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

Abstract

To provide a compound that can further improve the performance of an organic EL device, an organic EL device with improved device performance, and an electronic apparatus including such an organic EL device.SOLUTION: The invention provides a compound represented by the formula (1) in the figure.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] Generally, organic electroluminescent devices (hereinafter sometimes referred to as "organic EL devices") consist 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 and holes are injected from the anode 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, in order to obtain high-performance organic EL devices, it is important to find a combination of materials that efficiently transport electrons or holes to the light-emitting region, facilitate the recombination of electrons and holes, and efficiently emit excitons.

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

[0004] [Patent Document 1] Chinese Patent Publication No. 111675701 [Patent Document 2] Chinese Patent Publication No. 109096179 [Patent Document 3] Korean Patent Publication No. 10-2019-0035567 [Patent Document 4] Korean Patent Publication No. 10-2018-0066855 [Patent Document 5] US Patent Application Publication No. 2016 / 0293843 [Patent Document 6] US Patent Application Publication No. 2015 / 0179953 [Patent Document 7] US Patent Application Publication No. 2016 / 0301005 [Patent Document 8] Korean Patent Publication No. 10-2018-0116740 [Patent Document 9] US Patent Application Publication No. 2017 / 0194569 [Patent Document 10] US Patent Application Publication No. 2017 / 0186978 [Patent Document 11] US Patent Application Publication No. 2017 / 0186969 [Patent Document 12] Korean Patent Publication No. 10-2019-0005522 [Patent Document 13] International Publication No. 2021 / 045590 Summary of the Invention [Problem to be solved by the invention]

[0005] Although many compounds for organic EL devices have been reported, there is still a demand for further improvement in 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 that further improves the performance of an organic EL device, an organic EL device having further improved device performance, and an electronic device including such an organic EL device. [Means for solving the problem]

[0007] The present inventors have conducted extensive research into the performance of organic EL devices containing the compounds described in Patent Documents 1 to 13, and have found that organic EL devices containing a compound represented by the following formula (1) have improved performance.

[0008] In one aspect, the present invention provides a compound represented by formula (1): [ka] (In formula (1), N * is the central nitrogen atom. R a and R b One of the groups is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and the other is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. However, R a and R b may be bonded to each other to form a substituted or unsubstituted ring. R 2 , R 3 , R 6 and R 7 one selected from is a single bond bonded to *1, and R 1 , R 4 , R 5 , R 8 , and R that is not a single bond bonded to *1 2 , R 3 , R 6 and R 7 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 15 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. R 1 , R 4 , R 5 , R 8 and the R that is not a single bond. 2 , R 3 , R 6 and R 7 Adjacent two selected from are not bonded to each other and therefore do not form a ring. R 11 ~R 14 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms. R 11 ~R 14Adjacent two selected from are not bonded to each other and therefore do not form a ring. L 1 ~L 4 are each independently a single bond or an arylene group having 6 to 30 ring carbon atoms. Ar 1 and Ar 2 is a group represented by any one of the following formulas (1a) to (1g). [ka] (In formula (1a), *21 is L 1 or L 2 is the binding site to R 101 ~R 105 is a single bond bonded to *22, and R 106 ~R 110 one selected from is a single bond bonded to *23, and R 111 ~R 115 One selected from is a single bond bonded to *24. The R is not a single bond 101 ~R 115 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. The R is not a single bond 101 ~R 105 adjacent two selected from are not bonded to each other and therefore do not form a ring, The R is not a single bond 106 ~R 110 adjacent two selected from are not bonded to each other and therefore do not form a ring, The R is not a single bond 111 ~R 115 Adjacent two selected from are not bonded to each other and therefore do not form a ring. m is 0 or 1, n is 0 or 1, and l is 0 or 1. R 116 ~R 120are 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 heterocyclic group having 5 to 13 ring atoms. R 116 ~R 120 Adjacent two selected from are not bonded to each other and therefore do not form a ring. [ka] (In formula (1b), *25 is L 1 or L 2 is the binding site to R 121 ~R 128 One selected from is a single bond bonded to *26. The R is not a single bond 121 ~R 128 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. The R is not a single bond 121 ~R 128 Adjacent two selected from are not bonded to each other and therefore do not form a ring. However, L 1 is a p-phenylene group, and Ar 1 is represented by formula (1b), R in the group represented by formula (1b) bonded to the p-phenylene group 121 , R 124 , R 125 , and R 128 one selected from is a single bond bonded to *26, L 2 is a p-phenylene group, and Ar 2 is represented by formula (1b), R in the group represented by formula (1b) bonded to the p-phenylene group 121 , R 124 , R 125 , and R 128 One selected from is a single bond connecting to *26.) [ka] (In formula (1c), *27 is L 1 or L 2 is the binding site to R 131 ~R 140 One selected from is a single bond bonded to *28. The R is not a single bond 131 ~R 140 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. The R is not a single bond 131 ~R 140 Adjacent two selected from are not bonded to each other and therefore do not form a ring. [ka] (In formula (1d), *29 is L 1 or L 2 is the binding site to R 141 ~R 152 One selected from is a single bond bonded to *30. The R is not a single bond 141 ~R 152 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. The R is not a single bond 141 ~R 152 Adjacent two selected from are not bonded to each other and therefore do not form a ring structure. [ka] (In formula (1e), *31 is L 1 or L 2 is the binding site to R 161 ~R 165is a single bond bonded to *32, and R 161 ~R 165 The other one selected from is a single bond bonded to *33. R that is not a single bond bonded to said *32 and is not a single bond bonded to said *33 161 ~R 165 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group. R that is not a single bond bonded to *32 and is not a single bond bonded to *33 161 ~R 165 Adjacent two selected from are not bonded to each other and therefore do not form a ring. R 171 ~R 175 and R 181 ~R 185 are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms. R 171 ~R 175 adjacent two selected from may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore not form a ring; R 181 ~R 185 Any two adjacent groups selected from may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore not form a ring. [ka] (In formula (1f), *34 is L 1 or L 2 is the binding site to X is an oxygen atom, a sulfur atom, or NR A is. R 191 ~R 198 and R A One selected from is a single bond bonded to *35. The R is not a single bond Ais a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. The R is not a single bond 191 ~R 198 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. The R is not a single bond 191 ~R 198 Any two adjacent groups selected from may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore not form a ring. [ka] (In formula (1g), *36 is L 1 or L 2 is the binding site to R B , R C , and R 201 ~R 208 One selected from is a single bond bonded to *37. The R is not a single bond B and R C are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. The R is not a single bond B and R C may be bonded to each other to form a substituted or unsubstituted ring. The R is not a single bond 201 ~R 208 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. The R is not a single bond 201 ~R 208Adjacent two selected from are not bonded to each other and therefore do not form a ring.

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

[0010] In yet another aspect, the present invention provides an organic electroluminescence device comprising a cathode, an anode, and organic layers between the cathode and the anode, wherein the organic layers comprise an emitting layer, and at least one layer of the organic layers comprises a compound represented by formula (1).

[0011] In still another aspect, the present invention provides an electronic device including the organic electroluminescence device. [Effects of the Invention]

[0012] An organic EL device containing the compound represented by formula (1) exhibits improved device performance. [Brief explanation of the drawings]

[0013] [Figure 1] 1 is a schematic diagram illustrating an example of a layer structure of an organic EL element according to one embodiment of the present invention. [Figure 2] FIG. 2 is a schematic diagram showing another example of the layer structure of an organic EL element according to one embodiment of the present invention. [Figure 3] FIG. 2 is a schematic diagram showing yet another example of the layer structure of an organic EL element according to one embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0014] [Definition] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0015] In this specification, in a chemical structural formula, a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded to a possible bonding position that is not explicitly marked with a symbol such as "R" or "D" representing a deuterium atom.

[0016] 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. Furthermore, 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 the benzene ring substituted with an alkyl group is 6. Furthermore, when a 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.

[0017] 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 are 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.

[0018] 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" refers to 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.

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

[0020] In this specification, an unsubstituted ZZ group refers to a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to a case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group". In this specification, "unsubstituted" in the context 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. In this specification, "substituted" in the context 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 context 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.

[0021] "Substituents described herein" The substituents described in this specification will be explained below.

[0022] The "unsubstituted aryl group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30 ring carbon atoms, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30 ring atoms, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkyl group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification. Unless otherwise specified in this specification, the "unsubstituted alkenyl group" described in this specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms. Unless otherwise specified, the "unsubstituted alkynyl group" described in this specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms. The "unsubstituted cycloalkyl group" described in this specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted arylene group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30 ring carbon atoms, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted divalent heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30 ring atoms, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkylene group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.

[0023] "Substituted or unsubstituted aryl group" Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B). (Here, the term "unsubstituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and the term "substituted aryl group" refers to the case where the "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 a substituent. Examples of the "substituted aryl group" include groups in which one or more hydrogen atoms of the "unsubstituted aryl group" are replaced with a substituent, and examples of the substituted aryl group in the specific example group G1A below. The examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed here are merely examples, and the "substituted aryl group" described in this specification also includes groups in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent.

[0024] Unsubstituted aryl groups (specific example group G1A): phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, benzanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, chrysenyl group, benzochrysenyl group, a triphenylenyl group, benzotriphenylenyl group, tetracenyl group, pentacenyl group, fluorenyl groups, 9,9'-spirobifluorenyl group, benzofluorenyl groups, dibenzofluorenyl groups, fluoranthenyl group, benzofluoranthenyl group, perylenyl groups, and A monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[0025] [ka]

[0026] [ka]

[0027] 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 groups, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl groups, and A group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by any one of the general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0028] "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 groups" described herein are either monocyclic or fused ring groups. The "heterocyclic group" described herein may be an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group," and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group.") In this specification, the term "heterocyclic group" simply includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group." A "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with a substituent. Specific examples of the "substituted heterocyclic group" include the groups in which a hydrogen atom of the "unsubstituted heterocyclic group" in the specific example group G2A below is replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are also included. The examples of the "unsubstituted heterocyclic group" and the "substituted heterocyclic group" listed here are merely examples, and the "substituted heterocyclic group" described in this specification also includes groups in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" in the specific example group G2B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted heterocyclic group" in the specific example group G2B is further replaced with a substituent.

[0029] 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).

[0030] 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 a substituent (specific example group G2B4).

[0031] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): pyrrolyl group, imidazolyl group, pyrazolyl group, a triazolyl group, tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, isothiazolyl group, a thiadiazolyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, a triazinyl group, Indolyl groups, isoindolyl groups, an indolizinyl group, a quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, a quinazolinyl group, quinoxalinyl group, benzimidazolyl group, an indazolyl group, a phenanthrolinyl group, a phenanthridinyl group, acridinyl group, phenazinyl group, a carbazolyl group, a benzocarbazolyl group, morpholino group, phenoxazinyl group, a phenothiazinyl group, Azacarbazolyl group and diazacarbazolyl group.

[0032] Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl groups, benzoisoxazolyl group, phenoxazinyl group, morpholino group, a dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, an azanaphthobenzofuranyl group, and Diazanaphthobenzofuranyl group.

[0033] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): a thienyl group, a thiazolyl group, isothiazolyl group, a thiadiazolyl group, Benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), naphthobenzothiophenyl group (naphthobenzothienyl group), benzothiazolyl group, benzoisothiazolyl group, a phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), diazadibenzothiophenyl group (diazadibenzothienyl group), Azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and Diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0034] 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):

[0035] [ka]

[0036] [ka]

[0037] In the general formulae (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2. A and Y A At least one of is an oxygen atom, a sulfur atom, or NH. In the general formulae (TEMP-16) to (TEMP-33), X A and Y A When at least one of is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from NH or CH2.

[0038] 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, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, methylbenzimidazolyl group, ethylbenzimidazolyl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenylquinazolinyl group, and Biphenylylquinazolinyl group.

[0039] Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, t-butyldibenzofuranyl group, and A monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0040] Substituted heterocyclic groups containing sulfur atoms (specific example group G2B3): phenyldibenzothiophenyl group, methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and A monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0041] 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):

[0042] The above-mentioned "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.

[0043] "Substituted or unsubstituted alkyl groups" 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 unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereinafter, when simply referring to an "alkyl group," both an "unsubstituted alkyl group" and a "substituted alkyl group" are included. The term "substituted alkyl group" refers to an "unsubstituted alkyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkyl group" include the following "unsubstituted alkyl group" (specific example group G3A) in which one or more hydrogen atoms have been replaced with a substituent, and the examples of the substituted alkyl group (specific example group G3B). In this specification, the alkyl group in the "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the "unsubstituted alkyl group" includes a linear "unsubstituted alkyl group" and a branched "unsubstituted alkyl group." Note that the examples of the "unsubstituted alkyl group" and the "substituted alkyl group" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" in specific example group G3B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl group" in specific example group G3B is further replaced with a substituent.

[0044] Unsubstituted alkyl groups (specific example group G3A): methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group.

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

[0046] "Substituted or unsubstituted alkenyl group" Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described herein include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group G4B). (Here, the term "unsubstituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and the term "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply includes both an "unsubstituted alkenyl group" and a "substituted alkenyl group." A "substituted alkenyl group" refers to an "unsubstituted alkenyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl groups" (specific example group G4A) having a substituent, and the 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 the "substituted alkenyl groups" of specific example group G4B in which a hydrogen atom of the alkenyl group itself has been further replaced with a substituent, and groups in the "substituted alkenyl groups" of specific example group G4B in which a hydrogen atom of a substituent has been further replaced with a substituent.

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

[0048] Substituted alkenyl groups (specific example group G4B): 1,3-butadienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.

[0049] "Substituted or unsubstituted alkynyl group" Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl groups (specific example group G5A). (Here, the unsubstituted alkynyl group refers to a case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, when simply referring to an "alkynyl group," it includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group." A "substituted alkynyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced with substituents. Specific examples of the "substituted alkynyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl group" (specific example group G5A) are replaced with substituents, etc.

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

[0051] "Substituted or unsubstituted cycloalkyl groups" 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 unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group," and the substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group.") In this specification, when the term "cycloalkyl group" is simply used, it includes both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group." A "substituted cycloalkyl group" refers to an "unsubstituted cycloalkyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (specific example group G6A) in which one or more hydrogen atoms have been replaced with a substituent, 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 group" described in this specification also includes a group in the "substituted cycloalkyl group" of specific example group G6B in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself have been replaced with a substituent, and a group in the "substituted cycloalkyl group" of specific example group G6B in which a hydrogen atom of a substituent has been further replaced with a substituent.

[0052] Unsubstituted cycloalkyl groups (specific example group G6A): a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.

[0053] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.

[0054] -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 -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 the specific example group G6. The multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other. The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other. The multiple G1s in —Si(G1)(G1)(G2) are the same as or different from each other. The multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other. The multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The multiple G6s in -Si(G6)(G6)(G6) may be the same as or different from each other.

[0055] -O-(R 904 ) a group represented by As described herein, —O—(R 904 Specific examples (specific example group G8) of the group represented by -O(G1), -O(G2), -O(G3), and -O(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.

[0056] -S-(R 905 ) a group represented by -S-(R 905 Specific examples (specific example group G9) of the group represented by -S(G1), -S(G2), -S(G3), and -S(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.

[0057] -N(R 906 )(R 907 ) a group represented by -N(R 906 )(R 907 Specific examples (specific example group G10) of the group represented by -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6. -The multiple G1s in N(G1)(G1) are the same as or different from each other. The multiple G2's in -N(G2)(G2) are the same as or different from each other. The multiple G3s in -N(G3)(G3) are the same as or different from each other. The multiple G6s in -N(G6)(G6) are the same as or different from each other.

[0058] "Halogen atoms" 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.

[0059] "Substituted or unsubstituted fluoroalkyl groups" 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 the 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 are replaced with a fluorine atom.

[0060] "Substituted or unsubstituted haloalkyl groups" The term "substituted or unsubstituted haloalkyl 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 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. The term "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms in a "haloalkyl group" are replaced with a substituent. The term "substituted haloalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in a "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in a "substituted haloalkyl group" are further replaced with a substituent. Specific examples of "unsubstituted haloalkyl groups" include the examples of the above-mentioned "alkyl groups" (specific example group G3) in which one or more hydrogen atoms are replaced with halogen atoms. Haloalkyl groups are sometimes referred to as halogenated alkyl groups.

[0061] "Substituted or unsubstituted alkoxy group" A specific example of the "substituted or unsubstituted alkoxy group" described herein 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 herein, the "unsubstituted alkoxy group" has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms.

[0062] "Substituted or unsubstituted alkylthio group" A specific example of the "substituted or unsubstituted alkylthio group" described herein 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 herein, the "unsubstituted alkylthio group" has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms.

[0063] "Substituted or unsubstituted aryloxy group" A specific example of the "substituted or unsubstituted aryloxy group" described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

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

[0065] "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described herein is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) may be the same or different. Unless otherwise specified herein, 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.

[0066] "Substituted or unsubstituted aralkyl group" A specific example of the "substituted or unsubstituted aralkyl group" described herein is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. 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 herein. Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl groups.

[0067] Unless otherwise specified in the present specification, the substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, 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.

[0068] Unless otherwise specified in the present specification, the substituted or unsubstituted heterocyclic group described herein 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 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.

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

[0070] [ka]

[0071] In this specification, unless otherwise specified in this specification, a (9-phenyl)carbazolyl group specifically means any of the following groups:

[0072] [ka]

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

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

[0075] [ka]

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

[0077] 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.

[0078] "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group". Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1.

[0079] "Substituted or unsubstituted divalent heterocyclic group" Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom on the 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.

[0080] "Substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group." Specific examples of the "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3.

[0081] 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).

[0082] [ka]

[0083] [ka]

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

[0085] [ka]

[0086] In the general formulae (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent. Equations Q9 and Q 10 may be bonded to each other via a single bond to form a ring. In the general formulae (TEMP-53) to (TEMP-62), * represents a bonding position.

[0087] [ka]

[0088] In the general formulae (TEMP-63) to (TEMP-68), Q1 to Q8 each independently represent a hydrogen atom or a substituent. In the general formulae (TEMP-63) to (TEMP-68), * represents a bonding position.

[0089] Unless otherwise specified in the present specification, the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the groups represented by the following general formulae (TEMP-69) to (TEMP-102).

[0090] [ka]

[0091] [ka]

[0092] [ka]

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

[0094] [ka]

[0095] [ka]

[0096] [ka]

[0097] [ka]

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

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

[0100] - "When bonded to form a ring" In this specification, the phrase "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocycle, bond with each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocycle", the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted fused ring", or the case where "one or more pairs of adjacent groups do not bond with each other". In this specification, the cases where "one or more groups of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocyclic ring" and "one or more groups of two or more adjacent groups bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "a case where they bond to form a ring") will be explained below. The case of an anthracene compound represented by the following general formula (TEMP-103), in which the main skeleton is an anthracene ring, will be explained as an example.

[0101] [ka]

[0102] For example, R921 ~R 930 In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," 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 Pairs with and R 929 and R 921 It is paired with.

[0103] The above "one or more pairs" means that two or more pairs of adjacent two or more groups may simultaneously form a ring. For example, R 921 and R 922 and are bonded to each other to form ring Q A At the same time, 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).

[0104] [ka]

[0105] When a "set of two or more adjacent units" forms a ring, it includes not only the case where a set of two adjacent units is bonded, as in the example above, but also the case where a set of three or more adjacent units is bonded. For example, R 921 and R 922 and are bonded to each other to form ring Q A and R 922 and R923 and are bonded to each other to form ring Q C and form three adjacent (R 921 , R 922 and R 923 In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105): A and Ring Q C is R 922 Share.

[0106] [ka]

[0107] The "monocyclic ring" or "fused ring" formed may be a saturated ring or an unsaturated ring as the structure of only the ring formed. 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", respectively. A , and ring Q C is a "fused ring". A and Tamaki Q C That is, Tamaki Q A and Tamaki Q C The ring Q in the general formula (TEMP-104) is fused to form a fused ring. A If is a benzene ring, then ring Q A The ring Q in the general formula (TEMP-104) is a monocyclic ring. A If is a naphthalene ring, then ring Q A is a fused ring.

[0108] The term "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The term "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of the aromatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G1 are terminated with a hydrogen atom. Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in the specific example group G2 are terminated with a hydrogen atom. Specific examples of the aliphatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom. The term "forming a ring" means that a ring is formed 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 Q are bonded together to form a ring A is R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 It means a ring formed by the carbon atom of the anthracene skeleton to which R is bonded and one or more arbitrary elements. 921 and R 922 Todekan Q A In the case where R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 When a monocyclic unsaturated ring is formed with the carbon atom of the anthracene skeleton to which R is bonded and four carbon atoms, 921 and R 922 The ring formed by

[0109] Here, unless otherwise specified in this specification, the "arbitrary element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur. In the arbitrary element (for example, in the case of carbon or nitrogen), the bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below. When an arbitrary element other than carbon is included, the formed ring is a heterocycle. Unless otherwise specified in this specification, the "one or more arbitrary elements" constituting the monocyclic or fused ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less. Unless otherwise specified in this specification, of the "monocyclic ring" and the "fused ring", the "monocyclic ring" is preferred. Unless otherwise specified in this specification, of the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred. Unless otherwise specified herein, a "monocyclic ring" 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 groups" "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 groups 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.

[0110] When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, the substituent is, for example, the "optional substituent" described later. 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 in this specification." When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification." The above is an explanation of the case where "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring" ("when bonded to form a ring").

[0111] Substituents in "substituted or unsubstituted" In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituent" in the present specification) includes, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms; an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms; -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and Unsubstituted heterocyclic group having 5 to 50 ring atoms and the like, a group selected from the group consisting of where R 901 ~R 907 are each independently, hydrogen atoms, 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 It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 901 If there are two or more, there are two or more R 901 are identical to or different from each other, R 902 If there are two or more, there are two or more R 902 are identical to or different from each other, R 903If there are two or more, there are two or more R 903 are identical to or different from each other, R 904 If there are two or more, there are two or more R 904 are identical to or different from each other, R 905 If there are two or more, there are two or more R 905 are identical to or different from each other, R 906 If there are two or more, there are two or more R 906 are identical to or different from each other, R 907 If there are two or more, there are two or more R 907 are the same or different from each other.

[0112] In one embodiment, the substituents in the "substituted or unsubstituted" are: an alkyl group having 1 to 50 carbon atoms; an aryl group having 6 to 50 ring carbon atoms, and Heterocyclic groups with 5 to 50 ring atoms is a group selected from the group consisting of:

[0113] In one embodiment, the substituents in the "substituted or unsubstituted" are: an alkyl group having 1 to 18 carbon atoms; an aryl group having 6 to 18 ring carbon atoms, and Heterocyclic groups with 5 to 18 ring atoms is a group selected from the group consisting of:

[0114] 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."

[0115] Unless otherwise specified in this specification, any adjacent substituents may be bonded to each other to form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring. Unless otherwise specified in this specification, any optional substituent may further have a substituent. The substituent that the optional substituent further has is the same as the optional substituent described above.

[0116] 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.

[0117] The compounds of the present invention will be described below. The compound of the present invention is represented by the above formula (1). The symbols in formula (1) and each formula contained in formula (1) below will be explained below. Unless otherwise specified, the same symbols have the same meaning. The compounds of the present invention represented by formula (1) and the formulas contained in formula (1) described below may be referred to as "invention compounds."

[0118] [ka]

[0119] N * is the central nitrogen atom.

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

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

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

[0123] R a and R bThe unsubstituted aryl group having 6 to 30 ring carbon atoms represented by the formula (I) is, for example, a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, an anthryl group, a benzanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a picenyl group, a pentaphenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a fluorenyl group, a fluoranthenyl group, a perylenyl group, or a triphenylenyl group, and preferably a phenyl group, a biphenylyl group, The alkyl group is preferably a phenyl group, a terphenylyl group, or a naphthyl group, more preferably a phenyl group, a 2-, 3-, or 4-biphenylyl group, a 2-, 3-, or 4-o-terphenylyl group, a 2-, 3-, or 4-m-terphenylyl group, a 2-, 3-, or 4-p-terphenylyl group, or a 1- or 2-naphthyl group, still more preferably a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group, and particularly preferably a phenyl group.

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

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

[0126] [ka]

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

[0128] R 2 , R 3 , R 6 and R 7 one selected from is a single bond bonded to *1, and R 1 , R 4 , R 5 , R 8 , and R that is not a single bond bonded to *1 2 , R 3 , R 6 and R 7 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 18, more preferably 1 to 10, and even more preferably 1 to 6, carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 15, preferably 3 to 10, and more preferably 3 to 6 ring carbon atoms; a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms; or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. R 1 , R 4 , R 5 , R 8 and the R that is not a single bond. 2 , R 3 , R 6 and R 7Adjacent two selected from are not bonded to each other and therefore do not form a ring.

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

[0130] R 1 , R 4 , R 5 , R 8 , and R that is not a single bond bonded to *1 2 , R 3 , R 6 and R 7 For details of the unsubstituted alkyl group having 1 to 30 carbon atoms represented by R a and R b As described above.

[0131] R 1 , R 4 , R 5 , R 8 , and R that is not a single bond bonded to *1 2 , R 3 , R 6 and R 7 The unsubstituted cycloalkyl group having 3 to 15 ring carbon atoms represented by the formula (I) is, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, or a cyclooctyl group, and preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group.

[0132] R 1 , R 4 , R 5 , R 8 , and R that is not a single bond bonded to *1 2 , R 3 , R 6 and R 7 The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R a and R b As described above.

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

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

[0135] R 11 ~R 14 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 18, more preferably 1 to 10, and even more preferably 1 to 6, carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18, preferably 6 to 12, ring carbon atoms. R 11 ~R 14 Adjacent two selected from are not bonded to each other and therefore do not form a ring.

[0136] R 11 ~R 14 For details of the unsubstituted alkyl group having 1 to 30 carbon atoms represented by R a and R b As described above.

[0137] R 11 ~R 14 The details of the unsubstituted aryl group having 6 to 18 ring carbon atoms represented by R a and R b As described above.

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

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

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

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

[0142] Said L 1 ~L 4 The unsubstituted arylene group having 6 to 30 ring carbon atoms represented by the formula (I) is a divalent group obtained by removing one hydrogen atom from an unsubstituted aryl group having 6 to 30 ring carbon atoms. Details of the unsubstituted aryl group having 6 to 30 ring carbon atoms are as follows: a and R b As described above.

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

[0144] [ka]

[0145] In formula (1a), *21 is L 1 or L 2 is the binding site to R 101 ~R 105 is a single bond bonded to *22, and R 106 ~R 110 one selected from is a single bond bonded to *23, and R 111 ~R 115 One selected from is a single bond bonded to *24. The R is not a single bond 101 ~R 115 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. The R is not a single bond 101 ~R 105 adjacent two selected from are not bonded to each other and therefore do not form a ring, The R is not a single bond 106 ~R 110 adjacent two selected from are not bonded to each other and therefore do not form a ring, The R is not a single bond 111 ~R 115 Adjacent two selected from are not bonded to each other and therefore do not form a ring.

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

[0147] The R is not a single bond 101 ~R 115The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R are as follows, except that the number of carbon atoms is 1 to 10. a and R b As described above.

[0148] R 101 ~R 115 The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R a and R b As described above.

[0149] *22 non-single bond R 101 ~R 105 may all be hydrogen atoms, and R 106 ~R 110 may all be hydrogen atoms, and R 111 ~R 115 may all be hydrogen atoms.

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

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

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

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

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

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

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

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

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

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

[0160] R 116 ~R 120 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. R 116 ~R 120 Adjacent two selected from are not bonded to each other and therefore do not form a ring.

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

[0162] R 116 ~R 120 The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R a and R b As described above.

[0163] R 116 ~R 120 The details of the unsubstituted aryl group having 5 to 13 ring carbon atoms represented by R a and R b As described above.

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

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

[0166] Equation (1b) is expressed as follows:

[0167] [ka]

[0168] In formula (1b), *25 is L 1 or L 2 is the binding site to R 121 ~R 128 One selected from is a single bond bonded to *26. The R is not a single bond 121 ~R 128 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. The R is not a single bond 121 ~R 128 Adjacent two selected from are not bonded to each other and therefore do not form a ring. However, L 1 is a p-phenylene group, and Ar 1is represented by formula (1b), R in the group represented by formula (1b) bonded to the p-phenylene group 121 , R 124 , R 125 , and R 128 one selected from is a single bond bonded to *26, L 2 is a p-phenylene group, and Ar 2 is represented by formula (1b), R in the group represented by formula (1b) bonded to the p-phenylene group 121 , R 124 , R 125 , and R 128 One selected from is a single bond bonded to *26.

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

[0170] R 121 ~R 128 The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R are as follows, except that the number of carbon atoms is 1 to 10. a and R b As described above. R 121 ~R 128 The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R a and R b As described above.

[0171] In one embodiment of the present invention, R 121 is preferably a single bond attached to *26, and in other embodiments R 122 is preferably a single bond attached to *26. *26 non-single bond R121 ~R 128 may all be hydrogen atoms.

[0172] Equation (1c) is expressed as follows:

[0173] [ka]

[0174] In formula (1c), *27 is L 1 or L 2 is the binding site to R 131 ~R 140 One selected from is a single bond bonded to *28. The R is not a single bond 131 ~R 140 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 6, carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. The R is not a single bond 131 ~R 140 Adjacent two selected from are not bonded to each other and therefore do not form a ring.

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

[0176] R 131 ~R 140 The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R a and R b As described above. R 131 ~R 140The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R a and R b As described above. In one aspect of the present invention, R 131 However, in other embodiments, R 132 However, in still other embodiments, R 140 is preferably a single bond attached to *28. *28 non-single bond R 131 ~R 140 may all be hydrogen atoms.

[0177] Equation (1d) is expressed as follows:

[0178] [ka]

[0179] In formula (1d), *29 is L 1 or L 2 is the binding site to R 141 ~R 152 One selected from is a single bond bonded to *30. The R is not a single bond 141 ~R 152 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 6, carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. The R is not a single bond 141 ~R 152 Adjacent two selected from are not bonded to each other and therefore do not form a ring structure.

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

[0181] R 141 ~R 152 The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R are as follows, except that the number of carbon atoms is 1 to 10. a and R b As described above. R 141 ~R 152 The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R a and R b As described above. *30 is not a single bond 141 ~R 152 may all be hydrogen atoms.

[0182] Equation (1e) is expressed as follows:

[0183] [ka]

[0184] In formula (1e), *31 is L 1 or L 2 is the binding site to R 161 ~R 165 is a single bond bonded to *32, and R 161 ~R 165 The other one selected from is a single bond bonded to *33. R that is not a single bond bonded to said *32 and is not a single bond bonded to said *33 161 ~R 165 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, or an unsubstituted phenyl group. R that is not a single bond bonded to *32 and is not a single bond bonded to *33 161 ~R 165Adjacent two selected from are not bonded to each other and therefore do not form a ring.

[0185] L 1 When is a single bond, Ar 1 The *31 in the group represented by formula (1e) is the central nitrogen atom N * represents the bonding position to L 2 When is a single bond, Ar 2 The *31 in the group represented by formula (1e) is the central nitrogen atom N * represents the binding position to

[0186] R that is not a single bond bonded to said *32 and is not a single bond bonded to said *33 161 ~R 165 The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R are as follows, except that the number of carbon atoms is 1 to 10. a and R b As described above. R 141 ~R 152 The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R a and R b As described above. R that is not a single bond bonded to *32 and is not a single bond bonded to said *33 161 ~R 165 may all be hydrogen atoms.

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

[0188] R 171 ~R 175 and R 181 ~R 185 The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R are as follows, except that the number of carbon atoms is 1 to 10. a and R b As described above. R 171 ~R 175 and R 181 ~R 185 may all be hydrogen atoms.

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

[0190] [ka]

[0191] Equation (1f) is expressed as follows:

[0192] [ka]

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

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

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

[0196] R A The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R a and R b As described above. R A The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R a and R b As described above.

[0197] The R is not a single bond 191 ~R 198 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. The R is not a single bond 191 ~R 198 Adjacent two selected from the above may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore not form a ring.

[0198] The R is not a single bond 191 ~R 198 The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by Ra and R b As described above. The R is not a single bond 191 ~R 198 The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R a and R b As described above. The R is not a single bond 191 ~R 198 The details of the unsubstituted heterocyclic group having 5 to 13 ring atoms represented by R are as follows, except that the number of ring atoms is 5 to 13. a and R b As described above.

[0199] *35 is not a single bond, R 191 ~R 198 may all be hydrogen atoms.

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

[0201] Formula (1g) is expressed as follows:

[0202] [ka]

[0203] In formula (1g), *36 is L 1 or L 2 is the binding site to R B , RC , and R 201 ~R 208 One selected from is a single bond bonded to *37. The R is not a single bond B and R C are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. The R is not a single bond B and R C may be bonded to each other to form a substituted or unsubstituted ring.

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

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

[0206] The R is not a single bond B and R C The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R a and R b As described above. The R is not a single bond B and R C The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R a and R b As described above. The R is not a single bond B and RC The details of the unsubstituted heterocyclic group having 5 to 13 ring atoms represented by R are as follows, except that the number of ring atoms is 5 to 13. a and R b As described above. The R is not a single bond B and R C The details of the unsubstituted ring formed by bonding together are shown in R a and R b As described above.

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

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

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

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

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

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

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

[0214] As noted above, the term "hydrogen atom" as used herein encompasses protium, deuterium, and tritium atoms. Thus, compounds of the invention may contain naturally occurring deuterium atoms. Alternatively, deuterium atoms may be intentionally introduced into compound (1) by using compounds in which some or all of the raw materials are deuterated. Accordingly, in one embodiment of the present invention, compound (1) contains at least one deuterium atom. That is, the compound of the present invention may be a compound represented by formula (1), in which at least one of the hydrogen atoms contained in the compound is a deuterium atom.

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

[0216] The deuteration ratio of the invention compound depends on the deuteration ratio of the raw material compound used. Even if a raw material with a predetermined deuteration ratio is used, a certain proportion of naturally occurring proton isotopes may be contained. Therefore, the deuteration ratios of the invention compounds shown below include ratios that take into account trace amounts of naturally occurring isotopes, in addition to the proportions determined simply by counting the number of deuterium atoms represented by the chemical formula. The deuteration rate of the compound of the invention 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.

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

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

[0219] Those skilled in the art can easily prepare the compounds of the present invention by referring to the synthesis examples below and known synthesis methods.

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

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[0352] Materials for organic EL devices The material for organic EL devices of the present invention contains the compound of the present invention. The content of the compound of the present invention 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 of the present invention is useful for producing organic EL devices.

[0353] Organic EL element The organic EL device of the present invention comprises an anode, a cathode, and organic layers disposed between the anode and the cathode, the organic layers including a light-emitting layer, and at least one of the organic layers comprises the compound of the present invention. Examples of organic layers containing the compound of the invention include, but are not limited to, a hole transporting region (hole injection layer, hole transporting layer, electron blocking layer, exciton blocking layer, etc.) provided between an anode and an emitting layer, an emitting layer, a spacer layer, and an electron transporting region (electron injection layer, electron transporting layer, hole blocking layer, etc.) provided between a cathode and an emitting layer. The compound of the invention is preferably used as a material for the hole transporting region or the emitting layer of a fluorescent or phosphorescent EL device, more preferably as a material for the hole transporting region, 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.

[0354] The organic EL device 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 organic layers, at least one of which is a light-emitting layer, and emits light by recombination of injected holes and electrons.

[0355] For example, the following device configuration can be given as a typical device configuration of a simple type organic EL device. (1) Anode / light-emitting unit / cathode The light-emitting unit may also be a multi-layered structure having multiple phosphorescent or fluorescent light-emitting layers. In this case, a spacer layer may be provided between each light-emitting layer to prevent excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer. A typical layer structure of a simple light-emitting unit is shown below. The layers in parentheses are optional. (a) (hole injection layer / ) hole transport layer / fluorescent light-emitting layer / electron transport layer ( / electron injection layer) (b) (hole injection layer / ) hole transport layer / first fluorescent-emitting layer / second fluorescent-emitting layer / electron transport layer ( / electron injection layer) (c) (Hole injection layer / ) Hole transport layer / Phosphorescent emitting layer / Space layer / Fluorescent emitting layer / Electron transport layer ( / Electron injection layer) (d) (hole injection layer / ) hole transport layer / first phosphorescent-emitting layer / second phosphorescent-emitting layer / space layer / fluorescent-emitting layer / electron transport layer ( / electron injection layer) (e) (hole injection layer / ) hole transport layer / phosphorescent emitting layer / space layer / first fluorescent emitting layer / second fluorescent emitting layer / electron transport layer ( / electron injection layer) (f) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer) (g) (Hole injection layer / ) Hole transport layer / Exciton blocking layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer) (h) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light-emitting layer / electron transport layer ( / electron injection layer) (i) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light-emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer) (j) (Hole injection layer / ) Hole transport layer / Fluorescent light-emitting layer / Hole blocking layer / Electron transport layer ( / Electron injection layer) (k) (Hole injection layer / ) Hole transport layer / Fluorescent light-emitting layer / Exciton blocking layer / Electron transport layer ( / Electron injection layer) (l) (hole injection layer / ) first hole transport layer / second hole transport layer / first fluorescent-emitting layer / second fluorescent-emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer) (m) (hole injection layer / ) first hole transport layer / second hole transport layer / third hole transport layer / first fluorescent-emitting layer / second fluorescent-emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer) (n) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Third hole transport layer / Fluorescent light-emitting layer / First electron transport layer / Second electron transport layer ( / Electron injection layer)

[0356] The phosphorescent or fluorescent emitting layers may each emit a different color of light. Specifically, the light emitting unit (f) 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 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 the luminous efficiency.

[0357] Typical device configurations of tandem organic EL devices include the following. (2) Anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode Here, the first light-emitting unit and the second light-emitting unit can be, for example, independently selected from the light-emitting units described above. The intermediate layer is generally also called an intermediate electrode, intermediate conductive layer, charge generating layer, electron withdrawing layer, connecting layer, or intermediate insulating layer, and can be made of known materials that supply electrons to the first light-emitting unit and holes to the second light-emitting unit.

[0358] FIG. 1 is a schematic diagram showing an example of the configuration of an organic EL device of the present invention. The organic EL device 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-transporting region 6 (e.g., a hole-injection layer, a hole-transporting layer) is located between the emitting layer 5 and the anode 3, and an electron-transporting region 7 (e.g., an electron-injection layer, an electron-transporting 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.

[0359] 2 is a schematic diagram showing another configuration of an organic EL element of the present invention. The organic EL element 11 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.

[0360] 3 is a schematic diagram showing another configuration of an organic EL element 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.

[0361] In the present invention, a host combined with a fluorescent dopant material (fluorescent-emitting material) is referred to as a fluorescent host, and a host combined with a phosphorescent dopant material is referred to as a phosphorescent host. The fluorescent host and the phosphorescent host are not distinguished 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.

[0362] substrate The substrate is used as a support for the organic EL device. For example, a glass, quartz, or plastic plate can be used as the substrate. A flexible substrate can also be used. Examples of flexible substrates include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride. An inorganic vapor-deposited film can also be used.

[0363] anode The anode formed on the substrate is preferably made of a metal, alloy, electrically conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or higher). Specific examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium 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 these metals (e.g., titanium nitride).

[0364] 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 can be used for production include vacuum deposition, coating, inkjet printing, and spin coating.

[0365] hole transport band As described above, the organic layer may include a hole-transporting region between the anode and the light-emitting layer. The hole-transporting region is composed of a hole-injection layer, a hole-transporting layer, an electron-blocking layer, etc. It is preferable that the hole-transporting region contains the compound of the invention. It is preferable that at least one of these layers constituting the hole-transporting layer contains the compound of the invention, and it is particularly preferable that the compound of the invention be contained in the hole-transporting layer.

[0366] The hole injection layer formed in contact with the anode is formed using a material that easily injects holes regardless of the work function of the anode, and therefore materials that are commonly used as electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, and elements belonging to Group 1 or Group 2 of the periodic table) can be used. Materials with low work functions, such as elements belonging to Group 1 or 2 of the periodic table, can also be used. These include 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 metals (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these metals. Vacuum deposition and sputtering methods can be used to form the anode using alkali metals, alkaline earth metals, and alloys containing these metals. Furthermore, when using silver paste, coating methods and inkjet methods can be used.

[0367] 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.

[0368] 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.

[0369] The small organic compounds 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DNTPD), Examples of the hole injection layer material include aromatic amine compounds such as 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1).

[0370] Polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used. Examples include poly(N-vinylcarbazole) (abbreviated as PVK), poly(4-vinyltriphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD). Acid-added polymer compounds, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

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

[0372] [ka]

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

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

[0375] The hole transport layer may have a single-layer structure or a multi-layer 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. Alternatively, the hole transport layer may have a three-layer structure including, in order from the anode side, a first hole transport layer, a second hole transport layer, and a third hole transport layer. That is, the third hole transport layer may be disposed between the second hole transport layer and the light-emitting layer. In one embodiment of the present invention, the hole transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, and the hole transport layer closest to the cathode in the multilayer structure, for example, the second hole transport layer 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, which will be described later, may be interposed between the hole transport layer and the light-emitting layer of the single-layer structure, or between the hole transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer. When the hole transport layer has a two-layer structure, at least one of the first hole transport layer and the second hole transport layer contains the compound of the invention, i.e., the compound of the invention is contained only in the first hole transport layer, only in the second hole transport layer, or in both the first and second hole transport layers. In one embodiment of the present invention, the compound of the present invention is preferably contained in the second hole transport layer, i.e., the compound of the present invention is preferably contained only in the second hole transport layer, or the compound of the present invention is preferably contained in both the first and second hole transport layers. When the hole transport layer has a three-layer structure, at least one of the first to third hole transport layers contains the compound of the invention. That is, the compound of the invention is contained in only one layer selected from the first to third hole transport layers (only the first hole transport layer, only the second hole transport layer, or only the third hole transport layer), only two layers selected from the first to third hole transport layers (only the first and second hole transport layers, only the first and third hole transport layers, or only the second and third hole transport layers), or all of the first to third hole transport layers. In one embodiment of the present invention, the compound of the present invention is preferably contained in the third hole transport layer, i.e., the compound of the present invention is preferably contained only in the third hole transport layer, or the compound of the present invention is preferably contained in the third hole transport layer and one or both of the first and second hole transport layers. In one embodiment of the present invention, the invention compound contained in each hole transport layer is preferably a proteide compound from the viewpoint of production cost. The proteide compound is an invention compound in which all hydrogen atoms are protease atoms. Therefore, the present invention includes an organic EL device in which one or both of the first hole transport layer and the second hole transport layer (in the case of a two-layer structure), or at least one of the first to third hole transport layers, contains an invention compound consisting essentially of proteases. The term "invention compound consisting essentially of proteases" means that the content of proteases 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 of which include 100%).

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

[0377] 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.

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

[0379] [ka] [In the formula (11) and formula (12), L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, k is 1, 2, 3 or 4; When k is 1, L E2 represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, When k is 2, 3, or 4, 2, 3, or 4 L E2 are identical to or different from each other, When k is 2, 3, or 4, multiple L E2 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, L which does not form the monocyclic ring and does not form the fused ring E2represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, A 1 , B 1 , C 1 , A 2 , B 2 , C 2 , and D 2 each independently represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or —Si(R′ 901 )(R' 902 )(R' 903 ) and R' 901 , R' 902 and R' 903 each independently represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R' 901 When there are multiple R's, there are multiple R's. 901 are identical to or different from each other, R' 902 When there are multiple R's, there are multiple R's. 902 are identical to or different from each other, R' 903 When there are multiple R's, there are multiple R's. 903 are either identical to each other or different.]

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

[0381] The fluorenyl group which can be represented by A1, B1, C1, A2, B2, C2, and D2 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 be bonded together to form a ring, such as a fluorene skeleton or a xanthene skeleton.

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

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

[0384] [ka]

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

[0386] Examples of blue fluorescent materials that can be used in the light-emitting layer include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. Specific examples include N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), etc.

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

[0388] 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 (abbreviated as p-mPhTD) and 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviated as p-mPhAFD).

[0389] In one embodiment of the present invention, the light-emitting layer preferably contains a fluorescent light-emitting material (fluorescent dopant material).

[0390] Examples of blue phosphorescent materials that can be used in the light-emitting layer include metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Specific examples include bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) tetrakis(1-pyrazolyl)borate (abbreviated as FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviated as FIrpic), bis[2-(3',5'-bistrifluoromethylphenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviated as Ir(CF3ppy)2(pic)), and bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) acetylacetonate (abbreviated as FIracac).

[0391] 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)).

[0392] 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-porphyrinplatinum(II) (abbreviation: PtOEP).

[0393] 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 transitions between different multiplicities).

[0394] Host material for the emitting layer The light-emitting layer may be configured by dispersing the above-mentioned dopant material in another material (host material). It is preferable to use a material having a higher lowest unoccupied molecular orbital (LUMO) level and a lower highest occupied molecular orbital (HOMO) level than the dopant material.

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

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

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

[0398] [ka]

[0399] [ka]

[0400] [ka]

[0401] In one embodiment of the organic EL device according to the present invention, when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, at least one of the components constituting the first light-emitting layer is different from the components constituting the second light-emitting layer. For example, 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.

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

[0403] The main peak wavelength of a compound is measured 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 of this sample (vertical axis: emission intensity, horizontal axis: wavelength) 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 measurement device is not limited to the device used here. In the emission spectrum, the peak wavelength at which the emission intensity is maximum is defined as the main peak wavelength. In this specification, the main peak wavelength may also be referred to as the fluorescence emission main peak wavelength (FL-peak).

[0404] The fluorescent compound may be the dopant material or the host material.

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

[0406] electron transport layer The electron transport layer is a layer containing a material with high electron transporting properties (electron transport material), and is formed between the light emitting layer and the cathode, or, if present, between the electron injection layer and the light emitting layer. The electron transport layer may have a single-layer structure or a multilayer structure including two or more layers. For example, the electron transport layer may have a two-layer structure including a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one 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, for example, 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.

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

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

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

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

[0411] The above materials are 10 -6 cm 2 It is a material having an electron mobility of 1 / Vs or more. Note that materials other than those mentioned above may be used for the electron transport layer as long as they have a higher electron transport property than a hole transport property.

[0412] electron injection layer The electron injection layer is a layer containing a material with high electron injection properties. For the electron injection layer, alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), rare earth metals such as europium (Eu) and ytterbium (Yb), and compounds containing these metals can be used. Examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, rare earth metal halides, and rare earth metal-containing organic complexes. A mixture of these compounds can also be used. Alternatively, an electron-transporting material containing an alkali metal, alkaline earth metal, or a compound thereof, such as Alq containing magnesium (Mg), may be used. In this case, electrons can be injected from the cathode more efficiently. Alternatively, the electron injection layer may be formed using a composite material obtained by mixing an organic compound and an electron donor (donor). Such composite materials have excellent electron injection and 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 (TTF) can also be used.

[0413] cathode The cathode is preferably made of a metal, alloy, electrically conductive compound, or mixture thereof, each having 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), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these. When an alkali metal, an alkaline earth metal, or an alloy containing these is used to form a cathode, a vacuum deposition method or a sputtering method can be used. When a silver paste or the like is used, a coating method or an inkjet method can be used. By providing an electron injection layer, the cathode can be formed using various conductive materials, regardless of the magnitude of the work function, such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, etc. These conductive materials can be deposited by sputtering, inkjet printing, spin coating, etc.

[0414] Insulation layer In organic EL devices, pixel defects due to leakage and short circuits are likely to occur because an electric field is applied to an ultra-thin film. To prevent this, an insulating layer made of an insulating thin film may be inserted between a pair of electrodes. Examples of materials used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, etc. Mixtures or laminates of these may also be used.

[0415] Space 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 laminated, in order to prevent excitons generated in the phosphorescent-emitting layer from diffusing into the fluorescent-emitting layer or to adjust the carrier balance. The spacer layer can also be provided between multiple phosphorescent-emitting layers. Since the spacer layer is provided between the light-emitting layers, it is preferably made of a material that has both electron transport and hole transport properties. Furthermore, to prevent triplet energy diffusion in the adjacent phosphorescent light-emitting layer, it is preferable that the triplet energy be 2.6 eV or more. Materials used for the spacer layer include the same materials as those used for the hole transport layer described above.

[0416] blocking layer A blocking layer such as an electron blocking layer, a hole blocking layer, or an exciton blocking layer may be provided adjacent to the light-emitting layer. The electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer, and the hole blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron transport layer. The exciton blocking layer has 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.

[0417] Each layer of the organic EL device 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.

[0418] There are no particular restrictions on the thickness of each layer, but generally, if the thickness is too thin, defects such as pinholes are likely to occur, and conversely, 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.

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

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

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

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

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

[0424] Invention compounds used in the production of organic EL devices (I) in Examples 1 to 3 [ka]

[0425] Comparative compounds used in the production of organic EL devices (I) of Comparative Examples 1 and 2 [ka]

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

[0427] Fabrication of organic EL device (I) Example 1 A 25mm x 75mm x 1.1mm 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 130nm. The glass substrate with the ITO transparent electrode after cleaning was mounted on a substrate holder of 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, thereby forming a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-1 to compound HA (HT-1:HA) was 97:3. Next, the compound HT-1 was vapor-deposited on the hole injection layer to form a first hole transport layer having a thickness of 40 nm. Next, the compound Inv-1 was vapor-deposited on this first hole transport layer to form a second hole transport layer having a thickness of 40 nm. Next, the compound HT-2 was vapor-deposited on this second hole transport layer to form a third hole transport layer having a thickness of 5 nm. Next, a first light-emitting layer having a thickness of 20 nm was formed on the third hole-transporting layer by co-depositing compound BH-1 (host material) and compound BD-1 (dopant material). The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 99:1. Next, the compound ET-1 was vapor-deposited on the light-emitting layer to form a first electron-transporting layer having a thickness of 5 nm. Next, a second electron transport layer having a thickness of 25 nm was formed on the first electron transport layer by co-deposition of the compounds ET-2 and Liq. The mass ratio of the compounds ET-2 and Liq (ET-2:Liq) was 50:50. Next, Yb was vapor-deposited on the second electron transport layer to form an electron injection electrode having a thickness of 1 nm. Then, metal Al was vapor-deposited on this electron injecting electrode to form a metal cathode with a film thickness of 50 nm. The layer structure of the organic EL device of Example 1 thus obtained is shown below. ITO (130) / HT-1:HA=97:3 (10) / HT-1 (40) / Inv-1 (40) / HT-2 (5) / BH-1:BD-1=99:1 (20) / ET-1 (5) / ET-2:Liq=50:50 (25) / Yb (1) / Al (50) In the above layer configuration, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

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

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

[0430] Evaluation of organic EL elements (I) The driving voltage and external quantum efficiency of the obtained organic EL device (I) were measured. (1) Measurement of driving voltage Current density is 10mA / cm 2 The voltage (unit: V) was measured when a voltage was applied to the organic EL element (I) so that the voltage was 0.05 V. The results are shown in Table 1. (2) Measurement of external quantum efficiency (EQE) The obtained organic EL device (I) was operated at room temperature and a current density of 10 mA / cm 2 The device was driven with a constant DC current at 1000 Hz. The luminance was measured using a luminance meter (Minolta CS-1000 spectroradiometer), and the external quantum efficiency (%) was calculated from the results. The results are shown in Table 1.

[0431] [Table 1]

[0432] Invention compounds used in the production of organic EL devices (II) in Examples 4 to 7 [ka]

[0433] Comparative compounds used in the production of the organic EL device (II) of Comparative Example 2 [ka]

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

[0435] Fabrication of organic EL device (II) Example 4 A 25mm x 75mm x 1.1mm 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 130nm. The glass substrate with the ITO transparent electrode after cleaning was mounted on a substrate holder of a vacuum deposition apparatus, and Compound Inv-1 and Compound HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 10 nm. The mass ratio of Compound Inv-1 to Compound HA (Inv-1:HA) was 97:3. Next, the compound Inv-1 was vapor-deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, the compound HT-4 was vapor-deposited on this first hole transport layer to form a second hole transport layer having a thickness of 10 nm. Next, a 25 nm-thick light-emitting layer was formed on the second hole transport layer by co-deposition of Compound BH-2 (host material) and Compound BD-2 (dopant material). The mass ratio of Compound BH-2 to Compound BD-2 (BH-2:BD-2) was 96:4. Next, the compound ET-3 was vapor-deposited on the light-emitting layer to form a first electron-transporting layer having a thickness of 10 nm. Next, the compound ET-4 was vapor-deposited on the first electron transport layer to form a second electron transport layer having a thickness of 15 nm. Next, LiF was vapor deposited on this second electron transport layer to form an electron injection electrode having a thickness of 1 nm. Then, metal Al was vapor-deposited on this electron injecting electrode to form a metal cathode with a film thickness of 50 nm. The layer structure of the organic EL device (II) of Example 4 thus obtained is shown below. ITO (130) / Inv-1:HA=97:3 (10) / Inv-1 (80) / HT-4 (10) / BH-2:BD-2=96:4 (25) / ET-3 (10) / ET-4 (15) / LiF (1) / Al (50) In the above layer configuration, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

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

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

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

[0439] [Table 2]

[0440] Invention compounds used in the production of organic EL devices (III) in Examples 8 to 17 [ka]

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

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

[0443] [ka]

[0444] Fabrication of organic EL device (III) Example 8 A 25mm x 75mm x 1.1mm 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 130nm. The glass substrate with the ITO transparent electrode after cleaning was mounted on a substrate holder of 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, thereby forming a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-1 to compound HA (HT-1:HA) was 97:3. Next, the compound HT-1 was vapor-deposited on the hole injection layer to form a first hole transport layer having a thickness of 40 nm. Next, the compound Inv-2 was vapor-deposited on this first hole transport layer to form a second hole transport layer having a thickness of 45 nm. Next, the compound HT-6 was vapor-deposited on this second hole transport layer to form a third hole transport layer having a thickness of 5 nm. Next, a first light-emitting layer having a thickness of 5 nm was formed on the third hole-transporting layer by co-depositing Compound BH-1 (host material) and Compound BD-3 (dopant material). The mass ratio of Compound BH-1 to Compound BD-3 (BH-1:BD-3) was 99:1. Next, a second emitting layer with a thickness of 20 nm was formed on the first emitting layer by co-depositing Compound BH-5 (host material) and Compound BD-3 (dopant material). The mass ratio of Compound BH-5 to Compound BD-3 (BH-5:BD-3) was 99:1. Next, the compound ET-1 was vapor-deposited on the second light-emitting layer to form a first electron-transporting layer having a thickness of 5 nm. Next, a second electron transport layer having a thickness of 31 nm was formed on the first electron transport layer by co-deposition of the compounds ET-2 and Liq. The mass ratio of the compounds ET-2 and Liq (ET-2:Liq) was 50:50. Next, Liq was evaporated onto the second electron transport layer to form an electron injection electrode having a thickness of 1 nm. Then, metal Al was vapor-deposited on this electron injecting electrode to form a metal cathode with a film thickness of 80 nm. The layer structure of the organic EL device (III) of Example 8 thus obtained is shown below. ITO (130) / HT-1:HA=97:3 (10) / HT-1 (40) / Inv-2 (45) / HT-6 (5) / BH-1:BD-3=99:1 (5) / BH-5:BD-3=99:1 (20) / ET-1 (5) / ET-2:Liq=50:50 (31) / Liq (1) / Al (80) In the above layer configuration, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

[0445] Example 9 An organic EL device (III) was prepared in the same manner as in Example 8, except that compound Inv-3 was used instead of compound Inv-2.

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

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

[0448] Example 12 An organic EL device (III) was fabricated in the same manner as in Example 8, except that instead of forming a 20-nm-thick second emitting layer by co-depositing compound BH-5 (host material) and compound BD-3 (dopant material) on the first emitting layer, a 20-nm-thick second emitting layer was formed by co-depositing compound BH-4 (host material), compound BH-7 (host material), and compound BD-3 (dopant material). The mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 70:30, and the concentration of compound BD-3 was 1 mass% with respect to the entire second emitting layer.

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

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

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

[0452] Example 16 A 25mm x 75mm x 1.1mm 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 130nm. The glass substrate with the ITO transparent electrode after cleaning was mounted on a substrate holder of 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, thereby forming a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-1 to compound HA (HT-1:HA) was 97:3. Next, the compound HT-1 was vapor-deposited on the hole injection layer to form a first hole transport layer having a thickness of 40 nm. Next, the compound Inv-2 was vapor-deposited on this first hole transport layer to form a second hole transport layer having a thickness of 45 nm. Next, the compound HT-2 was vapor-deposited on this second hole transport layer to form a third hole transport layer having a thickness of 5 nm. Next, a first light-emitting layer having a thickness of 5 nm was formed on the third hole-transporting layer by co-depositing Compound BH-3 (host material) and Compound BD-5 (dopant material). The mass ratio of Compound BH-3 to Compound BD-5 (BH-3:BD-5) was 99:1. Next, a second emitting layer with a thickness of 20 nm was formed on the first emitting layer by co-depositing Compound BH-6 (host material) and Compound BD-5 (dopant material). The mass ratio of Compound BH-6 to Compound BD-5 (BH-6:BD-5) was 99:1. Next, the compound ET-3 was vapor-deposited on the second light-emitting layer to form a first electron-transporting layer having a thickness of 10 nm. Next, the compound ET-4 was vapor-deposited on the first electron transport layer to form a second electron transport layer having a thickness of 15 nm. Then, metal Al was vapor-deposited on this electron injecting electrode to form a metal cathode with a film thickness of 80 nm. The layer structure of the organic EL device (III) of Example 16 thus obtained is shown below. ITO (130) / HT-1:HA=97:3 (10) / HT-1 (40) / Inv-2 (45) / HT-2 (5) / BH-3:BD-5=99:1 (5) / BH-6:BD-5=99:1 (20) / ET-3 (10) / ET-4 (15) / Al (80) In the above layer configuration, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

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

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

[0455] Evaluation of organic EL elements (III) The external quantum efficiency of the obtained organic EL device (III) was measured in the same manner as for the organic EL device (I). The results are shown in Table 3. (3)95% lifespan (LT95) The obtained organic EL device (III) was subjected to a current density of 50 mA / cm 2 The time until the brightness decreased to 95% of the initial brightness was measured, and this was taken as the 95% lifespan (LT95). The results are shown in Table 3.

[0456] [Table 3]

[0457] Invention compounds used in the production of organic EL devices (IV) in Examples 18 to 34 [ka]

[0458] Comparative compounds used in the production of organic EL device (IV) of Comparative Example 6 [ka]

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

[0460] [ka]

[0461] Fabrication of organic EL device (IV) Example 18 A 25mm x 75mm x 1.1mm 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 130nm. The glass substrate with the ITO transparent electrode after cleaning was mounted on a substrate holder of a vacuum deposition apparatus, and Compound Inv-2 and Compound HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 10 nm. The mass ratio of Compound Inv-2 to Compound HA (Inv-2:HA) was 97:3. Next, the compound Inv-2 was vapor-deposited on the hole injection layer to form a first hole transport layer with a thickness of 85 nm. Next, the compound HT-6 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 5 nm. Next, a first light-emitting layer with a thickness of 5 nm was formed on the second hole-transporting layer by co-depositing Compound BH-1 (host material) and Compound BD-3 (dopant material). The mass ratio of Compound BH-1 to Compound BD-3 (BH-1:BD-3) was 99:1. Next, a second emitting layer with a thickness of 15 nm was formed on the first emitting layer by co-depositing Compound BH-5 (host material) and Compound BD-3 (dopant material). The mass ratio of Compound BH-5 to Compound BD-3 (BH-5:BD-3) was 99:1. Next, the compound ET-1 was vapor-deposited on the second light-emitting layer to form a first electron-transporting layer having a thickness of 5 nm. Next, a second electron transport layer having a thickness of 31 nm was formed on the first electron transport layer by co-deposition of the compounds ET-2 and Liq. The mass ratio of the compounds ET-2 and Liq (ET-2:Liq) was 50:50. Next, Liq was evaporated onto the second electron transport layer to form an electron injection electrode having a thickness of 1 nm. Then, metal Al was vapor-deposited on this electron injecting electrode to form a metal cathode with a film thickness of 80 nm. The layer structure of the organic EL device (IV) of Example 18 thus obtained is shown below. ITO (130) / Inv-2:HA=97:3 (10) / Inv-2 (85) / HT-6 (5) / BH-1:BD-3=99:1 (5) / BH-5:BD-3=99:1 (15) / ET-1 (5) / ET-2:Liq=50:50 (31) / Liq (1) / Al (80) In the above layer configuration, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

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

[0463] Example 22 An organic EL device (IV) was produced in the same manner as in Example 18, except that the compound HT-7 was used instead of the compound HT-6.

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

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

[0466] Example 25 A 25mm x 75mm x 1.1mm 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 130nm. The glass substrate with the ITO transparent electrode after cleaning was mounted on a substrate holder of a vacuum deposition apparatus, and Compound Inv-2 and Compound HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 10 nm. The mass ratio of Compound Inv-2 to Compound HA (Inv-2:HA) was 97:3. Next, the invention compound Inv-2 was vapor-deposited on the hole injection layer to form a first hole transport layer with a thickness of 85 nm. Next, the compound HT-8 was vapor-deposited on this first hole transport layer to form a second hole transport layer having a thickness of 5 nm. Next, a first light-emitting layer with a thickness of 5 nm was formed on the second hole-transporting layer by co-depositing Compound BH-3 (host material) and Compound BD-5 (dopant material). The mass ratio of Compound BH-3 to Compound BD-5 (BH-3:BD-5) was 99:1. Next, a second emitting layer with a thickness of 15 nm was formed on the first emitting layer by co-depositing Compound BH-6 (host material) and Compound BD-5 (dopant material). The mass ratio of Compound BH-6 to Compound BD-5 (BH-6:BD-5) was 99:1. Next, the compound ET-3 was vapor-deposited on the second light-emitting layer to form a first electron-transporting layer having a thickness of 10 nm. Next, the compound ET-4 was vapor-deposited on the first electron transport layer to form a second electron transport layer having a thickness of 15 nm. Then, metal Al was vapor-deposited on the second electron transport layer to form a metal cathode with a film thickness of 80 nm. The layer structure of the organic EL device (IV) of Example 25 thus obtained is shown below. ITO (130) / Inv-2:HA=97:3 (10) / Inv-2 (85) / HT-8 (5) / BH-3:BD-5=99:1 (5) / BH-6:BD-5=99:1 (15) / ET-3 (10) / ET-4 (15) / Al (80) In the above layer configuration, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

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

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

[0469] Example 28 An organic EL device (IV) was fabricated in the same manner as in Example 18, except that instead of forming a 15 nm-thick second emitting layer by co-depositing compound BH-5 (host material) and compound BD-3 (dopant material) on the first emitting layer, a 20 nm-thick second emitting layer was formed by co-depositing compound BH-4 (host material), compound BH-7 (host material), and compound BD-3 (dopant material). The mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 70:30, and the concentration of compound BD-3 was 1 mass% with respect to the entire second emitting layer.

[0470] Example 29 An organic EL device (IV) was prepared in the same manner as in Example 28, except that compound HT-7 was used instead of compound HT-6 and the mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 60:40.

[0471] Example 30 An organic EL device (IV) was fabricated in the same manner as in Example 18, except that instead of forming a 15-nm-thick second emitting layer on the first emitting layer by co-depositing compound BH-5 (host material) and compound BD-3 (dopant material), a 20-nm-thick second emitting layer was formed by co-depositing compound BH-8 (host material), compound BH-5 (host material), and compound BD-3 (dopant material). The mass ratio of compound BH-8 to compound BH-5 (BH-8:BH-5) was 70:30, and the concentration of compound BD-3 was 1 mass% with respect to the entire second emitting layer.

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

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

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

[0475] [Table 4]

[0476] As is clear from the results in Tables 1 to 4, the compounds Inv-1 to Inv-9 provide organic EL devices with lower driving voltages and higher external quantum efficiencies than the comparative compounds Ref-1 to Ref-5.

[0477] Compounds Inv-1 to Inv-9 synthesized in the synthesis examples [ka]

[0478] Intermediate synthesis example 1: Synthesis of intermediate A [ka]

[0479] Under an argon atmosphere, a mixture of 7.40 g (22.1 mmol) of 2-bromo9-phenyl-9-methyl-9H-fluorene, 5.08 g (23.2 mmol) of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, 0.404 g (0.441 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.845 g (1.77 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos), 33 mL of 2M aqueous potassium phosphate solution, and 110 mL of 1,4-dioxane was stirred at 80 °C for 7 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography to yield 7.67 g of a white solid (Intermediate A-1). The yield was 99%.

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

[0481] Intermediate synthesis example 2: Synthesis of intermediate B [ka]

[0482] Under an argon atmosphere, a mixture of 9.05 g (27.0 mmol) of 2-bromo9-phenyl-9-methyl-9H-fluorene, 5.07 g (32.4 mmol) of 2-chlorophenylboronic acid, 0.395 g (0.540 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, 40.5 mL of 2 M aqueous sodium carbonate, and 135 mL of DME was refluxed at the boiling point for 7 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography to give 9.82 g of a white solid. The yield was 99%.

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

[0484] The same procedure was followed as in the synthesis of Intermediate A, except that bromobenzene was used instead of 2-bromobiphenyl, to obtain a white solid in 75% yield.

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

[0486] Under an argon atmosphere, a mixture of 5.93 g (11.9 mmol) of Intermediate A, 3.89 g (14.2 mmol) of 2-bromo-9,9-dimethyl-9H-fluorene, 0.217 g (0.237 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.275 g (0.949 mmol) of tri-tert-butylphosphonium tetrafluoroborate, 23.7 mL of lithium bis(trimethylsilyl)amide (1 M toluene solution), and 119 mL of xylene was refluxed at the boiling point for 7 hours. The reaction mixture 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 3.29 g of a white solid. The yield was 40%. Mass spectrometry analysis showed that the obtained product was compound Inv-1, with m / e=692 for a molecular weight of 691.92.

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

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

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

[0490] The same procedure as in Synthesis Example 2 was carried out, except that 4-bromobiphenyl was used instead of 2-bromo-9,9-dimethyl-9H-fluorene, to obtain 3.51 g of a white solid in a yield of 54%. Mass spectrometry analysis showed that the obtained product was compound Inv-3, with m / e=652 for a molecular weight of 651.85.

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

[0492] Under an argon atmosphere, a mixture of 2.43 g (8.51 mmol) of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, 3.44 g (9.37 mmol) of Intermediate B, 0.156 g (0.170 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.280 g (0.681 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos), 1.15 g (11.9 mmol) of sodium t-butoxide, and 85 mL of xylene was stirred at 110 °C for 7 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography to obtain 1.88 g of a white solid. The yield was 35%. Mass spectrometry analysis showed that the obtained product was compound Inv-4, with m / e=616 for a molecular weight of 615.82.

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

[0494] The same procedures as in Synthesis Example 4 were carried out, except that Intermediate D was used instead of Intermediate B and Intermediate C was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, to obtain a white solid in a yield of 62%. Mass spectrometry analysis showed that the obtained product was compound Inv-5, with m / e=692 for a molecular weight of 691.92.

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

[0496] The same procedure was carried out as in Synthesis Example 4, except that N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-9H-fluoren-2-amine was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, to obtain a white solid in a yield of 48%. Mass spectrometry analysis showed that the obtained product was compound Inv-6, with m / e=692 for a molecular weight of 691.92.

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

[0498] The same procedure as in Synthesis Example 4 was carried out except that Intermediate E was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, to obtain a white solid in a yield of 47%. Mass spectrometry analysis showed that the obtained product was compound Inv-7, with m / e=754 for a molecular weight of 753.99.

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

[0500] The same procedure as in Synthesis Example 4 was carried out except that Intermediate F was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, to obtain a white solid. The yield was 55%. Mass spectrometry analysis showed that the obtained product was compound Inv-8, with m / e=768 for a molecular weight of 767.97.

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

[0502] The same procedure was carried out as in Synthesis Example 4, except that bis([1,1'-biphenyl]-4-yl-d9)amine was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, to obtain a white solid in a yield of 65%. Mass spectrometry analysis showed that the obtained product was compound Inv-9, with a molecular weight of 669.96 and an m / e of 670. [Explanation of symbols]

[0503] 1, 11, 12 Organic EL elements 2 boards 3 Anode 4 cathode 5. Light-emitting layer 5a First light-emitting layer 5b Second light-emitting layer 6. Hole transport zone (hole transport layer) 6a Hole injection layer 6b First hole transport layer 6c Second hole transport layer 6d Third hole transport layer 7 Electron transport zone (electron transport layer) 7a First electron transport layer 7b Second electron transport layer 10, 20, 30 light units

Claims

1. A compound represented by the following formula (1): 【Chemical 1】 (In formula (1), N ＊ is the central nitrogen atom. R ａ and R ｂ One of the groups is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and the other is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. However, R ａ and R ｂ may be bonded to each other to form a substituted or unsubstituted ring. R ２ , R ３ , R ６ and R ７ is a single bond bonded to *1, and R １ , R ４ , R ５ , R ８ , and R that is not a single bond bonded to *1 ２ , R ３ , R ６ and R ７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 15 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. R １ , R ４ , R ５ , R ８ and the R ２ , R ３ , R ６ and R ７ Adjacent two selected from are not bonded to each other and therefore do not form a ring. R １１ ~R １４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms. R １１ ~R １４ Adjacent two selected from are not bonded to each other and therefore do not form a ring. L １ ~L ４ are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms. Ar １ is a group represented by any one of the following formulas (1a) to (1c), (1f) and (1g), and Ar ２ is a group represented by the following formula (1b) or (1c): 【Chemistry 2】 (In formula (1a), *21 is L １ or L ２ is the binding site to R １０１ ~R １０５ one selected from is a single bond bonded to *22, and R １０６ ~R １１０ is a single bond bonded to *23, and R １１１ ~R １１５ One selected from is a single bond bonded to *24. The R that is not a single bond １０１ ~R １１５ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. The R that is not a single bond １０１ ~R １０５ adjacent two selected from are not bonded to each other and therefore do not form a ring, The R that is not a single bond １０６ ~R １１０ adjacent two selected from are not bonded to each other and therefore do not form a ring, The R that is not a single bond １１１ ~R １１５ Adjacent two selected from are not bonded to each other and therefore do not form a ring. m is 0 or 1, n is 0 or 1, and l is 0 or 1. R １１６ ~R １２０ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. R １１６ ~R １２０ Adjacent two selected from are not bonded to each other and therefore do not form a ring. 【Chemistry 3】 (In formula (1b), *25 is L １ or L ２ is the binding site to R １２１ ~R １２８ One selected from is a single bond bonded to *26. The R that is not a single bond １２１ ~R １２８ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. The R that is not a single bond １２１ ~R １２８ Adjacent two selected from are not bonded to each other and therefore do not form a ring. However, L １ is a p-phenylene group, and Ar １ is represented by formula (1b), R in the group represented by formula (1b) bonded to the p-phenylene group １２１ , R １２４ , R １２５ , and R １２８ one selected from is a single bond bonded to *26, L ２ is a p-phenylene group, and Ar ２ is represented by formula (1b), R in the group represented by formula (1b) bonded to the p-phenylene group １２１ , R １２４ , R １２５ , and R １２８ One selected from is a single bond bonded to *26.) 【Chemistry 4】 (In formula (1c), *27 is L １ or L ２ is the binding site to R １３１ ~R １４０ One selected from is a single bond bonded to *28. The R that is not a single bond １３１ ~R １４０ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. The R that is not a single bond １３１ ~R １４０ Adjacent two selected from are not bonded to each other and therefore do not form a ring. 【Chemistry 5】 (In formula (1f), *34 is L １ or L ２ is the binding site to X is an oxygen atom, a sulfur atom, or NR Ａ is. R １９１ ~R １９８ and R Ａ One selected from is a single bond bonded to *35. The R that is not a single bond Ａ is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. The R that is not a single bond １９１ ~R １９８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. The R that is not a single bond １９１ ~R １９８ Any two adjacent groups selected from may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore not form a ring. 【Chemistry 6】 (In formula (1g), *36 is L １ or L ２ is the binding site to R B , R C , and R ２０１ ~R ２０８ One selected from is a single bond bonded to *37. The R that is not a single bond B and R C are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. The R that is not a single bond B and R C may be bonded to each other to form a substituted or unsubstituted ring. The R that is not a single bond ２０１ ~R ２０８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. The R that is not a single bond ２０１ ~R ２０８ Adjacent two selected from are not bonded to each other and therefore do not form a ring.

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

3. R ２ or R ７ The compound according to claim 1 or 2, wherein is a single bond bonded to *1.

4. L ３ The compound according to any one of claims 1 to 3, wherein is a single bond.

5. L ４ The compound according to any one of claims 1 to 4, wherein is a single bond.

6. Ar １ is a group represented by formula (1a) or (1g).

7. Ar １ is a group represented by formula (1a), and the group represented by formula (1a) satisfies at least one of the following (i) to (iii): (i) R １０１ or R １０５ is a single bond that bonds to *22 (ii) R １０６ or R １１０ is a single bond that bonds to *23 (iii) R １１１ or R １１５ is a single bond that bonds to *24

8. Ar １ is a group represented by the formula (1g), and in the group represented by the formula (1g), R B and R C and each independently represent a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group.

9. Ar １ is a group represented by the formula (1g), and in the group represented by the formula (1g), R ２０２ or R ２０７ The compound according to any one of claims 1 to 6, wherein is a single bond attached to *37.

10. Ar １ The compound according to any one of claims 1 to 5, wherein: is a group represented by formula (1b).

11. L １ and L ２ and each independently represent a single bond or an arylene group having 6 to 12 ring carbon atoms.

12. Ar ２ The compound according to any one of claims 1 to 11, wherein: is a group represented by formula (1c).

13. The compound according to any one of claims 1 to 12, which contains at least one deuterium atom.

14. A material for an organic electroluminescence device, comprising the compound according to any one of claims 1 to 13.

15. A hole transport layer material comprising the compound according to any one of claims 1 to 13.

16. An organic electroluminescence device having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer includes the compound according to any one of claims 1 to 13.

17. 17. The organic electroluminescence device according to claim 16, wherein the organic layer comprises a hole transporting region between the anode and the light emitting layer, and the hole transporting region comprises the compound.

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

19. 19. The organic electroluminescence device according to claim 18, wherein the light-emitting layer and the second hole transport layer are in direct contact with each other.

20. 20. The organic electroluminescence device according to claim 18, 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.

21. 21. The organic electroluminescence device according to claim 16, wherein the light-emitting layer is a single layer.

22. 22. The organic electroluminescence device according to claim 16, wherein the light-emitting layer contains a light-emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less.

23. 23. The organic electroluminescence device according to claim 16, wherein the light-emitting layer contains a fluorescent dopant material.

24. An electronic device comprising the organic electroluminescence device according to any one of claims 16 to 23.

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