Compound, organic electroluminescent device, and electronic apparatus

Abstract

To provide a compound capable of improving the emission efficiency of an organic electroluminescent device.SOLUTION: The invention provides a compound represented by the formula (2), where: Ar2 is a substituted or unsubstituted aryl group having 6-50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5-50 ring-forming atoms; L2 is a single bond, a substituted or unsubstituted arylene group having 6-50 ring-forming carbon atoms, or a divalent substituted or unsubstituted heterocyclic group having 5-50 ring-forming atoms; and D21 is a group represented by the formula (20) in the figure.SELECTED DRAWING: None

Description

[Technical Field]

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

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

[0003] For example, it is expected that organic EL devices can emit light more efficiently by utilizing triplet excitons in addition to singlet excitons. Against this background, highly efficient fluorescent organic EL devices using thermally activated delayed fluorescence (hereinafter sometimes simply referred to as "delayed fluorescence") have been proposed and are being studied. The TADF (Thermally Activated Delayed Fluorescence) mechanism utilizes the phenomenon in which reverse intersystem crossing from triplet excitons to singlet excitons occurs thermally when a material with a small energy difference (ΔST) between the singlet and triplet levels is used. Thermally activated delayed fluorescence is described, for example, in "Device Properties of Organic Semiconductors," edited by Adachi Chinaya, Kodansha, April 1, 2012, pp. 261-268. Known examples of compounds exhibiting thermally activated delayed fluorescence (TADF) (hereinafter also referred to as TADF compounds) include compounds in which a donor moiety and an acceptor moiety are bonded within the molecule. For example, Patent Document 1 describes a compound exhibiting thermally activated delayed fluorescence. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] International Publication No. 2022 / 260119 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 improvements in the performance of organic EL elements are desired, including, for example, luminance, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan.

[0006] An object of the present invention is to provide a compound capable of improving the luminous efficiency of an organic electroluminescence device. Another object of the present invention is to provide an organic electroluminescence device having improved luminous efficiency. A further object of the present invention is to provide an electronic device equipped with the organic electroluminescence device. [Means for solving the problem]

[0007] According to one aspect of the present invention, there is provided a compound represented by the following formula (2):

[0008] [ka]

[0009] (In the formula (2), Ar2 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L2 is 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, When L2 is a single bond, Ar2 is D shown in the formula (2). 21 , R 21 , R 22 and a benzene ring to which two cyano groups are bonded via a carbon-carbon bond, When L2 is not a single bond, L2 is D shown in the formula (2). 21 , R 21 , R 22 and a benzene ring to which two cyano groups are bonded via a carbon-carbon bond, D 21 is a group represented by the following formula (20):

[0010] [ka]

[0011] (In the formula (2) and formula (20), R 21 , R 22 , R 201 , R 202 , R 203 , R 204 , R 205 , R 206 , R 207 , R 208 , R 209 , R 210 , R 211 and R 212 are each independently, hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted 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, -Si(R 281 )(R 282 )(R 283 ) a group represented by a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, -O-(R 284 ) a group represented by -S-(R 285 ) a group represented by -N(R 286 )(R 287 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 288 a group represented by -C(=O)(OR 289 ) a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R 290 )(R 291 ) a group represented by -Ge(R 292 )(R 293 )(R 294 ) a group represented by -B(R 295 )(R 296 ) a group represented by -B(OR 297 )(OR 298 ) a group represented by -OS(=O)2(R 299 ) is a group represented by R 21 , R 22 and R 201 ~R 212 is not a 9-carbazolyl group, R 201 , R 202 , R 203 , R 204 , R 205 , R206 , R 207 , R 208 , R 209 , R 210 , R 211 and R 212 At least one selected from the group consisting of is not a hydrogen atom, In the formula (20), * indicates a bonding position. In the compound represented by the formula (2), R 281 , R 282 , R 283 , R 284 , R 285 , R 286 , R 287 , R 288 , R 289 , R 290 , R 291 , R 292 , R 293 , R 294 , R 295 , R 296 , R 297 , R 298 and R 299 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 hydrocarbon ring group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 281 If there are multiple R 281 are the same or different from each other, R 282 If there are multiple R 282 are the same or different from each other, R 283 If there are multiple R 283 are the same or different from each other, R 284 If there are multiple R 284 are the same or different from each other, R 285 If there are multiple R285 are the same or different from each other, R 286 If there are multiple R 286 are the same or different from each other, R 287 If there are multiple R 287 are the same or different from each other, R 288 If there are multiple R 288 are the same or different from each other, R 289 If there are multiple R 289 are the same or different from each other, R 290 If there are multiple R 290 are the same or different from each other, R 291 If there are multiple R 291 are the same or different from each other, R 292 If there are multiple R 292 are the same or different from each other, R 293 If there are multiple R 293 are the same or different from each other, R 294 If there are multiple R 294 are the same or different from each other, R 295 If there are multiple R 295 are the same or different from each other, R 296 If there are multiple R 296 are the same or different from each other, R 297 If there are multiple R 297 are the same or different from each other, R 298 If there are multiple R 298 are the same or different from each other, R 299 If there are multiple R299 are either identical or different.)

[0012] According to one aspect of the present invention, there is provided an organic electroluminescence device comprising a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer includes one or more layers, at least one of the one or more layers includes a second compound, and the second compound is a compound according to one aspect of the present invention.

[0013] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescence element according to one aspect of the present invention. [Effects of the Invention]

[0014] According to one embodiment of the present invention, a compound capable of improving the luminous efficiency of an organic electroluminescence device can be provided. According to one embodiment of the present invention, an organic electroluminescence device having improved luminous efficiency can be provided. According to one embodiment of the present invention, an electronic device equipped with the organic electroluminescence device according to one embodiment of the present invention can be provided. [Brief explanation of the drawings]

[0015] [Figure 1] FIG. 1 is a schematic diagram of an apparatus for measuring transient PL. [Figure 2] FIG. 10 is a diagram showing an example of an attenuation curve of a transient PL. [Figure 3] FIG. 10 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a third embodiment of the present invention. [Figure 4] FIG. 10 is a diagram showing the energy levels of a first compound and a second compound in an emitting layer of an example of an organic electroluminescence element according to a third embodiment of the present invention, and the relationship between energy transfer. [Figure 5]FIG. 10 is a diagram showing the energy levels of a first compound, a second compound, and a third compound in an example of an emitting layer of an organic electroluminescence element according to a fourth embodiment of the present invention, as well as the relationship between energy transfer. [Figure 6] FIG. 10 is a diagram showing the energy levels of a second compound and a third compound in an example of an emitting layer of an organic electroluminescence element according to a fifth embodiment of the present invention, and a relationship between energy transfer. DETAILED DESCRIPTION OF THE INVENTION

[0016] [Definition] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0017] In this specification, in a chemical structural formula, a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded to a possible bonding position that is not explicitly marked with a symbol such as "R" or "D" representing a deuterium atom.

[0018] As used herein, the term "number of ring carbon atoms" refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. For example, a 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and a 9,9'-spirobifluorenyl group has 25 ring carbon atoms. Furthermore, when a benzene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of the benzene ring substituted with an alkyl group is 6. Furthermore, when a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.

[0019] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, and a ring assembly). Atoms that do not constitute the ring (e.g., hydrogen atoms terminating the bonds of atoms constituting the ring) and atoms contained in the substituent when the ring is substituted with a substituent are not included in the number of ring atoms. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms or atoms constituting a substituent bonded to the pyridine ring are not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. Furthermore, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring, so the number of ring atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

[0020] In this specification, the "number of carbon atoms XX to YY" in the expression "substituted or unsubstituted ZZ group having carbon atoms XX to YY" refers to the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0021] In this specification, the "number of atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having XX to YY atoms" refers to the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0022] In this specification, an unsubstituted ZZ group refers to a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to a case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group". In this specification, "unsubstituted" in the context of a "substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protist atom, a deuterium atom, or a tritium atom. In this specification, "substituted" in the context of "a substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. Similarly, "substituted" in the context of "a BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced with an AA group.

[0023] "Substituents described herein" The substituents described in this specification will be explained below.

[0024] The "unsubstituted aryl group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30 ring carbon atoms, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30 ring atoms, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkyl group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification. Unless otherwise specified in this specification, the "unsubstituted alkenyl group" described in this specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms. Unless otherwise specified, the "unsubstituted alkynyl group" described in this specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms. The "unsubstituted cycloalkyl group" described in this specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted arylene group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30 ring carbon atoms, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted divalent heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30 ring atoms, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkylene group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.

[0025] "Substituted or unsubstituted aryl group" Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B). (Here, the term "unsubstituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and the term "substituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" simply refers to both an "unsubstituted aryl group" and a "substituted aryl group." A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent. Examples of the "substituted aryl group" include groups in which one or more hydrogen atoms of the "unsubstituted aryl group" are replaced with a substituent, and examples of the substituted aryl group in the specific example group G1A below. The examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed here are merely examples, and the "substituted aryl group" described in this specification also includes groups in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent.

[0026] Unsubstituted aryl groups (specific example group G1A): phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, benzanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, chrysenyl group, benzochrysenyl group, a triphenylenyl group, benzotriphenylenyl group, tetracenyl group, pentacenyl groups, fluorenyl groups, 9,9'-spirobifluorenyl group, benzofluorenyl groups, dibenzofluorenyl groups, fluoranthenyl group, benzofluoranthenyl group, perylenyl groups, and A monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[0027] [ka]

[0028] [ka]

[0029] Substituted aryl groups (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, cyanophenyl groups, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl groups, and A group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by any one of the general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0030] "Substituted or unsubstituted heterocyclic group" The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom among the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom. The "heterocyclic groups" described herein are either monocyclic or fused ring groups. The "heterocyclic group" described herein may be an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group," and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group.") In this specification, the term "heterocyclic group" simply includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group." A "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with a substituent. Specific examples of the "substituted heterocyclic group" include the groups in which a hydrogen atom of the "unsubstituted heterocyclic group" in the specific example group G2A below is replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are also included. The examples of the "unsubstituted heterocyclic group" and the "substituted heterocyclic group" listed here are merely examples, and the "substituted heterocyclic group" described in this specification also includes groups in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" in the specific example group G2B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted heterocyclic group" in the specific example group G2B is further replaced with a substituent.

[0031] 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).

[0032] Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4).

[0033] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): pyrrolyl group, imidazolyl group, pyrazolyl group, a triazolyl group, tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, isothiazolyl group, a thiadiazolyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, a triazinyl group, Indolyl groups, isoindolyl groups, an indolizinyl group, a quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, a quinazolinyl group, quinoxalinyl group, benzimidazolyl group, an indazolyl group, a phenanthrolinyl group, a phenanthridinyl group, acridinyl group, phenazinyl group, a carbazolyl group, a benzocarbazolyl group, morpholino group, phenoxazinyl group, a phenothiazinyl group, Azacarbazolyl group and diazacarbazolyl group.

[0034] Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl groups, benzoisoxazolyl group, phenoxazinyl group, morpholino group, a dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, an azanaphthobenzofuranyl group, and Diazanaphthobenzofuranyl group.

[0035] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): thienyl group, a thiazolyl group, isothiazolyl group, a thiadiazolyl group, Benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), naphthobenzothiophenyl group (naphthobenzothienyl group), benzothiazolyl group, benzoisothiazolyl group, a phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), diazadibenzothiophenyl group (diazadibenzothienyl group), Azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and Diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0036] 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):

[0037] [ka]

[0038] [ka]

[0039] In the general formulae (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2. A and Y A At least one of is an oxygen atom, a sulfur atom, or NH. In the general formulae (TEMP-16) to (TEMP-33), X A and Y A When at least one of is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from NH or CH2.

[0040] Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): a (9-phenyl)carbazolyl group, a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a (9-naphthyl)carbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, methylbenzimidazolyl group, ethylbenzimidazolyl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenylquinazolinyl group, and Biphenylylquinazolinyl group.

[0041] 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].

[0042] 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].

[0043] 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):

[0044] The "one or more hydrogen atoms of the monovalent heterocyclic group" refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, X A and Y A a hydrogen atom bonded to a nitrogen atom when at least one of A and Y A or more hydrogen atoms selected from the hydrogen atoms of a methylene group when one of the groups is CH2.

[0045] "Substituted or unsubstituted alkyl groups" Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described herein include the following unsubstituted alkyl group (specific example group G3A) and substituted alkyl group (specific example group G3B). (Here, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereinafter, when simply referring to an "alkyl group," both an "unsubstituted alkyl group" and a "substituted alkyl group" are included. The term "substituted alkyl group" refers to an "unsubstituted alkyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkyl group" include the following "unsubstituted alkyl group" (specific example group G3A) in which one or more hydrogen atoms have been replaced with a substituent, and the examples of the substituted alkyl group (specific example group G3B). In this specification, the alkyl group in the "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the "unsubstituted alkyl group" includes a linear "unsubstituted alkyl group" and a branched "unsubstituted alkyl group." Note that the examples of the "unsubstituted alkyl group" and the "substituted alkyl group" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" in specific example group G3B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl group" in specific example group G3B is further replaced with a substituent.

[0046] 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.

[0047] Substituted alkyl groups (specific example group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.

[0048] "Substituted or unsubstituted alkenyl group" Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described herein include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group G4B). (Here, the term "unsubstituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and the term "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply includes both an "unsubstituted alkenyl group" and a "substituted alkenyl group." A "substituted alkenyl group" refers to an "unsubstituted alkenyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl groups" (specific example group G4A) having a substituent, and the examples of substituted alkenyl groups (specific example group G4B). The examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl group" described in this specification also includes groups in the "substituted alkenyl groups" of specific example group G4B in which a hydrogen atom of the alkenyl group itself has been further replaced with a substituent, and groups in the "substituted alkenyl groups" of specific example group G4B in which a hydrogen atom of a substituent has been further replaced with a substituent.

[0049] Unsubstituted alkenyl groups (specific example group G4A): vinyl groups, Allyl groups, a 1-butenyl group, 2-butenyl group, and 3-butenyl group.

[0050] Substituted alkenyl groups (specific example group G4B): 1,3-butadienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.

[0051] "Substituted or unsubstituted alkynyl group" Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl groups (specific example group G5A). (Here, the unsubstituted alkynyl group refers to a case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, when simply referring to an "alkynyl group," it includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group." A "substituted alkynyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced with substituents. Specific examples of the "substituted alkynyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl group" (specific example group G5A) are replaced with substituents, etc.

[0052] Unsubstituted alkynyl groups (specific example group G5A): Ethynyl group.

[0053] "Substituted or unsubstituted cycloalkyl groups" Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described herein include the following unsubstituted cycloalkyl group (specific example group G6A) and substituted cycloalkyl group (specific example group G6B). (Here, the unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group," and the substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group.") In this specification, when the term "cycloalkyl group" is simply used, it includes both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group." A "substituted cycloalkyl group" refers to an "unsubstituted cycloalkyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (specific example group G6A) in which one or more hydrogen atoms have been replaced with a substituent, and the examples of the substituted cycloalkyl group (specific example group G6B). The examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed here are merely examples, and the "substituted cycloalkyl group" described in this specification also includes a group in the "substituted cycloalkyl group" of specific example group G6B in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself have been replaced with a substituent, and a group in the "substituted cycloalkyl group" of specific example group G6B in which a hydrogen atom of a substituent has been further replaced with a substituent.

[0054] Unsubstituted cycloalkyl groups (specific example group G6A): a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.

[0055] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.

[0056] -Si(R 901 )(R 902 )(R 903 ) a group represented by -Si(R 901 )(R 902 )(R 903 Specific examples (specific example group G7) of the group represented by -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6. The multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other. The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other. The multiple G1s in —Si(G1)(G1)(G2) are the same as or different from each other. The multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other. The multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The multiple G6s in -Si(G6)(G6)(G6) may be the same as or different from each other.

[0057] -O-(R 904 ) a group represented by -O-(R 904 Specific examples (specific example group G8) of the group represented by -O(G1), -O(G2), -O(G3), and -O(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.

[0058] -S-(R 905 ) a group represented by -S-(R 905 Specific examples (specific example group G9) of the group represented by -S(G1), -S(G2), -S(G3), and -S(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.

[0059] -N(R 906 )(R 907 ) a group represented by -N(R 906 )(R 907 Specific examples (specific example group G10) of the group represented by -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6. -The multiple G1s in N(G1)(G1) are the same as or different from each other. The multiple G2's in -N(G2)(G2) are the same as or different from each other. -The multiple G3s in N(G3)(G3) are the same as or different from each other. The multiple G6s in -N(G6)(G6) are the same as or different from each other.

[0060] "Halogen atoms" Specific examples (specific example group G11) of the "halogen atom" described in this specification include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0061] "Substituted or unsubstituted fluoroalkyl groups" The term "substituted or unsubstituted fluoroalkyl group" as used herein refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). Unless otherwise specified herein, the number of carbon atoms in an "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The term "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. The term "substituted fluoroalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in a "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in a "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include the examples of the above-mentioned "alkyl group" (specific example group G3) in which one or more hydrogen atoms are replaced with a fluorine atom.

[0062] "Substituted or unsubstituted haloalkyl groups" The term "substituted or unsubstituted haloalkyl group" as used herein refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The number of carbon atoms in an "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. The term "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms in a "haloalkyl group" are replaced with a substituent. The term "substituted haloalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in a "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in a "substituted haloalkyl group" are further replaced with a substituent. Specific examples of "unsubstituted haloalkyl groups" include the examples of the above-mentioned "alkyl groups" (specific example group G3) in which one or more hydrogen atoms are replaced with halogen atoms. Haloalkyl groups are sometimes referred to as halogenated alkyl groups.

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

[0064] "Substituted or unsubstituted alkylthio group" A specific example of the "substituted or unsubstituted alkylthio group" described herein is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified herein, the "unsubstituted alkylthio group" has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms.

[0065] "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.

[0066] "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.

[0067] "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described herein is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) may be the same or different. Unless otherwise specified herein, the number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0068] "Substituted or unsubstituted aralkyl group" A specific example of the "substituted or unsubstituted aralkyl group" described herein is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. Thus, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one embodiment of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group," and the number of carbon atoms in the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified herein. Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl groups.

[0069] Unless otherwise specified in the present specification, the substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, or the like.

[0070] Unless otherwise specified in the present specification, the substituted or unsubstituted heterocyclic group described herein is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an aza Examples include a dibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group (a (9-phenyl)carbazol-1-yl group, a (9-phenyl)carbazol-2-yl group, a (9-phenyl)carbazol-3-yl group, or a (9-phenyl)carbazol-4-yl group), a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group.

[0071] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.

[0072] [ka]

[0073] In this specification, unless otherwise specified in this specification, a (9-phenyl)carbazolyl group specifically means any of the following groups:

[0074] [ka]

[0075] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0076] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0077] [ka]

[0078] In the general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.

[0079] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like.

[0080] "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.

[0081] "Substituted or unsubstituted divalent heterocyclic group" Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom on the heterocycle from the above-mentioned "substituted or unsubstituted heterocyclic group". Specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group" include divalent groups derived by removing one hydrogen atom on the heterocycle from the "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0082] "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.

[0083] Unless otherwise specified in the present specification, the substituted or unsubstituted arylene group described in the present specification is preferably any one of the groups represented by the following general formulae (TEMP-42) to (TEMP-68).

[0084] [ka]

[0085] [ka]

[0086] In the general formulae (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-42) to (TEMP-52), * represents a bonding position.

[0087] [ka]

[0088] In the general formulae (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent. Equations Q9 and Q 10 may be bonded to each other via a single bond to form a ring. In the general formulae (TEMP-53) to (TEMP-62), * represents a bonding position.

[0089] [ka]

[0090] In the general formulae (TEMP-63) to (TEMP-68), Q1 to Q8 each independently represent a hydrogen atom or a substituent. In the general formulae (TEMP-63) to (TEMP-68), * represents a bonding position.

[0091] Unless otherwise specified in the present specification, the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the groups represented by the following general formulae (TEMP-69) to (TEMP-102).

[0092] [ka]

[0093] [ka]

[0094] [ka]

[0095] In the general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 each independently represent a hydrogen atom or a substituent.

[0096] [ka]

[0097] [ka]

[0098] [ka]

[0099] [ka]

[0100] In the general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 each independently represent a hydrogen atom or a substituent.

[0101] The above is the explanation of "substituents described in this specification."

[0102] - "When bonded to form a ring" In this specification, the phrase "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocycle, bond with each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocycle", the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted fused ring", or the case where "one or more pairs of adjacent groups do not bond with each other". In this specification, the cases where "one or more groups of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocyclic ring" and "one or more groups of two or more adjacent groups bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "a case where they bond to form a ring") will be explained below. The case of an anthracene compound represented by the following general formula (TEMP-103), in which the main skeleton is an anthracene ring, will be explained as an example.

[0103] [ka]

[0104] For example, R921 ~R 930 In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," one pair of adjacent two groups is R 921 and R 922 Paired with R 922 and R 923 Paired with R 923 and R 924 Paired with R 924 and R 930 Paired with R 930 and R 925 Paired with R 925 and R 926 Paired with R 926 and R 927 Paired with R 927 and R 928 Paired with R 928 and R 929 Pairs with and R 929 and R 921 It is paired with.

[0105] The above "one or more pairs" means that two or more pairs of adjacent two or more groups may simultaneously form a ring. For example, R 921 and R 922 and are bonded to each other to form ring Q A At the same time, R 925 and R 926 and are bonded to each other to form ring Q B When the anthracene compound represented by the general formula (TEMP-103) is formed, the anthracene compound represented by the general formula (TEMP-104) is represented by the following general formula (TEMP-104).

[0106] [ka]

[0107] When a "set of two or more adjacent units" forms a ring, it does not only mean that a set of two adjacent units is bonded, as in the previous example, but also that a set of three or more adjacent units is bonded. For example, R 921 and R 922 and are bonded to each other to form ring Q A and R 922 and R923 and are bonded to each other to form ring Q C and form three adjacent (R 921 , R 922 and R 923 In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105): A and Ring Q C is R 922 Share.

[0108] [ka]

[0109] The "monocyclic ring" or "fused ring" formed may be a saturated ring or an unsaturated ring as the structure of only the ring formed. Even when "one pair of adjacent two" forms a "monocyclic ring" or a "fused ring", the "monocyclic ring" or the "fused ring" may form a saturated ring or an unsaturated ring. For example, in the case of the ring Q formed in the general formula (TEMP-104), A and Ring Q B are "monocyclic rings" or "fused rings", respectively. A , and ring Q C is a "fused ring". A and Tamaki Q C That is, Tamaki Q A and Tamaki Q C The ring Q in the general formula (TMEP-104) is fused to form a fused ring. A If is a benzene ring, then ring Q A The ring Q in the general formula (TMEP-104) is a monocyclic ring. A If is a naphthalene ring, then ring Q A is a fused ring.

[0110] The term "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The term "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of the aromatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G1 are terminated with a hydrogen atom. Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in the specific example group G2 are terminated with a hydrogen atom. Specific examples of the aliphatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom. The term "forming a ring" means that a ring is formed only with a plurality of atoms of the main skeleton, or with a plurality of atoms of the main skeleton and one or more optional elements. For example, R 921 and R 922 and are bonded to form a ring Q A is R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 It means a ring formed by the carbon atom of the anthracene skeleton to which R is bonded and one or more arbitrary elements. 921 and R 922 Todekan Q A In the case where R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 When a monocyclic unsaturated ring is formed with the carbon atom of the anthracene skeleton to which R is bonded and four carbon atoms, 921 and R 922 The ring formed by

[0111] Here, unless otherwise specified in this specification, the "arbitrary element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur. In the arbitrary element (for example, in the case of carbon or nitrogen), the bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below. When an arbitrary element other than carbon is included, the formed ring is a heterocycle. Unless otherwise specified in this specification, the "one or more arbitrary elements" constituting the monocyclic or fused ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less. Unless otherwise specified in this specification, of the "monocyclic ring" and the "fused ring", the "monocyclic ring" is preferred. Unless otherwise specified in this specification, of the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred. Unless otherwise specified herein, a "monocyclic ring" is preferably a benzene ring. Unless otherwise specified herein, the "unsaturated ring" is preferably a benzene ring. When "one or more pairs of adjacent two or more groups" "combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring," unless otherwise specified in this specification, preferably, one or more pairs of adjacent two or more groups combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0112] When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification." When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification." The above is an explanation of the case where "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring" ("when bonded to form a ring").

[0113] Substituents in "substituted or unsubstituted" In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituent" in the present specification) includes, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms; an unsubstituted alkenyl group having 2 to 50 carbon atoms; an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms; -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and Unsubstituted heterocyclic group having 5 to 50 ring atoms and the like, a group selected from the group consisting of where R 901 ~R 907 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 901 If there are two or more, there are two or more R 901 are identical to or different from each other, R 902 If there are two or more, there are two or more R 902 are identical to or different from each other, R903 If there are two or more, there are two or more R 903 are identical to or different from each other, R 904 If there are two or more, there are two or more R 904 are identical to or different from each other, R 905 If there are two or more, there are two or more R 905 are identical to or different from each other, R 906 If there are two or more, there are two or more R 906 are identical to or different from each other, R 907 If there are two or more, there are two or more R 907 are the same or different from each other.

[0114] In one embodiment, the substituents in the "substituted or unsubstituted" are: an alkyl group having 1 to 50 carbon atoms; an aryl group having 6 to 50 ring carbon atoms, and Heterocyclic groups with 5 to 50 ring atoms is a group selected from the group consisting of:

[0115] In one embodiment, the substituents in the "substituted or unsubstituted" are: an alkyl group having 1 to 18 carbon atoms; an aryl group having 6 to 18 ring carbon atoms, and Heterocyclic groups with 5 to 18 ring atoms is a group selected from the group consisting of:

[0116] 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."

[0117] Unless otherwise specified in this specification, any adjacent substituents may be bonded to each other to form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring. Unless otherwise specified in this specification, any optional substituent may further have a substituent. The substituent that the optional substituent further has is the same as the optional substituent described above.

[0118] In this specification, a numerical range expressed using "AA to BB" means a range that includes the number AA written before "AA to BB" as the lower limit and the number BB written after "AA to BB" as the upper limit.

[0119] In this specification, the expression "A≧B" means that the value of A is equal to the value of B, or the value of A is greater than the value of B. In this specification, the expression "A≦B" means that the value of A is equal to the value of B, or the value of A is smaller than the value of B.

[0120] First Embodiment <Compound> The compound according to the first embodiment is a compound represented by the following formula (2).

[0121] [ka]

[0122] (In the formula (2), Ar2 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L2 is 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, When L2 is a single bond, Ar2 is D shown in the formula (2). 21 , R 21 , R 22 and a benzene ring to which two cyano groups are bonded via a carbon-carbon bond, When L2 is not a single bond, L2 is D shown in the formula (2). 21 , R 21 , R 22 and a benzene ring to which two cyano groups are bonded via a carbon-carbon bond, D 21 is a group represented by the following formula (20):

[0123] [ka]

[0124] (In the formula (2) and formula (20), R 21 , R 22 , R 201 , R 202 , R 203 , R 204 , R 205 , R 206 , R 207 , R 208 , R 209 , R 210 , R 211 and R 212 are each independently, hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted 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, -Si(R 281 )(R 282 )(R 283 ) a group represented by a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, -O-(R 284 ) a group represented by -S-(R 285 ) a group represented by -N(R 286 )(R 287 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 288 a group represented by -C(=O)(OR 289 ) a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R 290 )(R 291 ) a group represented by -Ge(R 292 )(R 293 )(R 294 ) a group represented by -B(R 295 )(R 296 ) a group represented by -B(OR 297 )(OR 298 ) a group represented by -OS(=O)2(R 299 ) is a group represented by R 21 , R 22 and R 201 ~R 212 is not a 9-carbazolyl group, R 201 , R 202 , R 203 , R 204 , R 205 , R 206 , R 207 , R 208 , R 209 , R 210 , R 211 and R 212 At least one selected from the group consisting of is not a hydrogen atom, In the formula (20), * indicates a bonding position. In the compound represented by the formula (2), R 281 , R 282 , R 283 , R 284 , R 285 , R 286 , R 287 , R 288 , R 289 , R 290 , R 291 , R 292 , R 293 , R 294 , R 295 , R 296 , R 297 , R 298 and R 299 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 hydrocarbon ring group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 281 If there are multiple R 281 are the same or different from each other, R 282 If there are multiple R 282 are the same or different from each other, R 283 If there are multiple R 283 are the same or different from each other, R 284 If there are multiple R 284 are the same or different from each other, R 285 If there are multiple R 285 are the same or different from each other, R 286 If there are multiple R 286 are the same or different from each other, R 287 If there are multiple R 287are the same or different from each other, R 288 If there are multiple R 288 are the same or different from each other, R 289 If there are multiple R 289 are the same or different from each other, R 290 If there are multiple R 290 are the same or different from each other, R 291 If there are multiple R 291 are the same or different from each other, R 292 If there are multiple R 292 are the same or different from each other, R 293 If there are multiple R 293 are the same or different from each other, R 294 If there are multiple R 294 are the same or different from each other, R 295 If there are multiple R 295 are the same or different from each other, R 296 If there are multiple R 296 are the same or different from each other, R 297 If there are multiple R 297 are the same or different from each other, R 298 If there are multiple R 298 are the same or different from each other, R 299 If there are multiple R 299 are either identical or different.)

[0125] R in the compound according to the first embodiment 21 , R 22 and R 201 ~R 212is not a 9-carbazolyl group, and when L2 is a single bond, Ar2 is D shown in the formula (2). 21 , R 21 , R 22 and the benzene ring to which the two cyano groups are bonded via a carbon-carbon bond, and when L2 is not a single bond, L2 is D 21 , R 21 , R 22 and bonded to a benzene ring to which two cyano groups are bonded via a carbon-carbon bond. The compound according to the first embodiment having such a structure has increased electron mobility compared to conventional TADF materials. Therefore, by using the compound according to the first embodiment in an organic electroluminescence device, the device performance is improved. For example, by using the compound according to the first embodiment in an emitting layer, the amount of holes and the amount of electrons in the emitting layer are both increased, thereby improving the luminous efficiency of the organic electroluminescence device.

[0126] In addition, conventional TADF materials have a high ionization potential, which means that the hole injection into the light-emitting layer using conventional TADF materials is not high. As a result, organic EL devices using conventional TADF materials have the problem of high driving voltage. The compound according to the first embodiment is a dicyanobenzene compound having two cyano groups bonded thereto, and D 21 has a group represented by formula (20) as R 201 ~R 212 At least one selected from the group consisting of is not a hydrogen atom (i.e., R 201 ~R 212(wherein at least one selected from the group consisting of is a substituent). The compound according to the first embodiment has such a group represented by formula (20) and has a smaller ionization potential than conventional TADF materials. Therefore, by using the compound according to the first embodiment in an organic electroluminescence device, the device performance is improved. For example, by using the compound according to the first embodiment in the light-emitting layer of an organic electroluminescence device, the hole injection property into the light-emitting layer is improved. Therefore, in one aspect of an organic electroluminescence device using the compound according to the first embodiment in the light-emitting layer, the driving voltage is reduced.

[0127] In this specification, a cyano group is represented by —CN or —NC— in each formula.

[0128] In the first embodiment, the compound represented by formula (2) is preferably a compound represented by the following formula (2-1), (2-2) or (2-3).

[0129] [ka]

[0130] (In the formulas (2-1), (2-2) and (2-3), D 21 , Ar2, L2, R 21 and R 22 are the D in the above formula (2), respectively. 21 , Ar2, L2, R 21 and R 22 is equivalent to

[0131] The compound according to the first embodiment (the compound represented by the formula (2)) is preferably a compound represented by the formula (2-1).

[0132] The compound according to the first embodiment (the compound represented by the formula (2)) is preferably a compound represented by the following formula (2-11), formula (2-12), formula (2-13), formula (2-14), formula (2-15), formula (2-16), or formula (2-17).

[0133] [ka]

[0134] [ka]

[0135] [ka]

[0136] (In the above formulas (2-11), (2-12), (2-13), (2-14), (2-15), (2-16) and (2-17), D 21 , Ar2, L2, R 21 and R 22 are the D in the above formula (2), respectively. 21 , Ar2, L2, R 21 and R 22 is equivalent to

[0137] The compound according to the first embodiment (the compound represented by the formula (2)) is preferably a compound represented by the formula (2-11).

[0138] In the compound according to the first embodiment, D 21 is R 21 , R 22 and the group represented by -L2-Ar2 are preferably different groups.

[0139] In the compound according to the first embodiment, the group represented by -L2-Ar2 is R 21 , R 22 and D 21 It is preferable that the group is different from the group

[0140] In the compound according to the first embodiment, R 21 and R 22 are the same or different from each other.

[0141] In the compound according to the first embodiment, the group represented by -L2-Ar2, R 21 and R 22 are the same or different from each other.

[0142] In the compound according to the first embodiment, L2 is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, more preferably a single bond or a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, even more preferably a single bond or a substituted or unsubstituted arylene group having 6 to 13 ring carbon atoms, still more preferably a single bond or a substituted or unsubstituted arylene group having 6 to 10 ring carbon atoms, and still more preferably a single bond or a substituted or unsubstituted phenylene group.

[0143] The compound according to the first embodiment (the compound represented by the formula (2)) is preferably a compound represented by the following formula (2-111): The compound represented by the following formula (2-111) corresponds to the compound in which L2 in the formula (2-11) is a single bond, and Ar2 is bonded to the benzene ring to which two cyano groups are bonded via a carbon-carbon bond.

[0144] [ka]

[0145] (In the formula (2-111), D 21 , Ar2, R 21 and R 22 are the D in the above formula (2), respectively. 21 , Ar2, R 21 and R 22 is equivalent to

[0146] In the formula (2-111), Ar2 is bonded to the benzene ring to which two cyano groups are bonded via a carbon-carbon bond.

[0147] In the compound according to the first embodiment, R 21 and R22 In the compound according to the first embodiment, the pair consisting of R 201 ~R 212 Any pair of two or more adjacent R 201 ~R 212 For example, R 201 and R 202 A set consisting of R 202 and R 203 A set consisting of R 203 and R 204 A set consisting of R 205 and R 206 A set consisting of R 207 and R 208 A set consisting of R 209 and R 210 A set consisting of R 210 and R 211 and R 211 and R 212 A set consisting of:

[0148] In the compound according to the first embodiment, R 201 , R 202 , R 203 , R 204 , R 205 , R 206 , R 207 , R 208 , R 209 , R 210 , R 211 and R 212 at least one selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted 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, -Si(R 281 )(R 282 )(R 283 ), a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, -O-(R 284 ), a group represented by -S-(R 285), a group represented by -N(R 286 )(R 287 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 288 a group represented by -C(=O)(OR 289 ), a halogen atom, a cyano group, a nitro group, -P(=O)(R 290 )(R 291 ), a group represented by -Ge(R 292 )(R 293 )(R 294 ), a group represented by -B(R 295 )(R 296 ), a group represented by -B(OR 297 )(OR 298 ) or -OS(=O)2(R 299 ) is a group represented by the formula:

[0149] In the compound according to the first embodiment, R 201 , R 202 , R 203 , R 204 , R 205 , R 206 , R 207 , R 208 , R 209 , R 210 , R 211 and R 212 at least one selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, -Si(R 281 )(R 282 )(R 283 ) or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.

[0150] In the compound according to the first embodiment, R 201 , R 202 , R 203 , R 204 , R 205 , R 206 , R 207 , R 208 , R 209 , R210 , R 211 and R 212 At least one selected from the group consisting of the following is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0151] In the compound according to the first embodiment, R 201 , R 202 , R 203 , R 204 , R 205 , R 206 , R 207 , R 208 , R 209 , R 210 , R 211 and R 212 It is more preferable that at least one selected from the group consisting of is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms.

[0152] In the compound according to the first embodiment, R 201 , R 202 , R 203 , R 204 , R 205 , R 206 , R 207 , R 208 , R 209 , R 210 , R 211 and R 212 It is more preferable that at least one selected from the group consisting of: is a substituted or unsubstituted phenyl group.

[0153] In the compound according to the first embodiment, R 205 , R 206 , R 207 and R 208 It is preferred that at least one selected from the group consisting of is not a hydrogen atom.

[0154] In the compound according to the first embodiment, R 205, R 206 , R 207 and R 208 At least one selected from the group consisting of the following is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0155] In the compound according to the first embodiment, R 205 , R 206 , R 207 and R 208 It is more preferable that at least one selected from the group consisting of is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms.

[0156] In the compound according to the first embodiment, R 205 , R 206 , R 207 and R 208 It is more preferable that at least one selected from the group consisting of: is a substituted or unsubstituted phenyl group.

[0157] In the compound according to the first embodiment, R 201 and R 212 or both of the groups are preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms.

[0158] In the compound according to the first embodiment, R 201 and R 212 More preferably, one or both of the groups are substituted or unsubstituted phenyl groups.

[0159] In the compound according to the first embodiment, R 201 and R207 or both of the groups are preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms.

[0160] In the compound according to the first embodiment, R 201 and R 207 More preferably, one or both of the groups are substituted or unsubstituted phenyl groups.

[0161] In the compound according to the first embodiment, D 21 is preferably a group represented by the following formula (201), formula (202), formula (203), formula (204), formula (205), formula (206) or formula (207), and more preferably the following formula (201), formula (202), formula (203) or formula (204).

[0162] [ka]

[0163] [ka]

[0164] [ka]

[0165] (In the formulas (201), (202), (203), (204), (205), (206) and (207), * indicates a bonding position.)

[0166] In the compound according to the first embodiment, the formulae (201), (202), (203), (204), (205), (206), and (207) each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted 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, -Si(R 281 )(R 282 )(R 283 ), a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, -O-(R 284 ), a group represented by -S-(R 285 ), a group represented by -N(R 286 )(R 287 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 288 a group represented by -C(=O)(OR 289 ), a halogen atom, a cyano group, a nitro group, -P(=O)(R 290 )(R 291 ), a group represented by -Ge(R 292 )(R 293 )(R 294 ), a group represented by -B(R 295 )(R 296 ), a group represented by -B(OR 297 )(OR 298 ) and -OS(=O)2(R 299 The group may or may not have one or more substituents selected from the group consisting of groups represented by the following formula:

[0167] In the compound according to the first embodiment, R 21 and R 22 It is preferred that one or both of the groups is not a hydrogen atom.

[0168] In the compound according to the first embodiment, R 21 and R 22or both of the above are a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted 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, -Si(R 281 )(R 282 )(R 283 ), a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, -O-(R 284 ), a group represented by -S-(R 285 ), a group represented by -N(R 286 )(R 287 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 288 a group represented by -C(=O)(OR 289 ), a halogen atom, a cyano group, a nitro group, -P(=O)(R 290 )(R 291 ), a group represented by -Ge(R 292 )(R 293 )(R 294 ), a group represented by -B(R 295 )(R 296 ), a group represented by -B(OR 297 )(OR 298 ) or -OS(=O)2(R 299 ) is preferably a group represented by the formula (I).

[0169] In the compound according to the first embodiment, R 21 and R is not a hydrogen atom 22 is preferably bonded via a carbon-carbon bond to the benzene ring to which the two cyano groups in each formula representing the compound according to the first embodiment are bonded.

[0170] In the compound according to the first embodiment, R 21 and R 22 It is preferable that one or both of the groups be a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0171] In the compound according to the first embodiment, R 21 and R 22 It is more preferable that one or both of the groups be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms.

[0172] In the compound according to the first embodiment, R 21 and R 22 More preferably, one or both of the groups are substituted or unsubstituted phenyl groups.

[0173] The compound according to the first embodiment (the compound represented by the formula (2)) is preferably a compound represented by the following formula (2-112).

[0174] [ka]

[0175] (In the formula (2-112), D 21 and Ar2 are D in the formula (2), respectively. 21 and Ar2, R 221 , R 222 , R 223 , R 224 , R 225 , R 231 , R 232 , R 233 , R 234 and R 235 each independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted 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, -Si(R 281 )(R 282 )(R 283), a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, -O-(R 284 ), a group represented by -S-(R 285 ), a group represented by -N(R 286 )(R 287 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 288 a group represented by -C(=O)(OR 289 ), a halogen atom, a cyano group, a nitro group, -P(=O)(R 290 )(R 291 ), a group represented by -Ge(R 292 )(R 293 )(R 294 ), a group represented by -B(R 295 )(R 296 ), a group represented by -B(OR 297 )(OR 298 ) or -OS(=O)2(R 299 ) is a group represented by

[0176] In the above formula (2-112), Ar2 is bonded to the benzene ring to which two cyano groups are bonded via a carbon-carbon bond.

[0177] It is also preferable that the compound according to the first embodiment (the compound represented by the formula (2)) is a compound represented by the following formula (2-113).

[0178] [ka]

[0179] (In the formula (2-113), D 21 and Ar2 are D in the formula (2), respectively. 21 and Ar2, R 221 , R 222 , R 223 , R 224 , R 225 , R 231, R 232 , R 233 , R 234 and R 235 are R in the formula (2-112), respectively. 221 , R 222 , R 223 , R 224 , R 225 , R 231 , R 232 , R 233 , R 234 and R 235 is synonymous with The Four Rs 24 each independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted 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, -Si(R 281 )(R 282 )(R 283 ), a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, -O-(R 284 ), a group represented by -S-(R 285 ), a group represented by -N(R 286 )(R 287 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 288 a group represented by -C(=O)(OR 289 ), a halogen atom, a cyano group, a nitro group, -P(=O)(R 290 )(R 291 ), a group represented by -Ge(R 292 )(R 293 )(R 294 ), a group represented by -B(R 295 )(R 296 ), a group represented by -B(OR 297 )(OR 298 ) or -OS(=O)2(R 299 ) and a plurality of R 24 are either identical or different.)

[0180] In the compound according to the first embodiment, when L2 is not a single bond, Ar2 is also preferably a substituted or unsubstituted 9-carbazolyl group. For example, the compound represented by the formula (2-113) corresponds to a case where L2 is not a single bond but a substituted or unsubstituted phenylene group, and therefore Ar2 is also preferably a substituted or unsubstituted 9-carbazolyl group.

[0181] In the compound according to the first embodiment, Ar2 is It is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, It is more preferable that the aryl group is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, It is more preferably a substituted or unsubstituted aryl group having 6 to 13 ring carbon atoms, It is even more preferably a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms.

[0182] It is also preferable that the compound according to the first embodiment (the compound represented by the formula (2)) is a compound represented by the following formula (2-114).

[0183] [ka]

[0184] (In the formula (2-114), D 21 is D in the above formula (2) 21 is synonymous with R 221 , R 222 , R 223 , R 224 , R 225 , R 231 , R 232 , R 233 , R 234 , R 235 , R 251 , R 252 , R 253 , R 254 and R 255each independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted 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, -Si(R 281 )(R 282 )(R 283 ), a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, -O-(R 284 ), a group represented by -S-(R 285 ), a group represented by -N(R 286 )(R 287 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 288 a group represented by -C(=O)(OR 289 ), a halogen atom, a cyano group, a nitro group, -P(=O)(R 290 )(R 291 ), a group represented by -Ge(R 292 )(R 293 )(R 294 ), a group represented by -B(R 295 )(R 296 ), a group represented by -B(OR 297 )(OR 298 ) or -OS(=O)2(R 299 ) is a group represented by

[0185] In the compound according to the first embodiment, R 221 , R 222 , R 223 , R 224 and R 225 Any pair of two or more adjacent ones of these is not bonded to each other. In the compound according to the first embodiment, R 231 , R 232 , R 233 , R 234 and R 235 Any pair of two or more adjacent ones of these is not bonded to each other. In the compound according to the first embodiment, R 251 , R 252 , R 253 , R 254 and R 255 Any pair of two or more adjacent ones of these is not bonded to each other. In the compound according to the first embodiment, a plurality of R 24 Any pair of two or more adjacent ones of these is not bonded to each other.

[0186] In the compound according to the first embodiment, Ar2 is a substituted or unsubstituted heterocyclic group having 6 to 30 ring atoms, a substituted or unsubstituted heterocyclic group having 6 to 18 ring atoms, or It is also preferably a substituted or unsubstituted heterocyclic group having 6 to 13 ring atoms.

[0187] In the compound according to the first embodiment, Ar2 is also preferably a group represented by the following formula (21).

[0188] [ka]

[0189] (In the formula (21), X2 is an oxygen atom, a sulfur atom, or NR 260 and R 260 , R 261 , R 262 , R 263 , R 264 and the three R's 26 each independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted 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, -Si(R 281 )(R 282 )(R 283), a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, -O-(R 284 ), a group represented by -S-(R 285 ), a group represented by -N(R 286 )(R 287 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 288 a group represented by -C(=O)(OR 289 ), a halogen atom, a cyano group, a nitro group, -P(=O)(R 290 )(R 291 ), a group represented by -Ge(R 292 )(R 293 )(R 294 ), a group represented by -B(R 295 )(R 296 ), a group represented by -B(OR 297 )(OR 298 ) or -OS(=O)2(R 299 ) and a plurality of R 26 are either identical or different.)

[0190] In the compound according to the first embodiment, R 260 is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, even more preferably a substituted or unsubstituted aryl group having 6 to 13 ring carbon atoms, still more preferably a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms, and even more preferably a substituted or unsubstituted phenyl group.

[0191] It is also preferable that the compound according to the first embodiment (the compound represented by the formula (2)) is a compound represented by the following formula (2-115).

[0192] [ka]

[0193] (In the formula (2-115), D 21 is D in the above formula (2) 21 is synonymous with R 221 , R 222 , R 223 , R 224 , R 225 , R 231 , R 232 , R 233 , R 234 and R 235 are R in the formula (2-112), respectively. 221 , R 222 , R 223 , R 224 , R 225 , R 231 , R 232 , R 233 , R 234 and R 235 is synonymous with X2, R 26 , R 261 , R 262 , R 263 and R 264 are X2 and R in the formula (21), respectively. 26 , R 261 , R 262 , R 263 and R 264 is equivalent to

[0194] In the compound according to the first embodiment, R 221 ~R 225 , R 231 ~R 235 , R 24 , R 251 ~R 255 , R 26 , R 261 ~R 264 are preferably each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.

[0195] In the compound according to the first embodiment, R 221 ~R 225 , R 231 ~R 235 , R 24 , R 251 ~R 255 , R 26 , R 261 ~R 264 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.

[0196] In the compound according to the first embodiment, R 221 ~R 225 , R 231 ~R 235 , R 24 , R 251 ~R 255 , R 26 , R 261 ~R 264 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms.

[0197] In the compound according to the first embodiment, the substituent in the term "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted alkenyl group having 2 to 25 carbon atoms, an unsubstituted alkynyl group having 2 to 25 carbon atoms, an unsubstituted cycloalkyl group having 3 to 25 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 ), an unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 908a group represented by -COOR 909 a group represented by -P(=O)(R 931 )(R 932 ), a group represented by -Ge(R 933 )(R 934 )(R 935 ), a group represented by -B(R 936 )(R 937 ), a group represented by -S(=O)R 938 a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms, R 901 ~R 909 , and R 931 ~R 938 are preferably each independently a hydrogen atom, 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.

[0198] In the compound according to the first embodiment, the substituent in the term "substituted or unsubstituted" is preferably a halogen atom, 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.

[0199] In the compound according to the first embodiment, the substituent in the term "substituted or unsubstituted" is preferably an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted aryl group having 6 to 13 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 13 ring atoms.

[0200] In the compound according to the first embodiment, it is preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0201] The compound according to the first embodiment (the compound represented by the formula (2)) preferably contains at least one deuterium atom.

[0202] (thermally activated delayed fluorescence) The compound according to the first embodiment is preferably a thermally activated delayed fluorescent compound. In this specification, thermally activated delayed fluorescent compound may be referred to as delayed fluorescent compound.

[0203] Delayed fluorescence is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Adachi Chihaya, published by Kodansha). In that paper, the energy difference ΔE between the excited singlet state and the excited triplet state of a fluorescent material is 13 It has been explained that if the transition probability can be reduced, the reverse energy transfer from the excited triplet state, which normally has a low transition probability, to the excited singlet state occurs with high efficiency, resulting in the appearance of thermally activated delayed fluorescence (TADF). Furthermore, Figure 10.38 in this document explains the mechanism by which delayed fluorescence occurs. The compound according to the first embodiment is preferably a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism.

[0204] Generally, delayed fluorescence can be confirmed by transient PL (photoluminescence) measurement.

[0205] The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from transient PL measurements. Transient PL measurements are a technique in which a sample is excited by irradiating it with a pulsed laser, and then the decay behavior (transient characteristics) of the PL emission is measured after the irradiation is stopped. PL emission from TADF materials is classified into emission components from singlet excitons generated during the initial PL excitation, and emission components from singlet excitons generated via triplet excitons. The lifetime of singlet excitons generated during the initial PL excitation is extremely short, on the order of nanoseconds. Therefore, the emission from these singlet excitons decays quickly after irradiation with a pulsed laser. On the other hand, delayed fluorescence decays slowly because it is emitted from singlet excitons generated via triplet excitons, which have a long lifetime. Thus, there is a large time difference between the emission from the singlet excitons generated by the initial PL excitation and the emission from the singlet excitons generated via triplet excitons. Therefore, the emission intensity derived from delayed fluorescence can be measured.

[0206] A schematic diagram of an exemplary apparatus for measuring transient PL is shown in Figure 1. An example of a method for measuring transient PL and an analysis of the behavior of delayed fluorescence will be described below using Figure 1.

[0207] 1 includes a pulsed laser unit 101 capable of irradiating light of a predetermined wavelength, a sample chamber 102 for accommodating a measurement sample, a spectroscope 103 for dispersing the light emitted from the measurement sample, a streak camera 104 for forming a two-dimensional image, and a personal computer 105 for capturing and analyzing the two-dimensional image. Note that the measurement of transient PL is not limited to the device shown in FIG. 1.

[0208] The sample accommodated in the sample chamber 102 is obtained by forming a thin film on a quartz substrate, in which the matrix material is doped with a doping material at a concentration of 12 mass %.

[0209] A pulsed laser is irradiated from the pulsed laser unit 101 onto a thin film sample placed in the sample chamber 102 to excite the doping material. Emission light is extracted in a direction 90 degrees to the irradiation direction of the excitation light, and the extracted light is dispersed by the spectrometer 103, forming a two-dimensional image in the streak camera 104. As a result, a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and bright spots correspond to emission intensity. By cutting out this two-dimensional image along a predetermined time axis, an emission spectrum can be obtained in which the vertical axis represents emission intensity and the horizontal axis represents wavelength. Furthermore, by cutting out the two-dimensional image along the wavelength axis, a decay curve (transient PL) can be obtained in which the vertical axis represents the logarithm of emission intensity and the horizontal axis represents time.

[0210] For example, a thin film sample A was prepared as described above using the following compound HX1 as the matrix material and the following compound DX1 as the doping material, and transient PL measurement was carried out.

[0211] [ka]

[0212] Here, the attenuation curves were analyzed using the above-mentioned thin film sample A and thin film sample B. Thin film sample B was prepared as described above using the following compound HX2 as a matrix material and the above-mentioned compound DX1 as a doping material.

[0213] FIG. 2 shows the decay curves obtained from the transient PL measured for thin film sample A and thin film sample B.

[0214] [ka]

[0215] As described above, transient PL measurements can be used to obtain an emission decay curve with emission intensity on the vertical axis and time on the horizontal axis. Based on this emission decay curve, the fluorescence intensity ratio between the fluorescence emitted from the singlet excited state generated by photoexcitation and the delayed fluorescence emitted from the singlet excited state generated by back energy transfer via the triplet excited state can be estimated. In delayed fluorescent materials, the ratio of the intensity of the delayed fluorescence, which decays slowly, to the intensity of the fluorescence, which decays quickly, is somewhat larger.

[0216] Specifically, there are two types of luminescence from delayed fluorescent materials: prompt luminescence and delayed luminescence. Prompt luminescence is luminescence that is observed immediately from the excited state after being excited by pulsed light (light irradiated from a pulsed laser) with a wavelength that the delayed fluorescent material absorbs. Delayed luminescence is luminescence that is not observed immediately after excitation by the pulsed light, but is observed later.

[0217] The amounts of prompt luminescence and delay luminescence and their ratio can be determined by a method similar to that described in "Nature 492, 234-238, 2012" (Reference 1). Note that the device used to calculate the amounts of prompt luminescence and delay luminescence is not limited to the device described in Reference 1 or the device shown in FIG. 1.

[0218] Furthermore, to measure the delayed fluorescence of the compound according to the first embodiment, a sample prepared by the following method is used. For example, the compound according to the first embodiment is dissolved in toluene to prepare a dilute solution having an absorbance of 0.05 or less at the excitation wavelength to eliminate the contribution of self-absorption. To prevent quenching by oxygen, the sample solution is frozen and degassed, and then sealed in a cell with a lid under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the sample solution was measured using a spectrofluorometer FP-8600 (JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. The total fluorescence quantum yield was calculated using the fluorescence area intensities of both spectra according to equation (1) in Morris et al., J. Phys. Chem. 80 (1976) 969.

[0219] In the first embodiment, the amount of prompt luminescence (instant luminescence) of the compound to be measured is X P and the amount of delay light emission is X D When X D / X P It is preferable that the value is 0.05 or more. The amounts and ratio of prompt luminescence and delayed luminescence of compounds other than the compound according to the first embodiment in this specification are measured in the same manner as the amounts and ratio of prompt luminescence and delayed luminescence of the compound according to the first embodiment.

[0220] (ΔST) In this specification, the lowest excited singlet energy S1 and the energy gap T at 77 [K] 77K The difference between (S1-T 77K ) is defined as ΔST.

[0221] The lowest excited singlet energy S1(M2) of the compound according to the first embodiment and the energy gap T at 77 [K] of the compound according to the first embodiment 77KThe difference ΔST(M2) from (M2) is preferably less than 0.3 eV, more preferably less than 0.2 eV, even more preferably less than 0.1 eV, and even more preferably less than 0.01 eV. That is, ΔST(M2) preferably satisfies the relationship of the following mathematical formula (10), (11), (12), or (13). ΔST(M2)=S1(M2)-T 77K (M2)<0.3eV…(Number 10) ΔST(M2)=S1(M2)-T 77K (M2)<0.2eV …(Math. 11) ΔST(M2)=S1(M2)-T 77K (M2)<0.1eV …(Math. 12) ΔST(M2)=S1(M2)-T 77K (M2)<0.01eV…(Math 13)

[0222] (Relationship between triplet energy and energy gap at 77[K]) Here, the relationship between the triplet energy and the energy gap at 77 K will be explained. In this specification, the energy gap at 77 K differs from the triplet energy that is usually defined. Triplet energy is measured as follows. First, a sample is prepared by dissolving the compound to be measured in an appropriate solvent and sealing the solution in a quartz glass tube. The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this sample is measured at low temperature (77 K). A tangent line is drawn to the rising edge of the short wavelength side of this phosphorescence spectrum, and the triplet energy is calculated using a predetermined conversion formula based on the wavelength value at the intersection of the tangent line and the horizontal axis. Among the compounds according to the first embodiment, the thermally activated delayed fluorescent compound is preferably a compound with a small ΔST. When ΔST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at low temperatures (77 [K]), resulting in a mixture of excited singlet and excited triplet states. As a result, the spectrum measured in the same manner as above contains light emission from both the excited singlet and excited triplet states, and although it is difficult to clearly distinguish which state the light emission originates from, the triplet energy value is generally considered to be dominant. Therefore, in this specification, although the measurement method is the same as that of the ordinary triplet energy T, in order to distinguish between the two, the value measured as follows is referred to as the energy gap T 77K The compound to be measured is dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol / L, and this solution is placed in a quartz cell to serve as the measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this measurement sample is measured at low temperature (77 [K]), and a tangent line is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent line and the horizontal axis is determined. edge Based on the [nm], the amount of energy calculated using the following conversion formula (F1) is the energy gap T at 77 [K]. 77K Let's say. Conversion formula (F1):T 77K [eV]=1239.85 / λ edge

[0223] The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows: When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum of the spectral maxima, consider the tangent at each point on the curve toward the long wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope is at its maximum (i.e., the tangent at the inflection point) is the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that a maximum point having a peak intensity that is 15% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and the tangent drawn at the point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side is defined as the tangent to the rising edge on the short wavelength side of the phosphorescence spectrum. Phosphorescence can be measured using an F-4500 spectrofluorophotometer manufactured by Hitachi High-Technologies Corp. However, the measuring device is not limited to this, and measurements may be performed by combining a cooling device, a cryogenic container, an excitation light source, and a light-receiving device.

[0224] (Lowest excited singlet energy S1) The following method can be used to measure the lowest excited singlet energy S1 using a solution (sometimes referred to as a solution method). A 10 μmol / L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the absorption spectrum (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K). A tangent line is drawn to the falling edge on the long wavelength side of this absorption spectrum, and the wavelength value λedge [nm] at the intersection of this tangent line and the horizontal axis is substituted into the following conversion formula (F2) to calculate the lowest excited singlet energy. Conversion formula (F2): S1[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.

[0225] The tangent to the fall on the long wavelength side of the absorption spectrum is drawn as follows. When moving along the spectral curve from the longest maximum value on the longest wavelength side of the absorption spectrum toward longer wavelengths, consider the tangent at each point on the curve. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the slope is minimum on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is considered to be the tangent to the fall on the long wavelength side of the absorption spectrum. Note that maximum points with absorbance values ​​of 0.2 or less are not included in the maximum values ​​on the longest wavelength side.

[0226] (Method of producing the compound according to the first embodiment) The compound according to the first embodiment can be produced according to the synthesis method described in the examples below, or by imitating the synthesis method and using known alternative reactions and raw materials suited to the target compound.

[0227] (Specific examples of compounds according to the first embodiment) Specific examples of the compound according to the first embodiment include the following compounds. However, the present invention is not limited to these specific examples. In the specific examples of compounds in this specification, a deuterium atom may be represented as D in a chemical formula, a proton atom may be represented as H or may be omitted, a methyl group may be represented as Me, and a phenyl group may be represented as Ph.

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[0317] [Second form] <Materials for Organic Elastomer Materials> The material for an organic electroluminescence device according to the second embodiment contains the compound according to the first embodiment (the compound represented by the general formula (2)). The material for an organic electroluminescence device may be abbreviated as a material for an organic EL device. One aspect of the material for an organic EL device includes only the compound according to the first embodiment, and another aspect of the material for an organic EL device includes the compound according to the first embodiment and another compound different from the compound in the first embodiment. In the material for an organic EL device of the second embodiment, the compound according to the first embodiment is preferably a host material. In this case, the material for an organic EL device may contain the compound according to the first embodiment as a host material and other compounds such as a dopant material. In the material for an organic EL device of the second embodiment, the compound according to the first embodiment is preferably a thermally activated delayed fluorescent material.

[0318] Third Embodiment <Organic electroluminescence element> An organic EL element according to a third embodiment will be described. The organic EL device according to the third embodiment includes an organic layer between an anode and a cathode. The organic layer includes one or more layers. The organic layer includes at least one layer made of an organic compound. Alternatively, the organic layer is formed by stacking multiple layers made of organic compounds. The organic layer may further include an inorganic substance (at least one of an inorganic compound and a simple substance).

[0319] The organic layer may be composed of, for example, a single light-emitting layer, or may include a layer that can be used in an organic EL device. The layer that can be used in an organic EL device is not particularly limited, but may include, for example, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer. A zone consisting of one or more organic layers disposed between the light-emitting layer and the anode may be referred to as a hole transport zone, and a zone consisting of one or more organic layers disposed between the light-emitting layer and the cathode may be referred to as an electron transport zone.

[0320] FIG. 3 shows a schematic configuration of an example of an organic EL element according to the third embodiment. The organic EL element 1 includes a light-transmitting 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 configured by laminating, in this order from the anode 3 side, a hole injection layer 6, a hole transport layer 7, an emitting layer 5, an electron transport layer 8, and an electron injection layer 9. The present invention is not limited to the configuration of the organic EL element shown in FIG.

[0321] The organic EL device according to the third embodiment includes a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer including one or more layers, at least one of which contains a second compound, the second compound being the compound according to the first embodiment. The second compound may be referred to as compound M2.

[0322] (light-emitting layer) In the organic EL device according to the third embodiment, it is preferable that at least one of the one or more layers included in the organic layer is an emitting layer, and the emitting layer contains a second compound (the compound according to the first embodiment).

[0323] In the organic EL device according to the third embodiment, the light-emitting layer preferably contains a fluorescent first compound, which may be referred to as compound M1. In the organic EL device according to the third embodiment, the light-emitting layer preferably contains a second compound (the compound according to the first embodiment) and a fluorescent first compound. In this embodiment, the second compound is preferably a host material (sometimes referred to as a matrix material), and the first compound is preferably a dopant material (sometimes referred to as a guest material, an emitter, or a light-emitting material). In the third embodiment, when the light-emitting layer contains the second compound, the light-emitting layer preferably does not contain a phosphorescent metal complex, and preferably does not contain any metal complex other than the phosphorescent metal complex.

[0324] In one form of the third embodiment, the light-emitting layer may contain a metal complex. In one aspect of the third embodiment, the light-emitting layer preferably does not contain a metal complex. In one aspect of the third embodiment, the light-emitting layer preferably does not contain a phosphorescent material. In one embodiment of the third embodiment, the light-emitting layer preferably does not contain a heavy metal complex or a phosphorescent rare earth metal complex. Examples of heavy metal complexes include an iridium complex, an osmium complex, and a platinum complex.

[0325] (Second Compound) The second compound is the compound according to the first embodiment. In the organic EL device according to the third embodiment, the second compound is preferably a thermally activated delayed fluorescent compound.

[0326] (First Compound) The first compound is preferably a fluorescent compound. The first compound is preferably a compound that does not exhibit thermally activated delayed fluorescence. The first compound of this embodiment is not a phosphorescent metal complex. Preferably, the first compound is not a heavy metal complex. Also, it is preferable that the first compound is not a metal complex.

[0327] The first compound of this embodiment may be a fluorescent material. Specific examples of the fluorescent material include bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl-substituted pyrene derivatives, bisarylaminochrysene derivatives, aryl-substituted chrysene derivatives, bisarylaminofluoranthene derivatives, aryl-substituted fluoranthene derivatives, indenoperylene derivatives, acenaphthofluoranthene derivatives, compounds containing boron atoms, pyrromethene-boron complex compounds, compounds having a pyrromethene skeleton, metal complexes of compounds having a pyrromethene skeleton, diketopyrrolopyrrole derivatives, perylene derivatives, and naphthacene derivatives.

[0328] (Maximum peak wavelength) The first compound is preferably a compound that emits light with a maximum peak wavelength of 400 nm or more and 700 nm or less.

[0329] The first compound is preferably a compound that exhibits blue emission. In this specification, blue emission refers to emission having a maximum peak wavelength in the fluorescence spectrum within the range of 430 nm or more and 480 nm or less. When the first compound is a blue fluorescent compound, the maximum peak wavelength of the first compound is preferably 480 nm or less, and more preferably 475 nm or less. When the first compound is a blue fluorescent compound, the maximum peak wavelength of the first compound is preferably 430 nm or more, and more preferably 440 nm or more. In this specification, the maximum peak wavelength of fluorescent light may be referred to as the maximum peak wavelength of fluorescent light.

[0330] The first compound is also preferably a compound that exhibits red or green emission. In this specification, red light emission refers to light emission having a maximum peak wavelength in the fluorescence spectrum in the range of 600 nm or more and 660 nm or less. When the first compound is a red fluorescent compound, the maximum peak wavelength of the first compound is preferably 600 nm or more and 660 nm or less, more preferably 600 nm or more and 640 nm or less, and even more preferably 610 nm or more and 630 nm or less. In this specification, green light emission refers to light emission having a maximum peak wavelength in the fluorescence spectrum in the range of 500 nm or more and 560 nm or less. When the first compound is a green fluorescent compound, the maximum peak wavelength of the first compound is preferably 500 nm or more and 560 nm or less, more preferably 500 nm or more and 540 nm or less, and even more preferably 510 nm or more and 540 nm or less.

[0331] (Emission spectrum half width) In this embodiment, the full width at half maximum (FWHM) of the emission spectrum of the first compound as the fluorescent material is preferably 40 nm or less, more preferably 30 nm or less. In this embodiment, the full width at half maximum (FWHM) of the emission spectrum of the first compound as the fluorescent material is, for example, 5 nm or more, or 10 nm or more. FWHM is an abbreviation for full width at half maximum.

[0332] In this specification, the maximum peak wavelength of fluorescence emission is the wavelength at which the compound to be measured is 10 -6 moles / liter or more, 10 -5 The FWHM is the maximum peak wavelength of the fluorescence spectrum at which the emission intensity is greatest in a toluene solution in which the compound is dissolved at a concentration of 1 / 4 mole / liter or less. The FWHM of the emission spectrum is the full width at half maximum of the maximum peak of the fluorescence spectrum. A fluorescence spectrum measuring device or a fluorescence spectrophotometer can be used as a device for measuring the fluorescence spectrum. For example, a fluorescence spectrophotometer (manufactured by JASCO Corporation, device name: FP-8300) or a fluorescence spectrophotometer (manufactured by Hitachi High-Tech Science Corporation, device name: F-7000) can be used. Note that the fluorescence spectrophotometer is not limited to the devices exemplified here.

[0333] (Stokes shift) In this embodiment, the Stokes shift of the first compound as a fluorescent material is preferably 25 nm or less, more preferably 20 nm or less. In this embodiment, the Stokes shift of the first compound as a fluorescent material is preferably 5 nm or more, more preferably 10 nm or more. By making the Stokes shift of the first compound 20 nm or less, excitation energy can be reduced. By setting the Stokes shift of the first compound to 10 nm or more, self-absorption can be suppressed and loss of efficiency can be reduced. The Stokes shift can be measured by the following method. The compound to be measured is added to 2.0 × 10 -5 The compound is dissolved in toluene at a concentration of 1000 mol / L to prepare a measurement sample. The measurement sample is placed in a quartz cell and irradiated with continuous light in the ultraviolet-visible region at room temperature (300 K), and the absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength) is measured. A spectrophotometer can be used to measure the absorption spectrum, for example, the Hitachi High-Tech Science U-3900 / 3900H spectrophotometer. The compound to be measured is dissolved in toluene at a concentration of 4.9 x 10 -6 The measurement sample is prepared by dissolving it in toluene at a concentration of mol / L. The measurement sample is placed in a quartz cell and irradiated with excitation light at room temperature (300 K), and the fluorescence spectrum (vertical axis: fluorescence intensity, horizontal axis: wavelength) is measured. A spectrophotometer can be used to measure the fluorescence spectrum, such as the Hitachi High-Tech Science F-7000 fluorescence spectrophotometer. From these absorption and fluorescence spectra, the difference between the absorption maximum wavelength and the fluorescence maximum wavelength is calculated to determine the Stokes shift (SS). The unit of Stokes shift SS is nm.

[0334] (Compound represented by formula (1)) In the organic EL device according to the third embodiment, the first compound is preferably a compound represented by the following formula (1).

[0335] [ka]

[0336] (In the formula (1), Ring A1, ring B1 and ring C1 each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, L 11 and L 12 are each independently, NR 10 , oxygen atom, sulfur atom, selenium atom, C(R 11 )(R 12 ), or Si(R 13 )(R 14 ) and L 13 is a boron atom, a phosphorus atom, or P=O, R 10 ~R 14 are each independently, combines with ring A1, ring B1 or ring C1 to form a substituted or unsubstituted monocyclic ring, or combines with ring A1, ring B1 or ring C1 to form a substituted or unsubstituted fused ring, or not bonded to ring A1, ring B1, or ring C1, R 11 and R 12 teeth, joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 13 and R 14 teeth, joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 10 ~R 14 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, -C(R 15 an iminyl group represented by )=N; 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 15 teeth, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, R 10 If there are multiple R 10 are identical to or different from each other, R 11 If there are multiple R 11 are identical to or different from each other, R 12 If there are multiple R 12 are identical to or different from each other, R 13 If there are multiple R 13 are identical to or different from each other, R 14 If there are multiple R 14 are identical to or different from each other, R 15 If there are multiple R 15 are either identical or different.)

[0337] In this embodiment, the compound represented by the formula (1) is preferably a compound represented by the following formula (11).

[0338] [ka]

[0339] (In the formula (11), Ring A1, ring B1 and ring C1 each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, R 101 and R 102 are each independently, combines with ring A1, ring B1 or ring C1 to form a substituted or unsubstituted monocyclic ring, or combines with ring A1, ring B1 or ring C1 to form a substituted or unsubstituted fused ring, or not bonded to ring A1, ring B1, or ring C1, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 101 and R 102 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, -CR 15 an iminyl group represented by =N; 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.

[0340] In this embodiment, the compound represented by the formula (1) is preferably a compound selected from the group consisting of compounds represented by the following formulas (11-1) to (11-6).

[0341] [ka]

[0342] [ka]

[0343] [ka]

[0344] (In the formula (11-1), Xa is an oxygen atom, a sulfur atom, a selenium atom, or a C(R 103 )(R 104 ), or NR 105 and R 101 and R 121 Paired with R 121 ~R 123 A set of two or more adjacent 123 and R 102 Paired with R 102 and R 124 Paired with R 124 ~R 127 A set of two or more adjacent 127 and R 112 Pairs with and R 112 and R 111 and joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 101 and R 102 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, -CR 15 an iminyl group represented by =N; 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 103 ~R 105 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 111 , R 112 , and R 121 ~R 127 are each independently a hydrogen atom or a substituent R X and The substituent R X 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 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, 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, and R 902 If there are multiple R 902 are the same or different, and R 903 If there are multiple R 903 are the same or different, and R 904 If there are multiple R 904 are the same or different, and R 905 If there are multiple R 905 are the same or different, and R 906 If there are multiple R 906 are the same or different, and R 907 If there are multiple R 907 are either identical or different.)

[0345] (In the formula (11-2), Xa is an oxygen atom, a sulfur atom, a selenium atom, or a C(R 103 )(R 104 ), or NR 105 and R 101 and R 121 Paired with R 121 ~R 123 A set of two or more adjacent 123 and R 102 Paired with R 102 and R 124 Paired with R 124 ~R 127 A set of two or more adjacent 113 and R 114 Pairs with and R 114 and R 101 and joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 101 and R 102 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, -CR 15 an iminyl group represented by =N; 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 103 ~R 105 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 113 , R 114 , and R 121 ~R 127 are each independently a hydrogen atom or a substituent R X and the substituent R X represents the substituent R in the formula (11-1). X is synonymous with R 103 If there are multiple R 103 are identical to or different from each other, R 104 If there are multiple R 104 are identical to or different from each other, R 105 If there are multiple R 105 are either identical or different.)

[0346] (In the formula (11-3), Xa and Xb each independently represent an oxygen atom, a sulfur atom, a selenium atom, or a C(R 103 )(R 104 ), or NR 105 and R 101 and R 121 Paired with R 121 ~R 123 A set of two or more adjacent 123 and R 102 Paired with R 115 and R 116 Paired with R 116 and R 112 Pairs with and R 112 and R 111 and joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 101 and R 102 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, -CR 15 an iminyl group represented by =N; 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 103 ~R 105 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 111 , R 112 , R 115 , R 116 , and R 121 ~R 123are each independently a hydrogen atom or a substituent R X and the substituent R X represents the substituent R in the formula (11-1). X is synonymous with R 103 If there are multiple R 103 are identical to or different from each other, R 104 If there are multiple R 104 are identical to or different from each other, R 105 If there are multiple R 105 are either identical or different.)

[0347] (In the formula (11-4), Xa and Xb each independently represent an oxygen atom, a sulfur atom, a selenium atom, or a C(R 103 )(R 104 ), or NR 105 and R 101 and R 121 Paired with R 121 ~R 123 A set consisting of two or more adjacent R 123 and R 102 Paired with R 102 and R 118 Paired with R 118 and R 117 Pairs with and R 112 and R 111 and joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 101 and R 102 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, -CR 15 an iminyl group represented by =N; 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 103 ~R 105 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 111 , R 112 , R 117 , R 118 , and R 121 ~R 123 are each independently a hydrogen atom or a substituent R X and the substituent R X represents the substituent R in the formula (11-1). X is synonymous with R 103 If there are multiple R 103 are identical to or different from each other, R 104 If there are multiple R 104 are identical to or different from each other, R 105 If there are multiple R 105 are either identical or different.) (In the formula (11-5), Xa and Xb each independently represent an oxygen atom, a sulfur atom, a selenium atom, or a C(R 103 )(R 104 ), or NR 105 and R 101 and R 121 Paired with R 121 ~R 123 A set of two or more adjacent 123 and R 102 Paired with R 102 and R 118 Paired with R 118 and R117 Paired with R 113 and R 114 Pairs with and R 114 and R 101 and joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 101 and R 102 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, -CR 15 an iminyl group represented by =N; 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 103 ~R 105 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 113 , R 114 , R 117 , R 118 , and R 121 ~R 123 are each independently a hydrogen atom or a substituent R X and the substituent R X represents the substituent R in the formula (11-1). X is synonymous with R 103 If there are multiple R 103 are identical to or different from each other, R 104 If there are multiple R 104 are identical to or different from each other, R 105 If there are multiple R 105 are either identical or different.) (In the formula (11-6), R 101 and R 121 Paired with R 121 ~R 123 A set of two or more adjacent 123 and R 102 Paired with R 102 and R 124 Paired with R 124 ~R 127 A set of two or more adjacent 127 and R 128 Paired with R 128 ~R 131 A pair consisting of two or more adjacent 131 and R 101 and joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 101 and R 102 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, -CR 15 an iminyl group represented by =N; a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 121 ~R 131are each independently a hydrogen atom or a substituent R X and the substituent R X represents the substituent R in the formula (11-1). X is equivalent to (R in the formulas (11-1) to (11-6) 15 is R in the formula (1). 15 is equivalent to

[0348] In the compounds represented by the formulas (11-1) to (11-5), R 112 and R 111 Paired with R 113 and R 114 Paired with R 115 and R 116 Pairs with and R 117 and R 118 and

[0049] It is also preferred that one or more pairs selected from the group consisting of

[0050] and

[0051] are bonded to each other to form a substituted or unsubstituted monocyclic ring, or to form a substituted or unsubstituted fused ring.

[0349] In this embodiment, the compound represented by the formula (1) is also preferably a compound represented by the following formula (11-7).

[0350] [ka]

[0351] (In the formula (11-7), Xa is an oxygen atom, a sulfur atom, a selenium atom, or a C(R 103 )(R 104 ), or NR 105 and R 101 and R 121 Paired with R 121 ~R 123 A set of two or more adjacent 123 and R 102 Paired with R 102 and R 124 Paired with R 124 ~R 127 A pair consisting of two or more adjacent137 ~R 140 One or more pairs selected from the group consisting of pairs of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 101 and R 102 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 103 ~R 105 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 121 ~R 127 and R 137 ~R 140 are each independently a hydrogen atom or a substituent R X and the substituent R X represents the substituent R in the formula (11-1). X is equivalent to

[0352] In this embodiment, R 101 and R 102 are each independently preferably 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, more preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and even more preferably a group represented by the following formula (12):

[0353] [ka]

[0354] (In the formula (12), R 132 ~R 136 At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 132 ~R 136 are each independently a hydrogen atom or a substituent R X and the substituent R X represents the substituent R in the formula (11-1). X is synonymous with Multiple R 132 If there are multiple R 132 are the same or different from each other, Multiple R 133 If there are multiple R 133 are the same or different from each other, Multiple R 134 If there are multiple R 134 are the same or different from each other, Multiple R 135 If there are multiple R 135 are the same or different from each other, Multiple R 136 If there are multiple R 136 are the same or different from each other, * indicates the bond position.

[0355] In this embodiment, the compound represented by the formula (1) is also preferably a compound represented by the following formula (12-1).

[0356] [ka]

[0357] (In the formula (12-1), R 121 ~R 131 are R in the formula (11-6), respectively. 121 ~R 131 is synonymous with R 151 ~R 155 At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 156 ~R 160 At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 151 ~R 155 and R 156 ~R 160 are each independently a hydrogen atom or a substituent R X and the substituent R X represents the substituent R in the formula (11-1). X is equivalent to

[0358] In this embodiment, the compound represented by the formula (1) is also preferably a compound represented by the following formula (12-2).

[0359] [ka]

[0360] (In the formula (12-2), R 122 , R 126 , R129 , R 153 , and R 158 are each independently a hydrogen atom or a substituent R X and the substituent R X represents the substituent R in the formula (11-1). X is equivalent to

[0361] In this embodiment, the compound represented by the formula (1) is also preferably a compound represented by the following formula (12-3).

[0362] [ka]

[0363] (In the formula (12-3), R 121 ~R 127 , R 137 ~R 140 and Xa are R in the formula (11-7), respectively. 121 ~R 127 , R 137 ~R 140 and Xa, R 151 ~R 155 At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 156 ~R 160 At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 151 ~R 155 and R 156 ~R 160are each independently a hydrogen atom or a substituent R X and the substituent R X represents the substituent R in the formula (11-1). X is equivalent to

[0364] In this embodiment, the compound represented by the formula (1) is also preferably a compound represented by the following formula (12-4).

[0365] [ka]

[0366] (In the formula (12-4), Xa has the same meaning as Xa in the formula (11-7), and R 122 , R 126 , R 139 , R 153 , and R 158 are each independently a hydrogen atom or a substituent R X and the substituent R X represents the substituent R in the formula (11-1). X is equivalent to

[0367] In this embodiment, R in the first compound 122 , R 126 , R 129 , R 139 , R 153 , and R 158 are each independently preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, more preferably a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and even more preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0368] In this embodiment, it is preferable that Xa and Xb in the first compound each independently represent an oxygen atom or a sulfur atom.

[0369] (Method for producing the compound represented by formula (1)) The compound represented by formula (1) can be produced by a known method. Alternatively, the compound represented by formula (1) can be produced by following a known method and using known alternative reactions and raw materials suited to the target compound.

[0370] (Specific examples of compounds represented by formula (1)) Specific examples of the compound represented by formula (1) include the compounds shown below: In the specific examples below, Me represents a methyl group, tBu represents a tertiary butyl group, and Ph represents a phenyl group.

[0371] [ka]

[0372] [ka]

[0373] [ka]

[0374] [ka]

[0375] [ka]

[0376] In the first compound according to this embodiment, the substituent in the term "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted alkenyl group having 2 to 25 carbon atoms, an unsubstituted alkynyl group having 2 to 25 carbon atoms, an unsubstituted cycloalkyl group having 3 to 25 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 ), an unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 908 a group represented by -COOR 909 a group represented by -S(=O)R 941 a group represented by -P(=O)(R 942 )(R 943 ), a group represented by -Ge(R 944 )(R 945 )(R 946 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms, R 901 ~R 909 , and R 941 ~R 946 are preferably each independently a hydrogen atom, 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.

[0377] In the first compound according to the present embodiment, the substituent in the term "substituted or unsubstituted" is preferably a halogen atom, 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.

[0378] In the first compound according to the present embodiment, the substituent in the term "substituted or unsubstituted" is preferably 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.

[0379] In the first compound according to this embodiment, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0380] (Relationship between the first compound and the second compound in the light-emitting layer) In the organic EL device according to this embodiment, the light-emitting layer preferably contains a second compound and a fluorescent first compound, and the lowest excited singlet energy S1(M1) of the first compound and the lowest excited singlet energy S1(M2) of the second compound satisfy the relationship shown in the following mathematical formula (Mathematical Formula 1). S1(M2)>S1(M1)…(Math 1)

[0381] Energy gap T at 77[K] of the second compound 77K (M2) is the energy gap T of the first compound at 77[K]. 77K It is preferable that the value is larger than (M1). That is, it is preferable that the relationship of the following mathematical formula (Mathematical Formula 5) is satisfied. T 77K (M2)>T 77K (M1)…(Math 5)

[0382] When the organic EL device of this embodiment is caused to emit light, it is preferable that the first compound mainly emits light in the light-emitting layer.

[0383] (TADF mechanism) FIG. 4 is a diagram showing an example of the relationship between the energy levels of a first compound (compound M1) and a second compound (compound M2) in an emitting layer. In FIG. 4, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the first compound. T1(M1) represents the lowest excited triplet state of the first compound. S1(M2) represents the lowest excited singlet state of the second compound. T1(M2) represents the lowest excited triplet state of the second compound. The dashed arrow from S1(M2) to S1(M1) in FIG. 4 represents a Förster type energy transfer from the lowest excited singlet state of the second compound to the first compound. As shown in Figure 4, when a compound with a small ΔST(M2) is used as the second compound, the lowest excited triplet state T1(M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) due to thermal energy. Then, Förster-type energy transfer occurs from the lowest excited singlet state S1(M2) of the second compound to the first compound, generating the lowest excited singlet state S1(M1). As a result, fluorescence emission from the lowest excited singlet state S1(M1) of the first compound can be observed. It is believed that the internal quantum efficiency can theoretically be increased to 100% by utilizing delayed fluorescence via this TADF mechanism.

[0384] (Light emitted from organic EL elements) The organic EL device of this embodiment preferably emits blue, red, or green light. When the organic EL element of this embodiment emits blue light, the maximum peak wavelength of the light emitted from the organic EL element is preferably 430 nm or more and 480 nm or less. When the organic EL element of this embodiment emits green light, the maximum peak wavelength of the light emitted from the organic EL element is preferably 500 nm or more and 560 nm or less. When the organic EL element of this embodiment emits red light, the maximum peak wavelength of the light emitted from the organic EL element is preferably 600 nm or more and 660 nm or less.

[0385] The maximum peak wavelength of light emitted from the organic EL element is measured as follows. Current density is 10mA / cm 2 A voltage is applied to the organic EL element so that the spectral radiance spectrum is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is measured and this is defined as the maximum peak wavelength (unit: nm).

[0386] (Thickness of the light-emitting layer) The thickness of the light-emitting layer in the organic EL device of this embodiment is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and even more preferably 10 nm to 50 nm. When the thickness of the light-emitting layer is 5 nm or more, the formation of the light-emitting layer and the adjustment of chromaticity tend to be easy, and when the thickness of the light-emitting layer is 50 nm or less, an increase in driving voltage is easily suppressed.

[0387] (Compound content in the light-emitting layer) The contents of the first compound and the second compound contained in the light-emitting layer are preferably within the following ranges, for example. The content of the second compound in the light-emitting layer is preferably 10% by mass to 80% by mass, more preferably 10% by mass to 60% by mass, and even more preferably 20% by mass to 60% by mass. The content of the second compound in the light-emitting layer may be 90% by mass to 99.9% by mass, 95% by mass to 99.9% by mass, or 99% by mass to 99.9% by mass. The content of the first compound in the light-emitting layer is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 2% by mass or less. In this embodiment, the light-emitting layer may contain materials other than the first compound and the second compound. The light-emitting layer may contain only one type of first compound or two or more types thereof. The light-emitting layer may contain only one type of second compound or two or more types thereof.

[0388] The structure of the organic EL element according to this embodiment will be further described.

[0389] (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 include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. An inorganic vapor deposition film can also be used.

[0390] (anode) The anode formed on the substrate is preferably made of a metal, alloy, electrically conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or higher). Specific examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), and nitrides of metal materials (e.g., titanium nitride). These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1% by mass or more and 10% by mass or less of zinc oxide added to indium oxide. Furthermore, for example, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5% by mass or more and 5% by mass or less of tungsten oxide and 0.1% by mass or more and 1% by mass or less of zinc oxide relative to indium oxide. Alternatively, the films may be formed by vacuum deposition, coating, inkjet printing, spin coating, or the like. Of the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that easily injects holes regardless of the work function of the anode, so materials that can be used as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures of these, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used. Materials with low work functions, such as elements belonging to Group 1 or 2 of the periodic table, can also be used. These include alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these metals (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these metals. Vacuum deposition and sputtering methods can be used to form the anode using alkali metals, alkaline earth metals, and alloys containing these metals. Furthermore, when using silver paste, coating methods and inkjet methods can be used.

[0391] When the organic EL device is a bottom-emission type, the anode is preferably formed of a light-transmitting or semi-transmitting metal material that transmits light from the light-emitting layer. In this specification, light-transmitting or semi-transmitting means the property of transmitting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The light-transmitting or semi-transmitting metal material can be appropriately selected from the materials listed in the anode section.

[0392] When the organic EL device is a top-emission type, the anode is a reflective electrode having a reflective layer. The reflective layer is preferably formed of a metal material having light reflectivity. In this specification, light reflectivity means the property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The metal material having light reflectivity can be appropriately selected from the materials listed in the above section on the anode. The anode may be composed of only a reflective layer, or may have a multilayer structure including a reflective layer and a conductive layer (preferably a transparent conductive layer). When the anode has a reflective layer and a conductive layer, it is preferable that the conductive layer is disposed between the reflective layer and the hole transport region. The conductive layer can be appropriately selected from the materials listed in the anode section.

[0393] (hole injection layer) The hole injection layer is a layer containing a substance with high hole injection properties, such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, or manganese oxide. In addition, materials with high hole injection properties include low-molecular-weight organic compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), and 1, Other examples include aromatic amine compounds such as 3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1). Furthermore, polymeric compounds (oligomers, dendrimers, polymers, etc.) can also be used as materials with high hole injection properties. Examples include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD). Acid-added polymeric compounds such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can also be used.

[0394] (Hole transport layer) The organic EL device according to the third embodiment preferably includes a hole transport layer between the anode and the light-emitting layer. The hole transport layer is a layer containing a substance with high hole transport properties. For the hole transport layer, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: NPB), Aromatic amine compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) can be used. The substances mentioned here are mainly 10 -6 cm 2It is a material with a hole mobility of 1 / Vs or more. The hole transport layer may be made of carbazole derivatives such as CBP, CzPA, and PCzPA, or anthracene derivatives such as t-BuDNA, DNA, and DPAnth. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) may also be used. However, other substances may be used as long as they have a higher hole-transporting property than an electron-transporting property. The layer containing the substance having a high hole-transporting property may be a single layer or a layer in which two or more layers made of the above-mentioned substances are stacked.

[0395] (electron barrier layer) The organic EL device according to the third embodiment may include an electron blocking layer between the hole transport layer and the light emitting layer. The electron blocking layer is preferably a layer that transports holes and prevents electrons from reaching a layer (e.g., a hole transport layer) closer to the anode than the electron blocking layer. The compound contained in the electron blocking layer is, for example, a compound used in known electron blocking layers, and is preferably at least one compound selected from the group consisting of aromatic amine compounds and carbazole derivatives. The compound contained in the electron blocking layer may also be a monoamine compound having only one substituted or unsubstituted amino group in the molecule. The compound contained in the electron blocking layer may also be a compound having a substituted or unsubstituted carbazolyl group and one substituted or unsubstituted amino group in the molecule. The electron blocking layer may be a layer that prevents excitons generated in the light-emitting layer from migrating to a layer closer to the anode than the electron blocking layer (e.g., a hole transport layer and a hole injection layer) so that excitation energy does not leak from the light-emitting layer to a peripheral layer.

[0396] (hole blocking layer) The organic EL device according to the third embodiment may include a hole blocking layer between the light emitting layer and the electron transporting layer. The hole blocking layer is preferably a layer that transports electrons and prevents holes from reaching a layer (e.g., an electron transport layer) closer to the cathode than the hole blocking layer. The compound contained in the hole blocking layer is, for example, a compound used in known hole blocking layers. The compound contained in the hole blocking layer is preferably at least one compound selected from the group consisting of metal complexes, heteroaromatic compounds, and polymer compounds, similar to the compounds that can be used in the electron transport layer described below. The compound contained in the hole blocking layer may also be at least one compound selected from the group consisting of imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives. Examples of azine derivatives include pyridine derivatives, pyrimidine derivatives, and triazine derivatives. The hole blocking layer may contain one or more compounds selected from the group consisting of pyridine derivatives, pyrimidine derivatives, and triazine derivatives. It is also preferable that the hole blocking layer is a layer that prevents excitons generated in the light-emitting layer from migrating to a layer closer to the cathode than the hole blocking layer (for example, an electron transport layer or an electron injection layer) so that excitation energy does not leak from the light-emitting layer to a peripheral layer.

[0397] (electron transport layer) The organic EL device according to the third embodiment preferably includes an electron transport layer between the cathode and the light-emitting layer. The electron transport layer is a layer containing a substance with high electron transport properties. Examples of materials that can be used for the electron transport layer include: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymer compounds. Specifically, examples of low-molecular-weight organic compounds that can be used include metal complexes such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviated as BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), bathophenanthroline (abbreviated as BPhen), bathocuproine (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs) can also be used. The electron transport layer may contain one or more compounds selected from the group consisting of pyridine derivatives, pyrimidine derivatives, and triazine derivatives as azine derivatives. The substances mentioned here are mainly 10 -6 cm 2 The electron-transporting layer is a substance having an electron mobility of 1 / Vs or higher. Note that any substance other than those mentioned above may be used as the electron-transporting layer as long as it has a higher electron-transporting property than a hole-transporting property. The electron-transporting layer may be a single layer or a stack of two or more layers made of the above-mentioned substances. 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).

[0398] (electron injection layer) The electron injection layer is a layer containing a substance with high electron injection properties. For the electron injection layer, alkali metals, alkaline earth metals, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF), and lithium oxide (LiOx), or compounds thereof can be used. Alternatively, a substance having electron transport properties containing an alkali metal, alkaline earth metal, or a compound thereof, such as Alq containing magnesium (Mg), can be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, the electron injection layer may be formed using a composite material obtained by mixing an organic compound and an electron donor (donor). Such composite materials have excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material that is excellent at transporting the generated electrons. Specifically, for example, the above-mentioned substances constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor may be any substance that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides and alkaline earth metal oxides are also preferred, such as lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (TTF) can also be used.

[0399] (cathode) The cathode is preferably made of a metal, alloy, electrically conductive compound, or mixture thereof, each having a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these. When an alkali metal, an alkaline earth metal, or an alloy containing these is used to form a cathode, a vacuum deposition method or a sputtering method can be used. When a silver paste or the like is used, a coating method or an inkjet method can be used. By providing an electron injection layer, the cathode can be formed using various conductive materials, regardless of the magnitude of the work function, such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, etc. These conductive materials can be deposited by sputtering, inkjet printing, spin coating, or the like.

[0400] When the organic EL device is a bottom-emission type, the cathode is a reflective electrode. The reflective electrode is preferably formed of a metal material having light reflectivity. The metal material having light reflectivity can be appropriately selected from the materials listed in the cathode section.

[0401] When the organic EL device is a top-emission type, the cathode is preferably formed of a light-transmitting or semi-transmitting metal material that transmits light from the light-emitting layer. The light-transmitting or semi-transmitting metal material can be appropriately selected from the materials listed in the cathode section.

[0402] The organic EL element according to this embodiment may be a bottom-emission type organic EL element, or may be a top-emission type organic EL element. When the organic EL element is a bottom-emission type, it is preferable that the anode is a light-transmitting electrode having light transparency, and the cathode is a light-reflective electrode having light reflection. When the organic EL element is a top-emission type, it is preferable that the anode is a light-reflective electrode having light reflectivity, and the cathode is a light-transmitting electrode having light transmittance.

[0403] (capping layer) When the organic EL device is a top-emitting type, the organic EL device usually includes a capping layer on top of the cathode. The capping layer may contain, for example, at least one compound selected from the group consisting of polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitride, and silicon compounds (such as silicon oxide). The capping layer may also contain at least one compound selected from the group consisting of aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, and dibenzofuran derivatives. Furthermore, a laminate in which layers containing these substances are laminated can also be used as the capping layer.

[0404] (Layer formation method) The method for forming each layer of the organic EL element of this embodiment is not limited to those specifically mentioned above, but may be one or more of known methods such as dry film formation methods such as vacuum deposition, sputtering, plasma deposition, and ion plating, and wet film formation methods such as spin coating, dipping, flow coating, and inkjet deposition.

[0405] (film thickness) The thickness of each organic layer in the organic EL element of the present embodiment is not limited except as specifically mentioned above. However, in general, if the thickness is too thin, defects such as pinholes are likely to occur, whereas if the thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, a thickness in the range of several nm to 1 μm is usually preferred.

[0406] The organic EL device according to the third embodiment includes, in an emitting layer, the second compound according to the first embodiment and a first compound having a lowest excited singlet energy smaller than that of the second compound. According to the third embodiment, the device performance of the organic EL device can be improved, and in particular, the luminous efficiency of the organic EL device can be improved. The organic EL device according to the third embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0407] Fourth Embodiment <Organic electroluminescence element> The configuration of an organic EL element according to the fourth embodiment will be described. In the description of the fourth embodiment, the same components as those in the third embodiment will be denoted by the same reference numerals or names, and the description thereof will be omitted or simplified. Furthermore, in the fourth embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the third embodiment can be used.

[0408] The organic EL device according to the fourth embodiment differs from the organic EL device according to the third embodiment in that the light-emitting layer further contains a third compound. Other features are the same as those of the third embodiment. That is, in the fourth embodiment, the light-emitting layer contains a first compound, a second compound, and a third compound. In this embodiment, the second compound is preferably a host material, and the first compound is preferably a dopant material. The third compound may be referred to as compound M3.

[0409] (Third Compound) In the light-emitting layer of the organic EL device of the present embodiment, the third compound may be a thermally activated delayed fluorescence compound or a compound that does not exhibit thermally activated delayed fluorescence, but is preferably a compound that does not exhibit thermally activated delayed fluorescence.

[0410] The third compound is not particularly limited, but is preferably a compound other than an amine compound. For example, the third compound may be a carbazole derivative, a dibenzofuran derivative, or a dibenzothiophene derivative, but is not limited to these derivatives.

[0411] (Compound represented by formula (3)) In the organic EL device of this embodiment, the third compound is also preferably a compound represented by the following formula (3).

[0412] [ka]

[0413] (In the formula (3), A3 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L3 is single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms; a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, or a divalent group formed by bonding three groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, R 31 ~R 38 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 31 ~R 38 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 908 a group represented by -COOR 909 a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or It is a group represented by the following formula (3A):

[0414] [ka]

[0415] (In the formula (3A), R B teeth, 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 908 a group represented by -COOR 909 a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) 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 B When there are multiple R B are the same or different from each other, L 31 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the arylene group, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, a trivalent group, a tetravalent group, a pentavalent group, or a hexavalent group derived from the heterocyclic group, or a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, or a trivalent group, tetravalent group, pentavalent group or hexavalent group derived from the divalent group; L 32 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, n3 is 1, 2, 3, 4 or 5; L 31 is a single bond, n3 is 1, and L 32 is bonded to a carbon atom of the six-membered ring in the formula (3), L 32 When there are multiple L 32 are the same or different from each other, * is the bonding site to the carbon atom of the six-membered ring in the formula (3).

[0416] (In the third compound, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 908 , R 909 , R931 , R 932 , R 933 , R 934 , R 935 , R 936 and R 937 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 908 If there are multiple R 908 are the same or different from each other, R 909 If there are multiple R 909 are the same or different from each other, R 931 If there are multiple R 931are the same or different from each other, R 932 If there are multiple R 932 are the same or different from each other, R 933 If there are multiple R 933 are the same or different from each other, R 934 If there are multiple R 934 are the same or different from each other, R 935 If there are multiple R 935 are the same or different from each other, R 936 If there are multiple R 936 are the same or different from each other, R 937 If there are multiple R 937 are either identical or different.)

[0417] The compound represented by the formula (3) is also preferably a compound represented by any one of the following formulas (31) to (36).

[0418] [ka]

[0419] [ka]

[0420] [ka]

[0421] (In the formulas (31) to (36), A3 and L3 are defined as A3 and L3 in the formula (3), respectively. R 341 ~R 350 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, X 31 is a sulfur atom, an oxygen atom, and NR 352 or C(R 353 )(R 354 ) and R 353 and R 354 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 341 ~R 350 and R 352 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 353 and R 354 and R each independently represent a group that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 is equivalent to

[0422] In the compound represented by the formula (3), R 352 is preferably 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0423] In the compound represented by the formula (3), R 353 and R 354 are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form the substituted or unsubstituted monocycle and not to form the substituted or unsubstituted fused ring; 353 and R354 are preferably each independently 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0424] In the compound represented by the formula (3), X 31 is preferably a sulfur atom or an oxygen atom.

[0425] In the compound represented by the formula (3), A3 is preferably a group represented by any one of the following formulae (A31) to (A37).

[0426] [ka]

[0427] [ka]

[0428] (In the formulas (A31) to (A37), Multiple R 300 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 333 and R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 300 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 is synonymous with * in the formulae (A31) to (A37) indicates the bonding position with L3 of the compound represented by the formula (3).

[0429] In the compound represented by the formula (3), A3 is also preferably a group represented by the formula (A34), (A35) or (A37).

[0430] In the compound represented by the formula (3), A3 is preferably a group represented by any one of the following formulae (A371) to (A376).

[0431] [ka]

[0432] [ka]

[0433] [ka]

[0434] (In the formulas (A371) to (A376), Y3 is a sulfur atom, an oxygen atom, or NR 381 or C(R 382 )(R 383 ) and R 382 and R 383 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 371 ~R 380 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 381 R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 371 ~R380 and R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 382 and R 383 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 is synonymous with The * symbols in the formulae (A371) to (A376) indicate the bonding positions with L3 of the compound represented by the formula (3).

[0435] In the formulae (A371) to (A376), R 381 is preferably 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0436] In the formulae (A371) to (A376), R 382 and R 383 are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form a substituted or unsubstituted monocycle and not to form a substituted or unsubstituted fused ring; 382 and R 383 are preferably each independently 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0437] In the formulae (A371) to (A376), Y3 is preferably a sulfur atom or an oxygen atom.

[0438] The compound represented by the formula (3) is also preferably a compound represented by any one of the following formulae (311) to (316).

[0439] [ka]

[0440] [ka]

[0441] [ka]

[0442] [ka]

[0443] [ka]

[0444] [ka]

[0445] (In the formulas (311) to (316), L3 has the same meaning as L3 in formula (3), Multiple R 300 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 341 ~R 350 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 300and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 341 ~R 350 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 is equivalent to

[0446] The compound represented by the formula (3) is also preferably a compound represented by the following formula (321).

[0447] [ka]

[0448] (In the formula (321), L3 has the same meaning as L3 in formula (3), R 31 ~R 38 , and R 301 ~R 308 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 is equivalent to

[0449] In the compound represented by the formula (3), L3 is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0450] In the compound represented by the formula (3), L3 is preferably a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.

[0451] In the compound represented by the formula (3), L3 is preferably a group represented by the following formula (317).

[0452] [ka]

[0453] (In the formula (317), R 310 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 and * each independently indicates a bonding position.)

[0454] In the compound represented by the formula (3), it is also preferable that L3 contains a divalent group represented by the following formula (318) or formula (319). In the compound represented by the formula (3), L3 is also preferably a divalent group represented by the following formula (318) or formula (319).

[0455] The compound represented by the formula (3) is also preferably a compound represented by the following formula (322) or formula (323).

[0456] [ka]

[0457] [ka]

[0458] (In the formula (322) and formula (323), L 33 teeth, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms; a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, or a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, However, L 33includes a divalent group represented by the following formula (318) or formula (319): R 31 ~R 38 , R 300 , and R 321 ~R 328 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 is equivalent to

[0459] [ka]

[0460] (In the formula (319), Multiple R 304 a pair of adjacent two of these is bonded to each other to form a ring represented by the formula (320), In the formula (320), 1* and 2* each independently represent R 304 indicates the bonding position with the ring to which it is attached, R in the formula (318) 302 , R in the formula (319) 303 R which does not form a ring represented by the formula (320) 304 and R in the formula (320) 305 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 is synonymous with * in the formulas (318) to (320) indicates the bonding position.)

[0461] In the compound represented by formula (3), L3 or L 33 The group represented by the formula (319) is, for example, a group represented by the following formula (319A).

[0462] [ka]

[0463] (In the formula (319A), R 303 , R 304 and R 305 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 and * in the formula (319A) indicates the bonding position.)

[0464] The compound represented by the formula (3) is a compound represented by the formula (322), and L 33 is also preferably a group represented by the above formula (318).

[0465] The compound represented by the formula (3) is also preferably a compound represented by the following formula (324).

[0466] [ka]

[0467] (In the formula (324), R 31 ~R 38 , R 300 , and R 302 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 is equivalent to

[0468] In the compound represented by the formula (3), R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 are each independently a hydrogen atom, 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 a group represented by the formula (3A), and R in the formula (3A) Bis preferably 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0469] In the compound represented by the formula (3), R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the formula (3A), and R B is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0470] In the compound represented by the formula (3), R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, or a group represented by the formula (3A), and R B is preferably a substituted or unsubstituted phenyl group.

[0471] The compound represented by the formula (3) is also preferably a compound having no pyridine ring, no pyrimidine ring, and no triazine ring.

[0472] (Compound represented by formula (3B)) In the organic EL device of this embodiment, the third compound is also preferably a compound represented by the following formula (3B).

[0473] [ka]

[0474] In the formula (3B), X B is an oxygen atom or a sulfur atom, C1 is a carbon atom, n is 1, 2, or 3; k is 1, 2, or 3; m is 2, 3, or 4, and k+m=5; If m is 2 or more, multiple R L are the same or different from each other, R B1 ~R B8 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, When at least one of n and k is 2 or more, a plurality of R B1 are the same or different, and multiple R B2 are the same or different, and multiple R B3 are the same or different, and multiple R B4 are the same or different, and multiple R B5 are the same or different, and multiple R B6 are the same or different, and multiple R B7 are the same or different, and multiple R B8 are the same or different from each other, L B1 is a single bond or a linking group, provided that L B1 is a single bond, n is 1, If k is 2 or more, multiple L B1 are the same or different from each other, L as a linking group B1 teeth, a group derived from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a group derived from a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a group formed by bonding two groups selected from the group consisting of a group derived from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a group derived from a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, When k is 1 and m is 4, four R L are bonded to any of the carbon atoms at positions a, b, c, d, and e shown in the formula (3B), and one L B1 is the R L and bonded to a carbon atom at position a, b, c, d, or e that is not bonded to When k is 2 and m is 3, three R L are bonded to any of the carbon atoms at positions a, b, c, d, and e shown in the formula (3B), and two L B1 are the R L and bonded to any of the carbon atoms at positions a, b, c, d, and e that are not bonded to When k is 3 and m is 2, two R L are bonded to any of the carbon atoms at positions a, b, c, d, and e shown in the formula (3B), and three L B1 are the R L and bonded to any of the carbon atoms at positions a, b, c, d, and e that are not bonded to R B40 and R B45 ~R B48 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, However, the three R's B40 are the same or different from each other, and the three R B40 are bonded to any of the carbon atoms at positions f, g, h, and i shown in the formula (3B), and C1 is bonded to any of the carbon atoms at positions f, g, h, and i shown in the formula (3B), and C2 is bonded to any of the carbon atoms at positions f, g, h, and i shown in the formula (3B), and C3 is bonded to any of the carbon atoms at positions f, g, h, and i shown in the formula (3B), and C4 is bonded to any of the B40 and bonded to any of the carbon atoms at positions f, g, h, and i that are not bonded to R L , R B31 , R B32 , R B34 , R B35 R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring B1 ~R B8and R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. B40 and R B45 ~R B48 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 908 a group represented by -COOR 909 a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0475] In the compound represented by formula (3B), R 901 ~R 909 and R 931 ~R 937 are R in the formula (3), respectively. 901 ~R 909 and R 931 ~R 937 is synonymous with.

[0476] In the compound represented by the formula (3B), when n is 2 or 3, the nitrogen atom N* in the structure in parentheses enclosed by the subscript n is L B1 Combine with. In the compound represented by the formula (3B), L B1 is a single bond, the nitrogen atom N* in the structure in parentheses enclosed by the subscript n is bonded to a carbon atom at any of the positions a, b, c, d, and e. In the compound represented by the formula (3B), when k is 2 or 3, L in the structure in parentheses enclosed by the subscript k B1 are bonded to any of the carbon atoms at positions a, b, c, d, and e, respectively.

[0477] For example, in the compound represented by the formula (3B), n is 2, k is 1, and L B1 is bonded to the carbon atom at position c, and the carbon atom C1 is bonded to the carbon atom at position h, the compound represented by the formula (3B) is represented by the following formula (31B).

[0478] [ka]

[0479] (In the formula (31B), R B1 ~R B8 , R L , R B31 , R B32 , R B34 , R B35 , R B40 , R B45 ~R B48 , L B1 and X Bare as defined in the formula (3B).

[0480] For example, in the compound represented by the formula (3B), L B1 is a single bond, n is 2, one of the two nitrogen atoms N* in the structure in parentheses enclosed by the subscript n is bonded to the carbon atom at the position b, and the other is bonded to the carbon atom at the position b, and the carbon atom C1 is bonded to the carbon atom at the position h, the compound represented by the formula (3B) is represented by the following formula (32B).

[0481] [ka]

[0482] (In the formula (32B), R B1 ~R B8 , R L , R B31 , R B32 , R B34 , R B35 , R B40 , R B45 ~R B48 , and X B are as defined in the formula (3B).

[0483] (Compound represented by formula (MRX3)) In the organic EL device of this embodiment, the third compound is also preferably a compound represented by the following formula (MRX3).

[0484] [ka]

[0485] (In the formula (MRX3), Y 31 ~Y 36 are each independently C-R or a nitrogen atom, However, Y 31 ~Y 36 two or more of which are nitrogen atoms, When a plurality of R3's are present, one or more pairs of adjacent two or more of the plurality of R3's are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R3 that does not form a substituted or unsubstituted monocycle and does not form a substituted or unsubstituted fused ring each independently represents 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 908 a group represented by -COOR 909 a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or It is a group represented by the following formula (MRX3A):

[0486] [ka]

[0487] (In the formula (MRX3A), R B is R in the formula (3). B is synonymous with R B When there are multiple R B are the same or different from each other, L 31 and L 32 are the L in the formula (3A), respectively. 31 and L 32 is synonymous with n3 is 1, 2, 3, 4 or 5; L 31 is a single bond, n3 is 1, and L 32 is bonded to a carbon atom of the six-membered ring in formula (MRX3), L 32 When there are multiple L 32 are the same or different from each other, * represents the bonding site to the carbon atom of the six-membered ring in formula (MRX3).

[0488] In the compound represented by the formula (MRX3), R 901 ~R 909 and R 931 ~R 937 are R in the formula (3), respectively. 901 ~R 909 and R 931 ~R 937 is synonymous with.

[0489] The compound represented by the formula (MRX3) preferably does not contain a pyridine ring in the molecule.

[0490] The compound represented by the formula (MRX3) is also preferably a compound represented by the following formula (MRX31) or (MRX32).

[0491] [ka]

[0492] (In the formula (MRX32), R 35 ~R 37 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R in the formula (MRX31) 31 ~R 33 and R in the formula (MRX32) 34 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 35 ~R 37 each independently has the same meaning as R3 in the formula (MRX3).

[0493] The compound represented by the formula (MRX3) is also preferably a compound represented by the formula (MRX31).

[0494] It is preferable that each R3 in the formula (MRX3) is independently a hydrogen atom, 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 a group represented by the formula (MRX3A).

[0495] It is preferable that each R3 in the formula (MRX3) is independently a hydrogen atom, 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 a group represented by the formula (MRX3A).

[0496] The compound represented by the formula (MRX3) preferably has, in the molecule, at least one group selected from the group consisting of groups represented by the following formulae (MRXA31) to (MRXA44).

[0497] [ka]

[0498] [ka]

[0499] (In the formulae (MRXA31) to (MRXA38), Multiple R 300 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 331 and R 332 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 333 and R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 300 , R 331 and R 332 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 908 a group represented by -COOR 909 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, The * symbols in the formulae (MRXA31) to (MRXA38) indicate the bonding positions to other atoms in the molecule of the compound represented by the formula (MRX3).

[0500] [ka]

[0501] [ka]

[0502] [ka]

[0503] (In the formulae (MRXA39) to (MRXA44), R 341 ~R 350 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, However, R 341 ~R 351 at least one of the following represents a bonding position to another atom in the molecule of the compound represented by formula (MRX3); X 31 is a sulfur atom, an oxygen atom, and NR 352 or C(R 353 )(R 354 ) and R 353 and R 354 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 352 R which is not at a bonding position with another atom in the molecule of the compound represented by formula (MRX3), does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring 341 ~R 351 and R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 353 and R 354 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 908 a group represented by -COOR 909 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.

[0504] The compound represented by the formula (MRX3) preferably has at least one group selected from the group consisting of the groups represented by the formulas (MRXA38) to (MRXA44) in the molecule.

[0505] In the compound represented by the formula (MRX3), Y 31 ~Y 36 At least one of the groups is C-R3, and at least one of the groups is a group represented by the formula (MRX3A), and R B is preferably any one of the groups represented by the above formulae (MRXA31) to (MRXA44).

[0506] In the compound represented by the formula (MRX3), Y 31 ~Y 36 At least one of the groups is C-R3, and at least one of the groups is a group represented by the formula (MRX3A), and R B is preferably any one of the groups represented by the above formulae (MRXA38) to (MRXA44).

[0507] In the compound represented by the formula (MRX3), R 352 is preferably 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0508] In the compound represented by the formula (MRX3), R 353 and R 354 are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form a substituted or unsubstituted monocycle and not to form a substituted or unsubstituted fused ring; 353 and R 354 are preferably each independently 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0509] In the compound represented by the formula (3) and the compound represented by the formula (MRX3), L 31 represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a trivalent group, a tetravalent group, a pentavalent group, or a hexavalent group derived from the arylene group, or a divalent group formed by bonding two groups selected from the group consisting of substituted or unsubstituted arylene groups having 6 to 50 ring carbon atoms, or a trivalent group, a tetravalent group, a pentavalent group, or a hexavalent group derived from the divalent group; L 32 is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0510] In the compound represented by the formula (3) and the compound represented by the formula (MRX3), L 31 represents a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, n3 represents 1, and L 32 is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0511] In the compound represented by the formula (3) and the compound represented by the formula (MRX3), L 31 represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted phenylene group and a substituted or unsubstituted biphenylene group, or a trivalent group, tetravalent group, pentavalent group or hexavalent group derived from the divalent group; n3 is 1; L 32 is preferably a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0512] In the compound represented by the formula (3), the compound represented by the formula (3B), and the compound represented by the formula (MRX3), the substituent in the term "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 25 carbon atoms; an unsubstituted alkenyl group having 2 to 25 carbon atoms; an unsubstituted alkynyl group having 2 to 25 carbon atoms, an unsubstituted cycloalkyl group having 3 to 25 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 an unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 a group represented by -COOR 909 a group represented by -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935) a group represented by -B(R 936 )(R 937 ) a group represented by -S(=O)2R 938 a group represented by halogen atoms, cyano group, nitro group, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms, R 901 ~R 909 , and R 931 ~R 938 are each independently, hydrogen atoms, an unsubstituted alkyl group having 1 to 25 carbon atoms; an unsubstituted aryl group having 6 to 25 ring carbon atoms, or It is preferably an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[0513] In the compound represented by formula (3), the compound represented by formula (3B), and the compound represented by formula (MRX3), the substituent in the case of "substituted or unsubstituted" is preferably a halogen atom, 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.

[0514] In the compound represented by formula (3), the compound represented by formula (3B), and the compound represented by formula (MRX3), the substituent in the case of "substituted or unsubstituted" is preferably 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.

[0515] In the compound represented by the formula (3), the compound represented by the formula (3B), and the compound represented by the formula (MRX3), it is also preferable that all of the groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0516] (Method for producing the third compound) The third compound according to this embodiment can be produced by a known method.

[0517] (Specific Example of the Third Compound) Specific examples of the third compound of this embodiment include the following compounds, however, the present invention is not limited to these specific examples of compounds.

[0518] [ka]

[0519] [ka]

[0520] [ka]

[0521] [ka]

[0522] [ka]

[0523] [ka]

[0524] [ka]

[0525] [ka]

[0526] [ka]

[0527] [ka]

[0528] [ka]

[0529] [ka]

[0530] [ka]

[0531] (Relationship between the first compound, the second compound, and the third compound in the light-emitting layer) In the organic EL device according to the fourth embodiment, it is preferable that the light-emitting layer contains a second compound and a third compound, and that the lowest excited singlet energy S1(M2) of the second compound and the lowest excited singlet energy S1(M3) of the third compound satisfy the relationship shown in the following formula (Mathematical Formula 2). S1(M3)>S1(M2)…(Math 2)

[0532] In the organic EL device according to the fourth embodiment, the light-emitting layer contains a first compound, a second compound, and a third compound, the first compound being a fluorescent compound, and it is preferable that the lowest excited singlet energy S1(M1) of the first compound, the lowest excited singlet energy S1(M2) of the second compound, and the lowest excited singlet energy S1(M3) of the third compound satisfy the relationship shown in the following formula (3). S1(M3)>S1(M2)>S1(M1)…(Math 3)

[0533] Energy gap T at 77[K] of the third compound77K (M3) is the energy gap T of the first compound at 77[K]. 77K It is preferable that it is larger than (M1). Energy gap T at 77[K] of the third compound 77K (M3) is the energy gap T at 77[K] of the second compound 77K It is preferable that it is larger than (M2).

[0534] Energy gap T of the first compound at 77[K] 77K (M1) and the energy gap T at 77[K] of the second compound 77K (M2) and the energy gap T at 77[K] of the third compound 77K It is preferable that (M3) satisfies the relationship of the following mathematical formula (Mathematical Formula 2B). T 77K (M3)>T 77K (M2)>T 77K (M1) ... (Math 2B)

[0535] When the organic EL device of the fourth embodiment is caused to emit light, it is preferable that the fluorescent compound in the light-emitting layer mainly emits light. The organic EL element of the fourth embodiment preferably emits blue light, similarly to the organic EL element of the third embodiment. The organic EL element of the fourth embodiment preferably emits red or green light, similarly to the organic EL element of the third embodiment. The maximum peak wavelength of the light emitted from the organic EL element can be measured in the same manner as in the organic EL element of the third embodiment.

[0536] (Compound content in the light-emitting layer) In the organic EL device of the fourth embodiment, the contents of the first compound, the second compound, and the third compound contained in the light-emitting layer are preferably within the following ranges, for example. The content of the second compound in the light-emitting layer is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. The content of the first compound in the light-emitting layer is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 2% by mass or less. The content of the third compound in the light-emitting layer is preferably 10% by mass or more and 80% by mass or less. The upper limit of the total content of the first compound, the second compound, and the third compound in the light-emitting layer is 100 mass %. Note that the fourth embodiment does not exclude the case where the light-emitting layer contains materials other than the first compound, the second compound, and the third compound. The light-emitting layer may contain only one type of first compound or two or more types. The light-emitting layer may contain only one type of second compound or two or more types. The light-emitting layer may contain only one type of third compound or two or more types.

[0537] FIG. 5 shows an example of the relationship between the energy levels of a first compound (compound M1), a second compound (compound M2), and a third compound (compound M3) in an emitting layer. In FIG. 5, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the first compound, and T1(M1) represents the lowest excited triplet state of the first compound. S1(M2) represents the lowest excited singlet state of the second compound, and T1(M2) represents the lowest excited triplet state of the second compound. S1(M3) represents the lowest excited singlet state of the third compound, and T1(M3) represents the lowest excited triplet state of the third compound. The dashed arrow from S1(M2) to S1(M1) in FIG. 5 represents Förster energy transfer from the lowest excited singlet state of the second compound to the lowest excited singlet state of the first compound. As shown in Figure 5, when a compound with a small ΔST(M2) is used as the second compound, the lowest excited triplet state T1(M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) due to thermal energy. Then, Förster-type energy transfer occurs from the lowest excited singlet state S1(M2) of the second compound to the first compound, generating the lowest excited singlet state S1(M1). As a result, fluorescence emission from the lowest excited singlet state S1(M1) of the first compound can be observed. It is believed that the internal quantum efficiency can theoretically be increased to 100% by utilizing delayed fluorescence via this TADF mechanism.

[0538] The organic EL device according to the fourth embodiment includes, in an emitting layer, the second compound according to the first embodiment, a first compound having a minimum excited singlet energy smaller than that of the second compound, and a third compound having a minimum excited singlet energy larger than that of the second compound. According to the fourth embodiment, the device performance of the organic EL device can be improved, and in particular, the luminous efficiency of the organic EL device can be improved. The organic EL device according to the fourth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0539] Fifth Embodiment <Organic electroluminescence element> The configuration of an organic EL element according to the fifth embodiment will be described. In the description of the fifth embodiment, the same components as those in the third or fourth embodiment will be denoted by the same reference numerals or names, and the description thereof will be omitted or simplified. Furthermore, in the fifth embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the first to fourth embodiments can be used.

[0540] The organic EL device according to the fifth embodiment differs from the organic EL device according to the third or fourth embodiment in that the light-emitting layer contains a second compound and a third compound, but does not contain the first compound. The remaining features are the same as those of the third or fourth embodiment. That is, in the fifth embodiment, the light-emitting layer serving as the first organic layer contains a second compound and a third compound. In this case, the third compound is preferably a host material, and the second compound is preferably a dopant material. In the fifth embodiment, when the light-emitting layer contains the second compound according to the first embodiment, the light-emitting layer preferably does not contain a phosphorescent metal complex, and preferably does not contain any metal complex other than the phosphorescent metal complex.

[0541] <Second Compound> In the fifth embodiment, the second compound is the compound according to the first embodiment (the compound represented by formula (2)). In this embodiment, the compound represented by formula (2) is preferably a thermally activated delayed fluorescent compound.

[0542] <Third Compound> In the fifth embodiment, the third compound is the same as the third compound described in the fourth embodiment.

[0543] (Relationship between the second compound and the third compound in the light-emitting layer) In the organic EL device according to the fifth embodiment, it is preferable that the lowest excited singlet energy S1(M2) of the second compound and the lowest excited singlet energy S1(M3) of the third compound satisfy the relationship of the following mathematical formula (Mathematical Formula 2). S1(M3)>S1(M2)…(Math 2)

[0544] In the organic EL device according to the fifth embodiment, the energy gap T 77K (M3) is the energy gap T at 77[K] of the second compound 77K It is preferable that it is larger than (M2).

[0545] FIG. 6 is a diagram for explaining the principle of light emission according to an embodiment of the present invention. In Figure 6, S0 represents the ground state. S1(M2) represents the lowest excited singlet state of the second compound (compound M2), and T1(M2) represents the lowest excited triplet state of the second compound. S1(M3) represents the lowest excited singlet state of the third compound (compound M3), and T1(M3) represents the lowest excited triplet state of the third compound. As shown in Figure 6, when a compound with a small ΔST(M2) is used as the second compound, the lowest excited triplet state T1(M2) of the second compound can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) due to thermal energy. By utilizing the reverse intersystem crossing that occurs in this second compound, for example, luminescence as shown in the following (i-1) or (ii-1) can be observed. (i-1) When the light-emitting layer does not contain a fluorescent dopant having a lowest excited singlet state S1 smaller than the lowest excited singlet state S1(M2) of the second compound, light emission from the lowest excited singlet state S1(M2) of the second compound can be observed. (ii-1) When the emitting layer contains a fluorescent dopant (a fluorescent first compound in the third or fourth embodiment) whose lowest excited singlet state S1 is smaller than the lowest excited singlet state S1 (M2) of the second compound, light emission from the fluorescent dopant can be observed. In the organic EL element of the fifth embodiment, the light emission shown in (i-1) can be observed. In the organic EL element of the third or fourth embodiment, the light emission shown in (ii-1) can be observed.

[0546] (Compound content in the light-emitting layer) In the organic EL device according to the fifth embodiment, the content of the second compound and the third compound contained in the light-emitting layer is preferably within the following ranges, for example. The content of the second compound in the light-emitting layer is preferably 10% by mass or more and 90% by mass or less, more preferably 10% by mass or more and 80% by mass or less, even more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. The content of the third compound in the light-emitting layer is preferably 10% by mass or more and 90% by mass or less. The upper limit of the total content of the second compound and the third compound in the light-emitting layer is 100% by mass. In the organic EL device according to the fifth embodiment, the light-emitting layer may contain only one type of second compound or two or more types thereof. The light-emitting layer may contain only one type of third compound or two or more types thereof.

[0547] The organic EL device according to the fifth embodiment includes, in the light-emitting layer, the second compound according to the first embodiment and a third compound having a minimum excited singlet energy greater than that of the second compound. According to the fifth embodiment, the device performance of the organic EL device can be improved, and in particular, the driving voltage of the organic EL device can be reduced and the luminous efficiency can be improved. The organic EL device according to the fifth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0548] Sixth Embodiment (electronic equipment) The electronic device according to this embodiment is equipped with the organic electroluminescence element according to the above-described embodiment. Examples of the electronic device include a display device and a light-emitting device. Examples of the display device include display components (e.g., an organic EL panel module), televisions, mobile phones, tablets, and personal computers. Examples of the light-emitting device include lighting and vehicle lighting fixtures. The light-emitting device can be used in a display device, for example, as a backlight for a display device.

[0549] [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.

[0550] For example, the number of light-emitting layers is not limited to one, and multiple light-emitting layers may be stacked. When the organic EL element has multiple light-emitting layers, it is sufficient that at least one of the light-emitting layers satisfies the conditions described in the above embodiment. For example, the other light-emitting layers may be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize light emission due to electron transition from a triplet excited state directly to the ground state. Furthermore, when the organic EL element has a plurality of light-emitting layers, these light-emitting layers may be provided adjacent to each other, or the organic EL element may be a so-called tandem type organic EL element in which a plurality of light-emitting units are stacked via an intermediate layer.

[0551] Furthermore, for example, a blocking layer may be provided adjacent to at least one of the anode side and the cathode side of the light-emitting layer. The blocking layer is preferably disposed in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons. For example, when a blocking layer is disposed adjacent to the cathode side of the light-emitting layer, the blocking layer transports electrons and prevents holes from reaching a layer (e.g., an electron transport layer) located closer to the cathode than the blocking layer. When the organic EL device includes an electron transport layer, it is preferable to include the blocking layer between the light-emitting layer and the electron transport layer. Furthermore, when a blocking layer is disposed in contact with the light-emitting layer on the anode side, the blocking layer transports holes and prevents electrons from reaching a layer (e.g., a hole transport layer) located closer to the anode than the blocking layer. When the organic EL device includes a hole transport layer, it is preferable to include the blocking layer between the light-emitting layer and the hole transport layer. A barrier layer may be provided adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to surrounding layers, and prevents excitons generated in the light-emitting layer from migrating to layers closer to the electrode than the barrier layer (e.g., electron transport layer and hole transport layer). The light-emitting layer and the barrier layer are preferably in contact with each other.

[0552] In addition, the specific structure and shape in carrying out the present invention may be other structures within the scope of achieving the object of the present invention. [Example]

[0553] 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.

[0554] <Compound> The structures of the compounds represented by formula (2) used in the production of the organic EL devices according to Examples 1-1 to 1-3 and Examples 2-1 to 2-3 are shown below.

[0555] [ka]

[0556] The structures of the comparative compounds used in the production of the organic EL devices according to Comparative Examples 1-1 and 2-1 are shown below.

[0557] [ka]

[0558] The structures of other compounds used in the production of the organic EL devices according to Examples 1-1 to 1-3, Examples 2-1 to 2-3, and Comparative Examples 1-1 and 2-1 are shown below.

[0559] [ka]

[0560] [ka]

[0561] [ka]

[0562] <Fabrication of Organic EL Devices (1)> Example 1-1 A 25mm x 75mm x 1.1mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO transparent electrode had a film thickness of 130nm. The washed glass substrate with transparent electrode lines was mounted on a substrate holder in a vacuum deposition apparatus, and Compound HT-1 and Compound HA were co-deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, thereby forming a hole injection layer with 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. Compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 90 nm. Next, the compound HT-2 was vapor-deposited on the first hole transport layer to form an electron blocking layer (sometimes referred to as a second hole transport layer) having a thickness of 30 nm. On the electron blocking layer, a compound HOST (third compound), a compound A1 (second compound), and a compound GD (first compound) as a fluorescent material were co-deposited to form an emitting layer having a thickness of 25 nm, in which the proportion of compound HOST in the emitting layer was 74 mass %, the proportion of compound A1 was 25 mass %, and the proportion of compound GD was 1 mass %. The compound ET-1 was vapor-deposited on the light-emitting layer to form a first electron-transporting layer having a thickness of 5 nm. The first electron-transporting layer may also be referred to as a hole-blocking layer. On the first electron-transporting layer, the compounds ET-2 and Liq were co-deposited to form a second electron-transporting layer with a thickness of 50 nm. The proportion of the compound ET-2 in this second electron-transporting layer was 50 mass %, and the proportion of Liq was 50 mass %. Liq is an abbreviation for (8-quinolinolato)lithium. On the second electron transport layer, Yb (ytterbium) was evaporated to form an electron injection layer with a thickness of 1 nm. Metallic Al was vapor-deposited on the electron injection layer to form a cathode with a thickness of 80 nm. As described above, an organic EL element according to Example 1-1 was produced. The device configuration of the organic EL element according to Example 1-1 is shown in outline below. ITO(130) / HT-1:HA(10,97%:3%) / HT-1(90) / HT-2(30) / HOST:A1:GD(25,74%:25%:1%) / ET-1(5) / ET-2:Liq(50,50%:50%) / Yb(1) / Al(80) The numbers in parentheses indicate film thickness (unit: nm). Regarding the device configuration of the organic EL device according to Example 1-1, the percentages in parentheses (97%:3%) indicate the ratios (unit: mass%) of compound HT-1 and compound HA in the hole injection layer, the percentages (74%:25%:1%) indicate the ratios (unit: mass%) of compound HOST, compound A1, and compound GD in the light-emitting layer, and the percentages (50%:50%) indicate the ratios (unit: mass%) of compound ET-2 and Liq in the second electron transport layer. The same notations are used hereinafter.

[0563] Examples 1-2 and 1-3 The organic EL devices of Examples 1-2 and 1-3 were prepared in the same manner as in Example 1-1, except that the compound A1 used as the second compound in the light-emitting layer of Example 1-1 was changed to the second compound shown in Table 1.

[0564] Comparative Example 1-1 The organic EL device of Comparative Example 1-1 was prepared in the same manner as in Example 1-1, except that the compound A1 used as the second compound in the light-emitting layer of Example 1-1 was changed to the compound Ref-1 shown in Table 1.

[0565] <Evaluation of Organic EL Devices (1)> The fabricated organic EL devices were evaluated as follows. The evaluation results are shown in Table 1. Table 1 also shows the lowest excited singlet energy S1 of the first compound, second compound, and third compound used in the emitting layer of each example.

[0566] (CIE1931 chromaticity) The current density of the fabricated organic EL device was 10 mA / cm 2 The CIE1931 chromaticity coordinates (x, y) when a voltage was applied so as to satisfy the following equation were measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.).

[0567] (Maximum peak wavelength λ when the element is driven EL and emission half-width FWHM) The current density of the fabricated organic EL device was 10 mA / cm 2 The spectral radiance spectrum when a voltage was applied so that the maximum peak wavelength λ was obtained was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). EL The full width at half maximum (FWHM) (unit: nm) and the full width at half maximum (FWHM) were calculated.

[0568] (External quantum efficiency EQE) The current density of the fabricated organic EL device was 10 mA / cm 2 The spectral radiance spectrum when a voltage was applied so that the value was 1 / 2 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. Based on the measured EQE values ​​of each example (Examples 1-1 to 1-3 and Comparative Example 1-1) and the following formula (Mathematical Formula 1X), "EQE95 (relative value)" (unit: %) was calculated. EQE (relative value) = (EQE of each example / EQE of Comparative Example 1-1) × 100... (Number 1X)

[0569] [Table 1]

[0570] As shown in Table 1, the organic EL devices according to Examples 1-1 to 1-3, which used compound A1, A2, or A3 as the second compound, had improved luminous efficiency compared to the organic EL device according to Comparative Example 1-1, which used compound Ref-1.

[0571] <Fabrication of Organic EL Devices (2)> Example 2-1 A 25mm x 75mm x 1.1mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO transparent electrode had a film thickness of 130nm. The washed glass substrate with transparent electrode lines was mounted on a substrate holder in a vacuum deposition apparatus, and Compound HT-1 and Compound HA were co-deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, thereby forming a hole injection layer with 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. Compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 90 nm. Next, the compound HT-2 was vapor-deposited on the first hole transport layer to form an electron blocking layer (sometimes referred to as a second hole transport layer) having a thickness of 30 nm. On the electron blocking layer, a compound HOST (third compound) and a compound A1 (second compound) were co-deposited to form a light-emitting layer having a thickness of 25 nm, in which the proportion of the compound HOST in the light-emitting layer was 75 mass % and the proportion of the compound A1 in the light-emitting layer was 25 mass %. The compound ET-1 was vapor-deposited on the light-emitting layer to form a first electron-transporting layer having a thickness of 5 nm. The first electron-transporting layer may also be referred to as a hole-blocking layer. On the first electron transport layer, the compound ET-2 and Liq were co-deposited to form a second electron transport layer having a thickness of 50 nm, in which the proportion of the compound ET-2 in the second electron transport layer was 50% by mass and the proportion of Liq in the second electron transport layer was 50% by mass. On the second electron transport layer, Yb (ytterbium) was evaporated to form an electron injection layer with a thickness of 1 nm. Metallic Al was vapor-deposited on the electron injection layer to form a cathode with a thickness of 80 nm. As described above, an organic EL element according to Example 2-1 was produced. The device configuration of the organic EL element according to Example 2-1 is shown in outline below. ITO(130) / HT-1:HA(10,97%:3%) / HT-1(90) / HT-2(30) / HOST:A1(25,75%:25%) / ET-1(5) / ET-2:Liq(50,50%:50%) / Yb(1) / Al(80)

[0572] Examples 2-2 and 2-3 The organic EL devices of Examples 2-2 and 2-3 were prepared in the same manner as in Example 2-1, except that the compound A1 used as the second compound in the light-emitting layer of Example 2-1 was changed to the second compound shown in Table 2.

[0573] Comparative Example 2-1 The organic EL device of Comparative Example 2-1 was prepared in the same manner as in Example 2-1, except that the compound A1 used as the second compound in the light-emitting layer of Example 2-1 was changed to the compound Ref-1 shown in Table 2.

[0574] <Evaluation of Organic EL Devices (2)> The fabricated organic EL devices were evaluated as follows. The evaluation results are shown in Table 2. Table 2 also shows the lowest excited singlet energy S1 of the second compound and the third compound used in the emitting layer of each example.

[0575] (driving voltage) The current density between the anode and cathode of the fabricated organic EL device was 10 mA / cm 2 The driving voltage V (unit: V) was measured when current was applied so that ΔV (unit: V) was calculated based on the measured value of the driving voltage V of each example (Examples 2-1 to 2-3 and Comparative Example 2-1) and the following formula (Mathematical Formula 2X). ΔV = (driving voltage V of each example) - (driving voltage V of Comparative Example 2-1) ... (Equation 2X)

[0576] (CIE1931 chromaticity) The CIE1931 chromaticity coordinates (x, y) were measured in the same manner as described in "Evaluation of Organic EL Devices (1)."

[0577] (Maximum peak wavelength λ when the element is drivenEL and emission half-width FWHM) Maximum peak wavelength λ EL and FWHM were measured in the same manner as described in "Evaluation of Organic EL Device (1)."

[0578] (External quantum efficiency EQE) The external quantum efficiency EQE was measured and calculated in the same manner as described in "Evaluation of Organic EL Devices (1)." Based on the measured EQE values ​​of each example (Examples 2-1 to 2-3 and Comparative Example 2-1) and the following mathematical formula (Math 1Y), "EQE95 (relative value)" (unit: %) was calculated. EQE (relative value) = (EQE of each example / EQE of Comparative Example 2-1) × 100 (Equation 1Y)

[0579] [Table 2]

[0580] As shown in Table 2, the organic EL devices of Examples 2-1 to 2-3, which used compound A1, A2, or A3 as the second compound, had a lower driving voltage and improved luminous efficiency compared to the organic EL device of Comparative Example 2-1, which used compound Ref-1.

[0581] <Compound evaluation> (Delayed fluorescence of the compound) Delayed fluorescence was confirmed by measuring transient PL using the apparatus shown in Figure 1. Compound A1 was dissolved in toluene to prepare a dilute solution with an absorbance of 0.05 or less at the excitation wavelength to eliminate the contribution of self-absorption. To prevent quenching by oxygen, the sample solution was frozen and degassed, then sealed in a capped cell under an argon atmosphere to produce an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the sample solution was measured using a spectrofluorometer FP-8600 (JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. The total fluorescence quantum yield was calculated using the fluorescence area intensity of both spectra according to equation (1) in Morris et al. J. Phys. Chem. 80 (1976) 969. After being excited by pulsed light (light irradiated from a pulsed laser) having a wavelength absorbed by the compound A1, there are two types of emission: prompt emission (immediate emission) that is observed immediately from the excited state, and delayed emission (delayed emission) that is not observed immediately after the excitation but is observed later. In this example, delayed fluorescence emission means that the amount of delayed emission (delayed emission) is 5% or more of the amount of prompt emission (immediate emission). Specifically, when the amount of prompt emission (immediate emission) is X P and the amount of delay light emission is X D When X D / X P This means that the value of is 0.05 or more. The amounts of prompt luminescence and delay luminescence and their ratio can be determined by a method similar to that described in "Nature 492, 234-238, 2012" (Reference 1). Note that the device used to calculate the amounts of prompt luminescence and delay luminescence is not limited to the device described in Reference 1 or the device shown in FIG. 1. Compounds A2, A3, and the comparative compound Ref-1 were also measured in the same manner as for compound A1. It was confirmed that the amount of Delay luminescence (delayed luminescence) was 5% or more of the amount of Prompt luminescence (instant luminescence) for Compound A1, Compound A2, Compound A3, and Comparative Compound Ref-1. Specifically, for Compound A1, Compound A2, Compound A3, and Comparative Compound Ref-1, X D / X P The value was 0.05 or higher.

[0582] (Lowest excited singlet energy S1) The lowest excited singlet energy S1 of the compound to be measured was measured by the solution method described above.

[0583] <Synthesis example> The structures of the compounds represented by formula (2) synthesized in Synthesis Examples 1 to 8 are shown below.

[0584] [ka]

[0585] [ka]

[0586] [ka]

[0587] [Synthesis Example 1] Compound A1 was synthesized according to the following synthetic route.

[0588] (S1-1) Synthesis of phenyl derivative (compound MA-1)

[0589] [ka]

[0590] Under a nitrogen atmosphere, a 300 mL three-neck flask was charged with 3'-fluoro-5'-iodo-[1,1':4',1''-terphenyl]-2',6'-dicarbonitrile (20 g), phenylboronic acid (6.04 g), Pd2(dba)3 (0.432 g), XPhos (0.899 g), tripotassium phosphate (K3PO4) (25.02 g), and THF (118 mL) and stirred at 50 °C for 5 hours. After stirring, 100 mL of ion-exchanged water was added to the reaction solution, and the precipitated solid was purified by silica gel column chromatography to yield 15 g of a white solid. The resulting white solid was identified as compound MA-1 by ASAP-MS analysis (85% yield). ASAP-MS stands for Atmospheric Pressure Solid Analysis Probe Mass Spectrometry.

[0591] (S1-2) Synthesis of Compound A1

[0592] [ka]

[0593] Under a nitrogen atmosphere, 6-phenyl-14H-benzo[4,5]thieno[2,3-a]benzo[4,5]thieno[3,2-i]carbazole (3.54 g), synthesized by a known method, was added to a mixture of compound MA-1 (6'-fluoro-4'-phenyl-[1,1':2',1''-terphenyl]-3',5'-dicarbonitrile) (3.0 g), cesium fluoride (CsF) (11.80 g), and N,N-dimethylacetamide (DMAc) (52 mL). The bath temperature was raised to 130 °C and the mixture was stirred for 3 days. After stirring, the reaction mixture was allowed to cool to room temperature. Water was added to the cooled reaction mixture, and the resulting solid was collected by filtration. The resulting solid was purified by silica gel column chromatography (hexane / dichloromethane = 1 / 1 (volume ratio)). The crude product was dissolved in approximately five times the amount of dichloromethane, and the same amount of methanol as the dichloromethane was added. The precipitated solid was collected by filtration to obtain 4.16 g of a yellow solid, which was identified as Compound A1 by ASAP-MS analysis (yield 66%).

[0594] [Synthesis Example 2] Compound A2 was synthesized according to the following synthetic route.

[0595] (S2-1) Synthesis of biphenyl derivative (compound MA-2)

[0596] [ka]

[0597] Under a nitrogen atmosphere, 3'-fluoro-5'-iodo-[1,1':4',1''-terphenyl]-2',6'-dicarbonitrile (15.6 g), [1,1'-biphenyl]-4-ylboronic acid (22.26 g), Pd2(dba)3 (0.432 g), XPhos (0.899 g), K3PO4 (25.02 g), THF (318 ml), and water (31.8 ml) were placed in a 300 mL three-neck flask and stirred at 50 °C for 3 days. After stirring, water was added to the reaction solution, and the mixture was extracted twice with ethyl acetate. The organic layer was washed twice with water, dried over sodium sulfate, and insoluble matter was removed by filtration. The solvent was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 7.66 g of a white solid. The resulting white solid was identified as compound MA-2 by ASAP-MS analysis (yield 32%).

[0598] (S2-2) Synthesis of Compound A2

[0599] [ka]

[0600] Under a nitrogen atmosphere, 6-phenyl-14H-benzo[4,5]thieno[2,3-a]benzo[4,5]thieno[3,2-i]carbazole (1.28 g) was added to a mixture of compound MA-2 (6'-fluoro-4'-phenyl-[1,1':2',1'':4'',1'''-quaterphenyl]-3',5'-dicarbonitrile) (1.30 g), cesium fluoride (CsF) (4.26 g), and N,N-dimethylacetamide (DMAc) (14 mL). The bath temperature was raised to 130 °C and the mixture was stirred for 8 hours. After stirring, the reaction mixture was allowed to cool to room temperature. After cooling, water was added to the reaction mixture, and the resulting solid was collected by filtration. The resulting solid was purified by silica gel column chromatography (hexane / dichloromethane = 1 / 1 (volume ratio)). The crude product was dissolved in approximately five times the amount of dichloromethane, and the same amount of methanol as the dichloromethane was added. The precipitated solid was collected by filtration to obtain 0.93 g of a yellow solid, which was identified as Compound A2 by ASAP-MS analysis (yield 38%).

[0601] [Synthesis Example 3] Compound A3 was synthesized according to the following synthetic route.

[0602] (S3-1) Synthesis of compound MA-3

[0603] [ka]

[0604] Under a nitrogen atmosphere and ice cooling, 3'-fluoro-5'-iodo-[1,1':4',1''-terphenyl]-2',6'-dicarbonitrile (1.86 g) was added to a mixture of 6-phenyl-14H-benzo[4,5]thieno[2,3-a]benzo[4,5]thieno[3,2-i]carbazole (2 g), sodium hydride (NaH, 60% in mineral oil) (0.21 g), and 44 mL of THF. The mixture was warmed to room temperature and stirred for 8 hours. After stirring, the reaction mixture was allowed to cool to room temperature. After cooling, water was added to the reaction mixture, and the resulting solid was collected by filtration. The resulting solid was purified by silica gel column chromatography (hexane / dichloromethane = 1 / 1 (volume ratio)). The crude product was dissolved in dichloromethane, and an equal amount of methanol was added to the dichloromethane. The precipitated solid was collected by filtration, yielding 2 g of a yellow solid. The resulting yellow solid was identified as compound MA-3 by ASAP-MS analysis (yield 53%).

[0605] (S3-2) Synthesis of Compound A3

[0606] [ka]

[0607] Compound MA-3 (3'-iodo-5'-(6-phenyl-14H-benzo[4,5]thieno[2,3-a]benzo[4,5]thieno[3,2-i]carbazol-14-yl)-[1,1':4',1''-terphenyl]-2',6'-dicarbonitrile) (0.75 g), dibenzo[b,d]thiophen-4-ylboronic acid (0.30 g), PdCl2(amphos)2 (0.031 g), K3PO4 (0.56 g), THF (8 ml), and water (0.8 ml) were placed in a 50 mL three-neck flask under a nitrogen atmosphere and stirred at 50 °C for 8 hours. After stirring, water was added to the reaction solution, which was then extracted twice with ethyl acetate. The organic layer was washed twice with water, dried over sodium sulfate, and insoluble materials were removed by filtration. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.64 g of a yellow solid, which was identified as Compound A3 by ASAP-MS analysis (yield 80%).

[0608] [Synthesis Example 4] Compound A4 was synthesized according to the following synthetic route.

[0609] (S4-1) Synthesis of compound MA-4

[0610] [ka]

[0611] Under a nitrogen atmosphere, 3'-fluoro-5'-iodo-[1,1':4',1''-terphenyl]-2',6'-dicarbonitrile (2.88 g), dibenzo[b,d]thiophen-3-ylboronic acid (1.55 g), PdCl2(amphos)2 (0.24 g), K3PO4 (4.33 g), 1,4-dioxane (62 ml), and water (6.2 ml) were placed in a 300 mL three-neck flask and stirred at 80 °C for 1 day. After stirring, water was added to the reaction solution, and the mixture was extracted twice with ethyl acetate. The organic layer was washed twice with water, dried over sodium sulfate, and insoluble materials were removed by filtration. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2.51 g of a white solid. The resulting white solid was identified as compound MA-4 by ASAP-MS analysis (77% yield).

[0612] (S4-2) Synthesis of Compound A4

[0613] [ka]

[0614] Under a nitrogen atmosphere, 6-phenyl-14H-benzo[4,5]thieno[2,3-a]benzo[4,5]thieno[3,2-i]carbazole (2.37 g) was added to a mixture of 3'-(dibenzo[b,d]thiophen-3-yl)-5'-fluoro-[1,1':4',1''-terphenyl]-2',6'-dicarbonitrile (2.50 g), cesium fluoride (CsF) (7.90 g), and N,N-dimethylacetamide (DMAc) (26 mL). The bath temperature was raised to 130 °C and the mixture was stirred for 8 hours. After stirring, the reaction mixture was allowed to cool to room temperature. After cooling, water was added to the reaction mixture, and the resulting solid was collected by filtration. The resulting solid was purified by silica gel column chromatography (hexane / dichloromethane = 1 / 1 (volume ratio)). The crude product was dissolved in approximately five times the amount of dichloromethane, and the same amount of methanol as the dichloromethane was added. The precipitated solid was collected by filtration to obtain 1.47 g of a yellow solid, which was identified as Compound A4 by ASAP-MS analysis (yield 31%).

[0615] [Synthesis Example 5] Compound A5 was synthesized according to the following synthetic route.

[0616] (S5-1) Synthesis of compound MA-5

[0617] [ka]

[0618] Under a nitrogen atmosphere, 3'-fluoro-5'-iodo-[1,1':4',1''-terphenyl]-2',6'-dicarbonitrile (20 g, 47.1 mmol), (4-(9H-carbazol-9-yl)phenyl)boronic acid (14.2 g, 50 mmol), Pd(amphos)Cl2 (0.67 g, 0.94 mmol), tripotassium phosphate (25 g, 118 mmol), 1,4-dioxane (160 mL), and ion-exchanged water (80 mL) were placed in a 300 mL three-neck flask and stirred at 100 °C for 5 hours. After stirring, 100 mL of ion-exchanged water was added to the reaction solution, and the precipitated solid was purified by silica gel column chromatography to obtain 23 g of a white solid. The resulting white solid was identified as compound MA-5 by ASAP-MS analysis (yield 90%). Note that Pd(amphos)Cl2 is an abbreviation for bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II).

[0619] (S5-2) Synthesis of Compound A5

[0620] [ka]

[0621] Under a nitrogen atmosphere, 1-phenyl-14H-benzo[4,5]thieno[2,3-a]benzo[4,5]thieno[3,2-i]carbazole (2.3 g, 5.00 mmol) was added to a mixture of compound MA-5 (4"-(9H-carbazol-9-yl)-6'-fluoro-4'-phenyl-[1,1':2',1"-terphenyl]-3',5'-dicarbonitrile) (3.0 g, 5.56 mmol), cesium fluoride (CsF) (1.7 g, 11.1 mmol), and 28 mL of N,N-dimethylacetamide (DMAc). The bath temperature was raised to 130°C and the mixture was stirred for 2 hours. After stirring, the reaction mixture was allowed to cool to room temperature. After cooling, water was added to the reaction mixture, and the resulting solid was collected by filtration. The resulting solid was purified by silica gel column chromatography to obtain 3.6 g of a yellow solid. The resulting yellow solid was identified as Compound A5 by ASAP-MS analysis (yield 66%).

[0622] [Synthesis Example 6] Compound A6 was synthesized according to the following synthetic route.

[0623] (S6-1) Synthesis of Compound A6

[0624] [ka]

[0625] Under a nitrogen atmosphere, 1-phenyl-14H-benzo[4,5]thieno[2,3-a]benzo[4,5]thieno[3,2-i]carbazole (2.3 g, 5.00 mmol) was added to a mixture of compound MA-5 (4"-(9H-carbazol-9-yl)-6'-fluoro-4'-phenyl-[1,1':2',1"-terphenyl]-3',5'-dicarbonitrile) (3.0 g, 5.56 mmol), cesium fluoride (CsF) (1.7 g, 11.1 mmol), and 28 mL of bN,N-dimethylacetamide (DMAc). The bath temperature was raised to 130°C and the mixture was stirred for 2 hours. After stirring, the reaction mixture was allowed to cool to room temperature. After cooling, water was added to the reaction mixture, and the resulting solid was collected by filtration. The resulting solid was purified by silica gel column chromatography to obtain 4.1 g of a yellow solid. The resulting yellow solid was identified as Compound A6 by ASAP-MS analysis (yield 75%).

[0626] [Synthesis Example 7] Compound A7 was synthesized according to the following synthetic route.

[0627] (S7-1) Synthesis of compound MA-7

[0628] [ka]

[0629] Under a nitrogen atmosphere, 3'-fluoro-5'-iodo-[1,1':4',1''-terphenyl]-2',6'-dicarbonitrile (5.0 g, 11.8 mmol), (6-phenylpyridin-3-yl)boronic acid (2.81 g, 14.1 mmol), Pd(amphos)Cl2 (0.24 g, 0.17 mmol), tripotassium phosphate (7.5 g, 35.4 mmol), 1,4-dioxane (20 mL), and ion-exchanged water (10 mL) were placed in a 300 mL three-neck flask and stirred at 100 °C for 5 hours. After stirring, 100 mL of ion-exchanged water was added to the reaction solution, and the precipitated solid was purified by silica gel column chromatography to obtain 3.5 g of a white solid. The resulting white solid was identified as compound MA-7 by ASAP-MS analysis (yield 99%).

[0630] (S7-2) Synthesis of Compound A7

[0631] [ka]

[0632] Under a nitrogen atmosphere, 1-phenyl-14H-benzo[4,5]thieno[2,3-a]benzo[4,5]thieno[3,2-i]carbazole (1.5 g, 3.39 mmol) was added to a mixture of compound MA-7 (3'-fluoro-5'-(6-phenylpyridin-3-yl)-[1,1':4',1''-terphenyl]-2',6'-dicarbonitrile) (1.7 g, 3.8 mmol), cesium fluoride (CsF) (1.1 g, 7.5 mmol), and 20 mL of N,N-dimethylacetamide (DMAc). The bath temperature was raised to 130°C and the mixture was stirred for 2 hours. After stirring, the reaction mixture was allowed to cool to room temperature. After cooling, water was added to the reaction mixture, and the resulting solid was collected by filtration. The resulting solid was purified by silica gel column chromatography to obtain 2.3 g of a yellow solid. The resulting yellow solid was identified as Compound A7 by ASAP-MS analysis (yield 69%).

[0633] [Synthesis Example 8] Compound A8 was synthesized according to the following synthetic route.

[0634] (S8-1) Synthesis of compound MA-8

[0635] [ka]

[0636] Under a nitrogen atmosphere, 3'-fluoro-5'-iodo-[1,1':4',1''-terphenyl]-2',6'-dicarbonitrile (20 g, 47 mmol), dibenzo[b,d]furan-3-ylboronic acid (10 g, 47 mmol), Pd(amphos)Cl2 (0.67 g, 0.94 mmol), tripotassium phosphate (30 g, 141 mmol), 1,4-dioxane (120 mL), and ion-exchanged water (60 mL) were placed in a 300 mL three-neck flask and stirred at 100 °C for 5 hours. After stirring, 100 mL of ion-exchanged water was added to the reaction solution, and the precipitated solid was purified by silica gel column chromatography to obtain 20 g of a white solid. The resulting white solid was identified as compound MA-8 by ASAP-MS analysis (yield 90%).

[0637] (S8-2) Synthesis of Compound A8

[0638] [ka]

[0639] Under a nitrogen atmosphere, 1-phenyl-14H-benzo[4,5]thieno[2,3-a]benzo[4,5]thieno[3,2-i]carbazole (2.7 g, 5.8 mmol) was added to a mixture of compound MA-8 (3'-(dibenzo[b,d]furan-3-yl)-5'-fluoro-[1,1':4',1''-terphenyl]-2',6'-dicarbonitrile) (3.0 g, 6.5 mmol), cesium fluoride (CsF) (2.0 g, 13 mmol), and 35 mL of N,N-dimethylacetamide (DMAc). The bath temperature was raised to 130°C and the mixture was stirred for 2 hours. After stirring, the reaction mixture was allowed to cool to room temperature. After cooling, water was added to the reaction mixture, and the resulting solid was collected by filtration. The resulting solid was purified by silica gel column chromatography to obtain 4.0 g of a yellow solid. The resulting yellow solid was identified as Compound A8 by ASAP-MS analysis (yield 69%). [Explanation of symbols]

[0640] 1... organic electroluminescence element, 10... organic layer, 3... anode, 4... cathode, 5... light-emitting layer, 6... hole injection layer, 7... hole transport layer, 8... electron transport layer, 9... electron injection layer.

Claims

1. A compound represented by the following formula (2): 【Chemical 1】 (In the formula (2), Ar ２ 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, L ２ 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, L ２ is a single bond, Ar ２ is D shown in the formula (2) ２１ , R ２１ , R ２２ and bonded to the benzene ring to which the two cyano groups are bonded by a carbon-carbon bond, L ２ When is not a single bond, L ２ is D shown in the formula (2) ２１ , R ２１ , R ２２ and bonded to the benzene ring to which the two cyano groups are bonded by a carbon-carbon bond, D ２１ is a group represented by the following formula (20): 【Chemistry 2】 (In the formula (2) and formula (20), R ２１ , R ２２ , R ２０１ , R ２０２ , R ２０３ , R ２０４ , R ２０５ , R ２０６ , R ２０７ , R ２０８ , R ２０９ , R ２１０ , R ２１１ and R ２１２ are each independently, hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted 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, -Si(R ２８１ ) (R ２８２ ) (R ２８３ ) a group represented by a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, -O-(R ２８４ ) a group represented by -S-(R ２８５ ) a group represented by -N(R ２８６ ) (R ２８７ ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R ２８８ a group represented by -C(=O)(OR ２８９ ) a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R ２９０ ) (R ２９１ ) a group represented by -Ge(R ２９２ ) (R ２９３ ) (R ２９４ ) a group represented by -B(R ２９５ ) (R ２９６ ) a group represented by -B(OR ２９７ ) (OR ２９８ ) a group represented by -O-S(=O) ２ (R ２９９ ) is a group represented by R ２１ , R ２２ and R ２０１ ~R ２１２ is not a 9-carbazolyl group, R ２０１ , R ２０２ , R ２０３ , R ２０４ , R ２０５ , R ２０６ , R ２０７ , R ２０８ , R ２０９ , R ２１０ , R ２１１ and R ２１２ at least one selected from the group consisting of is not a hydrogen atom, In the formula (20), * indicates a bonding position. In the compound represented by formula (2), R ２８１ , R ２８２ , R ２８３ , R ２８４ , R ２８５ , R ２８６ , R ２８７ , R ２８８ , R ２８９ , R ２９０ , R ２９１ , R ２９２ , R ２９３ , R ２９４ , R ２９５ , R ２９６ , R ２９７ , R ２９８ and R ２９９ 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 hydrocarbon ring group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ２８１ If there are multiple R ２８１ are the same or different from each other, R ２８２ If there are multiple R ２８２ are the same or different from each other, R ２８３ If there are multiple R ２８３ are the same or different from each other, R ２８４ If there are multiple R ２８４ are the same or different from each other, R ２８５ If there are multiple R ２８５ are the same or different from each other, R ２８６ If there are multiple R ２８６ are the same or different from each other, R ２８７ If there are multiple R ２８７ are the same or different from each other, R ２８８ If there are multiple R ２８８ are the same or different from each other, R ２８９ If there are multiple R ２８９ are the same or different from each other, R ２９０ If there are multiple R ２９０ are the same or different from each other, R ２９１ If there are multiple R ２９１ are the same or different from each other, R ２９２ If there are multiple R ２９２ are the same or different from each other, R ２９３ If there are multiple R ２９３ are the same or different from each other, R ２９４ If there are multiple R ２９４ are the same or different from each other, R ２９５ If there are multiple R ２９５ are the same or different from each other, R ２９６ If there are multiple R ２９６ are the same or different from each other, R ２９７ If there are multiple R ２９７ are the same or different from each other, R ２９８ If there are multiple R ２９８ are the same or different from each other, R ２９９ If there are multiple R ２９９ are the same or different from each other.)

2. The compound according to claim 1, wherein the compound represented by formula (2) is a compound represented by the following formula (2-1): 【Chemistry 3】 (In the formula (2-1), D ２１ , Ar ２ , L ２ , R ２１ and R ２２ are the D in the formula (2), respectively. ２１ , Ar ２ , L ２ , R ２１ and R ２２ is synonymous with

3. The compound represented by formula (2) is a compound represented by formula (2-11):

3. The compound of claim 1 or claim 2. 【Chemistry 4】 (In the formula (2-11), D ２１ , Ar ２ , L ２ , R ２１ and R ２２ are the D in the formula (2), respectively. ２１ , Ar ２ , L ２ , R ２１ and R ２２ is synonymous with

4. L ２ is a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms; A compound according to any one of claims 1 to 3.

5. The compound represented by formula (2) is a compound represented by formula (2-111): A compound according to any one of claims 1 to 4. 【Chemistry 5】 (In the formula (2-111), D ２１ , Ar ２ , R ２１ and R ２２ are the D in the formula (2), respectively. ２１ , Ar ２ , R ２１ and R ２２ is synonymous with

6. R ２０１ , R ２０２ , R ２０３ , R ２０４ , R ２０５ , R ２０６ , R ２０７ , R ２０８ , R ２０９ , R ２１０ , R ２１１ and R ２１２ at least one selected from the group consisting of is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; 6. A compound according to any one of claims 1 to 5.

7. R ２０１ , R ２０２ , R ２０３ , R ２０４ , R ２０５ , R ２０６ , R ２０７ , R ２０８ , R ２０９ , R ２１０ , R ２１１ and R ２１２ wherein at least one selected from the group consisting of is a substituted or unsubstituted phenyl group.

7. A compound according to any one of claims 1 to 6.

8. R ２０５ , R ２０６ , R ２０７ and R ２０８ At least one selected from the group consisting of is not a hydrogen atom, A compound according to any one of claims 1 to 7.

9. R ２０５ , R ２０６ , R ２０７ and R ２０８ at least one selected from the group consisting of is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; A compound according to any one of claims 1 to 8.

10. R ２０５ , R ２０６ , R ２０７ and R ２０８ wherein at least one selected from the group consisting of is a substituted or unsubstituted phenyl group.

10. A compound according to any one of claims 1 to 9.

11. R ２１ and R ２２ one or both of are not hydrogen atoms, 11. A compound according to any one of claims 1 to 10.

12. R ２１ and R ２２ one or both of the above is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, 12. A compound according to any one of claims 1 to 11.

13. R ２１ and R ２２ one or both of the groups are substituted or unsubstituted phenyl groups; 13. A compound according to any one of claims 1 to 12.

14. The substituents in the case of "substituted or unsubstituted" are an unsubstituted alkyl group having 1 to 6 carbon atoms; an unsubstituted aryl group having 6 to 13 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 13 ring atoms; 14. A compound according to any one of claims 1 to 13.

15. Any group described as "substituted or unsubstituted" is an "unsubstituted" group.

14. A compound according to any one of claims 1 to 13.

16. The compound represented by formula (2) contains at least one deuterium atom.

16. A compound according to any one of claims 1 to 15.

17. An organic electroluminescence element, a cathode, an anode, and an organic layer contained between the cathode and the anode; The organic layer comprises one or more layers, at least one layer of the one or more layers included in the organic layer contains a second compound; The second compound is a compound according to any one of claims 1 to 16. Organic electroluminescent element.

18. at least one layer among the one or more layers included in the organic layer is an emitting layer, the light-emitting layer contains the second compound; 18. The organic electroluminescence device according to claim 17.

19. the light-emitting layer contains a fluorescent first compound; 19. The organic electroluminescence device according to claim 18.

20. The first compound is a compound represented by the following formula (1):

20. The organic electroluminescence device according to claim 19. 【Chemistry 6】 (In the formula (1), Ring A1, ring B1 and ring C1 each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, L １１ and L １２ are each independently N-R １０ , oxygen atom, sulfur atom, selenium atom, C(R １１ ) (R １２ ), or Si(R １３ ) (R １４ ) and L １３ is a boron atom, a phosphorus atom, or P═O, R １０ ~R １４ are each independently, bonding with ring A1, ring B1 or ring C1 to form a substituted or unsubstituted monocyclic ring, or combines with ring A1, ring B1 or ring C1 to form a substituted or unsubstituted fused ring, or not bonded to ring A1, ring B1, or ring C1; R １１ and R １２ teeth, joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R １３ and R １４ teeth, joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring １０ ~R １４ 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, -C(R １５ an iminyl group represented by )=N; 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 １５ teeth, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, R １０ If there are multiple R １０ are identical to or different from each other, R １１ If there are multiple R １１ are identical to or different from each other, R １２ If there are multiple R １２ are identical to or different from each other, R １３ If there are multiple R １３ are identical to or different from each other, R １４ If there are multiple R １４ are identical to or different from each other, R １５ If there are multiple R １５ are the same or different from each other.)

21. The lowest excited singlet energy S of the first compound １ (M1) and the lowest excited singlet energy S of the second compound １ (M2) satisfies the relationship of the following formula (Formula 1), 21. The organic electroluminescence device according to claim 19 or 20. S １ (M2)>S １ (M1)…(Number 1)

22. the light-emitting layer contains a third compound, The lowest excited singlet energy S of the second compound １ (M2) and the lowest excited singlet energy S of the third compound １ (M3) satisfies the relationship of the following formula (Formula 2):

22. The organic electroluminescence device according to claim 18. S １ (M3)>S １ (M2) …(number 2)

23. the light-emitting layer does not contain a metal complex; 23. The organic electroluminescence device according to claim 18.

24. the light-emitting layer does not contain a phosphorescent material; The organic electroluminescence device according to any one of claims 18 to 23.

25. a hole transport layer between the anode and the light-emitting layer; The organic electroluminescence device according to any one of claims 18 to 24.

26. an electron transport layer between the cathode and the light-emitting layer; 26. The organic electroluminescence device according to claim 18.

27. An electronic device equipped with the organic electroluminescence element according to any one of claims 17 to 26.

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