Compound, material for organic electroluminescence device, organic electroluminescence device and electronic device

Abstract

To provide an organic electroluminescence element having improved element performance.SOLUTION: In an organic electroluminescence device, a first hole transport layer includes a compound represented by the formula (1A).SELECTED DRAWING: None

Description

Technical Field

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

Background Art

[0002] Generally, an organic electroluminescent element (hereinafter sometimes referred to as "organic EL element") is composed of an anode, a cathode, and an organic layer sandwiched between the anode and the cathode. When a voltage is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side into the light-emitting region. The injected electrons and holes recombine in the light-emitting region to generate an excited state, and light is emitted when the excited state returns to the ground state. Therefore, the development of materials that efficiently transport electrons or holes to the light-emitting region and facilitate the recombination of electrons and holes is important for obtaining high-performance organic EL elements.

[0003] Patent Documents 1 to 3 disclose compounds used as materials for organic electroluminescent elements.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Patent Document 2

Patent Document 3

Summary of the Invention

Problems to be Solved by the Invention

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

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

Means for Solving the Problems

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

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

Chemical formula

Chemical formula

[0009] In formula (1B), N * is a central nitrogen atom. One selected from R 11 ~R 14 is a single bond bonded to *a. R 11 ~R 14 , R 15 ~R 18 , and R 7 ~R 10 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms. R 11 ~R 14 that are not the single bonds do not combine with each other to form a ring. R 7 ~R 10 Among them, a pair of adjacent groups may or may not combine with each other to form a ring. R 15 ~R 18 Among them, a pair of adjacent groups may or may not combine with each other to form a ring. R 1B 、R 2B 、R 5B 、and R 6B are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms. R 1B and R 2B may or may not combine with each other to form a ring. R 5B and R 6B may or may not combine with each other to form a ring. L 3 is a substituted or unsubstituted arylene group having 6 to 12 ring-forming carbon atoms. n3 is 0 or 1. When n3 is 0, Ar 3 is bonded to the central nitrogen atom N * . Ar 3 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a group represented by the following formula (2-1), or a group represented by the following formula (2-2).

Chemical formula

Chemical formula

[0010] In another aspect, the present invention provides a material for an organic electroluminescence device containing the compound represented by the above formula (1A) or formula (1B).

[0011] In still another aspect, the present invention provides an organic electroluminescence device having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer contains the compound represented by the above formula (1A) or formula (1B).

[0012] In still another aspect, the present invention provides an electronic device including the above organic electroluminescence device.

Advantages of the Invention

[0013] The organic EL device containing the compound represented by the above formula (1A) or formula (1B) exhibits improved device performance.

Brief Description of the Drawings

[0014]

Figure 1

Figure 2

Figure 3

Embodiments for Carrying Out the Invention

[0015] [Definitions] In this specification, the hydrogen atom includes isotopes having different numbers of neutrons, that is, protium, deuterium, and tritium.

[0016] In this specification, in a chemical structural formula, at a bondable position where a symbol such as "R" or "D" representing a deuterium atom is not explicitly shown, it is assumed that a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is bonded.

[0017] In this specification, the number of ring-forming carbon atoms represents the number of carbon atoms among the atoms constituting the ring itself in 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. Also, for example, the number of ring-forming carbon atoms of a 9,9-diphenylfluorenyl group is 13, and the number of ring-forming carbon atoms of a 9,9'-spirobifluorenyl group is 25. In addition, when, for example, an alkyl group is substituted as a substituent on a benzene ring, the number of carbon atoms of the alkyl group is not included in the number of ring-forming carbon atoms of the benzene ring. Therefore, the number of ring-forming carbon atoms of the benzene ring substituted with an alkyl group is 6. Further, when, for example, an alkyl group is substituted as a substituent on a naphthalene ring, the number of carbon atoms of the alkyl group is not included in the number of ring-forming carbon atoms of the naphthalene ring. Therefore, the number of ring-forming carbon atoms of the naphthalene ring substituted with an alkyl group is 10.

[0018] In this specification, the number of ring-forming atoms refers to the number of atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic ring, a condensed ring, and a ring assembly) (for example, a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, and a heterocyclic compound). Atoms that do not constitute the ring (for example, hydrogen atoms that terminate the bonds of the atoms constituting the ring) and atoms included in the substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms. The same shall apply to the "number of ring-forming atoms" described below unless otherwise specified. For example, the number of ring-forming atoms of a pyridine ring is 6, the number of ring-forming atoms of a quinazoline ring is 10, and the number of ring-forming atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or the number of atoms constituting a substituent is not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms of the pyridine ring to which a hydrogen atom or a substituent is bonded is 6. Further, for example, 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 the quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

[0019] 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 larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0020] In this specification, in the expression "ZZ group having XX to YY carbon atoms, which may be substituted or unsubstituted", "XX to YY carbon atoms" represents the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituents when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0021] In this specification, an unsubstituted ZZ group represents the case where the "ZZ group which may be substituted or unsubstituted" is an "unsubstituted ZZ group", and a substituted ZZ group represents the case where the "ZZ group which may be substituted or unsubstituted" is a "substituted ZZ group". In this specification, "unsubstituted" in the case of "ZZ group which may be substituted or unsubstituted" means that the hydrogen atom in the ZZ group is not replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom. Also, in this specification, "substituted" in the case of "ZZ group which may be substituted or unsubstituted" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. Similarly, "substituted" in the case of "BB group substituted with AA group" means that one or more hydrogen atoms in the BB group are replaced by the AA group.

[0022] "Substituents described in this specification" Hereinafter, the substituents described in this specification will be described. Unless otherwise specified, each substituent described in this specification is defined as follows.

[0023] Unless otherwise specified in this specification, the number of ring-forming carbon atoms of the "unsubstituted aryl group" described in this specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18. Unless otherwise specified in this specification, the number of ring-forming atoms of the "unsubstituted heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18. Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkyl group" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkenyl group" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkynyl group" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6. Unless otherwise specified in this specification, the number of ring-forming carbon atoms in the "unsubstituted cycloalkyl group" described in this specification is 3 to 50, preferably 3 to 20, more preferably 3 to 6. Unless otherwise specified in this specification, the number of ring-forming carbon atoms in the "unsubstituted arylene group" described in this specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18. Unless otherwise specified in this specification, the number of ring-forming atoms in the "unsubstituted divalent heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkylene group" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6.

[0024] · "Substituted or unsubstituted aryl group" Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B), etc. (Here, the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is the "unsubstituted aryl group", and the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is the "substituted aryl group".) In this specification, when simply referring to the "aryl group", it includes both the "unsubstituted aryl group" and the "substituted aryl group". "Aryl group for substitution" means a group in which one or more hydrogen atoms of "unsubstituted aryl group" are replaced by substituents. Examples of "aryl group for substitution" include, for example, a group in which one or more hydrogen atoms of the "unsubstituted aryl group" in the following specific example group G1A are replaced by substituents, and examples of the substituted aryl group in the following specific example group G1B. The examples of the "unsubstituted aryl group" and the "aryl group for substitution" listed here are only examples, and the "aryl group for substitution" described in this specification includes a group in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "aryl group for substitution" in the following specific example group G1B is further replaced by a substituent, and a group in which a hydrogen atom of the substituent in the "aryl group for substitution" in the following specific example group G1B is further replaced by a substituent.

[0025] · Unsubstituted aryl group (specific example group G1A): Phenyl group, p - Biphenyl group, m - Biphenyl group, o - Biphenyl group, p - Terphenyl - 4 - yl group, p - Terphenyl - 3 - yl group, p - Terphenyl - 2 - yl group, m - Terphenyl - 4 - yl group, m - Terphenyl - 3 - yl group, m - Terphenyl - 2 - yl group, m - Terphenyl - 3’ - yl group, o - Terphenyl - 4 - yl group, o - Terphenyl - 3 - yl group, o - Terphenyl - 2 - yl group, 1 - Naphthyl group, 2 - Naphthyl group, Anthryl group, 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, Benzofluoranhenyl group, Perylenyl group, and A monovalent aryl group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-1) to (TEMP-15).

[0026]

Chemical formula

[0027]

Chemical formula

[0028] · Substituted aryl group (specific example group G1B): o-Tolyl group, m-Tolyl group, p-Tolyl group, Para-Xylyl group, Meta-Xylyl group, Ortho-Xylyl group, Para-Isopropylphenyl group, Meta-Isopropylphenyl group, Ortho-Isopropylphenyl group, Para-t-Butylphenyl group, Meta-t-Butylphenyl group, Ortho-t-Butylphenyl group, 3,4,5-Trimethylphenyl group, 9,9-Dimethylfluorenyl group, 9,9-Diphenylfluorenyl group 9,9-Bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group 9,9-bis(4-t-butylphenyl)fluorenyl group cyanophenyl group triphenylsilylphenyl group trimethylsilylphenyl group phenylnaphthyl group naphthylphenyl group, and a group in which one or more hydrogen atoms of the monovalent group derived from the ring structure represented by the general formulas (TEMP-1) to (TEMP-15) are replaced with substituents

[0029] · "substituted or unsubstituted heterocyclic group" The "heterocyclic group" described in the present 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 the present specification is a monocyclic group or a condensed ring group The "heterocyclic group" described in the present 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 the present specification include the following unsubstituted heterocyclic groups (specific example group G2A), substituted heterocyclic groups (specific example group G2B), and the like. (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In the present specification, when simply referring to a "heterocyclic group", it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group" "Substituted heterocyclic group" means a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of the "substituted heterocyclic group" include groups in which the hydrogen atoms of the "unsubstituted heterocyclic group" in the following Specific Example Group G2A are replaced, and examples of the substituted heterocyclic group in the following Specific Example Group G2B. It should be noted that the examples of the "unsubstituted heterocyclic group" and the "substituted heterocyclic group" listed here are only examples, and the "substituted heterocyclic group" described in this specification includes groups in which the hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself in the "substituted heterocyclic group" of 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.

[0030] 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).

[0031] Specific Example Group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (Specific Example Group G2B1), substituted heterocyclic groups containing an oxygen atom (Specific Example Group G2B2), substituted heterocyclic groups containing a sulfur atom (Specific Example Group G2B3), and groups in which one or more hydrogen atoms of the monovalent heterocyclic groups derived from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (Specific Example Group G2B4).

[0032] ·Unsubstituted heterocyclic group containing a nitrogen atom (Specific Example Group G2A1): Pyrrolyl group, Imidazolyl group, Pyrazolyl group, Triazolyl group, Tetrazolyl group, Oxazolyl group, Isoxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolizinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, an indazolyl group, a phenanthrolinyl group, a phenanthridinyl group, an acridinyl group, a phenazinyl group, a carbazolyl group, a benzocarbazolyl group, a morpholino group, a phenoxazinyl group, a phenothiazinyl group, an azacarbazolyl group, and a diazacarbazolyl group.

[0033] · an unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): a furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a xanthenyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a benzoxazolyl group, a benzoisoxazolyl group, a phenoxazinyl group, a morpholino group, a dinaphthofuranyl group, Azadibenzofuranyl group, Diazadibenzofuranyl group, Azananofuranyl group, and Diazananofuranyl group.

[0034] ·Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3): Thienyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl group, Benzothiophenyl group (benzothienyl group), Isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), Naphthobenzothiophenyl group (naphthobenzothienyl group), Benzothiazolyl group, benzisothiazolyl group, Phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), Diazadibenzothiophenyl group (diazadibenzothienyl group), Azananobenzothiophenyl group (azananobenzothienyl group), and Diazananobenzothiophenyl group (diazananobenzothienyl group).

[0035] ·Monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0036]

Chemical formula

[0037]

Chemical formula

[0038] 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 .

[0039] · Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): (9-Phenyl)carbazolyl group, (9-Biphenylyl)carbazolyl group, (9-Phenyl)phenylcarbazolyl group, (9-Naphthyl)carbazolyl group, Diphenylcarbazol-9-yl group, Phenylcarbazol-9-yl group, Methylbenzimidazolyl group, Ethylbenzimidazolyl group, Phenyltriazinyl group, Biphenylyltriazinyl group, Diphenyltriazinyl group, Phenylquinazolinyl group, and biphenylylquinazolinyl group.

[0040] · Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): Phenyldibenzofuranyl group, Methyldibenzofuranyl group, t-Butyldibenzofuranyl group, and The monovalent residue of spiro[9H-xanthene-9,9’-[9H]fluorene].

[0041] · 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].

[0042] · A group in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific example group G2B4):

[0043] The above-mentioned "one or more hydrogen atoms of the monovalent heterocyclic group" means one or more hydrogen atoms selected from the hydrogen atoms bonded to the ring-forming carbon atoms of the monovalent heterocyclic group, the hydrogen atoms bonded to the nitrogen atom when at least one of XA and YA is NH, and the hydrogen atoms of the methylene group when one of XA and YA is CH2.

[0044] · "Substituted or unsubstituted alkyl group" Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B). (Here, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group", and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group".) Hereinafter, when simply referred to as "alkyl group", both "unsubstituted alkyl group" and "substituted alkyl group" are included. "Substituted alkyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced by substituents. Specific examples of the "substituted alkyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl group" (specific example group G3A) are replaced by substituents, and examples of the substituted alkyl group (specific example group G3B). In this specification, the alkyl group in the "unsubstituted alkyl group" means a chain alkyl group. Therefore, the "unsubstituted alkyl group" includes a linear "unsubstituted alkyl group" and a branched "unsubstituted alkyl group". Note that the examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" listed here are only examples, and the "substituted alkyl group" described in this specification includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" of specific example group G3B is further replaced by a substituent, and a group in which a hydrogen atom of the substituent in the "substituted alkyl group" of specific example group G3B is further replaced by a substituent.

[0045] · 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.

[0046] · Substituted alkyl group (specific example group G3B): Heptafluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-Trifluoroethyl group, and Trifluoromethyl group.

[0047] · "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. It should be noted that the examples of the "unsubstituted alkenyl group" and the "substituted alkenyl group" listed here are only examples, and the "substituted alkenyl group" described in this specification includes groups in which the hydrogen atoms of the alkenyl group itself in the "substituted alkenyl group" of specific example group G4B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted alkenyl group" of specific example group G4B are further replaced by substituents.

[0048] · Unsubstituted alkenyl groups (specific example group G4A): Vinyl group, Allyl group, 1-Butenyl group, 2-Butenyl group, and 3-Butenyl group.

[0049] · Substituted alkenyl groups (specific example group G4B): 1,3-Butadienyl group, 1-Methylvinyl group, 1-Methylallyl group, 1,1-Dimethylallyl group, 2-Methylallyl group, and 1,2-Dimethylallyl group.

[0050] · "Substituted or unsubstituted alkynyl group" Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl groups (specific example group G5A), etc. (Here, the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group"). Hereinafter, when simply referring to an "alkynyl group", it includes both "unsubstituted alkynyl group" and "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.

[0051] · Unsubstituted alkynyl group (specific example group G5A): Ethynyl group

[0052] · "Substituted or unsubstituted cycloalkyl group" Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described in this specification include the following unsubstituted cycloalkyl groups (specific example group G6A) and substituted cycloalkyl groups (specific example group G6B), etc. (Here, the unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group", and the substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group"). In this specification, when simply referring to a "cycloalkyl group", it includes both "unsubstituted cycloalkyl group" and "substituted cycloalkyl group". "Substituted cycloalkyl group" means a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced by substituents. Specific examples of the "substituted cycloalkyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl group" (specific example group G6A) are replaced by substituents, and examples of the substituted cycloalkyl group (specific example group G6B). The examples of the "unsubstituted cycloalkyl group" and the "substituted cycloalkyl group" listed here are only examples, and the "substituted cycloalkyl group" described in this specification includes a group 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 a group in which the hydrogen atoms of the substituents in the "substituted cycloalkyl group" of specific example group G6B are further replaced by substituents.

[0053] · Unsubstituted cycloalkyl group (specific example group G6A): Cyclopropyl group, Cyclobutyl group, Cyclopentyl group, Cyclohexyl group, 1-Adamantyl group, 2-Adamantyl group, 1-Norbornyl group, and 2-Norbornyl group.

[0054] · Substituted cycloalkyl group (specific example group G6B): 4-Methylcyclohexyl group.

[0055] · Group represented by "-Si(R 901 )(R 902 )(R 903 )" Specific examples (specific example group G7) of the group represented by -Si(R 901 )(R 902 )(R 903 ) described in this specification include -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) may be mentioned. Here, G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2. G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in the specific example group G6. The plurality of G1s in -Si(G1)(G1)(G1) are the same as or different from each other. The plurality of G2s in -Si(G1)(G2)(G2) are the same as or different from each other. The plurality of G1s in -Si(G1)(G1)(G2) are the same as or different from each other. The plurality of G2s in -Si(G2)(G2)(G2) are the same as or different from each other. The plurality of G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The plurality of G6s in -Si(G6)(G6)(G6) are the same as or different from each other.

[0056] · "Group represented by -O-(R 904 )" Specific examples (specific example group G8) of the group represented by -O-(R 904 ) described in this specification include -O(G1), -O(G2), -O(G3), and -O(G6) may be mentioned. Here, G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2. G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0057] · "A group represented by -S-(R 905 )" Specific examples (Specific Example Group G9) of the group represented by -S-(R 905 ) described in this specification include -S(G1), -S(G2), -S(G3), and -S(G6) are included. 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.

[0058] · "A group represented by -N(R 906 )(R 907 )" Specific examples (Specific Example Group G10) of the group represented by -N(R 906 )(R 907 ) described in this specification include -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) are included. Here, G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2. G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6. The plurality of G1s in -N(G1)(G1) are the same as or different from each other. The plurality of G2s in -N(G2)(G2) are the same as or different from each other. The plurality of G3s in -N(G3)(G3) are the same as or different from each other. The plurality of G6s in -N(G6)(G6) are the same as or different from each other.

[0059] · "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.

[0060] · "Substituted or unsubstituted fluoroalkyl group" The "substituted or unsubstituted fluoroalkyl group" described in this specification means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced by fluorine atoms (perfluoro group). Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, more preferably 1 to 18. The "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms in the "fluoroalkyl group" are replaced by substituents. In addition, the "substituted fluoroalkyl group" described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the "substituted fluoroalkyl group" are further replaced by substituents, and a group in which one or more hydrogen atoms of the substituents in the "substituted fluoroalkyl group" are further replaced by substituents. Specific examples of the "unsubstituted fluoroalkyl group" include examples of groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (Specific Example Group G3) are replaced by fluorine atoms.

[0061] · "Substituted or unsubstituted haloalkyl group" As used herein, the "substituted or unsubstituted haloalkyl group" means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced by halogen atoms. Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, more preferably 1 to 18. The "substituted haloalkyl group" means a group in which one or more hydrogen atoms in the "haloalkyl group" are replaced by substituents. It should be noted that the "substituted haloalkyl group" described herein also includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the "substituted haloalkyl group" are further replaced by substituents, and a group in which one or more hydrogen atoms of the substituents in the "substituted haloalkyl group" are further replaced by substituents. Specific examples of the "unsubstituted haloalkyl group" include examples of groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced by halogen atoms. The haloalkyl group may be referred to as a halogenated alkyl group.

[0062] · "Substituted or unsubstituted alkoxy group" Specific examples of the "substituted or unsubstituted alkoxy group" described herein are groups represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, more preferably 1 to 18.

[0063] · "Substituted or unsubstituted alkylthio group" Specific examples of the "substituted or unsubstituted alkylthio group" described in this specification are groups represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3. The number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0064] · "Substituted or unsubstituted aryloxy group" Specific examples of the "substituted or unsubstituted aryloxy group" described in this specification are groups represented by -O(G1), where G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1. The number of ring-forming carbon atoms in the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0065] · "Substituted or unsubstituted arylthio group" Specific examples of the "substituted or unsubstituted arylthio group" described in this specification are groups represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1. The number of ring-forming carbon atoms in the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0066] · "Substituted or unsubstituted trialkylsilyl group" Specific examples of the "trialkylsilyl group" described in this specification are groups represented by -Si(G3)(G3)(G3), where G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3. The plurality of G3 in -Si(G3)(G3)(G3) are the same as or different from each other. The number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.

[0067] · "Substituted or unsubstituted aralkyl group" Specific examples of the "substituted or unsubstituted aralkyl group" described in this specification include a group represented by -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3, and G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1. Therefore, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced by an "aryl group" as a substituent, and it is a form of a "substituted alkyl group". An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted by an "unsubstituted aryl group", and the number of carbon atoms of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification. Specific examples of the "substituted or unsubstituted aralkyl group" include 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.

[0068] Unless otherwise specified in this specification, 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.

[0069] The substituted or unsubstituted heterocyclic group described in this specification is preferably a pyridyl group, pyrimidinyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, benzimidazolyl group, phenanthrolinyl group, carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group, dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazol-4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyl dibenzothiophenyl group, etc., unless otherwise described in this specification.

[0070] In this specification, unless otherwise described in this specification, the carbazolyl group is specifically any of the following groups.

[0071]

Chemical formula

[0072] In this specification, unless otherwise described in this specification, the (9-phenyl)carbazolyl group is specifically any of the following groups.

[0073]

Chemical formula

[0074] In the general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents the bonding position.

[0075] In this specification, unless otherwise specified herein, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups.

[0076] [Chemical formula]

[0077] In the general formulas (TEMP-34) to (TEMP-41), * represents the bonding position.

[0078] 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.

[0079] · "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.

[0080] · "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.

[0081] · "Substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group". Specific examples (specific example group G14) of the "substituted or unsubstituted alkylene group" include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3, etc.

[0082] Unless otherwise specified in this specification, the substituted or unsubstituted arylene group described in this specification is preferably a group of any of the following general formulas (TEMP-42) to (TEMP-68).

[0083]

Chemical formula

[0084]

Chemical formula

[0085] 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.

[0086]

Chemical formula

[0087] 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.

[0088]

Chemical formula

[0089] 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.

[0090] Unless otherwise specified herein, the substituted or unsubstituted divalent heterocyclic group described herein is preferably any group of the following general formulas (TEMP-69) to (TEMP-102).

[0091]

Chemical formula

[0092]

Chemical formula

[0093]

Chemical formula

[0094] In the general formulas (TEMP-69) to (TEMP-82), Q 1 ~Q 9 are each independently a hydrogen atom or a substituent.

[0095]

Chemical formula

[0096] [Chemistry]

[0097] [Chemistry]

[0098] [Chemistry]

[0099] In the general formulas (TEMP-83) to (TEMP-102) above, Q 1 ~Q 8 are each independently a hydrogen atom or a substituent.

[0100] The above is the description of "the substituents described in this specification".

[0101] · "When bonding to form a ring" In this specification, the case of "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted monocyclic ring, or bond to each other to form a substituted or unsubstituted condensed ring, or do not bond to each other" means the case of "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted monocyclic ring", the case of "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted condensed ring", and the case of "one or more sets of two or more adjacent ones do not bond to each other". Regarding the cases 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 "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. The case of an anthracene compound represented by the following general formula (TEMP-103) whose mother skeleton is an anthracene ring will be described as an example.

[0102] [Chemical formula]

[0103] 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 refers to the pair of R 921 and R 922 , the pair of R 922 and R 923 , the pair of R 923 and R 924 , the pair of R 924 and R 930 , the pair of R 930 and R 925 , the pair of R 925 and R 926 , the pair of R 926 and R 927 , the pair of R 927 and R 928 , the pair of R 928 and R 929 , and the pair of R 929 and R 921 .

[0104] The above "one or more sets" means that two or more sets of the above-mentioned 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).

[0105] [Chemical formula]

[0106] The case where a "set consisting of two or more adjacent elements" forms a ring includes not only the case where a "set of two" adjacent elements combines as in the previous example, but also the case where a "set of three or more" adjacent elements combines. For example, R 921 and R 922 are combined with each other to form ring Q A and R 922 and R 923 are combined with each other to form ring Q C and a set consisting of three adjacent elements (R 921 , R 922 and R 923 ) combines with each other to form a ring and condenses with the anthracene backbone. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C share R 922 .

[0107]

Chemical formula

[0108] 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 pair of adjacent elements" 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 AIf 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.

[0109] The "unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The "saturated ring" means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of the aromatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G1 are terminated by hydrogen atoms. Specific examples of the aromatic heterocyclic ring include structures in which the aromatic heterocyclic 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 elements. For example, in the general formula (TEMP-104), R 921 and R 922 The ring Q formed by bonding to each other A is R 921 The carbon atom of the anthracene skeleton to which binds, R 922 The carbon atom of the anthracene skeleton to which binds, and one or more arbitrary elements. As a specific example, R 921 and R 922 In the case of forming ring Q A When R 921 The carbon atom of the anthracene skeleton to which binds, R 922 The carbon atom of the anthracene skeleton to which binds, and four carbon atoms form a monocyclic unsaturated ring, R 921 and R 922 The ring formed by is a benzene ring.

[0110] Here, "any element" is preferably at least one element selected from the group consisting of a carbon element, a nitrogen element, an oxygen element, and a sulfur element, unless otherwise described in this specification. In any element (for example, in the case of a carbon element or a nitrogen element), a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described later. When any element other than the carbon element is included, the formed ring is a heterocyclic ring. Unless otherwise described in this specification, "one or more arbitrary elements" constituting a monocyclic or condensed ring are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and still more preferably 3 or more and 5 or less. Unless otherwise described in this specification, among "monocyclic" and "condensed ring", "monocyclic" is preferably used. Unless otherwise described in this specification, among "saturated ring" and "unsaturated ring", "unsaturated ring" is preferably used. Unless otherwise described in this specification, "monocyclic" is preferably a benzene ring. Unless otherwise described in this specification, "unsaturated ring" is preferably a benzene ring. When "one or more sets of two or more adjacent ones" "are bonded to each other to form a substituted or unsubstituted monocyclic ring" or "are bonded to each other to form a substituted or unsubstituted condensed ring", unless otherwise described in this specification, preferably, one or more sets of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted "unsaturated ring" composed of a plurality of atoms of the main skeleton and at least one element selected from the group consisting of 1 to 15 carbon elements, nitrogen elements, oxygen elements, and sulfur elements.

[0111] When the above-mentioned "monocyclic" or "condensed ring" has a substituent, the substituent is, for example, an "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" mentioned 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 of 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").

[0112] · Substituents in the case of "substituted or unsubstituted" In one embodiment of this specification, the substituent in the case of "substituted or unsubstituted" (which may be referred to as "any substituent" in this specification) is, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms and the like selected from the group consisting of, 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.

[0113] 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.

[0114] 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 It is a group selected from the group consisting of.

[0115] 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 the Present Specification" mentioned above.

[0116] Unless otherwise specified in the present specification, any adjacent substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, and more preferably form a benzene ring. Unless otherwise specified in the present specification, any substituent may further have a substituent. The substituents that any substituent further has are the same as the above-mentioned any substituents.

[0117] In the present 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.

[0118] Hereinafter, the compounds of the present invention will be described. The compound according to one aspect of the present invention is represented by the following formula (1A) or formula (1B). However, hereinafter, the compound of the present invention represented by formula (1A) and each formula included in formula (1A) to be described later may be simply referred to as "compound (1A)", "invention compound (1A)" or "first invention compound". Also, the compound of the present invention represented by formula (1B) and each formula included in formula (1B) to be described later may be simply referred to as "compound (1B)", "invention compound (1B)" or "second invention compound". Furthermore, the above-mentioned first and second invention compounds may be collectively referred to simply as "invention compounds".

Chemical formula

Chemical formula

[0119] Hereinafter, the symbols in Formula (1A) and each formula included in Formula (1A) described later, and the symbols in Formula (1B) and each formula included in Formula (1B) described later will be explained. Note that the same symbol has the same meaning. Also, in this specification, as described below, in Formula (1A), the partial structure bonded to *a may be referred to as "partial structure A". Further, in Formula (1B), the partial structure bonded to *a may be referred to as "partial structure B".

Chemical formula

[0120] <Compound (1A)> In Formula (1A), N * is the central nitrogen atom.

[0121] In Formula (1A), Z 1 and Z 2 One selected from is a single bond bonded to *a, and preferably Z 2 is the single bond bonded to *a. In other words, the partial structure A in the above Formula (1A) is represented by the following Formula (1x-1) or (1x-2), and preferably represented by the following Formula (1x-2). When the partial structure A is represented by the following Formula (1x-2), the compound (1A) is represented by Formula (1A-1) described later.

Chemical formula

[0122] In Formulas (1x-1) to (1x-2), *x indicates the bonding position to *a. Details of Z 1 and Z 2 and other symbols are as described below.

[0123] Z that is not the above single bond 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group (aromatic heterocyclic group) having 5 to 13 ring-forming atoms, preferably each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring-forming carbon atoms, and more preferably a hydrogen atom. Z which is not the above single bond 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 All of may be hydrogen atoms. Z which is not the above single bond 1 and Z 2 , R 13A , and R 14A do not bond to each other to form a ring. R 7 ~R 10 Among them, a pair of adjacent groups may or may not bond to each other to form a ring. R 15 ~R 18 Among them, a pair of adjacent groups may or may not bond to each other to form a ring.

[0124] The unsubstituted alkyl group of the above substituted or unsubstituted alkyl group having 1 to 6 carbon atoms is, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, or a hexyl group; preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, or a pentyl group; more preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group; even more preferably a methyl group, an ethyl group, an isopropyl group or a t-butyl group; Particularly preferably, it is a methyl group.

[0125] The unsubstituted aryl group of the above-mentioned substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms is, for example, a phenyl group, a biphenyl group, or a naphthyl group; preferably, a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group; Particularly preferably, it is a phenyl group.

[0126] The above-mentioned substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms is, for example, a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, an imidazopyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, an isoxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a tetrazolyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolidinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, an indazolyl group, a benzoisoxazolyl group, a benzoisothiazolyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group (benzothienyl group, the same applies hereinafter), an isobenzothiophenyl group (isobenzothienyl group, the same applies hereinafter), a dibenzothiophenyl group (dibenzothienyl group, the same applies hereinafter), or a carbazolyl group (including a 9-carbazolyl group, or a 1-, 2-, 3- or 4-carbazolyl group. The same applies hereinafter); preferably, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group, more preferably, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.

[0127] In formula (1A), R 1Aand R 2A is, independently of one another, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, preferably, independently of one another, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring-forming carbon atoms, and more preferably a hydrogen atom. R 1A and R 2A may be a hydrogen atom. R 1A and R 2A may be bonded to each other to form a ring or may not form a ring.

[0128] The unsubstituted alkyl group of the above-mentioned substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 6 carbon atoms, is, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, or a dodecyl group; preferably, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, or a pentyl group; more preferably, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group; even more preferably, a methyl group, an ethyl group, an isopropyl group or a t-butyl group; particularly preferably a methyl group.

[0129] The unsubstituted aryl group of the above-mentioned substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, preferably 6 to 18, more preferably 6 to 12, is, for example, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a benzoanthryl group, a phenanthryl group, a benzophenanthryl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a fluorenyl group, a fluoranthenyl group, a perylenyl group, or a triphenylenyl group; preferably, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group; more preferably, a phenyl group, a 2-, 3-, or 4-biphenylyl group, a 2-, 3-, or 4-o-terphenylyl group, a 2-, 3-, or 4-m-terphenylyl group, a 2-, 3-, or 4-p-terphenylyl group, or a 1- or 2-naphthyl group; even more preferably, a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group; particularly preferably, a phenyl group.

[0130] The above-mentioned substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, preferably 5 to 20, more preferably 5 to 13, is, for example, a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, an imidazopyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, an isoxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a tetrazolyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolizinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, an indazolyl group, a benzoisoxazolyl group, a benzoisothiazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a phenothiazinyl group, a phenoxazinyl group, a xanthenyl group, a benzofuranyl group, an isobenzofuranyl group, a naphthobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group (benzothienyl group, the same applies hereinafter), an isobenzothiophenyl group (isobenzothienyl group, the same applies hereinafter), a naphthobenzothiophenyl group (naphthobenzothienyl group, the same applies hereinafter), a dibenzothiophenyl group (dibenzothienyl group, the same applies hereinafter), or a carbazolyl group (9-carbazolyl group, or including 1-, 2-, 3- or 4-carbazolyl group. The same applies hereinafter); preferably, a benzofuranyl group, an isobenzofuranyl group, a naphthobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, a naphthobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group, more preferably, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.

[0131] In formula (1A), Y 1 and Y 2 are hydrogen atoms.

[0132] In formula (1A), L 1is an arylene group having 6 to 12 carbon atoms in the ring, which may be substituted or unsubstituted, preferably a phenylene group, a naphthylene group, or a biphenylene group, which may be substituted or unsubstituted, more preferably a phenylene group, or a biphenylene group, which may be substituted or unsubstituted, and even more preferably a phenylene group, which may be substituted or unsubstituted.

[0133] The above-mentioned phenylene group is an o-phenylene group, an m-phenylene group, or a p-phenylene group, and a p-phenylene group is preferred. The above-mentioned biphenylene group is a 4,2'-biphenylene group, a 4,3'-biphenylene group, a 4,4'-biphenylene group, a 3,2'-biphenylene group, a 3,3'-biphenylene group, or a 2,2'-biphenylene group, preferably a 4,2'-biphenylene group, a 4,3'-biphenylene group, a 4,4'-biphenylene group, or a 3,3'-biphenylene group, and even more preferably a 4,4'-biphenylene group. The above-mentioned naphthylene group is preferably a 1,4-naphthylene group, a 2,6-naphthylene group, a 1,5-naphthylene group, or a 1,8-naphthylene group.

[0134] L which is an arylene group 1 The substituents are selected from an unsubstituted alkyl group having 1 to 6 carbon atoms and an aryl group having 6 to 12 carbon atoms in the ring, and the substituents do not bond to each other to form a ring. Details of the unsubstituted alkyl group having 1 to 6 carbon atoms as the above-mentioned substituent and details of the unsubstituted aryl group having 6 to 12 carbon atoms in the ring as the above-mentioned substituent are as described for Z 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 as described with respect to

[0135] In formula (1A), n1 is 0 or 1. When n1 is 0, Z 1 and Z 2One selected from the following is the central nitrogen atom N * is bonded to.

[0136] In formula (1A), X 1 is an oxygen atom, a sulfur atom, or =CR A R B and is preferably an oxygen atom or =CR A R B and more preferably an oxygen atom. R A , R B , and R 21 ~R 28 One selected from the following is a single bond bonded to *b1, or one selected from R A and R B is a divalent group bonded to *b1. Preferably, one of R 22 , R 24 , R 25 , R 27 , R C , and R D is a single bond bonded to *b1, or one selected from R A and R B is a divalent group bonded to *b1. X 1 is =CR A R B In this case, the compound (1A) is represented by formula (1A-2) described later.

[0137] R A and R B which are not the above single bond and not the divalent group bonded to the above *b1 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms. Preferably, they are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring-forming carbon atoms, and more preferably a hydrogen atom. R A and R B may be a hydrogen atom. R A and R B The details of the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, the substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms represented by R in formula (1A) are as described for R 1A and R 2A as described above. R A and R B The divalent group bonded to the above *b1 represented by R is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring-forming atoms. R A and R B As the above alkylene group, arylene group, and heteroarylene group represented by R are the divalent residues of the respective groups described for the above alkyl group, aryl group, and heteroaryl group represented by R A and R B and the same applies to the preferred ones.

[0138] R which is not the above single bond and not the divalent group bonded to the above *b1 A and R B may or may not be bonded to each other to form a ring. R which is not the above single bond and not the divalent group bonded to the above *b1 A and R B The ring formed by R and R bonding to each other is a substituted or unsubstituted spiro ring. The above spiro ring is a hydrocarbon ring or a heterocyclic ring and is selected from a monocyclic ring, a condensed ring, a bridged bicyclic ring, and a bridged tricyclic ring. Examples of the substituted or unsubstituted spiro ring are shown below, but are not limited thereto. * indicates the bonding position to the benzene ring of the fluorene skeleton.

Chemical formula

[0139] In one aspect, L of compound (1A) 2The partial structure that binds to is represented by any of the following formulas (1-a1) to (1-a5). [Chemical formula] [Chemical formula]

[0140] In formulas (1-a1) to (1-a5), ** represents the bonding position to L 2 and indicates the bonding position to L. R 21 ~R 28 , and *b1 are as defined in the above formula (1A). In formulas (1-a1) to (1-a5), R A1 ~R A3 , R A4 ~R A8 , R B1 ~R B3 , and R B4 ~R B8 are hydrogen atoms.

[0141] R 21 ~R 28 that are not the above single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms, preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring-forming carbon atoms, and more preferably a hydrogen atom. R 21 ~R 28 may all be hydrogen atoms. R 21 ~R 28 The details of the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, the substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms represented by are Z 1 and Z 2 in formula (1A), R 13A , R14A and R 15 ~R 18 R 7 ~R 10 is as described with respect to

[0142] In formula (1A), when one selected from R 21 ~R 24 is a single bond connecting to *b1, the R 21 ~R 24 that are not the above single bond do not bond to each other to form a ring, and R 25 ~R 28 may or may not bond to each other to form a ring. R 25 ~R 28 When one selected from R 25 ~R 28 is a single bond connecting to *b1, the R 21 ~R 24 that are not the above single bond do not bond to each other to form a ring, and R

[0143] In formula (1A), L 2 is a substituted or unsubstituted arylene group having 6 to 12 ring-forming carbon atoms. L 2 The details of the substituted or unsubstituted arylene group having 6 to 12 ring-forming carbon atoms represented by L 1 are as described with respect to L in formula (1A).

[0144] When L 1 and L 2 exist in formula (1A), they may be the same or different from each other. Only one of L 1 and L 2 may exist (that is, one of m or n may be 0 and the other may be 1), and both L 1 and L 2 do not have to exist (that is, m and n may be 0). Preferably, the above "-(L 1 ) n1 -" and "-(L2 ) n2 The combination of "-" is represented by any one of the following combinations [k1] to [k4]. · [k1]: single bond / single bond · [k2]: single bond / phenylene · [k3]: phenylene / single bond · [k4]: phenylene / phenylene

[0145] In formula (1A), n2 is 0 or 1. When n2 is 0, one selected from R 21 ~R 28 is bonded to the central nitrogen atom N * . In one embodiment, both n1 and n2 are 0. In another embodiment, both n1 and n2 are 1. In still another embodiment, n1 is 0 and n2 is 1. In still another embodiment, n1 is 1 and n2 is 0.

[0146] In formula (1A), Ar 1 is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring-forming carbon atoms, more preferably a hydrogen atom. Ar 1 The details of the substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms and the substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms represented by are the same as those described for R 1A and R 2A in formula (1A).

[0147] In formula (1A), Ar 2 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, preferably a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, more preferably a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms. Ar 1The details of the substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms represented by are as described for R in formula (1A). 1A and R 2A are as described.

[0148] In formula (1A), m is 0, 1, 2, 3, or 4, preferably 0, 1, 2, or 3, more preferably 0, 1, or 2, and still more preferably 0 or 1. However, when Ar 1 is a hydrogen atom, m is 0. When m is 1 to 4, one to four selected from R 31 to R 34 are single bonds bonded to *c. When m is 2 to 4, the plurality of existing Ar 2 may be the same or different from each other.

[0149] In formula (1A), R 31 to R 34 that are not the above single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms, preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring-forming carbon atoms, and more preferably a hydrogen atom. All of R 31 to R 34 that are not the above single bonds may be hydrogen atoms. R 31 to R 34 The details of the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, the substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms represented by are as described for Z in formula (1A). 1 and Z 2 , R 13A , R 14A , and R 15 to R 18 , R 7 to R 10 are as described.

[0150] In formula (1A), Ar which is not a hydrogen atom 1 , and R which is not a hydrogen atom 34 ~R 24 Among them, a pair of adjacent groups may or may not combine with each other to form a ring.

[0151] <Compound (1B)> In formula (1B), N * is the central nitrogen atom.

[0152] In formula (1B), one selected from R 11 ~R 14 is a single bond connecting to *a, preferably one selected from R 12 ~R 14 is a single bond connecting to *a, more preferably, one of R 12 or R 14 is a single bond connecting to *a, even more preferably, R 12 is a single bond connecting to *a. In other words, the partial structure B in the above formula (1B) is represented by any one of the following formulas (1y-1) to (1y-4), preferably represented by any one of the following formulas (1y-2) to (1y-4), more preferably represented by the following formula (1y-2) or formula (1y-4), and even more preferably represented by the following formula (1y-2).

Chemical formula

[0153] In formulas (1y-1) to (1y-4), *y indicates the bonding position to *a. The details of R 11 ~R 14 , and other symbols are as described below.

[0154] R which is not the above single bond 11 ~R 14 , R 15 ~R 18 , and R 7 ~R 10is, independently of each other, a hydrogen atom, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, preferably, independently of each other, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring-forming carbon atoms, and more preferably a hydrogen atom. R other than the above single bond 11 ~R 14 、R 15 ~R 18 、and R 7 ~R 10 All of may be hydrogen atoms. R other than the above single bond 11 ~R 14 do not combine with each other to form a ring. R 7 ~R 10 Among them, a pair of adjacent groups may combine with each other to form a ring or may not form a ring. R 15 ~R 18 Among them, a pair of adjacent groups may combine with each other to form a ring or may not form a ring. R 11 ~R 14 Details of the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms and the substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by are as described for Z 1 and Z 2 、R 13A 、R 14A 、and R 15 ~R 18 、R 7 ~R 10 as described.

[0155] In formula (1B), R 1B 、R 2B 、R 5B 、and R 6Bis, independently of each other, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, preferably, independently of each other, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring-forming carbon atoms, and more preferably a hydrogen atom. R 1B 、R 2B 、R 5B 、and R 6B may all be hydrogen atoms. R 1B and R 2B may be bonded to each other to form a ring or may not form a ring. R 5B and R 6B may be bonded to each other to form a ring or may not form a ring. R 1B 、R 2B 、R 5B 、and R 6B The details of the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, the substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms represented are as described for R 1A and R 2A in formula (1A).

[0156] In formula (1B), L 3 is a substituted or unsubstituted arylene group having 6 to 12 ring-forming carbon atoms. The details of the above-mentioned substituted or unsubstituted arylene group having 6 to 12 ring-forming carbon atoms are as described for L 1 in formula (1A).

[0157] In formula (1B), n3 is 0 or 1. When n3 is 0, Ar 3 is bonded to the central nitrogen atom N * 。

[0158] In formula (1B), Ar 3is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a group represented by the following formula (2-1), or a group represented by the following formula (2-2), preferably, an aryl group having 6 to 18 ring-forming carbon atoms, a group represented by the following formula (2-1), or a group represented by the following formula (2-2), more preferably an aryl group having 6 to 12 ring-forming carbon atoms.

Chemical formula

[0159] In formula (2-1), ** represents the bonding position to L 3 represents the bonding position to L.

[0160] In formula (2-1), X 3 is an oxygen atom or a sulfur atom, preferably an oxygen atom.

[0161] In formula (2-1), one selected from R 41 ~R 44 is a single bond bonding to *d, preferably one selected from R 41 , R 42 , and R 44 is a single bond bonding to *d, more preferably R 41 or R 44 is a single bond bonding to *d, still more preferably, R 44 is a single bond bonding to *d. R not being the above single bond 41 ~R 44 , R 45 ~R 48 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms, preferably, each independently, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring-forming carbon atoms, more preferably a hydrogen atom. R not being the above single bond 41 ~R 44 , R 45 ~R 48All of them may be hydrogen atoms. R that is not the above single bond 41 ~R 44 Among them, a pair of adjacent groups, and R 45 ~R 48 Among the pairs of adjacent groups, they may or may not combine with each other to form a ring. R 41 ~R 48 The details of the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, the substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms represented by R are as described for Z in formula (1A) 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 as described.

[0162] In formula (2-2), ** represents the bonding position to L 3

[0163] In formula (2-2), R 41 ~R 48 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms, preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring-forming carbon atoms, and more preferably a hydrogen atom. R 41 ~R 48 All of them may be hydrogen atoms. R 41 ~R 48 Among the pairs of adjacent groups, they may or may not combine with each other to form a ring. R 41 ~R 48 ​The details of the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, the substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms represented by are as described for Z in formula (1A). 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 are as described above with respect to. Ar 3 When is represented by the above formula (2-2), n3 is preferably 1.

[0164] In formula (1B), L 4 is a substituted or unsubstituted arylene group having 6 to 12 ring-forming carbon atoms. L 4 The details of the substituted or unsubstituted arylene group having 6 to 12 ring-forming carbon atoms represented by are as described for L in formula (1A). 1 are as described above with respect to.

[0165] In formula (1B), n4 is 0 or 1. When n4 is 0, Ar 4 is bonded to the central nitrogen atom N * . In one embodiment, n1, n3, and n4 are all 0, in another embodiment, n1, n3, and n4 are all 1, in still another embodiment, n1 and n3 are 0 and n4 is 1, in still another embodiment, n1 and n4 are 0 and n3 is 1, in still another embodiment, n3 and n4 are 0 and n1 is 1, in still another embodiment, n1 is 0 and n3 and n4 are 1, in still another embodiment, n3 is 0 and n1 and n4 are 1, and in still another embodiment, n4 is 0 and n1 and n3 are 1.

[0166] In formula (1B), Ar 4 is a group represented by the following formula (3-1) or a group represented by the following formula (3-2).

Chemical formula

[0167] In formula (3-1), *** represents the bonding position to L. 4 It represents the bonding position to.

[0168] In formula (3-1), X 2 is an oxygen atom, a sulfur atom, or =CR C R D and preferably an oxygen atom or =CR C R D and more preferably an oxygen atom.

[0169] In formula (3-1), R 21B ~R 24B , R C , and R D One selected from is a single bond bonding to *b2, or one selected from R C and R D is a divalent group bonding to *b2. X 2 When is an oxygen atom or a sulfur atom, one selected from R 21B ~R 28B is a single bond bonding to *b2, preferably one selected from R 21B , R 22B , R 24B , R 25B , R 27B , and R 28B is a single bond bonding to *b2, more preferably one selected from R 21B , R 24B , R 25B , and R 27B is a single bond bonding to *b2, even more preferably R 24B or R 25B is a single bond bonding to *b2. X 2 When is =CR C R D preferably R 21B ~R 23B , R 26B ~R 28B , R C , and R DOne selected from the following is a single bond that binds to *b2, or R C and R D One selected from the following is a divalent group that binds to *b2, more preferably R 23B R 26B R C or R D One selected from the following is a single bond that binds to *b2, or R C and R D One selected from the following is a divalent group that binds to *b2. R other than the above single bond 21B ~R 24B R 25B ~R 28B are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms, preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring-forming carbon atoms, and more preferably a hydrogen atom. R other than the above single bond 21B ~R 24B R 25B ~R 28B may all be hydrogen atoms. R 21B ~R 28B The details of the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, the substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms represented by are as described for Z 1 and Z 2 R 13A R 14A and R 15 ~R 18 R 7 ~R 10 as described.

[0170] In formula (3-1), when one selected from R 21B ~R 24B is a single bond that binds to *b2, R other than the single bond 21B ~R24B do not combine with each other to form a ring, and R 25B ~R 28B may or may not combine with each other to form a ring. R 25B ~R 28B When one selected from R 25B ~R 28B is a single bond that binds to *b2, R 21B ~R 24B which is not the single bond do not combine with each other to form a ring, and R

[0171] In formula (3-1), R C and R D which are not the single bond and are not a divalent group that binds to the above *b2 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring-forming carbon atoms, and more preferably a hydrogen atom. R C and R D which are not the single bond and are not a divalent group that binds to the above *b2 may be hydrogen atoms. R C and R D which are not the single bond and are not a divalent group that binds to the above *b2 may or may not combine with each other to form a ring. R C and R D The details of the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, the substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms represented by R 1A and R 2A are as described for R However, R C and R DWhen one selected from them is an aryl group, the two combine to form R C and R D do not form 1’,3’-dihydrospiro[fluorene-9,2’-indene] together with the fluorene ring to which they are attached. In other words, R C and R D do not combine with each other to form a structure represented by the following formula. In the following formula, *w indicates the bonding position to L4. Also, R is omitted in the following formula for simplicity. [Chemical formula]

[0172] In formula (3-1), when X 2 is an oxygen atom or a sulfur atom, n4 is 1.

[0173] In formula (3-2), *** represents the bonding position to L 4 .

[0174] In formula (3-2), R 21B ~R 28B are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms, preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring-forming carbon atoms, and more preferably a hydrogen atom. R 21B ~R 28B may all be hydrogen atoms. R 21B ~R 24B Among them, a pair of adjacent groups, and R 25B ~R 28B Among them, a pair of adjacent groups may or may not combine with each other to form a ring. R 21 ~R 28The details of the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, the substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms represented by are as described for Z in formula (1A). 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 are as described above with respect to.

[0175] In formula (3-2), *N * , L 1 , n1, R 7 ~R 10 , and R 15 ~R 18 are synonymous with those defined in formula (1A). Ar 4 When is represented by the above formula (3-2), n4 is preferably 1.

[0176] In formula (1B), when L 1 and L 2 and L 3 exist, the three may be the same, may be different from each other, or two of the three may be the same and the other one may be different. In formula (1B), only any two of L 1 and L 2 and L 3 may exist (that is, two of n1, n3, and n4 may be 1 and the other one may be 0). In this case, the two existing ones may be the same or may be different from each other. In formula (1B), only any one of L 1 and L 2 and L 3 may exist (that is, two of n1, n3, and n4 may be 0 and the other one may be 1). All of L 1 ~L 3 do not have to exist (that is, n1, n3, and n4 may be 0). Preferably, the above-mentioned "-(L 1) n1 -」and「-(L 3 ) n3 -」and「-(L 4 ) n4 The combination of "-" is represented by any one of the following combinations [k11] to [k18]. ·[k11]: single bond / single bond / single bond ·[k12]: single bond / single bond / phenylene ·[k13]: single bond / phenylene / single bond ·[k14]: phenylene / single bond / single bond ·[k15]: single bond / phenylene / phenylene ·[k16]: phenylene / single bond / phenylene ·[k17]: phenylene / phenylene / single bond ·[k18]: phenylene / phenylene / phenylene

[0177] In a preferred embodiment, the above compound (1A) is represented by the following formula (1A-1).

Chemical formula

[0178] In formula (1A-1), R 1A , R 2A , Y 1 , Y 2 , R 7 ~R 10 , Z 1 , R 13A , R 14A , R 15 ~R 18 , R 21 ~R 28 , X 1 , R 31 ~R 34 , N * , Ar 1 , Ar 2 , L 1 , L 2 , *b1, *c, m, n1, and n2 are as defined in the above formula (1A).

[0179] In one aspect, the above compound (1A) is represented by the following formula (1A-2).

Chemical formula

[0180] In formula (1A-2), R 1A , R 2A , Y 1 , Y 2 , R 7 ~R 10 , Z 1 , Z 2 , R 13A , R 14A , R 15 ~R 18 , R 21 ~R 28 , R A , R B , R 31 ~R 34 , N * , Ar 1 , Ar 2 , L 1 , L 2 , *a, *b1, *c, m, n1, and n2 are as defined in the above formula (1A).

[0181] In one aspect, in formula (1A-2), one of R 21 , R 22 , R 24 , R 25 , R 27 , and R 28 is a single bond that binds to *b1. In another aspect, one of R 21 , R 24 , R 25 , and R 28 is a single bond that binds to *b1. In yet another aspect, a single bond to which R 24 or R 28 binds to *b1.

[0182] In one aspect, the compound (1A) is represented by the above formula (1A), formula (1A-1), or formula (1A-2). When n1 is 1, L 1 is a phenylene group. When n2 is 1, L 2is a phenylene group.

[0183] In one aspect, the above compound (1A) is represented by any one of the following formulas (1A-3) to (1A-5).

Chemical formula

Chemical formula

Chemical formula

[0184] In formulas (1A-3) and (1A-5), R 51 ~R 55 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, preferably a hydrogen atom. However, one selected from R 51 ~R 55 is a single bond bonded to *d. All of R 51 ~R 55 that are not the single bond bonded to *d may all be hydrogen atoms. Among the above R 51 ~R 55 that are not the single bond, one adjacent pair does not bond to each other and does not form a ring. In formulas (1A-4) and (1A-5), R 61 ~R 65 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, preferably a hydrogen atom. However, one selected from R 61 ~R 65 is a single bond bonded to *e. All of R 61 ~R 65 that are not the single bond bonded to *e may all be hydrogen atoms. Among the above R 61 ~R 65 that are not the single bond, one adjacent pair does not bond to each other and does not form a ring.

[0185] R 51 ~R 55 、 and R 61 ~R 65 The unsubstituted alkyl group having 1 to 6 carbon atoms and the unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by ~R are Z in formula (1A) 1 and Z 2 、R 13A 、R 14A 、 and R 15 ~R 18 、R 7 ~R 10 are as described with respect to ~R

[0186] In formulas (1A-3) to (1A-5), R 1A 、R 2A 、Y 1 、Y 2 、R 7 ~R 10 、Z 1 、Z 2 、R 13A 、R 14A 、R 15 ~R 18 、R 21 ~R 28 、X 1 、R 31 ~R 34 、N * 、Ar 1 、Ar 2 、L 1 、L 2 、*a, *b1, *c, m, n1, and n2 are as defined in the above formula (1A).

[0187] In one embodiment, the above compound (1A) is represented by any one of the following formulas (1A-6) to (1A-8). [Chemical formula] [Chemical formula] [Chemical formula]

[0188] In formulas (1A-6) to (1A-8), R 1A , R 2A , Y 1 , Y 2 , R 7 ~R 10 , Z 1 , Z 2 , R 13A , R 14A , R 15 ~R 18 , R 21 ~R 28 , X 1 , R 31 ~R 34 , N * , Ar 1 , Ar 2 , L 1 , L 2 , *a, *b1, *c, m, n1, and n2 are as defined in the above formula (1A).

[0189] In one embodiment, the above compound (1A) is represented by the above formula (1A) and any one of formulas (1A-1) to (1A-8), ·Ar 1 is a hydrogen atom and m is 0, or ·Ar 1 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms and m is 0, or ·Ar 1 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms and m is 1.

[0190] In one embodiment, the above compound (1A) is represented by the above formula (1A) and any one of formulas (1A-1) to (1A-8), Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms.

[0191] In one embodiment, the above compound (1B) is represented by the following formula (1B-1).

Chemical formula

[0192] In formula (1B-1), R 1B and R 2B and R 5B and R 6B and R 7 to R 10 and R 11 and R 13 to R 18 and N * and Ar 3 and Ar 4 and L 1 and L 3 and L 4 n1, n3, and n4 are as defined in the above formula (1B).

[0193] In one aspect, the above compound (1B) is represented by the following formula (1B-2).

Chemical formula

[0194] In formula (1B-2), R 1B and R 2B and R 5B and R 6B and R 7 to R 10 and R 11 to R 18 and R 21B to R 28B and R C and R D and N * and Ar 3 and L 1 and L 3 and L 4 *a, *b2, n1, n3, and n4 are as defined in the above formula (1B).

[0195] In one aspect, in formula (1B-2), Ar 3 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

[0196] In one aspect, represented by any of the above formula (1B), formula (1B-1), and formula (1B-2), when n1 is 1, L1 is a phenylene group, and when n3 is 1, L 3 is a phenylene group, and when n4 is 1, L 4 is a phenylene group.

[0197] In one aspect, the above compound (1B) is represented by any one of the following formulas (1B-3) to (1B-9).

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0198] In formulas (1B-3), (1B-6), (1B-7), and (1B-9), R 51 ~R 55 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, preferably a hydrogen atom. However, one selected from R 51 ~R 55 is a single bond bonded to *d. All of R 51 ~R 55 that are not the single bond bonded to *d may be hydrogen atoms. For R 51 ~R 55Among them, a set of adjacent ones do not bond to each other and do not form a ring. In formula (1B-4), formula (1B-6), formula (1B-8), and formula (1B-9), R 71 ~R 75 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, preferably a hydrogen atom. However, one selected from R 71 ~R 75 is a single bond bonded to *f. All of R 71 ~R 75 that are not the single bond bonded to *f may all be hydrogen atoms. Among the R 71 ~R 75 that are not the single bond, a set of adjacent ones do not bond to each other and do not form a ring. In formula (1B-5), and formula (1B-7) to formula (1B-9), R 81 ~R 85 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, preferably a hydrogen atom. However, one selected from R 81 ~R 85 is a single bond bonded to *g. All of R 81 ~R 85 that are not the single bond bonded to *g may all be hydrogen atoms. Among the R 81 ~R 85 that are not the single bond, a set of adjacent ones do not bond to each other and do not form a ring.

[0199] R 51 ~R 55 、R 71 ~R 75 、and R 81 ~R 85 The unsubstituted alkyl group having 1 to 6 carbon atoms and the unsubstituted aryl group having 6 to 12 ring-forming carbon atoms represented by 1 and Z 2 、R 13A 、R 14A 、and R 15 ~R 18 、R 7 ~R 10It is as described with respect to

[0200] In formulas (1B-3) to (1B-9), R 1B , R 2B , R 5B , R 6B , R 7 ~R 10 , R 11 ~R 18 , N * , Ar 3 , Ar 4 , L 1 , L 3 , L 4 , *a, n1, n3, and n4 are as defined in the above formula (1B).

[0201] In one aspect, the above compound (1B) is represented by any of the above formula (1B), formula (1B-1), and formulas (1B-3) to (1B-9), Ar 3 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, Ar 4 is a group represented by the above formula (3-1), and X 2 is an oxygen atom or a sulfur atom, or is a group represented by the above formula (3-2).

[0202] In one aspect, the above compound (1B) is represented by the above formula (1B), Ar 3 is a group represented by the above formula (2-1) or formula (2-2), Ar 4 is a group represented by the above formula (3-1), and X 2 is an oxygen atom or a sulfur atom, or is a group represented by the above formula (3-2).

[0203] In one aspect, the above compound (1B) is represented by the above formula (1B) and any of formulas (1B-1) to (1B-9), and Ar 3 is represented by any of the following formulas (2A) to (2F).

Chemical formula

[0204] In formula (2A), *21 is the bonding position to L. 3 It is the bonding position to L.

[0205] In formula (2A), one selected from R 101 ~R 105 is a single bond that binds to *22, and one selected from R 106 ~R 110 is a single bond that binds to *23. R other than the above single bond 101 ~R 105 and R 106 ~R 110 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, preferably a hydrogen atom. R other than the above single bond 101 ~R 105 and R 106 ~R 110 may all be hydrogen atoms. The details of the above substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as described for R 1A and R 2A in formula (1A) except that the number of carbon atoms is 1 to 10. The details of the above substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms are as described for Z 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 in formula (1A). Two adjacent ones selected from R other than the above single bond 101 ~R 105 do not bond to each other and do not form a ring. Two adjacent ones selected from R other than the above single bond 106 ~R 110 do not bond to each other and do not form a ring.

[0206] In formula (2A), R111 ~R 115 is, independently of one another, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms, preferably, independently of one another, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring-forming carbon atoms, and more preferably a hydrogen atom. R 111 ~R 115 All of them may be hydrogen atoms. The details of the above-mentioned substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are the same as those described for R 1A and R 2A in formula (1A) except that the number of carbon atoms is 1 to 10. The details of the above-mentioned substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, and the details of the above-mentioned substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms are the same as those described for Z 1 and Z 2 in formula (1A), R 13A R 14A and R 15 ~R 18 R 7 ~R 10 in formula (1A). R 111 ~R 115 Two adjacent ones selected from R

[0207] In formula (2A), m11 is 0, 1 or 2, and n11 is 0 or 1. Except for the case where m11 is 2 and n11 is 0. When m11 = 0 and n11 = 0, *23 represents *21. When m11 = 0 and n11 = 1, *22 represents *21. When m11 = 1 and n11 = 0, *23 represents *22. Ar 3 When represented by formula (2A), it is preferable that n3 is 0. Also, Ar 3is represented by the formula (2A), and when m11 is 0 and n11 is 1, R 106 ~R 110 is preferably a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms. Furthermore, when Ar 3 is represented by the formula (2A) and m11 is 1 and n11 is 0, R which is not a single bond bonded to *22 101 ~R 105 is preferably a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.

[0208] The group represented by the formula (2A) is preferably represented by the following formula. In the following formula, R is omitted for simplicity.

Chemical formula

[0209]

Chemical formula

[0210] In the formula (2B), *24 is the bonding position to L 3 is.

[0211] In the formula (2B), one selected from R 121 ~R 128 is a single bond bonded to *25. R which is not the above single bond 121 ~R 128 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, and are preferably a hydrogen atom. R 111 ~R 115 may all be hydrogen atoms. The details of the above substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are the same as those described for R 1A and R 2A in the formula (1A) except that the number of carbon atoms is 1 to 10. Details of the above-mentioned substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms are as described for Z in formula (1A). 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 as described. Among the above R 121 ~R 128 selected that are not single bonds, any two adjacent ones do not bond to each other to form a ring.

[0212]

Chemical formula

[0213] In formula (2C), *26 is the bonding position to L 3 .

[0214] In formula (2C), one selected from R 131 ~R 140 is a single bond that bonds to *27. Among the above R 131 ~R 140 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, preferably a hydrogen atom. Among the above R 131 ~R 140 may all be hydrogen atoms. Details of the above-mentioned substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as described for R 1A and R 2A in formula (1A) except that the number of carbon atoms is 1 to 10. Details of the above-mentioned substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms are as described for Z 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R10 is as described with respect to R other than the above single bond 131 ~R 140 Two adjacent ones selected from do not bond to each other and do not form a ring.

Chemical formula

[0215] In formula (2D), *28 is the bonding position to L 3 is.

[0216] In formula (2D), n12 is 0 or 1. When n12 is 0, one selected from R 141 ~R 148 , R E , and R F selected from is a single bond that bonds to *29, or one selected from R E and R F selected is a divalent group that bonds to *29. When n12 is 1, R 141 and R 142 , R 142 and R 143 , or R 143 and R 144 One of is a single bond that bonds to *h, the other is a single bond that bonds to *i, and R that is not a single bond that bonds to *h and *i 141 ~R 144 , R 145 ~R 148 , R 200 ~R 203 , R E , and R F selected from is a single bond that bonds to *29, or one selected from R E and R F selected is a divalent group that bonds to *29.

[0217] In formula (2D), R other than the above single bond 141 ~R 148 and R other than the above single bond 200 ~R 203is, independently of one another, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms, preferably, independently of one another, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring-forming carbon atoms, and more preferably a hydrogen atom. R other than the above single bond 141 ~R 148 and R other than the above single bond 200 ~R 203 All of may be hydrogen atoms. Details of the above substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are the same as those described for R 1A and R 2A in Formula (1A) except that the number of carbon atoms is 1 to 10. Details of the above substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms and details of the above substituted or unsubstituted heteroaryl group having 5 to 13 ring-forming atoms are the same as those described for Z 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 in Formula (1A). R other than the above single bond 141 ~R 148 and R other than the above single bond 200 ~R 203 Two adjacent ones selected from do not bond to each other to form a ring.

[0218] In Formula (2D), R that is not the above single bond and is not a divalent group bonding to the above *29 E and R Fis, independently of each other, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, preferably, independently of each other, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring-forming carbon atoms, and more preferably a hydrogen atom. R which is not the above single bond and is not a divalent group bonded to the above *29 E and R F may be a hydrogen atom. Details of the above substituted or unsubstituted alkyl group having 1 to 30 carbon atoms are as described for R 1A and R 2A in formula (1A). Details of the above substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, and details of the above substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms are as described for Z 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 in formula (1A). R which is not the above single bond and is not a divalent group bonded to the above *29 E and R F may be bonded to each other to form a ring or may not form a ring. However, when one selected from R E and R F is an aryl group, the two are not bonded to form 1',3'-dihydrospiro[fluorene-9,2'-indene] together with the fluorene ring to which R E and R F are bonded. In other words, R E and R F do not bond to each other to form a structure represented by the following formula. In the following formula, *w2 indicates the bonding position to L3. Also, in the following formula, R is omitted for simplicity.

Chemical formula

[0219]

Chem.

[0220] In formula (2E), *30 is the bonding position to L 3 is the bonding position to L.

[0221] In formula (2E), one selected from R 151 ~R 155 is a single bond that binds to *31, and the other one selected from R 151 ~R 155 is a single bond that binds to *32. R 151 ~R 155 that is not the above single bond is, independently of each other, a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group, preferably a hydrogen atom. R 151 ~R 155 may all be hydrogen atoms. Details of the above substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as described for R 1A and R 2A in formula (1A) except that the number of carbon atoms is 1 to 10. R 151 ~R 155 selected from the above do not bond to each other and do not form a ring.

[0222] In formula (2E), R 161 ~R 165 and R 171 ~R 175 are, independently of each other, a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms, preferably a hydrogen atom. R 161 ~R 165 and R 171 ~R 175 may all be hydrogen atoms. Details of the above-mentioned substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are the same as those described for R in formula (1A) except that the number of carbon atoms is 1 to 10. 1A and R 2A are as described above. R that is not a hydrogen atom 161 ~R 165 At least one adjacent pair selected from may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and may not form a ring. R that is not a hydrogen atom 171 ~R 175 At least one adjacent pair selected from may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and thus may not form a ring.

[0223] Formula (2E) includes groups represented by the following formulas (2E-1) to (2E-5), and formula (2E-1), (2E-2), or (2E-5) is preferred.

Chemical formula

[0224]

Chemical formula

[0225] In formula (2F), *32 is the bonding position to L 3 .

[0226] In formula (2F), one selected from R 181 ~R 192 is a single bond that binds to *33. R that is not the above single bond 181 ~R 192 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, preferably a hydrogen atom. R that is not the above single bond 181 ~R 192 may all be hydrogen atoms. The details of the above-mentioned substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are the same as those described for R in formula (1A) except that the number of carbon atoms is 1 to 10. 1A and R 2A as described. The details of the above-mentioned substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms are the same as those described for Z in formula (1A), 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 as described. Two adjacent ones selected from the above R 181 ~R 192 that are not a single bond do not bond to each other and do not form a ring.

[0227] In one aspect, the inventive compound is represented by any one of the above formula (1A), formula (1A-1), and formulas (1A-3) to (1A-5), and X 1 is an oxygen atom.

[0228] In one aspect, the inventive compound is represented by any one of the above formula (1B), formula (1B-1), and formulas (1B-3) to (1B-9), and X 2 is an oxygen atom.

[0229] In one aspect, the inventive compound is represented by any one of the above formula (1B), formula (1B-1), and formulas (1B-3) to (1B-9), and X 3 is an oxygen atom.

[0230] In one aspect, R 1A , R 2A , R 7 ~R 10 , R 13A , R 14A , R 15 ~R 18 , the above Z that is not a single bond 1 and Z 2 , the above R that is not a single bond 31 ~R 34 , Ar 1, R that is not the above single bond 21 ~R 28 , R that is not the above single bond and is not a divalent group bonding to *b1 A and R B , R 1B , R 2B , R 5B , R 6B , R that is not the above single bond 11 ~R 14 , R that is not the above single bond 41 ~R 44 , R 45 ~R 48 , R that is not the above single bond 21B ~R 28B , R that is not the above single bond and is not a divalent group bonding to *b2 C and R D , R that is not the above single bond 101 ~R 105 , R that is not the above single bond 106 ~R 110 , R 111 ~R 115 , R that is not the above single bond 121 ~R 128 , R that is not the above single bond 131 ~R 140 , R that is not the above single bond 141 ~R 148 , R that is not the above single bond 200 ~R 203 , R that is not the above single bond 151 ~R 155 , R 161 ~R 165 , R 171 ~R 175 , and R that is not the above single bond 181 ~R 192 are all hydrogen atoms.

[0231] In one aspect, the compound represented by formula (1A) or formula (1B) contains at least one deuterium atom. The deuterium atoms contained in compound (1A) and compound (1B) will be described in detail later.

[0232] In one embodiment of compound (1A) and compound (1B), at least one of the following (1) to (9) is a deuterium atom. (1) R 1A 、R 2A 、Y 1 、Y 2 、R 7 ~R 10 、Z 1 、Z 2 、R 13A 、R 14A 、R 15 ~R 18 、R 21 ~R 28 、R 31 ~R 34 、R A 、R B 、Ar 1 、R 51 ~R 55 、R 61 ~R 65 、R 1B 、R 2B 、R 5B 、R 6B 、R 11 ~R 14 、R 41 ~R 48 、R 21B ~R 28B 、R C 、R D 、R 71 ~R 75 、R 81 ~R 85 、R 101 ~R 105 、R 106 ~R 110 、R 111 ~R 115 、R 121 ~R 128 、R 131 ~R 140 、R 141 ~R 148 、R 200 ~R 203 、R E 、R F 、R 151 ~R 155 、R 161 ~R 165 、R 171 ~R 175 、and R 181~R 192 represents a hydrogen atom; (2)R 1A 、R 2A 、R 7 ~R 10 、Z 1 、Z 2 、R 13A 、R 14A 、R 15 ~R 18 、R 21 ~R 28 、R 31 ~R 34 、R A 、R B 、R 51 ~R 55 、R 61 ~R 65 、R 1B 、R 2B 、R 5B 、R 6B 、R 11 ~R 14 、R 41 ~R 48 、R 21B ~R 28B 、R C 、R D 、R 71 ~R 75 、R 81 ~R 85 、R 101 ~R 105 、R 106 ~R 110 、R 111 ~R 115 、R 121 ~R 128 、R 131 ~R 140 、R 141 ~R 148 、R 200 ~R 203 、R E 、R F 、R 151 ~R 155 、R 161 ~R 165 、R 171 ~R 175 、and R 181 ~R 192 a hydrogen atom directly bonded to the alkyl group represented by; (3)R 1A 、R 2A, R 7 ~R 10 , Z 1 , Z 2 , R 13A , R 14A , R 7 ~R 10 , R 15 ~R 18 , R 21 ~R 28 , R 31 ~R 34 , Ar 1 , Ar 2 , R A , R B , R 51 ~R 55 , R 61 ~R 65 , R 1B , R 2B , R 5B , R 6B , R 11 ~R 14 , R 41 ~R 48 , R 21B ~R 28B , R C , R D , R 71 ~R 75 , R 81 ~R 85 , R 101 ~R 105 , R 106 ~R 110 , R 111 ~R 115 , R 121 ~R 128 , R 131 ~R 140 , R 141 ~R 148 , R 200 ~R 203 , R E , R F , R 151 ~R 155 , and R 181 ~R 192 a hydrogen atom directly bonded to the aryl group represented by; (4)R 1A , R 2A , R 7 ~R 10 , Z 1 , Z 2 , R13A , R 14A , R 15 ~R 18 , R 21 ~R 28 , R 31 ~R 34 , Ar 1 , R A , R B , R 1B , R 2B , R 5B , R 6B , R 41 ~R 48 , R 21B ~R 28B , R C , R D , R 111 ~R 115 , R 141 ~R 148 , R 200 ~R 203 , R E , and R F a hydrogen atom directly bonded to the heteroaryl group represented by; (5)R 1A , R 2A , R 7 ~R 10 , Z 1 , Z 2 , R 13A , R 14A , R 15 ~R 18 , R 21 ~R 28 , R 31 ~R 34 , R A , R B , R 1B , R 2B , R 5B , R 6B , R 11 ~R 14 , R 41 ~R 48 , R 21B ~R 28B , R C , R D , R 111 ~R 115 , R 121 ~R 128 , R 131 ~R 140 , R 141 ~R148 and R 200 to R 203 and R E and R F and R 181 to R 192 a hydrogen atom directly bonded to a substituent of the alkyl group represented by; (6)R 1A and R 2A and R 7 to R 10 and Z 1 and Z 2 and R 13A and R 14A and R 15 to R 18 and R 21 to R 28 and R 31 to R 34 and Ar 1 and Ar 2 and R A and R B and R 1B and R 2B and R 5B and R 6B and R 11 to R 14 and R 41 to R 48 and R 21B to R 28B and R C and R D and R 111 to R 115 and R 121 to R 128 and R 131 to R 140 and R 141 to R 148 and R 200 to R 203 and R E and R F and R 181 to R 192 a hydrogen atom directly bonded to a substituent of the aryl group represented by; (7)R 1A and R 2A and R 7 to R 10 and Z 1 and Z 2 and R 13A and R 14A and R 15 to R 18 and R21 ~R 28 、R 31 ~R 34 、Ar 1 、R A 、R B 、R 1B 、R 2B 、R 5B 、R 6B 、R 41 ~R 48 、R 21B ~R 28B 、R C 、R D 、R 111 ~R 115 、R 141 ~R 148 、R 200 ~R 203 、R E 、and a hydrogen atom directly bonded to a substituent of the heteroaryl group represented by R F ; (8)L 1 ~L 4 a hydrogen atom directly bonded to the arylene group represented by; and (9)L 1 ~L 4 a hydrogen atom directly bonded to a substituent of the arylene group represented by.

[0233] As described above, the "hydrogen atom" used in this specification includes protium, deuterium, and tritium. The compound of the first or second invention may contain deuterium atoms of natural origin. Alternatively, deuterium atoms may be intentionally introduced into the compound of the first or second invention by using a compound in which part or all of the starting compound is deuterated.

[0234] The deuteration rate of the compound of the first or second invention depends on the deuteration rate of the starting compound used. Even if starting materials with a predetermined deuteration rate are used, a certain proportion of light hydrogen isotopes may be contained naturally. Therefore, the embodiments of the deuteration rate of the invention compounds shown below include ratios considering trace amounts of isotopes of natural origin, as opposed to the ratios obtained simply by counting the number of deuterium atoms represented by the chemical formula. The deuteration rate of the first or second inventive compound is preferably 1% or more, more preferably 3% or more, still more preferably 5% or more, even more preferably 10% or more, and even more preferably 50% or more. The first or second inventive compound may be a deuterated form in which all hydrogen atoms are deuterium atoms (i.e., the deuteration rate of the inventive compound is 100%).

[0235] The first or second inventive compound may be a mixture containing a deuterated compound and a non-deuterated compound, or a mixture of two or more compounds having different deuteration rates. The deuteration rate of such a mixture is preferably 1% or more, more preferably 3% or more, still more preferably 5% or more, even more preferably 10% or more, and even more preferably 50% or more, and less than 100%. Also, the respective ratios of the number of deuterium atoms to the total number of hydrogen atoms in the first or second inventive compound are preferably 1% or more, more preferably 3% or more, still more preferably 5% or more, even more preferably 10% or more, and 100% or less.

[0236] Details of the substituents (any substituents) in the case of "substituted or unsubstituted" included in the definitions of the above formulas are as described in "Substituents in the case of'substituted or unsubstituted'".

[0237] A person skilled in the art can easily manufacture the first or second inventive compound with reference to the synthesis examples described below and known synthesis methods.

[0238] Specific examples of the first or second inventive compound are shown below, but the invention is not limited to the following exemplified compounds. In the following specific examples, D represents a deuterium atom.

[0239]

Chemical formula

[0240] [Chemistry]

[0241] [Chemistry]

[0242] [Chemistry]

[0243] [Chemistry]

[0244] [Chemistry]

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[0246] [Chemistry]

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[0249]

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[0250]

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[0255]

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[0256]

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[0258] [Chemical]

[0259] [Chemical]

[0260] [Chemical]

[0261] [Chemical]

[0262] [Chemical]

[0263] [Chemical]

[0264] [Chemical]

[0265] [Chemistry]

[0266] [Chemistry]

[0267] [Chemistry]

[0268] [Chemistry]

[0269] [Chemistry]

[0270] [Chemistry]

[0271] [Chemistry]

[0272] [Chemistry]

[0273] [Chemistry]

[0274]

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[0275]

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[0276]

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[0277]

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[0278]

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[0280]

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[0281]

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[0286]

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[0287]

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[0290]

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[0295]

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[0296]

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[0297]

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[0298]

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[0299]

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[0300]

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[0301]

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[0302]

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[0303]

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[0304]

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[0305]

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[0306]

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[0307]

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[0308]

Chem.

[0309] Materials for organic EL elements The material for organic EL elements according to one aspect of the present invention contains a first or second inventive compound. The content of the first or second inventive compound in the material for organic EL elements is 1% by mass or more (including 100%), preferably 10% by mass or more (including 100%), more preferably 50% by mass or more (including 100%), still more preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). The material for organic EL elements according to one aspect of the present invention is useful for the manufacture of organic EL elements. In one aspect of the present invention, it is preferable that the first or second inventive compound is a hole transport layer material.

[0310] In one aspect of the present invention, it is preferable that the material for organic EL elements further contains a light hydrogen form of the first or second inventive compound. The light hydrogen form refers to a compound in which all hydrogen atoms in the first or second inventive compound are light hydrogen atoms. The mixing molar ratio of the first or second inventive compound to the light hydrogen form of the first or second inventive compound (inventive compound: light hydrogen form) is preferably 10:90 to 90:10, more preferably 20:80 to 80:20, still more preferably 30:70 to 70:30, and particularly preferably 40:60 to 60:40.

[0311] The material for an organic electroluminescence element according to one aspect of the present invention is a hole transport layer material. The content of the inventive compound in the material for an organic electroluminescent device is preferably 1% by mass or more (including 100%), more preferably 10% by mass or more (including 100%), still more preferably 50% by mass or more (including 100%), even more preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%).

[0312] Organic EL device The organic EL device which is one aspect of the present invention includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer includes a light-emitting layer, and at least one layer of the organic layer contains the inventive compound. Examples of the organic layer containing the inventive compound include a hole transport region (hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer, etc.) provided between the anode and the light-emitting layer, a light-emitting layer, a spacer layer, an electron transport region (electron injection layer, electron transport layer, hole blocking layer, etc.) provided between the cathode and the light-emitting layer, etc., but are not limited thereto. The inventive compound is preferably a material for the hole transport region or the light-emitting layer of a fluorescent or phosphorescent EL device, more preferably a material for the hole transport region, still more preferably a material for the hole injection layer, hole transport layer, electron blocking layer, or exciton blocking layer, and particularly preferably a material for the hole injection layer or hole transport layer.

[0313] The organic EL device which is one aspect of the present invention may be a fluorescent or phosphorescent single-color light-emitting device, a fluorescent / phosphorescent hybrid white light-emitting device, a simple type having a single light-emitting unit, or a tandem type having a plurality of light-emitting units. Among them, a fluorescent light-emitting device is preferable. Here, the "light-emitting unit" refers to the minimum unit that includes an organic layer, at least one layer of which is a light-emitting layer, and emits light by recombination of injected holes and electrons.

[0314] For example, typical device configurations of a simple type organic EL device can include the following device configurations. (1) Anode / Light-emitting unit / Cathode In addition, the above light-emitting unit may be a multilayer type having a plurality of phosphorescent layers and fluorescent layers. In that case, a space layer may be provided between each light-emitting layer for the purpose of preventing excitons generated in the phosphorescent layer from diffusing into the fluorescent layer. Representative layer configurations of the simple type light-emitting unit are shown below. The layers in parentheses are optional. (a) (Hole injection layer / ) Hole transport layer / Fluorescent layer / Electron transport layer ( / Electron injection layer) (b) (Hole injection layer / ) Hole transport layer / First fluorescent layer / Second fluorescent layer / Electron transport layer ( / Electron injection layer) (c) (Hole injection layer / ) Hole transport layer / Phosphorescent layer / Space layer / Fluorescent layer / Electron transport layer ( / Electron injection layer) (d) (Hole injection layer / ) Hole transport layer / First phosphorescent layer / Second phosphorescent layer / Space layer / Fluorescent layer / Electron transport layer ( / Electron injection layer) (e) (Hole injection layer / ) Hole transport layer / Phosphorescent layer / Space layer / First fluorescent layer / Second fluorescent layer / Electron transport layer ( / Electron injection layer) (f) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Fluorescent layer / Electron transport layer ( / Electron injection layer) (g) (Hole injection layer / ) Hole transport layer / Exciton blocking layer / Fluorescent layer / Electron transport layer ( / Electron injection layer) (h) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Fluorescent layer / Electron transport layer ( / Electron injection layer) (i) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Fluorescent layer / First electron transport layer / Second electron transport layer ( / Electron injection layer) (j) (Hole injection layer / ) Hole transport layer / Fluorescent layer / Hole blocking layer / Electron transport layer ( / Electron injection layer) (k) (Hole injection layer / ) Hole transport layer / Fluorescent layer / Exciton blocking layer / Electron transport layer ( / Electron injection layer)

[0315] Each of the above phosphorescent or fluorescent layers can be made to exhibit mutually different emission colors. Specifically, in the above light-emitting unit (d), layer configurations such as (Hole injection layer / ) Hole transport layer / First phosphorescent layer (red emission) / Second phosphorescent layer (green emission) / Space layer / Fluorescent layer (blue emission) / Electron transport layer can be cited. Note that an electron blocking layer may be appropriately provided between each light-emitting layer and the hole transport layer or the spacer layer. Further, a hole blocking layer may be appropriately provided between each light-emitting layer and the electron transport layer. By providing an electron blocking layer or a hole blocking layer, electrons or holes can be confined within the light-emitting layer, increasing the probability of charge recombination in the light-emitting layer and improving the light-emitting efficiency.

[0316] As typical element configurations of the tandem organic EL element, the following element configurations can be cited. (2) Anode / First light-emitting unit / Intermediate layer / Second light-emitting unit / Cathode Here, as the first light-emitting unit and the second light-emitting unit, for example, they can be independently selected from the above-described light-emitting units. The intermediate layer is generally also called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, an intermediate insulating layer, and a known material configuration for supplying electrons to the first light-emitting unit and holes to the second light-emitting unit can be used.

[0317] FIG. 1 is a schematic diagram showing an example of the configuration of an organic EL element according to one aspect of the present invention. The organic EL element 1 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10 disposed between the anode 3 and the cathode 4. The light-emitting unit 10 has a light-emitting layer 5. A hole transport band 6 (such as a hole injection layer, a hole transport layer, etc.) is provided between the light-emitting layer 5 and the anode 3, and an electron transport band 7 (such as an electron injection layer, an electron transport layer, etc.) is provided between the light-emitting layer 5 and the cathode 4. Further, an electron blocking layer (not shown) may be provided on the anode 3 side of the light-emitting layer 5, and a hole blocking layer (not shown) may be provided on the cathode 4 side of the light-emitting layer 5, respectively. Thereby, electrons and holes can be confined in the light-emitting layer 5, and the generation efficiency of excitons in the light-emitting layer 5 can be further increased.

[0318] Figure 2 is a schematic diagram showing another configuration of an organic EL element according to an aspect of the present invention. The organic EL element 11 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 20 disposed between the anode 3 and the cathode 4. The light-emitting unit 20 has a light-emitting layer 5. The hole transport region disposed between the anode 3 and the light-emitting layer 5 is formed of a hole injection layer 6a, a first hole transport layer 6b, and a second hole transport layer 6c. Further, the electron transport region disposed between the light-emitting layer 5 and the cathode 4 is formed of a first electron transport layer 7a and a second electron transport layer 7b.

[0319] Figure 3 is a schematic diagram showing still another configuration of an organic EL element according to an aspect of the present invention. The organic EL element 12 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 30 disposed between the anode 3 and the cathode 4. The light-emitting unit 30 has a light-emitting layer 5. The hole transport region disposed between the anode 3 and the light-emitting layer 5 is formed of a hole injection layer 6a, a first hole transport layer 6b, a second hole transport layer 6c, and a third hole transport layer 6d. Further, the electron transport region disposed between the light-emitting layer 5 and the cathode 4 is formed of a first electron transport layer 7a and a second electron transport layer 7b.

[0320] In FIGS. 1 to 3, the light-emitting layer 5 includes at least one light-emitting layer. The light-emitting layer 5 may be a single layer or may include a plurality of layers (for example, a plurality of light-emitting layers, a plurality of light-emitting layers and a spacer layer).

[0321] In the present invention, a host combined with a fluorescent dopant material (fluorescent light-emitting material) is referred to as a fluorescent host, and a host combined with a phosphorescent dopant material is referred to as a phosphorescent host. The fluorescent host and the phosphorescent host are not distinguished only by their molecular structures. That is, the phosphorescent host means a material for forming a phosphorescent light-emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material for forming a fluorescent light-emitting layer. The same applies to the fluorescent host.

[0322] Substrate The substrate is used as a support for the organic EL element. As the substrate, for example, plates such as glass, quartz, and plastic can be used. Also, a flexible substrate may be used. Examples of the flexible substrate include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Further, an inorganic vapor deposition film can also be used.

[0323] Anode For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, and mixtures thereof having a large work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium oxide containing tungsten oxide and zinc oxide, graphene, etc. can be mentioned. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the above metals (for example, titanium nitride), etc. can be mentioned.

[0324] These materials are usually formed into a film by a sputtering method. For example, indium zinc oxide can be formed by sputtering using a target in which 1 to 10 wt% of zinc oxide is added to indium oxide, and indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5 to 5 wt% of tungsten oxide and 0.1 to 1 wt% of zinc oxide with respect to indium oxide. In addition, it may be produced by a vacuum evaporation method, a coating method, an inkjet method, a spin coating method, or the like.

[0325] Hole transport zone As described above, the organic layer may include a hole transport band between the anode and the light-emitting layer. The hole transport band is composed of a hole injection layer, a hole transport layer, an electron blocking layer, and the like. It is preferable that the hole transport band contains the inventive compound. It is preferable that at least one of these layers constituting the hole transport layer contains the inventive compound, and it is more preferable that the hole transport layer contains the inventive compound.

[0326] Since the hole injection layer formed in contact with the anode is formed using a material that allows easy hole injection regardless of the work function of the anode, materials generally used as electrode materials (for example, metals, alloys, electroconductive compounds, and mixtures thereof, elements belonging to Group 1 or Group 2 of the periodic table of elements) can be used. Elements belonging to Group 1 or Group 2 of the periodic table of elements, which are materials with a small work function, that is, alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these can also be used. When forming the anode using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Furthermore, when using a silver paste or the like, a coating method or an inkjet method can be used.

[0327] Hole injection layer The hole injection layer is a layer containing a material with high hole injection properties (hole injection material), and is formed between the anode and the light-emitting layer, or between the hole transport layer and the anode when present.

[0328] As hole injection materials other than the inventive compound, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. can be used.

[0329] Aromatic amine compounds such as 4,4’,4’’-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4’,4’’-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4’-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4’-bis(N-{4-[N’-(3-methylphenyl)-N’-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), etc. can also be mentioned as hole injection layer materials.

[0330] High molecular compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, high molecular compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N’-[4-(4-diphenylamino)phenyl]phenyl-N’-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N’-bis(4-butylphenyl)-N,N’-bis(phenyl)benzidine] (abbreviation: Poly-TPD) can be mentioned. Further, high molecular compounds added with acids such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can also be used.

[0331] Furthermore, it is also preferable to use acceptor materials such as hexaazatriphenylene (HAT) compounds represented by the following formula (K). [Chemical formula]

[0332] (In the above formula, R 221 ~R 226 each independently represents a cyano group, -CONH 2 , a carboxyl group, or -COOR 227 (R 227 represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms). Further, two adjacent ones selected from R 221 and R 222 , R 223 and R 224 , and R 225 and R 226 may be bonded to each other to form a group represented by -CO-O-CO-).) Examples of R 227 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, a cyclohexyl group, and the like.

[0333] Hole transport layer The hole transport layer is a layer containing a material with high hole transport properties (hole transport material), and is formed between the anode and the light-emitting layer, or, when present, between the hole injection layer and the light-emitting layer. The inventive compound may be used alone or in combination with the following compounds in the hole transport layer.

[0334] The hole transport layer may have a single-layer structure or a multilayer structure including two or more layers. For example, the hole transport layer may have a two-layer structure including a first hole transport layer (anode side) and a second hole transport layer (cathode side). That is, the above hole transport band may include a first hole transport layer on the anode side and a second hole transport layer on the cathode side. Further, the hole transport layer may have a three-layer structure including a first hole transport layer, a second hole transport layer, and a third hole transport layer in order from the anode side. That is, a third hole transport layer may be disposed between the second hole transport layer and the light-emitting layer. In one aspect of the present invention, it is preferable that the hole transport layer of the single-layer structure is adjacent to the light-emitting layer. Also, in the multilayer structure, the hole transport layer closest to the cathode, for example, the second hole transport layer of the above two-layer structure or the third hole transport layer of the above three-layer structure, is preferably adjacent to the light-emitting layer. In another aspect of the present invention, an electron blocking layer described later may be interposed between the hole transport layer of the single-layer structure and the light-emitting layer, or between the hole transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer. In one aspect of the organic electroluminescence device according to the present invention, at least one of the first hole transport layer and the second hole transport layer contains an inventive compound. Specifically, in the hole transport layer of the two-layer structure, the inventive compound may be contained in one of the first hole transport layer and the second hole transport layer, or may be contained in both. In another aspect, at least one of the first to third hole transport layers contains an inventive compound. Specifically, in the hole transport layer of the three-layer structure, the inventive compound may be contained in only one of the first to third hole transport layers, or may be contained in any two of them, or may be contained in all of them. In one aspect of the present invention, it is preferable that the inventive compound is contained in the second hole transport layer. Specifically, it is preferable that the inventive compound is contained only in the second hole transport layer, or that the inventive compound is contained in the first hole transport layer and the second hole transport layer. In one aspect of the present invention, the inventive compound contained in one or both of the first hole transport layer and the second hole transport layer, or the inventive compound contained in at least one or more of the first to third hole transport layers is preferably a light hydrogen form from the viewpoint of manufacturing cost. The light hydrogen form refers to an inventive compound in which all hydrogen atoms in the inventive compound are light hydrogen atoms. Therefore, the present invention includes an organic EL element containing an inventive compound in which one or both of the first hole transport layer and the second hole transport layer, and at least one or more of the first to third hole transport layers substantially consist of only light hydrogenated species. The "inventive compound substantially consisting of only light hydrogenated species" means that the content ratio of the light hydrogenated species to the total amount of the inventive compound is 90 mol% or more, preferably 95 mol% or more, more preferably 99 mol% or more (including 100% respectively).

[0335] As the hole transport layer material other than the inventive compound, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used. Examples of the aromatic amine compound include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The above compounds have a hole mobility of 10 -6 cm 2 / Vs or more.

[0336] Examples of the carbazole derivative include 4,4'-di(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA). Examples of anthracene derivatives include 2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth). Polymeric compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. However, any compound with higher hole transport properties than electron transport properties may be used instead of the above compounds.

[0337] In one aspect of the organic EL device according to the present invention, the first hole transport layer contains a compound represented by the following formula (21) or formula (22).

Chemical formula

[0338] Note that the first hole transport layer may contain one kind of the compound represented by formula (21) and formula (22), or may contain a plurality of kinds of the compounds represented by formula (21) and formula (22).

[0339] In formula (21) and formula (22), A1, B1, C1, A2, B2, C2, and D2 are preferably each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group. More preferably, in formula (21), at least one of A1, B1, and C1, and in formula (22), at least one of A2, B2, C2, and D2 is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group.

[0340] The fluorenyl group which can be A1, B1, C1, A2, B2, C2, and D2 may have a substituent at the 9-position, for example, a 9,9-dimethylfluorenyl group or a 9,9-diphenylfluorenyl group. In addition, the substituents at the 9-position may form a ring together, for example, a fluorene skeleton or a xanthene skeleton together.

[0341] L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 are preferably each independently a single bond or a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.

[0342] Specific examples of the compounds represented by formula (21) and formula (22) include the following compounds. [ka]

[0343] Dopant materials for the light-emitting layer The light-emitting layer is a layer containing a highly light-emitting material (dopant material), and various materials can be used. For example, fluorescent materials and phosphorescent materials can be used as dopant materials. Fluorescent materials are compounds that emit light from a singlet excited state, and phosphorescent materials are compounds that emit light from a triplet excited state. In one embodiment of the organic EL device according to the present invention, the light-emitting layer is a single layer. In another embodiment of the organic EL device according to the present invention, the light-emitting layer includes a first light-emitting layer and a second light-emitting layer.

[0344] As blue fluorescent light-emitting materials that can be used in the light-emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. can be used. Specifically, N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), etc. can be mentioned.

[0345] As green fluorescent light-emitting materials that can be used in the light-emitting layer, aromatic amine derivatives, etc. can be used. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracene-9-amine (abbreviation: DPhAPhA), etc. can be mentioned.

[0346] As red fluorescent light-emitting materials that can be used in the light-emitting layer, tetracene derivatives, diamine derivatives, etc. can be used. Specifically, N,N,N’,N’-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N’,N’-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), etc. can be mentioned.

[0347] In one aspect of the present invention, it is preferable that the light-emitting layer contains a fluorescent light-emitting material (fluorescent dopant material).

[0348] As blue phosphorescent light-emitting materials that can be used in the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used. Specifically, bis[2-(4’,6’-difluorophenyl)pyridinato-N,C2’]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4’,6’-difluorophenyl)pyridinato-N,C2’]iridium(III) picolinate (abbreviation: FIrpic), bis[2-(3’,5’ bistrifluoromethylphenyl)pyridinato-N,C2’]iridium(III) picolinate (abbreviation: Ir(CF3ppy)2(pic)), bis[2-(4’,6’-difluorophenyl)pyridinato-N,C2’]iridium(III) acetylacetonate (abbreviation: FIrracac), etc. can be mentioned.

[0349] As green phosphorescent light-emitting materials that can be used in the light-emitting layer, iridium complexes, etc. are used. Tris(2-phenylpyridinato-N,C2’)iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridinato-N,C2’)iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazolato)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)), etc. can be mentioned.

[0350] As red phosphorescent materials that can be used in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used. Specifically, bis[2-(2'-benzo[4,5-α]thienyl)pyridinato-N,C3']iridium(III) acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinolinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP), and other organometallic complexes can be mentioned.

[0351] In addition, rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: Eu(DBM)3(Phen)), and tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3(Phen)) can be used as phosphorescent materials because they emit light from rare earth metal ions (electronic transitions between different multiplicities).

[0352] Host material of the light-emitting layer The light-emitting layer may have a structure in which the above-described dopant material is dispersed in another material (host material). It is preferable to use a material having a higher lowest unoccupied molecular orbital level (LUMO level) and a lower highest occupied molecular orbital level (HOMO level) than the dopant material.

[0353] Examples of the host material include (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes, (2) A heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative, (3) A condensed aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or a chrysene derivative, (4) An aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative is used.

[0354] For example, metal complexes such as tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ); Heterocyclic compounds such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2’,2’’-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP); 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9'-bianthryl (abbreviation: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviation: DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 3,3',3''-(benzene-1,3,5-triyl)tripyrene (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenylchrysene and other condensed aromatic compounds; and N,N-Diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) and other aromatic amine compounds can be used. A plurality of host materials may be used.

[0355] In particular, in the case of a blue fluorescent element, it is preferable to use the following anthracene compound as a host material.

[0356]

Chemical formula

[0357]

Chemical formula

[0358]

Chemical formula

[0359] In one aspect of the organic EL element according to the present invention, when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, at least one of the components constituting the first light-emitting layer is different from the components constituting the second light-emitting layer. For example, there are aspects in which the dopant material contained in the first light-emitting layer is different from the dopant material contained in the second light-emitting layer, and aspects in which the host material contained in the first light-emitting layer is different from the host material contained in the second light-emitting layer.

[0360] In the organic EL element according to the present embodiment, the light-emitting layer may contain a light-emitting compound that exhibits fluorescence emission with a main peak wavelength of 500 nm or less.

[0361] The method for measuring the main peak wavelength of the compound is as follows. Prepare a 5 μmol / L toluene solution of the compound to be measured and put it in a quartz cell, and measure the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample at room temperature (300 K). The emission spectrum can be measured with a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Corporation. Note that the emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is defined as the main peak wavelength. In this specification, the main peak wavelength may sometimes be referred to as the fluorescence emission main peak wavelength (FL-peak).

[0362] The light-emitting compound that exhibits fluorescence emission with a main peak wavelength of 500 nm or less may be the above dopant material or the above host material.

[0363] When the light-emitting layer is a single layer, only one of the dopant material and the host material may be a light-emitting compound that exhibits fluorescence emission with a main peak wavelength of 500 nm or less, or both materials may be light-emitting compounds that exhibit fluorescence emission with a main peak wavelength of 500 nm or less. Further, when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, only one of the first light-emitting layer and the second light-emitting layer may contain a light-emitting compound that exhibits fluorescence emission with a main peak wavelength of 500 nm or less, or both light-emitting layers may contain a light-emitting compound that exhibits fluorescence emission with a main peak wavelength of 500 nm or less. And when the first light-emitting layer contains a light-emitting compound that exhibits fluorescence emission with a main peak wavelength of 500 nm or less, only one of the dopant material and the host material contained in the first light-emitting layer may be a light-emitting compound that exhibits fluorescence emission with a main peak wavelength of 500 nm or less, or both materials may be a light-emitting compound that exhibits fluorescence emission with a main peak wavelength of 500 nm or less. Also, when the second light-emitting layer contains a light-emitting compound that exhibits fluorescence emission with a main peak wavelength of 500 nm or less, only one of the dopant material and the host material contained in the second light-emitting layer may be a light-emitting compound that exhibits fluorescence emission with a main peak wavelength of 500 nm or less, or both materials may be a light-emitting compound that exhibits fluorescence emission with a main peak wavelength of 500 nm or less.

[0364] Electron transport layer The electron transport layer is a layer containing a material with high electron transport properties (electron transport material), and is formed between the light-emitting layer and the cathode, or between the electron injection layer and the light-emitting layer when present. The electron transport layer may have a single-layer structure or a multilayer structure including two or more layers. For example, the electron transport layer may have a two-layer structure including a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one aspect of the present invention, it is preferable that the single-layer electron transport layer is adjacent to the light-emitting layer, and also, the electron transport layer closest to the anode in the multilayer structure, for example, the first electron transport layer of the above two-layer structure, is preferably adjacent to the light-emitting layer. In another aspect of the present invention, a hole blocking layer described later may be interposed between the single-layer electron transport layer and the light-emitting layer, or between the electron transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer.

[0365] The electron transport layer includes, for example, (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, (2) Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives, (3) A polymer compound can be used.

[0366] Examples of the metal complex include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq 2 ), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).

[0367] Examples of the heteroaromatic compound include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs).

[0368] Examples of the high molecular compound include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).

[0369] The above material has an electron mobility of 10 -6 cm 2 / Vs or more. As long as the material has higher electron transportability than hole transportability, materials other than the above may be used for the electron transport layer.

[0370] Electron injection layer The electron injection layer is a layer containing a material with high electron injection properties. For the electron injection layer, alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), rare earth metals such as europium (Eu) and ytterbium (Yb), and compounds containing these metals can be used. Examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, rare earth metal halides, and rare earth metal-containing organic complexes. In addition, a plurality of these compounds can be mixed and used. In addition, materials having electron transport properties and containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, those containing magnesium (Mg) in Alq, etc. may be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, a composite material formed by mixing an organic compound and an electron donor may be used for the electron injection layer. Since such an organic compound receives electrons from the electron donor, it has excellent electron injection properties and electron transport properties. In this case, the organic compound is preferably a material excellent in transporting the received electrons. Specifically, for example, the materials constituting the above-described electron transport layer (such as metal complexes and heteroaromatic compounds) can be used. Any material that exhibits electron-donating properties with respect to the organic compound may be used as the electron donor. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and examples include lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. Also, alkali metal oxides and alkaline earth metal oxides are preferable, and examples include lithium oxide, calcium oxide, barium oxide, etc. Further, Lewis bases such as magnesium oxide can also be used. Also, organic compounds such as tetrathiafulvalene (abbreviation: TTF) can be used.

[0371] Cathode For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, and mixtures thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these. In addition, when forming the cathode using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Also, when using a silver paste or the like, a coating method or an inkjet method can be used. By providing an electron injection layer, regardless of the work function, a cathode can be formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium tin oxide containing silicon oxide. These conductive materials can be formed into a film using a sputtering method, an inkjet method, a spin coating method, or the like.

[0372] Insulating layer In an organic EL element, since an electric field is applied to an ultrathin film, pixel defects due to leakage or short circuit are likely to occur. To prevent this, an insulating layer composed of an insulating thin film layer may be inserted between a pair of electrodes. Examples of materials used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, and the like. Note that mixtures or laminates of these may also be used.

[0373] Spacer layer The spacer layer is, for example, a layer provided between a fluorescent light-emitting layer and a phosphorescent light-emitting layer when laminating the fluorescent light-emitting layer and the phosphorescent light-emitting layer, for the purpose of preventing excitons generated in the phosphorescent light-emitting layer from diffusing into the fluorescent light-emitting layer or adjusting the carrier balance. The spacer layer can also be provided between a plurality of phosphorescent light-emitting layers. Since the spacer layer is provided between the light-emitting layers, it is preferably a material having both electron transporting properties and hole transporting properties. Further, in order to prevent the diffusion of triplet energy in the adjacent phosphorescent light-emitting layers, the triplet energy is preferably 2.6 eV or more. Examples of materials used for the spacer layer include the same materials as those used for the hole transport layer described above.

[0374] Blocking layer Blocking layers such as an electron blocking layer, a hole blocking layer, and an exciton blocking layer may be provided adjacent to the light-emitting layer. The electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer, and the hole blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron transport layer. The exciton blocking layer has a function of preventing excitons generated in the light-emitting layer from diffusing to the surrounding layers and confining the excitons within the light-emitting layer.

[0375] Each layer of the organic EL element can be formed by a conventionally known vapor deposition method, coating method, or the like. For example, it can be formed by a vapor deposition method such as a vacuum vapor deposition method or a molecular beam epitaxy (MBE) method, or a known method by a coating method such as a dipping method, a spin coating method, a casting method, a bar coating method, or a roll coating method using a solution of a compound for forming the layer.

[0376] The film thickness of each layer is not particularly limited, but generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and conversely, if it is too thick, a high driving voltage is required and the efficiency deteriorates. Therefore, it is usually 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm.

[0377] In one aspect of the organic EL element of the present invention, the sum of the thicknesses of the first hole transport layer and the second hole transport layer is 30 nm or more and 150 nm or less. In this case, preferably, it is 40 nm or more and 130 nm or less. Further, in one aspect of the organic EL element of the present invention, the thickness of the second hole transport layer is 20 nm or more. Preferably it is 25 nm or more, more preferably 35 nm or more, and also preferably 100 nm or less. Further, in one aspect of the organic EL element of the present invention, the hole transport layer adjacent to the light-emitting layer is 20 nm or more. Preferably it is 25 nm or more, more preferably 30 nm or more, and also preferably 100 nm or less. Further, in one aspect of the organic EL element of the present invention, the film thickness D1 of the first hole transport layer and the film thickness D2 of the second hole transport layer satisfy the relationship of 0.3 < D2 / D1 < 4.0. Preferably, they satisfy the relationship of 0.5 < D2 / D1 < 3.5, and more preferably, they satisfy the relationship of 0.75 < D2 / D1 < 3.0.

[0378] Examples of embodiments of the organic EL element of the present invention include, for example, an organic EL element having the hole transport layer of the above two-layer structure, · A first embodiment in which the second hole transport layer contains the compound of the present invention and the first hole transport layer does not contain the compound of the present invention; · A second embodiment in which both the first hole transport layer and the second hole transport layer contain the compound of the present invention; · A third embodiment in which the first hole transport layer contains the compound of the present invention and the second hole transport layer does not contain the compound of the present invention; an organic EL element having the hole transport layer of the above three-layer structure, · A fourth embodiment in which the first hole transport layer contains the compound of the present invention and the second and third hole transport layers do not contain the compound of the present invention; · A fifth embodiment in which the second hole transport layer contains the compound of the present invention and the first and third hole transport layers do not contain the compound of the present invention; · A sixth embodiment in which the third hole transport layer contains the compound of the present invention and the first and second hole transport layers do not contain the compound of the present invention; · A seventh embodiment in which the first and second hole transport layers contain the compound of the present invention and the third hole transport layer does not contain the compound of the present invention; · An eighth embodiment in which the first and third hole transport layers contain the compound of the present invention and the second hole transport layer does not contain the compound of the present invention; · A tenth embodiment in which the second and third hole transport layers contain the compound of the present invention and the first hole transport layer does not contain the compound of the present invention; · A tenth embodiment in which all of the first to third hole transport layers contain the compound of the present invention; and the like.

[0379] Electronic device The organic EL element can be used in display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and electronic devices such as lighting and light-emitting devices for vehicle lamps.

Examples

[0380] Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited thereto.

[0381] Compound used in the production of the organic EL element of the example

Chemical formula

[0382] Comparative compound used in the production of the organic EL element of the comparative example

Chemical formula

[0383] Other compounds used in the production of the organic EL elements of the examples and comparative examples

Chemical formula

[0384]

Chemical formula

[0385]

Chemical formula

[0386] Fabrication of organic EL element Example 1-1 A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV-ozone cleaned for 30 minutes. The film thickness of ITO was 130 nm. The glass substrate with the transparent electrode after cleaning was mounted on the substrate holder of a vacuum evaporation apparatus, and first, Compound HI-1 was evaporated so as to cover the transparent electrode on the surface where the transparent electrode was formed, and a hole injection layer with a film thickness of 5 nm was formed. Next, Compound 1 as Compound HT-1 was evaporated on the hole injection layer to form a first hole transport layer with a film thickness of 75 nm. Next, compound HT-2 was vapor-deposited on this first hole transport layer to form a second hole transport layer with a film thickness of 15 nm. Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-vapor-deposited on this second hole transport layer to form a light-emitting layer with a film thickness of 20 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 98:2. Next, compound ET-1 was vapor-deposited on this light-emitting layer to form a first electron transport layer with a film thickness of 15 nm. Next, compound ET-2 and Li were co-vapor-deposited on this first electron transport layer to form a second electron transport layer with a film thickness of 15 nm. The mass ratio of compound ET-2 to Li (ET-2:Li) was 96:4. Next, metal Al was vapor-deposited on this second electron transport layer to form a metal cathode with a film thickness of 80 nm. The layer structure of the organic EL device of Example 1-1 obtained in this way is shown below. ITO(130) / HI-1(5) / HT-1(75) / HT-2(15) / BH-1:BD-1=98:2(20) / ET-1(15) / ET-2:Li=96:4(15) / Al(80) In the above layer structure, the numbers in parentheses are the film thickness (nm), and the ratio is the mass ratio. Comparative Examples 1-1 to 1-3 An organic EL device was fabricated in the same manner as in Example 1, except that the material of the second hole transport layer was replaced with Comparative Compounds 1, 2, and 3 from Compound 1, respectively.

[0387] Evaluation of Organic EL Devices For the organic EL devices fabricated in Example 1-1 and Comparative Examples 1-1 to 1-3, a voltage was applied to the organic EL device so that the current density was 10 mA / cm 2 The external quantum efficiency (EQE) was evaluated, and the voltage value at that time was measured and used as the driving voltage. The results are shown in Table 1.

[0388]

Table 1

[0389] As is clear from the results in Table 1, the compound (Compound 1 of Example 1-1) that satisfies the provisions of the present invention shows significantly improved drive voltage and EQE values compared to the monoamines (Comparative Compounds 1, 2, and 3 of Comparative Examples 1-1 to 1-3) that do not satisfy the provisions of the present invention.

[0390] Example 2-1 A glass substrate (manufactured by Geomatic Co., Ltd.) with a 25 mm × 75 mm × 1.1 mm ITO transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV-ozone cleaned for 30 minutes. The film thickness of the ITO was 130 nm. The glass substrate with the cleaned transparent electrode was mounted on the substrate holder of a vacuum deposition apparatus. First, Compound HI-1 was deposited so as to cover the transparent electrode on the surface where the transparent electrode was formed, and a hole injection layer with a film thickness of 5 nm was formed. Next, Compound HT-3 was deposited on the hole injection layer, and a first hole transport layer with a film thickness of 37.5 nm was formed. Next, Compound 1 as Compound HT-1 was deposited on this first hole transport layer, and a second hole transport layer with a film thickness of 37.5 nm was formed. Next, Compound HT-2 was deposited on this second hole transport layer, and a third hole transport layer with a film thickness of 15 nm was formed. Next, Compound BH-1 (host material) and Compound BD-1 (dopant material) were co-deposited on this third hole transport layer to form a light-emitting layer with a film thickness of 20 nm. The mass ratio of Compound BH-1 to Compound BD-1 (BH-1:BD-1) was 98:2. Next, Compound ET-1 was deposited on this light-emitting layer to form a first electron transport layer with a film thickness of 15 nm. Next, Compound ET-2 and Li were co-deposited on this first electron transport layer to form a second electron transport layer with a film thickness of 15 nm. The mass ratio of Compound ET-2 to Li (ET-2:Li) was 96:4. Next, metal Al was deposited on this second electron transport layer to form a metal cathode with a film thickness of 80 nm. The layer structure of the organic EL element of Example 2-1 thus obtained is shown below. ITO(130) / HI-1(5) / HT-3(37.5) / HT-1(37.5) / HT-2(15) / BH-1:BD-1 = 98:2(20) / ET-1(15) / ET-2:Li = 96:4(15) / Al(80) In the above layer structure, the numbers in parentheses are film thickness (nm), and the ratios are mass ratios.

[0391] Example 2-2 An organic EL element was fabricated in the same manner as in Example 2-1, except that the second hole transport layer material was changed from Compound 1 to Compound 2.

[0392] Comparative Examples 2-1, 2-2 An organic EL element was fabricated in the same manner as in Example 2-1, except that the second hole transport layer material was changed from Compound 1 to Comparative Compounds 1 and 3.

[0393] Evaluation of Organic EL Elements For the organic EL elements fabricated in Example 2-1, 2-2, Comparative Example 2-1, and Comparative Example 2-2, a voltage was applied to the organic EL element so that the current density became 10 mA / cm 2 and the external quantum efficiency (EQE) was evaluated. At the same time, the voltage value at that time was measured and used as the driving voltage. The results are shown in Table 2.

[0394]

Table 2

[0395] As is clear from the results in Table 2, the compounds (Compound 1 and Compound 2 in Example 2-1 and Example 2-2) that satisfy the provisions of the present invention show significantly improved driving voltage and EQE values compared to the monoamines (Comparative Compounds 1 and 3 in Comparative Example 2-1 and Comparative Example 2-2) that do not satisfy the provisions of the present invention.

[0396] Example 3-1 A glass substrate (manufactured by Geomatic Co., Ltd.) with a 25 mm × 75 mm × 1.1 mm ITO transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The film thickness of ITO was 130 nm. The glass substrate with the transparent electrode after cleaning was mounted on the substrate holder of a vacuum evaporation apparatus. First, compounds HT-4 and HI-2 were co-evaporated to cover the transparent electrode on the surface where the transparent electrode was formed, forming a hole injection layer with a film thickness of 10 nm. The mass ratio of compound HT-4 to compound HI-2 (HT-4:HI-2) was 95:5. Next, compound HT-4 was evaporated on the hole injection layer to form a first hole transport layer with a film thickness of 30 nm. Next, compound 1 was evaporated as the second hole transport material HT-1 on this first hole transport layer to form a second hole transport layer with a film thickness of 40 nm. Next, compound HT-2 was evaporated on this second hole transport layer to form a third hole transport layer with a film thickness of 15 nm. Next, compounds BH-1 (host material) and BD-1 (dopant material) were co-evaporated on this third hole transport layer to form a light-emitting layer with a film thickness of 20 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 98:2. Next, compound ET-1 was evaporated on this light-emitting layer to form a first electron transport layer with a film thickness of 10 nm. Next, compounds ET-2 and Li were co-evaporated on this first electron transport layer to form a second electron transport layer with a film thickness of 20 nm. The mass ratio of compound ET-2 to Li (ET-2:Li) was 96:4. Next, metal Al was evaporated on this second electron transport layer to form a metal cathode with a film thickness of 80 nm. The layer structure of the organic EL element of Example 2-1 obtained in this way is shown below. ITO(130) / HI-4:HI-2=95:5(10) / HT-4(30) / HT-1(40) / HT-2(15) / BH-1:BD-1=98:2(20) / ET-1(10) / ET-2:Li=96:4(20) / Al(80) In the above layer structure, the numbers in parentheses are the film thickness (nm), and the ratios are mass ratios.

[0397] Examples 3-2 to 3-6 An organic EL device was fabricated in the same manner as in Example 3-1, except that the second hole transport layer material HT-1 was changed from Compound 1 to Compounds 4 to 8, respectively.

[0398] Example 3-7 An organic EL device was fabricated in the same manner as in Example 3-1, except that the second hole transport layer material HT-1 was changed from Compound 1 to Compound 3.

[0399] Comparative Examples 3-1 and 3-2 An organic EL device was fabricated in the same manner as in Example 3-1, except that the second hole transport layer material HT-1 was changed from Compound 1 to Comparative Compounds 1 and 3, respectively.

[0400] Evaluation of Organic EL Devices For the organic EL devices fabricated in Examples 3-1 to 3-7, Comparative Example 3-1, and Comparative Example 3-2, a voltage was applied to the organic EL device so that the current density became 10 mA / cm 2 and the external quantum efficiency (EQE) was evaluated. At the same time, the voltage value at that time was measured and used as the driving voltage. The results are shown in Table 3.

[0401] [Table 3]

[0402] As is clear from the results in Table 3, the compounds satisfying the provisions of the present invention (Compound 1, Compounds 4 to 8, and Compound 3 in Examples 3-1 to 3-7) show significantly improved driving voltage and EQE values compared to the monoamines not satisfying the provisions of the present invention (Comparative Compounds 1 and 3 in Comparative Examples 3-1 and 3-2).

[0403] Example 4-1 A glass substrate (manufactured by Geomatic Co., Ltd.) with a 25 mm × 75 mm × 1.1 mm ITO transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV-ozone cleaned for 30 minutes. The film thickness of the ITO was 130 nm. The glass substrate with the transparent electrode after cleaning was mounted on the substrate holder of a vacuum evaporation apparatus. First, compound 1 and compound HI-2 were co-evaporated as the hole transport material HT-1 so as to cover the transparent electrode on the surface where the transparent electrode was formed, and a hole injection layer with a film thickness of 10 nm was formed. The mass ratio of compound HT-1 to compound HI-2 (HT-1:HI-2) was 97:3. Next, compound 1 was evaporated as the first hole transport material HT-1 on the hole injection layer to form a first hole transport layer with a film thickness of 80 nm. Next, compound HT-5 was evaporated on this first hole transport layer to form a second hole transport layer with a film thickness of 5 nm. Next, compound BH-2 (host material) and compound BD-2 (dopant material) were co-evaporated on this second hole transport layer to form a light-emitting layer with a film thickness of 20 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 99:1. Next, compound ET-5 was evaporated on this light-emitting layer to form a first electron transport layer with a film thickness of 5 nm. Next, compound ET-6 and Liq were co-evaporated on this first electron transport layer to form a second electron transport layer with a film thickness of 25 nm. The mass ratio of compound ET-6 to Liq (ET-6:Liq) was 50:50. Next, metal Yb was evaporated on this second electron transport layer to form an electron injection layer with a film thickness of 1 nm. Next, metal Al was evaporated on the electron injection layer to form a metal cathode with a film thickness of 50 nm. The layer structure of the organic EL element of Example 2-1 obtained in this way is shown below. ITO(130) / HT-1:HI-2=97:3(10) / HT-1(80) / HT-5(5) / BH-2:BD-2=99:1(20) / ET-5(5) / ET-6:Liq=50:50(25) / Yb(1) / Al(50) In the above layer structure, the numbers in parentheses are the film thickness (nm), and the ratios are the mass ratios.

[0404] Examples 4-2 and 4-3 An organic EL device was fabricated in the same manner as in Example 4-1, except that the hole transport material and the first hole transport material used in the hole injection layer were changed from Compound 1 to Compound 4 (Example 4-2), and from Compound 1 to Compound 6 (Example 4-3).

[0405] Comparative Examples 4-1 and 4-2 An organic EL device was fabricated in the same manner as in Example 4-1, except that the hole transport material and the first hole transport material used in the hole injection layer were changed from Compound 1 to Comparative Compound 3 (Comparative Example 4-1), and from Compound 1 to Comparative Compound 4 (Comparative Example 4-2).

[0406] Evaluation of the organic EL device For the organic EL devices fabricated in Examples 4-1 to 4-3, Comparative Example 4-1, and Comparative Example 4-2, a voltage was applied to the organic EL device so that the current density became 10 mA / cm 2 and the external quantum efficiency (EQE) was evaluated. At the same time, the voltage value at that time was measured and used as the driving voltage. The results are shown in Table 4.

[0407] [Table 4]

[0408] As is clear from the results in Table 4, the compounds satisfying the provisions of the present invention (Compound 1, 4, and 6 in Examples 4-1 to 4-3) show significantly improved driving voltage and EQE values compared to the monoamines not satisfying the provisions of the present invention (Comparative Compounds 3 and 4 in Comparative Examples 4-1 and 4-2).

[0409] Compounds synthesized in the synthesis examples [Chemical formula]

[0410] [Synthesis of compounds] Synthesis Example of Intermediate 1: Synthesis of Intermediate A

Chem.

[0411] Under an argon atmosphere, a THF solution (1.0 M) of 2-bromo-4'-chloro-1,1'-biphenyl (4.81 g, 18 mmol) was slowly added dropwise to a reactor containing magnesium (0.656 g, 27.0 mmol), and the mixture was stirred at room temperature. After all the addition was completed, the mixture was stirred under reflux for 1 hour to prepare an organomagnesium reagent. In another reactor, 1-indanone (1.98 g, 15 mmol) and THF (13 mL) were added under an argon atmosphere, and the previously prepared organomagnesium reagent was added dropwise. Then, the mixture was stirred under reflux for 5 hours. The reaction solution was cooled to room temperature, saturated aqueous ammonium chloride solution and ethyl acetate were added, and the mixture was stirred. After removing the aqueous layer using a separatory funnel, the obtained solution was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain an orange oil. The obtained oil was dissolved in xylene (75 mL), p-toluenesulfonic acid monohydrate (8.56 g, 45 mmol) was added, the temperature was raised to 140 °C, and the mixture was stirred for 5 hours. After cooling, water was added, the aqueous layer was removed, and the obtained solution was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain Intermediate A as a colorless solid (1.82 g). The yield in two steps was 40%.

[0412] Synthesis Example of Intermediate 2: Synthesis of Intermediate B

Chem.

[0413] The same operations as in Synthesis Example of Intermediate 1 were carried out except that 3,3-dimethyl-1-indanone was used instead of 1-indanone used in Synthesis Example of Intermediate 1 to obtain Intermediate B. The yield in two steps was 41%.

[0414] Synthesis Example 1: Synthesis of Compound 1

Chem.

[0415] A mixture of intermediate A (1.82 g, 6.01 mmol), 2-(2-biphenylyl)amino-9,9-dimethylfluorene (2.173 g, 6.01 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.11 g, 0.120 mmol), tri-t-butylphosphonium tetrafluoroborate (0.140 g, 0.481 mmol), sodium t-butoxide (0.809 g, 8.41 mmol), and xylene (40 mL) was stirred at 120 °C for 5 hours. After the reaction mixture was cooled to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain 2.98 g of a white solid. The yield was 79%. The obtained product was confirmed to be Compound 1 by mass spectrum analysis, with m / e = 627 for a molecular weight of 627.29.

[0416] Synthesis Example 2: Synthesis of Compound 2

Chemical formula

[0417] The same procedure as in Synthesis Example 1 was carried out, except that 2-bromo-1‘,3’-dihydrospiro[fluorene-9,2‘-indene] synthesized by the same method as described in International Publication No. 2004 / 110968 was used instead of intermediate A used in Synthesis Example 1 above, to obtain Compound 2. The obtained product was confirmed to be Compound 2 by mass spectrum analysis, with m / e = 627 for a molecular weight of 627.29.

[0418] Synthesis Example 3: Synthesis of Compound 3

Chemical formula

[0419] The same procedure as in Synthesis Example 1 was carried out, except that intermediate B was used instead of intermediate A used in Synthesis Example 1 above, to obtain Compound 3. The product was Compound 3 as a result of mass spectrometry analysis, with m / e = 655 for a molecular weight of 655.32.

[0420] Intermediate Synthesis Example 3: Synthesis of Intermediate C

Chemical formula

[0421] The same operations as in Intermediate Synthesis Example 1 were carried out except that 6-(tert-butyl)-2,3-dihydro-1H-inden-1-one was used instead of 1-indanone used in Intermediate Synthesis Example 1, and Compound C was obtained. The yield was 39%.

[0422] Synthesis Example 4: Synthesis of Compound 4

Chemical formula

[0423] The same operations as in Synthesis Example 1 were carried out except that N-([1,1’:4’,1’’-terphenyl]-2-yl)-9,9-dimethyl-9H-fluorene-2-amine was used instead of 2-(2-biphenylyl)amino-9,9-dimethylfluorene used in Synthesis Example 1, and Compound 4 was obtained. The product was Compound 4 as a result of mass spectrometry analysis, with m / e = 704 for a molecular weight of 703.93.

[0424] Synthesis Example 5: Synthesis of Compound 5

Chemical formula

[0425] The same operations as in Synthesis Example 1 were carried out except that Intermediate C was used instead of Intermediate A used in Synthesis Example 1, and Compound 5 was obtained. The product was Compound 5 as a result of mass spectrometry analysis, with m / e = 684 for a molecular weight of 683.94.

[0426] Synthesis Example 6: Synthesis of Compound 6

Chem.

[0427] The same procedure as in Synthesis Example 1 was carried out except that N-([1,1'-biphenyl]-2-yl)-9,9-diphenyl-9H-fluorene-2-amine was used instead of 2-(2-biphenylyl)amino-9,9-dimethylfluorene used in Synthesis Example 1 to obtain Compound 6. The obtained product was Compound 6 as a result of mass spectrum analysis, and m / e = 752 for a molecular weight of 751.97.

[0428] Synthesis Example 7: Synthesis of Compound 7

Chem.

[0429] The same procedure as in Synthesis Example 1 was carried out except that N-(2-(dibenzo[b,d]furan-4-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-amine was used instead of 2-(2-biphenylyl)amino-9,9-dimethylfluorene used in Synthesis Example 1 to obtain Compound 7. The obtained product was Compound 7 as a result of mass spectrum analysis, and m / e = 718 for a molecular weight of 717.91.

[0430] Synthesis Example 8: Synthesis of Compound 8

Chem.

[0431] The same procedure as in Synthesis Example 1 was carried out except that N-([1,1':2',1''-terphenyl]-2-yl)-9,9-dimethyl-9H-fluorene-2-amine was used instead of 2-(2-biphenylyl)amino-9,9-dimethylfluorene used in Synthesis Example 1 to obtain Compound 8. What was obtained was Compound 8 as a result of mass spectrometry analysis, with m / e = 704 for a molecular weight of 703.93.

Explanation of symbols

[0432] 1, 11, 12 Organic EL element 2 Substrate 3 Anode 4 Cathode 5 Light-emitting layer 6 Hole transport region (hole transport layer) 6a Hole injection layer 6b First hole transport layer 6c Second hole transport layer 6d Third hole transport layer 7 Electron transport region (electron transport layer) 7a First electron transport layer 7b Second electron transport layer 10, 20, 30 Light-emitting unit

Claims

1. A compound represented by the following formula (1A) or (1B): 【Chemistry 1】 【Chemistry 2】 [In formula (1A), N ＊ is the central nitrogen atom. Z １ and Z ２ One selected from is a single bond bonded to *a. The Z which is not a single bond １ and Z ２ , R １３Ａ , R １４Ａ , and R １５ ~R １８ , R ７ ~R １０ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms. The Z which is not a single bond １ and Z ２ , R １３Ａ , and R １４Ａ do not combine with each other to form a ring. R ７ ~R １０ Among these, a pair of adjacent groups may or may not be bonded to each other to form a ring. R １５ ~R １８ Among these, a pair of adjacent groups may or may not be bonded to each other to form a ring. R １Ａ and R ２Ａ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms. R １Ａ and R ２Ａ may or may not be bonded to each other to form a ring. Y １ and Y ２ is a hydrogen atom. L １ represents a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms. n1 is 0 or 1. When n1 is 0, Z １ and Z ２ One selected from the group consisting of the central nitrogen atom N ＊ Bind to. X １ is an oxygen atom, a sulfur atom, or ═CR Ａ R Ｂ It is. R Ａ , R Ｂ , and R ２１ ~R ２８ is a single bond bonded to *b1, or R Ａ and R Ｂ One selected from is a divalent group bonded to *b1. R which is not a single bond and is not a divalent group bonded to *b1 Ａ and R Ｂ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms. Ａ and R Ｂ may or may not be bonded to each other to form a ring. The R that is not a single bond ２１ ~R ２８ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms. R ２１ ~R ２４ is a single bond bonded to *b1, R ２１ ~R ２４ do not bond to each other to form a ring, and R ２５ ~R ２８ may or may not be bonded to each other to form a ring. R ２５ ~R ２８ is a single bond bonded to *b1, R ２５ ~R ２８ do not bond to each other to form a ring, and R ２１ ~R ２４ may or may not be bonded to each other to form a ring. L ２ represents a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms. n2 is 0 or 1. When n2 is 0, R ２１ ~R ２８ One selected from the group consisting of the central nitrogen atom N ＊ Bind to. Ar １ represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms. Ar ２ represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. m is 0, 1, 2, 3, or 4. １ When is a hydrogen atom, m is 0. When m is 1 to 4, R ３１ ~R ３４ One to four selected from are single bonds bonded to *c. When m is 2 to 4, multiple Ar ２ may be the same or different from each other. The R that is not a single bond ３１ ~R ３４ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms. Ar that is not a hydrogen atom １ and R is not a hydrogen atom ３４ ~R ２４ Among these, a pair of adjacent groups may or may not be bonded to each other to form a ring. In formula (1B), R １１ ~R １４ One selected from is a single bond bonded to *a. The R that is not a single bond １１ ~R １４ , R １５ ~R １８ , and R ７ ~R １０ each independently represents a hydrogen atom, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. The R that is not a single bond １１ ~R １４ do not combine with each other to form a ring. R ７ ~R １０ Among these, a pair of adjacent groups may or may not be bonded to each other to form a ring. R １５ ~R １８ Among these, a pair of adjacent groups may or may not be bonded to each other to form a ring. R １Ｂ , R ２Ｂ , R ５Ｂ , and R ６Ｂ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms. R １Ｂ and R ２Ｂ may or may not be bonded to each other to form a ring. R ５Ｂ and R ６Ｂ may or may not be bonded to each other to form a ring. L ３ represents a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms. n3 is 0 or 1. When n3 is 0, Ar ３ is the central nitrogen atom N ＊ Bind to. Ar ３ represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a group represented by the following formula (2-1), or a group represented by the following formula (2-2). 【Chemistry 3】 (In formula (2-1), ** is L ３ represents the bonding position to X ３ is an oxygen atom or a sulfur atom. R ４１ ~R ４４ One selected from is a single bond bonded to *d. The R that is not a single bond ４１ ~R ４４ , R ４５ ~R ４８ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms. The R that is not a single bond ４１ ~R ４４ adjacent pairs of groups among ４５ ~R ４８ Among these, adjacent pairs of groups may or may not be bonded to each other to form a ring. In formula (2-2), ** is L ３ represents the bonding position to R ４１ ~R ４８ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms. R ４１ ~R ４８ A pair of adjacent groups may or may not be bonded to each other to form a ring.) L ４ represents a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms. n4 is 0 or 1. When n4 is 0, Ar ４ is the central nitrogen atom N ＊ Bind to. Ar ４ is a group represented by the following formula (3-1) or a group represented by the following formula (3-2). 【Chemistry 4】 (In formula (3-1), *** is L ４ represents the bonding position to X ２ is an oxygen atom, a sulfur atom, or ═CR Ｃ R Ｄ It is. R ２１Ｂ ~R ２４Ｂ , R Ｃ , and R Ｄ one selected from is a single bond bonded to b2, or R Ｃ and R Ｄ One selected from is a divalent group bonded to *b2. The R that is not a single bond ２１Ｂ ~R ２４Ｂ , R ２５Ｂ ~R ２８Ｂ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms. R ２１Ｂ ~R ２４Ｂ is a single bond bonded to b2, R ２１Ｂ ~R ２４Ｂ do not bond to each other to form a ring, and R ２５Ｂ ~R ２８Ｂ may or may not be bonded to each other to form a ring. R ２５Ｂ ~R ２８Ｂ is a single bond bonded to b2, R ２５Ｂ ~R ２８Ｂ do not bond to each other to form a ring, and R ２１Ｂ ~R ２４Ｂ may or may not be bonded to each other to form a ring. R which is not a single bond and is not a divalent group bonded to *b2 Ｃ and R Ｄ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and may or may not be bonded to each other to form a ring. Ｃ and R Ｄ When one selected from is an aryl group, they are combined to form R Ｃ and R Ｄ does not form 1',3'-dihydrospiro[fluorene-9,2'-indene] together with the fluorene ring to which it is attached. X ２ is an oxygen atom or a sulfur atom, n4 is 1. In formula (3-2), *** is L ４ represents the bonding position to R ２１Ｂ ~R ２８Ｂ each independently represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms. R ２１Ｂ ~R ２４Ｂ adjacent pairs of groups among ２５Ｂ ~R ２８Ｂ Among these, adjacent pairs of groups may or may not be bonded to each other to form a ring.) In formula (1-B), N ＊ , L １ and n1 are as defined in formula (1A).

2. The compound according to claim 1, represented by the following formula (1A-1): 【Chemistry 5】 [In formula (1A-1), R １Ａ , R ２Ａ , Y １ , Y ２ , R ７ ~R １０ , Z １ , R １３Ａ , R １４Ａ , R １５ ~R １８ , R ２１ ~R ２８ , X １ , R ３１ ~R ３４ , N ＊ , Ar １ , Ar ２ , L １ , L ２ , *b1, *c, m, n1, and n2 are as defined in formula (1A).

3. The compound according to claim 1, represented by the following formula (1A-2): 【Chemistry 6】 [In formula (1A-2), R １Ａ , R ２Ａ , Y １ , Y ２ , R ７ ~R １０ , Z １ , Z ２ , R １３Ａ , R １４Ａ , R １５ ~R １８ , R ２１ ~R ２８ , R Ａ , R Ｂ , R ３１ ~R ３４ , N ＊ , Ar １ , Ar ２ , L １ , L ２ , *a, *b1, *c, m, n1, and n2 are as defined in formula (1A).

4. R ２１ , R ２２ , R ２４ , R ２５ , R ２７ , and R ２８ The compound according to claim 3, wherein one of is a single bond bonded to *b1.

5. Represented by the formula (1A), formula (1A-1), or formula (1A-2), when n1 is 1, L １ is a phenylene group, and when n2 is 1, L ２ The compound according to any one of claims 1 to 4, wherein is a phenylene group.

6. The compound according to claim 1, represented by any one of the following formulas (1A-3) to (1A-5): 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 [In formula (1A-3) and formula (1A-5), R ５１ ~R ５５ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. ５１ ~R ５５ One selected from is a single bond bonded to *d. ５１ ~R ５５ Adjacent pairs of these do not bond to each other to form a ring. In formula (1A-4) and formula (1A-5), R ６１ ~R ６５ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. ６１ ~R ６５ One selected from is a single bond bonded to *e. ６１ ~R ６５ Adjacent pairs of these do not bond to each other to form a ring. In formulas (1A-3) to (1A-5), R １Ａ , R ２Ａ , Y １ , Y ２ , R ７ ~R １０ , Z １ , Z ２ , R １３Ａ , R １４Ａ , R １５ ~R １８ , R ２１ ~R ２８ , X １ , R ３１ ~R ３４ , N ＊ , Ar １ , Ar ２ , L １ , L ２ , *a, *b1, *c, m, n1, and n2 are as defined in formula (1A).

7. The compound according to claim 1, represented by any one of the following formulas (1A-6) to (1A-8): 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 [In formulas (1A-6) to (1A-8), R １Ａ , R ２Ａ , Y １ , Y ２ , R ７ ~R １０ , Z １ , Z ２ , R １３Ａ , R １４Ａ , R １５ ~R １８ , R ２１ ~R ２８ , X １ , R ３１ ~R ３４ , N ＊ , Ar １ , Ar ２ , L １ , L ２ , *a, *b1, *c, m, n1, and n2 are as defined in formula (1A).

8. Represented by any one of the formula (1A) and formulas (1A-1) to (1A-8), Ar １ is a hydrogen atom and m is 0, or Ar １ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and m is 0, or Ar １ The compound according to any one of claims 1 to 7, wherein is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and m is 1.

9. Represented by any one of the formulas (1A) and (1A-1) to (1A-8), Ar １ and Ar ２ and each independently represent a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

10. The compound according to claim 1, represented by the following formula (1B-1): 【Chemistry 13】 [In formula (1B-1), R １Ｂ , R ２Ｂ , R ５Ｂ , R ６Ｂ , R ７ ~R １０ , R １１ , R １３ ~R １８ , N ＊ , Ar ３ , Ar ４ , L １ , L ３ , L ４ , n1, n3, and n4 are as defined in formula (1B).

11. The compound according to claim 1, represented by the following formula (1B-2): 【Chemistry 14】 [In formula (1B-2), R １Ｂ , R ２Ｂ , R ５Ｂ , R ６Ｂ , R ７ ~R １０ , R １１ ~R １８ , R ２１Ｂ ~R ２８Ｂ , R Ｃ , R Ｄ , N ＊ , Ar ３ , L １ , L ３ , L ４ , *a, *b2, n1, n3, and n4 are as defined in formula (1B).

12. Ar ３ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

13. Represented by any one of the formulas (1B), (1B-1), and (1B-2), when n1 is 1, L １ is a phenylene group, and when n3 is 1, L ３ is a phenylene group, and when n4 is 1, L ４ The compound according to any one of claims 1, 10 to 12, wherein is a phenylene group.

14. The compound according to claim 1, represented by any one of the following formulas (1B-3) to (1B-9): 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 [In formula (1B-3), formula (1B-6), formula (1B-7), and formula (1B-9), R ５１ ~R ５５ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. ５１ ~R ５５ One selected from is a single bond bonded to *d. The R that is not a single bond ５１ ~R ５５ Adjacent pairs of these do not bond to each other to form a ring. In formula (1B-4), formula (1B-6), formula (1B-8), and formula (1B-9), R ７１ ~R ７５ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. ７１ ~R ７５ One selected from is a single bond bonded to *f. The R that is not a single bond ７１ ~R ７５ Adjacent pairs of these do not bond to each other to form a ring. In formula (1B-5) and formulas (1B-7) to (1B-9), R ８１ ~R ８５ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. ８１ ~R ８５ One selected from is a single bond bonded to *g. The R that is not a single bond ８１ ~R ８５ Adjacent pairs of these do not bond to each other to form a ring. In formulas (1B-3) to (1B-9), R １Ｂ , R ２Ｂ , R ５Ｂ , R ６Ｂ , R ７ ~R １０ , R １１ ~R １８ , N ＊ , Ar ３ , Ar ４ , L １ , L ３ , L ４ , *a, n1, n3, and n4 are as defined in formula (1B).

15. Represented by any one of the formulas (1B), (1B-1), and (1B-3) to (1B-9), Ar ３ represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, Ar ４ is a group represented by the formula (3-1), and X ２ is an oxygen atom or a sulfur atom, or a group represented by formula (3-2).

16. Represented by the formula (1B), Ar ３ is a group represented by the formula (2-1) or (2-2), Ar ４ is a group represented by the formula (3-1), and X ２ is an oxygen atom or a sulfur atom, or a group represented by formula (3-2).

17. Represented by any one of the formulas (1B) and (1B-1) to (1B-9), Ar ３ The compound according to any one of claims 1 and 10 to 15, which is represented by any one of the following formulas (2A) to (2F). 【Chemical 22】 (In formula (2A), ・*21 is L ３ is the binding site to ・R １０１ ~R １０５ is a single bond bonded to *22, and R １０６ ~R １１０ One selected from is a single bond bonding to *23. R which is not a single bond １０１ ~R １０５ and R １０６ ~R １１０ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. R which is not a single bond １０１ ~R １０５ Adjacent two selected from the following are not bonded to each other to form a ring. R which is not a single bond １０６ ~R １１０ Adjacent two selected from the following are not bonded to each other to form a ring. ・R １１１ ~R １１５ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms. ・R １１１ ~R １１５ Adjacent two selected from the following are not bonded to each other to form a ring. m11 is 0, 1 or 2, and n11 is 0 or 1, except when m11 is 2 and n11 is 0. ・When m11 = 0 and n11 = 0, *23 represents *21. ・When m11 = 0 and n11 = 1, *22 represents *21. ・When m11 = 1 and n11 = 0, *23 represents *22.) 【Chemistry 23】 (In formula (2B), ・*24 is L ３ is the binding site to ・R １２１ ~R １２８ One selected from is a single bond bonding to *25. R which is not a single bond １２１ ~R １２８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. R which is not a single bond １２１ ~R １２８ Adjacent two selected from are not bonded to each other to form a ring. 【Chemistry 24】 (In formula (2C), ・*26 is L ３ is the binding site to ・R １３１ ~R １４０ One selected from is a single bond bonding to *27. R which is not a single bond １３１ ~R １４０ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. R which is not a single bond １３１ ~R １４０ Adjacent two selected from are not bonded to each other to form a ring. 【Chemistry 25】 (In formula (2D), ・*28 is L ３ is the binding site to ・n12 is 0 or 1. When n12 is 0, R １４１ ~R １４８ , R Ｅ , and R Ｆ one selected from is a single bond bonded to *29, or R Ｅ and R Ｆ One selected from is a divalent group bonded to *29. When n12 is 1, R １４１ and R １４２ , R １４２ and R １４３ , or R １４３ and R １４４ R is a single bond bonded to *h and the other is a single bond bonded to *i, and R is not a single bond bonded to *h and *i １４１ ~R １４４ , R １４５ ~R １４８ , R ２００ ~R ２０３ , R Ｅ , and R Ｆ is a single bond bonded to *29, or R Ｅ and R Ｆ One selected from is a divalent group bonded to *29. R which is not a single bond １４１ ~R １４８ and R which is not a single bond ２００ ~R ２０３ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms. R which is not a single bond １４１ ~R １４８ and R which is not a single bond ２００ ~R ２０３ Adjacent two selected from the following are not bonded to each other to form a ring. R that is not the single bond and is not a divalent group bonded to *29 Ｅ and R Ｆ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and may or may not be bonded to each other to form a ring. Ｅ and R Ｆ When one selected from is an aryl group, they are combined to form R Ｅ and R Ｆ does not form 1',3'-dihydrospiro[fluorene-9,2'-indene] together with the fluorene ring to which it is attached. 【Chemistry 26】 (In formula (2E), ・*30 is L ３ is the binding site to ・R １５１ ~R １５５ is a single bond bonded to *31, and R １５１ ~R １５５ The other one selected from is a single bond bonded to *32. R which is not a single bond １５１ ~R １５５ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group. R which is not a single bond １５１ ~R １５５ Adjacent two selected from the following are not bonded to each other to form a ring. ・R １６１ ~R １６５ and R １７１ ~R １７５ are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms. ・R that is not a hydrogen atom １６１ ~R １６５ At least one adjacent two selected from the following may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form a ring. ・R that is not a hydrogen atom １７１ ~R １７５ At least two adjacent ones selected from may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore may not form a ring. 【Chemical 27】 (In formula (2F), ・*32 is L ３ is the binding site to ・R １８１ ~R １９２ One selected from is a single bond bonding to *33. R which is not a single bond １８１ ~R １９２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. R which is not a single bond １８１ ~R １９２ Adjacent two selected from are not bonded to each other to form a ring.

18. X １ The compound according to any one of claims 1, 2, 6, and 7, wherein is an oxygen atom.

19. X ２ The compound according to any one of claims 1, 10, and 14 to 16, wherein is an oxygen atom.

20. X ３ The compound according to any one of claims 1, 10, 14, and 16, wherein is an oxygen atom.

21. The compound according to any one of claims 1 to 20, wherein the compound represented by formula (1A) or formula (1B) contains at least one deuterium atom.

22. The compound according to claim 1, which comprises any one of the following compounds 1 to 8: 【Chemistry 28】

23. A material for an organic electroluminescence device, comprising the compound according to any one of claims 1 to 22.

24. The material for an organic electroluminescence device according to claim 29, wherein the compound according to any one of claims 1 to 22 is a material for a hole transport layer.

25. 23. An organic electroluminescence device having a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer being composed of a single or multiple layers including a light-emitting layer, and at least one layer selected from the group consisting of a single layer and multiple layers constituting the organic layer comprising the compound according to any one of claims 1 to 22.

26. 26. The organic electroluminescence device according to claim 25, wherein the organic layer comprises a hole transporting zone between the anode and the light emitting layer, and the hole transporting zone comprises the compound according to any one of claims 1 to 22.

27. the hole transport zone includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side; The organic electroluminescence device according to claim 26, wherein at least one of the first hole transport layer and the second hole transport layer contains the compound according to any one of claims 1 to 22.

28. The organic electroluminescence device according to claim 27, wherein the second hole transport layer comprises the compound according to any one of claims 1 to 22.

29. 29. The organic electroluminescence device according to claim 27, wherein the light-emitting layer and the second hole transport layer are in direct contact with each other.

30. 30. The organic electroluminescence device according to claim 27, wherein a total thickness of the first hole transport layer and the second hole transport layer is 30 nm or more and 150 nm or less.

31. 31. The organic electroluminescence device according to claim 25, wherein the light-emitting layer comprises a layer containing a light-emitting compound that exhibits fluorescent emission having a main peak wavelength of 500 nm or less.

32. The organic electroluminescence device according to any one of claims 25 to 31, wherein the light-emitting layer is a single layer.

33. An electronic device comprising the organic electroluminescence device according to any one of claims 25 to 32.

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