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

Abstract

To provide a compound having an emission peak wavelength in a desired wavelength zone in a fluorescence spectrum waveform.SOLUTION: As a specific example, the compound of formula (BD-1) is illustrated.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 element (hereinafter sometimes referred to as an "organic EL element"), 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 laws of electron spin, singlet excitons are generated at a rate of 25% and triplet excitons are generated at a rate of 75%. Fluorescent organic electroluminescence (EL) elements that use light emitted from singlet excitons are being applied to full-color displays of mobile phones and televisions, but their internal quantum efficiency is said to be limited to 25%. Therefore, research is being conducted to improve the performance of organic EL elements.

[0003] For example, Patent Documents 1 to 3 disclose fused ring compounds containing a nitrogen atom and a boron atom as compounds that can be used in organic electroluminescence devices. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] US Patent Application Publication No. 2019 / 0067577 [Patent Document 2] International Publication No. 2020 / 135953 [Patent Document 3] Patent Publication No. 2021-095342 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 luminance, emission wavelength, half-width, chromaticity, luminous efficiency, driving voltage, and life. For example, a compound that expresses an emission peak wavelength in a desired wavelength range in a fluorescent spectrum waveform is required for a blue light-emitting material. An object of the present invention is to provide a compound having an emission peak wavelength in a desired wavelength range in a fluorescence spectrum waveform. Another object of the present invention is to provide a material for an organic electroluminescence device, an organic electroluminescence device, and an electronic device equipped with the organic electroluminescence device, the material including a compound having an emission peak wavelength in a desired wavelength range in a fluorescence spectrum waveform. [Means for solving the problem]

[0006] According to one aspect of the present invention, there is provided a compound represented by the following general formula (1):

[0007] [ka]

[0008] (In the general formula (1), Ring A 1 , ring B 1 , ring C 1 and Ring D 1 are each independently A substituted or unsubstituted ring having 5 to 60 ring atoms, Za and Zb are ring A 1 are the atoms that make up Zc and Zd are ring B 1 are the atoms that make up Za, Zb, Zc, and Zd each independently represent a nitrogen atom or a carbon atom; Ring C 1 and Ring D 1 teeth, 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 1 teeth, 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, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, -N(R 1A )(R 2A ) a group represented by -CN, or -O-(R 136 ) is a group represented by R 1 is 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, The R 1 teeth, Ring A 1 and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring A 1 and combine with each other to form a substituted or unsubstituted fused ring, or Ring A 1 and do not combine with each other, Ring B 1 and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring B 1 and Ring B 1 and do not combine with each other, R 1 , ring A 1 , ring B 1 , ring C 1 and Ring D 1 At least one of the substituents is -N(R 1A )(R 2A ) a group represented by R1A and R 2A A 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 1 As a substituent, -N(R 1A )(R 2A ) wherein R 1A and R 2A are each independently R 1 and combine with each other to form a substituted or unsubstituted monocyclic ring, or R 1 and R 1 and do not combine with each other, Ring A 1 As a substituent, -N(R 1A )(R 2A ) wherein R 1A and R 2A are each independently Ring A 1 and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring A 1 and Ring A 1 and do not combine with each other, Ring B 1 As a substituent, -N(R 1A )(R 2A ) wherein R 1A and R 2A are each independently Ring B 1 and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring B 1 and Ring B 1 and do not combine with each other, Ring C 1 As a substituent, -N(R 1A )(R 2A ) wherein R 1A and R 2A are each independently Ring C 1 and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring C 1 and Ring C 1 and do not combine with each other, Ring D 1 As a substituent, -N(R 1A )(R 2A ) wherein R 1A and R 2A are each independently Ring D 1 and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring D 1 and Ring D 1 and do not combine with each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 1A and R 2A 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, Ring A 1 Among these, a monocyclic ring having a bond connecting Za and Zb, and ring C 1 at least one of the monocycles closest to the bond connecting the boron atom and the nitrogen atom is a substituted or unsubstituted monocycle having 5 ring atoms; Y is Ring B 1 Atoms that make up the ring C 1 A single bond that connects the atoms that make up Oxygen atom, Sulfur atom, NR 21A , CR 22A R 23A or SiR 24A R 25A and R 22A and R 23A A 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 24A and R 25A A 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 21A and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 22A , R 23A , R 24A and R 25A 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 1 , ring A 1 , ring B 1 , ring C 1 and Ring D 1 When the group has a substituent, the substituent is each independently -N(R1A )(R 2A ) a group represented by 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, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 133 ~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 1A If there are multiple R 1A are the same or different from each other, R 2A If there are multiple R 2A 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 either identical or different.)

[0009] According to one aspect of the present invention, there is provided a material for an organic electroluminescence device, comprising the compound according to the above-described aspect of the present invention.

[0010] According to one aspect of the present invention, there is provided an organic electroluminescent device 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 a compound according to the above-mentioned one aspect of the present invention.

[0011] 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. Effect of the Invention

[0012] According to one aspect of the present invention, a compound having an emission peak wavelength in a desired wavelength range in a fluorescence spectrum waveform can be provided. Also, according to one aspect of the present invention, a material for an organic electroluminescence device, an organic electroluminescence device, and an electronic device equipped with the organic electroluminescence device can be provided, the material including the compound having an emission peak wavelength in a desired wavelength range in a fluorescence spectrum waveform. [Brief description of the drawings]

[0013] [Figure 1] FIG. 4 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a third embodiment of the present invention. [Diagram 2]FIG. 11 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a fourth embodiment of the present invention. [Diagram 3] FIG. 13 is a diagram showing a schematic configuration of another example of an organic electroluminescence element according to the fourth embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

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

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

[0016] In this specification, the number of ring carbon atoms represents the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. For example, the number of ring carbon atoms of a 9,9-diphenylfluorenyl group is 13, and the number of ring carbon atoms of a 9,9'-spirobifluorenyl group is 25. In addition, when a benzene ring is substituted with, for example, an alkyl group as a substituent, the carbon number of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of the benzene ring substituted with an alkyl group is 6. In addition, when a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the carbon number of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.

[0017] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic compound, a fused ring compound, and a ring assembly). The number of ring atoms does not include atoms that do not constitute a ring (e.g., a hydrogen atom that terminates the bond of an atom constituting a ring) or atoms contained in a substituent when the ring is substituted with a substituent. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms or atoms constituting a substituent bonded to a pyridine ring is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. For example, hydrogen atoms bonded to carbon atoms of a quinazoline ring or atoms constituting a substituent are not included in the number of ring atoms of the quinazoline ring. Therefore, the number of ring atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

[0018] In the present specification, the "number of carbon atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having carbon atoms XX to YY" represents the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

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

[0020] In this specification, the term "unsubstituted ZZ group" refers to the case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and the term "substituted ZZ group" refers to the case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group". In the present specification, "unsubstituted" in the case of "a substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom. In the present specification, "substituted" in the case of "a substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. Similarly, "substituted" in the case of "a BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced with an AA group.

[0021] "Substituents Described Herein" The substituents described in this specification will be described below.

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

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

[0024] Unsubstituted aryl groups (specific example group G1A): Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, Benzanthryl group, A phenanthryl group, Benzophenanthryl group, A phenalenyl group, Pyrenyl group, Chrysenyl group, benzochrysenyl group, A triphenylenyl group, Benzotriphenylenyl group, tetracenyl group, Pentacenyl group, fluorenyl group, 9,9'-spirobifluorenyl group, Benzofluorenyl group, Dibenzofluorenyl group, fluoranthenyl group, Benzofluoranthenyl group, Perylenyl groups, and A monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0025] [ka]

[0026] [ka]

[0027] Substituted aryl groups (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, Cyanophenyl group, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl group, and A group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by any one of the general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0028] "Substituted or unsubstituted heterocyclic groups" The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom as a ring-forming atom. 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, when the term "heterocyclic group" is simply used, it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group". The term "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with a substituent. Specific examples of the "substituted heterocyclic group" include the groups in which the hydrogen atoms of the "unsubstituted heterocyclic group" in the specific example group G2A below are replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are exemplified. The examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" listed here are merely examples, and the "substituted heterocyclic group" described in this specification also includes the groups in which the hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself in the "substituted heterocyclic group" in the specific example group G2B are further replaced with a substituent, and the groups in which the hydrogen atoms of the substituents in the "substituted heterocyclic group" in the specific example group G2B are further replaced with a substituent.

[0029] The specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0030] Specific example group G2B includes, for example, the following nitrogen atom-containing substituted heterocyclic groups (specific example group G2B1), oxygen atom-containing substituted heterocyclic groups (specific example group G2B2), sulfur atom-containing substituted heterocyclic groups (specific example group G2B3), and monovalent heterocyclic groups derived from ring structures represented by the following general formulae (TEMP-16) to (TEMP-33), in which one or more hydrogen atoms are replaced with substituents (specific example group G2B4).

[0031] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): Pyrrolyl group, imidazolyl group, A pyrazolyl group, A triazolyl group, Tetrazolyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, A thiazolyl group, isothiazolyl group, A thiadiazolyl group, Pyridyl group, pyridazinyl group, pyrimidinyl group, A pyrazinyl group, Triazinyl group, Indolyl groups, isoindolyl group, Indolizinyl group, A quinolizinyl group, A quinolyl group, isoquinolyl group, Cinnolyl group, phthalazinyl group, A quinazolinyl group, A quinoxalinyl group, Benzimidazolyl group, Indazolyl group, A phenanthrolinyl group, A phenanthridinyl group, acridinyl group, A phenazinyl group, A carbazolyl group, Benzocarbazolyl group, morpholino group, phenoxazinyl group, A phenothiazinyl group, Azacarbazolyl and diazacarbazolyl groups.

[0032] Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): Furyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, Dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzoisoxazolyl group, phenoxazinyl group, morpholino group, Dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, Azanaphthobenzofuranyl groups, and Diazanaphthobenzofuranyl group.

[0033] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): A thienyl group, A thiazolyl group, isothiazolyl group, A thiadiazolyl group, Benzothiophenyl group (benzothienyl group), Isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), Naphthobenzothiophenyl group (naphthobenzothienyl group), benzothiazolyl group, Benzisothiazolyl group, A phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), Diazadibenzothiophenyl group (diazadibenzothienyl group), Azanapthobenzothiophenyl group (azanaphthobenzothienyl group), and Diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0034] Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0035] [ka]

[0036] [ka]

[0037] In the general formulae (TEMP-16) to (TEMP-33), X A and Y A each independently represents an oxygen atom, a sulfur atom, NH, or CH 2 However, X 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 At least one of the groups is NH or CH 2 In this case, the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) may have any of these NH, CH 2 This includes monovalent groups obtained by removing one hydrogen atom from the group.

[0038] Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): A (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, methylbenzimidazolyl group, Ethyl benzimidazolyl group, phenyltriazinyl group, Biphenylyltriazinyl group, diphenyltriazinyl group, phenylquinazolinyl group, and Biphenylylquinazolinyl group.

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

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

[0041] Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4):

[0042] The above-mentioned "one or more hydrogen atoms of a monovalent heterocyclic group" 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 the above is NH, and X A and Y A One of them is CH 2 and methylene groups represented by the formula:

[0043] "Substituted or unsubstituted alkyl groups" Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl group (specific example group G3A) and substituted alkyl group (specific example group G3B). (Here, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group", and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group".) Hereinafter, when the term "alkyl group" is simply mentioned, it includes both the "unsubstituted alkyl group" and the "substituted alkyl group". The term "substituted alkyl group" refers to a group in which one or more hydrogen atoms in the "unsubstituted alkyl group" are replaced with a substituent. Specific examples of the "substituted alkyl group" include the following "unsubstituted alkyl group" (specific example group G3A) in which one or more hydrogen atoms are replaced with a substituent, and examples of the substituted alkyl group (specific example group G3B). In this specification, the alkyl group in the "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the "unsubstituted alkyl group" includes a straight-chain "unsubstituted alkyl group" and a branched "unsubstituted alkyl group". Note that the examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" in the specific example group G3B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl group" in the specific example group G3B is further replaced with a substituent.

[0044] Unsubstituted alkyl groups (specific example group G3A): Methyl group, Ethyl group, n-propyl group, isopropyl group, n-Butyl group, isobutyl group, s-Butyl group, and t-Butyl group.

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

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

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

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

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

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

[0051] "Substituted or unsubstituted cycloalkyl groups" Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described in this specification include the following unsubstituted cycloalkyl group (specific example group G6A) and substituted cycloalkyl group (specific example group G6B). (Here, the unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group", and the substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group".) In this specification, when the term "cycloalkyl group" is simply used, it includes both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group". The term "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl group" are replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (specific example group G6A) in which one or more hydrogen atoms are replaced with a substituent, and the examples of the substituted cycloalkyl group (specific example group G6B). The examples of the "unsubstituted cycloalkyl group" and the examples of the "substituted cycloalkyl group" listed here are merely examples, and the "substituted cycloalkyl group" described in this specification also includes a group in the "substituted cycloalkyl group" in the specific example group G6B in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself are replaced with a substituent, and a group in the "substituted cycloalkyl group" in the specific example group G6B in which a hydrogen atom of a substituent is further replaced with a substituent.

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

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

[0054] -Si(R 901 )(R 902 )(R 903 ) a group represented by As described herein, -Si(R 901 )(R 902 )(R 903 Specific examples (specific example group G7) of the group represented by -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. 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) are the same as or different from each other.

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

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

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

[0058] "Halogen atoms" Specific examples of the "halogen atom" described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0059] "Substituted or unsubstituted fluoroalkyl groups" The term "substituted or unsubstituted fluoroalkyl group" as used herein means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group (perfluoro group) in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with fluorine atoms. The number of carbon atoms in the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification. The term "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms in the "fluoroalkyl group" are replaced with a substituent. The term "substituted fluoroalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in the "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms in the substituent in the "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include the examples of the group in which one or more hydrogen atoms in the "alkyl group" (specific example group G3) are replaced with a fluorine atom.

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

[0061] "Substituted or unsubstituted alkoxy groups" A specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. The number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

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

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

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

[0065] "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) are the same or different from each other. The number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.

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

[0067] Unless otherwise specified in the present specification, the substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, and the like.

[0068] The substituted or unsubstituted heterocyclic group described in the present specification, unless otherwise specified in the present specification, is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an aza Examples of such groups include a dibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group (a (9-phenyl)carbazol-1-yl group, a (9-phenyl)carbazol-2-yl group, a (9-phenyl)carbazol-3-yl group, or a (9-phenyl)carbazol-4-yl group), a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group.

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

[0070] [ka]

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

[0072] [ka]

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

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

[0075] [ka]

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

[0077] The substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like, unless otherwise specified herein.

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

[0079] "Substituted or unsubstituted divalent heterocyclic group" Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom on the heterocycle from the above-mentioned "substituted or unsubstituted heterocyclic group". Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include divalent groups derived by removing one hydrogen atom on the heterocycle from the "substituted or unsubstituted heterocyclic group" described in specific example group G2.

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

[0081] The substituted or unsubstituted arylene group described in this specification is preferably any of the groups represented by the following general formulae (TEMP-42) to (TEMP-68), unless otherwise specified in this specification.

[0082] [ka]

[0083] [ka]

[0084] In the general formulae (TEMP-42) to (TEMP-52), Q 1 ~Q 10 are each independently a hydrogen atom or a substituent. In the above general formulae (TEMP-42) to (TEMP-52), * represents a bonding position.

[0085] [ka]

[0086] In the general formulae (TEMP-53) to (TEMP-62), Q 1 ~Q 10 are each independently a hydrogen atom or a substituent. formula Q 9 and Q 10may be bonded to each other via a single bond to form a ring. In the above general formulae (TEMP-53) to (TEMP-62), * represents a bonding position.

[0087] [ka]

[0088] In the general formulae (TEMP-63) to (TEMP-68), Q 1 ~Q 8 are each independently a hydrogen atom or a substituent. In the above general formulae (TEMP-63) to (TEMP-68), * represents a bonding position.

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

[0090] [ka]

[0091] [ka]

[0092] [ka]

[0093] In the general formulae (TEMP-69) to (TEMP-82), Q 1 ~Q 9 are each independently a hydrogen atom or a substituent.

[0094] [ka]

[0095] [ka]

[0096] [ka]

[0097] [ka]

[0098] In the general formulae (TEMP-83) to (TEMP-102), Q 1 ~Q 8 are each independently a hydrogen atom or a substituent.

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

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

[0101] [ka]

[0102] For example, R 921 ~R 930 In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," one pair of adjacent two groups is R 921 and R 922 With R 922 and R 923 With R 923 and R 924 With R 924 and R 930 With R 930 and R 925 With R 925 and R 926 With R 926 and R 927 With R 927 and R 928 With R 928 and R 929 and R 929 and R 921 It is paired with .

[0103] The above "one or more pairs" means that two or more pairs of adjacent two or more groups may simultaneously form a ring. For example, R 921 and R 922 and are bonded to ring Q A At the same time, R 925 and R 926 and are bonded to ring Q B When the above general formula (TEMP-103) is formed, the anthracene compound represented by the general formula (TEMP-104) is represented by the following general formula (TEMP-104).

[0104] [ka]

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

[0106] [ka]

[0107] The "monocyclic ring" or "condensed ring" formed may be a saturated or unsaturated ring as the structure of only the ring formed. Even when "one of the pairs of adjacent two" forms a "monocyclic ring" or a "condensed ring", the "monocyclic ring" or the "condensed ring" may form a saturated or unsaturated ring. For example, the ring Q formed in the general formula (TEMP-104) may be a saturated or unsaturated ring. A and Ring Q B are "monocyclic" or "condensed rings". In addition, the ring Q formed in the general formula (TEMP-105) A , and ring Q C is a "fused ring". The ring Q in the above general formula (TEMP-105) A and Kan Q C That is, Ring Q A and Kan Q C The ring Q in the general formula (TMEP-104) is condensed to form a condensed ring. AIf 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.

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

[0109] Here, unless otherwise specified in the present specification, the "arbitrary element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur. In the arbitrary element (for example, in the case of a carbon element or a nitrogen element), a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below. When an arbitrary element other than a carbon element is included, the ring formed is a heterocycle. Unless otherwise specified in this specification, the "one or more arbitrary elements" constituting a single ring or a condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less. Unless otherwise specified in this specification, of the "monocyclic ring" and the "condensed ring", the "monocyclic ring" is preferred. Unless otherwise specified in this specification, of the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred. Unless otherwise specified in this specification, a "monocyclic ring" is preferably a benzene ring. Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring. When "one or more of a set of two or more adjacent rings" "combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring", unless otherwise specified in this specification, preferably, one or more of a set of two or more adjacent rings combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of 1 to 15 carbon elements, nitrogen elements, oxygen elements, and sulfur elements.

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

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

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

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

[0114] Specific examples of each group of the above optional substituents are the specific examples of the substituents described above in the section "Substituents described in this specification."

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

[0116] In this specification, a numerical range expressed using "AA to BB" means a range including the number AA written before "AA to BB" as the lower limit and the number BB written after "AA to BB" as the upper limit.

[0117] First Embodiment (compound) The compound according to this embodiment is a compound represented by the following general formula (1).

[0118] [ka]

[0119] (In the general formula (1), Ring A 1 , ring B 1 , ring C 1 and Ring D 1 are each independently A substituted or unsubstituted ring having 5 to 60 ring atoms, Za and Zb are ring A 1 are the atoms that make up Zc and Zd are ring B 1are the atoms that make up Za, Zb, Zc, and Zd each independently represent a nitrogen atom or a carbon atom; Ring C 1 and Ring D 1 teeth, 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 1 teeth, 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, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, -N(R 1A )(R 2A ) a group represented by -CN, or -O-(R 136 ) is a group represented by R 1 is 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, The R 1 teeth, Ring A 1 and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring A 1 and combine with each other to form a substituted or unsubstituted fused ring, or Ring A 1 and do not combine with each other, Ring B 1 and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring B 1 and Ring B 1 and do not combine with each other, R1 , ring A 1 , ring B 1 , ring C 1 and Ring D 1 At least one of the substituents is -N(R 1A )(R 2A ) a group represented by R 1A and R 2A A 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 1 As a substituent, -N(R 1A )(R 2A ) wherein R 1A and R 2A are each independently R 1 and combine with each other to form a substituted or unsubstituted monocyclic ring, or R 1 and R 1 and do not combine with each other, Ring A 1 As a substituent, -N(R 1A )(R 2A ) wherein R 1A and R 2A are each independently Ring A 1 and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring A 1 and Ring A 1 and do not combine with each other, Ring B 1 As a substituent, -N(R 1A )(R 2A ) wherein R 1A and R 2Aare each independently Ring B 1 and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring B 1 and Ring B 1 and do not combine with each other, Ring C 1 As a substituent, -N(R 1A )(R 2A ) wherein R 1A and R 2A are each independently Ring C 1 and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring C 1 and Ring C 1 and do not combine with each other, Ring D 1 As a substituent, -N(R 1A )(R 2A ) wherein R 1A and R 2A are each independently Ring D 1 and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring D 1 and Ring D 1 and do not combine with each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 1A and R 2A 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, Ring A 1 Among these, a monocyclic ring having a bond connecting Za and Zb, and ring C 1 at least one of the monocycles closest to the bond connecting the boron atom and the nitrogen atom is a substituted or unsubstituted monocycle having 5 ring atoms; Y is Ring B 1 Atoms that make up the ring C 1 A single bond that connects the atoms that make up Oxygen atom, Sulfur atom, NR 21A , CR 22A R 23A or SiR 24A R 25A and R 22A and R 23A A 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 24A and R 25A A 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 21A and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 22A , R 23A , R 24A and R 25A 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 1 , ring A 1 , ring B 1 , ring C 1 and Ring D 1 When the group has a substituent, the substituent is each independently -N(R 1A )(R 2A ) a group represented by 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, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R133 ~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 1A If there are multiple R 1A are the same or different from each other, R 2A If there are multiple R 2A 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 either identical or different.)

[0120] According to the present embodiment, a compound having an emission peak wavelength in a desired wavelength band in a fluorescence spectrum waveform can be provided. The compound according to one embodiment emits light with a narrow half-width of the fluorescence emission spectrum. The compound according to one embodiment exhibits a high PLQY value. 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 the maximum peak wavelength.

[0121] 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.

[0122] In this specification, the maximum fluorescence emission peak wavelength is the wavelength at which the compound to be measured is within 10 -6 moles / liter or more, 10 -5 It means the maximum peak wavelength of the fluorescence spectrum at which the emission intensity is maximum in the fluorescence spectrum measured for a toluene solution in which the compound is dissolved at a concentration of mol / L or less. The measurement device may be a fluorescence spectrum measuring device (device name: FP-8300, manufactured by JASCO Corporation). Note that the fluorescence spectrum measuring device is not limited to the device exemplified here.

[0123] The compound according to this embodiment is preferably estimated to have 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 or more and 3.1 eV or less, and more preferably in the range of 2.6 eV or more and 3.0 eV or less. Therefore, according to one embodiment, it is considered that an electronic device such as a display equipped with an organic EL element containing the compound according to this embodiment can easily obtain the desired moderate blue light emission.

[0124] 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.

[0125] 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.

[0126] Methods for measuring PLQY include the following. The compound to be measured was dissolved in toluene and diluted with 5.0×10 -6 Prepare a mol / L solution, freeze and degas it, and then prepare an argon-saturated solution. Transfer the resulting solution to a quartz cell (optical path length 1.0 cm) and measure the photoluminescence quantum yield (PLQY) using an absolute PL quantum yield measurement device "Hamamatsu Quantaurus-QY C11347" (manufactured by Hamamatsu Photonics K.K.).

[0127] In the general formula (1), "Ring A 1 "A monocyclic ring having a bond connecting Za and Zb" and "Ring C 1 In the case of Compounds EX-1 and EX-2 shown below, the monocyclic ring closest to the bond connecting the boron atom and the nitrogen atom corresponds to the following monocyclic ring: In the case of compound EX-1, "ring A 1 Among them, the monocyclic ring having a bond connecting Za and Zb is a monocyclic benzene ring A. 1 Corresponding to "Ring C 1 The monocyclic ring closest to the bond connecting the boron atom and the nitrogen atom is the monocyclic pyrrole ring C 1 is equivalent to. In the case of compound EX-2, "ring A 1 Among them, the monocyclic ring having a bond connecting Za and Zb is a monocyclic benzene ring A. 1 Equivalent to Ring C 1 is a benzofuran ring, and the monocyclic furan ring C 11and benzene ring C 21 It is composed of "KanC 1 The ring closest to the bond connecting the boron atom and the nitrogen atom is the furan ring C. 11 is equivalent to.

[0128] [ka]

[0129] Among the compounds according to this embodiment, for example, "R 1 is a benzene ring, and the R 1 But ring A 1 and bond to each other to form a substituted or unsubstituted monocyclic ring" will be described with reference to the following compound EX-3 as an example. In compound EX-3, R 1 is a substituent -N(R 1A )(R 2A ) represented by the group (R 1A and R 2A is a benzene ring having a phenyl group, and ring A 1 is a benzene ring having a tertiary butyl group as a substituent, and R 1 The carbon atom at the 3* position of the benzene ring that constitutes the ring A 1 The carbon atom at the 4* position of the benzene ring that constitutes the pyrrole ring C is bonded to form a monocyclic pyrrole ring C. 12 It is formed.

[0130] Among the compounds according to this embodiment, for example, "R 1 is a benzene ring, and the substituent is -N(R 1A )(R 2A ) R 1A and R 2A R 1 The embodiment of "not being bonded to each other" will be explained using the following compound EX-3 as an example. In compound EX-3, R 1 is a substituent -N(R 1A )(R 2A ) represented by the group (R 1A and R 2Ais a benzene ring having a phenyl group, and R 1A and R 2A Both are R 1 and are not bonded to each other. Among the compounds according to this embodiment, for example, "R 1 is a benzene ring, and the substituent is -N(R 1A )(R 2A ) R 1A and R 2A are each independently R 1 and EX-4 are taken as examples to illustrate the embodiment in which "the rings are bonded to each other to form a substituted or unsubstituted monocycle." Compound EX-4 is R 1A (phenyl group) is R 1 and bond to each other to form a monocyclic pyrrole ring C 13 Specifically, compound EX-4 is a compound in which R 1A The carbon atom at the 2* position of the benzene ring that constitutes R 1 The carbon atom at position 1* of the benzene ring that constitutes the pyrrole ring C is bonded to the pyrrole ring C 13 It is formed.

[0131] [ka]

[0132] Among the compounds according to this embodiment, for example, “Ring C 1 is a benzene ring, and the substituent is -N(R 1A )(R 2A ) R 1A and R 2A each independently represents a ring C 1 and "Ring D 1 is a benzene ring, and the substituent is -N(R 1A )(R 2A ) R 1A and R 2Aeach independently represents a ring D 1 and EX-6 are taken as examples to explain the embodiment in which "the rings are bonded to each other to form a substituted or unsubstituted monocycle." In compound EX-5, ring C 1 is a substituent -N(R 1A )(R 2A ) represented by the group (R 1A and R 2A is a benzene ring having a phenyl group, and R 1A The carbon atom at position 6* of the benzene ring that constitutes the ring C 1 The carbon atom at the 5* position of the benzene ring that constitutes the pyrrole ring C is bonded to the pyrrole ring C 14 It is formed. In compound EX-6, ring D 1 is a substituent -N(R 1A )(R 2A ) represented by the group (R 1A and R 2A is a benzene ring having a phenyl group, and R 1A The carbon atom at position 8* of the benzene ring that constitutes the ring D 1 The carbon atom at position 7* of the benzene ring that constitutes the pyrrole ring C is bonded to the pyrrole ring C 15 It is formed.

[0133] [ka]

[0134] The compound represented by the general formula (1) is preferably a compound represented by the following general formula (11).

[0135] [ka]

[0136] (In the general formula (11), R 1 , ring A 1 , ring B 1 , ring C 1, Ring D 1 , Za, Zb, Zc and Zd each independently represent R 1 , ring A 1 , ring B 1 , ring C 1 , Ring D 1 , Za, Zb, Zc and Zd; However, Zc, Zd and Ze are ring B 1 are the atoms that make up Zf and Zg are ring C 1 are the atoms that make up Ze, Zf and Zg each independently represent a nitrogen atom or a carbon atom.

[0137] In the compound according to this embodiment, Ze, Zf, and Zg are preferably carbon atoms.

[0138] In the compounds according to this embodiment, Za, Zb, Zc, Zd, Ze, Zf, and Zg are preferably carbon atoms.

[0139] In the compound according to this embodiment, the ring A 1 , the ring B 1 , the ring C 1 and the ring D 1 It is preferable that the substituted or unsubstituted rings having 5 to 60 ring atoms as the rings each independently be a substituted or unsubstituted aryl ring having 6 to 60 ring carbon atoms, a substituted or unsubstituted heterocycle having 5 to 60 ring atoms, or a substituted or unsubstituted alicyclic hydrocarbon ring having 5 to 60 ring atoms.

[0140] In the compound according to this embodiment, R 1 , ring A 1 , ring B 1 , ring C 1 and Ring D 1 When R has a substituent, each of the substituents independently represents -N(R 1A )(R 2A), 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, -CN, or -O-(R 136 ) is preferably a group represented by the formula:

[0141] In the compound according to this embodiment, the compound represented by the general formula (1) is preferably a compound represented by the following general formula (12) or (13).

[0142] [ka]

[0143] (In the general formulas (12) to (13), R 1 is R in the general formula (1). 1 is synonymous with X 1 and X 2 each independently represents an oxygen atom, a sulfur atom, NRx, or C(Rx 1 )(Rx 2 ) and R 1 , R 11 ~R 13 , R 31A ~R 32A , Rx, Rx 1 , and Rx 2 At least one pair of adjacent pairs 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 1 , R 11 ~R 13 , R 41 ~R 42 , Rx, Rx 1 , and Rx 2 At least one pair of adjacent pairs 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 14 ~R 22 Of the two or more adjacent pairs, one or more pairs are 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 11 ~R 22 , R 31A ~R 32A , and R 41 ~R 42 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, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, -N(R 1A )(R 2A ) a group represented by -CN, or -O-(R 136 ) is a group represented by Rx, Rx which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring 1 , and Rx 2 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0144] However, in the general formula (12), R 31A and R 32A If pairs of 1 and R 11 ~R 22 And, R 31A ~R 32A At least one selected from the group consisting of -N(R 1A )(R 2A ) is a group represented by R 31A and R 32A A pair consisting of these is bonded to ring E 1 If R 1 and R 11 ~R 22 And, Ring E 1 and at least one selected from the group consisting of the substituents of -N(R 1A )(R 2A ) is a group represented by Ring E 1 As a substituent, -N(R 1A )(R 2A ) wherein R 1A and R 2A are each independently Ring E 1 and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring E 1 and Ring E 1 and do not combine with each other, In the general formula (13), R 41 and R 42 If pairs of 1 and R 11 ~R 22 And, R 41 ~R 42 At least one selected from the group consisting of -N(R 1A )(R 2A) is a group represented by R 41 and R 42 A pair of rings F 1 If R 1 and R 11 ~R 22 And, Ring F 1 and at least one selected from the group consisting of the substituents of -N(R 1A )(R 2A ) is a group represented by Ring F 1 As a substituent, -N(R 1A )(R 2A ) wherein R 1A and R 2A are each independently Ring F 1 and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring F 1 and Ring F 1 and do not combine with each other, The ring E 1 and ring F 1 are each independently a substituted or unsubstituted aryl ring having 6 to 57 ring carbon atoms; A substituted or unsubstituted heterocycle having 5 to 57 ring atoms, or It is a substituted or unsubstituted alicyclic hydrocarbon ring having 5 to 57 ring atoms.

[0145] In the compound according to this embodiment, it is preferable that the compound represented by the general formula (12) is represented by the following general formula (121), and the compound represented by the general formula (13) is represented by the following general formula (131).

[0146] [ka]

[0147] (In the general formulae (121) and (131), R 1 , R 11 ~R 16 , R 19 ~R 22 , X 1 and X 2 each independently represents R in the general formulas (12) and (13). 1 , R 11 ~R 16 , R 19 ~R 22 , X 1 and X 2 is synonymous with R 1 , R 11 ~R 13 , R 40 , Rx, Rx 1 , and Rx 2 At least one pair of adjacent pairs 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, Multiple R 40 are identical or different from each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 40 R each independently represents, in the general formulae (12) and (13), a ring that does not form the substituted or unsubstituted monocycle and a ring that does not form the substituted or unsubstituted fused ring. 11 is equivalent to

[0148] In the compounds according to this embodiment, it is preferable that the compound represented by the general formula (121) is represented by any one of the following general formulae (A121) to (A131), and the compound represented by the general formula (131) is represented by any one of the following general formulae (B131) to (B141).

[0149] [ka]

[0150] [ka]

[0151] [ka]

[0152] (In the above general formulae (A121) to (A129) and (B131) to (B139), R 1 , R 11 ~R 16 , R 19 ~R 22 , X 1 , X 2 , and R 40 each independently represents R in the general formulas (121) and (131). 1 , R 11 ~R 16 , R 19 ~R 22 , X 1 , X 2 , and R 40 is synonymous with R 50 and R B At least one pair of adjacent pairs 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, Multiple R 50 are identical or different from each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. B teeth, 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 50 each independently represents R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring in the general formulae (121) and (131). 40 is equivalent to

[0153] [ka]

[0154] (In the above general formulae (A130) to (A131) and (B140) to (B141), R 1 , R 11 ~R 16 , R 19 ~R 22 , X 1 , X 2 , and R 40 each independently represents R in the general formulas (121) and (131). 1 , R 11 ~R 16 , R 19 ~R 22 , X 1 , X 2 , and R 40 is synonymous with R 1A and R 2A each independently represents R in the general formula (1) 1A and R 2A is equivalent to

[0155] In the compound according to this embodiment, it is also preferable that the compound represented by the general formula (12) is represented by the following general formula (1201), and the compound represented by the general formula (13) is represented by the following general formula (1301).

[0156] [ka]

[0157] (In the general formulae (1201) and (1301), R 1 , R 11 ~R 16 , R 19 ~R 22 , R 31A ~R 32A , R 41 ~R 42 , X 1 and X 2 each independently represents R in the general formulas (12) and (13). 1 , R 11 ~R 16 , R 19 ~R 22 , R 31A ~R 32A , R 41 ~R 42 , X 1 and X 2 is synonymous with However, R 31A ~R 32A and R 41 ~R 42 R each independently represents, in the general formulae (12) and (13), a ring that does not form the substituted or unsubstituted monocycle and a ring that does not form the substituted or unsubstituted fused ring. 11 is equivalent to

[0158] In the compound according to this embodiment, the compound represented by the general formula (1201) is preferably represented by any one of the following general formulae (A1201) to (A1209), and the compound represented by the general formula (1301) is preferably represented by any one of the following general formulae (B1301) to (B1309).

[0159] [ka]

[0160] [ka]

[0161] [ka]

[0162] (In the above general formulae (A1201) to (A1209) and (B1301) to (B1309), R 1 , R 11 ~R 16 , R 19 ~R 22 , R 31A ~R 32A , R 41 ~R 42 , X 1 and X 2 R in the general formulas (1201) and (1301) is each independently 1 , R 11 ~R 16 , R 19 ~R 22 , R 31A ~R 32A , R 41 ~R 42 , X 1 and X 2 is synonymous with R 50 and R B At least one pair of adjacent pairs 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, Multiple R 50 are identical or different from each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. B teeth, 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 50each independently represents R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring in the general formulae (121) and (131). 40 is equivalent to

[0163] In the compound according to this embodiment, R 1 teeth, 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. In the compound according to this embodiment, R 11 ~R 22 , R 31A ~R 32A , R 40 , R 41 ~R 42 and R 50 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, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or -N(R 1A )(R 2A ) is preferably a group represented by the formula:

[0164] In the compound according to this embodiment, R 14 ~R 22 One of the following is -N(R 1A )(R 2A ) is a group represented by R 1A and R 2A are each independently 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. In the compound according to this embodiment, R 14 ~R 22 One of the following is -N(R 1A )(R 2A) is a group represented by R 1A and R 2A and more preferably each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0165] In the compound according to this embodiment, R 14 ~R 22 One of the following is -N(R 1A )(R 2A ) is a group represented by R 1A and R 2A A set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or It is also preferred that they are bonded to each other to form a substituted or unsubstituted fused ring.

[0166] In the compound according to this embodiment, X 1 and X 2 Each independently represents an oxygen atom or C(Rx 1 )(Rx 2 ) and Rx 1 and Rx 2 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms is preferred.

[0167] In the compound according to this embodiment, the compound represented by the general formula (1) is preferably a compound represented by the following general formula (14) or (15).

[0168] [ka]

[0169] (In the general formulas (14) to (15), R 1 is R in the general formula (1). 1 is synonymous with X 3 and X 4each independently represents an oxygen atom, a sulfur atom, NRx, or C(Rx 1 )(Rx 2 ) and R 1 , R 11 ~R 13 , and R 31 ~R 34 At least one pair of adjacent pairs 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 18 ~R 22 , R 51 ~R 52 , Rx, Rx 1 , and Rx 2 At least one pair of adjacent pairs 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 18 ~R 22 , R 61 ~R 62 , Rx, Rx 1 , and Rx 2 At least one pair of adjacent pairs 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 11 ~R 13 , R 18 ~R 22 , R 31 ~R 34 , R 51 ~R 52 , and R 61 ~R 62 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, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, -N(R 1A )(R 2A ) a group represented by -CN, or -O-(R 136 ) is a group represented by Rx, Rx which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring 1 , and Rx 2 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0170] In the compound according to this embodiment, the compound represented by the general formula (1) is preferably a compound represented by the following general formula (141) or (151).

[0171] [ka]

[0172] (In the general formulae (141) and (151), R 11 ~R 13 , R 18 ~R 22 , R 32 ~R 34 , R 51 ~R 52 , R 61 ~R 62 , X 3and X 4 each independently represents R in the general formulas (14) and (15). 11 ~R 13 , R 18 ~R 22 , R 32 ~R 34 , R 51 ~R 52 , R 61 ~R 62 , X 3 and X 4 is synonymous with R 1C ~R 4C At least one pair of adjacent pairs 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 1C ~R 4C each independently represents R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring in the general formulas (14) and (15). 11 is equivalent to

[0173] In the compounds according to this embodiment, the compound represented by the general formula (141) is preferably represented by any one of the following general formulae (C141) to (C150), and the compound represented by the general formula (151) is preferably represented by any one of the following general formulae (D151) to (D160).

[0174] [ka]

[0175] (In the above general formulae (C141) to (C142) and (D151) to (D152), X 3 , X 4 , R 11 ~R 13 , R 18 ~R22 , R 32 ~R 34 , R 51 ~R 52 , R 61 ~R 62 , and R 1C ~R 4C each independently represents X in the general formulas (141) and (151). 3 , X 4 , R 11 ~R 13 , R 18 ~R 22 , R 32 ~R 34 , R 51 ~R 52 , R 61 ~R 62 , and R 1C ~R 4C is synonymous with R 1A and R 2A each independently represents R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring in the general formula (1). 1A and R 2A is equivalent to

[0176] [ka]

[0177] [ka]

[0178] (In the above general formulae (C143) to (C145) and (D153) to (D155), X 3 , X 4 , R 11 ~R 13 , R 18 ~R 22 , R 32 ~R 34 , R 51 ~R 52 , R 61 ~R 62 , and R 1C~R 4C each independently represents X in the general formulas (141) and (151). 3 , X 4 , R 11 ~R 13 , R 18 ~R 22 , R 32 ~R 34 , R 51 ~R 52 , R 61 ~R 62 , and R 1C ~R 4C is synonymous with R 60 At least one pair of adjacent pairs 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, Multiple R 60 are identical or different from each other, R C teeth, 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 60 each independently represents R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring in the general formulae (141) and (151). 11 is equivalent to

[0179] [ka] (In the above general formulae (C146) to (C147) and (D156) to (D157), X 3 , X 4 , R 11 ~R 13 , R 18 ~R 22 , R 32 ~R 34 , and R 1C ~R 4C each independently represents X in the general formulas (141) and (151). 3 , X 4 , R 11 ~R 13 , R 18 ~R 22 , R 32 ~R 34 , and R 1C ~R 4C is synonymous with R 1A and R 2A each independently represents R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring in the general formula (1). 1A and R 2A is synonymous with R 70 At least one pair of adjacent pairs 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, Multiple R 70 are identical or different from each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 70 each independently represents R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring in the general formulae (141) and (151). 11 is equivalent to

[0180] [ka]

[0181] [ka]

[0182] (In the above general formulae (C148) to (C150) and (D158) to (D160), X 3 , X 4 , R 11 ~R 13 , R 18 ~R 22 , R 32 ~R 34 , and R 1C ~R 4C each independently represents X in the general formulas (141) and (151). 3 , X 4 , R 11 ~R 13 , R 18 ~R 22 , R 32 ~R 34 , and R 1C ~R 4C is synonymous with R 60 At least one pair of adjacent pairs 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, Multiple R 60 are identical or different from each other, R 70 At least one pair of adjacent pairs 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, Multiple R 70 are identical or different from each other, R C teeth, 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 60 and R 70 each independently represents R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring in the general formulae (141) and (151). 11 is equivalent to

[0183] In the compound according to this embodiment, R 11 ~R 13 , R 18 ~R 22 , R 31 ~R 34 , R 51 ~R 52 , R 61 ~R 62 , and R 1C ~R 4C 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, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or -N(R 1A )(R 2A ) is preferably a group represented by the formula: In the compound according to this embodiment, R 60 and R 70 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, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or -N(R 1A )(R 2A ) is preferably a group represented by the formula:

[0184] In the compound according to this embodiment, X 3 and X 4 Each independently represents an oxygen atom or C(Rx 1 )(Rx 2 ) and Rx 1 and Rx 2 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms is preferred.

[0185] In the general formulas (14) and (15), R 1 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 is also preferred. In the general formulas (14) and (15), R 1 represents a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms (preferably a substituted or unsubstituted phenyl group), The R 1 but, Ring A 1 and Ring A 1 and also preferably combine with each other to form a substituted or unsubstituted fused ring. In the general formulas (14) and (15), R 1 represents a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms (preferably a substituted or unsubstituted phenyl group), The R 1 but, Ring B 1 and Ring B 1 and also preferably combine with each other to form a substituted or unsubstituted fused ring.

[0186] In the compounds according to the present 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 An unsubstituted heterocyclic group having 5 to 25 ring atoms is preferred.

[0187] In the compounds according to the present 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 An unsubstituted heterocyclic group having 5 to 12 ring atoms is preferred.

[0188] In the compounds according to this embodiment, all groups described as "substituted or unsubstituted" are preferably "unsubstituted".

[0189] (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 following the synthesis method and using known alternative reactions and raw materials suited to the target compound.

[0190] (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 protium atom is represented as H or is omitted.

[0191] [ka]

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[0254] Second Embodiment (Materials for organic electroluminescence devices) The material for organic electroluminescence devices according to this embodiment contains the compound according to the first embodiment. One aspect of the material for organic electroluminescence devices includes only the compound according to the first embodiment, and another aspect of the material for organic electroluminescence devices includes the compound according to the first embodiment and another compound different from the compound in the first embodiment. In the material for organic electroluminescence devices of the present 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.

[0255] 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-light-emitting material for the light-emitting layer.

[0256] Third Embodiment [Organic electroluminescence element] The organic EL element according to this embodiment will be described. The organic EL element according to the present 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 an organic compound stacked together. The organic layer may further include an inorganic compound.

[0257] In the organic EL element according to this embodiment, the organic layer contains the compound according to the first embodiment. That is, the organic EL element 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. In the organic EL device of the present embodiment, the organic layer preferably includes an emitting layer, and the emitting layer preferably includes the compound according to the first embodiment.

[0258] 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.

[0259] 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 a compound according to one aspect of the present invention.

[0260] The organic EL element according to this embodiment may be, as a third embodiment, an organic EL element having a single light-emitting layer.

[0261] 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 a schematic configuration of one example of an organic EL element according to a third embodiment. An organic EL element 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. Each of the first organic layer 67 and the second organic layer 89 may be a single layer or may 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, and the like. 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, and the like. 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 element 1 may be configured by stacking a hole injection layer, a hole transport layer, a 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 element 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.

[0262] In the organic EL element according to the third embodiment, a compound according to one aspect of the present invention and a compound represented by general formula (H10) described later can be used in combination in the light-emitting layer of the organic EL element. The compound represented by general formula (H10) will be described below.

[0263] <Compound represented by general formula (H10)> The compound represented by general formula (H10) will be described.

[0264] [ka]

[0265] [In general formula (H10), R 101 ~R 110 Among the groups of two or more adjacent 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed 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 condensed 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, each of the two or more groups represented by the following general formula (H11) is the same or different from each other. -L 101 -Ar 101 (H11)

[0266] (In 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.)]

[0267] The compound represented by the above general formula (H10) may have a deuterium atom in place of a hydrogen atom.

[0268] In one embodiment, Ar in the general formula (H10) 101 At least one of these is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0269] In one embodiment, Ar in the general formula (H10) 101 At least one of the above is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0270] In one embodiment, all of Ar 101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. 101may be the same as or different from each other.

[0271] In one embodiment, Ar in the general formula (H10) 101 one of the Ar 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.

[0272] In one embodiment, L in the general formula (H10) 101 At least one of is a single bond. In one embodiment, L in the general formula (H10) 101 are all single bonds. In one embodiment, L in the general formula (H10) 101 At least one of these is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms. In one embodiment, L in the general formula (H10) 101 At least one of these is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

[0273] In one embodiment, -L in the 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 It is selected from the group consisting of substituted or unsubstituted carbazolyl groups.

[0274] 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 general formula (H10) above.

[0275] 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 general formula (H10) above.

[0276] 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 general formula (H10) above.

[0277] 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.

[0278] In one embodiment, the substituent in the "substituted or unsubstituted" state in general formula (H10) is an alkyl group having 1 to 5 carbon atoms.

[0279] In one embodiment, the compound represented by general formula (H10) is a compound represented by general formula (H20) below.

[0280] [ka]

[0281] (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.

[0282] 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 the general formula (H20) has two or three groups represented by the general formula (H11).

[0283] 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.

[0284] In one embodiment, the compound represented by general formula (H20) is a compound represented by the following general formula (H30).

[0285] [ka]

[0286] (In general formula (H30), L101 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 the general formula (H10).

[0287] That is, the compound represented by the above general formula (H30) is a compound having two groups represented by the above general formula (H11). The compound represented by the above general formula (H30) contains substantially only proton atoms as hydrogen atoms. Incidentally, "having substantially only protium atoms" means that the proportion of protium atoms to the total of a compound having only protium atoms as hydrogen atoms (protium atoms) and a compound having deuterium atoms (deuterium atoms) that have the same structure is 90 mol % or more, 95 mol % or more, or 99 mol % or more.

[0288] In one embodiment, the compound represented by general formula (H30) is a compound represented by the following general formula (H31):

[0289] [ka]

[0290] (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 R121 ~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 Among the groups of two or more adjacent 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, L 101 R is not a single bond bonded to R, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted condensed 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.)

[0291] In one embodiment, the compound represented by general formula (H31) is a compound represented by the following general formula (H32).

[0292] [ka]

[0293] (In general formula (H32), R 101A ~R 108A , L 101 , Ar 101 , R 121 ~R 128 , R 332 and R 333 is as defined in general formula (H31) above.

[0294] In one embodiment, the compound represented by general formula (H31) is a compound represented by the following general formula (H33).

[0295] [ka]

[0296] (In general formula (H33), R 101A ~R 108A , L 101 , Ar 101 , and R 121 ~R 128 is as defined in 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) above.

[0297] In one embodiment, the compound represented by general formula (H31) is a compound represented by the following general formula (H34).

[0298] [ka]

[0299] (In general formula (H34), R 101A ~R 108A , L 101 and Ar 101 is as defined in 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), 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 adjacent two or more of the 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 the general formula (H10).

[0300] In one embodiment, the compound represented by general formula (H31) is a compound represented by the following general formula (H35).

[0301] [ka]

[0302] [In general formula (H35), R 101A ~R 108A , L 101 , Ar 101 and X b is as defined in general formula (H31) above. R 121A ~R 124A Any pair of adjacent two or more of R125A and R 126A , R 126A and R 127A , and R 127A and R 128A Any one pair of these is bonded to each other to form a ring represented by the following general formula (H35a) or general formula (H35b).

[0303] [ka]

[0304] (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 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 which does not form a ring represented by the general formula (H35a) or (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 bonded to 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).

[0305] In one embodiment, the compound represented by general formula (H35) is a compound represented by the following general formula (H36).

[0306] [ka]

[0307] (In general formula (H36), R 101A ~R 108A , L 101 , 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

[0308] In one embodiment, the compound represented by general formula (H34) is a compound represented by the following general formula (H37):

[0309] [ka]

[0310] (In general formula (H37), R 101A ~R 108A , R 125A ~R 128A , L 101 and Ar 101 is as defined in the above general formula (H34).

[0311] In one embodiment, R in the general formulae (H30) to (H37) 101A ~R 108A is a hydrogen atom.

[0312] In one embodiment, the compound represented by general formula (H10) is a compound represented by general formula (H40) below.

[0313] [ka]

[0314] (In general formula (H40), L 101 and Ar 101 is as defined in general formula (H10), R 101A , and R 103A ~R 108A Among the groups of two or more adjacent 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 101A , and R 103A ~R 108A are each independently a hydrogen atom or a substituent R; The substituent R is as defined in the 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). In addition, the compound represented by the general formula (H40) has substantially only proton atoms as hydrogen atoms.

[0315] In one embodiment, the compound represented by general formula (H40) is represented by the following general formula (H41).

[0316] [ka]

[0317] (In general formula (H41), L 101 and Ar 101is as defined in general formula (H40) above.

[0318] In one embodiment, the compound represented by general formula (H40) is a compound represented by any one of the following general formulae (H42-1) to (H42-3).

[0319] [ka]

[0320] (In general formula (H42-1) ~ general formula (H42-3), R 101A ~R 108A , L 101 and Ar 101 is as defined in general formula (H40) above.

[0321] 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).

[0322] [ka]

[0323] (In general formula (H43-1) ~ general formula (H43-3), L 101 and Ar 101 is as defined in general formula (H40) above.

[0324] 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 It is selected from the group consisting of substituted or unsubstituted carbazolyl groups.

[0325] 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.

[0326] 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 possessed by a substituent of Ar 101 A hydrogen atom held by Ar 101 Hydrogen atoms of the substituents of At least one of the is a deuterium atom.

[0327] 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 general formulae (H30) to (H37) is a deuterium atom.

[0328] In one embodiment, the compound represented by general formula (H30) is a compound represented by the following general formula (H30D).

[0329] [ka]

[0330] (In general formula (H30D), R 101A ~R 108A , L 101 and Ar 101 is as defined in 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 possessed by a substituent of Ar 101 A hydrogen atom held by Ar 101 Hydrogen atoms of the substituents At least one of the is a deuterium atom.) That is, the compound represented by the above general formula (H30D) is a compound in which at least one of the hydrogen atoms of the compound represented by the above general formula (H30) is a deuterium atom.

[0331] In one embodiment, R which is a hydrogen atom in the general formula (H30D) 101A ~R 108A At least one of the is a deuterium atom.

[0332] In one embodiment, the compound represented by general formula (H30D) is a compound represented by the following general formula (H31D).

[0333] [ka]

[0334] (In general formula (H31D), R 101A ~R 108A , L 101 and Ar 101 is as defined in 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 Among the groups of two or more adjacent 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, L 101 R is not a single bond bonded to R, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted condensed 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 possessed by a substituent of Ar 101 a hydrogen atom possessed by Ar 101 Hydrogen atoms of the substituents of R is a hydrogen atom 121 ~R 128 , and The substituent R is R 121 ~R 128 Hydrogen atoms possessed by At least one of the is a deuterium atom.)

[0335] In one embodiment, the compound represented by general formula (H31D) is a compound represented by the following general formula (H32D).

[0336] [ka]

[0337] (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 the 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 a dibenzofuran skeleton in general formula (H32D), L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of Ar 101 A hydrogen atom held by Ar 101 Hydrogen atoms of the substituents of At least one of the is a deuterium atom.)

[0338] In one embodiment, the compound represented by general formula (H32D) is a compound represented by the following general formula (H32D-1) or general formula (H32D-2).

[0339] [ka]

[0340] (In the general formula (H32D-1) and the general formula (H32D-2), R 101A ~R 108A , R 125A ~R 128A , L 101 and Ar 101 is as defined in the above general formula (H32D). 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 possessed by a substituent of Ar 101 A hydrogen atom held by Ar 101 Hydrogen atoms of the substituents of At least one of the is a deuterium atom.)

[0341] In one embodiment, at least one of the hydrogen atoms possessed by the compound represented by the general formula (H40), general formula (H41), general formula (H42-1) to general formula (H42-3), or general formula (H43-1) to general formula (H43-3) is a deuterium atom.

[0342] 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.

[0343] In one embodiment, the compound represented by general formula (H40) is a compound represented by the following general formula (H40D).

[0344] [ka]

[0345] (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 adjacent two or more of the 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 possessed by a substituent of Ar 101 A hydrogen atom held by Ar 101 Hydrogen atoms of the substituents of At least one of the is a deuterium atom.)

[0346] In one embodiment, R in the general formula (H40D) 101A , and R 103A ~R 108A At least one of the is a deuterium atom.

[0347] In one embodiment, the compound represented by general formula (H40D) is a compound represented by the following general formula (H41D).

[0348] [ka]

[0349] (In general formula (H41D), L 101 and Ar 101 is as defined in general formula (H40D) above. However, in the general formula (H41D), A hydrogen atom bonded to a carbon atom constituting an anthracene skeleton, L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of Ar 101 A hydrogen atom held by Ar 101 Hydrogen atoms of the substituents At least one of the is a deuterium atom.)

[0350] 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).

[0351] [ka]

[0352] (In general formula (H42D-1) ~ general formula (H42D-3), R 101A ~R 108A , L 101 and Ar101 is as defined in general formula (H40D) above. However, in the above 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 possessed by a substituent of Ar 101 a hydrogen atom possessed by Ar 101 A hydrogen atom carried by a substituent of the formula: A hydrogen atom bonded to a carbon atom constituting a phenyl group in the above general formula (H42D-1) At least one of the groups is a deuterium atom, In the above 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 possessed by a substituent of Ar 101 a hydrogen atom possessed by Ar 101 A hydrogen atom carried by a substituent of the formula: A hydrogen atom bonded to a carbon atom constituting a naphthyl group in the above general formula (H42D-2) At least one of the groups is a deuterium atom, In the above general formula (H42D-3), R is a hydrogen atom 101A , and R 103A ~R 108A , The substituent R is R 101A , and R103A ~R 108A a hydrogen atom possessed by L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of Ar 101 a hydrogen atom possessed by Ar 101 A hydrogen atom carried by a substituent of the formula: A hydrogen atom bonded to a carbon atom constituting a naphthyl group in the above general formula (H42D-3) At least one of the is a deuterium atom.)

[0353] 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).

[0354] [ka]

[0355] (In general formula (H43D-1) ~ general formula (H43D-3), L 101 and Ar 101 is as defined in general formula (H40D) above. however, A hydrogen atom bonded to a carbon atom constituting the anthracene skeleton in the general formula (H43D-1), L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of 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 phenyl group in the above general formula (H43D-1) At least one of the groups is a deuterium atom, A hydrogen atom bonded to a carbon atom constituting an anthracene skeleton in the general formula (H43D-2), L101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of 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 above general formula (H43D-2) At least one of the groups is a deuterium atom, A hydrogen atom bonded to a carbon atom constituting the anthracene skeleton in the general formula (H43D-3), L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of 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 above general formula (H43D-3) At least one of the is a deuterium atom.)

[0356] In one embodiment, in the compound represented by the general formula (H20), Ar 101 At least one of these is a monovalent group having a structure represented by general formula (H50) below.

[0357] [ka]

[0358] (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 with 151~R 154 A pair of two or more adjacent 155 ~R 160 At least one pair of adjacent pairs 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 161 and R 162 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 161 and R 162 , and L 101 Instead of a single bond that bonds with and R does not form the substituted or unsubstituted saturated or unsaturated monocyclic ring and does not form the substituted or unsubstituted condensed 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 the structure represented by the general formula (H50) 101 teeth, 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.

[0359] L in the general formula (H50) 101 The position of the single bond with is not particularly limited. In one embodiment, R in the general formula (H50) 151 ~R 154 or R 155 ~R 160 One of them is L 101It is a single bond that bonds to

[0360] 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:

[0361] [ka]

[0362] (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 )

[0363] (Specific examples of compounds represented by formula (H10)) Specific examples of the compound represented by the general formula (H10) include the following compounds. The compound represented by the general formula (H10) is not limited to these specific examples. In the following specific examples, D represents a deuterium atom.

[0364] [ka]

[0365] [ka]

[0366] [ka]

[0367]

change

[0368]

change

[0369]

change

[0370]

change

[0371]

change

[0372]

change

[0373]

change

[0374]

change

[0375]

change

[0376]

change

[0377] [ka]

[0378] Specific examples of the above groups are as described in the [Definitions] section of this specification.

[0379] 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 used as long as they do not impair the effects of the present invention. 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.

[0380] In the organic EL device according to this embodiment, when the light-emitting layer contains the compound represented by the general formula (H10), the light-emitting layer preferably contains the compound represented by the 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 the general formula (H10) is preferably a host material. When the light-emitting layer contains the compound represented by the above-mentioned 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%.

[0381] Fourth Embodiment The organic EL element according to this embodiment may be, as a fourth embodiment, an organic EL element having two or more light-emitting layers. 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 omitted or simplified by using the same reference numerals or names, etc. In addition, 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.

[0382] The configuration 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 element 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 structure as the light-emitting layer of the organic EL element according to the third embodiment. In the following, differences from the first embodiment will be mainly described, and overlapping descriptions will be omitted or simplified.

[0383] The organic EL element according to this embodiment can have a longer life and improved luminous efficiency by utilizing Tripret-Tripret-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 International Publication WO 2010 / 134350.

[0384] 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 known in the past, the spin state is 25% singlet excitons and 75% triplet excitons. In conventionally known 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)), if it is assumed that higher-order excitons such as quintets immediately return to triplet states, triplet excitons (hereafter, 3 A * When the density of triplet excitons (hereinafter referred to as triplet excitons) increases, the triplet excitons collide with each other and the reaction shown in the following formula occurs. Here, 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 change to singlet excitons. Therefore, the singlet excitons that contribute as light will be 40%, which is the 25% initially generated plus 75% × (1 / 5) = 15%. In this case, the emission ratio of TTF-derived light in the total emission intensity (TTF ratio) will be 15 / 40, or 37.5%. In addition, if it is assumed that the 75% of the triplet excitons initially generated collide with each other to generate singlet excitons (one singlet exciton is generated from two triplet excitons), a very high internal quantum efficiency of 62.5% will be obtained by adding 75% × (1 / 2) = 37.5% to the 25% of the initially generated singlet excitons. In this case, the TTF ratio is 37.5 / 62.5 = 60%.

[0385] In the organic EL device according to this embodiment, from the viewpoint of realizing the TTF mechanism, the triplet energy T 1 (H1) and the triplet energy T 1 (H2) preferably satisfies the relationship of the following mathematical formula (Math. 1), and more preferably satisfies the relationship of the following mathematical formula (Math. 2). T 1 (H2)>T 1 (H1) …(Number 1) T 1 (H2)-T 1 (H1)>0.03eV …(Number 2)

[0386] In the organic EL device according to the present embodiment, by satisfying the relationship of the above formula (Mathematical formula 1), triplet excitons generated by recombination of holes and electrons in the second light-emitting layer are unlikely to be quenched at the interface between the second light-emitting layer and the organic layer even if there are excess carriers 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 due to excess electrons is considered. 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 due to excess holes is considered. The organic EL device according to this embodiment includes a first light-emitting layer and a second light-emitting layer so as to satisfy the relationship of the above formula (Mathematical formula 1), so that triplet excitons generated in the second light-emitting layer can be transferred to the first light-emitting layer without being quenched by excess carriers, and reverse transfer from the first light-emitting layer to the second light-emitting layer can be suppressed. As a result, the TTF mechanism is expressed in the first light-emitting layer, singlet excitons are efficiently generated, and the luminous efficiency is improved. In this way, the organic EL element has a second light-emitting layer that mainly generates triplet excitons, and a first light-emitting layer that mainly exerts the TTF mechanism by utilizing triplet excitons transferred from the second light-emitting layer, as different regions, and uses a compound having a smaller triplet energy than the second host material in the second light-emitting layer as the first host material in the first light-emitting layer, thereby providing a difference in triplet energy, thereby improving the luminous efficiency.

[0387] In the organic EL element 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 life of the element can be extended and the luminous efficiency can be improved.

[0388] (Triplet energy T 1 ) Triplet energy T 1 The measurement method includes the following methods. 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]), a tangent is drawn to the rising edge of the phosphorescence spectrum on the short wavelength side, and the wavelength value λ at the intersection of the tangent and the horizontal axis is determined. edge Based on [nm], the amount of energy calculated from the following conversion formula (F1) is the triplet energy T 1 Let us assume that. Conversion formula (F1):T1 [eV]=1239.85 / λ edge

[0389] 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 of 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 regarded as the tangent to the rising edge on the short wavelength side of the phosphorescence spectrum. Phosphorescence can be measured using a spectrofluorometer body, model F-4500, 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 low-temperature container, an excitation light source, and a light receiving device.

[0390] (Emitting 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.

[0391] (First Light-Emitting Layer) The first light-emitting layer includes a first host material and a first dopant material. The first host material is a compound different from the second host material contained in the second light-emitting layer. The first light-emitting layer according to this embodiment has the same structure as the light-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 element 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 emitting layer of the organic EL element.

[0392] In the organic EL element according to this embodiment, the first light-emitting layer preferably emits light having a maximum peak wavelength of 500 nm or less when the element is in operation. The maximum peak wavelength of the light emitted from the light-emitting layer when the device is in operation can be measured by the following method.

[0393] Maximum peak wavelength λp of light emitted from the light-emitting layer when the device is in operation The maximum peak wavelength λp of the light emitted from the first light-emitting layer when the device is operating 1 In the present study, an organic EL element was prepared by using the same material for the second emitting layer as for the first emitting layer, and the current density of the organic EL element was 10 mA / cm 2 The spectral radiance spectrum when a voltage is applied to the element is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). From the obtained spectral radiance spectrum, the maximum peak wavelength λp 1 Calculate the value (unit: nm). The maximum peak wavelength λp of the light emitted from the second light-emitting layer when the device is operating 2 In the present study, an organic EL element was prepared by using the same material for the first emitting layer as for the second emitting layer, and the current density of the organic EL element was 10 mA / cm 2 The spectral radiance spectrum when a voltage is applied to the element is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). From the obtained spectral radiance spectrum, the maximum peak wavelength λp 2 Calculate the value (unit: nm).

[0394] In the organic EL device according to this embodiment, the triplet energy T 1 (D1), and the triplet energy T of the first host material 1 It is preferable that (H1) satisfies the relationship of the following mathematical formula (Mathematical Formula 4A). T 1 (D1)>T 1 (H1) …(Number 4A)

[0395] In the organic EL device according to this embodiment, the first dopant material and the first host material satisfy the relationship of the above formula (Mathematical Formula 4A), so that triplet excitons generated in the second emitting layer transfer energy to the molecules of the first host material, not to the first dopant material having a higher triplet energy, when they move to the first emitting layer. Also, 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 the molecules of the first dopant material quickly transfer energy to the molecules of the first host material. Triplet excitons of the first host material do not transfer to the first dopant material, but efficiently collide with each other on the first host material due to the TTF phenomenon, thereby generating singlet excitons.

[0396] In the organic EL device according to this embodiment, the singlet energy S 1 (H1) and the singlet energy S of the first dopant material 1 It is preferable that (D1) satisfies the relationship of the following mathematical formula (Mathematical Formula 4). S 1 (H1)>S 1 (D1) ...(Number 4)

[0397] In the organic EL element 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 thus the singlet energy of the first dopant material is smaller than the singlet energy of the first host material. Thus, the singlet excitons generated by the TTF phenomenon transfer energy from the first host material to the first dopant material, and contribute to the emission (preferably fluorescent emission) of the first dopant material.

[0398] (Singlet energy S 1 ) Singlet energy S using solution 1 The measurement method (sometimes called the solution method) is as follows. 10 of the compounds to be measured -5 mol / L or more 10 -4 A toluene solution of less than mol / L is prepared and placed in a quartz cell, and the absorption spectrum of this sample (vertical axis: absorption intensity, horizontal axis: wavelength) is measured at room temperature (300K). 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 the tangent line and the horizontal axis is substituted into the following conversion formula (F2) to calculate the singlet energy. Conversion formula (F2):S 1 [eV]=1239.85 / λedge An example of an absorption spectrum measuring device is a spectrophotometer manufactured by Hitachi (device name: U3310), but is not limited to this.

[0399] The tangent to the falling edge on the long wavelength side of the absorption spectrum is drawn as follows. When moving along the spectral curve from the maximum value on the longest wavelength side among the maximum values ​​of the absorption spectrum in the direction towards 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 at its minimum value on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is regarded as the tangent to the falling edge 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 value on the longest wavelength side.

[0400] 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 formula (Mathematical Formula 3). When the first host material and the second host material satisfy the relationship of the following formula (Mathematical Formula 3), the recombination ability of holes and electrons in the second light-emitting layer is improved. μe(H1)>μe(H2) …(Equation 3)

[0401] In the organic EL element according to this embodiment, when the first emitting layer and the second emitting layer are stacked in the order of 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)

[0402] 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 of the following mathematical formula (Mathematical Formula 32). (μe(H1) / μh(H1))>(μe(H2) / μh(H2)) …(Math. 32)

[0403] The electron mobility can be measured by impedance measurement using a mobility evaluation element prepared by the following procedure. The mobility evaluation element is prepared, for example, by the following procedure. A compound "Target" for measuring electron mobility is vapor-deposited on a glass substrate with an aluminum electrode (anode) so as to cover the aluminum electrode to form a measurement target layer. The following compound ET-A is vapor-deposited on this measurement target layer to form an electron transport layer. LiF is vapor-deposited on the formed electron transport layer to form an electron injection layer. Metallic aluminum (Al) is vapor-deposited on the formed electron injection layer to form a metal cathode. The above-mentioned configuration of the element for evaluating mobility can be simply shown as follows. glass / Al(50) / Target(200) / ET-A(10) / LiF(1) / Al(50) The numbers in parentheses indicate the film thickness (nm).

[0404] [ka]

[0405] The element for evaluating the electron mobility is placed in an impedance measuring device, and impedance measurement is performed. The impedance measurement is performed by sweeping the measurement frequency from 1 Hz to 1 MHz. At that time, a DC voltage V is applied to the element at the same time as an AC amplitude of 0.1 V. The modulus M is calculated from the measured impedance Z using the relationship of 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 pi. 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 thickness of the organic thin films that constitute the element, and in the case of the element configuration for evaluating the electron mobility, d=210 [nm].

[0406] The hole mobility can be measured by impedance measurement using a mobility evaluation element prepared by the following procedure. The mobility evaluation element is prepared, for example, by the following procedure. On a glass substrate with an ITO transparent electrode (anode), the following compound HA-2 is 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 deposited to form a hole transport layer. Next, a compound Target, which is the target for measuring hole mobility, is deposited to form a measurement target layer. On top of this measurement target layer, metal aluminum (Al) is deposited to form a metal cathode. The above-mentioned configuration of the element for evaluating mobility can be simply shown as follows. ITO(130) / HA-2(5) / HT-A(10) / Target(200) / Al(80) The numbers in parentheses indicate the film thickness (nm).

[0407] [ka]

[0408] The element for evaluating the hole mobility is placed in an impedance measuring device, and impedance measurement is performed. The impedance measurement is performed by sweeping the measurement frequency from 1 Hz to 1 MHz. At that time, a DC voltage V is applied to the element at the same time as an AC amplitude of 0.1 V. The modulus M is calculated from the measured impedance Z using the relationship of the above-mentioned 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-mentioned calculation formula (C2). Using τ obtained from the above formula (C2), the hole mobility μh is calculated from the relationship in 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 constitute the element, and in the case of the element configuration for evaluating the hole mobility, d=215 [nm].

[0409] In this specification, the electron mobility and hole mobility 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 Model 1260 impedance measuring device, and for higher accuracy, a Solartron Model 1296 dielectric constant measuring interface can also be used.

[0410] 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, even 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 mass %. In this embodiment, the first emitting layer may contain materials other than the first host material and the first dopant material. The first emitting layer may contain only one type of first host material or may contain two or more types of first dopant materials.

[0411] In the organic EL device according to this embodiment, the thickness of the first light-emitting layer is preferably 5 nm or more, more preferably 15 nm or more. If the thickness of the first light-emitting layer is 5 nm or more, it is easy to prevent triplet excitons that have moved from the second light-emitting layer to the first light-emitting layer from returning to the second light-emitting layer. Also, if the thickness of the first light-emitting layer is 5 nm or more, triplet excitons can be sufficiently separated from the recombination portion in the second light-emitting layer. In the organic EL device according to the present embodiment, the thickness of the first light-emitting layer is preferably 20 nm or less. If the thickness of the first light-emitting layer is 20 nm or less, the density of triplet excitons in the first light-emitting layer can be improved, making the TTF phenomenon more likely to occur. In the organic EL element according to this embodiment, the first light-emitting layer preferably has a thickness of 5 nm or more and 20 nm or less.

[0412] (Second Light Emitting Layer) The second 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 emitting layer. The second dopant material is preferably a compound that exhibits luminescence with a maximum peak wavelength of 500 nm or less, and more preferably a compound that exhibits fluorescent emission 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.

[0413] In the organic EL device according to this embodiment, the second dopant material and the first dopant material are the same or different compounds.

[0414] In the organic EL device according to this embodiment, it is preferable that the second light-emitting layer does not contain a metal complex. Also, in the organic EL device according to this embodiment, it is preferable that the first light-emitting layer does not contain a boron-containing complex.

[0415] 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.

[0416] In the emission spectrum of the second dopant material, the peak at which the emission intensity is maximum is defined as the maximum peak, and the height of the maximum peak is defined as 1. It is preferable that the heights of other peaks appearing in the emission spectrum are less than 0.6. Note that the peaks in the emission spectrum are defined as maximum values. In addition, it is preferable that the emission spectrum of the second luminescent compound has less than three peaks.

[0417] In the organic EL element according to this embodiment, the second light-emitting layer preferably emits light having a maximum peak wavelength of 500 nm or less when the element is in operation.

[0418] (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, and 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 preferable that the compound is a pyrene derivative (a compound represented by the general formula (H100) described later). The second host material is Benzanthracene derivatives (compounds represented by the general formula (H1X) described below) or A benzoxanthene derivative (a compound represented by the general formula (H14X) described below) is also preferred.

[0419] When the second host material is a pyrene derivative, the second host material is preferably a compound represented by the following general formula (H100).

[0420] (Compound represented by general formula (H100))

[0421] [ka]

[0422] (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-(R905 ) 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 the above is a group represented by general formula (H110), 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 or different from each other, Ar 101 If there are two or more, there are two or more Ar 101 are identical or different from each other, In the general formula (H110), * indicates the bonding position to the pyrene ring in the general formula (H100).

[0423] (In the above 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.)

[0424] 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).

[0425] [ka]

[0426] (In the general formula (H111), 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; 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 )(R902 )(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 R's 121 are identical or different from each other, md is 3, The Three R's 122 are either identical or different.)

[0427] 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 placed at any one of positions *5 to *8. 112 is bonded, and R is placed in the remaining three positions from *5 to *8. 122 are combined.

[0428] [ka]

[0429] For example, in the group represented by the general formula (H111), L 111 is bonded to the carbon atom indicated by *2 in the ring structure represented by general formula (H111a), and L 112is bonded to the position of the carbon atom marked *7 in the ring structure represented by general formula (H111a), the group represented by general formula (H111) is represented by the following general formula (H111b).

[0430] [ka]

[0431] (In the general formula (H111b), X 10 , L 111 , L 112 , ma, mb, Ar 101 , R 121 , R 122 , R 123 , R 124 and 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 or different from each other, Multiple R 122 are either identical or different.)

[0432] 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).

[0433] In the organic EL element according to this embodiment, ma is 0, 1 or 2; It is preferred that mb is 0, 1 or 2.

[0434] In the organic EL element according to this embodiment, ma is 0 or 1; It is preferred that mb is 0 or 1.

[0435] 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.

[0436] 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.

[0437] 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).

[0438] [ka]

[0439] (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 The bond position is shown.)

[0440] In the organic EL element according to this embodiment, The second host material is preferably represented by the following formula (H101).

[0441] [ka]

[0442] (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.)

[0443] In the organic EL element according to this embodiment, L 101 teeth, A single bond, or A substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms is preferred.

[0444] In the organic EL element according to this embodiment, The second host material is preferably represented by the following general formula (H102).

[0445] [ka]

[0446] (In the general formula (H102), R 101 ~R 120 each 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 R's 121 are identical or different from each other, md is 3, The Three R's 122 are either identical or different.)

[0447] In the compound represented by the general formula (H102), ma is 0, 1 or 2; It is preferred that mb is 0, 1 or 2.

[0448] In the compound represented by the general formula (H102), ma is 0 or 1; It is preferred that mb is 0 or 1.

[0449] 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 general formula (H110).

[0450] 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.

[0451] 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.

[0452] 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.

[0453] 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.

[0454] In the organic EL device according to this embodiment, R 101 ~R 110 is preferably a hydrogen atom.

[0455] In the compound represented by the general formula (H100), all of the groups described as "substituted or unsubstituted" are preferably "unsubstituted".

[0456] The compound represented by the general formula (H100) can be produced by a known method.

[0457] (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.

[0458] [ka]

[0459] [ka]

[0460] [ka]

[0461] [ka]

[0462]

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[0473] [ka]

[0474] [ka]

[0475] [ka]

[0476] [ka]

[0477] [ka]

[0478] [ka]

[0479] [ka]

[0480] When the second host material is a benzanthracene derivative, the second host material is preferably a compound represented by the following general formula (H1X).

[0481] (Compound represented by general formula (H1X))

[0482] [ka]

[0483] (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 )(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 (H11X), However, R 101 ~R 112 At least one of the above is a group represented by 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 or different from each other, Ar 101 If there are two or more, there are two or more Ar 101 are identical 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).

[0484] 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).

[0485] [ka]

[0486] (In the above 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 R's 341 are identical or different from each other, md is 3, The Three R's 342 are either identical or different.)

[0487] 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 placed at any one of positions *5 to *8. 112 is bonded, and R is placed in the remaining three positions from *5 to *8. 342 are combined.

[0488] [ka]

[0489] For example, in the group represented by the general formula (H111X), L 111 is bonded to the carbon atom marked with *2 in the ring structure represented by the general formula (H111aX), and L 112 is bonded to the position of the carbon atom marked *7 in the ring structure represented by general formula (H111aX), the group represented by general formula (H111X) is represented by the following general formula (H111bX).

[0490] [ka]

[0491] (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 or different from each other, Multiple R 342 are either identical or different.)

[0492] 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).

[0493] In the compound represented by the general formula (H1X), it is preferable that ma is 1 or 2, and mb is 1 or 2.

[0494] In the compound represented by the general formula (H1X), it is preferable that ma is 1 and mb is 1.

[0495] 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.

[0496] 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.

[0497] The compound represented by the above general formula (H1X) is also preferably represented by the following general formula (H101X).

[0498] [ka]

[0499] (In the above 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 site with 111 or R 112 , and L 101 R is not a bond site 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, 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.)

[0500] 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.

[0501] The compound represented by the general formula (H1X) is also preferably represented by the following general formula (H102X).

[0502] [ka]

[0503] (In the above 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 site with 111 or R 112 And L 112 R is not a bond site 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 344and 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 R's 341 are identical or different from each other, md is 3, The Three R's 342 are either identical or different.)

[0504] 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.

[0505] 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.

[0506] 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).

[0507] [ka]

[0508] (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, The * in the general formula (H11AX) and the general formula (H11BX) each indicates a bonding position to the benz[a]anthracene ring in the general formula (H1X).

[0509] The compound represented by the general formula (H1X) is also preferably represented by the following general formula (H103X).

[0510] [ka]

[0511] (In the above general formula (H103X), R 101 ~R 110 And R 112 respectively represent R in the general formula (H1X). 101 ~R 110 And R 112 is synonymous with R 121 ~R 129、 R 330 , and R 331 , and L 131 and L 132 respectively represent R in the general formula (H11BX). 121 ~~R 129、 R 330 , and R 331 , and L 131 and L 132is equivalent to

[0512] 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.

[0513] 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.

[0514] 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 general formula (H110).

[0515] In the compound represented by the general formula (H1X), R 101 ~R 112 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.

[0516] 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 which 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 the formula (I) is not a substituted or unsubstituted benz[a]anthryl group.

[0517] In the compound represented by the general formula (H1X), R other than the group represented by the general formula (H11X) 101 ~R 112are 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.

[0518] In the compound represented by the general formula (H1X), R other than the group represented by the general formula (H11X) 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.

[0519] In the compound represented by the general formula (H1X), R other than the group represented by the general formula (H11X) 101 ~R 112 is preferably a hydrogen atom.

[0520] The compound represented by the general formula (H1X) can be produced by a known method.

[0521] (Specific examples of compounds represented by 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.

[0522] [ka]

[0523] [ka]

[0524] [ka]

[0525] [ka]

[0526] When the second host material is a benzoxanthene derivative, the second host material is preferably a compound represented by the following general formula (H14X).

[0527] (Compound represented by general formula (H14X))

[0528] [ka]

[0529] (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 the general formula (H141), However, R 1401 ~R 1410 At least one of the above is a group represented by general formula (H141), 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 or different from each other, Ar 1401 If there are two or more, there are two or more Ar 1401 are identical or different from each other, In the general formula (H141), * indicates the bonding position to the ring represented by the general formula (H14X).

[0530] The compound represented by the general formula (H14X) can be produced by a known method.

[0531] (Specific examples of compounds represented by 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.

[0532] [ka]

[0533] [ka]

[0534] (Second Dopant Material) The second dopant material may be, for example, 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.

[0535] (Compound represented by general formula (5))

[0536] [ka]

[0537] (In the general formula (5), R 501 ~R 507 and R 511 ~R 517 Among the groups of two or more adjacent 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 501 ~R 507 and R 511 ~R 517are 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.

[0538] "R 501 ~R 507 and R 511 ~R 517 "A set of two or more adjacent pairs of R 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 503 A combination of a set consisting of:

[0539] In one embodiment, R 501 ~R 507 and R 511 ~R 517 At least one, preferably two, of the formula (I) are -N(R 906 )(R 907 ) is a group represented by the formula:

[0540] 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.

[0541] In one embodiment, the compound represented by the general formula (5) is a compound represented by the following general formula (52).

[0542] [ka]

[0543] (In the general formula (52), R 531 ~R 534 and R 541 ~R 544 At least one pair of adjacent pairs 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 531 ~R 534 , R 541 ~R 544 , and R 551 and R 552 are 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.

[0544] In one embodiment, the compound represented by the general formula (5) is a compound represented by the following general formula (53).

[0545] [ka]

[0546] (In the general formula (53), R 551 , R 552 and R 561 ~R 564each independently represents R in the general formula (52) 551 , R 552 and R 561 ~R 564 is equivalent to

[0547] 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).

[0548] In one embodiment, R in the 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.

[0549] 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.

[0550] The compound represented by the above general formula (5) can be produced by a known method.

[0551] (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.

[0552]

change

[0553]

change

[0554]

change

[0555]

change

[0556]

change

[0557]

change

[0558]

change

[0559]

change

[0560]

change

[0561]

change

[0562]

change

[0563] [ka]

[0564] [ka]

[0565] [ka]

[0566] [ka]

[0567] (Compound represented by general formula (6))

[0568] [ka]

[0569] (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 heterocycle having 5 to 50 ring atoms, R 601 and R 602 each independently forms a substituted or unsubstituted heterocycle together with the ring a, ring b, or ring c, or does not form a substituted or unsubstituted heterocycle; R that does not form a 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.

[0570] 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 two-ring structure of the general formula (6) composed of a boron atom and two nitrogen atoms.

[0571] The "aromatic hydrocarbon rings" 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 "aryl group". The "aromatic hydrocarbon ring" of ring a contains the three carbon atoms on the central fused two-ring structure of 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.

[0572] 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 the "substituted or unsubstituted heterocycle having 5 to 50 ring-forming atoms" include compounds in which a hydrogen atom has been introduced into the "heterocyclic group" described in specific example group G2.

[0573] R 601 and R 602may each independently bond to ring a, ring b, or ring c to form a substituted or unsubstituted heterocycle. In this case, the heterocycle contains the nitrogen atom on the central fused two-ring structure of the general formula (6). In this case, the heterocycle may contain a heteroatom other than the nitrogen atom. R 601 and R 602 is bonded to the ring a, ring b, or ring c, specifically means that an atom constituting the 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. For example, R 601 is bonded to the a ring, R 601 A two-ring (or three-ring or more) nitrogen-containing heterocycle may be formed by condensing a ring containing the same with ring a. Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing two-ring or more condensed heterocyclic groups in specific example group G2. R 601 When is bonded to ring b, R 602 When R is bonded to ring a, 602 The same applies when is bonded to ring c.

[0574] 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, the ring b, and the ring c in the general formula (6) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.

[0575] In one embodiment, R in the 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.

[0576] In one embodiment, the compound represented by the general formula (6) is a compound represented by the following general formula (62).

[0577] [ka]

[0578] (In the general formula (62), R 601A is R 611 and R 621 or a substituted or unsubstituted heterocyclic ring is formed by combining with one or more selected from the group consisting of R 602A is R 613 and R 614 or a substituted or unsubstituted heterocyclic ring is formed by combining with one or more selected from the group consisting of R that does not form a substituted or unsubstituted heterocycle 601A and 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 At least one pair of adjacent pairs 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 does not form the substituted or unsubstituted heterocycle, does not form the substituted or unsubstituted monocycle, 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.

[0579] R in the above general formula (62) 601A and R 602A are R in the general formula (6), 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-ring or more) nitrogen-containing heterocycle in which a ring containing the ring is condensed with a benzene ring corresponding to the ring a. Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing two-ring or more condensed heterocyclic groups in the specific example group G2. R 601A and R 621 If R is bonded, 602A and R 613 When R is bonded, 602A and R 614 The same applies when is combined.

[0580] R 611 ~R621 At least one pair 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 the 6-membered ring 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 condensed with the 6-membered ring to which they are bonded, and the condensed ring formed is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring.

[0581] In one embodiment, R 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.

[0582] In one embodiment, R 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.

[0583] In one embodiment, R 611 ~R 621 are each independently A hydrogen atom, or It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0584] In one embodiment, R 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.

[0585] In one embodiment, the compound represented by the general formula (62) is a compound represented by the following general formula (63).

[0586] [ka]

[0587] (In the general formula (63), R 631 is R 646 or not forming a substituted or unsubstituted heterocycle, R 633 is R 647 or not forming a substituted or unsubstituted heterocycle, R 634 is R 651 or not forming a substituted or unsubstituted heterocycle, R 641 is R 642 or not forming a substituted or unsubstituted heterocycle, R 631 ~R 651 At least one pair of adjacent pairs 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 does not form the substituted or unsubstituted heterocycle, does not form the substituted or unsubstituted monocycle, and does not form the substituted or unsubstituted fused ring. 631 ~R651 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.

[0588] R 631 is R 646 may combine with R to form a substituted or unsubstituted heterocycle. For example, R 631 and R 646 Combined, R 646 may be bonded to a benzene ring, a ring containing N, and a benzene ring corresponding to ring a 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 ring group having three or more condensed rings in the specific example group G2. 633 and R 647 If R is bonded, 634 and R 651 When R is bonded, 641 and R 642 The same applies when is combined.

[0589] In one embodiment, R 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.

[0590] In one embodiment, R 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.

[0591] In one embodiment, R 631 ~R 651 are each independently A hydrogen atom, or It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0592] In one embodiment, R 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.

[0593] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63A):

[0594] [ka]

[0595] (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.

[0596] 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.

[0597] In one embodiment, R 661 ~R 665 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0598] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63B):

[0599] [ka]

[0600] (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 ~R 675 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.

[0601] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63B').

[0602] [ka]

[0603] (In the general formula (63B′), R 672 ~R 675 each independently represents R in the general formula (63B) 672 ~R 675 is equivalent to

[0604] 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.

[0605] 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.

[0606] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63C):

[0607] [ka]

[0608] (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.

[0609] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63C'):

[0610] [ka]

[0611] (In the general formula (63C'), R 683 ~R 686 each independently represents R in the general formula (63C) 683 ~R 686 is equivalent to

[0612] 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.

[0613] In one embodiment, R 681 ~R 686 each independently represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0614] The compound represented by the general formula (6) is first prepared by connecting the ring a, the ring b and the ring c to a linking group (NR 601 Groups containing NR 602 An intermediate can be produced by linking the a, b and c rings with a linking group (a group containing a boron atom) (reaction 2). In reaction 1, an amination reaction such as the Bachbrut-Hartwig reaction can be applied. In reaction 2, a tandem hetero Friedel-Crafts reaction can be applied.

[0615] The compound represented by the general formula (6) can be produced by a known method.

[0616] (Specific examples of compounds represented by formula (6)) Specific examples of the compound represented by formula (6) include the following compounds: However, the compound represented by formula (6) is not limited to the following specific examples.

[0617] [ka]

[0618] [ka]

[0619] [ka]

[0620] [ka]

[0621] [ka]

[0622] [ka]

[0623] [ka]

[0624] [ka]

[0625] [ka]

[0626] [ka]

[0627] [ka]

[0628] [ka]

[0629] In the organic EL device according to this embodiment, the singlet energy S 1 (H2) and the singlet energy S of the second dopant material 1 It is preferable that (D2) satisfies the relationship of the following mathematical formula (Mathematical formula 20). S 1 (H2)>S 1 (D2) ...(Number 20)

[0630] When the second host material and the second dopant material satisfy the relationship of the mathematical formula (Mathematical Formula 20), the singlet excitons generated on the second host material can easily transfer energy from the second host material to the second dopant material, and contribute to the emission (preferably fluorescent emission) of the second dopant material.

[0631] In the organic EL device according to this embodiment, the triplet energy T 1 (H2) and the triplet energy T of the second dopant material 1 It is preferable that (D2) satisfies the relationship of the following formula (Mathematical formula 20A). T 1 (D2)>T 1 (H2) ...(Number 20A)

[0632] 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 through the second host material rather than through the second dopant material having a higher triplet energy, and therefore are more likely to move to the first emitting layer.

[0633] In the organic EL device according to this embodiment, the second light-emitting layer preferably contains the second dopant material in an amount of 0.5 mass % or more of the total mass of the second light-emitting layer, more preferably more than 1.1 mass % of the total mass of the second light-emitting layer, even more preferably 1.2 mass % or more of the total mass of the second light-emitting layer, and even more preferably 1.5 mass % or more of the total mass of the second light-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.

[0634] In the organic EL device according to this embodiment, the second light-emitting layer preferably contains the second host material in an amount of 60 mass % or more of the total mass of the second light-emitting layer, more preferably 70 mass % or more of the total mass of the second light-emitting layer, even more preferably 80 mass % or more of the total mass of the second light-emitting layer, even more preferably 90 mass % or more of the total mass of the second light-emitting layer, and even more preferably 95 mass % or more of the total mass of the second light-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 mass %. In addition, the present 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.

[0635] In the organic EL device according to this embodiment, the thickness of the second light-emitting layer is preferably 3 nm or more, and more preferably 5 nm or more. If the thickness of the second light-emitting layer is 3 nm or more, the thickness 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. If the thickness of the second emitting layer is 15 nm or less, the thickness is thin enough for triplet excitons to move to the first emitting layer. In the organic EL element according to this embodiment, the thickness of the second light-emitting layer is more preferably 3 nm or more and 15 nm or less.

[0636] (Other layers of organic electroluminescence devices) 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.

[0637] The organic EL element 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 an anode, a first light-emitting layer, a second light-emitting layer, and a cathode in this order. In either case 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-mentioned mathematical formula (Mathematical formula 1) and by containing the compound according to the first embodiment in the first light-emitting layer, the effects of forming the light-emitting layer into a laminated structure (the effect of extending the life of the element and the effect of improving the luminous efficiency) can be expected.

[0638] The organic EL device according to this embodiment may be composed of 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.

[0639] The organic EL element 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 element 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.

[0640] 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.

[0641] 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.

[0642] 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 stacking 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 in this order from the anode 3 side. 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 configured by stacking 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 in this order from the anode 3 side. The present invention is not limited to the configurations of the organic EL element shown in FIGS.

[0643] (Third Light Emitting Layer) The organic EL device according to this embodiment may further include a third light-emitting layer. The third emitting layer includes a third host material, and the first host material, the second host material, and the third host material are different from each other. The third emitting layer includes 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 each other. The triplet energy T of the second host material is 1 The triplet energy T of (H2) and the third host material 1 It is preferable that (H3) satisfies the relationship of the following mathematical formula (Mathematical Formula 5). T 1 (H2)>T 1 (H3) …(Number 5)

[0644] The third dopant material is preferably a compound that exhibits luminescence with a maximum peak wavelength of 500 nm or less, and more preferably a compound that exhibits fluorescent emission with a maximum peak wavelength of 500 nm or less.

[0645] When the organic EL device according to this embodiment includes a third emitting layer, the triplet energy T 1 The triplet energy T of (H1) and the third host material 1 It is preferable that (H3) satisfies the relationship of the following mathematical formula (Mathematical Formula 6). T 1 (H1)>T 1 (H3) …(Number 6)

[0646] 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.

[0647] In the organic EL element according to this embodiment, it is preferable that the first light-emitting layer and the second light-emitting layer are in direct contact with each other.

[0648] In this specification, the layer structure in which "the first emitting layer and the second 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 a compound for the first emitting layer and the process of vapor-depositing a 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 deposition of the compound for the first emitting layer and the process of vapor deposition of 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.

[0649] 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.

[0650] In this specification, the layer structure in which "the first emitting layer and the third emitting layer are in direct contact with each other" 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 process of vapor-depositing 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. (LS5) When the first emitting layer and the third emitting layer each 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 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 third host material 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 the region is present at the interface between the first emitting layer and the third emitting layer.

[0651] 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.

[0652] The intermediate layer is preferably a non-doped layer. The intermediate layer is preferably a layer that does not contain a light-emitting compound (dopant material). The intermediate layer is preferably a layer that 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 the intervening layer material 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.

[0653] 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.

[0654] When the intervening layer contains a plurality of intervening layer materials, the content of each of the intervening layer materials is preferably 10 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 mass% or more of the total mass of the intervening layer, more preferably 70 mass% or more of the total mass of the intervening layer, even more preferably 80 mass% or more of the total mass of the intervening layer, even more preferably 90 mass% or more of the total mass of the intervening layer, and even more preferably 95 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 of intervening layer materials. 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 mass %. In the organic EL element according to the fourth embodiment, the intervening layer may contain a material other than the intervening layer material.

[0655] The intervening layer may be composed of a single layer, or may be composed of two or more laminated layers.

[0656] The thickness of the intermediate 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.

[0657] 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.

[0658] (substrate) The substrate is used as a support for the organic EL element. For example, glass, quartz, plastic, etc. can be used as the substrate. 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. An inorganic deposition film can also be used.

[0659] (anode) The anode formed on the substrate is made of a metal with a large work function (specifically, 4.0 eV or more), It is preferable to use alloys, electrically conductive compounds, and mixtures thereof. Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, etc. 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).

[0660] These materials are usually formed into a film by a sputtering method. For example, indium oxide-zinc oxide can be formed by a sputtering method by using a target in which zinc oxide is added to indium oxide at 1 mass % or more and 10 mass % or less. In addition, indium oxide containing tungsten oxide and zinc oxide can be formed by a sputtering method by using a target in which tungsten oxide is added to indium oxide at 0.5 mass % or more and 5 mass % or less and zinc oxide is added to indium oxide at 0.1 mass % or more and 1 mass % or less. In addition, it may be formed by a vacuum deposition method, a coating method, an inkjet method, a spin coating method, or the like.

[0661] 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 that materials that can be used as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures of these, as well as other elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0662] Materials with small work functions, such as elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these, can also be used. When alkali metals, alkaline earth metals, and alloys containing these are used to form the anode, vacuum deposition and sputtering methods can be used. Furthermore, when silver paste or the like is used, coating and inkjet methods can be used.

[0663] (cathode) For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof, each having a small work function (specifically, 3.8 eV or less). Specific examples of such a cathode material include elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.

[0664] 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.

[0665] By providing an electron injection layer, the cathode can be formed using various conductive materials, such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the magnitude of the work function. These conductive materials can be formed into films by a sputtering method, an inkjet method, a spin coating method, or the like.

[0666] (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, manganese oxide, etc.

[0667] In addition, examples of 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-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and other aromatic amine compounds, as well as dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) are also included.

[0668] In addition, as a substance with high hole injection properties, a polymer compound (oligomer, dendrimer, polymer, etc.) can be used. For example, polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD) can be used. In addition, a polymer compound to which an acid is added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) or polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can be used.

[0669] (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), Examples of aromatic amine compounds that can be used include 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The substances mentioned here are mainly 10 -6 cm 2 / (V s) or higher.

[0670] 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) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) may also be used.

[0671] 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 a single layer or a stack of two or more layers made of the above substances.

[0672] (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. For the electron transport layer, 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 can be used. Specifically, low-molecular organic compounds include Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq), 3 ), Bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq 2 Metal complexes such as BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(pt-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 (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: 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 any other substance may be used as the electron transport layer as long as it has a higher electron transporting property than a hole transporting property. The electron transport layer may be formed of a single layer or may be formed of two or more layers of the above substances.

[0673] 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).

[0674] (electron injection layer) The electron injection layer is a layer containing a substance with high electron injection properties. Examples of the electron injection layer include lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), and calcium fluoride (CaF 2 Alkaline metals, alkaline earth metals, or compounds thereof, such as lithium oxide (LiOx), can be used. In addition, a material having electron transport properties containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a material containing magnesium (Mg) in Alq, can be used. In this case, electron injection from the cathode can be performed more efficiently.

[0675] Alternatively, a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such a composite material has excellent electron injection and 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 in transporting the generated electrons, and 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, and examples thereof include lithium, cesium, magnesium, calcium, erbium, and ytterbium. Furthermore, alkali metal oxides and alkaline earth metal oxides are preferred, and examples thereof include lithium oxide, calcium oxide, and barium oxide. Furthermore, a Lewis base such as magnesium oxide can also be used. Furthermore, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.

[0676] (Layer formation method) The method for forming each layer of the organic EL element of the 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.

[0677] (Film thickness) The thickness of each organic layer of the organic EL element of the embodiment is not limited unless otherwise specified above. In general, 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 of the organic EL element is usually preferably in the range of several nm to 1 μm. Fifth Embodiment [Electronic equipment] The electronic device according to the present embodiment is equipped with any of the organic EL elements according to the above-mentioned embodiments. Examples of the electronic device include display devices and light-emitting devices. Examples of the display device include display components (e.g., organic EL panel modules), televisions, mobile phones, tablets, and personal computers. Examples of the light-emitting device include lighting and vehicle lamps.

[0678] [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.

[0679] For example, the light-emitting layer is not limited to one layer, and multiple light-emitting layers may be laminated. When the organic EL element has multiple light-emitting layers, at least one of the organic layers may satisfy the conditions described in the above embodiment, and at least one of the light-emitting layers preferably 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 electronic transition from a triplet excited state directly to a 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.

[0680] In addition, 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 in contact with the light-emitting layer on the cathode side, the blocking layer transports electrons and prevents holes from reaching a layer (e.g., an electron transport layer) on the cathode side of 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. In addition, 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) on the anode side of 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 the excitation energy from leaking from the light-emitting layer to the surrounding layers, and prevents excitons generated in the light-emitting layer from migrating to layers on the electrode side of the barrier layer (e.g., the electron transport layer and the hole transport layer, etc.). The light emitting layer and the barrier layer are preferably in contact with each other.

[0681] In addition, the specific structure and shape in carrying out the present invention may be other structures and shapes within the scope of the invention in which the object of the present invention can be achieved. EXAMPLES

[0682] 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.

[0683] <Compound> The structures of the compound according to Example 1 and the compound used in the production of the organic EL device according to Example 1A are shown below: Compound BD-1 corresponds to the compound represented by general formula (1).

[0684] [ka]

[0685] The structures of other compounds used in the production of the organic EL device according to Example 1A are shown below.

[0686] [ka]

[0687] [ka]

[0688] [ka]

[0689] [ka]

[0690] The structures of the comparative compounds according to Comparative Example 1 and Comparative Example 2 are shown below.

[0691] [ka]

[0692] <Compound evaluation 1> (Fluorescence emission maximum peak wavelength and emission spectrum half-width FWHM) Compound BD-1 was dissolved in toluene and diluted with 5.0 × 10 -6 A 1.0 mol / L solution was prepared. The resulting solution was placed in a quartz cell (optical path length 1.0 cm), and the maximum peak wavelength of fluorescent emission (unit: nm) and the half width at half maximum (FWHM) of the emission spectrum (unit: nm) when excited at 400 nm were measured using a fluorescence spectrum measuring device "Spectrofluorophotometer FP-8300" (manufactured by JASCO Corporation). FWHM is an abbreviation for Full Width at Half Maximum. The measurement results are shown in Table 1.

[0693] (Photoluminescence quantum yield) The compound to be measured, BD-1, was dissolved in toluene and diluted with 5.0×10 -6 A mol / L solution was prepared, and after freezing and degassing, an argon-saturated solution was prepared. The resulting solution was transferred to a quartz cell (optical path length 1.0 cm), and the photoluminescence quantum yield (PLQY) was measured using an absolute PL quantum yield measurement device "Hamamatsu Quantaurus-QY C11347" (manufactured by Hamamatsu Photonics K.K.). The measurement results are shown in Table 1.

[0694] [Table 1]

[0695] The compound BD-1 according to Example 1 had an emission peak wavelength in a desired wavelength band, a narrow half-width of the emission spectrum, and exhibited a high PLQY value.

[0696] <Fabrication of organic EL elements> An organic EL device was prepared as follows and evaluated.

[0697] Example 1A A glass substrate (size: 25 mm × 25 mm × 0.7 mm, manufactured by Geomatec Co., Ltd.) equipped with an indium tin oxide (ITO) transparent electrode having a thickness of 130 nm was used as the anode. The glass substrate equipped with the ITO transparent electrode was cleaned with nitrogen plasma for 100 seconds. The cleaned glass substrate was attached to a substrate holder and transferred into a vacuum evaporator. Then, a pressure of 10 -6 mbar or more than 10 -8 Compound HT-1 and compound HA were co-deposited at a deposition rate of 0.01 Å / min to 2 Å / min at 0.75 mbar or less to form a hole injection layer (HI) having a thickness of 10 nm. The proportion of compound HT-1 in this hole injection layer was 97% by mass, and the proportion of compound HA was 3% by mass. Next, following the formation of the hole injection layer, a compound HT-1 was evaporated to form a first hole transport layer (HT) having a thickness of 80 nm. Following the formation of the first hole-transporting layer, compound HT-2 was evaporated to form a second hole-transporting layer (also called an 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 ratio 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 called a hole-blocking layer) (HBL) having 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 deposited on the second electron transport layer to form an electron injection layer having a thickness of 1 nm. Metallic Al was evaporated onto the electron injection layer to form a cathode with a thickness of 80 nm. The fabricated device was sealed with a glass cover and a moisture absorbent in an inert nitrogen atmosphere containing less than 1 ppm of water and oxygen. The device configuration of Example 1A is shown in schematic form as follows. 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(80) The numbers in parentheses indicate the film thickness (unit: nm). The numbers expressed as percentages (97%:3%) indicate the ratios (mass%) of the compounds HT-1 and HA in the hole injection layer, and the numbers expressed as 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.

[0698] <Evaluation of organic EL elements> The organic EL devices thus fabricated were evaluated as follows. The evaluation results are shown in Table 2.

[0699] (Drive 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

[0700] (Maximum peak wavelength λp and emission spectrum half width FWHM) Current density is 10mA / cm 2 The spectral radiance spectrum when a voltage was applied to the element so that the spectral radiance spectrum was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) The maximum peak wavelength λp (unit: nm) and the emission spectrum half width FWHM (unit: nm) were calculated from the obtained spectral radiance spectrum.

[0701] (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 spectral radiance 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 performed.

[0702] [Table 2]

[0703] The organic EL element according to Example 1A had an emission peak wavelength in a desired wavelength band, a narrow half-width of the emission spectrum, and emitted light with high efficiency.

[0704] <Compound evaluation 2> (Lowest excited singlet energy level) The lowest excited singlet energy level (S1 energy level) of compound BD-1, comparative compound Ref-1 and comparative compound Ref-2 was calculated by TD-DFT calculation (using B3LYP as a hybrid paradigm and 6-31g* as a basis set). All calculations were performed using the Gaussian 16 software program available from Gaussian Inc. The results are shown in Table 3.

[0705] [Table 3]

[0706] As shown in Table 1, the compound BD-1 of Example 1 had a maximum peak wavelength of 446 nm. On the other hand, the comparative compound Ref-1 of Comparative Example 1 and the comparative compound Ref-2 of Comparative Example 2, which are estimated to have a higher S1 energy level than the compound BD-1, have an emission wavelength on the short wavelength side with respect to the blue emission wavelength (445 nm or more and 465 nm or less) that is preferable for display applications, and therefore, it is not preferable to use the comparative compounds Ref-1 and Ref-2 as organic EL element materials for display applications.

[0707] <Synthesis Example> (Synthesis of compound BD-1) The synthesis method of compound BD-1 is described below.

[0708] [ka]

[0709] [Production of Intermediate 1-1] 1-Bromo-9H-carbazole (10.0 g, 40.6 mmol), bis(pinacolato)diboron (13.4 g, 52.8 mmol) and potassium acetate (16.0 g, 168.2 mmol) were suspended in 100 mL of anhydrous N,N-dimethylformamide. The reaction vessel was degassed under high vacuum and flushed with argon. This procedure was repeated seven times, and then [1,1'-bis(diphenylphosphino)ferrocene-palladium(II) (2.32 g, 7 mol%) complexed with dichloromethane was added to the reaction mixture, after which the degassing and argon flushing were repeated twice. The reaction mixture was heated at 80 °C for 19 h. After cooling to room temperature, the reaction was diluted with 10 mL of diethyl ether and 50 mL of cyclohexane and filtered through a small pad of silica gel. The pad was washed with 300 mL of a mixture of cyclohexane and diethyl ether (cyclohexane:diethyl ether = 5:1). The solvent was removed on a rotary evaporator, and the residue was purified by silica gel column chromatography using cyclohexane as eluent. The fractions containing the product were combined, and the solvent was removed on a rotary evaporator until a white solid precipitated. The suspension was filtered to give intermediate 1-1 (10.25 g, 86% yield) as a white solid. 1 H NMR (300 MHz, DMSO-d6) δ 10.33 (s, 1H), 8.31-8.23 (m, 1H), 8.14-8.09 (m, 1H), 7.75 (dt, J=8.1, 0.9 Hz, 1H), 7.71 (dd, J=7.2, 1.3 Hz, 1H), 7.44-7.36 (m, 1H), 7.23-7.13 (m, 2H), 1.41 (s, 12H).

[0710] [ka]

[0711] [Preparation of Intermediate 1-2] Intermediate 1-1 (9.57 g, 32.6 mmol), 2-bromo-4-(tert-butyl)-1-nitrobenzene (8.26 g, 32.0 mmol), and sodium hydroxide (2.56 g, 64.0 mmol) were suspended in a mixture of tetrahydrofuran / water (100 / 50 (mL)). The suspension was degassed under an argon atmosphere, and tetrakis(triphenylphosphine)palladium(0) (555 mg, 1.5 mol%) was added to the reaction mixture. The reaction mixture was refluxed for 2.5 h. The reaction was cooled to room temperature and diluted with toluene / water. The layers were separated, and the aqueous layer was further extracted with toluene. The organic extract was washed with water and saturated brine, dried over sodium sulfate, filtered, and evaporated. The residue was purified by silica gel column chromatography using heptane / toluene as eluent to give intermediate 1-2 (10.01 g, 91% yield) as an orange solid. ESI-MS: 343.3 [M+H] +

[0712] [ka]

[0713] [Production of Intermediate 1-3] Intermediate 1-2 (9.30 g, 27.0 mmol), iodobenzene (18.13 mL, 162 mmol), potassium carbonate (11.19 g, 81.0 mmol), and copper (858 mg, 13.5 mmol) were suspended in 90 mL of nitrobenzene. The suspension was degassed with Ar and then heated at 200 °C for 6 h. The reaction was cooled to room temperature, diluted with toluene, and then filtered through Celite. The filtrate was concentrated and the resulting residue was dissolved in 500 mL of toluene, after which 60 g of silica gel was added and the suspension was stirred at room temperature. The suspension was filtered and the filtrate was diluted with toluene / water. The layers were separated and the organic layer was washed with more water, then dried over sodium sulfate, filtered, and the solution was concentrated. The crude solid was recrystallized from isopropanol / diisopropyl ether (180 mL, 1:1) to give intermediate 1-3 (9.65 g, 85% yield) as a yellow solid. ESI-MS: 421.4 [M+H] +

[0714] [ka]

[0715] [Preparation of Intermediate 1-4] Intermediate 1-3 (11.35 g, 27.0 mmol) and triphenylphosphine (85 g, 324 mmol) were combined and the solid mixture was heated at 200° C. for 3.5 h. After cooling to room temperature, the residue was purified by silica gel column chromatography using cyclohexane / toluene as eluent to give intermediate 1-4 (7.03 g, 67% yield) as a white solid. ESI-MS: 387.3 [MH] +

[0716] [ka]

[0717] [Preparation of Intermediate 1-5] Intermediate 1-4 (6.80 g, 17.5 mmol) was dissolved in a mixture of 30 mL of dimethylformamide and 60 mL of chloroform. The solution was cooled to 0° C., and then N-bromosuccinimide (3.11 g, 17.5 mmol) was added portionwise over 30 min. The reaction was allowed to warm to room temperature and stirred there for 1 h. After evaporation of the reaction mixture, the residue was purified by silica gel column chromatography using heptane / toluene as eluent to give intermediate 1-5 (7.81 g, 95% yield) as a white solid. ESI-MS: 465.2 [MH] +

[0718] [ka]

[0719] [Preparation of Intermediate 1-6] 1,3-Dibromo-5-(tert-butyl)benzene (48.0 g, 0.16 mol) was dissolved in 500 mL of tetrahydrofuran. 70.0 mL of n-butyllithium (2.5 M solution in hexane) was added dropwise at −71° C. for 45 min. Iodine (45.9 g, 0.18 mol) was added portionwise at −55° C. for 15 min, and the resulting suspension was stirred at −78° C. for another 45 min. 400 mL of 10% aqueous sodium sulfite was added and the reaction mixture was further stirred until it reached room temperature. The organic phase was separated and the aqueous phase was extracted twice with 150 mL of cyclohexane. The combined organic phase was washed twice with 200 mL of water and further with saturated aqueous sodium chloride. The organic phase was dried over sodium sulfate and concentrated under vacuum to give intermediate 1-6 (54.7 g, 83% yield) as an orange oil. 1 H NMR (300 MHz, DMSO-d6) δ 7.77 (t, 1H), 7.72 (t, 1H), 7.57 (t, 1H), 1.26 (s, 9H).

[0720] [ka]

[0721] [Preparation of intermediate 1-7] Intermediate 1-6 (7.46 g, 22.00 mmol), 4-(tert-butyl)aniline (3.28 g, 22.00 mmol), and sodium tert-butoxide (2.96 g, 30.08 mmol) were suspended in 100 mL of toluene. After the suspension was degassed with Ar, tris(dibenzylideneacetone)dipalladium(0) (242 mg, 1.2 mol%) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (611 mg, 4.8 mol%) were added to the mixture. The reaction mixture was stirred at 50 °C for 1 h. The reaction was cooled to room temperature, filtered, and rinsed with toluene. The filtrate was concentrated and the residue was purified by silica gel column chromatography using heptane / toluene as eluent to give intermediate 1-7 (6.25 g, 79% yield) as a yellow oil. ESI-MS: 358.3 [MH] +

[0722] [ka]

[0723] [Preparation of Intermediate 1-8] Intermediate 1-7 (6.09 g, 16.9 mmol), bis(pinacolato)diboron (5.58 g, 21.97 mmol) and potassium acetate (6.63 g, 67.6 mmol) were suspended in 50 mL of anhydrous N,N-dimethylformamide. The suspension was degassed by evacuating the reaction vessel under high vacuum and backfilling with argon. This procedure was repeated six times and [1,1'-bis(diphenylphosphino)ferrocene-palladium(II) (414 mg, 3 mol%) complexed with dichloromethane was added to the reaction. The reaction mixture was heated to 2.5 °C for 105 h. After cooling to room temperature, the reaction was diluted with toluene and filtered through a small pad of silica gel. The filtrate was concentrated and the residue was purified by silica gel column chromatography using heptane / toluene as eluent to give intermediate 1-8 (5.51 g, 80% yield) as a white solid. ESI-MS: 408.5 [M+H] +

[0724] [ka]

[0725] [Preparation of Intermediate 1-9] Intermediate 1-5 (5.84 g, 12.5 mmol), intermediate 1-8 (5.19 g, 12.75 mmol), and sodium hydroxide (1.00 g, 25.0 mmol) were suspended in a mixture of tetrahydrofuran / water (60 / 30 (mL)). The suspension was degassed with Ar and tetrakis(triphenylphosphine)palladium(0) (433 mg, 3 mol%) was added to the reaction mixture. The reaction mixture was refluxed for 7 h. The reaction was cooled to room temperature and diluted with toluene / water. After filtration, the layers were separated and the aqueous layer was further extracted with toluene. The organic extract was washed with water, brine, dried over sodium sulfate, filtered, and evaporated. The residue was purified by silica gel column chromatography using heptane / toluene as eluent to give intermediate 1-9 (8.00 g, 96% yield) as a beige solid. ESI-MS: 668.5 [M+H] +

[0726] [ka]

[0727] [Preparation of Intermediate 1-10] Intermediate 1-9 (8.02 g, 12.00 mmol), 3-bromobenzofuran (2.36 g, 12.00 mmol), and sodium tert-butoxide (2.88 g, 30.00 mmol) were suspended in 100 mL of toluene. The suspension was degassed with Ar, and then tris(dibenzylideneacetone)dipalladium(0) (220 mg, 2 mol%) and tri-tert-butylphosphonium tetrafluoroborate (279 mg, 8 mol%) were added to the mixture. The reaction mixture was stirred at 6.5 °C for 65 h. The reaction was cooled to room temperature and diluted with toluene / water. The layers were separated and the aqueous layer was further extracted with toluene. The organic extract was washed with water, saturated brine, dried over sodium sulfate, filtered, and evaporated. The filtrate was concentrated and the residue was purified by silica gel column chromatography using heptane / toluene as eluent to give intermediate 1-10 (6.86 g, 73% yield) as a beige solid. ESI-MS: 784.4 [M+H] +

[0728] [ka]

[0729] [Preparation of compound BD-1] Intermediate 1-10 (2.59 g, 3.30 mmol) was dissolved in 45 mL of tert-butylbenzene, degassed with Ar, and cooled to 0°C. tert-Butyllithium (4.33 mL, 6.93 mmol) (1.6 M solution in pentane) was added dropwise, which was then warmed to room temperature and stirred for 2 h. Tribromoborane (6.60 mL, 6.60 mmol) (1 M solution in heptane) was then added dropwise at 0°C, followed by N-ethyl-N-isopropylpropan-2-amine (2.26 mL, 13.20 mmol). The reaction mixture was stirred at 160°C for 6 h. The reaction was cooled to room temperature and diluted with methanol / water. The precipitate was filtered and washed with methanol, water, heptane, and toluene. The solid was recrystallized from xylene to give compound BD-1 (891 mg, 34% yield) as a yellow solid. ESI-MS: 792.6 [M+H]+ [Explanation of symbols]

[0730] Reference Signs List 1, 1A, 1B... organic EL element, 2... substrate, 3... anode, 4... cathode, 5... light-emitting layer, 6... hole injection layer, 7... hole transport layer, 8... electron transport layer, 9... electron injection layer, 67... first organic layer, 89... second organic layer.

Claims

1. A compound represented by the following general formula (1): 【Chemistry 1】 (In the general formula (1), Ring A １ , ring B １ , ring C １ and Ring D １ are each independently a substituted or unsubstituted ring having 5 to 60 ring atoms, Za and Zb are ring A １ are the atoms that make up Zc and Zd are ring B １ are the atoms that make up Za, Zb, Zc, and Zd each independently represent a nitrogen atom or a carbon atom; Ring C １ and Ring D １ teeth, 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 １ teeth, 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, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, -N(R １Ａ ) (R ２Ａ ) a group represented by -CN, or -O-(R １３６ ) is a group represented by R １ is 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, The R １ teeth, Ring A １ and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring A １ and combine with each other to form a substituted or unsubstituted fused ring, or Ring A １ and do not combine with each other, Ring B １ and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring B １ and Ring B １ and do not combine with each other, R １ , ring A １ , ring B １ , ring C １ and Ring D １ At least one of the substituents is -N(R １Ａ ) (R ２Ａ ) a group represented by R １Ａ and R ２Ａ A 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 １ As a substituent, -N(R １Ａ ) (R ２Ａ In the case where the compound has a group represented by the formula: R １Ａ and R ２Ａ are each independently R １ and combine with each other to form a substituted or unsubstituted monocyclic ring, or R １ and R １ and do not combine with each other, Ring A １ As a substituent, -N(R １Ａ ) (R ２Ａ In the case where the compound has a group represented by the formula: R １Ａ and R ２Ａ are each independently Ring A １ and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring A １ and Ring A １ and do not combine with each other, Ring B １ As a substituent, -N(R １Ａ ) (R ２Ａ In the case where the compound has a group represented by the formula: R １Ａ and R ２Ａ are each independently Ring B １ and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring B １ and Ring B １ and do not combine with each other, Ring C １ As a substituent, -N(R １Ａ ) (R ２Ａ In the case where the compound has a group represented by the formula: R １Ａ and R ２Ａ are each independently Ring C １ and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring C １ and Ring C １ and do not combine with each other, Ring D １ As a substituent, -N(R １Ａ ) (R ２Ａ In the case where the compound has a group represented by the formula: R １Ａ and R ２Ａ are each independently Ring D １ and combine with each other to form a substituted or unsubstituted monocyclic ring, or Ring D １ and Ring D １ and do not combine with each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. １Ａ and R ２Ａ 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, Ring A １ Among these, a monocyclic ring having a bond connecting Za and Zb, and ring C １ at least one of the monocycles closest to the bond connecting the boron atom and the nitrogen atom is a substituted or unsubstituted monocycle having 5 ring atoms; Y is, Ring B １ Atoms constituting the ring C １ A single bond that connects the atoms that make up Oxygen atom, Sulfur atom, NR ２１Ａ 、 CR ２２Ａ R ２３Ａ or SiR ２４Ａ R ２５Ａ and R ２２Ａ and R ２３Ａ A 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 ２４Ａ and R ２５Ａ A 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 ２１Ａ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. ２２Ａ , R ２３Ａ , R ２４Ａ , and R ２５Ａ 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 １ , ring A １ , ring B １ , ring C １ and Ring D １ When the group has a substituent, the substituent is each independently -N(R １Ａ ) (R ２Ａ ) a group represented by 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, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R １３３ ~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 １Ａ When there are multiple R １Ａ are the same or different from each other, R ２Ａ When there are multiple R ２Ａ are the same or different from each other, R １３３ When there are multiple R １３３ are the same or different from each other, R １３４ When there are multiple R １３４ are the same or different from each other, R １３５ When there are multiple R １３５ are the same or different from each other, R １３６ When there are multiple R １３６ are the same or different from each other, R １３７ When there are multiple R １３７ are the same or different from each other, R １３８ When there are multiple R １３８ are the same or different from each other, R １３９ When there are multiple R １３９ are the same or different from each other, R １４０ When there are multiple R １４０ are the same or different from each other, R １４１ When there are multiple R １４１ are the same or different from each other, R １４２ When there are multiple R １４２ are the same or different from each other, R １４３ When there are multiple R １４３ are the same or different from each other, R １４４ When there are multiple R １４４ are the same or different from each other, R １４５ When there are multiple R １４５ are the same or different from each other, R １４６ When there are multiple R １４６ are the same or different from each other.)

2. In the compound according to claim 1 , The compound represented by the general formula (1) is represented by the following general formula (11): compound. 【Chemistry 2】 (In the general formula (11), R １ , ring A １ , ring B １ , ring C １ , ring D １ , Za, Zb, Zc and Zd each independently represent R in the general formula (1). １ , ring A １ , ring B １ , ring C １ , ring D １ , Za, Zb, Zc and Zd are synonymous therewith; Here, Zc, Zd and Ze are ring B １ are the atoms that make up Zf and Zg are ring C １ are the atoms that make up Ze, Zf and Zg each independently represent a nitrogen atom or a carbon atom.

3. In the compound according to claim 2, Ze, Zf, and Zg are carbon atoms; compound.

4. In the compound according to any one of claims 1 to 3, Za, Zb, Zc, Zd, Ze, Zf, and Zg are carbon atoms; compound.

5. In the compound according to any one of claims 1 to 4, The ring A １ , the ring B １ , the ring C １ and the ring D １ The substituted or unsubstituted rings having 5 to 60 ring atoms as represented by the formula (I) are each independently a substituted or unsubstituted aryl ring having 6 to 60 ring carbon atoms; a substituted or unsubstituted heterocyclic ring having 5 to 60 ring atoms, or a substituted or unsubstituted alicyclic hydrocarbon ring having 5 to 60 ring atoms; compound.

6. In the compound according to any one of claims 1 to 5, R １ , ring A １ , ring B １ , ring C １ and Ring D １ When the group has a substituent, the substituent is each independently -N(R １Ａ ) (R ２Ａ ) a group represented by 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, -CN, or -O-(R １３６ ) is a group represented by compound.

7. In the compound according to claim 1 or 2, The compound represented by the general formula (1) is represented by the following general formula (12) or (13): compound. 【Chemistry 3】 (In the above general formulas (12) to (13), R １ is R in the general formula (1). １ is synonymous with X １ and X ２ Each independently represents an oxygen atom, a sulfur atom, NRx, or C(Rx １ ) (Rx ２ ) and R １ , R １１ ~R １３ , R ３１Ａ ~R ３２Ａ , Rx, Rx １ , and Rx ２ At least one pair of adjacent pairs 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 １ , R １１ ~R １３ , R ４１ ~R ４２ , Rx, Rx １ , and Rx ２ At least one pair of adjacent pairs 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 １４ ~R ２２ One or more of the adjacent pairs of two or more 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. １１ ~R ２２ , R ３１Ａ ~R ３２Ａ , and R ４１ ~R ４２ 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, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, -N(R １Ａ ) (R ２Ａ ) a group represented by -CN, or -O-(R １３６ ) is a group represented by Rx and Rx do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring. １ , and Rx ２ are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

8. In the compound according to claim 7, The compound represented by the general formula (12) is represented by the following general formula (121), and the compound represented by the general formula (13) is represented by the following general formula (131): compound. 【Chemistry 4】 (In the general formulae (121) and (131), R １ , R １１ ~R １６ , R １９ ~R ２２ , X １ and X ２ each independently represents R in the general formulas (12) and (13). １ , R １１ ~R １６ , R １９ ~R ２２ , X １ and X ２ is synonymous with R １ , R １１ ~R １３ , R ４０ , Rx, Rx １ , and Rx ２ At least one pair of adjacent pairs 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, Multiple R ４０ are identical or different from each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. ４０ each independently represents R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring in the general formulas (12) and (13). １１ (Same meaning as above.)

9. In the compound according to claim 7 or claim 8, R １ 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 １１ ~R ２２ , R ３１Ａ ~R ３２Ａ , R ４０ , and R ４１ ~R ４２ 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, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or -N(R １Ａ ) (R ２Ａ ) is a group represented by compound.

10. In the compound according to any one of claims 7 to 9, R １４ ~R ２２ Either one of -N(R １Ａ ) (R ２Ａ ) is a group represented by R １Ａ and R ２Ａ 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; compound.

11. In the compound according to any one of claims 7 to 9, R １４ ~R ２２ Either one of -N(R １Ａ ) (R ２Ａ ) is a group represented by R １Ａ and R ２Ａ A 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; compound.

12. In the compound according to claim 8, The compound represented by the general formula (121) is represented by any one of the following general formulae (A121) to (A131), and the compound represented by the general formula (131) is represented by any one of the following general formulae (B131) to (B141): compound. 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 (In the above general formulae (A121) to (A129) and (B131) to (B139), R １ , R １１ ~R １６ , R １９ ~R ２２ , X １ , X ２ , and R ４０ each independently represents R in the general formulas (121) and (131). １ , R １１ ~R １６ , R １９ ~R ２２ , X １ , X ２ , and R ４０ is synonymous with R ５０ and R Ｂ At least one pair of adjacent pairs 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, Multiple R ５０ are identical or different from each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. Ｂ teeth, 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. ５０ each independently represents, in the general formulae (121) and (131), R which does not form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring. ４０ (Same meaning as above.) 【Chemistry 8】 (In the above general formulae (A130) to (A131) and (B140) to (B141), R １ , R １１ ~R １６ , R １９ ~R ２２ , X １ , X ２ , and R ４０ each independently represents R in the general formulas (121) and (131). １ , R １１ ~R １６ , R １９ ~R ２２ , X １ , X ２ , and R ４０ is synonymous with R １Ａ and R ２Ａ each independently represents R in the general formula (1) １Ａ and R ２Ａ (Same meaning as above.)

13. In the compound according to claim 12, R １ 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 １１ ~R ２２ , R ４０ , and R ５０ 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, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or -N(R １Ａ ) (R ２Ａ ) is a group represented by compound.

14. In a compound according to any one of claims 7 to 13, X １ and X ２ Each independently represents an oxygen atom or C(Rx １ ) (Rx ２ ) and Rx １ and Rx ２ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; compound.

15. In the compound according to claim 1 or 2, The compound represented by the general formula (1) is represented by the following general formula (14) or (15): compound. 【Chemistry 9】 (In the general formulas (14) to (15), R １ is R in the general formula (1). １ is synonymous with X ３ and X ４ Each independently represents an oxygen atom, a sulfur atom, NRx, or C(Rx １ ) (Rx ２ ) and R １ , R １１ ~R １３ , and R ３１ ~R ３４ At least one pair of adjacent pairs 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 １８ ~R ２２ , R ５１ ~R ５２ , Rx, Rx １ , and Rx ２ At least one pair of adjacent pairs 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 １８ ~R ２２ , R ６１ ~R ６２ , Rx, Rx １ , and Rx ２ At least one pair of adjacent pairs 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. １１ ~R １３ , R １８ ~R ２２ , R ３１ ~R ３４ , R ５１ ~R ５２ , and R ６１ ~R ６２ 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, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, -N(R １Ａ ) (R ２Ａ ) a group represented by -CN, or -O-(R １３６ ) is a group represented by Rx, Rx which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring １ , and Rx ２ are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

16. In the compound according to claim 15, The compound represented by the general formula (1) is represented by the following general formula (141) or (151): compound. 【Chemistry 10】 (In the general formulae (141) and (151), R １１ ~R １３ , R １８ ~R ２２ , R ３２ ~R ３４ , R ５１ ~R ５２ , R ６１ ~R ６２ , X ３ and X ４ each independently represents R in the general formulas (14) and (15). １１ ~R １３ , R １８ ~R ２２ , R ３２ ~R ３４ , R ５１ ~R ５２ , R ６１ ~R ６２ , X ３ and X ４ is synonymous with R １Ｃ ~R ４Ｃ At least one pair of adjacent pairs 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. １Ｃ ~R ４Ｃ each independently represents R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring in the general formulas (14) and (15). １１ (Same meaning as above.)

17. In the compound according to claim 15 or 16, R １１ ~R １３ , R １８ ~R ２２ , R ３１ ~R ３４ , R ５１ ~R ５２ , R ６１ ~R ６２ , and R １Ｃ ~R ４Ｃ 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, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or -N(R １Ａ ) (R ２Ａ ) is a group represented by compound.

18. In the compound according to any one of claims 15 to 17, X ３ and X ４ Each independently represents an oxygen atom or C(Rx １ ) (Rx ２ ) and Rx １ and Rx ２ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; compound.

19. In the compound according to claim 15, R １ 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; compound.

20. In the compound according to claim 16, The compound represented by the general formula (141) is represented by any one of the following general formulae (C141) to (C150), and the compound represented by the general formula (151) is represented by any one of the following general formulae (D151) to (D160): compound. 【Chemistry 11】 (In the above general formulae (C141) to (C142) and (D151) to (D152), X ３ , X ４ , R １１ ~R １３ , R １８ ~R ２２ , R ３２ ~R ３４ , R ５１ ~R ５２ , R ６１ ~R ６２ , and R １Ｃ ~R ４Ｃ each independently represents X in the general formulas (141) and (151). ３ , X ４ , R １１ ~R １３ , R １８ ~R ２２ , R ３２ ~R ３４ , R ５１ ~R ５２ , R ６１ ~R ６２ , and R １Ｃ ~R ４Ｃ is synonymous with R １Ａ and R ２Ａ each independently represents R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring in the general formula (1). １Ａ and R ２Ａ (Same meaning as above.) 【Chemistry 12】 【Chemistry 13】 (In the above general formulae (C143) to (C145) and (D153) to (D155), X ３ , X ４ , R １１ ~R １３ , R １８ ~R ２２ , R ３２ ~R ３４ , R ５１ ~R ５２ , R ６１ ~R ６２ , and R １Ｃ ~R ４Ｃ each independently represents X in the general formulas (141) and (151). ３ , X ４ , R １１ ~R １３ , R １８ ~R ２２ , R ３２ ~R ３４ , R ５１ ~R ５２ , R ６１ ~R ６２ , and R １Ｃ ~R ４Ｃ is synonymous with R ６０ At least one pair of adjacent pairs 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, Multiple R ６０ are identical or different from each other, R Ｃ teeth, 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. ６０ each independently represents R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring in the general formulae (141) and (151). １１ (Same meaning as above.) 【Chemistry 14】 (In the above general formulae (C146) to (C147) and (D156) to (D157), X ３ , X ４ , R １１ ~R １３ , R １８ ~R ２２ , R ３２ ~R ３４ , and R １Ｃ ~R ４Ｃ each independently represents X in the general formulas (141) and (151). ３ , X ４ , R １１ ~R １３ , R １８ ~R ２２ , R ３２ ~R ３４ , and R １Ｃ ~R ４Ｃ is synonymous with R １Ａ and R ２Ａ each independently represents R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring in the general formula (1). １Ａ and R ２Ａ is synonymous with R ７０ At least one pair of adjacent pairs 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, Multiple R ７０ are identical or different from each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. ７０ each independently represents R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring in the general formulae (141) and (151). １１ (Same meaning as above.) 【Chemistry 15】 【Chemistry 16】 (In the above general formulae (C148) to (C150) and (D158) to (D160), X ３ , X ４ , R １１ ~R １３ , R １８ ~R ２２ , R ３２ ~R ３４ , and R １Ｃ ~R ４Ｃ each independently represents X in the general formulas (141) and (151). ３ , X ４ , R １１ ~R １３ , R １８ ~R ２２ , R ３２ ~R ３４ , and R １Ｃ ~R ４Ｃ is synonymous with R ６０ At least one pair of adjacent pairs 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, Multiple R ６０ are identical or different from each other, R ７０ At least one pair of adjacent pairs 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, Multiple R ７０ are identical or different from each other, R Ｃ teeth, 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. ６０ and R ７０ each independently represents R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring in the general formulae (141) and (151). １１ (Same meaning as above.)

21. A material for an organic electroluminescence device, comprising the compound according to any one of claims 1 to 20.

22. An organic electroluminescent element having a cathode, an anode, and an organic layer between the cathode and the anode, At least one of the organic layers comprises a compound according to any one of claims 1 to 20. Organic electroluminescent element.

23. the organic layer comprises an emitting layer, The light-emitting layer comprises the compound. The organic electroluminescence device according to claim 22.

24. The light-emitting layer contains a compound represented by the following general formula (H10): The organic electroluminescence device according to claim 22 or 23. 【Chemistry 17】 [In general formula (H10), R １０１ ~R １１０ Among the groups of two or more adjacent 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed 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 condensed ring. １０１ ~R １１０ At least one of the above is a group represented by general formula (H11) below: When two or more groups represented by the following general formula (H11) are present, each of the two or more groups represented by the following general formula (H11) is the same or different from each other. -L １０１ -Ar １０１ (H11) (In 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 When there are multiple R ９０１ are the same or different from each other, R ９０２ When there are multiple R ９０２ are the same or different from each other, R ９０３ When there are multiple R ９０３ are the same or different from each other, R ９０４ When there are multiple R ９０４ are the same or different from each other, R ９０５ When there are multiple R ９０５ are the same or different from each other, R ９０６ When there are multiple R ９０６ are the same or different from each other, R ９０７ When there are multiple R ９０７ are the same or different from each other.

25. An electronic device comprising the organic electroluminescence element according to any one of claims 22 to 24.

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