Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device

Abstract

The present invention provides a compound that further improves the performance of an organic EL element, and relates to a compound represented by formula (1) and containing at least one deuterium atom in the molecule. (Each symbol in the formula is as defined in the description.)

Description

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

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

[0002] Generally, an organic electroluminescent device (hereinafter sometimes referred to as "organic EL device") 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. The injected electrons and holes recombine in the light-emitting region to generate an excited state, and light is emitted when the excited state returns to the ground state. Therefore, the development of a material that efficiently transports electrons or holes to the light-emitting region and facilitates the recombination of electrons and holes is important for obtaining high-performance organic EL devices.

[0003] Patent Documents 1 to 6 disclose compounds used as materials for organic electroluminescence devices.

[0004] Chinese Patent Application Publication No. 116143734 Chinese Patent Application Publication No. 116082297 U.S. Patent Application Publication No. 2018 / 0083197 International Publication No. 2023 / 287228 International Publication No. 2023 / 068794 International Publication No. 2014 / 002873

[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 (particularly, external quantum efficiency and lifetime) of an organic EL device, an organic EL device with further improved device performance, and an electronic device including such an organic EL device.

[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 (1) has improved performance:

[0008] In one aspect, the present invention provides a compound represented by the following formula (1) (hereinafter, also referred to as compound (1)):

[0009] [In formula (1), ・N ＊ is the central nitrogen atom. X is an oxygen atom or a sulfur atom. Y ２ and Y ３ One selected from is a single bond bonded to *a. １ , R ４ and the Y which is not a single bond. ２ and Y ３ 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 do not bond to each other to form a ring. ５ ~R １０ are hydrogen atoms, or any two or more of them bond to each other to form a substituted or unsubstituted ring. １１ ~R １４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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. １１ ~R １４ are not bonded to each other and do not form a ring. １ and L ２ are each independently 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. m1 and m2 are each independently 0 or 1. When m1 is 0, Ar １ N ＊ When m2 is 0, Ar ２ N ＊ Bonds to L ３ and L４ are each independently a substituted or unsubstituted arylene group having 6 to 10 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 10 ring atoms. n1 is 0 or 1. When n1 is 0, R １３ and the carbon atom bonded to R １４ The carbon atoms bonded to both of the carbon atoms bonded to N ＊ n2 is 0 or 1. When n2 is 0, R １１ and the carbon atom bonded to R １４ The carbon atoms bonded to both of the carbon atoms bonded to Y ２ and Y ３ Ar binds to one selected from １ and Ar ２ are each independently a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 20 ring atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 ring atoms. １ is an unsubstituted 4,3'-biphenylene group, and Ar １ is a substituted or unsubstituted heteroaryl group having 3 to 20 ring atoms, １ , and m2 is 1, and L ２ is an unsubstituted 4,3'-biphenylene group, and Ar ２ is a substituted or unsubstituted heteroaryl group having 3 to 20 ring atoms, ２are each independently selected from a substituted or unsubstituted 1-carbazolyl group, a substituted or unsubstituted 2-carbazolyl group, a substituted or unsubstituted 3-carbazolyl group, a substituted or unsubstituted 4-carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted benzofurocarbazolyl group, a substituted or unsubstituted benzothienocarbazolyl group, and a substituted or unsubstituted indenocarbazolyl group. １ When Ar is a biphenyl group having a substituent, the substituent is the following substituent A. When m2 is 0 and Ar ２ When m1 is 1, L is a biphenyl group having a substituent, the substituent is the following substituent A. １ is a phenylene group, and Ar １ When m2 is 1, L is a phenyl group having a substituent, the substituent is the following substituent A. ２ is a phenylene group, and Ar ２ When Ar is a phenyl group having a substituent, the substituent is the following substituent A. １ and Ar ２ are both unsubstituted naphthyl groups, m1 and m2 are both 1, and L １ and L ２ When both are unsubstituted phenylene groups, L １ and L ２ One of the groups is an unsubstituted o-phenylene group, an unsubstituted m-phenylene group, or an unsubstituted p-phenylene group, and the other group is an unsubstituted o-phenylene group or an unsubstituted p-phenylene group. １ When Ar is a phenyl group having a substituent, the substituent is the following substituent B. When m2 is 0 and Ar ２ When Ar is a phenyl group having a substituent, the substituent is the following substituent B. １ and Ar ２are both unsubstituted dibenzofuranyl groups, m1 and m2 are both 1, and L １ and L ２ When both are unsubstituted phenylene groups, L １ and L ２ One of the groups is an unsubstituted o-phenylene group, an unsubstituted m-phenylene group, or an unsubstituted p-phenylene group, and the other group is an unsubstituted o-phenylene group or an unsubstituted m-phenylene group. １ When Ar is a phenyl group having a substituent, the substituent is the following substituent C. ２is a phenyl group having a substituent, the substituent is the following substituent C. However, the substituent A is selected from a group which the following substituent D may take, an unsubstituted dibenzofuranyl group, and an unsubstituted naphthyl group. The substituent B is selected from a group which the following substituent D may take, an unsubstituted 9-carbazolyl group, and an unsubstituted dibenzofuranyl group. The substituent C is selected from a group which the following substituent D may take, an unsubstituted naphthyl group, and an unsubstituted 9-carbazolyl group. the substituent D is a cyano group; a halogen atom; a phosphine oxide group substituted with an unsubstituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted alkyl group having 1 to 30 carbon atoms; an unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms; an unsubstituted aralkyl group having 7 to 36 carbon atoms; an unsubstituted alkoxy group having 1 to 30 carbon atoms; an unsubstituted aryloxy group having 6 to 30 ring carbon atoms; a mono-, di-, or tri-substituted silyl group having a substituent selected from an unsubstituted alkyl group having 1 to 30 carbon atoms and an unsubstituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted haloalkyl group having 1 to 30 carbon atoms; an unsubstituted haloalkoxy group having 1 to 30 carbon atoms; a boryl group substituted with an unsubstituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted alkylthio group having 1 to 30 carbon atoms; an unsubstituted arylthio group having 6 to 30 ring carbon atoms; and unsubstituted phenyl group, unsubstituted tolyl group, unsubstituted xylyl group, unsubstituted ethylphenyl group, unsubstituted anthryl group, unsubstituted phenanthryl group, unsubstituted biphenylyl group, and unsubstituted anthryl group; unsubstituted 1-carbazolyl group, unsubstituted 2-carbazolyl group, unsubstituted 3-carbazolyl group, unsubstituted 4-carbazolyl group, unsubstituted dibenzothiophenyl group, unsubstituted benzonaphthofuranyl group, unsubstituted benzonaphthothiophenyl group, unsubstituted indolocarbazolyl group, unsubstituted benzofurocarbazolyl group, unsubstituted benzothienocarbazolyl group, unsubstituted indenocarbazolyl group, and unsubstituted dibenzocarbazolyl group.

[0010] In another aspect, the present invention provides a material for an organic electroluminescence device, comprising compound (1).

[0011] In still another aspect, the present invention provides an organic electroluminescence device having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer consists of a single layer or multiple layers including an emitting layer, and at least one layer selected from the group consisting of a single layer and multiple layers constituting the organic layer contains compound (1).

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

[0013] An organic EL device including an organic EL device containing a compound represented by formula (1) exhibits improved device performance.

[0014] It is a schematic diagram showing the configuration of an organic EL element according to one embodiment of the present invention, a schematic diagram showing the configuration of an organic EL element according to another embodiment of the present invention, and a schematic diagram showing the configuration of an organic EL element according to still another embodiment of the present invention.

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

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

[0017] As used herein, the term "number of ring carbon atoms" refers to 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 (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are 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, a 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and a 9,9'-spirobifluorenyl group has 25 ring carbon atoms. When a benzene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms 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 a benzene ring substituted with an alkyl group is 6. Furthermore, when the naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms 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 ring, a fused ring, and a ring assembly). Atoms that do not constitute the ring (e.g., hydrogen atoms terminating the bonds of atoms constituting the ring) and atoms contained in the substituent when the ring is substituted with a substituent are not included in the number of ring atoms. 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 the 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. Furthermore, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring, so the number of ring atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

[0019] In this specification, the "number of carbon atoms XX to YY" in the expression "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 this specification, the "number of atoms XX to YY" in the expression "substituted or unsubstituted ZZ group having number of atoms XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of substituents when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0021] In this specification, an unsubstituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group". In this specification, "unsubstituted" in the case of a "substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protist atom, a deuterium atom, or a tritium atom. Furthermore, in this specification, "substituted" in the case of a "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced 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 in this specification" The substituents described in this specification are explained below. Unless otherwise specified, each substituent described in this specification is defined as follows.

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

[0024] "Substituted or Unsubstituted Aryl Group" Specific examples (Specific Example Group G1) of the "substituted or unsubstituted aryl group" described herein include the following unsubstituted aryl group (Specific Example Group G1A) and substituted aryl group (Specific Example Group G1B). (Here, an unsubstituted aryl group refers to a case where a "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and a substituted aryl group refers to a case where a "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" simply refers to both an "unsubstituted aryl group" and a "substituted aryl group." A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with substituents. Examples of the "substituted aryl group" include a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with substituents in the "unsubstituted aryl group" of the following Specific Example Group G1A, and examples of the substituted aryl group of the following Specific Example Group G1B. It should be noted that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl groups" described in this specification also include groups in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl groups" of the following specific example group G1B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted aryl groups" of the following specific example group G1B is further replaced with a substituent.

[0025] Unsubstituted aryl groups (specific example group G1A): a phenyl group, a p-biphenyl group, an 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, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an m-terphenyl-3'-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 benzanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a triphenylenyl group, a benzotriphenylenyl group, a tetracenyl group, pentacenyl group, fluorenyl group, 9,9'-spirobifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, fluoranthenyl group, benzofluoranthenyl group, perylenyl group, and monovalent aryl groups derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15):

[0026]

[0027]

[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 the above general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0029] "Substituted or Unsubstituted Heterocyclic Group" The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom among 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 fused ring group. The "heterocyclic group" described herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described herein include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, an unsubstituted heterocyclic group refers to when a "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and a substituted heterocyclic group refers to when a "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when simply referring to a "heterocyclic group", it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group". A "substituted heterocyclic group" means a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with substituents. Specific examples of the "substituted heterocyclic group" include groups in which hydrogen atoms of an "unsubstituted heterocyclic group" in the following specific example group G2A are replaced, and examples of substituted heterocyclic groups in the following specific example group G2B. The examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic groups" described in this specification also include groups in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic groups" of specific example group G2B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted heterocyclic groups" of specific example group G2B is further replaced with a substituent.

[0030] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from 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 substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced with substituents (specific example group G2B4).

[0032] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolidinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, an indazolyl group, a phenanthrolinyl group, a phenanthridinyl group, an acridinyl group, a phenazinyl group, a carbazolyl group, Benzocarbazolyl group, morpholino group, phenoxazinyl group, phenothiazinyl group, azacarbazolyl group, and diazacarbazolyl group.

[0033] Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): a furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a xanthenyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a benzoxazolyl group, a benzisoxazolyl group, a phenoxazinyl group, a morpholino group, a dinaphthofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, an azanaphthobenzofuranyl group, and a diazanaphthobenzofuranyl group.

[0034] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a benzothiophenyl group (benzothienyl group), an isobenzothiophenyl group (isobenzothienyl group), a dibenzothiophenyl group (dibenzothienyl group), a naphthobenzothiophenyl group (naphthobenzothienyl group), a benzothiazolyl group, a benzisothiazolyl group, a phenothiazinyl group, a dinaphthothiophenyl group (dinaphthothienyl group), an azadibenzothiophenyl group (azadibenzothienyl group), a diazadibenzothiophenyl group (diazadibenzothienyl group), an azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and a 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]

[0037]

[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 CH ２ However, X Ａ and Y Ａ At least one of X is an oxygen atom, a sulfur atom, or NH. Ａ and Y Ａ At least one of the groups is NH or CH ２ In this case, the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) may contain any of these NH, CH ２ and monovalent groups obtained by removing one hydrogen atom from the group consisting of:

[0039] Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): a (9-phenyl)carbazolyl group, a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a (9-naphthyl)carbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a methylbenzimidazolyl group, an ethylbenzimidazolyl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenylquinazolinyl group, and a biphenylylquinazolinyl group.

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

[0041] Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3): a phenyldibenzothiophenyl group, a methyldibenzothiophenyl group, a 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 "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 CH.

[0044] "Substituted or Unsubstituted Alkyl Group" Specific examples (Specific Example Group G3) of the "substituted or unsubstituted alkyl group" described herein include the following unsubstituted alkyl group (Specific Example Group G3A) and substituted alkyl group (Specific Example Group G3B). (Here, the term "unsubstituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and the term "substituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereinafter, the term "alkyl group" includes both an "unsubstituted alkyl group" and a "substituted alkyl group." A "substituted alkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced with substituents. 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 substituents, and the examples of the substituted alkyl group (Specific Example Group G3B). In this specification, the alkyl group in an "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the term "unsubstituted alkyl group" includes a straight-chain "unsubstituted alkyl group" and a branched "unsubstituted alkyl group." The examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes groups in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" of specific example group G3B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted alkyl group" of specific example group G3B is further replaced with a substituent.

[0045] Unsubstituted alkyl groups (specific example group G3A): a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, and a t-butyl group.

[0046] Substituted alkyl groups (specific example group G3B): a heptafluoropropyl group (including isomers), a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, and a trifluoromethyl group.

[0047] "Substituted or Unsubstituted Alkenyl Group" Specific examples (Specific Example Group G4) of the "substituted or unsubstituted alkenyl group" described herein include the following unsubstituted alkenyl group (Specific Example Group G4A) and substituted alkenyl group (Specific Example Group G4B). (Here, an unsubstituted alkenyl group refers to a case where a "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and a "substituted alkenyl group" refers to a case where a "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply refers to both an "unsubstituted alkenyl group" and a "substituted alkenyl group." A "substituted alkenyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced with substituents. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl groups" (specific example group G4A) having a substituent, and examples of substituted alkenyl groups (specific example group G4B). The examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl group" described in this specification also includes groups in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl groups" of specific example group G4B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted alkenyl groups" of specific example group G4B is further replaced with a substituent.

[0048] Unsubstituted alkenyl groups (specific example group G4A): a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, and a 3-butenyl group.

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

[0050] - "Substituted or Unsubstituted Alkynyl Group" Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl group (specific example group G5A). (Here, an unsubstituted alkynyl group refers to a case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, the term "alkynyl group" includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group." A "substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" have been replaced with a substituent. Specific examples of the "substituted alkynyl group" include a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" (specific example group G5A) have been replaced with a substituent.

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

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

[0053] Unsubstituted cycloalkyl groups (specific example group G6A): a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a 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 —Si(R ９０１ ) (R ９０２) (R ９０３ Specific examples (specific example group G7) of the group represented by the formula (G1) include -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6). 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 G1s in -Si(G1)(G1)(G1) may be the same or different. - Multiple G2 in Si(G1)(G2)(G2) are the same as or different from each other. - Multiple G1 in Si(G1)(G1)(G2) are the same as or different from each other. - Multiple G2 in Si(G2)(G2)(G2) are the same as or different from each other. - Multiple G3 in Si(G3)(G3)(G3) are the same as or different from each other. - Multiple G6 in Si(G6)(G6)(G6) are the same as or different from each other.

[0056] ・「-O-(R ９０４ A group represented by —O—(R ９０４ ) (Specific example group G8) includes -O(G1), -O(G2), -O(G3), and -O(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.

[0057] ・"-S-(R ９０５ A group represented by —S—(R ９０５) (Specific example group G9) includes -S(G1), -S(G2), -S(G3), and -S(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.

[0058] ・「-N(R ９０６ ) (R ９０７ A group represented by —N(R ９０６ ) (R ９０７ Specific examples (specific example group G10) of groups represented by the formula (G1) include -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. Multiple G1s in -N(G1)(G1) may be the same as or different from one another. Multiple G2s in -N(G2)(G2) may be the same as or different from one another. Multiple G3s in -N(G3)(G3) may be the same as or different from one another. -N(G6)(G6) may be the same or different from each other.

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

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

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

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

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

[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. Unless otherwise specified in this specification, 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.

[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. Unless otherwise specified in this specification, 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.

[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 specific example group G3. Multiple G3s in -Si(G3)(G3)(G3) are the same as or different from one another. Unless otherwise specified in this specification, 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.

[0067] "Substituted or unsubstituted aralkyl group" A specific example of the "substituted or unsubstituted aralkyl group" described in this specification is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. Therefore, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one embodiment of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group," and the number of carbon atoms in the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification. Specific examples of the "substituted or unsubstituted aralkyl group" include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group, an α-naphthylmethyl group, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group, a 1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, a β-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethyl group, a 1-β-naphthylisopropyl group, and a 2-β-naphthylisopropyl group.

[0068] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described in this specification is preferably a phenyl group, a p-biphenyl group, an 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, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an 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, or the like.

[0069] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic group described in this 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 this specification.

[0071]

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

[0073]

[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]

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

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

[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 (specific example group G12) of the "substituted or unsubstituted arylene group" include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1.

[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 (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group" 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 (specific example group G14) of the "substituted or unsubstituted alkylene group" include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3.

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

[0083]

[0084]

[0085] In the general formulae (TEMP-42) to (TEMP-52), Q １ ~Q １０ are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-42) to (TEMP-52), * represents a bonding position.

[0086]

[0087] In the general formulae (TEMP-53) to (TEMP-62), Q １ ~Q １０ are each independently a hydrogen atom or a substituent. ９ and Q １０ may be bonded to each other via a single bond to form a ring. In the general formulae (TEMP-53) to (TEMP-62), * represents the bonding position.

[0088]

[0089] In the general formulae (TEMP-63) to (TEMP-68), Q １ ~Q ８ are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-63) to (TEMP-68), * represents a bonding position.

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

[0091]

[0092]

[0093]

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

[0095]

[0096]

[0097]

[0098]

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

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

[0101] "When bonded to form a ring" In this specification, when "one or more pairs of 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 do not bond to each other," it means when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle," when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring," and when "one or more pairs of adjacent groups do not bond to each other." In this specification, the cases when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle" and "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "when bonded to form a ring") will be explained below. An anthracene compound represented by the following general formula (TEMP-103), in which the main skeleton is an anthracene ring, will be described as an example.

[0102]

[0103] For example, R ９２１~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," the pair of adjacent two groups is R ９２１ and R ９２２ Paired with R ９２２ and R ９２３ Paired with R ９２３ and R ９２４ Paired with R ９２４ and R ９３０ Paired with R ９３０ and R ９２５ Paired with R ９２５ and R ９２６ Paired with R ９２６ and R ９２７ Paired with R ９２７ and R ９２８ Paired with R ９２８ and R ９２９ and R ９２９ and R ９２１ It is paired with.

[0104] The above-mentioned "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 each other to form ring Q Ａ and simultaneously form R ９２５ and R ９２６ and are bonded to each other to form ring Q Ｂ When the anthracene compound represented by the 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]

[0106] The case where a "set of two or more adjacent groups" forms a ring includes not only the case where a set of two adjacent groups is bonded as in the above example, but also the case where a set of three or more adjacent groups is bonded. For example, R ９２１ and R ９２２ and are bonded to each other to form ring Q Ａ and R ９２２ and R ９２３ and are bonded to each other to form ring Q Ｃ and three adjacent (R ９２１ , R ９２２ and R９２３ In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105): Ａ and Ring Q Ｃ is R ９２２ Share.

[0107]

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

[0109] The term "unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The term "saturated ring" means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of aromatic hydrocarbon rings 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 aromatic heterocyclic rings include structures in which the aromatic heterocyclic groups given as specific examples in the specific example group G2 are terminated with a hydrogen atom. Specific examples of aliphatic hydrocarbon rings include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom. "Forming a ring" means forming a ring only with a plurality of atoms of the main skeleton, or with a plurality of atoms of the main skeleton and one or more optional elements. For example, R ９２１ and R ９２２ and a ring Q formed by bonding together Ａ is R ９２１ and the carbon atom of the anthracene skeleton to which R 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 and the carbon atom of the anthracene skeleton to which R ９２２ When a monocyclic unsaturated ring is formed by the carbon atom of the anthracene skeleton to which R is bonded and four carbon atoms, R ９２１ and R ９２２ The ring formed by

[0110] Here, unless otherwise specified herein, the "arbitrary element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur. In any element (for example, in the case of carbon or nitrogen), 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 any element other than a carbon element is included, the formed ring is a heterocycle. Unless otherwise specified herein, the "one or more arbitrary elements" constituting the monocycle or fused ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5. Unless otherwise specified herein, of the "monocycle" and the "fused ring," the "monocycle" is preferred. Unless otherwise specified herein, of the "saturated ring" and the "unsaturated ring," the "unsaturated ring" is preferred. Unless otherwise specified herein, the "monocycle" is preferably a benzene ring. Unless otherwise specified herein, the "unsaturated ring" is preferably a benzene ring. When "one or more pairs of adjacent two or more 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 pairs of adjacent two or more 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 atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0111] When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents Described Herein." 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 "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents Described Herein." The above is an explanation of the case where "one or more pairs of adjacent two or more rings are bonded to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent two or more rings are bonded to form a substituted or unsubstituted fused ring" ("when bonded to form a ring").

[0112] Substituents in the case of "substituted or unsubstituted" In one embodiment of the present specification, the substituents in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituents" in the present specification) include, 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 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and an unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ ~R ９０７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring 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. ９０１ When there are two or more R９０１ are the same or different from each other, R ９０２ When there are two or more R ９０２ are the same or different from each other, R ９０３ When there are two or more R ９０３ are the same or different from each other, R ９０４ When there are two or more R ９０４ are the same or different from each other, R ９０５ When there are two or more R ９０５ are the same or different from each other, R ９０６ When there are two or more R ９０６ are the same or different from each other, R ９０７ When there are two or more R ９０７ are the same or different from each other.

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

[0114] In one embodiment, the substituent in the "substituted or unsubstituted" is a group selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heterocyclic group having 5 to 18 ring atoms.

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

[0117] In this specification, a numerical range expressed using "AA to BB" means a range that includes 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 compound of the present invention will be described below. A compound according to one embodiment of the present invention (compound (1)) is represented by the following formula (1). Hereinafter, the compounds of the present invention represented by formula (1) and each formula included in formula (1) described below may be simply referred to as "compound (1)" or "invention compound (1)".

[0119]

[0120] Hereinafter, the symbols in formula (1) and each formula included in formula (1) described below, i.e., formula (1A), formula (1B), formulas (1Aa) to (1Ac), formulas (1Ba) to (1Bc), formulas (1Aa-1) to (1Aa-5), and formulas (1Ba-1) to (1Ba-5), as well as partial structural formulas (2A) to (2G), and (3A) to (3D), will be explained. Note that the same symbols have the same meaning. Therefore, hereinafter, when a specific symbol is explained following the description "in formula (1)," "in formula (1)," or "in invention compound (1)," if that symbol is included in each of the above formulas, the same explanation applies to that symbol in each of those formulas.

[0121] In formula (1), N ＊ is the central nitrogen atom.

[0122] In formula (1), X is an oxygen atom or a sulfur atom, and is preferably an oxygen atom.

[0123] In formula (1), Y ２ and Y ３ is a single bond bonded to *a. Therefore, compound (1) is represented by formula (1A) or formula (1B) described below.

[0124] In formula (1), R １ , R ４ and the Y which is not a single bond. ２ and Y ３ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 8, and more preferably 1 to 6, carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12, preferably 6 to 10, ring carbon atoms, and do not bond to each other to form a ring.

[0125] In the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, 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, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group; preferably, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, or a hexyl group; more preferably, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group; even more preferably, a methyl group or a t-butyl group; and particularly preferably, a t-butyl group.

[0126] In the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, the aryl group is a phenyl group, a biphenyl group, or a naphthyl group; preferably a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group; more preferably a phenyl group or a 1- or 2-naphthyl group; particularly preferably a phenyl group. In this specification, unless otherwise specified, the term "aryl" means a polyunsaturated, typically aromatic, hydrocarbon ring which may be a single ring or multiple rings condensed together.

[0127] In formula (1), R５ ~R １０ are hydrogen atoms, or any two or more of them are bonded to each other to form a substituted or unsubstituted ring. ５ ~R １０ is a hydrogen atom, so in this case, R ５ ~R １０ are not bonded to each other to form a ring. ５ ~R １０ The ring formed by the above R is preferably a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring, and more preferably a substituted or unsubstituted monocyclic ring. ５ ~R １０ The monocyclic ring formed by the above R is preferably a monocyclic ring having 3 to 6 ring atoms, more preferably a benzene ring, a furan ring, or a thiophene ring, and particularly preferably a benzene ring. The above benzene ring may form a phenanthrene ring, an anthracene ring, a phenalene ring, or a triphenylene ring together with ring B and ring C. ５ ~R １０ The fused ring formed by the formula (I) is preferably a fused ring having from 10 to 20 ring atoms, more preferably a naphthalene ring, a phenanthrene ring, an anthracene ring, or a phenalene ring, and particularly preferably a naphthalene ring. The naphthalene ring may form a tetracene ring, a chrysene ring, a benzanthracene ring, or a pyrene ring together with rings B and C.

[0128] In formula (1), R １１ ~R １４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10, preferably 2 to 6, carbon atoms, a substituted or unsubstituted aryl group having 6 to 12, preferably 6 to 10, ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms. １１ ~R １４ are not bonded to each other to form a ring. １１ ~R １４is a hydrogen atom. As used herein, the term "heteroaryl" refers to an aryl ring containing a heteroatom, and may be an aryl ring containing 1 to 5 heteroatoms selected from N, O, and S, wherein the nitrogen and sulfur atoms are optionally oxidized and the nitrogen atom is optionally quaternized. A heteroaryl group may be attached to the remainder of the molecule via a heteroatom.

[0129] Examples of the substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms include a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1,3-butadienyl group, a 1-methylvinyl group, a 1-methylallyl group, a 1,1-dimethylallyl group, a 2-methylallyl group, and a 1,2-dimethylallyl group.

[0130] In the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms, the heteroaryl group may be, for example, a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, an imidazopyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, an isoxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a tetrazolyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolidinyl group, a quinolin ... a benzoyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, an indazolyl group, a 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; Preferred are a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, 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 benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group (9-carbazolyl group, or a 1-, 2-, 3-, or 4-carbazolyl group). Examples of the substituted heteroaryl group having 5 to 13 ring atoms include a 9-phenylcarbazolyl group, a 9-biphenylylcarbazolyl group, a 9-phenylphenylcarbazolyl group, a 9-naphthylcarbazolyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group (a phenyldibenzothienyl group, the same applies hereinafter). The substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms includes isomeric groups, if any. R １１ ~R １４The heteroaryl group represented by R is preferably an unsubstituted heteroaryl group. １１ ~R １４ When the heteroaryl group represented by any of the groups below has a plurality of substituents, it is preferred that the plurality of substituents do not combine together to form a ring.

[0131] R １１ ~R １４ The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms represented by R and preferred examples thereof are as follows: １ As described above for R １１ ~R １４ The details and preferred examples of the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R １ As described above.

[0132] In formula (1), L １ and L ２ are each independently a substituted or unsubstituted arylene group having 6 to 30, preferably 6 to 25, and more preferably 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30, preferably 5 to 24, and more preferably 5 to 13 ring atoms.

[0133] L １ and L ２ The details of the arylene group are as described above in the section "Substituents Described in This Specification." The arylene group is preferably a phenylene group, a biphenylene group, or a naphthylene group, and more preferably a phenylene group.

[0134] L １ and L ２and the biphenylene group represented by each of the following is preferably a 4,2'-biphenylene group, a 4,3'-biphenylene group, a 4,4'-biphenylene group, a 2,2'-biphenylene group, or a 3,3'-biphenylene group, more preferably a 4,2'-biphenylene group, a 4,3'-biphenylene group, or a 4,4'-biphenylene group, and even more preferably a 4,2'-biphenylene group or a 4,4'-biphenylene group. In this specification, the term "biphenylene group" refers to a group derived by removing one hydrogen atom on the benzene ring from a "biphenyl group", and is also referred to as a "biphenylylene group" or a "biphenyldiyl group".

[0135] The naphthylene group is preferably a 1,4-naphthylene group, a 2,6-naphthylene group, a 1,5-naphthylene group, a 1,2-naphthylene group, or a 1,8-naphthylene group.

[0136] L １ and L ２In the substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms represented by the formula (I) and (II), the heteroarylene group contains 1 to 5, preferably 1 to 3, and more preferably 1 to 2 ring-forming heteroatoms. The ring-forming heteroatoms are selected from, for example, nitrogen atoms, sulfur atoms, and oxygen atoms. The free valence may be present on a ring-forming carbon atom, or, if structurally possible, on a nitrogen atom. Examples of the heteroarylene group include pyrrole, imidazole, pyrazole, triazole, furan, thiophene, oxazole, isoxazole, oxadiazole, thiazole, isothiazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, isoindole, indolizine, quinolizine, quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, quinoxaline, benzimidazole, indazole, phenanthroline, phenanthridine, acridine, phenazine, carbazole, benzocarbazole, xanthene, benzofuran, isobenzofuran, dibenzofuran, naphthobenzofuran, benzothiophene, dibenzothiophene, naphthobenzothiophene, benzoxazole, benzisoxazole, phenoxazine, Examples of the aromatic heterocyclic group include a divalent residue of an aromatic heterocycle selected from pyridine, pyrimidine, triazine, indole, quinoline, quinazoline, quinoxaline, benzimidazole, indazole, phenanthroline, phenanthridine, acridine, carbazole, benzocarbazole, benzofuran, dibenzofuran, naphthobenzofuran, benzothiophene, dibenzothiophene, naphthobenzothiophene, and benzoxazole; and more preferably a divalent residue of an aromatic heterocycle selected from pyridine, pyrimidine, triazine, carbazole, benzocarbazole, benzofuran, dibenzofuran, naphthobenzofuran, benzothiophene, and dibenzothiophene.

[0137] In formula (1), m1 and m2 each independently represent 0 or 1. When m1 is 0, Ar １ N ＊When m2 is 0, Ar ２ N ＊ Combine with.

[0138] In formula (1), L ３ and L ４ are each independently a substituted or unsubstituted arylene group having 6 to 10 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 10 ring atoms.

[0139] L ３ and L ４ In the substituted or unsubstituted arylene group having 6 to 10 ring carbon atoms represented by each of the above, the arylene group is preferably a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group, and more preferably a substituted or unsubstituted phenylene group.

[0140] L ３ and L ４ The phenylene group represented by each of the formulas is an o-phenylene group, an m-phenylene group, or a p-phenylene group. ３ and L ４ The phenylene group represented by each of the above is preferably an m-phenylene group or a p-phenylene group, more preferably a p-phenylene group.

[0141] 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.

[0142] L １ ~L ４ The substituent of the arylene group represented by is preferably an unsubstituted alkyl group having 1 to 10 carbon atoms. Details of the unsubstituted alkyl group having 1 to 10 carbon atoms and preferred examples thereof are given in R １ As described above.

[0143] L ３ and L ４and n is 0 or 1. In the substituted or unsubstituted heteroarylene group having 5 to 10 ring atoms represented by the formula (I), examples of the heteroarylene group include a divalent residue of an aromatic heterocycle selected from pyrrole, imidazole, pyrazole, triazole, furan, thiophene, oxazole, isoxazole, oxadiazole, thiazole, isothiazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, isoindole, indolizine, quinolizine, quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, quinoxaline, benzimidazole, and indazole.

[0144] L １ ~L ４ The substituent of the heteroarylene group represented by is preferably an unsubstituted alkyl group having 1 to 10 carbon atoms. Details of the unsubstituted alkyl group having 1 to 10 carbon atoms and preferred examples thereof are given in R １ As described above.

[0145] In formula (1), n1 is 0 or 1. When n1 is 0, R １３ and the carbon atom bonded to R １４ The carbon atoms bonded to both of the carbon atoms bonded to N ＊ Combine with.

[0146] In formula (1), n2 is 0 or 1. When n2 is 0, R １１ and the carbon atom bonded to R １４ The carbon atoms bonded to both of the carbon atoms bonded to Y ２ and Y ３ Bind to one selected from:

[0147] In formula (1), Ar １ and Ar ２are each independently a substituted or unsubstituted cycloalkyl group having 3 to 20, preferably 3 to 10, ring carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 3 to 20, preferably 3 to 10, ring atoms; a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 25, and more preferably 6 to 18 ring carbon atoms; or a substituted or unsubstituted heteroaryl group having 3 to 20, preferably 5 to 20, and more preferably 5 to 13 ring atoms.

[0148] Examples of the substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a 2-norbornyl group.

[0149] Examples of the substituted or unsubstituted heterocycloalkyl group having 3 to 20 ring atoms include an oxetanyl group, a tetrahydrofuranyl group, a tetrahydropyranyl group, an oxepanyl group, a dioxanyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a hexahydroazepinyl group, a hexahydrodiazepinyl group, a tetrahydrothiophenyl group, a thietanyl group, a tetrahydrothiopyranyl group, a thiepanyl group, and a morpholyl group.

[0150]

[0039] Examples of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms include a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, an acenaphthylenyl group, an anthryl group, a benzanthryl group, an aceanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a fluorenyl group, a spirofluorenyl group, a triphenylenyl group, a pentacenyl group, a picenyl group, a pentaphenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, an s-indacenyl group, an as-indacenyl group, a fluoranthenyl group, a benzofluoranthenyl group, and a perylenyl group. Preferred are a phenyl group, a biphenylyl group, a terphenylyl group, and a naphthyl group, more preferred are a phenyl group, a biphenylyl group, and a naphthyl group, and even more preferred is a phenyl group. As the substituted aryl group having the above number of ring carbon atoms, a 9,9-dimethylfluorenyl group and a 9,9-diphenylfluorenyl group are preferred.

[0151] In the substituted or unsubstituted heteroaryl group having 3 to 20 ring atoms, the heteroaryl group may be, for example, a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, an isoxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, an isobenzofuranyl group, a benzothiophenyl group (a benzothienyl group, the same applies hereinafter), an indolizinyl group, a quinolidinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidinyl group, a benzoimido ... Examples of the alkyl group include an aryl group, ... １ and Ar ２ The heteroaryl group represented by Ar is preferably an unsubstituted heteroaryl group. １ and Ar ２ When the heteroaryl group represented by the formula (I) has a substituent, it is preferable that the substituent does not form a ring. １ The aryl group represented by is preferably unsubstituted, and Ar １ It is more preferable that the cycloalkyl group, heterocycloalkyl group, aryl group, and heteroaryl group represented by are unsubstituted. ２ The aryl group represented by is preferably unsubstituted, and Ar ２It is more preferable that the cycloalkyl group, heterocycloalkyl group, aryl group, and heteroaryl group represented by the formula (I) are unsubstituted.

[0152] However, m1 is 1 and L １ is an unsubstituted 4,3'-biphenylene group, and Ar １ is a substituted or unsubstituted heteroaryl group having 3 to 20 ring atoms, １ , and m2 is 1, and L ２ is an unsubstituted 4,3'-biphenylene group, and Ar ２ is a substituted or unsubstituted heteroaryl group having 3 to 20 ring atoms, ２ are each independently selected from a substituted or unsubstituted 1-carbazolyl group, a substituted or unsubstituted 2-carbazolyl group, a substituted or unsubstituted 3-carbazolyl group, a substituted or unsubstituted 4-carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted benzofurocarbazolyl group, a substituted or unsubstituted benzothienocarbazolyl group, and a substituted or unsubstituted indenocarbazolyl group. The 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, and 9-carbazolyl group are respectively represented by the following formulas (C1), (C2), (C3), (C4), and (C5), respectively. In formulas (C1) to (C5), * represents L １ and L ２ represents a bond to one or both of the following:

[0153]

[0154] In formula (1), m1 is 0 and Ar １ When is a biphenyl group having a substituent, the substituent is the following substituent A.

[0155] In formula (1), m2 is 0 and Ar ２When is a biphenyl group having a substituent, the substituent is the following substituent A.

[0156] In formula (1), m1 is 1, L １ is a phenylene group, and Ar １ When is a phenyl group having a substituent, the substituent is the following substituent A.

[0157] In formula (1), m2 is 1, L ２ is a phenylene group, and Ar ２ When is a phenyl group having a substituent, the substituent is the following substituent A.

[0158] In formula (1), Ar １ and Ar ２ are both unsubstituted naphthyl groups, m1 and m2 are both 1, and L １ and L ２ When both are unsubstituted phenylene groups, L １ and L ２ One of the groups is an unsubstituted o-phenylene group, an unsubstituted m-phenylene group, or an unsubstituted p-phenylene group, and the other is an unsubstituted o-phenylene group or an unsubstituted p-phenylene group.

[0159] In formula (1), m1 is 0 and Ar １ When is a phenyl group having a substituent, the substituent is the following substituent B.

[0160] In formula (1), m2 is 0 and Ar ２ When is a phenyl group having a substituent, the substituent is the following substituent B.

[0161] In formula (1), Ar １ and Ar ２ are both unsubstituted dibenzofuranyl groups, m1 and m2 are both 1, and L １ and L ２ When both are unsubstituted phenylene groups, L １ and L ２ One of the groups is an unsubstituted o-phenylene group, an unsubstituted m-phenylene group, or an unsubstituted p-phenylene group, and the other is an unsubstituted o-phenylene group or an unsubstituted m-phenylene group.

[0162] In formula (1), m1 is 0 and Ar １ When is a phenyl group having a substituent, the substituent is the following substituent C.

[0163] In formula (1), m2 is 0 and Ar ２ When is a phenyl group having a substituent, the substituent is the following substituent C.

[0164] However, the substituent A is selected from groups which the following substituent D may take, an unsubstituted dibenzofuranyl group, and an unsubstituted naphthyl group.

[0165] In formula (1), the substituent B is selected from the groups that the following substituent D can take, an unsubstituted 9-carbazolyl group, and an unsubstituted dibenzofuranyl group.

[0166] In formula (1), the substituent C is selected from the groups which the following substituent D may take, an unsubstituted naphthyl group, and an unsubstituted 9-carbazolyl group.

[0167] In formula (1), the substituent D is a cyano group; a halogen atom; a phosphine oxide group substituted with an unsubstituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted alkyl group having 1 to 30 carbon atoms; an unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms; an unsubstituted aralkyl group having 7 to 36 carbon atoms; an unsubstituted alkoxy group having 1 to 30 carbon atoms; an unsubstituted aryloxy group having 6 to 30 ring carbon atoms; a mono-, di-, or tri-substituted silyl group having a substituent selected from an unsubstituted alkyl group having 1 to 30 carbon atoms and an unsubstituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted haloalkyl group having 1 to 30 carbon atoms; an unsubstituted haloalkoxy group having 1 to 30 carbon atoms; a boryl group substituted with an unsubstituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted alkylthio group having 1 to 30 carbon atoms; an unsubstituted arylthio group having 6 to 30 ring carbon atoms; and an unsubstituted phenyl group, an unsubstituted tolyl group, an unsubstituted xylyl group, an unsubstituted ethylphenyl group, an unsubstituted anthryl group, an unsubstituted phenanthryl group, an unsubstituted biphenylyl group, and an unsubstituted anthryl group; an unsubstituted 1-carbazolyl group, an unsubstituted 2-carbazolyl group, an unsubstituted 3-carbazolyl group, an unsubstituted 4-carbazolyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted benzonaphthofuranyl group, an unsubstituted benzonaphthothiophenyl group, an unsubstituted indolocarbazolyl group, an unsubstituted benzofurocarbazolyl group, an unsubstituted benzothienocarbazolyl group, an unsubstituted indenocarbazolyl group, and an unsubstituted dibenzocarbazolyl group.

[0168] In one embodiment of the present invention, compound (1) is represented by the following formula (1A):

[0169] In formula (1A), R １ , Y ３ , R ４ ~R １０ , R １１ ~R １４ , L １ ~L ４ , Ar １ , Ar ２ , N ＊ , X, m1, m2, n1, and n2 are as defined in formula (1) above.

[0170] In another embodiment of the present invention, compound (1) is represented by the following formula (1B):

[0171] In formula (1B), R １ , Y ２ , R ４ ~R １０ , R １１ ~R １４ , L １ ~L ４ , Ar １ , Ar ２ , N ＊ , X, m1, m2, n1, and n2 are as defined in formula (1) above.

[0172] In a preferred embodiment of the present invention, in the formulas (1A) and (1B), at least one of n1 and n2 is 0. In other words, the invention compound (1) is preferably represented by any one of the following formulas (1Aa) to (1Ac) and formulas (1Bc) to (1Bc). The following formulas (1Aa) and (1Ba) are more preferred.

[0173] In one embodiment, compound (1) is represented by the following formula (1Aa):

[0174] In formula (1Aa), R １ , Y ３ , R ４ ~R １０ , R １１ ~R １４ , L １ , L ２ , Ar １ , Ar ２ , N ＊ , X, m1, and m2 are as defined in formula (1) above.

[0175] In one embodiment, compound (1) is represented by the following formula (1Ab) or (1Ac):

[0176] In formula (1Ab) and formula (1Ac), R １ , Y ３ , R ４ ~R １０ , R １１ ~R １４ , L １ ~L４ , Ar １ , Ar ２ , N ＊ , X, m1, and m2 are as defined in formula (1) above.

[0177] In one embodiment, compound (1) is represented by the following formula (1Ba):

[0178] In formula (1Ba), R １ , Y ２ , R ４ ~R １０ , R １１ ~R １４ , L １ , L ２ , Ar １ , Ar ２ , N ＊ , X, m1, and m2 are as defined in formula (1) above.

[0179] In one embodiment, compound (1) is represented by the following formula (1Bb) or (1Bc):

[0180] In formula (1Bb) and formula (1Bc), R １ , Y ２ , R ４ ~R １０ , R １１ ~R １４ , L １ ~L ４ , Ar １ , Ar ２ , N ＊ , X, m1, and m2 are as defined in formula (1) above.

[0181] In one embodiment of the present invention, m1 is 0 and m2 is 0. In another embodiment, one of m1 and m2 is 0 and the other is 1. In yet another embodiment, m1 is 1 and m2 is 1.

[0182] In one embodiment of the present invention, compound (1) has any one of the structures selected from the following (L1) to (L4): (L1) m1 and m2 are 0; (L2) m1 is 1, and L １is a substituted or unsubstituted phenylene group, and m2 is 0. (L3) m2 is 1, and L ２ is a substituted or unsubstituted phenylene group, and m1 is 0. (L4) m1 and m2 are 0, and L １ and L ２ are each independently a substituted or unsubstituted phenylene group. In a preferred embodiment, compound (1) is represented by formula (1A) above and has any one of the structures (L1) to (L4) above. In a more preferred embodiment, compound (1) is represented by formula (1Aa) above and has any one of the structures (L1) to (L4) above. Therefore, in this case, compound (1) is represented by any one of formulas (1Aa-1) to (1Aa-3) below.

[0183] In formula (1Aa-2) and formula (1Aa-3), R ２１ ~R ２５ is a single bond bonded to *b, and R ２１ ~R ２５ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 8, and more preferably 1 to 6, carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10, preferably 2 to 6, carbon atoms, a substituted or unsubstituted aryl group having 6 to 12, preferably 6 to 10, ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms. ２１ ~R ２５ two or more of these bond to each other to form a substituted or unsubstituted ring of six or less members, or R ２１ ~R ２５ are not bonded to each other to form a ring. ３１ ~R ３５ is a single bond bonded to *c, and R ３１ ~R ３５ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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.３１ ~R ３５ two or more of these bond to each other to form a substituted or unsubstituted ring of six or less members, or R ３１ ~R ３５ are not bonded to each other to form a ring. １ , Y ３ , R ４ ~R １０ , R １１ ~R １４ , Ar １ , Ar ２ , N ＊ and X are as defined in the formula (1). Details and preferred examples of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and details and preferred examples of the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms are as follows: R １ The details and preferred examples of the substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, the details and preferred examples of the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms, and the details and preferred examples of the substituted or unsubstituted 6-membered or less ring are as described above with respect to R １１ ~R １３ As described above.

[0184] In another preferred embodiment, compound (1) is represented by formula (1B) above and has any one of the structures (L1) to (L4) above. In a more preferred embodiment, compound (1) is represented by formula (1Ba) above and has any one of the structures (L1) to (L4) above. Therefore, in this case, compound (1) is represented by any one of formulas (1Ba-1) to (1Ba-3) below.

[0185] In formula (1Ba-2) and formula (1Ba-3), R ２１ ~R ２５ is a single bond bonded to *b, and R ２１ ~R ２５are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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. ２１ ~R ２５ two or more of these bond to each other to form a substituted or unsubstituted ring of six or less members, or R ２１ ~R ２５ are not bonded to each other to form a ring. ３１ ~R ３５ is a single bond bonded to *c, and R ３１ ~R ３５ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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. ３１ ~R ３５ two or more of these bond to each other to form a substituted or unsubstituted ring of six or less members, or R ３１ ~R ３５ are not bonded to each other to form a ring. １ , Y ２ , R ４ ~R １０ , R １１ ~R １４ , Ar １ , Ar ２ , N ＊ and X are as defined in the formula (1). Details and preferred examples of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and details and preferred examples of the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms are as follows: R １The details and preferred examples of the substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, the details and preferred examples of the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms, and the details and preferred examples of the substituted or unsubstituted 6-membered or less ring are as described above with respect to R １１ ~R １３ As described above.

[0186] In one embodiment of the present invention, compound (1) has any one of the following structures: (L5) m1 is 1, and L １ is a substituted or unsubstituted biphenylene group, and m2 is 0. (L6) m2 is 1, and L ２ is a substituted or unsubstituted biphenylene group, and m1 is 0. (L7) m1 is 1, and L １ is a substituted or unsubstituted biphenylene group, and m2 is 1. (L8) m2 is 1, and L ２ is a substituted or unsubstituted biphenylene group, and m1 is 1. In a preferred embodiment, compound (1) is represented by formula (1A) above and has any one of the structures (L5) to (L8) above. In a more preferred embodiment, compound (1) has any one of the structures (1Aa) above and (L5) to (L8) above. Therefore, in this case, compound (1) is represented by formula (1Aa-4) or formula (1Aa-5) below.

[0187] In formula (1Aa-4) and formula (1Aa-5), R ４１ ~R ４５ is a single bond bonded to *d, and R ４１ ~R ４５ is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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. ４１ ~R ４５ two or more of these bond to each other to form a substituted or unsubstituted ring of six or less members, or R ４１ ~R４５ are not bonded to each other to form a ring. ５１ , R ５３ , and R ５５ is a single bond bonded to *e, and Y ５２ , Y ５４ and R which is not a single bond. ５１ , R ５３ , and R ５５ is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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. ５２ , Y ５４ and R which is not a single bond. ５１ , R ５３ , and R ５５ In formula (1Aa-4) and formula (1Aa-5), two or more of R are bonded to each other to form a substituted or unsubstituted ring of 6 or less, or they are not bonded to each other to form a ring. １ , Y ３ , R ４ ~R １０ , R １１ ~R １４ , L ２ , Ar １ , Ar ２ , N ＊ and X are as defined in the formula (1). Details and preferred examples of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and details and preferred examples of the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms are as follows: R １ The details and preferred examples of the substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, the details and preferred examples of the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms, and the details and preferred examples of the substituted or unsubstituted 6-membered or less ring are as described above with respect to R １１ ~R １３ As described above.

[0188] In a preferred embodiment, compound (1) is represented by formula (1B) above and has any one of the structures (L5) to (L8) above. In a more preferred embodiment, compound (1) is represented by formula (1Ba) above and has any one of the structures (L5) to (L8) above. Therefore, in this case, compound (1) is represented by formula (1Ba-4) or formula (1Ba-5) below.

[0189] In formula (1Ba-4) and formula (1Ba-5), R ４１ ~R ４５ is a single bond bonded to *d, and R ４１ ~R ４５ is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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. ４１ ~R ４５ two or more of these bond to each other to form a substituted or unsubstituted ring of six or less members, or R ４１ ~R ４５ are not bonded to each other to form a ring. ５１ , R ５３ , and R ５５ is a single bond bonded to *e, and Y ５２ , Y ５４ and R which is not a single bond. ５１ , R ５３ , and R ５５ is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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. ５２ , Y ５４ and R which is not a single bond. ５１ , R ５３ , and R ５５In formula (1Ba-4) and formula (1Ba-5), two or more of R are bonded to each other to form a substituted or unsubstituted ring of 6 or less members, or they are not bonded to each other to form a ring. １ , Y ２ , R ４ ~R １０ , R １１ ~R １４ , L ２ , Ar １ , Ar ２ , N ＊ and X are as defined in the formula (1). Details and preferred examples of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and details and preferred examples of the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms are as follows: R １ The details and preferred examples of the substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, the details and preferred examples of the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms, and the details and preferred examples of the substituted or unsubstituted 6-membered or less ring are as described above with respect to R １１ ~R １３ As described above.

[0190] In one embodiment of the present invention, Ar １ and Ar ２ are each independently a substituted or unsubstituted cycloalkyl group having 3 to 20, preferably 3 to 10, carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 20, preferably 3 to 10, ring atoms, or a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms.

[0191] In another embodiment of the present invention, Ar １ and Ar ２ are each independently a substituted or unsubstituted cycloalkyl group having 3 to 20, preferably 3 to 10, carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 20, preferably 3 to 10, ring atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20, preferably 5 to 20, more preferably 5 to 13 ring atoms.

[0192] In another embodiment of the present invention, Ar １ and Ar ２ one of which is a substituted or unsubstituted cycloalkyl group having 3 to 20, preferably 3 to 10, carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 20, preferably 3 to 10, ring atoms, or a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 25, and more preferably 6 to 18, ring carbon atoms, and the other is a substituted or unsubstituted cycloalkyl group having 3 to 20, preferably 3 to 10, carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 20, preferably 3 to 10, ring atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20, preferably 5 to 20, and more preferably 5 to 13 ring atoms.

[0193] In one embodiment of the present invention, Ar １ and Ar ２ are each independently represented by the following formula (2A), (2B), (2C), (2D), (2E), (2F), or (2G).

[0194]

[0195] In formula (2A), *21 represents L １ and L ２ represents a bond to one or both of the following:

[0196] In formula (2A), R １０１ ~R １０５ one selected from is a single bond bonded to *22, and R １０６ ~R １１０ One selected from is a single bond bonded to *23. １０１ ~R １０５ and R １０６ ~R １１０ are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms. Details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms and preferred examples thereof are as follows: R １ As described above.

[0197] The R that is not a single bond １０１ ~R １０５Any two adjacent R groups selected from the above are not bonded to each other to form a ring. １０６ ~R １１０ Adjacent two selected from the following are not bonded to each other to form a ring.

[0198] In formula (2A), 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 Adjacent two selected from the following are not bonded to each other to form a ring.

[0199] The details of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms and preferred examples thereof are as follows: １ The details and preferred examples of the substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms are as described above for R １ The details and preferred examples of the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms are as described above for R １１ As described above.

[0200] In formula (2A), j is 0, 1 or 2, and k is 0 or 1. Except when j is 2 and k is 0. When j = 0 and k = 0, *23 represents *21. When j = 0 and k = 1, *22 represents *21. When j = 1 and k = 0, *23 represents *22.

[0201] However, m1 is 0 and Ar １ is represented by formula (2A), j is 0, k is 0, and R １１１ ~R １１５ When at least one selected from the group consisting of is a substituent other than a hydrogen atom, the substituent is selected from the groups that can be taken by the above-mentioned substituent D and an unsubstituted 9-carbazolyl group. ２ is represented by formula (2A), j is 0, k is 0, and R １１１ ~R １１５When at least one selected from the group consisting of is a substituent other than a hydrogen atom, the substituent is selected from the groups that can be taken by the above-mentioned substituent D and an unsubstituted 9-carbazolyl group. １ is a phenylene group, and Ar １ is represented by formula (2A), j is 0, k is 0, and R １１１ ~R １１５ When at least one selected from the group consisting of is a substituent other than a hydrogen atom, the substituent is the above-mentioned substituent A. ２ is a phenylene group, and Ar ２ is represented by formula (2A), j is 0, k is 0, and R １１１ ~R １１５ When at least one selected from the group consisting of is a substituent other than a hydrogen atom, the substituent is the above-mentioned substituent A. １ is represented by formula (2A), j is 0, k is 1, and R １１１ ~R １１５ and the R that is not a single bond １０６ ~R １１０ is a substituent other than a hydrogen atom, and m1 is 0 and Ar １ is represented by formula (2A), j is 1, k is 0, and R １１１ ~R １１５ and the R that is not a single bond １０１ ~R １０５ When at least one of the groups is a substituent other than a hydrogen atom, the substituent is the above-mentioned substituent A. ２ is represented by formula (2A), j is 0, k is 1, and R １１１ ~R １１５ and the R that is not a single bond １０６ ~R １１０ is a substituent other than a hydrogen atom, and m2 is 0 and Ar ２ is represented by formula (2A), j is 1, k is 0, and R １１１ ~R １１５ and the R that is not a single bond １０１ ~R １０５ When at least one of the groups is a substituent other than a hydrogen atom, the substituent is the above-mentioned substituent A.

[0202] In one embodiment of the present invention, j is 0 and k is 0. In this case, *23 represents *21, and formula (2A) is represented by the following formula (2Aa).

[0203]

[0204] However, m1 is 0 and Ar １ is represented by formula (2Aa) (i.e., j is 0, k is 0), and R １１１ ~R １１５ In the case where at least one selected from the group consisting of is a substituent other than a hydrogen atom (i.e., a phenyl group having a substituent), the substituent is selected from the groups that can be taken by the above-mentioned substituent D and an unsubstituted 9-carbazolyl group. ２ is represented by formula (2Aa) (i.e., j is 0, k is 0), and R １１１ ~R １１５ When at least one selected from the group consisting of m1 and m2 is a substituent other than a hydrogen atom (i.e., a phenyl group having a substituent), the substituent is selected from the groups that can be taken by the above-mentioned substituent D and an unsubstituted 9-carbazolyl group. １ is a phenylene group, and Ar １ is represented by formula (2Aa) (i.e., j is 0, k is 0), and R １１１ ~R １１５ When at least one selected from is a substituent other than a hydrogen atom (i.e., a phenyl group having a substituent), the substituent is the above-mentioned substituent A. ２ is a phenylene group, and Ar ２ is represented by formula (2Aa) (i.e., j is 0, k is 0), and R １１１ ~R １１５ is a substituent other than a hydrogen atom (i.e., a phenyl group having a substituent), the substituent is the above-mentioned substituent A.

[0205] In another embodiment of the present invention, j is 0 and k is 1. In this case, *22 represents *21, and formula (2A) is represented by the following formula (2Ab1).

[0206]

[0207] In another embodiment of the present invention, j is 1 and k is 0. In this case, *23 represents *22, and formula (2A) is represented by the following formula (2Ab2).

[0208]

[0209] However, m1 is 0 and Ar １ is represented by formula (2Ab1) (i.e., j is 0 and k is 1), and R １１１ ~R １１５ and the R that is not a single bond １０６ ~R １１０ is a substituent other than a hydrogen atom (i.e., a biphenyl group having a substituent), and m1 is 0 and Ar １ is represented by formula (2Ab2) (i.e., j is 1 and k is 0), and R １１１ ~R １１５ and the R that is not a single bond １０１ ~R １０５ When at least one of Ar is a substituent other than a hydrogen atom (i.e., a biphenyl group having a substituent), the substituent is the above-mentioned substituent A. ２ is represented by formula (2Ab1) (i.e., j is 0 and k is 1), and R １１１ ~R １１５ and the R that is not a single bond １０６ ~R １１０ is a substituent other than a hydrogen atom (i.e., a biphenyl group having a substituent), and m2 is 0 and Ar ２ is represented by formula (2Ab2) (i.e., j is 1 and k is 0), and R １１１ ~R １１５ and the R that is not a single bond １０１ ~R １０５ When at least one of the groups is a substituent other than a hydrogen atom (that is, a biphenyl group having a substituent), the substituent is the above-mentioned substituent A.

[0210] In another embodiment of the present invention, j is 1 and k is 1. In this case, formula (2A) is represented by the following formula (2Ac):

[0211]

[0212] In another embodiment of the present invention, j is 2 and k is 1. In this case, formula (2A) is represented by the following formula (2Ad).

[0213]

[0214] The group represented by formula (2A) is preferably represented by the following formula: In the following formula, R has been omitted for simplicity.

[0215]

[0216] * R that is not a single bond bonded to 22 １０１ ~R １０５ , *23 is bonded to a non-single bond R １０６ ~R １１０ , and R １１１ ~R １１５ may all be hydrogen atoms.

[0217]

[0218] In formula (2B), *24 represents L １ and L ２ represents a bond to one or both of the following:

[0219] In formula (2B), R １２１ ~R １２８ One selected from is a single bond bonded to *25. 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 adjacent two selected from are not bonded to each other to form a ring. １ and Ar ２ are both represented by formula (2B), and the R １２１ ~R １２８ are all hydrogen atoms (i.e., unsubstituted naphthyl groups), m1 and m2 in formula (1) are both 1, and L in formula (1) １ and L ２ When both are unsubstituted phenylene groups, L １and L ２ One of the groups is an unsubstituted o-phenylene group, an unsubstituted m-phenylene group, or an unsubstituted p-phenylene group, and the other is an unsubstituted o-phenylene group or an unsubstituted p-phenylene group.

[0220] R １２１ ~R １２８ The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R １ As described above.

[0221] R １２１ ~R １２８ The unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R １ As described above.

[0222] In one embodiment of the present invention, preferably R １２１ , R １２４ , R １２５ , and R １２８ Preferably, one selected from is a single bond bonded to *25.

[0223] * R that is not a single bond bonded to 25 １２１ ~R １２８ may all be hydrogen atoms.

[0224]

[0225] In formula (2C), *26 represents L １ and L ２ represents a bond to one or both of the following:

[0226] In formula (2C), R １３１ ~R １４０ One selected from is a single bond bonded to *27. 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 Adjacent two selected from the following are not bonded to each other to form a ring.

[0227] R １３１~R １４０ The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R and preferred examples thereof are as follows: １ As described above.

[0228] R １３１ ~R １４０ The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R and preferred examples thereof are as follows: １ As described above.

[0229] In one embodiment of the present invention, preferably R １３７ , R １３８ and R １３９ is a single bond bonded to *27, and more preferably R １３７ and R １３９ is a single bond bonded to *27, and more preferably R １３９ is a single bond that bonds to *27.

[0230] * R that is not a single bond attached to 27 １３１ ~R １４０ may all be hydrogen atoms.

[0231]

[0232] In formula (2D), *28 is L １ and L ２ represents a bond to one or both of the following:

[0233] In formula (2D), X １ represents an oxygen atom, a sulfur atom, -CR ａ R ｂ , or -NR ｃ and preferably an oxygen atom or —CR ａ R ｂ is.

[0234] In formula (2D), X １ Ga-CR ａ R ｂ When R １４１ ~R １４８ is a single bond bonded to *29, or R ａ and R ｂ One of R is a single bond bonded to *29 or a divalent group bonded to *29.ａ or R ｂ Examples of the divalent group that can be taken by include an unsubstituted phenylene group, an unsubstituted biphenylene group, and an unsubstituted naphthylene group, and preferably an unsubstituted phenylene group, and more preferably an unsubstituted m-phenylene group or an unsubstituted p-phenylene group.

[0235] In formula (2D), X １ is an oxygen atom, a sulfur atom, or —NR ｃ When R １４１ ~R １４８ , one selected from is a single bond that bonds to *29.

[0236] In formula (2D), R １４１ ~R １４８ , R which is not the single bond and is not the divalent group ａ and R ｂ , and R ｃ 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 Adjacent two selected from the following are not bonded to each other to form a ring.

[0237] R １４１ ~R １４８ The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R and preferred examples thereof are as follows: １ As described above.

[0238] R １４１ ~R １４８ The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R and preferred examples thereof are as follows: １ As described above.

[0239] R １４１ ~R １４８ The details and preferred examples of the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms represented by R １１ However, Ar １ and Ar２ are both represented by formula (2D), and the R １２１ ~R １２８ are all hydrogen atoms, and X １ is an oxygen atom (i.e., an unsubstituted dibenzofuranyl group), m1 and m2 are both 1, and L １ and L ２ When both are unsubstituted phenylene groups, L １ and L ２ One of the groups is an unsubstituted o-phenylene group, an unsubstituted m-phenylene group, or an unsubstituted p-phenylene group, and the other is an unsubstituted o-phenylene group or an unsubstituted m-phenylene group.

[0240] The R that is not a single bond １４１ ~R １４８ , the R that is not a single bond ２００ ~R ２０３ and R which is not the single bond and is not the divalent group. ａ and R ｂ may all be hydrogen atoms.

[0241]

[0242] In formula (2E), *30 represents L １ and L ２ represents a bond to one or both of the following:

[0243] 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. １５１ ~R １５５ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group. １５１ ~R １５５ Adjacent two selected from R are not bonded to each other to form a ring. １６１ ~R １６５ and R １７１ ~R １７５are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms. １６１ ~R １６５ At least two adjacent R selected from 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. １７１ ~R １７５ At least two adjacent ones selected from the following may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore not form a ring.

[0244] R １５１ ~R １５５ , R １６１ ~R １６５ and R １７１ ~R １７５ The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R and preferred examples thereof are as follows: １ As described above.

[0245] In one embodiment of the present invention, R １６１ ~R １６５ Adjacent two selected from the group consisting of are bonded to each other to form a substituted or unsubstituted benzene ring. １６１ ~R １６５ In one embodiment of the present invention, two adjacent groups selected from R １７１ ~R １７５ In another embodiment of the present invention, adjacent two selected from R １７１ ~R １７５ Adjacent two selected from are not bonded to each other and therefore do not form a ring structure.

[0246] The R that is not a single bond １５１ ~R １５５ may all be hydrogen atoms, and R １６１ ~R １６５ may all be hydrogen atoms, and R １７１ ~R １７５ may all be hydrogen atoms.

[0247]

[0248] In formula (2F), *33 represents L １ and L ２ represents a bond to one or both of the following:

[0249] In formula (2F), R １８１ ~R １９２ One selected from is a single bond bonded to *34. 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 Adjacent two selected from the following are not bonded to each other to form a ring.

[0250] R １８１ ~R １９２ The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R １ As described above.

[0251] R １８１ ~R １９２ The details and preferred examples of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R １ As described above.

[0252] In one embodiment of the present invention, R １８１ is a single bond attached to *33, and in another embodiment, R １８２ is a single bond that bonds to *33.

[0253] The single bond is not １８１ ~R １９２ may all be hydrogen atoms.

[0254]

[0255] In formula (2G), *35 is L １ and L ２ represents a bond to one or both of the following:

[0256] In formula (2G), R ３０１ ~R３０８ 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. ３０１ ~R ３０８ adjacent two selected from are not bonded to each other to form a ring. １ is represented by formula (2G), and when m1 is 1, L １ , and Ar ２ is represented by formula (2G), and L when m2 is 1 ２ respectively represent a substituted or unsubstituted 4,2'-biphenylene group, a substituted or unsubstituted 4,4'-biphenylene group, a substituted or unsubstituted 2,2'-biphenylene group, a substituted or unsubstituted 3,3'-biphenylene group, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

[0257] R ３０１ ~R ３０８ The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R １ As described above.

[0258] R ３０１ ~R ３０８ The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R and preferred examples thereof are as follows: １ As described above.

[0259] R ３０１ ~R ３０８ The details and preferred examples of the substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms represented by R １１ As described above.

[0260] The R ３０１ ~R ３０８ may all be hydrogen atoms.

[0261] In formula (1), Ar １ and Ar ２are represented by the same formula among the above formulas (2A), (2B), (2C), (2D), (2E), (2F), and (2G), Ar １ and Ar ２ are the same as each other or different from each other.

[0262] In one embodiment of the present invention, -(L １ ) ｍ１ -Ar １ The skeleton of -(L ２ ) ｍ２ -Ar ２ In this case, the following embodiment is given as an example: [LA1] m1 and m2 are 0, and Ar １ and Ar ２ [LA2] m1 is 1, m2 is 0, and Ar １ and Ar ２ [LA3] m1 is 1, m2 is 0, and Ar １ and Ar ２ are different from each other, and -L １ -Ar １ and Ar ２ [LA4] m1 is 0, m2 is 1, and Ar １ and Ar ２ [LA5] m1 is 0, m2 is 1, and Ar １ and Ar ２ are different from each other, and -L ２ -Ar ２ and Ar １ [LA6] m1 and m2 are 1, and L １ and L ２ are different from each other, and Ar １ and Ar ２ [LA7] m1 and m2 are 1, and L １ and L ２ are different from each other, and Ar １ and Ar ２ are different from each other, and -L １ -Ar １ and-L ２ -Ar ２ [LA8] m1 and m2 are 1, and L １ and L ２ are the same, and Ar１ and Ar ２ are different from each other.

[0263] In another embodiment of the present invention, -(L １ ) ｍ１ -Ar １ The skeleton of -(L ２ ) ｍ２ -Ar ２ The skeleton of the compound is the same as that of the compound of the present invention. In this case, the following embodiment is given as an example: [LA9] m1 and m2 are 0, and Ar １ and Ar ２ has no substituent, and Ar １ and Ar ２ [LA10] m1 and m2 are 0, and Ar １ and Ar ２ have the same substituents, and Ar １ and Ar ２ [LA10] m1 and m2 are 1, and L １ and L ２ are the same, and Ar １ and Ar ２ [LA11] m1 is 1, m2 is 0, and Ar １ and Ar ２ are different from each other, and -L １ -Ar １ and Ar ２ [LA12] m1 is 0, m2 is 1, and Ar １ and Ar ２ are different from each other, and -L ２ -Ar ２ and Ar １ is the same.

[0264] In the invention compound (1), Ar １ and Ar ２ Examples of the combinations include the following [a1] to [g1]. [a1] Ar １ :Formula (2A);Ar ２ : Formula (2A) [a2]Ar １ :Formula (2A);Ar ２ : Formula (2B) [a3]Ar １ :Formula (2A);Ar ２ : Formula (2C) [a4]Ar １: Formula (2A); Ar ２ : Formula (2D) [a5]Ar １ : Formula (2A); Ar ２ :Formula (2E) [a6]Ar １ : Formula (2A); Ar ２ : Formula (2F) [a7]Ar １ : Formula (2A); Ar ２ : Formula (2G) [b1]Ar １ : Formula (2B); Ar ２ : Formula (2B) [b2]Ar １ : Formula (2B); Ar ２ :Formula (2C) [b3]Ar １ : Formula (2B); Ar ２ :Formula (2D) [b4]Ar １ : Formula (2B); Ar ２ : Formula (2E) [b5]Ar １ : Formula (2B); Ar ２ : Formula (2F) [b6]Ar １ : Formula (2B); Ar ２ :Formula (2G) [c1]Ar １ : Formula (2C); Ar ２ :Formula (2C) [c2]Ar １ : Formula (2C); Ar ２ : Formula (2D) [c3]Ar １ : Formula (2C); Ar ２ :Formula (2E) [c4]Ar １ : Formula (2C); Ar ２ : Formula (2F) [c5]Ar １ : Formula (2C); Ar ２ : Formula (2G) [d1]Ar １ : Formula (2D); Ar ２ : Formula (2D) [d2]Ar １ : Formula (2D); Ar ２ : Formula (2E) [d3]Ar １ : Formula (2D); Ar ２ : Formula (2F) [d4]Ar １ : Formula (2D); Ar ２ : Formula (2G) [e1]Ar １ : Formula (2E); Ar ２ : Formula (2E) [e2]Ar １ : Formula (2E); Ar ２ : Formula (2F) [e3]Ar１ Formula (2E): Ar ２ : Formula (2G) [f1]Ar １ :Formula (2F); Ar ２ : Formula (2F) [f2]Ar １ :Formula (2F); Ar ２ : Formula (2G) [g1]Ar １ :Formula (2G);Ar ２ : Formula (2G)

[0265] In one embodiment of the present invention, the entire unit composed of the following (i), (ii), and (iii) is preferably represented by the following formula: In the following formula, R is omitted for simplicity. (i)-(L ３ ) ｎ１ - (ii) Benzene ring D (iii) - (L ４ ) ｎ２ -

[0266]

[0267] In one embodiment of the present invention, m1 is 1 and L １ has a phenylene skeleton, and Ar １ When L has a dibenzofuranyl skeleton or a dibenzothiophene skeleton, it satisfies at least one of the following conditions (i) and (ii): m2 is 1, and L ２ has a phenylene skeleton, and Ar ２ When L has a dibenzofuranyl skeleton or a dibenzothiophene skeleton, it satisfies at least one of the following (iii) and (iv): １ (ii) Ar is a substituted or unsubstituted o-phenylene group or a substituted or unsubstituted p-phenylene group. １ (iii) L is an unsubstituted dibenzofuranyl group or an unsubstituted dibenzothiophene group. ２ (iv) Ar is a substituted or unsubstituted o-phenylene group or a substituted or unsubstituted p-phenylene group. ２ is an unsubstituted dibenzofuranyl group or an unsubstituted dibenzothiophene group.

[0268] In one embodiment of the present invention, compound (1) consists of any one of the following compounds 1 to 3:

[0269]

[0270] As described above, the term "hydrogen atom" used herein includes protium, deuterium, and tritium atoms. The compounds of the invention may contain naturally occurring deuterium atoms. Alternatively, deuterium atoms may be intentionally introduced into the compounds of the invention by using partially or entirely deuterated compounds as starting compounds.

[0271] In one embodiment of the present invention, compound (1) contains one or more deuterium atoms in the molecule. More specifically, in compound (1) according to one embodiment of the present invention, at least one selected from the group consisting of the following (A1a) to (A5d1) is a deuterium atom: (A1a)R １ , Y ２ , Y ３ , and R ４ (A1b) a hydrogen atom represented by R １ , Y ２ , Y ３ , and R ４ a hydrogen atom contained in an alkyl group represented by (A1c) R １ , Y ２ , Y ３ , and R ４ a hydrogen atom contained in an aryl group represented by (A1b1) R １ , Y ２ , Y ３ , and R ４ a hydrogen atom contained in a substituent of the alkyl group represented by (A1c1)R １ , Y ２ , Y ３ , and R ４ a hydrogen atom contained in a substituent of an aryl group represented by (A2a) R ５ ~R １０ (A2b) a hydrogen atom represented by R ５ ~R １０ a hydrogen atom contained in a ring formed by any two or more of (A2b1) R ５ ~R １０ a hydrogen atom contained in a substituent of a ring formed by any two or more of (A3a) R １１ ~R １４ (A3b) a hydrogen atom represented by R１１ ~R １４ a hydrogen atom contained in an alkyl group represented by (A3c) R １１ ~R １４ a hydrogen atom contained in an alkoxy group represented by (A3d) R １１ ~R １４ a hydrogen atom contained in an aryl group represented by (A3e) R １１ ~R １４ a hydrogen atom contained in a heteroaryl group represented by (A3b1) R １１ ~R １４ a hydrogen atom contained in a substituent of an alkyl group represented by (A3c1) R １１ ~R １４ a hydrogen atom contained in a substituent of an alkoxy group represented by (A3d1) R １１ ~R １４ a hydrogen atom contained in a substituent of an aryl group represented by (A3e1) R １１ ~R １４ a hydrogen atom contained in a substituent of a heteroaryl group represented by the formula (A4a) １ ~L ４ a hydrogen atom contained in an arylene group represented by (A4b) L １ ~L ４ a hydrogen atom contained in a heteroarylene group represented by (A4a1) L １ ~L ４ a hydrogen atom contained in a substituent of an arylene group represented by (A4b1) L １ ~L ４ (A5a) a hydrogen atom contained in a substituent of a heteroarylene group represented by the following formula: １ and Ar ２ (A5b) a hydrogen atom contained in a cycloalkyl group represented by Ar １ and Ar ２ (A5c) a hydrogen atom contained in a heterocycloalkyl group represented by １ and Ar ２ (A5d) a hydrogen atom contained in an aryl group represented by １ and Ar ２ a hydrogen atom contained in a heteroaryl group represented by (A5a1) Ar １ and Ar ２a hydrogen atom contained in a substituent of a cycloalkyl group represented by (A5b1) Ar １ and Ar ２ a hydrogen atom contained in a substituent of a heterocycloalkyl group represented by the following formula: １ and Ar ２ A hydrogen atom contained in a substituent of the aryl group represented by (A5d1) Ar １ and Ar ２ A hydrogen atom contained in a substituent of the heteroaryl group represented by the formula (I).

[0272] In a preferred embodiment of the present invention, among the above (A1a) to (A5d1), at least one selected from the group consisting of (A3a) to (A3e1) and (A4a) to (A4b1) is a deuterium atom. In a preferred embodiment of the present invention, at least one selected from the group consisting of the above (A4a) to (A4b1) is a deuterium atom.

[0273] Some of the hydrogen atoms in (A1a) may be deuterium atoms, or all of the hydrogen atoms in (A1a) may be deuterium atoms, but preferably all of the hydrogen atoms in (A1a) are deuterium atoms. The same applies to (A1b) to (A5d1).

[0274] In one embodiment of the present invention, R １１ ~R １４ At least one of the hydrogen atoms, the hydrogen atoms contained in the alkyl group, the hydrogen atoms contained in the substituent of the alkyl group, the hydrogen atoms contained in the alkenyl group, the hydrogen atoms contained in the substituent of the alkenyl group, the hydrogen atoms contained in the aryl group, the hydrogen atoms contained in the substituent of the aryl group, the hydrogen atoms contained in the heteroaryl group, and the hydrogen atoms contained in the substituent of the heteroaryl group represented by (A3a) to (A3e1) is a deuterium atom. In other words, in one embodiment of the present invention, at least one of the above (A3a) to (A3e1) is a deuterium atom. Two or more of these hydrogen atoms may be deuterium atoms, or all of them may be deuterium atoms.

[0275] In one embodiment of the present invention, Ar １ and Ar ２At least one of the hydrogen atoms contained in the cycloalkyl group, the hydrogen atoms contained in the substituent of the cycloalkyl group, the hydrogen atoms contained in the heterocycloalkyl group, the hydrogen atoms contained in the substituent of the heterocycloalkyl group, the hydrogen atoms contained in the aryl group, the hydrogen atoms contained in the substituent of the aryl group, the hydrogen atoms contained in the heteroaryl group, and the hydrogen atoms contained in the substituent of the heteroaryl group represented by Ar is a deuterium atom. １ and Ar ２ At least one of the hydrogen atoms contained in the cycloalkyl group, the heterocycloalkyl group, the aryl group, and the heteroaryl group represented by Ar is a deuterium atom. １ and Ar ２ At least one of the hydrogen atoms contained in the aryl group represented by (A5a) is a deuterium atom. In other words, in one embodiment of the present invention, at least one of the above (A5a) to (A5d1) is a deuterium atom, preferably at least one of the above (A5a) to (A5d) is a deuterium atom, and more preferably at least one of the above (A5c) is a deuterium atom. Two or more of these hydrogen atoms may be deuterium atoms, or all of them may be deuterium atoms.

[0276] When any of the above (A5a) to (A5d1) is a deuterium atom, Ar containing the deuterium atom １ L binds to １ or Ar containing the deuterium atom ２ L binds to ２ It is preferred that the hydrogen atom bonded to is a deuterium atom.

[0277] In one embodiment of the present invention, m1 is 1 and L １ is represented by any one of the following formulas (3A) to (3D), or m2 is 1, and L ２ is represented by any one of the following formulas (3A) to (3D), or m1 and m2 are 1, and L １ and L ２are each independently represented by any one of the following formulas (3A) to (3D), and a hydrogen atom contained in a benzene ring contained in formulas (3A) to (3C), a substituent R Ａ a hydrogen atom contained in the group (3B), a substituent R Ｂ１ and R Ｂ２ a hydrogen atom contained in at least one of the groups represented by the formula (3C), Ｃ１ and R Ｃ２ a hydrogen atom contained in at least one of the five-membered rings contained in formula (3D), and a substituent R Ｄ At least one of the hydrogen atoms contained in is a deuterium atom.

[0278] In formulas (3A) to (3D), R Ａ , R Ｂ１ , R Ｂ２ , R Ｃ１ , R Ｃ２ , and R Ｄ represents a substituent, and X ２ and X ３ represents an oxygen atom or a sulfur atom, p, q1, and q2 each independently represent an integer of 0 to 6, r1, r2, and s each independently represent an integer of 0 to 4, * represents the central nitrogen atom N ＊ represents a bond to Ar １ and Ar ２ In formulae (3A) to (3D), R Ｂ１ and R Ｂ２ are the same as or different from each other. Ｃ１ and R Ｃ２ In formulas (3A) to (3D), when p, q1, q2, r1, r2, and s are each 2 or more, there are two or more pairs of R Ａ , R Ｂ１ , R Ｂ２ , R Ｃ１ , R Ｃ２ , and R Ｄ are either identical to each other or different from each other.

[0279] Preferably, at least one of the hydrogen atoms contained in the benzene rings included in formulas (3A) to (3C) and the five-membered ring included in formula (3D) is a deuterium atom. More preferably, at least one of the hydrogen atoms contained in the benzene rings included in formulas (3A) to (3C) is a deuterium atom. Even more preferably, at least one of the hydrogen atoms contained in the benzene rings included in formulas (3A) and (3B) is a deuterium atom. Two or more of these hydrogen atoms may be deuterium atoms, or all of them may be deuterium atoms.

[0280] In one embodiment, some of the hydrogen atoms in (A1a) to (A5d1) are deuterium atoms and the others are protium atoms, and in another embodiment, all of (A1a) to (A5d1) are deuterium atoms.

[0281] In another embodiment of the present invention, all of the hydrogen atoms contained in the molecule of compound (1) are proton atoms, in other words, all of the above (A1a) to (A5d1) are proton atoms.

[0282] In another embodiment, among the hydrogen atoms selected from the group consisting of (A1a) to (A2b1), preferably at least one is a proton atom, more preferably two or more are proton atoms, even more preferably three or more are proton atoms, and particularly preferably all are proton atoms.

[0283] In another embodiment, Ar １ and Ar ２ - a hydrogen atom contained in a heteroaryl group; - a hydrogen atom contained in a substituent carried by a heteroaryl group; - a hydrogen atom contained in an aryl group having a fused ring, among aryl groups; and - a hydrogen atom contained in a substituent carried by an aryl group having a fused ring, among aryl groups. Of these, preferably at least one is a proton atom, more preferably two or more are proton atoms, and even more preferably all are proton atoms.

[0284] The deuteration rate of the invention compound depends on the deuteration rate of the raw material compound used. Even when a raw material with a predetermined deuteration rate is used, a certain proportion of naturally occurring proton 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 proportion determined simply by counting the number of deuterium atoms represented by the chemical formula. The deuteration rate of the 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 invention compound may be a deuterated form in which all hydrogen atoms are deuterium atoms (i.e., the deuteration rate of the invention compound is 100%).

[0285] The 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, 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 invention compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, and still more preferably 10% or more, and less than 100%.

[0286] Details of the substituents (optional substituents) in the case of "substituted or unsubstituted" included in the definition of each of the above formulae are as described in "Substituents in the case of 'substituted or unsubstituted'" unless otherwise specified.

[0287] The method for producing compound (1) is not particularly limited, and a person skilled in the art can easily produce compound (1) by the method described in the following examples or by a method modified by referring to a known synthesis method.

[0288] Specific examples of compound (1) are shown below, but are not limited to these. In the following specific examples, D represents a deuterium atom.

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357] Material for Organic EL Device The material for organic EL devices, which is one embodiment of the present invention, contains an invention compound. The content of the 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%), even more preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). The material for organic EL devices, which is one embodiment of the present invention, is useful for producing organic EL devices. In one embodiment of the present invention, the invention compound is preferably a hole transport layer material.

[0358] In one embodiment of the present invention, the material for an organic EL device preferably further contains a protonated form of the invention compound. The protonated form refers to a compound in which all hydrogen atoms in the invention compound are protonated. The molar ratio of the invention compound to the protonated form of the invention compound (invention compound:protonated form) 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.

[0359] The material for an organic electroluminescence device according to one embodiment of the present invention is a hole transport layer material. The content of the invention compound in the material for an organic electroluminescence device is preferably 1% by mass or more (including 100%), more preferably 10% by mass or more (including 100%), even more preferably 50% by mass or more (including 100%), still more preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%).

[0360] Organic EL Device An organic EL 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 a single or multiple layers, including an emitting layer, and at least one layer selected from the group consisting of the single layer and multiple layers constituting the organic layer comprises an invention compound. Examples of organic layers containing the invention compound include, but are not limited to, a hole transporting zone (e.g., hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer) disposed between the anode and the emitting layer, the emitting layer, a spacer layer, and an electron transporting zone (e.g., electron injection layer, electron transport layer, hole blocking layer) disposed between the cathode and the emitting layer. The invention compound is preferably used as a material for the hole transporting zone or the emitting layer of a fluorescent or phosphorescent EL device, more preferably as a material for the hole transporting 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.

[0361] The organic EL device according to one embodiment of the present invention may be a fluorescent or phosphorescent monochromatic light-emitting device, a fluorescent / phosphorescent hybrid white light-emitting device, a simple type having a single light-emitting unit, or a tandem type having multiple light-emitting units, and is preferably a fluorescent light-emitting device. Here, the term "light-emitting unit" refers to a minimum unit that includes an organic layer, is composed of a single or multiple layers that constitute the organic layer, and at least one layer selected from the group consisting of the single layer and the multiple layers is an emitting layer, and emits light by recombination of injected holes and electrons.

[0362] For example, a typical element configuration of a simple-type organic EL element can be the following: (1) Anode / Light-emitting unit / Cathode The light-emitting unit may also 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 configuration of a simple-type light-emitting unit is shown below. The layers in parentheses are optional. (a) (hole injection layer / ) hole transport layer / fluorescent-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-emitting layer / electron transport layer ( / electron injection layer) (h1) (hole injection layer / ) first hole transport layer / second hole transport layer / third hole transport layer / fluorescent-emitting layer / electron transport layer ( / electron injection layer). (i) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent-emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer) (i1) (hole injection layer / ) first hole transport layer / second hole transport layer / third hole transport layer / fluorescent-emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer) (j) (hole injection layer / ) hole transport layer / fluorescent-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)

[0363] The phosphorescent or fluorescent-emitting layers may each emit a different light 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-emitting) / second phosphorescent-emitting layer (green-emitting) / spacer layer / fluorescent-emitting layer (blue-emitting) / electron transport layer. An electron-blocking layer may be provided between each light-emitting layer and the hole transport layer or the spacer layer, as appropriate. A hole-blocking layer may also be provided between each light-emitting layer and the electron transport layer, as appropriate. 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 luminous efficiency.

[0364] A typical element configuration of a tandem organic EL element can be as follows: (2) Anode / First Emitting Unit / Intermediate Layer / Second Emitting Unit / Cathode. Here, the first and second emitting units can be, for example, independently selected from the emitting units described above. The intermediate layer is generally also called an intermediate electrode, intermediate conductive layer, charge generating layer, electron withdrawing layer, connecting layer, or intermediate insulating layer, and can be made of known materials that supply electrons to the first emitting unit and holes to the second emitting unit. Furthermore, when the hole transport layer has a multilayer structure including two or more hole transport layers, the hole transport layer adjacent to the emitting layer in the multilayer structure, such as the second hole transport layer in the two-layer structure or the third hole transport layer in the three-layer structure, may function as an electron blocking layer. That is, when the hole transport layer has a multilayer structure including two or more hole transport layers, the hole transport layer adjacent to the emitting layer in the multilayer structure can also be used as an electron blocking layer.

[0365] 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 shown in FIG. 1 includes 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 includes an emitting layer 5. A hole transport zone 6 (e.g., a hole injection layer, a hole transport layer) is located between the emitting layer 5 and the anode 3, and an electron transport zone 7 (e.g., an electron injection layer, an electron transport layer) is located between the emitting layer 5 and the cathode 4. 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, further increasing the exciton generation efficiency in the emitting layer 5.

[0366] Fig. 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 shown in Fig. 2 includes 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 includes an emitting layer 5. The hole transporting region disposed between the anode 3 and the emitting layer 5 is formed of a hole injection layer 6a, a first hole transporting layer 6b, and a second hole transporting layer 6c. The electron transporting region disposed between the emitting layer 5 and the cathode 4 is formed of a first electron transporting layer 7a and a second electron transporting layer 7b.

[0367] 3 is a schematic diagram showing yet another configuration of an organic EL element according to one embodiment of the present invention. The organic EL element 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 transporting region disposed between the anode 3 and the emitting layer 5 is formed of a hole injection layer 6a, a first hole transporting layer 6b, a second hole transporting layer 6c, and a third hole transporting layer 6d. The electron transporting region disposed between the emitting layer 5 and the cathode 4 is formed of a first electron transporting layer 7a and a second electron transporting layer 7b.

[0368] 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 spacer layer).

[0369] In the present invention, a host combined with a fluorescent dopant material (fluorescent-emitting material) is referred to as a fluorescent host, and a host combined with a phosphorescent dopant material is referred to as a phosphorescent host. The fluorescent host and the phosphorescent host are not distinguished solely by molecular structure. That is, the phosphorescent host refers to a material that forms a phosphorescent-emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material that forms a fluorescent-emitting layer. The same applies to the fluorescent host.

[0370] Substrate The substrate is used as a support for the organic EL element. For example, a glass, quartz, or plastic plate can be used as the substrate. Flexible substrates may also be used. Examples of flexible substrates include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Inorganic vapor-deposited films can also be used.

[0371] Anode For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or 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).

[0372] These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target in which 1 to 10 wt % of zinc oxide is added to indium oxide, and indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target in which 0.5 to 5 wt % of tungsten oxide and 0.1 to 1 wt % of zinc oxide are added to indium oxide. Other methods that may be used for production include vacuum deposition, coating, inkjet printing, and spin coating.

[0373] Hole Transporting Zone As described above, the organic layer may include a hole transporting zone between the anode and the light emitting layer. The hole transporting zone is composed of a hole injection layer, a hole transporting layer, an electron blocking layer, etc. It is preferable that the hole transporting zone contains the compound of the invention. It is preferable that the compound of the invention is contained in at least one layer selected from the group consisting of these layers (hole injection layer, hole transport layer, electron blocking layer, etc.) that constitute the hole transporting zone, and it is particularly preferable that the compound of the invention is contained in the hole transporting layer.

[0374] 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 commonly used as electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, 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 Group 2 of the periodic table, can also be used, including 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 forming an anode using alkali metals, alkaline earth metals, and alloys containing these, vacuum deposition or sputtering can be used. Furthermore, when using silver paste or the like, coating or inkjet printing can be used.

[0375] 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.

[0376] Examples of hole injection 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.

[0377] The low molecular weight 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), and 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-phenylaminophenyl]-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).

[0378] Polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used. Examples include 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), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD). Furthermore, 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.

[0379] Furthermore, it is also preferable to use an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K).

[0380]

[0381] (In the above formula, R ２２１ ~R ２２６ each independently represents a cyano group, —CONH ２ , a carboxyl group, or -COOR ２２７ (R ２２７ represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms). ２２１ and R ２２２ , R ２２３ and R ２２４ , and R ２２５ and R ２２６ Two adjacent groups selected from the following may be bonded to each other to form a group represented by —CO—O—CO—. 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.

[0382] Hole Transport Layer The hole transport layer is a layer containing a material with high hole transport properties (hole transport material), and is formed between the anode and the light-emitting layer, or, if present, between the hole injection layer and the light-emitting layer. The invention compound may be used alone or in combination with the following compounds in the hole transport layer.

[0383] 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. Furthermore, the hole transport layer closest to the cathode in the multilayer structure, for example, the second hole transport layer in the two-layer structure or the third hole transport layer in the three-layer structure, is preferably adjacent to the light-emitting layer. In another embodiment of the present invention, an electron blocking layer, as described below, may be interposed between the hole transport layer and the light-emitting layer in the single-layer structure, or between the hole transport layer closest to the light-emitting layer and the light-emitting layer in the multilayer structure. Furthermore, as described above, when the hole transport layer has a multilayer structure including two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer in the multilayer structure can also be used as an electron blocking layer. In one embodiment of the organic electroluminescent device according to the present invention, at least one selected from the group consisting of the first hole transport layer and the second hole transport layer contains the invention compound. Specifically, in the hole transport layer having a two-layer structure, the invention compound may be contained in either the first hole transport layer or the second hole transport layer, or in both. In another embodiment, at least one selected from the group consisting of the first to third hole transport layers contains the invention compound. Specifically, in the hole transport layer having a three-layer structure, the invention compound may be contained in only one, any two, or all of the first to third hole transport layers.

[0384] In one embodiment of the present invention, the invention compound is preferably contained in the second hole transport layer. Specifically, the invention compound is preferably contained only in the second hole transport layer, or the invention compound is preferably contained in both the first and second hole transport layers. In one embodiment of the present invention, the invention compound contained in one or both of the first and second hole transport layers, or the invention compound contained in at least one or more selected from the group consisting of the first to third hole transport layers, is preferably a proteide from the viewpoint of production cost. The proteide refers to an invention compound in which all hydrogen atoms are proteides. Therefore, the present invention includes an organic EL device in which one or both of the first and second hole transport layers, or one or more selected from the group consisting of the first to third hole transport layers, contains an invention compound substantially consisting of a proteide. The term "invention compound substantially consisting of a proteide" means that the content of the proteide 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 (all including 100%).

[0385] Examples of materials that can be used for the hole transport layer other than the compound of the present invention include aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. 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). －６ cm２ / Vs or more.

[0386] 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.

[0387] In one embodiment of the organic EL element according to the present invention, the first hole transport layer contains a compound represented by the following formula (21) or (22).

[0388] [In the formula (21) and the formula (22), L Ａ１ , L Ｂ１ , L Ｃ１ , L Ａ２ , L Ｂ２ , L Ｃ２ and L Ｄ２ are each independently 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, k1 is 1, 2, 3, or 4, and when k1 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, and when k1 is 2, 3, or 4, a plurality of L Ｅ２ are the same or different from each other, and when k1 is 2, 3 or 4, a plurality of L Ｅ２are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and L does not form a monocyclic ring or a fused ring; Ｅ２ A is 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, 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 R' are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; ９０１ When there are a plurality of R' ９０１ are the same or different from each other, and R' ９０２ When there are a plurality of R' ９０２ are the same or different from each other, and R' ９０３ When there are a plurality of R' ９０３ are the same as or different from each other.

[0389] The first hole transport layer may contain one kind of the compound represented by formula (21) and formula (22), or may contain two or more kinds of the compounds represented by formula (21) and formula (22).

[0390] In formula (21) and formula (22), A １ , B １ , C １ , A ２ , B ２ , C ２ , and D ２are preferably each independently selected from a substituted or unsubstituted phenyl 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. １ , B １ and C １ and in formula (22), A ２ , B ２ , C ２ , and D ２ At least one selected from the group consisting of 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.

[0391] A １ , B １ , C １ , A ２ , B ２ , C ２ , and D ２ The fluorenyl group represented by the formula (I) may have a substituent at the 9-position, such as a 9,9-dimethylfluorenyl group or a 9,9-diphenylfluorenyl group. The substituents at the 9-position may together form a ring, such as a fluorene skeleton or a xanthene skeleton.

[0392] 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.

[0393] Specific examples of the compounds represented by formula (21) and formula (22) include the following compounds.

[0394]

[0395] Dopant Material of 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 element according to the present invention, the light-emitting layer is a single layer. In another embodiment of the organic EL element according to the present invention, the light-emitting layer includes a first light-emitting layer and a second light-emitting layer.

[0396] 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, azaborine derivatives, and arylborane derivatives. 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), and 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA).

[0397] 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-carbazole-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-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), and the like.

[0398] 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) and 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD).

[0399] In one embodiment of the present invention, the light-emitting layer preferably contains a fluorescent light-emitting material (fluorescent dopant material).

[0400] 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).

[0401] Green phosphorescent materials that can be used in the light-emitting layer include iridium complexes, such as 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)).

[0402] As the red phosphorescent material that can be used in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used. Specific examples include organometallic complexes such as 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).

[0403] Furthermore, 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).

[0404] The light-emitting layer may have a structure in which the above-described dopant material is dispersed in another material (host material). It is preferable to use a material having a lower lowest unoccupied molecular orbital (LUMO) level and a lower highest occupied molecular orbital (HOMO) level than the dopant material.

[0405] Examples of host materials that can be used include: (1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; (2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives; (3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and chrysene derivatives; and (4) aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives.

[0406] 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-B uDNA), 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), 6,12-dimethoxy-5,11-diphenylchrysene, and other condensed aromatic compounds;and N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H Examples of the aromatic amine compounds that can be used include N,N'-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). Multiple types of host materials may be used.

[0407] In particular, in the case of a blue fluorescent element, it is preferable to use the following anthracene compound as the host material.

[0408]

[0409]

[0410]

[0411]

[0412] In one embodiment of the organic EL element according to the present invention, when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, at least one of the components constituting the first light-emitting layer is different from the components constituting the second light-emitting layer. For example, the dopant material contained in the first light-emitting layer may be different from the dopant material contained in the second light-emitting layer, or the host material contained in the first light-emitting layer may be different from the host material contained in the second light-emitting layer.

[0413] In the organic EL device according to this embodiment, the light-emitting layer may contain a light-emitting compound that exhibits fluorescent emission. The light-emitting compound may be a light-emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less.

[0414] 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 spectrofluorometer (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. The peak wavelength of the emission spectrum at which the emission intensity is maximum is defined as the main peak wavelength. Note that in this specification, the main peak wavelength may also be referred to as the fluorescence emission main peak wavelength (FL-peak).

[0415] The light-emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less may be the dopant material or the host material.

[0416] 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 with a main peak wavelength of 500 nm or less, or both materials may be light-emitting compounds that exhibit fluorescent emission with a main peak wavelength of 500 nm or less. When the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, only one of the first light-emitting layer and the second light-emitting layer may contain a light-emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less, or both light-emitting layers may contain a light-emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less. When the first light-emitting layer contains a light-emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less, only one of the dopant material and the host material contained in the first light-emitting layer may be a light-emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less, or both materials may be light-emitting compounds that exhibit fluorescent emission with a main peak wavelength of 500 nm or less. Furthermore, when the second light-emitting layer contains a light-emitting compound that exhibits fluorescent emission having a main peak wavelength of 500 nm or less, only one of the dopant material and the host material contained in the second light-emitting layer may be a light-emitting compound that exhibits fluorescent emission having a main peak wavelength of 500 nm or less, or both materials may be light-emitting compounds that exhibit fluorescent emission having a main peak wavelength of 500 nm or less.

[0417] Electron Transport Layer The electron transport layer is a layer containing a material with high electron transport properties (electron transport material) and is formed between the light-emitting layer and the cathode, or, if present, between the electron injection layer and the light-emitting layer. The electron transport layer may have a single-layer structure or a multilayer structure containing two or more layers. For example, the electron transport layer may have a two-layer structure containing 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 multilayer structure, such as the first electron transport layer in the two-layer structure, is preferably adjacent to the light-emitting layer. In another embodiment of the present invention, a hole-blocking layer, as described below, may be interposed between the electron transport layer and the light-emitting layer of the single-layer structure, or between the electron transport layer closest to the light-emitting layer and the light-emitting layer in the multilayer structure.

[0418] The electron transport layer may be made of, 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; or (3) polymer compounds.

[0419] Examples of metal complexes include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), and bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq). ２ ), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), and (8-quinolinolato)lithium (abbreviation: Liq).

[0420] 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, Examples of such benzophenanthroline include 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).

[0421] Examples of the polymer compound include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy).

[0422] The above material is 10 －６ cm ２ / 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 transport property than a hole transport property. The electron transport layer may be not only a single layer, but also a laminate of two or more layers each containing the above materials. When the electron transport layer has a two-layer structure, the layer on the anode side is referred to as the first electron transport layer, and the layer on the cathode side is referred to as the second electron transport layer.

[0423] 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 such as (8-quinolinolato)lithium (Liq), 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. A mixture of these compounds can also be used. Alternatively, a material having electron transport properties containing an alkali metal, alkaline earth metal, or a compound thereof, such as Alq containing magnesium (Mg), can be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, a composite material comprising 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 electron transport properties because the organic compound accepts electrons from the electron donor. In this case, the organic compound is preferably a material that is excellent at transporting the accepted electrons. Specifically, for example, the materials constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) described above 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, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides and alkaline earth metal oxides are also preferred, such as lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (abbreviated as TTF) can also be used.

[0424] Cathode For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof with a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), and ytterbium (Yb), and alloys containing these. When forming a cathode using alkali metals, alkaline earth metals, or alloys containing these, vacuum deposition or sputtering can be used. When using silver paste or the like, coating or inkjet printing can be used. By providing an electron injection layer, the cathode can be formed using various conductive materials, regardless of the magnitude of the work function, such as Al, Ag, ITO, graphene, and indium oxide-tin oxide containing silicon or silicon oxide. These conductive materials can be formed into films by sputtering, ink jetting, spin coating, or the like.

[0425] Insulating Layer Organic EL elements are prone to pixel defects due to leakage and short circuits 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. Materials used for the insulating layer include, for example, 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, and vanadium oxide. Mixtures or laminates of these materials may also be used.

[0426] Spacer Layer The spacer layer is a layer provided between a fluorescent-emitting layer and a phosphorescent-emitting layer, for example, when the fluorescent-emitting layer and the phosphorescent-emitting layer are stacked, for the purpose of preventing excitons generated in the phosphorescent-emitting layer from diffusing into the fluorescent-emitting layer or for the purpose of adjusting the carrier balance. Spacer layers can also be provided between multiple phosphorescent-emitting layers. Because the spacer layer is provided between the light-emitting layers, it is preferable that the spacer layer be made of a material that has both electron transport and hole transport properties. Furthermore, in order to prevent the diffusion of triplet energy in adjacent phosphorescent-emitting layers, it is preferable that the triplet energy be 2.6 eV or more. Materials used for the spacer layer include those similar to those used for the hole transport layer described above.

[0427] Blocking Layer A blocking layer such as an electron blocking layer, hole blocking layer, or exciton blocking layer may be provided adjacent to the light-emitting layer. An electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer, and a hole blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron transport layer. An exciton blocking layer has the function of preventing excitons generated in the light-emitting layer from diffusing to surrounding layers and confining the excitons within the light-emitting layer.

[0428] Each layer of the organic EL element can be formed by a conventionally known vapor deposition method, coating method, etc. For example, the layers can be formed by a conventionally known vapor deposition method such as vacuum vapor deposition or molecular beam deposition (MBE), or by a coating method using a solution of a compound that forms the layer, such as dipping, spin coating, casting, bar coating, or roll coating.

[0429] The thickness of each layer is not particularly limited, but generally, if the thickness is too thin, defects such as pinholes are likely to occur, whereas if the thickness is too thick, a high driving voltage is required, resulting in poor efficiency. Therefore, the thickness is usually 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm.

[0430] In one embodiment of the organic EL element of the present invention, the sum of the thicknesses of the first hole transport layer and the second hole transport layer is 30 nm or more and 150 nm or less. In this case, it is preferably 40 nm or more and 130 nm or less. In another embodiment of the organic EL element of the present invention, the thickness of the second hole transport layer is 20 nm or more. It is preferably 25 nm or more, more preferably 35 nm or more, and preferably 100 nm or less. In another embodiment of the organic EL element of the present invention, the thickness of the hole transport layer adjacent to the light-emitting layer is 20 nm or more. It is preferably 25 nm or more, more preferably 30 nm or more, and preferably 100 nm or less. In another embodiment of the organic EL element of the present invention, the thickness D1 of the first hole transport layer and the thickness D2 of the second hole transport layer satisfy the relationship 0.3<D2 / D1<4.0. It preferably satisfies the relationship 0.5<D2 / D1<3.5, and more preferably satisfies the relationship 0.75<D2 / D1<3.0.

[0431] Embodiments of the organic EL device of the present invention include, for example: an organic EL device having a hole transport layer of the above two-layer structure, in which: - a first embodiment in which the second hole transport layer contains the compound of the present invention, and the first hole transport layer does not contain the compound of the present invention; - a second embodiment in which both the first hole transport layer and the second hole transport layer contain the compound of the present invention; - a third embodiment in which the first hole transport layer contains the compound of the present invention, and the second hole transport layer does not contain the compound of the present invention; an organic EL device having a hole transport layer of the above three-layer structure, in which: - a fourth embodiment in which the first hole transport layer contains the compound of the present invention, and the second and third hole transport layers do not contain the compound of the present invention; - a fifth embodiment in which the second hole transport layer contains the compound of the present invention, and the first and third hole transport layers do not contain the compound of the present invention; - a sixth embodiment in which the third hole transport layer contains the compound of the present invention, and the first and second hole transport layers do not contain the compound of the present invention; - a seventh embodiment in which the first and second hole transport layers contain the compound of the present invention, and the third hole transport layer does not contain the compound of the present invention; An eighth embodiment in which the first and third hole transport layers contain a compound of the present invention, and the second hole transport layer does not contain a compound of the present invention; a ninth embodiment in which the second and third hole transport layers contain a compound of the present invention, and the first hole transport layer does not contain a compound of the present invention; and a tenth embodiment in which all of the first to third hole transport layers contain a compound of the present invention.

[0432] The organic EL element can be used in electronic devices such as display components such as organic EL panel modules, display devices for televisions, mobile phones, personal computers, etc., and light-emitting devices for lighting and vehicle lamps, etc. In other words, an electronic device according to an embodiment of the present invention includes any of the organic EL elements described above.

[0433] The present invention will be described in more detail below using examples, but the present invention is not limited to the following examples.

[0434] Compounds used in the production of organic EL devices in the examples

[0435]

[0436]

[0437] Comparative compounds used in the manufacture of organic EL devices of comparative examples

[0438]

[0439] Other compounds used in the production of organic EL devices in Examples and Comparative Examples

[0440]

[0441] A 25 mm x 75 mm x 1.1 mm glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) 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 cleaned glass substrate with the transparent electrode was attached to a substrate holder in a vacuum deposition apparatus, and first, compound HT-1 and compound HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, forming a hole injection layer with a film thickness of 10 nm. The mass ratio of compound HT-1 to compound HA (HT-1:HA) was 97:3. Next, compound HT-1 was vapor-deposited on the hole injection layer to form a first hole transport layer with a film thickness of 85 nm. Next, compound 1 was vapor-deposited on this first hole transport layer as compound HT-2 to form a second hole transport layer with a film thickness of 5 nm. Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited on this second hole-transporting layer to form an emitting layer with a thickness of 20 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 99:1. Next, compound ET-1 was deposited on this emitting layer to form a first electron-transporting layer with a thickness of 5 nm. Next, compound ET-2 and Liq were co-deposited on this first electron-transporting layer to form a second electron-transporting layer with a thickness of 31 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50. Next, Liq was deposited on this second electron-transporting layer to form an electron-injecting electrode with a thickness of 1 nm. Then, metal Al was deposited on this electron-injecting electrode to form a metal cathode with a thickness of 80 nm. The layer configuration of the organic EL device of Example 1-1 obtained in this manner is shown below. ITO (130) / HT-1:HA = 97:3 (10) / HT-1 (85) / HT-2 (5) / BH-1:BD-1 = 99:1 (20) / ET-1 (5) / ET-2:Liq = 50:50 (31) / Liq (1) / Al (80) In the above layer structure, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

[0442] Examples 2 to 11 Organic EL devices were fabricated in the same manner as in Example 1, except that the second hole transport layer material was changed from Compound 1 to Compound 2, Compound 3, Compound 4, Compound 5, Compound 6, Compound 7, Compound 8, Compound 9, Compound 10, or Compound 11, respectively, as shown in Table 1 below.

[0443] Comparative Examples 1 to 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 Compound 1, Comparative Compound 2, or Comparative Compound 3, as shown in Table 1 below.

[0444] Evaluation of Organic EL Devices (External Quantum Efficiency (EQE)) The organic EL devices fabricated in Examples and Comparative Examples were subjected to a current density of 10 mA / cm at room temperature. ２ The organic EL elements were driven at a constant DC current of 50 mA / cm and the external quantum efficiency (%) was measured using a luminance meter (Spectroradiometer CS-1000 manufactured by Konica Minolta, Inc.). ２ A voltage was applied to the organic EL element so that the 95% lifetime (LT95) was evaluated. Here, the 95% lifetime (LT95) refers to the time (hr) until the luminance decreases to 95% of the initial luminance when driven at a constant current. The results are shown in Table 1.

[0445]

[0446] As is clear from the results in Table 1, the amine compounds satisfying the requirements of the present invention (compounds 1 to 11 in Examples 1 to 11) exhibit significantly improved EQE and LT95 values ​​compared to the amine compounds not satisfying the requirements of the present invention (comparative compounds 1 to 3 in Comparative Examples 1 to 3).

[0447] <Synthesis of Compounds> Intermediate Synthesis Example 1: Synthesis of Intermediate A-1

[0448]

[0449] A mixture of the following components was refluxed at the boiling point under an argon atmosphere for 3 hours. Raw material 1: 8-bromonaphtho[1,2-b]benzofuran (2.97 g, 10 mmol) Raw material 2: (3-chlorophenyl)boronic acid (1.56 g, 10 mmol) Catalyst: bis(triphenylphosphine)palladium(II) dichloride (0.14 g, 0.2 mmol) Base: 2 M aqueous potassium carbonate solution (15 mL) Solvent: 1,2-dimethoxyethane (DME) (50 mL) The reaction solution was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain intermediate A-1 as a white solid (2.51 g). The yield was 76%.

[0450] Intermediate Synthesis Examples 2 to 4: Synthesis of Intermediate A-2, Intermediate A-3, and Intermediate A-4 Intermediates A-2 to A-4 were synthesized in the same manner as in the synthesis of Intermediate A-1, except that raw materials 1 and 2 were changed to the compounds shown in Table 2 below. Intermediates A-1 to A-4 are shown in Table 2 together with raw materials 1 and 2 and the yields.

[0451]

[0452] Synthesis Example 1: Synthesis of Compound 1

[0453]

[0454] A mixture of the following components was stirred at 110°C for 5 hours under an argon atmosphere. Intermediate A: Intermediate A-1 (3.29 g, 10 mmol) Intermediate B: Di([1,1'-biphenyl]-4-yl)amine (3.21 g, 10 mmol) Catalyst: Tris(dibenzylideneacetone)dipalladium(0) (0.183 g, 0.2 mmol) Ligand: Tri-tert-butylphosphonium tetrafluoroborate (0.232 g, 0.8 mmol) Base: Sodium t-butoxide (1.44 g, 15 mmol) Solvent: Xylene (50 mL) 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 3.12 g of a white solid. The yield was 51%. Mass spectrometry analysis showed that the obtained product was Compound 1, with a molecular weight of 613.76 and an m / e of 614.

[0455] Synthesis Examples 2 to 11: Synthesis of Compounds 2 to 11 Compounds 2, 3, 4, 5, 6, 7, 8, 9, 10, and 11 were synthesized in the same manner as in the synthesis of Compound 1, except that the compounds shown in Table 3 below were used as Intermediates A and B. Compounds 1 to 11 are shown in Tables 3-1 and 3-2 together with the raw materials Intermediates A and B and the yields.

[0456]

[0457]

[0458] REFERENCE SIGNS LIST 1, 11, 12 organic EL element 2 substrate 3 anode 4 cathode 5 light-emitting layer 6 hole-transporting region (hole-transporting layer) 6a hole-injecting layer 6b first hole-transporting layer 6c second hole-transporting layer 6d third hole-transporting layer 7 electron-transporting region (electron-transporting layer) 7a first electron-transporting layer 7b second electron-transporting layer 10, 20, 30 light-emitting unit

Claims

1. A compound represented by the following formula (1): [In formula (1), ・N ＊ is the central nitrogen atom. X is an oxygen atom or a sulfur atom. Y ２ and Y ３ One selected from is a single bond bonded to *a. １ , R ４ and the Y which is not a single bond ２ and Y ３ 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 do not bond to each other to form a ring. ５ ~R １０ is a hydrogen atom, or any two or more of them are bonded to each other to form a substituted or unsubstituted ring. １１ ~R １４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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. １１ ~R １４ are not bonded to each other and do not form a ring. １ and L ２ are each independently 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. m1 and m2 are each independently 0 or 1. When m1 is 0, Ar １ N ＊ When m2 is 0, Ar ２ N ＊ Binds to. L ３ and L ４ are each independently a substituted or unsubstituted arylene group having 6 to 10 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 10 ring atoms. n1 is 0 or 1. When n1 is 0, R １３ The carbon atom bonded to R １４ Carbon atoms bonded to both of the carbon atoms bonded to N ＊ n2 is 0 or 1. When n2 is 0, R １１ The carbon atom bonded to R １４ The carbon atoms bonded to both of the carbon atoms bonded to Y ２ and Y ３ Ar binds to one selected from １ and Ar ２ are each independently a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 20 ring atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 ring atoms. １ is an unsubstituted 4,3'-biphenylene group, and Ar １ is a substituted or unsubstituted heteroaryl group having 3 to 20 ring atoms, １ , and m2 is 1, L ２ is an unsubstituted 4,3'-biphenylene group, and Ar ２ is a substituted or unsubstituted heteroaryl group having 3 to 20 ring atoms, ２ are each independently selected from a substituted or unsubstituted 1-carbazolyl group, a substituted or unsubstituted 2-carbazolyl group, a substituted or unsubstituted 3-carbazolyl group, a substituted or unsubstituted 4-carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted benzofurocarbazolyl group, a substituted or unsubstituted benzothienocarbazolyl group, and a substituted or unsubstituted indenocarbazolyl group. １ When Ar is a biphenyl group having a substituent, the substituent is the following substituent A. ２ When m1 is 1, L is a biphenyl group having a substituent, the substituent is the following substituent A. １ is a phenylene group, and Ar １ When m2 is 1, L is a phenyl group having a substituent, the substituent is the following substituent A. ２ is a phenylene group, and Ar ２ When Ar is a phenyl group having a substituent, the substituent is the following substituent A. １ and Ar ２ are both unsubstituted naphthyl groups, m1 and m2 are both 1, and L １ and L ２ When both are unsubstituted phenylene groups, L １ and L ２ One of the groups is an unsubstituted o-phenylene group, an unsubstituted m-phenylene group, or an unsubstituted p-phenylene group, and the other group is an unsubstituted o-phenylene group or an unsubstituted p-phenylene group. １ When Ar is a phenyl group having a substituent, the substituent is the following substituent B. ２ When Ar is a phenyl group having a substituent, the substituent is the following substituent B. １ and Ar ２ are both unsubstituted dibenzofuranyl groups, m1 and m2 are both 1, and L １ and L ２ When both are unsubstituted phenylene groups, L １ and L ２ One of the groups is an unsubstituted o-phenylene group, an unsubstituted m-phenylene group, or an unsubstituted p-phenylene group, and the other group is an unsubstituted o-phenylene group or an unsubstituted m-phenylene group. １ When Ar is a phenyl group having a substituent, the substituent is the following substituent C. ２ is a phenyl group having a substituent, the substituent is the following substituent C. - However, the substituent A is selected from a group which the following substituent D may take, an unsubstituted dibenzofuranyl group, and an unsubstituted naphthyl group. - The substituent B is selected from a group which the following substituent D may take, an unsubstituted 9-carbazolyl group, and an unsubstituted dibenzofuranyl group. - The substituent C is selected from a group which the following substituent D may take, an unsubstituted naphthyl group, and an unsubstituted 9-carbazolyl group. the substituent D is a cyano group; a halogen atom; a phosphine oxide group substituted with an unsubstituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted alkyl group having 1 to 30 carbon atoms; an unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms; an unsubstituted aralkyl group having 7 to 36 carbon atoms; an unsubstituted alkoxy group having 1 to 30 carbon atoms; an unsubstituted aryloxy group having 6 to 30 ring carbon atoms; a mono-, di- or tri-substituted silyl group having a substituent selected from an unsubstituted alkyl group having 1 to 30 carbon atoms and an unsubstituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted haloalkyl group having 1 to 30 carbon atoms; an unsubstituted haloalkoxy group having 1 to 30 carbon atoms; a boryl group substituted with an unsubstituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted alkylthio group having 1 to 30 carbon atoms; an unsubstituted arylthio group having 6 to 30 ring carbon atoms; and unsubstituted phenyl group, unsubstituted tolyl group, unsubstituted xylyl group, unsubstituted ethylphenyl group, unsubstituted anthryl group, unsubstituted phenanthryl group, unsubstituted biphenylyl group, and unsubstituted anthryl group; unsubstituted 1-carbazolyl group, unsubstituted 2-carbazolyl group, unsubstituted 3-carbazolyl group, unsubstituted 4-carbazolyl group, unsubstituted dibenzothiophenyl group, unsubstituted benzonaphthofuranyl group, unsubstituted benzonaphthothiophenyl group, unsubstituted indolocarbazolyl group, unsubstituted benzofurocarbazolyl group, unsubstituted benzothienocarbazolyl group, unsubstituted indenocarbazolyl group, and unsubstituted dibenzocarbazolyl group.

2. The compound according to claim 1, represented by the following formula (1A): [In formula (1A), R １ , Y ３ , R ４ ~R １０ , R １１ ~R １４ , L １ ~L ４ , Ar １ , Ar ２ , N ＊ , X, m1, m2, n1, and n2 are as defined in formula (1).

3. The compound according to claim 1, represented by the following formula (1B): [In formula (1B), R １ , Y ２ , R ４ ~R １０ , R １１ ~R １４ , L １ ~L ４ , Ar １ , Ar ２ , N ＊ , X, m1, m2, n1, and n2 are as defined in formula (1).

4. The compound according to claim 1 or 2, represented by the following formula (1Aa): [In formula (1Aa), R １ , Y ３ , R ４ ~R １０ , R １１ ~R １４ , L １ , L ２ , Ar １ , Ar ２ , N ＊ , X, m1, and m2 are as defined in formula (1).

5. The compound according to claim 1 or 2, represented by the following formula (1Ab) or (1Ac): [In formula (1Ab) and formula (1Ac), R １ , Y ３ , R ４ ~R １０ , R １１ ~R １４ , L １ ~L ４ , Ar １ , Ar ２ , N ＊ , X, m1, and m2 are as defined in formula (1).

6. The compound according to claim 1 or 3, represented by the following formula (1Ba): [In formula (1Ba), R １ , Y ２ , R ４ ~R １０ , R １１ ~R １４ , L １ , L ２ , Ar １ , Ar ２ , N ＊ , X, m1, and m2 are as defined in formula (1).

7. The compound according to claim 1 or 3, represented by the following formula (1Bb) or (1Bc): [In formula (1Bb) and formula (1Bc), R １ , Y ２ , R ４ ~R １０ , R １１ ~R １４ , L １ ~L ４ , Ar １ , Ar ２ , N ＊ , X, m1, and m2 are as defined in formula (1).

8. The compound according to any one of claims 1 to 7, wherein m1 is 0 and m2 is 0.

9. The compound according to any one of claims 1 to 7, wherein one of m1 and m2 is 0 and the other is 1.

10. The compound according to any one of claims 1 to 7, wherein m1 is 1 and m2 is 1.

11. The compound according to any one of claims 1, 2, and 4, represented by any one of the following formulas (1Aa-1) to (1Aa-3): [In formula (1Aa-2) and formula (1Aa-3), R ２１ ~R ２５ is a single bond bonded to *b, and R ２１ ~R ２５ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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. ２１ ~R ２５ two or more of R are bonded to each other to form a substituted or unsubstituted ring of 6 or less members, or ２１ ~R ２５ are not bonded to each other to form a ring. ３１ ~R ３５ is a single bond bonded to *c, and R ３１ ~R ３５ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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. ３１ ~R ３５ two or more of R are bonded to each other to form a substituted or unsubstituted ring of 6 or less members, or ３１ ~R ３５ are not bonded to each other to form a ring. １ , Y ３ , R ４ ~R １０ , R １１ ~R １４ , Ar １ , Ar ２ , N ＊ and X is as defined in formula (1).

12. The compound according to any one of claims 1, 3, or 6, represented by any one of the following formulas (1Ba-1) to (1Ba-3): [In formula (1Ba-2) and formula (1Ba-3), R ２１ ~R ２５ is a single bond bonded to *b, and R ２１ ~R ２５ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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. ２１ ~R ２５ two or more of R are bonded to each other to form a substituted or unsubstituted ring of 6 or less members, or ２１ ~R ２５ are not bonded to each other to form a ring. ３１ ~R ３５ is a single bond bonded to *c, and R ３１ ~R ３５ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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. ３１ ~R ３５ two or more of R are bonded to each other to form a substituted or unsubstituted ring of 6 or less members, or ３１ ~R ３５ are not bonded to each other to form a ring. １ , Y ２ , R ４ ~R １０ , R １１ ~R １４ , Ar １ , Ar ２ , N ＊ and X is as defined in formula (1).

13. The compound according to any one of claims 1, 2, and 4, represented by the following formula (1Aa-4) or (1Aa-5): [In formula (1Aa-4) and formula (1Aa-5), R ４１ ~R ４５ is a single bond bonded to *d, and R ４１ ~R ４５ is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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. ４１ ~R ４５ two or more of R are bonded to each other to form a substituted or unsubstituted ring of 6 or less members, or ４１ ~R ４５ are not bonded to each other to form a ring. ５１ , R ５３ , and R ５５ is a single bond bonded to *e, and Y ５２ , Y ５４ and R which is not a single bond. ５１ , R ５３ , and R ５５ is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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. ５２ , Y ５４ and R which is not a single bond. ５１ , R ５３ , and R ５５ Two or more of R are bonded to each other to form a substituted or unsubstituted ring of 6 or less members, or they are not bonded to each other to form a ring. １ , Y ３ , R ４ ~R １０ , R １１ ~R １４ , L ２ , Ar １ , Ar ２ , N ＊ and X is as defined in formula (1).

14. The compound according to any one of claims 1, 3, or 6, represented by the following formula (1Ba-4) or formula (1Ba-5): [In formula (1Ba-4) and formula (1Ba-5), R ４１ ~R ４５ is a single bond bonded to *d, and R ４１ ~R ４５ is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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. ４１ ~R ４５ two or more of R are bonded to each other to form a substituted or unsubstituted ring of 6 or less members, or ４１ ~R ４５ are not bonded to each other to form a ring. ５１ , R ５３ , and R ５５ is a single bond bonded to *e, and Y ５２ , Y ５４ and R which is not a single bond. ５１ , R ５３ , and R ５５ is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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. ５２ , Y ５４ and R which is not a single bond. ５１ , R ５３ , and R ５５ Two or more of R are bonded to each other to form a substituted or unsubstituted ring of 6 or less members, or they are not bonded to each other to form a ring. １ , Y ２ , R ４ ~R １０ , R １１ ~R １４ , L ２ , Ar １ , Ar ２ , N ＊ and X is as defined in formula (1).

15. Ar １ and Ar ２ are each independently represented by the following formula (2A), (2B), (2C), (2D), (2E), (2F), or (2G): (In formula (2A), *21 is L １ and L ２ represents a bond to one or both of 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. １０１ ~R １０５ and R １０６ ~R １１０ are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms. １０１ ~R １０５ Two adjacent groups selected from the group consisting of R １０６ ~R １１０ Adjacent two selected from are not bonded to each other to form a ring. 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 adjacent two selected from are not bonded to each other to form a ring. j is 0, 1 or 2, and k is 0 or 1. Except when j is 2 and k is 0. When j=0 and k=0, *23 represents *21. When j=0 and k=1, *22 represents *21. When j=1 and k=0, *23 represents *22. When m1 is 0 and Ar １ is represented by formula (2A), j is 0, k is 0, and R １１１ ~R １１５ When at least one selected from is a substituent other than a hydrogen atom, the substituent is selected from the groups which the substituent D may have and an unsubstituted 9-carbazolyl group. ２ is represented by formula (2A), j is 0, k is 0, and R １１１ ~R １１５ When at least one selected from the group consisting of is a substituent other than a hydrogen atom, the substituent is selected from the groups which the substituent D may have and an unsubstituted 9-carbazolyl group. １ is a phenylene group, and Ar １ is represented by formula (2A), j is 0, k is 0, and R １１１ ~R １１５ When at least one selected from is a substituent other than a hydrogen atom, the substituent is the above-mentioned substituent A. ２ is a phenylene group, and Ar ２ is represented by formula (2A), j is 0, k is 0, and R １１１ ~R １１５ When at least one selected from the group consisting of is a substituent other than a hydrogen atom, the substituent is the above-mentioned substituent A. １ is represented by formula (2A), j is 0, k is 1, and R １１１ ~R １１５ and R which is not a single bond １０６ ~R １１０ is a substituent other than a hydrogen atom, and m1 is 0 and Ar １ is represented by formula (2A), j is 1, k is 0, and R １１１ ~R １１５ and R which is not a single bond １０１ ~R １０５ When at least one of the groups is a substituent other than a hydrogen atom, the substituent is the above-mentioned substituent A. ２ is represented by formula (2A), j is 0, k is 1, and R １１１ ~R １１５ and R which is not a single bond １０６ ~R １１０ is a substituent other than a hydrogen atom, and m2 is 0 and Ar ２ is represented by formula (2A), j is 1, k is 0, and R １１１ ~R １１５ and R which is not a single bond １０１ ~R １０５ When at least one of is a substituent other than a hydrogen atom, the substituent is the above-mentioned substituent A. (In formula (2B), *24 is L １ and L ２ represents a bond to one or both of １２１ ~R １２８ One selected from is a single bond bonded to *25. 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 Adjacent two selected from are not bonded to each other to form a ring. １ and Ar ２ are both represented by formula (2B), and R １２１ ~R １２８ are all hydrogen atoms, m1 and m2 in formula (1) are both 1, and L １ and L ２ When both are unsubstituted phenylene groups, L １ and L ２ one of which is an unsubstituted o-phenylene group, an unsubstituted m-phenylene group, or an unsubstituted p-phenylene group, and the other is an unsubstituted o-phenylene group or an unsubstituted p-phenylene group. (In formula (2C), *26 is L １ and L ２ represents a bond to one or both of １３１ ~R １４０ One selected from is a single bond bonded to *27. 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 Adjacent two selected from are not bonded to each other to form a ring. (In formula (2D), *28 is L １ and L ２ represents a bond to one or both of the following: １ is an oxygen atom, a sulfur atom, -CR ａ R ｂ , or -NR ｃ It is. １ -CR ａ R ｂ When R １４１ ~R １４８ is a single bond bonded to *29, or R ａ and R ｂ One of the groups is a single bond bonded to *29 or a divalent group bonded to *29. １ is an oxygen atom, a sulfur atom, or -NR ｃ When R １４１ ~R １４８ One selected from is a single bond bonded to *29. １４１ ~R １４８ R which is not a single bond and is not a divalent group ａ and R ｂ , and R ｃ 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 Adjacent two selected from are not bonded to each other to form a ring. １ and Ar ２ are both represented by formula (2D), and R １２１ ~R １２８ are all hydrogen atoms, and X １ is an oxygen atom, m1 and m2 are both 1, and L １ and L ２ When both are unsubstituted phenylene groups, L １ and L ２ one of which is an unsubstituted o-phenylene group, an unsubstituted m-phenylene group, or an unsubstituted p-phenylene group, and the other is an unsubstituted o-phenylene group or an unsubstituted m-phenylene group. (In formula (2E), *30 is L １ and L ２ represents a bond to one or both of １５１ ~R １５５ is a single bond bonded to *31, and R １５１ ~R １５５ Another one selected from is a single bond bonded to *32. １５１ ~R １５５ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group. １５１ ~R １５５ Adjacent two selected from are not bonded to each other to form a ring. 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. １６１ ~R １６５ At least two adjacent R selected from the group consisting of R 1 and R 2 are bonded to each other to form one or more unsubstituted benzene rings, or are not bonded to each other to form a ring. １７１ ~R １７５ At least two adjacent ones selected from are bonded to each other to form one or more unsubstituted benzene rings, or are not bonded to each other and therefore do not form a ring. (In formula (2F), *33 is L １ and L ２ represents a bond to one or both of １８１ ~R １９２ One selected from is a single bond bonded to *34. 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 Adjacent two selected from are not bonded to each other to form a ring. (In formula (2G), *35 is L １ and L ２ represents a bond to one or both of ３０１ ~R ３０８ 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. ３０１ ~R ３０８ Adjacent two selected from are not bonded to each other to form a ring. １ and Ar ２ are represented by the same formula among the above formulas (2A), (2B), (2C), (2D), (2E), (2F), and (2G), Ar １ and Ar ２ are the same as or different from each other, provided that Ar １ is represented by formula (2G), and L when m1 is 1 １ , and Ar ２ is represented by formula (2G), and L when m2 is 1 ２ respectively represent a substituted or unsubstituted 4,2'-biphenylene group, a substituted or unsubstituted 4,4'-biphenylene group, a substituted or unsubstituted 2,2'-biphenylene group, a substituted or unsubstituted 3,3'-biphenylene group, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

16. - (L １ ) ｍ１ -Ar １ The skeleton of -(L ２ ) ｍ２ -Ar ２ The compound according to any one of claims 1 to 15, wherein the skeletons of 17. - (L １ ) ｍ１ -Ar １ The skeleton of -(L ２ ) ｍ２ -Ar ２ The compound according to any one of claims 1 to 15, wherein the skeleton of 18. R ５ ~R １０ The compound according to any one of claims 1 to 17, wherein is a hydrogen atom.

19. R １１ ~R １４ The compound according to any one of claims 1 to 18, wherein is a hydrogen atom.

20. m1 is 1 and L １ has a phenylene skeleton, and Ar １ When L has a dibenzofuranyl skeleton or a dibenzothiophene skeleton, it satisfies at least one of the following (i) and (ii), m2 is 1, and L ２ has a phenylene skeleton, and Ar ２ The compound according to any one of claims 1 to 19, which satisfies at least one of the following (iii) and (iv) when L has a dibenzofuranyl skeleton or a dibenzothiophene skeleton. １ (ii) Ar is a substituted or unsubstituted o-phenylene group or a substituted or unsubstituted p-phenylene group. １ (iii) L is an unsubstituted dibenzofuranyl group or an unsubstituted dibenzothiophene group. ２ (iv) Ar is a substituted or unsubstituted o-phenylene group or a substituted or unsubstituted p-phenylene group. ２ is an unsubstituted dibenzofuranyl group or an unsubstituted dibenzothiophene group.

21. The compound according to any one of claims 1 to 20, wherein X is an oxygen atom.

22. A compound according to any one of claims 1 to 21, containing one or more deuterium atoms in the molecule.

23. m1 is 1 and L １ is represented by any one of the following formulas (3A) to (3D), m2 is 1, and L ２ is represented by any one of the following formulas (3A) to (3D), or m1 and m2 are 1, and L １ and L ２ are each independently represented by any one of the following formulas (3A) to (3D), Ａ a hydrogen atom contained in the formula (3B), a substituent R Ｂ１ and R Ｂ２ a hydrogen atom contained in at least one of the groups represented by the formula (3C), Ｃ１ and R Ｃ２ a hydrogen atom contained in at least one of the five-membered rings contained in formula (3D), and a substituent R Ｄ The compound according to any one of claims 1 to 22, wherein at least one of the hydrogen atoms included in is a deuterium atom. [In formulas (3A) to (3D), R Ａ , R Ｂ１ , R Ｂ２ , R Ｃ１ , R Ｃ２ , and R Ｄ represents a substituent, X ２ and X ３ represents an oxygen atom or a sulfur atom, p, q1, and q2 each independently represent an integer from 0 to 6, r1, r2, and s each independently represent an integer from 0 to 4, and * represents the central nitrogen atom N ＊ represents a bond to Ar １ and Ar ２ R Ｂ１ and R Ｂ２ are the same as or different from each other. Ｃ１ and R Ｃ２ When p, q1, q2, r1, r2, and s are each 2 or more, there are 2 or more pairs of R Ａ , R Ｂ１ , R Ｂ２ , R Ｃ１ , R Ｃ２ , and R Ｄ are the same as or different from each other.

24. R １１ ~R １４ The compound according to any one of claims 1 to 23, wherein at least one of a hydrogen atom, a hydrogen atom contained in an alkyl group, a hydrogen atom contained in a substituent carried by an alkyl group, a hydrogen atom contained in an alkenyl group, a hydrogen atom contained in a substituent carried by an alkenyl group, a hydrogen atom contained in an aryl group, a hydrogen atom contained in a substituent carried by an aryl group, a hydrogen atom contained in a heteroaryl group, and a hydrogen atom contained in a substituent carried by a heteroaryl group, represented by 25. Ar １ and Ar ２ The compound according to any one of claims 1 to 24, wherein at least one of the hydrogen atoms contained in a cycloalkyl group, the hydrogen atoms contained in a substituent of a cycloalkyl group, the hydrogen atoms contained in a heterocycloalkyl group, the hydrogen atoms contained in a substituent of a heterocycloalkyl group, the hydrogen atoms contained in an aryl group, the hydrogen atoms contained in a substituent of an aryl group, the hydrogen atoms contained in a heteroaryl group, and the hydrogen atoms contained in a substituent of a heteroaryl group, represented by 26. The compound of claim 1, which comprises any one of compounds 1 to 11 below.

27. A material for an organic electroluminescence device, comprising the compound according to any one of claims 1 to 26.

28. The material for an organic electroluminescence device according to claim 27, wherein the compound according to any one of claims 1 to 26 is a material for a hole transport layer.

29. An organic electroluminescence device having a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer consisting 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 contains the compound according to any one of claims 1 to 26.

30. The organic electroluminescence device according to claim 29, wherein the organic layer comprises a hole transporting zone between the anode and the light emitting layer, and the hole transporting zone comprises a compound according to any one of claims 1 to 26.

31. The organic electroluminescence device according to claim 30, wherein the hole transport zone comprises a first hole transport layer on the anode side and a second hole transport layer on the cathode side, and at least one of the first hole transport layer and the second hole transport layer comprises the compound according to any one of claims 1 to 26.

32. The organic electroluminescence device according to claim 31, wherein the second hole transport layer comprises a compound according to any one of claims 1 to 26.

33. The organic electroluminescence device according to claim 31 or 32, wherein the light-emitting layer and the second hole transport layer are in direct contact with each other.

34. The organic electroluminescence device according to any one of claims 31 to 33, wherein the sum of the thickness of the first hole transport layer and the thickness of the second hole transport layer is 30 nm or more and 150 nm or less.

35. The organic electroluminescence device according to any one of claims 29 to 34, wherein the light-emitting layer includes a layer containing a light-emitting compound that exhibits fluorescent emission.

36. The organic electroluminescence device according to any one of claims 29 to 35, wherein the light-emitting layer is a single layer.

37. An electronic device comprising the organic electroluminescence element according to any one of claims 29 to 36.

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