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

Abstract

To provide a compound among luminescent materials used for organic EL elements that improves element efficiency.SOLUTION: Specifically, a compound represented by the formula (BD-1) in the figure is presented, for example.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] When a voltage is applied to an organic electroluminescence device (hereinafter sometimes referred to as an "organic EL device"), holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical law of electron spin, singlet excitons are generated at a rate of 25% and triplet excitons are generated at a rate of 75%. Fluorescent organic EL devices that use light emitted from singlet excitons are being applied to full-color displays such as those for mobile phones and televisions, but their internal quantum efficiency is said to be limited to 25%. Therefore, efforts are being made to improve the performance of organic EL devices.

[0003] For example, Patent Documents 1 to 4 disclose cyclic boron compounds as compounds that can be used in organic electroluminescence devices. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] International Publication No. 2015 / 102118 [Patent Document 2] Korean Patent Registration No. 10-2094830 [Patent Document 3] International Publication No. 2020 / 217229 [Patent Document 4] Chinese Patent Application Publication No. 111471064 Summary of the Invention [Problem to be solved by the invention]

[0005] In order to improve the performance of electronic devices such as displays, further improvement in the performance of organic EL elements is desired. Examples of the performance of organic EL elements include brightness, emission wavelength, half-width, chromaticity, luminous efficiency, driving voltage, and lifespan. For example, a compound that exhibits an emission peak wavelength in a desired wavelength range in the fluorescence spectrum waveform is required for blue light-emitting materials.

[0006] An object of the present invention is to provide a compound that, among light-emitting materials used in organic EL devices, improves device efficiency when used as a blue-emitting material. Another object of the present invention is to provide a material for organic electroluminescence devices, an organic electroluminescence device, and an electronic device equipped with the organic electroluminescence device, which contains a compound that, among light-emitting materials used in organic EL devices, improves device efficiency when used as a blue-emitting material. [Means for solving the problem]

[0007] According to one aspect of the present invention, there is provided a compound represented by the following general formula (1):

[0008] [ka]

[0009] (In the general formula (1), Ring A1, ring B1, and ring C1 each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted aromatic heterocycle having 6 to 50 ring atoms, When ring A1 has two or more substituents, one or more pairs of adjacent two or more substituents may be joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, When ring B1 has two or more substituents, one or more pairs of adjacent two or more substituents may be joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, When ring C1 has two or more substituents, one or more pairs of adjacent two or more substituents are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, The substituent when ring A1 has a substituent, the substituent when ring B1 has a substituent, and the substituent when ring C1 has a substituent each independently represent: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 131 )(R 132 ) a group represented by -Si(R 133 )(R 134 )(R 135 ) a group represented by -O-(R 136 ) a group represented by -S-(R 137 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 138 a group represented by -COOR 139 a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R 140 )(R141 ) a group represented by -Ge(R 142 )(R 143 )(R 144 ) a group represented by -B(R 145 )(R 146 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, X is oxygen atoms, sulfur atoms, N(R 101 ), Si(R 102 )(R 103 ), or C(R 104 )(R 105 ) and R 101 teeth, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 133 )(R 134 )(R 135 ) a group represented by -O-(R 136 ) a group represented by -S-(R 137 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 138 a group represented by -COOR 139 a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R140 )(R 141 ) a group represented by -Ge(R 142 )(R 143 )(R 144 ) a group represented by -B(R 145 )(R 146 ) a group represented by 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 A group represented by the following general formula (3): The dashed line for U1 is and ring B1 bond together to form a substituted or unsubstituted monocycle, or and ring B1 bond to each other to form a substituted or unsubstituted fused ring, or and ring C1 together to form a substituted or unsubstituted monocyclic ring, or and the ring C1 bond to each other to form a substituted or unsubstituted fused ring, U1 is oxygen atoms, sulfur atoms, N(R 111 ), or B(R 112 ) and V1 is N(R 113 ), B(R 114 ), or C(=O), U1 and V1 are different from each other, R 102 ~R 105 , R 111 ~R 114、 and R 131 ~R 146 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 131 If there are multiple R 131 are the same or different from each other, R 132 If there are multiple R 132 are the same or different from each other, R 133 If there are multiple R 133 are the same or different from each other, R 134 If there are multiple R 134 are the same or different from each other, R 135 If there are multiple R 135 are the same or different from each other, R 136 If there are multiple R 136 are the same or different from each other, R 137 If there are multiple R 137 are the same or different from each other, R 138 If there are multiple R 138 are the same or different from each other, R 139 If there are multiple R 139 are the same or different from each other, R 140 If there are multiple R 140 are the same or different from each other, R 141 If there are multiple R 141 are the same or different from each other, R 142 If there are multiple R 142 are the same or different from each other, R 143 If there are multiple R 143 are the same or different from each other, R 144 If there are multiple R144 are the same or different from each other, R 145 If there are multiple R 145 are the same or different from each other, R 146 If there are multiple R 146 are either identical or different.)

[0010] [ka]

[0011] (In the general formula (3), The dashed line for U2 is and ring A1 bond together to form a substituted or unsubstituted monocycle, or and ring A1 bond together to form a substituted or unsubstituted fused ring, or and ring B1 together to form a substituted or unsubstituted monocyclic ring, or and ring B1 bond to each other to form a substituted or unsubstituted fused ring, U2 is oxygen atoms, sulfur atoms, N(R 121 ), or B(R 122 ) and V2 is N(R 123 ), B(R 124 ), or C(=O), U2 and V2 are different from each other, R 121 ~R 124 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, U1 in the general formula (1) and U2 in the general formula (3) are the same or different from each other, V1 in the general formula (1) and V2 in the general formula (3) are the same or different from each other, *v indicates the bonding position to X in general formula (1).

[0012] According to one aspect of the present invention, there is provided a material for an organic electroluminescence device, which comprises the compound according to the above-described aspect of the present invention.

[0013] According to one aspect of the present invention, there is provided an organic electroluminescent device material having a cathode, an anode, and an organic layer between the cathode and the anode, wherein at least one layer of the organic layer contains the compound according to the above-mentioned one aspect of the present invention as a first compound.

[0014] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescence element according to the above-described aspect of the present invention. [Effects of the Invention]

[0015] According to one aspect of the present invention, it is possible to provide a compound that, among light-emitting materials for use in organic EL devices, improves device efficiency when used as a blue-emitting material.The present invention also provides a material for organic electroluminescence devices, an organic electroluminescence device, and an electronic device equipped with the organic electroluminescence device, which contains the compound, among light-emitting materials for use in organic EL devices, that improves device efficiency when used as a blue-emitting material. [Brief explanation of the drawings]

[0016] [Figure 1] FIG. 10 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a third embodiment of the present invention. [Figure 2]FIG. 10 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a fourth embodiment of the present invention. [Figure 3] FIG. 10 is a diagram showing a schematic configuration of another example of an organic electroluminescence element according to a fourth embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0017] [Definition] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0018] 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.

[0019] 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.

[0020] 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.

[0021] 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.

[0022] 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.

[0023] 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.

[0024] "Substituents described herein" The substituents described in this specification will be explained below.

[0025] 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.

[0026] "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.

[0027] 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, A perylenyl group, or 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).

[0028] [ka]

[0029] [ka]

[0030] 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 monovalent groups derived from the ring structures represented by the general formulae (TEMP-1) to (TEMP-15) above, in which one or more hydrogen atoms are replaced with substituents.

[0031] "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.

[0032] 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).

[0033] 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).

[0034] 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.

[0035] 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, Azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.

[0036] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): 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).

[0037] 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):

[0038] [ka]

[0039] [ka]

[0040] 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.

[0041] 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, a phenylquinazolinyl group, and a biphenylylquinazolinyl group.

[0042] Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, t-Butyldibenzofuranyl group, and the monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0043] Substituted heterocyclic groups containing sulfur atoms (specific example group G2B3): phenyldibenzothiophenyl group, methyldibenzothiophenyl group, t-Butyldibenzothiophenyl group, and the monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0044] 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):

[0045] The "one or more hydrogen atoms of the monovalent heterocyclic group" refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, X A and Y A a hydrogen atom bonded to a nitrogen atom when at least one of A and Y A or more hydrogen atoms selected from the hydrogen atoms of a methylene group when one of the groups is CH2.

[0046] "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.

[0047] 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.

[0048] Substituted alkyl groups (specific example group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group and trifluoromethyl group.

[0049] "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.

[0050] Unsubstituted alkenyl groups (specific example group G4A): vinyl groups, Allyl groups, a 1-butenyl group, 2-butenyl group and 3-butenyl group.

[0051] 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.

[0052] "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.

[0053] Unsubstituted alkynyl groups (specific example group G5A): Ethynyl group.

[0054] "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.

[0055] 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.

[0056] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.

[0057] -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.

[0058] -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.

[0059] -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.

[0060] -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.

[0061] "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.

[0062] "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.

[0063] "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.

[0064] "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.

[0065] "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.

[0066] "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.

[0067] "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.

[0068] "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.

[0069] "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. Thus, 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.

[0070] 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.

[0071] 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.

[0072] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.

[0073] [ka]

[0074] In this specification, unless otherwise specified in this specification, a (9-phenyl)carbazolyl group specifically means any of the following groups:

[0075] [ka]

[0076] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0077] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0078] [ka]

[0079] In the general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.

[0080] 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.

[0081] "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.

[0082] "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.

[0083] "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.

[0084] 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).

[0085] [ka]

[0086] [ka]

[0087] 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.

[0088] [ka]

[0089] 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.

[0090] [ka]

[0091] 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.

[0092] 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).

[0093] [ka]

[0094] [ka]

[0095] [ka]

[0096] In the general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 each independently represent a hydrogen atom or a substituent.

[0097] [ka]

[0098] [ka]

[0099] [ka]

[0100] [ka]

[0101] In the general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 each independently represent a hydrogen atom or a substituent.

[0102] The above is the explanation of "substituents described in this specification."

[0103] - "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.

[0104] [ka]

[0105] For example, R921 ~R 930 In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," one pair of adjacent two groups is R 921 and R 922 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.

[0106] 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).

[0107] [ka]

[0108] When a "set of two or more adjacent units" forms a ring, it does not only mean that a set of two adjacent units is bonded, as in the previous example, but also that 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.

[0109] [ka]

[0110] 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 (TMEP-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 (TMEP-104) is a monocyclic ring. A If is a naphthalene ring, then ring Q A is a fused ring.

[0111] 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 are bonded to form a ring Q A is R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 It means a ring formed by the carbon atom of the anthracene skeleton to which R is bonded and one or more arbitrary elements. 921 and R 922 Todekan Q A In the case where R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 When 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

[0112] 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.

[0113] 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").

[0114] 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, a group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring carbon atoms and an unsubstituted heterocyclic group having 5 to 50 ring atoms, 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, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 901 If there are two or more, there are two or more R 901 are identical 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 903 If there are two or more, there are two or more R 903are 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.

[0115] In one embodiment, the substituents in the "substituted or unsubstituted" are: an alkyl group having 1 to 50 carbon atoms; The group is selected from the group consisting of aryl groups having 6 to 50 ring carbon atoms and heterocyclic groups having 5 to 50 ring atoms.

[0116] In one embodiment, the substituents in the "substituted or unsubstituted" are: an alkyl group having 1 to 18 carbon atoms; The group is selected from the group consisting of aryl groups having 6 to 18 ring carbon atoms and heterocyclic groups having 5 to 18 ring atoms.

[0117] 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."

[0118] 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.

[0119] 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.

[0120] First Embodiment (compound) The compound according to this embodiment is a compound represented by the following general formula (1).

[0121] [ka]

[0122] (In the general formula (1), Ring A1, ring B1, and ring C1 each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted aromatic heterocycle having 6 to 50 ring atoms, When ring A1 has two or more substituents, one or more pairs of adjacent two or more substituents may be joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, When ring B1 has two or more substituents, one or more pairs of adjacent two or more substituents may be joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, When ring C1 has two or more substituents, one or more pairs of adjacent two or more substituents are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, The substituent when ring A1 has a substituent, the substituent when ring B1 has a substituent, and the substituent when ring C1 has a substituent each independently represent: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 131 )(R 132 ) a group represented by -Si(R 133 )(R 134 )(R 135 ) a group represented by -O-(R 136 ) a group represented by -S-(R 137 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 138 a group represented by -COOR 139 a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R 140 )(R 141 ) a group represented by -Ge(R 142 )(R 143 )(R 144 ) a group represented by -B(R 145 )(R 146 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, X is oxygen atoms, sulfur atoms, N(R 101 ), Si(R 102 )(R 103 ), or C(R 104 )(R 105 ) and R 101 teeth, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 133 )(R 134 )(R 135 ) a group represented by -O-(R 136 ) a group represented by -S-(R 137 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 138 a group represented by -COOR 139 a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R 140 )(R 141 ) a group represented by -Ge(R 142 )(R 143 )(R 144 ) a group represented by -B(R 145 )(R 146 ) a group represented by 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 A group represented by the following general formula (3): The dashed line for U1 is and ring B1 bond together to form a substituted or unsubstituted monocycle, or and ring B1 bond to each other to form a substituted or unsubstituted fused ring, or and ring C1 together to form a substituted or unsubstituted monocyclic ring, or and the ring C1 bond to each other to form a substituted or unsubstituted fused ring, U1 is oxygen atoms, sulfur atoms, N(R 111 ), or B(R 112 ) and V1 is N(R 113 ), B(R 114 ), or C(=O), U1 and V1 are different from each other, R 102 ~R 105 , R 111 ~R 114、 and R 131 ~R 146 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 131 If there are multiple R 131 are the same or different from each other, R 132 If there are multiple R 132 are the same or different from each other, R 133 If there are multiple R133 are the same or different from each other, R 134 If there are multiple R 134 are the same or different from each other, R 135 If there are multiple R 135 are the same or different from each other, R 136 If there are multiple R 136 are the same or different from each other, R 137 If there are multiple R 137 are the same or different from each other, R 138 If there are multiple R 138 are the same or different from each other, R 139 If there are multiple R 139 are the same or different from each other, R 140 If there are multiple R 140 are the same or different from each other, R 141 If there are multiple R 141 are the same or different from each other, R 142 If there are multiple R 142 are the same or different from each other, R 143 If there are multiple R 143 are the same or different from each other, R 144 If there are multiple R 144 are the same or different from each other, R 145 If there are multiple R 145 are the same or different from each other, R 146 If there are multiple R 146 are either identical or different.)

[0123] [ka]

[0124] (In the general formula (3), The dashed line for U2 is and ring A1 bond together to form a substituted or unsubstituted monocycle, or and ring A1 bond together to form a substituted or unsubstituted fused ring, or and ring B1 together to form a substituted or unsubstituted monocyclic ring, or and ring B1 bond to each other to form a substituted or unsubstituted fused ring, U2 is oxygen atoms, sulfur atoms, N(R 121 ), or B(R 122 ) and V2 is N(R 123 ), B(R 124 ), or C(=O), U2 and V2 are different from each other, R 121 ~R 124 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, U1 in the general formula (1) and U2 in the general formula (3) are the same or different from each other, V1 in the general formula (1) and V2 in the general formula (3) are the same or different from each other, *v indicates the bonding position to X in the general formula (1).

[0125] According to this embodiment, it is possible to provide a compound that improves the efficiency of an organic EL device when used as a blue light-emitting material among light-emitting materials used in the device.

[0126] According to an embodiment of the compound, it is possible to provide a compound having an emission peak wavelength in a desired wavelength band in a fluorescence spectrum waveform. According to an embodiment of the compound, light having a narrow half-width of the fluorescence emission spectrum is emitted. According to an embodiment of the compound, a high PLQY value is exhibited. By using the compound according to one embodiment as a material for an organic EL device, it is possible to emit light having a narrow half-width of the fluorescent emission spectrum from the device, thereby improving the luminous efficiency of the organic EL device. In this specification, the maximum peak wavelength of fluorescent emission may be referred to as the maximum peak wavelength of fluorescent emission or maximum peak wavelength.

[0127] The compound according to this embodiment preferably has a maximum fluorescent emission peak wavelength of 445 nm or more. The compound according to this embodiment preferably has a maximum fluorescent emission peak wavelength of 480 nm or less, more preferably 465 nm or less. When the compound according to this embodiment has a maximum fluorescent emission peak wavelength of 445 nm or more, electronic devices such as displays equipped with an organic EL element containing the compound according to this embodiment are likely to emit the desired moderate blue light. When the compound according to this embodiment has a maximum fluorescent emission peak wavelength of 480 nm or less, electronic devices such as displays equipped with an organic EL element containing the compound according to this embodiment are likely to emit the desired moderate blue light.

[0128] In this specification, the maximum peak wavelength of fluorescence emission is the wavelength at which the compound to be measured is 10 -6 moles / liter or more, 10 -5The maximum peak wavelength of the fluorescence spectrum at which the emission intensity is maximum in a toluene solution in which the compound is dissolved at a concentration of 0.1 mole / liter or less is measured. A fluorescence spectrum measuring device (device name: FP-8300, manufactured by JASCO Corporation) can be used as the measuring device. Note that the fluorescence spectrum measuring device is not limited to the device exemplified here.

[0129] The compound according to this embodiment preferably has a low lowest excited singlet energy level (hereinafter sometimes referred to as the S1 energy level). For example, the S1 energy level of the compound according to this embodiment is preferably in the range of 2.6 eV to 3.1 eV, more preferably in the range of 2.6 eV to 3.0 eV. Therefore, according to one embodiment, it is believed that an electronic device such as a display equipped with an organic EL element containing the compound according to this embodiment can easily emit the desired moderate blue light.

[0130] Here, the S1 energy level is calculated using the B3LYP hybrid function and the 6-31g basis set. * can be calculated by TD-DFT calculations using the Gaussian 16 software program available from Gaussian Inc.

[0131] The compound according to this embodiment preferably has a high photoluminescence quantum yield (PLQY). The compound according to this embodiment preferably has a PLQY of 80% or more, and more preferably 85% or more.

[0132] The PLQY can be measured by the following method. The compound to be measured was dissolved in toluene and 5.0 × 10 -6A 200 mol / L solution is prepared, and after freeze-degassing, an argon-saturated solution is prepared. The resulting solution is transferred to a quartz cell (optical path length 1.0 cm) and the photoluminescence quantum yield (PLQY) is measured using an absolute PL quantum yield measurement system "Hamamatsu Quantaurus-QY C11347" (Hamamatsu Photonics K.K.).

[0133] In the compound represented by the general formula (1), R 101 is a group represented by the general formula (3), U1 in the general formula (1) and U2 in the general formula (3) are preferably the same as each other. In the compound represented by the general formula (1), R 101 is a group represented by the general formula (3), V1 in the general formula (1) and V2 in the general formula (3) are preferably the same as each other.

[0134] In the compound according to this embodiment, the compound represented by the general formula (1) may contain at least one ring structure selected from the group consisting of ring structures represented by the following general formula (10), the following general formula (20), and the following general formula (30) in the molecule. In the compound according to this embodiment, the compound represented by the general formula (1) may be, for example, a compound containing a ring structure represented by the following general formula (10), a compound containing a ring structure represented by the following general formula (20), or a compound containing ring structures represented by the following general formulas (10) and (30).

[0135] [ka]

[0136] (In the general formula (10), V1 has the same meaning as V1 in general formula (1), U1 has the same meaning as U1 in general formula (1), U1 and V1 are different from each other, One or more pairs of adjacent two or more of R1, R2, and R3 are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R1 to R3 that do not form a substituted or unsubstituted monocycle and that do not form a substituted or unsubstituted fused ring each independently represent: hydrogen atom a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 131 )(R 132 ) a group represented by -Si(R 133 )(R 134 )(R 135 ) a group represented by -O-(R 136 ) a group represented by -S-(R 137 ) a group represented by halogen atoms, cyano group, -B(R 145 )(R 146 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, *11 indicates the bonding position to ring B1 in general formula (1), *12 indicates the bonding position of B (boron atom) to the ring A1, ring B1, and ring C1 in the general formula (1), In the general formula (20), V1 has the same meaning as V1 in general formula (1), U1 has the same meaning as U1 in general formula (1), U1 and V1 are different from each other, The pair consisting of R4 and R5 is joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R4 and R5, which do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring, are each independently hydrogen atom a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 131 )(R 132 ) a group represented by -Si(R 133 )(R 134 )(R 135 ) a group represented by -O-(R 136 ) a group represented by -S-(R 137 ) a group represented by halogen atoms, cyano group, -B(R 145 )(R 146 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, *21 represents the bonding position of X, which is bonded to ring A1 and ring B1 in general formula (1), *22 indicates the bonding position of B (boron atom) which is bonded to ring A1, ring B1, and ring C1 in the general formula (1), *23 indicates the bonding position to ring C1 in general formula (1), In the general formula (30), V2 is R in the general formula (1). 101 is the same as V2 when V is a group represented by the general formula (3), U2 is R in the general formula (1). 101is the same as U2 when it is a group represented by the general formula (3), U2 and V2 are different from each other, One or more pairs of adjacent two or more of R6, R7, and R8 are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R6, R7, and R8, which do not form the substituted or unsubstituted monocyclic ring and the substituted or unsubstituted fused ring, are hydrogen atom a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 131 )(R 132 ) a group represented by -Si(R 133 )(R 134 )(R 135 ) a group represented by -O-(R 136 ) a group represented by -S-(R 137 ) a group represented by halogen atoms, cyano group, -B(R 145 )(R 146 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, *31 indicates the bonding position of B (boron atom) to the ring A1, ring B1, and ring C1 in the general formula (1), *32 indicates the bonding position to ring B1 in the general formula (1).

[0137] The ring structure represented by the general formula (10) is preferably a ring structure represented by the following general formula (11), (12), (13), (14), or (15). The ring structure represented by the general formula (10) is more preferably a ring structure represented by the following general formula (11) or (12).

[0138] The ring structure represented by the general formula (20) is preferably a ring structure represented by the following general formula (21), (22), (23), (24), or (25).

[0139] The ring structure represented by the general formula (30) is preferably a ring structure represented by the following general formula (31), (32), (33), (34), or (35).

[0140] [ka]

[0141] [ka]

[0142] [ka]

[0143] (In the general formulae (11), (12), (13), (14), (15), (21), (22), (23), (24), (25), (31), (32), (33), (34), and (35), R 111 , R 113 , R 121 , and R 123 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, 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, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, or a fluoroalkyl group having 1 to 50 carbon atoms, R 112 , R 114 , R 122 , and R 124 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R1, R2, and R3 each independently have the same meaning as R1 to R3 in general formula (10), R4 and R5 each independently have the same meaning as R4 and R5 in general formula (20), R6, R7, and R8 each independently have the same meaning as R6 to R8 in general formula (30), *11 and *12 are the same as *11 and *12 in the general formula (10), *21 to *23 are the same as *21 to *23 in general formula (20), *31 and *32 have the same meanings as *31 and *32 in the general formula (30).

[0144] In this embodiment, the compound represented by the general formula (1) is preferably a compound represented by the following general formula (110), (120), or (130).

[0145] [ka]

[0146] (In the general formula (110), Ring A1 and ring B1 each independently have the same meaning as ring A1 and ring B1 in general formula (1), X has the same meaning as X in general formula (1), V1 has the same meaning as V1 in general formula (1), U1 has the same meaning as U1 in general formula (1), U1 and V1 are different from each other, One or more pairs of adjacent two or more of R1, R2, and R3 are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R1 to R3 that do not form a substituted or unsubstituted monocycle and that do not form a substituted or unsubstituted fused ring each independently represent: hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 131 )(R 132 ) a group represented by -Si(R 133 )(R 134 )(R 135 ) a group represented by -O-(R 136 ) a group represented by -S-(R 137 ) a group represented by halogen atoms, cyano group, -B(R 145 )(R 146 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the general formula (120), Ring A1 and ring C1 each independently have the same meaning as ring A1 and ring C1 in general formula (1), X has the same meaning as X in general formula (1), V1 has the same meaning as V1 in general formula (1), U1 has the same meaning as U1 in general formula (1), U1 and V1 are different from each other, The pair consisting of R4 and R5 is joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R4 and R5, which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring, are each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 131 )(R 132 ) a group represented by -Si(R 133 )(R 134 )(R 135 ) a group represented by -O-(R 136 ) a group represented by -S-(R 137 ) a group represented by halogen atoms, cyano group, -B(R 145 )(R 146 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the general formula (130), Ring B1 has the same meaning as ring B1 in formula (1), V1 has the same meaning as V1 in general formula (1), U1 has the same meaning as U1 in general formula (1), V2 has the same meaning as V2 in general formula (3), U2 has the same meaning as U2 in the general formula (3), One or more pairs of adjacent two or more of R1, R2, and R3 are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R1 to R3 that do not form a substituted or unsubstituted monocycle and that do not form a substituted or unsubstituted fused ring each independently have the same meaning as R1 to R3 in general formula (110), One or more pairs of adjacent two or more of R6, R7, and R8 are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R6 to R8 that do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring each independently represent: hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 131 )(R 132 ) a group represented by -Si(R 133 )(R 134 )(R 135 ) a group represented by -O-(R 136 ) a group represented by -S-(R 137 ) a group represented by halogen atoms, cyano group, -B(R 145 )(R 146 ) a group represented by 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.

[0147] In this embodiment, it is preferable that R1 in the compound represented by the general formula (110) is not bonded to ring A1.

[0148] In this embodiment, R4 in the compound represented by the general formula (120) is preferably a hydrogen atom.

[0149] In this embodiment, it is preferable that R1 and R8 in the compound represented by the general formula (130) are not mutually bonded.

[0150] In this embodiment, the compound represented by the general formula (110) is preferably a compound represented by the following general formula (110A): The compound represented by the general formula (130) is preferably a compound represented by the following general formula (130A).

[0151] [ka]

[0152] (In the general formula (110A), Ring A1 has the same meaning as ring A1 in general formula (110). X has the same meaning as X in the general formula (110), V1 has the same meaning as V1 in general formula (110), U1 has the same meaning as U1 in general formula (110). U1 and V1 are different from each other, R1, R2, and R3 each independently have the same meaning as R1, R2, and R3 in general formula (110), R1 is not bonded to ring A1, In the general formula (130A), V1 and U1 have the same meanings as V1 and U1 in general formula (130), V2 and U2 have the same meanings as V2 and U2 in general formula (130), U1 and V1 are different from each other, U2 and V2 are different from each other, R1, R2, R3, R6, R7, and R8 each independently have the same meaning as R1, R2, R3, R6, R7, and R8 in general formula (130), R1 and R8 are not bonded to each other, In the general formula (110A) and the general formula (130A), R9, R 10 , and R 11 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R and R do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring. 10 , and R 11 are each independently, hydrogen atom a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 131 )(R 132 ) a group represented by -Si(R 133 )(R 134 )(R 135 ) a group represented by -O-(R 136 ) a group represented by -S-(R 137 ) a group represented by halogen atoms, cyano group, -B(R 145 )(R 146 ) a group represented by 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.

[0153] In this embodiment, the compound represented by the general formula (110A) is preferably a compound represented by the following general formula (111A).

[0154] [ka]

[0155] (In the general formula (111A), Ring A1 has the same meaning as ring A1 in general formula (110A). X has the same meaning as X in general formula (110A). R1, R2, R3, R9, R 10 , and R 11 each independently represents R1, R2, R3, R9, and R in the general formula (110A). 10 , and R 11 is synonymous with R 12 and R 13 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 12 teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 13 , R 14 , R 15 , R 16 , and R 17 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 13 , or R 17teeth, is bonded to R9 via a single bond, or Does not bind to R9 R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 13 , R 14 , R 15 , R 16 , and R 17 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 131 )(R 132 ) a group represented by -Si(R 133 )(R 134 )(R 135 ) a group represented by -O-(R 136 ) a group represented by -S-(R 137 ) a group represented by halogen atoms, cyano group, -B(R 145 )(R 146 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, However, R that does not form a ring 13 , and R 17 At least one of is a group other than a hydrogen atom or a halogen atom.

[0156] In the compound represented by the general formula (111A), R 13 , and R 17 It is preferable that none of these binds to R9. In the compound represented by the general formula (111A), R 13 , and R 17is preferably a group other than a hydrogen atom or a halogen atom.

[0157] In this embodiment, the compound represented by the general formula (110A) is preferably a compound represented by the following general formula (111B).

[0158] [ka]

[0159] (In the general formula (111B), Ring A1 has the same meaning as ring A1 in general formula (110A). X has the same meaning as X in general formula (110A). R1, R2, R3, R9, R 10 , and R 11 each independently represents R1, R2, R3, R9, and R in the general formula (110A). 10 , and R 11 is synonymous with R 13 , R 14 , R 15 , R 16 , and R 17 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 24 , R 25 , R 26 , R 27 , and R 28 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 13 teeth, R 28 or R 28 does not combine with R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 13 , R 14 , R 15 , R 16 , R 17 , R 24 , R 25 , R 26 , R 27 , and R 28 are each independently, hydrogen atom a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 131 )(R 132 ) a group represented by -Si(R 133 )(R 134 )(R 135 ) a group represented by -O-(R 136 ) a group represented by -S-(R 137 ) a group represented by halogen atoms, cyano group, -B(R 145 )(R 146 ) a group represented by 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.

[0160] In the compound represented by the general formula (111B), R 13 is R 28 It is preferable that it does not bind to

[0161] In this embodiment, in the general formula (111B), R1 and R3 that do not form a ring are preferably hydrogen atoms.

[0162] In this embodiment, the compound represented by the general formula (130A) is preferably a compound represented by the following general formula (131A).

[0163] [ka]

[0164] (In the general formula (131A), R1, R2, R3, R6, R7, R8, R9, R 10 , and R 11 each independently represents R1, R2, R3, R6, R7, R8, R9, and R in the general formula (130A). 10 , and R 11 is synonymous with R 12 , and R 13 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 23 , and R 22 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 13 , R 14 , R 15 , R 16 , and R 17 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 18 , R 19 , R 20 , R 21 , and R 22 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 13 , or R 17 teeth, is bonded to R9 via a single bond, or Does not bind to R9 R 18 , or R 22 teeth, R 11 or R 11 does not combine with R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 12 , and R 23 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 13 , R 14 , R 15 , R 16 , and R 17 and R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 18 , R 19 , R 20 , R 21 , and R 22 are each independently, hydrogen atom a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 131 )(R 132 ) a group represented by -Si(R 133 )(R 134)(R 135 ) a group represented by -O-(R 136 ) a group represented by -S-(R 137 ) a group represented by halogen atoms, cyano group, -B(R 145 )(R 146 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, However, R that does not form a ring 13 , and R 17 At least one of R is a group other than a hydrogen atom or a halogen atom, and R 18 , and R 22 At least one of is a group other than a hydrogen atom and a halogen atom.

[0165] In the compound represented by the general formula (131A), R 13 , and R 17 It is preferable that none of these binds to R9. In the compound represented by the general formula (131A), R 18 , and R 22 are all R 11 It is preferable that it does not bind to

[0166] In this embodiment, the compound represented by the general formula (111B) is preferably a compound represented by the following general formula (111C), (111D), (111E), (111F), (111G), (111H), (111J), or (111K).

[0167] [ka]

[0168] [ka]

[0169] [ka]

[0170] (In the general formula (111C), general formula (111D), general formula (111E), general formula (111F), general formula (111G), general formula (111H), general formula (111J), general formula (111K), X is oxygen atoms, sulfur atoms, N(R 101 ), Si(R 102 )(R 103 ), or C(R 104 )(R 105 ) and Y is oxygen atoms, sulfur atoms, N(R 106 ), Si(R 107 )(R 108 ), or C(R 109 )(R 110 ) and R in X 102 ~R 105 , and R in Y 107 ~R 110 are each independently R in the general formula (1). 102 ~R 105 is synonymous with R 106 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R1 to R3, and R9 to R 11 each independently represents R1 to R3 and R9 to R 11 is synonymous with R 13 , R 14 , R 15 , R16 , and R 17 are each independently R in the general formula (111B). 13 , R 14 , R 15 , R 16 , and R 17 is synonymous with R 13 is R 28 does not combine with R 24 , R 25 , R 26 , R 27 , and R 28 are each independently, R in the general formula (111B) 24 , R 25 , R 26 , R 27 , and R 28 is synonymous with R 29 , R 30 , R 31 , and R 32 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 29 , R 30 , R 31 , and R 32 are each independently defined as R1, R2, and R3 in general formula (111B), R 33 , R 34 , R 35 , and R 36 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 33 , R 34 , R 35 , and R 36 each independently has the same meaning as R1, R2, and R3 in general formula (111B), which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring, R 37 , and R 38 each independently has the same meaning as R1, R2, and R3 in general formula (111B), which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring, R 50 , and R 51 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 50 , and R 51 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 60 , and R 61 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 60 , and R 61 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 101 is represented by the following general formula (1116):

[0171] [ka]

[0172] (In the general formula (1116), R 39 , R 40 , R 41 , R 42 , and R 43 are each independently, R1, R2, and R3 have the same meanings as those of the general formula (111B), *61 represents N(R 101 ) indicates the bonding position with the nitrogen atom.

[0173] In the compounds represented by the general formula (111C) and the general formula (111D), X is an oxygen atom, N(R 101 ), or C(R 104 )(R 105 ), and an oxygen atom or N(R 101 ), and N(R 101 ) is more preferable.

[0174] In the compounds represented by the general formula (111D), the general formula (111G), and the general formula (111K), Y is an oxygen atom, a sulfur atom, or N(R 106 ) is preferred.

[0175] In the compound represented by the general formula (111E), R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 50 , and R 51 are preferably each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0176] In the compounds represented by the general formula (111F) and the general formula (111G), R which does not form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring 60 , and R 61 are preferably each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0177] In this embodiment, among the compounds represented by the general formula (111E), the general formula (111F), and the general formula (111G), the compound represented by the general formula (111E) is preferred. In this embodiment, among the compounds represented by the general formula (111H), the general formula (111J), and the general formula (111K), the compound represented by the general formula (111H) is preferred.

[0178] In the compound according to this embodiment, In the general formula (111C), R and R do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring. 3、 R9, R 11 , and R 32 is a hydrogen atom, In the general formula (111D), R and R do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring. 3、 R9 and R 11 is a hydrogen atom, In the general formula (111E), R and R do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring. 3、 R9, R 11 , and R 32 is a hydrogen atom, In the general formula (111F), R and R do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring. 3、 R9 and R 32 is a hydrogen atom, In the general formula (111G), R and R do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring.3、 and R9 is a hydrogen atom; In the general formula (111H), R and R do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring. 3、 R9, R 11 , and R 32 is a hydrogen atom, In the general formula (111J), R and R do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring. 3、 R9 and R 32 is a hydrogen atom, In the general formula (111K), R and R do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring. 3、 and R9 are preferably hydrogen atoms.

[0179] In the compound according to this embodiment, it is preferable that the compound represented by the general formula (111C) is represented by the following general formula (111C-1), and the compound represented by the general formula (111D) is represented by the following general formula (111D-1).

[0180] [ka]

[0181] (In the general formula (111C-1), X is an oxygen atom, or N(R 101 ) and R1, R3, R9, R 11 , and R 32 is a hydrogen atom, R2, R 10 , R 13 ~R 17 , R 24 ~R 28 , R 29 ~R 31 each independently represents R and R in the general formula (111C). 10 , R 13 ~R17 , R 24 ~R 28 , R 29 ~R 31 is synonymous with In the general formula (111D-1), X is an oxygen atom, or N(R 101 ) and Y is an oxygen atom, or is a sulfur atom, R9 and R 11 is a hydrogen atom, R1~R3, R 10 , R 13 ~R 17 , R 24 ~R 28 , R 33 ~R 36 each independently represents R1 to R3 and R in the general formula (111D). 10 , R 13 ~R 17 , R 24 ~R 28 , R 33 ~R 36 is synonymous with R 101 is represented by the following general formula (1116):

[0182] [ka]

[0183] (In the general formula (1116), R 39 ~R 43 are each independently defined as R1, R2, and R3 in general formula (111B), *61 represents N(R 101 ) indicates the bonding position with the nitrogen atom.

[0184] In the compounds represented by the general formula (111C-1) and the general formula (111D-1), X is N(R 101) is preferred.

[0185] In the compounds according to this embodiment, the substituent in the term "substituted or unsubstituted" is halogen atoms, an unsubstituted alkyl group having 1 to 25 carbon atoms; an unsubstituted aryl group having 6 to 25 ring carbon atoms, or It is preferably an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[0186] In the compounds according to this embodiment, the substituent in the term "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 10 carbon atoms; an unsubstituted aryl group having 6 to 12 ring carbon atoms, or It is preferably an unsubstituted heterocyclic group having 5 to 12 ring atoms.

[0187] In the compounds according to this embodiment, all groups described as "substituted or unsubstituted" are preferably "unsubstituted".

[0188] (Method of producing the compound according to this embodiment) The compound according to this embodiment can be produced according to the synthesis method described in the Examples below, or by imitating the synthesis method and using known alternative reactions and raw materials suited to the target compound.

[0189] (Specific examples of compounds according to this embodiment) Specific examples of the compound according to this embodiment include the following compounds. However, the present invention is not limited to these specific examples. In this specification, a deuterium atom is represented as D in a chemical formula, and a proton atom is represented as H or is not represented at all.

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[0255] [Second form] (Materials for organic electroluminescence devices) The material for an organic electroluminescence device according to this embodiment contains the compound according to the first embodiment. One aspect of the material for an organic electroluminescence device includes only the compound according to the first embodiment, and another aspect of the material for an organic electroluminescence device includes the compound according to the first embodiment and another compound different from the compound according to the first embodiment. In the material for organic electroluminescence devices of this embodiment, the compound according to the first embodiment is preferably a dopant material. In this case, the material for organic electroluminescence devices may contain the compound according to the first embodiment as a dopant material and other compounds such as a host material.

[0256] The compound according to the first embodiment is useful as a material for an organic EL device, and is useful as a material for the light-emitting layer of an organic EL device, and is particularly useful as a blue-emitting material for the light-emitting layer.

[0257] Third Embodiment [Organic electroluminescence element] The organic EL element according to this embodiment will be described. The organic EL device according to this embodiment includes an organic layer between an anode and a cathode. The organic layer includes at least one layer made of an organic compound. Alternatively, the organic layer includes a plurality of layers made of organic compounds stacked together. The organic layer may further include an inorganic compound.

[0258] In the organic EL device according to this embodiment, the organic layer contains the compound according to the first embodiment. That is, the organic EL device according to this embodiment has a cathode, an anode, and an organic layer between the cathode and the anode, and the organic layer contains the compound according to the first embodiment as a first compound. In the organic EL device of this embodiment, the organic layer preferably includes an emitting layer, and the emitting layer preferably contains the compound according to the first embodiment as a first compound.

[0259] The organic EL device according to this embodiment has a cathode, an anode, and one or more organic layers disposed between the cathode and the anode, and at least one of the one or more organic layers contains the compound according to the first embodiment as a first compound.

[0260] The organic EL device according to this embodiment includes a cathode, an anode, and one or more light-emitting layers disposed between the cathode and the anode, and at least one of the one or more light-emitting layers contains the compound according to an aspect of the present invention as a first compound.

[0261] The organic EL element according to this embodiment may be an organic EL element having a single light-emitting layer as a third embodiment.

[0262] The schematic configuration of an organic EL element according to one embodiment of the present invention will be described with reference to Fig. 1. Fig. 1 shows the schematic configuration of an example of an organic EL element according to a third embodiment. An organic EL device 1 according to one embodiment of the present invention includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is formed by laminating a first organic layer 67, an emitting layer 5, and a second organic layer 89 in this order from the anode 3 side. The first organic layer 67 and the second organic layer 89 may each be a single layer or may each be composed of multiple layers. The first organic layer 67 may also include a hole transport region. The hole transport region may include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, etc. The second organic layer 89 may also include an electron transport region. The electron transport region may include at least one layer selected from the group consisting of an electron injection layer, an electron transport layer, a hole blocking layer, etc. For example, the first organic layer 67 may be configured by stacking a hole injection layer and a hole transport layer in this order from the anode 3 side. The second organic layer 89 may be configured by stacking an electron transport layer and an electron injection layer in this order from the anode 3 side. The organic EL device 1 may be configured by stacking a hole injection layer, a hole transport layer, the light-emitting layer 5, an electron transport layer, and an electron injection layer in this order from the anode 3 side. The present invention is not limited to the organic EL device having the configuration shown in FIG. 1. The compound according to the first embodiment is included in the first organic layer 67, the light-emitting layer 5, or the second organic layer 89. In one embodiment, the compound according to the first embodiment is included in the light-emitting layer 5. The compound according to the first embodiment can function as a dopant material in the light-emitting layer 5.

[0263] In the organic EL element according to the third embodiment, a compound according to one aspect of the present invention can be used in combination as a first compound in the light-emitting layer of the organic EL element, and a compound represented by general formula (H10) described later can be used as a second compound. The compound represented by general formula (H10) will be explained below.

[0264] <Compound represented by general formula (H10)> The compound represented by general formula (H10) will be explained.

[0265] [ka]

[0266] [In the general formula (H10), R 101 ~R 110At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 101 ~R 110 are each independently, hydrogen atoms, a substituent R, or A group represented by the following general formula (H11): provided that R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 101 ~R 110 At least one of the above is a group represented by the following general formula (H11): When two or more groups represented by the following general formula (H11) are present, the two or more groups represented by the following general formula (H11) are the same or different.

[0267] -L 101 -Ar 101 (H11)

[0268] (In the general formula (H11), L 101 teeth, 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, Ar 101 teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, When two or more substituents R are present, the two or more substituents R are the same or different from each other, 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905are the same or different from each other, R 906 If there are multiple R 906 are the same or different from each other, R 907 If there are multiple R 907 are the same or different from each other.)

[0269] The compound represented by the above general formula (H10) may have a deuterium atom instead of a hydrogen atom.

[0270] In one embodiment, Ar in the general formula (H10) 101 At least one of the groups is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0271] In one embodiment, Ar in the general formula (H10) 101 At least one of the groups is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0272] In one embodiment, all of Ar in the general formula (H10) 101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. 101 may be the same as or different from each other.

[0273] In one embodiment, Ar in general formula (H10) 101 one of which is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and the remaining Ar 101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. 101 may be the same as or different from each other.

[0274] In one embodiment, L in general formula (H10) 101 At least one of is a single bond. In one embodiment, L in general formula (H10) 101 are all single bonds. In one embodiment, L in general formula (H10) 101 At least one of the groups is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms. In one embodiment, L in general formula (H10) 101 At least one of the groups is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.

[0275] In one embodiment, -L in general formula (H10) 101 -Ar 101 The group represented by a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and The group consisting of substituted or unsubstituted carbazolyl groups.

[0276] In one embodiment, the substituents R in the general formula (H10) are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907) a group represented by a halogen atom, a cyano group, a nitro group, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 901 ~R 907 is as defined in the general formula (H10) above.

[0277] In one embodiment, the "substituted or unsubstituted" substituents in the general formula (H10) are each independently: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 ~R 907 is as defined in the general formula (H10) above.

[0278] In one embodiment, the "substituted or unsubstituted" substituents in the general formula (H10) are each independently: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a halogen atom, a cyano group, a nitro group, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 901 ~R 907 is as defined in the general formula (H10) above.

[0279] In one embodiment, the substituent in the case of "substituted or unsubstituted" in the general formula (H10) is an alkyl group having 1 to 18 carbon atoms; an aryl group having 6 to 18 ring carbon atoms, and The heterocyclic group is selected from the group consisting of heterocyclic groups having 5 to 18 ring atoms.

[0280] In one embodiment, the substituent in the "substituted or unsubstituted" in general formula (H10) is an alkyl group having 1 to 5 carbon atoms.

[0281] In one embodiment, the compound represented by general formula (H10) is a compound represented by the following general formula (H20).

[0282] [ka]

[0283] (In general formula (H20), R 101 ~R 108 , L 101 and Ar 101 is as defined in general formula (H10) above. The compound represented by the above general formula (H20) may have a deuterium atom instead of a hydrogen atom.

[0284] That is, in one embodiment, the compound represented by the general formula (H10) or the general formula (H20) has at least two groups represented by the general formula (H11). In one embodiment, the compound represented by the general formula (H10) or (H20) has two or three groups represented by the general formula (H11).

[0285] In one embodiment, R in the general formula (H10) and the general formula (H20) 101 ~R 110 Any pair of two or more adjacent ones of these is not bonded to each other. In one embodiment, R in the general formula (H10) and the general formula (H20) 101 ~R 110 is a hydrogen atom.

[0286] In one embodiment, the compound represented by general formula (H20) is a compound represented by the following general formula (H30):

[0287] [ka]

[0288] (In general formula (H30), L 101 and Ar 101 is as defined in general formula (H10), R 101A ~R 108A Any pair of two or more adjacent groups of R 101A ~R 108A are each independently, a hydrogen atom or a substituent R, The substituent R is as defined in general formula (H10).

[0289] That is, the compound represented by the general formula (H30) above is a compound having two groups represented by the general formula (H11) above. The compound represented by the above general formula (H30) contains substantially only proton atoms as hydrogen atoms. The phrase "having substantially only proton atoms" means that the proportion of protons to the total of a compound having only protons as hydrogen atoms (protons) and a compound having deuterium atoms (deuterium compounds) is 90 mol % or more, 95 mol % or more, or 99 mol % or more.

[0290] In one embodiment, the compound represented by general formula (H30) is a compound represented by the following general formula (H31).

[0291] [ka]

[0292] (In general formula (H31), L 101 and Ar 101 is as defined in general formula (H10), R 101A ~R 108A is as defined in general formula (H30), X b is an oxygen atom, a sulfur atom, and N(R 331 ), or C(R 332 )(R 333 ) and R 121 ~R 128 , and R 331 ~R 333 One of them is L 101 is a single bond that bonds to L 101 R that is not a single bond 121 ~R 128 At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, L 101and R is not a single bond bonding to R, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring. 121 ~R 128 are each independently, a hydrogen atom, or is a substituent R, The substituent R is as defined in general formula (H10), L 101 R that is not a single bond 331 ~R 333 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 331 If there are multiple R 331 are the same or different from each other, R 332 If there are multiple R 332 are the same or different from each other, R 333 If there are multiple R 333 are either identical or different.)

[0293] In one embodiment, the compound represented by the general formula (H31) is a compound represented by the following general formula (H32).

[0294] [ka]

[0295] (In general formula (H32), R 101A ~R 108A , L 101 , Ar 101 , R 121 ~R 128 , R 332 and R333 is as defined in general formula (H31).

[0296] In one embodiment, the compound represented by the general formula (H31) is a compound represented by the following general formula (H33).

[0297] [ka]

[0298] (In general formula (H33), R 101A ~R 108A , L 101 , Ar 101 , and R 121 ~R 128 is as defined in the general formula (H31), X c is an oxygen atom, a sulfur atom, or NR 331 and R 331 is as defined in general formula (H31).

[0299] In one embodiment, the compound represented by the general formula (H31) is a compound represented by the following general formula (H34).

[0300] [ka]

[0301] (In general formula (H34), R 101A ~R 108A , L 101 and Ar 101 is as defined in the general formula (H31), X c is an oxygen atom, a sulfur atom, or NR 331 and R 331 is as defined in the general formula (H31), R 121A ~R 128A One of them is L 101 is a single bond that bonds to L 101 R that is not a single bond 121A ~R 128A Any pair of two or more adjacent groups of L 101 R that is not a single bond 121A ~R 128A are each independently, a hydrogen atom, or is a substituent R, The substituent R is as defined in general formula (H10).

[0302] In one embodiment, the compound represented by the general formula (H31) is a compound represented by the following general formula (H35).

[0303] [ka]

[0304] [In general formula (H35), R 101A ~R 108A , L 101 , Ar 101 and X b is as defined in the general formula (H31) above. R 121A ~R 124A Any pair of two or more adjacent groups of R 125A and R 126A , R 126A and R 127A , and R 127A and R 128A Any one pair of these may be bonded to each other to form a ring represented by the following general formula (H35a) or (H35b).

[0305] [ka]

[0306] (In the general formula (H35a) and the general formula (H35b), The two * are R 125A and R R126A , R 126A and R 127A , and R 127A and R 128A and combines with one of the following pairs: R 341 ~R 344 are each independently, a hydrogen atom, or is a substituent R, The substituent R is as defined in general formula (H10), X d is an oxygen atom or a sulfur atom. R 121A ~R 124A R that does not form a ring represented by general formula (H35a) or general formula (H35b) 125A ~R 128A , and R 341 ~R 344 One of them is L 101 is a single bond that bonds to L 101 R that is not a single bond 121A ~R 124A , and L 101 and R which is not a single bond bonding to R and does not form a ring represented by general formula (H35a) or general formula (H35b). 125A ~R 128A are each independently, a hydrogen atom, or is a substituent R, The substituent R is as defined in the general formula (H10).

[0307] In one embodiment, the compound represented by general formula (H35) is a compound represented by the following general formula (H36).

[0308] [ka]

[0309] (In general formula (H36), R 101A ~R 108A , L101 , and Ar 101 is as defined in the general formula (H35), and R 125B ~R 128B each independently represents R in general formula (H35). 125A ~R 128A is equivalent to

[0310] In one embodiment, the compound represented by general formula (H34) is a compound represented by the following general formula (H37).

[0311] [ka]

[0312] (In general formula (H37), R 101A ~R 108A , R 125A ~R 128A , L 101 and Ar 101 is as defined in the general formula (H34).

[0313] In one embodiment, R in the general formulae (H30) to (H37) 101A ~R 108A is a hydrogen atom.

[0314] In one embodiment, the compound represented by general formula (H10) is a compound represented by the following general formula (H40).

[0315] [ka]

[0316] (In general formula (H40), L 101 and Ar 101 is as defined in general formula (H10), R 101A , and R 103A ~R 108A At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 101A , and R 103A ~R 108A are each independently, a hydrogen atom or a substituent R, The substituent R is as defined in general formula (H10). That is, the compound represented by the general formula (H40) is a compound having three groups represented by the general formula (H11). Furthermore, the compound represented by the general formula (H40) has substantially only proton atoms as hydrogen atoms.

[0317] In one embodiment, the compound represented by general formula (H40) is represented by the following general formula (H41).

[0318] [ka]

[0319] (In general formula (H41), L 101 and Ar 101 is as defined in general formula (H40).

[0320] In one embodiment, the compound represented by the general formula (H40) is a compound represented by any one of the following general formulae (H42-1) to (H42-3).

[0321] [ka]

[0322] (In general formula (H42-1) ~ general formula (H42-3), R 101A ~R 108A , L 101 and Ar 101is as defined in general formula (H40).

[0323] In one embodiment, the compounds represented by the general formulae (H42-1) to (H42-3) are compounds represented by any of the following general formulae (H43-1) to (H43-3).

[0324] [ka]

[0325] (In general formula (H43-1) ~ general formula (H43-3), L 101 and Ar 101 is as defined in general formula (H40).

[0326] In one embodiment, -L in the general formula (H40), the general formula (H41), the general formulae (H42-1) to (H42-3), and the general formulae (H43-1) to (H43-3) 101 -Ar 101 The group represented by a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and The group consisting of substituted or unsubstituted carbazolyl groups.

[0327] In one embodiment, the compounds represented by the general formula (H10) or (H20) include compounds in which at least one of the hydrogen atoms contained in these compounds is a deuterium atom.

[0328] In one embodiment, in the general formula (H20), R is a hydrogen atom 101 ~R 108 , The substituent R is R 101 ~R 108 a hydrogen atom possessed by L 101 a hydrogen atom possessed by L 101 a hydrogen atom of the substituent Ar 101 a hydrogen atom in Ar 101 The hydrogen atoms of the substituents At least one of the atoms is a deuterium atom.

[0329] The compounds represented by the general formulae (H30) to (H37) include compounds in which at least one of the hydrogen atoms contained in these compounds is a deuterium atom. In one embodiment, at least one of the hydrogen atoms bonded to the carbon atoms constituting the anthracene skeleton in the compounds represented by the general formulae (H30) to (H37) is a deuterium atom.

[0330] In one embodiment, the compound represented by general formula (H30) is a compound represented by the following general formula (H30D).

[0331] [ka]

[0332] (In general formula (H30D), R 101A ~R 108A , L 101 and Ar 101 is as defined in the general formula (H30) above. however, R is a hydrogen atom 101A ~R 108A , The substituent R is R 101A ~R 108A a hydrogen atom possessed by L 101 a hydrogen atom possessed by L 101 a hydrogen atom of the substituent Ar 101 a hydrogen atom in Ar 101 The hydrogen atoms of the substituents At least one of the atoms is a deuterium atom.) That is, the compound represented by the general formula (H30D) is a compound in which at least one of the hydrogen atoms of the compound represented by the general formula (H30) is a deuterium atom.

[0333] In one embodiment, R which is a hydrogen atom in general formula (H30D) 101A ~R 108A At least one of the atoms is a deuterium atom.

[0334] In one embodiment, the compound represented by general formula (H30D) is a compound represented by the following general formula (H31D).

[0335] [ka]

[0336] (In general formula (H31D), R 101A ~R 108A , L 101 and Ar 101 is as defined in the general formula (H30D) above, X d is an oxygen atom or a sulfur atom, R 121 ~R 128 One of them is L 101 is a single bond that bonds to L 101 R that is not a single bond 121~R 128 At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, L 101 and R is not a single bond bonding to R, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring. 121 ~R 128 are each independently, a hydrogen atom, or is a substituent R, The substituent R is as defined in the general formula (H10). however, R is a hydrogen atom 101A ~R 108A , The substituent R is R 101A ~R 108A a hydrogen atom possessed by L 101 a hydrogen atom possessed by L 101 a hydrogen atom of the substituent Ar 101 a hydrogen atom possessed by Ar 101 The hydrogen atoms of the substituents R is a hydrogen atom 121 ~R 128 , and The substituent R is R 121 ~R 128 The hydrogen atom At least one of the atoms is a deuterium atom.)

[0337] In one embodiment, the compound represented by the general formula (H31D) is a compound represented by the following general formula (H32D).

[0338] [ka]

[0339] (In general formula (H32D), R 101A ~R 108A , L 101 and Ar 101 is as defined in the general formula (H31D), and R 125A ~R 128A each independently represents R in general formula (H31D). 125 ~R 128 is synonymous with. however, R is a hydrogen atom 101A ~R 108A , The substituent R is R 101A ~R 108A a hydrogen atom possessed by R is a hydrogen atom 125A ~R 128A , The substituent R is R 125A ~R 128A a hydrogen atom possessed by a hydrogen atom bonded to a carbon atom of the dibenzofuran skeleton in general formula (H32D), L 101 a hydrogen atom possessed by L 101 a hydrogen atom of the substituent Ar 101 a hydrogen atom in Ar 101 The hydrogen atoms of the substituents At least one of the atoms is a deuterium atom.)

[0340] In one embodiment, the compound represented by the general formula (H32D) is a compound represented by the following general formula (H32D-1) or (H32D-2).

[0341] [ka]

[0342] (In general formula (H32D-1) and general formula (H32D-2), R 101A ~R 108A , R 125A ~R 128A , L101 and Ar 101 is as defined in the general formula (H32D) above. however, R is a hydrogen atom 101A ~R 108A , The substituent R is R 101A ~R 108A a hydrogen atom possessed by R is a hydrogen atom 125A ~R 128A , The substituent R is R 125A ~R 128A a hydrogen atom possessed by a hydrogen atom bonded to a carbon atom of the dibenzofuran skeleton in general formulae (H32D-1) and (H32D-2), L 101 a hydrogen atom possessed by L 101 a hydrogen atom of the substituent Ar 101 a hydrogen atom in Ar 101 The hydrogen atoms of the substituents At least one of the atoms is a deuterium atom.)

[0343] In one embodiment, at least one of the hydrogen atoms possessed by the compound represented by the general formula (H40), the general formula (H41), the general formula (H42-1) to the general formula (H42-3), or the general formula (H43-1) to the general formula (H43-3) is a deuterium atom.

[0344] In one embodiment, at least one of the hydrogen atoms bonded to the carbon atoms constituting the anthracene skeleton in the compound represented by general formula (H41) is a deuterium atom.

[0345] In one embodiment, the compound represented by general formula (H40) is a compound represented by the following general formula (H40D).

[0346] [ka]

[0347] (In general formula (H40D), L 101 and Ar 101 is as defined in general formula (H10), R 101A , and R 103A ~R 108A Any pair of two or more adjacent groups of R 101A , and R 103A ~R 108A are each independently, a hydrogen atom, or is a substituent R, The substituent R is as defined in the general formula (H10). however, R is a hydrogen atom 101A , and R 103A ~R 108A , The substituent R is R 101A , and R 103A ~R 108A a hydrogen atom possessed by L 101 a hydrogen atom possessed by L 101 a hydrogen atom of the substituent Ar 101 a hydrogen atom in Ar 101 The hydrogen atoms of the substituents At least one of the atoms is a deuterium atom.)

[0348] In one embodiment, R in general formula (H40D) 101A , and R 103A ~R 108A At least one of the atoms is a deuterium atom.

[0349] In one embodiment, the compound represented by general formula (H40D) is a compound represented by the following general formula (H41D).

[0350] [ka]

[0351] (In general formula (H41D), L 101 and Ar 101 is as defined in the general formula (H40D) above. However, in the general formula (H41D), A hydrogen atom bonded to a carbon atom constituting the anthracene skeleton, L 101 a hydrogen atom possessed by L 101 a hydrogen atom of the substituent Ar 101 a hydrogen atom in Ar 101 The hydrogen atoms of the substituents At least one of the atoms is a deuterium atom.)

[0352] In one embodiment, the compound represented by the general formula (H40D) is a compound represented by any one of the following general formulae (H42D-1) to (H42D-3).

[0353] [ka]

[0354] (In general formula (H42D-1) ~ general formula (H42D-3), R 101A ~R 108A , L 101 and Ar 101 is as defined in the general formula (H40D) above. However, in the general formula (H42D-1), R is a hydrogen atom 101A , and R 103A ~R 108A , The substituent R is R 101A , and R 103A ~R 108A a hydrogen atom possessed by L 101 a hydrogen atom possessed by L 101 a hydrogen atom of the substituent Ar101 a hydrogen atom possessed by Ar 101 a hydrogen atom carried by a substituent of A hydrogen atom bonded to a carbon atom constituting a phenyl group in the general formula (H42D-1) at least one of which is a deuterium atom, In the general formula (H42D-2), R is a hydrogen atom 101A , and R 103A ~R 108A , The substituent R is R 101A , and R 103A ~R 108A a hydrogen atom possessed by L 101 a hydrogen atom possessed by L 101 a hydrogen atom of the substituent Ar 101 a hydrogen atom possessed by Ar 101 a hydrogen atom carried by a substituent of A hydrogen atom bonded to a carbon atom constituting a naphthyl group in the general formula (H42D-2) at least one of which is a deuterium atom, In the general formula (H42D-3), R is a hydrogen atom 101A , and R 103A ~R 108A , The substituent R is R 101A , and R 103A ~R 108A a hydrogen atom possessed by L 101 a hydrogen atom possessed by L 101 a hydrogen atom of the substituent Ar 101 a hydrogen atom possessed by Ar 101 a hydrogen atom carried by a substituent of A hydrogen atom bonded to a carbon atom constituting a naphthyl group in the general formula (H42D-3) At least one of the atoms is a deuterium atom.)

[0355] In one embodiment, the compounds represented by the general formulae (H42D-1) to (H42D-3) are compounds represented by any of the following general formulae (H43D-1) to (H43D-3).

[0356] [ka]

[0357] (In general formula (H43D-1) ~ general formula (H43D-3), L 101 and Ar 101 is as defined in the general formula (H40D) above. however, a hydrogen atom bonded to a carbon atom constituting the anthracene skeleton in general formula (H43D-1), L 101 a hydrogen atom possessed by L 101 a hydrogen atom of the substituent Ar 101 a hydrogen atom possessed by Ar 101 a hydrogen atom of the substituent of A hydrogen atom bonded to a carbon atom constituting a phenyl group in the general formula (H43D-1) at least one of which is a deuterium atom, a hydrogen atom bonded to a carbon atom constituting the anthracene skeleton in general formula (H43D-2), L 101 a hydrogen atom possessed by L 101 a hydrogen atom of the substituent Ar 101 a hydrogen atom possessed by Ar 101 a hydrogen atom of the substituent of A hydrogen atom bonded to a carbon atom constituting a naphthyl group in the general formula (H43D-2) at least one of which is a deuterium atom, a hydrogen atom bonded to a carbon atom constituting the anthracene skeleton in general formula (H43D-3), L 101 a hydrogen atom possessed by L 101 a hydrogen atom of the substituent Ar 101 a hydrogen atom possessed by Ar 101 a hydrogen atom of the substituent of A hydrogen atom bonded to a carbon atom constituting a naphthyl group in the general formula (H43D-3) At least one of the atoms is a deuterium atom.)

[0358] In one embodiment, in the compound represented by general formula (H20), Ar 101 At least one of the groups is a monovalent group having a structure represented by the following general formula (H50).

[0359] [ka]

[0360] (In general formula (H50), X 151 is an oxygen atom, a sulfur atom, or a C(R 161 )(R 162 ) and R 151 ~R 160 One of them is L 101 is a single bond that bonds to L 101 R is not a single bond that bonds to 151 ~R 154 and R 155 ~R 160 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 161 and R 162 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 161 and R 162 , and L 101 Instead of a single bond, and R does not form the substituted or unsubstituted saturated or unsaturated monocyclic ring and does not form the substituted or unsubstituted fused ring. 151 ~R 160 are each independently, is a hydrogen atom or a substituent R, The substituent R is as defined in general formula (H10), Ar which is not a monovalent group having a structure represented by the general formula (H50) 101 teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0361] L in the general formula (H50) 101 The position of the single bond with is not particularly limited. In one embodiment, R in general formula (H50) 151 ~R 154 One of the following, or R 155 ~R 160 One of them is L 101 It is a single bond that bonds to

[0362] In one embodiment, Ar 101 is represented by the following general formula (H50-R 152 ), general formula (H50-R 153 ), general formula (H50-R 154 ), general formula (H50-R 157 ) or the general formula (H50-R 158 ) is a monovalent group represented by the formula:

[0363] [ka]

[0364] (General formula (H50-R 152 ), general formula (H50-R 153 ), general formula (H50-R 154 ), general formula (H50-R 157 ) and the general formula (H50-R 158 ), X 151 , R 151 ~R 160 is as defined in general formula (H50), *L 101 )

[0365] (Specific examples of compounds represented by general formula (H10)) Specific examples of the compound represented by general formula (H10) include the compounds shown below. The compound represented by general formula (H10) is not limited to these specific examples. In the following specific examples, D represents a deuterium atom.

[0366] [ka]

[0367] [ka]

[0368] [ka]

[0369] [ka]

[0370] [ka]

[0371] [ka]

[0372] [ka]

[0373] [ka]

[0374] [ka]

[0375] [ka]

[0376] [ka]

[0377] [ka]

[0378] [ka]

[0379] [ka]

[0380] Specific examples of the above groups are as described in the [Definitions] section of this specification.

[0381] As described above, the organic EL device according to one aspect of the present invention has a cathode, an anode, and an emitting layer between the cathode and the anode. Except for the fact that the emitting layer contains the compound according to the first embodiment, conventionally known materials and device configurations can be applied as long as the effects of the present invention are not impaired.

[0382] The organic EL element of this embodiment preferably emits light having a maximum peak wavelength of 445 nm or more and 460 nm or less when the element is driven. The maximum peak wavelength of light emitted from the organic EL element when the element is driven is measured as follows: 2 A voltage is applied to the organic EL element so that the spectral radiance spectrum is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is measured and this is defined as the maximum peak wavelength (unit: nm).

[0383] The content of the compound according to the first embodiment in the light-emitting layer is preferably 1% by mass or more and 20% by mass or less with respect to the entire light-emitting layer. The compound according to the first embodiment is preferably a dopant material.

[0384] In the organic EL device according to this embodiment, when the light-emitting layer contains the compound represented by general formula (H10), the light-emitting layer preferably contains the compound represented by general formula (H10) in an amount of 60% by mass or more, more preferably 70% by mass or more, and even more preferably 80% by mass or more of the total mass of the light-emitting layer. The compound represented by general formula (H10) is preferably a host material. When the light-emitting layer contains the compound represented by the general formula (H10) as a host material and the compound according to the first embodiment as a dopant material, the upper limit of the total content of the host material and the dopant material is 100 mass %.

[0385] Fourth Embodiment The organic EL element according to this embodiment may be an organic EL element having two or more light-emitting layers as a fourth embodiment. The organic EL element of the fourth embodiment differs from the organic EL element of the third embodiment in that it has at least two light-emitting layers, but is otherwise similar to the organic EL element of the third embodiment. In the description of the fourth embodiment, the same components as those in the third embodiment will be denoted by the same reference numerals or names, and the description thereof will be omitted or simplified. Furthermore, in the fourth embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the first and third embodiments can be used.

[0386] The structure of the organic EL element according to this embodiment will be described. In the organic EL device according to this embodiment, the light-emitting layer includes a first light-emitting layer and a second light-emitting layer. The first light-emitting layer includes a first host material and a first dopant material. The second light-emitting layer includes a second host material and a second dopant material. The first host material and the second host material are different from each other. The first dopant material and the second dopant material are the same as or different from each other. The organic EL device according to this embodiment includes at least two light-emitting layers (a first light-emitting layer and a second light-emitting layer). The first light-emitting layer according to this embodiment has the same configuration as the light-emitting layer of the organic EL device according to the third embodiment. The following mainly describes the differences from the first embodiment, and redundant descriptions will be omitted or simplified.

[0387] The organic EL element according to this embodiment can have a longer life and improved luminous efficiency by utilizing Triplet-Triplet-Annhilation (sometimes referred to as TTA). TTA is a mechanism in which triplet excitons collide with each other to generate singlet excitons. The TTA mechanism is also sometimes called the TTF mechanism, as described in WO 2010 / 134350.

[0388] The TTF phenomenon will be explained. Holes injected from the anode and electrons injected from the cathode recombine in the light-emitting layer to generate excitons. As has been conventionally known, the spin state of these excitons is 25% singlet excitons and 75% triplet excitons. In conventional fluorescent elements, 25% of the singlet excitons emit light when they relax to the ground state, but the remaining 75% of the triplet excitons return to the ground state through a thermal deactivation process without emitting light. Therefore, the theoretical limit of the internal quantum efficiency of conventional fluorescent elements was said to be 25%. On the other hand, the behavior of triplet excitons generated inside organic materials has been theoretically investigated. According to S.M. Bachilo et al. (J.Phys.Chem.A,104,7711(2000)), assuming that higher-order excitons such as quintets immediately return to triplets, triplet excitons (hereinafter referred to as triplet excitons) 3 A * When the density of triplet excitons (hereinafter referred to as triplet excitons) increases, triplet excitons collide with each other, causing the reaction shown in the following formula: 1 A represents the ground state, 1 A * represents the lowest excited singlet exciton. 3 A * + 3 A * →(4 / 9) 1 A+(1 / 9) 1 A * +(13 / 9) 3 A * That is, 5 3 A * →4 1 A+1A *It is predicted that 1 / 5, or 20%, of the 75% of triplet excitons initially generated will convert to singlet excitons. Therefore, the singlet excitons contributing to light are 40%, calculated by adding 75% × (1 / 5) = 15% to the initially generated 25%. In this case, the TTF ratio (TTF ratio) of the total luminescence intensity is 15 / 40, or 37.5%. Furthermore, if we assume that singlet excitons are generated by collisions between the initially generated 75% triplet excitons (i.e., one singlet exciton is generated from two triplet excitons), then an extremely high internal quantum efficiency of 62.5% is obtained by adding 75% × (1 / 2) = 37.5% to the initially generated 25% singlet excitons. In this case, the TTF ratio is 37.5 / 62.5 = 60%.

[0389] In the organic EL device according to this embodiment, from the viewpoint of exhibiting the TTF mechanism, the triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 1), and more preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 2). T1(H2)>T1(H1) ... (Number 1) T1(H2)-T1(H1)>0.03 eV … (Equation 2)

[0390] In the organic EL device according to this embodiment, by satisfying the relationship of the above mathematical formula (Mathematical Formula 1), triplet excitons generated by recombination of holes and electrons in the second light-emitting layer are thought to be less likely to be quenched at the interface between the second light-emitting layer and the organic layer, even if excess carriers are present at the interface between the second light-emitting layer and the organic layer that is in direct contact with the second light-emitting layer. For example, when the recombination region is locally present at the interface between the second light-emitting layer and the hole transport layer or the electron blocking layer, quenching by excess electrons is thought to occur. On the other hand, when the recombination region is locally present at the interface between the second light-emitting layer and the electron transport layer or the hole blocking layer, quenching by excess holes is thought to occur. The organic EL device according to this embodiment includes a first light-emitting layer and a second light-emitting layer that satisfy the relationship of the above mathematical formula (1), so that triplet excitons generated in the second light-emitting layer can migrate to the first light-emitting layer without being quenched by excess carriers, and reverse migration from the first light-emitting layer to the second light-emitting layer can be suppressed. As a result, the TTF mechanism is exerted in the first light-emitting layer, and singlet excitons are efficiently generated, improving the luminous efficiency. In this way, the organic EL device has the second emitting layer, which mainly generates triplet excitons, and the first emitting layer, which mainly exhibits the TTF mechanism by utilizing triplet excitons transferred from the second emitting layer, as different regions, and uses a compound having a smaller triplet energy than the second host material in the second emitting layer as the first host material in the first emitting layer, thereby creating a difference in triplet energy, thereby improving the luminous efficiency.

[0391] In the organic EL device according to this embodiment, by selecting a combination of host materials that satisfies the relationship of the above mathematical formula (Mathematical Formula 1) and by containing the compound according to the first embodiment in the first emitting layer, the device can have a longer life and further improve its luminous efficiency.

[0392] (Triplet energy T1) The triplet energy T1 can be measured by the following method. The compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) at 10 -5 mol / L or more 10 -4 The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this sample is measured at low temperature (77[K]), and a tangent line is drawn to the rising edge of the short wavelength side of this phosphorescence spectrum. The wavelength value λ at the intersection of this tangent line and the horizontal axis is determined. edge The amount of energy calculated from the following conversion formula (F1) based on [nm] is taken as the triplet energy T1. Conversion formula (F1): T1[eV]=1239.85 / λ edge

[0393] The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows: When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum of the spectral maxima, consider the tangent at each point on the curve toward the long wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope is at its maximum (i.e., the tangent at the inflection point) is the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that a maximum point having a peak intensity that is 15% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and the tangent drawn at the point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side is defined as the tangent to the rising edge on the short wavelength side of the phosphorescence spectrum. Phosphorescence can be measured using an F-4500 spectrofluorophotometer manufactured by Hitachi High-Technologies Corp. However, the measuring device is not limited to this, and measurements may be performed by combining a cooling device, a cryogenic container, an excitation light source, and a light-receiving device.

[0394] (Emission wavelength of organic EL element) The organic EL element according to this embodiment preferably emits light having a maximum peak wavelength of 500 nm or less when the element is driven, more preferably emits light of 445 nm or more and 480 nm or less, and even more preferably emits light of 445 nm or more and 465 nm or less. The maximum peak wavelength of the light emitted by the organic EL element when the element is driven is measured as described above.

[0395] (First light-emitting layer) The first light-emitting layer includes a first host material and a first dopant material, and the first host material is a compound different from the second host material contained in the second light-emitting layer. The first emitting layer according to this embodiment has the same structure as the emitting layer according to the third embodiment. The first dopant material is preferably the compound according to the first embodiment (the compound represented by the general formula (1)). The first host material is preferably the compound represented by the general formula (H10). In the organic EL device according to the fourth embodiment, the compound according to the first embodiment and the compound represented by general formula (H10) can be used in combination in the first light-emitting layer of the organic EL device.

[0396] In the organic EL device according to this embodiment, the first light-emitting layer preferably emits light having a maximum peak wavelength of 500 nm or less when the device is in operation. The maximum peak wavelength of the light emitted from the light-emitting layer when the device is operating can be measured by the following method.

[0397] The maximum peak wavelength λp of the light emitted from the light-emitting layer when the device is operating The maximum peak wavelength λp1 of the light emitted from the first light-emitting layer when the device is driven is determined by the following equation: 2 The spectral radiance spectrum when a voltage is applied to the element so that: is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) From the obtained spectral radiance spectrum, the maximum peak wavelength λp1 (unit: nm) is calculated. The maximum peak wavelength λp2 of the light emitted from the second light-emitting layer when the device is driven is determined by the following equation: 2 The spectral radiance spectrum when a voltage is applied to the element so that: is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) From the obtained spectral radiance spectrum, the maximum peak wavelength λp2 (unit: nm) is calculated.

[0398] In the organic EL device according to this embodiment, it is preferable that the triplet energy T1(D1) of the first dopant material and the triplet energy T1(H1) of the first host material satisfy the relationship shown in the following formula (Mathematical Formula 4A). T1(D1)>T1(H1) ... (Math 4A)

[0399] In the organic EL device according to this embodiment, the first dopant material and the first host material satisfy the relationship of the above mathematical formula (Mathematical Formula 4A), so that triplet excitons generated in the second emitting layer transfer energy to molecules of the first host material, rather than to the first dopant material having a higher triplet energy, when they move to the first emitting layer. Furthermore, triplet excitons generated by recombination of holes and electrons on the first host material do not transfer to the first dopant material having a higher triplet energy. Triplet excitons generated by recombination on molecules of the first dopant material quickly transfer energy to molecules of the first host material. Triplet excitons in the first host material do not transfer to the first dopant material, but instead collide efficiently with each other on the first host material due to the TTF phenomenon, generating singlet excitons.

[0400] In the organic EL device according to this embodiment, it is preferable that the singlet energy S1(H1) of the first host material and the singlet energy S1(D1) of the first dopant material satisfy the relationship of the following mathematical formula (Mathematical Formula 4). S1(H1)>S1(D1) ... (Number 4)

[0401] In the organic EL device according to this embodiment, the first dopant material and the first host material satisfy the relationship of the above-mentioned mathematical formula (Mathematical Formula 4), and therefore the singlet energy of the first dopant material is smaller than the singlet energy of the first host material. Therefore, singlet excitons generated by the TTF phenomenon transfer energy from the first host material to the first dopant material, contributing to the emission (preferably fluorescent emission) of the first dopant material.

[0402] (singlet energy S1) The following method can be mentioned as a method for measuring the singlet energy S1 using a solution (sometimes referred to as a solution method). 10 of the compounds to be measured -5 mol / L or more 10 -4 A toluene solution of 1000 mol / L or less is prepared and placed in a quartz cell, and the absorption spectrum (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K). A tangent line is drawn to the falling edge on the long wavelength side of this absorption spectrum, and the wavelength value λedge [nm] at the intersection of this tangent line and the horizontal axis is substituted into the following conversion formula (F2) to calculate the singlet energy. Conversion formula (F2): S1[eV]=1239.85 / λedge An example of an absorption spectrum measuring device is a spectrophotometer (device name: U3310) manufactured by Hitachi, Ltd., but is not limited to this.

[0403] The tangent to the fall on the long wavelength side of the absorption spectrum is drawn as follows. When moving along the spectral curve from the longest maximum value on the longest wavelength side of the absorption spectrum toward longer wavelengths, consider the tangent at each point on the curve. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the slope is minimum on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is considered to be the tangent to the fall on the long wavelength side of the absorption spectrum. Note that maximum points with absorbance values of 0.2 or less are not included in the maximum values on the longest wavelength side.

[0404] In the organic EL element according to this embodiment, when the first light-emitting layer and the second light-emitting layer are stacked in the order of the second light-emitting layer and the first light-emitting layer from the anode side, it is preferable that the electron mobility μe(H2) of the second host material and the electron mobility μe(H1) of the first host material satisfy the relationship of the following mathematical formula (3). When the first host material and the second host material satisfy the relationship of the following mathematical formula (3), the recombination ability of holes and electrons in the second light-emitting layer is improved. μe(H1)>μe(H2) ... (Equation 3)

[0405] In the organic EL element according to this embodiment, when the stacking order of the first emitting layer and the second emitting layer is the second emitting layer and the first emitting layer from the anode side, it is also preferable that the hole mobility μh(H2) of the second host material and the hole mobility μh(H1) of the first host material satisfy the relationship of the following mathematical formula (Mathematical Formula 31). μh(H2)>μh(H1) …(Equation 31)

[0406] In the organic EL element according to this embodiment, when the stacking order of the first emitting layer and the second emitting layer is the second emitting layer and the first emitting layer from the anode side, it is also preferable that the hole mobility μh(H2) of the second host material, the electron mobility μe(H2) of the second host material, the hole mobility μh(H1) of the first host material, and the electron mobility μe(H1) of the first host material satisfy the relationship shown in the following formula (Formula 32). (μe(H1) / μh(H1))>(μe(H2) / μh(H2)) …(Math. 32)

[0407] The electron mobility can be measured by measuring impedance using a mobility evaluation element fabricated by the following procedure. The mobility evaluation element is fabricated, for example, by the following procedure. A compound (Target) whose electron mobility is to be measured is vapor-deposited on a glass substrate with an aluminum electrode (anode) so as to cover the aluminum electrode, thereby forming a measurement target layer. An electron transport layer is formed on this measurement target layer by vapor-depositing the following compound ET-A. An electron injection layer is formed on this electron transport layer by vapor-depositing LiF. A metal cathode is formed on this electron injection layer by vapor-depositing metallic aluminum (Al). The above-mentioned configuration of the device for evaluating mobility can be shown in simplified form as follows. glass / Al(50) / Target(200) / ET-A(10) / LiF(1) / Al(50) The numbers in parentheses indicate the film thickness (nm).

[0408] [ka]

[0409] The element for evaluating electron mobility is placed in an impedance measurement device and impedance measurement is performed. The impedance measurement is performed by sweeping the measurement frequency from 1 Hz to 1 MHz. At this time, a DC voltage V is applied to the element simultaneously with an AC amplitude of 0.1 V. The modulus M is calculated from the measured impedance Z using the relationship in the following calculation formula (C1). Calculation formula (C1): M=jωZ In the above calculation formula (C1), j is an imaginary unit whose square is -1, and ω is the angular frequency [rad / s]. In a Bode plot with the imaginary part of the modulus M on the vertical axis and frequency [Hz] on the horizontal axis, the electrical time constant τ of the mobility evaluation element is calculated from the frequency fmax showing the peak using the following calculation formula (C2). Calculation formula (C2): τ=1 / (2πfmax) In the above formula (C2), π is the symbol representing the ratio of the circumference of a circle to its diameter. Using the above τ, the electron mobility μe is calculated from the relationship of the following calculation formula (C3-1). Calculation formula (C3-1):μe=d 2 / (Vτ) In the above formula (C3-1), d is the total film thickness of the organic thin films that make up the device, and in the case of the device configuration for evaluating the electron mobility, d=210 [nm].

[0410] The hole mobility can be measured by measuring impedance using a mobility evaluation device fabricated by the following procedure. The mobility evaluation device is fabricated, for example, by the following procedure. On a glass substrate with an ITO transparent electrode (anode), the following compound HA-2 is vapor-deposited so as to cover the transparent electrode to form a hole injection layer. On top of this hole injection layer, the following compound HT-A is vapor-deposited to form a hole transport layer. Subsequently, a compound Target, whose hole mobility is to be measured, is vapor-deposited to form a measurement target layer. On top of this measurement target layer, metallic aluminum (Al) is vapor-deposited to form a metal cathode. The above-mentioned configuration of the device for evaluating mobility can be shown in simplified form as follows. ITO(130) / HA-2(5) / HT-A(10) / Target(200) / Al(80) The numbers in parentheses indicate the film thickness (nm).

[0411] [ka]

[0412] The hole mobility evaluation device is placed in an impedance measurement device, and impedance measurement is performed. The impedance measurement is performed by sweeping the measurement frequency from 1 Hz to 1 MHz. At this time, a DC voltage V is applied to the device simultaneously with an AC amplitude of 0.1 V. The modulus M is calculated from the measured impedance Z using the relationship in the above calculation formula (C1). In a Bode plot with the imaginary part of the modulus M on the vertical axis and frequency [Hz] on the horizontal axis, the electrical time constant τ of the mobility evaluation element is calculated from the frequency fmax showing the peak using the above calculation formula (C2). Using τ obtained from the above formula (C2), the hole mobility μh is calculated from the relationship of the following formula (C3-2). Calculation formula (C3-2):μh=d 2 / (Vτ) In the above formula (C3-2), d is the total film thickness of the organic thin films that make up the device, and in the case of the device configuration for evaluating hole mobility, d=215 [nm].

[0413] The electron and hole mobilities herein are expressed as the square root of the electric field strength, E 1 / 2 =500[V 1 / 2 / cm 1 / 2 The square root of the electric field strength E 1 / 2 can be calculated from the relationship of the following calculation formula (C4). Calculation formula (C4): E 1 / 2 =V 1 / 2 / d 1 / 2 The impedance measurement is performed using a Solartron 1260 model impedance measuring device, and for higher accuracy, a Solartron 1296 model dielectric constant measurement interface can also be used.

[0414] In the organic EL device according to this embodiment, the first light-emitting layer preferably contains the first dopant material in an amount of 0.5 mass % or more of the total mass of the first light-emitting layer, more preferably more than 1.1 mass % of the total mass of the first light-emitting layer, even more preferably 1.2 mass % or more of the total mass of the first light-emitting layer, and even more preferably 1.5 mass % or more of the total mass of the first light-emitting layer. The first light-emitting layer preferably contains the first dopant material in an amount of 10 mass % or less of the total mass of the first light-emitting layer, more preferably 7 mass % or less of the total mass of the first light-emitting layer, and even more preferably 5 mass % or less of the total mass of the first light-emitting layer. In the organic EL device according to this embodiment, the first light-emitting layer preferably contains the first host material in an amount of 60 mass % or more of the total mass of the first light-emitting layer, more preferably 70 mass % or more of the total mass of the first light-emitting layer, even more preferably 80 mass % or more of the total mass of the first light-emitting layer, still more preferably 90 mass % or more of the total mass of the first light-emitting layer, and even more preferably 95 mass % or more of the total mass of the first light-emitting layer. The first emitting layer preferably contains the first host material in an amount of 99% by mass or less of the total mass of the first emitting layer. However, when the first emitting layer contains a first host material and a first dopant material, the upper limit of the total content of the first host material and the first dopant material is 100% by mass. Note that this embodiment does not exclude the case where the first emitting layer contains materials other than the first host material and the first dopant material. The first light-emitting layer may contain only one type of first host material or two or more types of first dopant materials.

[0415] In the organic EL device according to this embodiment, the thickness of the first emitting layer is preferably 5 nm or more, more preferably 15 nm or more. When the thickness of the first emitting layer is 5 nm or more, triplet excitons that have migrated from the second emitting layer to the first emitting layer can be easily prevented from returning to the second emitting layer. Furthermore, when the thickness of the first emitting layer is 5 nm or more, triplet excitons can be sufficiently separated from the recombination moiety in the second emitting layer. In the organic EL device according to this embodiment, the thickness of the first light-emitting layer is preferably 20 nm or less, which can increase the density of triplet excitons in the first light-emitting layer and make the TTF phenomenon more likely to occur. In the organic EL device according to this embodiment, the thickness of the first light-emitting layer is preferably 5 nm or more and 20 nm or less.

[0416] (Second light-emitting layer) The second light-emitting layer includes a second host material and a second dopant material. The second host material is a compound different from the first host material contained in the first light-emitting layer. The second dopant material is preferably a compound that emits light with a maximum peak wavelength of 500 nm or less, and more preferably a compound that emits fluorescent light with a maximum peak wavelength of 500 nm or less. The method for measuring the maximum peak wavelength of the compound is as described above.

[0417] In the organic EL device according to this embodiment, the second dopant material and the first dopant material are the same or different compounds.

[0418] In the organic EL device according to this embodiment, it is preferable that the second emitting layer does not contain a metal complex, and it is also preferable that the first emitting layer does not contain a boron-containing complex.

[0419] In the organic EL device according to this embodiment, the second light-emitting layer preferably does not contain a phosphorescent material (dopant material). In addition, the second light-emitting layer preferably does not contain a heavy metal complex or a phosphorescent rare earth metal complex.

[0420] In the emission spectrum of the second dopant material, when the peak at which the emission intensity is greatest is defined as the maximum peak and the height of the maximum peak is defined as 1, the heights of other peaks appearing in the emission spectrum are preferably less than 0.6. Note that the peaks in the emission spectrum are defined as local maxima. In addition, it is preferable that the number of peaks in the emission spectrum of the second luminescent compound is less than three.

[0421] In the organic EL device according to this embodiment, the second light-emitting layer preferably emits light having a maximum peak wavelength of 500 nm or less when the device is in operation.

[0422] (Second Host Material) Examples of the second host material include: 1) Condensed aromatic compounds such as anthracene derivatives, phenanthrene derivatives, pyrene derivatives, benzanthracene derivatives, fluorene derivatives, fluoranthene derivatives, or chrysene derivatives; 2) Heterocyclic compounds such as carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, and benzoxanthene derivatives. The second host material is preferably a fused aromatic compound; It is more preferably a pyrene derivative (a compound represented by the general formula (H100) described below). The second host material is It is also preferable that the compound is a benzanthracene derivative (a compound represented by the general formula (H1X) described below) or a benzoxanthene derivative (a compound represented by the general formula (H14X) described below).

[0423] When the second host material is a pyrene derivative, the second host material is preferably a compound represented by the following general formula (H100).

[0424] (Compound represented by general formula (H100))

[0425] [ka]

[0426] (In the general formula (H100), R 101 ~R 110 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, 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 a group represented by the general formula (H110), However, R 101~R 110 at least one of is a group represented by general formula (H110) above, When a plurality of groups represented by the general formula (H110) are present, the plurality of groups represented by the general formula (H110) are the same or different from each other, L 101 teeth, 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, Ar 101 teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mx is 0, 1, 2, 3, 4 or 5; L 101 If there are two or more, there are two or more L 101 are identical to or different from each other, Ar 101 If there are two or more, there are two or more Ar 101 are identical to or different from each other, In the general formula (H110), * indicates the bonding position to the pyrene ring in the general formula (H100).

[0427] (In the general formula (H100), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 906 If there are multiple R 906 are the same or different from each other, R 907 If there are multiple R 907 are the same or different from each other, R 801 If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are either identical or different.)

[0428] In the organic EL device according to this embodiment, the group represented by the general formula (H110) is preferably a group represented by the following general formula (H111).

[0429] [ka]

[0430] (In the general formula (H111), X 10 is C(R 123 )(R 124 ), oxygen atom, sulfur atom, or NR 125 and L111 and L 112 are each independently, 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, ma is 0, 1, 2, 3 or 4; mb is 0, 1, 2, 3 or 4; ma+mb is 0, 1, 2, 3 or 4, Ar 101 represents Ar in the general formula (H110). 101 is synonymous with R 121 , R 122 , R 123 , R 124 and R 125 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mc is 3, The Three Rs 121 are identical to or different from each other, md is 3, The Three Rs 122 are either identical or different.)

[0431] In the group represented by the general formula (H111), L is located at any one of positions *1 to *4 among positions *1 to *8 of carbon atoms in the ring structure represented by the following general formula (H111a): 111 is bonded, and R is placed in the remaining three positions of *1 to *4. 121 is bonded, and L is at any one of positions *5 to *8. 112 is bonded, and R is placed in the remaining three positions of *5 to *8. 122 are combined.

[0432] [ka]

[0433] For example, in the group represented by the general formula (H111), L 111 is bonded to the carbon atom marked *2 in the ring structure represented by general formula (H111a), and L 112 When is bonded to the carbon atom at *7 in the ring structure represented by the general formula (H111a), the group represented by the general formula (H111) is represented by the following general formula (H111b).

[0434] [ka]

[0435] (In the general formula (H111b), X 10 , L 111 , L 112 , ma, mb, Ar 101 , R 121 , R 122 , R 123 , R 124and R 125 each independently represents X in the general formula (H111). 10 , L 111 , L 112 , ma, mb, Ar 101 , R 121 , R 122 , R 123 , R 124 and R 125 is synonymous with Multiple R 121 are identical to or different from each other, Multiple R 122 are either identical or different.)

[0436] In the organic EL device according to this embodiment, the group represented by the general formula (H111) is preferably a group represented by the general formula (H111b).

[0437] In the organic EL element according to this embodiment, ma is 0, 1 or 2; Preferably, mb is 0, 1 or 2.

[0438] In the organic EL element according to this embodiment, ma is 0 or 1, mb is preferably 0 or 1.

[0439] In the organic EL element according to this embodiment, Ar 101 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0440] In the organic EL element according to this embodiment, Ar 101 teeth, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted phenanthryl group, or A substituted or unsubstituted fluorenyl group is preferred.

[0441] In the organic EL element according to this embodiment, Ar 101 is also preferably a group represented by the following general formula (H120), general formula (H130) or general formula (H140).

[0442] [ka]

[0443] (In the general formula (H120), general formula (H130) and general formula (H140), R 111 ~R 120 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, * in the general formula (H120), the general formula (H130) and the general formula (H140) represents L in the general formula (H110). 101 or the bonding position of L in the general formula (H111) or the general formula (H111b). 112 )

[0444] In the organic EL element according to this embodiment, The second host material is preferably represented by the following general formula (H101).

[0445] [ka]

[0446] (In the general formula (H101), R 101 ~R 120 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, However, R 101 ~R 110 One of them is L 101 indicates the bond position with R 111 ~R 120 One of them is L 101 indicates the bonding position with L 101 teeth, 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, mx is 0, 1, 2, 3, 4 or 5; L 101 If there are two or more, there are two or more L 101 are either identical or different.)

[0447] In the organic EL element according to this embodiment, L 101 teeth, a single bond, or It is preferably a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0448] In the organic EL element according to this embodiment, The second host material is preferably represented by the following general formula (H102).

[0449] [ka]

[0450] (In the general formula (H102), R 101 ~R 120each independently represents R in general formula (H101). 101 ~R 120 is synonymous with However, R 101 ~R 110 One of them is L 111 indicates the bond position with R 111 ~R 120 One of them is L 112 indicates the bonding position with X 10 is C(R 123 )(R 124 ), oxygen atom, sulfur atom, or NR 125 and L 111 and L 112 are each independently, 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, ma is 0, 1, 2, 3 or 4; mb is 0, 1, 2, 3 or 4; ma+mb is 0, 1, 2, 3 or 4, R 121 , R 122 , R 123 , R 124 and R 125 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mc is 3, The Three Rs 121 are identical to or different from each other, md is 3, The Three Rs 122 are either identical or different.)

[0451] In the compound represented by the general formula (H102), ma is 0, 1 or 2; Preferably, mb is 0, 1 or 2.

[0452] In the compound represented by the general formula (H102), ma is 0 or 1, mb is preferably 0 or 1.

[0453] In the organic EL element according to this embodiment, R 101 ~R 110 It is preferable that two or more of the above are groups represented by the general formula (H110).

[0454] In the organic EL element according to this embodiment, R 101 ~R 110 two or more of the above are groups represented by general formula (H110), and Ar 101 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0455] In the organic EL element according to this embodiment, Ar 101 is not a substituted or unsubstituted pyrenyl group, L 101 is not a substituted or unsubstituted pyrenylene group, R which is not a group represented by the general formula (H110) 101 ~R 110 The substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms as represented by is preferably not a substituted or unsubstituted pyrenyl group.

[0456] In the organic EL element according to this embodiment, R which is not a group represented by the general formula (H110) 101 ~R 110 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 preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0457] In the organic EL element according to this embodiment, R which is not a group represented by the general formula (H110) 101 ~R 110 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms is preferred.

[0458] In the organic EL device according to this embodiment, R 101 ~R 110 is preferably a hydrogen atom.

[0459] In the compound represented by the general formula (H100), it is preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0460] The compound represented by the general formula (H100) can be produced by a known method.

[0461] (Specific examples of compounds represented by formula (H100)) Specific examples of the compound represented by the general formula (H100) include the following compounds: However, the compound represented by the general formula (H100) is not limited to the following specific examples.

[0462] [ka]

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[0483] [ka]

[0484] When the second host material is a benzanthracene derivative, the second host material is preferably a compound represented by the following general formula (H1X).

[0485] (Compounds represented by general formula (H1X))

[0486] [ka]

[0487] (In the general formula (H1X), R 101 ~R 112 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, 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 a group represented by the general formula (H11X), However, R 101 ~R 112 at least one of is a group represented by the general formula (H11X), When a plurality of groups represented by the general formula (H11X) are present, the plurality of groups represented by the general formula (H11X) are the same or different from each other, L 101 teeth, 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, Ar 101 teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mx is 1, 2, 3, 4 or 5; L 101 If there are two or more, there are two or more L 101 are identical to or different from each other, Ar 101 If there are two or more, there are two or more Ar 101 are identical to or different from each other, In the general formula (H11X), * indicates the bonding position to the benz[a]anthracene ring in the general formula (H1X).

[0488] In the organic EL device according to this embodiment, the group represented by the general formula (H11X) is preferably a group represented by the following general formula (H111X).

[0489] [ka]

[0490] (In the general formula (H111X), X 10 is C(R 343 )(R 344 ), oxygen atom, sulfur atom, or NR 345 and L 111 and L 112 are each independently, 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, ma is 1, 2, 3 or 4; mb is 1, 2, 3 or 4; ma+mb is 2, 3, or 4, Ar 101 represents Ar in the general formula (H11X). 101 is synonymous with R 341 , R 342 , R 343 , R 344 and R 345 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mc is 3, The Three Rs 341 are identical to or different from each other, md is 3, The Three Rs 342 are either identical or different.)

[0491] In the group represented by the general formula (H111X), L is located at any one of positions *1 to *4 among positions *1 to *8 of carbon atoms in the ring structure represented by the following general formula (H111aX): 111 is bonded, and R is placed in the remaining three positions of *1 to *4. 341 is bonded, and L is at any one of positions *5 to *8. 112 is bonded, and R is placed in the remaining three positions of *5 to *8. 342 are combined.

[0492] [ka]

[0493] For example, in the group represented by the general formula (H111X), L 111is bonded to the carbon atom marked *2 in the ring structure represented by the general formula (H111aX), and L 112 is bonded to the carbon atom at *7 in the ring structure represented by the general formula (H111aX), the group represented by the general formula (H111X) is represented by the following general formula (H111bX).

[0494] [ka]

[0495] (In the general formula (H111bX), X 10 , L 111 , L 112 , ma, mb, Ar 101 , R 341 , R 342 , R 343 , R 344 and R 345 each independently represents X in the general formula (H111X). 10 , L 111 , L 112 , ma, mb, Ar 101 , R 341 , R 342 , R 343 , R 344 and R 345 is synonymous with Multiple R 341 are identical to or different from each other, Multiple R 342 are either identical or different.)

[0496] In the organic EL device according to this embodiment, the group represented by the general formula (H111X) is preferably a group represented by the general formula (H111bX).

[0497] In the compound represented by the general formula (H1X), it is preferable that ma is 1 or 2, and mb is 1 or 2.

[0498] In the compound represented by the general formula (H1X), it is preferable that ma is 1 and mb is 1.

[0499] In the compound represented by the general formula (H1X), Ar 101 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0500] In the compound represented by the general formula (H1X), Ar 101 teeth, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted benz[a]anthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted phenanthryl group, or A substituted or unsubstituted fluorenyl group is preferred.

[0501] The compound represented by the general formula (H1X) is also preferably represented by the following general formula (H101X).

[0502] [ka]

[0503] (In the general formula (H101X), R 111 and R 112 One of them is L 101 indicates the bond position with R 333 and R 334 One of them is L 101 indicates the bonding position with R 101 ~R 110 , R 321 ~R 330 , L 101 R is not a bond position with 111 or R 112 , and L 101 R is not a bond position with 333 or R334 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L 101 teeth, 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, mx is 1, 2, 3, 4 or 5; L 101 If there are two or more, there are two or more L 101 are either identical or different.)

[0504] In the compound represented by the general formula (H1X), L 101 is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0505] The compound represented by the general formula (H1X) is also preferably represented by the following general formula (H102X).

[0506] [ka]

[0507] (In the general formula (H102X), R 111 and R 112 One of them is L 111 indicates the bond position with R 333 and R 334 One of them is L 112 indicates the bonding position with R 101 ~R 110 , R 321 ~R 330 , L 111 R is not a bond position with 111 or R 112 and L 112 R is not a bond position with 333 or R 334 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, X 10 is C(R 343 )(R 344 ), oxygen atom, sulfur atom, or NR 345 and L 111 and L 112 are each independently, 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, ma is 1, 2, 3 or 4; mb is 1, 2, 3 or 4; ma+mb is 2, 3, 4 or 5, R 341 , R 342 , R 343 , R 344 and R 345 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mc is 3, The Three Rs 341 are identical to or different from each other, md is 3, The Three Rs 342 are either identical or different.)

[0508] In the compound represented by the general formula (H1X), it is preferable that ma in the general formula (H102X) is 1 or 2, and mb is 1 or 2.

[0509] In the compound represented by the general formula (H1X), it is preferable that ma in the general formula (H102X) is 1 and mb is 1.

[0510] In the compound represented by the general formula (H1X), the group represented by the general formula (H11X) is also preferably a group represented by the following general formula (H11AX) or a group represented by the following general formula (H11BX).

[0511] [ka]

[0512] (In the general formula (H11AX) and the general formula (H11BX), R 121 ~R 129、 R 330 , and R 331 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, When a plurality of groups represented by the general formula (H11AX) are present, the plurality of groups represented by the general formula (H11AX) are the same or different from each other, When a plurality of groups represented by the general formula (H11BX) are present, the plurality of groups represented by the general formula (H11BX) are the same or different from each other, L 131 and L 132 are each independently, 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, * in the general formula (H11AX) and the general formula (H11BX) respectively indicates the bonding position to the benz[a]anthracene ring in the general formula (H1X).

[0513] The compound represented by the general formula (H1X) is also preferably represented by the following general formula (H103X).

[0514] [ka]

[0515] (In the general formula (H103X), R 101 ~R 110 and R 112 are R in the general formula (H1X), respectively. 101 ~R 110 and R 112 is synonymous with R 121 ~R 129、 R 330 , and R 331 , and L 131 and L 132 are R in the general formula (H11BX), respectively. 121 ~~R 129、 R 330 , and R 331 , and L 131 and L 132 is equivalent to

[0516] In the compound represented by the general formula (H1X), L 331 is also preferably a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0517] In the compound represented by the general formula (H1X), L 332 is also preferably a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0518] In the compound represented by the general formula (H1X), R 101 ~R 112 It is also preferable that two or more of the above are groups represented by the general formula (H110).

[0519] In the compound represented by the general formula (H1X), R 101 ~R 112 two or more of the above are groups represented by the general formula (H11X), and Ar 101 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0520] In the compound represented by the general formula (H1X), Ar 101 is not a substituted or unsubstituted benz[a]anthryl group, L 101 is not a substituted or unsubstituted benz[a]anthrylene group, R that is not a group represented by the general formula (H11X) 101 ~R 110 It is also preferable that the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms as represented by is not a substituted or unsubstituted benz[a]anthryl group.

[0521] In the compound represented by the general formula (H1X), R 101 ~R 112 are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0522] In the compound represented by the general formula (H1X), R 101 ~R 112 is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.

[0523] In the compound represented by the general formula (H1X), R 101 ~R 112is preferably a hydrogen atom.

[0524] The compound represented by the general formula (H1X) can be produced by a known method.

[0525] (Specific examples of compounds represented by general formula (H1X)) Specific examples of the compound represented by the general formula (H1X) include the following compounds: However, the compound represented by the general formula (H1X) is not limited to the following specific examples.

[0526] [ka]

[0527] [ka]

[0528] [ka]

[0529] [ka]

[0530] When the second host material is a benzoxanthene derivative, the second host material is preferably a compound represented by the following general formula (H14X).

[0531] (Compounds represented by general formula (H14X)

[0532] [ka]

[0533] (In the general formula (H14X), R 1401 ~R 1410 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, 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 a group represented by general formula (H141), However, R 1401 ~R 1410 at least one of is a group represented by general formula (H141) above, When a plurality of groups represented by the general formula (H141) are present, the plurality of groups represented by the general formula (H141) are the same or different from each other, L 1401 teeth, 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, Ar 1401 teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mx4 is 0, 1, 2, 3, 4 or 5, L 1401 If there are two or more, there are two or more L 1401 are identical to or different from each other, Ar 1401 If there are two or more, there are two or more Ar 1401 are identical to or different from each other, In the general formula (H141), * indicates the bonding position to the ring represented by the general formula (H14X).

[0534] The compound represented by the general formula (H14X) can be produced by a known method.

[0535] (Specific examples of compounds represented by general formula (H14X)) Specific examples of the compound represented by the general formula (H14X) include the following compounds: However, the compound represented by the general formula (H14X) is not limited to the following specific examples.

[0536] [ka]

[0537] [ka]

[0538] (Second Dopant Material) Examples of the second dopant material include: Examples of the compound according to the first embodiment include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, aromatic amine derivatives, and tetracene derivatives. The second dopant material is The compound according to the first embodiment, A compound represented by the following general formula (5): A compound represented by the following general formula (6) is preferred.

[0539] (Compound represented by general formula (5))

[0540] [ka]

[0541] (In the general formula (5), R 501 ~R 507 and R 511 ~R 517 At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 501 ~R 507 and R 511 ~R 517 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by halogen atoms, cyano group, nitro group, 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 521 and R 522 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by halogen atoms, cyano group, nitro group, 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.

[0542] "R 501 ~R 507 and R 511 ~R 517 "A set of two or more adjacent pairs of R" is, for example, 501 and R 502 A set consisting of R 502 and R 503 A set consisting of R 503 and R 504 A set consisting of R 505 and R 506 A set consisting of R 506 and R 507 A set consisting of R 501 and R 502 and R 503It is a combination of a set consisting of:

[0543] In one embodiment, R 501 ~R 507 and R 511 ~R 517 At least one, preferably two of the following are -N(R 906 )(R 907 ) is a group represented by the formula:

[0544] In one embodiment, R 501 ~R 507 and R 511 ~R 517 are each independently, hydrogen 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.

[0545] In one embodiment, the compound represented by the general formula (5) is a compound represented by the following general formula (52):

[0546] [ka]

[0547] (In the general formula (52), R 531 ~R 534 and R 541 ~R 544 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 531 ~R 534 , R 541 ~R 544 , and R 551 and R 552are each independently, hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 561 ~R 564 are each independently, 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.

[0548] In one embodiment, the compound represented by the general formula (5) is a compound represented by the following general formula (53):

[0549] [ka]

[0550] (In the general formula (53), R 551 , R 552 and R 561 ~R 564 are each independently R in the general formula (52). 551 , R 552 and R 561 ~R 564 is equivalent to

[0551] In one embodiment, R in the general formula (52) and the general formula (53) 561 ~R 564 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably a phenyl group).

[0552] In one embodiment, R in general formula (5) 521 and R 522 R in the general formula (52) and the general formula (53) 551 and R 552 is a hydrogen atom.

[0553] In one embodiment, the substituent in the case of “substituted or unsubstituted” in the general formula (5), the general formula (52), and the general formula (53) is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring 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.

[0554] The compound represented by the general formula (5) can be produced by a known method.

[0555] (Specific examples of compounds represented by formula (5)) Specific examples of the compound represented by the general formula (5) include the following compounds: However, the compound represented by the general formula (5) is not limited to the following specific examples.

[0556] [ka]

[0557] [ka]

[0558] [ka]

[0559] [ka]

[0560] [ka]

[0561] [ka]

[0562] [ka]

[0563] [ka]

[0564] [ka]

[0565] [ka]

[0566] [ka]

[0567] [ka]

[0568] [ka]

[0569] [ka]

[0570] [ka]

[0571] (Compound represented by general formula (6))

[0572] [ka]

[0573] (In the general formula (6), Ring a, ring b and ring c each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, R 601 and R 602 each independently bond to the ring a, ring b, or ring c to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle, R that does not form the substituted or unsubstituted heterocycle 601 and R 602 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring 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.

[0574] The rings a, b, and c are rings (substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring carbon atoms, or substituted or unsubstituted heterocyclic rings having 5 to 50 ring atoms) fused to the central fused bicyclic structure of the general formula (6) composed of a boron atom and two nitrogen atoms.

[0575] The "aromatic hydrocarbon rings" of rings a, b, and c have the same structure as the compounds in which a hydrogen atom has been introduced into the above-mentioned "aryl group." The "aromatic hydrocarbon ring" of ring a contains the three carbon atoms on the central fused two-ring structure of the general formula (6) as ring-forming atoms. The "aromatic hydrocarbon ring" of ring b and ring c contains the two carbon atoms on the central fused two-ring structure of general formula (6) as ring-forming atoms.

[0576] Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms" include compounds in which a hydrogen atom has been introduced into the "aryl group" described in specific example group G1. The "heterocycles" of ring a, ring b, and ring c have the same structure as the compounds in which a hydrogen atom has been introduced into the above-mentioned "heterocyclic group." The "heterocycle" of ring a contains three carbon atoms on the central fused bicyclic structure of general formula (6) as ring-forming atoms. The "heterocycle" of rings b and c contains two carbon atoms on the central fused bicyclic structure of general formula (6) as ring-forming atoms. Specific examples of "substituted or unsubstituted heterocycles having 5 to 50 ring atoms" include compounds in which a hydrogen atom has been introduced into the "heterocyclic group" described in specific example group G2.

[0577] R 601 and R 602 may each independently bond to ring a, ring b, or ring c to form a substituted or unsubstituted heterocyclic ring. In this case, the heterocyclic ring contains the nitrogen atom on the central fused bicyclic structure of the general formula (6). In this case, the heterocyclic ring may contain a heteroatom other than the nitrogen atom. R 601 and R 602 is bonded to ring a, ring b, or ring c specifically means that an atom constituting ring a, ring b, or ring c is bonded to R 601 and R 602 It means that the atoms that make up R are bonded together. 601 is bonded to the a ring, and R 601 and ring a may be fused to form a two-ring (or three- or more-ring) fused nitrogen-containing heterocycle. Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing two- or more-ring fused heterocyclic groups in specific example group G2. R 601 When is bonded to ring b, R 602When R is bonded to ring a, 602 The same applies when is bonded to ring c.

[0578] In one embodiment, the ring a, ring b, and ring c in the general formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms. In one embodiment, the ring a, ring b, and ring c in the general formula (6) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.

[0579] In one embodiment, R in general formula (6) 601 and R 602 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms is preferred.

[0580] In one embodiment, the compound represented by the general formula (6) is a compound represented by the following general formula (62):

[0581] [ka]

[0582] (In the general formula (62), R 601A is R 611 and R 621 to form a substituted or unsubstituted heterocycle, or not to form a substituted or unsubstituted heterocycle, R 602A is R 613 and R 614 to form a substituted or unsubstituted heterocycle, or not to form a substituted or unsubstituted heterocycle, R that does not form the substituted or unsubstituted heterocycle 601Aand R 602A are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 611 ~R 621 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted heterocyclic ring, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring 611 ~R 621 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by halogen atoms, cyano group, nitro group, 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.

[0583] R in the general formula (62) 601A and R 602A are R in the general formula (6), respectively. 601 and R 602 is a group corresponding to For example, R 601A and R 611 may be bonded to form a two-ring (or three- or more-ring) nitrogen-containing heterocyclic ring in which a ring containing the ring is fused with a benzene ring corresponding to ring a. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing two- or more-ring fused heterocyclic groups in specific example group G2. 601A and R 621 If R 602A and R 613 When R is bonded, 602A and R 614 The same applies when the two are combined.

[0584] R 611 ~R 621 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or They may be bonded to each other to form a substituted or unsubstituted fused ring. For example, R 611 and R 612 may be bonded to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like is fused to the six-membered ring to which they are bonded, and the fused ring formed is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring.

[0585] In one embodiment, R that does not contribute to ring formation 611 ~R 621 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 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.

[0586] In one embodiment, R that does not contribute to ring formation 611 ~R 621 are each independently, hydrogen 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.

[0587] In one embodiment, R that does not contribute to ring formation 611 ~R 621 are each independently, a hydrogen atom, or It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0588] In one embodiment, R that does not contribute to ring formation 611 ~R 621 are each independently, a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R 611 ~R 621 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0589] In one embodiment, the compound represented by the general formula (62) is a compound represented by the following general formula (63):

[0590] [ka]

[0591] (In the general formula (63), R 631 is R 646and either combine with each other to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle; R 633 is R 647 and either combine with each other to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle; R 634 is R 651 and either combine with each other to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle; R 641 is R 642 and either combine with each other to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle; R 631 ~R 651 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted heterocyclic ring, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring 631 ~R 651 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by halogen atoms, cyano group, nitro group, 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.

[0592] R 631 is R 646 may be bonded to form a substituted or unsubstituted heterocycle. For example, R 631 and R 646 are combined to form R 646 The benzene ring to which R is bonded, the ring containing N, and the benzene ring corresponding to ring a may be condensed to form a nitrogen-containing heterocyclic ring having three or more condensed rings. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing heterocyclic group having three or more condensed rings in the specific example group G2. 633 and R 647 If R 634 and R 651 When R is bonded, 641 and R 642 The same applies when the two are combined.

[0593] In one embodiment, R that does not contribute to ring formation 631 ~R 651 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 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.

[0594] In one embodiment, R that does not contribute to ring formation 631 ~R 651 are each independently, hydrogen 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.

[0595] In one embodiment, R that does not contribute to ring formation 631 ~R 651 are each independently, a hydrogen atom, or It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0596] In one embodiment, R that does not contribute to ring formation 631 ~R 651 are each independently, a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R 631 ~R 651 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0597] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63A):

[0598] [ka]

[0599] (In the general formula (63A), R 661 teeth, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 662 ~R 665 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0600] In one embodiment, R 661 ~R 665 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0601] In one embodiment, R 661 ~R 665 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0602] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63B):

[0603] [ka]

[0604] (In the general formula (63B), R 671 and R 672 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 673 ~R675 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 906 )(R 907 ) a group represented by It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0605] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63B').

[0606] [ka]

[0607] (In the general formula (63B'), R 672 ~R 675 are each independently R in the general formula (63B). 672 ~R 675 is equivalent to

[0608] In one embodiment, R 671 ~R 675 At least one of the a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 906 )(R 907 ) a group represented by It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0609] In one embodiment, R 672 teeth, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 671 and R 673 ~R 675 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, -N(R 906 )(R 907 ) a group represented by It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0610] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63C):

[0611] [ka]

[0612] (In the general formula (63C), R 681 and R 682 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. R 683 ~R 686 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0613] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63C'):

[0614] [ka]

[0615] (In the general formula (63C'), R 683 ~R 686 are each independently R in the general formula (63C). 683 ~R 686 is equivalent to

[0616] In one embodiment, R 681 ~R 686 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0617] In one embodiment, R 681 ~R 686 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0618] The compound represented by the general formula (6) is first prepared by connecting the ring a, ring b, and ring c to a linking group (NR 601 and groups containing NR 602The intermediate is produced by linking the rings a, b, and c with a linking group (a group containing a boron atom) (reaction 2), and the final product is produced by linking the rings a, b, and c with a linking group (a group containing a boron atom) (reaction 2). In reaction 1, an amination reaction such as the Bachburt-Hartwig reaction can be applied. In reaction 2, a tandem hetero-Friedel-Crafts reaction can be applied.

[0619] The compound represented by the general formula (6) can be produced by a known method.

[0620] (Specific examples of compounds represented by formula (6)) Specific examples of the compound represented by general formula (6) include the following compounds: However, the compound represented by general formula (6) is not limited to the following specific examples.

[0621] [ka]

[0622] [ka]

[0623] [ka]

[0624] [ka]

[0625] [ka]

[0626] [ka]

[0627] [ka]

[0628] [ka]

[0629] [ka]

[0630] [ka]

[0631] [ka]

[0632] [ka]

[0633] In the organic EL device according to this embodiment, it is preferable that the singlet energy S1(H2) of the second host material and the singlet energy S1(D2) of the second dopant material satisfy the relationship of the following mathematical formula (Mathematical Formula 20). S1(H2)>S1(D2)…(Number 20)

[0634] When the second host material and the second dopant material satisfy the relationship of the mathematical formula (Mathematical Formula 20), singlet excitons generated on the second host material can easily transfer energy from the second host material to the second dopant material, contributing to the emission (preferably fluorescent emission) of the second dopant material.

[0635] In the organic EL device according to this embodiment, it is preferable that the triplet energy T1(H2) of the second host material and the triplet energy T1(D2) of the second dopant material satisfy the relationship of the following mathematical formula (Mathematical Formula 20A). T1(D2)>T1(H2) ... (Math 20A)

[0636] When the second host material and the second dopant material satisfy the relationship of the mathematical formula (Mathematical Formula 20A), triplet excitons generated in the second emitting layer move on the second host material rather than the second dopant material having a higher triplet energy, and therefore are more likely to move to the first emitting layer.

[0637] In the organic EL device according to this embodiment, the second emitting layer preferably contains the second dopant material in an amount of 0.5 mass % or more of the total mass of the second emitting layer, more preferably more than 1.1 mass % of the total mass of the second emitting layer, even more preferably 1.2 mass % or more of the total mass of the second emitting layer, and even more preferably 1.5 mass % or more of the total mass of the second emitting layer. The second light-emitting layer preferably contains the second dopant material in an amount of 10 mass % or less of the total mass of the second light-emitting layer, more preferably 7 mass % or less of the total mass of the second light-emitting layer, and even more preferably 5 mass % or less of the total mass of the second light-emitting layer.

[0638] In the organic EL device according to this embodiment, the second emitting layer preferably contains the second host material in an amount of 60 mass % or more of the total mass of the second emitting layer, more preferably 70 mass % or more of the total mass of the second emitting layer, even more preferably 80 mass % or more of the total mass of the second emitting layer, still more preferably 90 mass % or more of the total mass of the second emitting layer, and even more preferably 95 mass % or more of the total mass of the second emitting layer. The second emitting layer preferably contains the second host material in an amount of 99% by mass or less of the total mass of the second emitting layer. However, when the second emitting layer contains a second host material and a second dopant material, the upper limit of the total content of the second host material and the second dopant material is 100% by mass. Note that this embodiment does not exclude the case where the second emitting layer contains a material other than the second host material and the second dopant material. The second light-emitting layer may contain only one type of second host material or two or more types of second dopant materials.

[0639] In the organic EL device according to this embodiment, the thickness of the second light-emitting layer is preferably 3 nm or more, more preferably 5 nm or more, which is sufficient to cause recombination of holes and electrons in the second light-emitting layer. In the organic EL device according to this embodiment, the thickness of the second emitting layer is preferably 15 nm or less, more preferably 10 nm or less, which is thin enough to allow triplet excitons to migrate to the first emitting layer. In the organic EL device according to this embodiment, the thickness of the second light-emitting layer is more preferably 3 nm or more and 15 nm or less.

[0640] (Other layers of organic EL element) The organic EL device according to this embodiment may have one or more organic layers in addition to the first and second light-emitting layers, such as at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, an electron transport layer, a hole blocking layer, and an electron blocking layer.

[0641] The organic EL device according to this embodiment may have, for example, an anode, a second light-emitting layer, a first light-emitting layer, and a cathode in this order, or the order of the second light-emitting layer and the first light-emitting layer may be reversed, and the organic EL device may have an anode, a first light-emitting layer, a second light-emitting layer, and a cathode in this order. Regardless of the order of the first light-emitting layer and the second light-emitting layer, by selecting a combination of host materials that satisfies the relationship of the above mathematical formula (Mathematical Formula 1), the effects of forming the light-emitting layers into a stacked structure can be expected.

[0642] The organic EL device according to this embodiment may be configured with only the first light-emitting layer and the second light-emitting layer, or may further include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, and the like.

[0643] The organic EL device according to this embodiment preferably includes the first light-emitting layer between the anode and the cathode, and the second light-emitting layer between the first light-emitting layer and the anode. The organic EL device according to this embodiment preferably includes the first light-emitting layer between the anode and the cathode, and the second light-emitting layer between the first light-emitting layer and the cathode.

[0644] In the organic EL device according to this embodiment, it is preferable that a hole transport layer is included between the light emitting layer and the anode.

[0645] In the organic EL device according to this embodiment, it is preferable that an electron transport layer is included between the light-emitting layer and the cathode.

[0646] FIG. 2 shows a schematic configuration of another example of the organic EL element according to the fourth embodiment. The organic EL element 1A includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10A disposed between the anode 3 and the cathode 4. The organic layer 10A is configured by laminating, in this order from the anode 3 side, a hole injection layer 6, a hole transport layer 7, a second light-emitting layer 52, a first light-emitting layer 51, an electron transport layer 8, and an electron injection layer 9. FIG. 3 shows a schematic configuration of another example of the organic EL element according to the fourth embodiment. The organic EL element 1B includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10B disposed between the anode 3 and the cathode 4. The organic layer 10B is formed by laminating, in this order from the anode 3 side, a hole injection layer 6, a hole transport layer 7, a first light-emitting layer 51, a second light-emitting layer 52, an electron transport layer 8, and an electron injection layer 9. The present invention is not limited to the configuration of the organic EL element shown in FIGS.

[0647] (Third light-emitting layer) The organic EL device according to this embodiment may further include a third light-emitting layer. The third emitting layer contains a third host material, and the first host material, the second host material, and the third host material are different from one another. The third emitting layer contains at least a third dopant material, and the first dopant material, the second dopant material, and the third dopant material are the same as or different from one another. It is preferable that the triplet energy T1(H2) of the second host material and the triplet energy T1(H3) of the third host material satisfy the relationship of the following mathematical formula (Mathematical Formula 5). T1(H2)>T1(H3) ... (Number 5)

[0648] The third dopant material is preferably a compound that emits light with a maximum peak wavelength of 500 nm or less, and more preferably a compound that emits fluorescent light with a maximum peak wavelength of 500 nm or less.

[0649] When the organic EL device according to this embodiment includes a third light-emitting layer, it is preferable that the triplet energy T1(H1) of the first host material and the triplet energy T1(H3) of the third host material satisfy the relationship shown in the following formula (6). T1(H1)>T1(H3) ... (Number 6)

[0650] The third host material is not particularly limited, and for example, the host materials exemplified as the first host material and the second host material in this embodiment can be used. The third dopant material is not particularly limited, and for example, the dopant materials exemplified as the first dopant material and the second dopant material in the above embodiment can be used.

[0651] In the organic EL device according to this embodiment, the first light-emitting layer and the second light-emitting layer are preferably in direct contact with each other.

[0652] In this specification, a layer structure in which "the first light-emitting layer and the second light-emitting layer are in direct contact with each other" can include, for example, any of the following embodiments (LS1), (LS2), and (LS3). (LS1) An embodiment in which a region in which both the first host material and the second host material are mixed is generated during the process of vapor-depositing the compound for the first emitting layer and the compound for the second emitting layer, and this region is present at the interface between the first emitting layer and the second emitting layer. (LS2) When the first emitting layer and the second emitting layer contain a luminescent compound (dopant material), a region in which the first host material, the second host material, and the luminescent compound are mixed is generated during the process of vapor-depositing the compound for the first emitting layer and the process of vapor-depositing the compound for the second emitting layer, and this region is present at the interface between the first emitting layer and the second emitting layer. (LS3) When the first emitting layer and the second emitting layer contain a light-emitting compound, a region made of the light-emitting compound, a region made of the first host material, or a region made of the second host material is generated during the process of vapor-depositing the compound for the first emitting layer and the compound for the second emitting layer, and the region is present at the interface between the first emitting layer and the second emitting layer.

[0653] When the organic EL element according to this embodiment includes a third light-emitting layer, it is preferable that the first light-emitting layer and the second light-emitting layer are in direct contact with each other, and that the first light-emitting layer and the third light-emitting layer are in direct contact with each other.

[0654] In this specification, a layer structure in which "the first light-emitting layer and the third light-emitting layer are in direct contact" can include, for example, any of the following embodiments (LS4), (LS5), and (LS6). (LS4) An embodiment in which a region in which both the first host material and the third host material are mixed is generated during the process of vapor-depositing the compound for the first emitting layer and the compound for the third emitting layer, and this region is present at the interface between the first emitting layer and the third emitting layer. (LS5) When the first emitting layer and the third emitting layer contain a luminescent compound (dopant material), a region in which the first host material, the third host material, and the luminescent compound are mixed is generated during the process of vapor-depositing the compound for the first emitting layer and the process of vapor-depositing the compound for the third emitting layer, and this region is present at the interface between the first emitting layer and the third emitting layer. (LS6) When the first emitting layer and the third emitting layer contain a luminescent compound, a region made of the luminescent compound, a region made of the first host material, or a region made of the third host material is generated during the process of vapor-depositing the compound for the first emitting layer and the compound for the third emitting layer, and the region is present at the interface between the first emitting layer and the third emitting layer.

[0655] When the organic EL device according to this embodiment has an intervening layer, the intervening layer is preferably disposed between the first light-emitting layer and the second light-emitting layer.

[0656] The intervening layer is preferably a non-doped layer, preferably a layer that does not contain a light-emitting compound (dopant material), and preferably does not contain metal atoms. The intervening layer includes an intervening layer material that is preferably not a light-emitting compound. The material for the intervening layer is not particularly limited, but is preferably a material other than a light-emitting compound. Examples of materials for the intervening layer include: 1) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives; 2) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and chrysene derivatives; and 3) aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives.

[0657] The intervening layer material may be one or both of the first host material contained in the first emitting layer and the second host material contained in the second emitting layer.

[0658] When the intervening layer contains a plurality of intervening layer materials, the content of each intervening layer material is preferably 10% by mass or more of the total mass of the intervening layer. The intervening layer preferably contains the intervening layer material in an amount of 60% by mass or more of the total mass of the intervening layer, more preferably 70% by mass or more of the total mass of the intervening layer, even more preferably 80% by mass or more of the total mass of the intervening layer, even more preferably 90% by mass or more of the total mass of the intervening layer, and even more preferably 95% by mass or more of the total mass of the intervening layer. The intervening layer may contain only one type of intervening layer material, or may contain two or more types. When the intervening layer contains two or more types of intervening layer materials, the upper limit of the total content of the two or more intervening layer materials is 100% by mass. In the organic EL element according to the fourth embodiment, the intervening layer may contain a material other than the intervening layer material.

[0659] The intervening layer may be composed of a single layer or may be composed of two or more layers laminated together.

[0660] The thickness of the intervening layer is not particularly limited, but is preferably 3 nm or more and 15 nm or less, and more preferably 5 nm or more and 10 nm or less per layer.

[0661] The configuration of the organic EL element will be further described. This configuration is common to the organic EL elements of the third and fourth embodiments. Hereinafter, the reference numerals may be omitted.

[0662] (substrate) The substrate is used as a support for the organic EL element. Examples of materials that can be used for the substrate include glass, quartz, and plastic. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate. Examples of materials for forming the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Inorganic vapor-deposited films may also be used.

[0663] (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, tungsten oxide, indium oxide containing 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 metal materials (e.g., titanium nitride).

[0664] These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1% by mass or more and 10% by mass or less of zinc oxide added to indium oxide. Furthermore, for example, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5% by mass or more and 5% by mass or less of tungsten oxide and 0.1% by mass or more and 1% by mass or less of zinc oxide relative to indium oxide. Alternatively, the films may be formed by vacuum deposition, coating, inkjet printing, spin coating, or the like.

[0665] Of the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that easily injects holes regardless of the work function of the anode, so materials that can be used as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures of these, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0666] 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.

[0667] (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.

[0668] 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.

[0669] 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.

[0670] (hole injection layer) The hole injection layer is a layer containing a substance with high hole injection properties, such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, or manganese oxide.

[0671] In addition, materials with high hole injection properties include low-molecular-weight organic compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DNTPD). [N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and other aromatic amine compounds, such as dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), are also included.

[0672] Furthermore, polymeric compounds (oligomers, dendrimers, polymers, etc.) can also be used as materials with high hole injection properties. Examples include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD). Acid-added polymeric compounds such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can also be used.

[0673] (Hole transport layer) The hole transport layer is a layer containing a substance with high hole transport properties. For the hole transport layer, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used. Specifically, 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: NPB), Aromatic amine compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) can be used. The substances mentioned here are mainly 10 -6 cm 2 A material with a hole mobility of at least / (V·s).

[0674] The hole transport layer may be made of carbazole derivatives such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (PCzPA), or anthracene derivatives such as t-BuDNA, DNA, and DPAnth. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) may also be used.

[0675] However, other substances may be used as long as they have a higher hole-transporting property than an electron-transporting property. Note that the layer containing the substance having a high hole-transporting property may be not only a single layer, but also a stack of two or more layers containing the above-mentioned substances.

[0676] (electron transport layer) In the organic EL device according to the above embodiment, it is preferable that an electron transport layer is included between the light emitting layer and the cathode. The electron transport layer is a layer containing a substance with high electron transport properties. Examples of materials that can be used for the electron transport layer include: 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; and 3) polymer compounds. Specifically, examples of low-molecular-weight organic compounds that can be used include metal complexes such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviated as BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ. In addition to metal complexes, 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: Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), bathophenanthroline (abbreviated as BPhen), bathocuproine (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs) can also be used. In the above embodiment, benzimidazole compounds can be preferably used. The substances mentioned here are mainly 10 -6 cm 2 / (V·s) or more. Note that other substances may be used as the electron-transporting layer as long as they have a higher electron-transporting property than a hole-transporting property. The electron-transporting layer may be formed as a single layer or as a stack of two or more layers made of the above-mentioned substances.

[0677] The electron transport layer can also be made of a polymer compound, such as poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) or poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).

[0678] (electron injection layer) The electron injection layer is a layer containing a substance with high electron injection properties. For the electron injection layer, alkali metals, alkaline earth metals, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF), and lithium oxide (LiOx), or compounds thereof can be used. Alternatively, a substance having electron transport properties containing an alkali metal, alkaline earth metal, or a compound thereof, such as Alq containing magnesium (Mg), can be used. In this case, electron injection from the cathode can be performed more efficiently.

[0679] 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 electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material that is excellent at transporting the generated electrons. Specifically, for example, the above-mentioned substances constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor may be any substance 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.

[0680] (Layer formation method) The method for forming each layer of the organic EL element of the above embodiment is not limited to those specifically mentioned above, but may be any known method such as a dry film formation method such as a vacuum deposition method, a sputtering method, a plasma method, or an ion plating method, or a wet film formation method such as a spin coating method, a dipping method, a flow coating method, or an inkjet method.

[0681] (film thickness) The thickness of each organic layer in the organic EL device of the embodiment is not limited unless otherwise specified above. Generally, if the thickness is too thin, defects such as pinholes are likely to occur, and if the thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the thickness of each organic layer in the organic EL device is usually preferably in the range of several nm to 1 μm.

[0682] Fifth Embodiment [Electronic equipment] The electronic device according to this embodiment is equipped with the organic EL element according to any one of the above-described embodiments. Examples of the electronic device include a display device and a light-emitting device. Examples of the display device include display components (e.g., an organic EL panel module), a television, a mobile phone, a tablet, and a personal computer. Examples of the light-emitting device include lighting and vehicle lighting fixtures.

[0683] [Modifications of the embodiment] The present invention is not limited to the above-described embodiment, and any modifications and improvements that can achieve the object of the present invention are included in the present invention.

[0684] For example, the number of light-emitting layers is not limited to one, and multiple light-emitting layers may be stacked. When the organic EL device has multiple light-emitting layers, it is sufficient that at least one of the organic layers satisfies the conditions described in the above embodiment, and it is preferable that at least one of the light-emitting layers contains the compound of the first embodiment. When one of the multiple light-emitting layers contains the compound of the first embodiment, for example, the other light-emitting layers may be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize light emission by electron transition from a triplet excited state directly to the ground state. Furthermore, when the organic EL element has a plurality of light-emitting layers, these light-emitting layers may be provided adjacent to each other, or the organic EL element may be a so-called tandem type organic EL element in which a plurality of light-emitting units are stacked via an intermediate layer.

[0685] Furthermore, for example, a blocking layer may be provided adjacent to at least one of the anode side and the cathode side of the light-emitting layer. The blocking layer is preferably disposed in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons. For example, when a blocking layer is disposed adjacent to the cathode side of the light-emitting layer, the blocking layer transports electrons and prevents holes from reaching a layer (e.g., an electron transport layer) located closer to the cathode than the blocking layer. When the organic EL device includes an electron transport layer, it is preferable to include the blocking layer between the light-emitting layer and the electron transport layer. Furthermore, when a blocking layer is disposed in contact with the light-emitting layer on the anode side, the blocking layer transports holes and prevents electrons from reaching a layer (e.g., a hole transport layer) located closer to the anode than the blocking layer. When the organic EL device includes a hole transport layer, it is preferable to include the blocking layer between the light-emitting layer and the hole transport layer. A barrier layer may be provided adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to surrounding layers, and prevents excitons generated in the light-emitting layer from migrating to layers closer to the electrode than the barrier layer (e.g., electron transport layer and hole transport layer). The light-emitting layer and the barrier layer are preferably in contact with each other.

[0686] In addition, the specific structure and shape in carrying out the present invention may be other structures within the scope that the object of the present invention can be achieved. [Example]

[0687] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples in any way.

[0688] <Compound> The structures of the compounds used in the production of the organic EL device according to Example 1 are shown below: Compound BD-1 corresponds to the compound represented by general formula (1).

[0689] [ka]

[0690] The structures of the comparative compounds used in the production of the organic EL devices according to Comparative Examples 1 and 2 are shown below.

[0691] [ka]

[0692] The structures of other compounds used in the production of the organic EL devices according to Example 1 and Comparative Examples 1 and 2 are shown below.

[0693] [ka]

[0694] [ka]

[0695] [ka]

[0696] [ka]

[0697] <Fabrication of organic EL elements> An organic EL device was fabricated and evaluated as follows.

[0698] Example 1 A glass substrate (size: 25 mm x 25 mm x 0.7 mm, manufactured by Geomatec Co., Ltd.) with a 130 nm thick indium tin oxide (ITO) transparent electrode to be used as the anode was prepared. The glass substrate with this ITO transparent electrode was cleaned with nitrogen plasma for 100 seconds. This cleaning process also improved the hole injection properties of the ITO. The cleaned glass substrate was attached to a substrate holder and transported into a vacuum deposition apparatus. Then, a pressure of 10 -6 mbar or more, 10 -8 The compound HT-1 and the compound HA were co-deposited at a pressure of 0.01 mbar or less and a deposition rate of 0.01 Å / min or more and 2 Å / min or less to form a hole injection layer (HI) with a thickness of 10 nm. The proportion of the compound HT-1 in this hole injection layer was 97% by mass, and the proportion of the compound HA was 3% by mass. Next, following the formation of the hole injection layer, the compound HT-1 was vapor deposited to form a first hole transport layer (HT) having a thickness of 80 nm. Following the formation of the first hole transport layer, compound HT-2 was evaporated to form a second hole transport layer (also called electron blocking layer) (EBL) having a thickness of 10 nm. On the second hole transport layer, compound BH-1 (first host material (BH)) and compound BD-1 (first dopant material (BD)) were co-deposited so that the proportion of compound BD-1 was 2 mass %, to form an emitting layer with a thickness of 25 nm. A compound ET-1 was evaporated on the light-emitting layer to form a first electron-transporting layer (also referred to as a hole-blocking layer) (HBL) with a thickness of 10 nm. A compound ET-2 was evaporated on the first electron transport layer (HBL) to form a second electron transport layer (ET) with a thickness of 15 nm. Lithium fluoride (LiF) was vapor deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm. Metallic Al was vapor-deposited on the electron injection layer to form a cathode with a thickness of 50 nm. The fabricated device was sealed in an inert nitrogen atmosphere containing less than 1 ppm of water and oxygen using a glass cover and a moisture absorbent. The device configuration of Example 1 is shown in outline below. ITO(130) / HT-1:HA(10:97%,3%) / HT-1(80) / HT-2(10) / BH-1:BD-1(25:98%,2%) / ET-1(10) / ET-2(15) / LiF(1) / Al(50) The numbers in parentheses indicate film thickness (unit: nm). The percentages (97%:3%) indicate the ratios (mass%) of Compound HT-1 and Compound HA in the hole injection layer, and the percentages (98%:2%) indicate the ratios (mass%) of the host material (Compound BH-1) and dopant material (Compound BD-1) in the light-emitting layer.

[0699] Comparative Examples 1 and 2 The organic EL devices according to Comparative Examples 1 and 2 were prepared in the same manner as in Example 1, except that the compound BD-1 in Example 1 was replaced with the compounds listed in Table 1.

[0700] <Evaluation of organic EL elements> The organic EL devices thus fabricated were evaluated as follows. The evaluation results are shown in Table 1.

[0701] (driving voltage) Current density is 10mA / cm 2 The voltage (unit: V) was measured when a current was passed between the anode and cathode so that

[0702] (Maximum peak wavelength λp and emission spectrum half width FWHM) Current density is 10mA / cm 2The spectral radiance spectrum when a voltage was applied to the element so that the spectral radiance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) The maximum peak wavelength λp (unit: nm) and the full width at half maximum (FWHM) of the emission spectrum (unit: nm) were determined from the obtained spectral radiance spectrum. FWHM is an abbreviation for Full Width at Half Maximum.

[0703] (External quantum efficiency EQE) Current density is 10mA / cm 2 The spectral radiance spectrum when a voltage was applied to the element so that the value was as follows was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit: %) was calculated, assuming that Lambertian radiation was used.

[0704] [Table 1]

[0705] The organic EL device of Example 1 prepared using compound BD-1 exhibited a higher external quantum efficiency EQE than the organic EL device of Comparative Example 1 prepared using comparative compound Ref-1 and the organic EL device of Comparative Example 2 prepared using comparative compound Ref-2. It was shown that compound BD-1 can achieve excellent external quantum efficiency (EQE) when used as a fluorescent material in organic electroluminescence (EL) devices.

[0706] <Synthesis example> (Synthesis of Compound BD-1) The synthesis method of compound BD-1 is described below.

[0707] [ka]

[0708] [Production of Intermediate 1-1] 2,2,6,6-Tetramethylpiperidine (42.0 mL, 249.0 mmol) was dissolved in 250 mL of tetrahydrofuran (THF). The solution was cooled to −78°C, and then 100 mL of a 2.5 M n-butyllithium solution in hexane (250 mmol) was added dropwise via cannula over 30 minutes. The solution was stirred at −78°C for 30 minutes. Triisopropyl borate (67.0 mL, 290.5 mmol) was added slowly over 30 minutes, and the mixture was stirred at −78°C for 1 hour. After that, a solution of 1,2-dibromo-4-(tert)-butyl)benzene (24.24 g, 83.0 mmol) in 50 mL of THF was added dropwise over 45 minutes at −78°C. The mixture was then allowed to warm to room temperature overnight. The reaction mixture was poured into 300 mL of ice-cold 1N HCl, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated. The crude product was used in the next reaction without purification. Intermediate (1-1) 1 The results of the H-NMR spectrum analysis are as follows: 1 H NMR (300 MHz, DMSO-d6) δ 8.44 (s, 2H), 7.62 (d, 1H), 7.27 (d, 1H), 1.25 (s, 9H).

[0709] [ka]

[0710] [Production of Intermediate 1-2] Intermediate 1-1 (27.86 g (82.96 mmol)) and 1.63 g (16.59 mmol) of potassium acetate were suspended in 332 mL of acetonitrile. Next, N-iodosuccinimide (22.4 g (99.55 mmol)) was added to the suspension at room temperature and the mixture was stirred overnight. After adding 300 mL of 10% sodium sulfite to the reaction mixture, the aqueous layer was extracted with toluene, and the organic layer was washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography using heptane as the eluent to give 22.1 g (61% yield) of intermediate 1-2 as a white solid. Intermediate (1-2) 1 The results of the H-NMR spectrum analysis are as follows: 1 H NMR (300 MHz, CD2Cl2) δ 7.87 (d, 1H), 7.67 (d, 1H), 1.31 (s, 9H).

[0711] [ka]

[0712] [Production of Intermediate 1-3] Intermediate 1-2 (12.41 g (29.70 mmol)), bis(4-tert-butyl)phenylamine (7.96 g (28.28 mmol)), and sodium tert-butoxide (3.81 g (39.60 mmol)) were added to 190 mL of toluene. The suspension was evacuated and backfilled with argon three times, and tris(dibenzylideneacetone)dipalladium(0) (777 mg (0.85 mmol)) and 982 mg (1.70 mmol) of Xantphos were added to the reaction mixture. The suspension was evacuated and backfilled with argon twice and heated at 90 °C for 19 h. The reaction was cooled to room temperature and diluted with toluene. The organic extract was washed with water, dried over magnesium sulfate, filtered, and the solution was concentrated. The residue was purified by silica gel column chromatography using cyclohexane as eluent to give 8.62 g (53% yield) of intermediate 1-3 as a white solid. The analysis results of the intermediate (1-3) by positive ion electrospray-ionization mass spectrometry (ESI-MS) are as follows: ESI-MS (positive, m / z): exact mass of C 30 H 37 Br2N = 569.13; found 570.2 [M+1] + .

[0713] [ka]

[0714] [Production of Intermediate 1-4] 2-Bromo-4-tert-butylaniline (1.60 g (7.00 mmol)) was dissolved in 65 mL of dichloromethane, and metachloroperbenzoic acid (4.83 g (7.00 mmol)) was added to the solution. The mixture was stirred at room temperature for 16 hours. The mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the organic layer was washed with 1N sodium isohexane to give 1.13 g (62% yield) of intermediate 1-4 as a yellow oil. Intermediate (1-4) 1 The results of the H-NMR spectrum analysis are as follows: 1 H NMR (600 MHz, CDCl3) δ 7.83 (d, J= 9.0 Hz, 1H), 7.72 (d, J= 1.8 Hz, 1H), 7.49 (dd, J= 1.8, 9.0 Hz, 1H), 1.35 (s, 9H).

[0715] [ka]

[0716] [Preparation of Intermediate 1-5] Intermediate 1-4 (25.2 g, 97.6 mmol) and 4-(tert-butyl)aniline (23.0 g, 154 mmol) were dissolved in 250 mL of toluene. Cesium carbonate (48.0 g, 147 mmol) and 25 mL of water were added. The orange reaction mixture was evacuated and backfilled with argon three times. 2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene (BINAP) (640 mg, 1.03 mmol)) and palladium(II) acetate (110 mg, 0.49 mmol) were added, and the suspension was evacuated and backfilled with argon three times before heating at 86 °C for 22 h. The dark reaction mixture was cooled to room temperature and washed first with water (2 × 150 mL), followed by 12% aqueous hydrochloric acid (2 × 150 mL), and water (2 × 100 mL). The organic phase was dried over sodium sulfate and filtered through a 12 cm pad of silica gel. The silica gel pad was washed with toluene, and the collected eluate was dried under vacuum to give 32.6 g of intermediate 1-5 as an orange oil. The product was used in the next step without further purification. Intermediate (1-5) 1 The results of the H-NMR spectrum analysis are as follows: 1 H NMR (300 MHz, DMSO-d6) δ 9.42 (s, 1H), 8.06 (d, 1H), 7.50 - 7.39 (m, 2H), 7.32 - 7.23 (m, 2H), 7.22 (d, 1H), 6.94 (dd, 1H), 1.31 (s, 9H), 1.19 (s, 9H).

[0717] [ka]

[0718] [Preparation of Intermediate 1-6] Intermediate 1-5 (28.0 g (85.8 mmol)) was dissolved in 80 ml of tetrahydrofuran and 300 ml of methanol. Ammonium chloride (148 g) and zinc (27.0 g (0.41 mol)) were added, followed by 1.5 ml of concentrated hydrochloric acid solution. The temperature was raised to a maximum of 50 °C, and the resulting orange reaction mixture was stirred for 15 minutes until the temperature dropped to 40 °C. Zinc (29.0 g (0.44 mol)) was added, and the reaction mixture was stirred for 1 hour. The gray suspension was filtered, and the remaining solid was washed with tetrahydrofuran. The collected eluent was concentrated under vacuum. The product was further purified by MPLC using a CombiFlash® Companion (silica gel, 0-4% gradient of heptane / ethyl acetate) to give the product as a yellow resin. The resin was dissolved in a mixture of heptane and dichloromethane, and the dichloromethane was removed under vacuum. The solution was allowed to stand at room temperature until a solid formed. The solid was filtered off and washed with a small amount of heptane to give 10.2 g of intermediate 1-6 as a white solid. The filtrate was concentrated to one-third of its volume under vacuum and kept at room temperature until a solid formed. The solid was filtered off and washed with a small amount of heptane to give an additional 4.5 g of intermediate 1-6 as a white solid. The analysis results of the intermediate (1-6) by positive ion electrospray-ionization mass spectrometry (ESI-MS) are as follows: ESI-MS (positive, m / z): exact mass of C 20 H 28 N2= 296.23; found 297.4 [M+1] + .

[0719] [ka]

[0720] [Preparation of Intermediate 1-7] Intermediate 1-3 (16.1 g (28.2 mmol)), Intermediate 1-6 (9.20 g (31.0 mmol)), and sodium tert-butoxide (5.40 g (56.2 mmol)) were suspended in 100 mL of toluene. The red suspension was evacuated three times, backfilled with argon, and heated to 60 °C. A catalyst solution was prepared by dissolving 740 mg (0.81 mmol) of tris(dibenzylideneacetone)dipalladium(0) and 1.04 g (1.67 mmol) of 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene (BINAP) in 20 mL of toluene and heating under reflux for 5 minutes. One-quarter of the catalyst solution was added to the red suspension. The dark reaction mixture was heated at 74 °C for 4 hours. The reaction mixture was cooled to room temperature and filtered through a 3 cm layer of Hyflo® filter aid. The organic phase was washed with water (2 × 100 mL) and 100 mL of saturated aqueous sodium chloride solution, followed by drying over sodium sulfate. The product was further purified by MPLC using a CombiFlash Companion (silica gel, 0-3% gradient of ethyl acetate in heptane) to give 16.8 g (75% yield) of intermediate 1-7 as a red resin. The analysis results of the intermediate (1-7) by positive ion electrospray-ionization mass spectrometry (ESI-MS) are as follows: ESI-MS (positive, m / z): exact mass of C 50 H 64 BrN3= 785.43; found 786.6 [M+1] + .

[0721] [ka]

[0722] [Preparation of Intermediate 1-8] 1-(tert-Butyl)-3,5-dimethylbenzene (100 g, 0.62 mol) was dissolved in 700 ml of acetic acid. Bromine (89.0 g, 0.56 mol) in 300 ml of acetic acid was slowly added at a maximum temperature of 10°C, and stirring was continued for 3 hours up to a temperature of 17°C. Stirring was continued at room temperature for 17 hours. 300 ml of a 3% aqueous solution of sodium thiosulfate was added dropwise, and the resulting reaction mixture was stirred for 30 minutes, followed by stirring at 5°C. The reaction mixture was filtered, and the solid was dissolved in 400 ml of dichloromethane. This solution was treated with 200 ml of water and 200 ml of saturated aqueous sodium bicarbonate solution, followed by stirring for 5 minutes. The organic phase was washed with 300 ml of water and 200 ml of saturated aqueous sodium chloride solution. The organic phase was dried over magnesium sulfate and concentrated under vacuum. The product was heated in 500 ml of methanol until a clear solution was formed. The solution was cooled to room temperature and stirred until a suspension was formed. The suspension was filtered to give 67.0 g of a white solid. An additional amount of solid was isolated from the filtrate by repeating the same crystallization procedure, giving a total of 101 g (75% yield) of Intermediate 1-8 as a white solid. Intermediate (1-8) 1 The results of the H-NMR spectrum analysis are as follows: 1 H NMR (300 MHz, CD2Cl2) δ 7.15 (s, 2H), 2.44 (s, 6H), 1.33 (s, 9H).

[0723] [ka]

[0724] [Preparation of Intermediate 1-9] Intermediate 1-8 (7.0 g, 29.0 mmol) in 70 ml of tert-butylbenzene was cooled to -10 °C. 30.6 ml of a 1.9 M pentane solution of tert-butyllithium was slowly added, and the temperature was raised to room temperature, followed by stirring at room temperature for 15 minutes. The yellow suspension was cooled to -32 °C, and 20.3 ml of a 1.0 M heptane solution of tribromoborane was added dropwise, followed by stirring at room temperature for 15 minutes. The resulting suspension of intermediate 1-9 was used directly in the next step.

[0725] [ka]

[0726] [Preparation of Intermediate 1-10] Intermediate 1-7 (7.10 g (9.02 mmol)) and N,N-diisopropyl-ethylamine (6.3 ml (36 mmol)) in 70 ml of tert-butylbenzene were slowly treated with half of the product suspension of Intermediate 1-9 at −54 °C. The green suspension was stirred until it reached room temperature. The other half of the product suspension of Intermediate 1-9 was added at −52 °C. The white suspension was stirred until it reached room temperature. 6.5 ml of N,N-diisopropyl-ethylamine was added and stirring was continued at room temperature for 22 h. The white suspension was treated with 200 ml of 10% aqueous sodium carbonate solution. The organic phase was washed with water (2 × 100 ml) and 100 ml of saturated aqueous sodium chloride solution, then dried over sodium sulfate and concentrated in vacuo. The product was further purified by MPLC using a CombiFlash Companion (silica gel, heptane / toluene). The resulting resin was heated in methanol under reflux until a suspension was formed. The suspension was cooled to room temperature and stirred for 1 hour. The suspension was filtered and the solid was washed with a small amount of methanol to give 3.1 g (36% yield) of intermediate 1-10 as a white solid. The analysis results of the intermediate (1-10) by positive ion electrospray-ionization mass spectrometry (ESI-MS) are as follows: ESI-MS (positive, m / z): exact mass of C 62 H79 BBrN3= 955.56; found 956.8 [M+1] +

[0727] [ka]

[0728] [Production of Compound BD-1] Intermediate 1-10 (2.58 g (2.70 mmol)) was dissolved in 50 mL of anhydrous tert-butylbenzene. 2.9 mL of a 1.6 M solution of tert-butyllithium in pentane was slowly added at -40°C, and the solution was stirred to room temperature for 1 hour. Stirring was continued at room temperature for 20 minutes. The solution wa...

Claims

1. A compound represented by the following general formula (1): 【Chemical 1】 (In the general formula (1), Ring A1, ring B1, and ring C1 each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted aromatic heterocycle having 6 to 50 ring atoms, When ring A1 has two or more substituents, one or more pairs of adjacent two or more substituents are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, When ring B1 has two or more substituents, one or more pairs of adjacent two or more substituents are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, When ring C1 has two or more substituents, one or more pairs of adjacent two or more substituents are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, The substituent when ring A1 has a substituent, the substituent when ring B1 has a substituent, and the substituent when ring C1 has a substituent each independently represent: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ ) a group represented by -Si(R １３３ ) (R １３４ ) (R １３５ ) a group represented by -O-(R １３６ ) a group represented by -S-(R １３７ ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R １３８ a group represented by -COOR １３９ a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R １４０ ) (R １４１ ) a group represented by -Ge(R １４２ ) (R １４３ ) (R １４４ ) a group represented by -B(R １４５ ) (R １４６ ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, X is oxygen atoms, sulfur atoms, N(R １０１ )、 Si(R １０２ ) (R １０３ ), or C (R １０４ ) (R １０５ ) and R １０１ teeth, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R １３３ ) (R １３４ ) (R １３５ ) a group represented by -O-(R １３６ ) a group represented by -S-(R １３７ ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R １３８ a group represented by -COOR １３９ a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R １４０ ) (R １４１ ) a group represented by -Ge(R １４２ ) (R １４３ ) (R １４４ ) a group represented by -B(R １４５ ) (R １４６ ) a group represented by 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 A group represented by the following general formula (3): The dashed line of U1 is and ring B1 bond together to form a substituted or unsubstituted monocycle, or and ring B1 bond to each other to form a substituted or unsubstituted fused ring, or and ring C1 together to form a substituted or unsubstituted monocyclic ring, or and the ring C1 bond to each other to form a substituted or unsubstituted fused ring, U1 is, oxygen atoms, sulfur atoms, N (R １１１ ), or B (R １１２ ) and V1 is, N(R １１３ )、 B (R １１４ ), or C(=O), U1 and V1 are different from each other, R １０２ ~R １０５ , R １１１ ~R １１４、 and R １３１ ~R １４６ 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R １３１ If there are multiple R １３１ are the same or different from each other, R １３２ If there are multiple R １３２ are the same or different from each other, R １３３ If there are multiple R １３３ are the same or different from each other, R １３４ If there are multiple R １３４ are the same or different from each other, R １３５ If there are multiple R １３５ are the same or different from each other, R １３６ If there are multiple R １３６ are the same or different from each other, R １３７ If there are multiple R １３７ are the same or different from each other, R １３８ If there are multiple R １３８ are the same or different from each other, R １３９ If there are multiple R １３９ are the same or different from each other, R １４０ If there are multiple R １４０ are the same or different from each other, R １４１ If there are multiple R １４１ are the same or different from each other, R １４２ If there are multiple R １４２ are the same or different from each other, R １４３ If there are multiple R １４３ are the same or different from each other, R １４４ If there are multiple R １４４ are the same or different from each other, R １４５ If there are multiple R １４５ are the same or different from each other, R １４６ If there are multiple R １４６ are the same or different from each other.) 【Chemistry 2】 (In the general formula (3), The dashed line for U2 is and ring A1 bond together to form a substituted or unsubstituted monocycle, or and ring A1 bond to each other to form a substituted or unsubstituted fused ring, or and ring B1 together to form a substituted or unsubstituted monocyclic ring, or and ring B1 bond to each other to form a substituted or unsubstituted fused ring, U2 is oxygen atoms, sulfur atoms, N (R １２１ ), or B (R １２２ ) and V2 is, N(R １２３ )、 B (R １２４ ), or C(=O), U2 and V2 are different from each other, R １２１ ~R １２４ 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, U1 in the general formula (1) and U2 in the general formula (3) are the same or different from each other, V1 in the general formula (1) and V2 in the general formula (3) are the same or different from each other, *v indicates the bonding position to X in the general formula (1).

2. In the compound of claim 1, The compound represented by the general formula (1) is a compound represented by the following general formula (110), the following general formula (120), or the following general formula (130). 【Chemistry 3】 (In the general formula (110), Ring A1 and Ring B1 each independently have the same meaning as Ring A1 and Ring B1 in formula (1), X has the same meaning as X in general formula (1), V1 has the same meaning as V1 in general formula (1), U1 has the same meaning as U1 in general formula (1), U1 and V1 are different from each other, R １ , R ２ , and R ３ At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring １ ~R ３ are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ ) a group represented by -Si(R １３３ ) (R １３４ ) (R １３５ ) a group represented by -O-(R １３６ ) a group represented by -S-(R １３７ ) a group represented by halogen atoms, cyano group, -B(R １４５ ) (R １４６ ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the general formula (120), Ring A1 and ring C1 each independently have the same meaning as ring A1 and ring C1 in general formula (1), X has the same meaning as X in general formula (1), V1 has the same meaning as V1 in general formula (1), U1 has the same meaning as U1 in general formula (1), U1 and V1 are different from each other, R ４ , and R ５ The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring ４ , and R ５ are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ ) a group represented by -Si(R １３３ ) (R １３４ ) (R １３５ ) a group represented by -O-(R １３６ ) a group represented by -S-(R １３７ ) a group represented by halogen atoms, cyano group, -B(R １４５ ) (R １４６ ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the general formula (130), Ring B1 has the same meaning as ring B1 in formula (1), V1 has the same meaning as V1 in general formula (1), U1 has the same meaning as U1 in general formula (1), V2 has the same meaning as V2 in general formula (3), U2 has the same meaning as U2 in general formula (3), R １ , R ２ , and R ３ At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring １ ~R ３ are each independently R in the general formula (110). １ ~R ３ is synonymous with R ６ , R ７ , and R ８ At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring ６ ~R ８ are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ ) a group represented by -Si(R １３３ ) (R １３４ ) (R １３５ ) a group represented by -O-(R １３６ ) a group represented by -S-(R １３７ ) a group represented by halogen atoms, cyano group, -B(R １４５ ) (R １４６ ) a group represented by 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.

3. In the compound according to claim 2, R in the compound represented by the general formula (110) １ are not bonded to ring A1, compound.

4. In the compound according to claim 2, R in the compound represented by the general formula (120) ４ is a hydrogen atom, compound.

5. In the compound according to claim 2, R in the compound represented by the general formula (130) １ But, R ８ and do not bond with each other, compound.

6. In the compound according to claim 2, The compound represented by the general formula (110) is represented by the following general formula (110A): The compound represented by the general formula (130) is represented by the following general formula (130A): compound. 【Chemistry 4】 (In the general formula (110A), Ring A1 has the same meaning as ring A1 in formula (110). X has the same meaning as X in the general formula (110), V1 has the same meaning as V1 in general formula (110), U1 has the same meaning as U1 in the general formula (110), U1 and V1 are different from each other, R １ , R ２ , and R ３ are each independently R in the general formula (110). １ , R ２ , and R ３ is synonymous with R １ are not bonded to ring A1, In the general formula (130A), V1 and U1 have the same meanings as V1 and U1 in general formula (130), V2 and U2 have the same meanings as V2 and U2 in general formula (130), U1 and V1 are different from each other, U2 and V2 are different from each other, R １ , R ２ , R ３ , R ６ , R ７ , and R ８ are each independently R in the general formula (130). １ , R ２ , R ３ , R ６ , R ７ , and R ８ is synonymous with R １ , and R ８ are not mutually bonded, In the general formula (110A) and the general formula (130A), R ９ , R １０ , and R １１ At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring ９ , R １０ , and R １１ are each independently, hydrogen atom a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ ) a group represented by -Si(R １３３ ) (R １３４ ) (R １３５ ) a group represented by -O-(R １３６ ) a group represented by -S-(R １３７ ) a group represented by halogen atoms, cyano group, -B(R １４５ ) (R １４６ ) a group represented by 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.

7. In the compound according to claim 6, The compound represented by the general formula (110A) is represented by the following general formula (111A): compound. 【Chemistry 5】 (In the general formula (111A), Ring A1 has the same meaning as ring A1 in general formula (110A). X has the same meaning as X in general formula (110A), R １ , R ２ , R ３ , R ９ , R １０ , and R １１ are each independently R in the general formula (110A). １ , R ２ , R ３ , R ９ , R １０ , and R １１ is synonymous with R １２ and R １３ The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring １２ teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R １３ , R １４ , R １５ , R １６ , and R １７ At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R １３ , or R １７ teeth, R ９ or R ９ does not combine with R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring １３ , R １４ , R １５ , R １６ , and R １７ are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ ) a group represented by -Si(R １３３ ) (R １３４ ) (R １３５ ) a group represented by -O-(R １３６ ) a group represented by -S-(R １３７ ) a group represented by halogen atoms, cyano group, -B(R １４５ ) (R １４６ ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, However, R that does not form a ring １３ , and R １７ At least one of is a group other than a hydrogen atom or a halogen atom.

8. In the compound according to claim 7, The compound represented by the general formula (110A) is represented by the following general formula (111B): compound. 【Chemistry 6】 (In the general formula (111B), Ring A1 has the same meaning as ring A1 in general formula (110A). X has the same meaning as X in general formula (110A), R １ , R ２ , R ３ , R ９ , R １０ , and R １１ are each independently R in the general formula (110A). １ , R ２ , R ３ , R ９ , R １０ , and R １１ is synonymous with R １３ , R １４ , R １５ , R １６ , and R １７ At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R ２４ , R ２５ , R ２６ , R ２７ , and R ２８ At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R １３ teeth, R ２８ or R ２８ does not combine with R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring １３ , R １４ , R １５ , R １６ , R １７ , R ２４ , R ２５ , R ２６ , R ２７ , and R ２８ are each independently, hydrogen atom a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ ) a group represented by -Si(R １３３ ) (R １３４ ) (R １３５ ) a group represented by -O-(R １３６ ) a group represented by -S-(R １３７ ) a group represented by halogen atoms, cyano group, -B(R １４５ ) (R １４６ ) a group represented by 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.

9. In the compound according to claim 8, In the general formula (111B), R １ , and R ３ is a hydrogen atom, compound.

10. In the compound according to claim 6, The compound represented by the general formula (130A) is represented by the following general formula (131A): compound. 【Chemistry 7】 (In the general formula (131A), R １ , R ２ , R ３ , R ６ , R ７ , R ８ , R ９ , R １０ , and R １１ are each independently R in the general formula (130A). １ , R ２ , R ３ , R ６ , R ７ , R ８ , R ９ , R １０ , and R １１ is synonymous with R １２ , and R １３ The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R ２３ , and R ２２ The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R １３ , R １４ , R １５ , R １６ , and R １７ At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R １８ , R １９ , R ２０ , R ２１ , and R ２２ At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R １３ , or R １７ teeth, R ９ or R ９ does not combine with R １８ , or R ２２ teeth, R １１ or R １１ does not combine with R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring １２ , and R ２３ are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring １３ , R １４ , R １５ , R １６ , and R １７ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. １８ , R １９ , R ２０ , R ２１ , and R ２２ are each independently, hydrogen atom a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ ) a group represented by -Si(R １３３ ) (R １３４ ) (R １３５ ) a group represented by -O-(R １３６ ) a group represented by -S-(R １３７ ) a group represented by halogen atoms, cyano group, -B(R １４５ ) (R １４６ ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, However, R that does not form a ring １３ , and R １７ At least one of R is a group other than a hydrogen atom or a halogen atom, and R １８ , and R ２２ At least one of is a group other than a hydrogen atom or a halogen atom.

11. In the compound according to claim 8, The compound represented by the general formula (111B) is represented by the following general formula (111C), (111D), (111E), (111F), (111G), (111H), (111J), or (111K): compound. 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 (In the general formula (111C), the general formula (111D), the general formula (111E), the general formula (111F), the general formula (111G), the general formula (111H), the general formula (111J), and the general formula (111K), X is oxygen atoms, sulfur atoms, N(R １０１ )、 Si(R １０２ ) (R １０３ ), or C (R １０４ ) (R １０５ ) and Y is, oxygen atoms, sulfur atoms, N(R １０６ )、 Si(R １０７ ) (R １０８ ), or C (R １０９ ) (R １１０ ) and R in X １０２ ~R １０５ , and R in Y １０７ ~R １１０ are each independently R in the general formula (1). １０２ ~R １０５ is synonymous with R １０６ are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R １ ~R ３ , and R ９ ~R １１ are each independently R in the general formula (111B). １ ~R ３ , and R ９ ~R １１ is synonymous with R １３ , R １４ , R １５ , R １６ , and R １７ are each independently R in the general formula (111B). １３ , R １４ , R １５ , R １６ , and R １７ is synonymous with R １３ is R ２８ does not combine with R ２４ , R ２５ , R ２６ , R ２７ , and R ２８ are each independently, R in the general formula (111B) ２４ , R ２５ , R ２６ , R ２７ , and R ２８ is synonymous with R ２９ , R ３０ , R ３１ , and R ３２ At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring ２９ , R ３０ , R ３１ , and R ３２ are each independently R in the general formula (111B). １ , R ２ , and R ３ is synonymous with R ３３ , R ３４ , R ３５ , and R ３６ At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring ３３ , R ３４ , R ３５ , and R ３６ each independently represents an R that does not form the substituted or unsubstituted monocycle in the general formula (111B) and does not form the substituted or unsubstituted fused ring. １ , R ２ , and R ３ is synonymous with R ３７ , and R ３８ each independently represents an R that does not form the substituted or unsubstituted monocycle in the general formula (111B) and does not form the substituted or unsubstituted fused ring. １ , R ２ , and R ３ is synonymous with R ５０ , and R ５１ The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring ５０ , and R ５１ are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ６０ , and R ６１ The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring ６０ , and R ６１ are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R １０１ is represented by the following general formula (1116): 【Chemistry 11】 (In the general formula (1116), R ３９ , R ４０ , R ４１ , R ４２ , and R ４３ are each independently, R in the general formula (111B) １ , R ２ , and R ３ is synonymous with *61 is N(R) in the general formula (111C) or the general formula (111D). １０１ ) and the nitrogen atom.

12. In the compound of claim 11, In the general formula (111C), R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. １ , R ３、 R ９ , R １１ , and R ３２ is a hydrogen atom, In the general formula (111D), R 1 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. １ , R ３、 R ９ , and R １１ is a hydrogen atom, In the general formula (111E), R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. １ , R ３、 R ９ , R １１ , and R ３２ is a hydrogen atom, In the general formula (111F), R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. １ , R ３、 R ９ , and R ３２ is a hydrogen atom, In the general formula (111G), R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. １ , R ３、 and R ９ is a hydrogen atom, In the general formula (111H), R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. １ , R ３、 R ９ , R １１ , and R ３２ is a hydrogen atom, In the general formula (111J), R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. １ , R ３、 R ９ , and R ３２ is a hydrogen atom, In the general formula (111K), R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. １ , R ３、 and R ９ is a hydrogen atom, compound.

13. In the compound according to claim 11 or 12, The compound represented by the general formula (111C) is represented by the following general formula (111C-1): The compound represented by the general formula (111D) is represented by the following general formula (111D-1): compound. 【Chemistry 12】 (In the general formula (111C-1), X is an oxygen atom, or N (R １０１ ) and R １ , R ３ , R ９ , R １１ , and R ３２ is a hydrogen atom, R ２ , R １０ , R １３ ~R １７ , R ２４ ~R ２８ , R ２９ ~R ３１ are each independently R in the general formula (111C). ２ , R １０ , R １３ ~R １７ , R ２４ ~R ２８ , R ２９ ~R ３１ is synonymous with In the general formula (111D-1), X is an oxygen atom, or N (R １０１ ) and Y is, an oxygen atom, or is a sulfur atom, R ９ , and R １１ is a hydrogen atom, R １ ~R ３ , R １０ , R １３ ~R １７ , R ２４ ~R ２８ , R ３３ ~R ３６ are each independently R in the general formula (111D). 1 ~R ３ , R １０ , R １３ ~R １７ , R ２４ ~R ２８ , R ３３ ~R ３６ is synonymous with R １０１ is represented by the following general formula (1116): 【Chemistry 13】 (In the general formula (1116), R ３９ ~R ４３ are each independently R in the general formula (111B). １ , R ２ , and R ３ is synonymous with *61 is N(R) in the general formula (111C-1) or the general formula (111D-1). １０１ ) and the nitrogen atom.

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

15. An organic electroluminescent device having a cathode, an anode, and an organic layer between the cathode and the anode, At least one of the organic layers contains the compound according to any one of claims 1 to 13 as a first compound. Organic electroluminescent element.

16. the organic layer includes an emitting layer; the light-emitting layer contains the first compound; The organic electroluminescence device according to claim 15 .

17. the light-emitting layer contains a second compound represented by the following general formula (H10): The organic electroluminescence device according to claim 16 . 【Chemistry 14】 [In the general formula (H10), R １０１ ~R １１０ One or more pairs of adjacent two or more of the joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring １０１ ~R １１０ are each independently, hydrogen atoms, a substituent R, or A group represented by the following general formula (H11): provided that R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. １０１ ~R １１０ At least one of the above is a group represented by the following general formula (H11): When two or more groups represented by the following general formula (H11) are present, the two or more groups represented by the following general formula (H11) are the same or different. -L １０１ -Ar １０１ (H11) (In the general formula (H11), L １０１ teeth, 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, Ar １０１ teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ) a group represented by -O-(R ９０４ ) a group represented by -S-(R ９０５ ) a group represented by -N(R ９０６ ) (R ９０７ ) a group represented by Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, When two or more substituents R are present, the two or more substituents R are the same or different from each other, 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ９０６ If there are multiple R ９０６ are the same or different from each other, R ９０７ If there are multiple R ９０７ are the same or different from each other.)

18. An electronic device equipped with the organic electroluminescence element according to any one of claims 15 to 17.

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