Organic electroluminescent element and electronic device

Abstract

To provide a high-performance organic electroluminescent element.SOLUTION: An organic electroluminescent device (1) includes an anode (3), a cathode (4), and a light-emitting layer (5) interposed between the anode (3) and the cathode (4), wherein the light-emitting layer (5) includes a compound M3 represented by the following general formula (1) and a delayed fluorescent compound M2, the compound M3 and the compound M2 are different in structure from each other, and a singlet energy S1 (M3) of the compound M3 and a singlet energy S1 (M2) of the compound M2 satisfy a relationship represented by the following formula (1): S1 (M3)> S1 (M2): (1) SELECTED DRAWING: Figure 1

Description

[Technical Field]

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

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

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

[0004] In order to improve the performance of organic EL devices, 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 devices. Patent Document 2 also discloses an organic EL device that utilizes the TADF mechanism. The performance of an organic EL element includes, for example, brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] International Publication No. 2013 / 011891 [Patent Document 2] International Publication No. 2020 / 122118 Summary of the Invention [Problem to be solved by the invention]

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

[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. [Means for solving the problem]

[0008] According to one aspect of the present invention, an anode; A cathode; a light-emitting layer between the anode and the cathode, The light-emitting layer contains a compound M3 represented by the following general formula (1) and a delayed fluorescent compound M2, The compound M3 and the compound M2 have different structures, There is provided an organic electroluminescence device in which the singlet energy S1(M3) of the compound M3 and the singlet energy S1(M2) of the compound M2 satisfy the relationship of the following mathematical formula (Mathematical Formula 1). S1(M3)>S1(M2) (Math 1)

[0009] [ka]

[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), Y1 is an oxygen atom or a sulfur atom, n is 0 or 1, R 21 ~R 28 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 100 and R that 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, hydrogen atoms, halogen atoms, 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, hydroxy groups, 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; a group represented by —N(Rz)2, thiol groups, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms; substituted germanium groups, substituted phosphine oxide groups, 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, Two Rz in —N(Rz)2 are the same or different, Multiple R 100 are identical to or different from each other, However, when n is 0 and X1 in the following general formulae (11A), (11B), (11C), (11D), (11E), and (11F) is an oxygen atom, R 25 is not a substituted or unsubstituted dibenzofuranyl group. In the general formula (1), * represents R 21 ~R 24 represents the bonding position of any one of the carbon atoms of the six-membered ring to which

[0011] [ka]

[0012] (In the general formulae (11A), (11B), (11C), (11D), (11E) and (11F), X1 is an oxygen atom or a sulfur atom, R 11 ~R 14 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 15 ~R 18 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 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 is synonymous with However, when n is 0, * represents 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, an anode; A cathode; a light-emitting layer between the anode and the cathode, The light-emitting layer contains a compound M3 represented by the following general formula (1) and a delayed fluorescent compound M2, The compound M3 and the compound M2 have different structures, There is provided an organic electroluminescence device in which the singlet energy S1(M3) of the compound M3 and the singlet energy S1(M2) of the compound M2 satisfy the relationship of the following mathematical formula (Mathematical Formula 1). S1(M3)>S1(M2) (Math 1)

[0014] [ka]

[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), Y1 is an oxygen atom or a sulfur atom, n is 0 or 1, R 21 ~R 28 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 100 and R that 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, hydrogen atoms, halogen atoms, 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, hydroxy groups, 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; a group represented by —N(Rz)2, thiol groups, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms; substituted germanium groups, substituted phosphine oxide groups, 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, Two Rz in —N(Rz)2 are the same or different, Multiple R 100 are identical to or different from each other, However, when n is 0 and X1 in the following general formulae (11A), (11B), (11C), (11D), (11E), and (11F) is an oxygen atom, R 25 is not a substituted or unsubstituted dibenzofuranyl group. In the general formula (1), * represents R 21 ~R 24 represents the bonding position of any one of the carbon atoms of the six-membered ring to which

[0016] [ka]

[0017] (In the general formulae (11A), (11B), (11C), (11D), (11E) and (11F), X1 is an oxygen atom or a sulfur atom, R 11 ~R 20 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 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 is synonymous with However, when n is 0, * represents 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] [ka]

[0021] (In the general formula (100), X1 is an oxygen atom or a sulfur atom, R 100 , R 11 ~R 20 , and R 22 ~R 28 are each independently, hydrogen atoms, -(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 multiple groups represented by -(L 101 )nx-R 101 are the same or different, Multiple R 100 are identical to or different from each other, R 101 teeth, 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): A monovalent group derived from a compound represented by the following general formula (106): L 101 teeth, 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): A divalent group derived from a compound represented by the following general formula (106): L 101 is 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, each of the substituents independently represents 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 101If there are two or more, there are two or more L 101 are identical to or different from each other, R 101 If there are two or more, there are two or more R 101 are identical to or different from each other, However, * indicates R 100 represents the bonding position of any one of the carbon atoms of the benzene ring to which

[0022] [ka]

[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, hydrogen atoms, 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 a compound of any one of the general formulae (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 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 bonded, and when nx is 1, 2, or 3, R 11X ~R 20X and the carbon atom of the six-membered ring to which R is attached. 21X One of the nitrogen atoms to which is bonded is L 101 and combine. L 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 is attached. 21X Of the 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 is attached. 21X Of the 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 ) [Effects of the Invention]

[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. [Brief explanation of the drawings]

[0025] [Figure 1] 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. [Figure 2] FIG. 1 is a schematic diagram of an apparatus for measuring transient PL. [Figure 3] FIG. 10 is a diagram showing an example of a decay curve of a transient PL. [Figure 4] FIG. 3 is a diagram showing the relationship between the energy levels of the compound M3 and the compound M2 in the light-emitting layer of the example organic electroluminescence device according to the first embodiment of the present invention. [Figure 5] FIG. 4 is a diagram showing the energy levels of compounds M3, M2, and M1 in an emitting layer of an example of an organic electroluminescence device according to a second embodiment of the present invention, and the relationship between energy transfer. DETAILED DESCRIPTION OF THE INVENTION

[0026] [Definition] 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, i.e., a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded to a possible bonding position that is not explicitly marked with a symbol such as "R" or "D" representing a deuterium atom.

[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. Furthermore, when a benzene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of the benzene ring substituted with an alkyl group is 6. Furthermore, when a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.

[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 are not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. Furthermore, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring, so the number of ring atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

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

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

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

[0033] "Substituents described herein" The substituents described in this specification will be explained below.

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

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

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

[0037] [ka]

[0038] [ka]

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

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

[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 a substituent (specific example group G2B4).

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

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

[0045] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): a thienyl group, a thiazolyl group, isothiazolyl group, a thiadiazolyl group, Benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), naphthobenzothiophenyl group (naphthobenzothienyl group), benzothiazolyl group, benzoisothiazolyl group, a phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), diazadibenzothiophenyl group (diazadibenzothienyl group), Azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[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] [ka]

[0048] [ka]

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

[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, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, methylbenzimidazolyl group, ethylbenzimidazolyl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, a phenylquinazolinyl group, and a biphenylylquinazolinyl group.

[0051] Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, t-Butyldibenzofuranyl group, and the monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

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

[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, A and Y A a hydrogen atom bonded to a nitrogen atom when at least one of A and Y A or more hydrogen atoms selected from the hydrogen atoms of a methylene group when one of the groups is CH2.

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

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

[0057] Substituted alkyl groups (specific example group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group and 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, the term "unsubstituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and the term "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply includes both an "unsubstituted alkenyl group" and a "substituted alkenyl group." A "substituted alkenyl group" refers to an "unsubstituted alkenyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl groups" (specific example group G4A) having a substituent, and the examples of substituted alkenyl groups (specific example group G4B). The examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl group" described in this specification also includes groups in the "substituted alkenyl groups" of specific example group G4B in which a hydrogen atom of the alkenyl group itself has been further replaced with a substituent, and groups in the "substituted alkenyl groups" of specific example group G4B in which a hydrogen atom of a substituent has been further replaced with a substituent.

[0059] Unsubstituted alkenyl groups (specific example group G4A): vinyl groups, Allyl groups, a 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 groups (specific example group G5A). (Here, the unsubstituted alkynyl group refers to a case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, when simply referring to an "alkynyl group," it includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group." A "substituted alkynyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced with substituents. Specific examples of the "substituted alkynyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl group" (specific example group G5A) are replaced with substituents, etc.

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

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

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

[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 -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. The multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other. The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other. The multiple G1s in —Si(G1)(G1)(G2) are the same as or different from each other. The multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other. The multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The multiple G6s in -Si(G6)(G6)(G6) may be the same as or different from each other.

[0067] -O-(R 904 ) a group represented by -O-(R 904 Specific examples (specific example group G8) of the group represented by -O(G1), -O(G2), -O(G3) and -O(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0068] -S-(R 905 ) a group represented by -S-(R 905 Specific examples (specific example group G9) of the group represented by -S(G1), -S(G2), -S(G3) and -S(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in 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 the group represented by -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3) and -N(G6)(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. -The multiple G1s in N(G1)(G1) are the same as or different from each other. The multiple G2's in -N(G2)(G2) are the same as or different from each other. -The multiple G3s in N(G3)(G3) are the same as or different from each other. -The multiple G6s in N(G6)(G6) are the same or different from each other.

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

[0071] "Substituted or unsubstituted fluoroalkyl groups" The term "substituted or unsubstituted fluoroalkyl group" as used herein refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). Unless otherwise specified herein, the number of carbon atoms in an "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The term "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. The term "substituted fluoroalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in a "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in a "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include the examples of the above-mentioned "alkyl group" (specific example group G3) in which one or more hydrogen atoms are replaced with a fluorine atom.

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

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

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

[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. The number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[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. The number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0077] "Substituted or unsubstituted trialkylsilyl group" A specific example of the "substituted or unsubstituted trialkylsilyl group" described herein is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Multiple G3 groups in -Si(G3)(G3)(G3) may be the same or different. Unless otherwise specified herein, the number of carbon atoms in each alkyl group of the "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 herein is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. Thus, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one embodiment of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group," and the number of carbon atoms in the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified herein. Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl groups.

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

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

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

[0082] [ka]

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

[0084] [ka]

[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] [ka]

[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 of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1.

[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 of the "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3.

[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] [ka]

[0095] [ka]

[0096] In the general formulae (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-42) to (TEMP-52), * represents a bonding position.

[0097] [ka]

[0098] In the general formulae (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent. Equations Q9 and Q 10 may be bonded to each other via a single bond to form a ring. In the general formulae (TEMP-53) to (TEMP-62), * represents a bonding position.

[0099] [ka]

[0100] In the general formulae (TEMP-63) to (TEMP-68), Q1 to Q8 each independently represent a hydrogen atom or a substituent. In the general formulae (TEMP-63) to (TEMP-68), * represents a bonding position.

[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] [ka]

[0103] [ka]

[0104] [ka]

[0105] In the general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 each independently represent a hydrogen atom or a substituent. In the general formulae (TEMP-69) to (TEMP-82), * represents a bonding position.

[0106] [ka]

[0107] [ka]

[0108] [ka]

[0109] [ka]

[0110] In the general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 each independently represent 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, the phrase "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocycle, bond with each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocycle", the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted fused ring", or the case where "one or more pairs of adjacent groups do not bond with each other". In this specification, the cases where "one or more groups of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocyclic ring" and "one or more groups of two or more adjacent groups bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "a case where they bond to form a ring") will be explained below. The case of an anthracene compound represented by the following general formula (TEMP-103), in which the main skeleton is an anthracene ring, will be explained as an example.

[0113] [ka]

[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," one pair of adjacent two groups is R 921 and R 922 Paired with R 922 and R 923 Paired with R 923 and R 924 Paired with R 924 and R 930 Paired with R 930 and R 925 Paired with R 925 and R 926 Paired with R 926 and R 927 Paired with R 927 and R 928 Paired with R 928 and R 929 Pairs with and R 929 and R 921 It is paired with.

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

[0116] [ka]

[0117] When a "set of two or more adjacent units" forms a ring, it does not only mean that a set of two adjacent units is bonded, as in the previous example, but also that a set of three or more adjacent units is bonded. For example, R921 and R 922 and are bonded to each other to form ring Q A and R 922 and R 923 and are bonded to each other to form ring Q C and form three adjacent (R 921 , R 922 and R 923 In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105): A and Ring Q C is R 922 Share.

[0118] [ka]

[0119] The "monocyclic ring" or "fused ring" formed may be a saturated ring or an unsaturated ring as the structure of only the ring formed. Even when "one pair of adjacent two" forms a "monocyclic ring" or a "fused ring", the "monocyclic ring" or the "fused ring" may form a saturated ring or an unsaturated ring. For example, in the case of the ring Q formed in the general formula (TEMP-104), A and Ring Q B are "monocyclic rings" or "fused rings", respectively. A , and ring Q C is a "fused ring". A and Tamaki Q C That is, Tamaki Q A and Tamaki Q C The ring Q in the general formula (TMEP-104) is fused to form a fused ring. A If is a benzene ring, then ring Q A The ring Q in the general formula (TMEP-104) is a monocyclic ring. A If is a naphthalene ring, then ring Q Ais 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] The "saturated ring" is at least one ring selected from an aliphatic hydrocarbon ring having no unsaturated bonds and a non-aromatic heterocyclic ring having no unsaturated bonds. The saturated ring has no double or triple bonds in the ring structure. Specific examples of the aromatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G1 are terminated with a hydrogen atom. Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in the specific example group G2 are terminated with a hydrogen atom. Specific examples of the aliphatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom. The term "forming a ring" means that a ring is formed only with a plurality of atoms in the main skeleton, or with a plurality of atoms in the main skeleton and one or more additional atoms. For example, R 921 and R 922 and are bonded to form a ring Q A is R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 It means a ring formed by the carbon atom of the anthracene skeleton to which R is bonded and one or more arbitrary atoms. 921 and R 922 Todekan Q A In the case where R921 The carbon atom of the anthracene skeleton to which R is bonded 922 When a monocyclic unsaturated ring is formed with the carbon atom of the anthracene skeleton to which R is bonded and four carbon atoms, 921 and R 922 The ring formed by

[0122] Here, unless otherwise specified in this specification, the "arbitrary atom" is preferably at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. In the arbitrary atom (for example, in the case of a carbon atom or a nitrogen atom), the bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below. When an arbitrary atom other than a carbon atom is included, the formed ring is a heterocycle. Unless otherwise specified in this specification, the "one or more arbitrary atoms" constituting the single ring or fused ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less. Unless otherwise specified in this specification, of the "monocyclic ring" and the "fused ring", the "monocyclic ring" is preferred. Unless otherwise specified in this specification, of the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred. Unless otherwise specified herein, a "monocyclic ring" is preferably a benzene ring. Unless otherwise specified herein, the "unsaturated ring" is preferably a benzene ring. When "one or more pairs of adjacent two or more 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 later. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification." When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "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 groups bond to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring" ("when bonded to form a ring").

[0124] Substituents in "substituted or unsubstituted" In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituent" in the present specification) includes, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms; an unsubstituted alkenyl group having 2 to 50 carbon atoms; an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms; -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring carbon atoms and an unsubstituted heterocyclic group having 5 to 50 ring atoms, where R 901 ~R907 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 901 If there are two or more, there are two or more R 901 are identical to or different from each other, R 902 If there are two or more, there are two or more R 902 are identical to or different from each other, R 903 If there are two or more, there are two or more R 903 are identical to or different from each other, R 904 If there are two or more, there are two or more R 904 are identical to or different from each other, R 905 If there are two or more, there are two or more R 905 are identical to or different from each other, R 906 If there are two or more, there are two or more R 906 are identical to or different from each other, R 907 If there are two or more, there are two or more R 907 are the same or different from each other.

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

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

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

[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 the organic EL element according to the first embodiment of the present invention will be described. The organic EL device 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 device 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 a layer that can be used in an organic EL device. The layer that can be used in an organic EL device is not particularly limited, and examples thereof 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 device of this embodiment has a light-emitting layer between an anode and a cathode.

[0131] FIG. 1 shows a schematic configuration of an example of an organic EL element according to this embodiment. The organic EL device 1 includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is configured by laminating, in this order from the anode 3 side, a hole injection layer 6, a hole transport layer 7, an emitting layer 5, an electron transport layer 8, and an electron injection layer 9.

[0132] The light-emitting layer 5 may contain a metal complex. The light-emitting layer 5 preferably does not contain a phosphorescent material (dopant material). The light-emitting layer 5 preferably does not contain a heavy metal complex or a phosphorescent rare earth metal complex. Examples of heavy metal complexes include an iridium complex, an osmium complex, and a platinum complex. 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, compound M2 is preferably a dopant material (sometimes referred to as a guest material, an emitter, or a light-emitting material), and 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, this compound may be referred to as the compound of Patent Document 2), and an organic EL device in which this compound is contained in an emitting layer together with a delayed fluorescent compound. However, the compound of Patent Document 2 has a low triplet energy and cannot sufficiently confine the triplet energy of the delayed fluorescent compound, which causes a problem in that the efficiency of the device cannot be sufficiently improved. The present inventors have found that a high-performance organic EL device can be realized by incorporating the compound M3 represented by the general formula (1) (compound M3 according to this embodiment) into the light-emitting layer together with the delayed fluorescent compound M2. Compound M3 according to this embodiment is a compound in which benzofuranocarbazole or benzothienocarbazole, which supplies an appropriate amount of holes to the light-emitting layer, and highly durable dibenzofuran or dibenzothiophene are bonded via a phenylene having a short conjugation length or a single bond. Compound M3 according to this embodiment exhibits high triplet energy, and can therefore sufficiently confine the triplet energy of a delayed fluorescent compound. Therefore, according to the organic EL element of this embodiment, a high-performance organic EL element, particularly an organic EL element that emits light with high efficiency, can be realized.

[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). The compound M3 in this embodiment may be a thermally activated delayed fluorescent 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] [ka]

[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), Y1 is an oxygen atom or a sulfur atom, n is 0 or 1, R 21 ~R 28 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 100 and R that 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, hydrogen atoms, halogen atoms, 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, hydroxy groups, 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; a group represented by —N(Rz)2, thiol groups, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms; substituted germanium groups, substituted phosphine oxide groups, 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, Two Rz in —N(Rz)2 are the same or different, Multiple R 100 are identical to or different from each other, However, when n is 0 and X1 in the following general formulae (11A), (11B), (11C), (11D), (11E), and (11F) is an oxygen atom, R 25 is not a substituted or unsubstituted dibenzofuranyl group. In the general formula (1), * represents R 21 ~R 24 represents the bonding position of any one of the carbon atoms of the six-membered ring to which

[0138] [ka]

[0139] (In one embodiment of the general formulae (11A), (11B), (11C), (11D), (11E), and (11F), X1 is an oxygen atom or a sulfur atom, R 11 ~R 20 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 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 is synonymous with However, when n is 0, * represents 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), X1 is an oxygen atom or a sulfur atom, R 11 ~R 14 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 15 ~R 18 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 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 is synonymous with However, when n is 0, * represents 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] [ka]

[0143] (In the general formulae (111A), (111B), (111C), (111D), (111E), and (111F), X1 has the same meaning as X1 in the general formula (11A), and 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 ~R 28 and * indicates the bonding position.)

[0144] The compound M3 represented by the 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 the general formula (1)) is a compound represented by the following general formula (1-1), (1-2), (1-3) or (1-4).

[0145] [ka]

[0146] (In the general formulae (1-1), (1-2), (1-3) and (1-4), A, R 100 , n, Y1 and R 21 ~R 28 each independently represents A and R in the general formula (1). 100 , n, Y1 and R 21 ~R 28 is synonymous with R 100 are the same as or different from each other. When n is 0, * in the general formulae (11A), (11B), (11C), (11D), (11E) and (11F) represents the bonding position to *1. When n is 1, * in the general formulae (11A), (11B), (11C), (11D), (11E) and (11F) represents 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 following general formula (2A) (compound M1), the external quantum efficiency can be improved compared to when a compound represented by the following general formula (12C) (compound M3) is used in combination with a compound represented by the following general formula (2A) (compound M1). In particular, by selecting a compound represented by the following general formula (12A) where X1 in A is a sulfur atom as compound M3, the external quantum efficiency and lifetime can be further improved.

[0149] [ka] (In the general formula (12A), A, R 100 , Y1 and R 21 ~R 28 each independently represents A and R in the general formula (1). 100 , Y1 and R 21 ~R 28 is synonymous with R 100 are the same or different from each other, except that * denotes R 21 ~R 24 represents the bonding position of 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] [ka]

[0152] (In the general formula (12B), A, R 100 , Y1 and R 21 ~R 28 each independently represents A and R in the general formula (1). 100 , Y1 and R 21 ~R 28 is synonymous with R 100 are the same or different from each other, except that * denotes R 21 ~R24 represents the bonding position of 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] [ka]

[0155] (In the general formula (12C), A, R 100 , Y1 and R 21 ~R 28 each independently represents A and R in the general formula (1). 100 , Y1 and R 21 ~R 28 is synonymous with R 100 are the same or different from each other, except that * denotes R 21 ~R 24 represents the bonding position of 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, X1 is an oxygen atom. In one embodiment of compound M3, X1 is a sulfur atom. In one embodiment of compound M3, Y1 is an oxygen atom. In one embodiment of compound M3, X1 and Y1 are oxygen atoms.

[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 28 is 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, compound M3 is a compound represented by the following general formula (12A-1).

[0168] [ka]

[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), R 100 , Y1 and R 21 ~R 28 are each independently R in the general formula (1). 100 , Y1 and R 21 ~R 28 is synonymous with R 100 are the same or different from each other, except that * denotes R 21 ~R 24 represents the bonding position of any one of the carbon atoms of the six-membered ring to which

[0170] [ka]

[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 emitting layer according to one embodiment, the compound M3 is the only compound having a singlet energy S1 greater than the singlet energy S1(M2) of the delayed fluorescent compound M2.

[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] [ka]

[0177] (In the general formula (100), X1 is an oxygen atom or a sulfur atom, R 100 , R 11 ~R 20 , and R 22 ~R 28 are each independently, hydrogen atoms, -(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 multiple groups represented by -(L 101 )nx-R 101 are the same or different, Multiple R 100 are identical to or different from each other, R 101 teeth, 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): A monovalent group derived from a compound represented by the following general formula (106): L 101 teeth, 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): A divalent group derived from a compound represented by the following general formula (106): L 101 is 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, each of the substituents independently represents 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, there are two or more L 101 are identical to or different from each other, R 101 If there are two or more, there are two or more R 101 are identical to or different from each other, However, * indicates R 100 represents the bonding position of any one of the carbon atoms of the benzene ring to which

[0178] [ka]

[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, hydrogen atoms, 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 a compound of any one of the general formulae (101) to (106), and when nx is 0, R 11X ~R 20X and the carbon atom of the six-membered ring to which R is attached. 21X One of the nitrogen atoms to which is bonded is R 11 ~R 20 , R 22 ~R28 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 ~R 20X and the carbon atom of the six-membered ring to which R is attached. 21X One of the nitrogen atoms to which is bonded is L 101 and combine. L 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 is attached. 21X Of the 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 is attached. 21X Of the 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 )

[0180] In one embodiment of the compound M3, 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 compound.

[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] [ka]

[0184] [ka]

[0185] [ka]

[0186] [ka]

[0187] [ka]

[0188] [ka]

[0189] [ka]

[0190] [ka]

[0191] [ka]

[0192] [ka]

[0193] [ka]

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

[0195] Delayed fluorescence Delayed fluorescence is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Adachi Chihaya, published by Kodansha). In that paper, the energy difference ΔE between the excited singlet state and the excited triplet state of a fluorescent material is 13 It is explained that if the energy transfer rate can be reduced, the reverse energy transfer from the excited triplet state, which normally has a low transition probability, to the excited singlet state occurs with high efficiency, resulting in the appearance of thermally activated delayed fluorescence (TADF). Furthermore, Figure 10.38 in this document explains the mechanism by which delayed fluorescence occurs. Compound M2 in this embodiment is preferably a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism.

[0196] Generally, 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 the decay behavior (transient characteristics) of the PL emission is measured after the irradiation is stopped. PL emission from TADF materials is classified into emission components from singlet excitons generated during the initial PL excitation, and emission components from singlet excitons generated via triplet excitons. The lifetime of singlet excitons generated during the initial PL excitation is extremely short, on the order of nanoseconds. Therefore, the emission from these singlet excitons decays quickly after irradiation with a pulsed laser. On the other hand, delayed fluorescence decays slowly because it is emitted from singlet excitons generated via triplet excitons, which have a long lifetime. Thus, there is a large time difference between the emission from the singlet excitons generated by the initial PL excitation and the emission from the singlet excitons generated via triplet excitons. Therefore, the emission intensity derived from delayed fluorescence can be measured.

[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 using Figure 2 will be described below.

[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 matrix material is doped with a doping material at a concentration of 12 mass %.

[0201] A pulsed laser is irradiated from the pulsed laser unit 101 onto a thin film sample placed in the sample chamber 102 to excite the doping material. Emission light is extracted in a direction 90 degrees to the irradiation direction of the excitation light, and the extracted light is dispersed by the spectrometer 103, forming a two-dimensional image in the streak camera 104. As a result, a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and bright spots correspond to emission intensity. By cutting out this two-dimensional image along a predetermined time axis, an emission spectrum can be obtained in which the vertical axis represents emission intensity and the horizontal axis represents wavelength. Furthermore, by cutting out the two-dimensional image along the wavelength axis, a decay curve (transient PL) can be obtained in which the vertical axis represents the logarithm of emission intensity and the horizontal axis represents time.

[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] [ka]

[0204] Here, the decay 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 the matrix material and the above-mentioned reference compound D1 as the 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] [ka]

[0207] As described above, transient PL measurements can be used to obtain an emission decay curve with emission intensity on the vertical axis and time on the horizontal axis. Based on this emission decay curve, the fluorescence intensity ratio between the fluorescence emitted from the singlet excited state generated by photoexcitation and the delayed fluorescence emitted from the singlet excited state generated by back energy transfer via the triplet excited state can be estimated. In delayed fluorescent materials, the ratio of the intensity of the delayed fluorescence, which decays slowly, to the intensity of the fluorescence, which decays quickly, is somewhat larger.

[0208] Specifically, there are two types of luminescence from delayed fluorescent materials: prompt luminescence and delayed luminescence. Prompt luminescence is luminescence that is observed immediately from the excited state after being excited by pulsed light (light irradiated from a pulsed laser) with a wavelength that the delayed fluorescent material absorbs. Delayed luminescence is luminescence that is not observed immediately after excitation by the pulsed light, but is observed later.

[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 this specification, the delayed fluorescence of compound M2 is measured using a sample prepared by the following method. 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 produce an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the sample solution was measured using a spectrofluorometer FP-8600 (JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. The total fluorescence quantum yield was calculated using the fluorescence area intensities of both spectra 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). 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. In this embodiment, the amount of prompt luminescence (instantaneous luminescence) of the compound to be measured (compound M2) is calculated as X P and the amount of delay light emission is X D When X D / X P It is preferable that the value is 0.05 or more. The amounts and ratios of prompt luminescence and delayed luminescence of compounds other than compound M2 herein are measured in the same manner as the amounts and ratios of prompt luminescence and delayed luminescence of compound M2.

[0212] Method for producing compound M2 of this embodiment The compound M2 of this embodiment can be produced by a known method.

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

[0214] [ka]

[0215] [ka]

[0216] [ka]

[0217] <Relationship between Compound M3 and Compound M2 in the Light-Emitting Layer> In the organic EL device of this embodiment, the singlet energy S1(M2) of the compound M2 and the singlet energy S1(M3) of the compound M3 satisfy the relationship of the following mathematical formula (Mathematical Formula 1). S1(M3)>S1(M2) (Math 1)

[0218] 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 value is larger than (M2). That is, it is preferable that the relationship of the following mathematical formula (Mathematical Formula 11) is satisfied. T 77K (M3)>T 77K (M2) …(Number 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 the 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 that is usually defined. Triplet energy is measured as follows. First, a sample is prepared by dissolving the compound to be measured in an appropriate solvent and sealing the solution in a quartz glass tube. The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this sample is measured at low temperature (77 K). A tangent line is drawn to the rising edge of the short wavelength side of this phosphorescence spectrum, and the triplet energy is calculated using a predetermined conversion formula based on the wavelength value at the intersection of the tangent line and the horizontal axis. Among the compounds according to this embodiment, the thermally activated delayed fluorescent compound is preferably a compound with a small ΔST. When ΔST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at low temperatures (77 [K]), resulting in a mixture of excited singlet and excited triplet states. As a result, the spectrum measured in the same manner as above contains light emission from both the excited singlet and excited triplet states, and although it is difficult to clearly distinguish which state the light emission originates from, the triplet energy value is generally considered to be dominant. Therefore, in this 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 the measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this measurement sample is measured at low temperature (77 [K]), and a tangent line is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent line and the horizontal axis is determined. edge Based on the [nm], the amount of energy calculated using the following conversion formula (F1) is the energy gap T at 77 [K]. 77K Let's say. Conversion formula (F1):T 77K [eV]=1239.85 / λ edge

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

[0222] Singlet energy S1 The following method can be mentioned as a method for measuring the singlet energy S1 using a solution (sometimes referred to as a solution method). A 10 μmol / L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the absorption spectrum (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K). A tangent line is drawn to the falling edge on the long wavelength side of this absorption spectrum, and the wavelength value λedge [nm] at the intersection of this tangent line and the horizontal axis is substituted into the following conversion formula (F2) to calculate the singlet energy. Conversion formula (F2): S1[eV]=1239.85 / λedge An example of an absorption spectrum measuring device is a spectrophotometer manufactured by Hitachi (device name: U3310), but is not limited to this.

[0223] The tangent to the fall on the long wavelength side of the absorption spectrum is drawn as follows. When moving along the spectral curve from the longest maximum value on the longest wavelength side of the absorption spectrum toward longer wavelengths, consider the tangent at each point on the curve. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the slope is minimum on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is considered to be the tangent to the fall on the long wavelength side of the absorption spectrum. Note that maximum points with absorbance values ​​of 0.2 or less are not included in the maximum values ​​on the longest wavelength side.

[0224] In this embodiment, the singlet energy S1 and the energy gap T at 77 [K] 77K The difference between (S1-T 77K ) is defined as ΔST.

[0225] In this embodiment, the singlet energy S1(M2) of the compound M2 and the energy gap T 77K The difference ΔST(M2) from (M2) is preferably less than 0.3 eV, more preferably less than 0.2 eV, even more preferably less than 0.1 eV, and even more preferably less than 0.01 eV. That is, ΔST(M2) preferably satisfies any one of the relationships of the following mathematical formulas (1A) to (1D). ΔST(M2)=S1(M2)-T 77K (M2)<0.3eV (several 1A) ΔST(M2)=S1(M2)-T 77K (M2)<0.2eV (several 1B) ΔST(M2)=S1(M2)-T 77K (M2)<0.1eV (several 1C) ΔST(M2)=S1(M2)-T 77K (M2)<0.01eV (number 1D)

[0226] Thickness of the light-emitting layer The thickness of the light-emitting layer in the organic EL device 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] Compound content in the light-emitting layer The content of the compound M2 and the compound M3 in the light-emitting layer is preferably, for example, in the following range. 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. In this embodiment, the light-emitting layer may contain materials other than the compound M2 and the 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 M3 or two or more types thereof.

[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 the reverse intersystem crossing that occurs in this 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 device 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 larger than that of the compound M2, thereby realizing a high-performance organic EL device. The organic EL device 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 explained.

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

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

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

[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 easily injects holes regardless of the work function of the anode, so materials that can be used as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures of these, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.

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

[0236] (cathode) The cathode is preferably made of a metal, alloy, electrically conductive compound, or mixture thereof, each having a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) 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 deposited by sputtering, inkjet printing, spin coating, etc.

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

[0241] Furthermore, polymeric compounds (oligomers, dendrimers, polymers, etc.) can also be used as materials with high hole injection properties. Examples include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD). Acid-added polymeric compounds such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can also be used.

[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), Aromatic amine compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) can be used. The substances mentioned here are mainly 10 -6 cm 2 A material with a hole mobility of at least / (V·s).

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

[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 used, it is preferable to place a material with a larger energy gap closer to the light emitting layer, such as 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. Examples of materials that can be used for the electron transport layer include: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymer compounds. Specifically, examples of low-molecular-weight organic compounds that can be used include metal complexes such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviated as BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), bathophenanthroline (abbreviated as BPhen), bathocuproine (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs) can also be used. In this embodiment, benzimidazole compounds can be preferably used. The substances mentioned here are mainly 10 -6 cm 2 / (V·s) or more. Note that other substances may be used as the electron-transporting layer as long as they have a higher electron-transporting property than a hole-transporting property. The electron-transporting layer may be formed as a single layer or as a stack of two or more layers made of the above-mentioned substances.

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

[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 above-mentioned substances constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor may be any substance that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides and alkaline earth metal oxides are also preferred, such as lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (TTF) can also be used. (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 known methods can be used, such as dry film formation methods such as vacuum deposition, sputtering, plasma deposition, and ion plating, and wet film formation methods such as spin coating, dipping, flow coating, and inkjet deposition.

[0250] (film thickness) The thickness of each organic layer in the organic EL element of the present embodiment is not limited except as specifically mentioned above. However, in general, if the thickness is too thin, defects such as pinholes are likely to occur, whereas if the thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, a thickness in the range of several nm to 1 μm is usually preferred.

[0251] Second Embodiment The configuration of an organic EL element according to a second embodiment will be described. In the description of the second embodiment, the same components as those in 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 device of the second embodiment differs from the organic EL device of the first embodiment in that the emitting layer further contains a fluorescent compound M1, but other points are the same as those of the first embodiment. That is, in the second embodiment, the light-emitting layer contains the compound M3 represented by the general formula (1), the delayed fluorescent compound M2, and the 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 light-emitting layer of this embodiment contains a fluorescent compound M1. The compound M1 of this embodiment is not a phosphorescent metal complex. The compound M1 of this embodiment is preferably not a heavy metal complex. Furthermore, the compound M1 of this embodiment is preferably not a metal complex. Furthermore, the compound M1 of this embodiment is preferably 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 compound M1 is a fluorescent compound, compound M1 preferably exhibits emission with a maximum peak wavelength of 400 nm or more and 700 nm or less. In this specification, the maximum peak wavelength is the wavelength at which the compound to be measured is 10 -6 moles / liter over 10 -5 This is the peak wavelength of the fluorescence spectrum at which the emission intensity is maximum in the fluorescence spectrum measured for a toluene solution in which the compound is dissolved at a concentration of 1 / 4 mole / liter or less. The measurement device is a spectrofluorometer (Hitachi High-Tech Science, F-7000).

[0256] Compound M1 preferably exhibits red or green emission. In this specification, red light emission refers to light emission whose maximum peak wavelength in the fluorescence spectrum is in the range of 600 nm or more and 660 nm or less. When compound M1 is a red fluorescent compound, the maximum peak wavelength of compound M1 is preferably 600 nm or more and 660 nm or less, more preferably 600 nm or more and 640 nm or less, and even more preferably 610 nm or more and 630 nm or less. In this specification, green light emission refers to light emission whose maximum peak wavelength in the fluorescence spectrum is in the range of 500 nm or more and 560 nm or less. When compound M1 is a green fluorescent compound, the maximum peak wavelength of compound M1 is preferably 500 nm or more and 560 nm or less, more preferably 500 nm or more and 540 nm or less, and even more preferably 510 nm or more and 540 nm or less. In this specification, blue light emission refers to light emission whose maximum peak wavelength in the fluorescence spectrum is in the range of 430 nm or more and 480 nm or less. 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. Current density is 10mA / cm 2 The spectral radiance spectrum when a voltage is applied to the organic EL element so that the spectral radiance is as follows: In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum where 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 this embodiment, the compound M1 is preferably a compound represented by the following general formula (2A): The compound M1 is preferably a compound that emits light with 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] [ka]

[0260] (In the general formula (2A), The Za ring, the Zb ring and the Zc ring 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 bonds with the Za ring or the Zb ring to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle; Rb bonds with the Za ring or the Zc ring to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle; The Ra and Rb that do not form the substituted or unsubstituted heterocycle 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 It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0261] (Compound represented by general formula (D11)) In this embodiment, the compound M1 is also preferably a compound represented by the following general formula (D11): The compound represented by the general formula (2A) is also preferably a compound represented by the following general formula (D11). When a compound represented by the following general formula (D11) is used as 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 compound M1. When a compound represented by the following general formula (D11) is used as compound M1, the external quantum efficiency and lifetime can be improved compared to when a compound having a pyrromethene skeleton is used as compound M1.

[0262] [ka]

[0263] (In the general formula (D11), Rb has the same meaning as Rb in the general formula (2A), X1 is CR1 or a nitrogen atom; X2 is CR2 or a nitrogen atom; X3 is CR3 or a nitrogen atom; X4 is CR4 or a nitrogen atom; X5 is CR5 or a nitrogen atom; X6 is CR6 or a nitrogen atom, X7 is CR7, a nitrogen atom, or a carbon atom bonded to X8 by a single bond; X8 is CR8, a nitrogen atom, or a carbon atom bonded to X7 by a single bond; X9 is CR9 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, R1 to R6 and R9 to R 11 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 3、 One or more pairs of adjacent two or more of R4 and Rb are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 3、At least one hydrogen atom in a single ring or a fused ring formed by bonding one or more pairs of adjacent two or more of R4 and Rb is 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, -O-(R 920 ), and -N(R 921 )(R 922 or is unsubstituted with at least one substituent selected from the group consisting of groups represented by at least one hydrogen atom in the substituent is either unsubstituted or substituted with an aryl group having 6 to 50 ring carbon atoms or an alkyl group having 1 to 50 carbon atoms; R to R do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring. 11 , and R 12 ~R 13 , and R Q are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 918 a group represented by -COOR919 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, The Rb which 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, R 911 ~R 922 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 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, R915 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 919 If 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 either identical or different.)

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

[0265] [ka]

[0266] (In the general formula (D13), R1 to R3, R5 to R 13 and R Q each independently represents R1 to R3 and R5 to R 13 and R Q is synonymous with R A1 ~R A4 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring A1 ~R A4 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -Si(R 931 )(R 932 )(R 933 ) a group represented by -O-(R 934 ) a group represented by -S-(R 935 ) a group represented by -N(R 936 )(R 937 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 938 a group represented by -COOR 939 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 931 ~R 939 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or 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 either identical or different.)

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

[0268] [ka]

[0269] (In the general formula (D13A), R1, R3, R5 to R 13 , R Q and R A1 ~RA4 each independently represents R1, R3, R5 to R in general formula (D13). 13 , R Q and R A1 ~R A4 is synonymous with R A5 ~R A9 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring A5 ~R A9 each independently represents an R in the 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 equivalent to

[0270] In the general formulae (D13) and (D13A), for example, a pair consisting of R5 and R6 may bond to each other to form a substituted or unsubstituted monocycle, or to form a substituted or unsubstituted fused ring, or not to be bonded to each other.

[0271] In the compound represented by the general formula (D11), R1 to R 13 and R Q are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or A substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms is also preferred.

[0272] In the compound represented by the general formula (D11), R1 to R 13 and R Q are each independently, hydrogen atoms, 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 is also preferred.

[0273] In the compounds represented by the general formulas (D13) and (D13A), R1 to R3, R5 to R 13 , R Q and R A1 ~R A9 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or A substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms is also preferred.

[0274] In the compounds represented by the general formulas (D13) and (D13A), R1 to R3, R5 to R 13 , R Q and R A1 ~R A9 are each independently, hydrogen atoms, 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 is also preferred.

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

[0276] [ka]

[0277] (In the compound represented by the general formula (D14), R2, R 6、 R 13、R Q and R A2 are each independently, hydrogen atoms, 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 It is a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms.

[0278] In the general formula (D14), R 13 and R Q are 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 is preferred.

[0279] In the compound represented by the general formula (D14), R6 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 this embodiment, the 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] [ka]

[0282] (In the compound represented by the general formula (16), R 161 ~R 177 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 161 ~R 177 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, 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 group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 961 ~R969 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or 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 964 If 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 either identical or different.)

[0283] In the compound represented by the general formula (16), R 161 ~R 177 are each independently, hydrogen atoms, 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 is preferred.

[0284] In the compound represented by the general formula (16), R 168 ~R 170 At least one of the a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

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

[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 be bonded to each other to form a ring represented by the following general formula (16A).

[0288] [ka]

[0289] (The dotted line in the general formula (16A) represents a bonding site, R X1 ~R X4 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, 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 group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[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 161 and 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 the pair consisting of these is 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] [ka]

[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 ~R177 and R in the general formula (16A) X1 ~R X4 is equivalent to

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

[0298] [ka]

[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 equivalent to

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

[0301] [ka]

[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 equivalent to

[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 by various methods, such as a solid line, a dashed line, an arrow, or omitted. In this specification, it is represented by a solid line, a dashed line, or is omitted.

[0306] [ka]

[0307] [ka]

[0308] [ka]

[0309] [ka]

[0310] [ka]

[0311] [ka]

[0312] [ka]

[0313] [ka]

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[0315]

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[0317]

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[0325] [ka]

[0326] <Relationship between Compound M3, Compound M2, and Compound M1 in the Light-Emitting Layer> In the organic EL device of this embodiment, it is preferable that the singlet energy S1(M1) of the compound M1 and the singlet energy S1(M2) of the compound M2 satisfy the relationship of the following mathematical formula (Mathematical Formula 2). S1(M2)>S1(M1) (Math 2)

[0327] Furthermore, the singlet energy S1(M3) of the compound M3 is preferably larger than the singlet energy S1(M1) of the compound M1.

[0328] The singlet energy S1(M3) of the compound M3, the singlet energy S1(M2) of the compound M2, and the singlet energy S1(M1) of the compound M1 preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 2A). S1(M3)>S1(M2)>S1(M1)…(Number 2A)

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

[0330] Compound content in the light-emitting layer The contents of the compounds M3, M2, and 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 compounds M3, M2, and M1 in the light-emitting layer is 100 mass %. Note that this embodiment does not exclude the light-emitting layer containing materials other than compounds M3, M2, and M1. The light-emitting layer may contain only one type of compound M3 or two or more types thereof. 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] FIG. 5 shows 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 via this TADF mechanism.

[0332] The organic EL device 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 larger 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 equipment] The electronic device according to this embodiment is equipped with the organic EL element according to any one of the above-described embodiments. Examples of the electronic device include a display device and a light-emitting device. Examples of the display device include display components (e.g., an organic EL panel module), a television, a mobile phone, a tablet, and a personal computer. Examples of the light-emitting device include lighting and vehicle lighting fixtures.

[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 according to the fourth embodiment, a high-performance organic EL device can be realized.

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

[0336] Fifth Embodiment [Materials for organic EL devices] 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, it is possible to realize a high-performance organic EL device and electronic equipment. 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 and improvements 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 due to electron transition from a triplet excited state directly to the ground state. Furthermore, when the organic EL element has a plurality of light-emitting layers, these light-emitting layers may be provided adjacent to each other, or the organic EL element may be a so-called tandem type organic EL element in which a plurality of light-emitting units are stacked via an intermediate layer.

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

[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. [Example]

[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] <Compound> 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] [ka]

[0344] [ka]

[0345] [ka]

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

[0347] [ka]

[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] [ka]

[0350] [ka]

[0351] [ka]

[0352] [ka]

[0353] <Fabrication of organic EL element 1> An organic EL device was fabricated and evaluated as follows.

[0354] Example 1 A 25mm x 75mm x 1.1mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 1 minute. The ITO film thickness was 130nm. The glass substrate with the cleaned transparent electrode lines was mounted on a substrate holder of a vacuum deposition apparatus, and the compound HT1 and the compound HA were co-deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 10 nm. The concentration of the compound HT1 in the hole injection layer was 97% by mass, and the concentration of the compound HA was 3% by mass. Next, the compound HT1 was vapor-deposited on the hole injection layer to form a first hole transport layer with a thickness of 110 nm on the hole injection layer. Next, the compound HT2 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 5 nm. Next, the compound HT3 was vapor-deposited on this second hole transport layer to form an electron blocking layer with a thickness of 5 nm. Next, on this electron blocking layer, compound M3-1 as compound M3 and compound TADF-1 as delayed fluorescent compound M2 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 75 mass %, and the concentration of compound TADF-1 was 25 mass %. Next, the compound HBL was vapor-deposited on this light-emitting layer to form a hole-blocking layer with a thickness of 5 nm. Next, the compound ET was vapor-deposited on this hole-blocking layer to form an electron-transporting layer with a thickness of 50 nm. Next, lithium fluoride (LiF) was vapor-deposited on this electron transport layer to form an electron injecting electrode (cathode) with a film thickness of 1 nm. Then, metallic aluminum (Al) was vapor-deposited on this electron injecting electrode to form a metallic Al cathode with a film thickness of 80 nm. The device configuration of the organic EL device according to Example 1 is shown in outline below. 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 of organic EL elements 1> Current density is 10mA / cm 2 It was confirmed that when a voltage was applied to the organic EL element produced in Example 1, light was emitted.

[0356] <Fabrication of organic EL element 2> An organic EL device was fabricated and evaluated as follows.

[0357] Example 2 A 25mm x 75mm x 1.1mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 1 minute. The ITO film thickness was 130nm. The glass substrate with the cleaned transparent electrode lines was mounted on a substrate holder of a vacuum deposition apparatus, and the compound HT4 and the compound HA were co-deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 10 nm. The concentration of the compound HT4 in the hole injection layer was 97% by mass, and the concentration of the compound HA was 3% by mass. Next, the compound HT4 was vapor-deposited on the hole injection layer to form a first hole transport layer with a thickness of 110 nm on the hole injection layer. Next, the compound HT2 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 5 nm. Next, the compound HT3 was vapor-deposited on this second hole transport layer 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 mass %, the concentration of compound TADF-2 was 20 mass %, and the concentration of compound FD was 0.8 mass %. Next, the compound HBL2 was vapor-deposited on this light-emitting layer to form a hole-blocking layer with a thickness of 5 nm. Next, on this hole blocking layer, the compound ET2 and the compound Liq were deposited by vapor deposition to form an electron transport layer with a thickness of 50 nm, in which the concentration of the compound ET2 was 50 mass % and the concentration of the compound Liq was 50 mass %. Next, Yb was vapor-deposited on this electron transport layer to form an electron injection electrode (cathode) with a film thickness of 1 nm. Then, metallic aluminum (Al) was vapor-deposited on this electron injecting electrode to form a metallic Al cathode with a film thickness of 80 nm. The device configuration of the organic EL device according to Example 2 is shown in outline below. 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 percentages (97%:3%) indicate the proportions (mass%) of compound HT4 and compound HA in the hole injection layer, the percentages (79.2%:20%:0.8%) indicate the proportions (mass%) of compound M3, compound M2, and compound M1 in the light-emitting layer, and the percentages (50%:50%) indicate the proportions (mass%) of compound ET2 and compound 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 and 9 The organic EL devices of Examples 8 and 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 of 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 Elements 2> The produced organic EL devices were evaluated as follows. The evaluation results are shown in Tables 1 and 2. The evaluation results for 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 is 10mA / 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 λ p (unit: nm) was calculated.

[0363] (External quantum efficiency EQE) Current density is 10mA / cm 2 The spectral radiance spectrum when a voltage was applied to the element so that the value was as follows was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit: %) was calculated, assuming that Lambertian radiation was used.

[0364] (Life span LT95) The organic EL device was fabricated with 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] [Table 1]

[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] [Table 2]

[0368] The organic EL devices of Examples 8 to 19, which contained the compound M3 represented by general formula (1), the delayed fluorescent compound M2, and the fluorescent compound M1 in the light-emitting layer, emitted light with higher efficiency than the organic EL device of Comparative Example 1. Furthermore, when Examples 8 to 14 are compared with Examples 15 to 19, the organic EL devices of Examples 8 to 14, which used the 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 the compound (FD-3) having a pyrromethene skeleton as the fluorescent compound M1. Comparing Examples 8 to 9 with Examples 10 to 11, Examples 8 to 9, which used the compound (FD) represented by general formula (16) as the fluorescent compound M1, had a longer lifetime than Examples 10 to 11, which used the compound (FD-2) represented by general formula (D11) as the fluorescent compound M1. On the other hand, Examples 10 to 11, which used the 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 the compound (FD) represented by general formula (16) as the fluorescent compound M1. Comparing Examples 10 to 14, 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, Example 11, which used compound (M3-12) represented by general formula (12A) where X1 in A is a sulfur atom, showed more significant improvements in external quantum efficiency and lifetime.

[0369] <Compound evaluation> 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 the compound TADF-1) Delayed fluorescence was confirmed by measuring transient PL using the apparatus shown in Figure 2. The 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 create an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the sample solution was measured using a spectrofluorometer FP-8600 (JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. The total fluorescence quantum yield was calculated using the fluorescence area intensity of both spectra according to equation (1) in Morris et al. J. Phys. Chem. 80 (1976) 969. After being excited by pulsed light (light irradiated from a pulsed laser) of a wavelength absorbed by the compound TADF-1, there are two types of emission: prompt emission (immediate emission) that is observed immediately from the excited state, and delayed emission (delayed emission) that is not observed immediately after the excitation but is observed later. In this example, delayed fluorescence emission means that the amount of delayed emission (delayed emission) is 5% or more of the amount of prompt emission (immediate emission). Specifically, when the amount of prompt emission (immediate emission) is X P and the amount of delay light emission is X D When X D / X P This means that the value of is 0.05 or more. The amounts of prompt luminescence and delay luminescence and their ratio can be determined by a method similar to that described in "Nature 492, 234-238, 2012" (Reference 1). Note that the device used to calculate the amounts of prompt luminescence and delay luminescence is not limited to the device described in Reference 1 or the device shown in FIG. 2. It was confirmed that the amount of delayed luminescence (delayed luminescence) of the compound TADF-1 was 5% or more of the amount of prompt luminescence (immediate luminescence). Specifically, for the compound TADF-1, X D / X P The value was 0.05 or higher.

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

[0372] Singlet energy S1 The singlet energies S1 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 were 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 dividing the energy gap T 77K It was measured by the measurement method of T 77K ΔST was confirmed from the measurement results and the value of the singlet energy S1 mentioned above.

[0374] The compound's maximum peak wavelength λ The maximum peak wavelength λ of the compound TADF-1, and the compounds 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 measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum was defined as the maximum peak wavelength λ.

[0375] [Table 3]

[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] [ka]

[0379] Under a nitrogen atmosphere, 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) was added to xylene (200 mL) and stirred at 140 °C for 5 h. After the reaction was completed, water was added, and the solid was filtered and recrystallized using toluene to obtain compound M3-1 (9.37 g, 46% yield). The product was identified as compound M3-1 by LC-MS (Liquid Chromatography-Mass Spectrometry).

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

[0381] [ka]

[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] [ka]

[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] [ka]

[0388] Under a nitrogen atmosphere, 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) was added to 1,2-dimethoxyethane (267 mL) and water (133 mL) and 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 give 1-(3-chlorophenyl)dibenzo[b,d]furan (10.8 g, 95% yield).

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

[0390] [ka]

[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] [ka]

[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] [ka]

[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. The mixture was stirred at 110 °C for 2 h. After the reaction was complete, 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] [ka]

[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] [ka]

[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] [ka]

[0406] Compound M3-9 was obtained in the same manner as in Synthesis Example 6 (6-1), except that 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] [ka]

[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. The mixture was stirred at 110 °C for 3.5 h. After the reaction was complete, the solid was collected by filtration, washed with methanol, and recrystallized using toluene to obtain compound M3-10 (1.44 g, 41% yield). LC-MS analysis identified the product as compound M3-10.

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

[0411] [ka]

[0412] Compound M3-11 was obtained in the same manner as in Synthesis Example 10 (10-1), except that 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%. LC-MS analysis identified the compound as M3-11.

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

[0414] [ka]

[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] [ka]

[0418] Compound M3-13 was obtained in the same manner as in Synthesis Example 10 (10-1), except that 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 in Synthesis Example 10 (10-1). The yield was 53%. LC-MS analysis identified the compound as M3-12.

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

[0420] [ka]

[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), dibenzylideneacetone palladium (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 the reaction was completed, the solid was filtered, 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 compound M3-15. [Explanation of symbols]

[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; a light-emitting layer between the anode and the cathode, The light-emitting layer contains a compound M3 represented by the following general formula (1) and a delayed fluorescent 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) satisfies the relationship of the following formula (Formula 1), Organic electroluminescent element. S １ (M3) > S １ (M2) (Number 1) 【Chemistry 1】 (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), 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 pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 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, hydrogen atoms, halogen atoms, 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, hydroxy groups, 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 group represented by thiol groups, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms, substituted germanium groups, substituted phosphine oxide groups, 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, Multiple R １００ are identical to 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. In the general formula (1), * represents R ２１ ~R ２４ represents the bonding position to any one of the carbon atoms of the six-membered ring to which 【Chemistry 2】 (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 pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R １５ ~R １８ One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 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 is synonymous with However, when n is 0, * represents 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

2. 2. The organic electroluminescent device according to claim 1, n is 1; Organic electroluminescent element.

3. 3. The organic electroluminescent device according to claim 1, The compound M3 is a compound represented by the following general formula (12A): Organic electroluminescent element. 【Transformation 3】 (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

4. 3. The organic electroluminescent device according to claim 1, The compound M3 is a compound represented by the following general formula (12B): Organic electroluminescent element. 【Chemistry 4】 (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

5. 3. The organic electroluminescent device according to claim 1, The compound M3 is a compound represented by the following general formula (12C): Organic electroluminescent element. 【Transformation 5】 (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

6. 2. The organic electroluminescent device according to claim 1, n is 0, or n is 1 and R １００ is a hydrogen atom, Organic electroluminescent element.

7. 7. The organic electroluminescent device according to claim 6, n is 0; Organic electroluminescent element.

8. The organic electroluminescent device according to any one of claims 1 to 7, A is a group represented by the general formula (11A), (11B), (11C), (11E) or (11F). Organic electroluminescent element.

9. The organic electroluminescent device according to any one of claims 1 to 7, A is a group represented by the general formula (11E) or (11F). Organic electroluminescent element.

10. The organic electroluminescence device according to claim 9, A is a group represented by the general formula (11F). Organic electroluminescent element.

11. The organic electroluminescence device according to any one of claims 1 to 10, X １ is an oxygen atom, Organic electroluminescent element.

12. The organic electroluminescence device according to any one of claims 1 to 10, X １ and Y １ is an oxygen atom, Organic electroluminescent element.

13. The organic electroluminescence device according to any one of claims 1 to 10, X １ is a sulfur atom, Organic electroluminescent element.

14. The organic electroluminescence device according to claim 13, The compound M3 is a compound represented by the following general formula (12A-1): Organic electroluminescent element. 【Transformation 6】 (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), 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 【Transformation 7】 (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.)

15. The organic electroluminescent device according to any one of claims 1 to 14, Y １ is an oxygen atom, Organic electroluminescent element.

16. The organic electroluminescent device according to any one of claims 1 to 5, The compound M3 is a compound represented by the following general formula (100): Organic electroluminescent element. 【Transformation 8】 (In the general formula (100), X １ is an oxygen atom or a sulfur atom, R １９ and R ２０ is a hydrogen atom, R １００ , R １１ ~R １８ , and R ２２ ~R ２８ are each independently, hydrogen atoms, - (L １０１ ) nx-R １０１ is a group represented by nx is 0, 1, 2 or 3; - (L １０１ ) nx-R １０１ When a plurality of groups represented by -(L １０１ ) nx-R １０１ are the same or different, Multiple R １００ are identical to or different from each other, R １０１ teeth, 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): A monovalent group derived from a compound represented by the following general formula (106): L １０１ teeth, 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): A divalent group derived from a compound represented by the following general formula (106): L １０１ is 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, each of the substituents independently represents 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, there are two or more L １０１ are identical to or different from each other, R １０１ When two or more R １０１ are identical to or different from each other, However, * is R １００ represents the bonding position of any one of the carbon atoms of the benzene ring to which 【Chemistry 9】 (In the general formulae (101) to (106), X １Ｘ is an oxygen atom or a sulfur atom, R １１Ｘ ~R ２１Ｘ are each independently, hydrogen atoms, 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 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 １８ , 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 ~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 L １０１ and combine. L 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 １８ , 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 １８ , R ２２ ~R ２８ and R １００ any one of the carbon atoms of the six-membered ring to which L is bonded １０１ )

17. 2. The organic electroluminescent device according to claim 1, When n is 0, R ２５ is not a substituted or unsubstituted dibenzofuranyl group, nor is it a substituted or unsubstituted dibenzothienyl group; Organic electroluminescent element.

18. The organic electroluminescence device according to claim 17, When n is 0, R ２１ ~R ２８ is not a substituted or unsubstituted dibenzofuranyl group, nor is it a substituted or unsubstituted dibenzothienyl group; Organic electroluminescent element.

19. The organic electroluminescence device according to claim 17 or 18, When n is 0, in the general formula (1), R ２２ The carbon atom of the six-membered ring to which is bonded is not bonded to *. Organic electroluminescent element.

20. 20. The organic electroluminescence device according to claim 1, In the general formulae (11A), (11B), (11C), (11D), (11E) and (11F), R １１ ~R １８ is a hydrogen atom, Organic electroluminescent element.

21. 2. The organic electroluminescent device according to claim 1, In the light-emitting layer, the singlet energy S １ (M2) Singlet energy S １ The compound having the formula: Organic electroluminescent element.

22. 22. The organic electroluminescence device according to claim 21, When n is 1, R １００ is not a substituted or unsubstituted dibenzofuranyl group, Organic electroluminescent element.

23. The organic electroluminescent device according to any one of claims 1 to 22, the light-emitting layer further comprises 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) satisfies the relationship of the following formula (Formula 2): Organic electroluminescent element. S １ (M2) > S １ (M1)…(Number 2)

24. 24. The organic electroluminescence device according to claim 23, The compound M1 is represented by the following general formula (2A), and the compound M1 exhibits emission having a maximum peak wavelength of 500 nm or more and 560 nm or less: Organic electroluminescent element. 【Chemistry 10】 (In the general formula (2A), The ring Za, the ring Zb and the 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 either bonds with the Za ring or the Zb ring to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle; Rb bonds with the Za ring or the Zc ring to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle; Ra and Rb that do not form the substituted or unsubstituted heterocycle 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 It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

25. The organic electroluminescent device according to any one of claims 1 to 24, The light-emitting layer does not contain a metal complex. Organic electroluminescent element.

26. An electronic device equipped with the organic electroluminescence element according to any one of claims 1 to 25.

27. A compound represented by the following general formula (100): 【Chemistry 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, hydrogen atoms, - (L １０１ ) nx-R １０１ is a group represented by nx is 0, 1, 2 or 3; - (L １０１ ) nx-R １０１ When a plurality of groups represented by -(L １０１ ) nx-R １０１ are the same or different, Multiple R １００ are identical to or different from each other, R １０１ teeth, 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): A monovalent group derived from a compound represented by the following general formula (106): L １０１ teeth, 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): A divalent group derived from a compound represented by the following general formula (106): L １０１ is 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, each of the substituents independently represents 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, there are two or more L １０１ are identical to or different from each other, R １０１ When two or more R １０１ are identical to or different from each other, However, * is R １００ represents the bonding position of any one of the carbon atoms of the benzene ring to which 【Chemistry 12】 (In the general formulae (101) to (106), X １Ｘ is an oxygen atom or a sulfur atom, R １１Ｘ ~R ２１Ｘ are each independently, hydrogen atoms, 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 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 ~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 L １０１ and combine. L 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 )

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