Organic electroluminescent element and electronic apparatus

Abstract

To provide an organic electroluminescent element capable of improving a light emission efficiency.SOLUTION: An organic electroluminescent element contains: a first layer 71 that is contained between a positive electrode 3 and a light emission layer 5; a second layer 72 that is contained between the first layer 71 and the light emission layer 5; and a third layer 73 that is contained between the positive electrode 3 and the first layer 71. The light emission layer 5 contains a delayed fluorescence property chemical compound as a second chemical compound, and a percentage content of the second chemical compound in the light emission layer 5 is 30 mass% or more and 50 mass% or less. The first layer 71 contains a fourth chemical compound, and the second layer 72 contains a fifth chemical compound. The third layer 73 contains a sixth chemical compound. Those compounds satisfy the following mathematical formula (a numerical expression 41) and mathematical formula (a numerical expression 42) in the organic electroluminescent element. (The numerical expression 41): |HOMO(M5)|≥5.70 eV, and (the numerical expression 42): NM6>NM4 (the HOMO(M5) is an energy level of the highest occupied molecular orbital of the fifth chemical compound, the NM4 is a refraction factor of the fourth chemical compound, and the NM6 is a refraction factor of the sixth chemical compound).SELECTED DRAWING: Figure 1

Description

[Technical field]

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

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

[0003] For example, it is expected that organic EL elements can emit light more efficiently by utilizing triplet excitons in addition to singlet excitons. In this context, highly efficient fluorescent organic EL elements using thermally activated delayed fluorescence (hereinafter sometimes simply referred to as "delayed fluorescence") have been proposed and are being studied. The TADF (Thermally Activated Delayed Fluorescence) mechanism utilizes the phenomenon that 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 examples of compounds that exhibit thermally activated delayed fluorescence (TADF) include 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. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] International Publication No. 2022 / 260117 [Patent Document 2] International Publication No. 2020 / 241580 Summary of the Invention [Problem to be solved by the invention]

[0006] In order to improve the performance of electronic devices such as displays, there is a demand for further improvement 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 electroluminescence element capable of improving the luminous efficiency, and to provide an electronic device incorporating the organic electroluminescence element. [Means for solving the problem]

[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, a second layer between the first layer and the emitting layer, and a third layer between the anode and the first layer, wherein the emitting layer contains a delayed fluorescent compound as a second compound, and a content of the second compound in the emitting layer is 30 mass% or more and 50 mass% or less, the first layer contains a fourth compound, the second layer contains a fifth compound, and the third layer contains a sixth compound, the fourth compound, the fifth compound, and the sixth compound are different from each other, and the fourth compound, the fifth compound, and the sixth compound satisfy the following mathematical formula (Mathematical Formula 41) and mathematical formula (Mathematical Formula 42). (Equation 41): |HOMO(M5)|≧5.70 eV (Number 42):NM 6 >NM 4 (HOMO(M5) is the energy level of the highest occupied molecular orbital of the fifth compound, and NM 4 is the refractive index of the fourth compound, N 6 is the refractive index of the sixth compound.

[0009] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescence element according to one aspect of the present invention. Effect of the Invention

[0010] According to one aspect of the present invention, it is possible to provide an organic electroluminescence element capable of improving light emission efficiency, and an electronic device equipped with the organic electroluminescence element. [Brief description of the drawings]

[0011] [Figure 1] 1 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a first embodiment of the present invention. [Diagram 2]FIG. 1 is a schematic diagram of an apparatus for measuring transient PL. [Diagram 3] FIG. 13 is a diagram showing an example of an attenuation curve of a transient PL. [Figure 4] FIG. 2 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 the first embodiment of the present invention, and a relationship between energy transfer. [Diagram 5] FIG. 11 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 device according to a second embodiment of the present invention, and a relationship of energy transfer. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

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

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

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

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

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

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

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

[0019] "Substituents Described Herein" The substituents described in this specification will be described below.

[0020] The "unsubstituted aryl group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkyl group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification. The "unsubstituted alkenyl group" described in this specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms, unless otherwise specified in this specification. The "unsubstituted alkynyl group" described in this specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms, unless otherwise specified in this specification. The "unsubstituted cycloalkyl group" described in this specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted arylene group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted divalent heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkylene group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.

[0021] "Substituted or unsubstituted aryl groups" Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B). (Here, the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group", and the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group".) In this specification, when the term "aryl group" is simply used, it includes both an "unsubstituted aryl group" and a "substituted aryl group". The term "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent. Examples of the "substituted aryl group" include the "unsubstituted aryl group" in the specific example group G1A below in which one or more hydrogen atoms are replaced with a substituent, and the substituted aryl group in the specific example group G1B below. The examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed here are merely examples, and the "substituted aryl group" described in this specification also includes the "substituted aryl group" in the specific example group G1B below in which a hydrogen atom bonded to a carbon atom of the aryl group itself is further replaced with a substituent, and the "substituted aryl group" in the specific example group G1B below in which a hydrogen atom of a substituent is further replaced with a substituent.

[0022] Unsubstituted aryl groups (specific example group G1A): Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, Benzanthryl group, A phenanthryl group, Benzophenanthryl group, A phenalenyl group, Pyrenyl group, Chrysenyl group, benzochrysenyl group, A triphenylenyl group, Benzotriphenylenyl group, tetracenyl group, Pentacenyl group, fluorenyl group, 9,9'-spirobifluorenyl group, Benzofluorenyl group, Dibenzofluorenyl group, fluoranthenyl group, Benzofluoranthenyl group, Perylenyl groups, and A monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0023] [ka]

[0024] [ka]

[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 any one of the general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

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

[0027] The specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).

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

[0029] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): Pyrrolyl group, imidazolyl group, A pyrazolyl group, A triazolyl group, Tetrazolyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, A thiazolyl group, isothiazolyl group, A thiadiazolyl group, Pyridyl group, pyridazinyl group, pyrimidinyl group, A pyrazinyl group, Triazinyl group, Indolyl groups, isoindolyl group, Indolizinyl group, A quinolizinyl group, A quinolyl group, isoquinolyl group, Cinnolyl group, phthalazinyl group, A quinazolinyl group, A quinoxalinyl group, Benzimidazolyl group, Indazolyl group, A phenanthrolinyl group, A phenanthridinyl group, acridinyl group, A phenazinyl group, A carbazolyl group, Benzocarbazolyl group, morpholino group, phenoxazinyl group, A phenothiazinyl group, Azacarbazolyl and diazacarbazolyl groups.

[0030] Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): Furyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, Dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzoisoxazolyl group, phenoxazinyl group, morpholino group, Dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, Azanaphthobenzofuranyl groups, and Diazanaphthobenzofuranyl group.

[0031] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): A thienyl group, A thiazolyl group, isothiazolyl group, A thiadiazolyl group, Benzothiophenyl group (benzothienyl group), Isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), Naphthobenzothiophenyl group (naphthobenzothienyl group), benzothiazolyl group, Benzisothiazolyl group, A phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), Diazadibenzothiophenyl group (diazadibenzothienyl group), Azanapthobenzothiophenyl group (azanaphthobenzothienyl group), and Diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[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] [ka]

[0034] [ka]

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

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

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

[0038] Substituted heterocyclic groups containing sulfur atoms (specific example group G2B3): Phenyldibenzothiophenyl group, methyldibenzothiophenyl group, t-Butyldibenzothiophenyl group, and A monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[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 above-mentioned "one or more hydrogen atoms of a monovalent heterocyclic group" refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, X A and Y A A hydrogen atom bonded to a nitrogen atom when at least one of the above is NH, and X A and Y A One of them is CH 2 and methylene groups represented by the formula:

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

[0042] Unsubstituted alkyl groups (specific example group G3A): Methyl group, Ethyl group, n-propyl group, isopropyl group, n-Butyl group, isobutyl group, s-Butyl group, and t-Butyl group.

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

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

[0045] Unsubstituted alkenyl groups (specific example group G4A): Vinyl group, Allyl groups, 1-butenyl group, 2-butenyl group, and 3-Butenyl group.

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

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

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

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

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

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

[0052] -Si(R 901 )(R 902 )(R 903 ) a group represented by As described herein, -Si(R 901 )(R 902 )(R 903 Specific examples (specific example group G7) of the group represented by -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. The multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other. The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other. The multiple G1s in -Si(G1)(G1)(G2) are the same as or different from each other. The multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other. The multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The multiple G6s in -Si(G6)(G6)(G6) are the same as or different from each other.

[0053] -O-(R 904 ) a group represented by As described herein, -O-(R 904 Specific examples (specific example group G8) of the group represented by -O(G1), -O(G2), -O(G3), and -O(G6) Examples include: Where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0054] -S-(R 905 ) a group represented by As described herein, -S-(R 905 Specific examples (specific example group G9) of the group represented by -S(G1), -S(G2), -S(G3), and -S(G6) Examples include: Where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0055] -N(R 906 )(R 907 ) a group represented by As described herein, -N(R 906 )(R 907 Specific examples (specific example group G10) of the group represented by -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) Examples include: Where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. -The multiple G1's in N(G1)(G1) are the same or different from each other. The multiple G2's in -N(G2)(G2) are the same or different from each other. -The multiple G3's in N(G3)(G3) are the same or different from each other. The multiple G6s in -N(G6)(G6) are the same or different from each other.

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

[0057] "Substituted or unsubstituted fluoroalkyl groups" The term "substituted or unsubstituted fluoroalkyl group" as used herein means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group (perfluoro group) in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with fluorine atoms. The number of carbon atoms in the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification. The term "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms in the "fluoroalkyl group" are replaced with a substituent. The term "substituted fluoroalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in the "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms in the substituent in the "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include the examples of the group in which one or more hydrogen atoms in the "alkyl group" (specific example group G3) are replaced with a fluorine atom.

[0058] "Substituted or unsubstituted haloalkyl groups" The term "substituted or unsubstituted haloalkyl group" as used herein means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The number of carbon atoms in the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification. The term "substituted haloalkyl group" means a group in which one or more hydrogen atoms in the "haloalkyl group" are replaced with a substituent. The term "substituted haloalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in the "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms in the substituent in the "substituted haloalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted haloalkyl group" include the examples of the group in which one or more hydrogen atoms in the "alkyl group" (specific example group G3) are replaced with a halogen atom. Haloalkyl groups are sometimes referred to as halogenated alkyl groups.

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

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

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

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

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

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

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

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

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

[0068] [ka]

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

[0070] [ka]

[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] [ka]

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

[0075] The substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like, unless otherwise specified herein.

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

[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 of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include divalent groups derived by removing one hydrogen atom on the heterocycle from the "substituted or unsubstituted heterocyclic group" described in specific example group G2.

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

[0079] The substituted or unsubstituted arylene group described in this specification is preferably any of the groups represented by the following general formulae (TEMP-42) to (TEMP-68), unless otherwise specified in this specification.

[0080] [ka]

[0081] [ka]

[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 above general formulae (TEMP-42) to (TEMP-52), * represents a bonding position.

[0083] [ka]

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

[0085] [ka]

[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 above general formulae (TEMP-63) to (TEMP-68), * represents a bonding position.

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

[0088] [ka]

[0089] [ka]

[0090] [ka]

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

[0092] [ka]

[0093] [ka]

[0094] [ka]

[0095] [ka]

[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 an explanation of "the substituents described in this specification".

[0098] - "When bonded to form a ring" In this specification, the phrase "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle, bond to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle", the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted fused ring", and the case where "one or more of a set consisting of two or more adjacent groups are not bonded to each other". In this specification, the cases where "one or more of a set of two or more adjacent rings are bonded to each other to form a substituted or unsubstituted monocyclic ring" and "one or more of a set of two or more adjacent rings are bonded to each other to form a substituted or unsubstituted condensed ring" (hereinafter, these cases may be collectively referred to as "a case where they are bonded to form a ring") will be explained below. The case of an anthracene compound represented by the following general formula (TEMP-103), in which the mother skeleton is an anthracene ring, will be explained as an example.

[0099] [ka]

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

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

[0102] [ka]

[0103] The case where a "set of two or more adjacent units" forms a ring includes not only the case where a set of two adjacent units is bonded as in the previous example, but also the case where a set of three or more adjacent units is bonded. For example, R 921 and R 922 and are bonded to ring Q A and R 922 and R 923 and are bonded to ring Q C The three adjacent (R 921 , R 922 and R 923 In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), the ring Q A and Ring Q C is R 922 Share.

[0104] [ka]

[0105] The "monocyclic ring" or "condensed ring" formed may be a saturated or unsaturated ring as the structure of only the ring formed. Even when "one of the pairs of adjacent two" forms a "monocyclic ring" or a "condensed ring", the "monocyclic ring" or the "condensed ring" may form a saturated or unsaturated ring. For example, the ring Q formed in the general formula (TEMP-104) may be a saturated or unsaturated ring. A and Ring Q B are "monocyclic" or "condensed rings". In addition, the ring Q formed in the general formula (TEMP-105) A , and ring Q C is a "fused ring". The ring Q in the above general formula (TEMP-105) A and Kan Q C That is, Ring Q A and Kan Q C The ring Q in the general formula (TMEP-104) is condensed to form a condensed ring. AIf is a benzene ring, then ring Q A The ring Q in the general formula (TMEP-104) is a monocyclic ring. A If is a naphthalene ring, then ring Q A is a fused ring.

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

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

[0108] When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above-mentioned section "Substituents described in this specification". When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification". The above is an explanation of the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted fused ring" ("combined to form a ring").

[0109] Substituents in the phrase "substituted or unsubstituted" In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituent" in the present specification) is, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms; an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms; an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms; -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and a group selected from the group consisting of unsubstituted heterocyclic groups having 5 to 50 ring atoms, Here, R 901 ~R 907 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 901 If there are two or more, there are two or more R 901 are identical or different from each other, R 902 If there are two or more, there are two or more R 902 are identical or different from each other, R 903 If there are two or more, there are two or more R 903 are identical or different from each other, R 904 If there are two or more, there are two or more R 904 are identical or different from each other, R 905 If there are two or more, there are two or more R 905 are identical or different from each other, R 906 If there are two or more, there are two or more R 906 are identical or different from each other, R 907 If there are two or more, there are two or more R 907 are the same or different from each other.

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

[0111] In one embodiment, the substituent in the above "substituted or unsubstituted" is: an alkyl group having 1 to 18 carbon atoms; An aryl group having 6 to 18 ring carbon atoms, and The group is selected from the group consisting of heterocyclic groups 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, any adjacent substituents may be combined with each other to form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring. Unless otherwise specified in the present specification, the optional substituent may further have a substituent. The substituent that the optional substituent further has is the same as the optional substituent described above.

[0114] In this specification, a numerical range expressed using "AA to BB" means a range including the number AA written before "AA to BB" as the lower limit and the number BB written after "AA to BB" as the upper limit.

[0115] In this specification, a mathematical expression expressed as "A≧B" means that the value of A is equal to the value of B, or the value of A is greater than the value of B. In this specification, a mathematical expression expressed as "A≦B" means that the value of A is equal to the value of B, or the value of A is smaller than the value of B.

[0116] In this specification, the ordinal expressions "first", "second" and "third" are intended to distinguish components and do not imply an order.

[0117] First Embodiment <Organic electroluminescence 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 includes a plurality of layers made of an organic compound stacked together. The organic layer may further include an inorganic compound. In the first embodiment, at least four of the organic layers are an emitting layer included between the anode and the cathode, a first layer included between the anode and the emitting layer, a second layer included between the first layer and the emitting layer, and a third layer included between the anode and the first layer. In one aspect of the organic EL device of the first embodiment, the first layer and the second layer are electron blocking layers, and in one aspect of the organic EL device of the first embodiment, the third layer is a hole transport layer. The organic layer may be composed of, for example, a light-emitting layer, a first layer, a second layer, and a third layer, or may include a layer that can be employed in an organic EL device. The layer that can be used in the organic EL device is not particularly limited, and may be, for example, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer other than the third layer, an electron blocking layer other than the first layer and the second layer, an electron injection layer, an electron transport layer, and a hole blocking layer. In one aspect of the organic EL device of the first embodiment, the hole injection layer is included between the anode and the third layer. In one aspect of the organic EL device of the first embodiment, the electron transport layer is included between the cathode and the light-emitting layer.

[0118] The organic EL element according to the first 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, a second layer between the first layer and the emitting layer, and a third layer between the anode and the first layer. The light-emitting layer contains a delayed fluorescent compound as a second compound, and the content of the second compound in the light-emitting layer is 30% by mass or more and 50% by mass or less. The first layer comprises a fourth compound, the second layer comprises a fifth compound, and the third layer comprises a sixth compound, wherein the fourth compound, the fifth compound, and the sixth compound are different from each other. The fourth compound, the fifth compound, and the sixth compound satisfy the following formula (Formula 41) and formula (Formula 42). (Equation 41): |HOMO(M5)|≧5.70 eV (Number 42):NM 6 >NM4 (HOMO(M5) is the energy level of the highest occupied molecular orbital of the fifth compound, and NM 4 is the refractive index of the fourth compound, N 6 is the refractive index of the sixth compound.

[0119] In this specification, the first layer may be referred to as a first electron blocking layer, and the second layer may be referred to as a second electron blocking layer. In the laminated structure (the third layer, the first layer, and the second layer) from the anode side of this embodiment, the third layer is preferably a hole transport layer having a large thickness. Therefore, the third layer may be called a thick-film hole transport layer or a thick-film HT layer.

[0120] In organic EL elements, when a TADF material is added to the light-emitting layer and the concentration of the TADF material is higher (30% by mass or more) than the conventional concentration (approximately 25% by mass), the device life can be extended, but the problem of a significant drop in luminous efficiency has been recognized. Because TADF materials have high electron transport properties, it is believed that increasing the concentration of TADF material in the light-emitting layer causes the light-emitting layer to have an excess of electrons, disrupting the charge balance, and as a result, reducing the luminous efficiency. In order to solve the above-mentioned problems, the present inventors have discovered that by laminating a first layer (first electron blocking layer (anode side)) and a second layer (second electron blocking layer (light-emitting layer side)) and incorporating a fifth compound satisfying the above-mentioned mathematical formula (Mathematical formula 41) in the second electron blocking layer, the amount of holes in the light-emitting layer is increased, making it possible to adjust the charge balance, and as a result, improving the light-emitting efficiency. Furthermore, the present inventors have discovered that by incorporating a third layer (preferably a thick-film HT layer) between the anode and the first layer and adjusting the refractive index NM of the fourth compound contained in the first layer, the amount of holes in the light-emitting layer is increased, making it possible to adjust the charge balance. 4 is the refractive index NM of the sixth compound contained in the third layer. 6 (the above-mentioned mathematical formula (Mathematical formula 42)), it was found that the light extraction efficiency is improved and the luminous efficiency is further improved.

[0121] <Hole transport band> In this specification, a zone consisting of a plurality of organic layers arranged between the anode and the light-emitting layer may be referred to as a hole-transporting zone. In this embodiment, the first layer (first electron blocking layer), the second layer (second electron blocking layer), and the third layer (thick-film hole-transporting layer) are layers included in the hole-transporting zone. In addition to the first layer, the second layer, and the third layer, the hole-transporting zone may include one or more organic layers (e.g., a hole-injecting layer). In one aspect of the organic EL element of the first embodiment, the hole transport zone includes a hole injection layer, a third layer, a first layer, and a second 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 the third layer, the first layer, and the second layer in this order from the anode side.

[0122] In one aspect of the organic EL element of the first embodiment, the anode and the third layer are in direct contact with each other. In one aspect of the organic EL element of the first embodiment, when a hole injection layer is included between the anode and the third layer, the anode and the hole injection layer are in direct contact with each other, and the hole injection layer and the third layer are in direct contact with each other. In one aspect of the organic EL element of the first embodiment, the first layer and the third layer are in direct contact with each other. In one aspect of the organic EL element of the first embodiment, the first layer and the second layer are in direct contact with each other. In one aspect of the organic EL element of the first embodiment, the light-emitting layer and the second layer are in direct contact with each other.

[0123] In one aspect of the organic EL element of the first embodiment, the thickness of the first layer is 35 nm or less, or 30 nm or less.

[0124] In one aspect of the organic EL element of the first embodiment, the thickness of the second layer is 10 nm or less, 8 nm or less, or 5 nm or less.

[0125] In one aspect of the organic EL element of the first embodiment, the thickness TL of the first layer 1 and the thickness TL of the second layer 2 satisfies the relationship of the following formula (Math A1). (Math A1): TL 1 >TL 2 (TL 1 is the thickness of the first layer, and TL 2 is the film thickness of the second layer, and the unit of the film thickness is nm. In one aspect of the organic EL element of the first embodiment, the thickness of the first layer and the thickness of the third layer satisfy the relationship of the following mathematical formula (Mathematical Formula A2). (Number A2): TL 3 >TL 1 (TL 1 is the thickness of the first layer, and TL 3 is the film thickness of the third layer, and the unit of the film thickness is nm. In one aspect of the organic EL element of the first embodiment, the thickness of the first layer, the thickness of the second layer, and the thickness of the third layer satisfy the relationship of the following mathematical formula (Math A3). (Math A3): TL 3 >TL 1 >TL 2 (TL 1 is the thickness of the first layer, and TL 2 is the thickness of the second layer, and TL 3 is the film thickness of the third layer, and the unit of the film thickness is nm.

[0126] In one aspect of the organic EL element of the first embodiment, the sum of the thickness of the first layer, the thickness of the second layer, and the thickness of the third layer is 160 nm or less, 150 nm or less, 140 nm or less, or 130 nm or less. In one aspect of the organic EL element of the first embodiment, the total thickness of the first layer, the second layer, and the third layer is 80 nm or more.

[0127] In one aspect of the organic EL element of the first embodiment, the third layer (thick hole transport layer) has a thickness of 30 nm or more, 50 nm or more, 70 nm or more, or 80 nm or more. In one aspect of the organic EL element of the first embodiment, the third layer (thick film hole transport layer) has a thickness of 130 nm or less.

[0128] In one aspect of the organic EL element of the first embodiment, the fifth compound satisfies the following formula (Formula 41), formula (Formula 41A), or formula (Formula 41B). When the fifth compound satisfies the following formula (Formula 41), the luminous efficiency is easily improved. (Equation 41): |HOMO(M5)|≧5.70 eV (Number 41A): |HOMO(M5)|≧5.80 eV (Number 41B): |HOMO(M5)|≧5.85 eV (HOMO(M5) is the energy level of the highest occupied molecular orbital of the fifth compound.)

[0129] In one aspect of the organic EL element of the first embodiment, |HOMO(M5)| is, for example, 6.0 eV or less.

[0130] In one aspect of the organic EL element of the first embodiment, the fourth compound and the fifth compound satisfy the following Formula 43, Formula 43A, or Formula 43B. When the fourth compound and the fifth compound satisfy the following formula (Formula 43), the luminous efficiency is easily improved. (Math. 43):0<|HOMO(M4)-HOMO(M5)|≦0.40eV (Number 43A):0.05<|HOMO(M4)-HOMO(M5)|≦0.40eV (Number 43B):0.05<|HOMO(M4)-HOMO(M5)|≦0.35eV (HOMO(M4) is the energy level of the highest occupied molecular orbital of the fourth compound, and HOMO(M5) is the energy level of the highest occupied molecular orbital of the fifth compound.)

[0131] In one aspect of the organic EL element of the first embodiment, the fourth compound and the fifth compound satisfy the following mathematical formula (Mathematical Formula 46). When the fourth compound and the fifth compound satisfy the following formula (Formula 46), the luminous efficiency is easily improved. (Number 46): |HOMO(M5)|>|HOMO(M4)| (HOMO(M4) is the energy level of the highest occupied molecular orbital of the fourth compound, and HOMO(M5) is the energy level of the highest occupied molecular orbital of the fifth compound.)

[0132] In one aspect of the organic EL element of the first embodiment, the second compound, the fourth compound, and the fifth compound satisfy the following mathematical formula (Mathematical Formula 47). When the second compound, the fourth compound, and the fifth compound satisfy the following formula (Formula 47), the luminous efficiency is easily improved. (Number 47): |HOMO(M2)|>|HOMO(M5)|>|HOMO(M4)| (HOMO(M2) is the energy level of the highest occupied molecular orbital of the second compound, HOMO(M4) is the energy level of the highest occupied molecular orbital of the fourth compound, and HOMO(M5) is the energy level of the highest occupied molecular orbital of the fifth compound).

[0133] (Method of measuring ionization potential Ip and energy level of highest occupied molecular orbital HOMO) In the present specification, the ionization potential and the energy level of the highest occupied molecular orbital (HOMO) of a compound are measured under atmospheric conditions using a photoelectron spectrometer. Specifically, the ionization potential and the energy level of the highest occupied molecular orbital (HOMO) of a compound can be measured by the method described in the Examples.

[0134] In one aspect of the organic EL element of the first embodiment, the fourth compound and the sixth compound satisfy the following formula (Formula 42), (Formula 411), or (Formula 411A). (Number 42): NM 6 >NM 4 (Number 411): NM 6 -NM 4 >0.10 (Number 411A): NM 6 -NM 4 >0.12 (NM 4 is the refractive index of the fourth compound, N 6 is the refractive index of the sixth compound.

[0135] In one aspect of the organic EL element of the first embodiment, "NM 6 -NM 4 " is, for example, 2.5 or less.

[0136] In one aspect of the organic EL element of the first embodiment, the fourth compound satisfies the following formula (Formula 412), (Formula 412A), or (Formula 412B). (Number 412): NM 4 ≧1.65 (Number 412A): NM 4 ≧1.66 (Number 412B): NM 4 ≧1.69 (NM 4 is the refractive index of the fourth compound.

[0137] In one aspect of the organic EL element of the first embodiment, NM 4 is, for example, 1.75 or less.

[0138] In one aspect of the organic EL element of the first embodiment, the sixth compound satisfies the following formula (Formula 413), (Formula 413A), or (Formula 413B). (Number 413): NM 6 ≧1.75 (Number 413A): NM 6 ≧1.80 (Number 413B): NM 6 ≧1.85 (NM 6 is the refractive index of the sixth compound.

[0139] In one aspect of the organic EL element of the first embodiment, NM 6 is, for example, less than or equal to 2.0.

[0140] The refractive index can be measured by the measurement method described in the Examples below. In this specification, the refractive index of the material to be measured is the value measured by multi-angle spectroscopic ellipsometry at 2.25 eV in the substrate parallel direction (ordinary direction). The refractive index at 2.25 eV corresponds to the refractive index at 550 nm.

[0141] In one aspect of the organic EL element of the first embodiment, the fourth compound satisfies the following Formula (53), Formula (53A), or Formula (53B). When the fourth compound satisfies the following formula (Formula 53), the driving voltage is easily reduced. (Number 53):μ H (M4) ≧ 1.0 × 10 -4 cm 2 / Vs (Number 53A):μ H (M4) ≧ 1.0 × 10 -3 cm 2 / Vs (Number 53B): μ H (M4) ≧ 1.0 × 10 -2 cm 2 / Vs (μ H (M4) is the hole mobility of the fourth compound.

[0142] (Method of measuring hole mobility) The hole mobility can be measured by impedance measurement using a mobility evaluation element prepared by the following procedure. The mobility evaluation element is prepared, for example, by the following procedure. On a glass substrate with an ITO transparent electrode (anode), the following compounds HT-1 and HA are co-deposited so as to cover the transparent electrode to form a hole injection layer. On this hole injection layer, compound HT-1 is deposited by deposition to form a first hole transport layer. Then, on the first hole mobility layer, the following compound HT-2 is deposited by deposition to form a second hole transport layer. Then, on the second hole mobility layer, a hole mobility μ H A measurement target layer is formed by evaporating a compound (Target) to be measured. Metallic aluminum (Al) is evaporated onto this measurement target layer to form a metal cathode. The above-mentioned configuration of the element for evaluating mobility can be simply shown as follows. ITO(130) / HT-1:HA(10,97%:3%) / HT-1(10) / HT-2(10) / Target(200) / Al(80) In the configuration of the device for evaluating mobility, the numbers in parentheses indicate the film thickness (unit: nm). Similarly, in the configuration of the device for evaluating mobility, the numbers in parentheses expressed as percentages (97%:3%) indicate the ratios (mass%) of the compounds HT-1 and HA in the hole injection layer.

[0143] [ka]

[0144] The element for evaluating the hole mobility is placed in an impedance measuring device, and impedance measurement is performed. The impedance measurement is performed by sweeping the measurement frequency from 1 Hz to 1 MHz. At that time, a DC voltage V is applied to the element at the same time as an AC amplitude of 0.1 V. The modulus M is calculated from the measured impedance Z using the relationship of the following calculation formula (C1). Calculation formula (C1): M=jωZ In the above calculation formula (C1), j is an imaginary unit whose square is -1, and ω is the angular frequency [rad / s]. In a Bode plot with the imaginary part of the modulus M on the vertical axis and frequency [Hz] on the horizontal axis, the electrical time constant τ of the mobility evaluation element is calculated from the frequency fmax showing the peak using the following calculation formula (C2). Calculation formula (C2): τ=1 / (2πfmax) In the above formula (C2), π is the symbol representing pi. Using the τ calculated from the above formula (C2), the hole mobility μ H Calculate. Calculation formula (C3-2):μ H =d 2 / (Vτ) In the above formula (C3-2), d is the total thickness of the organic thin films that constitute the element, and in the case of the element configuration for evaluating the hole mobility, d=230 [nm].

[0145] In this specification, the hole mobility is expressed as the square root of the electric field strength E 1 / 2 =500[V 1 / 2 / cm 1 / 2 The square root of the electric field strength E 1 / 2 can be calculated from the relationship of the following calculation formula (C4). Calculation formula (C4): E 1 / 2 =V 1 / 2 / d 1 / 2 The impedance measurement is performed using a Solartron Model 1260 impedance measuring device, and for higher accuracy, a Solartron Model 1296 dielectric constant measuring interface can also be used.

[0146] FIG. 1 shows a schematic configuration of an example of an organic EL element according to the first embodiment. 1 includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 includes, in order from the anode 3 side, a hole transporting region 7, an emitting layer 5, and an electron transporting region 8. The hole transporting region 7 includes, in order from the anode 3 side, a hole injection layer 74, a third layer 73, a first layer 71, and a second layer 72. The electron transporting region 8 includes, in order from the anode 3 side, an electron transporting layer 81 and an electron injection layer 82.

[0147] The present invention is not limited to the configuration of the organic EL element shown in Fig. 1. As an organic EL element having a different configuration, for example, an organic EL element in which the light-emitting layer 5 is composed of two organic layers can be mentioned.

[0148] (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 (Mathematical formula 41), but is preferably an amine compound. One aspect of the fifth compound is, for example, a compound that satisfies the above formula (Mathematical formula 41) and is represented by the following general formula (5). As the fifth compound, for example, a compound satisfying the above formula (Mathematical formula 41) can be selected from the compounds represented by the following general formula (5) and used.

[0149] [ka]

[0150] (In the general formula (5), L A1 , L A2 and L A3 are each independently Single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, *2 is L A1 , L A2 Or L A3 is the bonding position with Ar 511 , Ar 512 and Ar 513 are each independently 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 ) a group represented by A group represented by the general formula (5A), However, Ar 511 , Ar 512 , and Ar 513 At least one of the groups is a group represented by general formula (5A), When two or more groups represented by the general formula (5A) are present, the two or more groups represented by the general formula (5A) are the same or different from each other, R C1 , R C2 and R C3 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R C1 If there are multiple R C1 are identical or different from each other, R C2 If there are multiple R C2 are identical or different from each other, R C3 If there are multiple R C3 are identical or different from each other, In the general formula (5A), X 5 is an oxygen atom, a sulfur atom, a C(R 51A )(R 52A ) or N(R 53A ) and R 51A and R 52A A set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 51 ~R 58 Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 51 ~R 58 , R 51A , R 52A and R 53A One of the bonds is a single bond bonded to *1, *1 is not a single bond bonded to R, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted condensed ring51 ~R 58 , R 51A , R 52A and R 53A are each independently Hydrogen atoms, 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 group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the general formula (5A), R 901 ~R 904 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are either identical or different.)

[0151] In the general formula (5), L A1 , L A2 Or L A3 When is a single bond, *2 is the bonding position with the nitrogen atom in the general formula (5).

[0152] In one embodiment of the fifth 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. In one embodiment of the fifth compound, L A1 , L A2 and L A3 each independently represents 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.

[0153] In one aspect of the organic EL device of the first embodiment, the fifth compound is a compound represented by the following general formula (50).

[0154] [ka]

[0155] (In the general formula (50), Ar 511 , Ar 512 and Ar 513 respectively represent Ar in the general formula (5). 511 , Ar 512 and Ar 513 is synonymous with n1 is 4, and 4 Ra11 are the same or different from each other, The four Ra 11 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, n2 is 4, and 4 Ra 12 are the same or different from each other, The four Ra 12 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, n3 is 4, and 4 Ra 13 are the same or different from each other, The four Ra 13 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, Ra does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 11 , Ra 12 and Ra 13 are each independently Hydrogen atoms, 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 group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the general formula (50), R 901 ~R 904 are R in the general formula (5A), 901 ~R 904 is equivalent to

[0156] In one aspect of the organic EL device of the first embodiment, the fifth compound is a compound represented by the following general formula (500).

[0157] [ka]

[0158] (In the above general formula (500), Ar 511 , Ar 512 , Ar 513 , Ra 12 , Ra 13 , n2 and n3 are each Ar 511 , Ar 512 , Ar 513 , Ra 12 , Ra 13 , n2 and n3.)

[0159] In one aspect of the organic EL element of the first embodiment, Ar in the fifth compound 511 , Ar 512 , and Ar 513 At least one of these is a group represented by any one of the following general formulae (51) and (61) to (64).

[0160] [ka]

[0161] (In the general formulae (51) and (61) to (64), R 51 ~R 58 are R in the general formula (5A), 51 ~R58 is synonymous with In the general formulae (51) and (61) to (64), * each independently represents L in the general formula (5). A1 , L A2 and L A3 (the bonding position with a carbon atom constituting a benzene ring in the general formula (50) or the bonding position with a nitrogen atom or a carbon atom constituting a benzene ring in the general formula (500).

[0162] In one embodiment of the fifth compound, Ar 511 , Ar 512 , and Ar 513 At least one of these is a group represented by any one of the following general formulas (51) to (80).

[0163] [ka]

[0164] (In the general formulae (51) to (55), R 51 ~R 58 and R 53A are, respectively, R in the general formula (5A) 51 ~R 58 and R 53A is synonymous with * each independently represents L in the general formula (5). A1 , L A2 and L A3 (the bonding position with a carbon atom constituting a benzene ring in the general formula (50) or the bonding position with a nitrogen atom or a carbon atom constituting a benzene ring in the general formula (500).

[0165] [ka]

[0166] (In the general formulae (56) to (60), R 51 ~R 58 , R 51A and R 52A are R in the general formula (5A), 51 ~R 58 , R 51A and R 52A is synonymous with * each independently represents L in the general formula (5). A1 , L A2 and L A3 (the bonding position with a carbon atom constituting a benzene ring in the general formula (50) or the bonding position with a nitrogen atom or a carbon atom constituting a benzene ring in the general formula (500).

[0167] [ka]

[0168] (In the general formulae (61) to (68), R 51 ~R 58 are R in the general formula (5A), 51 ~R 58 Each * is independently the same as L in the general formula (5). A1 , L A2 and L A3 (the bonding position with a carbon atom constituting a benzene ring in the general formula (50) or the bonding position with a nitrogen atom or a carbon atom constituting a benzene ring in the general formula (500).

[0169] [ka]

[0170] [ka]

[0171] (In the general formulae (69) to (80), R 51 ~R 58 and X 5 are R in the general formula (5A), 51 ~R 58 and X 5 is synonymous with R 51B ~R 54B Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 51B ~R 54B 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 (5A). 51 ~R 58 is synonymous with * each independently represents L in the general formula (5). A1 , L A2 and L A3 (the bonding position with a carbon atom constituting a benzene ring in the general formula (50) or the bonding position with a nitrogen atom or a carbon atom constituting a benzene ring in the general formula (500).

[0172] In one embodiment of the fifth compound, Ar 511 , Ar 512 , and Ar 513 At least one of these is a group represented by general formula (51).

[0173] In one embodiment of the fifth compound, Ar 511 , Ar 512 , and Ar 513 At least one of these is a group represented by general formula (64).

[0174] In one embodiment of the fifth compound, Ar 511 , Ar 512 , and Ar 513 At least one of these is a group represented by any one of the general formulae (51) to (80). In one embodiment of the fifth compound, Ar 511 , Ar 512 , and Ar 513 Among these, two are groups represented by any one of the general formulae (51) to (80). In one embodiment of the fifth compound, Ar 511 , Ar 512 , and Ar 513 Among these, three are groups represented by any one of the general formulae (51) to (80). In one embodiment of the fifth compound, Ar 511 , Ar 512 , and Ar 513 Among these, three are groups represented by any one of the general formulae (51) and (61) to (64). In one embodiment of the fifth compound, Ar 511 , Ar 512 , and Ar 513 When two or three of the groups are represented by any one of the general formulae (51) to (80), two or three of the Ar 511 , Ar 512 , and Ar 513 are either identical to or different from each other.

[0175] In one embodiment of the fifth compound, Ar 511 , Ar 512 , and Ar 513 Among them, Ar is not a group represented by the general formula (5A). 511 , Ar 512 , and Ar 513 are each independently a group represented by any one of the following general formulas (5B) to (12B). In one embodiment of the fifth compound, Ar 511 , Ar 512 , and Ar 513When two of the groups are not a group represented by general formula (5A), the two groups are the same or different.

[0176] [ka]

[0177] (In the general formulae (5B) to (7B), R 41 ~R 45 Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 40A , R 40B and R 40C Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, Multiple R 40A are identical or different from each other, Multiple R 40B are identical or different from each other, Multiple R 40C are identical or different from each other, In the general formulae (8B) to (10B), R 40 ~R 43 , R 46 ~R 49 and R 40A Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, Multiple R 40A are identical or different from each other, In the general formulae (11B) to (12B), X 6 is an oxygen atom, a sulfur atom, a C(R 51C )(R 52C ) or N(R 53C ) and R 51C and R 52C A set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 41A ~R 44A Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, In the general formulae (5B) to (12B), R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 40 ~R 49 , R 40A , R 40B , R 40C , R 41A ~R 44A , R 51C , R 52C , and R 53C 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 (5A). 51 ~R 58 is synonymous with * each independently represents L in the general formula (5). A1 , L A2 and L A3 or a bonding position to a carbon atom constituting a benzene ring in the general formula (50), or a bonding position to a nitrogen atom or a carbon atom constituting a benzene ring in the general formula (500).

[0178] In one embodiment of the fifth compound, R 51 ~R 58 , R 51A , R 52A and R 53A 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. In one embodiment of the fifth compound, R 51 ~R 58 , R 51A , R 52A and R 53A 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.

[0179] In one embodiment of the fifth compound, R 40 ~R 49 , R 40A , R 40B , R 40C , R 41A ~R 44A , R 51B ~R 54B , R 51C , R 52C , R 53C , 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. In one embodiment of the fifth compound, R 40 ~R 49 , R 40A , R 40B , R 40C , R41A ~R 44A , R 51B ~R 54B , R 51C , R 52C , R 53C , 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.

[0180] In one embodiment of the fifth compound, the substituents in the case of “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 each independently represents R in the general formula (5A) 901 ~R 904 is synonymous with R 906 If there are multiple R 906 are the same or different, R 907 If there are multiple R 907 are the same or different from each other.

[0181] In one embodiment of the fifth compound, the substituents in the case of "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 ) is a group represented by the formula: In one embodiment of the fifth compound, the substituent in the term "substituted or unsubstituted" is an "unsubstituted" group or -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 fifth compound, the substituent in the case of "substituted or unsubstituted" is an "unsubstituted" group.

[0182] In one aspect of the organic EL element according to the first embodiment, the second layer contains the fifth compound in an amount of 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, 95% by mass or more, or 99% by mass or more. In one aspect of the organic EL element according to the first embodiment, the second layer may be a layer containing only the fifth compound.

[0183] (Fifth method for producing compound) The fifth compound can be produced by a known method.

[0184] (Fifth Specific Example of Compound) Specific examples of the fifth compound include the following compounds, however, the present invention is not limited to these specific examples of compounds.

[0185] [ka]

[0186] [ka]

[0187] [ka]

[0188] [ka]

[0189] [ka]

[0190] [ka]

[0191] [ka]

[0192] [ka]

[0193] [ka]

[0194] [ka]

[0195] [ka]

[0196] (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 satisfies the above formula (Formula 42), but is preferably an amine compound. One aspect of the fourth compound is, for example, a compound that satisfies the relationship of the above formula (Formula 42) and is represented by the following general formula (4). As the fourth compound, for example, a compound satisfying the above formula (Formula 42) can be selected from the compounds represented by the following general formula (4) and used.

[0197] [ka]

[0198] (In the general formula (4), L A1 , L A2 and L A3 are each independently Single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, *4 is L A1 , L A2 Or L A3 is the bonding position with Ar 411 , Ar 412 and Ar 413 are each independently 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 ) a group represented by A group represented by the general formula (4A), However, Ar 411 , Ar 412 , and Ar 413 At least one of the above is a group represented by general formula (4A), 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 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R C1 If there are multiple R C1 are identical or different from each other, R C2 If there are multiple R C2 are identical or different from each other, R C3 If there are multiple R C3 are identical or different from each other, In the general formula (4A), X 5 is an oxygen atom, a sulfur atom, a C(R 51A )(R 52A ) or N(R 53A ) and R 51A and R 52A A set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 51 ~R 58 Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 51 ~R 58 , R 51A , R 52A and R 53A One of the bonds is a single bond bonded to *3, *3 is not a single bond bonded to R, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted condensed ring 51 ~R 58 , R 51A , R 52A and R 53A are each independently Hydrogen atom, 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 group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the general formula (5A), R 901 ~R 904 are each independently 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 either identical or different.)

[0199] In the general formula (4), L A1 , L A2 Or L A3 When is a single bond, *4 is the bonding position with the nitrogen atom in the general formula (4).

[0200] In one embodiment of the fourth compound, L A1 , L A2 and L A3 each independently represents 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, a substituted or unsubstituted phenanthrylene group, or a substituted or unsubstituted fluorenylene group. In one aspect of the organic EL element of the first embodiment, L A1 , L A2 and L A3 each independently represents a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0201] In one aspect of the organic EL device of the first embodiment, the fourth compound is a compound represented by the following general formula (40), (41), or (42).

[0202] [ka]

[0203] (In the general formulae (40) to (42), Ar 411 , Ar 412 and Ar 413 respectively represent Ar in the general formula (4). 411 , Ar 412 and Ar 413 is synonymous with n2 is 4, and 4 Ra 12 are the same or different from each other, The four Ra 12 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, n3 is 4, and 4 Ra 13are the same or different from each other, The four Ra 13 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, Ra does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 12 and Ra 13 are each independently Hydrogen atoms, 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 group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the general formula (40), R 901 ~R 904 are R in the general formula (4A), 901 ~R 904 is equivalent to

[0204] In one embodiment of the fourth compound, Ar 411 , Ar 412 , and Ar 413 At least one of these is a group represented by any one of the general formulae (56A) to (68A).

[0205] [ka]

[0206] (In the general formulae (56A) to (60A), R51 ~R 58 , R 51A and R 52A are R in the general formula (4A), 51 ~R 58 , R 51A and R 52A is synonymous with * each independently represents L in the general formula (4). A1 , L A2 and L A3 (the bonding position with a nitrogen atom or a carbon atom constituting a benzene ring in the general formulas (40) to (41), or the bonding position with a nitrogen atom in the general formula (42).

[0207] [ka]

[0208] (In the general formulae (61A) to (68A), R 51 ~R 58 are R in the general formula (4A), 51 ~R 58 is synonymous with * each independently represents L in the general formula (4). A1 , L A2 and L A3 (the bonding position with a nitrogen atom or a carbon atom constituting a benzene ring in the general formulas (40) to (41), or the bonding position with a nitrogen atom in the general formula (42).

[0209] In one embodiment of the fourth compound, Ar 411 , Ar 412 , and Ar 413 At least one of these is a group represented by any one of the general formulae (56A) to (68A). In one embodiment of the fourth compound, Ar 411 , Ar 412 , and Ar 413At least one of these is a group represented by any one of the general formulae (56A) to (60A). In one embodiment of the fourth compound, Ar 411 , Ar 412 , and Ar 413 Among these, two are groups represented by any one of the general formulae (56A) to (68A). In one embodiment of the fourth compound, Ar 411 , Ar 412 , and Ar 413 Among these, two are groups represented by any one of the general formulae (56A) to (60A). In one embodiment of the fourth compound, Ar 411 , Ar 412 , and Ar 413 Among these, three are groups represented by any one of the general formulae (56A) to (68A). In one embodiment of the fourth compound, Ar 411 , Ar 412 , and Ar 413 Among these, three are groups represented by any one of the general formulae (56A) to (60A). In one embodiment of the fourth compound, Ar 411 , Ar 412 , and Ar 413 When two or three of the groups are represented by any one of the general formulae (56A) to (68A), two or three of the Ar 411 , Ar 412 , and Ar 413 are either identical to or different from each other.

[0210] 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 413 each independently represents 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 phenanthryl group. 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 413 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group. In one embodiment of the fourth compound, Ar 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.

[0211] In one embodiment of the fourth compound, R 51 ~R 58 , R 51A , R 52A , R 53A , 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. In one embodiment of the fourth compound, R 51 ~R 58 , R 51A , R 52A , R 53A , 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.

[0212] In one embodiment of the fourth compound, the substituents in the case of "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.

[0213] In one embodiment of the fourth compound, the substituents in the case of "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 fourth compound, the substituent in the term "substituted or unsubstituted" is an "unsubstituted" group.

[0214] In one aspect of the organic EL element according to the first embodiment, the first layer contains the fourth compound in an amount of 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, 95% by mass or more, or 99% by mass or more. In one aspect of the organic EL element according to the first embodiment, the first layer may be a layer containing only the fourth compound.

[0215] (Production method of the fourth compound) The fourth compound can be produced by a known method.

[0216] (Example of the fourth compound) Specific examples of the fourth compound include the following compounds, however, the present invention is not limited to these specific examples of the compound.

[0217] [ka]

[0218] [ka]

[0219] [ka]

[0220] (Third layer (thick film hole transport layer)) In the organic EL element of the first embodiment, the third layer contains a sixth compound. The sixth compound is not particularly limited as long as it satisfies the above formula (Formula 42). 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 be a compound having a substituted or unsubstituted carbazolyl group and one substituted or unsubstituted amino group in the molecule. As the sixth compound, for example, a compound satisfying the formula (Mathematical Formula 42) can be selected from the compounds represented by the general formula (4), the compounds represented by the general formula (5), and the compounds represented by the following general formula (620).

[0221] [ka]

[0222] (In the general formula (620), p2 is 4, p3 is 4, p5 is 4, p7 is 3, p8 is 4, Multiple R 42 are the same or different, and multiple R 42 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, Multiple R 43 are the same or different, and multiple R 43At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, Multiple R 45 are the same or different, and multiple R 45 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, Multiple R 47 are the same or different from each other, Multiple R 48 are the same or different from each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 42 , R 43 , R 45 , R 47 and R 48 are each independently 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 A group represented by -COOR 909 A group represented by Cyano group, Nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 411 ~R 415 A set of two or more adjacent 441 ~R 445 A pair of two or more adjacent 461 ~R 465 one or more pairs selected from the group consisting of adjacent pairs of two or more of the following are bonded to each other to form a ring represented by the general formula (621) or (622), or are not bonded to each other; R which does not form a ring represented by the general formula (621) or (622) 411 ~R 415 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 42 is synonymous with R which does not form a ring represented by the general formula (621) or (622) 441 ~R 445 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 42 is synonymous with R which does not form a ring represented by the general formula (621) or (622) 461 ~R 465R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 42 is synonymous with In the general formula (621), R 401 ~R 404 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 401 ~R 404 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 42 is synonymous with *a and *b each represent a bonding position; In the general formula (622), X 41 is C(Rc 4 )(Rd 4 ), oxygen atom, sulfur atom, or N(Rf 4 ) and Rc 4 and Rd 4 A set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 405 ~R 408 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, Rf 4、 R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 405~R 408 and Rc which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 4 and Rd 4 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 42 is synonymous with *c and *d indicate the binding positions, respectively.)

[0223] In one aspect of the organic EL element according to the first embodiment, the third layer contains the sixth compound in an amount of 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, 95% by mass or more, or 99% by mass or more. In one aspect of the organic EL element according to the first embodiment, the third layer may be a layer containing only the sixth compound.

[0224] (Hole injection layer) One aspect of the organic EL element of the first embodiment includes a hole injection layer between the anode and the third layer. For the hole injection layer, for example, the "substance with high hole injection properties" described in the <Structure of the organic EL element> described later can be used. 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. As the first organic material, a compound represented by the general formula (5) may be used, a compound represented by the general formula (4) may be used, or a compound represented by the general formula (620) may be used. 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 third layer are the same as or different from each other. In one aspect of the organic EL device of the first embodiment, the content of the acceptor material in the hole injection layer is less than 50% by mass.

[0225] (Light Emitting Layer) In the organic EL device of the first embodiment, the light-emitting layer contains a delayed fluorescent compound as the second compound. In the following, of the organic EL element of the first embodiment, an 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.

[0226] In the organic EL element of the first embodiment, the first compound is preferably a dopant material (also referred to as a guest material, an emitter, or a light-emitting material), the second compound is preferably a host material (also referred to as a matrix material), and the third compound is preferably a host material.

[0227] In the organic EL device of the first embodiment, the first compound, the second compound, and the third compound are preferably contained in the same layer, that is, the first compound, the second compound, and the third compound are preferably contained in the same light-emitting layer.

[0228] 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 a phosphorescent metal complex. In one embodiment, the light-emitting layer may include a metal complex. In one embodiment, it is also preferable that the light-emitting layer does not contain a metal complex. In one embodiment, the light-emitting layer preferably does not contain a phosphorescent material. In one embodiment, the light-emitting layer preferably does not contain a heavy metal complex or a phosphorescent rare earth metal complex. Examples of the heavy metal complex include an iridium complex, an osmium complex, and a platinum complex.

[0229] (Second Compound) In the organic EL device according to the first embodiment, the second compound is, for example, a delayed fluorescent compound represented by the following general formula (1).

[0230] [ka]

[0231] (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, D 11 and D. 12 are each independently a group represented by the following general formula (11), (12) or (13), h is an integer equal to or greater than 2; k is an integer equal to or greater than 1, m is an integer equal to or greater than 0, D 11 and D. 12 are the same or different from each other, Multiple D's 11 are the same or different from each other, Multiple D's 12 are either identical or different.)

[0232] [ka]

[0233] [ka]

[0234] [ka]

[0235] (R in the general formula (11) 1 ~R 8 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R in the general formula (12) 11 ~R 18 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R in the general formula (13) 111 ~R 118 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R in the general formula (11) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. 1 ~R 8 R in the general formula (12) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring. 11 ~R 18 and R in the general formula (13) which 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 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 A group represented by -COOR 909 A group represented by Halogen atoms, Cyano group, Nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the general formula (12) and the general formula (13), Ring A, ring B and ring C each independently represent a 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 the adjacent ring at any position; p, px and py are each independently 1, 2, 3 or 4; When p is 2, 3 or 4, the rings A are the same or different from each other, When px is 2, 3 or 4, the rings B are the same or different from each other, When py is 2, 3 or 4, the rings C are the same or different from each other; In the general formulae (11) to (13), * indicates the bonding position with L in the general formula (1).

[0236] [ka]

[0237] (In the general formula (14), r is 0, 2 or 4; Multiple R 19 A set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, In the general formula (15), X 1 is a sulfur atom, an oxygen atom, and a C(R 151 )(R 152 ) or N(R 153 ) and R 151 and R 152 A set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 153 R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed 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 condensed ring. 19 are each independently 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 A group represented by -COOR 909 A group represented by Halogen atoms, Cyano group, Nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, Multiple R 19 are the same or different from each other, Multiple X's 1 are either identical or different.)

[0238] In the second compound, R 901 ~R 907 and R 931 ~R 937 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 906 If there are multiple R 906 are the same or different from each other, R 907 If there are multiple R 907 are the same or different from each other, R 908 If there are multiple R 908 are the same or different from each other, R 909 If there are multiple R 909 are the same or different from each other, R 931 If there are multiple R 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 933are 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.

[0239] In one aspect of the organic EL element according to the first embodiment, at least one D 11 But R 1 ~R 8 one or more pairs of adjacent two or more of the above-mentioned groups are bonded to each other to form the substituted or unsubstituted monocycle or the substituted or unsubstituted fused ring, which are represented by general formula (11), (12), or (13).

[0240] The second compound is also preferably a compound represented by the following general formula (100).

[0241] [ka]

[0242] (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; R is independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 A group represented by -COOR 909 A group represented by Cyano group, Nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, 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 the general formula (100) via a carbon-carbon bond; n is an integer equal to or greater than 1, The multiple R's are the same or different.

[0243] 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 as L is preferably a benzene ring, a naphthalene ring, a fluorene ring or a phenanthrene ring.

[0244] 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).

[0245] In the organic EL device according to the first embodiment, the compound (second compound) represented by the general formula (1) is preferably represented by the following general formula (101).

[0246] [ka]

[0247] (In the general formula (101), D 11 and D. 12 respectively represent D in the general formula (1). 11 and D. 12 is synonymous with 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; h+k+m+n=6, R is independently 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 A group represented by -COOR 909 A group represented by Cyano group, Nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, The multiple R's are the same or different.

[0248] In the second compound, the benzene ring of the general formula (101) to which the groups represented by the general formulae (11) to (13) are bonded is the benzene ring explicitly shown in the general formula (101), and R, D 11 and D. 12 It is not a benzene ring contained in

[0249] 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, with the proviso that at least one R is a substituent, and at least one R as the substituent is preferably bonded to the benzene ring in the general formula (101) via a carbon-carbon bond.

[0250] In the second compound, h is preferably 2 or 3, and more preferably 2.

[0251] 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).

[0252] [ka]

[0253] (In the above 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.)

[0254] It is preferred that in the second compound, k is 1, m is 1 and n is 2.

[0255] 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 (126) or (127).

[0256] [ka]

[0257] (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 (1), k is 1 or 2, m is 0 or 1, and k+m is 2.

[0258] 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).

[0259] [ka]

[0260] (In the general formula (126A), general formula (127A) and 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 (1).

[0261] In the organic EL device according to the first embodiment, the compound represented by the general formula (1) is, in the general formulae (126A), (127A), and (127B), 11 and D. 12 are preferably different groups from each other.

[0262] 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).

[0263] [ka]

[0264] (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 (1), k is 1 or 2, m is 0 or 1, and k+m is 2.

[0265] 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).

[0266] [ka]

[0267] (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 (1).

[0268] In the second compound, at least one D 11 is preferably a group represented by the general formula (12) or (13).

[0269] In the second compound, at least one D 11 is preferably a group represented by the following general formula (121), (122) or (131).

[0270] [ka]

[0271] [ka]

[0272] [ka]

[0273] (In the general formulae (121) and (122), R 11 ~R 18 are R in the general formula (12), 11 ~R 18 is synonymous with Ring A 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), In the general formula (131), R 111 ~R 118 are R in the general formula (13), 111 ~R 118 is synonymous with Ring B 1 and Ring B 2 one of the ring structures represented by the general formula (14) is ring B 1 and Ring B 2 the other is a ring structure represented by general formula (15), 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 general formula (15), In the general formulae (121), (122) and (131), * indicates the bonding position with L in the general formula (1), or the bonding position with the benzene ring in the general formulae (101), (110), (120), (126), (126A), (126C), (126D), (127), (127A), (127B), (127C), (127D) or (130).

[0274] In the second compound, ring A 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). In the second compound, ring B 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). In the second compound, ring C 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).

[0275] In the second compound, at least one D 11 is preferably a group represented by the above general formula (131).

[0276] In the second compound, at least one D 11 is preferably a group represented by the following general formula (123), (124), (125) or (132).

[0277] [ka]

[0278] [ka]

[0279] [ka]

[0280] [ka]

[0281] (In the above general formulae (123), (124) and (125), R 11 ~R 18 are R in the general formula (12), 11 ~R 18 is synonymous with R 191 ~R 194 each independently represents R in the general formula (14). 19 is synonymous with In the general formula (132), R 111 ~R 118 are R in the general formula (13), 111 ~R 118 is synonymous with R 195 ~R 198 each independently represents R in the general formula (14). 19 is synonymous with In the general formulae (123), (124), (125) and (132), X 13 and X 14 each independently represents X in the general formula (15). 1 and * 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).

[0282] In the second compound, X 13 is preferably a sulfur atom.

[0283] In the second compound, at least one D 11 is preferably a group represented by the above general formula (132).

[0284] In the second compound, m is preferably an integer of 1 or more.

[0285] In the second compound, D 12 is a group represented by the above general formula (11) or (12), and m is preferably an integer of 1 or more.

[0286] In the second compound, it is preferred that k and m are 1.

[0287] In the second compound, at least one D 12 is also preferably a group represented by the general formula (11).

[0288] In the second compound, at least one D 12 is also preferably a group represented by the general formula (12).

[0289] 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).

[0290] [ka]

[0291] [ka]

[0292] [ka]

[0293] [ka]

[0294] [ka]

[0295] [ka]

[0296] (In the general formulae (12A), (12B), (12C), (12D), (12E) and (12F), R 11 ~R 18 are R in the general formula (12), 11 ~R 18 is synonymous with R 19 and R 20 each independently represents R in the general formula (14). 19 is synonymous with X 1 is X in the general formula (15). 1 is synonymous with 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 formulae (101), ((110), (120), (126), (126A), (126C), (126D), (127), (127A), (127B), (127C), (127D) or (130).

[0297] In the second compound, X 1 is preferably an oxygen atom or a sulfur atom.

[0298] In the second compound, R 1 ~R 8 It is also preferred that adjacent pairs of two or more of the above are not bonded to each other. In the second compound, R 11 ~R 18 It is also preferred that adjacent pairs of two or more of the above are not bonded to each other. In the second compound, R111 ~R 118 It is also preferred that adjacent pairs of two or more of the above are not bonded to each other.

[0299] 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.

[0300] 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.

[0301] 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.

[0302] 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) 19are preferably 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.

[0303] 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, 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.

[0304] 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, 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 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.

[0305] In the second compound, 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 ) a group represented by an unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 A group represented by -COOR 909 A group represented by -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by -S(=O) 2 R 938 A group represented by Halogen atoms, Cyano group, Nitro group, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms, R 901 ~R 909 , and R 931 ~R 938 are each independently Hydrogen atoms, an unsubstituted alkyl group having 1 to 25 carbon atoms; an unsubstituted aryl group having 6 to 25 ring carbon atoms, or An unsubstituted heterocyclic group having 5 to 25 ring atoms is preferred.

[0306] In the second compound, 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.

[0307] In the second compound, 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.

[0308] 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.

[0309] As used herein, -O-(R 904 ) is a group represented by R 904 When is a hydrogen atom, it is a hydroxy group. As used herein, -S-(R 905 ) is a group represented by R 905 When is a hydrogen atom, it is a thiol group. As used herein, -P(=O)(R 931 )(R 932 ) is a group represented by R 931 and R 932 is a substituent, it is a substituted phosphine oxide group, R 931 and R 932 When is an aryl group, it is an arylphosphoryl group. As used herein, -Ge(R 933 )(R 934 )(R 935 ) is a group represented by R 933 , R 934 and R 935When is a substituent, it is a substituted germanium group. As used herein, -B(R 936 )(R 937 ) is a group represented by R 936 and R 937 When is a substituent, it is a substituted boryl group.

[0310] (Delayed fluorescence) Delayed fluorescence is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Adachi Chihaya, published by Kodansha). In that paper, the energy difference ΔE between the excited singlet state and the excited triplet state of a fluorescent material is 13 It is explained that if it is possible to reduce the energy transfer efficiency, the reverse energy transfer from the excited triplet state, which usually has a low transition probability, to the excited singlet state occurs with high efficiency, and thermally activated delayed fluorescence (TADF) is expressed. Furthermore, the mechanism of delayed fluorescence generation is explained in FIG. 10.38 of the document. The second compound according to the first embodiment is preferably a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism.

[0311] In general, delayed fluorescence emission can be confirmed by transient PL (Photoluminescence) measurement.

[0312] The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from transient PL measurements. Transient PL measurements are a method of exciting a sample with a pulsed laser and 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 first PL excitation and emission components from singlet excitons generated via triplet excitons. The lifetime of singlet excitons generated during the first PL excitation is on the order of nanoseconds, which is very short. Therefore, the emission from the singlet excitons decays quickly after irradiation with a pulsed laser. On the other hand, delayed fluorescence decays slowly because it is emitted from singlet excitons generated via triplet excitons, which have a long life span. Thus, there is a large time difference between the emission from singlet excitons generated by the initial PL excitation and the emission from singlet excitons generated via triplet excitons. Therefore, it is possible to obtain the emission intensity derived from delayed fluorescence.

[0313] A schematic diagram of an exemplary apparatus for measuring transient PL is shown in Fig. 2. An example of a method for measuring transient PL and an analysis of the behavior of delayed fluorescence using Fig. 2 will be described.

[0314] 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.

[0315] The sample accommodated in the sample chamber 102 is obtained by forming a thin film, in which a doping material is doped at a concentration of 12 mass % relative to a matrix material, on a quartz substrate.

[0316] A pulsed laser is irradiated from a pulsed laser unit 101 to a thin film sample accommodated in a sample chamber 102 to excite the doping material. Emission light is extracted in a direction at 90 degrees to the irradiation direction of the excitation light, and the extracted light is dispersed by a spectrometer 103 to form 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. By cutting out this two-dimensional image at a predetermined time axis, an emission spectrum can be obtained in which the vertical axis is emission intensity and the horizontal axis is wavelength. Furthermore, by cutting out the two-dimensional image at the wavelength axis, a decay curve (transient PL) can be obtained in which the vertical axis is the logarithm of emission intensity and the horizontal axis is time.

[0317] For example, the following compound HX1 was used as the matrix material, and the following compound DX1 was used as the doping material to prepare thin film sample A as described above, and transient PL measurement was performed.

[0318] [ka]

[0319] 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.

[0320] FIG. 3 shows the decay curves obtained from the transient PL measured for thin film sample A and thin film sample B.

[0321] [ka]

[0322] As described above, the transient PL measurement can provide an emission decay curve with the emission intensity on the vertical axis and the time on the horizontal axis. Based on this emission decay curve, the fluorescence intensity ratio between the fluorescence emitted from the singlet excited state generated by photoexcitation and the delayed fluorescence emitted from the singlet excited state generated by reverse energy transfer via the triplet excited state can be estimated. In delayed fluorescent materials, the ratio of the intensity of the delayed fluorescence that decays slowly to the intensity of the fluorescence that decays quickly is somewhat large.

[0323] Specifically, there are two types of luminescence from delayed fluorescent materials: prompt luminescence and delayed luminescence. Prompt luminescence is luminescence that is observed immediately from the excited state after being excited by pulsed light (light irradiated from a pulsed laser) 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.

[0324] The amount and ratio of prompt luminescence and delayed luminescence 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 amount of prompt luminescence and delayed luminescence is not limited to the device described in Reference 1 or the device shown in FIG. 2.

[0325] In addition, 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 in order to eliminate the contribution of self-absorption. In addition, in order to prevent quenching due to oxygen, the sample solution is frozen and degassed, and then sealed in a cell with a lid under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the above 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. The total fluorescence quantum yield is calculated using the fluorescence area intensity of both spectra according to formula (1) in Morris et al. J. Phys. Chem. 80 (1976) 969.

[0326] In the first embodiment, the amount of prompt luminescence (instantaneous luminescence) of the compound to be measured is X P and the amount of delay light emission is X D When X D / X P It is preferable that the value is 0.05 or more. The amounts and ratio of prompt luminescence and delayed luminescence of compounds other than the second compound according to the first embodiment in this specification are measured in the same manner as the amounts and ratio of prompt luminescence and delayed luminescence of the second compound according to the first embodiment.

[0327] (ΔST) In the first embodiment, the lowest excited singlet energy S 1 and the energy gap T at 77[K]77K Difference with (S 1 -T 77K ) is defined as ΔST.

[0328] 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) from (M2) is preferably less than 0.3 eV, more preferably less than 0.2 eV, even more preferably less than 0.1 eV, and even more preferably less than 0.01 eV. That is, ΔST(M2) preferably satisfies the relationship of the following formula (10), (11), (12), or (13). ΔST(M2)=S 1 (M2)-T 77K (M2)<0.3eV…(Number 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)

[0329] Relationship between triplet energy and energy gap at 77[K] Here, the relationship between the triplet energy and the energy gap at 77 [K] will be described. In the first embodiment, the energy gap at 77 [K] is different from the triplet energy that is usually defined. The triplet energy is measured as follows. First, a sample is prepared by dissolving the compound to be measured in an appropriate solvent and sealing the solution in a quartz glass tube. The phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) of this sample is measured at low temperature (77[K]), a tangent is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the triplet energy is calculated from a predetermined conversion formula based on the wavelength value at the intersection of the tangent and the horizontal axis. Here, the second compound according to the first embodiment is preferably a thermally activated delayed fluorescent compound having a small ΔST. When ΔST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at low temperatures (77[K]), and the excited singlet state and the excited triplet state are mixed. As a result, the spectrum measured in the same manner as above includes light emission from both the excited singlet state and the excited triplet state, and it is difficult to distinguish which state the light emission is from, but the triplet energy value is basically considered to be dominant. Therefore, in the first embodiment, the measurement method is the same as that of the normal triplet energy T, but in order to distinguish the difference 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 be used as a measurement sample. Measure the phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) at low temperature (77[K]), draw a tangent to the rising edge on the short wavelength side of this phosphorescence spectrum, and measure the wavelength value λ at the intersection of the tangent and the horizontal axis. edge Based on [nm], the amount of energy calculated from the following conversion formula (F1) is the energy gap T at 77[K]. 77K Let us assume that. Conversion formula (F1):T 77K [eV]=1239.85 / λ edge

[0330] The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows. When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum of the spectral maxima, consider the tangent at each point on the curve toward the long wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope is at its maximum (i.e., the tangent at the inflection point) is the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that a maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and the tangent drawn at the point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side is regarded as the tangent to the rising edge on the short wavelength side of the phosphorescence spectrum. Phosphorescence can be measured using a spectrofluorometer body, model F-4500, manufactured by Hitachi High-Technologies Corp. However, the measuring device is not limited to this, and measurements may be performed by combining a cooling device, a low-temperature container, an excitation light source, and a light receiving device.

[0331] The lowest excited singlet energy S 1 The lowest excited singlet energy S using a solution 1 The measurement method (sometimes called the solution method) is as follows. Prepare a 10 μmol / L toluene solution of the compound to be measured and place it in a quartz cell, then measure the absorption spectrum of this sample (vertical axis: absorption intensity, horizontal axis: wavelength) at room temperature (300 K). Draw a tangent to the falling edge on the long wavelength side of this absorption spectrum, and substitute the wavelength value λedge [nm] at the intersection of the tangent and the horizontal axis into the following conversion formula (F2) to calculate the lowest excited singlet energy. Conversion formula (F2):S 1 [eV]=1239.85 / λedge An example of an absorption spectrum measuring device is a spectrophotometer manufactured by Hitachi (device name: U3310), but is not limited to this.

[0332] The tangent to the falling edge on the long wavelength side of the absorption spectrum is drawn as follows. When moving along the spectral curve from the maximum value on the longest wavelength side among the maximum values ​​of the absorption spectrum in the direction towards longer wavelengths, consider the tangent at each point on the curve. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the slope is at its minimum value on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is regarded as the tangent to the falling edge on the long wavelength side of the absorption spectrum. Note that maximum points with absorbance values ​​of 0.2 or less are not included in the maximum value on the longest wavelength side.

[0333] (Method for Producing Second Compound According to the First Embodiment) The second compound can be produced by a known method. The second compound can also be produced by following a known method and using known alternative reactions and raw materials suited to the target compound.

[0334] (Specific Example of the Second Compound) 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.

[0335] [ka]

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[0354] (First Compound) In one aspect of the organic EL device 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. It is preferred that the first compound is not a heavy metal complex. It is also preferred that the first compound is not a metal complex.

[0355] 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.

[0356] The first compound is preferably a compound that emits light having a maximum peak wavelength of 400 nm or more and 700 nm or less. In this specification, the maximum peak wavelength is the wavelength at which the compound to be measured -6 moles / liter > 10 -5 The peak wavelength of the fluorescence spectrum at which the emission intensity is maximum in the fluorescence spectrum measured for a toluene solution in which the compound is dissolved at a concentration of mol / L or less is used. The measurement device used is a spectrofluorophotometer (F-7000, manufactured by Hitachi High-Tech Science Corporation).

[0357] 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 or more and 660 nm or less. When the first compound is a red fluorescent compound, the maximum peak wavelength of the first compound is preferably 600 nm or more and 660 nm or less, more preferably 600 nm or more and 640 nm or less, and further preferably 610 nm or more and 630 nm or less. In this specification, green emission refers to emission having a maximum peak wavelength in the fluorescence spectrum within the range of 500 nm or more and 560 nm or less. When the first compound is a green fluorescent compound, the maximum peak wavelength of the first compound is preferably 500 nm or more and 560 nm or less, more preferably 500 nm or more and 540 nm or less, and further preferably 510 nm or more and 540 nm or less. In this specification, blue emission refers to emission having a maximum peak wavelength in the fluorescence spectrum within the range of 430 nm or more and 480 nm or less. When the first compound is a blue fluorescent compound, the maximum peak wavelength of the first compound is preferably 430 nm or more and 480 nm or less, more preferably 440 nm or more and 480 nm or less.

[0358] It is preferable that the first compound satisfies the following formula (Mathematical formula 21): |HOMO(M1)| is synonymous with the ionization potential Ip(M1) of the first compound. It is believed that when |HOMO(M1)| of the first compound satisfies the following formula (Mathematical formula 21), holes are less likely to be trapped by the dopant material, and holes are widely distributed in the light-emitting layer. (Equation 21): |HOMO(M1)| ≧ 5.25 eV (HOMO(M1) is the energy level of the highest occupied molecular orbital of the first compound.)

[0359] It is preferable that the first compound satisfies the following formula (Mathematical formula 2C). When |HOMO(M1)| of the first compound satisfies the following formula (Mathematical formula 2C), the relationship |HOMO(M1)|<|HOMO(M3)| is easily established, and the charge balance in the light-emitting layer is easily adjusted. 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. (Math 2C): |HOMO(M1)|≦5.65 eV

[0360] The first compound is not particularly limited, but is preferably a compound that satisfies the above formula (Mathematical formula 21). Examples of the first compound include compounds represented by the following general formula (D1), general formula (D11), general formula (D10) and general formula (D20). As the first compound, it is preferable to select and use a compound that satisfies the above-mentioned mathematical formula (Mathematical Formula 21) from among the above-mentioned fluorescent materials and the compounds represented by the following general formulas (D1), (D11), (D10) and (D20).

[0361] (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).

[0362] [ka]

[0363] (In the general formula (D1), Ring Ax, ring Bx, ring Dx, ring Ex and ring Fx each independently represent a substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms, and a ring structure selected from the group consisting of substituted or unsubstituted heterocycles 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, it is a nitrogen atom or a carbon atom; When the ring Bx does not exist, oxygen atom, sulfur atom, NRb, C(Rb 1 )(Rb 2 ) or Si(Rb 3 )(Rb 4) and Zc is a nitrogen atom or a carbon atom; Zd is When ring Dx is present, it is a nitrogen atom or a carbon atom; When ring Dx is not present, it is an oxygen atom, a sulfur atom, or NRd. Ze is, When ring Ex is present, it is a nitrogen atom or a carbon atom; When the ring Ex is absent, it is an oxygen atom, a sulfur atom, or NRe; Zf is a nitrogen atom or a carbon atom; Zg is When ring Fx is present, it is a nitrogen atom or a carbon atom; When ring Fx is not present, oxygen atom, sulfur atom, NRg, C(Rg 1 )(Rg 2 ) or Si(Rg 3 )(Rg 4 ) and 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 4 and Rh are each independently a hydrogen atom or a substituent; 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 are each independently 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 ) a group represented by -N(R 916 )(R 917 ) is a group represented by However, the bond between Y and Za, the bond between Y and Zd, and the bond between Y and Ze are all single bonds.)

[0364] 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 are not coordinate bonds.

[0365] In the present specification, examples of the heterocycle include a ring structure (heterocycle) obtained by removing a bond from the "heterocyclic group" exemplified in the above-mentioned "substituents described in the present specification". These heterocycles may have a substituent or may be unsubstituted. In the present specification, examples of the aryl ring include ring structures (aryl rings) obtained by removing a bond from the "aryl group" exemplified in the above-mentioned "substituents described in the present specification". These aryl rings may have a substituent or may be unsubstituted.

[0366] (Compound represented by general formula (D11)) In the organic EL device according to the first embodiment, the first compound is preferably a compound represented by the following formula (D11): The compound represented by the general formula (D1) is preferably a compound represented by the following general formula (D11).

[0367] [ka]

[0368] (In the general formula (D11), Ring Ax, ring Dx and ring Ex each independently represent a substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms, and a ring structure selected from the group consisting of substituted or unsubstituted heterocycles having 5 to 30 ring atoms, Za is a nitrogen atom or a carbon atom; Zb is an oxygen atom, a sulfur atom, NRb, C(Rb 1 )(Rb 2 ) or Si(Rb 3 )(Rb 4 ) and 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 ) and 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.)

[0369] (Compound represented by general formula (D10)) In the organic EL device according to the first embodiment, the first compound is preferably a compound represented by the following formula (D10): The compound represented by the general formula (D1) is preferably a compound represented by the following general formula (D10).

[0370] [ka]

[0371] (In the general formula (D10), X 1 CR 1 or a nitrogen atom, X 2 CR 2 or a nitrogen atom, X 3 CR 3 or a nitrogen atom, X 4 CR 4 or a nitrogen atom, X 5 CR 5 or a nitrogen atom, X 6 CR 6 or a nitrogen atom, X 7 CR 7 or a nitrogen atom, or X 8 is a carbon atom bonded to X 8 CR 8 or a nitrogen atom, or X 7 is a carbon atom bonded to X 9 CR 9 or a nitrogen atom, X 10 CR 10 or a nitrogen atom, X 11 CR 11 or a nitrogen atom, X 12CR 12 or a nitrogen atom, Q is CR Q or a nitrogen atom, 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 R 9 ~R 11 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 3、 R 4 and R Y1 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 3、 R 4 and R Y1 At least one hydrogen atom in a single ring or a condensed ring formed by bonding one or more adjacent pairs of an alkyl group having 1 to 50 carbon atoms; an aryl group having 6 to 50 ring carbon atoms; a heterocyclic group having 5 to 50 ring atoms, -O-(R 920 ) and -N(R 921 )(R 922 or is unsubstituted, and at least one hydrogen atom in the substituent is either unsubstituted or substituted with an aryl group having 6 to 50 ring carbon atoms or an alkyl group having 1 to 50 carbon atoms; R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 1 ~R 11 , and R 12 ~R 13 , and R Q are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 911 )(R 912 )(R 913 ) a group represented by -O-(R 914 ) a group represented by -S-(R 915 ) a group represented by -N(R 916 )(R 917 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 918 A group represented by -COOR 919 A group represented by Halogen atoms, Cyano group, Nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. Y1 teeth, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R Y2 and R Y3 A set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. Y2 and R Y3 , and R Y4 and R Y5 are each independently Hydrogen atoms, Halogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 911 ~R 922 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 911 If there are multiple R 911 are the same or different from each other, R 912 If there are multiple R 912are 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 either identical or different.)

[0372] In the compound represented by the general formula (D10), X 7 X 8 A carbon atom that is bonded to X by a single bond. 8 X 7 is a carbon atom bonded to by a single bond, for example, the general formula (D10) is represented by the following general formula (D10A).

[0373] [ka]

[0374] (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).

[0375] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D12).

[0376] [ka]

[0377] (In the general formula (D12), R 1 ~R 13 , R Y1 , R Q are each independently as defined in general formula (D10).

[0378] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D12A).

[0379] [ka]

[0380] (In the general formula (D12A), R 1 ~R 6 , R 9 ~R 13 , R Y1 , R Q are each independently as defined in general formula (D10).

[0381] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D13).

[0382] [ka]

[0383] (In the general formula (D13), R 1 ~R 3 , R 5 ~R 13 and R Q are each independently as defined in general formula (D10), R x1 ~R x4 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. X1 ~R x4 are each independently 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 938 A group represented by -COOR 939A group represented by Halogen atoms, Cyano group, Nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 931 ~R 939 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 931 If there are multiple R 931 are the same or different from each other, R 932 If there are multiple R 932 are the same or different from each other, R 933 If there are multiple R 933 are the same or different from each other, R 934 If there are multiple R 934 are the same or different from each other, R 935 If there are multiple R 935 are the same or different from each other, R 936 If there are multiple R 936 are the same or different from each other, R 937 If there are multiple R 937 are the same or different from each other, R 938 If there are multiple R 938 are the same or different from each other, R 939 If there are multiple R 939 are either identical or different.)

[0384] 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.

[0385] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D13A).

[0386] [ka]

[0387] (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).

[0388] In the compound represented by the general formula (D10), R 1 ~R 13 and R Q are each independently 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 is also preferred.

[0389] In the compound represented by the general formula (D10), R 1 ~R 13 and R Q are each independently 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 is also preferred.

[0390] 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 Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or A substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms is also preferred.

[0391] 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 Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or A substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms is also preferred.

[0392] In the compound represented by the general formula (D10), R 1 ~R 13 , R Q and R x1 ~R x4 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is preferably a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

[0393] In the compound represented by the general formula (D10), R 1 ~R 13 , R Q and R x1 ~R x4 are each independently 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 is preferred.

[0394] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D14).

[0395] [ka]

[0396] (In the general formula (D14), R 2 , R 6、 R 13、 R Q and R x2 are each independently 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 It is a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms.

[0397] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D15).

[0398] [ka]

[0399] (In the general formula (D15), R 2 , R 6、 R 13、 R Q and R x2 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or It is a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms.

[0400] In the compound represented by the general formula (D10), R 13 and R Q are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group, or A substituted or unsubstituted dibenzofuranyl group is preferred.

[0401] In the compound represented by the general formula (D10), R 6 and R x2 It is preferable that each of the is independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0402] (Compound represented by general formula (D20)) In the organic EL device according to the first embodiment, the first compound is also preferably a compound represented by the following general formula (D20).

[0403] [ka]

[0404] 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; 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 of the pairs of Y and R as Substituents 21 ~R 26 are 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; Halogen atoms, Carboxy group, a substituted or unsubstituted ester group; a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted amino group, Nitro group, Cyano group, a substituted or unsubstituted silyl group, and selected from the group consisting of substituted or unsubstituted siloxanyl groups; Z 21 and Z 22 are each independently a substituent or Z 21 and Z 22 are bonded together to form a ring, Z as a Substituent 21 and Z 22 are each independently Halogen atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted 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 The aryloxy group is selected from the group consisting of substituted or unsubstituted aryloxy groups having 6 to 30 ring carbon atoms.

[0405] 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 ) a group represented by an unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 A group represented by -COOR 909 A group represented by -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 group represented by Halogen atoms, Cyano group, Nitro group, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms, R 901 ~R 909 , and R 941 ~R 946 are each independently 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 is preferred.

[0406] 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.

[0407] 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.

[0408] In the first compound according to the first embodiment, it is also preferable that all of the groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0409] (Specific examples of compounds represented by formula (D1), (D11), (D10) or (D20) Specific examples of the compound represented by the general formula (D1), (D11), (D10) or (D20) include the following compounds, although the present invention is not limited to these specific examples.

[0410] [ka]

[0411] [ka]

[0412] (Third Compound) In the light-emitting layer of the organic EL element of the first embodiment, the third compound may be a compound having thermally activated delayed fluorescence or a compound not exhibiting thermally activated delayed fluorescence, but is preferably a compound not exhibiting thermally activated delayed fluorescence.

[0413] The third compound is not particularly limited. The third compound is preferably a compound represented by the following general formula (3) or a compound represented by the following general formula (MRX3).

[0414] (Compound represented by general formula (3)) In the light-emitting layer of the organic EL device of the first embodiment, the third compound is also preferably a compound represented by the following general formula (3).

[0415] [ka]

[0416] (In the general formula (3), A3 teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L 3 teeth, Single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms; a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, A divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, or a divalent group formed by bonding three groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, R 31 ~R 38 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 31 ~R 38 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 A group represented by -COOR 909 A group represented by Halogen atoms, Cyano group, Nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or It is a group represented by the following general formula (3A).

[0417] [ka]

[0418] (In the general formula (3A), R B teeth, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 A group represented by -COOR 909 A group represented by Halogen atoms, Cyano group, Nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R B When there are multiple R B are the same or different from each other, L 31 teeth, Single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the arylene group, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, a trivalent group, a tetravalent group, a pentavalent group, or a hexavalent group derived from the heterocyclic group, or a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, or a trivalent group, tetravalent group, pentavalent group or hexavalent group derived from the divalent group, L 32 teeth, Single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, n 3 is 1, 2, 3, 4 or 5, L 31 If 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), L 32 When there are multiple L 32 are the same or different from each other, * is the bonding site to the carbon atom of the six-membered ring in the general formula (3).

[0419] (In the compound represented by the general formula (3), 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 937 are each independently 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 R935 are the same or different from each other, R 936 If there are multiple R 936 are the same or different from each other, R 937 If there are multiple R 937 are either identical or different.)

[0420] 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).

[0421] [ka]

[0422] [ka]

[0423] [ka]

[0424] (In the general formulas (31) to (36), A 3 and L 3 respectively represent A in the general formula (3). 3 and L 3 is synonymous with R 341 ~R 350 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, X 31 is a sulfur atom, an oxygen atom, and NR 352 or CR 353 R 354 and R 353 and R354 A set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed 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 R each independently represents a ring that does not form the substituted or unsubstituted monocycle and a ring that does not form the substituted or unsubstituted condensed ring. 31 ~R 38 is equivalent to

[0425] In the compound represented by the general formula (3), R 352 teeth, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0426] In the compound represented by the general formula (3), R 353 and R 354 A set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring. 353 and R 354 are 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 It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0427] In the compound represented by the general formula (3), X 31 is preferably a sulfur atom or an oxygen atom.

[0428] In the compound represented by the general formula (3), A 3 is preferably a group represented by any one of the following general formulas (A31) to (A37).

[0429] [ka]

[0430] [ka]

[0431] (In the general formulae (A31) to (A37), Multiple R 300 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 300 , and R 333 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 31 ~R 38 is synonymous with In the general formulae (A31) to (A37), * represents L of the compound represented by the general formula (3). 3 The bond position is shown.)

[0432] In the compound represented by the general formula (3), A 3is also preferably a group represented by the above general formula (A34), (A35) or (A37).

[0433] In the compound represented by the general formula (3), A 3 is preferably a group represented by any of the following general formulas (A371) to (A376).

[0434] [ka]

[0435] [ka]

[0436] [ka]

[0437] (In the general formulae (A371) to (A376), Y 3 is a sulfur atom, an oxygen atom, and N(R 381 ) or C(R 382 )(R 383 ) and R 382 and R 383 A set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 371 ~R 380 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 381 R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring.371 ~R 380 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 382 and R 383 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 31 ~R 38 is synonymous with In the general formulae (A371) to (A376), * represents L of the compound represented by the general formula (3). 3 The bond position is shown.)

[0438] In the general formulae (A371) to (A376), R 381 teeth, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0439] In the general formulae (A371) to (A376), R 382 and R 383 A set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring. 382 and R 383 are 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 It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0440] In the general formulae (A371) to (A376), Y 3is preferably a sulfur atom or an oxygen atom.

[0441] 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).

[0442] [ka]

[0443] [ka]

[0444] [ka]

[0445] [ka]

[0446] [ka]

[0447] [ka]

[0448] (In the general formulae (311) to (316), L 3 is L in the general formula (3). 3 is synonymous with Multiple R 300 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 341 ~R350 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 300 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 341 ~R 350 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 31 ~R 38 is equivalent to

[0449] The compound represented by the general formula (3) is also preferably a compound represented by the following general formula (321).

[0450] [ka]

[0451] (In the general formula (321), L 3 is L in the general formula (3). 3 is synonymous with R 31 ~R 38 , and R 301 ~R 308 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 31 ~R 38 is equivalent to

[0452] 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.

[0453] In the compound represented by the general formula (3), L 3 teeth, Single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or A substituted or unsubstituted terphenylene group is preferred.

[0454] In the compound represented by the general formula (3), L 3 is preferably a group represented by the following general formula (317).

[0455] [ka]

[0456] (In the general formula (317), R 310 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 31 ~R 38 and each * independently indicates a bonding position.)

[0457] In the compound represented by the general formula (3), L 3 It is also preferable that the compound contains a divalent group represented by the following general formula (318) or (319). In the compound represented by the general formula (3), L 3 is also preferably a divalent group represented by the following general formula (318) or general formula (319).

[0458] The compound represented by the general formula (3) is also preferably a compound represented by the following general formula (322) or (323).

[0459] [ka]

[0460] [ka]

[0461] (In the general formula (322) and the general formula (323), L 31 teeth, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms; a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, or a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, However, L 31 includes a divalent group represented by the following general formula (318) or general formula (319), R 31 ~R 38 , R 300 , and R 321 ~R 328 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 31 ~R 38 is equivalent to

[0462] [ka]

[0463] (In the general formula (319), Multiple R 304 adjacent pairs of these are bonded to each other to form a ring represented by the general formula (320), In the general formula (320), 1* and 2* each independently represent R 304 indicates the position of attachment to the ring to which it is attached, R in the general formula (318) 302 R in the general formula (319) 303 R which does not form a ring represented by the general formula (320) 304 and R in the general formula (320)305 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 31 ~R 38 is synonymous with In the general formulae (318) to (320), * indicates a bonding position.

[0464] 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).

[0465] [ka]

[0466] (In the general formula (319A), R 303 , R 304 and R 305 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 31 ~R 38 and * in the general formula (319A) indicates a bonding position.)

[0467] The compound represented by the general formula (3) is a compound represented by the general formula (322), 31 is also preferably a group represented by the above general formula (318).

[0468] The compound represented by the general formula (3) is also preferably a compound represented by the following general formula (324).

[0469] [ka]

[0470] (In the general formula (324), R 31 ~R 38 , R300 , and R 302 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 31 ~R 38 is equivalent to

[0471] 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 each independently represents 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.

[0472] 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.

[0473] 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.

[0474] It is also preferable that the compound represented by the general formula (3) is a compound having no pyridine ring, no pyrimidine ring, and no triazine ring.

[0475] (Compound represented by general formula (3B)) In the light-emitting layer of the organic EL device of the first embodiment, the third compound is also preferably a compound represented by the following general formula (3B).

[0476] [ka]

[0477] In the general formula (3B), X B is an oxygen atom or a sulfur atom, C 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; If m is 2 or more, multiple R L are the same or different, R B1 ~R B8 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, When at least one of n and k is 2 or more, a plurality of R B1 are the same or different, and multiple R B2 are the same or different, and multiple R B3 are the same or different, and multiple R B4 are the same or different, and multiple R B5 are the same or different, and multiple R B6 are the same or different, and multiple R B7are the same or different, and multiple R B8 are the same or different, L B1 is a single bond or a linking group, with the proviso that L B1 is a single bond, n is 1; If k is 2 or more, multiple L B1 are the same or different, L as a linking group B1 teeth, a group derived from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a group derived from a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a group formed by bonding two groups selected from the group consisting of a group derived from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a group derived from a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, When k is 1 and m is 4, four R L Each of them is bonded to any of the carbon atoms at the positions a, b, c, d, and e shown in the general formula (3B), and one L B1 R L is bonded to a carbon atom at position a, b, c, d, or e that is not bonded to When k is 2 and m is 3, three R L are bonded to any of the carbon atoms at positions a, b, c, d, and e shown in the general formula (3B), and two L B1 are the above R L and bonded to any of the carbon atoms at positions a, b, c, d, and e that are not bonded to When k is 3 and m is 2, two R L are bonded to any of the carbon atoms at positions a, b, c, d, and e shown in the general formula (3B), and three L B1 are the above R L and bonded to any of the carbon atoms at positions a, b, c, d, and e that are not bonded to R B40 and R B45 ~R B48 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, However, the three R's B40 are the same or different, and the three R B40 are bonded to any of the carbon atoms at positions f, g, h, and i in the general formula (3B), 1 R B40 bonded to any of the carbon atoms at positions f, g, h, and i that are not bonded to R L , R B31 , R B32 , R B34 , R B35 R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. B1 ~R B8 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. B40 and R B45 ~R B48 are each independently 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 A group represented by -COOR 909 A group represented by Halogen atoms, Cyano group, Nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0478] 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 Bind to. In the compound represented by the general formula (3B), L B1 is a single bond, the nitrogen atom N* of the structure in parentheses enclosed with the subscript n is bonded to any of the carbon atoms at 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 parentheses enclosed by the subscript k B1 are bonded to any of the carbon atoms at positions a, b, c, d, and e, respectively.

[0479] 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 When is bonded to the carbon atom at position h, the compound represented by general formula (3B) is represented by the following general formula (31B).

[0480] [ka]

[0481] (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).

[0482] For example, in the compound represented by the general formula (3B), L B1 is a single bond, n is 2, and 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 b, 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).

[0483] [ka]

[0484] (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).

[0485] (Compound represented by general formula (MRX3)) In the light-emitting layer of the organic EL device of the first embodiment, the third compound is also preferably a compound represented by the following general formula (MRX3).

[0486] [ka]

[0487] (In the general formula (MRX3), Y 31 ~Y 36 are each independently 3 or a nitrogen atom, However, Y 31 ~Y 36 Two or more of the groups are nitrogen atoms, R 3 If there are multiple R 3 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 3 are each independently 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R908 A group represented by -COOR 909 A group represented by Halogen atoms, Cyano group, Nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or It is a group represented by the following general formula (MRX3A).

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[0489] (In the general formula (MRX3A), R B is R in the general formula (3). B is synonymous with R B When there are multiple R B are the same or different from each other, L 31 and L 32 respectively represent L in the general formula (3). 31 and L 32 is synonymous with n 3 is 1, 2, 3, 4 or 5, L 31 If is a single bond, n 3 is 1, and L 32 is bonded to a carbon atom of a six-membered ring in general formula (MRX3), L 32 When there are multiple L 32are the same or different from each other, * represents the bonding site to the carbon atom of the six-membered ring in general formula (MRX3).

[0490] The compound represented by the general formula (MRX3) preferably does not contain a pyridine ring in the molecule.

[0491] The compound represented by the general formula (MRX3) is also preferably a compound represented by the following general formula (MRX31) or (MRX32).

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[0493] (In the general formula (MRX32), R 35 ~R 37 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R in the general formula (MRX31) 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 condensed ring. 35 ~R 37 each independently represents R in the general formula (MRX3). 3 is equivalent to

[0494] The compound represented by the general formula (MRX3) is also preferably a compound represented by the general formula (MRX31).

[0495] R in the general formula (MRX3) 3are 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, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by general formula (MRX3A) above.

[0496] 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.

[0497] 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 formulas (MRXA31) to (MRXA44).

[0498] [ka]

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[0500] (In the above general formulae (MRXA31) to (MRXA38), Multiple R 300 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 331 and R 332 A set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 300 , R 331 and R 332 , and R 333 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 A group represented by -COOR 909 A group represented by Halogen atoms, Cyano group, Nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the general formulae (MRXA31) to (MRXA38), * indicates the bonding position to other atoms in the molecule of the compound represented by the general formula (MRX3).

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[0504] (In the above general formulae (MRXA39) to (MRXA44), R 341 ~R 350 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, However, R 341 ~R 351 at least one of the following represents a bonding position to another atom in the molecule of the compound represented by general formula (MRX3): X 31 is a sulfur atom, an oxygen atom, and NR 352 or CR 353 R 354 and R 353 and R 354 A set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R which is not a bonding position with other atoms in the molecule of the compound represented by the general formula (MRX3), does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring 341 ~R 351 And, R 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, independently, 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 A group represented by -COOR 909 A group represented by Halogen atoms, Cyano group, Nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0505] The compound represented by the general formula (MRX3) preferably has, in the molecule, at least one group selected from the group consisting of the groups represented by the general formulae (MRXA38) to (MRXA44).

[0506] 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 of the groups represented by general formulae (MRXA31) to (MRXA44).

[0507] 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 of the groups represented by general formulae (MRXA38) to (MRXA44).

[0508] 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.

[0509] In the compound represented by the general formula (MRX3), R 353 and R 354 A set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed 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.

[0510] In the compound represented by the general formula (3) and the compound represented by the general formula (MRX3), L 31 teeth, Single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a trivalent group, a tetravalent group, a pentavalent group, or a hexavalent group derived from the arylene group, 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, tetravalent group, pentavalent group, or hexavalent group derived from the divalent group, L 32 is preferably a single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0511] In the compound represented by the general formula (3) 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, 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.

[0512] In the compound represented by the general formula (3) and the compound represented by the general formula (MRX3), L 31 teeth, Single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or 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, n 3 is 1, L 32 is preferably a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0513] In the compound represented by the general formula (3) 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 ) a group represented by an unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 A group represented by -COOR 909 A group represented by -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by -S(=O) 2 R 938 A group represented by Halogen atoms, Cyano group, Nitro group, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms, R 901 ~R 909 , and R 931 ~R 938 are each independently Hydrogen 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 is preferred.

[0514] In the compound represented by the general formula (3) and the compound 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.

[0515] In the compound represented by the general formula (3) and the compound 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.

[0516] In the compound represented by the general formula (3) and the compound represented by the general formula (MRX3), it is also preferable that all of the groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0517] (Production method of the third compound) The third compound according to the first embodiment can be produced by a known method.

[0518] (Specific Example of the Third Compound) Specific examples of the third compound of the first embodiment include the following compounds. However, the present invention is not limited to these specific examples of compounds.

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[0535] (Relationship between the first compound, the second compound and the third compound in the light-emitting layer) In the organic EL device according to the first embodiment, the first compound and the second compound preferably satisfy the following mathematical formula (Mathematical Formula 2). (Number 2):S 1 (M2)>S 1 (M1) (S 1 (M1) is the lowest excited singlet energy of the first compound, S 1 (M2) is the lowest excited singlet energy of the second compound.

[0536] In the organic EL device according to the first embodiment, the second compound and the third compound preferably satisfy the following mathematical formula (Mathematical Formula 3). (Number 3):S 1 (M3)>S 1 (M2) (S 1 (M2) is the lowest excited singlet energy of the second compound; S 1 (M3) is the lowest excited singlet energy of the third compound.

[0537] 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 It is preferable that (M3) satisfies the relationship of the following mathematical formula (Mathematical formula 3A). S 1(M3)>S 1 (M2)>S 1 (M1) …(Number 3A)

[0538] Energy gap T at 77[K] for 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). Energy gap T at 77[K] for the third compound 77K (M3) is the energy gap T of the first compound at 77[K] 77K It is preferable that it is larger than (M1).

[0539] 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). T 77K (M3)>T 77K (M2)>T 77K (M1) …(Number 3B)

[0540] In one aspect of the organic EL element of the first embodiment, the second compound satisfies the following formula (Formula 44) or formula (44A). When the second compound satisfies the following formula (Formula 44), the luminous efficiency is easily improved. (Equation 44): |HOMO(M2)| ≧ 6.0 eV (Number 44A):|HOMO(M2)|≧6.1eV (HOMO(M2) is the energy level of the highest occupied molecular orbital of the second compound.)

[0541] In one aspect of the organic EL element of the first embodiment, the third compound satisfies the following formula (Formula 45) or formula (45A). When the third compound satisfies the following formula (Formula 45), the luminous efficiency is easily improved. (Equation 45): |HOMO(M3)| ≧ 5.8 eV (Number 45A):|HOMO(M3)|≧5.9eV (HOMO(M3) is the energy level of the highest occupied molecular orbital of the third compound.) The upper limit of the |HOMO(M3)| value of the third compound is preferably 6.2 eV or less.

[0542] When the organic EL device of the first embodiment is caused to emit light, it is preferable that the fluorescent compound mainly emits light in the light-emitting layer.

[0543] 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.

[0544] The maximum peak wavelength of the light emitted from the organic EL element is measured as follows. Current density is 10mA / cm 2 A voltage is applied to the organic EL element so that the spectral radiance spectrum is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta). In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum where the emission intensity is maximum is measured, and this is defined as the maximum peak wavelength (unit: nm).

[0545] (Compound content in light-emitting layer) The contents of the first compound, the second compound, and the third compound 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 preferably 0.3 mass% or more and 4.0 mass% or less, more preferably 0.3 mass% or more and 3.0 mass% or less, and even more preferably 0.3 mass% or more and 2.0 mass% or less. 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 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 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 the first compound or may contain two or more types. The light-emitting layer may contain only one type of the second compound or may contain two or more types. The light-emitting layer may contain only one type of the third compound or may contain two or more types.

[0546] (TADF mechanism) FIG. 4 is a diagram showing an example of the relationship between the energy levels of the first compound, the second compound, and the third compound in the light-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 the Förster type 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) by 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.

[0547] (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. When the thickness is 5 nm or more, the formation of the light-emitting layer and the adjustment of the chromaticity tend to be easy, and when the thickness is 50 nm or less, an increase in the driving voltage is easily suppressed.

[0548] <Structure of organic EL element> The structure of the organic EL element will be further described.

[0549] (substrate) The substrate is used as a support for the organic EL element. For example, glass, quartz, plastic, etc. can be used as the substrate. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate. Examples of materials for forming the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. An inorganic deposition film can also be used.

[0550] (anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or a 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. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), Examples of the metal include chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), and nitrides of metal materials (for example, titanium nitride).

[0551] These materials are usually formed into a film by a sputtering method. For example, indium oxide-zinc oxide can be formed by a sputtering method by using a target in which zinc oxide is added to indium oxide at 1 mass % or more and 10 mass % or less. In addition, indium oxide containing tungsten oxide and zinc oxide can be formed by a sputtering method by using a target in which tungsten oxide is added to indium oxide at 0.5 mass % or more and 5 mass % or less and zinc oxide is added to indium oxide at 0.1 mass % or more and 1 mass % or less. In addition, it may be formed by a vacuum deposition method, a coating method, an inkjet method, a spin coating method, or the like.

[0552] Of the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that easily injects holes regardless of the work function of the anode, so that materials that can be used as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures of these, as well as other elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0553] Materials with small work functions, such as elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these, can also be used. When alkali metals, alkaline earth metals, and alloys containing these are used to form the anode, vacuum deposition and sputtering methods can be used. Furthermore, when silver paste or the like is used, coating and inkjet methods can be used.

[0554] 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 optical transparency or semi-transparency metal material can be appropriately selected from the materials listed in the above section on the anode.

[0555] When the organic EL element is a top emission type, the anode is a reflective electrode having a reflective layer. The reflective layer is preferably formed of a metal material having light reflectivity. In this specification, light reflectivity means a property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light emitting layer. The metal material having light reflectivity can be appropriately selected from the materials listed in the above section on the anode. The anode may be composed of only a reflective layer, but may also have a multi-layer 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 is disposed between the reflective layer and the hole transport zone. The conductive layer can be appropriately selected from the materials listed in the above section on the anode.

[0556] (cathode) For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof, each having a small work function (specifically, 3.8 eV or less). Specific examples of such a cathode material include elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.

[0557] 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.

[0558] By providing an electron injection layer, the cathode can be formed using various conductive materials, such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the magnitude of the work function. These conductive materials can be formed into films by a sputtering method, an inkjet method, a spin coating method, or the like.

[0559] When the organic EL element is a bottom emission type, the cathode is a reflective electrode. The reflective electrode is preferably made of a metal material having light reflectivity. The metal material having light reflectivity can be appropriately selected from the materials listed in the cathode section.

[0560] When the organic EL element is a top-emission type, the cathode is preferably formed of a metal material having optical transparency or semi-transparency that transmits light from the light-emitting layer. The optical transparency or semi-transparency metal material can be appropriately selected from the materials listed in the cathode section.

[0561] The organic EL element according to the first embodiment may be a bottom-emission type organic EL element. Also, the organic EL element according to the first embodiment may be a top-emission type organic EL element. When the organic EL element is of a bottom emission type, it is preferable that the anode is a light-transmitting electrode having light transparency, and the cathode is a light-reflective electrode having light reflection. When the organic EL element is of a top emission type, it is preferable that the anode is a light reflective electrode having light reflectivity, and the cathode is a light transmissive electrode having light transmittance.

[0562] (capping layer) When the organic EL device is of a top-emitting type, the organic EL device usually includes a capping layer on top of the cathode. The capping layer may contain, for example, at least one compound selected from the group consisting of polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitride, and silicon compounds (such as silicon oxide). The capping layer may contain at least one compound selected from the group consisting of aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, and dibenzofuran derivatives. Furthermore, a laminate in which layers containing these substances are laminated can also be used as the capping layer.

[0563] (Hole injection layer) The hole injection layer is a layer containing a substance with high hole injection properties, such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. In addition, examples of materials with high hole injection properties include low-molecular-weight organic compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), and 1, Other examples of aromatic amine compounds 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). In addition, as a substance with high hole injection properties, a polymer compound (oligomer, dendrimer, polymer, etc.) can be used. For example, polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD) can be used. In addition, a polymer compound to which an acid is added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) or polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can be used.

[0564] (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 A material having a hole mobility of 0.1 V or more. The hole transport layer may be made of carbazole derivatives such as CBP, CzPA, and PCzPA, or anthracene derivatives such as t-BuDNA, DNA, and DPAnth. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) may also be used. However, other substances may be used as long as they have a higher hole transporting property than an electron transporting property. Note that the layer containing the substance having a high hole transporting property may be a single layer or a layer in which two or more layers made of the above-mentioned substances are stacked.

[0565] (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 include Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq), 3 ), Bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq 2 Metal complexes such as BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(pt-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), bathophenanthroline (abbreviated as BPhen), bathocuproine (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs) can also be used. The substances mentioned here are mainly 10 -6 cm 2 The electron transport layer is a material having an electron mobility of 1 / Vs or more. Note that, as long as the material has a higher electron transporting property than a hole transporting property, any material other than the above may be used as the electron transport layer. The electron transport layer may be a single layer or a layer in which two or more layers made of the above materials are stacked. The electron transport layer can also be made of a polymer compound, such as poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) or poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).

[0566] (electron injection layer) The electron injection layer is a layer containing a substance with high electron injection properties. Examples of the electron injection layer include lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), and calcium fluoride (CaF 2 Alkaline metals, alkaline earth metals, such as lithium oxide (LiOx), or compounds thereof can be used. In addition, a substance having electron transport properties containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a substance containing magnesium (Mg) in Alq, etc. can be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such a composite material has excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material that is excellent in transporting the generated electrons, and specifically, for example, the above-mentioned substances constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor may be any substance that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples thereof include lithium, cesium, magnesium, calcium, erbium, and ytterbium. Furthermore, alkali metal oxides and alkaline earth metal oxides are preferred, and examples thereof include lithium oxide, calcium oxide, and barium oxide. Furthermore, a Lewis base such as magnesium oxide can also be used. Furthermore, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.

[0567] (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, e.g., a vacuum deposition method, a sputtering method, a plasma method, or an ion plating method, or a wet film formation method, e.g., a spin coating method, a dipping method, a flow coating method, or an inkjet method.

[0568] (Film thickness) The thickness of each organic layer of the organic EL element according to the first embodiment is not limited unless otherwise specified above. In general, if the thickness is too thin, defects such as pinholes are likely to occur, and if the thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the thickness of each organic layer of the organic EL element is usually preferably in the range of several nm to 1 μm.

[0569] The organic EL element according to the first embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0570] Second Embodiment The configuration of the organic EL element according to the second embodiment will be described. In the description of the second embodiment, the same components as those in the first embodiment will be omitted or simplified by using the same reference numerals or names. In the second embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the first embodiment can be used.

[0571] 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 a phosphorescent metal complex.

[0572] (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.

[0573] (Third Compound) As the third compound, the third compound described in the first embodiment can be used.

[0574] (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 singlet energy S 1 (M2) and the singlet energy S of the third compound 1 It is preferable that (M3) satisfies the relationship of the following mathematical formula (Mathematical Formula 3). S 1 (M3)>S 1 (M2) …(Math 3)

[0575] Energy gap T at 77[K] for 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).

[0576] FIG. 5 is a diagram for explaining the principle of light emission according to the second embodiment. In Figure 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) by thermal energy. By utilizing the reverse intersystem crossing that occurs in this second compound, for example, luminescence as shown in the following (i-1) or (ii-1) can be observed. (i-1) When the light-emitting layer does not contain a fluorescent dopant having a lowest excited singlet state S1 smaller than the lowest excited singlet state S1(M2) of the second compound, light emission from the lowest excited singlet state S1(M2) of the second compound can be observed. (ii-1) When the light-emitting layer contains a fluorescent dopant (the first compound in the first embodiment) having a lowest excited singlet state S1 smaller than the lowest excited singlet state S1 (M2) of the second compound, light emission from the fluorescent dopant can be observed. In the organic EL element of the second embodiment, the light emission shown in the above (i-1) can be observed. In the organic EL element of the first embodiment, the light emission shown in the above (ii-1) can be observed.

[0577] (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 mass %. In the organic EL device according to the second embodiment, the light-emitting layer may contain only one type of the second compound or two or more types thereof. The light-emitting layer may contain only one type of the third compound or two or more types thereof. According to the second embodiment, it is possible to realize an organic EL element that allows a reduction in the driving voltage and an improvement in the luminous efficiency. The organic EL element according to the second embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0578] Third Embodiment (electronic equipment) The electronic device according to the third embodiment is equipped with the organic EL element according to any one of the above-mentioned embodiments. Examples of the electronic device include display devices and light-emitting devices. Examples of the display devices include display components (e.g., organic EL panel modules), televisions, mobile phones, tablets, and personal computers. Examples of the light-emitting devices include lighting and vehicle lamps.

[0579] The display device as the electronic device according to the third embodiment is preferably an organic EL display device equipped with organic EL elements as red, green and blue pixels. In the organic EL display device, the red or green pixel is preferably the organic EL element according to any of the above-mentioned embodiments. In one aspect of the organic EL display device, the blue pixel may be the organic EL element according to any of the above-mentioned embodiments.

[0580] [Modification 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.

[0581] For example, the light-emitting layer is not limited to one layer, and multiple light-emitting layers may be laminated. When the organic EL element has multiple light-emitting layers, at least one of the light-emitting layers may satisfy 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 a ground state. Furthermore, when the organic EL element has a plurality of light-emitting layers, these light-emitting layers may be provided adjacent to each other, or the organic EL element may be a so-called tandem type organic EL element in which a plurality of light-emitting units are stacked via an intermediate layer.

[0582] In addition, for example, a blocking layer may be provided adjacent to at least one of the anode side and the cathode side of the light-emitting layer. The blocking layer is preferably disposed in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons. For example, when a blocking layer is disposed in contact with the light-emitting layer on the cathode side, the blocking layer transports electrons and prevents holes from reaching a layer (e.g., an electron transport layer) on the cathode side of the blocking layer. When the organic EL device includes an electron transport layer, it is preferable to include the blocking layer between the light-emitting layer and the electron transport layer. In addition, when a blocking layer is disposed in contact with the light-emitting layer on the anode side, the blocking layer transports holes and prevents electrons from reaching a layer (e.g., a hole transport layer) on the anode side of the blocking layer. When the organic EL device includes a hole transport layer, it is preferable to include the blocking layer between the light-emitting layer and the hole transport layer. A barrier layer may be provided adjacent to the light-emitting layer to prevent the excitation energy from leaking from the light-emitting layer to the surrounding layers, and prevents excitons generated in the light-emitting layer from migrating to layers on the electrode side of the barrier layer (e.g., the electron transport layer and the hole transport layer, etc.). The light emitting layer and the barrier layer are preferably in contact with each other.

[0583] In addition, the specific structure and shape in carrying out the present invention may be other structures and shapes within the scope of the invention in which the object of the present invention can be achieved. EXAMPLES

[0584] 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.

[0585] <Compound> The structure of the fourth compound used in the production of the organic EL devices according to Examples 1-1 to 1-5 and Examples 2-1 to 2-5 is shown below.

[0586] [ka]

[0587] The structures of the comparative compounds used in the production of the organic EL devices according to Comparative Examples 1-1 to 1-2 and 2-1 to 2-2 are shown below.

[0588] [ka]

[0589] The structures of other compounds used in the production of the organic EL devices according to Examples 1-1 to 1-5, Examples 2-1 to 2-5, Comparative Examples 1-1 to 1-2, and Comparative Examples 2-1 to 2-2 are shown below.

[0590] [ka]

[0591] [ka]

[0592] [ka]

[0593] <Fabrication of organic EL elements> An organic EL device was prepared as follows and evaluated.

[0594] (Example 1-1) A 25mm x 75mm x 1.1mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 1 minute. The ITO film thickness was 130nm. The glass substrate having the transparent electrode lines after cleaning is mounted on a substrate holder of a vacuum deposition apparatus; First, the compound HT-1 and the compound HA were co-deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, to form a hole injection layer having a thickness of 10 nm. The proportion of the compound HT-1 in the hole injection layer was 97% by mass, and the proportion of the compound HA was 3% by mass. Next, the compound HT-1 as a sixth compound was deposited on the hole injection layer to form a hole transport layer having a thickness of 90 nm. Next, on the hole transporting layer, a compound EBL-1a as a fourth compound was evaporated to form a first layer (also referred to as a first electron blocking layer) having a thickness of 25 nm. Next, compound EBL-2 as a fifth compound was evaporated on the first layer to form a second layer (also referred to as a second electron blocking layer) having a thickness of 5 nm. Next, on the second layer, the compound Matrix-1 as a host material (third compound), the compound TADF-1 as a delayed fluorescent compound (second compound), and the compound GD-1 as a fluorescent compound (first compound) were co-deposited to form an emission layer having a thickness of 40 nm. The ratio of the compound Matrix-1 in the emission layer was 64.4 mass%, the ratio of the compound TADF-1 was 35 mass%, and the ratio of the compound GD-1 was 0.6 mass%. Next, compound ET-1 was deposited on the light-emitting layer to form a hole blocking layer having a thickness of 5 nm. Next, the compound ET-2 and the compound Liq were co-deposited on the hole blocking layer to form an electron transport layer having a thickness of 35 nm. The concentration of the compound ET-2 in the electron transport layer was set to 50 mass %, and the concentration of the compound Liq was set to 50 mass %. Liq is an abbreviation for (8-quinolinolato)lithium. Next, ytterbium (Yb) was evaporated onto this electron transport layer to form an electron injection layer with a thickness of 1 nm. Then, metallic aluminum (Al) was vapor-deposited on the electron injection layer to form a metallic Al cathode with a thickness of 50 nm. In the manner described above, an organic EL element according to Example 1-1 was produced. The device configuration of the organic EL element according to Example 1-1 is roughly shown as follows. ITO(130) / HT-1:HA(10,97%:3%) / HT-1(90) / EBL-1a(25) / EBL-2(5) / Matrix-1:TAD F-1:GD-1(40,64.4%:35%:0.6%) / ET-1(5) / ET-2:Liq(35,50%:50%) / Yb(1) / Al(50) In the above device configuration, the numbers in parentheses indicate the film thickness (unit: nm). Similarly, in the above device configuration, the numbers in parentheses indicated as percentages (97%:3%) indicate the ratios (mass%) of the compounds HT-1 and HA in the hole injection layer, the numbers in percentages (64.4%:35%:0.6%) indicate the ratios (mass%) of the compounds Matrix-1, TADF-1, and GD-1 in the light-emitting layer, and the numbers in percentages (50%:50%) indicate the ratios (mass%) of the compounds ET-2 and Liq in the electron transport layer. The same notations are used below.

[0595] (Examples 1-2 to 1-5) The organic EL devices of Examples 1-2 to 1-5 were prepared in the same manner as in Example 1-1, except that the fourth compound used in the first layer of Example 1-1 was changed to the fourth compound shown in Table 1.

[0596] (Comparative Examples 1-1 to 1-2) The organic EL devices of Comparative Examples 1-1 and 1-2 were prepared in the same manner as in Example 1-1, except that the fourth compound used in the first layer of Example 1-1 was changed to the fourth compound shown in Table 2.

[0597] (Example 2-1) The organic EL device of Example 2-1 was prepared in the same manner as in Example 1-1, except that the contents of the third compound and the second compound contained in the emitting layer of Example 1-1 were changed to the contents of the third compound and the second compound shown in Table 2.

[0598] (Examples 2-2 to 2-5) The organic EL devices of Examples 2-2 to 2-5 were prepared in the same manner as in Example 2-1, except that the fourth compound used in the first layer of Example 2-1 was changed to the fourth compound shown in Table 2.

[0599] (Comparative Examples 2-1 to 2-2) The organic EL devices of Comparative Examples 2-1 and 2-2 were prepared in the same manner as in Example 2-1, except that the fourth compound used in the first layer of Example 2-1 was changed to the fourth compound shown in Table 2.

[0600] <Evaluation of organic EL elements> The organic EL devices thus fabricated were evaluated as follows. The evaluation results are shown in Tables 1 and 2.

[0601] (CIE1931 chromaticity) The current density of the organic EL element is 10mA / cm 2 The spectral radiance spectrum when a voltage was applied to the element so as to satisfy the following formula was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) CIEx and CIEy were calculated from the obtained spectral radiance spectrum.

[0602] (External quantum efficiency EQE) The current density of the organic EL device was 10.00mA / 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 "EQE (relative value)" (unit: %) was calculated. Tables 1 and 2 show the "EQE (relative value)" (unit: %). The "EQE (relative value)" of Examples 1-1 to 1-5 and Comparative Examples 1-1 to 1-2 was calculated based on the EQE of each example and the following formula (Math 1X). EQE (relative value) = (EQE of each example / EQE of Comparative Example 1-1) x 100... (Number 1X) The "EQE (relative value)" of Examples 2-1 to 2-5 and Comparative Examples 2-1 to 2-2 was calculated based on the EQE of each example and the following formula (Math 2X). EQE (relative value) = (EQE of each example / EQE of Comparative Example 2-1) x 100 ... (number 2X)

[0603] [Table 1]

[0604] [Table 2]

[0605] Examples 1-1 to 1-5 in which the TADF material is highly concentrated are compared with Comparative Examples 1-1 to 1-2. As shown in Table 1, Examples 1-1 to 1-5 in which the sixth compound, the fourth compound, and the fifth compound contained in the third layer (thick HT layer), the first layer (first electron blocking layer), and the second layer (second electron blocking layer) respectively satisfy the formula (Formula 41) and the formula (Formula 42) have improved luminous efficiency compared to Comparative Examples 1-1 and 1-2 in which the formula (Formula 42) is not satisfied. As shown in Table 2, the results were similar when comparing Examples 2-1 to 2-5, in which the TADF material was highly concentrated, with Comparative Examples 2-1 to 2-2.

[0606] <Compound evaluation> The above-mentioned compounds were evaluated as follows. The evaluation results are shown in Tables 1 and 2.

[0607] (Ionization potential Ip and energy level of the highest occupied molecular orbital HOMO) The ionization potential and the energy level of the highest occupied molecular orbital (HOMO) of the compound were measured under atmospheric conditions using a photoelectron spectrometer (manufactured by Riken Keiki Co., Ltd., "AC-3"). Specifically, the ionization potential and the energy level of the highest occupied molecular orbital (HOMO) of the compound were measured by irradiating the material with light and measuring the amount of electrons generated by charge separation. The ionization potential may be written as Ip. The value of the energy level of the highest occupied molecular orbital (HOMO) corresponds to the value of the ionization potential with a negative sign.

[0608] (The lowest excited singlet energy S 1 ) The lowest excited singlet energy S of the compound to be measured 1 was measured by the above-mentioned solution method.

[0609] (Maximum peak wavelength λ of compound) The maximum peak wavelength λ of the compound was measured by the following method. A 5 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample was measured at room temperature (300K). In this example, the emission spectrum was measured using a spectrofluorophotometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. The emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum was defined as the maximum peak wavelength λ.

[0610] (Delayed fluorescence of compounds) The delayed fluorescence was confirmed by measuring the 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 in order to eliminate the contribution of self-absorption. In order to prevent quenching by oxygen, the sample solution was frozen and degassed, and then sealed in a cell with a lid under an argon atmosphere to prepare an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the above sample solution was measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. The total fluorescence quantum yield was calculated using the fluorescence area intensity of both spectra according to formula (1) in Morris et al. J. Phys. Chem. 80 (1976) 969. After being excited by pulsed light (light irradiated from a pulsed laser) of a wavelength absorbed by the compound TADF-1, there are prompt luminescence (instantaneous luminescence) that is observed immediately from the excited state, and delayed luminescence (delayed luminescence) that is not observed immediately after the excitation and is observed later. In this embodiment, delayed fluorescent luminescence means that the amount of delayed luminescence (delayed luminescence) is 5% or more of the amount of prompt luminescence (instantaneous luminescence). Specifically, when the amount of prompt luminescence (instantaneous luminescence) is X P and the amount of delay light emission is X D When X D / X P This means that the value is 0.05 or more. The amount and ratio of prompt luminescence and delayed luminescence 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 amount of prompt luminescence and delayed luminescence is not limited to the device described in Reference 1 or the device shown in FIG. 2. It was confirmed that the amount of Delay luminescence (delayed luminescence) of the compound TADF-1 was 5% or more of the amount of Prompt luminescence (immediate luminescence). Specifically, for the compound TADF-1, X D / X P The value was 0.05 or higher.

[0611] (Energy gap T 77K and ΔST) Energy gap T of the target compound 77K is the energy gap T 77K The measurement was performed according to the method described above. For the compound TADF-1, the energy gap T 77K The value of the lowest excited singlet energy S 1 The value of "<0.01" in the table indicates that ΔST is less than 0.01 eV.

[0612] (Refractive Index) The refractive index of the fourth compound contained in the first layer and the refractive index of the sixth compound contained in the third layer were measured as follows. The material to be measured was vacuum-deposited on a glass substrate to a thickness of about 50 nm, and incident light (ultraviolet, visible, and near-infrared) was irradiated at 5° intervals in the measurement angle range of 45° to 75° using a spectroscopic ellipsometry device (JA Woollam, USA, M-2000UI) to measure the change in the polarization state of the light reflected from the sample surface. In order to improve the measurement accuracy of the extinction coefficient, the transmission spectrum in the normal direction of the substrate (perpendicular to the surface of the organic EL element substrate) was also measured using the same device. Similarly, the same measurement was performed on only the glass substrate on which the material to be measured was not deposited. The obtained measurement information was fitted using JA Woollam's analysis software (Complete EASE). The fitting conditions used were an anisotropic model with uniaxial rotational symmetry, and the parameter MSE, which indicates the root mean square error, was set to 3.0 or less in the software to calculate the in-plane and normal direction refractive index, in-plane and normal direction extinction coefficient, and order parameter of the organic film formed on the substrate. The order parameter was calculated by the peak wavelength of S1, with the peak of the extinction coefficient (in-plane direction) on the long wavelength side being taken as S1. The fitting conditions for the glass substrate were an isotropic model. A film of a low molecular weight material vacuum-deposited on a substrate usually has uniaxial rotational symmetry with the normal direction of the substrate as the axis of rotation. If the angle between the molecular axis in the thin film formed on the substrate and the normal direction of the substrate is θ, and the extinction coefficients in the direction parallel to the substrate (ordinary direction) and perpendicular to the substrate (extra-ordinary direction) obtained by multi-angle spectroscopic ellipsometry measurement of the thin film are ko and ke, respectively, then S' expressed by the following formula is the order parameter. S'=1-<cos2θ> =2ko / (ke+2ko)=2 / 3(1-S) S=(1 / 2)<3cos2θ-1>=(ke-ko) / (ke+2ko) The method for evaluating the molecular orientation is a known method, and the details are described in Organic Electronics, 2009, Vol. 10, page 127. The method for forming the thin film is a vacuum deposition method. The order parameter S' obtained from multi-angle spectroscopic ellipsometry is 1.0 when all molecules are aligned parallel to the substrate, and 0.66 when the molecules are not aligned randomly. In this specification, the refractive index value at 2.25 eV in the substrate parallel direction (ordinary direction) measured above is taken as the refractive index of the material to be measured. The refractive index at 2.25 eV corresponds to the refractive index at 550 nm. In this specification, the refractive index at 2.25 eV (550 nm) in the substrate parallel direction (ordinary direction) is taken as n ORD and the refractive index at 2.25 eV (550 nm) in the direction perpendicular to the substrate (extra-ordinary direction) is n EXT It may be written as:

[0613] When a layer contains multiple compounds, the refractive index of the layer can be measured using a spectroscopic ellipsometry device in the same manner as described above for a film obtained by co-evaporating multiple compounds as the material to be measured onto a glass substrate, or for a film obtained by vapor-depositing a mixture containing multiple compounds as the material to be measured.

[0614] [Table 3] [Explanation of symbols]

[0615] Reference Signs List 1... organic electroluminescence element, 2... substrate, 3... anode, 4... cathode, 5... light-emitting layer, 7... hole transporting region, 8... electron transporting region, 10... organic layer, 71... first layer, 72... second layer, 73... third layer, 74... hole injection layer, 81... electron transporting layer, 82... electron injection layer.

Claims

1. An anode, a cathode, a light-emitting layer included between the anode and the cathode; a first layer included between the anode and the light-emitting layer; a second layer between the first layer and the light-emitting layer; a third layer contained between the anode and the first layer; the light-emitting layer contains a delayed fluorescent compound as a second compound, the content of the second compound in the light-emitting layer is 30% by mass or more and 50% by mass or less, the first layer comprises a fourth compound; the second layer comprises a fifth compound; the third layer comprises a sixth compound; the fourth compound, the fifth compound, and the sixth compound are different from each other; The fourth compound, the fifth compound, and the sixth compound satisfy the following formula (Formula 41) and formula (Formula 42): Organic electroluminescent element. (Equation 41): |HOMO(M5)|≧5.70 eV (Number 42): NM ６ >NM ４ (HOMO(M5) is the energy level of the highest occupied molecular orbital of the fifth compound, and N ４ is the refractive index of the fourth compound, N ６ is the refractive index of the sixth compound.

2. The fourth compound and the fifth compound satisfy the following formula (Formula 43): The organic electroluminescence device according to claim 1 . (Math. 43): 0<|HOMO(M4)-HOMO(M5)|≦0.40eV (HOMO(M4) is the energy level of the highest occupied molecular orbital of the fourth compound, and HOMO(M5) is the energy level of the highest occupied molecular orbital of the fifth compound.)

3. the content of the second compound in the light-emitting layer is 30% by mass or more and 45% by mass or less; The organic electroluminescence device according to claim 1 or 2.

4. the content of the second compound in the light-emitting layer is 30% by mass or more and 40% by mass or less; The organic electroluminescence device according to claim 1 .

5. The second compound satisfies the following formula (Formula 44): The organic electroluminescence device according to claim 1 . (Equation 44): |HOMO(M2)|≧6.0 eV (HOMO(M2) is the energy level of the highest occupied molecular orbital of the second compound.)

6. the light-emitting layer further contains a third compound, the second compound and the third compound are different from each other, The third compound satisfies the following formula (Formula 45): The organic electroluminescence device according to claim 1 . (Equation 45): |HOMO(M3)|≧5.8 eV (HOMO(M3) is the energy level of the highest occupied molecular orbital of the third compound.)

7. The second compound and the third compound satisfy the following formula (Formula 3): The organic electroluminescence device according to claim 6 . (number 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.

8. The fourth compound and the fifth compound satisfy the following formula (Formula 46): The organic electroluminescence device according to claim 1 . (Equation 46): |HOMO(M5)|>|HOMO(M4)| (HOMO(M4) is the energy level of the highest occupied molecular orbital of the fourth compound, and HOMO(M5) is the energy level of the highest occupied molecular orbital of the fifth compound.)

9. The second compound, the fourth compound, and the fifth compound satisfy the following formula (Formula 47): The organic electroluminescence device according to claim 8 . (Equation 47): |HOMO(M2)|>|HOMO(M5)|>|HOMO(M4)| (HOMO(M2) is the energy level of the highest occupied molecular orbital of the second compound, HOMO(M4) is the energy level of the highest occupied molecular orbital of the fourth compound, and HOMO(M5) is the energy level of the highest occupied molecular orbital of the fifth compound).

10. the light-emitting layer further comprises a first compound, the first compound and the second compound are different from each other, The first compound satisfies the following formula (Formula 21): The organic electroluminescence device according to claim 1 . (Equation 21): |HOMO(M1)|≧5.25 eV (HOMO(M1) is the energy level of the highest occupied molecular orbital of the first compound.)

11. The first compound and the second compound satisfy the following formula (Mathematical Formula 2): The organic electroluminescence device according to claim 10. (number 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.

12. The fourth compound and the sixth compound satisfy the following formula (Formula 411): The organic electroluminescence device according to claim 1 . (number 411): NM ６ -NM ４ >0.10 (N.M. ４ is the refractive index of the fourth compound, N ６ is the refractive index of the sixth compound.

13. The fourth compound satisfies the following formula (Formula 412): The organic electroluminescence device according to claim 1 . (number 412): NM ４ ≧1.65 (N.M. ４ is the refractive index of the fourth compound.

14. The sixth compound satisfies the following formula (413): The organic electroluminescence device according to claim 1 . (number 413): NM ６ ≧1.75 (N.M. ６ is the refractive index of the sixth compound.

15. The first layer has a thickness of 35 nm or less. The organic electroluminescence device according to claim 1 .

16. The second layer has a thickness of 10 nm or less. The organic electroluminescence device according to claim 1 .

17. The thickness TL of the first layer １ and the thickness TL of the second layer ２ satisfies the relationship of the following formula (Math A1): The organic electroluminescence device according to claim 1 . (Number A1): TL １ > TL ２ (TL １ is the thickness of the first layer, and TL ２ is the film thickness of the second layer, and the unit of the film thickness is nm.)

18. The film thickness of the first layer and the film thickness of the third layer satisfy the relationship of the following mathematical formula (Math A2): The organic electroluminescence device according to claim 1 . (Number A2): TL ３ > TL １ (TL １ is the thickness of the first layer, and TL ３ is the film thickness of the third layer, and the unit of the film thickness is nm.)

19. The film thickness of the first layer, the film thickness of the second layer, and the film thickness of the third layer satisfy the relationship of the following mathematical formula (Math A3): The organic electroluminescence device according to claim 1 . <h2 style=";text-align:left;direction:ltr">(Other): TL<h2 style=";text-align:left;direction:ltr"> ３ <h2 style=";text-align:left;direction:ltr"> 5>TL<h2 style=";text-align:left;direction:ltr"> １ <h2 style=";text-align:left;direction:ltr"> 5>TL<h2 style=";text-align:left;direction:ltr"> ２ (TL １ is the thickness of the first layer, and TL ２ is the thickness of the second layer, and TL ３ is the film thickness of the third layer, and the unit of the film thickness is nm.)

20. The light-emitting layer and the second layer are in direct contact with each other. The organic electroluminescence device according to claim 1 .

21. The first layer and the second layer are in direct contact with each other. The organic electroluminescence device according to claim 1 .

22. The light-emitting layer does not contain a metal complex. The organic electroluminescence device according to claim 1 .

23. The light-emitting layer does not contain a phosphorescent material. The organic electroluminescence device according to claim 1 .

24. The third layer has a thickness of 30 nm or more. The organic electroluminescence device according to claim 1 .

25. The first layer and the third layer are in direct contact with each other. The organic electroluminescence device according to claim 1 .

26. an electron transport layer between the cathode and the light emitting layer; The organic electroluminescence device according to claim 1 .

27. An electronic device comprising the organic electroluminescence element according to any one of claims 1 to 26.

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