Organic electroluminescent element, compound, and electronic device

Abstract

An organic electroluminescent element (1) has an anode (3), a cathode (4), and a light-emitting layer (5) provided between the anode (3) and the cathode (4). The light-emitting layer (5) contains a compound M3 represented by general formula (1) below and a delayed fluorescent compound M2. The structure of the compound M3 is different from that of the compound M2, and the singlet energy S1 (M3) of the compound M3 and the singlet energy S1 (M2) of the compound M2 satisfy the relationship in the mathematical expression (expression 1) below.　(Expression 1) S1 (M3) > S1 (M2) (in general formula (1), A is a group represented by any of general formula (11A), (11B), (11C), (11D), (11E), or (11F), and Y1 is an oxygen atom or sulfur atom).

Description

Organic electroluminescent element, compound, and electronic device

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

[0002] When a voltage is applied to an organic electroluminescence element (hereinafter sometimes referred to as an "organic EL element"), holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. The injected holes and electrons then recombine in the light-emitting layer to form excitons. According to the statistical law of electron spin, singlet excitons are generated at a rate of 25% and triplet excitons at a rate of 75%. Fluorescent organic EL elements that utilize light emission from singlet excitons are increasingly 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 elements.

[0003] Furthermore, it is expected that organic EL elements will emit light more efficiently by utilizing triplet excitons in addition to singlet excitons. Against this background, highly efficient fluorescent organic EL elements utilizing thermally activated delayed fluorescence (hereinafter sometimes simply referred to as "delayed fluorescence") have been proposed and studied. For example, the TADF (thermally activated delayed fluorescence) mechanism has been studied. This TADF 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 level and the triplet level is used. Thermally activated delayed fluorescence is described, for example, in "Device Properties of Organic Semiconductors," edited by Adachi Chinaya, Kodansha, published April 1, 2012, pages 261-268.

[0004] In order to improve the performance of organic EL elements, for example, Patent Documents 1 and 2 disclose compounds having a benzofurocarbazole ring or a benzothienocarbazole ring as compounds that can be used in organic EL elements. Patent Document 2 also discloses an organic EL element that utilizes the TADF mechanism. Examples of the performance of organic EL elements include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan.

[0005] International Publication No. 2013 / 011891 International Publication No. 2020 / 122118

[0006] Further improvements in performance are required for organic EL elements that utilize the TADF mechanism.

[0007] An object of the present invention is to provide a high-performance organic electroluminescence element, a compound capable of realizing a high-performance organic electroluminescence element, and an electronic device equipped with the organic EL element.

[0008] According to one aspect of the present invention, there is provided an organic EL device comprising: an anode; a cathode; and an emitting layer disposed between the anode and the cathode, wherein the emitting layer comprises a compound M3 represented by the following general formula (1) and a delayed fluorescent compound M2, wherein the compound M3 and the compound M2 have different structures, and the singlet energy S １ (M3) and the singlet energy S of the compound M2 １ (M2) satisfies the relationship of the following mathematical formula (1): １ (M3) > S １ (M2) (Math. 1)

[0009]

[0010] (In the general formula (1), A is a group represented by any one of the following general formulas (11A), (11B), (11C), (11D), (11E), and (11F), and Y １ is an oxygen atom or a sulfur atom, n is 0 or 1, R ２１ ~R ２８one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １００ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ２１ ~R ２８ are each independently a hydrogen atom, a halogen atom, a cyano group, 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 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms, a hydroxy group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, -N(Rz) ２ a thiol group, a substituted or unsubstituted alkylthio group having 1 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms, a substituted germanium group, a substituted phosphine oxide group, a nitro group, a substituted boryl group, or a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, Rz is 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, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, -N(Rz) ２ In the formula, two Rz are the same or different, and a plurality of R １００are the same or different from each other, provided that n is 0 and X in the following general formulae (11A), (11B), (11C), (11D), (11E) and (11F) １ is an oxygen atom, R ２５ is not a substituted or unsubstituted dibenzofuranyl group. ２１ ~R ２４ represents the bonding position to any one of the carbon atoms of the six-membered ring to which

[0011]

[0012] (In the general formulae (11A), (11B), (11C), (11D), (11E) and (11F), X １ is an oxygen atom or a sulfur atom, R １１ ~R １４ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １５ ~R １８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １９ and R ２０ is a hydrogen atom, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring １１ ~R １８ each independently represents R that does not form the substituted or unsubstituted monocyclic ring in the general formula (1) and does not form the substituted or unsubstituted fused ring. ２１ ~R ２８ where n is 0, * is the same as R ２１ ~R ２４ represents the bonding position of any one of the carbon atoms of the six-membered ring to which n is bonded, and when n is 1, * represents R １００ represents the bonding position of any one of the carbon atoms of the benzene ring to which

[0013] According to one aspect of the present invention, there is provided an organic EL device comprising: an anode; a cathode; and an emitting layer disposed between the anode and the cathode, wherein the emitting layer comprises a compound M3 represented by the following general formula (1) and a delayed fluorescent compound M2, wherein the compound M3 and the compound M2 have different structures, and the singlet energy S １ (M3) and the singlet energy S of the compound M2 １ (M2) satisfies the relationship of the following mathematical formula (1): １ (M3) > S １ (M2) (Math. 1)

[0014]

[0015] (In the general formula (1), A is a group represented by any one of the following general formulas (11A), (11B), (11C), (11D), (11E), and (11F), and Y １ is an oxygen atom or a sulfur atom, n is 0 or 1, R ２１ ~R ２８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １００ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ２１ ~R ２８are each independently a hydrogen atom, a halogen atom, a cyano group, 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 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms, a hydroxy group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, -N(Rz) ２ a thiol group, a substituted or unsubstituted alkylthio group having 1 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms, a substituted germanium group, a substituted phosphine oxide group, a nitro group, a substituted boryl group, or a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, Rz is 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, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, -N(Rz) ２ In the formula, two Rz are the same or different, and a plurality of R １００ are the same or different from each other, provided that n is 0 and X in the following general formulae (11A), (11B), (11C), (11D), (11E) and (11F) １ is an oxygen atom, R ２５ is not a substituted or unsubstituted dibenzofuranyl group. ２１ ~R ２４ represents the bonding position to any one of the carbon atoms of the six-membered ring to which

[0016]

[0017] (In the general formulae (11A), (11B), (11C), (11D), (11E) and (11F), X １ is an oxygen atom or a sulfur atom, R １１ ~R ２０ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring １１ ~R ２０ each independently represents R that does not form the substituted or unsubstituted monocyclic ring in the general formula (1) and does not form the substituted or unsubstituted fused ring. ２１ ~R ２８ where n is 0, * is the same as R ２１ ~R ２４ represents the bonding position of any one of the carbon atoms of the six-membered ring to which n is bonded, and when n is 1, * represents R １００ represents the bonding position of any one of the carbon atoms of the benzene ring to which

[0018] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescence element according to the above-described aspect of the present invention.

[0019] According to one aspect of the present invention, there is provided a compound represented by the following general formula (100):

[0020]

[0021] (In the general formula (100), X １ is an oxygen atom or a sulfur atom, R １００ , R １１ ~R ２０ , and R ２２ ~R ２８ are each independently a hydrogen atom, -(L １０１ ) nx-R １０１ nx is 0, 1, 2 or 3; -(L１０１ ) nx-R １０１ When a plurality of groups represented by -(L １０１ ) nx-R １０１ The groups represented by R are the same or different from each other, １００ are the same or different from each other, R １０１ is an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted phenyl group, an unsubstituted (9-phenyl)carbazolyl group, an unsubstituted 9-carbazolyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothienyl group, an unsubstituted (9-dibenzofuranyl)carbazolyl group, an unsubstituted (9-dibenzothienyl)carbazolyl group, a monovalent group derived from a compound represented by the following general formula (101), a monovalent group derived from a compound represented by the following general formula (102), a monovalent group derived from a compound represented by the following general formula (103), a monovalent group derived from a compound represented by the following general formula (104), a monovalent group derived from a compound represented by the following general formula (105), or a monovalent group derived from a compound represented by the following general formula (106), １０１ is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted phenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothienylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted (9-dibenzofuranyl)carbazolylene group, a substituted or unsubstituted (9-dibenzothienyl)carbazolylene group, a divalent group derived from a compound represented by the following general formula (101), a divalent group derived from a compound represented by the following general formula (102), a divalent group derived from a compound represented by the following general formula (103), a divalent group derived from a compound represented by the following general formula (104), a divalent group derived from a compound represented by the following general formula (105), or a divalent group derived from a compound represented by the following general formula (106), １０１is a substituted alkylene group having 1 to 30 carbon atoms, a substituted phenylene group, a substituted dibenzofuranylene group, a substituted dibenzothienylene group, a substituted carbazolylene group, a substituted (9-dibenzofuranyl)carbazolylene group, or a substituted (9-dibenzothienyl)carbazolylene group, the substituents are each independently an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted phenyl group, an unsubstituted (9-phenyl)carbazolyl group, an unsubstituted 9-carbazolyl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothienyl group; １０１ When there are two or more, there are two or more L １０１ are the same or different from each other, R １０１ When two or more R １０１ are the same or different from each other, provided that * is R １００ represents the bonding position of any one of the carbon atoms of the benzene ring to which

[0022]

[0023] (In the general formulae (101) to (106), X １Ｘ is an oxygen atom or a sulfur atom, R １１Ｘ ~R ２１Ｘ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted phenyl group, an unsubstituted (9-phenyl)carbazolyl group, an unsubstituted 9-carbazolyl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothienyl group, with the proviso that R １０１ is a monovalent group derived from a compound of any one of the general formulas (101) to (106), and when nx is 0, R １１Ｘ ~R ２０Ｘ and the carbon atom of the six-membered ring to which R ２１Ｘ is bonded to a nitrogen atom, １１ ~R ２０ , R ２２ ~R ２８ and R １００ is bonded to any one of the carbon atoms of the six-membered ring to which nx is bonded, and when nx is 1, 2, or 3, R １１Ｘ ~R２０Ｘ and the carbon atom of the six-membered ring to which R ２１Ｘ Any one of the nitrogen atoms to which is bonded is L １０１ Combines with. １０１ is a divalent group derived from a compound of any one of the general formulae (101) to (106), and when nx is 1, R １１Ｘ ~R ２０Ｘ and the carbon atom of the six-membered ring to which R ２１Ｘ Of any two nitrogen atoms to which is bonded, one is R １０１ and the other is R １１ ~R ２０ , R ２２ ~R ２８ and R １００ is bonded to any one of the carbon atoms of the six-membered ring to which L １０１ is a divalent group derived from a compound of any one of the general formulae (101) to (106), and when nx is 2 or 3, R １１Ｘ ~R ２０Ｘ and the carbon atom of the six-membered ring to which R ２１Ｘ Of any two nitrogen atoms to which is bonded, one is R １０１ or L １０１ and the other is R １１ ~R ２０ , R ２２ ~R ２８ and R １００ any one of the carbon atoms of the six-membered ring to which L is bonded １０１ Combine with

[0024] According to one embodiment of the present invention, it is possible to provide a high-performance organic electroluminescence element, a compound capable of realizing a high-performance organic electroluminescence element, and an electronic device equipped with the organic electroluminescence element.

[0025] Fig. 1 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a first embodiment of the present invention. Fig. 2 is a diagram showing a schematic view of an apparatus for measuring transient PL. Fig. 3 is a diagram showing an example of a decay curve of transient PL. Fig. 4 is a diagram showing the relationship between the energy levels of compounds M3 and M2 in the emitting layer of an example of an organic electroluminescence element according to a first embodiment of the present invention. Fig. 5 is a diagram showing the energy levels of compounds M3, M2 and M1 in the emitting layer of an example of an organic electroluminescence element according to a second embodiment of the present invention, as well as the relationship between energy transfer.

[0026] [Definitions] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0027] In this specification, in a chemical structural formula, a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded to a possible bonding position that is not explicitly marked with a symbol such as "R" or "D" representing a deuterium atom.

[0028] As used herein, the term "number of ring carbon atoms" refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. For example, a 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and a 9,9'-spirobifluorenyl group has 25 ring carbon atoms. When a benzene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of a benzene ring substituted with an alkyl group is 6. Furthermore, when the naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.

[0029] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, and a ring assembly). Atoms that do not constitute the ring (e.g., hydrogen atoms terminating the bonds of atoms constituting the ring) and atoms contained in the substituent when the ring is substituted with a substituent are not included in the number of ring atoms. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms or atoms constituting a substituent bonded to the pyridine ring is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. Furthermore, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring, so the number of ring atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

[0030] In this specification, the "number of carbon atoms XX to YY" in the expression "substituted or unsubstituted ZZ group having carbon atoms XX to YY" represents the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0031] In this specification, the "number of atoms XX to YY" in the expression "substituted or unsubstituted ZZ group having number of atoms XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of substituents when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0032] In this specification, an unsubstituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group". In this specification, "unsubstituted" in the case of a "substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protist atom, a deuterium atom, or a tritium atom. Furthermore, in this specification, "substituted" in the case of a "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. Similarly, "substituted" in the case of a "BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced with an AA group.

[0033] "Substituents Described in This Specification" The substituents described in this specification are explained below.

[0034] The number of ring carbon atoms of an "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring atoms of an "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms of an "unsubstituted alkyl group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein. The number of carbon atoms of an "unsubstituted alkenyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of carbon atoms of an "unsubstituted alkynyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of ring carbon atoms of an "unsubstituted cycloalkyl group" described herein is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified herein. Unless otherwise specified herein, the number of ring carbon atoms of an "unsubstituted arylene group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18. Unless otherwise specified herein, the number of ring atoms of an "unsubstituted divalent heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18. Unless otherwise specified herein, the number of carbon atoms of an "unsubstituted alkylene group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0035] "Substituted or Unsubstituted Aryl Group" Specific examples (Specific Example Group G1) of the "substituted or unsubstituted aryl group" described herein include the following unsubstituted aryl group (Specific Example Group G1A) and substituted aryl group (Specific Example Group G1B). (Here, an unsubstituted aryl group refers to a case where a "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and a substituted aryl group refers to a case where a "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" simply refers to both an "unsubstituted aryl group" and a "substituted aryl group." A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with substituents. Examples of the "substituted aryl group" include a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with substituents in the "unsubstituted aryl group" of the following Specific Example Group G1A, and examples of the substituted aryl group of the following Specific Example Group G1B. It should be noted that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl groups" described in this specification also include groups in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl groups" of the following specific example group G1B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted aryl groups" of the following specific example group G1B is further replaced with a substituent.

[0036] Unsubstituted aryl groups (specific example group G1A): a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a benzanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a triphenylenyl group, a benzotriphenylenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, 9,9'-spirobifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, fluoranthenyl group, benzofluoranthenyl group, perylenyl group, and monovalent aryl groups derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15):

[0037]

[0038]

[0039] Substituted aryl groups (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, cyanophenyl group, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl groups, and monovalent groups derived from the ring structures represented by the above general formulae (TEMP-1) to (TEMP-15), in which one or more hydrogen atoms are replaced with substituents.

[0040] "Substituted or Unsubstituted Heterocyclic Group" The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom among the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom. The "heterocyclic group" described herein is a monocyclic group or a fused ring group. The "heterocyclic group" described herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described herein include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, an unsubstituted heterocyclic group refers to when a "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and a substituted heterocyclic group refers to when a "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when simply referring to a "heterocyclic group", it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group". A "substituted heterocyclic group" means a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with substituents. Specific examples of the "substituted heterocyclic group" include groups in which hydrogen atoms of an "unsubstituted heterocyclic group" in the following specific example group G2A are replaced, and examples of substituted heterocyclic groups in the following specific example group G2B. The examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic groups" described in this specification also include groups in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic groups" of specific example group G2B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted heterocyclic groups" of specific example group G2B is further replaced with a substituent.

[0041] 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).

[0042] Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced with substituents (specific example group G2B4).

[0043] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolidinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, an indazolyl group, a phenanthrolinyl group, a phenanthridinyl group, an acridinyl group, a phenazinyl group, a carbazolyl group, Benzocarbazolyl group, morpholino group, phenoxazinyl group, phenothiazinyl group, azacarbazolyl group, and diazacarbazolyl group.

[0044] Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): a furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a xanthenyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a benzoxazolyl group, a benzisoxazolyl group, a phenoxazinyl group, a morpholino group, a dinaphthofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, an azanaphthobenzofuranyl group, and a diazanaphthobenzofuranyl group.

[0045] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a benzothiophenyl group (benzothienyl group), an isobenzothiophenyl group (isobenzothienyl group), a dibenzothiophenyl group (dibenzothienyl group), a naphthobenzothiophenyl group (naphthobenzothienyl group), a benzothiazolyl group, a benzisothiazolyl group, a phenothiazinyl group, a dinaphthothiophenyl group (dinaphthothienyl group), an azadibenzothiophenyl group (azadibenzothienyl group), a diazadibenzothiophenyl group (diazadibenzothienyl group), an azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and a diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0046] 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):

[0047]

[0048]

[0049] In the general formulae (TEMP-16) to (TEMP-33), X Ａ and Y Ａ are each independently an oxygen atom, a sulfur atom, NH, or CH ２ However, X Ａ and Y Ａ At least one of X is an oxygen atom, a sulfur atom, or NH. Ａ and Y Ａ At least one of the groups is NH or CH ２ In this case, the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) may contain any of these NH, CH ２ and monovalent groups obtained by removing one hydrogen atom from the group consisting of:

[0050] Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): a (9-phenyl)carbazolyl group, a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a (9-naphthyl)carbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a methylbenzimidazolyl group, an ethylbenzimidazolyl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenylquinazolinyl group, and a biphenylylquinazolinyl group.

[0051] 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].

[0052] Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3): phenyldibenzothiophenyl group, methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and a monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0053] 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):

[0054] 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 One of them is CH ２ and n is 0 or more. The methylene group in the formula (I) is one or more hydrogen atoms selected from the hydrogen atoms of the methylene group in the formula (I).

[0055] "Substituted or Unsubstituted Alkyl Group" Specific examples (Specific Example Group G3) of the "substituted or unsubstituted alkyl group" described herein include the following unsubstituted alkyl group (Specific Example Group G3A) and substituted alkyl group (Specific Example Group G3B). (Here, the term "unsubstituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and the term "substituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereinafter, the term "alkyl group" includes both an "unsubstituted alkyl group" and a "substituted alkyl group." A "substituted alkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced with substituents. Specific examples of the "substituted alkyl group" include the following "unsubstituted alkyl group" (Specific Example Group G3A) in which one or more hydrogen atoms are replaced with substituents, and the examples of the substituted alkyl group (Specific Example Group G3B). In this specification, the alkyl group in an "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the term "unsubstituted alkyl group" includes a straight-chain "unsubstituted alkyl group" and a branched "unsubstituted alkyl group." The examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes groups in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" of specific example group G3B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted alkyl group" of specific example group G3B is further replaced with a substituent.

[0056] Unsubstituted alkyl groups (specific example group G3A): a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, and a t-butyl group.

[0057] Substituted alkyl groups (specific example group G3B): a heptafluoropropyl group (including isomers), a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, and a trifluoromethyl group.

[0058] "Substituted or Unsubstituted Alkenyl Group" Specific examples (Specific Example Group G4) of the "substituted or unsubstituted alkenyl group" described herein include the following unsubstituted alkenyl group (Specific Example Group G4A) and substituted alkenyl group (Specific Example Group G4B). (Here, an unsubstituted alkenyl group refers to a case where a "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and a "substituted alkenyl group" refers to a case where a "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply refers to both an "unsubstituted alkenyl group" and a "substituted alkenyl group." A "substituted alkenyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced with substituents. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl groups" (specific example group G4A) having a substituent, and examples of substituted alkenyl groups (specific example group G4B). The examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl group" described in this specification also includes groups in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl groups" of specific example group G4B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted alkenyl groups" of specific example group G4B is further replaced with a substituent.

[0059] Unsubstituted alkenyl groups (specific example group G4A): vinyl group, allyl group, 1-butenyl group, 2-butenyl group, and 3-butenyl group.

[0060] 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.

[0061] - "Substituted or Unsubstituted Alkynyl Group" Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl group (specific example group G5A). (Here, an unsubstituted alkynyl group refers to a case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, the term "alkynyl group" includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group." A "substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" have been replaced with a substituent. Specific examples of the "substituted alkynyl group" include a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" (specific example group G5A) have been replaced with a substituent.

[0062] Unsubstituted alkynyl groups (specific example group G5A): ethynyl group.

[0063] "Substituted or Unsubstituted Cycloalkyl Group" Specific examples (Specific Example Group G6) of the "substituted or unsubstituted cycloalkyl group" described herein include the following unsubstituted cycloalkyl group (Specific Example Group G6A) and substituted cycloalkyl group (Specific Example Group G6B). (Here, the term "unsubstituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group," and the term "substituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group.") In this specification, the term "cycloalkyl group" simply refers to both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group." A "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced with substituents. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (Specific Example Group G6A) in which one or more hydrogen atoms are replaced with substituents, and the examples of the substituted cycloalkyl group (Specific Example Group G6B). The examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed here are merely examples, and the "substituted cycloalkyl groups" described in this specification also include groups in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl groups" of specific example group G6B are replaced with substituents, and groups in which a hydrogen atom of a substituent in the "substituted cycloalkyl groups" of specific example group G6B is further replaced with a substituent.

[0064] Unsubstituted cycloalkyl groups (specific example group G6A): a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a 2-norbornyl group.

[0065] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.

[0066] -Si(R ９０１ ) (R ９０２ ) (R ９０３ A group represented by —Si(R ９０１ ) (R ９０２) (R ９０３ Specific examples (specific example group G7) of the group represented by the formula (G1) include -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. The multiple G1s in -Si(G1)(G1)(G1) may be the same or different. - Multiple G2 in Si(G1)(G2)(G2) are the same as or different from each other. - Multiple G1 in Si(G1)(G1)(G2) are the same as or different from each other. - Multiple G2 in Si(G2)(G2)(G2) are the same as or different from each other. - Multiple G3 in Si(G3)(G3)(G3) are the same as or different from each other. - Multiple G6 in Si(G6)(G6)(G6) are the same as or different from each other.

[0067] ・「-O-(R ９０４ A group represented by —O—(R ９０４ ) (Specific example group G8) includes -O(G1), -O(G2), -O(G3), and -O(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0068] ・"-S-(R ９０５ A group represented by —S—(R ９０５) (Specific example group G9) includes -S(G1), -S(G2), -S(G3), and -S(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0069] ・「-N(R ９０６ ) (R ９０７ A group represented by —N(R ９０６ ) (R ９０７ Specific examples (specific example group G10) of groups represented by the formula (G1) include -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. Multiple G1s in -N(G1)(G1) may be the same as or different from one another. Multiple G2s in -N(G2)(G2) may be the same as or different from one another. Multiple G3s in -N(G3)(G3) may be the same as or different from one another. -N(G6)(G6) may be the same or different from each other.

[0070] "Halogen Atom" Specific examples (specific example group G11) of the "halogen atom" described in this specification include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0071] "Substituted or unsubstituted fluoroalkyl group" As used herein, a "substituted or unsubstituted fluoroalkyl group" refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a 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. A "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. Note that the "substituted fluoroalkyl group" described herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in a "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include the examples of the above-mentioned "alkyl group" (specific example group G3) in which one or more hydrogen atoms have been replaced with fluorine atoms.

[0072] "Substituted or unsubstituted haloalkyl group" As used herein, a "substituted or unsubstituted haloalkyl group" refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The number of carbon atoms in an "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. A "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of a "haloalkyl group" are replaced with a substituent. Note that the "substituted haloalkyl group" described herein also includes a "substituted haloalkyl group" in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain are further replaced with a substituent, and a "substituted haloalkyl group" in which one or more hydrogen atoms of the substituent are further replaced with a substituent. Specific examples of the "unsubstituted haloalkyl group" include the examples of the above-mentioned "alkyl group" (specific example group G3) in which one or more hydrogen atoms are replaced with halogen atoms. A haloalkyl group may also be referred to as a halogenated alkyl group.

[0073] - "Substituted or unsubstituted alkoxy group" A specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0074] - "Substituted or unsubstituted alkylthio group" A specific example of the "substituted or unsubstituted alkylthio group" described in this specification is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0075] - "Substituted or unsubstituted aryloxy group" A specific example of the "substituted or unsubstituted aryloxy group" described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. Unless otherwise specified in this specification, the number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0076] - "Substituted or unsubstituted arylthio group" A specific example of the "substituted or unsubstituted arylthio group" described in this specification is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. Unless otherwise specified in this specification, the number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0077] - "Substituted or unsubstituted trialkylsilyl group" A specific example of the "substituted or unsubstituted trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Multiple G3s in -Si(G3)(G3)(G3) are the same as or different from one another. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the "unsubstituted trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0078] "Substituted or unsubstituted aralkyl group" A specific example of the "substituted or unsubstituted aralkyl group" described in this specification is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. Therefore, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one embodiment of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group," and the number of carbon atoms in the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification. Specific examples of the "substituted or unsubstituted aralkyl group" include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group, an α-naphthylmethyl group, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group, a 1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, a β-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethyl group, a 1-β-naphthylisopropyl group, and a 2-β-naphthylisopropyl group.

[0079] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described in this specification is preferably a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, or the like.

[0080] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic group described in this specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an aza Examples of such groups include a dibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group (a (9-phenyl)carbazol-1-yl group, a (9-phenyl)carbazol-2-yl group, a (9-phenyl)carbazol-3-yl group, or a (9-phenyl)carbazol-4-yl group), a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group.

[0081] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.

[0082]

[0083] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically any of the following groups:

[0084]

[0085] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0086] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0087]

[0088] In the general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.

[0089] 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.

[0090] "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group". Specific examples (specific example group G12) of the "substituted or unsubstituted arylene group" include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1.

[0091] "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.

[0092] "Substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group". Specific examples (specific example group G14) of the "substituted or unsubstituted alkylene group" include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3.

[0093] 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).

[0094]

[0095]

[0096] In the general formulae (TEMP-42) to (TEMP-52), Q １ ~Q １０ are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-42) to (TEMP-52), * represents a bonding position.

[0097]

[0098] In the general formulae (TEMP-53) to (TEMP-62), Q １ ~Q １０ are each independently a hydrogen atom or a substituent. ９ and Q １０ may be bonded to each other via a single bond to form a ring. In the general formulae (TEMP-53) to (TEMP-62), * represents the bonding position.

[0099]

[0100] In the general formulae (TEMP-63) to (TEMP-68), Q １ ~Q ８ are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-63) to (TEMP-68), * represents a bonding position.

[0101] 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).

[0102]

[0103]

[0104]

[0105] In the general formulae (TEMP-69) to (TEMP-82), Q １ ~Q ９ are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-69) to (TEMP-82), * represents a bonding position.

[0106]

[0107]

[0108]

[0109]

[0110] In the general formulae (TEMP-83) to (TEMP-102), Q １ ~Q ８ are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-83) to (TEMP-102), * represents a bonding position.

[0111] The above is the explanation of "substituents described in this specification."

[0112] "When bonded to form a ring" In this specification, when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle, bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other," it means when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle," when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring," and when "one or more pairs of adjacent groups do not bond to each other." In this specification, the cases when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle" and "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "when bonded to form a ring") will be explained below. An anthracene compound represented by the following general formula (TEMP-103), in which the main skeleton is an anthracene ring, will be described as an example.

[0113]

[0114] For example, R ９２１ ~R ９３０ In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," the pair of adjacent two groups is R ９２１ and R ９２２ Paired with R ９２２ and R ９２３ Paired with R ９２３ and R ９２４ Paired with R ９２４ and R ９３０ Paired with R ９３０ and R ９２５ Paired with R ９２５ and R ９２６ Paired with R ９２６ and R ９２７ Paired with R ９２７ and R ９２８ Paired with R ９２８ and R ９２９ and R ９２９ and R ９２１ It is paired with.

[0115] The above-mentioned "one or more pairs" means that two or more pairs of adjacent two or more groups may simultaneously form a ring. For example, R ９２１ and R ９２２ and are bonded to each other to form ring Q Ａ and simultaneously form R ９２５ and R ９２６ and are bonded to each other to form ring Q Ｂ When the anthracene compound represented by the general formula (TEMP-103) is formed, the anthracene compound represented by the general formula (TEMP-104) is represented by the following general formula (TEMP-104).

[0116]

[0117] The case where a "set of two or more adjacent groups" forms a ring includes not only the case where a set of "two" adjacent groups is bonded as in the above example, but also the case where a set of "three or more" adjacent groups is bonded. For example, R ９２１ and R ９２２ and are bonded to each other to form ring Q Ａ and R ９２２ and R９２３ and are bonded to each other to form ring Q Ｃ and 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.

[0118]

[0119] The "monocyclic ring" or "fused ring" formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when "one pair of adjacent two" forms a "monocyclic ring" or a "fused ring", the "monocyclic ring" or the "fused ring" may form a saturated ring or an unsaturated ring. For example, in the case of the ring Q formed in the general formula (TEMP-104), Ａ and Ring Q Ｂ are "monocyclic rings" or "fused rings". Ａ , and ring Q Ｃ is a "fused ring". Ａ and Tamaki Q Ｃ That is, Ring Q Ａ and Tamaki Q Ｃ The ring Q in the general formula (TMEP-104) is fused to form a fused ring. Ａ is a benzene ring, then ring Q Ａ The ring Q in the general formula (TMEP-104) is a monocyclic ring. Ａ is a naphthalene ring, then ring Q Ａ is a fused ring.

[0120] The "unsaturated ring" is at least one ring selected from the group consisting of an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring having an unsaturated bond in its ring structure, and a non-aromatic heterocyclic ring having an unsaturated bond in its ring structure. The unsaturated bond in the ring structure of the unsaturated ring is one or both of a double bond and a triple bond. Examples of aliphatic hydrocarbon rings having an unsaturated bond in their ring structure include cyclohexene and cyclohexadiene. Examples of non-aromatic heterocyclic rings having an unsaturated bond in their ring structure include dihydropyran, imidazoline, pyrazoline, quinolizine, indoline, and isoindoline.

[0121] A "saturated ring" is at least any ring selected from an aliphatic hydrocarbon ring having no unsaturated bond and a non-aromatic heterocyclic ring having no unsaturated bond. A saturated ring does not have a double bond or a triple bond in the ring structure. Specific examples of aromatic hydrocarbon rings include structures in which the groups given as specific examples in the specific example group G1 are terminated with a hydrogen atom. Specific examples of aromatic heterocyclic rings include structures in which the aromatic heterocyclic groups given as specific examples in the specific example group G2 are terminated with a hydrogen atom. Specific examples of aliphatic hydrocarbon rings include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom. "Forming a ring" means forming a ring only with multiple atoms of the parent skeleton, or with multiple atoms of the parent skeleton and one or more optional atoms. For example, R ９２１ and R ９２２ and a ring Q formed by bonding together Ａ is R ９２１ and the carbon atom of the anthracene skeleton to which R ９２２ It means a ring formed by the carbon atom of the anthracene skeleton to which R is bonded and one or more arbitrary atoms. ９２１ and R ９２２ Todekan Q Ａ In the case where R ９２１ and the carbon atom of the anthracene skeleton to which R ９２２ When a monocyclic unsaturated ring is formed by the carbon atom of the anthracene skeleton to which R is bonded and four carbon atoms, R ９２１and R ９２２ The ring formed by

[0122] Here, unless otherwise specified herein, the "any atom" is preferably at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. In any atom (for example, in the case of a carbon atom or a nitrogen atom), a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "any substituent" described below. When any atom other than a carbon atom is included, the formed ring is a heterocycle. Unless otherwise specified herein, the "one or more any atoms" constituting the monocycle or fused ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5. Unless otherwise specified herein, of the "monocycle" and the "fused ring," the "monocycle" is preferred. Unless otherwise specified herein, of the "saturated ring" and the "unsaturated ring," the "unsaturated ring" is preferred. Unless otherwise specified herein, the "monocycle" is preferably a benzene ring. Unless otherwise specified herein, the "unsaturated ring" is preferably a benzene ring. When "one or more pairs of adjacent two or more rings" "combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring," unless otherwise specified in this specification, preferably, one or more pairs of adjacent two or more rings combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and at least one atom selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0123] When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents Described 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 "saturated ring" or "unsaturated 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 two or more rings bond to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent two or more rings bond to each other to form a substituted or unsubstituted fused ring" ("when bonded to form a ring").

[0124] Substituents in the case of "substituted or unsubstituted" In one embodiment of the present specification, the substituents in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituents" in the present specification) include, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ), -O-(R ９０４ ), -S-(R ９０５ ), -N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and an unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ ~R ９０７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. ９０１ When there are two or more R９０１ are the same or different from each other, R ９０２ When there are two or more R ９０２ are the same or different from each other, R ９０３ When there are two or more R ９０３ are the same or different from each other, R ９０４ When there are two or more R ９０４ are the same or different from each other, R ９０５ When there are two or more R ９０５ are the same or different from each other, R ９０６ When there are two or more R ９０６ are the same or different from each other, R ９０７ When there are two or more R ９０７ are the same or different from each other.

[0125] In one embodiment, the substituent in the "substituted or unsubstituted" is a group selected from the group consisting of an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and a heterocyclic group having 5 to 50 ring atoms.

[0126] In one embodiment, the substituent in the "substituted or unsubstituted" is a group selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heterocyclic group having 5 to 18 ring atoms.

[0127] 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."

[0128] Unless otherwise specified in this specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring. Unless otherwise specified in this specification, the optional substituent may further have a substituent. The substituent further possessed by the optional substituent is the same as the optional substituent described above. When a plurality of optional substituents is present, the multiple optional substituents may be the same or different from each other.

[0129] 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.

[0130] First Embodiment The structure of an organic EL element according to a first embodiment of the present invention will be described. The organic EL element includes an organic layer between an anode and a cathode. The organic layer includes at least one layer made of an organic compound. Alternatively, the organic layer is formed by stacking multiple layers made of organic compounds. The organic layer may further include an inorganic compound. In the organic EL element of this embodiment, at least one of the organic layers is an emitting layer. Therefore, the organic layer may be, for example, a single emitting layer, or may include layers that can be used in an organic EL element. Layers that can be used in an organic EL element are not particularly limited, but include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a blocking layer. The organic EL element of this embodiment has an emitting layer between the anode and the cathode.

[0131] 1 shows a schematic configuration of an example of an organic EL element according to this 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 formed by laminating, in this order from the anode 3 side, a hole injection layer 6, a hole transport layer 7, a light-emitting layer 5, an electron transport layer 8, and an electron injection layer 9.

[0132] The light-emitting layer 5 may contain a metal complex. It is preferable that the light-emitting layer 5 does not contain a phosphorescent material (dopant material). It is preferable that the light-emitting layer 5 does not contain a heavy metal complex or a phosphorescent rare earth metal complex. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes. It is also preferable that the light-emitting layer 5 does not contain a metal complex. In the organic EL device 1 of this embodiment, the light-emitting layer 5 contains a delayed fluorescent compound M2 and a compound M3 represented by general formula (1). In this embodiment, the compound M2 is preferably a dopant material (sometimes referred to as a guest material, emitter, or light-emitting material), and the compound M3 is preferably a host material (sometimes referred to as a matrix material). The compound M3 may be a delayed fluorescent compound or a compound that does not exhibit delayed fluorescence.

[0133] Patent Document 2 discloses a compound in which benzofuranocarbazole or benzothienocarbazole is bonded to dibenzofuran or dibenzothiophene via a biphenylene having a long conjugation length (hereinafter, sometimes referred to as the compound of Patent Document 2), and an organic EL device in which the compound is incorporated into the light-emitting layer together with a delayed fluorescent compound. However, the compound of Patent Document 2 has a low triplet energy and is unable to sufficiently trap the triplet energy of the delayed fluorescent compound, resulting in an insufficient improvement in the device efficiency. The present inventors have discovered that a high-performance organic EL device can be realized by incorporating compound M3 (compound M3 of the present embodiment) represented by the general formula (1) together with delayed fluorescent compound M2 into the light-emitting layer. Compound M3 of the present embodiment is a compound in which benzofuranocarbazole or benzothienocarbazole, which supplies an appropriate amount of holes to the light-emitting layer, is bonded to highly durable dibenzofuran or dibenzothiophene via a phenylene having a short conjugation length or by a single bond. The compound M3 according to this embodiment exhibits high triplet energy, and therefore can sufficiently confine the triplet energy of the delayed fluorescent compound. Therefore, the organic EL device according to this embodiment can realize a high-performance organic EL device, particularly an organic EL device that emits light with high efficiency.

[0134] The structure of the organic EL element of this embodiment will be described in detail below. Hereinafter, the reference numerals will be omitted.

[0135] <Light-emitting layer> (Compound M3) The light-emitting layer in this embodiment contains a compound M3 represented by the following general formula (1): Compound M3 in this embodiment 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.

[0136]

[0137] (In the general formula (1), A is a group represented by any one of the following general formulas (11A), (11B), (11C), (11D), (11E), and (11F), and Y １is an oxygen atom or a sulfur atom, n is 0 or 1, R ２１ ~R ２８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １００ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ２１ ~R ２８ are each independently a hydrogen atom, a halogen atom, a cyano group, 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 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms, a hydroxy group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, -N(Rz) ２ a thiol group, a substituted or unsubstituted alkylthio group having 1 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms, a substituted germanium group, a substituted phosphine oxide group, a nitro group, a substituted boryl group, or a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, Rz is 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, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, -N(Rz) ２ In the formula, two Rz are the same or different, and a plurality of R １００are the same or different from each other, provided that n is 0 and X in the following general formulae (11A), (11B), (11C), (11D), (11E) and (11F) １ is an oxygen atom, R ２５ is not a substituted or unsubstituted dibenzofuranyl group. ２１ ~R ２４ represents the bonding position to any one of the carbon atoms of the six-membered ring to which

[0138]

[0139] In one embodiment of the general formulae (11A), (11B), (11C), (11D), (11E) and (11F), X １ is an oxygen atom or a sulfur atom, R １１ ~R ２０ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring １１ ~R ２０ each independently represents R that does not form the substituted or unsubstituted monocyclic ring in the general formula (1) and does not form the substituted or unsubstituted fused ring. ２１ ~R ２８ where n is 0, * is the same as R ２１ ~R ２４ represents the bonding position of any one of the carbon atoms of the six-membered ring to which n is bonded, and when n is 1, * represents R １００ represents the bonding position of any one of the carbon atoms of the benzene ring to which

[0140] In one embodiment of the general formulae (11A), (11B), (11C), (11D), (11E) and (11F), X １ is an oxygen atom or a sulfur atom, R １１ ~R １４one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １５ ~R １８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １９ and R ２０ is a hydrogen atom, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring １１ ~R １８ each independently represents R that does not form the substituted or unsubstituted monocyclic ring in the general formula (1) and does not form the substituted or unsubstituted fused ring. ２１ ~R ２８ where n is 0, * is the same as R ２１ ~R ２４ represents the bonding position of any one of the carbon atoms of the six-membered ring to which n is bonded, and when n is 1, * represents R １００ represents the bonding position of any one of the carbon atoms of the benzene ring to which

[0141] One embodiment of the general formulae (11A), (11B), (11C), (11D), (11E), and (11F) is represented by the following general formulae (111A), (111B), (111C), (111D), (111E), and (111F), respectively.

[0142]

[0143] (In the general formulae (111A), (111B), (111C), (111D), (111E) and (111F), X １ represents X in the general formula (11A). １ is synonymous with R １１ ~R １８ each independently represents R that does not form the substituted or unsubstituted monocyclic ring in the general formula (1) and does not form the substituted or unsubstituted fused ring. ２１ ~R２８ and * indicates the bonding position.)

[0144] Compound M3 represented by general formula (1) can also be represented by the following general formula (1-1), (1-2), (1-3), or (1-4). The compound of this embodiment (compound M3 represented by general formula (1)) is a compound represented by the following general formula (1-1), (1-2), (1-3), or (1-4).

[0145]

[0146] (In the general formulae (1-1), (1-2), (1-3) and (1-4), A, R １００ , n, Y １ and R ２１ ~R ２８ each independently represents A and R in the general formula (1). １００ , n, Y １ and R ２１ ~R ２８ and plural R １００ are the same or different. When n is 0, * in the general formulae (11A), (11B), (11C), (11D), (11E) and (11F) represents the bonding position with *1. When n is 1, * in the general formulae (11A), (11B), (11C), (11D), (11E) and (11F) represents the bonding position with R １００ represents the bonding position of any one of the carbon atoms of the benzene ring to which

[0147] In one embodiment, n is 1 in compound M3.

[0148] In one embodiment, compound M3 is a compound represented by the following general formula (12A). When a compound represented by the following general formula (12A) (compound M3) is used in combination with a compound represented by the below-described general formula (2A) (compound M1), the external quantum efficiency can be improved compared to when a compound represented by the below-described general formula (12C) (compound M3) is used in combination with a compound represented by the below-described general formula (2A) (compound M1). Among them, compound M3 is a compound represented by the following general formula (12A) in which X in A is １By selecting a compound in which is a sulfur atom, the external quantum efficiency and the lifetime can be further improved.

[0149] (In the general formula (12A), A, R １００ , Y １ and R ２１ ~R ２８ each independently represents A and R in the general formula (1). １００ , Y １ and R ２１ ~R ２８ and plural R １００ are the same or different from each other, provided that * is R ２１ ~R ２４ represents the bonding position to any one of the carbon atoms of the six-membered ring to which

[0150] In one embodiment, compound M3 is a compound represented by the following general formula (12B):

[0151]

[0152] (In the general formula (12B), A, R １００ , Y １ and R ２１ ~R ２８ each independently represents A and R in the general formula (1). １００ , Y １ and R ２１ ~R ２８ and plural R １００ are the same or different from each other, provided that * is R ２１ ~R ２４ represents the bonding position to any one of the carbon atoms of the six-membered ring to which

[0153] In one embodiment, compound M3 is a compound represented by the following general formula (12C):

[0154]

[0155] (In the general formula (12C), A, R １００ , Y １ and R ２１ ~R ２８ each independently represents A and R in the general formula (1).１００ , Y １ and R ２１ ~R ２８ and plural R １００ are the same or different from each other, provided that * is R ２１ ~R ２４ represents the bonding position to any one of the carbon atoms of the six-membered ring to which

[0156] In one embodiment, compound M3, n is 0, or n is 1 and R １００ is a hydrogen atom.

[0157] In one embodiment, n is 0 in compound M3.

[0158] In compound M3 according to one embodiment, A is a group represented by formula (11A), (11B), (11C), (11E), or (11F).

[0159] In compound M3 according to one embodiment, A is a group represented by general formula (11E) or (11F).

[0160] In compound M3 according to one embodiment, A is a group represented by general formula (11F).

[0161] In one embodiment of compound M3, X １ In one embodiment of the compound M3, X １ is a sulfur atom. In one embodiment of compound M3, Y １ In one embodiment of the compound M3, X １ and Y １ is an oxygen atom.

[0162] In one embodiment of compound M3, when n is 0, R ２５ is not a substituted or unsubstituted dibenzofuranyl group, nor is it a substituted or unsubstituted dibenzothienyl group.

[0163] In one embodiment of compound M3, when n is 0, R ２１ ~R ２８is not a substituted or unsubstituted dibenzofuranyl group, nor is it a substituted or unsubstituted dibenzothienyl group.

[0164] In the compound M3 according to one embodiment, when n is 0, R ２２ The carbon atom of the six-membered ring to which is bonded is not bonded to *.

[0165] In the compound M3 according to one embodiment, in the general formulae (11A), (11B), (11C), (11D), (11E), and (11F), R １９ and R ２０ is a hydrogen atom.

[0166] In the compound M3 according to one embodiment, in the general formulae (11A), (11B), (11C), (11D), (11E), and (11F), R １１ ~R ２０ is a hydrogen atom.

[0167] In one embodiment, the compound M3 is a compound represented by the following general formula (12A-1).

[0168]

[0169] (In the general formula (12A-1), A １２ is a group represented by any one of the following general formulas (11A-1), (11B-1), (11C-1), (11D-1), (11E-1) and (11F-1), and R １００ , Y １ and R ２１ ~R ２８ are each independently R in the general formula (1). １００ , Y １ and R ２１ ~R ２８ and plural R １００ are the same or different from each other, provided that * is R ２１ ~R ２４ represents the bonding position to any one of the carbon atoms of the six-membered ring to which

[0170]

[0171] (In the general formulae (11A-1), (11B-1), (11C-1), (11D-1), (11E-1) and (11F-1), R １１ ~R １８ are each independently R in the general formula (1). １１ ~R １８ and * indicates the bonding position.)

[0172] In the compound M3 according to one embodiment, in the general formulae (11A-1), (11B-1), (11C-1), (11D-1), (11E-1) and (11F-1), R １１ ~R １８ is a hydrogen atom.

[0173] In the light-emitting layer according to one embodiment, the singlet energy S １ (M2) Singlet energy S １ The only compound having this is compound M3.

[0174] In one embodiment of compound M3, when n is 1, R １００ is not a substituted or unsubstituted dibenzofuranyl group.

[0175] In one embodiment, the compound M3 is a compound represented by the following general formula (100).

[0176]

[0177] (In the general formula (100), X １ is an oxygen atom or a sulfur atom, R １００ , R １１ ~R ２０ , and R ２２ ~R ２８ are each independently a hydrogen atom, -(L １０１ ) nx-R １０１ nx is 0, 1, 2 or 3; -(L １０１ ) nx-R １０１ When a plurality of groups represented by -(L １０１ ) nx-R １０１ The groups represented by R are the same or different from each other, １００are the same or different from each other, R １０１ is an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted phenyl group, an unsubstituted (9-phenyl)carbazolyl group, an unsubstituted 9-carbazolyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothienyl group, an unsubstituted (9-dibenzofuranyl)carbazolyl group, an unsubstituted (9-dibenzothienyl)carbazolyl group, a monovalent group derived from a compound represented by the following general formula (101), a monovalent group derived from a compound represented by the following general formula (102), a monovalent group derived from a compound represented by the following general formula (103), a monovalent group derived from a compound represented by the following general formula (104), a monovalent group derived from a compound represented by the following general formula (105), or a monovalent group derived from a compound represented by the following general formula (106), １０１ is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted phenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothienylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted (9-dibenzofuranyl)carbazolylene group, a substituted or unsubstituted (9-dibenzothienyl)carbazolylene group, a divalent group derived from a compound represented by the following general formula (101), a divalent group derived from a compound represented by the following general formula (102), a divalent group derived from a compound represented by the following general formula (103), a divalent group derived from a compound represented by the following general formula (104), a divalent group derived from a compound represented by the following general formula (105), or a divalent group derived from a compound represented by the following general formula (106), １０１is a substituted alkylene group having 1 to 30 carbon atoms, a substituted phenylene group, a substituted dibenzofuranylene group, a substituted dibenzothienylene group, a substituted carbazolylene group, a substituted (9-dibenzofuranyl)carbazolylene group, or a substituted (9-dibenzothienyl)carbazolylene group, the substituents are each independently an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted phenyl group, an unsubstituted (9-phenyl)carbazolyl group, an unsubstituted 9-carbazolyl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothienyl group; １０１ When there are two or more, there are two or more L １０１ are the same or different from each other, R １０１ When two or more R １０１ are the same or different from each other, provided that * is R １００ represents the bonding position of any one of the carbon atoms of the benzene ring to which

[0178]

[0179] (In the general formulae (101) to (106), X １Ｘ is an oxygen atom or a sulfur atom, R １１Ｘ ~R ２１Ｘ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted phenyl group, an unsubstituted (9-phenyl)carbazolyl group, an unsubstituted 9-carbazolyl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothienyl group, with the proviso that R １０１ is a monovalent group derived from a compound of any one of the general formulas (101) to (106), and when nx is 0, R １１Ｘ ~R ２０Ｘ and the carbon atom of the six-membered ring to which R ２１Ｘ is bonded to a nitrogen atom, １１ ~R ２０ , R ２２ ~R ２８ and R １００ is bonded to any one of the carbon atoms of the six-membered ring to which nx is bonded, and when nx is 1, 2, or 3, R １１Ｘ ~R２０Ｘ and the carbon atom of the six-membered ring to which R ２１Ｘ Any one of the nitrogen atoms to which is bonded is L １０１ Combines with. １０１ is a divalent group derived from a compound of any one of the general formulae (101) to (106), and when nx is 1, R １１Ｘ ~R ２０Ｘ and the carbon atom of the six-membered ring to which R ２１Ｘ Of any two nitrogen atoms to which is bonded, one is R １０１ and the other is R １１ ~R ２０ , R ２２ ~R ２８ and R １００ is bonded to any one of the carbon atoms of the six-membered ring to which L １０１ is a divalent group derived from a compound of any one of the general formulae (101) to (106), and when nx is 2 or 3, R １１Ｘ ~R ２０Ｘ and the carbon atom of the six-membered ring to which R ２１Ｘ Of any two nitrogen atoms to which is bonded, one is R １０１ or L １０１ and the other is R １１ ~R ２０ , R ２２ ~R ２８ and R １００ any one of the carbon atoms of the six-membered ring to which L is bonded １０１ Combine with

[0180] In the compound M3 according to one embodiment, in the general formula (100), R １９ and R ２０ is a hydrogen atom.

[0181] - Method for producing compound M3 of this embodiment Compound M3 of this embodiment can be produced, for example, by the method described in the Examples below. Compound M3 of this embodiment can be produced by following the reactions described in the Examples below and using known alternative reactions and raw materials suited to the target product.

[0182] Specific examples of compound M3 of this embodiment include the following compounds: However, the present invention is not limited to these specific examples of compounds.

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194] (Compound M2) The light-emitting layer of this embodiment contains a delayed fluorescent compound M2.

[0195] Delayed fluorescence is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Adachi Chihaya, published by Kodansha). In that document, 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 to the excited singlet state, which usually has a low transition probability, occurs with high efficiency, resulting in the expression of thermally activated delayed fluorescence (TADF). Furthermore, Figure 10.38 in this document explains the mechanism by which delayed fluorescence occurs. Compound M2 in this embodiment is preferably a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism.

[0196] In general, delayed fluorescence can be confirmed by transient PL (Photo Luminescence) measurement.

[0197] 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 measuring the decay behavior (transient characteristics) of PL emission after the irradiation is stopped. PL emission in 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 on the order of nanoseconds, which is very short. Therefore, emission from these singlet excitons decays quickly after irradiation with a pulsed laser. On the other hand, delayed fluorescence decays slowly because it is emission from singlet excitons generated via triplet excitons, which have a long lifetime. Thus, there is a large time difference between emission from singlet excitons generated during the initial PL excitation and emission from singlet excitons generated via triplet excitons. Therefore, the emission intensity derived from delayed fluorescence can be determined.

[0198] A schematic diagram of an exemplary apparatus for measuring transient PL is shown in Figure 2. An example of a method for measuring transient PL and analyzing the behavior of delayed fluorescence will be described below using Figure 2.

[0199] 2 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. 2.

[0200] The sample accommodated in the sample chamber 102 is obtained by forming a thin film on a quartz substrate, in which the doping material is doped at a concentration of 12 mass % relative to the matrix material.

[0201] A pulsed laser is irradiated from the pulsed laser unit 101 onto a thin film sample housed 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 a spectrometer 103, forming a two-dimensional image in a 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. Cutting out this two-dimensional image along a predetermined time axis yields an emission spectrum in which the vertical axis represents emission intensity and the horizontal axis represents wavelength. Furthermore, cutting out the two-dimensional image along the wavelength axis yields a decay curve (transient PL) in which the vertical axis represents the logarithm of emission intensity and the horizontal axis represents time.

[0202] For example, a thin film sample A was prepared as described above using the following reference compound H1 as the matrix material and the following reference compound D1 as the doping material, and transient PL measurement was carried out.

[0203]

[0204] 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 reference compound H2 as a matrix material and the above-mentioned reference compound D1 as a doping material.

[0205] FIG. 3 shows the decay curves obtained from the transient PL measured for thin film sample A and thin film sample B.

[0206]

[0207] As described above, transient PL measurement can be used to obtain an emission decay curve with the vertical axis representing emission intensity and the horizontal axis representing time. 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 reverse 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 large.

[0208] Specifically, luminescence from delayed fluorescent materials includes prompt luminescence and delay 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) having a wavelength that the delayed fluorescent material absorbs. Delay luminescence is luminescence that is not observed immediately after excitation by the pulsed light, but is observed later.

[0209] 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. 2.

[0210] In addition, in this specification, a sample prepared by the following method is used to measure the delayed fluorescence of compound M2. For example, compound M2 is 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 is frozen and degassed, and then sealed in a lidded cell under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the sample solution is measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene is also measured under the same conditions. Using the fluorescence area intensities of both spectra, the total fluorescence quantum yield is calculated according to equation (1) in Morris et al. J. Phys. Chem. 80 (1976) 969.

[0211] 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). 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. 2. In this embodiment, the amount of prompt luminescence (prompt luminescence) of the compound to be measured (compound M2) is calculated as X ＰThe amount of delayed light emission is set to X Ｄ When this is done, X Ｄ / X Ｐ The amount and ratio of prompt luminescence and delay luminescence of compounds other than compound M2 herein are measured in the same manner as the amount and ratio of prompt luminescence and delay luminescence of compound M2.

[0212] Method for Producing Compound M2 of the Present Embodiment Compound M2 of the present embodiment can be produced by a known method.

[0213] Specific examples of the compound M2 of this embodiment include the following compounds: However, the present invention is not limited to these specific examples of compounds.

[0214]

[0215]

[0216]

[0217] <Relationship between Compound M3 and Compound M2 in the Emitting Layer> In the organic EL device of this embodiment, the singlet energy S １ (M2) and the singlet energy S of compound M3 １ (M3) satisfies the relationship of the following formula (Formula 1): S １ (M3) > S １ (M2) (Math. 1)

[0218] The energy gap T of compound M3 at 77 K ７７Ｋ (M3) is the energy gap T of compound M2 at 77 [K] ７７Ｋ It is preferable that the relationship between the saturation voltage and the saturation voltage is larger than (M2). That is, it is preferable that the relationship of the following mathematical formula (Formula 11) is satisfied. T ７７Ｋ (M3) > T ７７Ｋ (M2) ...(Math. 11)

[0219] When the organic EL device of this embodiment is caused to emit light, it is preferable that the compound M3 does not mainly emit light in the light-emitting layer.

[0220] Relationship Between Triplet Energy and Energy Gap at 77 K: Here, the relationship between triplet energy and the energy gap at 77 K will be described. In this embodiment, the energy gap at 77 K differs from the triplet energy as typically defined. Triplet energy is measured as follows. First, a sample is prepared by dissolving a compound to be measured in an appropriate solvent and sealing the solution in a quartz glass tube. A phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) is measured for this sample at low temperature (77 K). A tangent 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 and the horizontal axis. Among the compounds according to this embodiment, the thermally activated delayed fluorescence compound is preferably a compound with a small ΔST. A small ΔST makes it easier for intersystem crossing and reverse intersystem crossing 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 state and the excited triplet state, and it is difficult to clearly distinguish which state the light emission is from, but the triplet energy value is considered to be basically dominant. Therefore, in this embodiment, although the measurement method is the same as that of the normal triplet energy T, in order to distinguish that it is different in the strict sense, 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 a 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 energy gap T at 77 [K], the amount of energy calculated from the following conversion formula (F1) is ７７Ｋ Conversion formula (F1): T ７７Ｋ [eV]=1239.85 / λ ｅｄｇｅ

[0221] 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 among 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 taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that maximum points with peak intensities of 15% or less of the maximum peak intensity of the spectrum are not included in the shortest wavelength maximum, and the tangent drawn at the point where the slope is closest to the shortest wavelength maximum is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Phosphorescence can be measured using an F-4500 spectrofluorophotometer manufactured by Hitachi High-Technologies Corporation. 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.

[0222] Singlet energy S １ Singlet energy S using solution １ The following method can be used as a measurement method (sometimes referred to as the 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 of this sample (vertical axis: absorption intensity, horizontal axis: wavelength) is measured at room temperature (300 K). A tangent line is drawn to the trailing edge on the long wavelength side of this absorption spectrum, and the wavelength value λedge [nm] at the intersection of this tangent line and the horizontal axis is substituted into the following conversion formula (F2) to calculate the singlet energy. Conversion formula (F2): S １ [eV]=1239.85 / λedge. The absorption spectrum measuring device may be, for example, a spectrophotometer manufactured by Hitachi (device name: U3310), but is not limited to this.

[0223] A tangent to the fall of the absorption spectrum on the long wavelength side is drawn as follows: When moving along the spectral curve from the longest maximum value on the longest wavelength side among the maximum values ​​of the absorption spectrum in the direction of 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 of the absorption spectrum on the long wavelength side. Note that maximum points with absorbance values ​​of 0.2 or less are not included in the maximum value on the longest wavelength side.

[0224] In this embodiment, the singlet energy S １ and the energy gap T at 77[K] ７７Ｋ The difference between １ -T ７７Ｋ ) is defined as ΔST.

[0225] In this embodiment, the singlet energy S of compound M2 １ (M2) and the energy gap T of compound M2 at 77 [K] ７７Ｋ The difference ΔST(M2) between ΔST(M2) and ΔST(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 any of the relationships of the following formulas (1A) to (1D). ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.3eV (several 1A) ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.2eV (Math 1B) ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.1eV (Math. 1C) ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.01eV (Math. 1D)

[0226] The thickness of the light-emitting layer in the organic EL element according to this embodiment is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and most preferably 10 nm to 50 nm. A thickness of 5 nm or more facilitates the formation of the light-emitting layer and the adjustment of chromaticity, while a thickness of 50 nm or less facilitates the suppression of an increase in driving voltage.

[0227] - Content of Compounds in Light-Emitting Layer The contents of Compound M2 and Compound M3 contained in the light-emitting layer are preferably within the following ranges, for example. The content of Compound M2 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 Compound M3 is preferably 20% by mass or more and 90% by mass or less, more preferably 40% by mass or more and 90% by mass or less, and even more preferably 40% by mass or more and 80% by mass or less. Note that this embodiment does not exclude the case where the light-emitting layer contains materials other than Compound M2 and Compound M3. The light-emitting layer may contain only one type of Compound M2, or may contain two or more types. The light-emitting layer may contain only one type of Compound M3, or may contain two or more types.

[0228] FIG. 4 shows an example of the relationship between the energy levels of compounds M3 and M2 in the light-emitting layer. In FIG. 4, S0 represents the ground state. S1(M2) represents the lowest excited singlet state of compound M2, and T1(M2) represents the lowest excited triplet state of compound M2. S1(M3) represents the lowest excited singlet state of compound M3, and T1(M3) represents the lowest excited triplet state of compound M3. As shown in FIG. 4, when a material with a small ΔST(M2) is used as compound M2, the lowest excited triplet state T1 of compound M2 can undergo reverse intersystem crossing to the lowest excited singlet state S1 by thermal energy. By utilizing this reverse intersystem crossing that occurs in compound M2, light emission from the lowest excited singlet state S1(M2) of compound M2 can be observed when the light-emitting layer does not contain a fluorescent dopant with a lowest excited singlet state S1 smaller than the lowest excited singlet state S1(M2) of compound M2. It is believed that the internal quantum efficiency can theoretically be increased to 100% by utilizing delayed fluorescence due to this TADF mechanism.

[0229] The organic EL element of this embodiment includes, in the light-emitting layer, a delayed fluorescent compound M2 and a compound M3 (compound M3 represented by the general formula (1)) having a singlet energy greater than that of the compound M2, thereby realizing a high-performance organic EL element. The organic EL element of this embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0230] The structure of the organic EL element will be further described.

[0231] (Substrate) The substrate is used as a support for the organic EL element. For example, glass, quartz, plastic, etc. can be used as the substrate. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate. Examples of materials for forming the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Inorganic vapor deposition films can also be used.

[0232] (Anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, etc. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metal materials (e.g., titanium nitride).

[0233] 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 mass % to 10 mass % 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 mass % to 5 mass % of tungsten oxide and 0.1 mass % to 1 mass % of zinc oxide relative to indium oxide. Alternatively, the films may be formed by vacuum deposition, coating, inkjet printing, spin coating, or the like.

[0234] 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 facilitates hole injection regardless of the work function of the anode, and therefore materials that can be used as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures thereof, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0235] Materials with low work functions, such as elements belonging to Group 1 or 2 of the periodic table, can also be used, including alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these. When forming an anode using alkali metals, alkaline earth metals, and alloys containing these, vacuum deposition or sputtering can be used. Furthermore, when using silver paste or the like, coating or inkjet printing can be used.

[0236] (Cathode) For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof 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), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.

[0237] 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.

[0238] 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 formed into films by a sputtering method, an inkjet method, a spin coating method, or the like.

[0239] (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.

[0240] Furthermore, examples of the substance with high hole injection properties include low-molecular-weight organic compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DNTPD). [N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and other aromatic amine compounds, such as dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).

[0241] Furthermore, as a substance with high hole injection properties, a polymer compound (oligomer, dendrimer, polymer, etc.) can also be used. Examples of such polymer compounds include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD). Furthermore, a polymer compound to which an acid has been added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) or polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[0242] (Hole Transport Layer) The hole transport layer is a layer containing a substance with high hole transport properties. For the hole transport layer, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: NPB), Examples of aromatic amine compounds that can be used include 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The substances mentioned here are mainly 10 －６ cm ２ The material has a hole mobility of 1 / (V·s) or more.

[0243] The hole transport layer may be formed using carbazole derivatives such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (PCzPA), or anthracene derivatives such as t-BuDNA, DNA, and DPAnth. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) may also be used.

[0244] However, other substances may be used as long as they have a higher hole-transporting property than an electron-transporting property. Note that the layer containing the substance having a high hole-transporting property may be not only a single layer, but also a stack of two or more layers containing the above-mentioned substances.

[0245] When two or more hole transport layers are arranged, it is preferable to arrange a material having a larger energy gap closer to the light emitting layer. An example of such a material is HT-2, which is used in the examples described below.

[0246] (Electron Transport Layer) The electron transport layer is a layer containing a substance with high electron transport properties. For the electron transport layer, 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds can be used. Specifically, low-molecular organic compounds such as Alq and tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq) can be used. ３ ), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq ２), BAlq, Znq, ZnPBO, ZnBTZ, and other metal complexes can be used. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(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: OXD-8), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-9 ... Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) can also be used. In this embodiment, benzimidazole compounds can be preferably used. The substances mentioned here are mainly 10 －６ cm ２ The electron-transport layer is a substance having an electron mobility of 1 / (V·s) or more. Note that any substance other than those mentioned above may be used as the electron-transport layer as long as it has a higher electron-transporting property than a hole-transporting property. The electron-transport layer may be formed as a single layer or as a stack of two or more layers made of the above-mentioned substances.

[0247] 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).

[0248] (Electron Injection Layer) The electron injection layer is a layer containing a substance with high electron injection properties. Examples of the electron injection layer include lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), and calcium fluoride (CaF ２For example, alkali metals, alkaline earth metals, or compounds thereof, such as lithium oxide (LiOx), 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.

[0249] 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 substances constituting the electron transport layer described above (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 (abbreviated as TTF) can also be used. (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 any known method such as a dry film formation method such as a vacuum deposition method, a sputtering method, a plasma method, or an ion plating method, or a wet film formation method such as a spin coating method, a dipping method, a flow coating method, or an inkjet method.

[0250] (Film Thickness) The film 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 film thickness is too thin, defects such as pinholes are likely to occur, whereas if the film thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, a range of several nm to 1 μm is usually preferred.

[0251] [Second Embodiment] The configuration of an organic EL element of a second embodiment will be described. In the description of the second embodiment, the same components as those of the first embodiment will be denoted by the same reference numerals or names, and the description thereof will be omitted or simplified. Furthermore, in the second embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the first embodiment can be used.

[0252] The organic EL element of the second embodiment differs from the organic EL element of the first embodiment in that the emitting layer further contains a fluorescent compound M1. Other points are the same as those of the first embodiment. That is, in the second embodiment, the emitting layer contains a compound M3 represented by the general formula (1), a delayed fluorescent compound M2, and a fluorescent compound M1. In this embodiment, compound M1 is preferably a dopant material, compound M2 is preferably a host material, and compound M3 is preferably a host material. One of compound M2 and compound M3 may be referred to as a first host material, and the other may be referred to as a second host material.

[0253] (Compound M1) The emitting layer of this embodiment contains a fluorescent compound M1. The compound M1 of this embodiment is not a phosphorescent metal complex. It is preferable that the compound M1 of this embodiment is not a heavy metal complex. It is also preferable that the compound M1 of this embodiment is not a metal complex. It is also preferable that the compound M1 of this embodiment is a compound that does not exhibit thermally activated delayed fluorescence.

[0254] The compound M1 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.

[0255] When the compound M1 is a fluorescent compound, the compound M1 preferably exhibits emission with a maximum peak wavelength of 400 nm or more and 700 nm or less. －６ 10 moles / liter or more －５ The peak wavelength of the fluorescence spectrum at which the emission intensity is maximum is measured for a toluene solution in which the compound is dissolved at a concentration of 1 / 4 mole / L or less. The measurement device used is a spectrofluorometer (F-7000, manufactured by Hitachi High-Tech Science Corporation).

[0256] Compound M1 preferably exhibits red or green emission. In this specification, red emission refers to emission having a maximum peak wavelength in the fluorescence spectrum in the range of 600 nm to 660 nm. When compound M1 is a red fluorescent compound, the maximum peak wavelength of compound M1 is preferably 600 nm to 660 nm, more preferably 600 nm to 640 nm, and even more preferably 610 nm to 630 nm. In this specification, green emission refers to emission having a maximum peak wavelength in the fluorescence spectrum in the range of 500 nm to 560 nm. When compound M1 is a green fluorescent compound, the maximum peak wavelength of compound M1 is preferably 500 nm to 560 nm, more preferably 500 nm to 540 nm, and even more preferably 510 nm to 540 nm. In this specification, blue emission refers to emission having a maximum peak wavelength in the fluorescence spectrum in the range of 430 nm to 480 nm. When compound M1 is a blue fluorescent compound, the maximum peak wavelength of compound M1 is preferably 430 nm or more and 480 nm or less, more preferably 440 nm or more and 480 nm or less.

[0257] The maximum peak wavelength of light emitted from the organic EL element is measured as follows: ２ A voltage is applied to the organic EL element so that the spectral radiance spectrum obtained 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).

[0258] (Compound Represented by General Formula (2A)) In the present embodiment, compound M1 is preferably a compound represented by the following general formula (2A). Compound M1 is preferably a compound that emits light having a maximum peak wavelength of 500 nm or more and 560 nm or less. When a compound represented by the following general formula (2A) is used as compound M1, the lifetime can be significantly improved compared to when a compound having a pyrromethene skeleton is used as compound M1.

[0259]

[0260] (In the general formula (2A), ring Za, ring Zb, and ring Zc 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; Ra is bonded to ring Za or ring Zb to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring; Rb is bonded to ring Za or ring Zc to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring; Ra and Rb that do not form a substituted or unsubstituted heterocyclic ring each independently represent 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.

[0261] (Compound Represented by General Formula (D11)) In the present embodiment, it is also preferable that the compound M1 is a compound represented by the following general formula (D11). It is also preferable that the compound represented by the general formula (2A) is a compound represented by the following general formula (D11). When a compound represented by the following general formula (D11) is used as the compound M1, the external quantum efficiency can be improved compared to when a compound represented by the below-described general formula (16) is used as the compound M1. When a compound represented by the following general formula (D11) is used as the compound M1, the external quantum efficiency and lifetime can be improved compared to when a compound having a pyrromethene skeleton is used as the compound M1.

[0262]

[0263] (In the general formula (D11), Rb has the same meaning as Rb in the general formula (2A), and X １ is CR １ or a nitrogen atom, X ２ is CR２ or a nitrogen atom, X ３ is CR ３ or a nitrogen atom, X ４ is CR ４ or a nitrogen atom, X ５ is CR ５ or a nitrogen atom, X ６ is CR ６ or a nitrogen atom, X ７ is CR ７ or a nitrogen atom, or X ８ is a carbon atom bonded to X by a single bond; ８ is CR ８ or a nitrogen atom, or X ７ is a carbon atom bonded to X by a single bond; ９ is CR ９ or a nitrogen atom, X １０ is CR １０ or a nitrogen atom, X １１ is CR １１ or a nitrogen atom, X １２ is CR １２ or a nitrogen atom, Q is CR Ｑ or a nitrogen atom, R １ ~R ６ and R ９ ~R １１ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ３、 R ４ and Rb, one or more pairs of adjacent two or more of Rb are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ３、 R ４and Rb, and at least one hydrogen atom in a single ring or a condensed ring formed by bonding together one or more pairs of adjacent two or more Rb is selected from the group consisting of: an alkyl group having 1 to 50 carbon atoms; an aryl group having 6 to 50 ring carbon atoms; a heterocyclic group having 5 to 50 ring atoms; ９２０ ), and a group represented by —N(R ９２１ ) (R ９２２ at least one hydrogen atom in the substituent is substituted with an aryl group having 6 to 50 ring carbon atoms or an alkyl group having 1 to 50 carbon atoms, or is not substituted; R does not form a substituted or unsubstituted monocycle and does not form a substituted or unsubstituted fused ring; １ ~R １１ , and R １２ ~R １３ , and R Ｑ are each independently a hydrogen atom, 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 ９１１ ) (R ９１２ ) (R ９１３ a group represented by —O—(R ９１４ a group represented by —S—(R ９１５ a group represented by —N(R ９１６ ) (R ９１７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９１８ a group represented by -COOR ９１９a halogen atom, a cyano group, a 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, wherein Rb that does not form a substituted or unsubstituted monocycle and does not form a substituted or unsubstituted fused ring is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and R ９１１ ~R ９２２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９１１ If there are multiple R ９１１ are the same or different from each other, R ９１２ If there are multiple R ９１２ are the same or different from each other, R ９１３ If there are multiple R ９１３ are the same or different from each other, R ９１４ If there are multiple R ９１４ are the same or different from each other, R ９１５ If there are multiple R ９１５ are the same or different from each other, R ９１６ If there are multiple R ９１６ are the same or different from each other, R ９１７ If there are multiple R ９１７ are the same or different from each other, R ９１８ If there are multiple R ９１８ are the same or different from each other, R ９１９If there are multiple R ９１９ are the same or different from each other, R ９２０ If there are multiple R ９２０ are the same or different from each other, R ９２１ If there are multiple R ９２１ are the same or different from each other, R ９２２ If there are multiple R ９２２ are the same or different from each other.)

[0264] The compound represented by the general formula (D11) is also preferably represented by the following general formula (D13).

[0265]

[0266] (In the general formula (D13), R １ ~R ３ , R ５ ~R １３ and R Ｑ each independently represents R in general formula (D11). １ ~R ３ , R ５ ~R １３ and R Ｑ is synonymous with R Ａ１ ~R Ａ４ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring Ａ１ ~R Ａ４ are each independently a hydrogen atom, 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 aralkyl group having 7 to 50 carbon atoms, -Si(R ９３１ ) (R ９３２ ) (R ９３３ a group represented by —O—(R９３４ ), a group represented by —S—(R ９３５ a group represented by —N(R ９３６ ) (R ９３７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９３８ a group represented by -COOR ９３９ a halogen atom, a cyano group, a 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, ９３１ ~R ９３９ 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, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９３１ If there are multiple R ９３１ are 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 the same or different from each other, R ９３８ If there are multiple R ９３８ are the same or different from each other, R ９３９ If there are multiple R ９３９ are the same or different from each other.)

[0267] The compound represented by the general formula (D11) is also preferably represented by the following general formula (D13A).

[0268]

[0269] (In the general formula (D13A), R １ , R ３ , R ５ ~R １３ , R Ｑ and R Ａ１ ~R Ａ４ each independently represents R in general formula (D13). １ , R ３ , R ５ ~R １３ , R Ｑ and R Ａ１ ~R Ａ４ is synonymous with R Ａ５ ~R Ａ９ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring Ａ５ ~R Ａ９ each independently represents R in general formula (D13) that does not form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring. Ａ１ ~R Ａ４ is synonymous with

[0270] In the general formulae (D13) and (D13A), for example, R ５ and R ６ are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0271] In the compound represented by the general formula (D11), R １ ~R １３ and R Ｑare also preferably 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, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

[0272] In the compound represented by the general formula (D11), R １ ~R １３ and R Ｑ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms.

[0273] In the compounds represented by the general formulas (D13) and (D13A), R １ ~R ３ , R ５ ~R １３ , R Ｑ and R Ａ１ ~R Ａ９ are also preferably 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, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

[0274] In the compounds represented by the general formulas (D13) and (D13A), R １ ~R ３ , R ５ ~R １３ , R Ｑ and R Ａ１ ~R Ａ９ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms.

[0275] The compound represented by the general formula (D11) is also preferably represented by the following general formula (D14).

[0276]

[0277] (In the compound represented by the general formula (D14), R ２ , R ６、 R １３、 R Ｑ and R Ａ２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms.

[0278] In the general formula (D14), R １３ and R Ｑ are preferably each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted dibenzofuranyl group.

[0279] In the compound represented by the general formula (D14), R ６ and R Ａ２ are preferably each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0280] (Compound Represented by General Formula (16)) In the present embodiment, compound M1 is also preferably a compound represented by the following general formula (16). The compound represented by the general formula (2A) is also preferably a compound represented by the following general formula (16). When a compound represented by the following general formula (16) is used as compound M1, the lifetime can be improved compared to when a compound represented by the general formula (D11) is used as compound M1. When a compound represented by the following general formula (16) is used as compound M1, the lifetime can be significantly improved compared to when a compound having a pyrromethene skeleton is used as compound M1.

[0281]

[0282] (In the compound represented by the general formula (16), R １６１~R １７７ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring １６１ ~R １７７ are each independently a hydrogen atom, 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 aralkyl group having 7 to 50 carbon atoms, -Si(R ９６１ ) (R ９６２ ) (R ９６３ a group represented by —O—(R ９６４ ), a group represented by —S—(R ９６５ a group represented by —N(R ９６６ ) (R ９６７ a group represented by —C(═O)R ９６８ a group represented by -COOR ９６９ a halogen atom, a cyano group, a 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, ９６１ ~R ９６９ 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, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９６１ If there are multiple R ９６１ are the same or different from each other, R ９６２ If there are multiple R ９６２ are the same or different from each other, R ９６３ If there are multiple R ９６３ are the same or different from each other, R ９６４If there are multiple R ９６４ are the same or different from each other, R ９６５ If there are multiple R ９６５ are the same or different from each other, R ９６６ If there are multiple R ９６６ are the same or different from each other, R ９６７ If there are multiple R ９６７ are the same or different from each other, R ９６８ If there are multiple R ９６８ are the same or different from each other, R ９６９ If there are multiple R ９６９ are the same or different from each other.)

[0283] In the compound represented by the general formula (16), R １６１ ~R １７７ are preferably 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, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0284] In the compound represented by the general formula (16), R １６８ ~R １７０ At least one of the groups is 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.

[0285] In the compound represented by the general formula (16), R １６１ ~R １７７ are each preferably independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0286] In the compound represented by the general formula (16), R １６１ ~R １７７ is also preferably a hydrogen atom.

[0287] In the compound represented by the general formula (16), R １６１~R １７７ It is also preferred that at least one pair of adjacent two or more of the above groups be bonded to each other to form a ring represented by the following general formula (16A).

[0288]

[0289] (The dotted line in the general formula (16A) represents a bonding site, and R Ｘ１ ~R Ｘ４ are each independently a hydrogen atom, 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 aralkyl group having 7 to 50 carbon atoms, -Si(R ９６１ ) (R ９６２ ) (R ９６３ a group represented by —O—(R ９６４ a group represented by —S—(R ９６５ a group represented by —N(R ９６６ ) (R ９６７ a group represented by —C(═O)R ９６８ a group represented by -COOR ９６９ a halogen atom, a cyano group, a 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.

[0290] R Ｘ１ If there are multiple R Ｘ１ are the same or different from each other, R Ｘ２ If there are multiple R Ｘ２ are the same or different from each other, R Ｘ３ If there are multiple R Ｘ３ are the same or different from each other, R Ｘ４ If there are multiple R Ｘ４ are the same or different from each other.

[0291] In the general formula (16), R １６１and R １６２ A set consisting of R １６５ and R １６６ A set consisting of R １７２ and R １７３ and R １７６ and R １７７ It is also preferred that at least one of the groups consisting of:

[0292] In the general formula (16), R １６１ and R １６２ and R １７６ and R １７７ It is preferred that the pair consisting of the following does not simultaneously form a ring represented by the general formula (16A).

[0293] In the general formula (16), R １６５ and R １６６ are bonded to each other to form a ring represented by the general formula (16A), and R １７２ and R １７３ It is also preferable that a pair consisting of: be bonded to each other to form a ring represented by the general formula (16A), and in this case, the compound M1 is represented by the following general formula (161).

[0294] The compound represented by the general formula (16) is also preferably a compound represented by the following general formula (161).

[0295]

[0296] (In the general formula (161), R １６１ ~R １６４ , R １６７ ~R １７１ , R １７４ ~R １７７ and R Ｘ１ ~R Ｘ４ are each independently R in the general formula (16). １６１ ~R １６４ , R １６７ ~R １７１ , R １７４ ~R １７７ and R in the general formula (16A) Ｘ１ ~R Ｘ４is synonymous with

[0297] The compound represented by the general formula (16) is also preferably a compound represented by the following general formula (162).

[0298]

[0299] (In the general formula (162), R １６１ ~R １６３ , R １６８ ~R １７０ and R １７５ ~R １７７ are each independently R in the general formula (16). １６１ ~R １６３ , R １６８ ~R １７０ and R １７５ ~R １７７ is synonymous with

[0300] The compound represented by the general formula (16) is also preferably a compound represented by the following general formula (163).

[0301]

[0302] (In the general formula (163), R １６２ , R １６９ and R １７６ are each independently R in the general formula (16). １６２ , R １６９ and R １７６ is synonymous with

[0303] In the compound M1, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0304] Method for Producing Compound M1 Compound M1 can be produced by a known method.

[0305] Specific examples of compound M1 of this embodiment are shown below. However, the present invention is not limited to these specific examples of compounds. The coordinate bond between the boron atom and the nitrogen atom in the pyrromethene skeleton can be represented in various ways, such as by a solid line, a dashed line, an arrow, or by omission. In this specification, it is represented by a solid line, a dashed line, or is omitted.

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326] <Relationship between Compound M3, Compound M2, and Compound M1 in the Emitting Layer> In the organic EL device of this embodiment, the singlet energy S １ (M1) and the singlet energy S of the compound M2 １ It is preferable that (M2) satisfies the relationship of the following mathematical formula (Mathematical Formula 2): S １ (M2) > S １(M1) (Equation 2)

[0327] In addition, the singlet energy S of compound M3 １ (M3) is the singlet energy S of compound M1 １ It is preferable that it is larger than (M1).

[0328] The singlet energy S of compound M3 １ (M3) and the singlet energy S of compound M2 １ (M2) and the singlet energy S of compound M1 １ It is preferable that (M1) satisfies the relationship of the following mathematical formula (Mathematical Formula 2A): S １ (M3) > S １ (M2) > S １ (M1) ...(Math 2A)

[0329] When the organic EL device of this embodiment is caused to emit light, it is preferable that the fluorescent compound M1 mainly emits light in the light-emitting layer. The organic EL device of this embodiment preferably emits red or green light.

[0330] - Content of Compounds in the Light-Emitting Layer The contents of Compound M3, Compound M2, and Compound M1 contained in the light-emitting layer are preferably within the following ranges, for example. The content of Compound M3 is preferably 10% by mass or more and 80% by mass or less. The content of Compound M2 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 Compound M1 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 1% by mass or less. The upper limit of the total content of Compound M3, Compound M2, and Compound M1 in the light-emitting layer is 100% by mass. Note that this embodiment does not exclude the possibility that the light-emitting layer contains materials other than Compound M3, Compound M2, and Compound M1. The light-emitting layer may contain only one type of Compound M3, or may contain two or more types of Compound M3. The light-emitting layer may contain only one type of compound M2 or two or more types thereof. The light-emitting layer may contain only one type of compound M1 or two or more types thereof.

[0331] 5 is a diagram showing an example of the relationship between the energy levels of compounds M3, M2, and M1 in the light-emitting layer. In FIG. 5, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of compound M1, and T1(M1) represents the lowest excited triplet state of compound M1. S1(M2) represents the lowest excited singlet state of compound M2, and T1(M2) represents the lowest excited triplet state of compound M2. S1(M3) represents the lowest excited singlet state of compound M3, and T1(M3) represents the lowest excited triplet state of compound M3. The dashed arrow from S1(M2) to S1(M1) in FIG. 5 represents Förster energy transfer from the lowest excited singlet state of compound M2 to the lowest excited singlet state of compound M1. As shown in Figure 5, when a compound with a small ΔST (M2) is used as compound M2, 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 compound M2 to compound M1, generating the lowest excited singlet state S1 (M1). As a result, fluorescence emission from the lowest excited singlet state S1 (M1) of compound M1 can be observed. It is believed that the internal quantum efficiency can theoretically be increased to 100% by utilizing delayed fluorescence due to this TADF mechanism.

[0332] The organic EL element of the second embodiment includes, in an emitting layer, a delayed fluorescent compound M2, a compound M3 (compound M3 represented by general formula (1)) having a singlet energy greater than that of the delayed fluorescent compound M2, and a compound M1 having a singlet energy smaller than that of the delayed fluorescent compound M2. According to the second embodiment, a high-performance organic EL element is realized. The organic EL element of the second embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0333] Third Embodiment Electronic Device An electronic device according to this embodiment is equipped with the organic EL element according to any one of the above-described embodiments. Examples of the electronic device include a display device and a light-emitting device. Examples of the display device include display components (e.g., an organic EL panel module), a television, a mobile phone, a tablet, and a personal computer. Examples of the light-emitting device include lighting and vehicle lighting fixtures.

[0334] [Fourth Embodiment] [Compound] The compound according to the fourth embodiment is the compound represented by the general formula (100) described in the first embodiment. According to the compound of the fourth embodiment, a high-performance organic EL device can be realized.

[0335] [Organic EL element] An organic EL element according to one aspect of the fourth embodiment is an organic EL element containing the compound according to the fourth embodiment (the compound represented by the general formula (100)) in any of the organic layers disposed between an anode and a cathode. The compound according to the fourth embodiment is a compound that can realize a high-performance organic EL element. Therefore, the organic EL element according to one aspect of the fourth embodiment also has high performance.

[0336] [Fifth Embodiment] [Material for Organic EL Device] The material for an organic EL device of the fifth embodiment contains the compound of the fourth embodiment. According to the material for an organic EL device of the sixth embodiment, a high-performance organic EL device and electronic device can be realized. The material for an organic EL device of the sixth embodiment may further contain other compounds. When the material for an organic EL device of the sixth embodiment further contains other compounds, the other compounds may be solid or liquid.

[0337] [Modifications of the Embodiment] The present invention is not limited to the above-described embodiment, and any modifications, improvements, etc. that can achieve the object of the present invention are included in the present invention.

[0338] 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 by electron transition from a triplet excited state directly to the ground state. Furthermore, when the organic EL element has multiple 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 organic EL element in which multiple light-emitting units are stacked via an intermediate layer.

[0339] Furthermore, for example, a barrier layer may be provided adjacent to at least one of the anode side and the cathode side of the light-emitting layer. The barrier 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 barrier layer is disposed in contact with the cathode side of the light-emitting layer, the barrier layer transports electrons and blocks holes from reaching a layer (e.g., an electron transport layer) closer to the cathode than the barrier layer. When the organic EL device includes an electron transport layer, the barrier layer is preferably provided between the light-emitting layer and the electron transport layer. When a barrier layer is disposed in contact with the anode side of the light-emitting layer, the barrier layer transports holes and blocks electrons from reaching a layer (e.g., a hole transport layer) closer to the anode than the barrier layer. When the organic EL device includes a hole transport layer, the barrier layer is preferably provided between the light-emitting layer and the hole transport layer. Furthermore, the barrier layer may be provided adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to its surrounding layers. The blocking layer prevents excitons generated in the light-emitting layer from migrating to layers closer to the electrode than the blocking layer (for example, the electron transport layer and the hole transport layer).The light-emitting layer and the blocking layer are preferably in contact with each other.

[0340] 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.

[0341] 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.

[0342] <Compounds> The compound M3 and delayed fluorescent compound M2 used in the production of the organic EL devices of Examples 1 to 19 are shown below.

[0343]

[0344]

[0345]

[0346] The compounds used in the production of the organic EL device of Comparative Example 1 are shown below.

[0347]

[0348] The structures of other compounds used in the production of the organic EL devices of Examples 1 to 19 and Comparative Example 1 are shown below.

[0349]

[0350]

[0351]

[0352]

[0353] <Preparation of Organic EL Device 1> An organic EL device was prepared as follows and evaluated.

[0354] Example 1: A 25 mm x 75 mm x 1.1 mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 1 minute. The ITO film thickness was 130 nm. The cleaned glass substrate with transparent electrode lines was attached to a substrate holder in a vacuum deposition apparatus. First, compound HT1 and compound HA were co-deposited on the surface on which the transparent electrode lines were formed, covering the transparent electrode, to form a hole injection layer with a thickness of 10 nm. The concentration of compound HT1 in the hole injection layer was 97% by mass, and the concentration of compound HA was 3% by mass. Next, compound HT1 was vapor-deposited on the hole injection layer, forming a first hole transport layer with a thickness of 110 nm on the hole injection layer. Next, compound HT2 was vapor-deposited on this first hole transport layer to form a second hole transport layer with a thickness of 5 nm. Next, compound HT3 was vapor-deposited on this second hole transport layer to form a 5 nm thick electron blocking layer. Next, compound M3-1 as compound M3 and compound TADF-1 as delayed fluorescent compound M2 were co-deposited on this electron blocking layer to form a 25 nm thick light-emitting layer. The concentration of compound M3-1 in the light-emitting layer was 75 mass %, and the concentration of compound TADF-1 was 25 mass %. Next, compound HBL was vapor-deposited on this light-emitting layer to form a 5 nm thick hole blocking layer. Next, compound ET was vapor-deposited on this hole blocking layer to form a 50 nm thick electron transport layer. Next, lithium fluoride (LiF) was vapor-deposited on this electron transport layer to form a 1 nm thick electron injection electrode (cathode). Then, metal aluminum (Al) was vapor-deposited on this electron injection electrode to form a metal Al cathode with a thickness of 80 nm. The device configuration of the organic EL device according to Example 1 is shown in outline as follows: ITO(130) / HT1:HA(10,97%:3%) / HT1(110) / HT2(5) / HT3(5) / M3-1:TADF-1(25,75%:25%) / HBL(5) / ET(50) / LiF(1) / Al(80) The numbers in parentheses indicate the film thickness (unit: nm).Similarly, in parentheses, the percentages (97%:3%) indicate the proportions (mass%) of compound HT1 and compound HA in the hole injection layer, and the percentages (75%:25%) indicate the proportions (mass%) of compound M3 and compound M2 in the light-emitting layer.

[0355] <Evaluation 1 of Organic EL Device> Current density: 10 mA / cm ２ It was confirmed that when a voltage was applied to the organic EL element produced in Example 1, light was emitted.

[0356] <Preparation of Organic EL Device 2> An organic EL device was prepared as follows and evaluated.

[0357] Example 2: A 25 mm x 75 mm x 1.1 mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 1 minute. The ITO film thickness was 130 nm. The cleaned glass substrate with transparent electrode lines was attached to a substrate holder in a vacuum deposition apparatus. First, compound HT4 and compound HA were co-deposited on the surface on which the transparent electrode lines were formed, covering the transparent electrode, to form a hole injection layer with a thickness of 10 nm. The concentration of compound HT4 in the hole injection layer was 97% by mass, and the concentration of compound HA was 3% by mass. Next, compound HT4 was deposited on the hole injection layer, forming a first hole transport layer with a thickness of 110 nm on the hole injection layer. Next, compound HT2 was deposited on this first hole transport layer to form a second hole transport layer with a thickness of 5 nm. Next, on this second hole transport layer, compound HT3 was vapor-deposited to form an electron blocking layer with a thickness of 5 nm. Next, on this electron blocking layer, compound M3-1 as compound M3, compound TADF-2 as delayed fluorescent compound M2, and compound FD as compound M1 were co-deposited to form an emitting layer with a thickness of 25 nm. The concentration of compound M3-1 in the emitting layer was 79.2% by mass, the concentration of compound TADF-2 was 20% by mass, and the concentration of compound FD was 0.8% by mass. Next, compound HBL2 was vapor-deposited on this emitting layer to form a hole blocking layer with a thickness of 5 nm. Next, compound ET2 and compound Liq were vapor-deposited on this hole blocking layer to form an electron transport layer with a thickness of 50 nm. The concentration of compound ET2 in the electron transport layer was 50% by mass, and the concentration of compound Liq was 50% by mass. Next, Yb was vapor-deposited on the electron transport layer to form an electron injection electrode (cathode) with a thickness of 1 nm. Metallic aluminum (Al) was then vapor-deposited on the electron injection electrode to form a metallic Al cathode with a thickness of 80 nm. The device configuration of the organic EL device according to Example 2 is schematically shown as follows.ITO (130) / HT4:HA (10,97%:3%) / HT4 (110) / HT2 (5) / HT3 (5) / M3-1:TADF-2:FD (25,79.2%:20%:0.8%) / HBL2 (5) / ET2:Liq (50,50%:50%) / Yb (1) / Al (80) The numbers in parentheses indicate the film thickness (unit: nm). Also in parentheses, the percentage numbers (97%:3%) indicate the proportions (mass%) of compounds HT4 and HA in the hole injection layer, the percentage numbers (79.2%:20%:0.8%) indicate the proportions (mass%) of compounds M3, M2, and M1 in the emitting layer, and the percentage numbers (50%:50%) indicate the proportions (mass%) of compounds ET2 and Liq in the electron transport layer.

[0358] [Examples 3 to 7 and Comparative Example 1] The organic EL devices according to Examples 3 to 7 and Comparative Example 1 were fabricated in the same manner as in Example 2, except that the compound M3-1 used in Example 2 was changed to a compound shown in Table 1.

[0359] Examples 8 to 9 Organic EL devices according to Examples 8 to 9 were fabricated in the same manner as in Example 2, except that the compound M3-1 used in Example 2 was changed to a compound shown in Table 2.

[0360] [Examples 10 to 19] The organic EL devices according to Examples 10 to 19 were fabricated in the same manner as in Example 2, except that the compound M3-1 used in Example 2 was changed to a compound shown in Table 2, and the compound FD used in Example 2 was changed to a compound shown in Table 2.

[0361] <Evaluation of Organic EL Device 2> The prepared organic EL devices were evaluated as follows. The evaluation results are shown in Tables 1 and 2. The evaluation results of Comparative Example 1 are shown in both Tables 1 and 2. In Table 2, "-" indicates that no measurement was performed.

[0362] (Maximum peak wavelength λp) Current density 10 mA / cm ２ The spectral radiance spectrum when a voltage was applied to the element was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). From the obtained spectral radiance spectrum, the maximum peak wavelength λｐ (unit: nm) was determined.

[0363] (External quantum efficiency EQE) Current density 10 mA / cm ２ The spectral radiance spectrum when a voltage was applied to the element so that the spectral radiance was 1.0 V 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.

[0364] (Lifespan LT95) The fabricated organic EL element was subjected to a current density of 50 mA / cm ２ The time required for the luminance to reach 95% of the initial luminance (LT95 (unit: hr)) was measured as the lifetime. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.).

[0365]

[0366] The organic EL devices of Examples 2 to 7, which contained the compound M3 represented by general formula (1) and the delayed fluorescent compound M2 in the light-emitting layer, emitted light with higher efficiency than the organic EL device of Comparative Example 1, in which the compound M3 was replaced with the compound Ref-1.

[0367]

[0368] The organic EL devices of Examples 8 to 19, which contained a compound M3 represented by general formula (1), a delayed fluorescent compound M2, and a fluorescent compound M1 in the light-emitting layer, emitted light with higher efficiency than the organic EL device of Comparative Example 1. Furthermore, when comparing Examples 8 to 14 with Examples 15 to 19, the organic EL devices of Examples 8 to 14, which used a compound (FD or FD-2) represented by general formula (2A) as the fluorescent compound M1, had significantly longer lifetimes than the organic EL devices of Examples 15 to 19, which used a compound (FD-3) having a pyrromethene skeleton as the fluorescent compound M1. When comparing Examples 8 to 9 with Examples 10 to 11, the organic EL devices of Examples 8 to 9, which used a compound (FD) represented by general formula (16) as the fluorescent compound M1, had longer lifetimes than the organic EL devices of Examples 10 to 11, which used a compound (FD) represented by general formula (D11) as the fluorescent compound M1. On the other hand, Examples 10 to 11, which used compound (FD-2) represented by general formula (D11) as the fluorescent compound M1, emitted light with higher efficiency than Examples 8 to 9, which used compound (FD) represented by general formula (16) as the fluorescent compound M1. When Examples 10 to 14 are compared, Examples 10 to 11, which used compounds (M3-11, M3-12) represented by general formula (12A) as compound M3, emitted light with higher efficiency than Examples 12 to 14, which used compounds (M3-13, M3-2 and M3-15) represented by general formula (12C) as compound M3. Among Examples 10 to 14, compounds represented by general formula (12A) and in which X in A １ In Example 11, which used a compound (M3-12) in which is a sulfur atom, the external quantum efficiency and the lifetime were more significantly improved.

[0369] <Evaluation of Compounds> The physical properties of the compounds were measured by the following methods. The measurement results are shown in Tables 1 to 3.

[0370] Thermally activated delayed fluorescence (delayed fluorescence of compound TADF-1) Delayed fluorescence was confirmed by measuring transient PL using the apparatus shown in Figure 2. Compound TADF-1 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 obtain an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the sample solution was measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation). The fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. The fluorescence area intensities of both spectra were used to calculate the total fluorescence quantum yield 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 TADF-1, there are two types of luminescence: prompt luminescence (immediate luminescence) that is observed immediately from the excited state, and delay luminescence (delayed luminescence) that is not observed immediately after the excitation but is observed later. In this example, delayed fluorescence luminescence means that the amount of delay luminescence (delayed luminescence) is 5% or more of the amount of prompt luminescence (immediate luminescence). Specifically, the amount of prompt luminescence (immediate luminescence) is X Ｐ The amount of delayed light emission is set to X Ｄ When this is done, X Ｄ / X Ｐ This means that the value of X 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). 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 Figure 2. It was confirmed that the amount of delay luminescence (delayed luminescence) was 5% or more of the amount of prompt luminescence (immediate luminescence) for compound TADF-1. Specifically, for compound TADF-1, X Ｄ / X Ｐ The value was 0.05 or more.

[0371] Delayed fluorescence of compound TADF-2 The delayed fluorescence of compound TADF-2 was confirmed in the same manner as above, except that compound TADF-2 was used instead of compound TADF-1. Ｄ / X Ｐ The value of was 0.05 or more.

[0372] Singlet energy S １ The singlet energy S of compounds M3-1, M3-6 to M3-15, compounds TADF-1 to TADF-2, compounds FD, FD-2, FD-3, and compound Ref-1 １ was measured by the solution method described above.

[0373] Energy gap T at 77 [K] ７７Ｋ T of compounds M3-1, M3-6 to M3-15, compounds TADF-1 to TADF-2, and compound Ref-1 ７７Ｋ is calculated by the energy gap T ７７Ｋ It was measured by the measurement method of T ７７Ｋ The measurement results and the above singlet energy S １ ΔST was confirmed from the value of

[0374] Maximum Peak Wavelength λ of Compounds The maximum peak wavelength λ of compounds TADF-1, FD, FD-2, and FD-3 was measured by the following method. A 5 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample was measured at room temperature (300 K). In this example, the emission spectrum was measured using a spectrophotometer (device name: F-7000) manufactured by Hitachi. Note that the emission spectrum measurement device is not limited to the device used here. The peak wavelength of the emission spectrum at which the emission intensity is maximum was defined as the maximum peak wavelength λ.

[0375]

[0376] <Synthesis of Compounds> Compounds M3-1 to M3-10, which are compound M3, were synthesized.

[0377] [Synthesis Example 1: Synthesis of Compound M3-1] (1-1) Synthesis of Compound M3-1

[0378]

[0379] Under a nitrogen atmosphere, xylene (200 mL) was added to a mixture of 12H-benzofuro[2,3-a]carbazole (10.3 g, 40.0 mmol), 2-(4-bromophenyl)dibenzo[b,d]furan (12.9 g, 40.0 mmol), tris(dibenzylideneacetone)dipalladium (0.549 g, 0.600 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.696 g, 2.40 mmol), and sodium tert-butoxide (11.5 g, 120 mmol), and the mixture was stirred at 140° C. for 5 hours. After completion of the reaction, water was added, and the solid was collected by filtration and recrystallized using toluene to obtain compound M3-1 (9.37 g, yield 46%). The compound was identified as compound M3-1 by LC-MS (Liquid Chromatography-Mass Spectrometry) analysis.

[0380] [Synthesis Example 2: Synthesis of Compound M3-2] (2-1) Synthesis of Compound M3-2

[0381]

[0382] Compound M3-2 was obtained in the same manner as in Synthesis Example 1 (1-1), except that 2-(3-bromophenyl)dibenzo[b,d]furan was used instead of 2-(4-bromophenyl)dibenzo[b,d]furan in Synthesis Example 1 (1-1). The yield was 71%. LC-MS analysis identified the compound as M3-2.

[0383] [Synthesis Example 3: Synthesis of Compound M3-3] (3-1) Synthesis of Compound M3-3

[0384]

[0385] Compound M3-3 was obtained in the same manner as in Synthesis Example 1 (1-1), except that 1-(4-chlorophenyl)dibenzo[b,d]furan was used instead of 2-(4-bromophenyl)dibenzo[b,d]furan in Synthesis Example 1 (1-1). The yield was 57%. LC-MS analysis identified the compound as M3-3.

[0386] Synthesis Example 4: Synthesis of Compound M3-4 (4-1) Synthesis of 1-(3-chlorophenyl)dibenzo[b,d]furan

[0387]

[0388] Under a nitrogen atmosphere, 1,2-dimethoxyethane (267 mL) and water (133 mL) were added to a mixture of 1-bromo-3-chlorobenzene (7.66 g, 40.0 mmol), 2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (11.8 g, 40.0 mmol), tetrakis(triphenylphosphine)palladium (2.3 g, 2.00 mmol), and sodium carbonate (12.7 g, 120 mmol), and the mixture was stirred at 80° C. for 3 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, the solvent was evaporated, and the mixture was purified by silica gel column chromatography to obtain 1-(3-chlorophenyl)dibenzo[b,d]furan (10.8 g, yield 95%).

[0389] (4-2) Synthesis of Compound M3-4

[0390]

[0391] Compound M3-4 was obtained in the same manner as in Synthesis Example 1 (1-1), except that 1-(3-chlorophenyl)dibenzo[b,d]furan was used instead of 2-(4-bromophenyl)dibenzo[b,d]furan in Synthesis Example 1 (1-1). The yield was 57%. LC-MS analysis identified the compound as M3-4.

[0392] [Synthesis Example 5: Synthesis of Compound M3-5] (5-1) Synthesis of Compound M3-5

[0393]

[0394] Compound M3-5 was obtained in the same manner as in Synthesis Example 1 (1-1), except that 2-bromodibenzo[b,d]furan was used instead of 2-(4-bromophenyl)dibenzo[b,d]furan in Synthesis Example 1 (1-1). The yield was 61%. LC-MS analysis identified the compound as M3-5.

[0395] [Synthesis Example 6: Synthesis of Compound M3-6] (6-1) Synthesis of Compound M3-6

[0396]

[0397] Toluene (30 mL) was added to a mixture of 12H-benzofuro[2,3-a]carbazole (1.70 g, 6.61 mmol), 4-(4-bromophenyl)dibenzo[b,d]furan (1.94 g, 6.01 mmol), dibenzylideneacetonepalladium (0.104 g, 0.18 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.172 g, 0.36 mmol), and sodium tert-butoxide (0.866 g, 9.02 mmol) under a nitrogen atmosphere, and the mixture was stirred at 110°C for 2 hours. After completion of the reaction, the solid was collected by filtration, washed with methanol, and recrystallized using toluene to obtain Compound M3-6 (2.43 g, 81% yield). LC-MS analysis identified the product as Compound M3-6.

[0398] [Synthesis Example 7: Synthesis of Compound M3-7] (7-1) Synthesis of Compound M3-7

[0399]

[0400] Compound M3-7 was obtained in the same manner as in Synthesis Example 6 (6-1), except that 4-(3-bromophenyl)dibenzo[b,d]furan was used instead of 4-(4-bromophenyl)dibenzo[b,d]furan in Synthesis Example 6 (6-1). The yield was 80%. LC-MS analysis identified the compound as M3-7.

[0401] [Synthesis Example 8: Synthesis of Compound M3-8] (8-1) Synthesis of Compound M3-8

[0402]

[0403] Compound M3-8 was obtained in the same manner as in Synthesis Example 6 (6-1), except that 2-(4-bromophenyl)dibenzo[b,d]thiophene was used instead of 4-(4-bromophenyl)dibenzo[b,d]furan in Synthesis Example 6 (6-1). The yield was 61%. LC-MS analysis identified the compound as M3-8.

[0404] [Synthesis Example 9: Synthesis of Compound M3-9] (9-1) Synthesis of Compound M3-9

[0405]

[0406] Compound M3-9 was obtained in the same manner as in Synthesis Example 6 (6-1), except that in Synthesis Example 6 (6-1), 5H-benzofuro[3,2-c]carbazole was used instead of 12H-benzofuro[2,3-a]carbazole and 2-(4-bromophenyl)dibenzo[b,d]furan was used instead of 4-(4-bromophenyl)dibenzo[b,d]furan. The yield was 67%. LC-MS analysis identified the compound as M3-9.

[0407] [Synthesis Example 10: Synthesis of Compound M3-10] (10-1) Synthesis of Compound M3-10

[0408]

[0409] Toluene (35 mL) was added to a mixture of 7H-benzofuro[2,3-b]carbazole (1.98 g, 7.71 mmol), 2-(4-bromophenyl)dibenzo[b,d]furan (2.26 g, 7.01 mmol), dibenzylideneacetonepalladium (0.08 g, 0.14 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.13 g, 0.36 mmol), and sodium tert-butoxide (1.01 g, 10.5 mmol) under a nitrogen atmosphere, and the mixture was stirred at 110°C for 3.5 hours. After completion of the reaction, the solid was collected by filtration, washed with methanol, and recrystallized using toluene to obtain Compound M3-10 (1.44 g, yield 41%). The product was identified as Compound M3-10 by LC-MS analysis.

[0410] [Synthesis Example 11: Synthesis of Compound M3-11] (11-1) Synthesis of Compound M3-11

[0411]

[0412] Compound M3-11 was obtained in the same manner as in Synthesis Example 10 (10-1), except that in Synthesis Example 10 (10-1), 12H-benzofuro[2,3-a]carbazole was used instead of 7H-benzofuro[2,3-b]carbazole and 2-(4-bromophenyl)-4-phenyldibenzo[b,d]furan was used instead of 2-(4-bromophenyl)dibenzo[b,d]furan. The yield was 46%. The compound was identified as Compound M3-11 by LC-MS analysis.

[0413] [Synthesis Example 12: Synthesis of Compound M3-12] (12-1) Synthesis of Compound M3-12

[0414]

[0415] Compound M3-12 was obtained in the same manner as in Synthesis Example 10 (10-1), except that 12H-benzo[4,5]thieno[2,3-a]carbazole was used instead of 7H-benzofuro[2,3-b]carbazole in Synthesis Example 10 (10-1). The yield was 53%. LC-MS analysis identified the compound as M3-12.

[0416] [Synthesis Example 13: Synthesis of Compound M3-13] (13-1) Synthesis of Compound M3-13

[0417]

[0418] Compound M3-13 was obtained in the same manner as in Synthesis Example 10 (10-1), except that in Synthesis Example 10 (10-1), 5H-benzofuro[3,2-c]carbazole was used instead of 7H-benzofuro[2,3-b]carbazole and 2-(3-bromophenyl)dibenzo[b,d]furan was used instead of 2-(4-bromophenyl)dibenzo[b,d]furan. The yield was 53%. LC-MS analysis identified the compound as Compound M3-12.

[0419] [Synthesis Example 15: Synthesis of Compound M3-15] (13-1) Synthesis of Compound M3-15

[0420]

[0421] Under a nitrogen atmosphere, dimethoxyethane (30 mL) and water (6 mL) were added to a mixture of 12-(5-chloro-[1,1'-biphenyl]-3-yl)-12H-benzo[4,5]thieno[2,3-a]carbazole (2.34 g, 5.09 mmol), dibenzo[b,d]furan-2-ylboronic acid (1.08 g, 5.09 mmol), dibenzylideneacetonepalladium (0.09 g, 0.15 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.15 g, 0.31 mmol), and sodium carbonate (0.81 g, 7.6 mmol), and the mixture was stirred at 80°C for 7 hours. After completion of the reaction, the solid was collected by filtration, washed with methanol, and recrystallized using a mixed solvent of toluene and methanol to obtain compound M3-15 (1.37 g, yield 46%). LC-MS analysis identified the compound as M3-15.

[0422] 1... organic EL element, 2... substrate, 3... anode, 4... cathode, 5... light-emitting layer, 6... hole injection layer, 7... hole transport layer, 8... electron transport layer, 9... electron injection layer

Claims

1. An anode, a cathode, and a light-emitting layer contained between the anode and the cathode, and having: The light-emitting layer contains a compound M3 represented by the following general formula (12A) and a delayed fluorescence compound M2, The compound M3 and the compound M2 have different structures, The singlet energy S of the compound M3 １ (M3) and the singlet energy S of the compound M2 １ (M2) satisfy the relationship of the following mathematical formula (Formula 1): An organic electroluminescence element. S １ (M3) > S １ (M2) (Equation 1) 【Chemical 1】 A is a group represented by any one of the following general formulas (11B), (11D), and (11F), Y １ is an oxygen atom or a sulfur atom, R ２１ ~R ２８ Among them, one or more sets consisting of two or more adjacent ones of them are Combined with each other to form a substituted or unsubstituted monocyclic ring, Combined with each other to form a substituted or unsubstituted condensed ring, or Not combined with each other, R １００ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring ２１ to R ２８ are each independently A hydrogen atom, A halogen atom, A cyano group, A substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 ring-forming carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 60 ring-forming carbon atoms, A substituted or unsubstituted arylphosphoryl group having 6 to 60 ring-forming carbon atoms, A hydroxy group, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring-forming carbon atoms, -N(Rz) ２ a group represented by A thiol group, A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 30 ring-forming carbon atoms, A substituted germanium group, A substituted phosphine oxide group, A nitro group, A substituted boryl group, or A substituted or unsubstituted arylthio group having 6 to 30 ring-forming carbon atoms, However, R １００ is not an aryl group having 6 to 30 carbon atoms for ring formation by substitution, Rz is A substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms, or A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, -N(Rz) ２ The two Rz in are the same or different, A plurality of Rs １００ are the same as or different from each other, In the general formula (12A), * represents the bonding position with any one of the carbon atoms of the six-membered ring to which R ２１ ~R ２４ is bonded. ) 【Chemical 2】 (In the general formulas (11B), (11D), and (11F), X １ is an oxygen atom or a sulfur atom, R １１ ~R １４ at least one set consisting of two or more adjacent ones among them is Combined with each other to form a substituted or unsubstituted monocyclic ring, Combined with each other to form a substituted or unsubstituted condensed ring, or Not combined with each other, R １５ to R １８ one or more sets, each set consisting of two or more adjacent ones among them, Combined with each other to form a substituted or unsubstituted monocyclic ring, Combined with each other to form a substituted or unsubstituted condensed ring, or Not combined with each other, R １９ and R ２０ are hydrogen atoms, Do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring R that does not form １１ ~R １８ each independently does not form the substituted or unsubstituted monocyclic ring in the general formula (12A) and does not form the substituted or unsubstituted condensed ring, R ２１ ~R ２８ is synonymous with * represents a bonding position.) **Claim 2** In the organic electroluminescence device according to Claim 1, A is a group represented by the general formula (11D) or (11F), an organic electroluminescence device. **Claim 3** In the organic electroluminescence device according to Claim 2, A is a group represented by the general formula (11F), an organic electroluminescence device. **Claim 4** In the organic electroluminescence device according to Claim 2, A is a group represented by the general formula (11D), an organic electroluminescence device. **Claim 5** In the organic electroluminescence device according to any one of Claims 1 to 4, X1 is a sulfur atom, an organic electroluminescence device. **Claim 6** In the organic electroluminescence device according to any one of Claims 1 to 5, Y1 is an oxygen atom, an organic electroluminescence device. **Claim 7** In the organic electroluminescence device according to any one of Claims 1 to 4, X １ is an oxygen atom, an organic electroluminescence device. **Claim 8** In the organic electroluminescence device according to any one of Claims 1 to 4, X １ and Y １ are oxygen atoms, an organic electroluminescence device. **Claim 9** In the organic electroluminescence device according to any one of Claims 1 to 3, In the general formula (12A), A is a group represented by the general formula (11F), Y1 is an oxygen atom, * is the bonding position with the carbon atom of the six-membered ring to which R21 is bonded, an organic electroluminescence device. **Claim 10** In the organic electroluminescence device according to Claim 9, In the general formulas (12A) and (11F), R １００ , R １１ ~R １８ , and R ２２ ~R ２８ are each independently a hydrogen atom, or -(L １０１ )nx-R １０１ is a group represented by nx is 0, 1, 2, or 3, -(L １０１ )nx-R １０１ When there are a plurality of groups represented by, a plurality of -(L １０１ )nx-R １０１ represented by the groups are the same as or different from each other, A plurality of Rs １００ are identical to or different from each other, R １０１ is an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted phenyl group, an unsubstituted (9-phenyl)carbazolyl group, an unsubstituted 9-carbazolyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothienyl group, an unsubstituted (9-dibenzofuranyl)carbazolyl group, an unsubstituted (9-dibenzothienyl)carbazolyl group, a monovalent group derived from a compound represented by the following general formula (101), a monovalent group derived from a compound represented by the following general formula (102), a monovalent group derived from a compound represented by the following general formula (103), A monovalent group derived from a compound represented by the following general formula (104), a monovalent group derived from a compound represented by the following general formula (105), or a monovalent group derived from a compound represented by the following general formula (106), L １０１ is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted phenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothienylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted (9-dibenzofuranyl)carbazolylene group, a substituted or unsubstituted (9-dibenzothienyl)carbazolylene group, a divalent group derived from a compound represented by the following general formula (101), a divalent group derived from a compound represented by the following general formula (102), a divalent group derived from a compound represented by the following general formula (103), a divalent group derived from a compound represented by the following general formula (104), a divalent group derived from a compound represented by the following general formula (105), or a divalent group derived from a compound represented by the following general formula (106), However, R １００ is a group represented by -(L １０１ )nx - R １０１ in the case of a group represented by -(L １００ )nx - R １０１ )nx - R １０１ as R １０１ is not a substituted or unsubstituted phenylene group L １０１ When is an alkylene group having 1 to 30 carbon atoms of substitution, a substituted phenylene group, a substituted dibenzofuranylene group, a substituted dibenzothienylene group, a substituted carbazolylene group, a substituted (9-dibenzofuranyl)carbazolylene group, or a substituted (9-dibenzothienyl)carbazolylene group, the substituents are each independently, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted phenyl group, an unsubstituted (9-phenyl)carbazolyl group, an unsubstituted 9-carbazolyl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothienyl group, L １０１ If there are two or more Ls present, the two or more Ls １０１ are the same as each other or different from each other, R １０１ When two or more Rs exist, the two or more Rs １０１ are the same as each other or different an organic electroluminescence element. 【Chemical Formula 9】 (In the general formulas (101) to (106), X １Ｘ is an oxygen atom or a sulfur atom, R １１Ｘ to R ２１Ｘ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted phenyl group, an unsubstituted (9-phenyl)carbazolyl group, an unsubstituted 9-carbazolyl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothienyl group, However, R １０１ is a monovalent group derived from any of the compounds represented by the general formulas (101) to (106). When nx is 0, any one of the carbon atom of the six-membered ring to which R １１Ｘ to R ２０Ｘ are attached and the nitrogen atom to which R ２１Ｘ is attached is attached to any one of the carbon atoms of the six-membered ring to which R １１ to R １８ , R ２２ to R ２８ and R １００ are attached. When nx is 1, 2, or 3, any one of the carbon atom of the six-membered ring to which R １１Ｘ to R ２０Ｘ are attached and the nitrogen atom to which R ２１Ｘ is attached is attached to L １０１ . L １０１ is a divalent group derived from any of the compounds of the general formulas (101) to (106), and when nx is 1, R １１Ｘ ~R ２０Ｘ Of the two carbon atoms of the six-membered ring to which binds and the nitrogen atom to which R ２１Ｘ binds, one binds to R １０１ and the other binds to one of the carbon atoms of the six-membered ring to which R １１ ~R １８ , R ２２ ~R ２８ and R １００ bind, L １０１ is a divalent group derived from any one of the compounds of the general formulas (101) to (106), and when nx is 2 or 3, R １１Ｘ to R ２０Ｘ of the carbon atom of the six-membered ring to which is attached and the nitrogen atom to which R ２１Ｘ is attached, of any two of them, one is R １０１ or L １０１ and the other is R １１ to R １８ , R ２２ to R ２８ and R １００ is attached to any one of the carbon atoms of the six-membered ring to which is attached or L １０１ is attached. )

11. In the organic electroluminescence element according to any one of Claims 1 to 10, R100 is a hydrogen atom, an organic electroluminescence element.

12. In the organic electroluminescence element according to any one of Claims 1 to 11, R １１ to R １８ is a hydrogen atom an organic electroluminescence element.

13. In the organic electroluminescence element according to any one of Claims 1 to 12, In the light-emitting layer, the singlet energy S of the compound M2 １ The compound having a singlet energy S greater than that of (M2) １ is only the compound M3 an organic electroluminescence element.

14. In the organic electroluminescence element according to Claim 13, R １００ is not a substituted or unsubstituted dibenzofuranyl group, an organic electroluminescence element.

15. In the organic electroluminescence element according to any one of Claims 1 to 14, The light-emitting layer further contains a fluorescent compound M1, The singlet energy S of the compound M1 １ (M1) and the singlet energy S of the compound M2 １ (M2) satisfy the relationship of the following mathematical formula (Formula 2): Organic electroluminescence device. S １ (M2) > S １ (M1) … (Number 2)

16. In the organic electroluminescence device according to claim 15, The compound M1 is represented by the following general formula (2A), and the compound M1 exhibits luminescence with a maximum peak wavelength of 500 nm or more and 560 nm or less. Organic electroluminescence device. 【Chemical Formula 10】 (In the general formula (2A), The Za ring, Zb ring, and Zc ring are each independently, A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms, Ra is bonded to the Za ring or the Zb ring to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring, Rb is bonded to the Za ring or the Zc ring to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring, Ra and Rb that do not form the substituted or unsubstituted heterocyclic ring 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-forming carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.)

17. In the organic electroluminescence device according to any one of claims 1 to 16, The light-emitting layer does not contain a metal complex. Organic electroluminescence device.

18. An electronic device equipped with the organic electroluminescence device according to any one of claims 1 to 17.

19. A compound represented by the following general formula (100). 【Chemical 11】 (In the general formula (100), X １ is an oxygen atom or a sulfur atom, R １００ 、R １１ ~R ２０ 、and R ２２ ~R ２８ are each independently, A hydrogen atom, or -(L １０１ )nx - R １０１ is a group represented by nx is 0, 1, 2, or 3, -(L １０１ )nx-R １０１ When there are a plurality of groups represented by, the plurality of -(L １０１ )nx-R １０１ represented by groups are the same as or different from each other, A plurality of Rs １００ are identical to or different from each other, R １０１ is An unsubstituted alkyl group having 1 to 30 carbon atoms, An unsubstituted phenyl group, An unsubstituted (9-phenyl)carbazolyl group, An unsubstituted 9-carbazolyl group, An unsubstituted dibenzofuranyl group, An unsubstituted dibenzothienyl group, An unsubstituted (9-dibenzofuranyl)carbazolyl group, An unsubstituted (9-dibenzothienyl)carbazolyl group, A monovalent group derived from a compound represented by the following general formula (101), A monovalent group derived from a compound represented by the following general formula (102), A monovalent group derived from a compound represented by the following general formula (103), A monovalent group derived from a compound represented by the following general formula (104), A monovalent group derived from a compound represented by the following general formula (105), or A monovalent group derived from a compound represented by the following general formula (106), L １０１ is A substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, A substituted or unsubstituted phenylene group, A substituted or unsubstituted dibenzofuranylene group, A substituted or unsubstituted dibenzothienylene group, A substituted or unsubstituted carbazolylene group, A substituted or unsubstituted (9-dibenzofuranyl)carbazolylene group, A substituted or unsubstituted (9-dibenzothienyl)carbazolylene group, A divalent group derived from a compound represented by the following general formula (101), A divalent group derived from a compound represented by the following general formula (102), A divalent group derived from a compound represented by the following general formula (103), A divalent group derived from a compound represented by the following general formula (104), A divalent group derived from a compound represented by the following general formula (105), or A divalent group derived from a compound represented by the following general formula (106), L １０１ When is an alkylene group having 1 to 30 carbon atoms of substitution, a substituted phenylene group, a substituted dibenzofuranylene group, a substituted dibenzothienylene group, a substituted carbazolylene group, a substituted (9-dibenzofuranyl) carbazolylene group, or a substituted (9-dibenzothienyl) carbazolylene group, the substituents are each independently, An unsubstituted alkyl group having 1 to 30 carbon atoms, An unsubstituted phenyl group, An unsubstituted (9-phenyl)carbazolyl group, An unsubstituted 9-carbazolyl group, An unsubstituted dibenzofuranyl group, or An unsubstituted dibenzothienyl group, L １０１ When there are two or more Ls １０１ they may be the same as or different from each other R １０１ When there are two or more Rs １０１ they may be the same as or different from each other However, * represents the bonding position with any one of the carbon atoms of the benzene ring to which R １００ is bonded.) 【Chemical Formula 12】 (In the general formulas (101) to (106), X １Ｘ is an oxygen atom or a sulfur atom, R １１Ｘ ~R ２１Ｘ are each independently A hydrogen atom, An unsubstituted alkyl group having 1 to 30 carbon atoms, An unsubstituted phenyl group, An unsubstituted (9-phenyl)carbazolyl group, An unsubstituted 9-carbazolyl group, An unsubstituted dibenzofuranyl group, or An unsubstituted dibenzothienyl group, However, R １０１ is a monovalent group derived from any one of the compounds of the general formulas (101) to (106), and when nx is 0, R １１Ｘ ~R ２０Ｘ and the carbon atom of the six-membered ring to which R ２１Ｘ Any one of the nitrogen atoms to which is bonded is R １１ ~R ２０ , R ２２ ~R ２８ and R １００ is bonded to any one of the carbon atoms of the six-membered ring to which nx is 1, 2 or In the case of 3, R １１Ｘ ~R ２０Ｘ is bonded to either one of the carbon atoms of the six-membered ring to which R ２１Ｘ is bonded and the nitrogen atom to which R １０１ is bonded to L. L １０１ is a divalent group derived from any of the compounds of the general formulas (101) to (106), and when nx is 1, R １１Ｘ to R ２０Ｘ of the six-membered ring carbon atom to which is bonded and the nitrogen atom to which R ２１Ｘ is bonded, of any two of them, one is bonded to R １０１ and the other is bonded to any one of the six-membered ring carbon atoms to which R １１ to R ２０ , R ２２ to R ２８ and R １００ is bonded, L １０１ is a divalent group derived from any of the compounds of the general formulas (101) to (106), and when nx is 2 or 3, R １１Ｘ to R ２０Ｘ of the carbon atom of the six-membered ring to which is attached and the nitrogen atom to which R ２１Ｘ is attached, of any two of them, one is R １０１ or L １０１ and the other is R １１ to R ２０ , R ２２ to R ２８ and R １００ is attached to any one of the carbon atoms of the six-membered ring to which is attached or L １０１ is attached. )​

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