Compound and Organic Electroluminescence Element

Abstract

A compound represented by formula (1). At least one of Ra-Rd is a substituted or unsubstituted biphenyl-2-yl group. At least one of Ra-Rd has a specific substituent.

Description

Technical Field

[0001] The present invention relates to novel compounds and organic electroluminescent devices.

Background Art

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

[0003] Conventional organic EL devices have not yet had sufficient device performance. Although improvements in materials used for organic EL devices have been gradually advanced to enhance device performance, further high performance is required. In particular, since the improvement of the lifetime of organic EL devices is an important issue leading to the lifetime of commercialized products, materials capable of realizing long-life organic EL devices are required.

[0004] Patent Document 1 discloses using a compound having a specific structure in the light-emitting layer of an organic EL device.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Summary of the Invention

[0006] An object of the present invention is to provide a compound capable of manufacturing a long-life organic EL device.

[0007] As a result of intensive studies to achieve the above object, the present inventors have found that a long-life organic EL device can be obtained by using a compound having a specific structure, and completed the present invention. According to the present invention, the following compounds and the like are provided. The compound represented by the following formula (1). [Chemical formula] (In the above formula (1), R a ~R d are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and at least one of R a ~R d is a substituted or unsubstituted biphenyl-2-yl group. At least one of R a ~R d contains a substituent A. The substituent A is 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, and -Si(R 31 )(R 32 )(R 33 ), and is one or more selected from the group consisting of them. At least one set of two or more adjacent ones among R 1 ~R 6 and R 11 ~R 16 form a substituted or unsubstituted saturated or unsaturated ring, or do not form the substituted or unsubstituted saturated or unsaturated ring. R 21 、R 22 、and R 1 ~R 6 and R 11 ~R 16 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -Si(R31 )(R 32 )(R 33 )、 -C(=O)R 34 、 -COOR 35 、 -N(R 36 )(R 37 )、 a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. R 31 ~R 37 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. R 31 ~R 37 When there are a plurality of each of R 31 ~R 37 , each of the plurality of R

[0008] According to the present invention, a compound capable of manufacturing a long-life organic EL element can be provided.

Brief Description of Drawings

[0009]

Figure 1

Embodiments for Carrying Out the Invention

[0010] [Definitions] In this specification, the hydrogen atom includes isotopes having different numbers of neutrons, that is, protium, deuterium, and tritium.

[0011] 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.

[0012] 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.

[0013] In this specification, the number of ring-forming atoms refers to the number of atoms that constitute the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic ring, a condensed ring, and a ring assembly) (for example, a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, and a heterocyclic compound). Atoms that do not constitute the ring (for example, hydrogen atoms that terminate the bonds of the atoms constituting the ring) and atoms included in the substituent when the ring is substituted by a substituent 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 of a pyridine ring is 6, the number of ring-forming atoms of a quinazoline ring is 10, and the number of ring-forming atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or the number of atoms constituting a substituent is not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms of 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 of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

[0014] In this specification, in the expression "substituted or unsubstituted ZZ group having XX to YY carbon atoms", "XX to YY carbon atoms" represents the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0015] 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 the substituent when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0016] In this specification, an unsubstituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to 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 a hydrogen atom in the ZZ group has not been 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 have been 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 have been replaced by an AA group.

[0017] "Substituents described in this specification" Hereinafter, the substituents described in this specification will be described.

[0018] 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. Unless otherwise specified herein, 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 herein, 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 herein, 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 herein, 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.

[0019] · "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 examples of 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.

[0020] ·Aryl groups 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).

[0021]

Chemical formula

[0022] [Chemistry]

[0023] ·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.

[0024] ·"Substituted or unsubstituted heterocyclic group" The "heterocyclic group" described in this specification is a cyclic group containing at least one heteroatom in the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom. The "heterocyclic group" described in this specification is a monocyclic group or a condensed-ring group. The "heterocyclic group" described in this specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B), etc. (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group"). In this specification, when simply referring to a "heterocyclic group", it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group". The "substituted heterocyclic group" means a group in which one or more hydrogen atoms of the "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of the "substituted heterocyclic group" include groups in which the hydrogen atoms of the "unsubstituted heterocyclic group" in the following specific example group G2A are replaced, and examples of the substituted heterocyclic groups in the following specific example group G2B, etc. Note that the examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" listed here are merely 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 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 specific example group G2B are further replaced by substituents.

[0025] 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).

[0026] 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 by substituents (specific example group G2B4).

[0027] · Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1): Pyrrolyl group, Imidazolyl group, Pyrazolyl group, Triazolyl group, Tetrazolyl group, Oxazolyl group, Isooxazolyl 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.

[0028] ·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.

[0029] ·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), Azananofbenzothiophenyl group (azananofbenzothienyl group), and Diazaazananofbenzothiophenyl group (diazaazananofbenzothienyl group).

[0030] · A monovalent heterocyclic group derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0031]

Chemical formula

[0032]

Chemical formula

[0033] In the general formulas (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH 2 . However, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH. In the general formulas (TEMP-16) to (TEMP-33), when at least one of X A and Y A is NH, or CH 2 , the monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH, or CH 2 .

[0034] · 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.

[0035] ·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].

[0036] ·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].

[0037] ·A group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structures represented by the general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific example group G2B4):

[0038] 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 atom when at least one of XA and YA is NH, and the hydrogen atoms of the methylene group when one of XA and YA is CH2.

[0039] · "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. The "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 the substituted alkyl groups (specific example group G3B). In this specification, the alkyl group in the "unsubstituted alkyl group" means a chain alkyl group. Therefore, the "unsubstituted alkyl group" includes a linear "unsubstituted alkyl group" and a branched "unsubstituted alkyl group". Note that the examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" listed here are only examples, and the "substituted alkyl group" described in this specification includes a group in which the hydrogen atoms of the alkyl group itself in the "substituted alkyl group" of the specific example group G3B are further replaced by substituents, and a group in which the hydrogen atoms of the substituents in the "substituted alkyl group" of the specific example group G3B are further replaced by substituents.

[0040] · 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.

[0041] · Substituted alkyl group (specific example group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group, and trifluoromethyl group.

[0042] · "Substituted or unsubstituted alkenyl group" Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described in this specification include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group", and the substituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group"). In this specification, when simply referring to an "alkenyl group", it includes both 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), etc. Note 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.

[0043] ·Alkenyl group without substitution (specific example group G4A): Vinyl group, Allyl group, 1-Butenyl group, 2-Butenyl group, and 3-Butenyl group.

[0044] ·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.

[0045] ·"Substituted or unsubstituted alkynyl group" Specific examples of the "substituted or unsubstituted alkynyl group" described in this specification (specific example group G5) 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.

[0046] ·Unsubstituted alkynyl group (specific example group G5A): Ethynyl group

[0047] ·"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), substituted cycloalkyl groups (specific example group G6B), and the like. (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 the "cycloalkyl group", it includes both the "unsubstituted cycloalkyl group" and the "substituted cycloalkyl group". The "substituted cycloalkyl group" means a group in which one or more hydrogen atoms in the "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 groups" (specific example group G6A) are replaced by substituents, and examples of the substituted cycloalkyl group (specific example group G6B). Note that the examples of the "unsubstituted cycloalkyl group" and the "substituted cycloalkyl group" listed here are merely 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.

[0048] · Unsubstituted cycloalkyl groups (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.

[0049] · Substituted cycloalkyl groups (specific example group G6B): 4 - Methylcyclohexyl group.

[0050] · "A group represented by -Si(R 901 )(R 902 )(R 903 )" The specific examples (specific example group G7) of the group represented by -Si(R 901 )(R 902 )(R 903 ) described in this specification include -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) are mentioned. Here,[[]] G1 is the "substituted or unsubstituted aryl group" described in specific example group G1.[[]] G2 is the "substituted or unsubstituted heterocyclic group" described in specific example group G2.[[]] G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3.[[]] G6 is the "substituted or unsubstituted cycloalkyl group" described in specific example group G6.[[]] The plurality of G1 in -Si(G1)(G1)(G1) are the same as or different from each other.[[]] The plurality of G2 in -Si(G1)(G2)(G2) are the same as or different from each other.[[]] The plurality of G1 in -Si(G1)(G1)(G2) are the same as or different from each other.[[]] The plurality of G2 in -Si(G2)(G2)(G2) are the same as or different from each other.[[]] The plurality of G3 in -Si(G3)(G3)(G3) are the same as or different from each other.[[]] The plurality of G6 in -Si(G6)(G6)(G6) are the same as or different from each other.[[]]

[0051] · "A group represented by -O-(R 904 )" The -O-(R904 ) The specific examples (specific example group G8) of the group represented by -O(G1), -O(G2), -O(G3), and -O(G6) are as follows. 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.

[0052] · The group represented by "-S-(R 905 )" The specific examples (specific example group G9) of the group represented by -S-(R 905 ) described in this specification are as follows. -S(G1), -S(G2), -S(G3), and -S(G6) are as follows. 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.

[0053] · The group represented by "-N(R 906 )(R 907 )" The specific examples (specific example group G10) of the group represented by -N(R 906 )(R 907 ) described in this specification are as follows. -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) may be mentioned. Here, G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2. G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6. The plurality of G1 in -N(G1)(G1) are the same as or different from each other. The plurality of G2 in -N(G2)(G2) are the same as or different from each other. The plurality of G3 in -N(G3)(G3) are the same as or different from each other. The plurality of G6 in -N(G6)(G6) are the same as or different from each other

[0054] · "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.

[0055] · "Substituted or unsubstituted fluoroalkyl group" As used herein, the term "substituted or unsubstituted fluoroalkyl 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 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 herein, the number of carbon atoms in the "unsubstituted fluoroalkyl group" is from 1 to 50, preferably from 1 to 30, more preferably from 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. It should be noted that the "substituted fluoroalkyl group" described herein 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.

[0056] · "substituted or unsubstituted haloalkyl group" As used herein, the term "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 from 1 to 50, preferably from 1 to 30, more preferably from 1 to 18. The "substituted haloalkyl group" means a group in which one or more hydrogen atoms in the "haloalkyl group" are replaced by substituents. 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 substituents, and a group in which one or more hydrogen atoms of the substituents in the "substituted haloalkyl group" are further replaced by substituents. Specific examples of the "unsubstituted haloalkyl group" include examples of groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced by halogen atoms. The haloalkyl group may be referred to as a halogenated alkyl group.

[0057] · "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 from 1 to 50, preferably from 1 to 30, more preferably from 1 to 18.

[0058] · "Substituted or unsubstituted alkylthio group" Specific examples of the "substituted or unsubstituted alkylthio group" as described herein are groups represented by -S(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 alkylthio group" is from 1 to 50, preferably from 1 to 30, more preferably from 1 to 18.

[0059] · "Substituted or unsubstituted aryloxy group" Specific examples of the "substituted or unsubstituted aryloxy group" described in the present 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 the present specification.

[0060] · "Substituted or unsubstituted arylthio group" Specific examples of the "substituted or unsubstituted arylthio group" described in the present 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 the present specification.

[0061] · "Substituted or unsubstituted trialkylsilyl group" Specific examples of the "trialkylsilyl group" described in the present 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 the present specification.

[0062] · "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 a "substituted or unsubstituted alkyl group" described in Specific Example Group G3, and G1 is a "substituted or unsubstituted aryl group" described in Specific Example Group G1. Therefore, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is a form of a "substituted alkyl group". An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the number of carbon atoms of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, more preferably 7 to 18, unless otherwise specified in this specification. Specific examples of the "substituted or unsubstituted aralkyl group" include a benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group, etc.

[0063] The substituted or unsubstituted aryl group described in this specification is preferably a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group, pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, 9,9'-spirobifluorenyl group, 9,9-dimethylfluorenyl group, and 9,9-diphenylfluorenyl group, etc., unless otherwise specified in this specification.

[0064] Unless otherwise specified herein, the substituted or unsubstituted heterocyclic group described herein is preferably a pyridyl group, pyrimidinyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, benzimidazolyl group, phenanthrolinyl group, carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group, dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazol-4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group, etc.

[0065] In this specification, unless otherwise specified herein, the carbazolyl group is specifically any one of the following groups.

[0066]

Chemical formula

[0067] In this specification, unless otherwise specified herein, the (9-phenyl)carbazolyl group is specifically any one of the following groups.

[0068]

Chemical formula

[0069] In the general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents the bonding position.

[0070] In this specification, unless otherwise specified herein, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups.

[0071]

Chemical formula

[0072] In the general formulas (TEMP-34) to (TEMP-41), * represents the bonding position.

[0073] 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.

[0074] · "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.

[0075] · "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.

[0076] · "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, and the like.

[0077] Unless otherwise specified in this specification, the substituted or unsubstituted arylene group described in this specification is preferably a group represented by any of the following general formulas (TEMP-42) to (TEMP-68).

[0078]

Chemical formula

[0079]

Chemical formula

[0080] In the general formulas (TEMP-42) to (TEMP-52), Q 1 ~Q 10 are each independently a hydrogen atom or a substituent. In the general formulas (TEMP-42) to (TEMP-52), * represents the bonding position.

[0081]

Chemical formula

[0082] In the general formulas (TEMP-53) to (TEMP-62), Q 1 ~Q 10 are each independently a hydrogen atom or a substituent. Formula Q 9 and Q 10They 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.

[0083]

Chemical formula

[0084] In the general formulas (TEMP-63) to (TEMP-68), Q 1 ~Q 8 are each independently a hydrogen atom or a substituent. In the general formulas (TEMP-63) to (TEMP-68), * represents the bonding position.

[0085] Unless otherwise described herein, the substituted or unsubstituted divalent heterocyclic group described in this specification is preferably a group of any of the following general formulas (TEMP-69) to (TEMP-102).

[0086]

Chemical formula

[0087]

Chemical formula

[0088]

Chemical formula

[0089] In the general formulas (TEMP-69) to (TEMP-82), Q 1 ~Q 9 are each independently a hydrogen atom or a substituent.

[0090]

Chemical formula

[0091] [Chem.]

[0092] [Chem.]

[0093] [Chem.]

[0094] In the general formulas (TEMP-83) to (TEMP-102) above, Q 1 ~Q 8 are each independently a hydrogen atom or a substituent.

[0095] The above is the description of "the substituents described in this specification".

[0096] · "When bonding to form a ring" In this specification, the case of "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted monocyclic ring, or bond to each other to form a substituted or unsubstituted condensed ring, or do not bond to each other" means the case where "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted monocyclic ring", the case where "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted condensed ring", and the case where "one or more sets of two or more adjacent ones do not bond to each other". Regarding the case in this specification where "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted condensed ring" (hereinafter, these cases may be collectively referred to as "the case of bonding to form a ring"), the following will be described. Taking the case of an anthracene compound represented by the following general formula (TEMP-103) whose mother skeleton is an anthracene ring as an example.

[0097]

Chem.

[0098] For example, R 921 ~R 930 In the case where "one or more sets of two or more adjacent ones are combined with each other to form a ring", the set of two adjacent ones that forms one set means R 921 and R 922 's set, R 922 and R 923 's set, R 923 and R 924 's set, R 924 and R 930 's set, R 930 and R 925 's set, R 925 and R 926 's set, R 926 and R 927 's set, R 927 and R 928 's set, R 928 and R 929 's set, and R 929 and R 921 's set.

[0099] The above "one or more sets" means that two or more sets of the above sets of two or more adjacent ones may form a ring simultaneously. For example, when 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 , the anthracene compound represented by the general formula (TEMP - 103) is represented by the following general formula (TEMP - 104).

[0100]

Chem.

[0101] The case where a "set consisting of two or more adjacent members" forms a ring includes not only the case where a "set of two" adjacent members combines as in the above example, but also the case where a "set of three or more" adjacent members combines. For example, R 921 and R 922 combine with each other to form ring Q A and R 922 and R 923 combine with each other to form ring Q C , and a set consisting of three adjacent members (R 921 , R 922 and R 923 ) combines with each other to form a ring and condenses with the anthracene skeleton. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C share R 922 .

[0102]

Chemical Formula

[0103] The "monocyclic ring" or "condensed ring" formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when "one set of a set consisting of two adjacent members" 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". 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 . Ring Q A in the general formula (TMEP-104)If it is a benzene ring, ring Q A is a monocyclic ring. Ring Q in the general formula (TMEP-104) A If it is a naphthalene ring, ring Q A is a condensed ring.

[0104] The "unsaturated ring" includes, in addition to the aromatic hydrocarbon ring and the aromatic heterocyclic ring, an aliphatic hydrocarbon ring having an unsaturated bond, i.e., a double bond and / or a triple bond, in the ring structure (e.g., cyclohexene, cyclohexadiene, etc.), and a non-aromatic heterocyclic ring having an unsaturated bond (e.g., dihydropyran, imidazoline, pyrazoline, quinolizine, indoline, isoindoline, etc.). The "saturated ring" includes an aliphatic hydrocarbon ring having no unsaturated bond or a non-aromatic heterocyclic ring having no unsaturated bond. Specific examples of the aromatic hydrocarbon ring include structures in which the groups exemplified as specific examples in specific example group G1 are terminated by hydrogen atoms. Specific examples of the aromatic heterocyclic ring include structures in which the aromatic heterocyclic ring groups exemplified as specific examples in specific example group G2 are terminated by hydrogen atoms. Specific examples of the aliphatic hydrocarbon ring include structures in which the groups exemplified as specific examples in specific example group G6 are terminated by hydrogen atoms. "Forming a ring" means forming a ring with only a plurality of atoms of the mother skeleton or a plurality of atoms of the mother skeleton and one or more arbitrary atoms. For example, in the general formula (TEMP-104), R 921 and R 922 are bonded to each other to form ring Q A 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 atoms. As a specific example, when R 921 and R 922 form ring Q A , when a monocyclic unsaturated ring is 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 four carbon atoms, R921 and R 922 The ring formed by and is a benzene ring.

[0105] Here, "any atom" is, unless otherwise specified in this specification, preferably at least one atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom. In any atom (for example, in the case of a carbon atom or a nitrogen atom), the bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described later. When any atom other than a carbon atom is included, the formed ring is a heterocyclic ring. "One or more arbitrary atoms" constituting a monocyclic or condensed ring are, unless otherwise specified in this specification, 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 "monocyclic" and "condensed ring", "monocyclic" is preferred. Unless otherwise specified in this specification, among "saturated ring" and "unsaturated ring", "unsaturated ring" is preferred. Unless otherwise specified in this specification, the "monocyclic" is preferably a benzene ring. Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring. When "one or more sets consisting of two or more adjacent ones" "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 condensed ring", unless otherwise specified in this specification, preferably, one or more sets consisting of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted "unsaturated ring" composed of a plurality of atoms of the main skeleton and at least one atom selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0106] The substituent when the above-mentioned "monocyclic" or "condensed ring" has a substituent is, for example, the "arbitrary substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic" or "condensed ring" has a substituent are the substituents described in the section of "substituents described in this specification" described above. When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "any substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the section of "substituents described in this specification" mentioned above. The above is the explanation for the case where "one or more sets of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted monocyclic ring", and the case where "one or more sets of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted condensed ring" (the case of "bonding to form a ring").

[0107] · Substituent 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 groups selected from the group consisting of, etc., Here, R 901 ~R 907 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, an aryl group having 6 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, or a heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted. R 901 When two or more Rs are present, the two or more Rs 901 may be the same as or different from each other, R 902 When two or more Rs are present, the two or more Rs 902 may be the same as or different from each other, R 903 When two or more Rs are present, the two or more Rs 903 may be the same as or different from each other, R 904 When two or more Rs are present, the two or more Rs 904 may be the same as or different from each other, R 905 When two or more Rs are present, the two or more Rs 905 may be the same as or different from each other, R 906 When two or more Rs are present, the two or more Rs 906 may be the same as or different from each other, R 907 When two or more Rs are present, the two or more Rs 907 may be the same as or different from each other.

[0108] In one embodiment, the substituent in the case of "substituted or unsubstituted" is an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring-forming carbon atoms, and a heterocyclic group having 5 to 50 ring-forming atoms selected from the group consisting of.

[0109] 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 is a group selected from the group consisting of.

[0110] Specific examples of each group of the above-mentioned optional substituents are the specific examples of the substituents described in the section of "Substituents Described in this Specification" mentioned above.

[0111] Unless otherwise specified in this specification, any adjacent substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, and more preferably form a benzene ring. Unless otherwise specified in this specification, any substituent may further have a substituent. The substituents that any substituent further has are the same as the above-mentioned any substituents.

[0112] In this specification, 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.

[0113] [Novel compound] The compound according to one aspect of the present invention is represented by the following formula (1). [Chemical formula] (In the above formula (1), R a ~R d are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and R a ~R d at least one of which is a substituted or unsubstituted biphenyl-2-yl group. R a ~R d at least one of which contains a substituent A. The substituent A is 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, and -Si(R 31 )(R 32)(R 33 ) is one or more selected from the group consisting of R 1 ~R 6 and R 11 ~R 16 Among them, one or more pairs of two or more adjacent ones form a substituted or unsubstituted saturated or unsaturated ring, or do not form the substituted or unsubstituted saturated or unsaturated ring. R 21 R 22 , and R 1 ~R 6 and R 11 ~R 16 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -Si(R 31 )(R 32 )(R 33 ), -C(=O)R 34 , -COOR 35 , -N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. R 31 ~R 37 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. R 31~R 37 When there are a plurality of each of them, the plurality of Rs 31 ~R 37 may each be the same or different. )

[0114] By using the compound according to one aspect of the present invention, a long-life organic EL element can be manufactured. Hereinafter, the compound represented by formula (1) will be described.

[0115] In the compound represented by formula (1), R a ~R d at least one of which is a substituted or unsubstituted biphenyl-2-yl group.

Chemical formula

[0116] Also, the compound represented by formula (1) has a structure in which a specific substituent (substituent A) is bonded to at least one of R a ~R d That is, the substituent A is bonded to at least one of the aryl groups having 6 to 50 ring-forming carbon atoms of R a ~R d The bonding site of the substituent A may be the above biphenyl-2-yl group. Further, when the aryl group having 6 to 50 ring-forming carbon atoms has another substituent, the substituent A may be bonded to the substituent.

[0117] The substituent A is one or more selected from the group consisting of 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, and -Si(R 31 )(R 32 )(R 33 ). When there are a plurality of substituents A in the compound represented by formula (1), the plurality of substituents A may each be the same or different.

[0118] In one embodiment, R a ~R dAt least two (e.g., two, three, or four) of them are substituted or unsubstituted biphenyl-2-yl groups.

[0119] In one embodiment, R a and R b at least one of which is a substituted or unsubstituted biphenyl-2-yl group, and R c and R d at least one of which is a substituted or unsubstituted biphenyl-2-yl group. In one embodiment, R a and R c are substituted or unsubstituted biphenyl-2-yl groups, and R b and R d are substituted or unsubstituted aryl groups having 6 to 50 ring-forming carbon atoms other than substituted or unsubstituted biphenyl-2-yl groups.

[0120] In one embodiment, all or some of the hydrogen atoms included in R a to R d may be deuterium atoms. Also, all or some of the hydrogen atoms included in the substituted or unsubstituted biphenyl-2-yl group may be deuterium atoms, and all or some of the hydrogen atoms included in the substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms other than the substituted or unsubstituted biphenyl-2-yl group may be deuterium atoms.

[0121] In one embodiment, the substituent A is one or more selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, and -Si(R 31 )(R 32 )(R 33 ).

[0122] In one embodiment, the substituent A is one or more selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms and -Si(R 31 )(R 32 )(R 33 ). In the above embodiment, R31 ~R 33 is preferably, independently of one another, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

[0123] In one embodiment, the substituent A is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0124] In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (1-1).

Chemical formula

[0125] In one embodiment, R b and R d are a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

[0126] In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (1-2).

Chemical formula

[0127] In one embodiment, at least one of R 61 ~R 69 , and at least one of R 71 ~R 79 is the substituent A.

[0128] In one embodiment, at least one of R 61 ~R 69 , and at least one of R 71 ~R 79 is, independently of one another, the substituent A.

[0129] In one embodiment, at least one of R 81 ~R 85 , and R91 ~R 95 At least one of them is the substituent A.

[0130] In one embodiment, R 81 ~R 85 At least one of, and R 91 ~R 95 At least one of is each independently the substituent A.

[0131] In one embodiment, R 61 ~R 69 , and R 71 ~R 79 At least one of, as well as R 81 ~R 85 , and R 91 ~R 95 At least one of is each independently the substituent A.

[0132] In one embodiment, R 63 and R 73 are each independently the substituent A. In one embodiment, R 67 and R 77 are each independently the substituent A.

[0133] "R 1 ~R 6 and R 11 ~R 16 Among them, one or more sets of two or more adjacent ones form a substituted or unsubstituted saturated or unsaturated ring, or do not form the substituted or unsubstituted saturated or unsaturated ring" will be described. "One set of two or more adjacent ones among R 1 ~R 6 and R 11 ~R 16 ", for example, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 11 and R12 , R 1 and R 2 and R 3 and the like. When the substituent in the case of "substituted or unsubstituted" for the above saturated or unsaturated ring is the same as the substituent in the case of "substituted or unsubstituted" described later.

[0134] The "saturated or unsaturated ring" means, for example, when forming a ring with R 1 and R 2 it means a ring formed by the carbon atom to which R 1 is bonded, the carbon atom to which R 2 is bonded, and one or more arbitrary atoms. Specifically, when forming a ring with R 1 and R 2 in the case where the carbon atom to which R 1 is bonded, the carbon atom to which R 2 is bonded, and four carbon atoms form an unsaturated ring, the ring formed by R 1 and R 2 is a benzene ring.

[0135] The "arbitrary atom" is preferably a C atom, an N atom, an O atom, or an S atom. In the case of an arbitrary atom (for example, in the case of a C atom or an N atom), the bond that does not form a ring may be terminated with a hydrogen atom or the like. The "one or more arbitrary atoms" are preferably two or more and 15 or less, more preferably three or more and 12 or less, and still more preferably three or more and five or less arbitrary atoms. Hereinafter, the expression "two or more adjacent ones among X to Y form a substituted or unsubstituted saturated or unsaturated ring, or do not form the substituted or unsubstituted saturated or unsaturated ring" has the same meaning when X is substituted with the above R 1 and Y is substituted with the above R 6 .

[0136] In one embodiment, R 1 ~R 6 , and R 11 ~R 16at least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and R 21 and R 22 is a hydrogen atom. In one embodiment, at least one of R 1 ~R 6 and at least one of R 11 ~R 16 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and R 21 and R 22 are hydrogen atoms.

[0137] In one embodiment, R 1 ~R 6 , R 11 ~R 16 , R 21 and R 22 are hydrogen atoms.

[0138] In one embodiment, R 81 ~R 85 , and R 91 ~R 95 are hydrogen atoms. In this case, all or part of R 81 ~R 85 , and R 91 ~R 95 may be deuterium atoms.

[0139] In one embodiment, R 61 ~R 69 , and R 71 ~R 79 are hydrogen atoms. In this case, all or part of R 61 ~R 69 , and R 71 ~R 79 may be deuterium atoms. For example, R 61 ~R 64 , and R 71 ~R 74 are protium atoms, and R 65 ~R 69 , and R 75 ~R 79 may be deuterium atoms.

[0140] In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (1-3).

Chemical formula

[0141] In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (1-4).

Chemical formula

[0142] In one embodiment, R 3 and R 13 are hydrogen atoms.

[0143] In one embodiment, R 3 and R 13 are a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0144] In one embodiment, R 82 and R 92 are each independently the substituent A.

[0145] In one embodiment, R 83 and R 93 are each independently the substituent A.

[0146] In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (1-5). [Chemical formula] (In the formula (1-5), R 63 , R 73 , R 83 , and R 93 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -Si(R 31 )(R 32 )(R 33 ), -C(=O)R 34 , -COOR 35 , -N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. R 63 and R 73 At least one of them is the substituent A.)

[0147] In one embodiment, R 83 and R 93 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0148] In the case of "substituted or unsubstituted" in the compound represented by formula (1), the substituents are an alkyl group having 1 to 50 carbon atoms, a haloalkyl group having 1 to 50 carbon atoms, an alkenyl group having 2 to 50 carbon atoms, an alkynyl group having 2 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring-forming carbon atoms, an alkoxy group having 1 to 50 carbon atoms, an alkylthio group having 1 to 50 carbon atoms, an aryloxy group having 6 to 50 ring-forming carbon atoms, an arylthio group having 6 to 50 ring-forming carbon atoms, an aralkyl group having 7 to 50 carbon atoms, -Si(R 41 )(R 42 )(R 43 ), -C(=O)R 44 , -COOR 45 , -S(=O) 2 R 46 , -P(=O)(R 47 )(R 48 ), -Ge(R 49 )(R 50 )(R 51 ), -N(R 52 )(R 53 ) (wherein R 41 to R 53 are each independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring-forming atoms. When two or more of R 41 to R 53 are present, each of the two or more R 41 to R 53 may be the same or different.), a hydroxy group, a halogen atom, a cyano group, a nitro group, an aryl group having 6 to 50 ring-forming carbon atoms, and a monovalent heterocyclic group having 5 to 50 ring-forming atoms.

[0149] In one embodiment, the substituents in the case of "substituted or unsubstituted" in the compound represented by formula (1) are an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring-forming carbon atoms, and a monovalent heterocyclic group having 5 to 50 ring-forming atoms.

[0150] In one embodiment, the substituent in the case of "substituted or unsubstituted" in the compound represented by formula (1) is selected from the group consisting of an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 ring-forming carbon atoms, and a monovalent heterocyclic group having 5 to 30 ring-forming atoms.

[0151] In one embodiment, the substituent in the case of "substituted or unsubstituted" in the compound represented by formula (1) is selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring-forming carbon atoms, and a monovalent heterocyclic group having 5 to 18 ring-forming atoms.

[0152] Specific examples of each substituent of the compound represented by formula (1), the substituent in the case of "substituted or unsubstituted", and the halogen atom are the same as those described above, respectively.

[0153] The compound represented by formula (1) can be synthesized by following the examples and using known alternative reactions and raw materials according to the target product.

[0154] Specific examples of the compound represented by formula (1) are described below, but these are merely illustrative and the compound represented by formula (1) is not limited to the following specific examples.

[0155]

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0156] [Materials for organic EL devices] The compound according to one aspect of the present invention is useful as a material for an organic EL device, useful as a material for the light-emitting layer of an organic EL device, and particularly useful as a dopant material for the light-emitting layer. By using the compound according to one aspect of the present invention in the light-emitting layer of an organic EL device, it becomes possible to obtain an organic EL device with a long lifespan.

[0157] [Organic EL device] The organic EL device according to one aspect of the present invention has a cathode, an anode, and at least one organic layer disposed between the cathode and the anode, and at least one of the at least one organic layer contains the compound represented by the formula (1).

[0158] The schematic configuration of the organic EL device according to one aspect of the present invention will be described with reference to FIG. 1. The organic EL device 1 according to one aspect of the present invention has a substrate 2, an anode 3, a light-emitting layer 5 which is an organic layer, a cathode 10, an organic layer 4 between the anode 3 and the light-emitting layer 5, and an organic layer 6 between the light-emitting layer 5 and the cathode 10. The organic layer 4 and the organic layer 6 may each be a single layer or may be composed of a plurality of layers. Further, the organic layer 4 may include a hole transport region. The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, and the like. The organic layer 6 may include an electron transport region. The electron transport region may include an electron injection layer, an electron transport layer, a hole blocking layer, and the like. The compound represented by the formula (1) is included in the organic layer 4, the light-emitting layer 5, or the organic layer 6. In one embodiment, the compound represented by the formula (1) is included in the light-emitting layer 5. The compound represented by the formula (1) can function as a dopant material in the light-emitting layer 5.

[0159] In the organic EL element according to one aspect of the present invention, at least one of the at least one organic layer includes a first compound and a second compound, and the first compound is a compound represented by the formula (1).

[0160] In the organic EL element according to one aspect of the present invention, the second compound is a heterocyclic compound or a condensed aromatic compound. In the organic EL element according to one aspect of the present invention, the second compound is an anthracene derivative.

[0161] In the organic EL element according to one aspect of the present invention, the second compound is a compound represented by the following formula (10).

[0162] <Compound represented by formula (10)> The compound represented by formula (10) will be described.

[0163]

Chemical formula

[0164] [In formula (10), R 101 ~R 110 Among them, one or more sets of two or more adjacent ones form a substituted or unsubstituted saturated or unsaturated ring, or do not form the substituted or unsubstituted saturated or unsaturated ring. R which does not form the above-mentioned substituted or unsubstituted saturated or unsaturated ring 101 ~R 110 are each independently a hydrogen atom, a substituent R, or a group represented by the following formula (11). -L 101 -Ar 101 (11)

[0165] (In formula (11), L 101 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.) Ar 101 is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.) The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.) When there are two or more of the substituents R, the two or more substituents R may be the same or different. R 901 ~R 907 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. R 901 ~R 907 When there are two or more of them, the two or more Rs 901 ~R 907 each may be the same or different. However, at least one of the R 101 ~R 110 that does not form a substituted or unsubstituted saturated or unsaturated ring is a group represented by the formula (11). When there are two or more of the formula (11), each of the two or more groups represented by the formula (11) may be the same or different. The compound represented by the above formula (10) may have a deuterium atom as a hydrogen atom.

[0166] In one embodiment, at least one of the Ar 101 in the formula (10) is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

[0167] In one embodiment, at least one of the Ar 101 in the formula (10) is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.

[0168] In one embodiment, all of the Ar 101 in the formula (10) are substituted or unsubstituted aryl groups having 6 to 50 ring-forming carbon atoms. The plurality of Ar 101 may be the same as or different from each other.

[0169] In one embodiment, Ar in the formula (10) 101 is one of a monovalent heterocyclic group having 5 to 50 ring-forming atoms which may be substituted or unsubstituted, and the remaining Ar 101 is an aryl group having 6 to 50 ring-forming carbon atoms which may be substituted or unsubstituted. A plurality of Ar 101 may be the same as or different from each other.

[0170] In one embodiment, at least one of L in the formula (10) 101 is a single bond. In one embodiment, all of L in the formula (10) 101 are single bonds. In one embodiment, at least one of L in the formula (10) 101 is an arylene group having 6 to 50 ring-forming carbon atoms which may be substituted or unsubstituted. In one embodiment, at least one of L in the formula (10) 101 is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthyl group.

[0171] In one embodiment, the group represented by -L 101 -Ar 101 in the formula (10) is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and is selected from the group consisting of a substituted or unsubstituted carbazolyl group.

[0172] In one embodiment, each of the substituents R in the formula (10) is independently 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, -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, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms. R 901 ~R 907 are as defined in the formula (10).

[0173] In one embodiment, each of the "substituted or unsubstituted" substituents in the formula (10) is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. R 901 ~R 907 is as defined in the above formula (10).

[0174] In one embodiment, the substituents of "substituted or unsubstituted" in the formula (10) are each independently 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, -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, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms. R 901 ~R 907 is as defined in the above formula (10).

[0175] In one embodiment, the substituents in the case of "substituted or unsubstituted" in the formula (10) are an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring-forming carbon atoms, and a monovalent heterocyclic group having 5 to 18 ring-forming atoms, selected from the group consisting of.

[0176] In one embodiment, the substituents in the case of "substituted or unsubstituted" in the formula (10) are an alkyl group having 1 to 5 carbon atoms.

[0177] In one embodiment, the compound represented by the formula (10) is a compound represented by the following formula (20).

[0178]

Chemical formula

[0179] (In formula (20), R 101 ~R 108 , L 101 and Ar 101 are as defined in the above formula (10).) The compound represented by the above formula (20) may have a deuterium atom as a hydrogen atom.

[0180] That is, in one embodiment, the compound represented by the formula (10) or formula (20) has at least two groups represented by the formula (11). In one embodiment, the compound represented by the formula (10) or formula (20) has two or three groups represented by the formula (11).

[0181] In one embodiment, R 101 ~R 110 in the formulas (10) and (20) do not form a substituted or unsubstituted saturated or unsaturated ring. In one embodiment, R 101 ~R 110 in the formulas (10) and (20) are hydrogen atoms.

[0182] In one embodiment, the compound represented by the formula (20) is a compound represented by the following formula (30).

[0183] [Chemical formula]

[0184] (In formula (30), L 101 and Ar 101 are as defined in the above formula (10). Of R 101A ~R 108A , two adjacent ones do not form a substituted or unsubstituted saturated or unsaturated ring. R 101A ~R 108A are each independently a hydrogen atom, or It is the substituent R. The substituent R is as defined in the formula (10).)

[0185] That is, the compound represented by the above formula (30) is a compound having two groups represented by the formula (11). The compound represented by the above formula (30) has substantially only light hydrogen atoms as hydrogen atoms. In addition, "having substantially only light hydrogen atoms" means that, for a compound having the same structure and having only light hydrogen atoms as hydrogen atoms (light hydrogen form) and a compound having deuterium atoms (deuterium form), the ratio of the light hydrogen form is 90 mol% or more, 95 mol% or more, or 99 mol% or more with respect to the total.

[0186] In one embodiment, the compound represented by the formula (30) is a compound represented by the following formula (31).

[0187]

Chemical formula

[0188] (In the formula (31), L 101 and Ar 101 are as defined in the formula (10). R 101A ~R 108A are as defined in the formula (30). X b is O, S, N(R 131 ), or C(R 132 )(R 133 ). R 121 ~R 128 , and one of R 131 ~R 133 is a single bond that binds to L 101 . L 101 The R that is not a single bond binding to 121 ~R 128Among them, one or more sets of two or more adjacent ones form a substituted or unsubstituted saturated or unsaturated ring, or do not form the substituted or unsubstituted saturated or unsaturated ring. L 101 is not a single bond connecting to, and does not form the substituted or unsubstituted saturated or unsaturated ring, R 121 ~R 128 each independently is a hydrogen atom, or a substituent R. The substituent R is as defined in the formula (10). L 101 R that is not a single bond connecting to 131 ~R 133 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. R 131 ~R 133 When two or more Rs 131 ~R 133 are present, each of the two or more Rs

[0189] In one embodiment, the compound represented by the formula (31) is a compound represented by the following formula (32).

[0190]

Chemical formula

[0191] (In the formula (32), R 101A ~R 108A , L 101 , Ar 101 , R 121 ~R 128 , R 132 and R 133is as defined in the above formula (31).)

[0192] In one embodiment, the compound represented by the formula (31) is a compound represented by the following formula (33).

[0193] [Chemical formula]

[0194] (In formula (33), R 101A ~R 108A , L 101 , Ar 101 , and R 121 ~R 128 are as defined in the above formula (31). X c is O, S, or NR 131 . R 131 is as defined in the above formula (31).)

[0195] In one embodiment, the compound represented by the formula (31) is a compound represented by the following formula (34).

[0196] [Chemical formula]

[0197] (In formula (34), R 101A ~R 108A , L 101 and Ar 101 are as defined in the above formula (31). X c is O, S, or NR 131 . R 131 is as defined in the above formula (31). R 121A ~R 128A One of them is a single bond that binds to L 101 . L 101 The R that is not a single bond binding to 121A ~R128A Among them, at least one set of two or more adjacent ones does not form a substituted or unsubstituted saturated or unsaturated ring. L 101 R that is not a single bond connecting to 121A ~R 128A are each independently a hydrogen atom, or a substituent R. The substituent R is as defined in the formula (10).)

[0198] In one embodiment, the compound represented by the formula (31) is a compound represented by the following formula (35).

[0199]

Chemical formula

[0200] [In the formula (35), R 101A ~R 108A , L 101 , Ar 101 and X b are as defined in the formula (31). R 121A ~R 124A Among them, at least one set of two or more adjacent ones do not bond to each other to form a substituted or unsubstituted saturated or unsaturated ring. R 125B and R 126B , R 126B and R 127B , and R 127B and R 128B Among any one set of them, they bond to each other to form a ring represented by the following formula (35a) or (35b).

[0201]

Chemical formula

[0202] (In the formulas (35a) and (35b), The two * are each, R 125B and R R126B , R126B and R 127B , and R 127B and R 128B combines with any one of the following groups. R 141 ~R 144 are each independently a hydrogen atom, or a substituent R. The substituent R is as defined in the formula (10). X d is O or S.) R 121A ~R 124A R that does not form a ring represented by the formula (35a) or (35b) 125B ~R 128B , and R 141 ~R 144 One of them is a single bond that binds to L 101 101 L 101 R that is not a single bond that binds to L 121A ~R 124A , and L 101 is not a single bond that binds to L and does not form a ring represented by the formula (35a) or (35b) 125B ~R 128B are each independently a hydrogen atom, or a substituent R. The substituent R is as defined in the formula (10).]

[0203] In one embodiment, the compound represented by the formula (35) is a compound represented by the following formula (36).

[0204]

Chemical formula

[0205] (In formula (36), R 101A ~R 108A , L 101 , Ar 101 , and R 125B ~R 128B are as defined in the formula (35).)

[0206] In one embodiment, the compound represented by the formula (34) is a compound represented by the following formula (37).

[0207] [Chemical Formula]

[0208] (In formula (37), R 101A ~R 108A , R 125A ~R 128A , L 101 and Ar 101 are as defined in the formula (34).)

[0209] In one embodiment, R 101A ~R 108A in the formulas (30) to (37) are hydrogen atoms.

[0210] In one embodiment, the compound represented by the formula (10) is a compound represented by the following formula (40).

[0211] [Chemical Formula]

[0212] (In formula (40), L 101 and Ar 101 are as defined in the formula (10). R 101A , and R 103A ~R 108A among two or more adjacent ones form a substituted or unsubstituted saturated or unsaturated ring, or do not form the substituted or unsubstituted saturated or unsaturated ring. R 101A and R 103A ~R 108A that do not form the substituted or unsubstituted saturated or unsaturated ring are each independently a hydrogen atom, or a substituent R. The substituent R is as defined in the formula (10).) That is, the compound represented by the formula (40) is a compound having three groups represented by the formula (11). Further, the compound represented by the formula (40) has substantially only light hydrogen atoms as hydrogen atoms.

[0213] In one embodiment, the compound represented by the formula (40) is represented by the following formula (41).

[0214] [Chemical formula]

[0215] (In the formula (41), L 101 and Ar 101 are as defined in the formula (40).)

[0216] In one embodiment, the compound represented by the formula (40) is a compound represented by any one of the following formulas (42-1) to (42-3).

[0217] [Chemical formula]

[0218] (In the formulas (42-1) to (42-3), R 101A ~R 108A , L 101 and Ar 101 are as defined in the formula (40).)

[0219] In one embodiment, the compounds represented by the formulas (42-1) to (42-3) are compounds represented by any one of the following formulas (43-1) to (43-3).

[0220] [Chemical formula]

[0221] (In the formulas (43-1) to (43-3), L101 and Ar 101 is as defined in the above formula (40).)

[0222] In one embodiment, -L in the above formulas (40), (41), (42-1) to (42-3), and (43-1) to (43-3) 101 -Ar 101 The group represented by is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and is selected from the group consisting of a substituted or unsubstituted carbazolyl group.

[0223] In one embodiment, the compound represented by the above formula (10) or formula (20) includes a compound in which at least one of the hydrogen atoms of these compounds is a deuterium atom.

[0224] In one embodiment, in the above formula (20) R which is a hydrogen atom 101 ~R 108 , R which is the above substituent R 101 ~R 108 the hydrogen atoms possessed by, L 101 the hydrogen atoms possessed by, L 101 the hydrogen atoms possessed by the substituents of, Ar 101 the hydrogen atoms possessed by, and Ar 101 the hydrogen atoms possessed by the substituents of At least one of the is a deuterium atom.

[0225] The compounds represented by the formulas (30) to (37) include compounds in which at least one of the hydrogen atoms contained in these compounds is a deuterium atom. In one embodiment, at least one of the hydrogen atoms bonded to the carbon atoms constituting the anthracene skeleton in the compounds represented by the formulas (30) to (37) is a deuterium atom.

[0226] In one embodiment, the compound represented by formula (30) is a compound represented by formula (30D):

[0227] [ka]

[0228] (In formula (30D), R 101A ~R 108A , L 101 and Ar 101 is as defined in the above formula (30). However, R is a hydrogen atom. 101A ~R 110A , The substituent R is R 101A ~R 110A a hydrogen atom possessed by L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of Ar 101 A hydrogen atom held by Ar 101 Hydrogen atoms of the substituents of At least one of the is a deuterium atom.) That is, the compound represented by the above formula (30D) is a compound in which at least one of the hydrogen atoms of the compound represented by the above formula (30) is a deuterium atom.

[0229] In one embodiment, R which is a hydrogen atom in formula (30D)101A ~R 108A At least one of them is a deuterium atom.

[0230] In one embodiment, the compound represented by the formula (30D) is a compound represented by the following formula (31D).

[0231]

Chemical formula

[0232] (In the formula (31D), R 101A ~R 108A , L 101 and Ar 101 are as defined in the formula (30D). X d is O or S. R 121 ~R 128 One of them is a single bond connecting to L 101 . L 101 For R that is not a single bond connecting to 121 ~R 128 Among two or more adjacent ones, one or more sets form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring. L 101 For R that is not a single bond connecting to and does not form the substituted or unsubstituted saturated or unsaturated ring 121 ~R 128 are each independently a hydrogen atom, or a substituent R. The substituent R is as defined in the formula (10). However, for R that is a hydrogen atom 101A ~R 110A , for R that is the substituent R 101A ~R 110A the hydrogen atoms they have, L 101 the hydrogen atoms it has, L 101 the hydrogen atoms of the substituents of Ar 101 a hydrogen atom possessed by Ar 101 Hydrogen atoms of the substituents of R is a hydrogen atom 121 ~R 128 , and The substituent R is R 121 ~R 128 Hydrogen atoms possessed by At least one of the is a deuterium atom.)

[0233] In one embodiment, the compound represented by formula (31D) is a compound represented by formula (32D):

[0234] [ka]

[0235] (In formula (32D), R 101A ~R 108A , R 125A ~R 128A , L 101 and Ar 101 is as defined in formula (31D) above. however, R is a hydrogen atom 101A ~R 108A , The substituent R is R 101A ~R 108A a hydrogen atom possessed by R is a hydrogen atom 125A ~R 128A , The substituent R is R 125A ~R 128A a hydrogen atom possessed by A hydrogen atom bonded to a carbon atom of the dibenzofuran skeleton in formula (32D), L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of Ar 101 A hydrogen atom held by Ar 101 Hydrogen atoms of the substituents of At least one of them is a deuterium atom.)

[0236] In one embodiment, the compound represented by the formula (32D) is a compound represented by the following formula (32D-1) or (32D-2).

[0237] [Chemical formula]

[0238] (In the formulas (32D-1) and (32D-2), R 101A ~R 108A , R 125A ~R 128A , L 101 and Ar 101 are as defined in the formula (32D). However,[[]] R 101A ~R 108A which is a hydrogen atom, R 101A ~R 108A which is the hydrogen atom possessed by the substituent R, R 125A ~R 128A which is a hydrogen atom, R 125A ~R 128A which is the hydrogen atom possessed by the substituent R, the hydrogen atom bonded to the carbon atom of the dibenzofuran skeleton in the formulas (32D-1) and (32D-2), L 101 the hydrogen atom possessed by it, L 101 the hydrogen atom possessed by the substituent of it, Ar 101 the hydrogen atom possessed by it, and Ar 101 the hydrogen atom possessed by the substituent of it At least one of them is a deuterium atom.)

[0239] In one embodiment, at least one of the hydrogen atoms possessed by the compound represented by the formula (40), (41), (42-1) to (42-3) or (43-1) to (43-3) is a deuterium atom.

[0240] In one embodiment, at least one of the hydrogen atoms (R being a hydrogen atom) bonded to the carbon atoms constituting the anthracene skeleton in the compound represented by the formula (41) is a deuterium atom. 101A ~R 108A ) is a deuterium atom.

[0241] In one embodiment, the compound represented by the formula (40) is a compound represented by the following formula (40D).

[0242] [Chemical formula]

[0243] (In the formula (40D), L 101 and Ar 101 are as defined in the formula (10). R 101A , and R 103A ~R 108A Among two or more adjacent pairs of them do not form a substituted or unsubstituted saturated or unsaturated ring. R 101A , and R 103A ~R 108A are each independently a hydrogen atom, or a substituent R. The substituent R is as defined in the formula (10). However, R being a hydrogen atom 101A , and R 103A ~R 108A , R being the substituent R 101A , and R 103A ~R 108A The hydrogen atoms they have, The hydrogen atoms that L 101 has, The hydrogen atoms that the substituent of L 101 has, The hydrogen atoms that Ar 101 has, and Ar 101 The hydrogen atoms that the substituent of At least one of them is a deuterium atom.)

[0244] In one embodiment, R in the formula (40D) 101A , and R 103A ~R 108A At least one of them is a deuterium atom.

[0245] In one embodiment, the compound represented by the formula (40D) is a compound represented by the following formula (41D).

[0246]

Chemical formula

[0247] (In the formula (41D), L 101 and Ar 101 are as defined in the formula (40D). However, in the formula (41D), The hydrogen atom bonded to the carbon atom constituting the anthracene skeleton,[[]] The hydrogen atom that L 101 has,[[]] The hydrogen atom that the substituent of L 101 has,[[]] The hydrogen atom that Ar 101 has, and The hydrogen atom that the substituent of Ar 101 has,[[]] At least one of them is a deuterium atom.)

[0248] In one embodiment, the compound represented by the formula (40D) is a compound represented by any one of the following formulas (42D-1) to (42D-3).

[0249]

Chemical formula

[0250] (In the formulas (42D-1) to (42D-3), R 101A ~R 108A , L 101 and Ar 101is as defined by the formula (40D). However, in the formula (42D-1), R which is a hydrogen atom 101A , and R 103A ~R 108A , R which is the substituent R 101A , and R 103A ~R 108A and the hydrogen atoms possessed by them, the hydrogen atoms possessed by L 101 , the hydrogen atoms possessed by the substituents of L 101 , the hydrogen atoms possessed by Ar 101 , the hydrogen atoms possessed by the substituents of Ar 101 , and at least one of the hydrogen atoms bonded to the carbon atoms constituting the phenyl group in the formula (42D-1) is a deuterium atom. R which is a hydrogen atom in the formula (42D-2) 101A , and R 103A ~R 108A , R which is the substituent R 101A , and R 103A ~R 108A and the hydrogen atoms possessed by them, the hydrogen atoms possessed by L 101 , the hydrogen atoms possessed by the substituents of L 101 , the hydrogen atoms possessed by Ar 101 , the hydrogen atoms possessed by the substituents of Ar 101 , and at least one of the hydrogen atoms bonded to the carbon atoms constituting the naphthyl group in the formula (42D-2) is a deuterium atom. R which is a hydrogen atom in the formula (42D-3) 101A , and R 103A ~R 108A , R which is the substituent R 101A , and R 103A ~R 108A and the hydrogen atoms possessed by them, the hydrogen atoms possessed by L 101 , L 101 The hydrogen atom(s) of the substituent of Ar 101 the hydrogen atom(s) of Ar 101 the hydrogen atom(s) of the substituent of, and the hydrogen atom(s) bonded to the carbon atom(s) constituting the naphthyl group in the formula (42D-3) at least one of which is a deuterium atom.)

[0251] In one embodiment, the compound represented by the formula (42D-1) to (42D-3) is a compound represented by any one of the following formula (43D-1) to (43D-3).

[0252]

Chemical formula

[0253] (In the formula (43D-1) to (43D-3), L 101 and Ar 101 are as defined in the formula (40D). However, the hydrogen atom(s) bonded to the carbon atom(s) constituting the anthracene skeleton in the formula (43D-1), L 101 the hydrogen atom(s) of L 101 the hydrogen atom(s) of the substituent of Ar 101 the hydrogen atom(s) of Ar 101 the hydrogen atom(s) of the substituent of, and at least one of the hydrogen atom(s) bonded to the carbon atom(s) constituting the phenyl group in the formula (43D-1) is a deuterium atom.) The hydrogen atom(s) bonded to the carbon atom(s) constituting the anthracene skeleton in the formula (43D-2), L 101 the hydrogen atom(s) of L 101 the hydrogen atom(s) of the substituent of Ar 101 the hydrogen atom(s) of Ar 101The hydrogen atom(s) of the substituent, and at least one of the hydrogen atoms bonded to the carbon atoms constituting the naphthyl group in the formula (43D-2) is a deuterium atom. The hydrogen atom(s) bonded to the carbon atoms constituting the anthracene skeleton in the formula (43D-3), L 101 the hydrogen atom(s) it has, L 101 the hydrogen atom(s) of the substituent it has, Ar 101 the hydrogen atom(s) it has, Ar 101 the hydrogen atom(s) of the substituent it has, and the hydrogen atom(s) bonded to the carbon atoms constituting the naphthyl group in the formula (43D-3) of which at least one is a deuterium atom.)

[0254] In one embodiment, in the compound represented by the formula (20), at least one of Ar 101 is a monovalent group having a structure represented by the following formula (50).

[0255]

Chemical formula

[0256] (In the formula (50), X 151 is O, S or C(R 161 )(R 162 ). R 151 ~R 160 One of them is a single bond that binds to L 101 . L 101 Of the R 151 ~R 154 that are not a single bond binding to, two or more adjacent ones, and of the R 155 ~R 160 Two or more adjacent ones of them, one or more sets of which are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring. R161 and R 162 either combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring. R that does not form a substituted or unsubstituted saturated or unsaturated ring 161 and R 162 , and L 101 is not a single bond that binds to, and does not form a substituted or unsubstituted saturated or unsaturated ring 151 ~R 160 are each independently a hydrogen atom or a substituent R. The substituent R is as defined in the formula (10). Ar which is not a monovalent group having the structure represented by the formula (50) 101 is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms. )

[0257] L in the formula (50) 101 The position of the single bond that binds to is not particularly limited. In one embodiment, R 151 ~R 154 among them, or R 155 ~R 160 among them, is a single bond that binds to L 101

[0258] In one embodiment, Ar 101 is a monovalent group represented by the following formula (50-R 152 ), (50-R 153 ), (50-R 154 ), (50-R 157 ) or (50-R 158 ).

Chemical formula

[0259] (Formula (50-R 152 ), (50-R​153 ), (50 - R 154 ), (50 - R 157 ), and (50 - R 158 ), in which X 151 , R 151 ~R 160 are as defined in the said formula (50). * is bonded to L 101 ).

[0260] Examples of the compound represented by formula (10) include, for example, the compounds shown below. The compound represented by formula (10) is not limited to these specific examples. In the following specific examples, D represents a deuterium atom.

[0261]

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0262] As described above, the organic EL element according to one aspect of the present invention has a cathode, an anode, and a light-emitting layer between the cathode and the anode. As long as the light-emitting layer contains the compound represented by the formula (1) and does not impair the effects of the present invention, conventionally known materials and element configurations can be applied. The content of the compound represented by the formula (1) in the light-emitting layer is preferably 1% by mass or more and 20% by mass or less with respect to the entire light-emitting layer.

[0263] Typical element configurations of the organic EL element of the present invention include (1) Anode / Light-emitting layer / Cathode (2) Anode / Hole injection layer / Light-emitting layer / Cathode (3) Anode / Light-emitting layer / Electron injection / transport layer / Cathode (4) Anode / Hole injection layer / Light-emitting layer / Electron injection / transport layer / Cathode (5) Anode / Organic semiconductor layer / Light-emitting layer / Cathode (6) Anode / Organic semiconductor layer / Electron barrier layer / Light-emitting layer / Cathode (7) Anode / Organic semiconductor layer / Light-emitting layer / Adhesion improvement layer / Cathode (8) Anode / Hole injection / transport layer / Light-emitting layer / Electron injection / transport layer / Cathode (9) Anode / Insulating layer / Light-emitting layer / Insulating layer / Cathode (10) Anode / Inorganic semiconductor layer / Insulating layer / Light-emitting layer / Insulating layer / Cathode (11) Anode / Organic semiconductor layer / Insulating layer / Light-emitting layer / Insulating layer / Cathode (12) Anode / Insulating layer / Hole injection / transport layer / Light-emitting layer / Insulating layer / Cathode (13) Anode / Insulating layer / Hole injection / transport layer / Light-emitting layer / Electron injection / transport layer / Cathode Structures such as the above can be cited. Among the above, the configuration of (8) is preferably used, but is not limited thereto.

[0264] In this specification, the "hole injection / transport layer" means "at least one of the hole injection layer and the hole transport layer", and the "electron injection / transport layer" means "at least one of the electron injection layer and the electron transport layer".

[0265] Hereinafter, members that can be used in the organic EL element according to one aspect of the present invention, and materials other than the above compounds that constitute each layer will be described.

[0266] (Substrate) The substrate is used as a support for the light-emitting element. As the substrate, for example, glass, quartz, plastic, etc. can be used. Also, a flexible substrate may be used. A flexible substrate is a substrate that can be bent (flexible), and examples include plastic substrates made of polycarbonate and polyvinyl chloride.

[0267] (Anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electroconductive compound, and mixtures thereof having a large work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, etc. can be mentioned. In addition, gold (Au), platinum (Pt), or nitrides of metal materials (for example, titanium nitride) etc. can be mentioned.

[0268] (Hole injection layer) The hole injection layer is a layer containing a substance with high hole injection properties. As substances with high hole injection properties, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compounds, or polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used.

[0269] (Hole transport layer) The hole transport layer is a layer containing a substance with high hole transportability. In the hole transport layer, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used. High molecular compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. However, as long as it is a substance with higher hole transportability than electrons, other substances may be used. In addition, the layer containing a substance with high hole transportability may be not only a single layer but also a laminate of two or more layers composed of the above substances.

[0270] (Guest (dopant) material of the light-emitting layer) The light-emitting layer is a layer containing a highly light-emitting substance. In addition to the materials (compounds represented by formula (1)) used in the present invention described above, various materials can be used. For example, as the highly light-emitting substance, a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used. A fluorescent compound is a compound that can emit light from the singlet excited state, and a phosphorescent compound is a compound that can emit light from the triplet excited state. As a blue fluorescent light-emitting material that can be used in the light-emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. can be used. As a green fluorescent light-emitting material that can be used in the light-emitting layer, aromatic amine derivatives, etc. can be used. As a red fluorescent light-emitting material that can be used in the light-emitting layer, tetracene derivatives, diamine derivatives, etc. can be used. As a blue phosphorescent light-emitting material that can be used in the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used. As a green phosphorescent light-emitting material that can be used in the light-emitting layer, iridium complexes, etc. are used. As a red phosphorescent light-emitting material that can be used in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used.

[0271] (Host material of the light-emitting layer) As the light-emitting layer, a configuration in which the above-described highly luminescent substance (guest material) is dispersed in another substance (host material) may be used. As the substance for dispersing the highly luminescent substance, various substances can be used in addition to the material used in the present invention described above (compound represented by formula (10)), and it is preferable to use a substance having a higher lowest unoccupied molecular orbital level (LUMO level) and a lower highest occupied molecular orbital level (HOMO level) than the highly luminescent substance. As the substance (host material) for dispersing the highly luminescent substance, 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, naphthacene derivatives, fluoranthene derivatives, triphenylene derivatives, fluorene derivatives, or chrysene derivatives, 4) aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives are used. In addition, a compound having delayed fluorescence (thermally activated delayed fluorescence) can also be used as the host material. It is also preferable that the light-emitting layer contains the material used in the present invention described above and a host compound having delayed fluorescence.

[0272] (Electron transport layer) The electron transport layer is a layer containing a substance having high electron transport properties. For the electron transport layer, 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.

[0273] (Electron injection layer) The electron injection layer is a layer containing a substance having high electron injection properties. For the electron injection layer, metal complex compounds such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), 8-hydroxyquinolinolato-lithium (Liq), etc., lithium oxide (LiOx ) Alkali metals, alkaline earth metals, or their compounds such as can be used.

[0274] (Cathode) For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof with a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, that is, alkali metals such as lithium (Li) and cesium (Cs), 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, etc.

[0275] In the organic EL element according to one aspect of the present invention, the formation method of each layer is not particularly limited. A formation method by a conventionally known vacuum evaporation method, spin coating method, etc. can be used. Each layer such as the light-emitting layer can be formed by a known method such as a vacuum evaporation method, a molecular beam epitaxy method (MBE method), or a coating method such as a dipping method, spin coating method, casting method, bar coating method, roll coating method, etc. of a solution dissolved in a solvent.

[0276] In the organic EL element according to one aspect of the present invention, the film thickness of each layer is not particularly limited, but generally, in order to suppress defects such as pinholes, keep the applied voltage low, and improve the light emission efficiency, a range of usually several nm to 1 μm is preferable.

[0277] [Electronic device] An electronic device according to one aspect of the present invention is characterized by including an organic EL element according to one aspect of the present invention. Specific examples of the electronic device include display components such as organic EL panel modules, display devices such as televisions, mobile phones, or personal computers, and light-emitting devices such as lighting or vehicle lamps.

Example

[0278] Hereinafter, examples according to the present invention will be described. The present invention is not limited by these examples at all.

[0279] <Compound> The compound represented by formula (1) used in the examples is shown below.

Chemical formula

[0280] The compound used in the comparative example is shown below.

Chemical formula

[0281] The compounds used in the examples and comparative examples are shown below.

Chemical formula

[0282] Example 1 <Fabrication of organic EL element> A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) having a size of 25 mm × 75 mm × 1.1 mm in thickness was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The film thickness of ITO was 130 nm. The glass substrate with the transparent electrode after cleaning was mounted on the substrate holder of a vacuum evaporation apparatus. First, compound HI-1 was evaporated so as to cover the transparent electrode on the surface where the transparent electrode was formed, and a compound HI-1 film with a film thickness of 5 nm was formed. This HI-1 film functions as a hole injection layer.

[0283] Subsequent to the formation of this HI-1 film, compound HT-1 was evaporated, and an HT-1 film with a film thickness of 80 nm was formed on the HI-1 film. This HT-1 film functions as a first hole transport layer. Subsequent to the formation of the HT-1 film, compound EBL-1 was evaporated, and an EBL-1 film with a film thickness of 10 nm was formed on the HT-1 film. This EBL-1 film functions as a second hole transport layer. On the EBL-1 film, BH-1 (host material) and BD-1 (dopant material) were co-evaporated so that the ratio (weight ratio) of the compound BD-1 was 2%, and a light-emitting layer with a film thickness of 25 nm was formed.

[0284] On this light-emitting layer, the compound HBL-1 was evaporated to form an electron transport layer with a film thickness of 10 nm. On this electron transport layer, the compound ET-1, which is an electron injection material, was evaporated to form an electron injection layer with a film thickness of 15 nm. On this electron injection layer, LiF was evaporated to form a LiF film with a film thickness of 1 nm. On this LiF film, metal Al was evaporated to form a metal cathode with a film thickness of 80 nm.

[0285] The device structure of the organic EL device of Example 1 is schematically shown as follows. ITO(130) / HI-1(5) / HT-1(80) / EBL-1(10) / BH-1:BD-1(25:2%) / HBL-1(10) / ET-1(15) / LiF(1) / Al(80) The numbers in parentheses represent the film thickness (unit: nm).

[0286] <Evaluation of Organic EL Device> (Device Lifetime) Regarding the obtained organic EL device, at room temperature, a voltage was applied to the organic EL device so that the current density was 50 mA / cm 2 and the time (LT95 (unit: hours)) until the luminance reached 95% of the initial luminance was measured. The values in the table are relative values when Comparative Example 1 described later is set to 100%.

[0287] (Luminescence Efficiency) At room temperature, when a voltage was applied to the organic EL device so that the current density was 10 mA / cm 2 the spectral emission luminance spectrum was measured with a spectral emission luminance meter CS-2000 (manufactured by Konica Minolta Inc.). From the obtained spectral emission luminance spectrum, the current density (cd / A) was calculated. Also, by the same method, the chromaticity CIE-y was calculated. In this example, the value obtained by dividing the current density by the chromaticity was defined as the luminescence efficiency taking into account the chromaticity. The values in the table are relative values when the comparative example described later is set to 100%.

[0288] Examples 2 to 7 An organic EL device was fabricated and evaluated in the same manner as in Example 1, except that the compound described in Table 1 was used as the dopant material for the light-emitting layer. The results are shown in Table 1. Note that "-" in Table 1 indicates that the evaluation was not performed. The same applies to Table 2 and subsequent tables.

[0289] Comparative Example 1 An organic EL device was fabricated and evaluated in the same manner as in Example 1, except that the compound described in Table 1 was used as the dopant material for the light-emitting layer. The results are shown in Table 1.

[0290]

Table 1

[0291] Example 8 An organic EL device was fabricated and evaluated in the same manner as in Example 1, except that the compound described in Table 2 was used as the host material for the light-emitting layer. Note that the numerical values in the table are relative values when Comparative Example 2 described later is set to 100%. The results are shown in Table 2.

[0292] Examples 9 to 14 An organic EL device was fabricated and evaluated in the same manner as in Example 8, except that the compound described in Table 2 was used as the dopant material for the light-emitting layer. The results are shown in Table 2.

[0293] Comparative Example 2 An organic EL device was fabricated and evaluated in the same manner as in Example 8, except that the compound described in Table 2 was used as the dopant material for the light-emitting layer. The results are shown in Table 2.

[0294]

Table 2

[0295] Example 15 An organic EL device was fabricated and evaluated in the same manner as in Example 1, except that the compound described in Table 3 was used as the host material for the light-emitting layer. The numerical values in the table are relative values when Comparative Example 3 described later is taken as 100%. The results are shown in Table 3.

[0296] Examples 16 to 21 An organic EL device was fabricated and evaluated in the same manner as in Example 15, except that the compound described in Table 3 was used as the dopant material for the light-emitting layer. The results are shown in Table 3.

[0297] Comparative Example 3 An organic EL device was fabricated and evaluated in the same manner as in Example 15, except that the compound described in Table 3 was used as the dopant material for the light-emitting layer. The results are shown in Table 3.

[0298]

Table 3

[0299] Example 22 In Example 1, an organic EL device was fabricated in the same manner as in Example 1, except that HT-1 was changed to HT-2, EBL-1 was changed to EBL-2, BH-1 was changed to BH-4, HBL-1 was changed to HBL-2, and ET-1 was changed to ET-2, and the device lifetime was evaluated. The numerical values in the table are relative values when Comparative Example 4 described later is taken as 100%. The results are shown in Table 4.

[0300] Examples 23 to 28 An organic EL device was fabricated and evaluated in the same manner as in Example 22, except that the compound described in Table 4 was used as the dopant material for the light-emitting layer. The results are shown in Table 4.

[0301] Comparative Example 4 An organic EL device was fabricated and evaluated in the same manner as in Example 22, except that the compound described in Table 4 was used as the dopant material for the light-emitting layer. The results are shown in Table 4.

[0302]

Table 4

[0303] Example 29 An organic EL device was fabricated and the device lifetime was evaluated in the same manner as in Example 22, except that the compound described in Table 5 was used as the host material of the light-emitting layer. The numerical values in the table are relative values when Comparative Example 5 described later is taken as 100%. The results are shown in Table 5.

[0304] Examples 30 to 35 An organic EL device was fabricated and evaluated in the same manner as in Example 29, except that the compound described in Table 5 was used as the dopant material of the light-emitting layer. The results are shown in Table 5.

[0305] Comparative Example 5 An organic EL device was fabricated and evaluated in the same manner as in Example 29, except that the compound described in Table 5 was used as the dopant material of the light-emitting layer. The results are shown in Table 5.

[0306]

Table 5

[0307] From the results of Tables 1 to 5, it can be seen that the organic EL devices using BD-1 to BD-7 have a longer lifetime than the organic EL device using BD-Ref.

[0308] <Synthesis of Compound> Synthesis of BD-1 Compound BD-1 was synthesized according to the following synthetic route.

Chemical Formula

[0309] ·Synthesis of Intermediate 1-1 Under an argon atmosphere, 2-bromo-4-(tert-butyl)aniline (5.00 g, 21.9 mmol), phenylboronic acid (5.34 g, 43.8 mmol), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh 3 ) 4 , 0.253 g, 0.219 mmol), 2.7 M Na 2 CO3 20 mL of an aqueous solution, 20 mL of toluene, and 20 mL of ethanol were added, and the mixture was heated with stirring at 80 °C for 6 hours. After completion of the reaction, water and ethyl acetate were added, the organic phase was extracted, the solvent was distilled off, and the resulting crude product was purified by column chromatography and recrystallization to obtain a colorless solid (3.20 g, yield 65%). As a result of mass spectrum analysis, the obtained solid was Compound 1-1, the target compound, and had m / e = 225 corresponding to a molecular weight of 225.

[0310] · Synthesis of Intermediate 1-2 Under an argon atmosphere, Intermediate 1-1 (3.90 g, 17.3 mmol), bromobenzene (3.26 g, 20.8 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 (0.237 g, 0.259 mmol), rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (rac-BINAP, 0.322 g, 5.17 mmol), and NaOt-Bu (2.33 g, 24.2 mmol) were dissolved in toluene (30 mL), and the mixture was heated with stirring at 90 °C for 3 hours. After completion of the reaction, water and ethyl acetate were added, the organic phase was extracted, the solvent was distilled off, and the resulting crude product was purified by column chromatography to obtain an orange oily compound (4.20 g, yield 81%). As a result of mass spectrum analysis, the obtained compound was Compound 1-2, the target compound, and had m / e = 301 corresponding to a molecular weight of 301.

[0311] · Synthesis of BD-1 Under an argon atmosphere, a known intermediate 1-3 (synthesized by the method described in US10,249,832, 3.33 g, 4.75 mmol), Intermediate 1-2 (3.14 g, 10.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3, 0.218 g, 0.238 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.226 g, 0.475 mmol) was dissolved in xylene (240 mL), and a tetrahydrofuran solution of 1 M lithium bis(trimethylsilyl)amide (10.9 mL, 10.9 mmol) was added. The mixture was refluxed at 135 °C for 3 hours. After completion of the reaction, methanol was added, and the mixture was filtered. The obtained solid was purified by column chromatography and recrystallization to obtain a yellow solid (3.82 g, yield 80%). The obtained solid was the target BD-1 according to the results of mass spectrum analysis, and m / e = 1002 for a molecular weight of 1002.

[0312] Synthesis of BD-2 Compound BD-2 was synthesized according to the following synthetic route.

Chemical formula

[0313] ·Synthesis of Intermediate 2-1 Under an argon atmosphere, 2-bromobiphenyl (20.0 g, 86.0 mmol), 4-tert-butylaniline (14.1 g, 94.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 1.18 g, 1.29 mmol), rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (rac-BINAP, 1.60 g, 2.57 mmol), and NaOt-Bu (11.5 g, 120 mmol) were dissolved in toluene (500 ml), and the mixture was heated and stirred at 90 °C for 5 hours. Water and ethyl acetate were added, and the organic phase was extracted. The crude product obtained by distilling off the solvent was purified by column chromatography to obtain an orange oily compound (21.5 g, yield 83%). The obtained compound was the target Compound 2-1 according to the results of mass spectrum analysis, and m / e = 301 for a molecular weight of 301.

[0314] ·Synthesis of BD-2 Under an argon atmosphere, known intermediate 1-2 (synthesized by the method described in US10,249,832, 1.48 g, 2.11 mmol), intermediate 2-1 (1.34 mg, 4.44 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , 97 mg, 0.106 mmol), and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (101 mg, 0.211 mmol) were dissolved in xylene (120 mL), and a tetrahydrofuran solution of 1 M lithium bis(trimethylsilyl)amide (4.9 mL, 4.9 mmol) was added, followed by refluxing for 5 hours. After completion of the reaction, methanol was added, and the mixture was filtered. The obtained solid was purified by column chromatography to obtain a yellow solid (1.20 mg, yield 57%). As a result of mass spectrometry analysis, the obtained solid was the target BD-2, and for a molecular weight of 1002, m / e = 1002.

[0315] Synthesis of BD-3 Compound BD-3 was synthesized according to the following synthetic route.

Chemical formula

[0316] ·Synthesis of intermediate 3-1 Under an argon atmosphere, p-bromotoluene (3.00 g, 17.5 mmol), 4-tert-butyl-2-phenylaniline (4.35 g, 19.3 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3, 0.241 g, 0.263 mmol), rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP, 0.328 g, 0.526 mmol), and NaOt-Bu (2.36 g, 24.6 mmol) were dissolved in toluene (900 ml), and the mixture was heated and stirred at 90 °C for 5 hours. Water and ethyl acetate were added, the organic layer was extracted, the solvent was distilled off, and the resulting crude product was purified by column chromatography to obtain a white solid compound (4.6 g, yield 83%). The obtained compound was the target intermediate 3-1, and as a result of mass spectrometry analysis, m / e = 315 corresponding to a molecular weight of 315.

[0317] ·Synthesis of BD-3 Under an argon atmosphere, intermediate 1-3 (3.03 g, 4.33 mmol), intermediate 3-1 (2.87 g, 9.09 mmol), and XPhosPdG4 (186 mg, 0.217 mmol) were dissolved in xylene (100 mL), and a tetrahydrofuran solution of 1 M lithium bis(trimethylsilyl)amide (9.96 mL, 9.96 mmol) was added, followed by refluxing for 5 hours. After completion of the reaction, methanol was added, and the mixture was filtered. The resulting solid was purified by column chromatography to obtain a yellow solid (3.71 g, yield 83%). The obtained solid was the target BD-3, and as a result of mass spectrometry analysis, m / e = 1031 corresponding to a molecular weight of 1031.

[0318] Synthesis of BD-4 Compound BD-4 was synthesized according to the following synthetic route. [Chemical formula]

[0319] Under an argon atmosphere, known intermediate 1-4 (0.600 g, 1.03 mmol), intermediate 4-1 (0.679 g, 2.25 mmol), and XPhosPdG4 (44 mg, 0.051 mmol) were dissolved in xylene (50 mL), and a tetrahydrofuran solution of 1 M lithium bis(trimethylsilyl)amide (2.46 mL, 2.46 mmol) was added, followed by refluxing for 5 hours. After completion of the reaction, methanol was added, and the mixture was filtered. The obtained solid was purified by column chromatography to obtain a yellow solid (595 mg, yield 52%). The obtained solid was the target product BD-4, and as a result of mass spectrum analysis, for a molecular weight of 1115, m / e = 1115.

[0320] Synthesis of BD-5 Compound BD-5 was synthesized according to the following synthetic route.

Chemical formula

[0321] It was synthesized in the same manner as the synthesis of compound BD-1, except that the corresponding secondary amine intermediate 5-1 was used instead of intermediate 3-1 as the reaction raw material. The molecular weight of BD-5 is 1013, and as a result of the analysis of the mass spectrum of the obtained compound, m / z (mass-to-charge ratio) = 1013, so it was identified as compound BD-5.

[0322] Synthesis of BD-6 Compound BD-6 was synthesized according to the following synthetic route.

Chemical formula

[0323] ·Synthesis of intermediate 6-1 Intermediate 6-1 was synthesized in the same manner as intermediate 3-1 using 2'-bromo-1,1'-biphenyl-2,3,4,5,6-d5 and m-tert-butylaniline as reaction raw materials.

[0324] ·Synthesis of BD-6 Compound BD-6 was synthesized in the same manner as the synthesis of compound BD-1, except that the corresponding secondary amine intermediate 6-1 was used instead of intermediate 3-1 as the reaction raw material. The molecular weight of BD-6 was 1013, and the analysis result of the mass spectrum of the obtained compound showed that m / z (mass-to-charge ratio) = 1013, so it was identified as compound BD-6.

[0325] Synthesis of BD-7 Compound BD-7 was synthesized according to the following synthetic route.

Chemical formula

[0326] ·Synthesis of intermediate 7-1 Intermediate 7-1 was synthesized in the same manner as intermediate 3-1, using bromobenzene-d5 and 2-(4-tert-butylphenyl)aniline as the reaction raw materials.

[0327] ·Synthesis of compound BD-7 Compound BD-7 was synthesized in the same manner as the synthesis of compound BD-1, except that the corresponding secondary amine intermediate 7-1 was used instead of intermediate 3-1 as the reaction raw material. The molecular weight of BD-7 was 1013, and the analysis result of the mass spectrum of the obtained compound showed that m / z (mass-to-charge ratio) = 1013, so it was identified as compound BD-7.

[0328] Although several embodiments and / or examples of the present invention have been described in detail above, those skilled in the art can easily make many changes to these exemplary embodiments and / or examples without substantially departing from the novel teachings and effects of the present invention. Therefore, many of these changes are included in the scope of the present invention. All the documents described in this specification and the content of the application that forms the basis of the priority under the Paris Convention of this application are incorporated by reference.

Claims

1. A compound represented by the following formula (1-2). 【Chemical 1】 (In the formula (1-2), R １ to R ６ , R １１ to R １６ , R ２１ , and R ２２ is a hydrogen atom. R １ to R ６ and R １１ to R １６ Among them, two or more adjacent pairs do not form a substituted or unsubstituted saturated or unsaturated ring. R ６１ ~R ６９ at least one of, and R ７１ ~R ７９ at least one of is, independently of one another, substituent A. substituent A is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. R ８１ to R ８５ and R ９１ to R ９５ , and R other than the substituent A ６１ to R ６９ and R ７１ to R ７９ is each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. The substituent in the case of "substituted or unsubstituted" is an alkyl group having 1 to 6 carbon atoms.)

2. The compound according to Claim 1, represented by the following formula (1-3). 【Chemical 2】 (In the formula (1-3), R ６１ to R ６９ and R ７１ to R ７９ are as defined in the formula (1-2).)

3. A material for an organic electroluminescent element containing the compound according to Claim 1 or 2.

4. A cathode, an anode, at least one organic layer disposed between the cathode and the anode, having, an organic electroluminescent element in which at least one layer of the at least one organic layer contains the compound according to Claim 1 or 2.

5. The organic electroluminescent element according to Claim 4, wherein at least one layer of the at least one organic layer contains a second compound different from the first compound according to Claim 1 or 2.

6. The organic electroluminescent element according to Claim 5, wherein the second compound is a heterocyclic compound or a condensed aromatic compound.

7. The organic electroluminescent element according to Claim 5 or 6, wherein the second compound is an anthracene derivative.

8. The organic electroluminescent element according to any one of Claims 5 to 7, wherein the second compound is a compound represented by the following formula (20). [Chemical Formula 3] R １０１ to R １０８ Among two or more adjacent pairs of them, one or more pairs form a substituted or unsubstituted saturated or unsaturated ring, or do not form the substituted or unsubstituted saturated or unsaturated ring. R which does not form the above-mentioned substituted or unsubstituted saturated or unsaturated ring １０１ ~R １０８ are each independently A hydrogen atom, or a group represented by substituent R. L １０１ is A single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms. Ar １０１ is A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R ９０１ )(R ９０２ )(R ９０３ ), -O-(R ９０４ ), -S-(R ９０５ ), -N(R ９０６ )(R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. Two Ars １０１ may be the same as or different from each other. The two Ls １０１ may be the same as or different from each other. When two or more of the substituents R are present, the two or more substituents R may be the same or different. R ９０１ ~R ９０７ are each independently A hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, an aryl group having 6 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, or a monovalent heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted. R ９０１ ~R ９０７ If two or more R ９０１ ~R ９０７ exist, each of the two or more R ~R may be the same or different.

9. The organic electroluminescence device according to any one of claims 4 to 8, wherein at least one layer of the at least one organic layer is a light-emitting layer.

10. The organic electroluminescence device according to claim 9, having a hole transport layer between the anode and the light-emitting layer.

11. The organic electroluminescence device according to claim 9 or 10, having an electron transport layer between the cathode and the light-emitting layer.

12. The organic electroluminescence device according to any one of claims 9 to 11, wherein the light-emitting layer contains a compound represented by the formula (20).

13. The organic electroluminescence device according to any one of claims 9 to 12, wherein the light-emitting layer further contains a host compound having delayed fluorescence properties.

14. An electronic device including the organic electroluminescence device according to any one of claims 4 to 13.

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