Organic electroluminescent element and electronic device

Abstract

Provided is an organic electroluminescent element (1A) comprising a positive electrode (3), a first layer (71), a light-emitting layer (5), a second layer (81), and a negative electrode (4) in this order, wherein the light-emitting layer (5) contains a delayed fluorescence compound as a second compound, the content of the second compound in the light-emitting layer (5) is 30-50 mass%, the first layer (71) contains a fourth compound, the second layer (72) contains a fifth compound, the fourth compound and the fifth compound are different from each other, and expression 51 and expression 52 are satisfied.　Expression 51: |HOMO(M4)|≥5.74 eV Expression 52: T77K(M5)≤2.90 eV (HOMO(M4) is the energy level of the highest occupied molecular orbital, and T77K(M5) is the energy gap at 77[K].)

Description

Organic electroluminescence element and electronic device

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

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

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

[0004] For example, Patent Documents 1 and 2 describe organic EL devices having an emitting layer containing a delayed fluorescent compound, and Patent Documents 1 and 2 also describe organic EL devices having an electron blocking layer containing a specific compound.

[0005] International Publication No. WO 2022 / 260117 International Publication No. WO 2020 / 241580

[0006] In order to improve the performance of electronic devices such as displays, there is a demand for further improvements in the performance of organic EL elements, such as luminance, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan.

[0007] An object of the present invention is to provide an organic electroluminescent element capable of improving luminous efficiency or realizing a longer life, and to provide an electronic device incorporating the organic electroluminescent element.

[0008] According to one aspect of the present invention, there is provided an organic electroluminescence device comprising an anode, a cathode, an emitting layer between the anode and the cathode, a first layer between the anode and the emitting layer, and a second layer between the cathode and the emitting layer, wherein the emitting layer contains a delayed fluorescent compound as a second compound, the content of the second compound in the emitting layer being 30% by mass or more and 50% by mass or less, the first layer contains a fourth compound, the second layer contains a fifth compound, the fourth compound and the fifth compound are different from each other, the fourth compound satisfies the following mathematical formula (Mathematical Formula 51), and the fifth compound satisfies the following mathematical formula (Mathematical Formula 52). ７７Ｋ (M5)≦2.90 eV (HOMO(M4) is the energy level of the highest occupied molecular orbital of the fourth compound, T ７７Ｋ (M5) is the energy gap of the fifth compound at 77 K.

[0009] 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.

[0010] According to one embodiment of the present invention, it is possible to provide an organic electroluminescence element capable of improving luminous efficiency or realizing a long life, and to provide an electronic device equipped with the organic electroluminescence element.

[0011] 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; 2 is a schematic diagram of an apparatus for measuring transient PL; 3 is a diagram showing an example of a decay curve of transient PL; 4 is a diagram showing the energy levels of a first compound, a second compound, and a third compound in an emitting layer of an example of an organic electroluminescence element according to a first embodiment of the present invention, and the relationship between energy transfer; 5 is a diagram showing the energy levels of a second compound and a third compound in an emitting layer of an example of an organic electroluminescence element according to a second embodiment of the present invention, and the relationship between energy transfer;

[0012] [Definitions] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0013] In this specification, in a chemical structural formula, a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded to a possible bonding position that is not explicitly indicated with a symbol such as "R" or "D" representing a deuterium atom.

[0014] As used herein, the term "number of ring carbon atoms" refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. For example, a 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and a 9,9'-spirobifluorenyl group has 25 ring carbon atoms. When a benzene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of a benzene ring substituted with an alkyl group is 6. Furthermore, when the naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.

[0015] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, and a ring assembly). Atoms that do not constitute the ring (e.g., hydrogen atoms terminating the bonds of atoms constituting the ring) and atoms contained in the substituent when the ring is substituted with a substituent are not included in the number of ring atoms. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms or atoms constituting a substituent bonded to the pyridine ring is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. Furthermore, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring, so the number of ring atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

[0016] In this specification, the "number of carbon atoms XX to YY" in the expression "substituted or unsubstituted ZZ group having carbon atoms XX to YY" represents the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0017] In this specification, the "number of atoms XX to YY" in the expression "substituted or unsubstituted ZZ group having number of atoms XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of substituents when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0018] In this specification, an unsubstituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group". In this specification, "unsubstituted" in the case of a "substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protist atom, a deuterium atom, or a tritium atom. Furthermore, in this specification, "substituted" in the case of a "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. Similarly, "substituted" in the case of a "BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced with an AA group.

[0019] "Substituents Described in This Specification" The substituents described in this specification are explained below.

[0020] The number of ring carbon atoms of an "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring atoms of an "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms of an "unsubstituted alkyl group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein. The number of carbon atoms of an "unsubstituted alkenyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of carbon atoms of an "unsubstituted alkynyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of ring carbon atoms of an "unsubstituted cycloalkyl group" described herein is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified herein. Unless otherwise specified herein, the number of ring carbon atoms of an "unsubstituted arylene group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18. Unless otherwise specified herein, the number of ring atoms of an "unsubstituted divalent heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18. Unless otherwise specified herein, the number of carbon atoms of an "unsubstituted alkylene group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0021] "Substituted or Unsubstituted Aryl Group" Specific examples (Specific Example Group G1) of the "substituted or unsubstituted aryl group" described herein include the following unsubstituted aryl group (Specific Example Group G1A) and substituted aryl group (Specific Example Group G1B). (Here, an unsubstituted aryl group refers to a case where a "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and a substituted aryl group refers to a case where a "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" simply refers to both an "unsubstituted aryl group" and a "substituted aryl group." A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with substituents. Examples of the "substituted aryl group" include a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with substituents in the "unsubstituted aryl group" of the following Specific Example Group G1A, and examples of the substituted aryl group of the following Specific Example Group G1B. It should be noted that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl groups" described in this specification also include groups in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl groups" of the following specific example group G1B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted aryl groups" of the following specific example group G1B is further replaced with a substituent.

[0022] Unsubstituted aryl groups (specific example group G1A): a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a benzanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a triphenylenyl group, a benzotriphenylenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, A 9,9'-spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a fluoranthenyl group, a benzofluoranthenyl group, a perylenyl group, and a monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0023]

[0024]

[0025] Substituted aryl groups (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, cyanophenyl group, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl group, and A group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by the above general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0026] "Substituted or Unsubstituted Heterocyclic Group" The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom among the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom. The "heterocyclic group" described herein is a monocyclic group or a fused ring group. The "heterocyclic group" described herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described herein include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, an unsubstituted heterocyclic group refers to when a "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and a substituted heterocyclic group refers to when a "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when simply referring to a "heterocyclic group", it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group". A "substituted heterocyclic group" means a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with substituents. Specific examples of the "substituted heterocyclic group" include groups in which hydrogen atoms of an "unsubstituted heterocyclic group" in the following specific example group G2A are replaced, and examples of substituted heterocyclic groups in the following specific example group G2B. The examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic groups" described in this specification also include groups in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic groups" of specific example group G2B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted heterocyclic groups" of specific example group G2B is further replaced with a substituent.

[0027] 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).

[0028] Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced with substituents (specific example group G2B4).

[0029] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolidinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, an indazolyl group, a phenanthrolinyl group, a phenanthridinyl group, an acridinyl group, a phenazinyl group, a carbazolyl group, Benzocarbazolyl group, morpholino group, phenoxazinyl group, phenothiazinyl group, azacarbazolyl group, and diazacarbazolyl group.

[0030] Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): a furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a xanthenyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a benzoxazolyl group, a benzisoxazolyl group, a phenoxazinyl group, a morpholino group, a dinaphthofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, an azanaphthobenzofuranyl group, and a diazanaphthobenzofuranyl group.

[0031] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a benzothiophenyl group (benzothienyl group), an isobenzothiophenyl group (isobenzothienyl group), a dibenzothiophenyl group (dibenzothienyl group), a naphthobenzothiophenyl group (naphthobenzothienyl group), a benzothiazolyl group, a benzisothiazolyl group, a phenothiazinyl group, a dinaphthothiophenyl group (dinaphthothienyl group), an azadibenzothiophenyl group (azadibenzothienyl group), a diazadibenzothiophenyl group (diazadibenzothienyl group), an azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and a diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0032] 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):

[0033]

[0034]

[0035] In the general formulae (TEMP-16) to (TEMP-33), X Ａ and Y Ａ are each independently an oxygen atom, a sulfur atom, NH, or CH ２ However, X Ａ and Y Ａ At least one of X is an oxygen atom, a sulfur atom, or NH. Ａ and Y Ａ At least one of the groups is NH or CH ２ In this case, the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) may contain any of these NH, CH ２ and monovalent groups obtained by removing one hydrogen atom from the group consisting of:

[0036] Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): a (9-phenyl)carbazolyl group, a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a (9-naphthyl)carbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a methylbenzimidazolyl group, an ethylbenzimidazolyl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenylquinazolinyl group, and a biphenylylquinazolinyl group.

[0037] Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): a phenyldibenzofuranyl group, a methyldibenzofuranyl group, a t-butyldibenzofuranyl group, and a monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0038] Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3): a phenyldibenzothiophenyl group, a methyldibenzothiophenyl group, a t-butyldibenzothiophenyl group, and a monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0039] 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):

[0040] The "one or more hydrogen atoms of the monovalent heterocyclic group" refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, X Ａ and Y Ａ a hydrogen atom bonded to a nitrogen atom when at least one of Ａ and Y Ａ One of them is CH ２ and n is 0 or more. The methylene group in the formula (I) is one or more hydrogen atoms selected from the hydrogen atoms of the methylene group in the formula (I).

[0041] "Substituted or Unsubstituted Alkyl Group" Specific examples (Specific Example Group G3) of the "substituted or unsubstituted alkyl group" described herein include the following unsubstituted alkyl group (Specific Example Group G3A) and substituted alkyl group (Specific Example Group G3B). (Here, the term "unsubstituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and the term "substituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereinafter, the term "alkyl group" includes both an "unsubstituted alkyl group" and a "substituted alkyl group." A "substituted alkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced with substituents. Specific examples of the "substituted alkyl group" include the following "unsubstituted alkyl group" (Specific Example Group G3A) in which one or more hydrogen atoms are replaced with substituents, and the examples of the substituted alkyl group (Specific Example Group G3B). In this specification, the alkyl group in an "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the term "unsubstituted alkyl group" includes a straight-chain "unsubstituted alkyl group" and a branched "unsubstituted alkyl group." The examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes groups in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" of specific example group G3B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted alkyl group" of specific example group G3B is further replaced with a substituent.

[0042] Unsubstituted alkyl groups (specific example group G3A): a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, and a t-butyl group.

[0043] Substituted alkyl groups (specific example group G3B): a heptafluoropropyl group (including isomers), a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, and a trifluoromethyl group.

[0044] "Substituted or Unsubstituted Alkenyl Group" Specific examples (Specific Example Group G4) of the "substituted or unsubstituted alkenyl group" described herein include the following unsubstituted alkenyl group (Specific Example Group G4A) and substituted alkenyl group (Specific Example Group G4B). (Here, an unsubstituted alkenyl group refers to a case where a "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and a "substituted alkenyl group" refers to a case where a "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply refers to both an "unsubstituted alkenyl group" and a "substituted alkenyl group." A "substituted alkenyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced with substituents. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl groups" (specific example group G4A) having a substituent, and examples of substituted alkenyl groups (specific example group G4B). The examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl group" described in this specification also includes groups in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl groups" of specific example group G4B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted alkenyl groups" of specific example group G4B is further replaced with a substituent.

[0045] Unsubstituted alkenyl groups (specific example group G4A): a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, and a 3-butenyl group.

[0046] Substituted alkenyl groups (specific example group G4B): a 1,3-butadienyl group, a 1-methylvinyl group, a 1-methylallyl group, a 1,1-dimethylallyl group, a 2-methylallyl group, and a 1,2-dimethylallyl group.

[0047] - "Substituted or Unsubstituted Alkynyl Group" Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl group (specific example group G5A). (Here, an unsubstituted alkynyl group refers to a case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, the term "alkynyl group" includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group." A "substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" have been replaced with a substituent. Specific examples of the "substituted alkynyl group" include a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" (specific example group G5A) have been replaced with a substituent.

[0048] Unsubstituted alkynyl groups (specific example group G5A): ethynyl groups.

[0049] "Substituted or Unsubstituted Cycloalkyl Group" Specific examples (Specific Example Group G6) of the "substituted or unsubstituted cycloalkyl group" described herein include the following unsubstituted cycloalkyl group (Specific Example Group G6A) and substituted cycloalkyl group (Specific Example Group G6B). (Here, the term "unsubstituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group," and the term "substituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group.") In this specification, the term "cycloalkyl group" simply refers to both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group." A "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced with substituents. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (Specific Example Group G6A) in which one or more hydrogen atoms are replaced with substituents, and the examples of the substituted cycloalkyl group (Specific Example Group G6B). The examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed here are merely examples, and the "substituted cycloalkyl groups" described in this specification also include groups in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl groups" of specific example group G6B are replaced with substituents, and groups in which a hydrogen atom of a substituent in the "substituted cycloalkyl groups" of specific example group G6B is further replaced with a substituent.

[0050] Unsubstituted cycloalkyl groups (specific example group G6A): a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a 2-norbornyl group.

[0051] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.

[0052] -Si(R ９０１ ) (R ９０２ ) (R ９０３ A group represented by —Si(R ９０１ ) (R ９０２) (R ９０３ Specific examples (specific example group G7) of the group represented by the formula (G1) include -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. The multiple G1s in -Si(G1)(G1)(G1) may be the same or different. - Multiple G2 in Si(G1)(G2)(G2) are the same as or different from each other. - Multiple G1 in Si(G1)(G1)(G2) are the same as or different from each other. - Multiple G2 in Si(G2)(G2)(G2) are the same as or different from each other. - Multiple G3 in Si(G3)(G3)(G3) are the same as or different from each other. - Multiple G6 in Si(G6)(G6)(G6) are the same as or different from each other.

[0053] ・「-O-(R ９０４ A group represented by —O—(R ９０４ ) (Specific example group G8) includes -O(G1), -O(G2), -O(G3), and -O(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0054] ・"-S-(R ９０５ A group represented by —S—(R ９０５) (Specific example group G9) includes -S(G1), -S(G2), -S(G3), and -S(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0055] ・「-N(R ９０６ ) (R ９０７ A group represented by —N(R ９０６ ) (R ９０７ Specific examples (specific example group G10) of groups represented by the formula (G1) include -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. Multiple G1s in -N(G1)(G1) may be the same as or different from one another. Multiple G2s in -N(G2)(G2) may be the same as or different from one another. Multiple G3s in -N(G3)(G3) may be the same as or different from one another. The multiple G6s in -N(G6)(G6) are the same as or different from each other.

[0056] "Halogen Atom" Specific examples (specific example group G11) of the "halogen atom" described in this specification include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0057] "Substituted or unsubstituted fluoroalkyl group" As used herein, a "substituted or unsubstituted fluoroalkyl group" refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). Unless otherwise specified herein, the number of carbon atoms in an "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. A "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. Note that the "substituted fluoroalkyl group" described herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in a "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include the examples of the above-mentioned "alkyl group" (specific example group G3) in which one or more hydrogen atoms have been replaced with fluorine atoms.

[0058] "Substituted or unsubstituted haloalkyl group" As used herein, a "substituted or unsubstituted haloalkyl group" refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The number of carbon atoms in an "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. A "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of a "haloalkyl group" are replaced with a substituent. Note that the "substituted haloalkyl group" described herein also includes a "substituted haloalkyl group" in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain are further replaced with a substituent, and a "substituted haloalkyl group" in which one or more hydrogen atoms of the substituent are further replaced with a substituent. Specific examples of the "unsubstituted haloalkyl group" include the examples of the above-mentioned "alkyl group" (specific example group G3) in which one or more hydrogen atoms are replaced with halogen atoms. A haloalkyl group may also be referred to as a halogenated alkyl group.

[0059] - "Substituted or unsubstituted alkoxy group" A specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0060] - "Substituted or unsubstituted alkylthio group" A specific example of the "substituted or unsubstituted alkylthio group" described in this specification is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0061] - "Substituted or unsubstituted aryloxy group" A specific example of the "substituted or unsubstituted aryloxy group" described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. Unless otherwise specified in this specification, the number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0062] - "Substituted or unsubstituted arylthio group" A specific example of the "substituted or unsubstituted arylthio group" described in this specification is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. Unless otherwise specified in this specification, the number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0063] - "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Multiple G3s in -Si(G3)(G3)(G3) are the same as or different from one another. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0064] "Substituted or unsubstituted aralkyl group" A specific example of the "substituted or unsubstituted aralkyl group" described in this specification is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. Therefore, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one embodiment of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group," and the number of carbon atoms in the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification. Specific examples of the "substituted or unsubstituted aralkyl group" include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group, an α-naphthylmethyl group, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group, a 1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, a β-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethyl group, a 1-β-naphthylisopropyl group, and a 2-β-naphthylisopropyl group.

[0065] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described in this specification is preferably a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, or the like.

[0066] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic group described in this specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an aza Examples of such groups include a dibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group (a (9-phenyl)carbazol-1-yl group, a (9-phenyl)carbazol-2-yl group, a (9-phenyl)carbazol-3-yl group, or a (9-phenyl)carbazol-4-yl group), a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group.

[0067] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.

[0068]

[0069] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically any of the following groups:

[0070]

[0071] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0072] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0073]

[0074] In the general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.

[0075] 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.

[0076] "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group". Specific examples (specific example group G12) of the "substituted or unsubstituted arylene group" include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1.

[0077] "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.

[0078] "Substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group". Specific examples (specific example group G14) of the "substituted or unsubstituted alkylene group" include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3.

[0079] 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).

[0080]

[0081]

[0082] In the general formulae (TEMP-42) to (TEMP-52), Q １ ~Q １０ are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-42) to (TEMP-52), * represents a bonding position.

[0083]

[0084] In the general formulae (TEMP-53) to (TEMP-62), Q １ ~Q １０ are each independently a hydrogen atom or a substituent. ９ and Q １０ may be bonded to each other via a single bond to form a ring. In the general formulae (TEMP-53) to (TEMP-62), * represents the bonding position.

[0085]

[0086] In the general formulae (TEMP-63) to (TEMP-68), Q １ ~Q ８ are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-63) to (TEMP-68), * represents a bonding position.

[0087] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any one of the groups represented by the following general formulae (TEMP-69) to (TEMP-102).

[0088]

[0089]

[0090]

[0091] In the general formulae (TEMP-69) to (TEMP-82), Q １ ~Q ９ are each independently a hydrogen atom or a substituent.

[0092]

[0093]

[0094]

[0095]

[0096] In the general formulae (TEMP-83) to (TEMP-102), Q １ ~Q ８ are each independently a hydrogen atom or a substituent.

[0097] The above is the explanation of "substituents described in this specification."

[0098] "When bonded to form a ring" In this specification, when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle, bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other," it means when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle," when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring," and when "one or more pairs of adjacent groups do not bond to each other." In this specification, the cases when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle" and "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "when bonded to form a ring") will be explained below. An anthracene compound represented by the following general formula (TEMP-103), in which the main skeleton is an anthracene ring, will be described as an example.

[0099]

[0100] For example, R ９２１~R ９３０ In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," the pair of adjacent two groups is R ９２１ and R ９２２ With the pair, R ９２２ and R ９２３ With the pair, R ９２３ and R ９２４ With the pair, R ９２４ and R ９３０ With the pair, R ９３０ and R ９２５ With the pair, R ９２５ and R ９２６ With the pair, R ９２６ and R ９２７ With the pair, R ９２７ and R ９２８ With the pair, R ９２８ and R ９２９ and R ９２９ and R ９２１ It is paired with.

[0101] The above-mentioned "one or more pairs" means that two or more pairs of adjacent two or more groups may simultaneously form a ring. For example, R ９２１ and R ９２２ and are bonded to each other to form ring Q Ａ and simultaneously form R ９２５ and R ９２６ and are bonded to each other to form ring Q Ｂ When the anthracene compound represented by the general formula (TEMP-103) is formed, the anthracene compound represented by the general formula (TEMP-104) is represented by the following general formula (TEMP-104).

[0102]

[0103] The case where a "set of two or more adjacent groups" forms a ring includes not only the case where a set of "two" adjacent groups is bonded as in the above example, but also the case where a set of "three or more" adjacent groups is bonded. For example, R ９２１ and R ９２２ and are bonded to each other to form ring Q Ａ and R ９２２ and R ９２３ and are bonded to each other to form ring Q Ｃ and three adjacent (R ９２１ , R ９２２ and R９２３ 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.

[0104]

[0105] The "monocyclic ring" or "fused ring" formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when "one pair of adjacent two" forms a "monocyclic ring" or a "fused ring", the "monocyclic ring" or the "fused ring" may form a saturated ring or an unsaturated ring. For example, in the case of the ring Q formed in the general formula (TEMP-104), Ａ and Ring Q Ｂ are "monocyclic rings" or "fused rings". Ａ , and ring Q Ｃ is a "fused ring". Ａ and Tamaki Q Ｃ That is, Ring Q Ａ and Tamaki Q Ｃ The ring Q in the general formula (TMEP-104) is fused to form a fused ring. Ａ is a benzene ring, then ring Q Ａ The ring Q in the general formula (TMEP-104) is a monocyclic ring. Ａ is a naphthalene ring, then ring Q Ａ is a fused ring.

[0106] The term "unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The term "saturated ring" means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of aromatic hydrocarbon rings include structures in which the groups given as specific examples in the specific example group G1 are terminated with a hydrogen atom. Specific examples of aromatic heterocyclic rings include structures in which the aromatic heterocyclic groups given as specific examples in the specific example group G2 are terminated with a hydrogen atom. Specific examples of aliphatic hydrocarbon rings include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom. "Forming a ring" means forming a ring only with a plurality of atoms of the main skeleton, or with a plurality of atoms of the main skeleton and one or more optional elements. For example, R ９２１ and R ９２２ and a ring Q formed by bonding together Ａ is R ９２１ and the carbon atom of the anthracene skeleton to which R ９２２ It means a ring formed by the carbon atom of the anthracene skeleton to which R is bonded and one or more arbitrary elements. ９２１ and R ９２２ Todekan Q Ａ In the case where R ９２１ and the carbon atom of the anthracene skeleton to which R ９２２ When a monocyclic unsaturated ring is formed by the carbon atom of the anthracene skeleton to which R is bonded and four carbon atoms, R ９２１ and R ９２２ The ring formed by

[0107] Here, unless otherwise specified herein, the "arbitrary element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur. In any element (for example, in the case of carbon or nitrogen), a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below. When any element other than a carbon element is included, the formed ring is a heterocycle. Unless otherwise specified herein, the "one or more arbitrary elements" constituting the monocycle or fused ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5. Unless otherwise specified herein, of the "monocycle" and the "fused ring," the "monocycle" is preferred. Unless otherwise specified herein, of the "saturated ring" and the "unsaturated ring," the "unsaturated ring" is preferred. Unless otherwise specified herein, the "monocycle" is preferably a benzene ring. Unless otherwise specified herein, the "unsaturated ring" is preferably a benzene ring. When "one or more pairs of adjacent two or more rings" "combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring," unless otherwise specified in this specification, preferably, one or more pairs of adjacent two or more rings combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0108] When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents Described Herein." When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents Described Herein." The above is an explanation of the case where "one or more pairs of adjacent two or more rings are bonded to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent two or more rings are bonded to form a substituted or unsubstituted fused ring" ("when bonded to form a ring").

[0109] Substituents in the case of "substituted or unsubstituted" In one embodiment of the present specification, the substituents in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituents" in the present specification) include, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ), -O-(R ９０４ ), -S-(R ９０５ ), -N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and an unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ ~R ９０７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. ９０１ When there are two or more R９０１ are the same or different from each other, R ９０２ When there are two or more R ９０２ are the same or different from each other, R ９０３ When there are two or more R ９０３ are the same or different from each other, R ９０４ When there are two or more R ９０４ are the same or different from each other, R ９０５ When there are two or more R ９０５ are the same or different from each other, R ９０６ When there are two or more R ９０６ are the same or different from each other, R ９０７ When there are two or more R ９０７ are the same or different from each other.

[0110] In one embodiment, the substituent in the "substituted or unsubstituted" is a group selected from the group consisting of an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and a heterocyclic group having 5 to 50 ring atoms.

[0111] In one embodiment, the substituent in the "substituted or unsubstituted" is a group selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heterocyclic group having 5 to 18 ring atoms.

[0112] 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."

[0113] Unless otherwise specified in this specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring. Unless otherwise specified in this specification, any optional substituent may further have a substituent. The substituents further possessed by the optional substituent are the same as those of the optional substituents described above.

[0114] 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.

[0115] First Embodiment Organic Electroluminescent Element The organic EL element according to the first embodiment includes an organic layer between an anode and a cathode. The organic layer includes at least one layer made of an organic compound. Alternatively, the organic layer is formed by stacking multiple layers made of organic compounds. The organic layer may further include an inorganic compound. In the first embodiment, at least three of the organic layers include an emitting layer between the anode and the cathode, a first layer between the anode and the emitting layer, and a second layer between the cathode and the emitting layer. In one aspect of the organic EL element of the first embodiment, the first layer is an electron blocking layer, and the second layer is a hole blocking layer. The organic layer may be composed of, for example, an emitting layer, a first layer, and a second layer, or may include a layer that can be used in an organic EL element. Layers that can be employed in the organic EL device are 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 blocking layer other than the first layer, an electron injection layer, an electron transport layer, and a hole blocking layer other than the second layer. In one aspect of the organic EL device of the first embodiment, a hole transport layer is included between the anode and the first layer. In one aspect of the organic EL device of the first embodiment, a hole transport layer and a hole injection layer are included between the anode and the first layer. In one aspect of the organic EL device of the first embodiment, an electron transport layer is included between the cathode and the light-emitting layer. In one aspect of the organic EL device of the first embodiment, an electron transport layer is included between the cathode and the second layer. In one aspect of the organic EL device of the first embodiment, an electron transport layer and an electron injection layer are included between the cathode and the second layer.

[0116] The organic electroluminescent device according to this embodiment includes an anode, a cathode, an emitting layer between the anode and the cathode, a first layer between the anode and the emitting layer, and a second layer between the cathode and the emitting layer. The emitting layer contains a delayed fluorescent compound as a second compound, and the content of the second compound in the emitting layer is 30% by mass or more and 50% by mass or less. The first layer contains a fourth compound, and the second layer contains a fifth compound, and the fourth compound and the fifth compound are different from each other. The fourth compound satisfies the following mathematical formula (51), and the fifth compound satisfies the following mathematical formula (52). (Mathematical formula 51): |HOMO(M4)|≧5.74 eV (Mathematical formula 52): T ７７Ｋ (M5)≦2.90 eV (HOMO(M4) is the energy level of the highest occupied molecular orbital of the fourth compound, T ７７Ｋ (M5) is the energy gap of the fifth compound at 77 K.

[0117] In organic EL devices, when a TADF material is incorporated into the light-emitting layer and the TADF material is incorporated at a higher concentration (30% by mass or more) than the conventional concentration (approximately 25% by mass), the device's lifespan can be extended, but the luminous efficiency is significantly reduced. Because the TADF material has high electron transport properties, increasing the concentration of the TADF material in the light-emitting layer is thought to cause the light-emitting layer to have an excess of electrons, disrupting the charge balance and resulting in a decrease in luminous efficiency. To address this issue, the present inventors have discovered that by stacking a first layer (e.g., an electron blocking layer) and a second layer (e.g., a hole blocking layer) via the light-emitting layer, and incorporating a fourth compound satisfying the formula (51) in the first layer and a fifth compound satisfying the formula (52) in the second layer, the luminous efficiency can be improved or the device's lifespan can be extended. It is believed that by incorporating the fourth compound satisfying the above formula (51) into the first layer (e.g., electron blocking layer), the amount of holes injected into the light-emitting layer is increased, the charge balance in the light-emitting layer is adjusted, and the efficiency of the device is improved. However, simply incorporating the fourth compound into the first layer shortens the device's lifetime. The fifth compound satisfying the above formula (52) has an energy gap of 2.90 eV or less at 77 K, making it a highly durable material. Therefore, it is believed that incorporating the fourth compound into the first layer and further incorporating the fifth compound into the second layer (e.g., hole blocking layer) improves the device's luminous efficiency or extends the device's lifetime. Furthermore, in one aspect of the organic EL device of the first embodiment, the luminous efficiency is improved and the device's lifetime is extended.

[0118] In one aspect of the organic EL element of the first embodiment, the fourth compound satisfies the following mathematical formula (51) or the following mathematical formula (51A). When the fourth compound satisfies the following mathematical formula (51), the luminous efficiency is likely to be improved. (Mathematical formula 51): |HOMO(M4)|≧5.74 eV (Mathematical formula 51A): |HOMO(M4)|≧5.80 eV (HOMO(M4) is the energy level of the highest occupied molecular orbital of the fourth compound.)

[0119] In one aspect of the organic EL element of the first embodiment, the fifth compound satisfies the following formula (Formula 52) or the following formula (Formula 52A): When the fourth compound satisfies the formula (Formula 51) and the fifth compound satisfies the following formula (Formula 52), the luminous efficiency is likely to be improved and the lifetime is likely to be extended. (Formula 52):T ７７Ｋ (M5)≦2.90 eV (Number 52A): T ７７Ｋ (M5)≦2.70eV (T ７７Ｋ (M5) is the energy gap of the fifth compound at 77 K.

[0120] In one aspect of the organic EL element of the first embodiment, the second compound satisfies the following formula (Formula 53A) or the following formula (Formula 53B): (Formula 53A): T ７７Ｋ (M2) > T ７７Ｋ (M5) (Number 53B): T ７７Ｋ (M2) < T ７７Ｋ (M5) (T ７７Ｋ (M2) is the energy gap of the second compound at 77 K.

[0121] In one aspect of the organic EL element of the first embodiment, the second compound satisfies the following formula (Formula 54): |T ７７Ｋ (M2)-T ７７Ｋ (M5)|≦0.10eV

[0122] <Hole Transport Zone> In this specification, a region consisting of a plurality of organic layers disposed between the anode and the light-emitting layer may be referred to as a hole transport zone.

[0123] The hole transport region of the organic EL element of the first embodiment preferably further includes at least one of a hole injection layer and a hole transport layer in addition to the first layer. In one aspect of the organic EL element of the first embodiment, a hole transport layer is included between the anode and the first layer. In one aspect of the organic EL element of the first embodiment, the hole transport region includes a hole injection layer and the first layer, in this order from the anode side. In one aspect of the organic EL element of the first embodiment, the hole transport region includes a hole injection layer, a hole transport layer, and the first layer, in this order from the anode side.

[0124] In one aspect of the organic EL element of the first embodiment, the anode and the hole injection layer are in direct contact. In one aspect of the organic EL element of the first embodiment, the hole injection layer and the first layer are in direct contact. In one aspect of the organic EL element of the first embodiment, the hole injection layer and the hole transport layer are in direct contact. In one aspect of the organic EL element of the first embodiment, the first layer and the hole transport layer are in direct contact. The hole transport layer may include two or more organic layers. When the hole transport layer is composed of two organic layers, the two organic layers may be referred to as the first hole transport layer and the second hole transport layer. In one aspect of the organic EL element of the first embodiment, the hole transport zone includes the hole injection layer, the first hole transport layer, the second hole transport layer, and the first layer, in this order from the anode side. In one aspect of the organic EL element of the first embodiment, the first layer and the light-emitting layer are in direct contact.

[0125] Fig. 1 shows a schematic configuration of an example of an organic EL element according to the first embodiment. The organic EL element 1A shown in Fig. 1 includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10A disposed between the anode 3 and the cathode 4. The organic layer 10A includes, in order from the anode 3 side, a hole-transporting region 7A, an emitting layer 5, and an electron-transporting region 8A. The hole-transporting region 7A includes, in order from the anode 3 side, a hole-injection layer 6, a hole-transporting layer 7, and a first layer 71. The electron-transporting region 8A includes, in order from the emitting layer 5 side, a second layer 81, an electron-transporting layer 8, and an electron-injection layer 9.

[0126] The present invention is not limited to the configuration of the organic EL element shown in Fig. 1 . Examples of organic EL elements with different configurations include an organic EL element in which the hole transport layer 7 is composed of a first hole transport layer and a second hole transport layer, and the hole transport zone includes, in order from the anode 3 side, a hole injection layer 6, a first hole transport layer, a second hole transport layer, and a first layer 71. Examples of organic EL elements with different configurations include an organic EL element in which the light-emitting layer 5 is composed of two organic layers. Examples of organic EL elements with different configurations include an organic EL element in which the electron transport layer 8 is composed of a first electron transport layer and a second electron transport layer, and the electron transport zone 8A includes, in order from the light-emitting layer 5 side, a second layer 81, a first electron transport layer, a second electron transport layer, and an electron injection layer 9.

[0127] (Hole Transport Layer) One aspect of the organic EL element of the first embodiment includes a hole transport layer between the anode and the first layer. The hole transport layer includes a sixth compound. Examples of the sixth compound include the "materials that can be used in the hole transport layer (e.g., aromatic amine compounds, carbazole derivatives, and anthracene derivatives)" described in the <Configuration of Organic EL Element> section below. The sixth compound is, for example, a monoamine compound having one substituted or unsubstituted amino group in the molecule, or a diamine compound having two substituted or unsubstituted amino groups in the molecule. The sixth compound may also be a compound having a substituted or unsubstituted carbazolyl group and one substituted or unsubstituted amino group in the molecule. The sixth compound may also be a compound represented by the following general formula (4) described below.

[0128] (Hole Injection Layer) One aspect of the organic EL element of the first embodiment includes a hole injection layer between the anode and the hole transport layer. The hole injection layer may be, for example, a "substance with high hole injection properties" as described in the <Configuration of Organic EL Element> section below. In one aspect of the organic EL element of the first embodiment, the hole injection layer may be composed of only one material. In one aspect of the organic EL element of the first embodiment, the hole injection layer contains an acceptor material. In one aspect of the organic EL element of the first embodiment, the hole injection layer contains a first organic material and an acceptor material. The first organic material and the acceptor material are different compounds. The first organic material is, for example, a monoamine compound having one substituted or unsubstituted amino group in the molecule, or a diamine compound having two substituted or unsubstituted amino groups in the molecule. The first organic material may be a compound represented by the following general formula (4) as described below. In one aspect of the organic EL element of the first embodiment, the first organic material contained in the hole injection layer and the sixth compound contained in the hole transport layer are the same or different. In one aspect of the organic EL element of the first embodiment, the content of the acceptor material in the hole injection layer is less than 50 mass %.

[0129] (First Layer) In the organic EL element of the first embodiment, the first layer contains a fourth compound. The fourth compound is not particularly limited as long as it is a compound that satisfies the above mathematical formula (51). The fourth compound in the first embodiment is, for example, a compound that satisfies the above mathematical formula (51) and is represented by the following general formula (4). As the fourth compound, a compound that satisfies the above mathematical formula (51) can be selected from the compounds represented by the following general formula (4). The fourth compound and the fifth compound are different compounds.

[0130]

[0131] (In the general formula (4), L Ａ１ , L Ａ２ and L Ａ３ each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, ４１１ , Ar ４１２ and Ar ４１３ each independently represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, —Si(R Ｃ１ ) (R Ｃ２ ) (R Ｃ３ ) or a group represented by the general formula (4A), ４１１ , Ar ４１２ , and Ar ４１３ At least one of the groups represented by the general formula (4A) is a group represented by the general formula (4A), and when two or more groups represented by the general formula (4A) are present, the two or more groups represented by the general formula (4A) are the same as or different from each other, and R Ｃ１ , R Ｃ２ and R Ｃ３ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, RＣ１ If there are multiple R Ｃ１ are the same or different from each other, R Ｃ２ If there are multiple R Ｃ２ are the same or different from each other, R Ｃ３ If there are multiple R Ｃ３ are the same or different from each other, and in the general formula (4A), X ４ is an oxygen atom, a sulfur atom, C(R ４１Ａ ) (R ４２Ａ ) or N(R ４３Ａ ) and R ４１Ａ and R ４２Ａ are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and R ４１ ~R ４８ At least one pair of adjacent two or more of the groups bond to each other to form a substituted or unsubstituted monocyclic ring, bond to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, *2 represents L Ａ１ , L Ａ２ or L Ａ３ is the bonding position with R ４１ ~R ４８ , R ４１Ａ , R ４２Ａ and R ４３Ａ one of R is a single bond bonding to *1, R is not a single bond bonding to *1, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring ４１ ~R ４８ , R ４１Ａ , R ４２Ａ and R ４３Ａ are each independently a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R９０４ a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ ~R ９０４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other.)

[0132] In the general formula (4), L Ａ１ , L Ａ２ or L Ａ３ is a single bond, *2 is the bonding position to the nitrogen atom in the general formula (4).

[0133] In one embodiment of the fourth compound, L Ａ１ , L Ａ２ and L Ａ３ are each independently a single bond, a substituted or unsubstituted furanylene group, a substituted or unsubstituted thienylene group, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothienylene group. Ａ１ , L Ａ２ and LＡ３ are each independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted phenanthrylene group.

[0134] In at least one group represented by the general formula (4A), R ４１ ~R ４８ It is also preferred that one of is a single bond bonded to *1.

[0135] In one aspect of the organic EL element of the first embodiment, the fourth compound is a compound represented by the following general formula (40A).

[0136]

[0137] (In the general formula (40A), Ar ４１１ , Ar ４１２ , L Ａ１ , L Ａ２ and L Ａ３ are respectively Ar in the general formula (4). ４１１ , Ar ４１２ , L Ａ１ , L Ａ２ and L Ａ３ is synonymous with R ４１ ~R ４８ are R in the general formula (4), respectively. ４１ ~R ４８ where R ４１ ~R ４４ One of them is L Ａ３ is a single bond that bonds to X ４ represents X in the general formula (4). ４ is synonymous with

[0138] In one aspect of the organic EL element of the first embodiment, the fourth compound is a compound represented by the following general formula (40).

[0139]

[0140] (In the general formula (40), Ar ４１１ , Ar ４１２ and Ar ４１３are respectively Ar in the general formula (4). ４１１ , Ar ４１２ and Ar ４１３ n1 is 4, and four Ra １１ are the same or different from each other, and the four Ra １１ one or more pairs of adjacent two or more of １２ are the same or different from each other, and the four Ra １２ one or more pairs of adjacent two or more of １３ are the same or different from each other, and the four Ra １３ one or more pairs of adjacent two or more of Ra are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused ring; １１ , Ra １２ and Ra １３ each independently represents a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ ~R ９０４ are R in the general formula (4A), respectively. ９０１ ~R ９０４ is synonymous with

[0141] In one embodiment of the fourth compound, Ar ４１１ , Ar ４１２ , and Ar ４１３ At least one of the groups is a group represented by any one of the following general formulae (451) to (480): When a plurality of groups represented by any one of the following general formulae (451) to (480) are present, the plurality of groups represented by any one of the general formulae (451) to (480) are the same as or different from each other.

[0142]

[0143] (In the general formulae (451) to (455), R ４１ ~R ４８ and R ４３Ａ are R in the general formula (4A), respectively. ４１ ~R ４８ and R ４３Ａ * each independently represents L in formula (4). Ａ１ , L Ａ２ and L Ａ３ (*2 in the general formula (4)) or the bonding position to the carbon atom constituting the benzene ring in the general formula (40).

[0144]

[0145] (In the general formulae (456) to (460), R ４１ ~R ４８ , R ４１Ａ and R ４２Ａ are R in the general formula (4A), respectively. ４１ ~R ４８ , R ４１Ａ and R ４２Ａ * each independently represents L in formula (4). Ａ１ , L Ａ２ and L Ａ３ (*2 in the general formula (4)) or the bonding position to the carbon atom constituting the benzene ring in the general formula (40).

[0146]

[0147] (In the general formulae (461) to (468), R ４１ ~R ４８ are R in the general formula (4A), respectively. ４１ ~R ４８ and * each independently represents L in formula (4). Ａ１ , L Ａ２ and L Ａ３ (*2 in the general formula (4)) or the bonding position to the carbon atom constituting the benzene ring in the general formula (40).

[0148]

[0149]

[0150] (In the general formulae (469) to (480), R ４１ ~R ４８ and X ４ are R in the general formula (4A), respectively. ４１ ~R ４８ and X ４ is synonymous with R ４１Ｂ ~R ４４Ｂ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused ring ４１Ｂ ~R ４４Ｂ are each independently a single bond bonded to *1, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring, R in the general formula (4A). ４１ ~R ４８ * each independently represents L in formula (4). Ａ１ , L Ａ２ and L Ａ３ (*2 in the general formula (4)) or the bonding position to the carbon atom constituting the benzene ring in the general formula (40).

[0151] In the fourth compound, the benzene ring of the general formula (40) to which the groups represented by the general formulas (451) to (480) are bonded is the benzene ring itself explicitly shown in the general formula (40), and Ra １１ , Ra １２ and Ra １３ It is not a benzene ring contained in

[0152] In one aspect of the organic EL element of the first embodiment, Ar in the fourth compound ４１１ , Ar ４１２ , and Ar ４１３ At least one of the above is a group represented by any one of the following general formulae (451), (457), and (461) to (464).

[0153]

[0154] (In the general formulae (451), (457), and (461) to (464), R ４１ ~R ４８ are R in the general formula (4A), respectively. ４１ ~R ４８ is synonymous with R ４１Ａ and R ４２Ａ are R in the general formula (4A), respectively. ４１Ａ and R ４２Ａ * in the general formulae (451), (457), and (461) to (464) each independently represents L in the general formula (4). Ａ１ , L Ａ２ and L Ａ３ (*2 in the general formula (4)) or the bonding position to the carbon atom constituting the benzene ring in the general formula (40).

[0155] In one aspect of the organic EL element of the first embodiment, Ar in the fourth compound ４１１ , Ar ４１２ , and Ar ４１３At least one of the groups is a group represented by any one of the general formulae (457), (461), or (464), and when two or more groups represented by any one of the general formulae (457), (461), or (464) are present, the two or more groups represented by any one of the general formulae (457), (461), or (464) are the same as or different from each other.

[0156]

[0157] (In the general formulae (457), (461), and (464), R ４１ ~R ４８ are R in the general formula (4A), respectively. ４１ ~R ４８ is synonymous with R ４１Ａ and R ４２Ａ are R in the general formula (4A), respectively. ４１Ａ and R ４２Ａ * in the general formulae (457), (461), and (464) each independently represents L in the general formula (4). Ａ１ , L Ａ２ and L Ａ３ or a bonding position to a carbon atom constituting a benzene ring in the general formula (40).

[0158] In one embodiment of the fourth compound, Ar ４１１ , Ar ４１２ , and Ar ４１３ At least one of these is a group represented by the general formula (457).

[0159] In one embodiment of the fourth compound, Ar ４１１ , Ar ４１２ , and Ar ４１３ At least one of these is a group represented by the general formula (461).

[0160] In one embodiment of the fourth compound, Ar ４１１ , Ar ４１２ , and Ar ４１３ At least one of these is a group represented by the general formula (464).

[0161] In one embodiment of the compound represented by the general formula (40A) in the fourth compound, L Ａ３ is a group represented by any one of the general formulas (451) to (480), and Ar ４１１ and Ar ４１２ At least one of the groups represented by any one of the general formulae (451) to (480) is a group represented by any one of the general formulae (451) to (480). When a plurality of groups represented by any one of the general formulae (451) to (480) are present, the plurality of groups represented by any one of the general formulae (451) to (480) are the same or different from each other. In the general formulae (451) to (480), * each independently represents L in the general formula (40A). Ａ１ , L Ａ２ and L Ａ３ This is the bonding position with

[0162] In one embodiment of the compound represented by the general formula (40A) in the fourth compound, L Ａ３ The group bonded to Ar is a group represented by any one of the general formulas (457), (461), or (464). ４１１ and Ar ４１２ At least one of the groups represented by the general formula (457), (461), or (464) is a group represented by any one of the general formulae (457), (461), or (464). When a plurality of groups represented by any one of the general formulae (457), (461), or (464) are present, the plurality of groups represented by any one of the general formulae (457), (461), or (464) are the same or different from each other. In the general formulae (457), (461), and (464), * each independently represents L in the general formula (40A). Ａ１ , L Ａ２ and L Ａ３ This is the bonding position with

[0163] In one embodiment of the fourth compound, Ar ４１１ , Ar ４１２ , and Ar ４１３ Among them, Ar is not a group represented by the general formula (4A). ４１１ , Ar ４１２ , and Ar ４１３are each independently a group represented by any one of the following general formulas (45B), (46B), (47B), (48B), (49B), (410B), (411B), and (412B). ４１１ , Ar ４１２ , and Ar ４１３ When two of the groups are not the group represented by general formula (4A), the two groups are the same or different.

[0164]

[0165] (In the general formula (45B), R ４４１ ~R ４４５ In the general formulae (46B) and (47B), one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ４４０Ａ , R ４４０Ｂ and R ４４０Ｃ At least one pair of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and a plurality of R ４４０Ａ are the same or different from each other, and a plurality of R ４４０Ｂ are the same or different from each other, and a plurality of R ４４０Ｃ are the same or different from each other, and in the general formulae (48B), (49B), and (410B), R ４４０ ~R ４４３ , R ４４６ ~R ４４９ and R ４４０Ａ At least one pair of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and a plurality of R ４４０Ａ are the same or different from each other, and in the general formulae (411B) and (412B), X ６ is an oxygen atom, a sulfur atom, C(R４１Ｃ ) (R ４２Ｃ ) or N(R ４３Ｃ ) and R ４１Ｃ and R ４２Ｃ are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and R ４４１Ａ ~R ４４４Ａ at least one pair of adjacent two or more of the following is bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or not bonded to each other; and in the general formulae (45B), (46B), (47B), (48B), (49B), (410B), (411B), and (412B), ４４０ ~R ４４９ , R ４４０Ａ , R ４４０Ｂ , R ４４０Ｃ , R ４４１Ａ ~R ４４４Ａ , R ４１Ｃ , R ４２Ｃ , and R ４３Ｃ are each independently a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and * each independently represents L in formula (4). Ａ１ , L Ａ２ and L Ａ３ or a bonding position to a carbon atom constituting a benzene ring in the general formula (40).

[0166] In the fourth compound, the benzene ring of the general formula (40) to which the group represented by any one of the general formulas (45B), (46B), (47B), (48B), (49B), (410B), (411B), or (412B) is bonded is the benzene ring itself explicitly shown in the general formula (40), and Ra １１ , Ra １２ and Ra １３ It is not a benzene ring contained in

[0167] In one embodiment of the compound represented by the general formula (40A) in the fourth compound, Ar ４１１ and Ar ４１２ Ar , one of which is a group represented by the general formula (4A), and Ar , which is not a group represented by the general formula (4A), ４１１ and Ar ４１２ is a group represented by any one of the general formulae (45B) to (412B). In one embodiment of the compound represented by the general formula (40A) in the fourth compound, Ar ４１１ and Ar ４１２ When two of the groups are not the group represented by general formula (4A), the two groups are the same or different.

[0168] In one embodiment of the fourth compound, R ４１ ~R ４８ , R ４１Ａ , R ４２Ａ and R ４３Ａ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. ４１ ~R ４８ , R ４１Ａ , R ４２Ａ and R ４３Ａare each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 18 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0169] In one embodiment of the fourth compound, R ４４０ ~R ４４９ , R ４４０Ａ , R ４４０Ｂ , R ４４０Ｃ , R ４４１Ａ ~R ４４４Ａ , R ４１Ｂ ~R ４４Ｂ , R ４１Ｃ , R ４２Ｃ , R ４３Ｃ , Ra １１ , Ra １２ and Ra １３ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. ４４０ ~R ４４９ , R ４４０Ａ , R ４４０Ｂ , R ４４０Ｃ , R ４４１Ａ ~R ４４４Ａ , R ４１Ｂ ~R ４４Ｂ , R ４１Ｃ , R ４２Ｃ , R ４３Ｃ , Ra １１ , Ra １２ and Ra １３ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 18 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0170] In one embodiment of the fourth compound, the substituents in the term "substituted or unsubstituted" are each independently a substituted or unsubstituted 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 aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or -N(R ９０６ ) (R ９０７ ) is a group represented by R ９０６ and R ９０７ are each independently R in the general formula (4A). ９０１ ~R ９０４ is synonymous with R ９０６ If there are multiple R ９０６ are the same or different from each other, R ９０７ If there are multiple R ９０７ are the same or different from each other.

[0171] In one embodiment of the fourth compound, the substituents in the term "substituted or unsubstituted" are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, or -N(R ９０６ ) (R ９０７ In one embodiment of the fourth compound, the substituent in the case of "substituted or unsubstituted" is an "unsubstituted" group or a group represented by -N(R ９０６ ) (R ９０７ ) is a group represented by —N(R ９０６ ) (R ９０７ ) in R ９０６ and R ９０７ are all unsubstituted groups. In one embodiment of the fourth compound, the substituent in the term "substituted or unsubstituted" is an "unsubstituted" group.

[0172] (Method for Producing the Fourth Compound According to the First Embodiment) The fourth compound according to the first embodiment can be produced by a known method.

[0173] (Specific Examples of the Fourth Compound According to the First Embodiment) Specific examples of the fourth compound according to the first embodiment include the following compounds. However, the present invention is not limited to these specific examples of the compound.

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194] (Light-emitting layer) In the organic EL element of the first embodiment, the light-emitting layer contains a delayed fluorescent compound as the second compound. Below, an embodiment of the organic EL element of the first embodiment in which the light-emitting layer contains a delayed fluorescent compound (second compound), a first compound (preferably a fluorescent compound), and a third compound will be described. The first compound, the second compound, and the third compound are different compounds.

[0195] In the organic EL element of the first embodiment, the first compound is preferably a dopant material (which may also be referred to as a guest material, an emitter, or a light-emitting material), the second compound is preferably a host material (which may also be referred to as a matrix material), and the third compound is preferably a host material.

[0196] In the organic EL element of the first embodiment, the first compound, the second compound, and the third compound are preferably contained in the same layer, i.e., the first compound, the second compound, and the third compound are preferably contained in the same light-emitting layer.

[0197] In the first embodiment, the light-emitting layer preferably does not contain a phosphorescent metal complex, and preferably does not contain any metal complex other than the phosphorescent metal complex. In one embodiment, the light-emitting layer may contain a metal complex. In one embodiment, it is also preferable that the light-emitting layer does not contain a metal complex. In one embodiment, it is preferable that the light-emitting layer does not contain a phosphorescent material. In one embodiment, it is preferable that the light-emitting layer does not contain a heavy metal complex or a phosphorescent rare earth metal complex. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.

[0198] (Second Compound) In the organic EL element according to the first embodiment, the second compound is, for example, a delayed fluorescent compound represented by the following general formula (1).

[0199]

[0200] (In the general formula (1), CN is a cyano group, L is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, and D １１ and D １２ are each independently a group represented by the following general formula (11), (12) or (13), h is an integer of 2 or more, k is an integer of 1 or more, m is an integer of 0 or more, D １１ and D １２ are the same or different from each other, and a plurality of D １１ are the same or different from each other, and a plurality of D １２ are the same or different from each other.)

[0201]

[0202]

[0203]

[0204] (R in the general formula (11) １ ~R ８ at least one pair of adjacent two or more of R in the general formula (12) is bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or is not bonded to each other, １１ ~R １８ at least one pair of adjacent two or more of R in the general formula (13) are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １１１ ~R １１８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form a substituted or unsubstituted monocycle in the general formula (11) and do not form a substituted or unsubstituted fused ring. １ ~R ８R in the general formula (12) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. １１ ~R １８ and R in the general formula (13) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. １１１ ~R １１８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９０８ a group represented by -COOR ９０９ a halogen atom, a cyano group, a nitro group, -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, in the general formula (12) and the general formula (13), ring A, ring B, and ring C are each independently any ring structure selected from the group consisting of ring structures represented by the following general formulas (14) and (15), ring A, ring B, and ring C are fused to an adjacent ring at any position, p, px, and py are each independently 1, 2, 3, or 4, when p is 2, 3, or 4, multiple rings A are the same or different from each other, when px is 2, 3, or 4, multiple rings B are the same or different from each other, when py is 2, 3, or 4, multiple rings C are the same or different from each other, and * in the general formulas (11) to (13) indicates the bonding position with L in the general formula (1).

[0205]

[0206] (In the general formula (14), r is 0, 2 or 4, and a plurality of R １９ are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and in the general formula (15), X １ is a sulfur atom, an oxygen atom, C(R １５１ ) (R １５２ ) or N(R １５３ ) and R １５１ and R １５２ are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and R １５３ R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring １５１ and R １５２ and R which does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. １９are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９０８ a group represented by -COOR ９０９ a halogen atom, a cyano group, a nitro group, -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７ a 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, １９ are the same or different from each other, and a plurality of X １ are the same or different from each other.)

[0207] In the second compound, R ９０１ ~R ９０９ and R ９３１ ~R ９３７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９０１ If there are multiple R９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ９０６ If there are multiple R ９０６ are the same or different from each other, R ９０７ If there are multiple R ９０７ are the same or different from each other, R ９０８ If there are multiple R ９０８ are the same or different from each other, R ９０９ If there are multiple R ９０９ are the same or different from each other, R ９３１ If there are multiple R 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.

[0208] In one aspect of the organic EL element according to the first embodiment, at least one D １１But, R １ ~R ８ and one or more pairs of adjacent two or more of the following are bonded to each other to form the substituted or unsubstituted monocycle or substituted or unsubstituted fused ring:

[0209] The second compound is also preferably a compound represented by the following general formula (100).

[0210]

[0211] (In the general formula (100), L, D １１ , D １２ , h, k and m are L, D in the general formula (1), respectively. １１ , D １２ , h, k and m are synonymous with each other, and each R independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９０８ a group represented by -COOR ９０９ a cyano group, a nitro group, a group represented by -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７a 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, provided that at least one R is a substituent, and at least one R as the substituent is bonded to L of the compound represented by general formula (100) via a carbon-carbon bond, n is an integer of 1 or more, and the multiple Rs are the same or different.

[0212] In the compound represented by the general formula (1) or (100), L is preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 14 ring carbon atoms, and more preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 10 ring carbon atoms. In the compound represented by the general formula (1) or (100), the aromatic hydrocarbon ring having 6 to 14 ring carbon atoms represented by L is preferably a benzene ring, a naphthalene ring, a fluorene ring, or a phenanthrene ring.

[0213] In the compound represented by the general formula (1) or (100), L is preferably a benzene ring. When L is a benzene ring, the compound represented by the general formula (100) is represented by the following general formula (101).

[0214] In the organic EL element according to the first embodiment, the compound (second compound) represented by the general formula (1) is preferably represented by the following general formula (101).

[0215]

[0216] (In the general formula (101), D １１ and D １２ are D in the general formula (1), respectively. １１ and D １２wherein h is 2, 3, 4, or 5, k is 1, 2, 3, or 4, m is 0, 1, 2, or 3, n is 0, 1, 2, or 3, and h+k+m+n=6, and each R is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９０８ a group represented by -COOR ９０９ a cyano group, a nitro group, a group represented by -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７ a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and the multiple R's are the same or different.

[0217] In the second compound, the benzene ring of the general formula (101) to which the groups represented by the general formulas (11) to (13) are bonded is the benzene ring itself explicitly shown in the general formula (101), and R, D １１ and D １２ It is not a benzene ring contained in

[0218] In the second compound, h is 2, 3, or 4, k is 1, 2, or 3, m is 0, 1, or 2, and n is 1, 2, or 3, provided that at least one R is a substituent, and that at least one R as the substituent is preferably bonded to the benzene ring in general formula (101) via a carbon-carbon bond.

[0219] In the second compound, h is preferably 2 or 3, and more preferably 2.

[0220] In the organic EL device according to the first embodiment, the compound represented by the general formula (1) is preferably a compound represented by the following general formula (110), (120), or (130).

[0221]

[0222] (In the general formulae (110), (120) and (130), D １１ , D １２ , R, k, m and n are each the D in the general formula (1) or (101). １１ , D １２ , R, k, m, and n are synonymous with each other.)

[0223] In the second compound, it is preferred that k is 1, m is 1, and n is 2.

[0224] In the organic EL device according to the first embodiment, the compound represented by the general formula (1) is preferably represented by the following general formula (126) or (127).

[0225]

[0226] (In the general formula (126) and the general formula (127), D １１ is D in the general formula (1). １１ is synonymous with D １２ is D in the general formula (1). １２ is synonymous with R １０１ ~R １０４ are each independently defined as R in the general formula (101), k is 1 or 2, m is 0 or 1, and k+m is 2.

[0227] In the organic EL device according to the first embodiment, the compound represented by the general formula (1) is also preferably represented by the following general formula (126A), general formula (127A), or general formula (127B).

[0228]

[0229] (In the general formula (126A), the general formula (127A) and the general formula (127B), D １１ is D in the general formula (1). １１ is synonymous with D １２ is D in the general formula (1). １２ is synonymous with R １０１ ~R １０４ each independently has the same meaning as R in the general formula (101).

[0230] In the organic EL device according to the first embodiment, the compound represented by the general formula (1) is a compound represented by the general formula (126A), the general formula (127A), and the general formula (127B), １１ and D １２ are preferably different groups.

[0231] In the organic EL device according to the first embodiment, the compound represented by the general formula (1) is also preferably represented by the following general formula (126C) or (127C).

[0232]

[0233] (In the general formula (126C) and the general formula (127C), D １１ is D in the general formula (1). １１ is synonymous with D １２ is D in the general formula (1). １２ is synonymous with R １３１ ~R １４０ and R １４１ ~R １５０ are each independently defined as R in the general formula (101), k is 1 or 2, m is 0 or 1, and k+m is 2.

[0234] In the organic EL device according to the first embodiment, the compound represented by the general formula (1) is also preferably represented by the following general formula (126D) or (127D).

[0235]

[0236] (In the general formulae (126D) and (127D), D １１ is D in the general formula (1). １１ is synonymous with D １２ is D in the general formula (1). １２ is synonymous with R １３１ ~R １４０ and R １４１ ~R １５０ each independently has the same meaning as R in the general formula (101).

[0237] In the second compound, at least one D １１ is preferably a group represented by the general formula (12) or (13).

[0238] In the second compound, at least one D １１ is preferably a group represented by the following general formula (121), (122) or (131).

[0239]

[0240]

[0241]

[0242] (In the general formulas (121) and (122), R １１ ~R １８ are R in the general formula (12), respectively. １１ ~R １８ and ring A is the same as １、 Ring A ２ , ring A ３ and Ring A ４ Among these, two are ring structures represented by the general formula (14) and the remaining two are ring structures represented by the general formula (15), and in the general formula (131), R １１１ ~R １１８ are R in the general formula (13), respectively.１１１ ~R １１８ and ring B １ and Ring B ２ one of the ring structures represented by the general formula (14) is a ring structure represented by the general formula (14), and ring B １ and Ring B ２ the other is a ring structure represented by the general formula (15), and Ring C １ and Ring C ２ is a ring structure represented by the general formula (14), and ring C １ and Ring C ２ the other is a ring structure represented by the general formula (15), and * in the general formulae (121), (122) and (131) indicates the bonding position to L in the general formula (1), or the bonding position to the benzene ring in the general formula (101), (110), (120), (126), (126A), (126C), (126D), (127), (127A), (127B), (127C), (127D) or (130).

[0243] In the second compound, ring A in the general formula (121) １ and Ring A ３ is a ring structure represented by the general formula (14), and ring A ２ and Ring A ４ is preferably a ring structure represented by the general formula (15). １ is a ring structure represented by the general formula (14), and ring B ２ is preferably a ring structure represented by the general formula (15). １ is a ring structure represented by the general formula (14), and ring C ２ is preferably a ring structure represented by the general formula (15).

[0244] In the second compound, at least one D １１ is preferably a group represented by the general formula (131).

[0245] In the second compound, at least one D １１is preferably a group represented by the following general formula (123), (124), (125) or (132).

[0246]

[0247]

[0248]

[0249]

[0250] (In the general formulae (123), (124) and (125), R １１ ~R １８ are R in the general formula (12), respectively. １１ ~R １８ is synonymous with R １９１ ~R １９４ are each independently R in the general formula (14). １９ In the general formula (132), R １１１ ~R １１８ are R in the general formula (13), respectively. １１１ ~R １１８ is synonymous with R １９５ ~R １９８ are each independently R in the general formula (14). １９ In the general formulae (123), (124), (125) and (132), X １３ and X １４ each independently represents X in the general formula (15). １ * indicates the bonding position to L in the general formula (1) or the bonding position to the benzene ring in the general formula (101), (110), (120), (126), (126A), (126C), (126D), (127), (127A), (127B), (127C), (127D) or (130).

[0251] In the second compound, X １３ is preferably a sulfur atom.

[0252] In the second compound, at least one D １１ is preferably a group represented by the general formula (132).

[0253] In the second compound, m is preferably an integer of 1 or more.

[0254] In the second compound, D １２ is a group represented by the general formula (11) or (12), and m is preferably an integer of 1 or more.

[0255] In the second compound, k and m are preferably 1.

[0256] In the second compound, at least one D １２ is also preferably a group represented by the general formula (11).

[0257] In the second compound, at least one D １２ is also preferably a group represented by the general formula (12).

[0258] In the second compound, the group represented by the general formula (12) is preferably any group selected from the group consisting of groups represented by the following general formulae (12A), (12B), (12C), (12D), (12E), and (12F):

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265] (In the general formulae (12A), (12B), (12C), (12D), (12E) and (12F), R １１ ~R １８ are R in the general formula (12), respectively. １１ ~R １８ is synonymous with R １９ and R ２０ are each independently R in the general formula (14). １９is synonymous with X １ represents X in the general formula (15). １ and * in the general formulae (12A), (12B), (12C), (12D), (12E) and (12F) indicates the bonding position to L in the general formula (1), or the bonding position to the benzene ring in the general formula (101), (110), (120), (126), (126A), (126C), (126D), (127), (127A), (127B), (127C), (127D) or (130).

[0266] In the second compound, X １ is preferably an oxygen atom or a sulfur atom.

[0267] In the second compound, R １ ~R ８ It is also preferred that adjacent pairs of two or more of R １１ ~R １８ It is also preferred that adjacent pairs of two or more of R １１１ ~R １１８ It is also preferred that any pair of two or more adjacent groups of the above is not bonded to each other.

[0268] In the second compound, it is preferable that R in the general formula (100) or (101) is each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0269] In the second compound, it is preferable that R in the general formula (100) or (101) is each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0270] In the second compound, R in the general formula (11) １ ~R ８ , R in the general formula (12)１１ ~R １８ , R in the general formula (13) １１１ ~R １１８ and R in the general formula (14) １９ are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0271] In the second compound, R in the general formula (11) １ ~R ８ , R in the general formula (12) １１ ~R １８ , R in the general formula (13) １１１ ~R １１８ and R in the general formula (14) １９ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0272] In the second compound, R in the general formula (100) or (101) is each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and R in the general formula (11) １ ~R ８ , R in the general formula (12) １１ ~R １８ , R in the general formula (13) １１１ ~R １１８ and R in the general formula (14) １９ are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0273] In the second compound, R in the general formula (100) or (101) is each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, and R in the general formula (11) is １ ~R ８ , R in the general formula (12) １１ ~R １８ , R in the general formula (13) １１１ ~R １１８ and R in the general formula (14) １９ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0274] In the second compound, the substituent in the term "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted alkenyl group having 2 to 25 carbon atoms, an unsubstituted alkynyl group having 2 to 25 carbon atoms, an unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ an unsubstituted aralkyl group having 7 to 50 carbon atoms; —C(═O)R ９０８ a group represented by -COOR ９０９ a group represented by -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７ a group represented by —S(═O) ２ R ９３８a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms, ９０１ ~R ９０９ , and R ９３１ ~R ９３８ are preferably each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[0275] In the second compound, the substituent in the term "substituted or unsubstituted" is preferably a halogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[0276] In the second compound, the substituent in the term "substituted or unsubstituted" is preferably an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 12 ring atoms.

[0277] In the organic EL device according to the first embodiment, it is also preferable that all of the groups described as "substituted or unsubstituted" in the second compound are "unsubstituted" groups.

[0278] In this specification, —O—(R ９０４ ) is a group represented by R ９０４ is a hydrogen atom, it is a hydroxy group. ９０５ ) is a group represented by R ９０５ is a hydrogen atom, it is a thiol group. ９３１ ) (R ９３２ ) is a group represented by R ９３１ and R ９３２ is a substituent, it is a substituted phosphine oxide group, and R ９３１ and R ９３２ When -Ge(R ９３３ ) (R ９３４) (R ９３５ ) is a group represented by R ９３３ , R ９３４ and R ９３５ is a substituent, it is a substituted germanium group. ９３６ ) (R ９３７ ) is a group represented by R ９３６ and R ９３７ is a substituent, it is a substituted boryl group.

[0279] (Delayed Fluorescence) Delayed fluorescence is explained on pages 261 to 268 of "Device Properties of Organic Semiconductors" (edited by Adachi Chihaya, published by Kodansha). In this document, the energy difference ΔE between the excited singlet state and the excited triplet state of a fluorescent material is １３ It has been explained that if the transition probability can be reduced, the reverse energy transfer from the excited triplet state to the excited singlet state, which usually has a low transition probability, occurs with high efficiency, resulting in the expression of thermally activated delayed fluorescence (TADF). Furthermore, Figure 10.38 in this document explains the mechanism by which delayed fluorescence occurs. The second compound according to the first embodiment is preferably a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism.

[0280] In general, delayed fluorescence can be confirmed by transient PL (Photoluminescence) measurement.

[0281] The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from transient PL measurements. Transient PL measurements are a technique in which a sample is excited by irradiating it with a pulsed laser and then measuring the decay behavior (transient characteristics) of PL emission after the irradiation is stopped. PL emission in TADF materials is classified into emission components from singlet excitons generated during the initial PL excitation and emission components from singlet excitons generated via triplet excitons. The lifetime of singlet excitons generated during the initial PL excitation is on the order of nanoseconds, which is very short. Therefore, emission from these singlet excitons decays quickly after irradiation with a pulsed laser. On the other hand, delayed fluorescence decays slowly because it is emission from singlet excitons generated via triplet excitons, which have a long lifetime. Thus, there is a large time difference between emission from singlet excitons generated during the initial PL excitation and emission from singlet excitons generated via triplet excitons. Therefore, the emission intensity derived from delayed fluorescence can be determined.

[0282] 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 an analysis of the behavior of delayed fluorescence will be described below using Figure 2.

[0283] 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.

[0284] The sample accommodated in the sample chamber 102 is obtained by forming a thin film on a quartz substrate, in which the doping material is doped at a concentration of 12 mass % relative to the matrix material.

[0285] A pulsed laser is irradiated from the pulsed laser unit 101 onto a thin film sample housed in the sample chamber 102 to excite the doping material. Emission light is extracted in a direction 90 degrees to the irradiation direction of the excitation light, and the extracted light is dispersed by a spectrometer 103, forming a two-dimensional image in a streak camera 104. As a result, a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and bright spots correspond to emission intensity. Cutting out this two-dimensional image along a predetermined time axis yields an emission spectrum in which the vertical axis represents emission intensity and the horizontal axis represents wavelength. Furthermore, cutting out the two-dimensional image along the wavelength axis yields a decay curve (transient PL) in which the vertical axis represents the logarithm of emission intensity and the horizontal axis represents time.

[0286] For example, a thin film sample A was prepared as described above using the following compound HX1 as the matrix material and the following compound DX1 as the doping material, and transient PL measurement was carried out.

[0287]

[0288] Here, the attenuation curves were analyzed using the above-mentioned thin film sample A and thin film sample B. Thin film sample B was prepared as described above using the following compound HX2 as a matrix material and the above-mentioned compound DX1 as a doping material.

[0289] FIG. 3 shows the decay curves obtained from the transient PL measured for thin film sample A and thin film sample B.

[0290]

[0291] As described above, transient PL measurement can be used to obtain an emission decay curve with the vertical axis representing emission intensity and the horizontal axis representing time. Based on this emission decay curve, the fluorescence intensity ratio between the fluorescence emitted from the singlet excited state generated by photoexcitation and the delayed fluorescence emitted from the singlet excited state generated by reverse energy transfer via the triplet excited state can be estimated. In delayed fluorescent materials, the ratio of the intensity of the delayed fluorescence, which decays slowly, to the intensity of the fluorescence, which decays quickly, is somewhat large.

[0292] Specifically, luminescence from delayed fluorescent materials includes prompt luminescence and delay luminescence. Prompt luminescence is luminescence that is observed immediately from the excited state after being excited by pulsed light (light irradiated from a pulsed laser) having a wavelength that the delayed fluorescent material absorbs. Delay luminescence is luminescence that is not observed immediately after excitation by the pulsed light, but is observed later.

[0293] 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.

[0294] Furthermore, a sample prepared by the following method is used to measure the delayed fluorescence of the second compound according to the first embodiment. For example, the second compound according to the first embodiment is dissolved in toluene to prepare a dilute solution having an absorbance of 0.05 or less at the excitation wavelength to eliminate the contribution of self-absorption. To prevent quenching by oxygen, the sample solution is frozen and degassed, and then sealed in a lidded cell under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the sample solution is measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene is also measured under the same conditions. Using the fluorescence area intensities of both spectra, the total fluorescence quantum yield is calculated according to equation (1) in Morris et al. J. Phys. Chem. 80 (1976) 969.

[0295] In the first embodiment, the amount of prompt luminescence (prompt luminescence) of the compound to be measured is calculated as X Ｐ The amount of delayed light emission is set to X Ｄ When this is done, X Ｄ / X ＰThe measurement of the amounts of prompt luminescence and delay luminescence and their ratio for compounds other than the second compound according to the first embodiment herein is similar to the measurement of the amounts of prompt luminescence and delay luminescence and their ratio for the second compound according to the first embodiment.

[0296] (ΔST) In the first embodiment, the lowest excited singlet energy S １ and the energy gap T at 77[K] ７７Ｋ The difference between １ -T ７７Ｋ ) is defined as ΔST.

[0297] The lowest excited singlet energy S of the second compound according to the first embodiment １ (M2) and the energy gap T at 77 [K] of the second compound according to the first embodiment ７７Ｋ The difference ΔST(M2) between ΔST(M2) and ΔST(M2) is preferably less than 0.3 eV, more preferably less than 0.2 eV, even more preferably less than 0.1 eV, and even more preferably less than 0.01 eV. That is, ΔST(M2) preferably satisfies the relationship of the following formula (10), (11), (12), or (13): ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.3eV...(Math. 10) ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.2eV...(Math. 11) ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.1eV...(Math. 12) ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.01eV...(Math. 13)

[0298] Relationship Between Triplet Energy and Energy Gap at 77 K: Here, the relationship between triplet energy and energy gap at 77 K will be described. In the first embodiment, the energy gap at 77 K differs from the triplet energy as typically defined. Triplet energy is measured as follows. First, a sample is prepared by dissolving a compound to be measured in an appropriate solvent and sealing the solution in a quartz glass tube. A phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) is measured for this sample at low temperature (77 K). A tangent 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. Here, the second compound according to the first embodiment is preferably a thermally activated delayed fluorescence 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 state and the excited triplet state, and it is difficult to clearly distinguish which state the light emission is from, but the triplet energy value is considered to be basically dominant. Therefore, in the first embodiment, although the measurement method is the same as that of the normal triplet energy T, in order to distinguish that it is different in the strict sense, the value measured as follows is referred to as the energy gap T ７７Ｋ The compound to be measured is dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol / L, and this solution is placed in a quartz cell to serve as a measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this measurement sample is measured at low temperature (77 [K]), and a tangent line is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent line and the horizontal axis is determined. ｅｄｇｅ Based on the energy gap T at 77 [K], the amount of energy calculated from the following conversion formula (F1) is ７７Ｋ Conversion formula (F1): T ７７Ｋ [eV]=1239.85 / λｅｄｇｅ

[0299] The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows: When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum among the spectral maxima, consider the tangent at each point on the curve toward the long wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope is at its maximum (i.e., the tangent at the inflection point) is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that maximum points with peak intensities of 15% or less of the maximum peak intensity of the spectrum are not included in the shortest wavelength maximum, and the tangent drawn at the point where the slope is closest to the shortest wavelength maximum is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Phosphorescence can be measured using an F-4500 spectrofluorophotometer manufactured by Hitachi High-Technologies Corporation. However, the measuring device is not limited to this, and measurements may be performed by combining a cooling device, a cryogenic container, an excitation light source, and a light receiving device.

[0300] Lowest excited singlet energy S １ The lowest excited singlet energy S using a solution １ The following method can be used as a measurement method (sometimes referred to as the solution method): A 10 μmol / L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the absorption spectrum of this sample (vertical axis: absorption intensity, horizontal axis: wavelength) is measured at room temperature (300 K). A tangent line is drawn to the falling edge on the long wavelength side of this absorption spectrum, and the wavelength value λ at the intersection of this tangent line and the horizontal axis is determined. ｅｄｇｅ The lowest excited singlet energy is calculated by substituting [nm] into the following conversion formula (F2): Conversion formula (F2): S １ [eV]=1239.85 / λ ｅｄｇｅ An example of an absorption spectrum measuring device is a spectrophotometer (device name: U3310) manufactured by Hitachi, Ltd., but is not limited to this.

[0301] A tangent to the fall of the absorption spectrum on the long wavelength side is drawn as follows: When moving along the spectral curve from the longest maximum value on the longest wavelength side among the maximum values ​​of the absorption spectrum in the direction of longer wavelengths, consider the tangent at each point on the curve. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the slope is minimum on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is considered to be the tangent to the fall of the absorption spectrum on the long wavelength side. Note that maximum points with absorbance values ​​of 0.2 or less are not included in the maximum value on the longest wavelength side.

[0302] (Method for Producing Second Compound According to First Embodiment) The second compound can be produced by a known method. Alternatively, the second compound can be produced by following a known method and using known alternative reactions and raw materials suited to the target compound.

[0303] (Specific Examples of the Second Compound According to the First Embodiment) Specific examples of the second compound according to the first embodiment include the following compounds. However, the present invention is not limited to these specific examples. In this specification, a deuterium atom is represented as D in a chemical formula, and a protium atom is represented as H or is omitted. In this specification, a methyl group may be represented as Me, and a phenyl group may be represented as Ph.

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327] (First Compound) In one aspect of the organic EL element of the first embodiment, the first compound is a fluorescent compound. The first compound is preferably a compound that does not exhibit thermally activated delayed fluorescence. The first compound of the first embodiment is not a phosphorescent metal complex. The first compound is preferably not a heavy metal complex. Furthermore, the first compound is preferably not a metal complex.

[0328] The first compound of the first embodiment can 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.

[0329] The first compound is preferably a compound that exhibits luminescence with a maximum peak wavelength of 400 nm or more and 700 nm or less. －６ mol / liter or more 10 －５ The peak wavelength of the fluorescence spectrum at which the emission intensity is maximum is measured for a toluene solution in which the compound is dissolved at a concentration of 1 / 4 mole / L or less. The measurement device used is a spectrofluorometer (F-7000, manufactured by Hitachi High-Tech Science Corporation).

[0330] The first compound preferably exhibits red or green emission. In this specification, red emission refers to emission having a maximum peak wavelength in the fluorescence spectrum within the range of 600 nm to 660 nm. When the first compound is a red fluorescent compound, the maximum peak wavelength of the first compound is preferably 600 nm to 660 nm, more preferably 600 nm to 640 nm, and even more preferably 610 nm to 630 nm. In this specification, green emission refers to emission having a maximum peak wavelength in the fluorescence spectrum within the range of 500 nm to 560 nm. When the first compound is a green fluorescent compound, the maximum peak wavelength of the first compound is preferably 500 nm to 560 nm, more preferably 500 nm to 540 nm, and even more preferably 510 nm to 540 nm. In this specification, blue emission refers to emission having a maximum peak wavelength in the fluorescence spectrum within the range of 430 nm to 480 nm. When the first compound is a blue fluorescent compound, the maximum peak wavelength of the first compound is preferably 430 nm or more and 480 nm or less, more preferably 440 nm or more and 480 nm or less.

[0331] (Method for measuring ionization potential Ip and energy level HOMO of highest occupied molecular orbital) The ionization potential Ip of a measurement object (compound or material) is calculated by the following mathematical formula (Math Y1). The value of the energy level HOMO of the highest occupied molecular orbital corresponds to the value of the ionization potential Ip with a negative sign. The units of the ionization potential Ip and the energy level HOMO of the highest occupied molecular orbital are eV. The energy level of the highest occupied molecular orbital may be expressed as HOMO. (Math Y1): Ip = -1.40 x (Eox - Efc) - 4.60 eV In the mathematical formula (Math Y1), Eox and Efc are as follows. Eox: first oxidation potential of the object to be measured (DPV, positive scan) Efc: first oxidation potential of ferrocene (DPV, positive scan), (ca. +0.55 V vs Ag / AgCl) The redox potential can be measured by differential pulse voltammetry (DPV) using, for example, an electrochemical analyzer (manufactured by ALS: CHI852D). The sample solution used for the measurement is prepared by dissolving the substance to be measured in N,N-dimethylformamide (DMF) as a solvent to a concentration of 1.0 mmol / L and dissolving tetrabutylammonium hexafluorophosphate (TBHP) as a supporting electrolyte to a concentration of 100 mmol / L. A glassy carbon electrode is used as the working electrode. A platinum (Pt) electrode is used as the counter electrode. (References) M. E. Thompson, et. al., Organic Electronics, 6 (2005), p. 11-20, Organic Electronics, 10 (2009), p. 515-520

[0332] It is preferable that the first compound satisfies the following mathematical formula (21). |HOMO(M1)| is synonymous with the ionization potential Ip(M1) of the first compound. When |HOMO(M1)| of the first compound satisfies the following mathematical formula (21), it is believed that holes are less likely to be trapped by the dopant material, and holes are widely distributed in the light-emitting layer. (Mathematical formula 21): |HOMO(M1)|≧5.25 eV (HOMO(M1) is the energy level of the highest occupied molecular orbital of the first compound.)

[0333] The first compound preferably satisfies the following mathematical formula (Mathematical Formula 2C). When the |HOMO(M1)| of the first compound satisfies the following mathematical formula (Mathematical Formula 2C), the relationship |HOMO(M1)|<|HOMO(M3)| is likely to hold, making it easier to adjust the charge balance in the light-emitting layer. HOMO(M3) represents the energy level of the highest occupied molecular orbital of the third compound. |HOMO(M3)| is synonymous with the ionization potential Ip(M3) of the third compound. (Mathematical Formula 2C): |HOMO(M1)|≦5.65 eV

[0334] The first compound is not particularly limited, but is preferably a compound that satisfies the above mathematical formula (Mathematical Formula 21). Examples of the first compound include compounds represented by the following general formulas (D1), (D11), (D10), and (D20). As the first compound, it is preferable to select and use a compound that satisfies the above mathematical formula (Mathematical Formula 21) from the above-mentioned fluorescent material and the compounds represented by the following general formulas (D1), (D11), (D10), and (D20).

[0335] (Compound Represented by General Formula (D1)) In the first embodiment, the first compound is also preferably a compound represented by the following general formula (D1).

[0336]

[0337] (In the general formula (D1), ring Ax, ring Bx, ring Dx, ring Ex, and ring Fx each independently represent a ring structure selected from the group consisting of a substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heterocycle having 5 to 30 ring atoms, one of ring Bx and ring Dx is present, or both ring Bx and ring Dx are present, when both ring Bx and ring Dx are present, ring Bx and ring Dx share a bond connecting Zc and Zh, one of ring Ex and ring Fx is present, or both ring Ex and ring Fx are present, when both ring Ex and ring Fx are present, ring Ex and ring Fx share a bond connecting Zf and Zi, Za is a nitrogen atom or a carbon atom, Zb is, when ring Bx is present, a nitrogen atom or a carbon atom, When the ring Bx does not exist, an oxygen atom, a sulfur atom, NRb, C(Rb １ ) (Rb ２ ) or Si(Rb ３ ) (Rb ４ ), Zc is a nitrogen atom or a carbon atom, Zd is a nitrogen atom or a carbon atom when ring Dx is present, and is an oxygen atom, a sulfur atom or NRd when ring Dx is not present, Ze is a nitrogen atom or a carbon atom when ring Ex is present, and is an oxygen atom, a sulfur atom or NRe when ring Ex is not present, Zf is a nitrogen atom or a carbon atom, Zg is a nitrogen atom or a carbon atom when ring Fx is present, and is an oxygen atom, a sulfur atom, NRg, C(Rg １ ) (Rg ２ ) or Si(Rg ３ ) (Rg ４ ), Zh is a nitrogen atom or a carbon atom, Zi is a nitrogen atom or a carbon atom, Y is a boron atom, a phosphorus atom, SiRh, P=O or P=S, Rb, Rb １ , Rb ２ , Rb ３ , Rb ４ , Rd, Re, Rg, Rg １ , Rg ２ , Rg ３ , Rg ４and Rh are each independently a hydrogen atom or a substituent, and Rb, Rb as a substituent １ , Rb ２ , Rb ３ , Rb ４ , Rd, Re, Rg, Rg １ , Rg ２ , Rg ３ , Rg ４ and Rh each independently represent 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 cycloalkyl group having 3 to 30 ring carbon atoms, -Si(R ９１１ ) (R ９１２ ) (R ９１３ a group represented by —O—(R ９１４ ), a group represented by —S—(R ９１５ ), or a group represented by —N(R ９１６ ) (R ９１７ ) wherein the bond between Y and Za, the bond between Y and Zd, and the bond between Y and Ze are all single bonds.

[0338] In the first compound, the bond between Y and Za, the bond between Y and Zd, and the bond between Y and Ze are all single bonds, and these single bonds are covalent bonds and not coordinate bonds.

[0339] In this specification, examples of heterocycles include ring structures (heterocycles) obtained by removing a bond from the "heterocyclic group" exemplified in the above-mentioned "substituents described in this specification." These heterocycles may have a substituent or may be unsubstituted. In this specification, examples of aryl rings include ring structures (aryl rings) obtained by removing a bond from the "aryl group" exemplified in the above-mentioned "substituents described in this specification." These aryl rings may have a substituent or may be unsubstituted.

[0340] (Compound Represented by General Formula (D11)) In the organic EL element according to the first embodiment, the first compound is preferably a compound represented by the following general formula (D11): The compound represented by the general formula (D1) is preferably a compound represented by the following general formula (D11):

[0341]

[0342] (In the general formula (D11), ring Ax, ring Dx, and ring Ex each independently represent a ring structure selected from the group consisting of a substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heterocycle having 5 to 30 ring atoms; Za represents a nitrogen atom or a carbon atom; Zb represents an oxygen atom, a sulfur atom, NRb, C(Rb １ ) (Rb ２ ) or Si(Rb ３ ) (Rb ４ ), Zc is a nitrogen atom or a carbon atom, Zd is a nitrogen atom or a carbon atom, Ze is a nitrogen atom or a carbon atom, Zf is a nitrogen atom or a carbon atom, Zg is an oxygen atom, a sulfur atom, NRg, C(Rg １ ) (Rg ２ ) or Si(Rg ３ ) (Rg ４ ), Zh is a nitrogen atom or a carbon atom, Zi is a nitrogen atom or a carbon atom, Y is a boron atom, a phosphorus atom, SiRh, P=O or P=S, Rb, Rb １ , Rb ２ , Rb ３ , Rb ４ , Rg, Rg １ , Rg ２ , Rg ３ , Rg ４ and Rh each independently represent Rb, Rb １ , Rb ２ , Rb ３ , Rb ４ , Rg, Rg １ , Rg ２ , Rg ３ , Rg ４ and Rh.)

[0343] (Compound Represented by General Formula (D10)) In the organic EL element according to the first embodiment, the first compound is preferably a compound represented by the following general formula (D10): The compound represented by general formula (D1) is preferably a compound represented by the following general formula (D10):

[0344]

[0345] (In the general formula (D10), X １ is CR １ or a nitrogen atom, X ２ is CR ２ or a nitrogen atom, X ３ is CR ３ or a nitrogen atom, X ４ is CR ４ or a nitrogen atom, X ５ is CR ５ or a nitrogen atom, X ６ is CR ６ or a nitrogen atom, X ７ is CR ７ or a nitrogen atom, or X ８ is a carbon atom bonded to X by a single bond; ８ is CR ８ or a nitrogen atom, or X ７ is a carbon atom bonded to X by a single bond; ９ is CR ９ or a nitrogen atom, X １０ is CR １０ or a nitrogen atom, X １１ is CR １１ or a nitrogen atom, X １２ is CR １２ or a nitrogen atom, Q is CR Ｑ or a nitrogen atom, and Y is NR Ｙ１ , oxygen atom, sulfur atom, C(R Ｙ２ ) (R Ｙ３ ) or Si(R Ｙ４ ) (R Ｙ５ ) and R １ ~R ６ and R９ ~R １１ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ３、 R ４ and R Ｙ１ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ３、 R ４ and R Ｙ１ At least one hydrogen atom in a single ring or a condensed ring formed by bonding together one or more pairs of adjacent groups selected from the group consisting of -O-(R ９２０ ), and a group represented by —N(R ９２１ ) (R ９２２ at least one hydrogen atom in the substituent is substituted with an aryl group having 6 to 50 ring carbon atoms or an alkyl group having 1 to 50 carbon atoms, or is not substituted; R １２ , R １３ , and R Ｑ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. １ ~R １１ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９１１ ) (R ９１２ ) (R ９１３ a group represented by —O—(R ９１４ ), a group represented by —S—(R９１５ a group represented by —N(R ９１６ ) (R ９１７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９１８ a group represented by -COOR ９１９ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, wherein R does not form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring. Ｙ１ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and R Ｙ２ and R Ｙ３ are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and R Ｙ４ and R Ｙ５ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. Ｙ２ and R Ｙ３ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0346] In the first compound, R ９１１ ~R ９２２are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９１１ If there are multiple R ９１１ are the same or different from each other, R ９１２ If there are multiple R ９１２ are the same or different from each other, R ９１３ If there are multiple R ９１３ are the same or different from each other, R ９１４ If there are multiple R ９１４ are the same or different from each other, R ９１５ If there are multiple R ９１５ are the same or different from each other, R ９１６ If there are multiple R ９１６ are the same or different from each other, R ９１７ If there are multiple R ９１７ are the same or different from each other, R ９１８ If there are multiple R ９１８ are the same or different from each other, R 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 the same or different from each other.

[0347] In the compound represented by the general formula (D10), X ７ is X ８ is a carbon atom bonded to X by a single bond, ８ is X ７and is a carbon atom bonded to by a single bond, for example, general formula (D10) is represented by the following general formula (D10A).

[0348]

[0349] (In the general formula (D10A), X １ ~X ６ , X ９ ~X １２ , Y, Q, and R １３ are each independently as defined in general formula (D10).

[0350] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D12).

[0351]

[0352] (In the general formula (D12), R １ ~R １３ , R Ｙ１ , and R Ｑ are each independently as defined in general formula (D10).

[0353] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D12A).

[0354]

[0355] (In the general formula (D12A), R １ ~R ６ , R ９ ~R １３ , R Ｙ１ , and R Ｑ are each independently as defined in general formula (D10).

[0356] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D13).

[0357]

[0358] (In the general formula (D13), R １ ~R ３ , R ５ ~R １３ , and RＱ are each independently as defined in formula (D10), ｘ１ ~R ｘ４ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring Ｘ１ ~R ｘ４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -Si(R 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 substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９３８ a group represented by -COOR ９３９ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ９３１ ~R ９３９ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９３１ If there are multiple R ９３１ are the same or different from each other, R ９３２ If there are multiple R ９３２are the same or different from each other, R ９３３ If there are multiple R ９３３ are the same or different from each other, R ９３４ If there are multiple R ９３４ are the same or different from each other, R ９３５ If there are multiple R ９３５ are the same or different from each other, R ９３６ If there are multiple R ９３６ are the same or different from each other, R ９３７ If there are multiple R ９３７ are the same or different from each other, R ９３８ If there are multiple R ９３８ are the same or different from each other, R ９３９ If there are multiple R ９３９ are the same or different from each other.)

[0359] In the general formula (D13), for example, R ５ and R ６ are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0360] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D13A).

[0361]

[0362] (In the general formula (D13A), R １ ~R ３ , R ５ ~R ６ , R ９ ~R １３ , and R Ｑ are each independently as defined in general formula (D10), and R ｘ１ ~R ｘ４ are each independently as defined in general formula (D13).

[0363] In the compound represented by the general formula (D10), R１ ~R １３ and R Ｑ are also preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

[0364] In the compound represented by the general formula (D10), R １ ~R １３ and R Ｑ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms.

[0365] In the compound represented by the general formula (D10), R １ ~R ３ , R ５ ~R １３ , R Ｑ and R ｘ１ ~R ｘ４ are also preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

[0366] In the compound represented by the general formula (D10), R １ ~R ３ , R ５ ~R １３ , R Ｑ and R ｘ１ ~R ｘ４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms.

[0367] In the compound represented by the general formula (D10), R １ ~R１３ , R Ｑ and R ｘ１ ~R ｘ４ are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

[0368] In the compound represented by the general formula (D10), R １ ~R １３ , R Ｑ and R ｘ１ ~R ｘ４ are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms.

[0369] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D14).

[0370]

[0371] (In the general formula (D14), R ２ , R ６、 R １３、 R Ｑ and R ｘ２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms.

[0372] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D15).

[0373]

[0374] (In the general formula (D15), R ２ , R ６、 R １３、 R Ｑ and R ｘ２are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms.

[0375] In the compound represented by the general formula (D10), R １３ and R Ｑ are preferably each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted dibenzofuranyl group.

[0376] In the compound represented by the general formula (D10), R ６ and R ｘ２ are preferably each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0377] (Compound Represented by General Formula (D20)) In the organic EL element according to the first embodiment, the first compound is also preferably a compound represented by the following general formula (D20).

[0378]

[0379] In the general formula (D20), X is a nitrogen atom or a carbon atom bonded to Y, Y is a hydrogen atom or a substituent, and R ２１ ~R ２６ are each independently a hydrogen atom or a substituent, or R ２１ and R ２２ Group R ２２ and R ２３ Group R ２４ and R ２５ and R ２５ and R ２６ any one or more pairs of Y and R are bonded to each other to form a ring; ２１ ~R ２６are each independently 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 aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a halogen atom, a carboxy group, a substituted or unsubstituted ester group, is selected from the group consisting of a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted silyl group, and a substituted or unsubstituted siloxanyl group; ２１ and Z ２２ are each independently a substituent, or Z ２１ and Z ２２ are bonded to each other to form a ring, and Z as a substituent ２１ and Z ２２ are each independently selected from the group consisting of a halogen atom, 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 aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.

[0380] In the first compound according to the first embodiment, the substituent in the term "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted alkenyl group having 2 to 25 carbon atoms, an unsubstituted alkynyl group having 2 to 25 carbon atoms, an unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ an unsubstituted aralkyl group having 7 to 50 carbon atoms; —C(═O)R ９０８ a group represented by -COOR ９０９ a group represented by -S(=O) ２ R ９４１ a group represented by -P(=O)(R ９４２ ) (R ９４３ a group represented by —Ge(R ９４４ ) (R ９４５ ) (R ９４６ ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms, ９０１ ~R ９０９ , and R ９４１ ~R ９４６ are preferably each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[0381] In the first compound according to the first embodiment, the substituent in the case of being “substituted or unsubstituted” is preferably a halogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[0382] In the first compound according to the first embodiment, the substituent in the case of being “substituted or unsubstituted” is preferably an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 12 ring atoms.

[0383] In the first compound according to the first embodiment, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0384] (Specific Examples of the First Compound According to the First Embodiment) Specific examples of the first compound according to the first embodiment include the following compounds, however, the present invention is not limited to these specific examples.

[0385]

[0386]

[0387] (Third Compound) In the light-emitting layer of the organic EL element of the first embodiment, the third compound may be a thermally activated delayed fluorescence compound or a compound that does not exhibit thermally activated delayed fluorescence, but is preferably a compound that does not exhibit thermally activated delayed fluorescence.

[0388] The third compound is not particularly limited, and is preferably a compound represented by the following general formula (3), a compound represented by the following general formula (3B), or a compound represented by the following general formula (MRX3):

[0389] (Compound Represented by General Formula (3)) In the light-emitting layer of the organic EL element of the first embodiment, the third compound is also preferably a compound represented by the following general formula (3).

[0390]

[0391] (In the general formula (3), A ３ 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, L ３is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, a divalent group formed by bonding together two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, or a divalent group formed by bonding together three groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, R ３１ ~R ３８ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring ３１ ~R ３８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９０８ a group represented by -COOR ９０９ a halogen atom, a cyano group, a nitro group, -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５), a group represented by —B(R ９３６ ) (R ９３７ ) a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the following general formula (3A):

[0392]

[0393] (In the general formula (3A), R Ｂ represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９０８ a group represented by -COOR ９０９ a halogen atom, a cyano group, a nitro group, -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７ a 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, Ｂ When there are multiple R Ｂ are the same or different from each other, and L ３１is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a trivalent group, a tetravalent group, a pentavalent group, or a hexavalent group derived from the arylene group, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, a trivalent group, a tetravalent group, a pentavalent group, or a hexavalent group derived from the heterocyclic group, or a divalent group formed by bonding two groups selected from the group consisting of substituted or unsubstituted arylene groups having 6 to 50 ring carbon atoms and substituted or unsubstituted divalent heterocyclic groups having 5 to 50 ring atoms, or a trivalent group, a tetravalent group, a pentavalent group, or a hexavalent group derived from the divalent group, ３２ represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, ３ is 1, 2, 3, 4 or 5, and L ３１ When is a single bond, n ３ is 1, and L ３２ is bonded to a carbon atom of the six-membered ring in the general formula (3), and L ３２ When there are multiple L ３２ are the same or different, and * is the bonding site to the carbon atom of the six-membered ring in the general formula (3).

[0394] In the third compound, R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ , R ９０７ , R ９０８ , R ９０９ , R ９３１ , R ９３２ , R ９３３ , R ９３４ , R ９３５ , R ９３６ and R ９３７are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ９０６ If there are multiple R ９０６ are the same or different from each other, R ９０７ If there are multiple R ９０７ are the same or different from each other, R ９０８ If there are multiple R ９０８ are the same or different from each other, R ９０９ If there are multiple R ９０９ are the same or different from each other, R ９３１ If there are multiple R 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 ９３６If 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.

[0395] The compound represented by the general formula (3) is also preferably a compound represented by any one of the following general formulae (31) to (36).

[0396]

[0397]

[0398]

[0399] (In the general formulae (31) to (36), A ３ and L ３ are the same as A in the general formula (3), respectively. ３ and L ３ is synonymous with R ３４１ ~R ３５０ one or more pairs of adjacent two or more of X are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ３１ represents a sulfur atom, an oxygen atom, and NR ３５２ or CR ３５３ R ３５４ and R ３５３ and R ３５４ are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring. ３４１ ~R ３５０ And, R ３５２ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ３５３ and R ３５４ and R each independently represent a group that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ３１ ~R３８ is synonymous with

[0400] In the compound represented by the general formula (3), R ３５２ is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0401] In the compound represented by the general formula (3), R ３５３ and R ３５４ are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form a substituted or unsubstituted monocycle and a substituted or unsubstituted fused ring ３５３ and R ３５４ are preferably each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0402] In the compound represented by the general formula (3), X ３１ is preferably a sulfur atom or an oxygen atom.

[0403] In the compound represented by the general formula (3), A ３ is preferably a group represented by any one of the following general formulae (A31) to (A37).

[0404]

[0405]

[0406] (In the general formulae (A31) to (A37), a plurality of R ３００one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring ３００ , and R ３３３ each independently represents R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring; ３１ ~R ３８ * in the general formulae (A31) to (A37) respectively represents L of the compound represented by the general formula (3). ３ indicates the bonding position with

[0407] In the compound represented by the general formula (3), A ３ is also preferably a group represented by the general formula (A34), (A35) or (A37).

[0408] In the compound represented by the general formula (3), A ３ is preferably a group represented by any one of the following general formulae (A371) to (A376).

[0409]

[0410]

[0411]

[0412] (In the general formulae (A371) to (A376), Y ３ is a sulfur atom, an oxygen atom, N(R ３８１ ) or C(R ３８２ ) (R ３８３ ) and R ３８２ and R ３８３ are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and R ３７１ ~R ３８０one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ３８１ R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring ３７１ ~R ３８０ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ３８２ and R ３８３ each independently represents R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring; ３１ ~R ３８ * in the general formulae (A371) to (A376) represents L of the compound represented by the general formula (3), respectively. ３ indicates the bonding position with

[0413] In the general formulae (A371) to (A376), R ３８１ is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0414] In the general formulae (A371) to (A376), R ３８２ and R ３８３ are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form a substituted or unsubstituted monocycle and a substituted or unsubstituted fused ring ３８２ and R ３８３ are preferably each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0415] In the general formulae (A371) to (A376), Y ３is preferably a sulfur atom or an oxygen atom.

[0416] The compound represented by the general formula (3) is also preferably a compound represented by any one of the following general formulae (311) to (316).

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423] (In the general formulae (311) to (316), L ３ represents L in the general formula (3). ３ and plural R ３００ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ３４１ ~R ３５０ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring ３００ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ３４１ ~R ３５０ each independently represents R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring; ３１ ~R ３８ is synonymous with

[0424] The compound represented by the general formula (3) is also preferably a compound represented by the following general formula (321).

[0425]

[0426] (In the general formula (321), L ３ represents L in the general formula (3). ３ is synonymous with R ３１ ~R ３８ , and R ３０１ ~R ３０８ each independently represents R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring; ３１ ~R ３８ is synonymous with

[0427] In the compound represented by the general formula (3), L ３ is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0428] In the compound represented by the general formula (3), L ３ is preferably a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.

[0429] In the compound represented by the general formula (3), L ３ is preferably a group represented by the following general formula (317).

[0430]

[0431] (In the general formula (317), R ３１０ each independently represents R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring; ３１ ~R ３８ and * each independently indicates a bonding position.)

[0432] In the compound represented by the general formula (3), L ３ It is also preferable that L contains a divalent group represented by the following general formula (318) or general formula (319). ３is also preferably a divalent group represented by the following general formula (318) or general formula (319).

[0433] The compound represented by the general formula (3) is also preferably a compound represented by the following general formula (322) or (323).

[0434]

[0435]

[0436] (In the general formula (322) and the general formula (323), L ３１ represents a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, with the proviso that L ３１ R contains a divalent group represented by the following general formula (318) or general formula (319): ３１ ~R ３８ , R ３００ , and R ３２１ ~R ３２８ each independently represents R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring; ３１ ~R ３８ is synonymous with

[0437]

[0438] (In the general formula (319), a plurality of R ３０４ a pair of adjacent two of these is bonded to each other to form a ring represented by the general formula (320), and in the general formula (320), 1* and 2* each independently represent R ３０４ represents the bonding position with the ring to which R is bonded, ３０２ , R in the general formula (319) ３０３ and R which does not form a ring represented by the general formula (320). ３０４ and R in the general formula (320)３０５ each independently represents R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring; ３１ ~R ３８ In the general formulae (318) to (320), * indicates the bonding position.

[0439] In the compound represented by the general formula (3), L ３ or L ３１ The group represented by the general formula (319) as is, for example, a group represented by the following general formula (319A).

[0440]

[0441] (In the general formula (319A), R ３０３ , R ３０４ and R ３０５ each independently represents R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring; ３１ ~R ３８ and * in the general formula (319A) indicates a bonding position.)

[0442] The compound represented by the general formula (3) is a compound represented by the general formula (322), and L ３１ is also preferably a group represented by the general formula (318).

[0443] The compound represented by the general formula (3) is also preferably a compound represented by the following general formula (324).

[0444]

[0445] (In the general formula (324), R ３１ ~R ３８ , R ３００ , and R ３０２ each independently represents R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring; ３１ ~R ３８ is synonymous with

[0446] In the compound represented by the general formula (3), R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ３１ ~R ３８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the general formula (3A), and R in the general formula (3A) Ｂ is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0447] In the compound represented by the general formula (3), R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ３１ ~R ３８ are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the general formula (3A), and R Ｂ is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0448] In the compound represented by the general formula (3), R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ３１ ~R ３８ are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, or a group represented by the general formula (3A), and R Ｂ is preferably a substituted or unsubstituted phenyl group.

[0449] The compound represented by the general formula (3) is also preferably a compound having no pyridine ring, no pyrimidine ring, and no triazine ring.

[0450] (Compound Represented by General Formula (3B)) In the light-emitting layer of the organic EL element of the first embodiment, the third compound is also preferably a compound represented by the following general formula (3B).

[0451]

[0452] (In the general formula (3B), X Ｂ is an oxygen atom or a sulfur atom, １ is a carbon atom, n is 1, 2, or 3, k is 1, 2, or 3, m is 2, 3, or 4, and k+m=5, and when m is 2 or more, a plurality of R Ｌ are the same or different from each other, R Ｂ１ ~R Ｂ８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and when at least one of n and k is 2 or more, a plurality of R Ｂ１ are the same or different, and a plurality of R Ｂ２ are the same or different, and a plurality of R Ｂ３ are the same or different, and a plurality of R Ｂ４ are the same or different, and a plurality of R Ｂ５ are the same or different, and a plurality of R Ｂ６ are the same or different, and a plurality of R Ｂ７ are the same or different, and a plurality of R Ｂ８ are the same or different from each other, L Ｂ１ is a single bond or a linking group, provided that L Ｂ１ is a single bond, n is 1, and when k is 2 or more, a plurality of L Ｂ１ are the same or different from each other, and L as a linking group Ｂ１ represents a group derived from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a group derived from a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a group formed by bonding two groups selected from the group consisting of a group derived from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a group derived from a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and when k is 1 and m is 4, four R Ｌare bonded to any of the carbon atoms at positions a, b, c, d, and e shown in the general formula (3B), and one L Ｂ１ is the R Ｌ When k is 2 and m is 3, the carbon atom at the position a, b, c, d, or e is bonded to the carbon atom at which the carbon atom at the position a ... Ｌ are bonded to any of the carbon atoms at positions a, b, c, d, and e shown in the general formula (3B), and two L Ｂ１ are the R Ｌ When k is 3 and m is 2, the carbon atom bonded to any of the carbon atoms at positions a, b, c, d, and e that are not bonded to two R Ｌ are bonded to any of the carbon atoms at positions a, b, c, d, and e shown in the general formula (3B), and three L Ｂ１ are the R Ｌ and R is bonded to any of the carbon atoms at positions a, b, c, d, and e that are not bonded to R Ｂ４０ and R Ｂ４５ ~R Ｂ４８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, provided that three R Ｂ４０ are the same or different from each other, and three R Ｂ４０ are bonded to any of the carbon atoms at positions f, g, h, and i in the general formula (3B), and C １ is the R Ｂ４０ bonded to any of carbon atoms at positions f, g, h, and i that are not bonded to R Ｌ , R Ｂ３１ , R Ｂ３２ , R Ｂ３４ , R Ｂ３５ R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring Ｂ１ ~R Ｂ８ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. Ｂ４０ and R Ｂ４５ ~R Ｂ４８are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９０８ a group represented by -COOR ９０９ a halogen atom, a cyano group, a nitro group, -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７ a 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.

[0453] In the compound represented by the general formula (3B), when n is 2 or 3, the nitrogen atom N* in the structure in parentheses enclosed by the subscript n is, respectively, L Ｂ１ In the compound represented by the general formula (3B), L Ｂ１ is a single bond, the nitrogen atom N* in the structure in the parentheses enclosed by the subscript n is bonded to any of the carbon atoms at the positions a, b, c, d, and e. In the compound represented by the general formula (3B), when k is 2 or 3, L in the structure in the parentheses enclosed by the subscript k is bonded to any of the carbon atoms at the positions a, b, c, d, and e. Ｂ１ are bonded to any of the carbon atoms at positions a, b, c, d, and e, respectively.

[0454] For example, in the compound represented by the general formula (3B), n is 2, k is 1, and L Ｂ１ is bonded to the carbon atom at position c, and carbon atom C １ is bonded to the carbon atom at position h, the compound represented by general formula (3B) is represented by the following general formula (31B).

[0455]

[0456] (In the general formula (31B), R Ｂ１ ~R Ｂ８ , R Ｌ , R Ｂ３１ , R Ｂ３２ , R Ｂ３４ , R Ｂ３５ , R Ｂ４０ , R Ｂ４５ ~R Ｂ４８ , L Ｂ１ and X Ｂ are as defined in the general formula (3B).

[0457] For example, in the compound represented by the general formula (3B), L Ｂ１ is a single bond, n is 2, one of the two nitrogen atoms N* in the structure in parentheses enclosed by the subscript n is bonded to the carbon atom at position b, and the other is bonded to the carbon atom at position d, and the carbon atom C １ When is bonded to the carbon atom at position h, the compound represented by general formula (3B) is represented by the following general formula (32B).

[0458]

[0459] (In the general formula (32B), R Ｂ１ ~R Ｂ８ , R Ｌ , R Ｂ３１ , R Ｂ３２ , R Ｂ３４ , R Ｂ３５ , R Ｂ４０ , R Ｂ４５ ~R Ｂ４８ , and X Ｂ are as defined in the general formula (3B).

[0460] (Compound Represented by General Formula (MRX3)) In the light-emitting layer of the organic EL element of the first embodiment, the third compound is also preferably a compound represented by the following general formula (MRX3).

[0461]

[0462] (In the general formula (MRX3), Y ３１ ~Y ３６ are each independently CR ３ or a nitrogen atom, provided that Y ３１ ~Y ３６ two or more of R are nitrogen atoms; ３ If there are multiple R ３ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring ３ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９０８ a group represented by -COOR ９０９ a halogen atom, a cyano group, a nitro group, -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７ ) a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the following general formula (MRX3A):

[0463]

[0464] (In the general formula (MRX3A), R Ｂ is R in the general formula (3A). Ｂ is synonymous with R Ｂ When there are multiple R Ｂ are the same or different from each other, and L ３１ and L ３２ respectively represent L in the general formula (3A). ３１ and L ３２ is synonymous with n ３ is 1, 2, 3, 4 or 5, and L ３１ When is a single bond, n ３ is 1, and L ３２ is bonded to a carbon atom of the six-membered ring in general formula (MRX3), ３２ When there are multiple L ３２ are the same or different, and * represents the bonding site to the carbon atom of the six-membered ring in general formula (MRX3).

[0465] The compound represented by the general formula (MRX3) preferably does not contain a pyridine ring in the molecule.

[0466] The compound represented by the general formula (MRX3) is also preferably a compound represented by the following general formula (MRX31) or (MRX32).

[0467]

[0468] (In the general formula (MRX32), R ３５ ~R ３７one or more pairs of adjacent two or more of R in the general formula (MRX31) are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ３１ ~R ３３ and R in the general formula (MRX32) ３４ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ３５ ~R ３７ each independently represents R in general formula (MRX3). ３ is synonymous with

[0469] The compound represented by the general formula (MRX3) is also preferably a compound represented by the general formula (MRX31).

[0470] R in the general formula (MRX3) ３ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by general formula (MRX3A).

[0471] R in the general formula (MRX3) ３ are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by general formula (MRX3A) above.

[0472] The compound represented by the general formula (MRX3) preferably has, in the molecule, at least one group selected from the group consisting of groups represented by the following general formulae (MRXA31) to (MRXA44).

[0473]

[0474]

[0475] (In the general formulae (MRXA31) to (MRXA38), a plurality of R ３００one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ３３１ and R ３３２ are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring. ３００ , R ３３１ and R ３３２ , and R ３３３ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９０８ a group represented by -COOR ９０９ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and * in the general formulae (MRXA31) to (MRXA38) respectively indicates the bonding position to other atoms in the molecule of the compound represented by the general formula (MRX3).

[0476]

[0477]

[0478]

[0479] (In the general formulae (MRXA39) to (MRXA44), R ３４１ ~R ３５０ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, with the proviso that R ３４１ ~R ３５１ at least one of the following represents a bonding position to another atom in the molecule of the compound represented by general formula (MRX3); ３１ represents a sulfur atom, an oxygen atom, and NR ３５２ or CR ３５３ R ３５４ and R ３５３ and R ３５４ are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and are not at a bonding position with another atom in the molecule of the compound represented by general formula (MRX3), and do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring. ３４１ ~R ３５１ And, R ３５２ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ３５３ and R ３５４ and each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９０８ a group represented by -COOR ９０９ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0480] The compound represented by the general formula (MRX3) preferably has at least one group selected from the group consisting of the groups represented by the general formulae (MRXA38) to (MRXA44) in the molecule.

[0481] In the compound represented by the general formula (MRX3), Y ３１ ~Y ３６ At least one of the following is CR ３ and at least one R ３ is a group represented by the general formula (MRX3A), and R Ｂ is preferably any one of the groups represented by the general formulae (MRXA31) to (MRXA44).

[0482] In the compound represented by the general formula (MRX3), Y ３１ ~Y ３６ At least one of the following is CR ３ and at least one R ３ is a group represented by the general formula (MRX3A), and R Ｂ is preferably any one of the groups represented by the general formulae (MRXA38) to (MRXA44).

[0483] In the compound represented by the general formula (MRX3), R ３５２ is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0484] In the compound represented by the general formula (MRX3), R ３５３ and R ３５４are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form a substituted or unsubstituted monocycle and a substituted or unsubstituted fused ring ３５３ and R ３５４ are preferably each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0485] In the compound represented by the general formula (3), the compound represented by the general formula (3B), and the compound represented by the general formula (MRX3), L ３１ is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the arylene group, or a divalent group formed by bonding two groups selected from the group consisting of substituted or unsubstituted arylene groups having 6 to 50 ring carbon atoms, or a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the divalent group, ３２ is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0486] In the compound represented by the general formula (3), the compound represented by the general formula (3B), and the compound represented by the general formula (MRX3), L ３１ represents a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, and n ３ is 1, and L ３２ is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0487] In the compound represented by the general formula (3), the compound represented by the general formula (3B), and the compound represented by the general formula (MRX3), L ３１represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted phenylene group and a substituted or unsubstituted biphenylene group, or a trivalent group, tetravalent group, pentavalent group or hexavalent group derived from the divalent group; ３ is 1, and L ３２ is preferably a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0488] In the compound represented by the general formula (3), the compound represented by the general formula (3B), and the compound represented by the general formula (MRX3), the substituent in the case of "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted alkenyl group having 2 to 25 carbon atoms, an unsubstituted alkynyl group having 2 to 25 carbon atoms, an unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ an unsubstituted aralkyl group having 7 to 50 carbon atoms; —C(═O)R ９０８ a group represented by -COOR ９０９ a group represented by -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７ a group represented by —S(═O) ２ R ９３８ a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms, ９０１ ~R９０９ , and R ９３１ ~R ９３８ are preferably each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[0489] In the compounds represented by the general formula (3), the compounds represented by the general formula (3B), and the compounds represented by the general formula (MRX3), the substituent in the case of "substituted or unsubstituted" is preferably a halogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[0490] In the compounds represented by the general formula (3), the compounds represented by the general formula (3B), and the compounds represented by the general formula (MRX3), the substituent in the case of "substituted or unsubstituted" is preferably an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 12 ring atoms.

[0491] In the compound represented by the general formula (3), the compound represented by the general formula (3B), and the compound represented by the general formula (MRX3), it is also preferable that the groups described as "substituted or unsubstituted" are all "unsubstituted" groups.

[0492] (Method for Producing the Third Compound According to the First Embodiment) The third compound according to the first embodiment can be produced by a known method.

[0493] (Specific Examples of the Third Compound According to the First Embodiment) Specific examples of the third compound according to the first embodiment include the following compounds. However, the present invention is not limited to these specific examples of the compound.

[0494]

[0495]

[0496]

[0497]

[0498]

[0499]

[0500]

[0501]

[0502]

[0503]

[0504]

[0505]

[0506]

[0507]

[0508]

[0509]

[0510] (Relationship Between First Compound, Second Compound, and Third Compound in Emitting Layer) In the organic EL element according to the first embodiment, it is preferable that the first compound and the second compound satisfy the following mathematical formula (Mathematical Formula 2): (Mathematical Formula 2): S １ (M2) > S １ (M1) (S １ (M1) is the lowest excited singlet energy of the first compound, and S １ (M2) is the lowest excited singlet energy of the second compound.

[0511] In the organic EL element according to the first embodiment, the second compound and the third compound preferably satisfy the following formula (Formula 3): (Formula 3): S １ (M3) > S １ (M2) (S １ (M2) is the lowest excited singlet energy of the second compound, and S １ (M3) is the lowest excited singlet energy of the third compound.

[0512] In the organic EL device according to the first embodiment, the lowest excited singlet energy S １ (M1) and the lowest excited singlet energy S of the second compound １ (M2) and the lowest excited singlet energy S of the third compound １ (M3) preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 3A): (Mathematical Formula 3A): S １ (M3) > S １ (M2) > S １ (M1)

[0513] The energy gap T at 77 [K] of the third compound ７７Ｋ (M3) is the energy gap T at 77 [K] of the second compound ７７Ｋ The energy gap T at 77 [K] of the third compound is preferably larger than (M2). ７７Ｋ (M3) is the energy gap T of the first compound at 77 [K] ７７Ｋ It is preferable that it is larger than (M1).

[0514] Energy gap T at 77 [K] of the first compound ７７Ｋ (M1) and the energy gap T at 77 [K] of the second compound ７７Ｋ (M2) and the energy gap T at 77 [K] of the third compound ７７Ｋ It is preferable that (M3) satisfies the relationship of the following mathematical formula (Mathematical Formula 3B): (Mathematical Formula 3B): T ７７Ｋ (M3) > T ７７Ｋ (M2) > T ７７Ｋ (M1)

[0515] In one aspect of the organic EL element of the first embodiment, the second compound satisfies the following mathematical formula (44) or mathematical formula (44A). When the second compound satisfies the following mathematical formula (44), the luminous efficiency is likely to be improved. (Mathematical formula 44): |HOMO(M2)|≧6.0 eV (Mathematical formula 44A): |HOMO(M2)|≧6.1 eV (HOMO(M2) is the energy level of the highest occupied molecular orbital of the second compound.)

[0516] In one aspect of the organic EL element of the first embodiment, the third compound satisfies the following mathematical formula (Mathematical Formula 45) or mathematical formula (Mathematical Formula 45A). When the third compound satisfies the following mathematical formula (Mathematical Formula 45), the luminous efficiency is likely to be improved. (Mathematical Formula 45): |HOMO(M3)|≧5.8 eV (Mathematical Formula 45A): |HOMO(M3)|≧5.9 eV (HOMO(M3) is the energy level of the highest occupied molecular orbital of the third compound.) It is preferable that the upper limit of the value of |HOMO(M3)| of the third compound is 6.2 eV or less.

[0517] When the organic EL element of the first embodiment is caused to emit light, it is preferable that the fluorescent compound in the light-emitting layer mainly emits light.

[0518] The organic EL element of the first embodiment preferably emits red or green light. When the organic EL element of the first embodiment emits green light, the maximum peak wavelength of the light emitted from the organic EL element is preferably 500 nm or more and 560 nm or less. When the organic EL element of the first embodiment emits red light, the maximum peak wavelength of the light emitted from the organic EL element is preferably 600 nm or more and 660 nm or less. When the organic EL element of the first embodiment emits blue light, the maximum peak wavelength of the light emitted from the organic EL element is preferably 430 nm or more and 480 nm or less.

[0519] The maximum peak wavelength of light emitted from the organic EL element is measured as follows: ２ A voltage is applied to the organic EL element so that the spectral radiance spectrum obtained is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is measured, and this is defined as the maximum peak wavelength (unit: nm).

[0520] (Compound Content in Light-Emitting Layer) The contents of the first compound, second compound, and third compound contained in the light-emitting layer are preferably within the following ranges, for example. The content of the first compound in the light-emitting layer is more preferably 0.3% by mass or more and 4.0% by mass or less, more preferably 0.3% by mass or more and 3.0% by mass or less, and even more preferably 0.3% by mass or more and 2.0% by mass or less. The content of the second compound in the light-emitting layer is preferably 30% by mass or more and 50% by mass or less. The content of the second compound in the light-emitting layer is preferably 30% by mass or more and 45% by mass or less, and even more preferably 30% by mass or more and 40% by mass or less. The content of the third compound in the light-emitting layer is preferably 46% by mass or more and 69.7% by mass or less, more preferably 52% by mass or more and 69.7% by mass or less, and even more preferably 58% by mass or more and 69.7% by mass or less. The upper limit of the total content of the first compound, the second compound, and the third compound in the light-emitting layer is 100% by mass. Note that the first embodiment does not exclude the light-emitting layer containing materials other than the first compound, the second compound, and the third compound. The light-emitting layer may contain only one type of first compound, or two or more types. The light-emitting layer may contain only one type of second compound, or two or more types. The light-emitting layer may contain only one type of third compound, or two or more types.

[0521] (TADF mechanism) FIG. 4 is a diagram showing an example of the relationship between the energy levels of a first compound, a second compound, and a third compound in an emitting layer. In FIG. 4, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the first compound, and T1(M1) represents the lowest excited triplet state of the first compound. S1(M2) represents the lowest excited singlet state of the second compound, and T1(M2) represents the lowest excited triplet state of the second compound. S1(M3) represents the lowest excited singlet state of the third compound, and T1(M3) represents the lowest excited triplet state of the third compound. The dashed arrow from S1(M2) to S1(M1) in FIG. 4 represents Förster energy transfer from the lowest excited singlet state of the second compound to the lowest excited singlet state of the first compound. As shown in Figure 4, when a compound with a small ΔST (M2) is used as the second compound, the lowest excited triplet state T1 (M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1 (M2) due to thermal energy. Then, Förster-type energy transfer occurs from the lowest excited singlet state S1 (M2) of the second compound to the first compound, generating the lowest excited singlet state S1 (M1). As a result, fluorescence emission from the lowest excited singlet state S1 (M1) of the first compound can be observed. It is believed that the internal quantum efficiency can theoretically be increased to 100% by utilizing delayed fluorescence due to this TADF mechanism.

[0522] (Thickness of the Light-Emitting Layer) The thickness of the light-emitting layer in the organic EL element of the first embodiment is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less. 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.

[0523] <Electron Transporting Region> In this specification, a region consisting of multiple organic layers arranged between the light-emitting layer and the cathode may be referred to as an electron transporting region. The electron transporting region of the organic EL element according to this embodiment preferably further includes at least one of an electron transporting layer and an electron injection layer in addition to the second layer. In one aspect of the organic EL element according to the first embodiment, an electron transporting layer is included between the cathode and the second layer. In one aspect of the organic EL element according to the first embodiment, the electron transporting region includes the second layer and the electron injection layer, in this order from the anode side. In one aspect of the organic EL element according to the first embodiment, the electron transporting region includes the second layer, the electron transporting layer, and the electron injection layer, in this order from the light-emitting layer side.

[0524] In one aspect of the organic EL element of the first embodiment, the cathode and the electron injection layer are in direct contact. In one aspect of the organic EL element of the first embodiment, the electron injection layer and the second layer are in direct contact. In one aspect of the organic EL element of the first embodiment, the electron injection layer and the electron transport layer are in direct contact. In one aspect of the organic EL element of the first embodiment, the light-emitting layer and the second layer are in direct contact. The electron transport layer may include two or more organic layers. When the electron transport layer is composed of two organic layers, the two organic layers may be referred to as a first electron transport layer and a second electron transport layer. In one aspect of the organic EL element of the first embodiment, the electron transport zone includes, in this order from the anode side, the second layer, the first electron transport layer, the second electron transport layer, and the electron injection layer. In one aspect of the organic EL element of the first embodiment, the second layer and the electron transport layer are in direct contact.

[0525] (Second Layer) In the organic EL element of the first embodiment, the second layer contains a fifth compound. The fifth compound is not particularly limited as long as it satisfies the above formula (Formula 52).

[0526] In one aspect of the organic EL element of the first embodiment, the fifth compound is a compound represented by the following general formula (5A): As the fifth compound, a compound that satisfies the above mathematical formula (Mathematical Formula 52) can be selected from the compounds represented by the following general formula (5A). The fourth compound and the fifth compound are different compounds.

[0527]

[0528] (In the general formula (5A), A is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms; B is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms; L is a substituted or unsubstituted (m+n+1)-valent aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted (m+n+1)-valent heterocyclic group having 5 to 13 ring atoms, or an (m+n+1)-valent group having a structure in which two or three different groups are bonded together, selected from the group consisting of substituted or unsubstituted aromatic hydrocarbon ring groups having 6 to 18 ring carbon atoms and substituted or unsubstituted heterocyclic groups having 5 to 13 ring atoms; Ar ５ is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms, m is an integer of 0 or 1 or more, and a plurality of Ar ５ are the same or different from each other, Cz is a group represented by the general formula (Cz0), n is an integer of 2 or more, a plurality of Cz are the same or different from each other, and in the group represented by the general formula (Cz0), X ５０ is an oxygen atom, a sulfur atom, C(R ５１Ａ ) (R ５２Ａ ) or N(R ５３Ａ ) and R ５１Ａ and R ５２Ａ are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and R ５１１ ~R ５１８ one or more pairs of adjacent two or more of these are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, *4 is the bonding position to L, R ５１１~R ５１８ , R ５１Ａ , R ５２Ａ , and R ５３Ａ one of R is a single bond bonded to *3, R is not a single bond bonded to *3, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring ５１１ ~R ５１８ , R ５１Ａ , R ５２Ａ , and R ５３Ａ each independently represents a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ , R ９０２ , R ９０３ and R ９０４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other.)

[0529] In one aspect of the organic EL element of the first embodiment, the group represented by the general formula (Cz0) is a group represented by any one of the following general formulae (561) to (567).

[0530]

[0531] (In the general formulae (561) to (567), R ５１１ ~R ５１８ , R ５１Ａ and R ５２Ａ respectively represent R in the general formula (Cz0). ５１１ ~R ５１８ , R ５１Ａ and R ５２Ａ and * each independently represents a bonding position to L in the general formula (Cz0) (*4 in the general formula (Cz0)). When two or more groups represented by any one of the general formulae (561) to (567) are present, the two or more groups represented by any one of the general formulae (561) to (567) are the same as or different from each other.)

[0532] In one aspect of the organic EL element of the first embodiment, the fifth compound is a compound represented by the following general formula (5): As the fifth compound, a compound that satisfies the above mathematical formula (Mathematical Formula 52) can be selected from the compounds represented by the following general formula (5).

[0533]

[0534] (In the general formula (5), A is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms; B is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms; L is a substituted or unsubstituted (m+n+1)-valent aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted (m+n+1)-valent heterocyclic group having 5 to 13 ring atoms, or an (m+n+1)-valent group having a structure in which two or three different groups are bonded together, selected from the group consisting of substituted or unsubstituted aromatic hydrocarbon ring groups having 6 to 18 ring carbon atoms and substituted or unsubstituted heterocyclic groups having 5 to 13 ring atoms; Ar ５ is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms, m is an integer of 0 or 1 or more, and a plurality of Ar ５ are the same or different from each other, Cz is a group represented by the general formula (Cz1), n ​​is an integer of 2 or more, a plurality of Cz are the same or different from each other, and in the group represented by the general formula (Cz1), R ５１１ ~R ５１８ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring ５１１ ~R ５１８ each independently represents a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, * in general formula (Cz1) is bonded to L, and in the fifth compound, R ９０１ , R ９０２ , R ９０３ and R ９０４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other.)

[0535] In one aspect of the organic EL element of the first embodiment, the fifth compound is a group represented by the following general formula (50A):

[0536]

[0537] (In the general formula (50A), A, B, Ar ５ , L, and Cz are A, B, Ar in the general formula (5), respectively. ５ , L, and Cz; and in the group represented by formula (Cz1), R ５１１ ~R ５１８ respectively represent R in the general formula (Cz1) in the general formula (5). ５１１ ~R ５１８ is synonymous with

[0538] In one aspect of the organic EL element of the first embodiment, the fifth compound is a group represented by the following general formula (51):

[0539]

[0540] (In the general formula (51), A, B, and Cz are the same as A, B, and Cz in the general formula (5), respectively, and R ５８１ , R ５８３ , and R ５８５ each independently represents a hydrogen atom, a cyano group, an alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; Ar ５、 or a group represented by the general formula (Cz1), ５ is R in the general formula (5). ９０１ ~R ９０４ is synonymous with R ９０１ ~R ９０４ are R in the general formula (5), respectively. ９０１ ~R ９０４ is synonymous with

[0541] In one embodiment of the compound represented by general formula (51), A is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and B is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

[0542] In the fifth compound according to the first embodiment, A and B are the same or different.

[0543] In one aspect of the organic EL element of the first embodiment, the fifth compound is a compound represented by the following general formula (52):

[0544]

[0545] (In the general formula (52), R ５８１ , R ５８３ , and R ５８５are R in the general formula (51), respectively. ５８１ , R ５８３ , and R ５８５ is synonymous with R ５８６ ~R ５９５ are each independently a hydrogen atom, 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 ), a group represented by —S—(R ９０５ a halogen atom, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ ~R ９０３ are R in the general formula (5), respectively. ９０１ ~R ９０３ is synonymous with R ９０５ is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and R ９０５ If there are multiple R ９０５ are the same or different from each other.)

[0546] In one embodiment of the compound represented by the general formula (52), R ５８９ represents a hydrogen atom, 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 ), a group represented by —S—(R ９０５ a halogen atom, a nitro group, or an unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0547] In one embodiment of the compound represented by the general formula (52), R ５８１ , R ５８３ , R ５８５ , R ５８６ ~R ５８８ , and R ５９０ ~R ５９５ are each independently a hydrogen atom or a substituted or unsubstituted phenyl group; R ５８９ is a hydrogen atom.

[0548] In one embodiment of the fifth compound, the substituents in the term "substituted or unsubstituted" are each independently a substituted or unsubstituted 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 aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0549] In one embodiment of the fifth compound, the substituents in the term "substituted or unsubstituted" are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthrenyl group. In one embodiment of the fifth compound, the substituents in the term "substituted or unsubstituted" are an "unsubstituted" group.

[0550] (Method for Producing Fifth Compound According to First Embodiment) The fifth compound according to the first embodiment can be produced by a known method.

[0551] (Specific Examples of the Fifth Compound According to the First Embodiment) Specific examples of the fifth compound according to the first embodiment include the following compounds. However, the present invention is not limited to these specific examples of the compound.

[0552]

[0553]

[0554]

[0555]

[0556] (Electron Transport Layer) One aspect of the organic EL element of the first embodiment includes an electron transport layer between the light-emitting layer and the cathode. As the electron transport layer, for example, "a substance with high electron transport properties (such as a metal complex, a heteroaromatic compound, or a polymer compound)" described in the <Configuration of Organic EL Element> below can be used.

[0557] (Electron Injection Layer) One aspect of the organic EL element of the first embodiment includes an electron injection layer between the electron transport layer and the cathode. As the hole injection layer, for example, the "substance with high hole injection properties" described in the <Configuration of Organic EL Element> described later can be used.

[0558] <Configuration of Organic EL Element> The configuration of the organic EL element will be further described.

[0559] (Substrate) The substrate is used as a support for the organic EL element. For example, glass, quartz, plastic, etc. can be used as the substrate. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate. Examples of materials for forming the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Inorganic vapor deposition films can also be used.

[0560] (Anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, etc. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metal materials (e.g., titanium nitride).

[0561] These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1 mass % to 10 mass % of zinc oxide added to indium oxide. Furthermore, for example, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5 mass % to 5 mass % of tungsten oxide and 0.1 mass % to 1 mass % of zinc oxide relative to indium oxide. Alternatively, the films may be formed by vacuum deposition, coating, inkjet printing, spin coating, or the like.

[0562] Of the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that facilitates hole injection regardless of the work function of the anode, and therefore materials that can be used as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures thereof, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0563] Materials with low work functions, such as elements belonging to Group 1 or 2 of the periodic table, can also be used, including alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these. When forming an anode using alkali metals, alkaline earth metals, and alloys containing these, vacuum deposition or sputtering can be used. Furthermore, when using silver paste or the like, coating or inkjet printing can be used.

[0564] When the organic EL element is a bottom-emission type, the anode is preferably formed of a metal material having optical transparency or semi-transparency that transmits light from the light-emitting layer. In this specification, optical transparency or semi-transparency means a property that transmits 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The optically transparent or semi-transparent metal material can be appropriately selected from the materials listed in the anode section.

[0565] When the organic EL device is a top-emission type, the anode is a reflective electrode having a reflective layer. The reflective layer is preferably formed of a metal material having optical reflectivity. In this specification, optical reflectivity means the property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The metal material having optical reflectivity can be appropriately selected from the materials listed in the anode section. The anode may be composed of only a reflective layer, or may have a multilayer structure having a reflective layer and a conductive layer (preferably a transparent conductive layer). When the anode has a reflective layer and a conductive layer, it is preferable that the conductive layer be disposed between the reflective layer and the hole-transporting region. The conductive layer can be appropriately selected from the materials listed in the anode section.

[0566] (Cathode) For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such a cathode material include elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.

[0567] 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.

[0568] By providing an electron injection layer, the cathode can be formed using various conductive materials, regardless of the magnitude of the work function, such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, etc. These conductive materials can be formed into films by a sputtering method, an inkjet method, a spin coating method, or the like.

[0569] When the organic EL element is a bottom-emission type, the cathode is a reflective electrode. The reflective electrode is preferably formed of a metal material having light reflectivity. The metal material having light reflectivity can be appropriately selected from the materials listed in the section on the cathode.

[0570] When the organic EL element is a top-emission type, the cathode is preferably formed of a light-transmitting or semi-transmitting metal material that transmits light from the light-emitting layer. The light-transmitting or semi-transmitting metal material can be appropriately selected from the materials listed in the cathode section.

[0571] The organic EL element according to the first embodiment may be a bottom-emission organic EL element. Alternatively, the organic EL element according to the first embodiment may be a top-emission organic EL element. When the organic EL element is a bottom-emission organic EL element, it is preferable that the anode is a light-transmitting electrode having light transparency, and the cathode is a light-reflective electrode having light reflectivity. When the organic EL element is a top-emission organic EL element, it is preferable that the anode is a light-reflective electrode having light reflectivity, and the cathode is a light-transmitting electrode having light transparency.

[0572] (Capping Layer) When the organic EL element is a top-emission type, the organic EL element usually has a capping layer on the cathode. The capping layer may contain, for example, at least one compound selected from the group consisting of polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitride, and silicon compounds (such as silicon oxide). The capping layer may also contain, for example, at least one compound selected from the group consisting of aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, or dibenzofuran derivatives. A laminate obtained by stacking layers containing these substances can also be used as the capping layer.

[0573] (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. Furthermore, examples of the material 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, Examples of the aromatic amine compound include 3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1). Furthermore, a polymer compound (such as an oligomer, dendrimer, or polymer) can also be used as the substance with high hole injection properties. Examples of such polymer compounds include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD).Furthermore, polymer compounds to which an acid has been added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[0574] (Hole Transport Layer) The hole transport layer is a layer containing a substance with high hole transport properties. For the hole transport layer, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: NPB), Examples of aromatic amine compounds that can be used include 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The substances mentioned here are mainly 10 －６ cm ２ The hole-transporting layer may be a material having a hole mobility of 1 / Vs or more. Carbazole derivatives such as CBP, CzPA, and PCzPA, or anthracene derivatives such as t-BuDNA, DNA, and DPAnth may be used for the hole-transporting layer. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) may also be used. However, other materials may also be used as long as they have a higher hole-transporting property than electron-transporting property. The layer containing the material having a high hole-transporting property may be a single layer or a layer in which two or more layers made of the above-mentioned materials are stacked.

[0575] (Electron Transport Layer) The electron transport layer is a layer containing a substance with high electron transport properties. For the electron transport layer, 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds can be used. Specifically, low-molecular organic compounds such as Alq and tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq) can be used. ３ ), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq ２ ), BAlq, Znq, ZnPBO, ZnBTZ, and other metal complexes can be used. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: OXD-8), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-9 ... Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) can also be used. 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 a single layer or a stack of two or more layers made of the above-mentioned substances. A polymer compound may also be used for the electron-transporting layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy), or the like may be used.

[0576] (Electron Injection Layer) The electron injection layer is a layer containing a substance with high electron injection properties. Examples of the electron injection layer include lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), and calcium fluoride (CaF ２Alkali metals, alkaline earth metals, or compounds thereof, such as lithium oxide (LiOx), may be used. Alternatively, a material having electron transport properties containing an alkali metal, alkaline earth metal, or compound thereof, such as magnesium (Mg) in Alq, may be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, a composite material containing an organic compound and an electron donor (donor) may be used for the electron injection layer. 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, the above-mentioned materials constituting the electron transport layer (e.g., metal complexes and heteroaromatic compounds) may be used. The electron donor may be any material 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. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, such as lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (abbreviated as TTF) can also be used.

[0577] (Layer Formation Method) The method for forming each layer of the organic EL element according to any of the above-described embodiments is not limited to those specifically mentioned above, but may be any known method such as a dry film formation method such as a vacuum deposition method, a sputtering method, a plasma method, or an ion plating method, or a wet film formation method such as a spin coating method, a dipping method, a flow coating method, or an inkjet method.

[0578] (Film Thickness) The film thickness of each organic layer in the organic EL element according to the first embodiment is not limited unless specifically mentioned above. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and if the film thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the film thickness of each organic layer in the organic EL element is usually preferably in the range of several nm to 1 μm.

[0579] The organic EL element according to the first embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0580] Second Embodiment The configuration of an organic EL element according to a second embodiment will be described. In the second embodiment, the same materials and compounds as those described in the first embodiment can be used for materials and compounds not specifically mentioned.

[0581] The organic EL device according to the second embodiment differs from the organic EL device according to the first embodiment in that the light-emitting layer contains the second compound and the third compound, but does not contain the first compound. The other points are the same as those of the first embodiment. The third compound is preferably a host material, and the second compound is preferably a dopant material. In the second embodiment, the light-emitting layer preferably does not contain a phosphorescent metal complex, and preferably does not contain any metal complex other than the phosphorescent metal complex.

[0582] (Second Compound) As the second compound, the second compound described in the first embodiment can be used. The second compound is a thermally activated delayed fluorescent compound.

[0583] (Third Compound) As the third compound, the third compound described in the first embodiment can be used.

[0584] (Relationship between the second compound and the third compound in the light-emitting layer) In the organic EL device according to the second embodiment, the lowest excited singlet energy S １ (M2) and the lowest excited singlet energy S of the third compound １ (M3) preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 3): S １ (M3) > S １ (M2) …(Math 3)

[0585] The energy gap T at 77 [K] of the third compound ７７Ｋ (M3) is the energy gap T at 77 [K] of the second compound ７７Ｋ It is preferable that it is larger than (M2).

[0586] FIG. 5 is a diagram illustrating the principle of light emission according to the second embodiment. In FIG. 5, S0 represents the ground state. S1(M2) represents the lowest excited singlet state of the second compound, and T1(M2) represents the lowest excited triplet state of the second compound. S1(M3) represents the lowest excited singlet state of the third compound, and T1(M3) represents the lowest excited triplet state of the third compound. As shown in FIG. 5, when a compound with a small ΔST(M2) is used as the second compound, the lowest excited triplet state T1(M2) of the second compound can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) due to thermal energy. By utilizing the reverse intersystem crossing that occurs in this second compound, for example, light emission as shown in (i-1) or (ii-1) below can be observed. (i-1) When the emitting layer does not contain a fluorescent dopant whose lowest excited singlet state S1 is lower than the lowest excited singlet state S1(M2) of the second compound, light emission from the lowest excited singlet state S1(M2) of the second compound can be observed. (ii-1) When the emitting layer contains a fluorescent dopant (the first compound in the first embodiment) whose lowest excited singlet state S1 is lower than the lowest excited singlet state S1(M2) of the second compound, light emission from the fluorescent dopant can be observed. Note that in the organic EL element of the second embodiment, the light emission shown in (i-1) above can be observed. In the organic EL element of the first embodiment described above, the light emission shown in (ii-1) above can be observed.

[0587] (Compound Content in Light-Emitting Layer) In the organic EL element according to the second embodiment, the contents of the second compound and the third compound contained in the light-emitting layer are preferably within the following ranges, for example. The content of the second compound in the light-emitting layer is 30% by mass or more and 50% by mass or less. The content of the second compound in the light-emitting layer is preferably 30% by mass or more and 45% by mass or less, and more preferably 30% by mass or more and 40% by mass or less. The content of the third compound in the light-emitting layer is preferably 50% by mass or more and 70% by mass or less, more preferably 55% by mass or more and 70% by mass or less, and even more preferably 60% by mass or more and 70% by mass or less. The upper limit of the total content of the second compound and the third compound in the light-emitting layer is 100% by mass. In the organic EL element according to the second embodiment, the light-emitting layer may contain only one type of second compound or may contain two or more types. The light-emitting layer may contain only one type of third compound or may contain two or more types.

[0588] According to the second embodiment, it is possible to improve the luminous efficiency and realize an organic EL element having a long life. The organic EL element according to the second embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0589] Third Embodiment (Electronic Device) An electronic device according to a third 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.

[0590] The display device as the electronic device according to the third embodiment is preferably an organic EL display device having organic EL elements mounted thereon as red, green, and blue pixels, in which at least one of the red and green pixels is preferably an organic EL element according to any of the above-described embodiments, and the green pixel is more preferably an organic EL element according to any of the above-described embodiments.

[0591] [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.

[0592] For example, the number of light-emitting layers is not limited to one, and multiple light-emitting layers may be stacked. When the organic EL element has multiple light-emitting layers, it is sufficient that at least one of the light-emitting layers satisfies the conditions described in the above embodiment. For example, the other light-emitting layers may be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize light emission by electron transition from a triplet excited state directly to the ground state. Furthermore, when the organic EL element has multiple light-emitting layers, these light-emitting layers may be provided adjacent to each other, or the organic EL element may be a so-called tandem organic EL element in which multiple light-emitting units are stacked via an intermediate layer.

[0593] Furthermore, for example, a barrier layer may be provided adjacent to at least one of the anode side and the cathode side of the light-emitting layer. The barrier layer is preferably disposed in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons. For example, when a barrier layer is disposed in contact with the cathode side of the light-emitting layer, the barrier layer transports electrons and blocks holes from reaching a layer (e.g., an electron transport layer) closer to the cathode than the barrier layer. When the organic EL device includes an electron transport layer, the barrier layer is preferably provided between the light-emitting layer and the electron transport layer. When a barrier layer is disposed in contact with the anode side of the light-emitting layer, the barrier layer transports holes and blocks electrons from reaching a layer (e.g., a hole transport layer) closer to the anode than the barrier layer. When the organic EL device includes a hole transport layer, the barrier layer is preferably provided between the light-emitting layer and the hole transport layer. Furthermore, the barrier layer may be provided adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to its surrounding layers. The blocking layer prevents excitons generated in the light-emitting layer from migrating to layers closer to the electrode than the blocking layer (for example, the electron transport layer and the hole transport layer).The light-emitting layer and the blocking layer are preferably in contact with each other.

[0594] In addition, the specific structure and shape in carrying out the present invention may be other structures within the scope that the object of the present invention can be achieved.

[0595] 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.

[0596] <Compounds> The structures of the second compound, the fourth compound, and the fifth compound used in the production of the organic EL devices according to Examples 1 to 9 are shown below.

[0597]

[0598]

[0599]

[0600] The structures of the comparative compounds used in the production of the organic EL devices according to Comparative Examples 1 to 4 are shown below.

[0601]

[0602]

[0603] The structures of other compounds used in the production of the organic EL devices according to Examples 1 to 9 and Comparative Examples 1 to 4 are shown below.

[0604]

[0605] <Preparation of Organic EL Device> An organic EL device was prepared as follows and evaluated.

[0606] Example 1 A 25 mm x 75 mm x 1.1 mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 1 minute. The ITO film thickness was 130 nm. The cleaned glass substrate with transparent electrode lines was attached to a substrate holder in a vacuum deposition apparatus, and first, compound HT-1 and compound HA were co-deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, forming a hole injection layer with a film thickness of 10 nm. The proportion of compound HT-1 in the hole injection layer was 97% by mass, and the proportion of compound HA was 3% by mass. Next, compound HT-1 as a sixth compound was deposited on the hole injection layer to form a hole transport layer with a film thickness of 115 nm. Next, compound EBL-1 as a fourth compound was deposited on the hole transport layer to form a first layer (also referred to as an electron blocking layer) with a film thickness of 5 nm. Next, on the first layer, compound Matrix-1 as a host material (third compound), compound TADF-1 as a delayed fluorescent compound (second compound), and compound GD-1 as a fluorescent compound (first compound) were co-deposited to form an emitting layer with a film thickness of 25 nm. The proportion of compound Matrix-1 in the emitting layer was 69.4% by mass, the proportion of compound TADF-1 was 30% by mass, and the proportion of compound GD-1 was 0.6% by mass. Next, compound HBL-1 as a fifth compound was deposited on the emitting layer to form a second layer (also referred to as a hole blocking layer) with a film thickness of 30 nm. Next, compound ET-2 and compound Liq were co-deposited on the hole blocking layer to form an electron transport layer with a film thickness of 25 nm. The concentration of compound ET-2 in the electron transport layer was 50% by mass, and the concentration of compound Liq was 50% by mass. It should be noted that Liq is an abbreviation for (8-quinolinolato)lithium. Next, ytterbium (Yb) was vapor-deposited on the electron transport layer to form an electron injection layer with a thickness of 1 nm. Then, metal aluminum (Al) was vapor-deposited on the electron injection layer to form a metal Al cathode with a thickness of 80 nm. In this manner, the organic EL element according to Example 1 was fabricated. The element configuration of the organic EL element according to Example 1 is schematically shown as follows:ITO(130) / HT-1:HA(10,97%:3%) / HT-1(115) / EBL-1(5) / Matrix-1:TADF-1:GD-1(25,69.4%:30%:0.6%) / HBL-1(30) / ET-2:Liq(25,50%:50%) / Yb(1) / Al(80) In the above element configuration, the numbers in parentheses indicate the film thickness (unit: nm). Similarly, in the above element configuration, the percentages in parentheses (97%:3%) indicate the proportions (mass%) of Compound HT-1 and Compound HA in the hole injection layer, the percentages (69.4%:30%:0.6%) indicate the proportions (mass%) of Compound Matrix-1, Compound TADF-1, and Compound GD-1 in the light-emitting layer, and the percentages (50%:50%) indicate the proportions (mass%) of Compound ET-2 and Liq in the electron transport layer. The same notation is used hereinafter.

[0607] (Examples 2 and 3) The organic EL element of Example 2 was fabricated in the same manner as in Example 1, except that the fifth compound used in the second layer of Example 1 was changed to the fifth compound shown in Table 1.

[0608] (Examples 4 and 7) The organic EL devices of Examples 4 and 7 were fabricated in the same manner as in Example 1, except that the fourth compound used in the first layer of Example 1 was changed to the fourth compound shown in Table 1.

[0609] (Examples 5, 6, 8, and 9) The organic EL devices of Examples 5, 6, 8, and 9 were fabricated in the same manner as in Example 1, except that the fourth compound used in the first layer and the fifth compound used in the second layer of Example 1 were changed to the fourth compound and the fifth compound shown in Table 1, respectively.

[0610] Comparative Examples 1, 3, and 4 The organic EL devices of Comparative Examples 1, 3, and 4 were fabricated in the same manner as in Example 1, except that the fourth compound used in the first layer and the fifth compound used in the second layer of Example 1 were changed to the fourth compound and the fifth compound shown in Table 1, respectively.

[0611] Comparative Example 2 The organic EL element of Comparative Example 2 was fabricated in the same manner as in Example 1, except that the fifth compound used in the second layer of Example 1 was changed to the fifth compound shown in Table 1.

[0612] <Evaluation of Organic EL Device> The fabricated organic EL device was evaluated as follows. The evaluation results are shown in Table 1.

[0613] (Drive voltage) Current density: 10 mA / cm ２ The voltage was measured when a current was applied between the anode and cathode of the prepared organic EL element so that the following was true. Based on the measured values ​​of the driving voltage for each example (Examples 1 to 9 and Comparative Examples 1 to 4) and the following formula (Formula 1X), the "driving voltage difference ΔV" (unit: V) was calculated (Formula 1X): driving voltage difference ΔV = (driving voltage for each example) - (driving voltage for Comparative Example 1).

[0614] (CIE 1931 chromaticity) The current density of the organic EL element is 10 mA / cm ２ The spectral radiance spectrum when a voltage was applied to the element so that the spectral radiance spectrum was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) CIE x and CIE y were calculated from the obtained spectral radiance spectrum.

[0615] (External quantum efficiency EQE and maximum peak wavelength λ ＥＬ The organic EL device thus fabricated was subjected to a current density of 10.00 mA / cm ２ The spectral radiance spectrum when a voltage was applied so that the maximum peak wavelength λ was obtained was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming that Lambertian radiation was performed. In addition, from the obtained spectral radiance spectrum, the maximum peak wavelength λ ＥＬ The emission constant (unit: nm) and emission half-width FWHM (unit: nm) were determined. FWHM is an abbreviation for Full Width at Half Maximum. Table 1 shows the "EQE (relative value)" (unit: %). The "EQE (relative value)" of Examples 1 to 9 and Comparative Examples 1 to 4 was calculated based on the EQE of each example and the following mathematical formula (Math. 11X). (Math. 11X): EQE (relative value) = (EQE of each example / EQE of Comparative Example 1) × 100

[0616] (Lifespan (LT95)) The obtained organic EL element was subjected to a current density of 50 mA / cm ２ A voltage was applied so that the voltage was such that the voltage was 0.01 V, and the time (LT95 (unit: hours)) until the luminance reached 95% of the initial luminance was measured. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). Table 1 shows the "LT95 (relative value)" (unit: %). The LT95 (relative value) of Examples 1 to 9 and Comparative Examples 1 to 4 was calculated based on the following formula (Formula 12X). (Formula 12X): LT95 (relative value) = (LT95 of each Example / LT95 of Comparative Example 1) × 100

[0617]

[0618] In the element of Comparative Example 2, in which the fourth compound contained in the first layer in Comparative Example 1 was changed from Ref-EBL, which does not satisfy the relationship of Formula 51, to EBL-1, which satisfies the relationship of Formula 51, a lower voltage and higher efficiency of the element were observed, but the lifetime was shortened. The elements of Examples 1 to 5 and 7 to 9, in which the fourth compounds contained in the first layer and the second layer respectively satisfy the relationship of Formula 51 and the fifth compound satisfy the relationship of Formula 52, showed improved luminous efficiency and longer lifetimes than the element of Comparative Example 1 which does not satisfy the relationships of Formulas 51 and 52, and the elements of Comparative Examples 2 to 4 which do not satisfy the relationship of Formula 52. The element of Example 6, which satisfies the relationship of the above formulas (51) and (52), had a longer life than the element of Comparative Example 1, which does not satisfy the relationship of the above formulas (51) and (52), and the elements of Comparative Examples 2 to 4, which do not satisfy the relationship of the above formula (52).

[0619] <Evaluation of Compounds> The above-mentioned compounds were evaluated as follows. The evaluation results are shown in Table 1.

[0620] (Ionization potential Ip and energy level HOMO of highest occupied molecular orbital) The ionization potential Ip of the measurement object (compound or material) was calculated using the following formula (Y1). The value of the energy level HOMO of the highest occupied molecular orbital corresponds to the value of the ionization potential Ip with a negative sign. The units of the ionization potential Ip and the energy level HOMO of the highest occupied molecular orbital are eV. Table 1 shows the value of |HOMO| (value of Ip). (Y1): Ip = -1.40 x (Eox - Efc) - 4.60 eV In the formula (Y1), Eox and Efc are as follows. Eox: first oxidation potential of the object to be measured (DPV, positive scan) Efc: first oxidation potential of ferrocene (DPV, positive scan), (ca. +0.55 V vs Ag / AgCl) The redox potential was measured by differential pulse voltammetry (DPV) using an electrochemical analyzer (ALS: CHI852D). The sample solution used for the measurement was prepared by dissolving the substance to be measured to a concentration of 1.0 mmol / L in N,N-dimethylformamide (DMF) as the solvent, and dissolving tetrabutylammonium hexafluorophosphate (TBHP) as the supporting electrolyte to a concentration of 100 mmol / L. A glassy carbon electrode was used as the working electrode, and a platinum (Pt) electrode was used as the counter electrode.

[0621] (Delayed Fluorescence of Compound) 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 obtain an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the sample solution was measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation). The fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. The 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. After being excited by pulsed light (light irradiated from a pulsed laser) having a wavelength absorbed by the compound TADF-1, prompt luminescence (immediate luminescence) is observed immediately from the excited state, and delay luminescence (delayed luminescence) is not observed immediately after the excitation but is observed later. In this example, delayed fluorescence means that the amount of delay luminescence (delayed luminescence) is 5% or more of the amount of prompt luminescence (immediate luminescence). Specifically, the amount of prompt luminescence (immediate luminescence) is X Ｐ The amount of delayed light emission is set to X Ｄ When this is done, X Ｄ / X Ｐ This means that the value of X is 0.05 or more. The amounts of prompt luminescence and delay luminescence and their ratio can be determined by a method similar to that described in "Nature 492, 234-238, 2012" (Reference 1). The device used to calculate the amounts of prompt luminescence and delay luminescence is not limited to the device described in Reference 1 or the device shown in Figure 2. It was confirmed that the amount of delay luminescence (delayed luminescence) was 5% or more of the amount of prompt luminescence (immediate luminescence) for compound TADF-1. Specifically, for compound TADF-1, X Ｄ / X Ｐ The value was 0.05 or more.

[0622] (energy gap T７７Ｋ ) Energy gap T of the compound to be measured ７７Ｋ is the energy gap T described in the above "Relationship between triplet energy and energy gap at 77 [K]" ７７Ｋ The energy gap T of the compound TADF-1 as the second compound was measured by the method described above. ７７Ｋ The value of was 2.76 eV.

[0623] 1A...organic electroluminescence element, 10A...organic layer, 2...substrate, 3...anode, 4...cathode, 5...light-emitting layer, 6...hole injection layer, 7...hole transport layer, 7A...hole transport region, 8...electron transport layer, 8A...electron transport region, 9...electron injection layer, 71...first layer, 81...second layer.

Claims

1. An organic electroluminescence device comprising an anode, a cathode, an emitting layer between the anode and the cathode, a first layer between the anode and the emitting layer, and a second layer between the cathode and the emitting layer, wherein the emitting layer contains a delayed fluorescent compound as a second compound, the content of the second compound in the emitting layer is 30% by mass or more and 50% by mass or less, the first layer contains a fourth compound, and the second layer contains a fifth compound, the fourth compound and the fifth compound are different from each other, the fourth compound satisfies the following formula (Formula 51), and the fifth compound satisfies the following formula (Formula 52). (Formula 51): |HOMO(M4)|≧5.74 eV (Formula 52): T ７７Ｋ (M5)≦2.90 eV (HOMO(M4) is the energy level of the highest occupied molecular orbital of the fourth compound, T ７７Ｋ (M5) is the energy gap at 77 [K] of the fifth compound.) 2. The organic electroluminescence device according to claim 1, wherein the fourth compound satisfies the following formula (Formula 51A): |HOMO(M4)| ≧ 5.80 eV.

3. The organic electroluminescence device according to claim 1 or 2, wherein the fifth compound satisfies the following formula (Formula 52A): T ７７Ｋ (M5)≦2.70eV 4. The organic electroluminescence device according to claim 1, wherein the second compound satisfies the following formula (Formula 54): |T ７７Ｋ (M2)-T ７７Ｋ (M5)|≦0.10eV 5. The organic electroluminescence device according to any one of claims 1 to 4, wherein the content of the second compound in the light-emitting layer is 30% by mass or more and 45% by mass or less.

6. The organic electroluminescence device according to any one of claims 1 to 5, wherein the content of the second compound in the light-emitting layer is 30% by mass or more and 40% by mass or less.

7. The organic electroluminescence device according to any one of claims 1 to 6, wherein the first layer and the light-emitting layer are in direct contact with each other.

8. The organic electroluminescence device according to any one of claims 1 to 7, wherein the light-emitting layer and the second layer are in direct contact with each other.

9. The organic electroluminescence device according to any one of claims 1 to 8, wherein the light-emitting layer does not contain a metal complex.

10. The organic electroluminescence device according to any one of claims 1 to 9, wherein the light-emitting layer does not contain a phosphorescent material.

11. The organic electroluminescence device according to any one of claims 1 to 10, further comprising a hole transport layer between the anode and the first layer.

12. The organic electroluminescence device according to claim 11, wherein the first layer and the hole transport layer are in direct contact with each other.

13. The organic electroluminescence device according to any one of claims 1 to 12, further comprising an electron transport layer between the cathode and the second layer.

14. The organic electroluminescence device according to claim 13, wherein the second layer and the electron transport layer are in direct contact with each other.

15. The organic electroluminescence device according to any one of claims 1 to 14, wherein the fourth compound is a compound represented by the following general formula (4): (In the general formula (4), L Ａ１ , L Ａ２ and L Ａ３ each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; ４１１ , Ar ４１２ and Ar ４１３ each independently represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; Ｃ１ ) (R Ｃ２ ) (R Ｃ３ ) or a group represented by the general formula (4A), ４１１ , Ar ４１２ , and Ar ４１３ At least one of the groups represented by the general formula (4A) is a group represented by the general formula (4A), and when two or more groups represented by the general formula (4A) are present, the two or more groups represented by the general formula (4A) are the same or different from each other, R Ｃ１ , R Ｃ２ and R Ｃ３ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; R Ｃ１ When there are multiple R Ｃ１ are the same or different from each other, R Ｃ２ When there are multiple R Ｃ２ are the same or different from each other, R Ｃ３ When there are multiple R Ｃ３ are the same or different, and in the general formula (4A), X ４ is an oxygen atom, a sulfur atom, C(R ４１Ａ ) (R ４２Ａ ) or N(R ４３Ａ ) and R ４１Ａ and R ４２Ａ are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other, and R ４１ ~R ４８ Among adjacent pairs of two or more of the above, one or more pairs are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other, and *2 represents L Ａ１ , L Ａ２ Or L Ａ３ is the bonding position with R ４１ ~R ４８ , R ４１Ａ , R ４２Ａ and R ４３Ａ one of R is a single bond bonded to *1, R is not a single bond bonded to *1, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted condensed ring ４１ ~R ４８ , R ４１Ａ , R ４２Ａ and R ４３Ａ each independently represents a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ) group represented by -O-(R ９０４ a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ ~R ９０４ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; R ９０１ When there are multiple R ９０１ are the same or different from each other, R ９０２ When there are multiple R ９０２ are the same or different from each other, R ９０３ When there are multiple R ９０３ are the same or different from each other, R ９０４ When there are multiple R ９０４ are the same or different from each other.) 16. In at least one group represented by the general formula (4A), R ４１ ~R ４８ The organic electroluminescence device according to claim 15 , wherein one of the groups is a single bond bonded to *1.

17. The organic electroluminescence device according to claim 15, wherein the fourth compound is a compound represented by the following general formula (40A): (In the above general formula (40A), Ar ４１１ , Ar ４１２ , L Ａ１ , L Ａ２ and L Ａ３ respectively represent Ar in the general formula (4). ４１１ , Ar ４１２ , L Ａ１ , L Ａ２ and L Ａ３ is synonymous with R ４１ ~R ４８ are R in the general formula (4), ４１ ~R ４８ where R ４１ ~R ４４ One of them is L. Ａ３ is a single bond that bonds to X ４ is X in the general formula (4). ４ (Same meaning as above.) 18. The organic electroluminescence device according to claim 15, wherein the fourth compound is a compound represented by the following general formula (40): (In the general formula (40), Ar ４１１ , Ar ４１２ and Ar ４１３ respectively represent Ar in the general formula (4). ４１１ , Ar ４１２ and Ar ４１３ n1 is 4, and four Ra １１ are the same or different from each other, and four Ra １１ one or more pairs of adjacent two or more of the groups are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, n2 is 4, and four Ra １２ are the same or different from each other, and four Ra １２ one or more pairs of adjacent two or more of the groups are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, n3 is 4, and four Ra １３ are the same or different from each other, and four Ra １３ one or more pairs of adjacent two or more of Ra are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused ring. １１ , Ra １２ and Ra １３ each independently represents a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ) group represented by -O-(R ９０４ a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ ~R ９０４ are R in the general formula (4A), ９０１ ~R ９０４ (Same meaning as above.) 19. In the fourth compound, Ar ４１１ , Ar ４１２ , and Ar ４１３ at least one of the following general formulae (457), (461), and (464) is a group represented by any one of the following general formulae (457), (461), and (464), and when two or more groups represented by any one of the general formulae (457), (461), and (464) are present, the two or more groups represented by any one of the general formulae (457), (461), and (464) are the same as or different from each other. The organic electroluminescence element according to claim 15, claim 16, or claim 18. (In the general formulae (457), (461), and (464), R ４１ ~R ４８ are R in the general formula (4A), ４１ ~R ４８ is synonymous with R ４１Ａ and R ４２Ａ are R in the general formula (4A), ４１Ａ and R ４２Ａ In the general formulae (457), (461), and (464), * each independently represents L in the general formula (4). Ａ１ , L Ａ２ and L Ａ３ or a bonding position to a carbon atom constituting a benzene ring in the general formula (40).

20. The organic electroluminescence device according to any one of claims 1 to 19, wherein the fifth compound is a compound represented by the following general formula (5): (In the above general formula (5), A is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms; B is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms; L is a substituted or unsubstituted (m+n+1)-valent aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted (m+n+1)-valent heterocyclic group having 5 to 13 ring atoms, or a (m+n+1)-valent group having a structure in which two or three different groups are bonded together, which are selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms; Ar ５ is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms, m is an integer of 0 or 1 or more, ５ are the same or different from each other, Cz is a group represented by the general formula (Cz1), n ​​is an integer of 2 or more, and a plurality of Cz are the same or different from each other, and in the group represented by the general formula (Cz1), R ５１１ ~R ５１８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring. ５１１ ~R ５１８ each independently represents a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ) group represented by -O-(R ９０４ a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, * in general formula (Cz1) is bonded to L, ９０１ , R ９０２ , R ９０３ and R ９０４ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; R ９０１ When there are multiple R ９０１ are the same or different from each other, R ９０２ When there are multiple R ９０２ are the same or different from each other, R ９０３ When there are multiple R ９０３ are the same or different from each other, R ９０４ When there are multiple R ９０４ are the same or different from each other.) 21. The organic electroluminescence device according to claim 20, wherein the fifth compound is a compound represented by the following general formula (51): In the general formula (51), A, B, and Cz are the same as A, B, and Cz in the general formula (5), respectively; ５８１ , R ５８３ , and R ５８５ each independently represents a hydrogen atom, a cyano group, an alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ) group represented by -O-(R ９０４ a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; Ar ５、 or a group represented by the general formula (Cz1), ５ is Ar in the general formula (5). ５ is synonymous with R ９０１ ~R ９０４ are R in the general formula (5), ９０１ ~R ９０４ (Same meaning as above.) 22. The organic electroluminescence device according to claim 21, wherein in the compound represented by general formula (51), A is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and B is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

23. The organic electroluminescence device according to any one of claims 20 to 22, wherein the fifth compound is a compound represented by the following general formula (52): (In the general formula (52), R ５８１ , R ５８３ , and R ５８５ are R in the general formula (51), ５８１ , R ５８３ , and R ５８５ is synonymous with R ５８６ ~R ５９５ each independently represents a hydrogen atom, 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 ) group represented by -S-(R ９０５ a halogen atom, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ ~R ９０３ are R in the general formula (5), ９０１ ~R ９０３ is synonymous with R ９０５ is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９０５ When there are multiple R ９０５ are the same or different from each other.) 24. In the compound represented by the general formula (52), R ５８９ is a hydrogen atom; 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 ) group represented by -S-(R ９０５ 24. The organic electroluminescence device according to claim 23, wherein the aryl group is a group represented by the formula:

25. In the compound represented by the general formula (52), R ５８１ , R ５８３ , R ５８５ , R ５８６ ~R ５８８ , and R ５９０ ~R ５９５ are each independently a hydrogen atom or a substituted or unsubstituted phenyl group; R ５８９ The organic electroluminescence device according to claim 23 or 24, wherein: is a hydrogen atom.

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

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