosphorescent light-emitting layer / Second phosphorescent light-emitting layer / Space layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer) (e) (Hole injection layer / ) Hole transport layer / Phosphorescent light-emitting layer / Space layer / First fluorescent light-emitting layer / Second fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer) (f) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer) (g) (Hole injection layer / ) Hole transport layer / Exciton blocking layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer) (h) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer) (i) (Positive hole injection layer / ) First hole transport layer / Second hole transport layer / Fluorescent emission layer / First electron transport layer / Second electron transport layer ( / Electron injection layer) (j) (Positive hole injection layer / ) Hole transport layer / Fluorescent emission layer / Hole blocking layer / Electron transport layer ( / Electron injection layer) (k) (Positive hole injection layer / ) Hole transport layer / Fluorescent emission layer / Exciton blocking layer / Electron transport layer ( / Electron injection layer) (l) (Positive hole injection layer / ) First hole transport layer / Second hole transport layer / First fluorescent emission layer / Second fluorescent emission layer / First electron transport layer / Second electron transport layer ( / Electron injection layer) (m) (Positive hole injection layer / ) First hole transport layer / Second hole transport layer / Third hole transport layer / First fluorescent emission layer / Second fluorescent emission layer / First electron transport layer / Second electron transport layer ( / Electron injection layer) (n) (Positive hole injection layer / ) First hole transport layer / Second hole transport layer / Third hole transport layer / Fluorescent emission layer / First electron transport layer / Second electron transport layer ( / Electron injection layer)

[0356] Each of the above phosphorescent or fluorescent emission layers can be configured to exhibit mutually different emission colors. Specifically, in the above emission unit (f), layer configurations such as (positive hole injection layer / ) hole transport layer / first phosphorescent emission layer (red emission) / second phosphorescent emission layer (green emission) / space layer / fluorescent emission layer (blue emission) / electron transport layer can be cited. Note that an electron blocking layer may be appropriately provided between each emission layer and the hole transport layer or the space layer. Also, a hole blocking layer may be appropriately provided between each emission layer and the electron transport layer. By providing an electron blocking layer or a hole blocking layer, electrons or holes can be confined within the emission layer, increasing the charge recombination probability in the emission layer and improving the emission efficiency.

[0357] Typical element configurations of tandem organic EL elements include the following element configurations. (2) Anode / First emission unit / Intermediate layer / Second emission unit / Cathode Here, as the above first emission unit and second emission unit, for example, they can each be independently selected from the above-mentioned emission units. The above-mentioned intermediate layer is generally also called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, or an intermediate insulating layer, and a known material configuration that supplies electrons to the first light-emitting unit and holes to the second light-emitting unit can be used.

[0358] FIG. 1 is a schematic diagram showing an example of the configuration of the organic EL element of the present invention. The organic EL element 1 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10 disposed between the anode 3 and the cathode 4. The light-emitting unit 10 has a light-emitting layer 5. A hole transport band 6 (such as a hole injection layer, a hole transport layer, etc.) is provided between the light-emitting layer 5 and the anode 3, and an electron transport band 7 (such as an electron injection layer, an electron transport layer, etc.) is provided between the light-emitting layer 5 and the cathode 4. Further, an electron blocking layer (not shown) may be provided on the anode 3 side of the light-emitting layer 5, and a hole blocking layer (not shown) may be provided on the cathode 4 side of the light-emitting layer 5. Thereby, electrons and holes can be confined in the light-emitting layer 5, and the generation efficiency of excitons in the light-emitting layer 5 can be further increased.

[0359] FIG. 2 is a schematic diagram showing another configuration of the organic EL element of the present invention. The organic EL element 11 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 20 disposed between the anode 3 and the cathode 4. The light-emitting unit 20 has a light-emitting layer 5. The hole transport band disposed between the anode 3 and the light-emitting layer 5 is formed of a hole injection layer 6a, a first hole transport layer 6b, and a second hole transport layer 6c. The electron transport band disposed between the light-emitting layer 5 and the cathode 4 is formed of a first electron transport layer 7a and a second electron transport layer 7b.

[0360] FIG. 3 is a schematic diagram showing another configuration of the organic EL element of the present invention. The organic EL element 12 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 30 disposed between the anode 3 and the cathode 4. The light-emitting unit 30 has a light-emitting layer 5. The hole transport band disposed between the anode 3 and the light-emitting layer 5 is formed of a hole injection layer 6a, a first hole transport layer 6b, a second hole transport layer 6c, and a third hole transport layer 6d. The electron transport band disposed between the light-emitting layer 5 and the cathode 4 is formed of a first electron transport layer 7a and a second electron transport layer 7b.

[0361] In the present invention, a host combined with a fluorescent dopant material (fluorescent emitting material) is referred to as a fluorescent host, and a host combined with a phosphorescent dopant material is referred to as a phosphorescent host. The fluorescent host and the phosphorescent host are not distinguished only by their molecular structures. That is, the phosphorescent host means a material for forming a phosphorescent emitting layer containing a phosphorescent dopant, and does not necessarily mean that it cannot be used as a material for forming a fluorescent emitting layer. The same applies to the fluorescent host.

[0362] Substrate The substrate is used as a support for the organic EL element. As the substrate, for example, plates such as glass, quartz, and plastic can be used. Also, a flexible substrate may be used. Examples of the flexible substrate include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. In addition, an inorganic vapor deposition film can also be used.

[0363] Anode For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture 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, indium oxide containing tungsten and zinc oxide, graphene, etc. can be mentioned. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the above metals (for example, titanium nitride) can be mentioned.

[0364] These materials are usually formed into a film by a sputtering method. For example, indium oxide-zinc oxide can be formed by sputtering using a target in which 1 to 10 wt% of zinc oxide is added to indium oxide, and indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5 to 5 wt% of tungsten oxide and 0.1 to 1 wt% of zinc oxide with respect to indium oxide. In addition, it may be produced by a vacuum evaporation method, a coating method, an inkjet method, a spin coating method, or the like.

[0365] Hole transport region As described above, the organic layer may include a hole transport region between the anode and the light emitting layer. The hole transport region is composed of a hole injection layer, a hole transport layer, an electron blocking layer, and the like. It is preferable that the hole transport region contains the inventive compound. It is preferable that at least one of these layers constituting the hole transport layer contains the inventive compound, and it is more preferable that the hole transport layer contains the inventive compound.

[0366] Since the hole injection layer formed in contact with the anode is formed using a material that facilitates hole injection regardless of the work function of the anode, materials generally used as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures thereof, elements belonging to Group 1 or Group 2 of the periodic table) can be used. Elements belonging to Group 1 or Group 2 of the periodic table, which are materials with a small work function, that is, alkali metals such as lithium (Li) and cesium (Cs), and 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 can also be used. When forming the anode using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Further, when using a silver paste or the like, a coating method or an inkjet method can be used.

[0367] Hole injection layer The hole injection layer is a layer containing a material with high hole injection property (hole injection material), and is formed between the anode and the light emitting layer, or between the hole transport layer and the anode when present.

[0368] As hole injection materials other than the inventive compounds, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. can be used.

[0369] Aromatic amine compounds such as 4,4’,4’’-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4’,4’’-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4’-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4’-bis(N-{4-[N’-(3-methylphenyl)-N’-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), etc., which are low molecular weight organic compounds, can also be mentioned as hole injection layer materials.

[0370] High molecular compounds (such as oligomers, dendrimers, polymers, etc.) can also be used. For example, high molecular compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N’-[4-(4-diphenylamino)phenyl]phenyl-N’-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N’-bis(4-butylphenyl)-N,N’-bis(phenyl)benzidine] (abbreviation: Poly-TPD) can be mentioned. In addition, high molecular compounds added with acids such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can also be used.

[0371] Furthermore, it is also preferable to use acceptor materials such as hexaazatriphenylene (HAT) compounds represented by the following formula (K).

[0372] [Chemical formula]

[0373] (In the above formula, R 221 ~R 226 each independently represents a cyano group, -CONH2, a carboxyl group, or -COOR 227 (R 227 represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms)). Also, two adjacent ones selected from R 221 and R 222 , R 223 and R 224 , and R 225 and R 226 may be bonded to each other to form a group represented by -CO-O-CO-). Examples of R 227 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, a cyclohexyl group, etc.

[0374] Hole transport layer The hole transport layer is a layer containing a material with high hole transport properties (hole transport material), and is formed between the anode and the light-emitting layer, or between the hole injection layer and the light-emitting layer when present. The inventive compound may be used alone or in combination with the following compounds in the hole transport layer.

[0375] The hole transport layer may have a single-layer structure or a multilayer structure including two or more layers. For example, the hole transport layer may have a two-layer structure including a first hole transport layer (anode side) and a second hole transport layer (cathode side). That is, the above hole transport band may include a first hole transport layer on the anode side and a second hole transport layer on the cathode side. Further, the hole transport layer may have a three-layer structure including a first hole transport layer, a second hole transport layer, and a third hole transport layer in order from the anode side. That is, a third hole transport layer may be disposed between the second hole transport layer and the light-emitting layer. In one aspect of the present invention, it is preferable that the hole transport layer having the single-layer structure is adjacent to the light-emitting layer, and the hole transport layer closest to the cathode in the multilayer structure, for example, the second hole transport layer of the above two-layer structure or the third hole transport layer of the above three-layer structure, is preferably adjacent to the light-emitting layer. In another aspect of the present invention, an electron blocking layer described later may be interposed between the hole transport layer having the single-layer structure and the light-emitting layer, or between the hole transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer. When the hole transport layer has a two-layer structure, at least one of the first hole transport layer and the second hole transport layer contains the inventive compound. That is, the inventive compound is contained only in the first hole transport layer, only in the second hole transport layer, or in both the first hole transport layer and the second hole transport layer. In one aspect of the present invention, it is preferable that the inventive compound is contained in the second hole transport layer. That is, it is preferable that the inventive compound is contained only in the second hole transport layer or the inventive compound is contained in both the first hole transport layer and the second hole transport layer. When the positive hole transport layer has a three-layer structure, at least one of the first to third positive hole transport layers contains the inventive compound. That is, the inventive compound is only in one layer selected from the first to third positive hole transport layers (only the first positive hole transport layer, only the second positive hole transport layer, or only the third positive hole transport layer), only in two layers selected from the first to third positive hole transport layers (only the first positive hole transport layer and the second positive hole transport layer, only the first positive hole transport layer and the third positive hole transport layer, or only the second positive hole transport layer and the third positive hole transport layer), or is contained in all of the first to third positive hole transport layers. In one aspect of the present invention, it is preferable that the inventive compound is contained in the third positive hole transport layer. That is, it is preferable that the inventive compound is contained only in the third positive hole transport layer, or the inventive compound is contained in the third positive hole transport layer and one or both of the first positive hole transport layer and the second positive hole transport layer. In one aspect of the present invention, from the viewpoint of manufacturing cost, the inventive compound contained in each of the positive hole transport layers is preferably a light hydrogen form. The light hydrogen form refers to an inventive compound in which all hydrogen atoms in the inventive compound are light hydrogen atoms. Therefore, the present invention includes an organic EL element including one or both of the first positive hole transport layer and the second positive hole transport layer (in the case of a two-layer structure), and at least one of the first to third positive hole transport layers contains an inventive compound substantially composed of only the light hydrogen form. "The inventive compound substantially composed of only the light hydrogen form" means that the content ratio of the light hydrogen form to the total amount of the inventive compound is 90 mol% or more, preferably 95 mol% or more, more preferably 99 mol% or more (including 100% respectively).

[0376] As a positive hole transport layer material other than the inventive compound, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used. Examples of the aromatic amine compound include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The above compounds have a hole mobility of 10 -6 cm 2 / Vs or more.

[0377] Examples of the carbazole derivative include 4,4'-di(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA). Examples of the anthracene derivative include 2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth). Polymeric compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. However, as long as the compound has a higher hole transport property than the electron transport property, compounds other than the above may be used.

[0378] In the organic EL device having the two-layer hole transport layer of the present invention, it is preferable that the first hole transport layer contains one or more compounds represented by the following formula (11) or formula (12). In the organic EL device having the three-layer hole transport layer of the present invention, it is preferable that one or both of the first hole transport layer and the second hole transport layer contain one or more compounds represented by the following formula (11) or (12). In the organic EL device having the n-layer hole transport layer (n is an integer of 4 or more) of the present invention, it is preferable that at least one layer of the first hole transport layer to the (n - 1)th hole transport layer contains one or more compounds represented by the following formula (11) or formula (12).

[0379]

Chemical formula

[0380] In Formula (11) and Formula (12), A1, B1, C1, A2, B2, C2, and D2 are preferably each independently selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group. More preferably, at least one of A1, B1, and C1 in formula (11), and at least one of A2, B2, C2, and D2 in formula (12) are a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0381] The fluorenyl group which can be A1, B1, C1, A2, B2, C2, and D2 may have a substituent at the 9-position, for example, a 9,9-dimethylfluorenyl group or a 9,9-diphenylfluorenyl group. In addition, the substituents at the 9-position may form a ring together, for example, a fluorene skeleton or a xanthene skeleton together.

[0382] L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 are preferably each independently a single bond or a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.

[0383] Specific examples of the compounds represented by formula (11) and formula (12) include the following compounds.

[0384] [ka]

[0385] Dopant materials for the light-emitting layer The light-emitting layer is a layer containing a highly light-emitting material (dopant material), and various materials can be used. For example, fluorescent materials and phosphorescent materials can be used as dopant materials. Fluorescent materials are compounds that emit light from a singlet excited state, and phosphorescent materials are compounds that emit light from a triplet excited state. In one aspect of the organic EL element according to the present invention, the light-emitting layer is a single layer. Also, in another aspect of the organic EL element according to the present invention, the light-emitting layer includes a first light-emitting layer and a second light-emitting layer.

[0386] As the 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. Specifically, N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), etc. can be mentioned.

[0387] As the green fluorescent light-emitting material that can be used in the light-emitting layer, aromatic amine derivatives, etc. can be used. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), etc. can be mentioned.

[0388] As red fluorescent light-emitting materials that can be used in the light-emitting layer, tetracene derivatives, diamine derivatives, etc. can be used. Specifically, N,N,N’,N’-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N’,N’-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), etc. can be mentioned.

[0389] In one aspect of the present invention, it is preferable that the light-emitting layer contains a fluorescent light-emitting material (fluorescent dopant material).

[0390] As blue phosphorescent light-emitting materials that can be used in the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used. Specifically, bis[2-(4’,6’-difluorophenyl)pyridinato-N,C2’]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4’,6’-difluorophenyl)pyridinato-N,C2’]iridium(III) picolinate (abbreviation: FIrpic), bis[2-(3’,5’-bis(trifluoromethyl)phenyl)pyridinato-N,C2’]iridium(III) picolinate (abbreviation: Ir(CF3ppy)2(pic)), bis[2-(4’,6’-difluorophenyl)pyridinato-N,C2’]iridium(III) acetylacetonate (abbreviation: FIrracac), etc. can be mentioned.

[0391] As green phosphorescent light-emitting materials that can be used in the light-emitting layer, iridium complexes, etc. are used. Tris(2-phenylpyridinato-N,C2’)iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridinato-N,C2’)iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazolato)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)), etc. can be mentioned.

[0392] As red phosphorescent materials that can be used in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used. Specifically, bis[2-(2'-benzo[4,5-α]thienyl)pyridinato-N,C3']iridium(III) acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinolinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP), and other organometallic complexes can be mentioned.

[0393] In addition, rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: Eu(DBM)3(Phen)), and tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3(Phen)) can be used as phosphorescent materials because they emit light from rare earth metal ions (electron transitions between different multiplicities).

[0394] Host material of the light-emitting layer The light-emitting layer may have a structure in which the above-described dopant material is dispersed in another material (host material). It is preferable to use a material having a higher lowest unoccupied molecular orbital level (LUMO level) and a lower highest occupied molecular orbital level (HOMO level) than the dopant material.

[0395] Examples of the host material include (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes, (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives, (3) Condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives, (4) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives are used.

[0396] For example, metal complexes such as tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ); Heterocyclic compounds such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2’,2’’-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP); 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9'-bianthryl (abbreviation: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviation: DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 3,3',3''-(benzene-1,3,5-triyl)tripyrene (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenylchrysene and other condensed aromatic compounds; and N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) and other aromatic amine compounds can be used. A plurality of host materials may be used.

[0397] In particular, in the case of a blue fluorescent element, it is preferable to use the following anthracene compounds as the host material.

[0398]

Chemical formula

[0399]

Chemical formula

[0400]

Chemical formula

[0401] In one aspect of the organic EL element according to the present invention, when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, at least one of the components constituting the first light-emitting layer is different from the components constituting the second light-emitting layer. For example, there are aspects where the dopant material contained in the first light-emitting layer is different from the dopant material contained in the second light-emitting layer, and aspects where the host material contained in the first light-emitting layer is different from the host material contained in the second light-emitting layer.

[0402] In the organic EL element of the present invention, the light-emitting layer may contain a light-emitting compound (hereinafter, may also be simply referred to as "fluorescent light-emitting compound") that exhibits fluorescent light emission with a main peak wavelength of 500 nm or less.

[0403] The method for measuring the main peak wavelength of the compound is as follows. Prepare a 5 μmol / L toluene solution of the compound to be measured and put it in a quartz cell, and measure the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample at room temperature (300K). The emission spectrum can be measured with a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Corporation. Note that the emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength of the emission spectrum with the maximum emission intensity is defined as the main peak wavelength. In this specification, the main peak wavelength may sometimes be referred to as the fluorescent emission main peak wavelength (FL-peak).

[0404] The fluorescent light-emitting compound may be the above dopant material or the above host material.

[0405] When the light-emitting layer is a single layer, only one of the dopant material and the host material may be the fluorescent light-emitting compound, or both may be the fluorescent light-emitting compound. In addition, when the light-emitting layer includes a first light-emitting layer (anode side) and a second light-emitting layer (cathode side), only one of the first light-emitting layer and the second light-emitting layer may contain the fluorescent compound, or both light-emitting layers may contain the fluorescent compound. When the first light-emitting layer contains the fluorescent compound, only one of the dopant material and the host material contained in the first light-emitting layer may be the fluorescent compound, or both may be the fluorescent compound. Further, when the second light-emitting layer contains the fluorescent compound, only one of the dopant material and the host material contained in the second light-emitting layer may be the fluorescent compound, or both may be the fluorescent compound.

[0406] Electron transport layer The electron transport layer is a layer containing a material with high electron transport properties (electron transport material), and is formed between the light-emitting layer and the cathode, or, if present, between the electron injection layer and the light-emitting layer. The electron transport layer may have a single-layer structure or a multilayer structure including two or more layers. For example, the electron transport layer may have a two-layer structure including a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one aspect of the present invention, it is preferable that the single-layer electron transport layer is adjacent to the light-emitting layer, and in addition, the electron transport layer closest to the anode in the multilayer structure, for example, the first electron transport layer in the above two-layer structure, is preferably adjacent to the light-emitting layer. In another aspect of the present invention, a hole blocking layer or the like described later may be interposed between the single-layer electron transport layer and the light-emitting layer, or between the electron transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer.

[0407] For the electron transport layer, for example, (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, (2) Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, (3) Polymer compounds can be used.

[0408] Examples of the metal complex include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).

[0409] Examples of the heteroaromatic compound include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs).

[0410] Examples of the polymer compound include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).

[0411] The above materials are materials having an electron mobility of 10 -6 cm 2 / Vs or more. In addition, materials other than the above may be used for the electron transport layer as long as they have higher electron transport properties than hole transport properties.

[0412] Electron injection layer The electron injection layer is a layer containing a material with high electron injection properties. For the electron injection layer, alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), rare earth metals such as europium (Eu) and ytterbium (Yb), and compounds containing these metals can be used. Examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, rare earth metal halides, and rare earth metal-containing organic complexes. Also, a plurality of these compounds can be mixed and used. In addition, materials having electron transporting properties and containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, those containing magnesium (Mg) in Alq, etc. may be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, a composite material formed by mixing an organic compound and an electron donor may be used for the electron injection layer. Since such a composite material has the organic compound receiving electrons from the electron donor, it is excellent in electron injection properties and electron transporting properties. In this case, the organic compound is preferably a material excellent in transporting the received electrons. Specifically, for example, materials constituting the above-described electron transport layer (such as metal complexes and heteroaromatic compounds) can be used. As the electron donor, any material that exhibits electron donating properties with respect to the organic compound may be used. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and examples include lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. Also, alkali metal oxides and alkaline earth metal oxides are preferable, and examples include lithium oxide, calcium oxide, barium oxide, etc. Also, a Lewis base such as magnesium oxide can be used. Also, organic compounds such as tetrathiafulvalene (abbreviation: TTF) can be used.

[0413] 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, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these. When forming the cathode using an alkali metal, alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. When using a silver paste or the like, a coating method or an inkjet method can be used. In addition, by providing an electron injection layer, regardless of the work function, a cathode can be formed using various conductive materials such as Al, Ag, ITO, graphene, indium tin oxide containing silicon or silicon oxide. These conductive materials can be formed into a film using a sputtering method, an inkjet method, a spin coating method, or the like.

[0414] Insulating layer In an organic EL element, since an electric field is applied to an ultrathin film, pixel defects due to leakage or short circuit are likely to occur. To prevent this, an insulating layer composed of an insulating thin film layer may be inserted between a pair of electrodes. Examples of materials used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, etc. Note that mixtures or laminates of these may also be used.

[0415] Spacer layer The above-mentioned space layer is, for example, a layer provided between a fluorescent emission layer and a phosphorescent emission layer when laminating the fluorescent emission layer and the phosphorescent emission layer, for the purpose of preventing excitons generated in the phosphorescent emission layer from diffusing into the fluorescent emission layer or adjusting the carrier balance. Also, the space layer can be provided between a plurality of phosphorescent emission layers. Since the space layer is provided between the emission layers, it is preferably a material having both electron transporting properties and hole transporting properties. Also, in order to prevent the diffusion of triplet energy in the adjacent phosphorescent emission layer, the triplet energy is preferably 2.6 eV or more. Examples of the material used for the space layer include the same materials as those used for the above-mentioned hole transport layer.

[0416] Blocking layer Blocking layers such as an electron blocking layer, a hole blocking layer, and an exciton blocking layer may be provided adjacent to the emission layer. The electron blocking layer is a layer that prevents electrons from leaking from the emission layer to the hole transport layer, and the hole blocking layer is a layer that prevents holes from leaking from the emission layer to the electron transport layer. The exciton blocking layer has a function of preventing excitons generated in the emission layer from diffusing into the surrounding layers and confining the excitons within the emission layer.

[0417] Each layer of the organic EL element can be formed by a conventionally known vapor deposition method, coating method, etc. For example, it can be formed by a vapor deposition method such as a vacuum vapor deposition method or a molecular beam epitaxy method (MBE method), or a known method by a coating method such as a dipping method, a spin coating method, a casting method, a bar coating method, or a roll coating method using a solution of a compound for forming the layer.

[0418] The film thickness of each layer is not particularly limited, but generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and conversely, if it is too thick, a high driving voltage is required and the efficiency deteriorates. Therefore, it is usually 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm.

[0419] In the organic EL element having a two-layer or three-layer hole transport layer of the present invention, the total thickness of the first hole transport layer and the second hole transport layer is preferably 30 nm or more and 150 nm or less, more preferably 40 nm or more and 130 nm or less. Further, in one aspect of the present invention, the thickness of the second hole transport layer of the two-layer or three-layer structure is preferably 5 nm or more, more preferably 20 nm or more, still more preferably 25 nm or more, particularly preferably 35 nm or more, and is also preferably 100 nm or less. Further, in one aspect of the present invention, the thickness of the hole transport layer adjacent to the light-emitting layer is preferably 5 nm or more, more preferably 20 nm or more, still more preferably 25 nm or more, particularly preferably 30 nm or more, and is also preferably 100 nm or less. Further, in the organic EL element having a two-layer or three-layer hole transport layer of the present invention, the ratio of the film thickness D2 of the second hole transport layer to the film thickness D1 of the first hole transport layer is preferably 0.3 < D2 / D1 < 4.0, more preferably 0.5 < D2 / D1 < 3.5, still more preferably 0.75 < D2 / D1 < 3.0.

[0420] Preferred embodiments of the organic EL element of the present invention include, for example, (1) An organic EL element having a two-layer hole transport layer · A first embodiment in which the second hole transport layer contains the inventive compound and the first hole transport layer does not contain the inventive compound; · A second embodiment in which both the first hole transport layer and the second hole transport layer contain the inventive compound; · A third embodiment in which the first hole transport layer contains the inventive compound and the second hole transport layer does not contain the inventive compound; (2) An organic EL element having a three-layer hole transport layer · A fourth embodiment in which the first hole transport layer contains the inventive compound and the second and third hole transport layers do not contain the inventive compound; · A fifth embodiment in which the second hole transport layer contains the inventive compound and the first and third hole transport layers do not contain the inventive compound; · A sixth embodiment in which the third hole transport layer contains the inventive compound and the first and second hole transport layers do not contain the inventive compound; · The seventh embodiment in which the first and second hole transport layers contain the inventive compound and the third hole transport layer does not contain the inventive compound; · The eighth embodiment in which the first and third hole transport layers contain the inventive compound and the second hole transport layer does not contain the inventive compound; · The tenth embodiment in which the second and third hole transport layers contain the inventive compound and the first hole transport layer does not contain the inventive compound; · The tenth embodiment in which all of the first to third hole transport layers contain the inventive compound; and the like.

[0421] Electronic device The organic EL element according to an embodiment of the present invention can be used in electronic devices such as display devices and light-emitting devices. Examples of the display device include display components such as organic EL panel modules, televisions, mobile phones, tablets, or personal computers. Examples of the light-emitting device include lighting or vehicle lamps.

[0422] The organic EL element can be used in electronic devices such as display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and light-emitting devices such as lighting and vehicle lamps.

Examples

[0423] Hereinafter, the present invention will be described in more detail using examples, but the present invention is not limited to the following examples.

[0424] The inventive compound used in the production of the organic EL elements (I) of Examples 1 to 3

Chemical formula

[0425] The comparative compounds used in the production of the organic EL elements (I) of Comparative Examples 1 and 2

Chemical formula

[0426] Other compounds used in the production of the organic EL elements (I) of Examples 1 to 3 and Comparative Examples 1 and 2 [Chemical formula]

[0427] Fabrication of the organic EL element (I) [Example 1] A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV-ozone cleaned for 30 minutes. The film thickness of the ITO was 130 nm. The glass substrate with the cleaned ITO transparent electrode was mounted on the substrate holder of a vacuum deposition apparatus. First, compound HT-1 and compound HA were co-evaporated so as 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. The mass ratio of compound HT-1 to compound HA (HT-1:HA) was 97:3. Next, compound HT-1 was evaporated on the hole injection layer to form a first hole transport layer with a film thickness of 40 nm. Next, compound Inv-1 was evaporated on this first hole transport layer to form a second hole transport layer with a film thickness of 40 nm. Next, compound HT-2 was evaporated on this second hole transport layer to form a third hole transport layer with a film thickness of 5 nm. Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated on this third hole transport layer to form a first light-emitting layer with a film thickness of 20 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 99:1. Next, compound ET-1 was evaporated on this light-emitting layer to form a first electron transport layer with a film thickness of 5 nm. Next, compound ET-2 and Liq were co-evaporated on this first electron transport layer to form a second electron transport layer with a film thickness of 25 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50. Next, Yb was evaporated on this second electron transport layer to form an electron injection electrode with a film thickness of 1 nm. Then, metal Al was vapor-deposited on this electron-injecting electrode to form a metal cathode with a film thickness of 50 nm. The layer structure of the organic EL element of Example 1 obtained in this way is shown below. ITO (130) / HT-1:HA = 97:3 (10) / HT-1 (40) / Inv-1 (40) / HT-2 (5) / BH-1:BD-1 = 99:1 (20) / ET-1 (5) / ET-2:Liq = 50:50 (25) / Yb (1) / Al (50) In the above layer structure, the numbers in parentheses are the film thickness (nm), and the ratios are mass ratios.

[0428] <Examples 2 and 3> Each organic EL element (I) was produced in the same manner as in Example 1, except that compound Inv-4 was used in Example 2 and compound Inv-5 was used in Example 3 instead of compound Inv-1.

[0429] <Comparative Examples 1 and 2> Each organic EL element (I) was produced in the same manner as in Example 1, except that comparative compound Ref-1 was used in Comparative Example 1 and comparative compound Ref-2 was used in Comparative Example 2 instead of compound Inv-1.

[0430] Evaluation of the organic EL element (I) For the obtained organic EL element (I), the driving voltage and the external quantum efficiency were measured. (1) Measurement of the driving voltage The voltage (unit: V) when a voltage was applied to the organic EL element (I) so that the current density became 10 mA / cm 2 was measured. The results are shown in Table 1. (2) Measurement of the external quantum efficiency (EQE) The obtained organic EL element (I) was driven with a direct current constant current at a current density of 10 mA / cm 2 at room temperature. The luminance was measured using a luminance meter (spectroscopic luminance radiometer CS-1000 manufactured by Minolta Co., Ltd.), and the external quantum efficiency (%) was obtained from the results. The results are shown in Table 1.

[0431]

Table 1

[0432] Inventive compounds used in the production of the organic EL elements (II) of Examples 4 to 7 [Chemical formula]

[0433] Comparative compound used in the production of the organic EL element (II) of Comparative Example 2 [Chemical formula]

[0434] Other compounds used in the production of the organic EL elements (II) of Examples 4 to 7 and Comparative Example 3 [Chemical formula]

[0435] Fabrication of the organic EL element (II) [Example 4] A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV-ozone cleaned for 30 minutes. The film thickness of the ITO was 130 nm. The glass substrate with the cleaned ITO transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, Compound Inv-1 and Compound HA were co-evaporated so as 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. The mass ratio of Compound Inv-1 to Compound HA (Inv-1:HA) was 97:3. Next, Compound Inv-1 was evaporated on the hole injection layer to form a first hole transport layer with a film thickness of 80 nm. Next, Compound HT-4 was evaporated on this first hole transport layer to form a second hole transport layer with a film thickness of 10 nm. Next, compound BH-2 (host material) and compound BD-2 (dopant material) were co-evaporated on this second hole transport layer to form a light-emitting layer with a film thickness of 25 nm. The mass ratio of compound BH-2 to compound BD-2 (BH-2:BD-2) was 96:4. Next, compound ET-3 was evaporated on this light-emitting layer to form a first electron transport layer with a film thickness of 10 nm. Next, compound ET-4 was evaporated on this first electron transport layer to form a second electron transport layer with a film thickness of 15 nm. Next, LiF was evaporated on this second electron transport layer to form an electron-injecting electrode with a film thickness of 1 nm. Then, metal Al was evaporated on this electron-injecting electrode to form a metal cathode with a film thickness of 50 nm. The layer structure of the organic EL device (II) of Example 4 obtained in this way is shown below. ITO (130) / Inv-1:HA = 97:3 (10) / Inv-1 (80) / HT-4 (10) / BH-2:BD-2 = 96:4 (25) / ET-3 (10) / ET-4 (15) / LiF (1) / Al (50) In the above layer structure, the numbers in parentheses are the film thickness (nm), and the ratios are mass ratios.

[0436] <Examples 5 to 7> Organic EL devices (II) were fabricated in the same manner as in Example 4, except that compound Inv-6 was used in Example 5, compound Inv-7 was used in Example 6, and compound Inv-8 was used in Example 7 instead of compound Inv-1.

[0437] <Comparative Example 3> Each organic EL device (II) was fabricated in the same manner as in Example 4, except that comparative compound Ref-2 was used instead of the inventive compound Inv-1.

[0438] Evaluation of the organic EL device (II) For the obtained organic EL device (II), the driving voltage and external quantum efficiency were measured in the same manner as for the organic EL device (I). The results are shown in Table 2.

[0439]

Table 2

[0440] Inventive compounds used in the production of the organic EL elements (III) of Examples 8 to 17

Chem.

[0441] Comparative compounds used in the production of the organic EL elements (III) of Comparative Examples 4 and 5

Chem.

[0442] Other compounds used in the production of the organic EL elements of Examples 8 to 17 and Comparative Examples 4 and 5

Chem.

[0443]

Chem.

[0444] Fabrication of the organic EL element (III) <Example 8> A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV-ozone cleaned for 30 minutes. The film thickness of the ITO was 130 nm. The glass substrate with the cleaned ITO transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus, and first, Compound HT-1 and Compound HA were co-evaporated so as to cover the transparent electrode on the surface where the transparent electrode was formed, to form a hole injection layer with a film thickness of 10 nm. The mass ratio of Compound HT-1 to Compound HA (HT-1:HA) was 97:3. Next, Compound HT-1 was evaporated on the hole injection layer to form a first hole transport layer with a film thickness of 40 nm. Next, Compound Inv-2 was vapor-deposited on this first hole transport layer to form a second hole transport layer with a film thickness of 45 nm. Next, Compound HT-6 was vapor-deposited on this second hole transport layer to form a third hole transport layer with a film thickness of 5 nm. Next, Compound BH-1 (host material) and Compound BD-3 (dopant material) were co-vapor-deposited on this third hole transport layer to form a first light-emitting layer with a film thickness of 5 nm. The mass ratio of Compound BH-1 to Compound BD-3 (BH-1:BD-3) was 99:1. Next, Compound BH-5 (host material) and Compound BD-3 (dopant material) were co-vapor-deposited on this first light-emitting layer to form a second light-emitting layer with a film thickness of 20 nm. The mass ratio of Compound BH-5 to Compound BD-3 (BH-5:BD-3) was 99:1. Next, Compound ET-1 was vapor-deposited on this second light-emitting layer to form a first electron transport layer with a film thickness of 5 nm. Next, Compound ET-2 and Liq were co-vapor-deposited on this first electron transport layer to form a second electron transport layer with a film thickness of 31 nm. The mass ratio of Compound ET-2 to Liq (ET-2:Liq) was 50:50. Next, Liq was vapor-deposited on this second electron transport layer to form an electron-injecting electrode with a film thickness of 1 nm. Then, metal Al was vapor-deposited on this electron-injecting electrode to form a metal cathode with a film thickness of 80 nm. The layer structure of the organic EL element (III) of Example 8 thus obtained is shown below. ITO (130) / HT-1:HA = 97:3 (10) / HT-1 (40) / Inv-2 (45) / HT-6 (5) / BH-1:BD-3 = 99:1 (5) / BH-5:BD-3 = 99:1 (20) / ET-1 (5) / ET-2:Liq = 50:50 (31) / Liq (1) / Al (80) In the above layer structure, the numbers in parentheses are the film thickness (nm), and the ratios are mass ratios.

[0445] <Example 9> An organic EL element (III) was fabricated in the same manner as in Example 8, except that Compound Inv-3 was used instead of Compound Inv-2.

[0446] <Example 10> An organic EL element (III) was produced in the same manner as in Example 8, except that compound Inv-9 was used instead of compound Inv-2.

[0447] <Example 11> An organic EL element (III) was produced in the same manner as in Example 8, except that compound BD-4 was used instead of compound BD-3.

[0448] <Example 12> In Example 8, instead of co-evaporating compound BH-5 (host material) and compound BD-3 (dopant material) on the first light-emitting layer to form a second light-emitting layer with a film thickness of 20 nm, an organic EL element (III) was produced in the same manner, except that compound BH-4 (host material), compound BH-7 (host material), and compound BD-3 (dopant material) were co-evaporated to form a second light-emitting layer with a film thickness of 20 nm. The mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 70:30, and the concentration of compound BD-3 was 1% by mass based on the entire second light-emitting layer.

[0449] <Example 13> An organic EL element (III) was produced in the same manner as in Example 12, except that the mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was changed to 50:50.

[0450] <Example 14> An organic EL element (III) was produced in the same manner as in Example 12, except that the mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was changed to 30:70.

[0451] <Example 15> An organic EL element (III) was produced in the same manner as in Example 12, except that the mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was changed to 20:80.

[0452] <Example 16> A glass substrate (manufactured by Geomatic Co., Ltd.) with a 25 mm × 75 mm × 1.1 mm 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 the ITO was 130 nm. The cleaned glass substrate with the ITO transparent electrode was mounted on the substrate holder of a vacuum deposition apparatus. First, compound HT-1 and compound HA were co-evaporated to cover the transparent electrode on the surface where the transparent electrode was formed, forming a hole injection layer with a film thickness of 10 nm. The mass ratio of compound HT-1 to compound HA (HT-1:HA) was 97:3. Next, compound HT-1 was evaporated onto the hole injection layer to form a first hole transport layer with a film thickness of 40 nm. Next, compound Inv-2 was evaporated onto this first hole transport layer to form a second hole transport layer with a film thickness of 45 nm. Next, compound HT-2 was evaporated onto this second hole transport layer to form a third hole transport layer with a film thickness of 5 nm. Next, compound BH-3 (host material) and compound BD-5 (dopant material) were co-evaporated onto this third hole transport layer to form a first light-emitting layer with a film thickness of 5 nm. The mass ratio of compound BH-3 to compound BD-5 (BH-3:BD-5) was 99:1. Next, compound BH-6 (host material) and compound BD-5 (dopant material) were co-evaporated onto this first light-emitting layer to form a second light-emitting layer with a film thickness of 20 nm. The mass ratio of compound BH-6 to compound BD-5 (BH-6:BD-5) was 99:1. Next, compound ET-3 was evaporated onto this second light-emitting layer to form a first electron transport layer with a film thickness of 10 nm. Next, compound ET-4 was evaporated onto this first electron transport layer to form a second electron transport layer with a film thickness of 15 nm. Then, metal Al was evaporated onto this electron injection electrode to form a metal cathode with a film thickness of 80 nm. The layer structure of the organic EL element (III) of Example 16 obtained in this way is shown below. ITO (130) / HT-1:HA = 97:3 (10) / HT-1 (40) / Inv-2 (45) / HT-2 (5) / BH-3:BD-5 = 99:1 (5) / BH-6:BD-5 = 99:1 (20) / ET-3 (10) / ET-4 (15) / Al (80) In the above layer structure, the numbers in parentheses are the film thickness (nm), and the ratios are mass ratios.

[0453] <Example 17> An organic EL element (III) was fabricated in the same manner as in Example 8, except that compound HT-5 was used instead of compound HT-1 and compound Inv-1 was used instead of compound Inv-2.

[0454] <Comparative Examples 4 and 5> An organic EL element (III) was fabricated in the same manner as in Example 8, except that comparative compound Ref-3 or comparative compound Ref-4 was used instead of compound Inv-2.

[0455] Evaluation of the organic EL element (III) For the obtained organic EL element (III), the external quantum efficiency was measured in the same manner as for the organic EL element (I). The results are shown in Table 3. (3) 95% lifetime (LT95) The obtained organic EL element (III) was driven at a direct current constant current of 50 mA / cm 2 The time until the luminance decreased to 95% of the initial luminance was measured and defined as the 95% lifetime (LT95). The results are shown in Table 3.

[0456]

Table 3

[0457] Inventive compounds used in the production of the organic EL elements (IV) of Examples 18 to 34

Chemical formula

[0458] Comparative compound used in the production of the organic EL element (IV) of Comparative Example 6

Chem.

[0459] Other compounds used in the production of the organic EL elements of Examples 18 to 34 and Comparative Example 6

Chem.

[0460]

Chem.

[0461] Fabrication of the organic EL element (IV) <Example 18> A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV-ozone cleaned for 30 minutes. The film thickness of the ITO was 130 nm. The glass substrate with the cleaned ITO transparent electrode was mounted on the substrate holder of a vacuum deposition apparatus. First, Compound Inv-2 and Compound HA were co-evaporated so as 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. The mass ratio of Compound Inv-2 to Compound HA (Inv-2:HA) was 97:3. Next, Compound Inv-2 was deposited on the hole injection layer to form a first hole transport layer with a film thickness of 85 nm. Next, Compound HT-6 was deposited on this first hole transport layer to form a second hole transport layer with a film thickness of 5 nm. Next, Compound BH-1 (host material) and Compound BD-3 (dopant material) were co-evaporated on this second hole transport layer to form a first light-emitting layer with a film thickness of 5 nm. The mass ratio of Compound BH-1 to Compound BD-3 (BH-1:BD-3) was 99:1. Next, on this first light-emitting layer, compound BH-5 (host material) and compound BD-3 (dopant material) were co-evaporated to form a second light-emitting layer with a film thickness of 15 nm. The mass ratio of compound BH-5 to compound BD-3 (BH-5:BD-3) was 99:1. Next, on this second light-emitting layer, compound ET-1 was evaporated to form a first electron transport layer with a film thickness of 5 nm. Next, on this first electron transport layer, compound ET-2 and Liq were co-evaporated to form a second electron transport layer with a film thickness of 31 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50. Next, on this second electron transport layer, Liq was evaporated to form an electron-injecting electrode with a film thickness of 1 nm. Then, on this electron-injecting electrode, metal Al was evaporated to form a metal cathode with a film thickness of 80 nm. The layer structure of the organic EL element (IV) of Example 18 obtained in this way is shown below. ITO (130) / Inv-2:HA = 97:3 (10) / Inv-2 (85) / HT-6 (5) / BH-1:BD-3 = 99:1 (5) / BH-5:BD-3 = 99:1 (15) / ET-1 (5) / ET-2:Liq = 50:50 (31) / Liq (1) / Al (80) In the above layer structure, the numbers in parentheses are the film thickness (nm), and the ratios are mass ratios.

[0462] <Examples 19 to 21> Organic EL elements (IV) were fabricated in the same manner as in Example 18, except that compound Inv-4 was used in Example 19, compound Inv-3 was used in Example 20, and compound Inv-9 was used in Example 21 instead of compound Inv-2.

[0463] <Example 22> Organic EL elements (IV) were fabricated in the same manner as in Example 18, except that compound HT-7 was used instead of compound HT-6.

[0464] <Example 23> An organic EL element (IV) was fabricated in the same manner as in Example 18, except that compound BH-9 was used instead of compound BH-5.

[0465] <Example 24> An organic EL element (IV) was fabricated in the same manner as in Example 18, except that compound BH-3 was used instead of compound BH-1, compound BH-6 was used instead of compound BH-5, and compound BD-4 was used instead of compound BD-3.

[0466] <Example 25> A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) of 25 mm × 75 mm × 1.1 mm 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 cleaned ITO transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, compound Inv-2 and compound HA were co-evaporated so as 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. The mass ratio of compound Inv-2 to compound HA (Inv-2:HA) was 97:3. Next, the inventive compound Inv-2 was evaporated on the hole injection layer to form a first hole transport layer with a film thickness of 85 nm. Next, compound HT-8 was evaporated on this first hole transport layer to form a second hole transport layer with a film thickness of 5 nm. Next, compound BH-3 (host material) and compound BD-5 (dopant material) were co-evaporated on this second hole transport layer to form a first light-emitting layer with a film thickness of 5 nm. The mass ratio of compound BH-3 to compound BD-5 (BH-3:BD-5) was 99:1. Next, compound BH-6 (host material) and compound BD-5 (dopant material) were co-evaporated on this first light-emitting layer to form a second light-emitting layer with a film thickness of 15 nm. The mass ratio of compound BH-6 to compound BD-5 (BH-6:BD-5) was 99:1. Next, compound ET-3 was evaporated on this second light-emitting layer to form a first electron transport layer with a film thickness of 10 nm. Next, compound ET-4 was vapor-deposited on this first electron transport layer to form a second electron transport layer with a film thickness of 15 nm. Then, metal Al was vapor-deposited on this second electron transport layer to form a metal cathode with a film thickness of 80 nm. The layer structure of the organic EL element (IV) of Example 25 thus obtained is shown below. ITO (130) / Inv-2:HA=97:3 (10) / Inv-2 (85) / HT-8 (5) / BH-3:BD-5=99:1 (5) / BH-6:BD-5=99:1 (15) / ET-3 (10) / ET-4 (15) / Al (80) In the above layer structure, the numbers in parentheses are the film thickness (nm), and the ratios are mass ratios.

[0467] <Example 26> An organic EL element (IV) was fabricated in the same manner as in Example 18, except that compound HT-9 was used instead of compound HT-6.

[0468] <Example 27> An organic EL element (IV) was fabricated in the same manner as in Example 18, except that compound HT-10 was used instead of compound HT-6.

[0469] <Example 28> In Example 18, instead of co-vapor-depositing compound BH-5 (host material) and compound BD-3 (dopant material) on the first light-emitting layer to form a second light-emitting layer with a film thickness of 15 nm, compound BH-4 (host material), compound BH-7 (host material), and compound BD-3 (dopant material) were co-vapor-deposited to form a second light-emitting layer with a film thickness of 20 nm. The mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 70:30, and the concentration of compound BD-3 was 1 mass% with respect to the entire second light-emitting layer. An organic EL element (IV) was fabricated in the same manner otherwise.

[0470] <Example 29> In Example 28, an organic EL element (IV) was fabricated in the same manner except that compound HT-7 was used instead of compound HT-6, and the mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 60:40.

[0471] <Example 30> In Example 18, instead of co-evaporating compound BH-5 (host material) and compound BD-3 (dopant material) on the first light-emitting layer to form a second light-emitting layer with a film thickness of 15 nm, compound BH-8 (host material), compound BH-5 (host material), and compound BD-3 (dopant material) were co-evaporated to form a second light-emitting layer with a film thickness of 20 nm. An organic EL element (IV) was fabricated in the same manner. The mass ratio of compound BH-8 to compound BH-5 (BH-8:BH-5) was 70:30, and the concentration of compound BD-3 was 1% by mass based on the entire second light-emitting layer.

[0472] <Examples 31 to 34> An organic EL element (IV) was fabricated in the same manner as in Example 18, except that compound HT-11 was used in Example 31, compound HT-4 was used in Example 32, compound HT-12 was used in Example 33, and compound HT-13 was used in Example 34 instead of compound HT-6.

[0473] <Comparative Example 6> An organic EL element (IV) was fabricated in the same manner as in Example 17, except that compound Ref-5 was used instead of compound Inv-2 and compound HT-13 was used instead of compound HT-6.

[0474] Evaluation of Organic EL Element (IV) For the obtained organic EL element (IV), the external quantum efficiency was measured in the same manner as for the organic EL element (I), and the 95% lifetime was measured in the same manner as for the organic EL element (III). The results are shown in Table 4.

[0475]

Table 4

[0476] As is clear from the results in Tables 1 to 4, Compounds Inv-1 to Inv-9 provide an organic EL element having a lower driving voltage and a higher external quantum efficiency than Comparative Compounds Ref-1 to Ref-5.

[0477] Inventive Compounds Inv-1 to Inv-9 synthesized in the Synthesis Examples

Chemical Formula

[0478] Intermediate Synthesis Example 1: Synthesis of Intermediate A

Chemical Formula

[0479] Under an argon atmosphere, a mixture of 7.40 g (22.1 mmol) of 2-bromo-9-phenyl-9-methyl-9H-fluorene, 5.08 g (23.2 mmol) of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, 0.404 g (0.441 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.845 g (1.77 mmol) of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos), 33 ml of 2M aqueous potassium phosphate solution, and 110 mL of 1,4-dioxane was stirred at 80°C for 7 hours. After cooling the reaction solution to room temperature, it was concentrated under reduced pressure. The obtained solid was purified by silica gel column chromatography to obtain 7.67 g of a white solid (Intermediate A-1). The yield was 99%.

[0480] Under an argon atmosphere, a mixture of 7.67 g (22.1 mmol) of intermediate A-1, 5.15 g (22.1 mmol) of 2-bromobiphenyl, 0.406 g (0.443 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.552 g (0.886 mmol) of BINAP, 2.343 g (24.4 mmol) of sodium tert-butoxide, and 111 mL of toluene was stirred at 100 °C for 30 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained solid was purified by silica gel column chromatography to obtain 6.93 g of a white solid. The yield was 63%.

[0481] Synthesis Example of Intermediate 2: Synthesis of Intermediate B

Chemical Structure

[0482] Under an argon atmosphere, a mixture of 9.05 g (27.0 mmol) of 2-bromo-9-phenyl-9-methyl-9H-fluorene, 5.07 g (32.4 mmol) of 2-chlorophenylboronic acid, 0.395 g (0.540 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, 40.5 mL of 2M aqueous sodium carbonate solution, and 135 mL of DME was refluxed at the boiling point for 7 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained solid was purified by silica gel column chromatography to obtain 9.82 g of a white solid. The yield was 99%.

[0483] Synthesis Example of Intermediate 3: Synthesis of Intermediate C

Chemical Structure

[0484] In the synthesis of intermediate A, the same operation was carried out except that bromobenzene was used instead of 2-bromobiphenyl, and a white solid was obtained. The yield was 75%.

[0485] Synthesis Example 1: Synthesis of Compound Inv-1 [Chemistry]

[0486] Under an argon atmosphere, a mixture of 5.93 g (11.9 mmol) of Intermediate A, 3.89 g (14.2 mmol) of 2-bromo-9,9-dimethyl-9H-fluorene, 0.217 g (0.237 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.275 g (0.949 mmol) of tri-tert-butylphosphonium tetrafluoroborate, 23.7 mL of lithium bis(trimethylsilyl)amide (1 M toluene solution), and 119 mL of xylene was refluxed at the boiling point for 7 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 3.29 g of a white solid. The yield was 40%. As a result of mass spectrum analysis, the obtained product was Compound Inv-1, and m / e = 692 for a molecular weight of 691.92.

[0487] Synthesis Example 2: Synthesis of Compound Inv-2 [Chemistry]

[0488] Under an argon atmosphere, a mixture of 3.47 g (10.0 mmol) of Intermediate A-1, 6.28 g (23.0 mmol) of 2-bromo-9,9-dimethyl-9H-fluorene, 0.366 g (0.400 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.464 g (1.60 mmol) of tri-tert-butylphosphonium tetrafluoroborate, 2.69 g (28.0 mmol) of sodium tert-butoxide, and 100 mL of xylene was stirred at 110 °C for 7 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained solid was purified by silica gel column chromatography to obtain 1.88 g of a white solid. The yield was 26%. As a result of mass spectrum analysis, the obtained product was Compound Inv-2, and m / e = 732 for a molecular weight of 731.98.

[0489] Synthesis Example 3: Synthesis of Compound Inv-3

Chem.

[0490] In Synthesis Example 2, the same procedure was carried out except that 4-bromobiphenyl was used instead of 2-bromo-9,9-dimethyl-9H-fluorene, and 3.51 g of a white solid was obtained. The yield was 54%. As a result of mass spectrum analysis, the obtained product was Compound Inv-3, and m / e = 652 for a molecular weight of 651.85.

[0491] Synthesis Example 4: Synthesis of Compound Inv-4

Chem.

[0492] Under an argon atmosphere, a mixture of 2.43 g (8.51 mmol) of 9,9-dimethyl-N-phenyl-9H-fluorene-2-amine, 3.44 g (9.37 mmol) of Intermediate B, 0.156 g (0.170 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.280 g (0.681 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos), 1.15 g (11.9 mmol) of sodium tert-butoxide, and 85 mL of xylene was stirred at 110 °C for 7 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained solid was purified by silica gel column chromatography to obtain 1.88 g of a white solid. The yield was 35%. As a result of mass spectrum analysis, the obtained product was Compound Inv-4, and m / e = 616 for a molecular weight of 615.82.

[0493] Synthesis Example 5: Synthesis of Compound Inv-5

Chem.

[0494] In Synthesis Example 4, the same operations were carried out except that Intermediate D was used instead of Intermediate B and Intermediate C was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, to obtain a white solid. The yield was 62%. As a result of mass spectrum analysis, the obtained product was Compound Inv-5, and m / e = 692 with respect to a molecular weight of 691.92.

[0495] Synthesis Example 6: Synthesis of Compound Inv-6

Chemical Structure

[0496] In Synthesis Example 4, the same operations were carried out except that N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-9H-fluoren-2-amine was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, to obtain a white solid. The yield was 48%. As a result of mass spectrum analysis, the obtained product was Compound Inv-6, and m / e = 692 with respect to a molecular weight of 691.92.

[0497] Synthesis Example 7: Synthesis of Compound Inv-7

Chemical Structure

[0498] In Synthesis Example 4, the same operations were carried out except that Intermediate E was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, to obtain a white solid. The yield was 47%. As a result of mass spectrum analysis, the obtained product was Compound Inv-7, and m / e = 754 with respect to a molecular weight of 753.99.

[0499] Synthesis Example 8: Synthesis of Compound Inv-8

Chemical Structure

[0500] In Synthesis Example 4, the same operations were carried out except that intermediate F was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, and a white solid was obtained. The yield was 55%. As a result of mass spectrum analysis, the obtained product was Compound Inv-8, and m / e = 768 with respect to a molecular weight of 767.97.

[0501] Synthesis Example 9: Synthesis of Compound Inv-9

Chemical Structure

[0502] In Synthesis Example 4, the same operations were carried out except that bis([1,1'-biphenyl]-4-yl-d9)amine was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, and a white solid was obtained. The yield was 65%. As a result of mass spectrum analysis, the obtained product was Compound Inv-9, and m / e = 670 with respect to a molecular weight of 669.96.

Explanation of Symbols

[0503] 1, 11, 12 Organic EL element 2 Substrate 3 Anode 4 Cathode 5 Light-emitting layer 5a First light-emitting layer 5b Second light-emitting layer 6 Hole transport region (hole transport layer) 6a Hole injection layer 6b First hole transport layer 6c Second hole transport layer 6d Third hole transport layer 7 Electron transport region (electron transport layer) 7a First electron transport layer 7b Second electron transport layer 10, 20, 30 Light-emitting unit

Claims

1. A compound represented by the following formula (1). 【Chemical 1】 (In formula (1), N ＊ is the central nitrogen atom. R ａ and R ｂ One of them is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and the other is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms. However, R ａ and R ｂ may be combined with each other to form a substituted or unsubstituted ring. R ２ 、 R ３ 、 R ６ and R ７ One selected from is a single bond connecting to *1, and R １ 、 R ４ 、 R ５ 、 R ８ 、 and R that is not a single bond connecting to *1 ２ 、 R ３ 、 R ６ and R ７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 15 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms. R １ 、 R ４ 、 R ５ 、 R ８ 、 and the R other than the single bond ２ 、 R ３ 、 R ６ and R ７ selected from two adjacent ones do not bond to each other, and thus do not form a ring. R １１ to R １４ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms. R １１ ~R １４ Any two adjacent ones selected from them are not bonded to each other and thus do not form a ring. L １ to L ４ are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms. Ar １ and Ar ２ is a group represented by any of the following formulas (1a), (1f) and (1g), and Ar １ and Ar ２ at least one of which is a group represented by the formula (1a) or (1g). [Chemical 2] In formula (1a), *21 is the connection position to L １ or L ２ and is the connection position to it. R １０１ ~R １０５ One selected from them is a single bond that binds to *22, and R １０６ ~R １１０ One selected from them is a single bond that binds to *23, and R １１１ ~R １１５ One selected from them is a single bond that binds to *24. The R that is not the single bond １０１ ~R １１５ is each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms. The R that is not the single bond １０１ ~R １０５ Two adjacent ones selected from them do not bond to each other and thus do not form a ring The R that is not the single bond １０６ ~R １１０ Two adjacent ones selected from them do not bond to each other and thus do not form a ring. The R that is not the single bond １１１ ~R １１５ Two adjacent ones selected from them are not bonded to each other and thus do not form a ring. m is 0 or 1, n is 0 or 1, l is 0 or 1, and m + n + l is 0 or 1. R １１６ to R １２０ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms. R １１６ ~R １２０ Two adjacent ones selected from them are not bonded to each other and thus do not form a ring.) 【Chemical Formula 3】 In formula (1f), *34 is the connection position to L １ or L ２ and is the connection position to it. X is an oxygen atom, a sulfur atom, or NR Ａ wherein R is as defined below. R １９１ ~R １９８ and R Ａ One selected from them is a single bond that binds to *35. The R that is not the single bond Ａ is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms. The R that is not a single bond １９１ ~R １９８ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms. The R that is not a single bond １９１ ~R １９８ Two adjacent ones selected from them may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and thus may not form a ring.) 【Chemical 4】 In formula (1g), *36 is the connection position to L １ or L ２ and is the connection position to L R Ｂ , R Ｃ , and R ２０１ ~R ２０８ One selected from them is a single bond that binds to *37. The non-monovalent R Ｂ and R Ｃ are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms. The R that is not the single bond Ｂ and R Ｃ do not combine with each other to form a substituted or unsubstituted ring. The R that is not the single bond ２０１ ~R ２０８ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms. The R that is not the single bond ２０１ ~R ２０８ Two adjacent ones selected from them are not bonded to each other and thus do not form a ring.))

2. R ａ and R ｂ wherein one of them is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms and the other is a substituted or unsubstituted phenyl group, the compound according to claim 1.

3. R ２ or R ７ is a single bond that binds to *1, the compound according to claim 1 or 2.

4. L ３ The compound according to claim 1 or 2, wherein L is a single bond.

5. L ４ The compound according to claim 1 or 2, wherein L is a single bond.

6. Ar １ or Ar ２ is a group represented by the formula (1a), and the group represented by the formula (1a) satisfies at least one of the following (i) to (iii). The compound according to claim 1 or 2. (i) R １０１ or R １０５ is a single bond that binds to *22 (ii) R １０６ or R １１０ is a single bond that binds to *23 (iii) R １１１ or R １１５ is a single bond that binds to *24

7. Ar １ or Ar ２ is a group represented by the formula (1g), and in the group represented by the formula (1g), R B and R C are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. The compound according to claim 1 or 2.

8. Ar １ or Ar ２ is a group represented by the formula (1g), and in the group represented by the formula (1g), R ２０２ or R ２０７ is a single bond that binds to *37. The compound according to claim 1 or 2

9. L １ and L ２ The compound according to claim 1 or 2, wherein each of them is independently a single bond or an arylene group having 6 to 12 carbon atoms forming a ring.

10. L １ and L ２ is a single bond, the compound according to claim 1 or 2.

11. R １１ ~R １４ The compound according to claim 1 or 2, wherein all of R １１ ~R １４ are hydrogen atoms.

12. The compound according to claim 1 or 2, containing at least one deuterium atom.

13. A material for an organic electroluminescence device containing the compound according to claim 1 or 2.

14. A hole transport layer material containing the compound according to claim 1 or 2.

15. An organic electroluminescence device having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer contains the compound according to claim 1 or 2.

16. The organic electroluminescence device according to claim 15, wherein the organic layer includes a hole transport band between the anode and the light-emitting layer, and the hole transport band contains the compound.

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

18. The organic electroluminescence device according to claim 17, wherein the light-emitting layer is in direct contact with the second hole transport layer.

19. The organic electroluminescence device according to claim 17, wherein the total thickness of the first hole transport layer and the second hole transport layer is 30 nm or more and 150 nm or less.

20. The organic electroluminescence device according to claim 15, wherein the light-emitting layer is a single layer.

21. The organic electroluminescence device according to claim 15, wherein the light-emitting layer contains a light-emitting compound that exhibits fluorescence emission with a main peak wavelength of 500 nm or less.

22. The organic electroluminescence device according to claim 15, wherein the light-emitting layer contains a fluorescent dopant material.

23. An electronic device including the organic electroluminescence device according to claim 15.

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