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

Abstract

Provided are: a compound and a material for an organic electroluminescent element that further improve the performance of organic EL elements; an organic electroluminescent element having improved element performance; and an electronic device containing such an organic electroluminescent element, the compound being represented by formula (1A) or formula (1B) (each of the symbols in the formulas are as defined in the specification.), the material for an organic electroluminescent element containing the compound, the organic electroluminescent element containing the compound, and the electronic device containing such an organic electroluminescent element.

Description

[Technical field]

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

[0002] Generally, an organic electroluminescence 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 cathode. When a voltage is applied between the two electrodes, electrons are injected from the cathode side and holes are injected from the anode side into the light-emitting region, where they recombine 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 electroluminescence devices. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] U.S. Pat. No. 7,598,667 [Patent Document 2] China Patent Application Publication No. 114133333 [Patent Document 3] US Patent Application Publication No. 2022 / 0059771 Summary of the Invention [Problem to be solved by the invention]

[0005] Although many compounds for organic EL devices have been reported, there is still a demand for compounds that further improve the performance of organic EL devices.

[0006] The present invention has been made to solve the above-mentioned problems, and an object of the present invention is to provide a compound and a material for an organic electroluminescence device that further improve the performance of an organic EL device, an organic EL device having further improved device performance, and an electronic device including such an organic EL device. [Means for solving the problem]

[0007] The present inventors have conducted extensive research into the performance of organic EL devices containing novel compounds and have found that an organic EL device containing a compound represented by the following formula (1A) or formula (1B) has improved performance.

[0008] In one aspect, the present invention provides a compound represented by formula (1A) or (1B): [ka] [ka] [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 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 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 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. 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 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 Bare 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. R which is not the single bond and is not a divalent group bonded to *b1 A and R B may or may not be bonded to each other to form a ring. R that is not a group bonded to *b1 21 ~R 28 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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms. R 21 ~R 24 is a group bonded to b1, R that is not a group bonded to b1 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 group bonded to b1, R that is not a group bonded to b1 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 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 the group consisting of a single bond bonded to *c. When m is 2 to 4, a plurality of Ar 2 may be the same or different from each other. The R that is not a single bond 31 ~R 34 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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms. Ar, 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.

[0009] In formula (1B), N * is the central nitrogen atom. 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 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. 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 The central nitrogen atom is 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). [ka] 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 48are 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 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 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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms. R 41 ~R 48 Among these, 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 The central nitrogen atom is 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). [ka] 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 , RC , and R D 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 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 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 combine with 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 combine with 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 that 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 Ddoes not form 1',3'-dihydrospiro[fluorene-9,2'-indene] 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 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 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. formula (1B) Medium, L 1 and n1 is as defined in formula (1A).

[0010] In another aspect, the present invention provides a material for an organic electroluminescence device, comprising a compound represented by 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, the organic layer including an emitting layer, and at least one layer of the organic layer including a compound represented by Formula (1A) or Formula (1B).

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

[0013] An organic EL device containing a compound represented by the formula (1A) or (1B) exhibits improved device performance. [Brief description of the drawings]

[0014] [Figure 1] FIG. 1 is a schematic diagram showing an example of a layer structure of an organic EL element according to one embodiment of the present invention. [Diagram 2] FIG. 2 is a schematic diagram showing another example of a layer structure of an organic EL element according to an embodiment of the present invention. [Diagram 3] FIG. 2 is a schematic diagram showing still another example of a layer structure of an organic EL element according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0015] [Definition] In this specification, hydrogen atoms include isotopes having different numbers of neutrons, namely protium, deuterium, and tritium.

[0016] In the present specification, in a chemical structural formula, a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded to a possible bonding position that is not explicitly indicated with a symbol such as "R" or "D" representing a deuterium atom.

[0017] In this specification, the number of ring carbon atoms represents the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. For example, the number of ring carbon atoms of a 9,9-diphenylfluorenyl group is 13, and the number of ring carbon atoms of a 9,9'-spirobifluorenyl group is 25. In addition, when a benzene ring is substituted with, for example, an alkyl group as a substituent, the carbon number of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of the benzene ring substituted with an alkyl group is 6. In addition, when a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the carbon number of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.

[0018] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic compound, a fused ring compound, and a ring assembly). The number of ring atoms does not include atoms that do not constitute a ring (e.g., a hydrogen atom that terminates the bond of an atom constituting a ring) or atoms contained in a substituent when the ring is substituted with a substituent. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms or atoms constituting a substituent bonded to a pyridine ring is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. For example, hydrogen atoms bonded to carbon atoms of a quinazoline ring or atoms constituting a substituent are not included in the number of ring atoms of the quinazoline ring. Therefore, the number of ring atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

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

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

[0022] "Substituents Described Herein" The substituents described herein are explained below. Unless otherwise specified, each substituent described herein is defined as follows.

[0023] The "unsubstituted aryl group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkyl group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification. The "unsubstituted alkenyl group" described in this specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms, unless otherwise specified in this specification. The "unsubstituted alkynyl group" described in this specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms, unless otherwise specified in this specification. The "unsubstituted cycloalkyl group" described in this specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted arylene group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted divalent heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkylene group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.

[0024] "Substituted or unsubstituted aryl groups" Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B). (Here, the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group", and the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group".) In this specification, when the term "aryl group" is simply used, it includes both an "unsubstituted aryl group" and a "substituted aryl group". The term "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent. Examples of the "substituted aryl group" include the "unsubstituted aryl group" in the specific example group G1A below in which one or more hydrogen atoms are replaced with a substituent, and the substituted aryl group in the specific example group G1B below. The examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed here are merely examples, and the "substituted aryl group" described in this specification also includes the "substituted aryl group" in the specific example group G1B below in which a hydrogen atom bonded to a carbon atom of the aryl group itself is further replaced with a substituent, and the "substituted aryl group" in the specific example group G1B below in which a hydrogen atom of a substituent is further replaced with a substituent.

[0025] Unsubstituted aryl groups (specific example group G1A): Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, 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, Benzanthryl group, A phenanthryl group, Benzophenanthryl group, phenalenyl group, Pyrenyl group, Chrysenyl group, benzochrysenyl group, A triphenylenyl group, Benzotriphenylenyl group, tetracenyl group, Pentacenyl group, fluorenyl group, 9,9'-spirobifluorenyl group, Benzofluorenyl group, Dibenzofluorenyl group, fluoranthenyl group, Benzofluoranthenyl group, Perylenyl groups, and A monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0026] [ka]

[0027] [ka]

[0028] Substituted aryl groups (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, Cyanophenyl group, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl group, and A group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by any one of the general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0029] "Substituted or unsubstituted heterocyclic groups" The "heterocyclic group" described herein is a cyclic group that contains 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 herein is a monocyclic group or a condensed ring group. The "heterocyclic group" described herein may be an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when the term "heterocyclic group" is simply used, it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group". The term "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with a substituent. Specific examples of the "substituted heterocyclic group" include the groups in which the hydrogen atoms of the "unsubstituted heterocyclic group" in the specific example group G2A below are replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are exemplified. The examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" listed here are merely examples, and the "substituted heterocyclic group" described in this specification also includes the groups in which the hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself in the "substituted heterocyclic group" in the specific example group G2B are further replaced with a substituent, and the groups in which the hydrogen atoms of the substituents in the "substituted heterocyclic group" in the specific example group G2B are further replaced with a substituent.

[0030] The specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).

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

[0032] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): Pyrrolyl group, imidazolyl group, A pyrazolyl group, A triazolyl group, Tetrazolyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, A thiazolyl group, isothiazolyl group, A thiadiazolyl group, Pyridyl group, pyridazinyl group, pyrimidinyl group, A pyrazinyl group, Triazinyl group, Indolyl groups, isoindolyl group, Indolizinyl group, quinolizinyl group, A quinolyl group, isoquinolyl group, Cinnolyl group, phthalazinyl group, A quinazolinyl group, quinoxalinyl group, Benzimidazolyl group, Indazolyl group, A phenanthrolinyl group, A phenanthridinyl group, acridinyl group, A phenazinyl group, A carbazolyl group, Benzocarbazolyl group, morpholino group, phenoxazinyl group, A phenothiazinyl group, Azacarbazolyl and diazacarbazolyl groups.

[0033] Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): Furyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, Dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzoisoxazolyl group, phenoxazinyl group, morpholino group, Dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, Azanaphthobenzofuranyl groups, and Diazanaphthobenzofuranyl group.

[0034] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): A thienyl group, A thiazolyl group, isothiazolyl group, A thiadiazolyl group, Benzothiophenyl group (benzothienyl group), Isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), Naphthobenzothiophenyl group (naphthobenzothienyl group), benzothiazolyl group, benzisothiazolyl group, A phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), Diazadibenzothiophenyl group (diazadibenzothienyl group), Azanapthobenzothiophenyl group (azanaphthobenzothienyl group), and Diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

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

[0036] [ka]

[0037] [ka]

[0038] In the general formulae (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2. A and Y A At least one of is an oxygen atom, a sulfur atom, or NH. In the general formulae (TEMP-16) to (TEMP-33), X A and Y A When at least one of is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from NH or CH2.

[0039] Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): A (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, Ethyl benzimidazolyl group, phenyltriazinyl group, Biphenylyltriazinyl group, Diphenyltriazinyl group, a phenylquinazolinyl group, and a biphenylylquinazolinyl group.

[0040] Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, t-butyldibenzofuranyl group, and A monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0041] Substituted heterocyclic groups containing sulfur atoms (specific example group G2B3): Phenyldibenzothiophenyl group, methyldibenzothiophenyl group, t-Butyldibenzothiophenyl group, and A monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0042] Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4):

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

[0044] "Substituted or unsubstituted alkyl groups" Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl group (specific example group G3A) and substituted alkyl group (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 the term "alkyl group" is simply mentioned, it includes both the "unsubstituted alkyl group" and the "substituted alkyl group". The term "substituted alkyl group" refers to a group in which one or more hydrogen atoms in the "unsubstituted alkyl group" are replaced with a substituent. Specific examples of the "substituted alkyl group" include the following "unsubstituted alkyl group" (specific example group G3A) in which one or more hydrogen atoms are replaced with a substituent, and examples of the substituted alkyl group (specific example group G3B). In this specification, the alkyl group in the "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the "unsubstituted alkyl group" includes a straight-chain "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 merely examples, and the "substituted alkyl group" described in this specification also includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" in the specific example group G3B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl group" in the specific example group G3B is further replaced with a substituent.

[0045] Unsubstituted alkyl groups (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 groups (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 group (specific example group G4A) and substituted alkenyl group (specific example group G4B). (Here, the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group", and the "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group".) In this specification, the term "alkenyl group" simply includes both an "unsubstituted alkenyl group" and a "substituted alkenyl group". The term "substituted alkenyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced with a substituent. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl group" (specific example group G4A) having a substituent, and examples of substituted alkenyl groups (specific example group G4B). The examples of the "unsubstituted alkenyl group" and the examples of the "substituted alkenyl group" listed here are merely examples, and the "substituted alkenyl group" described in this specification also includes a group in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl group" in specific example group G4B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkenyl group" in specific example group G4B is further replaced with a substituent.

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

[0049] Substituted alkenyl groups (specific example group G4B): 1,3-butanedienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-Dimethylallyl group.

[0050] "Substituted or unsubstituted alkynyl groups" 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). (Here, the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group".) Hereinafter, when simply referring to an "alkynyl group", it includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group". The term "substituted alkynyl group" refers to an "unsubstituted alkynyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkynyl group" include the following "unsubstituted alkynyl groups" (specific example group G5A) in which one or more hydrogen atoms have been replaced with a substituent.

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

[0052] "Substituted or unsubstituted cycloalkyl groups" Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described in this specification include the following unsubstituted cycloalkyl group (specific example group G6A) and substituted cycloalkyl group (specific example group G6B). (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 the term "cycloalkyl group" is simply used, it includes both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group". The term "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl group" are replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (specific example group G6A) in which one or more hydrogen atoms are replaced with a substituent, and the examples of the substituted cycloalkyl group (specific example group G6B). The examples of the "unsubstituted cycloalkyl group" and the examples of the "substituted cycloalkyl group" listed here are merely examples, and the "substituted cycloalkyl group" described in this specification also includes a group in the "substituted cycloalkyl group" in the specific example group G6B in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself are replaced with a substituent, and a group in the "substituted cycloalkyl group" in the specific example group G6B in which a hydrogen atom of a substituent is further replaced with a substituent.

[0053] Unsubstituted cycloalkyl groups (specific example group G6A): A cyclopropyl group, A cyclobutyl group, Cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-Norbornyl group.

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

[0055] -Si(R 901 )(R 902 )(R 903 ) a group represented by As described herein, —Si(R 901 )(R 902 )(R 903 Specific examples (specific example group G7) of the group represented by -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. Multiple G1's in -Si(G1)(G1)(G1) are the same or different. The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other. The multiple G1s in -Si(G1)(G1)(G2) are the same as or different from each other. The multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other. The multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The multiple G6s in -Si(G6)(G6)(G6) are the same as or different from each other.

[0056] -O-(R 904 ) a group represented by As described herein, -O-(R 904 Specific examples (specific example group G8) of the group represented by -O(G1), -O(G2), -O(G3), and -O(G6) Examples include: Where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0057] -S-(R 905 ) a group represented by As described herein, -S-(R 905 Specific examples (specific example group G9) of the group represented by -S(G1), -S(G2), -S(G3), and -S(G6) Examples include: Where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0058] -N(R 906 )(R 907 ) a group represented by As described herein, -N(R 906 )(R 907 Specific examples (specific example group G10) of the group represented by -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. -The multiple G1's in N(G1)(G1) are the same or different from each other. The multiple G2's in -N(G2)(G2) are the same or different from each other. -The multiple G3's in N(G3)(G3) are the same or different from each other. -N(G6)(G6) may be the same or different.

[0059] "Halogen atoms" Specific examples of the "halogen atom" described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0060] "Substituted or unsubstituted fluoroalkyl groups" The term "substituted or unsubstituted fluoroalkyl group" as used herein 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 with a fluorine atom, and also includes a group (perfluoro group) in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with fluorine atoms. The number of carbon atoms in the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification. The term "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms in the "fluoroalkyl group" are replaced with a substituent. The term "substituted fluoroalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in the "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms in the substituent in the "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include the examples of the group in which one or more hydrogen atoms in the "alkyl group" (specific example group G3) are replaced with a fluorine atom.

[0061] "Substituted or unsubstituted haloalkyl groups" The term "substituted or unsubstituted haloalkyl group" as used herein 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 with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The number of carbon atoms in the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification. The term "substituted haloalkyl group" means a group in which one or more hydrogen atoms in the "haloalkyl group" are replaced with a substituent. The term "substituted haloalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in the "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms in the substituent in the "substituted haloalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted haloalkyl group" include the examples of the group in which one or more hydrogen atoms in the "alkyl group" (specific example group G3) are replaced with a halogen atom. Haloalkyl groups are sometimes referred to as halogenated alkyl groups.

[0062] "Substituted or unsubstituted alkoxy groups" A specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. The number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

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

[0064] "Substituted or unsubstituted aryloxy group" A specific example of the "substituted or unsubstituted aryloxy group" described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0065] "Substituted or unsubstituted arylthio group" A specific example of the "substituted or unsubstituted arylthio group" described in this specification is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0066] "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) are the same 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" A specific example of the "substituted or unsubstituted aralkyl group" described in the present specification is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. Thus, the "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one aspect of a "substituted alkyl group". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the carbon number of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in the present specification. Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl.

[0068] Unless otherwise specified in the present specification, the substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, and the like.

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

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

[0071] [ka]

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

[0073] [ka]

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

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

[0076] [ka]

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

[0078] The substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like, unless otherwise specified in the present specification.

[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-mentioned "substituted or unsubstituted aryl group". Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) 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.

[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 heterocycle from the above-mentioned "substituted or unsubstituted heterocyclic group". Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include divalent groups derived by removing one hydrogen atom on the heterocycle from the "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[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 of the "substituted or unsubstituted alkylene group" (specific example group G14) 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.

[0082] The substituted or unsubstituted arylene group described in this specification is preferably any of the groups represented by the following general formulae (TEMP-42) to (TEMP-68), unless otherwise specified in this specification.

[0083] [ka]

[0084] [ka]

[0085] In the general formulae (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent. In the above general formulae (TEMP-42) to (TEMP-52), * represents a bonding position.

[0086] [ka]

[0087] In the general formulae (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent. Equations Q9 and Q 10 may be bonded to each other via a single bond to form a ring. In the above general formulae (TEMP-53) to (TEMP-62), * represents a bonding position.

[0088] [ka]

[0089] In the general formulae (TEMP-63) to (TEMP-68), Q1 to Q8 each independently represent a hydrogen atom or a substituent. In the above general formulae (TEMP-63) to (TEMP-68), * represents a bonding position.

[0090] The substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any of the groups represented by the following general formulae (TEMP-69) to (TEMP-102), unless otherwise specified in this specification.

[0091] [ka]

[0092] [ka]

[0093] [ka]

[0094] In the general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 each independently represent a hydrogen atom or a substituent.

[0095] [ka]

[0096] [ka]

[0097] [ka]

[0098] [ka]

[0099] In the general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 each independently represent a hydrogen atom or a substituent.

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

[0101] - "When bonded to form a ring" In this specification, the phrase "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle, bond to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle", the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted fused ring", and the case where "one or more of a set consisting of two or more adjacent groups are not bonded to each other". In this specification, the cases where "one or more of a set of two or more adjacent rings are bonded to each other to form a substituted or unsubstituted monocyclic ring" and "one or more of a set of two or more adjacent rings are bonded to each other to form a substituted or unsubstituted condensed ring" (hereinafter, these cases may be collectively referred to as "a case where they are bonded to form a ring") will be explained below. The case of an anthracene compound represented by the following general formula (TEMP-103), in which the mother skeleton is an anthracene ring, will be explained as an example.

[0102] [ka]

[0103] For example, R921 ~R 930 In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," one pair of adjacent two groups is R 921 and R 922 With R 922 and R 923 With R 923 and R 924 With R 924 and R 930 With R 930 and R 925 With R 925 and R 926 With R 926 and R 927 With R 927 and R 928 With R 928 and R 929 and R 929 and R 921 It is paired with .

[0104] The above "one or more pairs" means that two or more pairs of adjacent two or more groups may simultaneously form a ring. For example, R 921 and R 922 and are bonded to ring Q A At the same time, R 925 and R 926 and are bonded to ring Q B When the above general formula (TEMP-103) is formed, the anthracene compound represented by the general formula (TEMP-104) is represented by the following general formula (TEMP-104).

[0105] [ka]

[0106] The case where a "set of two or more adjacent units" forms a ring includes not only the case where a set of two adjacent units is bonded as in the previous example, but also the case where a set of three or more adjacent units is bonded. For example, R 921 and R 922 and are bonded to ring Q A and R 922 and R923 and are bonded to ring Q C The three adjacent (R 921 , R 922 and R 923 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), the ring Q A and Ring Q C is R 922 Share.

[0107] [ka]

[0108] The "monocyclic ring" or "condensed ring" formed may be a saturated or unsaturated ring as the structure of only the ring formed. Even when "one of the pairs of adjacent two" forms a "monocyclic ring" or a "condensed ring", the "monocyclic ring" or the "condensed ring" may form a saturated or unsaturated ring. For example, the ring Q formed in the general formula (TEMP-104) may be a saturated or unsaturated ring. A and Ring Q B are "monocyclic" or "condensed rings". In addition, the ring Q formed in the general formula (TEMP-105) A , and ring Q C is a "fused ring". The ring Q in the above general formula (TEMP-105) A and Kan Q C That is, Ring Q A and Kan Q C The ring Q in the general formula (TMEP-104) is condensed to form a condensed ring. A If is a benzene ring, then ring Q A The ring Q in the general formula (TMEP-104) is a monocyclic ring. A If is a naphthalene ring, then ring Q A is a fused ring.

[0109] The term "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The term "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of the aromatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G1 are terminated with a hydrogen atom. Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in the specific example group G2 are terminated with a hydrogen atom. Specific examples of the aliphatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom. The term "form a ring" means that a ring is formed only with a plurality of atoms of the parent skeleton, or with a plurality of atoms of the parent skeleton and one or more optional elements. For example, R 921 and R 922 and are bonded together to form a ring Q A is R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 It means a ring formed by the carbon atom of the anthracene skeleton to which R is bonded and one or more arbitrary elements. 921 and R 922 Todekan Q A In the case where R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 When the carbon atom of the anthracene skeleton to which R is bonded forms a monocyclic unsaturated ring with four carbon atoms, R 921 and R 922 The ring formed by this is a benzene ring.

[0110] Here, unless otherwise specified in the present specification, the "arbitrary element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur. In the arbitrary element (for example, in the case of a carbon element or a nitrogen element), a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below. When an arbitrary element other than a carbon element is included, the ring formed is a heterocycle. Unless otherwise specified in this specification, the "one or more arbitrary elements" constituting a single ring or a condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less. Unless otherwise specified in this specification, of the "monocyclic ring" and the "condensed ring", the "monocyclic ring" is preferred. Unless otherwise specified in this specification, of the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred. Unless otherwise specified in this specification, a "monocyclic ring" is preferably a benzene ring. Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring. When "one or more of a set of two or more adjacent rings" "combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring", unless otherwise specified in this specification, preferably, one or more of a set of two or more adjacent rings combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent 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 ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above-mentioned section "Substituents described in this specification". When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification". The above is an explanation of the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted fused ring" ("combined to form a ring").

[0112] Substituents in the phrase "substituted or unsubstituted" In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituent" in the present specification) is, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms; an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms; -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and Unsubstituted heterocyclic group having 5 to 50 ring atoms and the like, Here, R 901 ~R 907 are each independently Hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 901 If there are two or more, there are two or more R 901 are identical or different from each other, R 902 If there are two or more, there are two or more R 902 are identical or different from each other, R 903If there are two or more, there are two or more R 903 are identical or different from each other, R 904 If there are two or more, there are two or more R 904 are identical or different from each other, R 905 If there are two or more, there are two or more R 905 are identical or different from each other, R 906 If there are two or more, there are two or more R 906 are identical or different from each other, R 907 If there are two or more, there are two or more R 907 are the same or different from each other.

[0113] In one embodiment, the substituent in the above "substituted or unsubstituted" is: an alkyl group having 1 to 50 carbon atoms; an aryl group having 6 to 50 ring carbon atoms, and Heterocyclic groups with 5 to 50 ring atoms is a group selected from the group consisting of:

[0114] In one embodiment, the substituent in the above "substituted or unsubstituted" is: an alkyl group having 1 to 18 carbon atoms; An aryl group having 6 to 18 ring carbon atoms, and Heterocyclic groups with 5 to 18 ring atoms is a group selected from the group consisting of:

[0115] Specific examples of each group of the above optional substituents are the specific examples of the substituents described above in the section "Substituents described in this specification."

[0116] Unless otherwise specified in this specification, any adjacent substituents may be combined with each other to 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, more preferably a benzene ring. Unless otherwise specified in the present specification, the optional substituent may further have a substituent. The substituent that the optional substituent further has is the same as the optional substituent described above.

[0117] In this specification, a numerical range expressed using "AA to BB" means a range including the number AA written before "AA to BB" as the lower limit and the number BB written after "AA to BB" as the upper limit.

[0118] The compounds of the present invention will be described below. A compound according to one embodiment of the present invention is represented by the following formula (1A) or (1B). However, hereinafter, the compounds of the present invention represented by formula (1A) and each formula contained in formula (1A) described later may be simply referred to as "compound (1A)", "invention compound (1A)", or "first invention compound". Further, the compounds of the present invention represented by formula (1B) and each formula contained in formula (1B) described later may be simply referred to as "compound (1B)", "invention compound (1B)", or "second invention compound". Furthermore, the first and second invention compounds may be collectively referred to simply as "invention compounds". [ka] [ka]

[0119] The symbols in formula (1A) and each formula contained in formula (1A) described later, and the symbols in formula (1B) and each formula contained in formula (1B) described later will be explained below. The same symbols have the same meaning. In this specification, as shown below, the partial structure bonded to *a in formula (1A) may be referred to as "partial structure A". In addition, in formula (1B), the partial structure bonded to *a may be referred to as "partial structure B". [ka]

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

[0121] In formula (1A), Z 1 and Z 2 is a single bond bonded to *a, and preferably Z 2 is a single bond that bonds 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 is 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 the below-described formula (1A-1). [ka]

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

[0123] The above Z that is not a single bond 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10are 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 carbon atoms, or a substituted or unsubstituted heteroaryl group (aromatic heterocyclic group) having 5 to 13 ring 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 carbon atoms, and more preferably a hydrogen atom. The above Z that is not a single bond 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 may all be hydrogen atoms. The above Z that 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.

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

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

[0126] The substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms is, for example, Pyrrolyl group, furyl group, thienyl group, pyridyl group, imidazopyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyrazolyl group, isoxazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, indolyl group, isoindolyl group, indolizinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzoyl group, a midazolyl group, a benzoxazolyl group, a benzothiazolyl group, an indazolyl group, a benzisoxazolyl group, a benzisothiazolyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group (a benzothienyl group, the same applies hereinafter), an isobenzothiophenyl group (an isobenzothienyl group, the same applies hereinafter), a dibenzothiophenyl group (a 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); Preferred are a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group. More preferred are a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.

[0127] In formula (1A), R 1Aand R 2A 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, 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 carbon atoms, and more preferably a hydrogen atom. R 1A and R 2A may be a hydrogen atom. R 1A and R 2A may or may not be bonded to each other to form a ring.

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

[0129] The unsubstituted aryl group of the above-mentioned substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 18, and more preferably 6 to 12 ring carbon atoms is, for example, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a benzanthryl 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; Preferred is a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group; More preferably, it is 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; More preferably, it is a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group; Particularly preferred is a phenyl group.

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

[0131] In formula (1A), Y 1 and Y 2 is a hydrogen atom.

[0132] In formula (1A), L 1represents a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms, preferably a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group, preferably a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, and more preferably a substituted or unsubstituted phenylene group.

[0133] The phenylene group is an o-phenylene group, an m-phenylene group, or a p-phenylene group, with a p-phenylene group being preferred. The 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 more preferably a 4,4'-biphenylene group. The 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] The arylene group, L 1 The substituents are selected from unsubstituted alkyl groups having 1 to 6 carbon atoms and aryl groups having 6 to 12 ring carbon atoms, 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 the unsubstituted aryl group having 6 to 12 ring carbon atoms as the above-mentioned substituent are given in Z 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 As described above.

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

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

[0137] R that 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, 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 carbon atoms, and more preferably a hydrogen atom. R that is not a single bond and is not a divalent group bonded to *b1 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 carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms represented by R in formula (1A) are as follows: 1A and R 2A As described above. R A and R B The divalent group bonded to the above *b1 represented by is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms. R A and R B The alkylene group, arylene group, and heteroarylene group represented by R A and R B The divalent residues of the alkyl, aryl and heteroaryl groups represented by the formula (I) are mentioned above, and the same applies to the preferred divalent residues of the alkyl, aryl and heteroaryl groups represented by the formula (I).

[0138] R that is not a single bond and is not a divalent group bonded to *b1 A and R B may or may not be bonded to each other to form a ring. R that is not a single bond and is not a divalent group bonded to *b1 A and R B The ring formed by bonding to each other is a substituted or unsubstituted spiro ring. The spiro ring is a hydrocarbon ring or a heterocycle, and is selected from a monocycle, a condensed ring, a bridged bicyclo ring, and a bridged tricyclo ring. Examples of substituted or unsubstituted spiro rings are shown below, but are not limited to these. * indicates the bonding position of the fluorene skeleton to the benzene ring. [ka]

[0139] In one embodiment, L of compound (1A) 2The partial structure bonded to is represented by any one of the following formulas (1-a1) to (1-a5). [ka] [ka]

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

[0141] The R that is not a single bond 21 ~R 28 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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring 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 carbon atoms, and more preferably a hydrogen atom. The R that is not a single bond 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 carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms represented by Z in formula (1A) are as follows: 1 and Z 2 , R 13A , R14A , and R 15 ~R 18 , R 7 ~R 10 As described above.

[0142] In formula (1A), 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.

[0143] In formula (1A), L 2 represents a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms. L 2 The details of the substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms represented by L of formula (1A) are as follows: 1 As described above.

[0144] In formula (1A), L 1 and L 2 When present, they may be the same or different. 1 and L 2 Only one of m and n may be present (i.e., one of m and n may be 0 and the other may be 1), and L 1 and L 2 may not both be present (i.e., m and n may be 0). Preferably, the above-mentioned "-(L 1 ) n1 -" and "-(L2 ) n2 The combination of "-" is represented by one of the combinations [k1] to [k4] shown below. · [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, R 21 ~R 28 One selected from the central nitrogen atom N * Bind to. In one embodiment, n1 and n2 are both 0; in another embodiment, n1 and n2 are both 1; in yet another embodiment, n1 is 0 and n2 is 1; and in yet another embodiment, n1 is 1 and n2 is 0.

[0146] In formula (1A), 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, 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 carbon atoms, and more preferably a hydrogen atom. Ar 1 The details of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and the substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms represented by R in formula (1A) are as follows: 1A and R 2A As described above.

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

[0148] In formula (1A), m is 0, 1, 2, 3, or 4, preferably 0, 1, 2, or 3, preferably 0, 1, or 2, and more preferably 0 or 1. 1 When is a hydrogen atom, m is 0. When m is 1 to 4, R 31 ~R 34 One to four selected from the group consisting of a single bond bonded to *c. When m is 2 to 4, a plurality of Ar 2 may be the same or different from each other.

[0149] In formula (1A), R 31 ~R 34 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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring 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 carbon atoms, and more preferably a hydrogen atom. The R that is not a single bond 31 ~R 34 may all be hydrogen atoms. R 31 ~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 carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms represented by Z in formula (1A) are as follows: 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 As described above.

[0150] In formula (1A), Ar 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.

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

[0152] In formula (1B), R 11 ~R 14 is a single bond bonded to *a, preferably R 12 ~R 14 is a single bond bonded to *a, and more preferably, R 12 or R 14 is a single bond bonded to *a, and more preferably R 12 is a single bond that bonds 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 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). [ka]

[0153] In formulae (1y-1) to (1y-4), *y represents the bonding position to *a. 11 ~R 14 Details of and other symbols are as explained below.

[0154] The R that is not a single bond 11 ~R 14 , R 15 ~R 18 , and R 7 ~R 10are 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 carbon atoms, preferably are 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 carbon atoms, and more preferably a hydrogen atom. The R that is not a single bond 11 ~R 14 , R 15 ~R 18 , and R 7 ~R 10 may all be hydrogen 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 11 ~R 14 The 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 carbon atoms represented by the formula (1A) are as follows: 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 As described above.

[0155] In formula (1B), R 1B , R 2B , R 5B , and R 6Bare 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, 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 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 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. 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 carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms represented by R in formula (1A) are as follows: 1A and R 2A As described above.

[0156] In formula (1B), L 3 represents a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms. The details of the substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms are as follows: 1 As described above.

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

[0158] In formula (1B), Ar 3represents 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), preferably an aryl group having 6 to 18 ring 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 carbon atoms. [ka]

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

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

[0161] In formula (2-1), R 41 ~R 44 is a single bond bonded to *d, preferably R 41 , R 42 , and R 44 is a single bond bonded to *d, more preferably R 41 or R 44 is a single bond bonded to *d, and more preferably R 44 is a single bond bonded to *d. The R that is not a 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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring 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 carbon atoms, and more preferably a hydrogen atom. The R that is not a single bond 41 ~R 44 , R 45 ~R 48may all be hydrogen 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. 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 carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms represented by Z in formula (1A) are as follows: 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 As described above.

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

[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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring 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 carbon atoms, and more preferably a hydrogen atom. R 41 ~R 48 may all be hydrogen atoms. R 41 ~R 48 Among these, a pair of adjacent groups may or may not be bonded to each other to form a ring. R 41 ~R 48The 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 carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms represented by Z in formula (1A) are as follows: 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 As described above. Ar 3 When represented by the above formula (2-2), n3 is preferably 1.

[0164] In formula (1B), L 4 represents a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms. L 4 The details of the substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms represented by L of formula (1A) are as follows: 1 As described above.

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

[0167] In formula (3-1), *** represents L 4 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 is a single bond bonded to *b2, or R C and R D One selected from is a divalent group bonded to *b2. X 2 is an oxygen atom or a sulfur atom, R 21B ~R 28B is a single bond bonded to b2, preferably R 21B , R 22B , R 24B , R 25B , R 27B , and R 28B is a single bond bonded to b2, more preferably R 21B , R 24B , R 25B , and R 27B is a single bond bonded to b2, and more preferably R 24B or R 25B is a single bond that bonds to *b2. X 2 But, =CR C R D When R 21B ~R 23B , R 26B ~R 28B , R C , and R Dis a single bond bonded to *b2, or R C and R D is a divalent group bonded to *b2, and more preferably R 23B , R 26B , R C , or R D 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 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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring 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 carbon atoms, and more preferably a hydrogen atom. The R that is not a 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 carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms represented by Z in formula (1A) are as follows: 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 As described above.

[0170] In formula (3-1), R 21B ~R 24B is a single bond bonded to b2, R 21B ~R24B do not combine with 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 combine with each other to form a ring, and R 21B ~R 24B may or may not be bonded to each other to form a ring.

[0171] In formula (3-1), R which is not the 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, 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 carbon atoms, and more preferably a hydrogen atom. R that is not a single bond and is not a divalent group bonded to *b2 above C and R D may be a hydrogen atom. R that is not a single bond and is not a divalent group bonded to *b2 above C and R D may or may not be bonded to 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 carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms represented by R in formula (1A) are as follows: 1A and R 2A As described above. However, R C and R DWhen 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] with the fluorene ring to which it is attached. In other words, R C and R D do not bond to each other to form a structure represented by the following formula. In the following formula, *w indicates the bonding position to L4. In the following formula, R is omitted for simplification. [ka]

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

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

[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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring 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 carbon atoms, and more preferably a hydrogen atom. R 21B ~R 28B may all be hydrogen 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. 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 carbon atoms, and the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms represented by Z in formula (1A) are as follows: 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 As described above.

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

[0176] In formula (1B), L 1 and L 2 and L 3 When present, the three may be the same or different, or two of the three may be the same and one may be different. In formula (1B), L 1 and L 2 and L 3 Only two of n1, n3, and n4 may be present (i.e., two of n1, n3, and n4 may be 1 and the other may be 0), in which case the two present may be the same or different from each other. In formula (1B), L 1 and L 2 and L 3 Only one of n1, n3, and n4 may be present (i.e., two of n1, n3, and n4 may be 0 and the other may be 1), and L 1 ~L 3 may not all be present (i.e., 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 one of the combinations [k11] to [k18] shown below. · [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 compound (1A) is represented by the following formula (1A-1). [ka]

[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 formula (1A) above.

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

[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 formula (1A) above.

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

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

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

[0184] 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, and are preferably a hydrogen atom. 51 ~R 55 One selected from is a single bond bonded to *d. R that is not a single bond bonded to *d 51 ~R 55 may all be hydrogen atoms. 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 (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, and are preferably a hydrogen atom. 61 ~R 65 One selected from is a single bond bonded to *e. R that is not a single bond bonded to *e 61 ~R 65 may all be hydrogen atoms. The R that is not a single bond 61 ~R 65 Adjacent pairs of these do not bond to each other to 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 carbon atoms represented by the formula (1A) are Z 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 As described above.

[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 formula (1A) above.

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

[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 formula (1A) above.

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

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

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

[0192] 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) above.

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

[0194] 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) above.

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

[0196] In one embodiment, the compound represented by any one of the above formulas (1B), (1B-1), and (1B-2) is1 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 embodiment, the compound (1B) is represented by any one of the following formulas (1B-3) to (1B-9). [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0198] 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, and are preferably a hydrogen atom. 51 ~R 55 One selected from is a single bond bonded to *d. R that is not a single bond bonded to *d 51 ~R 55 may all be hydrogen atoms. The R that is not a single bond 51 ~R 55Adjacent 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, and are preferably a hydrogen atom. 71 ~R 75 One selected from is a single bond bonded to *f. R that is not a single bond bonded to *f 71 ~R 75 may all be hydrogen atoms. 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, and are preferably a hydrogen atom. 81 ~R 85 One selected from is a single bond bonded to *g. R that is not a single bond bonded to *g 81 ~R 85 may all be hydrogen atoms. 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.

[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 carbon atoms represented by the formula (1A) are Z 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10As described above.

[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 formula (1B) above.

[0201] In one embodiment, the compound (1B) is represented by any one of the above formulas (1B), (1B-1), and (1B-3) to (1B-9), Ar 3 is a substituted or unsubstituted aryl group having 6 to 30 ring 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 a group represented by the above formula (3-2).

[0202] In one embodiment, the compound (1B) is represented by the 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 a group represented by the above formula (3-2).

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

[0204] In formula (2A), *21 is L 3 is the binding site to

[0205] In formula (2A), R 101 ~R 105 is a single bond bonded to *22, and R 106 ~R 110 One selected from is a single bond bonded to *23. The R that 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, and are preferably a hydrogen atom. The R that is not a single bond 101 ~R 105 and R 106 ~R 110 may all be hydrogen atoms. The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as follows: R 1A and R 2A As described above. The details of the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms are as follows: 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 As described above. The R that is not a single bond 101 ~R 105 Adjacent two selected from the following are not bonded to each other to form a ring. The R that is not a single bond 106 ~R 110 Adjacent two selected from the following are not bonded to each other to form a ring.

[0206] In formula (2A), R111 ~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, 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 carbon atoms, and more preferably a hydrogen atom. R 111 ~R 115 may all be hydrogen atoms. The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as follows: R 1A and R 2A As described above. The details of the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms and the details of the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms are described in Z of formula (1A). 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 As described above. R 111 ~R 115 Adjacent two selected from the following are not bonded to each other to form a ring.

[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 expressed by formula (2A), 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. In addition, Ar 3 is represented by formula (2A), m11 is 1 and n11 is 0, R that 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 formula (2A) is preferably represented by the following formula: In the following formula, R has been omitted for simplicity. [ka]

[0209] [ka]

[0210] In formula (2B), *24 is L 3 is the binding site to

[0211] In formula (2B), R 121 ~R 128 One selected from is a single bond bonded to *25. The R that 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, and are preferably a hydrogen atom. R 111 ~R 115 may all be hydrogen atoms. The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as follows: R 1A and R 2A As described above. The details of the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms are as follows: 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 As described above. The R that is not a single bond 121 ~R 128 Adjacent two selected from the following are not bonded to each other to form a ring.

[0212] [ka]

[0213] In formula (2C), *26 is L 3 is the binding site to

[0214] In formula (2C), R 131 ~R 140 One selected from is a single bond bonded to *27. The R that 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, and are preferably a hydrogen atom. The R that is not a single bond 131 ~R 140 may all be hydrogen atoms. The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as follows: R 1A and R 2A As described above. The details of the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms are as follows: 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R10 As described above. The R that is not a single bond 131 ~R 140 Adjacent two selected from the following are not bonded to each other to form a ring. [ka]

[0215] In formula (2D), *28 is L 3 is the binding site to

[0216] In formula (2D), n12 is 0 or 1. When n12 is 0, R 141 ~R 148 , 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. 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 that bonds to *h on one side and a single bond that bonds to *i on the other side, and is not a single bond that bonds to both *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.

[0217] In formula (2D), R which is not a single bond 141 ~R 148 and R which is not a single bond 200 ~R 203are 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, 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 carbon atoms, and more preferably a hydrogen atom. The R that is not a single bond 141 ~R 148 and R that is not a single bond 200 ~R 203 may all be hydrogen atoms. The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as follows: R 1A and R 2A As described above. The details of the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms and the details of the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms are described in Z of formula (1A). 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 As described above. The R that is not a single bond 141 ~R 148 and R that is not a single bond 200 ~R 203 Adjacent two selected from the following are not bonded to each other to form a ring.

[0218] In formula (2D), R is not the single bond and is not a divalent group bonded to *29. E and R Fare 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, 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 carbon atoms, and more preferably a hydrogen atom. R that is not a single bond and is not a divalent group bonded to *29 above E and R F may be a hydrogen atom. The details of the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms are as follows: 1A and R 2A As described above. The details of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and the details of the substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms are described in Z of formula (1A). 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 As described above. R that is not a single bond and is not a divalent group bonded to *29 above E and R F may or may not be bonded to each other to form a ring. However, R 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] with the fluorene ring to which it is attached. 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. In the following formula, R is omitted for simplification. [ka]

[0219] [ka]

[0220] In formula (2E), *30 is L 3 is the binding site to

[0221] In formula (2E), 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. The R that 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, and are preferably a hydrogen atom. The R that is not a single bond 151 ~R 155 may all be hydrogen atoms. The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as follows: R 1A and R 2A As described above. The R that is not a single bond 151 ~R 155 Adjacent two selected from the following are not bonded to each other to form a ring.

[0222] In formula (2E), 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, and preferably a hydrogen atom. R 161 ~R 165 and R 171 ~R 175 may all be hydrogen atoms. The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as follows: R 1A and R 2A As described above. R is not a hydrogen atom 161 ~R 165 At least one adjacent two selected from the above 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 is not a hydrogen atom 171 ~R 175 At least one adjacent two selected from the group consisting of 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.

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

[0224] [ka]

[0225] In formula (2F), *32 is L 3 is the binding site to

[0226] In formula (2F), R 181 ~R 192 One selected from is a single bond bonded to *33. The R that 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, and are preferably a hydrogen atom. The R that is not a single bond 181 ~R 192 may all be hydrogen atoms. The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms are as follows: R 1A and R 2A As described above. The details of the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms are as follows: 1 and Z 2 , R 13A , R 14A , and R 15 ~R 18 , R 7 ~R 10 As described above. The R that is not a single bond 181 ~R 192 Adjacent two selected from the following are not bonded to each other to form a ring.

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

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

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

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

[0231] In one embodiment, the compound of 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 Represented by 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 an alkyl group represented by the formula: (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 an 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 a heteroaryl group represented by the formula: (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 , R 200 ~R 203 , R E , R F , and R 181 ~R 192 A hydrogen atom directly bonded to a substituent of the alkyl group represented by the formula: (6)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 , Ar 1 , Ar 2 , 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 ~R 148 , R 200 ~R 203 , R E , R F , and R 181 ~R 192 A hydrogen atom directly bonded to a substituent of the aryl group represented by the formula (I); (7)R 1A , R 2A , R 7 ~R 10 , Z 1 , Z 2 , R 13A , R 14A , R 15 ~R 18 , 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 R F A hydrogen atom directly bonded to a substituent of the heteroaryl group represented by the formula (I); (8) L 1 ~L 4 A hydrogen atom directly bonded to the arylene group represented by the formula: (9) L 1 ~L 4 A hydrogen atom directly bonded to a substituent of the arylene group represented by the formula:

[0233] As described above, the term "hydrogen atom" as used herein includes protium, deuterium, and tritium atoms. The first or second invention compound may contain naturally occurring deuterium atoms. Moreover, deuterium atoms may be intentionally introduced into the first or second invention compound by using a compound in which some or all of the raw material compounds are deuterated.

[0234] The deuteration rate of the first or second invention compound depends on the deuteration rate of the raw material compound used. Even if a raw material with a specific deuteration rate is used, a certain proportion of naturally occurring light hydrogen isotopes may be contained. Therefore, the deuteration rate of the invention compound shown below includes a ratio that takes into account trace amounts of naturally occurring isotopes, in addition to the ratio calculated by simply counting the number of deuterium atoms represented by the chemical formula. The deuteration rate of the first or second invention compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, still more preferably 10% or more, and even more preferably 50% or more. The first or second compound of the invention may be a deuterated form in which all hydrogen atoms are deuterium atoms (that is, the deuteration rate of the compound of the invention is 100%).

[0235] The first or second invention 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, even more preferably 5% or more, still more preferably 10% or more, and even more preferably 50% or more and less than 100%. Furthermore, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the first or second invention compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, and even more preferably 10% or more and 100% or less.

[0236] Details of the substituents (optional substituents) in the case of "substituted or unsubstituted" included in the definition of each formula above are as described in "Substituents in the case of "substituted or unsubstituted".

[0237] The first or second invention compound can be easily produced by a person skilled in the art by referring to the synthesis examples described below and known synthesis methods.

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

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[0309] Materials for organic electroluminescence devices The material for organic EL devices according to one embodiment of the present invention contains the first or second invention compound. The content of the first or second invention compound in the material for organic EL devices is 1% by mass or more (including 100%), preferably 10% by mass or more (including 100%), more preferably 50% by mass or more (including 100%), further preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). The material for organic EL devices according to one embodiment of the present invention is useful for the production of organic EL devices. In one embodiment of the present invention, the first or second invention compound is preferably a hole transport layer material.

[0310] In one embodiment of the present invention, the material for an organic EL device preferably further contains a protium derivative of the first or second invention compound. The protium derivative is a compound in which all hydrogen atoms in the first or second invention compound are protium atoms. The mixing molar ratio of the first or second invention compound to the protium derivative of the first or second invention compound (invention compound:protium derivative) is preferably 10:90 to 90:10, more preferably 20:80 to 80:20, even more preferably 30:70 to 70:30, and particularly preferably 40:60 to 60:40.

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

[0312] Organic EL element The organic electroluminescence device according to one embodiment of the present invention comprises an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer comprises an emitting layer, and at least one of the organic layers comprises the compound of the present invention. Examples of the organic layer containing the compound of the invention include, but are not limited to, a hole transport zone (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 zone (electron injection layer, electron transport layer, hole blocking layer, etc.) provided between the cathode and the light emitting layer, etc. The compound of the invention is preferably used as a material for the hole transport zone or light emitting layer of a fluorescent or phosphorescent EL device, more preferably as a material for the hole transport zone, even more preferably as a material for the hole injection layer, hole transport layer, electron blocking layer, or exciton blocking layer, and particularly preferably as a material for the hole injection layer or hole transport layer.

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

[0314] For example, the following device configuration can be given as a representative device configuration of a simple type organic EL device. (1) Anode / light-emitting unit / cathode The light-emitting unit may be a multi-layer type having a plurality of phosphorescent or fluorescent light-emitting layers, in which case a spacer layer may be provided between each light-emitting layer to prevent excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer. A typical layer structure of a simple light-emitting unit is shown below. The layers in parentheses are optional. (a) (hole injection layer / ) hole transport layer / fluorescent light-emitting layer / electron transport layer ( / electron injection layer) (b) (hole injection layer / ) hole transport layer / first fluorescent-emitting layer / second fluorescent-emitting layer / electron transport layer ( / electron injection layer) (c) (hole injection layer / ) hole transport layer / phosphorescent emitting layer / space layer / fluorescent emitting layer / electron transport layer ( / electron injection layer) (d) (hole injection layer / ) hole transport layer / first phosphorescent emitting layer / second phosphorescent emitting layer / space layer / fluorescent emitting layer / electron transport layer ( / electron injection layer) (e) (hole injection layer / ) hole transport layer / phosphorescent emitting layer / space layer / first fluorescent emitting layer / second fluorescent emitting layer / electron transport layer ( / electron injection layer) (f) (hole injection layer / ) hole transport layer / electron blocking layer / fluorescent emitting layer / electron transport layer ( / electron injection layer) (g) (hole injection layer / ) hole transport layer / exciton blocking layer / fluorescent emitting layer / electron transport layer ( / electron injection layer) (h) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light-emitting layer / electron transport layer ( / electron injection layer) (i) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light-emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer) (j) (hole injection layer / ) hole transport layer / fluorescent light-emitting layer / hole blocking layer / electron transport layer ( / electron injection layer) (k) (hole injection layer / ) hole transport layer / fluorescent emitting layer / exciton blocking layer / electron transport layer ( / electron injection layer)

[0315] The phosphorescent or fluorescent emitting layers may each emit light of a different color. Specifically, the light emitting unit (d) may have a layer structure such as (hole injection layer / ) hole transport layer / first phosphorescent emitting layer (red light emission) / second phosphorescent emitting layer (green light emission) / space layer / fluorescent emitting layer (blue light emission) / electron transport layer. An electron blocking layer may be provided between each light-emitting layer and the hole transport layer or between each spacer layer as needed. Also, a hole blocking layer may be provided between each light-emitting layer and the electron transport layer as needed. 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] Representative device configurations of tandem-type organic EL devices include the following. (2) Anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode Here, the first light-emitting unit and the second light-emitting unit can be, for example, independently selected from the light-emitting units described above. The intermediate layer is generally also called an intermediate electrode, intermediate conductive layer, charge generating layer, electron extracting layer, connecting layer, or intermediate insulating layer, and can be made of a known material configuration that supplies electrons to the first light-emitting unit and holes to the second light-emitting unit.

[0317] FIG. 1 is a schematic diagram showing an example of the configuration of an organic EL device according to one embodiment of the present invention. The organic EL device 1 has a substrate 2, an anode 3, a cathode 4, and an emitting unit 10 disposed between the anode 3 and the cathode 4. The emitting unit 10 has an emitting layer 5. A hole transport zone 6 (hole injection layer, hole transport layer, etc.) is provided between the emitting layer 5 and the anode 3, and an electron transport zone 7 (electron injection layer, electron transport layer, etc.) is provided between the emitting layer 5 and the cathode 4. In addition, an electron blocking layer (not shown) may be provided on the anode 3 side of the emitting layer 5, and a hole blocking layer (not shown) may be provided on the cathode 4 side of the emitting layer 5. This allows electrons and holes to be trapped in the emitting layer 5, thereby further increasing the efficiency of generating excitons in the emitting layer 5.

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

[0319] 3 is a schematic diagram showing yet another configuration of an organic EL device according to one embodiment of the present invention. The organic EL device 12 includes a substrate 2, an anode 3, a cathode 4, and an emitting unit 30 disposed between the anode 3 and the cathode 4. The emitting unit 30 includes an emitting layer 5. The hole transport zone disposed between the anode 3 and the emitting layer 5 is formed of a hole injection layer 6a, a first hole transport layer 6b, a second hole transport layer 6c, and a third hole transport layer 6d. The electron transport zone disposed between the emitting layer 5 and the cathode 4 is formed of a first electron transport layer 7a and a second electron transport layer 7b.

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

[0321] In the present invention, a host combined with a fluorescent dopant material (fluorescent light-emitting material) is called a fluorescent host, and a host combined with a phosphorescent dopant material is called 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 that forms a phosphorescent light-emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material that forms 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. For example, a plate such as glass, quartz, or plastic can be used as the substrate. A flexible substrate can also be used. For example, a plastic substrate made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride can be used as the flexible substrate. An inorganic 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, or a mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the above metals (e.g., titanium nitride).

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

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

[0326] The hole injection layer formed in contact with the anode is formed using a material that easily injects holes regardless of the work function of the anode, and therefore materials that are commonly used as electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, and elements belonging to Group 1 or Group 2 of the periodic table) can be used. Materials with small work functions, such as elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these, can also be used. When alkali metals, alkaline earth metals, and alloys containing these are used to form the anode, vacuum deposition and sputtering methods can be used. Furthermore, when silver paste or the like is used, coating and inkjet methods 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, if present, between the hole transport layer and the anode.

[0328] Examples of hole-injecting materials that can be used other than the compound of the present invention include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.

[0329] The small organic compounds 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DNTPD), Examples of the hole injection layer material include aromatic amine compounds such as 3-[N-(9-phenylcarbazol-3-yl)-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), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1).

[0330] Polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, polymer 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 used. In addition, polymer compounds to which an acid has been added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[0331] Furthermore, it is also preferable to use an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K). [ka]

[0332] (In the above formula, R 221 ~R 226 each independently represents a cyano group, -CONH2, a carboxyl group, or -COOR 227 (R 227 represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms. 221 and R 222 , R 223 and R 224 , and R 225 and R 226 adjacent two selected from may be bonded to each other to form a group represented by -CO-O-CO-.) R 227 Examples of the alkyl group 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, and a cyclohexyl group.

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

[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 hole transport zone may include a first hole transport layer on the anode side and a second hole transport layer on the cathode side. The hole transport layer may also have a three-layer structure including, in order from the anode side, a first hole transport layer, a second hole transport layer, and a third hole transport layer. That is, the third hole transport layer may be disposed between the second hole transport layer and the light-emitting layer. In one embodiment of the present invention, the hole transport layer of the single layer structure is preferably adjacent to the light emitting layer, and the hole transport layer closest to the cathode in the multilayer structure, for example, the second hole transport layer of the two-layer structure or the third hole transport layer of the three-layer structure, is preferably adjacent to the light emitting layer. In another embodiment of the present invention, an electron blocking layer, which will be described later, may be interposed between the hole transport layer and the light emitting layer of the single layer structure, or between the hole transport layer closest to the light emitting layer in the multilayer structure and the light emitting layer. In one embodiment 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 the invention compound. Specifically, in the hole transport layer of the two-layer structure, the invention compound may be contained in either the first hole transport layer or the second hole transport layer, or may be contained in both. In another embodiment, at least one of the first to third hole transport layers contains the invention compound. Specifically, in the hole transport layer of the three-layer structure, the invention compound may be contained in only one of the first to third hole transport layers, or may be contained in only two of them, or may be contained in all of them. In one embodiment of the present invention, the compound of the present invention is preferably contained in the second hole transport layer, specifically, the compound of the present invention is preferably contained only in the second hole transport layer, or the compound of the present invention is preferably contained in both the first hole transport layer and the second hole transport layer. In one embodiment of the present invention, the compound of the invention contained in one or both of the first hole transport layer and the second hole transport layer, and the compound of the invention contained in at least one or more of the first to third hole transport layers are preferably protonated compounds from the viewpoint of production costs. The proton derivative refers to a compound of the invention in which all hydrogen atoms are proton atoms. Therefore, the present invention includes an organic EL device 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, contain an invention compound substantially consisting of protium compounds. The term "invention compound substantially consisting of protium compounds" means that the content of protium compounds relative to the total amount of the invention compound is 90 mol % or more, preferably 95 mol % or more, and more preferably 99 mol % or more (each including 100%).

[0335] As the hole transport layer material other than the compound of the present invention, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used. Examples of aromatic amine compounds 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'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The above compounds are -6 cm 2 / Vs or higher.

[0336] Examples of carbazole derivatives 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). Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. However, compounds other than those mentioned above may be used as long as they have a higher hole transporting property than an electron transporting property.

[0337] In one embodiment 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). [ka] [In the formula (21) and formula (22), L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, k is 1, 2, 3 or 4; When k is 1, L E2 represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, When k is 2, 3, or 4, multiple L E2 are identical or different from each other, When k is 2, 3, or 4, multiple L E2 are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, L which does not form a single ring and does not form a condensed ring E2represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, A 1 , B 1 , C 1 , A 2 , B 2 , C 2 , and D 2 each independently represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or -Si(R' 901 )(R' 902 )(R' 903 ) and R' 901 , R' 902 and R' 903 each independently represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R' 901 When multiple R's are present, multiple R's 901 are identical or different from each other, R' 902 When multiple R's are present, multiple R's 902 are identical or different from each other, R' 903 When multiple R's are present, multiple R's 903 are the same as or different from each other. R 901 ~R 907 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 If there are multiple R 901 are identical or different from each other, R 902 If there are multiple R 902 are identical or different from each other, R 903 If there are multiple R 903 are identical or different from each other, R 904 If there are multiple R 904 are identical or different from each other, R 905 If there are multiple R 905 are identical or different from each other, R 906 If there are multiple R 906 are identical or different from each other, R 907 If there are multiple R 907 are either identical to each other or different.]

[0338] The first hole transport layer may contain one type of compound represented by formula (21) and formula (22), or may contain multiple types of 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 selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group. More preferably, at least one of A1, B1, and C1 in formula (21), and at least one of A2, B2, C2, and D2 in formula (22) are a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[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] Examples of blue fluorescent materials that can be used in the light-emitting layer include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. Specific examples include 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.

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

[0346] Red fluorescent materials that can be used in the light-emitting layer include tetracene derivatives, diamine derivatives, etc. Specific examples include 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.

[0347] In one embodiment of the present invention, the light-emitting layer preferably contains a fluorescent light-emitting material (fluorescent dopant material).

[0348] As blue phosphorescent materials that can be used in the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used.Specific examples include 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)), and bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) acetylacetonate (abbreviation: FIracac).

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

[0350] As red phosphorescent light-emitting 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. Specific examples of the organic metal complex include 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)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP).

[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 (electron transition between different multiplicities).

[0352] Host material for the emissive layer The light-emitting layer may be configured by dispersing the above-mentioned dopant material in another material (host material). It is preferable to use a material having a lower lowest unoccupied molecular orbital (LUMO) level and a lower highest occupied molecular orbital (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) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives, (3) Condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and chrysene derivatives; (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), and 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), and bathocuproine (abbreviation: BCP); 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-Bu condensed aromatic compounds such as DNA), 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)tripylene (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), and 6,12-dimethoxy-5,11-diphenylchrysene; 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 Aromatic amine compounds such as -carbazole-3-amine (abbreviation: 2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) can be used. Multiple 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 the host material.

[0356] [ka]

[0357] [ka]

[0358] [ka]

[0359] In one embodiment of the organic EL device 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, a dopant material contained in the first light-emitting layer is different from a dopant material contained in the second light-emitting layer, or a host material contained in the first light-emitting layer is different from a host material contained in the second light-emitting layer.

[0360] In the organic EL device according to this embodiment, the light-emitting layer may contain a light-emitting compound that exhibits fluorescent emission having a main peak wavelength of 500 nm or less.

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

[0362] The light-emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less may be the above-mentioned dopant material or the above-mentioned 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 fluorescent emission having a main peak wavelength of 500 nm or less, or both of the materials may be light-emitting compounds that exhibit fluorescent emission having a main peak wavelength of 500 nm or less. In addition, 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 exhibiting a fluorescent emission having a main peak wavelength of 500 nm or less, or both light-emitting layers may contain a light-emitting compound exhibiting a fluorescent emission having a main peak wavelength of 500 nm or less. In addition, when the first light-emitting layer includes a light-emitting compound exhibiting a fluorescent emission having a main peak wavelength of 500 nm or less, only one of the dopant material and the host material included in the first light-emitting layer may be a light-emitting compound exhibiting a fluorescent emission having a main peak wavelength of 500 nm or less, or both materials may be light-emitting compounds exhibiting a fluorescent emission having a main peak wavelength of 500 nm or less. In addition, when the second light-emitting layer includes a light-emitting compound exhibiting a fluorescent emission having a main peak wavelength of 500 nm or less, only one of the dopant material and the host material included in the second light-emitting layer may be a light-emitting compound exhibiting a fluorescent emission having a main peak wavelength of 500 nm or less, or both materials may be light-emitting compounds exhibiting a fluorescent emission having 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 transporting properties (electron transporting material), and is formed between the light emitting layer and the cathode, or, if present, between the electron injection layer and the light emitting layer. The electron transport layer may have a single-layer structure or a multi-layer 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 embodiment of the present invention, the electron transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, and the electron transport layer closest to the anode in the multi-layer structure, for example, the first electron transport layer of the two-layer structure, is preferably adjacent to the light-emitting layer. In another embodiment of the present invention, a hole blocking layer, which will be described later, may be interposed between the electron transport layer of the single-layer structure and the light-emitting layer, or between the electron transport layer closest to the light-emitting layer in the multi-layer structure and the light-emitting layer.

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

[0366] Examples of metal complexes include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).

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

[0368] Examples of polymer compounds 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 materials are 10 -6 cm 2 A material having an electron mobility of 1 / Vs or more. Note that materials other than those mentioned above may be used for the electron transport layer as long as they have a higher electron transporting property than a hole transporting property.

[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 mixture of a plurality of these compounds can be used. In addition, materials having electron transport properties containing alkali metals, alkaline earth metals, or compounds thereof, specifically, materials 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 obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such a composite material has excellent electron injection and transport properties because the organic compound receives electrons from the electron donor. In this case, the organic compound is preferably a material that is excellent in transporting the received electrons, and specifically, for example, the above-mentioned materials constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor may be any material that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples of such materials include lithium, cesium, magnesium, calcium, erbium, and ytterbium. Furthermore, alkali metal oxides and alkaline earth metal oxides are preferred, and examples of such materials include lithium oxide, calcium oxide, and barium oxide. Furthermore, a Lewis base such as magnesium oxide can also be used. Furthermore, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.

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

[0372] Insulation layer In organic EL elements, pixel defects due to leakage and short circuits are likely to occur because an electric field is applied to an ultra-thin film. To prevent this, an insulating layer made of an insulating thin film may be inserted between a pair of electrodes. Examples of materials used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, etc. Mixtures or laminates of these materials may also be used.

[0373] Space Layer The spacer layer is a layer provided between a fluorescent light-emitting layer and a 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 for the purpose of adjusting the carrier balance when the fluorescent light-emitting layer and the phosphorescent light-emitting layer are laminated, for example. 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 preferable that the spacer layer is made of a material having both electron transport properties and hole transport properties. In addition, in order to prevent the diffusion of triplet energy in the adjacent phosphorescent light-emitting layer, it is preferable that the triplet energy is 2.6 eV or more. 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 into 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 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 a 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 total thickness 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] As an embodiment of the organic EL element of the present invention, for example, An organic EL element having the above two-layer hole transport layer, a first embodiment in which the second hole transport layer comprises a compound according to the invention and the first hole transport layer does not comprise a compound according to the invention; a second embodiment, in which both the first hole transport layer and the second hole transport layer comprise a compound according to the invention; A third embodiment in which the first hole transport layer comprises a compound according to the invention and the second hole transport layer does not comprise a compound according to the invention; An organic EL element having the above three-layer hole transport layer, a fourth embodiment, in which the first hole transport layer comprises a compound according to the invention and the second and third hole transport layers do not comprise a compound according to the invention; a fifth embodiment, in which the second hole transport layer comprises a compound according to the invention and the first and third hole transport layers do not comprise a compound according to the invention; a sixth embodiment, in which the third hole transport layer comprises a compound according to the invention and the first and second hole transport layers do not comprise a compound according to the invention; a seventh embodiment, in which the first and second hole transport layers comprise a compound of the invention and the third hole transport layer does not comprise a compound of the invention; an eighth embodiment, in which the first and third hole transport layers comprise a compound of the invention and the second hole transport layer does not comprise a compound of the invention; a tenth embodiment, in which the second and third hole transport layers comprise a compound of the invention and the first hole transport layer does not comprise a compound of the 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 equipment The organic EL element can be used in display components such as organic EL panel modules, display devices for televisions, mobile phones, personal computers, and electronic devices such as light-emitting devices for lighting and vehicle lamps. EXAMPLES

[0380] The present invention will be described in more detail below using examples, but the present invention is not limited to the following.

[0381] Compounds used in the production of organic EL devices in the examples [ka]

[0382] Comparative compounds used in the manufacture of organic EL devices of comparative examples [ka]

[0383] Other compounds used in the manufacture of organic EL devices in the examples and comparative examples [ka]

[0384] [ka]

[0385] [ka]

[0386] Fabrication of organic electroluminescence devices Example 1-1 A 25 mm x 75 mm x 1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm. The glass substrate with the cleaned transparent electrode was attached to a substrate holder in a vacuum deposition apparatus, and compound HI-1 was deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 5 nm. Next, compound 1 was deposited as compound HT-1 on the hole injection layer to form a first hole transport layer having a thickness of 75 nm. Next, the compound HT-2 was deposited on the first hole transport layer to form a second hole transport layer having a thickness of 15 nm. Next, on the second hole transport layer, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited to form a light-emitting layer having a thickness of 20 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 98:2. Next, the compound ET-1 was deposited on the light-emitting layer to form a first electron transport layer having a thickness of 15 nm. Next, a second electron transport layer having a thickness of 15 nm was formed on the first electron transport layer by co-evaporation of the compound ET-2 and Li. The mass ratio of the compound ET-2 to Li (ET-2:Li) was 96:4. Next, metallic Al was evaporated onto the second electron transport layer to form a metal cathode having a thickness of 80 nm. The layer structure of the organic EL device of Example 1-1 thus obtained 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 configuration, the numbers in parentheses indicate film thicknesses (nm) and the ratios are mass ratios. Comparative Examples 1-1 to 1-3 Organic EL devices were prepared in the same manner as in Example 1, except that the second hole transport layer material was changed from Compound 1 to Comparative Compounds 1, 2, and 3, respectively.

[0387] Evaluation of organic EL elements For the organic EL devices prepared in Example 1-1 and Comparative Examples 1-1 to 1-3, the current density was 10 mA / cm 2 A voltage was applied to the organic EL element so as to satisfy the following formula: 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 satisfying the requirements of the present invention (Compound 1 in Example 1-1) exhibits significantly improved driving voltage and EQE values ​​compared to monoamines not satisfying the requirements of the present invention (Comparative Compounds 1, 2, and 3 in Comparative Examples 1-1 to 1-3).

[0390] Example 2-1 A 25 mm x 75 mm x 1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm. The glass substrate with the cleaned transparent electrode was attached to a substrate holder in a vacuum deposition apparatus, and compound HI-1 was deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 5 nm. Next, compound HT-3 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 37.5 nm. Next, compound 1 was deposited as compound HT-1 on the first hole transport layer to form a second hole transport layer having a thickness of 37.5 nm. Next, the compound HT-2 was deposited on the second hole transport layer to form a third hole transport layer having a thickness of 15 nm. Next, on the third hole transport layer, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited to form a light-emitting layer having a thickness of 20 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 98:2. Next, the compound ET-1 was vapor-deposited on this light-emitting layer to form a first electron transport layer having a thickness of 15 nm. Next, a second electron transport layer having a thickness of 15 nm was formed on the first electron transport layer by co-evaporation of the compound ET-2 and Li. The mass ratio of the compound ET-2 to Li (ET-2:Li) was 96:4. Next, metallic Al was evaporated onto the second electron transport layer to form a metal cathode having a thickness of 80 nm. The layer structure of the organic EL device 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 configuration, the numbers in parentheses indicate film thicknesses (nm) and the ratios are mass ratios.

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

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

[0393] Evaluation of organic EL elements For the organic EL devices prepared in Examples 2-1, 2-2, Comparative Example 2-1, and Comparative Example 2-2, the current density was 10 mA / cm 2 A voltage was applied to the organic EL element so as to satisfy the following formula: 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 2.

[0394] [Table 2]

[0395] As is clear from the results in Table 2, the compounds satisfying the requirements of the present invention (Example 2-1, compounds 1 and 2 in Example 2-2) exhibit significantly improved drive voltage and EQE values ​​compared to the monoamines not satisfying the requirements of the present invention (Comparative Example 2-1, comparative compounds 1 and 3 in Comparative Example 2-2).

[0396] Example 3-1 A glass substrate (Geomatec Co., Ltd.) with an ITO transparent electrode (anode) measuring 25 mm x 75 mm x 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm. The glass substrate with the transparent electrode after cleaning was attached to a substrate holder of a vacuum deposition apparatus, and the compounds HT-4 and HI-2 were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 10 nm. The mass ratio of the compounds HT-4 and HI-2 (HT-4:HI-2) was 95:5. Next, the compound HT-4 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 30 nm. Next, Compound 1 was deposited as a second hole transport material HT-1 on the first hole transport layer to form a second hole transport layer having a thickness of 40 nm. Next, the compound HT-2 was deposited on the second hole transport layer to form a third hole transport layer having a thickness of 15 nm. Next, on the third hole transport layer, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited to form a light-emitting layer having a thickness of 20 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 98:2. Next, the compound ET-1 was vapor-deposited on this light-emitting layer to form a first electron transport layer having a thickness of 10 nm. Next, a second electron transport layer having a thickness of 20 nm was formed on the first electron transport layer by co-evaporation of the compound ET-2 and Li. The mass ratio of the compound ET-2 to Li (ET-2:Li) was 96:4. Next, metallic Al was evaporated onto the second electron transport layer to form a metal cathode having a thickness of 80 nm. The layer structure of the organic EL device of Example 2-1 thus obtained 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 configuration, the numbers in parentheses indicate film thicknesses (nm) and the ratios are mass ratios.

[0397] Examples 3-2 to 3-6 Organic EL devices were produced 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] Examples 3-7 An organic EL device was prepared 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 Organic EL devices were prepared 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 elements For the organic EL devices prepared in Examples 3-1 to 3-7, Comparative Example 3-1, and Comparative Example 3-2, the current density was 10 mA / cm 2 A voltage was applied to the organic EL element so as to satisfy the following formula: 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 3.

[0401] [Table 3]

[0402] As is clear from the results in Table 3, the compounds satisfying the requirements of the present invention (compounds 1, 4 to 8, and compound 3 in Examples 3-1 to 3-7) exhibit significantly improved drive voltage and EQE values ​​compared to monoamines not satisfying the requirements of the present invention (comparative example 3-1, comparative compound 1, and comparative compound 3 in comparative example 3-2).

[0403] Example 4-1 A 25 mm x 75 mm x 1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm. The glass substrate with the transparent electrode after cleaning was attached to a substrate holder of a vacuum deposition apparatus, and the compound 1 as a hole transport material HT-1 and the compound HI-2 were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, to form a hole injection layer with a thickness of 10 nm. The mass ratio of the compound HT-1 to the compound HI-2 (HT-1:HI-2) was 97:3. Next, Compound 1 was deposited as a first hole transport material HT-1 on the hole injection layer to form a first hole transport layer having a thickness of 80 nm. Next, the compound HT-5 was deposited on the first hole transport layer to form a second hole transport layer having a thickness of 5 nm. Next, on the second hole transport layer, compound BH-2 (host material) and compound BD-2 (dopant material) were co-deposited to form a light-emitting layer having a thickness of 20 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 99:1. Next, the compound ET-5 was evaporated onto the light-emitting layer to form a first electron transport layer having a thickness of 5 nm. Next, the compounds ET-6 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer having a thickness of 25 nm. The mass ratio of the compounds ET-6 and Liq (ET-6:Liq) was 50:50. Next, metal Yb was evaporated onto the second electron transport layer to form an electron injection layer having a thickness of 1 nm. Next, metallic Al was evaporated onto the electron injection layer to form a metal cathode with a thickness of 50 nm. The layer structure of the organic EL device of Example 2-1 thus obtained 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 configuration, the numbers in parentheses indicate film thicknesses (nm) and the ratios are mass ratios.

[0404] Examples 4-2 and 4-3 Organic EL devices were prepared 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 Organic EL devices were prepared 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 organic EL elements For the organic EL devices prepared in Examples 4-1 to 4-3, Comparative Example 4-1, and Comparative Example 4-2, the current density was 10 mA / cm 2 A voltage was applied to the organic EL element so as to satisfy the following formula: 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 4.

[0407] [Table 4]

[0408] As is clear from the results in Table 4, the compounds satisfying the requirements of the present invention (compounds 1, 4, and 6 in Examples 4-1 to 4-3) exhibit significantly improved drive voltage and EQE values ​​compared to monoamines not satisfying the requirements of the present invention (comparative compounds 3 and 4 in Comparative Example 4-1 and Comparative Example 4-2).

[0409] Compounds synthesized in the synthesis examples [ka]

[0410] <Synthesis of Compounds> Intermediate synthesis example 1: Synthesis of intermediate A [ka]

[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 stirred at room temperature. After adding all the components, the mixture was stirred under reflux for 1 hour to prepare an organomagnesium reactant. In a separate reactor, 1-indanone (1.98 g, 15 mmol) and THF (13 mL) were added under an argon atmosphere, and the previously prepared organomagnesium reactant was added dropwise. The mixture was then stirred under reflux for 5 hours. The reaction solution was cooled to room temperature, and saturated aqueous ammonium chloride solution and ethyl acetate were added and stirred. After removing the aqueous layer using a separatory funnel, the resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain an orange oil. The resulting oil was dissolved in xylene (75 mL), p-toluenesulfonic acid monohydrate (8.56 g, 45 mmol) was added, and the mixture was heated to 140°C and stirred for 5 hours. After cooling, water was added, the aqueous layer was removed, and the resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain intermediate A as a colorless solid (1.82 g). The yield in the two steps was 40%.

[0412] Intermediate synthesis example 2: Synthesis of intermediate B [ka]

[0413] Intermediate B was obtained by the same procedure as in Intermediate Synthesis Example 1, except that 3,3-dimethyl-1-indanone was used instead of 1-indan used in Intermediate Synthesis Example 1. The yield in the two steps was 41%.

[0414] Synthesis Example 1: Synthesis of Compound 1 [ka]

[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. The reaction solution was cooled to room temperature and then 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%. Mass spectrometry revealed that the product obtained was Compound 1, with an m / e of 627 for a molecular weight of 627.29.

[0416] Synthesis Example 2: Synthesis of Compound 2 [ka]

[0417] Compound 2 was obtained by the same procedure as in Synthesis Example 1, except that 2-bromo-1',3'-dihydrospiro[fluorene-9,2'-indene] synthesized by a method similar to that described in WO 2004 / 110968 was used instead of intermediate A used in Synthesis Example 1. Mass spectrometry revealed that the product was compound 2, with a molecular weight of 627.29 and an m / e of 627.

[0418] Synthesis Example 3: Synthesis of Compound 3 [ka]

[0419] Compound 3 was obtained in the same manner as in Synthesis Example 1, except that Intermediate B was used instead of Intermediate A used in Synthesis Example 1. Mass spectrometry revealed that the product was compound 3, with a molecular weight of 655.32 and an m / e of 655.

[0420] Intermediate synthesis example 3: Synthesis of intermediate C [ka]

[0421] Compound C was obtained in a yield of 39% by the same procedure as in Intermediate Synthesis Example 1, except that 6-(tert-butyl)-2,3-dihydro-1H-inden-1-one was used instead of 1-indanone used in Intermediate Synthesis Example 1.

[0422] Synthesis Example 4: Synthesis of Compound 4 [ka]

[0423] Compound 4 was obtained by carrying out the same procedure as in Synthesis Example 1, except that N-([1,1':4',1''-terphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-2-amine was used instead of 2-(2-biphenylyl)amino-9,9-dimethylfluorene used in Synthesis Example 1. Mass spectrometry revealed that the product obtained was Compound 4, with an m / e of 704 for a molecular weight of 703.93.

[0424] Synthesis Example 5: Synthesis of Compound 5 [ka]

[0425] Compound 5 was obtained in the same manner as in Synthesis Example 1, except that Intermediate C was used instead of Intermediate A used in Synthesis Example 1. Mass spectrometry revealed that the product obtained was Compound 5, with an m / e of 684 for a molecular weight of 683.94.

[0426] Synthesis Example 6: Synthesis of Compound 6 [ka]

[0427] Compound 6 was obtained by carrying out the same procedure as in Synthesis Example 1, except that N-([1,1'-biphenyl]-2-yl)-9,9-diphenyl-9H-fluoren-2-amine was used instead of 2-(2-biphenylyl)amino-9,9-dimethylfluorene used in Synthesis Example 1. Mass spectrometry revealed that the product obtained was Compound 6, with an m / e of 752 for a molecular weight of 751.97.

[0428] Synthesis Example 7: Synthesis of Compound 7 [ka]

[0429] Compound 7 was obtained by carrying out the same procedure as in Synthesis Example 1, except that N-(2-(dibenzo[b,d]furan-4-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine was used instead of 2-(2-biphenylyl)amino-9,9-dimethylfluorene used in Synthesis Example 1. Mass spectrometry revealed that the product obtained was Compound 7, with an m / e of 718 for a molecular weight of 717.91.

[0430] Synthesis Example 8: Synthesis of Compound 8 [ka]

[0431] Compound 8 was obtained by carrying out the same procedure as in Synthesis Example 1, except that N-([1,1':2',1''-terphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-2-amine was used instead of 2-(2-biphenylyl)amino-9,9-dimethylfluorene used in Synthesis Example 1. Mass spectrometry revealed that the product obtained was compound 8, with an m / e of 704 for a molecular weight of 703.93. [Explanation of symbols]

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

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. Z １ , Z ２ , R １３Ａ , R １４Ａ , R １５ ~R １８ , and R ７ ~R １０ The substituent which the alkyl group, the aryl group, and the heteroaryl group represented by the formula (I) may have is selected from an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 12 ring carbon atoms, and a heteroaryl group having 5 to 18 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, adjacent pairs of groups do not bond to each other to form a ring. R １５ ~R １８ Among these, adjacent pairs of groups do not bond to each other to form a ring. R １Ａ , R ２Ａ , Y １ , and Y ２ is a protium atom. L １ represents an 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 , = CR Ａ R Ｂ It is. R ２１ ~R ２４ One selected from is a single bond bonding to *b1. R Ａ and R Ｂ are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. Ａ and R Ｂ may or may not be bonded to each other to form a ring. R Ａ and R Ｂ The substituent which the alkyl group and the aryl group represented by the formula (I) may have is selected from an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heteroaryl group having 5 to 18 ring atoms. The R that is not a single bond ２１ ~R ２４ , and R ２５ ~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 ２８ The substituent which the alkyl group, the aryl group, and the heteroaryl group represented by the formula (I) may have is selected from an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heteroaryl group having 5 to 18 ring atoms. The R that is not a single bond ２１ ~R ２４ do not bond to each other to form a ring, and R ２５ ~R ２８ do not bond to each other to form a ring. L ２ represents an unsubstituted arylene group having 6 to 12 ring carbon atoms. n2 is 0 or 1. When n2 is 0, R ２１ ~R ２４ One selected from the group consisting of the central nitrogen atom N ＊ Bind to. Ar １ represents 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 １ The substituent which the aryl group and the heteroaryl group represented by the formula (I) may have is selected from an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 12 ring carbon atoms, and a heteroaryl group having 5 to 18 ring atoms. Ar ２ represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. m is 0. R ３１ ~R ３４ is a hydrogen atom. 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 is a hydrogen atom or R １１ ~R １４ , R １５ ~R １８ , and R ７ ~R １０ one of which is an unsubstituted alkyl group having 1 to 30 carbon atoms or an unsubstituted aryl group having 6 to 12 ring carbon atoms, and the other is a hydrogen atom. 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, adjacent pairs of groups do not bond to each other to form a ring. R １５ ~R １８ Among these, adjacent pairs of groups do not bond to each other to form a ring. R １Ｂ , R ２Ｂ , R ５Ｂ , and R ６Ｂ is a hydrogen atom. R １Ｂ and R ２Ｂ do not combine with each other to form a ring. R ５Ｂ and R ６Ｂ do not combine with each other to form a ring. L ３ represents an 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 Ar is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. ３ The substituent which the aryl group represented by formula (I) may have is selected from an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 12 ring carbon atoms, and a heteroaryl group having 5 to 18 ring atoms. L ４ represents an 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). 【Chemistry 3】 (In formula (3-1), *** is L ４ represents the bonding position to X ２ , = CR Ｃ R Ｄ It is. R ２１Ｂ ~R ２４Ｂ One selected from is a single bond bonding to *b2. The R that is not a single bond ２１Ｂ ~R ２４Ｂ , R ２５Ｂ ~R ２８Ｂ are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. ２１Ｂ ~R ２８Ｂ The substituent that the alkyl group represented by the formula (I) may have is selected from an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heteroaryl group having 5 to 18 ring atoms. The R that is not a single bond ２１Ｂ ~R ２４Ｂ do not bond to each other to form a ring, and R ２５Ｂ ~R ２８Ｂ do not bond to each other to form a ring. R Ｃ and R Ｄ are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. Ｃ and R Ｄ The substituent that the alkyl group represented by the formula (I) may have is selected from an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heteroaryl group having 5 to 18 ring atoms. In formula (1B), 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 4】 [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. R ２１ , R ２２ , and R ２４ The compound according to claim 2, wherein one of is a single bond bonded to *b1.

4. Represented by the formula (1A) or (1A-1), 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 3, wherein is a phenylene group.

5. The compound according to claim 1, represented by any one of the following formulas (1A-3) to (1A-5): 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 [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. 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 (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. The R that is not a single bond 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).

6. The compound according to claim 1, represented by any one of the following formulas (1A-6) to (1A-8): 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 [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).

7. Represented by any one of the formulas (1A), (1A-1), and (1A-3) to (1A-8), Ar １ The compound according to any one of claims 1 to 3, wherein is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

8. Represented by any one of the formulas (1A), (1A-1), and (1A-3) 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.

9. The compound according to claim 1, represented by the following formula (1B-1): 【Chemistry 11】 [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).

10. Ar ３ is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

11. Represented by any one of the formulas (1B) and (1B-1), 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 of claim 1 , wherein is a phenylene group.

12. The compound according to claim 1, represented by any one of the following formulas (1B-3) to (1B-9): 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 [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).

13. Represented by any one of the formulas (1B), (1B-1), and (1B-3) to (1B-9), Ar ３ The compound according to claim 1, represented by any one of the following formulas (2A) to (2F): 【Chemistry 19】 (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. １１１ ~R １１５ The substituent which the alkyl group, the aryl group, and the heteroaryl group represented by the formula (I) may have is selected from an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heteroaryl group having 5 to 18 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 20】 (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. １２１ ~R １２８ The substituent which the alkyl group and the aryl group represented by the formula (I) may have is selected from an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heteroaryl group having 5 to 18 ring 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 21】 (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. １３１ ~R １４０ The substituent which the alkyl group and the aryl group represented by the formula (I) may have is selected from an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heteroaryl group having 5 to 18 ring 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. 【Chemical 22】 (In formula (2D), ・*28 is L ３ is the binding site to ・n12 is 0. ・R １４１ ~R １４４ One selected from is a single bond binding to *29. R which is not a single bond １４１ ~R １４４ , R １４５ ~R １４８ , and R 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. １４１ ~R １４８ The substituent which the alkyl group, the aryl group, and the heteroaryl group represented by the formula (I) may have is selected from an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heteroaryl group having 5 to 18 ring atoms. R which is not a single bond １４１ ~R １４４ , R １４５ ~R １４８ , and R ２００ ~R ２０３ Adjacent two selected from the following are not bonded to each other to form a ring. ・R Ｅ and R Ｆ are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon 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 bonded to each other 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. Ｅ and R Ｆ The substituents which the alkyl group and the aryl group represented by the formula (I) may have are selected from an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heteroaryl group having 5 to 18 ring atoms. 【Chemistry 23】 (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 two adjacent ones selected from the group consisting of 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. 【Chemistry 24】 (In formula (2F), ・*32 is L ３ is the binding site to ・R １８１ ~R １９２ One selected from is a single bond bonded 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. １８１ ~R １９２ The substituent which the alkyl group and the aryl group represented by the formula (I) may have is selected from an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heteroaryl group having 5 to 18 ring 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.

14. Ar １ The compound according to any one of claims 1 to 3, wherein is a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.

15. The compound according to any one of claims 1 to 3, wherein the compound represented by formula (1A) or formula (1B) contains at least one deuterium atom.

16. The compound according to claim 1, which is any one of compounds 1, 2, 4 to 8 below. 【Chemistry 25】

17. A material for an organic electroluminescence device, comprising the compound according to any one of claims 1 to 3.

18. The material for an organic electroluminescence device according to claim 17 , wherein the compound is a hole transport layer material.

19. 4. An organic electroluminescence element having a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer being composed of a single layer 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 comprises the compound according to any one of claims 1 to 3.

20. 20. The organic electroluminescent device of claim 19, wherein the organic layer comprises a hole transporting zone between the anode and the light emitting layer, the hole transporting zone comprising the compound.

21. 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 20 , wherein at least one of the first hole transport layer and the second hole transport layer contains the compound.

22. The organic electroluminescent device according to claim 21 , wherein the second hole transport layer comprises the compound.

23. 22. The organic electroluminescence device according to claim 21, wherein the light-emitting layer and the second hole transport layer are in direct contact with each other.

24. 22. The organic electroluminescence device according to claim 21, 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.

25. the hole transport zone includes a first hole transport layer on the anode side, a second hole transport layer on the cathode side, and a third layer on the cathode side; The organic electroluminescence device according to claim 20 , wherein at least one of the first hole transport layer and the second hole transport layer contains the compound.

26. 21. The organic electroluminescence device according to claim 20, wherein the light-emitting layer includes a layer containing a light-emitting compound that exhibits fluorescent emission having a main peak wavelength of 500 nm or less.

27. 20. The organic electroluminescence device according to claim 19, wherein the light-emitting layer is a single layer.

28. An electronic device comprising the organic electroluminescence device according to claim 19.

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