Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device

Abstract

Provided is a compound represented by formula (1). In formula (1), L represents a substituted or unsubstituted arylene group having 6-18 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5-18 ring-forming atoms; one selected from the group consisting of R101, R102, R103, R104, R105, R106, R107, and 108 represents a single bond bonded to *a; one selected from the group consisting of R111, R112, R113, R114, R115, R116, R117, and R118 represents a single bond bonded to *b; and one or more selected from the group consisting of R1 to R5, R101 to R108, R111 to R118, and R121 to R128 represent deuterium atoms.

Description

Compounds, materials for organic electroluminescent elements, organic electroluminescent elements and electronic devices

[0001] The present invention relates to compounds, materials for organic electroluminescent elements, organic electroluminescent elements, and electronic devices.

[0002] When a voltage is applied to an organic electroluminescent 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 EL elements that use light emission from singlet excitons are being applied to full-color displays in mobile phones and televisions, but the internal quantum efficiency of 25% is said to be the limit. Various studies have been conducted on compounds used in organic EL elements to improve their performance (see, for example, Patent Document 1). Examples of organic EL element performance include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime.

[0003] U.S. Patent Application Publication No. 2020 / 0343457

[0004] The object of the present invention is to provide a compound that can improve the lifespan of an organic electroluminescent element, to provide a material for an organic electroluminescent element containing the compound, to provide an organic electroluminescent element containing the compound, and to provide an electronic device equipped with the organic electroluminescent element.

[0005] According to one aspect of the present invention, a compound represented by the following formula (1) is provided.

[0006]

[0007] (In formula (1) above, L is a substituted or unsubstituted arylene group having 6 to 18 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 18 ring-forming atoms, R １ , R２ , R ３ , R ４ and R ５ One or more sets of two or more adjacent ones of, and R １０１ , R １０２ , R １０３ , R １０４ , R １０５ , R １０６ , R １０７ and R １０８ One selected from the group consisting of and R １０１ ~R １０８ One or more sets of two or more adjacent ones of, and R １１１ , R １１２ , R １１３ , R １１４ , R １１５ , R １１６ , R １１７ and R １１８ One selected from the group consisting of and R １１１ ~R １１８ One or more sets of two or more adjacent ones of, and R １２１ , R １２２ , R １２３ , R １２４ , R １２５ , R １２６ , R １２７ and R １２８ One or more sets of two or more adjacent ones of, and R do not form the unsubstituted or substituted monocyclic ring, and do not form the unsubstituted or substituted condensed ring１ ~R ５ , R １０１ ~R １０８ , R １１１ ~R １１８ , and R １２１ ~R １２８ Each of these independently consists of a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 haloalkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group, and -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ A group represented by ) -O-(R ９０４ A group represented by ) -S-(R ９０５ A group represented by ) -N(R ９０６ ) (Caution ９０７ Groups represented by ), substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, -C(=O)R ８０１ The base represented by -COOR ８０２ Groups represented by, halogen atoms, cyano groups, nitro groups, -P(=O)(R ９３１ ) (Caution ９３２ The group represented by ) -Ge(R ９３３ ) (Caution ９３４ ) (Caution ９３５ A group represented by ) -B(R ９３６ ) (Caution ９３７ A base represented by ) -B(OR ９３８ ) ( OR ９３９ The group represented by ) -O-S (=O) ２ (R ９４０ A group represented by ), a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms, provided that R １ ~R ５ , R １０１ ~R １０８ , R １１１ ~R １１８ , and R １２１ ~R １２８One or more selected from the group consisting of are deuterium atoms, and R ９０１ ~R ９０７ 、R ８０１ ~R ８０２ 、and R ９３１ ~R ９４０ is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms, and when there are a plurality of R ９０１ s, the plurality of R ９０１ s are the same as or different from each other, and when there are a plurality of R ９０２ s, the plurality of R ９０２ s are the same as or different from each other, and when there are a plurality of R ９０３ s, the plurality of R ９０３ s are the same as or different from each other, and when there are a plurality of R ９０４ s, the plurality of R ９０４ s are the same as or different from each other, and when there are a plurality of R ９０５ s, the plurality of R ９０５ s are the same as or different from each other, and when there are a plurality of R ９０６ s, the plurality of R ９０６ s are the same as or different from each other, and when there are a plurality of R ９０７ s, the plurality of R ９０７ s are the same as or different from each other, and when there are a plurality of R ８０１ s, the plurality of R ８０１ s are the same as or different from each other, and when there are a plurality of R ８０２ s, the plurality of R ８０２ s are the same as or different from each other, and when there are a plurality of R9] ９３１ s, the plurality of R ９３１ s are the same as or different from each other, and when there are a plurality of R ９３２ s, the plurality of R ９３２ s are the same as or different from each other, and when there are a plurality of R ９３３ s, the plurality of R ９３３ s are the same as or different from each other, and when there are a plurality of R ９３４If multiple R ９３４ They are either identical or different from each other, R ９３５ If multiple R ９３５ They are either identical or different from each other, R ９３６ If multiple R ９３６ They are either identical or different from each other, R ９３７ If multiple R ９３７ They are either identical or different from each other, R ９３８ If multiple R ９３８ They are either identical or different from each other, R ９３９ If multiple R ９３９ They are either identical or different from each other, R ９４０ If multiple R ９４０ (They are either identical or different to each other.)

[0008] According to one aspect of the present invention, a material for an organic electroluminescent device is provided, which contains a compound according to one aspect of the present invention.

[0009] According to one aspect of the present invention, an organic electroluminescent element is provided, having a cathode, an anode, and a light-emitting unit disposed between the cathode and the anode, wherein the light-emitting unit contains a compound according to one aspect of the present invention.

[0010] According to one aspect of the present invention, an electronic device equipped with an organic electroluminescent element according to one aspect of the present invention is provided.

[0011] According to one aspect of the present invention, it is possible to provide a compound that can improve the lifespan of an organic electroluminescent element, a material for an organic electroluminescent element containing the compound, an organic electroluminescent element containing the compound, and an electronic device equipped with the organic electroluminescent element.

[0012] This is a schematic diagram of an apparatus for measuring transient PL. This is a diagram showing an example of a transient PL decay curve. This is a diagram showing a schematic configuration of an example of an organic electroluminescent element according to the third embodiment of the present invention. This is a diagram showing the relationship between the energy levels and energy transfer of the first host material, sensitizing material and fluorescent material in the light-emitting layer of an example of an organic electroluminescent element according to the fourth embodiment of the present invention. This is a diagram showing the relationship between the energy levels and energy transfer of the first host material, sensitizing material and fluorescent material in the light-emitting layer of an example of an organic electroluminescent element according to the fourth embodiment of the present invention. This is a diagram showing the relationship between the energy levels and energy transfer of the first host material, second host material, sensitizing material and fluorescent material in the light-emitting layer of an example of an organic electroluminescent element according to the fifth embodiment of the present invention. This is a diagram showing the relationship between the energy levels and energy transfer of the sensitizing material and fluorescent material in the light-emitting layer of an example of an organic electroluminescent element according to the sixth embodiment of the present invention. This is a diagram showing the relationship between the energy levels and energy transfer of the second host material, sensitizing material and fluorescent material in the light-emitting layer of an example of an organic electroluminescent element according to the seventh embodiment of the present invention.

[0013] [Definition] In this specification, the term "hydrogen atom" includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0014] In this specification, in chemical structural formulas, any bondable positions where symbols such as "R" or "D" representing a deuterium atom are not explicitly indicated shall be assumed to be bonded to hydrogen atoms, i.e., light hydrogen atoms, deuterium atoms, or tritium atoms.

[0015] In this specification, the ring-forming carbon number refers to the number of carbon atoms among the atoms constituting the ring itself in a compound with a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, fused ring compounds, crosslinked compounds, carbocyclic compounds, and heterocyclic compounds). If the ring is substituted by a substituent, the carbon atoms in the substituent are not included in the ring-forming carbon number. The same applies to "ring-forming carbon number" as described below unless otherwise specified. For example, a benzene ring has 6 ring-forming carbon atoms, a naphthalene ring has 10 ring-forming carbon atoms, a pyridine ring has 5 ring-forming carbon atoms, and a furan ring has 4 ring-forming carbon atoms. Also, for example, a 9,9-diphenylfluorenyl group has 13 ring-forming carbon atoms, and a 9,9'-spirobifluorenyl group has 25 ring-forming carbon atoms. Furthermore, if a benzene ring is substituted with an alkyl group as a substituent, the number of carbon atoms in the alkyl group is not included in the ring-forming carbon number of the benzene ring. Therefore, the ring-forming carbon number of a benzene ring substituted with an alkyl group is 6. Furthermore, if an alkyl group is substituted as a substituent on the naphthalene ring, the number of carbon atoms in that alkyl group is not included in the number of ring-forming carbon atoms of the naphthalene ring. Therefore, the number of ring-forming carbon atoms in a naphthalene ring substituted with an alkyl group is 10.

[0016] In this specification, the number of ring-forming atoms refers to the number of atoms that constitute the ring itself in compounds with a ring-bonded structure (e.g., monocyclic compounds, fused rings, and ring assemblies) (e.g., monocyclic compounds, fused ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of ring-forming atoms) and atoms included in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. The same applies to "number of ring-forming atoms" as described below unless otherwise specified. For example, the number of ring-forming atoms in a pyridine ring is 6, the number of ring-forming atoms in a quinazoline ring is 10, and the number of ring-forming atoms in a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring, or the number of atoms constituting a substituent, are not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms in a pyridine ring to which hydrogen atoms or substituents are bonded is 6. Furthermore, for example, hydrogen atoms bonded to the carbon atom of the quinazoline ring, or atoms constituting substituents, are not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring-forming atoms of a quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

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

[0018] In this specification, the expression "ZZ group with substituted or unsubstituted atoms number XX to YY" means that "number of atoms XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, and does not include the number of substituent atoms when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0019] In this specification, an unsubstituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group," and a substituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is a "substituted ZZ group." In this specification, "unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that the hydrogen atoms in the ZZ group are not replaced by substituents. The hydrogen atoms in an "unsubstituted ZZ group" are light hydrogen atoms, deuterium atoms, or tritium atoms. Also, in this specification, "substituted" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by substituents. Similarly, "substituted" in the case of "BB group substituted with AA group" means that one or more hydrogen atoms in the BB group are replaced by AA group.

[0020] "Substituents described herein" Hereinafter, substituents described herein will be explained.

[0021] The number of ring-forming carbon atoms in the "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified herein. The number of ring-forming atoms in the "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkyl group" described herein is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkenyl group" described herein is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkynyl group" described herein is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted cycloalkyl group" described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted arylene group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring-forming atoms in the "unsubstituted divalent heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkylene group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein.

[0022] ・"Substitutable or unsubstituted aryl groups" Specific examples of "substituted or unsubstituted aryl groups" as described herein (Specific Example Group G1) include the following unsubstituted aryl groups (Specific Example Group G1A) and substituted aryl groups (Specific Example Group G1B). (Here, "unsubstituted aryl group" refers to the case where "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and "substituted aryl group" refers to the case where "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, when simply referred to as "aryl group," it includes both "unsubstituted aryl groups" and "substituted aryl groups." A "substituted aryl group" means a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced by substituents. Examples of "substituted aryl groups" include the group in which one or more hydrogen atoms of an "unsubstituted aryl group" in Specific Example Group G1A below are replaced by substituents, and the example of a substituted aryl group in Specific Example Group G1B below. The examples of "unsubstituted aryl groups" and "substituted aryl groups" listed herein are merely examples. The "substituted aryl groups" described herein also include groups in which the hydrogen atoms bonded to the carbon atom of the aryl group itself in the "substituted aryl groups" of specific examples group G1B below are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted aryl groups" of specific examples group G1B below are further replaced by substituents.

[0023] - Unsubstituted aryl groups (specific examples 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, benzoantryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, crisenyl group, benzocrisenyl group, triphenylenyl group, benzotriphenylenyl group, tetracerenyl group, pentaceryl group, fluorenyl group, 9,9'-spirobifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, fluoranthenyl group, benzofluoranthenyl group, perilenyl group, and monovalent aryl groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0024]

[0025]

[0026] Substitutive aryl groups (specific examples 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, A naphthylphenyl group, and a monovalent group derived from the ring structure represented by the general formulas (TEMP-1) to (TEMP-15) in which one or more hydrogen atoms are replaced by substituents.

[0027] - "Substituted or unsubstituted heterocyclic groups" The "heterocyclic groups" described herein are cyclic groups containing at least one heteroatom in the ring-forming atoms. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron. The "heterocyclic groups" described herein are monocyclic groups or fused ring groups. The "heterocyclic groups" described herein are aromatic heterocyclic groups or non-aromatic heterocyclic groups. Specific examples of "substituted or unsubstituted heterocyclic groups" described herein (Specific Examples Group G2) include the following unsubstituted heterocyclic groups (Specific Examples Group G2A) and substituted heterocyclic groups (Specific Examples Group G2B). (Here, "unsubstituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group," and "substituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group.") In this specification, the term "heterocyclic group" alone includes both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups." A "substituted heterocyclic group" means a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of "substituted heterocyclic groups" include the groups in the following example group G2A in which hydrogen atoms of an "unsubstituted heterocyclic group" are replaced, and the examples of substituted heterocyclic groups in the following example group G2B. Furthermore, the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic groups" described herein also include groups in which the hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself in the "substituted heterocyclic groups" of specific examples group G2B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted heterocyclic groups" of specific examples group G2B are further replaced by substituents.

[0028] The specific examples group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (Specific Examples Group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (Specific Examples Group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (Specific Examples Group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (Specific Examples Group G2A4).

[0029] Specific examples group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (Specific Examples Group G2B1), substituted heterocyclic groups containing an oxygen atom (Specific Examples Group G2B2), substituted heterocyclic groups containing a sulfur atom (Specific Examples Group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (Specific Examples Group G2B4).

[0030] ・Unsubstituted heterocyclic groups containing nitrogen atoms (specific examples group G2A1): Pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyridyl group, pyridadinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, indolyl group, isoindolyl group, indolidinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, indazolyl group, phenanthrolinyl group, phenanthridineyl group, acridinyl group, phenadinyl group, carbazolyl group, Benzocarbazolyl group, morpholino group, phenoxazinyl group, phenothiazinyl group, azacarbazolyl group, and diazacarbazolyl group.

[0031] - Unsubstituted heterocyclic groups containing an oxygen atom (specific examples group G2A2): furyl group, oxazolyl group, 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, azanaftobenzofuranyl group, and diazanaftobenzofuranyl group.

[0032] - Unsubstituted heterocyclic groups containing a sulfur atom (specific examples group G2A3): thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), dibenzothiophenyl group (dibenzothienyl group), naphthobenzothiophenyl group (naphthobenzothienyl group), benzothiazolyl group, benzoisothiazolyl group, phenothiazinyl group, dinaphthothiophenyl group (dinaphthothienyl group), azadibenzothiophenyl group (azadibenzothienyl group), diazadibenzothiophenyl group (diazadibenzothienyl group), azanaphttobenzothiophenyl group (azanaphthobenzothienyl group), and diazanaphttobenzothiophenyl group (diazanaphttobenzothienyl group).

[0033] - Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (Specific examples group G2A4):

[0034]

[0035]

[0036] In the above general formulas (TEMP-16) to (TEMP-33), X Ａ and Y Ａ Each of these independently consists of an oxygen atom, a sulfur atom, NH, or CH. ２ However, X Ａ and Y Ａ At least one of them is an oxygen atom, a sulfur atom, or NH. In the general formulas (TEMP-16) to (TEMP-33), X Ａ and Y Ａ At least one of them is NH or CH ２ In this case, the monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) contains these NH or CH ２ It contains a monovalent group obtained by removing one hydrogen atom from the original.

[0037] - Substitutive heterocyclic groups containing a nitrogen atom (specific examples group G2B1): (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazole-9-yl group, phenylcarbazole-9-yl group, methylbenzimidazolyl group, ethylbenzimidazolyl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenylquinazolinyl group, and biphenylylquinazolinyl group.

[0038] - Heterocyclic groups with oxygen atoms substituted (specific examples group G2B2): Phenyldibenzofuranyl group, methyldibenzofuranyl group, t-butyldibenzofuranyl group, and monovalent residues of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0039] - Substitutive heterocyclic groups containing a sulfur atom (specific examples group G2B3): Phenyldibenzothiophenyl group, methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and monovalent residues of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0040] - Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific examples group G2B4):

[0041] The aforementioned "one or more hydrogen atoms of a monovalent heterocyclic group" refers to hydrogen atoms bonded to the ring-forming carbon atoms of the monovalent heterocyclic group, X Ａ and Y Ａ A hydrogen atom bonded to a nitrogen atom when at least one of them is NH, and X Ａ and Y Ａ One of them is CH ２ This refers to one or more hydrogen atoms selected from the hydrogen atoms of the methylene group in that case.

[0042] ・"Substitutable or unsubstituted alkyl groups" Specific examples of "substituted or unsubstituted alkyl groups" as described herein (Specific Examples Group G3) include the following unsubstituted alkyl groups (Specific Examples Group G3A) and substituted alkyl groups (Specific Examples Group G3B). (Here, "unsubstituted alkyl group" refers to the case where "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and "substituted alkyl group" refers to the case where "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereafter, when simply referred to as "alkyl group," it includes both "unsubstituted alkyl groups" and "substituted alkyl groups." "Substitutable alkyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced by substituents. Specific examples of "substituted alkyl groups" include the group in which one or more hydrogen atoms in the following "unsubstituted alkyl group" (Specific Examples Group G3A) are replaced by substituents, and examples of substituted alkyl groups (Specific Examples Group G3B). In this specification, the alkyl group in "unsubstituted alkyl group" means a chain-like alkyl group. Therefore, "unsubstituted alkyl groups" include both linear and branched "unsubstituted alkyl groups." The examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed here are merely examples; the "substituted alkyl groups" described herein also include groups in which the hydrogen atoms of the alkyl group itself are further replaced by substituents, as well as groups in which the hydrogen atoms of the substituents are further replaced by substituents.

[0043] Unsubstituted alkyl groups (specific examples group G3A): methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group.

[0044] Substitutive alkyl groups (specific examples group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group, and trifluoromethyl group.

[0045] - "Substitutable or unsubstituted alkenyl groups" Specific examples of "substituted or unsubstituted alkenyl groups" as described herein (Specific Examples Group G4) include the following unsubstituted alkenyl groups (Specific Examples Group G4A) and substituted alkenyl groups (Specific Examples Group G4B). (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply includes both "unsubstituted alkenyl groups" and "substituted alkenyl groups." A "substituted alkenyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced by substituents. Specific examples of "substituted alkenyl groups" include groups in which the "unsubstituted alkenyl groups" (specific example group G4A) have substituents, and examples of substituted alkenyl groups (specific example group G4B). Note that the examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl groups" described herein also include groups in which the hydrogen atoms of the alkenyl group itself in the "substituted alkenyl groups" of specific example group G4B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted alkenyl groups" of specific example group G4B are further replaced by substituents.

[0046] - Unsubstituted alkenyl groups (specific examples group G4A): vinyl group, allyl group, 1-butenyl group, 2-butenyl group, and 3-butenyl group.

[0047] Substitutable alkenyl groups (specific examples group G4B): 1,3-butanedienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.

[0048] ・"Substituted or unsubstituted alkynyl groups" Specific examples of "substituted or unsubstituted alkynyl groups" as described herein (Specific Examples Group G5) include the following unsubstituted alkynyl groups (Specific Examples Group G5A), etc. (Here, an unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl groups" is an "unsubstituted alkynyl group.") Hereafter, when simply referred to as "alkynyl group," it includes both "unsubstituted alkynyl groups" and "substituted alkynyl groups." A "substituted alkynyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced by substituents. Specific examples of "substituted alkynyl groups" include the following groups in which one or more hydrogen atoms in an "unsubstituted alkynyl group" (Specific Examples Group G5A) are replaced by substituents, etc.

[0049] • Unsubstituted alkynyl groups (specific examples group G5A): Ethynyl group

[0050] ・"Substituted or unsubstituted cycloalkyl groups" Specific examples of "substituted or unsubstituted cycloalkyl groups" as described herein (Specific Examples Group G6) include the following unsubstituted cycloalkyl groups (Specific Examples Group G6A) and substituted cycloalkyl groups (Specific Examples Group G6B). (Here, "unsubstituted cycloalkyl group" refers to the case where "substituted or unsubstituted cycloalkyl group" is "unsubstituted cycloalkyl group," and "substituted cycloalkyl group" refers to the case where "substituted or unsubstituted cycloalkyl group" is "substituted cycloalkyl group.") In this specification, "cycloalkyl group" simply includes both "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups." "Substituted cycloalkyl group" means a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced by substituents. Specific examples of "substituted cycloalkyl groups" include the following groups in which one or more hydrogen atoms in the "unsubstituted cycloalkyl group" (Specific Examples Group G6A) are replaced by substituents, and examples of substituted cycloalkyl groups (Specific Examples Group G6B). The examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed herein are merely examples. The "substituted cycloalkyl groups" described herein also include groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself are replaced by substituents, as well as groups in which the hydrogen atoms of the substituents in the "substituted cycloalkyl groups" of specific examples group G6B are further replaced by substituents.

[0051] Unsubstituted cycloalkyl groups (specific examples group G6A): cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.

[0052] Substitutive cycloalkyl groups (specific examples group G6B): 4-methylcyclohexyl group.

[0053] - "-Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ The group represented by ) as described herein -Si(R ９０１ ) (Caution ９０２) (Caution ９０３ Specific examples of the group represented by (Specific Examples Group G7) include -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6). Here, G1 is a "substituted or unsubstituted aryl group" as described in Specific Examples Group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in Specific Examples Group G2. G3 is a "substituted or unsubstituted alkyl group" as described in Specific Examples Group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Examples Group G6. In -Si(G1)(G1)(G1), the multiple G1s are either identical or different from one another. - In Si(G1)(G2)(G2), multiple G2s are either identical or different from each other. - In Si(G1)(G1)(G2), multiple G1s are either identical or different from each other. - In Si(G2)(G2)(G2), multiple G2s are either identical or different from each other. - In Si(G3)(G3)(G3), multiple G3s are either identical or different from each other. - In Si(G6)(G6)(G6), multiple G6s are either identical or different from each other.

[0054] ・"-O-(R ９０４ The group represented by ) as described herein -O-(R ９０４ Specific examples of the group represented by (Specific Examples Group G8) include -O(G1), -O(G2), -O(G3), and -O(G6). Here, G1 is a "substituted or unsubstituted aryl group" as described in Specific Examples Group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in Specific Examples Group G2. G3 is a "substituted or unsubstituted alkyl group" as described in Specific Examples Group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Examples Group G6.

[0055] ・"-S-(R ９０５ The group represented by ) as described herein -S-(R ９０５Specific examples of the group represented by (Specific Examples Group G9) include -S (G1), -S (G2), -S (G3), and -S (G6). Here, G1 is a "substituted or unsubstituted aryl group" as described in Specific Examples Group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in Specific Examples Group G2. G3 is a "substituted or unsubstituted alkyl group" as described in Specific Examples Group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Examples Group G6.

[0056] -N(R) ９０６ ) (Caution ９０７ The group represented by ) as described herein -N(R ９０６ ) (Caution ９０７ Specific examples of the group represented by (Specific Examples Group G10) include -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6). Here, G1 is a "substituted or unsubstituted aryl group" as described in Specific Examples Group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in Specific Examples Group G2. G3 is a "substituted or unsubstituted alkyl group" as described in Specific Examples Group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Examples Group G6. In -N(G1)(G1), the multiple G1s are either identical or different from each other. In -N(G2)(G2), the multiple G2s are either identical or different from each other. In -N(G3)(G3), the multiple G3s are either identical or different from each other. -N(G6)(G6) The multiple G6s are either identical or different from one another.

[0057] ・"Halogen atom" Specific examples of "halogen atom" as described herein (Specific Examples Group G11) include fluorine atom, chlorine atom, bromine atom, and iodine atom.

[0058] - "Substituted or unsubstituted fluoroalkyl groups" The "substituted or unsubstituted fluoroalkyl groups" described herein refer to groups in which at least one hydrogen atom bonded to the carbon atoms constituting the alkyl group is replaced by a fluorine atom, and also include groups in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group are replaced by fluorine atoms (perfluoro groups). The number of carbon atoms in an "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. "Substituted fluoroalkyl groups" refer to groups in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced by substituents. The "substituted fluoroalkyl groups" described herein also include groups in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent are further replaced by substituents. Specific examples of "unsubstituted fluoroalkyl groups" include groups in which one or more hydrogen atoms in the aforementioned "alkyl group" (specific example group G3) are replaced by fluorine atoms.

[0059] - "Substituted or unsubstituted haloalkyl groups" The "substituted or unsubstituted haloalkyl groups" described herein refer to groups in which at least one hydrogen atom bonded to the carbon atoms constituting the alkyl group is replaced by a halogen atom, and also include groups in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group are replaced by halogen atoms. The number of carbon atoms in an "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. "Substituted haloalkyl groups" refer to groups in which one or more hydrogen atoms of a "haloalkyl group" are replaced by substituents. The "substituted haloalkyl groups" described herein also include groups in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent are further replaced by substituents. Specific examples of "unsubstituted haloalkyl groups" include groups in which one or more hydrogen atoms in the aforementioned "alkyl group" (specific example group G3) are replaced by halogen atoms. Haloalkyl groups are sometimes referred to as alkyl halides.

[0060] - "Substituted or unsubstituted alkoxy groups" Specific examples of "substituted or unsubstituted alkoxy groups" as described herein include the 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 herein.

[0061] - "substituted or unsubstituted alkylthio group" A specific example of the "substituted or unsubstituted alkylthio group" described herein is the group represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in 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 herein.

[0062] - "substituted or unsubstituted aryloxy group" A specific example of the "substituted or unsubstituted aryloxy group" described herein is a group represented by -O(G1), where G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.

[0063] - "substituted or unsubstituted arylthio group" A specific example of the "substituted or unsubstituted arylthio group" described herein is the group represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.

[0064] - "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described herein is a group represented by -Si(G3)(G3)(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) are either 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 herein.

[0065] - "Substituted or unsubstituted aralkyl group" A specific example of the "substituted or unsubstituted aralkyl group" described herein is a group represented by -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3, and G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. Therefore, an "aralkyl group" is a group in which the hydrogen atom of an "alkyl group" is replaced by an "aryl group" as a substituent, and is one form of a "substituted alkyl group". An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" in which an "unsubstituted aryl group" is substituted, and the number of carbon atoms in the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified herein. Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.

[0066] Unless otherwise specified herein, the substituted or unsubstituted aryl groups are preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, pyrenyl, chrysenyl, triphenylenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl.

[0067] Unless otherwise specified herein, the substituted or unsubstituted heterocyclic groups are preferably pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, benzimidazolyl, phenanthrolinyl, carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, or 9-carbazolyl), benzocarbazolyl, azacarbazolyl, diazacarbazolyl, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, aza These include dibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazole-1-yl group, (9-phenyl)carbazole-2-yl group, (9-phenyl)carbazole-3-yl group, or (9-phenyl)carbazole-4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazole-9-yl group, phenylcarbazole-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group, etc.

[0068] In this specification, unless otherwise specified, the carbazolyl group is specifically one of the following groups:

[0069]

[0070] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically one of the following groups:

[0071]

[0072] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents the bond position.

[0073] In this specification, unless otherwise specified, the dibenzofuranyl group and the dibenzothiophenyl group specifically refer to any of the following groups:

[0074]

[0075] In the general formulas (TEMP-34) to (TEMP-41) above, * indicates a bond position.

[0076] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t-butyl groups.

[0077] - "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described herein is a divalent group derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described above. Specific examples of "substituted or unsubstituted arylene groups" (Specific Examples Group G12) include divalent groups derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described in Specific Examples Group G1.

[0078] - "Substitutable or unsubstituted divalent heterocyclic groups" Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic groups" described herein are divalent groups derived by removing one hydrogen atom from the heterocycle of the "substituted or unsubstituted heterocyclic groups" described above. Specific examples of "substituted or unsubstituted divalent heterocyclic groups" (Specific Examples Group G13) include divalent groups derived by removing one hydrogen atom from the heterocycle of the "substituted or unsubstituted heterocyclic groups" described in Specific Examples Group G2.

[0079] - "Substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described herein is a divalent group derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl group" described above. Specific examples of the "substituted or unsubstituted alkylene group" (Specific Examples Group G14) include the divalent group derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl group" described in Specific Examples Group G3.

[0080] Unless otherwise specified herein, the substituted or unsubstituted arylene groups are preferably any of the following general formulas (TEMP-42) to (TEMP-68).

[0081]

[0082]

[0083] In the above general formulas (TEMP-42) to (TEMP-52), Q １ ~Q １０ Each of these is independently a hydrogen atom or a substituent. In the general formulas (TEMP-42) to (TEMP-52) above, * represents a bond position.

[0084]

[0085] In the above general formulas (TEMP-53) to (TEMP-62), Q １ ~Q １０ Each of these is independently either a hydrogen atom or a substituent. Formula Q ９ and Q １０ These elements may be bonded to each other via single bonds to form a ring. In the general formulas (TEMP-53) to (TEMP-62), * indicates a bond position.

[0086]

[0087] In the above general formulas (TEMP-63) to (TEMP-68), Q １ ~Q ８ Each of these is independently a hydrogen atom or a substituent. In the general formulas (TEMP-63) to (TEMP-68), * represents a bond position.

[0088] Unless otherwise specified herein, the substituted or unsubstituted divalent heterocyclic groups described herein are preferably any of the following general formulas (TEMP-69) to (TEMP-102).

[0089]

[0090]

[0091]

[0092] In the above general formulas (TEMP-69) to (TEMP-82), Q １ ~Q ９ Each of these is independently either a hydrogen atom or a substituent.

[0093]

[0094]

[0095]

[0096]

[0097] In the above general formulas (TEMP-83) to (TEMP-102), Q １ ~Q ８ Each of these is independently either a hydrogen atom or a substituent.

[0098] The above is a description of the substituents described herein.

[0099] ・"When they combine to form a ring" In this specification, "one or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine with each other" means the case in which "one or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring," the case in which "one or more pairs of adjacent elements combine to form a substituted or unsubstituted fused ring," and the case in which "one or more pairs of adjacent elements do not combine with each other." The cases in this specification where "one or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring" and the case where "one or more pairs of adjacent elements combine to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "when they combine to form a ring") will be explained below. We will explain using the example of an anthracene compound represented by the following general formula (TEMP-103), whose parent skeleton is an anthracene ring.

[0100]

[0101] For example, R ９２１~R ９３０ In the case where "one or more pairs of adjacent groups are joined together to form a ring," the pairs of adjacent groups that make up one set are R ９２１ and R ９２２ The group, R ９２２ and R ９２３ The group, R ９２３ and R ９２４ The group, R ９２４ and R ９３０ The group, R ９３０ and R ９２５ The group, R ９２５ and R ９２６ The group, R ９２６ and R ９２７ The group, R ９２７ and R ９２８ The group, R ９２８ and R ９２９ The pair with, and R ９２９ and R ９２１ They are a pair.

[0102] The phrase "one or more sets" above means that two or more sets of the above-mentioned sets of two or more adjacent elements may simultaneously form a ring. For example, R ９２１ and R ９２２ and are joined to each other to form a ring Q Ａ Forms R ９２５ and R ９２６ and are joined to each other to form a ring Q Ｂ If the above general formula (TEMP-103) is formed, the anthracene compound represented by the above general formula (TEMP-104) is represented by the following general formula (TEMP-104).

[0103]

[0104] The case where "two or more adjacent elements form a ring" includes not only cases where two adjacent elements are joined, as in the example above, but also cases where three or more adjacent elements are joined. For example, R ９２１ and R ９２２ and are joined to each other to form a ring Q Ａ Forms R ９２２ and R ９２３ and are joined to each other to form a ring Q Ｃ It forms three adjacent (R ９２１ , R ９２２ and R９２３ This means that a set consisting of ) combines with each other to form a ring and condenses onto the anthracene matrix skeleton, in which case the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q Ａ and ring Q Ｃ R ９２２ Share.

[0105]

[0106] The formed "mono-ring" or "condensed-ring" may be saturated or unsaturated, as a structure of the formed ring alone. Even when "a pair of adjacent rings" forms a "mono-ring" or "condensed-ring," the "mono-ring" or "condensed-ring" can form a saturated or unsaturated ring. For example, ring Q formed in the general formula (TEMP-104) Ａ and ring Q Ｂ These are, respectively, a "single ring" or a "condensed ring". Also, ring Q formed in the general formula (TEMP-105) Ａ , and ring Q Ｃ This is a "condensed ring". The ring Q of the general formula (TEMP-105) Ａ and Q Ｃ This refers to the Q environment. Ａ and Q Ｃ The ring Q of the general formula (TMEP-104) is formed by the condensation of the two rings. Ａ If it is a benzene ring, then ring Q Ａ It is a single ring. The ring Q of the general formula (TMEP-104) Ａ If it is a naphthalene ring, then ring Q Ａ It is a condensed ring.

[0107] An "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocycle. A "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocycle. Specific examples of aromatic hydrocarbon rings include structures in which the groups listed as examples in specific example group G1 are terminated by hydrogen atoms. Specific examples of aromatic heterocycles include structures in which the aromatic heterocyclic groups listed as examples in specific example group G2 are terminated by hydrogen atoms. Specific examples of aliphatic hydrocarbon rings include structures in which the groups listed as examples in specific example group G6 are terminated by hydrogen atoms. "To form a ring" means to form a ring using only multiple atoms of the parent skeleton, or with multiple atoms of the parent skeleton and one or more additional arbitrary elements. For example, as shown in the general formula (TEMP-104), R ９２１ and R ９２２ Ring Q is formed when these two elements are bonded together. Ａ R ９２１ The carbon atoms of the anthracene skeleton to which are bonded, and R ９２２ It refers to a ring formed by the carbon atoms of the anthracene skeleton to which the R bond is attached, and one or more arbitrary elements. A specific example is R ９２１ and R ９２２ And the environment Q Ａ When forming R ９２１ The carbon atoms of the anthracene skeleton to which are bonded, and R ９２２ When the carbon atoms of the anthracene skeleton bonded to the four carbon atoms form a monocyclic unsaturated ring, R ９２１ and R ９２２ The ring formed by these two is a benzene ring.

[0108] Here, "any element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur, unless otherwise specified herein. In any element (for example, carbon or nitrogen), bonds that do not form a ring may be terminated with a hydrogen atom or the like, or substituted with "any substituent" as described later. If any element other than carbon is included, the formed ring is a heterocycle. Unless otherwise specified herein, "one or more any elements" constituting a monocycle or fused ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5. Unless otherwise specified herein, of "monocycle" and "fused ring," "monocycle" is preferred. Unless otherwise specified herein, of "saturated ring" and "unsaturated ring," "unsaturated ring" is preferred. Unless otherwise specified herein, "monocycle" is preferably a benzene ring. Unless otherwise specified herein, "unsaturated ring" is preferably a benzene ring. When "one or more sets of two or more adjacent elements" "bond to each other to form a substituted or unsubstituted monoring" or "bond to each other to form a substituted or unsubstituted fused ring", unless otherwise specified herein, preferably, one or more sets of two or more adjacent elements bond to each other to form a substituted or unsubstituted "unsaturated ring" consisting of multiple atoms of the parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur elements, ranging from one to fifteen.

[0109] The substituents in the case where the above-mentioned "mono-ring" or "fused ring" has substituents are, for example, "any substituents" as described later. Specific examples of substituents in the case where the above-mentioned "mono-ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described in this specification" above. The substituents in the case where the above-mentioned "saturated ring" or "unsaturated ring" has substituents are, for example, "any substituents" as described later. Specific examples of substituents in the case where the above-mentioned "mono-ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described in this specification" above. The above explains the cases where "one or more sets of two or more adjacent elements are bonded to each other to form a substituted or unsubstituted mono-ring" and where "one or more sets of two or more adjacent elements are bonded to each other to form a substituted or unsubstituted fused ring" ("when they are bonded to form a ring").

[0110] - Substituents in the case of "substituted or unsubstituted" In one embodiment of this specification, the substituents in the case of "substituted or unsubstituted" (which may be referred to as "any substituents" in this specification) are, for example, unsubstituted C1-C50 alkyl groups, unsubstituted C2-C50 alkenyl groups, unsubstituted C2-C50 alkynyl groups, unsubstituted ring-forming C3-C50 cycloalkyl groups, -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ ), -O-(R ９０４ ), -S-(R ９０５ ), -N(R ９０６ ) (Caution ９０７ ), a group selected from the group consisting of halogen atoms, cyano groups, nitro groups, unsubstituted aryl groups with 6 to 50 ring-forming atoms, and unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms, where R ９０１ ~R ９０７ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group. ９０１ If there are two or more of them, then there are two or more R９０１ They are either identical or different from each other, R ９０２ If there are two or more of them, then there are two or more R ９０２ They are either identical or different from each other, R ９０３ If there are two or more of them, then there are two or more R ９０３ They are either identical or different from each other, R ９０４ If there are two or more of them, then there are two or more R ９０４ They are either identical or different from each other, R ９０５ If there are two or more of them, then there are two or more R ９０５ They are either identical or different from each other, R ９０６ If there are two or more of them, then there are two or more R ９０６ They are either identical or different from each other, R ９０７ If there are two or more of them, then there are two or more R ９０７ They are either identical or different from one another.

[0111] In one embodiment, the substituent in the case of "substituted or unsubstituted" is a group selected from the group consisting of alkyl groups having 1 to 50 carbon atoms, aryl groups having 6 to 50 ring-forming carbon atoms, and heterocyclic groups having 5 to 50 ring-forming atoms.

[0112] In one embodiment, the substituent in the case of "substituted or unsubstituted" is a group selected from the group consisting of alkyl groups having 1 to 18 carbon atoms, aryl groups having 6 to 18 ring-forming carbon atoms, and heterocyclic groups having 5 to 18 ring-forming atoms.

[0113] Specific examples of each of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents as described herein" above.

[0114] Unless otherwise specified herein, any adjacent substituents may form a "saturated ring" or an "unsaturated ring," preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, and more preferably a benzene ring. Unless otherwise specified herein, any substituent may have further substituents, the same as those described above for any substituent.

[0115] In this specification, a numerical range expressed using "AA to BB" means a range that includes the numerical value AA, which is written before "AA to BB", as the lower limit, and the numerical value BB, which is written after "AA to BB", as the upper limit.

[0116] [First Embodiment] <Compound> The compound according to the first embodiment is a compound represented by the following formula (1).

[0117]

[0118] (In formula (1) above, L is a substituted or unsubstituted arylene group having 6 to 18 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 18 ring-forming atoms, R １ , R ２ , R ３ , R ４ and R ５ One or more pairs of adjacent elements from among them either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine with each other, R １０１ , R １０２ , R １０３ , R １０４ , R １０５ , R １０６ , R １０７ and R １０８ One of the groups selected is a single bond that connects to *a, and R is not a single bond. １０１ ~R １０８One or more pairs of adjacent elements from among them either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine with each other, R １１１ , R １１２ , R １１３ , R １１４ , R １１５ , R １１６ , R １１７ and R １１８ One of the groups selected is a single bond that connects to *b, and R is not a single bond. １１１ ~R １１８ One or more pairs of adjacent elements from among them either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine with each other, R １２１ , R １２２ , R １２３ , R １２４ , R １２５ , R １２６ , R １２７ and R １２８ One or more pairs of adjacent R elements either bond to each other to form a substituted or unsubstituted monoring, or bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other, are not single-bonded, do not form the substituted or unsubstituted monoring, and do not form the substituted or unsubstituted fused ring. １ ~R ５ , R １０１ ~R １０８ , R １１１ ~R １１８ , and R １２１ ~R １２８ Each of these independently consists of a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 haloalkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group, and -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３A group represented by ) -O-(R ９０４ A group represented by ) -S-(R ９０５ A group represented by ) -N(R ９０６ ) (Caution ９０７ Groups represented by ), substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, -C(=O)R ８０１ The base represented by -COOR ８０２ Groups represented by, halogen atoms, cyano groups, nitro groups, -P(=O)(R ９３１ ) (Caution ９３２ The group represented by ) -Ge(R ９３３ ) (Caution ９３４ ) (Caution ９３５ A group represented by ) -B(R ９３６ ) (Caution ９３７ A base represented by ) -B(OR ９３８ ) ( OR ９３９ The group represented by ) -O-S (=O) ２ (R ９４０ A group represented by ), a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms, provided that R １ ~R ５ , R １０１ ~R １０８ , R １１１ ~R １１８ , and R １２１ ~R １２８ One or more atoms selected from the group consisting of are deuterium atoms, and R ９０１ ~R ９０７ , R ８０１ ~R ８０２ , and R ９３１ ~R ９４０ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heterocyclic group, R ９０１ If multiple R ９０１ They are either identical or different from each other, R ９０２If multiple R ９０２ They are either identical or different from each other, R ９０３ If multiple R ９０３ They are either identical or different from each other, R ９０４ If multiple R ９０４ They are either identical or different from each other, R ９０５ If multiple R ９０５ They are either identical or different from each other, R ９０６ If multiple R ９０６ They are either identical or different from each other, R ９０７ If multiple R ９０７ They are either identical or different from each other, R ８０１ If multiple R ８０１ They are either identical or different from each other, R ８０２ If multiple R ８０２ They are either identical or different from each other, R ９３１ If multiple R ９３１ They are either identical or different from each other, R ９３２ If multiple R ９３２ They are either identical or different from each other, R ９３３ If multiple R ９３３ They are either identical or different from each other, R ９３４ If multiple R ９３４ They are either identical or different from each other, R ９３５ If multiple R ９３５ They are either identical or different from each other, R ９３６ If multiple R ９３６ They are either identical or different from each other, R ９３７ If multiple R ９３７ They are either identical or different from each other, R ９３８ If multiple R ９３８ They are either identical or different from each other, R ９３９ If multiple R ９３９They are either identical or different from each other, R ９４０ If multiple R ９４０ (They are either identical or different to each other.)

[0119] According to the compound of the first embodiment, the lifespan of the organic EL element can be improved. According to one embodiment of the compound of the first embodiment, in addition to improving the lifespan, other elemental performance of the organic EL element can be improved, for example, at least one of the luminous efficiency, brightness, emission wavelength, chromaticity, and driving voltage can be improved.

[0120] In the compound according to the first embodiment (the compound represented by formula (1) above), R does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring. １２１ ~R １２８ However, it is preferable that it be a deuterium atom.

[0121] In the compound according to the first embodiment, R does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring. １ ~R ５ However, it is preferable that it be a deuterium atom.

[0122] In the compound according to the first embodiment, R does not form a single bond, nor does it form a substituted or unsubstituted monoring, nor does it form a substituted or unsubstituted fused ring. １０１ ~R １０８ However, it is preferable that it be a deuterium atom.

[0123] In the compound according to the first embodiment, R does not form a single bond, nor does it form a substituted or unsubstituted monoring, nor does it form a substituted or unsubstituted fused ring. １１１ ~R １１８ However, it is preferable that it be a deuterium atom.

[0124] In the compound according to the first embodiment, it is also preferable that all hydrogen atoms other than those identified as deuterium atoms are light hydrogen atoms.

[0125] In the compound according to the first embodiment (the compound represented by formula (1) above), R １ ~R５ , R １０１ ~R １０８ , and R １１１ ~R １１８ Preferably, one or more elements selected from the group consisting of are deuterium atoms.

[0126] In the compound according to the first embodiment, R does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring. １ ~R ５ Furthermore, R that does not form a single bond, nor a substituted or unsubstituted monoring, nor a substituted or unsubstituted fused ring １０１ ~R １０８ However, it is also preferable that the atom be a deuterium atom.

[0127] In the compound according to the first embodiment, R does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring. １ ~R ５ and R １２１ ~R １２８ Furthermore, R that does not form a single bond, nor a substituted or unsubstituted monoring, nor a substituted or unsubstituted fused ring １０１ ~R １０８ and R １１１ ~R １１８ However, it is also preferable that the atom be a deuterium atom.

[0128] In the compound according to the first embodiment, L is preferably a substituted or unsubstituted arylene group having 6 to 14 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 14 ring-forming atoms.

[0129] In the compound according to the first embodiment, L is preferably a substituted or unsubstituted ring-forming arylene group having 6 to 12 carbon atoms, and more preferably a substituted or unsubstituted ring-forming arylene group having 6 to 10 carbon atoms.

[0130] In the compound according to the first embodiment, L is preferably a group represented by the following formula (L1), formula (L2), or formula (L3).

[0131]

[0132] (In formula (L1), formula (L2), or formula (L3), R １３１ , R １３２ , R １３３ , R １３４ and R １３５ Each of these is independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1-C18 alkyl group, a substituted or unsubstituted ring-forming C6-C18 aryl group, or a substituted or unsubstituted ring-forming C5-C18 heterocyclic group, and * indicates the bond position.

[0133] In the compound according to the first embodiment, it is preferable that all hydrogen atoms in L are deuterium atoms.

[0134] In the compound according to the first embodiment, R does not form a single bond, nor does it form a substituted or unsubstituted monoring, nor does it form a substituted or unsubstituted fused ring. １１１ ~R １１８ However, it is also preferable that all hydrogen atoms in L are deuterium atoms.

[0135] In the compound according to the first embodiment, R does not form a single bond, nor does it form a substituted or unsubstituted monoring, nor does it form a substituted or unsubstituted fused ring. １１１ ~R １１８ However, is a deuterium atom, and L is a group represented by formula (L1), formula (L2), or formula (L3), R １３１ ~R １３５ However, it is also preferable that the atom be a deuterium atom.

[0136] In the compound according to the first embodiment, R does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring. １ ~R ５ and R １２１ ~R １２８ However, R is a deuterium atom, does not have a single bond, does not form the substituted or unsubstituted monoring, and does not form the substituted or unsubstituted fused ring. １０１ ~R １０８ and R １１１ ~R １１８ However, it is also preferable that all hydrogen atoms in L are deuterium atoms.

[0137] In the compound according to the first embodiment, R does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring. １ ~R ５ and R １２１ ~R １２８ However, R is a deuterium atom, does not have a single bond, does not form the substituted or unsubstituted monoring, and does not form the substituted or unsubstituted fused ring. １０１ ~R １０８ and R １１１ ~R １１８ However, is a deuterium atom, and L is a group represented by formula (L1), formula (L2), or formula (L3), R １３１ ~R １３５ However, it is also preferable that the atom be a deuterium atom.

[0138] In the compound according to the first embodiment, it is preferable that L is a group represented by the formula (L2).

[0139] In the compound according to the first embodiment, R １３１ , R １３２ , R １３３ , R １３４ and R １３５ No two or more adjacent pairs of these pairs can be combined with each other.

[0140] In the compound according to the first embodiment, R １３１ , R １３２ , R １３３ , R １３４ and R １３５ It is preferable that it is a deuterium atom.

[0141] In the compound according to the first embodiment, R １３１ , R １３２ , R １３３ , R １３４ and R １３５ It is also preferable that it be a light hydrogen atom.

[0142] In the compound according to the first embodiment, it is preferable that all hydrogen atoms in the molecule of the compound represented by formula (1) are deuterium atoms.

[0143] In the compound according to the first embodiment, R １０３ , R１０４ , R １０５ and R １０６ It is preferable that one selected from the group consisting of is a single bond that binds to *a.

[0144] In the compound according to the first embodiment, R １０６ However, it is preferable that the bond to *a is a single bond. R in formula (1) above １０６ However, when *a is a single bond, the compound according to the first embodiment is a compound represented by the following formula (11).

[0145]

[0146] (In formula (11) above, L, R １ ~R ５ , R １０１ ~R １０５ , R １０７ , R １０８ , R １１１ ~R １１８ , R １２１ ~R １２８ And *b are L and R in formula (1), respectively. １ ~R ５ , R １０１ ~R １０５ , R １０７ , R １０８ , R １１１ ~R １１８ , R １２１ ~R １２８ (And *b is synonymous.)

[0147] In the compound according to the first embodiment, R １１３ , R １１４ , R １１５ and R １１６ It is preferable that one selected from the group consisting of is a single bond that binds to *b. R in formula (1) １１３ However, when *b is a single bond, the compound according to the first embodiment is the compound represented by the following formula (12).

[0148]

[0149] (In formula (12) above, L, R １ ~R ５ , R １０１ ~R１０８ , R １１１ , R １１２ , R １１４ ~R １１８ , R １２１ ~R １２８ And *a are L and R in formula (1), respectively. １ ~R ５ , R １０１ ~R １０８ , R １１１ , R １１２ , R １１４ ~R １１８ , R １２１ ~R １２８ (And is synonymous with *a.)

[0150] In the compound according to the first embodiment, R １０３ , R １０４ , R １０５ and R １０６ One of the groups consisting of is a single bond that binds to *a, R １１３ , R １１４ , R １１５ and R １１６ It is preferable that one selected from the group consisting of is a single bond that binds to *b.

[0151] In the first embodiment, the compound represented by formula (1) is preferably represented by the following formula (10). R in formula (1) １０６ However, it is a single bond that connects to *a, R １１３ However, when *b is a single bond, the compound according to the first embodiment is a compound represented by the following formula (10).

[0152]

[0153] (In formula (10) above, L, R １ ~R ５ , R １０１ ~R １０５ , R １０７ , R １０８ , R １１１ , R １１２ , R １１４ ~R １１８ , and R １２１ ~R １２８ These are L and R in formula (1) above, respectively. １ ~R５ , R １０１ ~R １０５ , R １０７ , R １０８ , R １１１ , R １１２ , R １１４ ~R １１８ , and R １２１ ~R １２８ (This is synonymous with...)

[0154] In the first embodiment, the compound represented by formula (1) is preferably represented by the following formula (13). R in formula (1) １０６ However, it is a single bond that connects to *a, R １１３ However, when *b is a single bond and L is a group represented by the above formula (L2), the compound according to the first embodiment is a compound represented by the following formula (13).

[0155]

[0156] (In formula (13) above, R １ ~R ５ , R １０１ ~R １０５ , R １０７ , R １０８ , R １１１ , R １１２ , R １１４ ~R １１８ and R １２１ ~R １２８ These are, respectively, R in formula (1) above. １ ~R ５ , R １０１ ~R １０５ , R １０７ , R １０８ , R １１１ , R １１２ , R １１４ ~R １１８ and R １２１ ~R １２８ It is synonymous with R １３１ , R １３２ , R １３３ and R １３５ These are, respectively, R in the above formula (L2). １３１ , R １３２ , R １３３ and R １３５ (This is synonymous with...)

[0157] In the compound according to the first embodiment, R does not form a single bond, nor does it form a substituted or unsubstituted monoring, nor does it form a substituted or unsubstituted fused ring. １ ~R ５ , R １０１ ~R １０８ , R １１１ ~R １１８ and R １２１ ~R １２８ Preferably, each of these is independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C14 aryl group, or a substituted or unsubstituted ring-forming C5-C14 heterocyclic group.

[0158] In the compound according to the first embodiment, R does not form a single bond, nor does it form a substituted or unsubstituted monoring, nor does it form a substituted or unsubstituted fused ring. １ ~R ５ , R １０１ ~R １０８ , R １１１ ~R １１８ and R １２１ ~R １２８ Preferably, each of these is independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C12 heterocyclic group.

[0159] In the compound according to the first embodiment, R １ ~R ５ It is preferable that no pairs of adjacent elements are combined with each other.

[0160] In the compound according to the first embodiment, R １ ~R ５Each of these is preferably independently a hydrogen atom, a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; more preferably a hydrogen atom, a substituted or unsubstituted ring-forming aryl group having 6 to 10 carbon atoms, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; and even more preferably a hydrogen atom.

[0161] In the compound according to the first embodiment, R １ ~R ５ It is also preferable that one or more selected from the group consisting of the above are groups represented by the following formula (Ar1).

[0162]

[0163] (In the above formula (Ar1), R １４１ , R １４２ , R １４３ , R １４４ and R １４５ Each of these is independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1-C18 alkyl group, a substituted or unsubstituted ring-forming C6-C18 aryl group, or a substituted or unsubstituted ring-forming C5-C18 heterocyclic group, and * indicates the bond position.

[0164] In the compound according to the first embodiment, R in formula (Ar1) １４１ ~R １４５ It is also preferable that R is a deuterium atom. In the compound according to the first embodiment, R in formula (Ar1) １４１ ~R １４５ It is also preferable that it be a light hydrogen atom.

[0165] In the compound according to the first embodiment, R ２ or R ４ However, it is also preferable that the group be represented by the above formula (Ar1).

[0166] In the compound according to the first embodiment, R １ or R ５ However, it is also preferable that the group be represented by the above formula (Ar1).

[0167] In the compound according to the first embodiment, R１０１ ~R １０８ It is preferable that no pairs of adjacent elements are combined with each other.

[0168] In the compound according to the first embodiment, R １０１ ~R １０８ Each of these is preferably independently a hydrogen atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; more preferably a hydrogen atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; and even more preferably a hydrogen atom.

[0169] In the compound according to the first embodiment, R １１１ ~R １１８ It is preferable that no pairs of adjacent elements are combined with each other.

[0170] In the compound according to the first embodiment, R １１１ ~R １１８ Each of these is preferably independently a hydrogen atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; more preferably a hydrogen atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; and even more preferably a hydrogen atom.

[0171] In the compound according to the first embodiment, R １２１ ~R １２８ It is preferable that no pairs of adjacent elements are combined with each other.

[0172] In the compound according to the first embodiment, R １２１ ~R １２８ Each of these is preferably independently a hydrogen atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; more preferably a hydrogen atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; and even more preferably a hydrogen atom.

[0173] In the compound according to the first embodiment, R １ ~R ５ Of these, any set of two or more adjacent items is not combined with each other, R １０１~R １０８ Of these, any set of two or more adjacent items is not combined with each other, R １１１ ~R １１８ Of these, any set of two or more adjacent items is not combined with each other, R １２１ ~R １２８ It is preferable that no pairs of adjacent elements are combined with each other.

[0174] In the compound according to the first embodiment, the substituent in the case of "substituted or unsubstituted" is preferably an unsubstituted C1-C18 alkyl group, an unsubstituted ring-forming C6-C18 aryl group, or an unsubstituted ring-forming C5-C18 heterocyclic group.

[0175] In the compound according to the first embodiment, it is also preferable that the substituent in the case of "substituted or unsubstituted" is an unsubstituted C1-C6 alkyl group, an unsubstituted ring-forming C3-C10 cycloalkyl group, an unsubstituted ring-forming C6-C12 aryl group, or an unsubstituted ring-forming C5-C13 heterocyclic group.

[0176] In the compound according to the first embodiment, it is preferable that any group described as "substituted or unsubstituted" is an "unsubstituted" group.

[0177] The compound according to the first embodiment is preferably a material used in the light-emitting layer. The compound according to the first embodiment is preferably a host material. The compound according to the first embodiment is preferably a thermally activated delayed fluorescence compound. The compound according to the first embodiment may be a sensitizing material. The compound according to the first embodiment may be a sensitizing material and a thermally activated delayed fluorescence compound. In this specification, thermally activated delayed fluorescence may be referred to as delayed fluorescence. In this specification, the compound according to the first embodiment may be referred to as the first compound.

[0178] (Thermally activated delayed fluorescence) Delayed fluorescence is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Chihaya Adachi, published by Kodansha). In that document, the energy difference ΔE between the excited singlet state and the excited triplet state of a fluorescent material is described. １３It is explained that if the energy difference (ΔST) between the singlet and triplet states can be reduced, the reverse energy transfer from the excited triplet state to the excited singlet state, which normally has a low transition probability, can occur with high efficiency, resulting in the expression of thermally activated delayed fluorescence (TADF). Furthermore, the mechanism of delayed fluorescence generation is explained in Figure 10.38 of the aforementioned document. The TADF mechanism is a mechanism that utilizes the phenomenon in which reverse intersystem crossing from triplet excitons to singlet excitons occurs thermally when a material with a small energy difference (ΔST) between the singlet and triplet states is used. As for compounds that exhibit thermally activated delayed fluorescence (TADF property) (hereinafter also referred to as TADF compounds), for example, compounds in which a donor site and an acceptor site are bound within the molecule are known.

[0179] Generally, delayed fluorescence emission can be confirmed by transient PL (Photoluminescence) measurement.

[0180] The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from transient PL measurements. Transient PL measurement is a technique in which a sample is excited by irradiating it with a pulsed laser, and the decay behavior (transient characteristics) of the PL emission after the irradiation is stopped is measured. PL emission in TADF compounds can be classified into two components: one from singlet excitons generated by the initial PL excitation, and another from singlet excitons generated via triplet excitons. The lifetime of singlet excitons generated by the initial PL excitation is on the order of nanoseconds, which is very short. Therefore, the emission from these singlet excitons decays rapidly after irradiation with the pulsed laser. On the other hand, delayed fluorescence decays slowly because it is emitted from singlet excitons generated via long-lived triplet excitons. 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, the emission intensity originating from delayed fluorescence can be determined.

[0181] Figure 1 shows a schematic diagram of an exemplary apparatus for measuring transient PL. An example of a transient PL measurement method using Figure 1, and an example of delayed fluorescence behavior analysis, will be explained.

[0182] The transient PL measuring device 100 shown in Figure 1 comprises a pulsed laser unit 101 capable of irradiating light of a predetermined wavelength, a sample chamber 102 for containing the measurement sample, a spectrometer 103 for spectrally analyzing 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 Figure 1.

[0183] The sample to be placed in the sample chamber 102 is obtained by depositing a thin film on a quartz substrate in which a doping material is doped with a matrix material at a concentration of 12% by mass.

[0184] A pulsed laser is irradiated from the pulsed laser unit 101 onto a thin film sample housed in the sample chamber 102 to excite the doping material. The emitted light is extracted at a 90-degree angle to the direction of the excitation light irradiation, and the extracted light is spectrally analyzed by the spectrometer 103 to form a two-dimensional image in the streak camera 104. As a result, a two-dimensional image is obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and the bright spots correspond to emission intensity. By cropping this two-dimensional image along a predetermined time axis, an emission spectrum is obtained in which the vertical axis is emission intensity and the horizontal axis is wavelength. Furthermore, by cropping the same two-dimensional image along the wavelength axis, a decay curve (transient PL) is obtained in which the vertical axis is the logarithm of the emission intensity and the horizontal axis is time.

[0185] For example, thin film sample A was prepared as described above using compound HX1 as the matrix material and compound DX1 as the doping material, and transient PL measurements were performed.

[0186]

[0187] Here, the decay curves were analyzed using the thin film samples A and B mentioned above. Thin film sample B was prepared using compound HX2 as the matrix material and compound DX1 as the doping material, as described above.

[0188] Figure 2 shows the decay curves obtained from transient PL measurements for thin film sample A and thin film sample B.

[0189]

[0190] As described above, transient PL measurement allows us to obtain an emission decay curve with emission intensity on the vertical axis and time on the horizontal axis. Based on this emission decay curve, we can estimate the fluorescence intensity ratio between fluorescence emitted from a singlet excited state generated by photoexcitation and delayed fluorescence emitted from a singlet excited state generated by reverse energy transfer via a triplet excited state. In materials exhibiting delayed fluorescence, the ratio of the intensity of the slowly decaying delayed fluorescence to the intensity of the rapidly decaying fluorescence is relatively large.

[0191] Specifically, there are two types of emission from delayed-fluorescence materials: prompt emission (immediate emission) and delayed emission (delayed emission). Prompt emission (immediate emission) is emission observed immediately after the delayed-fluorescence material is excited by pulsed light (light emitted from a pulsed laser) at a wavelength absorbed by the material. Delayed emission (delayed emission) is emission that is not observed immediately after excitation by the pulsed light, but is observed later.

[0192] The amounts and ratios of Prompt emission and Delay emission can be determined by a method similar to that described in "Nature 492, 234-238, 2012" (Reference 1). The apparatus used to calculate the amounts of Prompt emission and Delay emission is not limited to the apparatus described in Reference 1 or the apparatus shown in Figure 1.

[0193] Furthermore, if the compound according to the first embodiment is a delayed-fluorescence compound, a sample prepared by the following method is used to measure the delayed fluorescence of the delayed-fluorescence compound. For example, the delayed-fluorescence compound according to the first embodiment is dissolved in toluene to prepare a dilute solution with an absorbance of 0.05 or less at the excitation wavelength in order to remove the contribution of self-absorption. In addition, to prevent quenching by oxygen, the sample solution is frozen and degassed, then sealed in a lidded cell under an argon atmosphere to obtain an argon-saturated, oxygen-free sample solution. 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 measured under the same conditions. The total fluorescence quantum yield is calculated using the fluorescence area intensities of both spectra according to equation (1) in Morris et al. J. Phys. Chem. 80 (1976) 969.

[0194] In the first embodiment, the amount of Prompt emission (immediate emission) of the compound to be measured is X Ｐ Let X be the amount of delayed emission. Ｄ When that happens, X Ｄ / X Ｐ It is preferable that the value of is 0.05 or higher. The measurement of the amount and ratio of Prompt emission and Delay emission of compounds other than delayed fluorescent compounds in this specification is the same as the measurement of the amount and ratio of Prompt emission and Delay emission of delayed fluorescent compounds in the first embodiment.

[0195] (ΔST) In the first embodiment, the lowest excitation singlet energy S １ And the energy gap T at 77 [K] ７７Ｋ The difference (S １ -T ７７Ｋ Define ) as ΔST.

[0196] (Relationship between Triplet Energy and Energy Gap at 77 K) Here, the relationship between triplet energy and the energy gap at 77 K will be explained. In this specification, the energy gap at 77 K differs from the commonly defined triplet energy. The triplet energy is measured as follows. First, a sample is prepared by dissolving the compound to be measured in a suitable solvent and sealing the solution in a quartz glass tube. For this sample, the phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at a low temperature (77 K), a tangent is drawn to the rise of 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, among the compounds according to the first embodiment, it is preferable that the thermally activated delayed fluorescence compound is a compound with a small ΔST. When ΔST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at low temperatures (77 K), and excited singlet states and excited triplet states coexist. As a result, the spectrum measured in the same manner as above includes emission from both the excited singlet state and the excited triplet state, making it difficult to distinguish which state emitted the light. However, the triplet energy value is considered to be dominant. Therefore, in this specification, although the measurement method is the same as that for the usual triplet energy T, in order to distinguish that it is different in a strict sense, the value measured as follows is referred to as the energy gap T. ７７Ｋ This method is called [method name]. The compound to be measured is dissolved in EPA (diethyl ether:isopentane:ethanol = 5:5:2 (volume ratio)) to obtain a solution with a concentration of 10 μmol / L, and this solution is placed in a quartz cell to be used as the measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) of this measurement sample is measured at a low temperature (77 [K]), and a tangent line is drawn to the rising edge of the short-wavelength side of this phosphorescence spectrum, and the wavelength value λ at the intersection of the tangent line and the horizontal axis is measured. ｅｄｇｅ Based on [nm], the energy amount calculated from the following conversion formula (F1) is the energy gap T at 77 [K]. ７７Ｋ Let's assume the following. Conversion formula (F1): T ７７Ｋ [eV]=1239.85 / λｅｄｇｅ

[0197] The tangent to the rise 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 wavelength maximum value of the spectrum, 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 value is maximum (i.e., the tangent at the inflection point) is taken as the tangent to the rise of the phosphorescence spectrum on the short-wavelength side. Note that maximum values ​​with a peak intensity of 15% or less of the maximum peak intensity of the spectrum are not included in the shortest wavelength maximum value mentioned above, and the tangent drawn at the point closest to the shortest wavelength maximum value where the slope value is maximum is taken as the tangent to the rise of the phosphorescence spectrum on the short-wavelength side. For phosphorescence measurement, the Hitachi High-Technologies Corporation F-4500 spectrofluorometer can be used. However, the measuring apparatus is not limited to this; measurements may also be taken by combining a cooling device, a low-temperature container, an excitation light source, and a light-receiving device.

[0198] (Lowest excitation singlet energy S) １ ) Lowest excitation singlet energy S using solution １ The following method can be used to measure absorption (sometimes referred to as the solution method): Prepare a 10 μmol / L toluene solution of the compound to be measured and place it in a quartz cell. Measure the absorption spectrum of this sample at room temperature (300 K) (vertical axis: absorption intensity, horizontal axis: wavelength). Draw a tangent line to the falling edge of the long-wavelength side of this absorption spectrum, and measure the wavelength λ at the intersection of this tangent line and the horizontal axis. ｅｄｇｅ Substitute [nm] into the following conversion formula (F2) to calculate the lowest excitation singlet energy. Conversion formula (F2): S １ [eV]=1239.85 / λ ｅｄｇｅ Examples of absorption spectrum measuring devices include, but are not limited to, Hitachi's spectrophotometer (device name: U3310).

[0199] The tangent to the falling edge of the absorption spectrum on the longer wavelength side is drawn as follows: Consider the tangent at each point on the spectral curve as you move along the curve in the longer wavelength direction from the maximum value on the longest wavelength side of the absorption spectrum. 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 value of the slope is minimized on the longest wavelength side (except when the absorbance is 0.1 or less) is taken as the tangent to the falling edge of the absorption spectrum on the longer wavelength side. Note that maximum values ​​with absorbance of 0.2 or less are not included in the maximum value on the longest wavelength side mentioned above.

[0200] (Method for producing the compound according to the first embodiment) The compound according to the first embodiment can be produced according to the synthesis method described in the examples below, or by following that synthesis method and using known alternative reactions and raw materials suited to the target product.

[0201] (Specific Examples of Compounds According to the First Embodiment) Examples of compounds according to the first embodiment include the following compounds. However, the present invention is not limited to these examples. In this specification, in the examples of compounds, D may represent a deuterium atom, Me may represent a methyl group, Ph may represent a phenyl group, tBu may represent a tert-butyl group, and tAm may represent a tert-amyl group.

[0202]

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[0224] [Second Embodiment] <Material for Organic Electroluminescent Device> The material for organic electroluminescent device according to the second embodiment contains the compound according to the first embodiment. One embodiment is a material for organic electroluminescent device containing only the compound according to the first embodiment, and another embodiment is a material for organic electroluminescent device containing the compound according to the first embodiment and a compound different from the compound in the first embodiment. In the material for organic electroluminescent device of the second embodiment, the compound according to the first embodiment is preferably a host material. In this specification, when the compound according to the first embodiment is a host material, the host material is referred to as the first host material. The material for organic electroluminescent device according to one embodiment may contain the first host material (compound according to the first embodiment) and another compound, such as a dopant material. The material for organic electroluminescent device according to one embodiment may contain the first host material (compound according to the first embodiment), a second host material different from the first host material, and a dopant material. In the material for organic electroluminescent device according to one embodiment, the first host material may be a sensitizer. In one embodiment of a material for an organic electroluminescent element, the first host material may be a sensitizing material and a delayed-fluorescence compound.

[0225] [Third Embodiment] <Organic Electroluminescent Element> (Light-emitting Unit) One embodiment of the organic EL element according to the third embodiment includes a cathode, an anode, and a light-emitting unit disposed between the cathode and the anode. In one embodiment, the light-emitting unit contains the compound according to the first embodiment.

[0226] According to the organic EL element of this embodiment, the lifespan can be improved. According to one embodiment of the organic EL element of this embodiment, in addition to improving the luminous efficiency, other element performance can be improved, for example, at least one of the brightness, emission wavelength, chromaticity, driving voltage, and luminous efficiency can be improved.

[0227] In the organic EL element according to this embodiment, the light-emitting band is included in the light-emitting unit. In addition to the one or more light-emitting layers included in the light-emitting band, the light-emitting unit may have one or more layers containing at least one selected from the group consisting of organic compounds and inorganic materials. The inorganic material is at least one of an inorganic compound and an element. Preferably, the light-emitting unit includes one or more layers selected from the group consisting of a layer composed of an organic compound, a layer composed of an inorganic material, and a layer composed of both an organic compound and an inorganic material. Examples of layers that may be included in the light-emitting unit in addition to the one or more light-emitting layers include layers that can be used in organic EL elements. There are no particular limitations on layers that can be used in organic EL elements, but examples include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a barrier layer.

[0228] In one embodiment of the third embodiment, a hole transport layer is included between the anode and the light-emitting layer closest to the anode among one or more light-emitting layers. In one embodiment of the third embodiment, an electron transport layer is included between the cathode and the light-emitting layer closest to the cathode among one or more light-emitting layers.

[0229] Figure 3 shows a schematic configuration of an example of an organic EL element according to the third embodiment. The organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10 disposed between the anode 3 and the cathode 4. The light-emitting unit 10 is constructed by stacking a hole injection layer 6, a hole transport layer 7, a light-emitting layer 5, an electron transport layer 8, and an electron injection layer 9 in that order, starting from the anode 3 side. The present invention is not limited to the configuration of the organic EL element shown in Figure 3.

[0230] (Emitting layer) In the third embodiment, the light-emitting unit has one or more light-emitting layers. In the third embodiment, at least one of the one or more light-emitting layers contains the compound according to the first embodiment as the first compound. In the third embodiment, at least one of the one or more light-emitting layers contains the first compound as the first host material.

[0231] In the organic EL element according to this embodiment, the lifespan is easily improved by containing the compound according to the first embodiment as a host material in the light-emitting layer, and in one embodiment of the third embodiment, the luminous efficiency is easily improved.

[0232] In one embodiment of the third embodiment, at least one of the one or more light-emitting layers contains a first host material and a phosphorescent metal complex or a fluorescent material. In one embodiment of the third embodiment, if at least one of the one or more light-emitting layers contains a fluorescent material, the light-emitting layer does not contain a phosphorescent metal complex. In one embodiment of the third embodiment, if at least one of the one or more light-emitting layers contains a phosphorescent metal complex, the light-emitting layer does not contain a fluorescent material. In one embodiment of the third embodiment, at least one of the one or more light-emitting layers may further contain a second host material.

[0233] In one embodiment of the third embodiment, at least one of one or more light-emitting layers contains a first host material and a dopant material. In one embodiment of the third embodiment, the dopant material is a phosphorescent metal complex or a fluorescent material. In one embodiment of the third embodiment, the first host material and the dopant material are contained in a single layer. For example, if the organic EL element has one light-emitting layer, the first host material and the dopant material are contained in that single light-emitting layer, and if it has multiple light-emitting layers, the first host material and the dopant material are contained in one of the multiple light-emitting layers.

[0234] [First Host Material] In the third embodiment, the first host material is the compound according to the first embodiment (the first compound). The first host material may be a sensitizing material. Embodiments in which the first host material is a sensitizing material will be described in the sixth and seventh embodiments.

[0235] [Second host material] In the third embodiment, the second host material can be the second host material in the fifth embodiment described later.

[0236] [Dopant Material] In one embodiment of the third embodiment, the dopant material is a phosphorescent metal complex or a fluorescent material.

[0237] (Phosphorescent Metal Complex) In the third embodiment, the phosphorescent metal complex preferably contains heavy metal atoms. In the third embodiment, the phosphorescent metal complex preferably contains one or more metal atoms selected from the group consisting of platinum (Pt), iridium (Ir), osmium (Os), ruthenium (Ru), rhodium (Rh), palladium (Pd), copper (Cu), silver (Ag), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm).

[0238] In the third embodiment, the phosphorescent metal complex is preferably a compound represented by the following formula (21): M(L １ ) ｎ１ (L ２ ) ｎ２ ... (21)

[0239]

[0240] (In the above formulas (21), (211), (212), and (213), M is a transition metal selected from the group consisting of a first transition metal, a second transition metal, and a third transition metal, L １ n1 is at least one ligand selected from the group consisting of the ligand represented by formula (211), the ligand represented by formula (212), and the ligand represented by formula (213), where n1 is 1, 2, or 3, and L ２ n2 is at least one ligand selected from the group consisting of monodentate ligands, bidentate ligands, and tridentate ligands, and n2 is 0, 1, 2, 3, or 4. １ Tamaki, C.Y. ２ Tamaki, C.Y. ３ Ring and CY ４ Each ring is independently selected from the group consisting of a carbon ring group with 5 to 30 ring-forming carbon atoms and a heterocyclic group with 1 to 30 ring-forming carbon atoms, Y １ ~Y ４These are, independently, single bonds, double bonds, substituted or unsubstituted ring-forming arylene groups with 6 to 50 carbon atoms, substituted or unsubstituted divalent heterocyclic groups with 5 to 50 ring-forming atoms, *a-O-*b, *a-S-*b, *a-C(=O)-*b, *a-S(=O)-*b, *a-C(R ５ ) (Caution ６ )-*b, *a-C(R ５ ) = C(R ６ )-*b, *a-C(R ５ )=*b, *a-Si(R ５ ) (Caution ６ )-*b, *a-B(R ５ )-*b, *a-N(R ５ )-*b, and *a-P(R ５ ) - Selected from the group consisting of *b, a1, a2 and a3 are each independently 1, 2 or 3, a4 is 0, 1, 2 or 3, and if a4 is 0, CY １ Ring and CY ４ The rings are not connected to each other, T １ , T ２ , T ３ and T ４ These are, independently, chemical bonds: *a-O-*b, *a-S-*b, *a-B(R) ７ )-*b, *a-N(R ７ )-*b, *a-P(R ７ )-*b, *a-C(R ７ ) (Caution ８ )-*b, *a-Si(R ７ ) (Caution ８ )-*b, *a-Ge(R ７ ) (Caution ８ Selected from the group consisting of )-*b, *a-C(=O)-*b and *a-C(=S)-*b, where *a and *b are independently bond positions with adjacent atoms, *1, *2, *3 and *4 are bond positions with M, and R １ ~R ８Each of these independently consists of a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C3-C50 heterocycloalkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkenyl group, a substituted or unsubstituted ring-forming C3-C50 heterocycloalkenyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, a substituted or unsubstituted ring-forming C5-C50 heterocyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group. -Si(R ２５１ ) (Caution ２５２ ) (Caution ２５３ A group represented by ) -O-(R ２５４ A group represented by ) -S-(R ２５５ A group represented by ) -N(R ２５６ ) (Caution ２５７ The group represented by -C(=O)R ２５８ The group represented by -C(=O)(OR ２５９ A base represented by ), -S (=O) ２ (OR ２６０ The group represented by ) -O-P(=O)(OR ２６１ ) ( OR ２６２ A group represented by ) -C(R ２６３ ) (Caution ２６４ ) (Caution ２６５ A group represented by ) -B(R ２６６ ) (Caution ２６７ A group represented by ) -P(R ２６８ ) (Caution ２６９ A group represented by ) -S (=O) (R ２７０ A base represented by ), -S (=O) ２ (R ２７１ A group represented by -P(=O)(R ２７２ ) (Caution ２７３The group represented by ) and -P(=S)(R ２７４ ) (Caution ２７５ A group is selected from among those represented by ), R １ ~R ８ One or more pairs of adjacent elements from among them either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine with each other, R １ ~R ８ , and Y １ ~Y ４ One or more pairs of adjacent elements from among them either bond to each other to form a substituted or unsubstituted monoring, or bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other, and b1, b2, b3 and b4 are each independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, R ２５１ ~R ２７５ These are, independently, a hydrogen atom, a halogen atom, and -O-(R). ２７６ A group represented by ) -N(R ２７７ ) (Caution ２７８Groups represented by ), cyano groups, nitro groups, amidino groups, hydrazino groups, hydrazono groups, substituted or unsubstituted C1-C50 alkyl groups, substituted or unsubstituted C2-C50 alkenyl groups, substituted or unsubstituted C2-C50 alkynyl groups, substituted or unsubstituted ring-forming C3-C50 cycloalkyl groups, substituted or unsubstituted ring-forming C3-C50 heterocycloalkyl groups, substituted or unsubstituted ring-forming C3-C50 cycloalkenyl groups, substituted or unsubstituted ring-forming C3-C50 heterocycloalkenyl groups, substituted or unsubstituted ring-forming C6-C50 aryl groups, ring-forming C6-C50 aryl groups substituted with substituted or unsubstituted C1-C50 alkyl groups, Selected from the group consisting of substituted or unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic groups, biphenylyl groups, and terphenylyl groups, R ２７６ ~R ２７８ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group.

[0241] In this specification, a ring-forming carbon-numbered

[0242] In this specification, a heterocyclic group having 1 to 30 ring-forming carbon atoms means a group having the same structure as a carbocyclic group having 5 to 30 ring-forming carbon atoms, but containing, as ring-forming atoms, at least one heteroatom selected from N (nitrogen atom), O (oxygen atom), Si (silicon atom), P (phosphorus atom), and S (sulfur atom) in addition to carbon (the number of carbon atoms may be 1 to 30).

[0243] In this specification, a heterocycloalkyl group having 3 to 50 ring-forming atoms means a monovalent monocyclic group having 3 to 50 ring-forming atoms, which includes at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom. Specific examples include the 1,2,3,4-oxatriazolidinyl group, the tetrahydrofuranyl group, and the tetrahydrothiophenyl group. In this specification, a heterocycloalkylene group having 3 to 50 ring-forming atoms means a divalent group having the same structure as a heterocycloalkyl group having 3 to 50 ring-forming atoms.

[0244] In this specification, a ring-forming cycloalkenyl group having 3 to 50 carbon atoms means a monovalent monocyclic group having 3 to 50 carbon atoms and having at least one double bond within the ring, but lacking aromaticity. Specific examples include the cyclopentenyl group, the cyclohexenyl group, and the cycloheptenyl group. In this specification, a ring-forming cycloalkenylene group having 3 to 50 carbon atoms means a divalent group having the same structure as a ring-forming cycloalkenyl group having 3 to 50 carbon atoms.

[0245] In this specification, a heterocycloalkenyl group having 3 to 50 ring-forming atoms is a monovalent monocyclic group having 3 to 50 ring-forming atoms, containing at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, and having at least one double bond within the ring. Specific examples of heterocycloalkenyl groups having 3 to 50 ring-forming atoms include the 4,5-dihydro-1,2,3,4-oxatriazolyl group, the 2,3-dihydrofuranyl group, and the 2,3-dihydrothiophenyl group. In this specification, a heterocycloalkenylene group having 3 to 50 ring-forming atoms means a divalent group having the same structure as a heterocycloalkenyl group having 3 to 50 ring-forming atoms.

[0246] According to one embodiment, in the compound represented by formula (21), the substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms preferably has 3 to 10 ring-forming carbon atoms, the substituted or unsubstituted heterocycloalkyl group having 3 to 50 ring-forming atoms preferably has 3 to 10 ring-forming atoms, the substituted or unsubstituted cycloalkenyl group having 3 to 50 ring-forming carbon atoms preferably has 3 to 10 ring-forming carbon atoms, and the substituted or unsubstituted heterocycloalkenyl group having 3 to 50 ring-forming atoms preferably has 3 to 10 ring-forming atoms.

[0247] In this specification, a monovalent non-aromatic condensed polycyclic group means a monovalent group (for example, having 8 to 60 carbon atoms) in which two or more rings are fused to each other, containing only carbon as the ring-forming atom, and the entire molecule being non-aromatic. In this specification, a divalent non-aromatic condensed polycyclic group means a divalent group having the same structure as a monovalent non-aromatic condensed polycyclic group.

[0248] In this specification, a monovalent non-aromatic heterocondensed polycyclic group means a monovalent group (for example, having 1 to 60 carbon atoms) in which two or more rings are fused to each other, and which contains at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom in addition to carbon, and the entire molecule is non-aromatic. In this specification, a divalent non-aromatic heterocondensed polycyclic group means a divalent group having the same structure as a monovalent non-aromatic heterocondensed polycyclic group.

[0249] In this specification, "biphenylyl group" means "phenyl group substituted with a phenyl group." A "biphenylyl group" belongs to the category of "substituted phenyl groups" whose substituent is an "aryl group having 6 to 50 ring-forming carbon atoms."

[0250] In this specification, "terphenylyl group" means "phenyl group substituted with a biphenylyl group." The "terphenylyl group" belongs to the category of "substituted phenyl groups" whose substituent is "an aryl group having 6 to 50 ring-forming carbon atoms substituted with an aryl group having 6 to 50 ring-forming carbon atoms."

[0251] In the compound represented by formula (21), T １ , T ２ , T ３ and T ４ The chemical bond is preferably a single bond.

[0252] In the compound represented by formula (21), M is preferably one or more metal atoms selected from the group consisting of platinum (Pt), iridium (Ir), osmium (Os), ruthenium (Ru), rhodium (Rh), palladium (Pd), copper (Cu), silver (Ag), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm), and more preferably platinum (Pt) or iridium (Ir).

[0253] According to one embodiment, in the compound represented by formula (21), CY １ Ring ~ CY ４The rings are, independently, benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, chrysene, cyclopentadiene, 1,2,3,4-tetrahydronaphthalene, carbene, thiophene, furan, selenofen, indole, benzoborol, benzophosphole, indene, benzosilol, benzogermol, benzothiophene, benzoselenophen, benzofuran, carbazole, dibenzoborol, dibenzophosphole, fluorene, dibenzosilol, dibenzogermol, dibenzothiophene, dibenzoselenophen, dibenzofuran, dibenzothiophene 5-oxide, 9H-fluoren-9-one, dibenzothiophene 5,5-dioxide, azaindole, azabenzoborol, azabenzophosphole, azaindene, azabenzosilol, azabenzogermol, azabenzothiophene, azabenzoselenophen, azabenzofuran, The group may be selected from azacarbazole, azadibenzobolol, azadibenzophosphorus, azafluorene, azadibenzosilol, azadibenzogermol, azadibenzothiophene, azadibenzoselenophene, azadibenzofuran, azadibenzothiophene 5-oxide, aza-9H-fluoren-9-one, azadibenzothiophene 5,5-dioxide, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, phenanthroline, pyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, benzopyrazole, benzimidazole, benzoxazole, benzothiazole, benzoxadiazole, benzothiadiazole, benzothiadiazole, 5,6,7,8-tetrahydroisoquinoline, and 5,6,7,8-tetrahydroquinoline.

[0254] According to one embodiment, CY in formula (211) １ Ring and CY ２ At least one of the rings, CY in equation (212) １ Ring ~ CY ３ At least one of the rings, and CY in formula (213) １ Ring ~ CY ４At least one of the rings may be a carbene.

[0255] According to one embodiment, Y in formulas (211) to (213) １ ~Y ４ These are, independently, single bonds, double bonds, *a-O-*b, *a-S-*b, and *a-C(R). ５ ) (Caution ６ ) - *b and *a - N (R ５ ) - *b may be selected from the group consisting of at least one.

[0256] According to one embodiment, in formula (211), R １ and R ２ At least one of the following, in equation (212), R １ ~R ３ At least one of the following, and in formula (213), R １ ~R ４ At least one of these may be an electron-donating group.

[0257] For example, the electron-donating group may be an iso-propyl group, a tert-butyl group, and a substituent selected from the group consisting of the following formulas (10-1) to (10-61).

[0258]

[0259]

[0260] In the above formulas (10-1) to (10-61), * represents the bond position with an adjacent atom.

[0261] In this specification, deuterium atoms are denoted as D in chemical formulas, and light hydrogen atoms are denoted as H or omitted. In this specification, methyl groups may be denoted as Me, phenyl groups as Ph, isopropyl groups as i-Pr, and t-butyl groups as t-Bu in chemical formulas.

[0262] According to one embodiment, R in formula (211) １ and R ２ At least one of them is a substituent other than hydrogen, and / or Y １ *a-N(R ５) - *b, R ５ However, it may also be a substituted ring-forming aryl group having 6 to 50 carbon atoms.

[0263] According to one embodiment, R in formula (212) １ ~R ３ At least one of them is a substituent other than hydrogen, and / or Y １ and Y ２ At least one of them is *a-N(R ５ ) - *b, R ５ However, it may also be a substituted ring-forming aryl group having 6 to 50 carbon atoms.

[0264] According to one embodiment, R in formula (213) １ ~R ４ At least one of them is a substituent other than hydrogen, and / or Y １ ~Y ４ At least one of them is *a-N(R ５ ) - *b, R ５ However, it may also be a substituted ring-forming aryl group having 6 to 50 carbon atoms.

[0265] (Specific examples of phosphorescent metal complexes) Examples of phosphorescent metal complexes of the third embodiment include the following compounds. However, the present invention is not limited to these specific examples of compounds.

[0266]

[0267]

[0268]

[0269] (Fluorescent Material) In the third embodiment, the fluorescent material is preferably a compound that does not exhibit thermally activated delayed fluorescence. In the third embodiment, the fluorescent material is not a phosphorescent metal complex. In the third embodiment, the fluorescent material is preferably not a metal complex. In this specification, the compound used as the fluorescent material may be referred to as the third compound.

[0270] Examples of fluorescent materials 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, bisarylaminofluorantene derivatives, aryl-substituted fluorantene derivatives, indenoperylene derivatives, acenaphthofluorantene derivatives, compounds containing boron atoms, pyrometenoboron complex compounds, compounds having a pyrometene skeleton, metal complexes of compounds having a pyrometene skeleton, diketopyrrolopyrrole derivatives, perylene derivatives, and naphthacene derivatives.

[0271] In the third embodiment, the fluorescent material is one or more compounds selected from the group consisting of a third compound represented by the following formula (41).

[0272]

[0273] (In formula (41) above, the a-ring, b-ring, and c-ring are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle having 5 to 50 ring-forming atoms, L ４０１ and L ４０２ These are O, S, Se, and NR, respectively, independently. ４０ , C(R ４１ ) (Caution ４２ ), or Si (R ４３ ) (Caution ４４ ) and L ４０３ is B, P, or P=O, and R ４０ ~R ４４ Each of them independently either bonds with the a, b, or c ring to form a substituted or unsubstituted monoring, or bonds with the a, b, or c ring to form a substituted or unsubstituted fused ring, or does not bond with the a, b, and c rings, R ４１ and R ４２ They either bond to each other to form a substituted or unsubstituted monoring, or bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other, R ４３ and R４４ R is either bonded to each other to form a substituted or unsubstituted monoring, or bonded to each other to form a substituted or unsubstituted fused ring, or does not bond to each other, does not form the substituted or unsubstituted monoring, and does not form the substituted or unsubstituted fused ring. ４０ ~R ４４ Each of these independently consists of a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -CR ４５ = an iminyl group represented by N, a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms, R ４５ R is a substituted or unsubstituted ring-forming aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 60 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms. ４０ If multiple R ４０ They are either identical or different from each other, R ４１ If multiple R ４１ They are either identical or different from each other, R ４２ If multiple R ４２ They are either identical or different from each other, R ４３ If multiple R ４３ They are either identical or different from each other, R ４４ If multiple R ４４ They are either identical or different from each other, R ４５ If multiple R ４５ They are either identical or different to one another.

[0274] In the third embodiment, the compound represented by formula (41) is preferably the compound represented by the following formula (410).

[0275]

[0276] (In formula (410) above, the a-ring, b-ring, and c-ring are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle having 5 to 50 ring-forming atoms, R ４０１ and R ４０２ Each of these rings independently either bonds with the a, b, or c ring to form a substituted or unsubstituted monoring, or bonds with the a, b, or c ring to form a substituted or unsubstituted condensed ring, or does not bond with the a, b, and c rings, and does not form the substituted or unsubstituted monoring, nor does it form the substituted or unsubstituted condensed ring. ４０１ and R ４０２ Each of these independently consists of a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -CR ４５ (= This refers to an iminyl group represented by N, a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms.)

[0277] In the third embodiment, the compound represented by formula (41) is preferably a compound selected from the group consisting of compounds represented by the following formulas (41-1) to (41-6).

[0278]

[0279]

[0280]

[0281] (In the above formula (41-1), Xa is O, S, Se, C(R) ４０３ ) (Caution ４０４ ), or NR ４０５ And R ４０１ and R ４２１ The group, R ４２１ ~R ４２３ A set consisting of two or more adjacent elements, R ４２３and R ４０２ The group, R ４０２ and R ４２４ The group, R ４２４ ~R ４２７ A set consisting of two or more adjacent elements, R ４２７ and R ４１２ The pair with, and R ４１２ and R ４１１ One or more pairs selected from the group consisting of the following combinations either combine with each other to form a substituted or unsubstituted monoring, or combine with each other to form a substituted or unsubstituted fused ring, or do not combine with each other to form the aforementioned substituted or unsubstituted monoring and do not form the aforementioned substituted or unsubstituted fused ring R ４０１ and R ４０２ Each of these independently consists of a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -CR ４５ = an iminyl group represented by N, a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms, R ４０３ ~R ４０５ , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring ４１１ , R ４１２ , and R ４２１ ~R ４２７ Each of these independently comprises a hydrogen atom or a substituent R. Ｘ The substituent R Ｘ Each of these independently consists of a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ A group represented by ) -O-(R ９０４ A group represented by ) -S-(R ９０５ A group represented by ) -N(R９０６ ) (Caution ９０７ A group represented by ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R ９０１ ~R ９０７ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group, and R ９０１ If multiple R ９０１ They are either identical or different from each other, R ９０２ If multiple R ９０２ They are either identical or different from each other, R ９０３ If multiple R ９０３ They are either identical or different from each other, R ９０４ If multiple R ９０４ They are either identical or different from each other, R ９０５ If multiple R ９０５ They are either identical or different from each other, R ９０６ If multiple R ９０６ They are either identical or different from each other, R ９０７ If multiple R ９０７ (These are either the same as or different from each other.) (In the above formula (41-2), Xa is O, S, Se, C(R ４０３ ) (Caution ４０４ ), or NR ４０５ And R ４０１ and R ４２１ The group, R ４２１ ~R ４２３ A set consisting of two or more adjacent elements, R ４２３ and R ４０２ The group, R ４０２ and R ４２４ The group, R ４２４ ~R ４２７ A set consisting of two or more adjacent elements, R ４１３ and R４１４ The pair with, and R ４１４ and R ４０１ One or more pairs selected from the group consisting of the following combinations either combine with each other to form a substituted or unsubstituted monoring, or combine with each other to form a substituted or unsubstituted fused ring, or do not combine with each other to form the aforementioned substituted or unsubstituted monoring and do not form the aforementioned substituted or unsubstituted fused ring R ４０１ and R ４０２ Each of these independently consists of a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -CR ４５ = an iminyl group represented by N, a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms, R ４０３ ~R ４０５ , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring ４１３ , R ４１４ , and R ４２１ ~R ４２７ Each of these independently comprises a hydrogen atom or a substituent R. Ｘ The substituent R Ｘ This is the substituent R in formula (41-1) above. Ｘ This is synonymous with R ４０３ If multiple R ４０３ They are either identical or different from each other, R ４０４ If multiple R ４０４ They are either identical or different from each other, R ４０５ If multiple R ４０５ (These are either identical or different from each other.) (In the above formula (41-3), Xa and Xb are independently O, S, Se, C(R) ４０３ ) (Caution ４０４ ), or NR ４０５ And R ４０１ and R ４２１ The group, R ４２１ ~R４２３ A set consisting of two or more adjacent elements, R ４２３ and R ４０２ The group, R ４１５ and R ４１６ The group, R ４１６ and R ４１２ The pair with, and R ４１２ and R ４１１ One or more pairs selected from the group consisting of the following combinations either combine with each other to form a substituted or unsubstituted monoring, or combine with each other to form a substituted or unsubstituted fused ring, or do not combine with each other to form the aforementioned substituted or unsubstituted monoring and do not form the aforementioned substituted or unsubstituted fused ring R ４０１ and R ４０２ Each of these independently consists of a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -CR ４５ = an iminyl group represented by N, a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms, R ４０３ ~R ４０５ , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring ４１１ , R ４１２ , R ４１５ , R ４１６ , and R ４２１ ~R ４２３ Each of these independently comprises a hydrogen atom or a substituent R. Ｘ The substituent R Ｘ This is the substituent R in formula (41-1) above. Ｘ This is synonymous with R ４０３ If multiple R ４０３ They are either identical or different from each other, R ４０４ If multiple R ４０４ They are either identical or different from each other, R ４０５ If multiple R ４０５are the same as or different from each other. ) (In the formula (41-4), Xa and Xb are each independently O, S, Se, C(R ４０３ )(R ４０４ ), or NR ４０５ , and the group consisting of one or more selected from the group consisting of the pair of R ４０１ and R ４２１ , the pair of two or more adjacent ones among R ４２１ to R ４２３ , the pair of R ４２３ and R ４０２ , the pair of R ４０２ and R ４１８ , the pair of R ４１８ and R[[ID=Y]] ４１７ , and the pair of R ４１２ and R ４１１ are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, and do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring. R ４０１ and R ４０２ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, an iminyl group represented by -CR ４５ =N, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and R ４０３ to R ４０５ , and R ４１１ , R ４１２ , RD ４１７ , R ４１８ , and R ４２１ to R[[ID=Z]] ４２３ are each independently a hydrogen atom or a substituent R Ｘ , and the substituent R Ｘ is synonymous with the substituent R Ｘ in the formula (D1-1), and R ４０３ It should be noted that there are some tags like ４０３ etc. in the original text which seem to be some kind of specific identifiers in a certain system. If there are specific requirements or corrections regarding these tags, please let me know. Also, the translation might need to be adjusted according to the specific context of the patent content as some parts might be a bit ambiguous without further context.If multiple R ４０３ They are either identical or different from each other, R ４０４ If multiple R ４０４ They are either identical or different from each other, R ４０５ If multiple R ４０５ (These are either identical or different from each other.) (In the above formula (41-5), Xa and Xb are independently O, S, Se, C(R) ４０３ ) (Caution ４０４ ), or NR ４０５ And R ４０１ and R ４２１ The group, R ４２１ ~R ４２３ A set consisting of two or more adjacent elements, R ４２３ and R ４０２ The group, R ４０２ and R ４１８ The group, R ４１８ and R ４１７ The group, R ４１３ and R ４１４ The pair with, and R ４１４ and R ４０１ One or more pairs selected from the group consisting of the following combinations either combine with each other to form a substituted or unsubstituted monoring, or combine with each other to form a substituted or unsubstituted fused ring, or do not combine with each other to form the aforementioned substituted or unsubstituted monoring and do not form the aforementioned substituted or unsubstituted fused ring R ４０１ and R ４０２ Each of these independently consists of a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -CR ４５ = an iminyl group represented by N, a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms, R ４０３ ~R ４０５ , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring ４１３ , R ４１４, R ４１７ , R ４１８ , and R ４２１ ~R ４２３ are each independently a hydrogen atom or a substituent R Ｘ , and the substituent R Ｘ is synonymous with the substituent R Ｘ in the formula (41-1), and when there are a plurality of R ４０３ , the plurality of R ４０３ are the same as or different from each other, and when there are a plurality of R ４０４ , the plurality of R ４０４ are the same as or different from each other, and when there are a plurality of R ４０５ , the plurality of R ４０５ are the same as or different from each other. ) (In the formula (41-6), the pair of R ４０１ and R ４２１ , the pair consisting of two or more adjacent ones among R ４２１ ~R ４２３ , the pair of R ４２３ and R ４０２ , the pair of R ４０２ and R ４２４ , the pair consisting of two or more adjacent ones among R ４２４ ~R ４２７ , the pair of R ４２７ and R ４２８ , the pair consisting of two or more adjacent ones among R ４２８ ~R ４３１ , and the pair of R ４３１ and R ４０１ selected from the group consisting of one or more pairs combine with each other to form a substituted or unsubstituted monocyclic ring, combine with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other, do not form the substituted or unsubstituted monocyclic ring, and do not form the substituted or unsubstituted condensed ring. R ４０１ and R ４０２ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -CR ４５= an iminyl group represented by N, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, wherein R does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted fused ring. ４２１ ~R ４３１ Each of these independently comprises a hydrogen atom or a substituent R. Ｘ The substituent R Ｘ This is the substituent R in formula (41-1) above. Ｘ (This is synonymous with...)

[0282] In the compounds represented by the above formulas (41-1) to (41-5), R ４１２ and R ４１１ The group, R ４１３ and R ４１４ The group, R ４１５ and R ４１６ The pair with, and R ４１７ and R ４１８ It is also preferable that one or more pairs selected from the group consisting of these pairs combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring.

[0283] In the third embodiment, the compound represented by formula (41) is also preferably the compound represented by the following formula (41-7).

[0284]

[0285] (In the above formula (41-7), Xa is O, S, Se, C(R) ４０３ ) (Caution ４０４ ), or NR ４０５ And R ４０１ and R ４２１ The group, R ４２１ ~R ４２３ A set consisting of two or more adjacent elements, R ４２３ and R ４０２ The group, R ４０２ and R ４２４ The group, R ４２４ ~R ４２７ A set consisting of two or more adjacent items, and R ４３７ ~R ４４０From a group consisting of two or more adjacent elements, one or more elements are selected to bond with each other to form a substituted or unsubstituted monoring, or to bond with each other to form a substituted or unsubstituted fused ring, or not bond with each other, not forming the substituted or unsubstituted monoring, and not forming the substituted or unsubstituted fused ring. ４０１ and R ４０２ Each of these is independently a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming heterocyclic group with 5-50 atoms, R ４０３ ~R ４０５ , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring ４２１ ~R ４２７ and R ４３７ ~R ４４０ Each of these independently comprises a hydrogen atom or a substituent R. Ｘ The substituent R Ｘ This is the substituent R in formula (41-1) above. Ｘ (This is synonymous with...)

[0286] (Method for producing the compound represented by formula (41)) The compound represented by formula (41) can be produced by known methods. The compound represented by formula (41) can also be produced by following known methods and using known alternative reactions and raw materials that are suitable for the target product.

[0287] (Specific examples of compounds represented by formula (41)) Examples of compounds represented by formula (41) include the following compounds. In the following examples, D represents a deuterium atom, Me represents a methyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296] In one embodiment, the substituents in the "substituted or unsubstituted" cases of each formula are an unsubstituted C1-C50 alkyl group, an unsubstituted C2-C50 alkenyl group, an unsubstituted C2-C50 alkynyl group, an unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R ９０１ａ ) (Caution ９０２ａ ) (Caution ９０３ａ ), -O-(R ９０４ａ ), -S-(R ９０５ａ ), -N(R ９０６ａ ) (Caution ９０７ａ ), halogen atoms, cyano groups, nitro groups, unsubstituted aryl groups with 6 to 50 ring-forming carbon atoms, or unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms, R ９０１ａ ~R ９０７ａ Each of these is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R ９０１ａ If there are two or more, then there are two or more R ９０１ａ They are either identical or different from each other, R ９０２ａ If there are two or more, then there are two or more R ９０２ａ They are either identical or different from each other, R ９０３ａ If there are two or more, then there are two or more R ９０３ａ They are either identical or different from each other, R ９０４ａ If there are two or more, then there are two or more R ９０４ａ They are either identical or different from each other, R ９０５ａ If there are two or more, then there are two or more R ９０５ａ They are either identical or different from each other, R ９０６ａ If there are two or more, then there are two or more R９０６ａ They are either identical or different from each other, R ９０７ａ If there are two or more, then there are two or more R ９０７ａ They are either identical or different from one another.

[0297] In one embodiment, the substituent in the phrase "substituted or unsubstituted" in each of the above formulas is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.

[0298] In one embodiment, the substituent in the phrase "substituted or unsubstituted" in each of the above formulas is an unsubstituted C1-C18 alkyl group, an unsubstituted ring-forming C6-C18 aryl group, or an unsubstituted ring-forming C5-C18 heterocyclic group.

[0299] (Maximum Peak Wavelength) In the third embodiment, the maximum peak wavelength of the phosphorescent metal complex and the maximum peak wavelength of the third compound as a fluorescent material are preferably 480 nm or less, and more preferably 475 nm or less, independently of each other. In the third embodiment, the maximum peak wavelength of the phosphorescent metal complex and the maximum peak wavelength of the third compound as a fluorescent material are preferably 430 nm or more, and more preferably 440 nm or more, independently of each other. In this specification, the maximum peak wavelength of fluorescence emission may be referred to as the maximum peak wavelength of fluorescence emission, and the maximum peak wavelength of phosphorescence emission may be referred to as the maximum peak wavelength of phosphorescence emission. In the organic EL element of the third embodiment, the phosphorescent metal complex and the fluorescent material preferably exhibit blue emission. In this specification, blue emission means emission in which the maximum peak wavelength of the emission spectrum (fluorescence spectrum or phosphorescence spectrum) is in the range of 430 nm or more and 480 nm or less.

[0300] (Emission Spectrum Half Width) In the third embodiment, the emission spectrum half width FWHM of the third compound as a fluorescent material is preferably 40 nm or less, and more preferably 30 nm or less. In the third embodiment, the emission spectrum half width FWHM of the third compound as a fluorescent material is preferably 5 nm or more, and more preferably 10 nm or more. FWHM is an abbreviation for full width at half maximum.

[0301] In this specification, the maximum fluorescence emission peak wavelength is defined as the wavelength at which the compound being measured is 10 －６ Moles / liter or more, 10 －５ For a toluene solution dissolved at a concentration of moles / liter or less, the fluorescence spectrum measured is defined as the wavelength at which the emission intensity is maximized. The emission spectrum half-width (FWHM) is the full width at half-width at the peak of the fluorescence spectrum. A fluorescence spectrum analyzer can be used to measure the fluorescence spectrum. For example, a fluorescence spectrum analyzer manufactured by JASCO Corporation (model name: FP-8300) can be used. However, the fluorescence spectrum analyzer is not limited to the example given here.

[0302] The maximum phosphorescence peak wavelength can be measured by the following method: The compound to be measured is placed in EPA (diethyl ether:isopentane:ethanol = 5:5:2 (volume ratio)) and 10 －５ mol / L or more 10 －４ Dissolve the EPA to a concentration of mol / L or less, and place this EPA solution in a quartz cell to prepare the measurement sample. Measure the phosphorescence spectrum of this sample at a low temperature (77 K) (vertical axis: phosphorescence intensity, horizontal axis: wavelength). The maximum value at the shortest wavelength among the maximum values ​​of this phosphorescence spectrum is defined as the maximum phosphorescence peak wavelength. A spectrofluorometer F-7000 (manufactured by Hitachi High-Tech Science Corporation) can be used to measure phosphorescence. However, the measurement apparatus is not limited to this; a combination of a cooling device, a low-temperature container, an excitation light source, and a light-receiving device may also be used.

[0303] (Stokes shift) In the third embodiment, the Stokes shift of the third compound as a fluorescent material is preferably 25 nm or less, and more preferably 20 nm or less. In the third embodiment, the Stokes shift of the third compound as a fluorescent material is preferably 5 nm or more, and more preferably 10 nm or more. By having a Stokes shift of 20 nm or less of the third compound, the excitation energy can be reduced. By having a Stokes shift of 10 nm or more of the third compound, self-absorption can be suppressed and the loss of efficiency can be reduced. The Stokes shift can be measured by the method described below. The compound to be measured is measured in 2.0 × 10⁻⁶ －５ Prepare the sample for measurement by dissolving the compound in toluene at a concentration of mol / L. Irradiate the sample, placed in a quartz cell, with continuous ultraviolet-visible light at room temperature (300 K) and measure the absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength). A spectrophotometer can be used for absorption spectrum measurement; for example, Hitachi High-Tech Science's U-3900 / 3900H spectrophotometer can be used. Also, the compound to be measured should be 4.9 × 10⁻⁶ －６ Prepare a sample for measurement by dissolving the substance in toluene at a concentration of mol / L. Irradiate the sample, placed in a quartz cell, with excitation light at room temperature (300 K) and measure the fluorescence spectrum (vertical axis: fluorescence intensity, horizontal axis: wavelength). A spectrophotometer can be used for fluorescence spectrum measurement; for example, the Hitachi High-Tech Science F-7000 spectrofluorometer can be used. From these absorption and fluorescence spectra, calculate the difference between the absorption maximum wavelength and the fluorescence maximum wavelength to determine the Stokes shift (SS). The unit of Stokes shift SS is nm.

[0304] In the third embodiment, if at least one of the one or more light-emitting layers contains a first host material and a fluorescent material, it is preferable that when the organic EL element is made to emit light, the fluorescent compound in the light-emitting layer emits light primarily.

[0305] The maximum peak wavelength of light emitted from an organic EL element is measured as follows: Current density is 10 mA / cm². ２The spectral radiance spectrum of an organic EL element is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta) when a voltage is applied to the element in such a manner. The peak wavelength of the emission spectrum with the maximum emission intensity is measured from the obtained spectral radiance spectrum and defined as the maximum peak wavelength (unit: nm).

[0306] (Compound content in the light-emitting layer) The content of the first host material (first compound) and the dopant material contained in the light-emitting layer is preferably within the following ranges, for example. In this specification, the compound content in the light-emitting layer refers to the compound content contained in a single layer. The content of the first host material is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. The content of the first host material may also be 90% by mass or more and 99.9% by mass or less, 95% by mass or more and 99% by mass or less, or 99% by mass or more and 99.9% by mass or less. The content of the dopant material is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less. The third embodiment does not exclude the case in which at least one of the one or more light-emitting layers contains materials other than the first host material and the dopant material. At least one of the one or more light-emitting layers may contain only one type of first host material, or two or more types. At least one of the one or more light-emitting layers may contain only one type of dopant material, or two or more types.

[0307] (Thickness of the light-emitting layer) The thickness of the light-emitting layer in the organic EL element of the third 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 of the light-emitting layer is 5 nm or more, it is easier to form the light-emitting layer and adjust the chromaticity, and when the thickness of the light-emitting layer is 50 nm or less, it is easier to suppress the rise in the driving voltage. In this specification, the thickness of the light-emitting layer refers to the thickness of a single light-emitting layer when the organic EL element has one light-emitting layer, and refers to the thickness of each layer of the multiple light-emitting layers when the element has multiple light-emitting layers. In other words, when the element has multiple light-emitting layers, the thickness of each layer is preferably 5 nm or more and 50 nm or less.

[0308] Let's further explain the configuration of the organic EL element.

[0309] (Substrate) The substrate is used as a support for the organic EL element. Examples of substrates include glass, quartz, and plastic. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples include plastic substrates. Examples of materials for forming a plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. An inorganic vapor-deposited film may also be used.

[0310] (Anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or more). Specifically, examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, etc. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metallic materials (e.g., titanium nitride).

[0311] These materials are typically deposited by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1% to 10% by mass of zinc oxide relative to indium oxide. Similarly, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5% to 5% by mass of tungsten oxide and 0.1% to 1% by mass of zinc oxide relative to indium oxide. Other methods such as vacuum deposition, coating, inkjet, and spin coating may also be used.

[0312] Of the layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that facilitates hole injection regardless of the anode's work function. Therefore, any material suitable for electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0313] Materials with low work functions, such as elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these, can also be used. When forming an anode using alkali metals, alkaline earth metals, or alloys containing these, vacuum deposition or sputtering methods can be used. Furthermore, when using silver paste or similar materials, coating methods or inkjet methods can be employed.

[0314] When the organic EL element is of the bottom emission type, the anode is preferably formed of a metallic material that is light-transmitting or semi-transparent, allowing light from the light-emitting layer to pass through. In this specification, light-transmitting or semi-transparent means the property of transmitting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The metallic material having light transmission or semi-transparency can be appropriately selected from the materials listed in the anode section.

[0315] When the organic EL element is of the top-emission type, the anode is a reflective electrode having a reflective layer. The reflective layer is preferably formed of a metallic material having light reflectivity. In this specification, light reflectivity means the property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The metallic material having light reflectivity can be appropriately selected from the materials listed in the anode section. The anode may consist only of a reflective layer, or it may be a multilayer structure having a reflective layer and a conductive layer (preferably a transparent conductive layer). When the anode has a reflective layer and a conductive layer, it is preferable that the conductive layer is placed between the reflective layer and the hole transport band. The conductive layer can be appropriately selected from the materials listed in the anode section.

[0316] (Cathode) For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof that have a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.

[0317] Furthermore, when forming a cathode using alkali metals, alkaline earth metals, or alloys containing these, vacuum deposition or sputtering methods can be used. Additionally, when using silver paste or similar materials, coating or inkjet methods can be employed.

[0318] Furthermore, by providing an electron injection layer, cathodes can be formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium oxide-tin oxide containing silicon oxide, regardless of the magnitude of the work function. These conductive materials can be deposited using methods such as sputtering, inkjet printing, or spin coating.

[0319] When the organic EL element is of the bottom emission type, the cathode is a reflective electrode. The reflective electrode is preferably formed from a light-reflecting metallic material. The light-reflecting metallic material can be appropriately selected from the materials listed in the cathode section.

[0320] When the organic EL element is of the top-emission type, the cathode is preferably formed of a metallic material that is light-transmitting or semi-transparent, allowing light from the light-emitting layer to pass through. The light-transmitting or semi-transparent metallic material can be appropriately selected from the materials listed in the cathode section.

[0321] The organic EL element according to the third embodiment may be a bottom-emission type organic EL element. Alternatively, the organic EL element according to this embodiment may be a top-emission type organic EL element. When the organic EL element is a bottom-emission type, it is preferable that the anode is a light-transmitting electrode and the cathode is a light-reflecting electrode. When the organic EL element is a top-emission type, it is preferable that the anode is a light-reflecting electrode and the cathode is a light-transmitting electrode.

[0322] (Capping Layer) When an organic EL element is of the top-emission type, the organic EL element usually has a capping layer above the cathode. The capping layer may contain, for example, at least one compound selected from the group consisting of polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitride, and silicon compounds (such as silicon oxide). The capping layer may also contain, for example, at least one compound selected from the group consisting of aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, or dibenzofuran derivatives. A laminate in which layers containing these materials are stacked can also be used as a capping layer.

[0323] (Hole Injection Layer) The hole injection layer is a layer containing a material with high hole injection properties. Examples of materials with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide. Furthermore, substances with high hole injection potential include low-molecular-weight organic compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviated as DNTPD), 1, Aromatic amine compounds such as 3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviated as DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviated as PCzPCN1) can also be used. Furthermore, high molecular weight compounds (oligomers, dendrimers, polymers, etc.) can be used as substances with high hole injection capabilities. Examples of high molecular weight compounds include poly(N-vinylcarbazole) (abbreviated as PVK), poly(4-vinyltriphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD).Furthermore, polymer compounds to which acids such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) have been added can also be used.

[0324] (Hole Transport Layer) The hole transport layer is a layer containing a substance with high hole transport properties. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used in the hole transport layer. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl Aromatic amine compounds such as phenyl (abbreviated as DFLDPBi), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB) can be used. The substances described here are mainly 10 －６ cm ２ The material has a hole mobility of 1 / Vs or higher. Carbazole derivatives such as CBP, CzPA, and PCzPA, or anthracene derivatives such as t-BuDNA, DNA, and DPANth may be used for the hole transport layer. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) may also be used. However, other materials may be used as long as they have higher hole transport capabilities than electron transport capabilities. The layer containing the material with high hole transport capabilities may be a single layer or a layer consisting of two or more layers of the above materials stacked together.

[0325] (Electron Transport Layer) The electron transport layer is a layer containing a material with high electron transport properties. The electron transport layer can contain: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymer compounds. Specifically, low-molecular-weight organic compounds such as Alq and tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq) can be used. ３ ), bis(10-hydroxybenzo[h]quinolinate)beryllium (abbreviation: BeBq) ２ ), BAlq, Znq, ZnPBO, ZnBTZ and other metal complexes can be used. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: Heteroaromatic compounds such as (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), vasophenanthroline (abbreviated as BPhen), vasocuproin (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviated as BzOs) can also be used. The substances described here are mainly 10 －６ cm ２The material has an electron mobility of 1 / Vs or higher. However, any material with higher electron transport properties than hole transport properties may be used as the electron transport layer. Furthermore, the electron transport layer may be a single layer or a layer consisting of two or more layers of the above material. Polymer compounds can also be used for the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy), etc., can be used.

[0326] (Electron injection layer) The electron injection layer is a layer containing a material with high electron injection potential. The electron injection layer contains lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF) ２Alkali metals such as lithium oxide (LiOx), alkaline earth metals, or compounds thereof can be used. In addition, materials containing alkali metals, alkaline earth metals, or compounds thereof in an electron-transporting substance, specifically those containing magnesium (Mg) in Alq, may be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, a composite material made by mixing an organic compound and an electron donor may be used in 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 substances that constitute the electron transport layer described above (metal complexes, heteroaromatic compounds, etc.) can be used. As for the electron donor, any substance that exhibits electron-donating properties to the organic compound is acceptable. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples include lithium, cesium, magnesium, calcium, erbium, and ytterbium. Furthermore, alkali metal oxides and alkaline earth metal oxides are preferred, including lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (abbreviated as TTF) can also be used.

[0327] (Layer Formation Method) The method for forming each layer of the organic EL element according to any of the embodiments described above is not limited to those specifically mentioned above, but known methods such as dry deposition methods such as vacuum deposition, sputtering, plasma deposition, and ion plating, and wet deposition methods such as spin coating, dipping, flow coating, and inkjet deposition can be employed.

[0328] (Film Thickness) The film thickness of each layer included in the light-emitting unit of the organic EL element according to the third embodiment is not limited unless otherwise specifically mentioned above. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and if the film thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the film thickness of each layer included in the light-emitting unit of the organic EL element is usually preferably in the range of a few nanometers to 1 μm.

[0329] According to the organic EL element of the third embodiment, the lifespan of the organic EL element can be improved. According to one embodiment of the organic EL element of the third embodiment, the lifespan of the organic EL element can be improved by incorporating a phosphorescent complex (preferably a blue phosphorescent complex) and a compound according to the first embodiment (first compound) as a first host material into the light-emitting layer. According to one embodiment of the organic EL element of the third embodiment, the lifespan of the organic EL element can be improved by incorporating a fluorescent material (preferably a blue fluorescent material) and a compound according to the first embodiment (first compound) as a first host material into the light-emitting layer. The organic EL element of the third embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0330] [Fourth Embodiment] The configuration of the organic EL element according to the fourth embodiment will now be described. In the description of the fourth embodiment, components identical to those in the third embodiment will be given the same reference numerals and names, and their descriptions will be omitted or simplified. In addition, in the fourth embodiment, materials and compounds not specifically mentioned can be the same as those described in the third embodiment.

[0331] (Light-emitting layer) In the organic EL element according to the fourth embodiment, at least one of the one or more light-emitting layers contains a first host material, a sensitizing material, and a fluorescent material. In other respects, it is the same as the organic EL element according to the third embodiment. The first host material, the sensitizing material, and the fluorescent material are different materials from each other. In the fourth embodiment, the compound used as the sensitizing material may be referred to as the second compound. That is, in the fourth embodiment, at least one of the one or more light-emitting layers contains a first host material (first compound), a sensitizing material (second compound), and a fluorescent material (third compound).

[0332] In the fourth embodiment, the sensitizing material is one or more compounds selected from the group consisting of phosphorescent metal complexes and delayed-fluorescence compounds. In one aspect of the fourth embodiment, at least one of the one or more light-emitting layers contains a first host material, a delayed-fluorescence compound as a sensitizing material, and a fluorescent material. In this aspect, it is preferable that at least one of the one or more light-emitting layers does not contain a phosphorescent metal complex. In one aspect of the fourth embodiment, at least one of the one or more light-emitting layers contains a first host material, a phosphorescent metal complex as a sensitizing material, and a fluorescent material.

[0333] In the fourth embodiment, the first host material, the sensitizing material, and the fluorescent material are contained in a single layer. For example, if the organic EL element has one light-emitting layer, the first host material, the sensitizing material, and the fluorescent material are contained in that single light-emitting layer. If it has multiple light-emitting layers, the first host material, the sensitizing material, and the fluorescent material are contained in one of the single light-emitting layers.

[0334] [First host material] In the fourth embodiment, the first host material is the compound according to the first embodiment (the compound represented by formula (1) above (the first compound)).

[0335] [Fluorescent material] In the fourth embodiment, the fluorescent material can be the same material as the fluorescent material (third compound) described in the third embodiment.

[0336] [Sensitizing material] In the fourth embodiment, the sensitizing material is one or more compounds selected from the group consisting of phosphorescent metal complexes and delayed-fluorescence compounds.

[0337] (Phosphorescent metal complex) In the fourth embodiment, the phosphorescent metal complex can be the same material as the phosphorescent metal complex described in the third embodiment.

[0338] (Delayed fluorescence compound) In the fourth embodiment, the delayed fluorescence compound is not a phosphorescent metal complex. In the fourth embodiment, it is preferable that the delayed fluorescence compound is not a metal complex.

[0339] In the fourth embodiment, the delayed-fluorescence compound is preferably a compound represented by the following formula (H1).

[0340]

[0341] (In the above formula (H1), A Ｈ D is a group having at least one substructure selected from the group consisting of the following formulas (a-1), (a-2), (a-3), (a-4), (a-5), (a-6), (a-7), and (a-8), Ｈ L is a group represented by the following formulas (221), (222), or (223). Ｈ m is a single-bonded, substituted, or unsubstituted aryl ring with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle with 5 to 50 ring-forming atoms, where m is 1, 2, 3, 4, or 5, and there are multiple A Ｈ They are either identical or different from each other, n is 1, 2, 3, 4 or 5, and there are multiple D Ｈ (They are either identical or different to each other.)

[0342]

[0343] (In formulas (a-1) to (a-8) above, * independently indicates the bonding position with other atoms in the molecule of the delayed-fluorescence compound.)

[0344]

[0345]

[0346]

[0347] (R in formula (221) above) ２１ ~R ２８ One or more pairs of adjacent elements from among them either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine with each other, and R in formula (222) ２２１ ~R ２２８ One or more pairs of adjacent elements from among them either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine with each other, and R in formula (223) ２３１ ~R ２３８ One or more pairs of adjacent R elements either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine to form a substituted or unsubstituted monoring in formula (221) and do not form a substituted or unsubstituted fused ring. ２１ ~R ２８ R that does not form a substituted or unsubstituted monoring in formula (222) and does not form a substituted or unsubstituted condensed ring. ２２１ ~R ２２８ Furthermore, R that does not form a substituted or unsubstituted monoring in formula (223) and does not form a substituted or unsubstituted fused ring. ２３１ ~R ２３８ Each of these independently consists of a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C1-C50 haloalkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ A group represented by ) -O-(R ９０４ A group represented by ) -S-(R ９０５A group represented by ) -N(R ９０６ ) (Caution ９０７ A group represented by ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R ９０８ The base represented by -COOR ９０９ Groups represented by, halogen atoms, cyano groups, nitro groups, -P(=O)(R ９３１ ) (Caution ９３２ The group represented by ) -Ge(R ９３３ ) (Caution ９３４ ) (Caution ９３５ A group represented by ) -B(R ９３６ ) (Caution ９３７ A group represented by ), a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, in formulas (222) and (223), each ring A, ring B and ring C are independently selected from the group consisting of ring structures represented by formulas (224) and (225) below, each ring A, ring B and ring C are condensed with adjacent rings at any position, each p, px and py are independently 1, 2, 3 or 4, when p is 2, 3 or 4, the multiple rings A are either identical or different from each other, when px is 2, 3 or 4, the multiple rings B are either identical or different from each other, when py is 2, 3 or 4, the multiple rings C are either identical or different from each other, and in formulas (221) to (223), * is L Ｈ (This indicates the bonding position.)

[0348]

[0349] (In the above formula (224), r is 0, 2, or 4, and multiple R ２９ A set consisting of these elements may combine with each other to form a substituted or unsubstituted monoring, or combine with each other to form a substituted or unsubstituted fused ring, or not combine with each other, in formula (225), X Ａ is a sulfur atom, an oxygen atom, or C(R) ２９１ ) (Caution ２９２ ) and R ２９１ and R ２９２A set consisting of these elements may bond to each other to form a substituted or unsubstituted monoring, or bond to each other to form a substituted or unsubstituted fused ring, or not bond to each other, not form a substituted or unsubstituted monoring, and not form a substituted or unsubstituted fused ring. ２９ , R ２９１ and R ２９２ Each of these independently consists of a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C1-C50 haloalkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ A group represented by ) -O-(R ９０４ A group represented by ) -S-(R ９０５ A group represented by ) -N(R ９０６ ) (Caution ９０７ A group represented by ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R ９０８ The base represented by -COOR ９０９ Groups represented by, halogen atoms, cyano groups, nitro groups, -P(=O)(R ９３１ ) (Caution ９３２ The group represented by ) -Ge(R ９３３ ) (Caution ９３４ ) (Caution ９３５ A group represented by ) -B(R ９３６ ) (Caution ９３７ A group represented by ), a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and multiple R ２９ These are either identical or different from each other, and multiple R ２９１ These are either identical or different from each other, and multiple R ２９２ These are either identical or different from each other, multiple X Ａ (They are either identical or different to each other.)

[0350] (Among the delayed-fluorescence compounds, 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 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group, and R ９０１ If multiple R ９０１ They are either identical or different from each other, R ９０２ If multiple R ９０２ They are either identical or different from each other, R ９０３ If multiple R ９０３ They are either identical or different from each other, R ９０４ If multiple R ９０４ They are either identical or different from each other, R ９０５ If multiple R ９０５ They are either identical or different from each other, R ９０６ If multiple R ９０６ They are either identical or different from each other, R ９０７ If multiple R ９０７ They are either identical or different from each other, R ９０８ If multiple R ９０８ They are either identical or different from each other, R ９０９ If multiple R ９０９ They are either identical or different from each other, R ９３１ If multiple R ９３１ They are either identical or different from each other, R９３２ If multiple R ９３２ They are either identical or different from each other, R ９３３ If multiple R ９３３ They are either identical or different from each other, R ９３４ If multiple R ９３４ They are either identical or different from each other, R ９３５ If multiple R ９３５ They are either identical or different from each other, R ９３６ If multiple R ９３６ They are either identical or different from each other, R ９３７ If multiple R ９３７ (They are either identical or different to each other.)

[0351] In the fourth embodiment, the delayed-fluorescence compound is preferably a compound represented by the following formula (H10).

[0352]

[0353] (In the above formula (H10), CN is a cyano group, L Ｈ D is a substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 30 carbon atoms. １１ and D １２ Each of these is independently a group represented by the above formulas (221), (222), or (223), where m is 1, 2, 3, 4, or 5, nx is 0, 1, 2, 3, 4, or 5, ny is 0, 1, 2, 3, 4, or 5, nx + ny is 1, 2, 3, 4, or 5, D １１ and D １２ These are either identical or different from each other, and multiple D １１ These are either identical or different from each other, and multiple D １２ (They are either identical or different to each other.)

[0354] In the fourth embodiment, the delayed-fluorescence compound is preferably a compound represented by the following formula (H100).

[0355]

[0356] (In the above formula (H100), L Ｈ , D １１ , D １２ , m, nx, and ny are, respectively, L in formula (H10) Ｈ , D １１ , D １２ ,m,nx and ny are synonymous, and R is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C1-C50 haloalkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ A group represented by ) -O-(R ９０４ A group represented by ) -S-(R ９０５ A group represented by ) -N(R ９０６ ) (Caution ９０７ A group represented by ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R ９０８ The base represented by -COOR ９０９ The group represented by, cyano group, nitro group, -P(=O)(R ９３１ ) (Caution ９３２ The group represented by ) -Ge(R ９３３ ) (Caution ９３４ ) (Caution ９３５ A group represented by ) -B(R ９３６ ) (Caution ９３７ A group represented by (H100), a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, wherein at least one R is a substituent, and at least one R as a substituent is L of the compound represented by the formula (H100). Ｈ (Bonded to each other by carbon-carbon bonds, where k is an integer greater than or equal to 1, and multiple Rs are either identical or different from each other.)

[0357] In the fourth embodiment, the delayed-fluorescence compound is preferably a compound represented by the following formula (H101).

[0358]

[0359] (In the above formula (H101), D １１ and D １２ These are, respectively, D in the above formula (H10). １１ and D １２ This is equivalent to the above equation (H100), where R is independently equivalent to R in the above equation (H100), m is 1, 2, 3 or 4, nx is 0, 1, 2, 3 or 4, ny is 0, 1, 2, 3 or 4, k is 1, 2, 3 or 4, nx + ny is 1, 2, 3 or 4, and m + nx + ny + k = 6.

[0360] In the fourth embodiment, the delayed-fluorescence compound is preferably a compound represented by the following formulas (H110), (H120), or (H130).

[0361]

[0362] (In the above formulas (H110), (H120), and (H130), D １１ and D １２ These are, respectively, D in the above formula (H10). １１ and D １２ This is equivalent to the above equation (H100), where R is independently equivalent to R in the above equation (H100), nx is 0, 1, 2, or 3, ny is 0, 1, 2, or 3, k is 1, 2, or 3, nx + ny is 1, 2, or 3, and nx + ny + k = 4.

[0363] In the fourth embodiment, the group represented by formula (222) in the delayed-fluorescence compound is preferably one of the groups selected from the group consisting of the following formulas (22A), (22B), (22C), (22D), (22E), and (22F).

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370] (In the above formulas (22A), (22B), (22C), (22D), (22E), and (22F), R ２２１ ~R ２２８ These are, respectively, R in formula (222) above. ２２１ ~R ２２８ This is synonymous with R ２２９ and R ２３０ Each of these independently corresponds to R in equation (224) above. ２９ This is synonymous with X Ａ X in equation (225) is Ａ This is synonymous, and the * in formulas (22A), (22B), (22C), (22D), (22E), and (22F) indicates the bonding position.

[0371] In the organic EL element according to the fourth embodiment, when the delayed fluorescence compound is a compound represented by formula (H101), the * in formulas (22A), (22B), (22C), (22D), (22E), and (22F) is bonded to the benzene ring itself, as explicitly shown in formula (H101).

[0372] In the delayed fluorescence compound of the fourth embodiment, X Ａ It is also preferable that this atom be a sulfur atom or an oxygen atom.

[0373] In the delayed fluorescence compound of the fourth embodiment, X Ａ However, C(R ２９１ ) (Caution ２９２ ) If R ２９１ and R ２９２Each of these is preferably independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group, and more preferably a substituted or unsubstituted C1-C50 alkyl group, or a substituted or unsubstituted ring-forming C6-C50 aryl group.

[0374] In the delayed fluorescence compound of the fourth embodiment, R ２１ ~R ２８ It is also preferable that no two or more adjacent pairs of these pairs are bonded to each other. In the delayed fluorescence compound of the fourth embodiment, R ２２１ ~R ２２８ It is also preferable that no two or more adjacent pairs of these pairs are bonded to each other. In the delayed fluorescence compound of the fourth embodiment, R ２３１ ~R ２３８ It is also preferable that any set of two or more adjacent elements does not combine with each other.

[0375] In the delayed-fluorescence compound of the fourth embodiment, R is preferably independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heterocyclic group.

[0376] In the delayed-fluorescence compound of the fourth embodiment, R is preferably independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted ring-forming C6-C18 aryl group, or a substituted or unsubstituted ring-forming C5-C18 heterocyclic group.

[0377] R in the delayed fluorescence compound of the fourth embodiment ２１ ~R ２８ , R ２２１ ~R ２２８ , R ２３１ ~R ２３８、 And R ２９Preferably, each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heterocyclic group.

[0378] R in the delayed fluorescence compound of the fourth embodiment ２１ ~R ２８ , R ２２１ ~R ２２８ , R ２３１ ~R ２３８、 And R ２９ Preferably, each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted ring-forming C6-C18 aryl group, or a substituted or unsubstituted ring-forming C5-C18 heterocyclic group.

[0379] In the delayed fluorescence compound of the fourth embodiment, R is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heterocyclic group. ２１ ~R ２８ , R ２２１ ~R ２２８ , R ２３１ ~R ２３８、 And R ２９ Preferably, each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heterocyclic group.

[0380] In the delayed fluorescence compound of the fourth embodiment, R is independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted ring-forming C6-C18 aryl group, or a substituted or unsubstituted ring-forming C5-C18 heterocyclic group. ２１ ~R ２８ , R ２２１ ~R ２２８ , R ２３１ ~R ２３８、 And R２９ Preferably, each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted ring-forming C6-C18 aryl group, or a substituted or unsubstituted ring-forming C5-C18 heterocyclic group.

[0381] In the compound according to the fourth embodiment, the substituents in the case of "substituted or unsubstituted" are: an unsubstituted C1-C25 alkyl group, an unsubstituted C2-C25 alkenyl group, an unsubstituted C2-C25 alkynyl group, an unsubstituted ring-forming C3-C25 cycloalkyl group, and -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ A group represented by ) -O-(R ９０４ A group represented by ) -S-(R ９０５ A group represented by ) -N(R ９０６ ) (Caution ９０７ A group represented by ), an unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R ９０８ The base represented by -COOR ９０９ The group represented by -P(=O)(R ９３１ ) (Caution ９３２ The group represented by ) -Ge(R ９３３ ) (Caution ９３４ ) (Caution ９３５ A group represented by ) -B(R ９３６ ) (Caution ９３７ A base represented by ), -S (=O) ２ R ９３８ The group represented by , a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group with 6 to 25 ring-forming carbon atoms, or an unsubstituted heterocyclic group with 5 to 25 ring-forming atoms, R ９０１ ~R ９０９ , and R ９３１ ~R ９３８ Preferably, each of these is independently a hydrogen atom, an unsubstituted C1-C25 alkyl group, an unsubstituted ring-forming C6-C25 aryl group, or an unsubstituted ring-forming C5-C5 heterocyclic group.

[0382] In the compound according to the fourth embodiment, the substituent in the case of "substituted or unsubstituted" is preferably a halogen atom, an unsubstituted C1 to C25 alkyl group, an unsubstituted ring-forming C6 to C25 aryl group, or an unsubstituted ring-forming C5 to C25 heterocyclic group.

[0383] In the compound according to the fourth embodiment, the substituent in the case of "substituted or unsubstituted" is preferably an unsubstituted C1-C10 alkyl group, an unsubstituted ring-forming C6-C12 aryl group, or an unsubstituted ring-forming C5-C12 heterocyclic group.

[0384] In the compound according to the fourth embodiment, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0385] In this specification, when a delayed-fluorescence compound is a sensitizing material, the lowest excitation singlet energy of the delayed-fluorescence compound is S. １ (GT2) refers to the energy gap of a delayed-fluorescence compound at 77 [K] as T ７７Ｋ (GT2) is called S １ (GT2) and T ７７Ｋ The difference from (GT2) is sometimes referred to as ΔST(GT2).

[0386] (Method for producing delayed-fluorescence compounds) The delayed-fluorescence compounds in the fourth embodiment can be produced by known methods. Alternatively, the delayed-fluorescence compounds can also be produced by following known methods and using known alternative reactions and raw materials tailored to the target product.

[0387] (Specific examples of delayed-fluorescence compounds) Specific examples of delayed-fluorescence compounds in the fourth embodiment include, for example, the following compounds. However, the present invention is not limited to these specific examples.

[0388]

[0389]

[0390]

[0391]

[0392]

[0393] (Relationship between the first host material, sensitizing material, and fluorescent material in the light-emitting layer) In one embodiment of the fourth embodiment, the sensitizing material is a delayed-fluorescence compound. In one embodiment of the fourth embodiment, at least one of the one or more light-emitting layers contains a delayed-fluorescence compound as the sensitizing material and does not need to contain a phosphorescent metal complex.

[0394] Figure 4 shows an example of the relationship between the energy levels of the first host material (first compound), the delayed-fluorescence compound (second compound) as a sensitizer, and the fluorescent material (third compound) in the light-emitting layer. In Figure 4, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the first host material, and T1(M1) represents the lowest excited triplet state of the first host material. S1(M2) represents the lowest excited singlet state of the delayed-fluorescence compound, and T1(M2) represents the lowest excited triplet state of the delayed-fluorescence compound. S1(M3) represents the lowest excited singlet state of the fluorescent material, and T1(M3) represents the lowest excited triplet state of the fluorescent material. The dashed arrow from S1(M2) to S1(M3) in Figure 4 represents the Förster-type energy transfer from the lowest excited singlet state of the delayed-fluorescence compound to the lowest excited singlet state of the fluorescent material. As shown in Figure 4, when a compound with a small ΔST(M2) is used as the delayed fluorescence compound, the lowest excited triplet state T1(M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) due to thermal energy. Then, a Förster-type energy transfer occurs from the lowest excited singlet state S1(M2) of the delayed fluorescence compound to the fluorescent material, generating the lowest excited singlet state S1(M3). As a result, fluorescence emission from the lowest excited singlet state S1(M3) of the fluorescent material can be observed. It is believed that by utilizing delayed fluorescence through this TADF mechanism, the internal quantum efficiency can theoretically be increased to 100%.

[0395] In one embodiment, the lowest excitation singlet energy S of the delayed-fluorescence compound １ (GT2) and the lowest excitation singlet energy S of the fluorescent material １It is also preferable that (D) and satisfy the relationship shown in the following formula (Equation 4). １ (GT2) > S １ (D) ... (Math 4)

[0396] In one embodiment, the lowest excitation singlet energy S of the first host material １ (H1) and the lowest excitation singlet energy S of the delayed fluorescence compound １ It is also preferable that (GT2) and satisfy the relationship shown in the following formula (Equation 4A). １ (H1) > S １ (GT2) ... (Math 4A)

[0397] In one embodiment, the lowest excitation singlet energy S of the first host material, the delayed fluorescence compound, and the fluorescence-emitting material is １ It is also preferable that the following equation (Mathematics 4B) satisfies the relationship. １ (H1) > S １ (GT2) > S １ (D) ... (Math 4B)

[0398] In one embodiment, the energy gap T at 77 [K] between the first host material and the delayed fluorescence compound is ７７Ｋ It is also preferable that the following equation (Equation 6) satisfies the relationship T. ７７Ｋ (H1)>T ７７Ｋ (GT2) ... (Math 6)

[0399] In one embodiment, the energy gap T of the delayed-fluorescence compound at 77 [K] ７７Ｋ (GT2) and the energy gap T at 77 [K] for fluorescent materials. ７７Ｋ It is also preferable that (D) and satisfy the relationship shown in the following formula (Equation 6A). ７７Ｋ (GT2) > T ７７Ｋ (D) ... (Math 6A)

[0400] In one embodiment, the first host material, the delayed fluorescence compound, and the fluorescence-emitting material have an energy gap T at 77 [K]. ７７Ｋ It is also preferable that the following equation (Mathematics 6B) satisfies the relationship. ７７Ｋ (H1)>T ７７Ｋ (GT2) > T ７７Ｋ (D) ...(Math 6B)

[0401] In one embodiment, the sensitizing material is a phosphorescent metal complex. In one embodiment, at least one of the one or more light-emitting layers contains a phosphorescent metal complex as the sensitizing material and does not necessarily contain a delayed-fluorescence compound.

[0402] Figure 5 shows an example of the relationship between the energy levels of the first host material (first compound), the phosphorescent metal complex as a sensitizer (second compound), and the fluorescent material (third compound) in the light-emitting layer. In Figure 5, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the first host material, and T1(M1) represents the lowest excited triplet state of the first host material. S1(M2) represents the lowest excited singlet state of the phosphorescent metal complex, and T1(M2) represents the lowest excited triplet state of the phosphorescent metal complex. S1(M3) represents the lowest excited singlet state of the fluorescent material, and T1(M3) represents the lowest excited triplet state of the fluorescent material. The dashed arrow in Figure 5, pointing from T1(M2) to S1(M3), represents dipole-type energy transfer from the lowest excited triplet state of the phosphorescent metal complex to the lowest excited singlet state of the fluorescent material. As shown in Figure 5, when a phosphorescent metal complex is used as a sensitizer, the lowest excited singlet state S1(M2) of the phosphorescent metal complex can inter-system cross to the lowest excited triplet state T1(M2) due to spin-orbit interaction and heavy atom effects. Then, dipole-type energy transfer occurs from the lowest excited triplet state T1(M2) of the phosphorescent metal complex to the fluorescent material, generating the lowest excited singlet state S1(M3). As a result, fluorescence emission from the lowest excited singlet state S1(M3) of the fluorescent material can be observed. It is believed that by utilizing this mechanism, the internal quantum efficiency can be theoretically increased to 100%.

[0403] In one embodiment, the energy gap T at 77 [K] of the phosphorescent metal complex ７７Ｋ (GP2) and the lowest excitation singlet energy S of the fluorescent material １ It is also preferable that (D) and satisfy the relationship shown in the following formula (Equation 3). ７７Ｋ (GP2) > S １(D) ... (Math 3)

[0404] In one embodiment, the energy gap T at 77 [K] between the first host material and the phosphorescent metal complex is ７７Ｋ It is also preferable that the following equation (Mathematics 3A) satisfies the relationship. ７７Ｋ (H1)>T ７７Ｋ (GP2) …(Math 3A)

[0405] In one embodiment, the energy gap T at 77 [K] between the first host material and the phosphorescent metal complex is ７７Ｋ And the lowest excitation singlet energy S of the fluorescent material １ It is also preferable that (D) and satisfy the following relationship (Mathematics 3B). ７７Ｋ (H1)>T ７７Ｋ (GP2) > S １ (D) ...(Math 3B)

[0406] The lowest singlet excitation energy S of a fluorescent material １ (D) and the energy gap T at 77 [K] of the fluorescent material. ７７Ｋ (D) usually satisfies the following relationship (Equation 3C). １ (D) > T ７７Ｋ (D) ...(Math 3C)

[0407] In one embodiment, the lowest excitation singlet energy S of the first host material １ (H1) and the lowest excitation singlet energy S of the phosphorescent metal complex １ It is also preferable that (GP2) and satisfy the relationship shown in the following formula (Equation 5). １ (H1) > S １ (GP2) ... (Math 5)

[0408] In one embodiment, the lowest excitation singlet energy S of the phosphorescent metal complex １ (GP2) and the lowest excitation singlet energy S of the fluorescent material １ It is also preferable that (D) and satisfy the relationship shown in the following formula (Equation 5A). １ (GP2) > S １ (D) ...(Number 5A)

[0409] In one embodiment, the lowest excitation singlet energy S of the first host material, the phosphorescent metal complex, and the fluorescent material. １ It is also preferable that the following equation (Mathematics 5B) satisfies the relationship. １ (H1) > S １ (GP2) > S １ (D) ...(Number 5B)

[0410] When the organic EL element of the fifth embodiment is made to emit light, it is preferable that at least one of the one or more light-emitting layers emits light mainly from a fluorescent compound.

[0411] (Compound content in the light-emitting layer) The content of the first host material (first compound), sensitizing material (second compound), and fluorescent material (third compound) contained in the light-emitting layer is preferably within the following ranges, for example.

[0412] The content of the first host material (first compound) in the light-emitting layer is preferably 50% by mass or more, and more preferably 70% by mass or more. The content of the first host material (first compound) in the light-emitting layer is preferably 95% by mass or less, and more preferably 90% by mass or less.

[0413] When the sensitizing material (second compound) is a delayed-fluorescence compound, the content of the delayed-fluorescence compound in the light-emitting layer is preferably 5% by mass or more, and more preferably 10% by mass or more. The content of the delayed-fluorescence compound in the light-emitting layer is preferably 50% by mass or less, and more preferably 30% by mass or less.

[0414] When the sensitizing material (second compound) is a phosphorescent metal complex, the content of the phosphorescent metal complex in the light-emitting layer is preferably 5% by mass or more, and more preferably 10% by mass or more. The content of the phosphorescent metal complex in the light-emitting layer is preferably 50% by mass or less, and more preferably 30% by mass or less.

[0415] The content of the fluorescent material (third compound) in the light-emitting layer is preferably 0.5% by mass or more, and more preferably 1% by mass or more. The content of the fluorescent material (third compound) in the light-emitting layer is preferably 10% by mass or less, and more preferably 5% by mass or less. The upper limit of the total content of the first host material (first compound), sensitizing material (second compound), and fluorescent material (third compound) in the light-emitting layer is 100% by mass. Note that this embodiment does not exclude the case in which at least one of the one or more light-emitting layers contains materials other than the first host material, sensitizing material, and fluorescent material. In the fourth embodiment, at least one of the one or more light-emitting layers may contain only one type of the first host material, sensitizing material, and fluorescent material, or two or more types.

[0416] According to the organic EL element of the fourth embodiment, the lifespan of the organic EL element can be improved. In one embodiment of the organic EL element of the fourth embodiment, the lifespan of the organic EL element can be improved by including a sensitizing material (preferably a blue sensitizing material), a compound according to the first embodiment as a first host material (first compound), and a fluorescent material (third compound) in the light-emitting layer. The organic EL element of the fourth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0417] [Fifth Embodiment] The configuration of the organic EL element according to the fifth embodiment will now be described. In the description of the fifth embodiment, components identical to those in the third and fourth embodiments will be given the same reference numerals and names, and their descriptions will be omitted or simplified. Furthermore, in the fifth embodiment, materials and compounds not specifically mentioned can be the same as those described in the third and fourth embodiments.

[0418] (Emitting Layer) In the organic EL element according to the fifth embodiment, at least one of the one or more emitting layers further contains a fourth compound as a second host material. In one embodiment of the organic EL element according to the fifth embodiment, at least one of the one or more emitting layers contains a first host material (first compound), a sensitizing material (second compound), a fluorescent material (third compound), and a fourth compound as a second host material. The first host material (first compound) and the second host material (fourth compound) are different from each other. In other respects, it is the same as the organic EL element according to the fourth embodiment. In the fifth embodiment, the first host material, the second host material, the sensitizing material, and the fluorescent material are different materials. In one embodiment of the fifth embodiment, at least one of the one or more emitting layers contains a first host material, a second host material, a delayed-fluorescence compound as a sensitizing material, and a fluorescent material. In this embodiment, it is preferable that at least one of the one or more emitting layers does not contain a phosphorescent metal complex. In one embodiment of the fifth embodiment, at least one of the one or more light-emitting layers contains a first host material, a second host material, a phosphorescent metal complex as a sensitizing material, and a fluorescent material.

[0419] In the fifth embodiment, a first host material, a second host material, a sensitizing material, and a fluorescent material are contained in a single layer. For example, if the organic EL element has one light-emitting layer, the first host material, the second host material, the sensitizing material, and the fluorescent material are contained in that single light-emitting layer. If the element has multiple light-emitting layers, the first host material, the second host material, the sensitizing material, and the fluorescent material are contained in one of the single light-emitting layers.

[0420] [First host material] In the fifth embodiment, the first host material is the compound according to the first embodiment (the compound represented by formula (1)).

[0421] [Fluorescent material] In the fifth embodiment, the fluorescent material can be the same material as the fluorescent material (third compound) described in the third embodiment.

[0422] [Sensitizing Material] In the fifth embodiment, the phosphorescent metal complex used as the sensitizing material can be the same material as the phosphorescent metal complex described in the third embodiment. In the fifth embodiment, the delayed-fluorescence compound used as the sensitizing material can be the same material as the delayed-fluorescence compound described in the fourth embodiment.

[0423] [Second host material] In the fifth embodiment, the second host material is a fourth compound containing one or more substructures selected from the group consisting of substructures represented by the following formulas (301) to (318) in a single molecule.

[0424]

[0425]

[0426] (In the above formula (301), A １１ ~A １６ These are, independently, nitrogen atoms and CR １１ , or a carbon atom that is bonded to another atom or other structure in the molecule of the fourth compound, provided that A １１ ~A １６ At least one of these is a carbon atom that is bonded to another atom or structure in the molecule of the fourth compound, R １１ If multiple R １１ These are either identical or different from each other, and multiple R １１ One or more pairs of adjacent elements from among them either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine with each other, in formula (302), A １ ~A ４ These are, independently, nitrogen atoms and CR １２ , or a carbon atom that is bonded to another atom or other structure in the molecule of the fourth compound, R １２ Each of these is independently either a hydrogen atom or a substituent, or adjacent to R １２ One or more pairs of elements join together to form a ring, R １２If multiple R １２ These are either identical or different from each other, and multiple R １２ One or more pairs of adjacent elements from among them either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine with each other, X １０ NR １３ , C(R １４ ) (Caution １５ ), Si (R １６ ) (Caution １７ ), oxygen atom, sulfur atom, nitrogen atom bonded to other atoms or other structures in the molecule of the fourth compound, R １８ and carbon atoms, or R, that are bonded to other atoms or other structures in the molecule of the fourth compound, respectively. １９ and silicon atoms that bond to other atoms or other structures in the molecule of the fourth compound, respectively, provided that A １ ~A ４ Carbon atoms in X １０ Nitrogen atom in X １０ Carbon atoms and X in １０ At least one of the silicon atoms in is bonded to other atoms or structures in the molecule of the fourth compound, R １４ and R １５ A set consisting of these elements may bond to each other to form a substituted or unsubstituted monoring, or bond to each other to form a substituted or unsubstituted fused ring, or not bond to each other, R １６ and R １７ A set consisting of these elements may bond to each other to form a substituted or unsubstituted monoring, or bond to each other to form a substituted or unsubstituted fused ring, or not bond to each other, in formula (303), R １１５ and R １１６ A set consisting of these elements may bond to each other to form a substituted or unsubstituted monoring, or bond to each other to form a substituted or unsubstituted fused ring, or not bond to each other, and in formulas (301) to (304), R may not form the substituted or unsubstituted monoring and may not form the substituted or unsubstituted fused ring.１１ , R １２ , R １４ , R １５ , R １６ , R １７ , R １１５ and R １１６ , and R １３ , R １８ , R １９ and R １１７ Each of these independently consists of a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C1-C50 haloalkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ A group represented by ) -O-(R ９０４ A group represented by ) -S-(R ９０５ A group represented by ) -N(R ９０６ ) (Caution ９０７ The group represented by -C(=O)R ９０８ The base represented by -COOR ９０９ The group represented by -P(=O)(R ９１０ ) (Caution ９１１ A group represented by -P(=O)(OR ９１２ ) ( OR ９１３ The group represented by ) -Ge(R ９１４ ) (Caution ９１５ ) (Caution ９１６ A group represented by ) -B(R ９１７ ) (Caution ９１８The group is represented by (301) to (304), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, where, in formulas (303) to (318), * represents a bonding site with another atom or other structure in the molecule of the fourth compound, and if the fourth compound has multiple substructures represented by formulas (301) to (304), the multiple substructures represented by formula (301) are either identical or different from each other, the multiple substructures represented by formula (302) are either identical or different from each other, the multiple substructures represented by formula (303) are either identical or different from each other, and the multiple substructures represented by formula (304) are either identical or different from each other.

[0427] (Among the fourth compound, R ９０１ ~R ９１８ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group, and R ９０１ If multiple R ９０１ They are either identical or different from each other, R ９０２ If multiple R ９０２ They are either identical or different from each other, R ９０３ If multiple R ９０３ They are either identical or different from each other, R ９０４ If multiple R ９０４ They are either identical or different from each other, R ９０５ If multiple R ９０５ They are either identical or different from each other, R ９０６ If multiple R ９０６ They are either identical or different from each other, R ９０７ If multiple R ９０７They are either identical or different from each other, R ９０８ If multiple R ９０８ They are either identical or different from each other, R ９０９ If multiple R ９０９ They are either identical or different from each other, R ９１０ If multiple R ９１０ They are either identical or different from each other, R ９１１ If multiple R ９１１ They are either identical or different from each other, R ９１２ If multiple R ９１２ They are either identical or different from each other, R ９１３ If multiple R ９１３ They are either identical or different from each other, R ９１４ If multiple R ９１４ They are either identical or different from each other, R ９１５ If multiple R ９１５ They are either identical or different from each other, R ９１６ If multiple R ９１６ They are either identical or different from each other, R ９１７ If multiple R ９１７ They are either identical or different from each other, R ９１８ If multiple R ９１８ (They are either identical or different to each other.)

[0428] In the above formula (302), X １０ When is "a nitrogen atom bonded to another atom or structure in the molecule of the fourth compound", then formula (302) is represented by the following formula (302-1). In formula (302), X １０ R １８ When X is a carbon atom bonded to another atom or structure in the molecule of the fourth compound, the above formula (302) is represented by the following formula (302-2). In the above formula (302), X １０ R １９In the case of "a silicon atom that is bonded to other atoms or other structures in the molecule of the fourth compound," formula (302) is represented by the following formula (302-3). In formulas (302-1) to (302-3), A １ ~A ４ Each of these independently corresponds to A in formula (302) above. １ ~A ４ It is synonymous with R １８ and R １９ Each of these independently corresponds to R in formula (302) above. １２ This is synonymous with the above, and * indicates a bonding site with another atom or structure within the molecule of the fourth compound.

[0429]

[0430] In one embodiment, the second host material has at least one substructure represented by formula (301). In one embodiment, the substructure represented by formula (301) is at least one selected from the group consisting of substructures represented by the following formulas (A11) to (A19).

[0431]

[0432]

[0433] (In the above formulas (A11) to (A16), A １２ ~A １６ Each is independently a nitrogen atom or CR １１ And R １１ R in formula (301) is １１ This is synonymous with, where * is a bonding site with another atom or structure in the molecule of the fourth compound, and in formulas (A17) and (A18), A １１ ~A ２２ Each of these is independently a nitrogen atom or CR １１ or is a carbon atom that is bonded to another atom or structure in the molecule of the fourth compound, R １１ Each of these independently corresponds to R in formula (301) １１ It is synonymous with A １１ ~A ２２At least one of them is a carbon atom that is bonded to another atom or structure in the molecule of the fourth compound, and in formula (A19), A １１ ~A １８ Each of these is independently a nitrogen atom or CR １１ It is either a carbon atom that is bonded to another atom or structure in the molecule of the fourth compound, R １１ Each of these independently corresponds to R in formula (301) １１ It is synonymous with X １１ and X １２ Each of these independently corresponds to X in formula (302) above. １０ It is synonymous with A １１ ~A １８ Carbon atoms in X １１ and X １２ Nitrogen atom in X １１ and X １２ The carbon atoms in, and X １１ and X １２ At least one of the silicon atoms in the compound is bonded to another atom or structure in the molecule of the fourth compound.

[0434] In one embodiment, the second host material has at least one substructure represented by formula (302). In one embodiment, the substructure represented by formula (302) is at least one selected from the group consisting of substructures represented by the following formulas (B11) to (B24).

[0435]

[0436] (In the above formulas (B11) to (B16), Ax １ ~Ax ４ Each is independently a nitrogen atom or CR １２ And R １２ Each of these independently corresponds to R in formula (302) above. １２ It is synonymous with X １０ X in formula (302) is １０ This is synonymous with, where * is a bonding site with another atom or other structure in the molecule of the fourth compound, and in formula (B17), Ax １ Ax２ and Ay １ ~Ay ４ Each of these is independently a nitrogen atom or CR １２ It is either a carbon atom that is bonded to another atom or structure in the molecule of the fourth compound, R １２ Each of these independently corresponds to R in formula (302) above. １２ It is synonymous with X １０ X in formula (302) is １０ It is synonymous with Ax １ Ax ２ and Ay １ ~Ay ４ Carbon atoms in X １０ Nitrogen atom in X １０ Carbon atoms and X in １０ At least one of the silicon atoms in is bonded to another atom or structure in the molecule of the fourth compound, and in formula (B18), Ay １ ~Ay ８ Each of these is independently a nitrogen atom or CR １２ It is either a carbon atom that is bonded to another atom or structure in the molecule of the fourth compound, R １２ Each of these independently corresponds to R in formula (302) above. １２ It is synonymous with X １０ X in formula (302) is １０ It is synonymous with Ay １ ~Ay ８ Carbon atoms in X １０ Nitrogen atom in X １０ Carbon atoms and X in １０ At least one of the silicon atoms in the compound is bonded to another atom or structure in the molecule of the fourth compound.

[0437]

[0438] (In the above formulas (B19) to (B24), Ay １ ~Ay ８ and Ay ９ ~Ay １２ Each of these is independently a nitrogen atom or CR １２It is either a carbon atom that is bonded to another atom or structure in the molecule of the fourth compound, R １２ Each of these independently corresponds to R in formula (302) above. １２ It is synonymous with X ９ and X １０ Each of these independently corresponds to X in formula (302) above. １０ It is synonymous with Ay １ ~Ay ８ and Ay ９ ~Ay １２ Carbon atoms in X ９ and X １０ Nitrogen atom in X ９ and X １０ The carbon atoms in, and X ９ and X １０ At least one of the silicon atoms in the compound is bonded to another atom or structure in the molecule of the fourth compound.

[0439] In the fourth compound of the fifth embodiment, R １１、 R １２ and R １１５ ~R １１７ Preferably, each of these is independently a hydrogen atom, a halogen atom, a cyano group, an unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, an unsubstituted heterocyclic group having 5 to 30 carbon atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 30 carbon atoms, an unsubstituted arylsilyl group having 6 to 60 carbon atoms, an unsubstituted arylphosphoryl group having 6 to 60 carbon atoms, an unsubstituted alkoxy group having 1 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an amino group, an unsubstituted alkylamino group having 2 to 30 carbon atoms, an unsubstituted arylamino group having 6 to 60 carbon atoms, a thiol group, an unsubstituted alkylthio group having 1 to 30 carbon atoms, or an unsubstituted arylthio group having 6 to 30 carbon atoms. In the fourth compound of the fifth embodiment, R １１、 R １２ and R １１５ ~R １１７It is more preferable that each of these independently be a hydrogen atom, a halogen atom, a cyano group, an unsubstituted ring-forming aryl group having 6 to 14 carbon atoms, an unsubstituted ring-forming heterocyclic group having 5 to 14 carbon atoms, an unsubstituted C1 to C6 alkyl group, an unsubstituted C1 to C6 halogenated alkyl group, an unsubstituted C3 to C6 alkylsilyl group, an unsubstituted ring-forming arylsilyl group having 6 to 60 carbon atoms, an unsubstituted ring-forming arylphosphoryl group having 6 to 60 carbon atoms, an unsubstituted C1 to C6 alkoxy group, an unsubstituted ring-forming aryloxy group having 6 to 14 carbon atoms, an amino group, an unsubstituted C2 to C12 alkylamino group, an unsubstituted ring-forming arylamino group having 6 to 60 carbon atoms, a thiol group, an unsubstituted C1 to C6 alkylthio group, or an unsubstituted ring-forming arylthio group having 6 to 14 carbon atoms. In the fourth compound of the fifth embodiment, R １１、 R １２ and R １１５ ~R １１７ It is even more preferable that it be a hydrogen atom.

[0440] In the fourth compound of the fifth embodiment, X １０ In R １３ ~R １９ , and X ９ In R １３ ~R １９ (X １０ In R １３ ~R １９ (Synonymous with) preferably each independently be a hydrogen atom, an unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, an unsubstituted ring-forming heterocyclic group having 5 to 30 carbon atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms. In the fourth compound of the fifth embodiment, X １０ In R １３ ~R １９ , and X ９ In R １３ ~R １９ It is more preferable that each of these independently be a hydrogen atom, an unsubstituted ring-forming aryl group having 6 to 14 carbon atoms, an unsubstituted ring-forming heterocyclic group having 5 to 14 carbon atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 6 carbon atoms. In the fourth compound of the fifth embodiment, X １０ In R１３ ~R １９ , and X ９ In R １３ ~R １９ It is even more preferable that each of these is independently an unsubstituted ring-forming aryl group having 6 to 14 carbon atoms, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0441] Examples of substructures represented by any of the above formulas (301) to (318) include the substructures represented by the following formulas (A101) to (A121) and (B101) to (B125). The fourth compound also preferably contains at least one of the substructures represented by the following formulas (A101) to (A121) and (B101) to (B125) in a single molecule.

[0442]

[0443] In the above formulas (A101) to (A107), R １０１ ~R １０６ Each of these independently corresponds to R in formula (301) １１ It is synonymous with R １０１ ~R １０６ At least one of these is a single bond that connects to another atom or structure in the molecule of the fourth compound. In formulas (A101) to (A107), adjacent R １０１ and R １０２ Group R １０２ and R １０３ Group R １０３ and R １０４ Group R １０４ and R １０５ Group R １０５ and R １０６ The group, and R １０６ and R １０１ One or more of these pairs either combine with each other to form a substituted or unsubstituted monoring, or combine with each other to form a substituted or unsubstituted fused ring, or do not combine with each other.

[0444]

[0445] In the above formulas (A108) to (A109), R １１０ Each of these independently corresponds to R in formula (301)１１ It is synonymous with R １１０ At least one of these is a single bond that connects to another atom or structure in the molecule of the fourth compound, and multiple R １１０ These are multiple Rs, which are either identical or different from each other. １１０ One or more pairs of adjacent elements from among them either combine to form a substituted or unsubstituted monoring, combine to form a substituted or unsubstituted fused ring, or do not combine with each other.

[0446]

[0447] In the above formulas (A110) to (A114), R １１０ and R １１２ ~R １１４ Each of these independently corresponds to R in formula (301) １１ It is synonymous with X １１０ Each of these independently corresponds to X in formula (302) above. １０ It is synonymous with R １１０ and R １１２ ~R １１４ At least one of these is a single bond that connects to another atom or structure in the molecule of the fourth compound, or X １１０ At least one of the nitrogen, carbon, and silicon atoms in the compound is bonded to other atoms or structures in the molecule of the fourth compound, and multiple R １１０ These are either the same or different from each other. In formulas (A110) to (A114) above, multiple R １１０ A set of two or more adjacent elements, R １１２ and R １１３ The set of, and X １１０ In R １４ and R １５ The group (X １０ In R １４ and R １５ (Synonymous with the group) X １１０ In R １６ and R １７ The group (X １０ In R １６ and R １７One or more pairs (synonymous with a pair) combine to form a substituted or unsubstituted monoring, combine to form a substituted or unsubstituted fused ring, or do not combine with each other.

[0448]

[0449] In the above formulas (A115) to (A119), R １１０ and R １１２ ~R １１４ Each of these independently corresponds to R in formula (301) １１ It is synonymous with R １１０ and R １１２ ~R １１４ At least one of these is a single bond that connects to another atom or structure in the molecule of the fourth compound, and multiple R １１０ These are either the same or different from each other. In formulas (A115) to (A119) above, multiple R １１０ A set of two or more adjacent items, and R １１２ and R １１３ One or more of these pairs combine to form a substituted or unsubstituted monoring, a substituted or unsubstituted fused ring, or do not combine with each other.

[0450]

[0451] In the above formulas (A120) to (A121), R １１０ Each of these independently corresponds to R in formula (301) １１ It is synonymous with R １１０ At least one of these is a single bond that connects to another atom or structure in the molecule of the fourth compound, and multiple R １１０ These are either the same or different from each other. In formulas (A120) to (A121) above, multiple R １１０ One or more pairs of adjacent elements from among them either combine to form a substituted or unsubstituted monoring, combine to form a substituted or unsubstituted fused ring, or do not combine with each other.

[0452]

[0453] In the above formulas (B101) to (B109), R １１４ and R １２１ ~R １３１ Each of these independently corresponds to R in formula (302) above. １２ It is synonymous with R １１４ and R １２１ ~R １３１ At least one of these is a single bond that connects to another atom or structure in the molecule of the fourth compound. In formulas (B101) to (B102), R １２２ and R １２３ Group R １２３ and R １１４ The group, and R １１４ and R １２１ One or more of the pairs either combine with each other to form a substituted or unsubstituted monoring, or combine with each other to form a substituted or unsubstituted fused ring, or do not combine with each other. In formulas (B105) to (B106), R １２４ and R １２５ Group R １２５ and R １２６ Group R １２６ and R １２７ Group R １２７ and R １２８ The group, and R １２８ and R １２９ One or more of the pairs either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine with each other. In formula (B107), R １２４ and R １２５ Group R １２５ and R １２６ Group R １２６ and R １２７ Group R １２７ and R １２８ Group R １２８ and R １２９ Group R １２９ and R １１４ The group, and R １１４ and R １２４One or more of the pairs either combine with each other to form a substituted or unsubstituted monoring, or combine with each other to form a substituted or unsubstituted fused ring, or do not combine with each other. In formulas (B108) to (B109), R １２４ and R １２５ Group R １２５ and R １２６ Group R １３０ and R １３１ The group, and R １３１ and R １２９ One or more of these pairs either combine with each other to form a substituted or unsubstituted monoring, or combine with each other to form a substituted or unsubstituted fused ring, or do not combine with each other.

[0454]

[0455] In the above formulas (B110) to (B117), R １１０ and R １３２ ~R １３５ Each of these independently corresponds to R in formula (302) above. １２ It is synonymous with R １１０ and R １３２ ~R １３５ At least one of these is a single bond that connects to another atom or structure in the molecule of the fourth compound, and multiple R １１０ These are either the same or different from each other. In formulas (B110) to (B117) above, multiple R １１０ A set of two or more adjacent items, and R １３２ and R １３３ One or more of these pairs either combine with each other to form a substituted or unsubstituted monoring, or combine with each other to form a substituted or unsubstituted fused ring, or do not combine with each other.

[0456]

[0457] In the above formulas (B118) to (B123), R １１０ Each of these independently corresponds to R in formula (302) above. １２ This is equivalent to X in formula (302), where Xa and Xb are each independently X １０ It is synonymous with R １１０At least one of them is a single bond that connects to another atom or structure in the molecule of the fourth compound, or at least one of the nitrogen, carbon, and silicon atoms in Xa and Xb is bonded to another atom or structure in the molecule of the fourth compound, and multiple R １１０ These are either the same or different from each other. In formulas (B118) to (B123) above, multiple R １１０ A set of two or more adjacent items, R in Xa １４ and R １５ The set and R in Xb １４ and R １５ The group (X １０ In R １４ and R １５ (Synonymous with the pair), and R in Xa １６ and R １７ The set and R in Xb １６ and R １７ The group (X １０ In R １６ and R １７ One or more pairs (synonymous with a pair) combine to form a substituted or unsubstituted monoring, combine to form a substituted or unsubstituted fused ring, or do not combine with each other.

[0458]

[0459] In the above formulas (B124) to (B125), R １１０ Each of these independently corresponds to R in formula (302) above. １２ This is synonymous with Xa, Xb, and Xc, each independently, being X in formula (302). １０ It is synonymous with R １１０ At least one of them is a single bond that connects to another atom or structure in the molecule of the fourth compound, or at least one of the nitrogen, carbon, and silicon atoms in Xa, Xb, and Xc is bonded to another atom or structure in the molecule of the fourth compound, and multiple R １１０ These are either the same or different from each other. In formulas (B124) to (B125) above, multiple R １１０A set of two or more adjacent items among them, R in Xa, Xb, and Xc １４ and R １５ The group (X １０ In R １４ and R １５ (Synonymous with the set of), and R in Xa, Xb and Xc １６ and R １７ The group (X １０ nioke R １６ and R １７ One or more pairs (synonymous with a pair) combine to form a substituted or unsubstituted monoring, combine to form a substituted or unsubstituted fused ring, or do not combine with each other.

[0460] In the above formulas (A101) to (A121) and (B101) to (B125), R １１０ , R １０１ ~R １０６ , R １１２ ~R １１４ , R １２１ ~R １３１ and R １３２ ~R １３５ Each of these is preferably independently a hydrogen atom, an unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, an unsubstituted ring-forming heterocyclic group having 5 to 30 carbon atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms; more preferably a hydrogen atom, an unsubstituted ring-forming aryl group having 6 to 14 carbon atoms, an unsubstituted ring-forming heterocyclic group having 5 to 14 carbon atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 6 carbon atoms; and even more preferably a hydrogen atom, an unsubstituted ring-forming aryl group having 6 to 14 carbon atoms, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0461] In the above formulas (A101) to (A121) and (B101) to (B125), Xa, Xb, Xc and X １１０ In R １３ ~R １９ (X １０ In R １３ ~R １９(Synonymous with) is preferably, independently, a hydrogen atom, an unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, an unsubstituted heterocyclic group having 5 to 30 carbon atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms; more preferably, a hydrogen atom, an unsubstituted ring-forming aryl group having 6 to 14 carbon atoms, an unsubstituted heterocyclic group having 5 to 14 carbon atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 6 carbon atoms; and even more preferably, an unsubstituted ring-forming aryl group having 6 to 14 carbon atoms, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0462] In the fifth embodiment, the fourth compound preferably has at least one monovalent or greater residue derived from any of the following: (I) a cyano group, an amino group, a substituted or unsubstituted C2-C30 alkylamino group, or a substituted or unsubstituted ring-forming C6-C60 arylamino group; or (II) a monovalent or greater residue derived from any of the following: substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted indole, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted silafluorene, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridine, substituted or unsubstituted pyridazine, substituted or unsubstituted pyrazine, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, substituted or unsubstituted phenanthrene, or substituted or unsubstituted triphenylene.

[0463] In the fifth embodiment, the fourth compound is more preferably having at least one (III) cyano group, or (IV) at least one monovalent or greater residue derived from any of the following: substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted silafluorene, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridine, and substituted or unsubstituted triphenylene.

[0464] In the fifth embodiment, the fourth compound is more preferably having at least one monovalent or greater residue derived from any of the following: a substituted or unsubstituted carbazole, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted triazine, and a substituted or unsubstituted pyrimidine.

[0465] In the fifth embodiment, the fourth compound may also preferably contain one or more substructures in a single molecule that are represented by any of the formulas selected from the group consisting of (A101), (A102), (A103), and (A106).

[0466] In the fifth embodiment, the fourth compound contains one or more substructures represented by formula (A101) in a single molecule, and R in formula (A101) １０１ ~R １０６ One or more selected from the group consisting of are single bonds that bond to other atoms or other structures in the molecule of the fourth compound, and R is not a single bond. １０１ ~R １０６ It is also preferable that one or more selected from the group consisting of are cyano groups.

[0467] In the fifth embodiment, the fourth compound contains one or more substructures represented by formula (A102) in a single molecule, and R in formula (A102) １０２ , R １０４ and R １０６ One or more selected from the group consisting of are single bonds that bond to other atoms or other structures in the molecule of the fourth compound, and R is not a single bond. １０２ , R１０４ and R １０６ It is also preferable that one or more selected from the group consisting of are cyano groups.

[0468] In the fifth embodiment, the fourth compound contains one or more substructures represented by formula (A103) in a single molecule, and R in formula (A103) １０１ , R １０２ , R １０４ and R １０６ One or more selected from the group consisting of are single bonds that bond to other atoms or other structures in the molecule of the fourth compound, and R is not a single bond. １０１ , R １０２ , R １０４ and R １０６ It is also preferable that one or more selected from the group consisting of are cyano groups.

[0469] In the fifth embodiment, the fourth compound contains one or more substructures represented by formula (A106) in a single molecule, and R in formula (A106) １０２ ~R １０６ One or more selected from the group consisting of are single bonds that bond to other atoms or other structures in the molecule of the fourth compound, and R is not a single bond. １０２ ~R １０６ It is also preferable that one or more selected from the group consisting of are cyano groups.

[0470] In the fifth embodiment, the fourth compound preferably has at least one monovalent or greater residue derived from a substituted or unsubstituted carbazole.

[0471] In the fifth embodiment, the fourth compound preferably has at least one substructure represented by the following formula (15).

[0472]

[0473] (In formula (15) above, R １５０ ~R １５８ Of these, at least one is a single bond that connects to another atom or structure in the molecule of the fourth compound, and R is not a single bond. １５０ ~R １５８Each of these independently consists of a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C1-C50 haloalkyl group, a substituted or unsubstituted C2-C50 alkenyl group, a substituted or unsubstituted C2-C50 alkynyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ A group represented by ) -O-(R ９０４ A group represented by ) -S-(R ９０５ A group represented by ) -N(R ９０６ ) (Caution ９０７ The group represented by -C(=O)R ９０８ The base represented by -COOR ９０９ The group represented by -P(=O)(R ９１０ ) (Caution ９１１ The group represented by ) -Ge(R ９１２ ) (Caution ９１３ ) (Caution ９１４ A group represented by ) -B(R ９１５ ) (Caution ９１６ The group is represented by ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.

[0474] In the above formula (15), R １５０ It is preferably a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, more preferably a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and even more preferably a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.

[0475] (Fourth compound represented by formula (161) or (162)) In the fifth embodiment, the fourth compound may also be a compound represented by the following formula (161) or formula (162).

[0476]

[0477] (In the above formula (161), Ar １６１ m1 is a substituted or unsubstituted aromatic hydrocarbon ring with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle with 5 to 30 ring-forming atoms, where m1 is 1, 2, 3, 4, 5, or 6, and R １６１ It is an electron-donating base, and R １６１ These are, respectively, Ar １６１ Bonded to the constituent elements, if m1 is 2 or more, multiple R １６１ They are either identical or different from each other, however Ar １６１ Ar is not an electron-accepting aromatic hydrocarbon ring or heterocycle. １６１ If the substituent has a substituent, the substituent is not an electron-accepting group, but rather, in formula (162), Ar １６２ is a substituted or unsubstituted aromatic hydrocarbon ring with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle with 5 to 30 ring-forming atoms, where n1 is 1, 2, 3, 4, 5 or 6, and R １６２ R is an electron-accepting group, １６２ These are, respectively, Ar １６２ Bonded to the constituent elements, if n1 is 2 or more, multiple R １６２ They are either identical or different from each other, however Ar １６２ Ar is not an electron-donating aromatic hydrocarbon ring or heterocycle. １６２ (If the compound has substituents, those substituents are not electron-donating groups.)

[0478] In the above formulas (161) and (162), Ar １６１ and Ar １６２ Preferably, each of these is a monovalent or greater residue derived independently from either of the compounds represented by the following formulas (A61) and (A62).

[0479]

[0480] In the fifth embodiment, R in formula (161) １６１ Preferably, each of these is independently a monovalent or greater residue derived from any of the compounds represented by the following formulas (DN1) to (DN6) and (DN8) to (DN10), or a group represented by the following formula (DN7).

[0481]

[0482] (In the above formula (DN7), * represents Ar １６１ (This represents the bonding site with the constituent elements.)

[0483] In the fifth embodiment, R in formula (162) １６２ Preferably, each of these is independently a monovalent or greater residue derived from any of the compounds represented by the following formulas (AC4) to (AC18) and (AC22) to (AC23), or any of the groups represented by the following formulas (AC1) to (AC3), (AC19) to (AC21), and (AC24).

[0484]

[0485]

[0486] (In the above formula (AC1), n Ａ is 1, 2, or 3, and in the above formulas (AC22) to (AC23), X １ ~X ８ Each of them independently, CR １６３ or a carbon atom that is bonded to another atom or other structure in the molecule of the fourth compound, provided that X １ ~X ８ At least one of the carbon atoms in is Ar １６２ It combines with the elements that make up the, and in the above formula (AC24), X １ ~X ８ Each of these is independently a nitrogen atom or CR １６３ is or Ar １６２ A carbon atom that bonds with the elements that make up the, and in the above formulas (AC22) to (AC24), R １６３ If multiple R １６３These are either identical or different from each other, and multiple R １６３ R consists of two or more adjacent groups of which either combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine to form a substituted or unsubstituted monoring and do not form a substituted or unsubstituted fused ring. １６３ Each of these independently corresponds to R in formula (302) above. １２ This is equivalent to, and in the above formulas (AC1) to (AC3), (AC19) to (AC21) and (AC24), * represents Ar １６２ (This represents the bonding site with the constituent elements.)

[0487] In the fifth embodiment, the fourth compound may also be a compound represented by the following formula (130).

[0488]

[0489] (In the above formula (130), X １３ This is a group represented by an oxygen atom, a sulfur atom, or N-Rb, and Z １ ~Z １２ These are groups that are independently represented by a nitrogen atom or C-Rc, and Ar １４ and Ar １５ Each is independently a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms, L １４ and L １５ Each is independently a single bond, a substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, and Rb and Rc are independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, and -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３The group represented by -C(=O)R ９０８ The base represented by -COOR ９０９ The group represented by -P(=O)(R ９１０ ) (Caution ９１１ The group represented by ) -Ge(R ９１２ ) (Caution ９１３ ) (Caution ９１４ The group is represented by ), a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and if multiple Rc groups are present, the multiple Rc groups are either identical or different from one another.

[0490] In the compound represented by the above formula (130), -L １４ -Ar １４ The group represented by -L １５ -Ar １５ If the substituent is the same as the group represented by Z １ and Z １２ Z ２ and Z １１ Z ３ and Z １０ Z ４ and Z ９ Z ５ and Z ８ , and Z ６ and Z ７ It is also preferable that none of them are the same group as each other. In this case, in formula (130), X １３ A structure condensed on the right side of a five-membered ring containing X １３ Unlike the structure in which the five-membered ring containing the compound is condensed on the left side, the compound represented by formula (130) is a compound having an asymmetric structure.

[0491] In the compound represented by the above formula (130), -L １４ -Ar １４ The group represented by -L １５ -Ar １５ It is preferable that the groups represented by and are different from each other. In this case as well, as described above, the compound represented by formula (130) is a compound having an asymmetric structure.

[0492] In the fifth embodiment, the fourth compound is also preferably a compound represented by the following formula (120).

[0493]

[0494] (In the above formula (120), Ar １１ and Ar １２ Each is independently a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms, L １１ and L １２ Each is independently an arylene group with 6 to 50 ring-forming carbon atoms, either single-bonded, substituted, or unsubstituted, or a divalent heterocyclic group with 5 to 50 ring-forming atoms, L １３ m is a substituted or unsubstituted monocyclic hydrocarbon group with 6 or fewer ring-forming carbon atoms, or a substituted or unsubstituted monocyclic heterocyclic group with 6 or fewer ring-forming atoms, m is 0, 1, 2, or 3, and there are multiple L １３ They are either identical or different from each other, X １ ~X ８ and Y １ ~Y ８ Each is independently N or CRa, where X ５ ~X ８ One of the following, Y １ ~Y ４ One of them is L １３ Ra is either a carbon atom bonded via or directly bonded to, and Ra is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ The group represented by ) is a halogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and if there are multiple Ras, the multiple Ras are either the same or different from each other, and the compound represented by formula (120) satisfies one or both of the following (i) and (ii). (i) Ar １１ and Ar １２At least one of them is an aryl group with 6 to 50 ring-forming carbon atoms substituted with a cyano group, or a heterocyclic group with 5 to 50 ring-forming atoms substituted with a cyano group. (ii) X １ ~X ４ and Y ５ ~Y ８ At least one of them is CRa, and X １ ~X ４ and Y ５ ~Y ８ At least one of the Ra atoms in this compound is an aryl group with 6 to 50 ring-forming carbon atoms substituted with a cyano group, or a heterocyclic group with 5 to 50 ring-forming atoms substituted with a cyano group.

[0495] In the compound represented by formula (120), the cyano-substituted aromatic hydrocarbon group having 6 to 50 ring-forming carbon atoms and the cyano-substituted heterocyclic group having 5 to 50 ring-forming atoms may further have substituents other than cyano groups.

[0496] In the compound represented by formula (120), m is preferably 0, 1, or 2, and more preferably 0 or 1. In the compound represented by formula (120), when m is 0, X ５ ~X ８ One of them, Y １ ~Y ４ One of them is directly bonded to the other via a single bond.

[0497] In the compound represented by the above formula (120), X ６ and Y ３ The pair, X ６ and Y ２ The pair with, and X ７ and Y ３ From the group consisting of pairs, any pair selected is L １３ It is preferable that the carbon atom is bonded via or directly bonded to the atom.

[0498] X ６ and Y ３ The pair with L １３ If the carbon atom is bonded via or directly bonded, the compound represented by formula (120) can be represented by the following formula (121).

[0499]

[0500] (In the above formula (121), Ar １１ Ar １２ , L １１ , L １２ , L １３ , m, X １ ~X ５ , X ７ ~X ８ , Y １ ~Y ２ and Y ４ ~Y ８ These are, respectively, Ar in formula (120) above. １１ Ar １２ , L １１ , L １２ , L １３ , m, X １ ~X ５ , X ７ ~X ８ , Y １ ~Y ２ and Y ４ ~Y ８ This is equivalent to the above, and the compound represented by formula (121) satisfies at least one of the conditions of (i) and (ii).

[0501] In the compound represented by the above formula (120), -Ar １１ -L １１ A group represented by -Ar １２ -L １２ It is preferable that the groups represented by are different from each other.

[0502] L １３ The monocyclic hydrocarbon group having 6 or fewer carbon atoms that forms the ring is preferably at least one group selected from the group consisting of, for example, phenylene, cyclopentenylene, cyclopentadienylene, cyclohexylene, and cyclopentylene, and more preferably a phenylene group. １３ The monocyclic heterocyclic group having six or fewer ring-forming atoms is preferably at least one group selected from the group consisting of, for example, a pyrrolylene group, a pyrazinylene group, a pyridinylene group, a flirene group, and a thiophenylene group.

[0503] In one embodiment, at least one of the one or more light-emitting layers may contain two or more fourth compounds with different molecular structures. Mixing compounds with different charge transport properties is expected to improve the charge balance within the light-emitting layer and enhance the luminescence efficiency. Furthermore, the formation of an exciplex by two or more fourth compounds (second host materials) reduces the excitation energy, enabling lower voltage operation than when only one second host material is contained in the light-emitting layer.

[0504] (Method for producing the second host material) The second host material, as the fourth compound, can be produced by known methods. The fourth compound can also be produced by following known methods and using known alternative reactions and raw materials suited to the target product.

[0505] (Specific examples of the second host material) Specific examples of the second host material as the fourth compound in the fifth embodiment include, for example, the following compounds. However, the present invention is not limited to these specific examples of compounds.

[0506]

[0507]

[0508]

[0509]

[0510]

[0511]

[0512]

[0513]

[0514]

[0515]

[0516]

[0517]

[0518]

[0519]

[0520]

[0521]

[0522]

[0523]

[0524]

[0525]

[0526]

[0527]

[0528]

[0529]

[0530]

[0531]

[0532]

[0533]

[0534]

[0535]

[0536]

[0537]

[0538]

[0539] (Relationship between the first host material, second host material, sensitizing material, and fluorescent material in the light-emitting layer) In one embodiment of the fifth embodiment, the sensitizing material is a delayed-fluorescence compound. In one embodiment of the fifth embodiment, at least one of the one or more light-emitting layers contains a delayed-fluorescence compound as the sensitizing material and does not necessarily contain a phosphorescent metal complex.

[0540] In one embodiment of the fifth embodiment, it is preferable that at least one of the one or more light-emitting layers satisfies at least one of the relationships in formula (Equation 4), formula (Equation 4A), formula (Equation 4B), formula (Equation 6), formula (Equation 6A), and formula (Equation 6B) in the fourth embodiment. In one embodiment, the lowest excitation singlet energy S of the second host material １ (H2) and the lowest excitation singlet energy S of the delayed fluorescence compound １ It is preferable that (GT2) and satisfy the relationship shown in the following formula (Equation 41A). １ (H2) > S １ (GT2) ... (Mathematics 41A)

[0541] In one embodiment, the lowest excited singlet energy S of the second host material, the delayed fluorescence compound, and the fluorescent material. １ It is preferable that the following relationship (Equation 41B) is satisfied. １ (H2) > S １ (GT2) > S １ (D) ...(Number 41B)

[0542] In one embodiment, when the sensitizing material is a delayed-fluorescence compound, the energy gap T at 77 [K] of the second host material is ７７Ｋ (H2), and the energy gap T at 77 [K] of the delayed-fluorescence compound. ７７Ｋ (GT2) preferably satisfies the relationship shown in the following formula (Equation 61). ７７Ｋ (H2)>T ７７Ｋ (GT2) ... (Number 61)

[0543] In one embodiment, the energy gap T at 77 [K] of the second host material, the delayed fluorescence compound, and the fluorescent material is present. ７７Ｋ It is preferable that the following relationship (Equation 61B) is satisfied. ７７Ｋ (H2)>T ７７Ｋ (GT2) > T ７７Ｋ (D) ...(Number 61B)

[0544] In one embodiment of the fifth embodiment, the sensitizing material is a phosphorescent metal complex. In one embodiment of the fifth embodiment, at least one of the one or more light-emitting layers contains a phosphorescent metal complex as the sensitizing material and does not necessarily contain a delayed fluorescence compound.

[0545] Figure 6 shows an example of the relationship between the energy levels of the first host material (first compound), the second host material (fourth compound), the phosphorescent metal complex as a sensitizer (second compound), and the fluorescent material (third compound) in the light-emitting layer. In Figure 6, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the first host material, and T1(M1) represents the lowest excited triplet state of the first host material. S1(M4) represents the lowest excited singlet state of the second host material, and T1(M4) represents the lowest excited triplet state of the second host material. S1(M2) represents the lowest excited singlet state of the phosphorescent metal complex, and T1(M2) represents the lowest excited triplet state of the phosphorescent metal complex. S1(M3) represents the lowest excited singlet state of the fluorescent material, and T1(M3) represents the lowest excited triplet state of the fluorescent material. The dashed arrow in Figure 6, pointing from T1(M2) to S1(M3), represents dipole-type energy transfer from the lowest excited triplet state of the phosphorescent metal complex to the lowest excited singlet state of the fluorescent material. As shown in Figure 6, when a phosphorescent metal complex is used as a sensitizer, the lowest excited singlet state S1(M2) of the phosphorescent metal complex can inter-system cross to the lowest excited triplet state T1(M2) due to spin-orbit interaction and heavy atom effects. Then, dipole-type energy transfer occurs from the lowest excited triplet state T1(M2) of the phosphorescent metal complex to the fluorescent material, generating the lowest excited singlet state S1(M3). As a result, fluorescence emission from the lowest excited singlet state S1(M3) of the fluorescent material can be observed. It is believed that by utilizing this mechanism, the internal quantum efficiency can be theoretically increased to 100%. Note that the relative magnitudes of the energy levels S1(M1) and S1(M4), as well as the relative magnitudes of the energy levels T1(M1) and T1(M4), are not limited to those shown in Figure 6.

[0546] In one embodiment of the fifth embodiment, it is preferable that at least one of the one or more light-emitting layers satisfies at least one of the relationships of formula (Equation 3), formula (Equation 3A), formula (Equation 3B), formula (Equation 3C), formula (Equation 5), formula (Equation 5A), and formula (Equation 5B).

[0547] In one embodiment, when the sensitizing material is a phosphorescent metal complex, the energy gap T at 77 [K] of the second host material ７７Ｋ (H2), and the energy gap T at 77 [K] of the phosphorescent metal complex ７７Ｋ (GP2) is expressed by the following formula (Equation 31A). ７７Ｋ (H2)>T ７７Ｋ (GP2) ... (Mathematics 31A)

[0548] In one embodiment, the energy gap T at 77 [K] between the second host material and the phosphorescent metal complex is ７７Ｋ And the lowest excitation singlet energy S of the fluorescent material １ It is preferable that (D) and satisfy the relationship shown in the following formula (Equation 31B). ７７Ｋ (H2)>T ７７Ｋ (GP2) > S １ (D) ...(Number 31B)

[0549] In one embodiment, the lowest excited singlet energy S of the second host material １ (H2) and the lowest excitation singlet energy S of the phosphorescent metal complex １ It is also preferable that (GP2) and satisfy the relationship shown in the following formula (Equation 51). １ (H2) > S １ (GP2) ... (Number 51)

[0550] In one embodiment, the lowest excitation singlet energy S of the second host material, the phosphorescent metal complex, and the fluorescent material. １ It is also preferable that the following equation (Equation 51B) satisfies the relationship. １ (H2) > S １ (GP2) > S １ (D) ...(Number 51B)

[0551] When the organic EL element of the fifth embodiment is made to emit light, it is preferable that at least one of the one or more light-emitting layers emits light mainly from a fluorescent compound.

[0552] (Compound content in the light-emitting layer) The content of the first host material (first compound), second host material (fourth compound), sensitizing material (second compound), and fluorescent material (third compound) contained in the light-emitting layer is preferably within the following ranges, for example.

[0553] The total content of the first host material and the second host material in the light-emitting layer is preferably 70% by mass or more, and more preferably 80% by mass or more. The total content of the first host material and the second host material in the light-emitting layer is preferably 90% by mass or less, and more preferably 85% by mass or less.

[0554] When the sensitizing material (second compound) is a delayed-fluorescence compound, the content of the delayed-fluorescence compound in the light-emitting layer is preferably 5% by mass or more, and more preferably 10% by mass or more. The content of the delayed-fluorescence compound in the light-emitting layer is preferably 50% by mass or less, and more preferably 30% by mass or less.

[0555] When the sensitizing material (second compound) is a phosphorescent metal complex, the content of the phosphorescent metal complex in the light-emitting layer is preferably 5% by mass or more, and more preferably 10% by mass or more. The content of the phosphorescent metal complex in the light-emitting layer is preferably 50% by mass or less, and more preferably 30% by mass or less.

[0556] The content of the fluorescent material (third compound) in the light-emitting layer is preferably 0.5% by mass or more, and more preferably 1% by mass or more. The content of the fluorescent material (third compound) in the light-emitting layer is preferably 10% by mass or less, and more preferably 5% by mass or less. The upper limit of the total content of the first host material (first compound), second host material (fourth compound), sensitizing material (second compound), and fluorescent material (third compound) in the light-emitting layer is 100% by mass. The fifth embodiment does not exclude the inclusion of materials other than the first host material, second host material, sensitizing material, and fluorescent material in the light-emitting layer. In the fifth embodiment, the light-emitting layer may contain only one type of the first host material, second host material, sensitizing material, and fluorescent material, or two or more types.

[0557] The organic EL element according to the fifth embodiment can improve the lifespan of the organic EL element. According to one embodiment of the organic EL element according to the fifth embodiment, the lifespan of the organic EL element can be improved by including a sensitizing material (preferably a blue sensitizing material), a compound according to the first embodiment as a first host material (first compound), a second host material (fourth compound), and a fluorescent material (third compound) in the light-emitting layer. The organic EL element according to the fifth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0558] [Sixth Embodiment] The configuration of the organic EL element according to the sixth embodiment will now be described. In the description of the sixth embodiment, components that are the same as those in the third to fifth embodiments will be given the same reference numerals and names, and their descriptions will be omitted or simplified. In addition, in the sixth embodiment, materials and compounds that are not specifically mentioned can be the same as those described in the third to fifth embodiments.

[0559] (Emitting layer) In the sixth embodiment, the compound according to the first embodiment (the first compound), which was used as the first host material in the organic EL element according to the third embodiment, is used as a sensitizing material. In the sixth embodiment, the organic EL element according to the third embodiment is otherwise the same as the organic EL element according to the third embodiment. In the sixth embodiment, at least one of the one or more emitting layers contains the compound according to the first embodiment (the first compound) as a sensitizing material and a fluorescent material. In the sixth embodiment, the sensitizing material and the fluorescent material are different materials. In one aspect of the sixth embodiment, the sensitizing material is a delayed-fluorescence compound. In this aspect, at least one of the one or more emitting layers does not contain a phosphorescent metal complex.

[0560] [Sensitizing material] In the sixth embodiment, the sensitizing material is the compound according to the first embodiment (the first compound). In the sixth embodiment, if the sensitizing material is a delayed-fluorescence compound, a compound having delayed fluorescence (for example, a compound in which a donor site and an acceptor site are bound within the molecule) can be selected and used as the delayed-fluorescence compound.

[0561] [Fluorescent material] In the sixth embodiment, the fluorescent material can be the same material as the fluorescent material (third compound) described in the third embodiment.

[0562] (Relationship between sensitizing material and fluorescent material in the light-emitting layer) In one embodiment of the sixth embodiment, the sensitizing material (first compound) is a delayed-fluorescence compound. In one embodiment of the sixth embodiment, at least one of the one or more light-emitting layers contains a delayed-fluorescence compound as a sensitizing material and does not necessarily contain a phosphorescent metal complex.

[0563] Figure 7 shows an example of the relationship between the energy levels of a sensitizing material and a fluorescent material when the light-emitting layer includes a delayed-fluorescence compound as a sensitizing material (first compound) and a fluorescent material (third compound). In Figure 7, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the delayed-fluorescence compound, and T1(M1) represents the lowest excited triplet state of the delayed-fluorescence compound. S1(M3) represents the lowest excited singlet state of the fluorescent material, and T1(M3) represents the lowest excited triplet state of the fluorescent material. The dashed arrow from S1(M1) to S1(M3) in Figure 7 represents the Förster-type energy transfer from the lowest excited singlet state of the delayed-fluorescence compound to the lowest excited singlet state of the fluorescent material. As shown in Figure 7, when a compound with a small ΔST(M1) is used as the delayed fluorescence compound, the lowest excited triplet state T1(M1) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M1) due to thermal energy. Then, a Förster-type energy transfer occurs from the lowest excited singlet state S1(M1) of the delayed fluorescence compound to the fluorescent material, generating the lowest excited singlet state S1(M3). As a result, fluorescence emission from the lowest excited singlet state S1(M3) of the fluorescent material can be observed. It is believed that by utilizing delayed fluorescence through this TADF mechanism, the internal quantum efficiency can theoretically be increased to 100%.

[0564] In the sixth embodiment, when the sensitizing material is a delayed-fluorescence compound, the lowest excitation singlet energy S of the delayed-fluorescence compound is... １ (GT1) and the lowest excitation singlet energy S of the fluorescent material １ It is preferable that (D) and satisfy the relationship shown in the following formula (Equation 41). １ (GT1) > S １ (D) ... (Number 41)

[0565] In the sixth embodiment, when the sensitizing material is a delayed-fluorescence compound, the energy gap T at 77 [K] of the delayed-fluorescence compound is... ７７Ｋ (GT1) and the energy gap T at 77 [K] of the fluorescent material. ７７Ｋ It is also preferable that (D) and satisfy the relationship shown in the following formula (Equation 61A).７７Ｋ (GT1) > T ７７Ｋ (D) ...(Number 61A)

[0566] When the organic EL element of the sixth embodiment is made to emit light, it is preferable that at least one of the one or more light-emitting layers emits light mainly from a fluorescent compound.

[0567] (Compound content in the light-emitting layer) The content of the sensitizing material (first compound) and the fluorescent material (third compound) contained in at least one of the one or more light-emitting layers is preferably within the following ranges, for example. The content of the sensitizing material (first compound) is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. The content of the sensitizing material may also be 90% by mass or more and 99.9% by mass or less, 95% by mass or more and 99% by mass or less, or 99% by mass or more and 99.9% by mass or less. The content of the fluorescent material (third compound) is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less. Note that the sixth embodiment does not exclude the case in which at least one of the one or more light-emitting layers contains materials other than the sensitizing material and the fluorescent material. At least one of the one or more light-emitting layers may contain only one type of sensitizing material, or two or more types. The light-emitting layer may contain only one type of fluorescent material, or two or more types.

[0568] The organic EL element according to the sixth embodiment can improve the lifespan of the organic EL element. The organic EL element according to the sixth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0569] [Seventh Embodiment] The configuration of the organic EL element according to the seventh embodiment will now be described. In the description of the seventh embodiment, components identical to those in the third to sixth embodiments will be given the same reference numerals and names, and their descriptions will be omitted or simplified. Furthermore, in the seventh embodiment, materials and compounds not specifically mentioned can be the same as those described in the third to sixth embodiments.

[0570] (Emitting Layer) In the seventh embodiment, similar to the sixth embodiment, the compound according to the first embodiment (the first compound) is used as a sensitizing material. In the organic EL element according to the seventh embodiment, at least one of the one or more emitting layers contains the compound according to the first embodiment (the first compound) as a sensitizing material, a fluorescent material, and a second host material different from the first compound. Other aspects are the same as the organic EL element according to the sixth embodiment. In the seventh embodiment, the second host material, the sensitizing material, and the fluorescent material are different materials from each other. In one aspect of the seventh embodiment, at least one of the one or more emitting layers contains a second host material (the fourth compound), a delayed-fluorescence compound as a sensitizing material (the first compound), and a fluorescent material (the third compound). In this embodiment, at least one of the one or more emitting layers does not contain a phosphorescent metal complex.

[0571] [Second host material] In the seventh embodiment, the second host material can be the same material as the second host material described in the fifth embodiment.

[0572] [Sensitizing material] In the seventh embodiment, the sensitizing material can be the same material as the sensitizing material described in the sixth embodiment.

[0573] [Fluorescent material] In the seventh embodiment, the fluorescent material can be the same material as the fluorescent material (third compound) described in the third embodiment.

[0574] (Relationship between the second host material, sensitizing material, and fluorescent material in the light-emitting layer) In one embodiment of the seventh embodiment, the sensitizing material (first compound) is a delayed-fluorescence compound. In one embodiment of the seventh embodiment, at least one of the one or more light-emitting layers contains a delayed-fluorescence compound as a sensitizing material and does not necessarily contain a phosphorescent metal complex.

[0575] Figure 8 shows an example of the relationship between the energy levels of the second host material, the sensitizer, and the fluorescent material when the light-emitting layer includes a second host material (fourth compound), a delayed-fluorescence compound as a sensitizer (first compound), and a fluorescent material (third compound). In Figure 8, S0 represents the ground state. S1 (M4) represents the lowest excited singlet state of the second host material, and T1 (M4) represents the lowest excited triplet state of the second host material. S1 (M1) represents the lowest excited singlet state of the delayed-fluorescence compound, and T1 (M1) represents the lowest excited triplet state of the delayed-fluorescence compound. S1 (M3) represents the lowest excited singlet state of the fluorescent material, and T1 (M3) represents the lowest excited triplet state of the fluorescent material. The dashed arrow in Figure 8, pointing from S1(M1) to S1(M3), represents the Förster-type energy transfer from the lowest excited singlet state of the delayed-fluorescence compound to the lowest excited singlet state of the fluorescent material. As shown in Figure 8, when a compound with a small ΔST(M1) is used as the delayed-fluorescence compound, the lowest excited triplet state T1(M1) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M1) due to thermal energy. Then, a Förster-type energy transfer occurs from the lowest excited singlet state S1(M1) of the delayed-fluorescence compound to the fluorescent material, generating the lowest excited singlet state S1(M3). As a result, fluorescence emission from the lowest excited singlet state S1(M3) of the fluorescent material can be observed. It is believed that by utilizing this delayed fluorescence mechanism, the internal quantum efficiency can be theoretically increased to 100%.

[0576] In one embodiment of the seventh embodiment, it is preferable that at least one of the one or more light-emitting layers satisfies at least one of the relationships in formula (Equation 41) and formula (Equation 61A).

[0577] In the seventh embodiment, when the sensitizing material is a delayed-fluorescence compound, the energy gap T at 77 [K] of the second host material is ７７Ｋ (H2) and the energy gap T at 77 [K] of the delayed-fluorescence compound. ７７Ｋ It is preferable that (GT1) and satisfy the relationship shown in the following formula (Equation 11). ７７Ｋ (H2)>T ７７Ｋ (GT1) ... (Number 11)

[0578] In the seventh embodiment, when the sensitizing material is a delayed-fluorescence compound, the lowest excitation singlet energy S of the second host material is １ (H2) and the lowest excitation singlet energy S of the delayed fluorescence compound １ It is also preferable that (GT1) and satisfy the relationship shown in the following formula (Equation 42A). １ (H2) > S １ (GT1) ... (Mathematics 42A)

[0579] In the seventh embodiment, when the sensitizing material is a delayed-fluorescence compound, the lowest excitation singlet energy S of the second host material, the delayed-fluorescence compound, and the fluorescent material is... １ It is also preferable that the following relationship (Equation 42B) is satisfied. １ (H2) > S １ (GT1) > S １ (D) ...(Number 42B)

[0580] In the seventh embodiment, when the sensitizing material is a delayed-fluorescence compound, the energy gap T at 77 [K] of the second host material, the delayed-fluorescence compound, and the fluorescent material is... ７７Ｋ It is also preferable that the following equation (Equation 62B) satisfies the relationship. ７７Ｋ (H2)>T ７７Ｋ (GT1) > T ７７Ｋ (D) ...(Number 62B)

[0581] (Compound content in the light-emitting layer) In the seventh embodiment, the content of the second host material (fourth compound), sensitizing material (first compound), and fluorescent material (third compound) contained in at least one of the one or more light-emitting layers is preferably within the same range as the content of the first host material, delayed-fluorescence compound as a sensitizing material (second compound), and fluorescent material (third compound) contained in at least one of the one or more light-emitting layers in the fourth embodiment.

[0582] The organic EL element according to the seventh embodiment can improve the lifespan of the organic EL element. The organic EL element according to the seventh embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0583] [Eighth Embodiment] (Electronic Device) The electronic device according to the eighth embodiment is equipped with an organic electroluminescent element of any of the embodiments described above. Examples of electronic devices include display devices and light-emitting devices. Examples of display devices include display components (e.g., organic EL panel modules), televisions, mobile phones, tablets, and personal computers. Examples of light-emitting devices include lighting and vehicle lights. The light-emitting device can also be used in a display device, for example, as a backlight for a display device.

[0584] The display device as an electronic device according to the eighth embodiment is preferably an organic EL display device equipped with organic EL elements as red pixels, green pixels, and blue pixels. In this organic EL display device, the blue pixels are preferably at least one of the organic EL elements according to the third, fourth, fifth, sixth, and seventh embodiments, as well as the modified examples described later.

[0585] [Modification of Embodiments] The present invention is not limited to the embodiments described above, and any modifications, improvements, etc., that can achieve the objectives of the present invention are included in the present invention.

[0586] For example, the light-emitting layer is not limited to one layer, but may consist of multiple light-emitting layers stacked together. When an organic EL element has multiple light-emitting layers, it is sufficient that one or more light-emitting layers 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 due to electron transitions from a triplet excited state to a direct ground state. Furthermore, when an organic EL element has multiple light-emitting layers, these light-emitting layers may be arranged adjacent to each other, or it may be a so-called tandem type organic EL element in which multiple light-emitting units are stacked with an intermediate layer in between.

[0587] Furthermore, for example, a barrier layer may be provided adjacent to at least one of the anode and cathode sides of the light-emitting layer. The barrier layer is preferably placed in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons. For example, if the barrier layer is placed in contact with the cathode side of the light-emitting layer, the barrier layer transports electrons and prevents holes from reaching the layer on the cathode side of the barrier layer (e.g., the electron transport layer). If the organic EL element includes an electron transport layer, it is preferable to include the barrier layer between the light-emitting layer and the electron transport layer. Also, if the barrier layer is placed in contact with the anode side of the light-emitting layer, the barrier layer transports holes and prevents electrons from reaching the layer on the anode side of the barrier layer (e.g., the hole transport layer). If the organic EL element includes a hole transport layer, it is preferable to include the barrier layer between the light-emitting layer and the hole transport layer. Furthermore, the barrier layer may be provided adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to its surrounding layers. The barrier layer prevents excitons generated in the light-emitting layer from moving to the electrode-side layer (e.g., the electron transport layer and the hole transport layer). It is preferable that the light-emitting layer and the barrier layer are joined together.

[0588] Furthermore, the specific structure and shape in the implementation of the present invention may be other structures, etc., to the extent that the objectives of the present invention can be achieved.

[0589] The present invention will be described in more detail below with reference to examples. The present invention is not limited to these examples.

[0590] <Compounds> The structure of the compound represented by formula (1) used in the manufacture of the organic EL elements according to Examples 1 to 5 is shown below.

[0591]

[0592]

[0593]

[0594] The structure of the comparative compound used in the manufacture of the organic EL element according to Comparative Example 1 is shown below.

[0595]

[0596] The structures of other compounds used in the production of organic EL elements in Examples 1 to 5 and Comparative Example 1 are shown below.

[0597]

[0598]

[0599]

[0600] <Fabrication of Organic EL Devices> Organic EL devices were fabricated as follows.

[0601] [Example 1] A glass substrate (manufactured by Geomatec Co., Ltd.) with a 25 mm x 75 mm x 1.1 mm thick ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 1 minute. The film thickness of the ITO transparent electrode was set to 130 nm. The glass substrate with the transparent electrode line after cleaning was mounted in the substrate holder of a vacuum deposition apparatus, and first, compound HT-1 and compound HI-1 were co-deposited on the side where the transparent electrode line was formed, so as to cover the transparent electrode, forming a hole injection layer with a film thickness of 10 nm. The content of compound HT-1 in the hole injection layer was set to 97% by mass, and the content of compound HI-1 was set to 3% by mass. Next, compound HT-1 was deposited on top of the hole injection layer to form a first hole transport layer with a film thickness of 60 nm. Next, compound EBL-1 was deposited on the first hole transport layer to form a second hole transport layer (also called an electron barrier layer) with a thickness of 5 nm. Then, compound h-host-1 as the first host material (first compound), compound e-host as the second host material (fourth compound), compound PD-1 (second compound) as a sensitizing material, and compound BD-1 as a fluorescent material (third compound) were co-deposited on the second hole transport layer to form an emissive layer with a thickness of 30 nm. The content of compound h-host-1 in the emissive layer was set to 43.9% by mass, the content of compound e-host to 43.9% by mass, the content of compound PD-1 to 11.0% by mass, and the content of compound BD-1 to 1.2% by mass. Next, compound HBL-1 was deposited on the emissive layer to form a hole barrier layer with a thickness of 5 nm. Next, compound ET-1 and Liq were co-deposited on the hole barrier layer to form an electron transport layer with a thickness of 30 nm. The content of compound ET-1 in the electron transport layer was 50% by mass, and the content of Liq was 50% by mass. Liq is an abbreviation for (8-Quinolinolato)lithium. Next, LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 1 nm. Then, metallic aluminum (Al) was deposited on the electron injection layer to form a metallic Al cathode with a thickness of 50 nm. In this manner, an organic EL device according to Example 1 was fabricated.The element configuration of the organic EL element according to Example 1 is schematically shown as follows: ITO(130) / HT-1:HI-1(10,97%:3%) / HT-1(60) / EBL-1(5) / h-host-1:e-host:PD-1:BD-1(30,43.9%:43.9%:11.0%:1.2%) / HBL-1(5) / ET-1:Liq(30,50%:50%) / LiF(1) / Al(50) In the schematically shown element configuration, the numbers in parentheses indicate the film thickness (unit: nm). Similarly, within the parentheses, the percentage figures (97%:3%) indicate the mass %) content of compound HT-1 and compound HI-1 in the hole injection layer, the percentage figures (43.9%:43.9%:11.0%:1.2%) indicate the mass %) content of compound h-host-1, compound e-host, compound PD-1, and compound BD-1 in the light-emitting layer, and the percentage figures (50%:50%) indicate the mass %) content of compound ET-1 and Liq in the electron transport layer.

[0602] [Examples 2 to 5] The organic EL elements of Examples 2 to 5 were fabricated in the same manner as the organic EL element of Example 1, except that the compound h-host-1 used to form the light-emitting layer of Example 1 was replaced with the compounds shown in Table 1.

[0603] [Comparative Example 1] The organic EL element of Comparative Example 1 was prepared in the same manner as in Example 1, except that the compound h-host-1 used in the light-emitting layer of Example 1 was replaced with one of the compounds listed in Table 1.

[0604] <Evaluation of Organic EL Devices> The fabricated organic EL devices were evaluated as follows. The evaluation results are shown in Table 1.

[0605] (Lifespan (LT95)) The fabricated organic EL element has a current density of 50 mA / cm². ２A voltage was applied to achieve the desired brightness, and the time it took for the brightness to reach 95% of the initial brightness (LT95 (unit: hours)) was measured as the lifespan. Brightness was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). Table 1 shows the "LT95 (relative value)" (unit: %). The LT95 (relative value) for each example (Examples 1 to 5 and Comparative Example 1) was calculated based on the following formula (Number X1): (Number X1): LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 1) × 100

[0606]

[0607] The organic EL elements of Examples 1 to 5, which contain the compound represented by formula (1) (the first compound) as the first host material in the light-emitting layer, had a longer lifespan compared to the organic EL element of Comparative Example 1, in which the first compound was replaced with compound Ref-1. By having one or more deuterium atoms in compounds h-host-1 to h-host-5 used in the organic EL elements of Examples 1 to 5, a longer lifespan was achieved compared to compound Ref-1, which does not contain any deuterium atoms. A tendency was observed for the lifespan of the organic EL element to increase as the number of deuterium atoms in the compound represented by formula (1) increased. Comparing Examples 1, 3, and 4, the R of the compound represented by formula (1) １２１ ~R １２８ The fact that the atom in that position is a deuterium atom greatly contributed to extending its lifespan.

[0608] <Synthesis Example> The structure of the compound synthesized in the synthesis example is shown below.

[0609]

[0610]

[0611]

[0612] [Synthesis Example 1: Synthesis of Compound h-host-1] Compound h-host-1 was synthesized using the following synthetic route.

[0613]

[0614] (Step 1: Synthesis of Intermediate M1) Under an argon atmosphere, compound m1 (1-bromo-3-iodobenzene d4 (5.00 g)), compound m2 (9-phenylcarbazole-3-boronic acid (5.50 g)), tris(dibenzylideneacetone)dipalladium (0) (319 mg), and 2,2'-bis(diphenylphosphin)-1,1'-binaphthyl (434 mg) were added to 1,4-dioxane (50 mL) and 2M potassium carbonate aqueous solution (15 mL), and the mixture was stirred at 100°C for 7 hours. After cooling, the mixture was extracted with ethyl acetate and the organic layer was collected. The obtained organic layer was concentrated, and the residue was purified by column chromatography to obtain a white solid (4.35 g). The obtained solid was the target intermediate M1, and mass spectral analysis showed a molecular weight of 402 with a m / e ratio of 403. The yield of intermediate M1 was 62%.

[0615] (Step 2: Synthesis of Intermediate M2) Under an argon atmosphere, intermediate M1 (4.00 g), compound m3 (3-chloro-9H-carbazole (2.28 g)), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (218 mg), and sodium tert-butoxide (1.43 g) were added to xylene (50 mL), and the mixture was stirred at 140°C for 7 hours. After cooling, the mixture was extracted with ethyl acetate, and the organic layer was collected. The obtained organic layer was concentrated, and the residue was purified by column chromatography to obtain a white solid (4.06 g). The obtained solid was the target product, intermediate M2, and mass spectral analysis showed a molecular weight of 530 with a m / e ratio of 531. The yield of intermediate M2 was 77%.

[0616] (Step 3: Synthesis of compound h-host-1) Intermediate M2 (4.00 g), 9H-carbazole (1.32 g), SPhosPdG4 (180 mg), and sodium tert-butoxide (1.09 g) were suspended in xylene (80 mL) and heated and stirred at 140°C for 7 hours. After cooling, methanol was added and the precipitated solid was collected. The obtained solid was purified by column chromatography to obtain a white solid (3.24 g). The obtained solid was the target compound h-host-1, and mass spectral analysis showed a molecular weight of 660 and a m / e ratio of 661. The yield of compound h-host-1 was 65%.

[0617] [Synthesis Examples 2-5: Synthesis of Compounds h-host-2 to h-host-5] In Synthesis Examples 2-5, the compounds h-host-2 to h-host-5 were synthesized in the same manner as in Synthesis Example 1, except that compounds m1, m2, and m3 in the synthesis route of Synthesis Example 1 were replaced with compounds m1, m2, and m3 shown in Table 2, respectively, and steps 1 and 2 were performed to synthesize compounds h-host-2 to h-host-5.

[0618] Table 2 shows the products synthesized in each synthesis example, the compounds m1 to m3 used in the synthesis route, and the reaction yield at each step.

[0619]

[0620] [Synthesis Example 6: Synthesis of Compound h-host-6] Compound h-host-6 was synthesized using the following synthetic route.

[0621]

[0622] Under an argon atmosphere, intermediate M3 (1.10 g), intermediate M4 (1.00 g), and PdCl ２ (Amphos) ２77 mg of the compound was mixed with 1,4-dioxane (20 mL) and 2 M potassium carbonate aqueous solution (5 mL) and stirred at 100°C for 7 hours. After cooling, the mixture was extracted with ethyl acetate and the organic layer was collected. The obtained organic layer was concentrated, and the residue was purified by column chromatography to obtain a white solid (0.935 g). The obtained solid was the target compound h-host-6, and mass spectral analysis showed a molecular weight of 681 with a m / e ratio of 682. The yield of compound h-host-6 was 63%.

[0623] 1...Organic EL element, 2...Substrate, 3...Anode, 4...Cathode, 5...Light-emitting layer, 6...Hole injection layer, 7...Hole transport layer, 8...Electron transport layer, 9...Electron injection layer, 10...Light-emitting unit.

Claims

A compound represented by the following formula (1). (In formula (1) above, L is A substituted or unsubstituted ring-forming arylene group having 6 to 18 carbon atoms, or A divalent heterocyclic group having 5 to 18 substituted or unsubstituted ring-forming atoms, R １ , R ２ , R ３ , R ４ and R ５ Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R １０１ 、 R １０２ 、 R １０３ 、 R １０４ 、 R １０５ 、 R １０６ 、 R １０７ and R １０８ One selected from the group consisting of is a single bond bonded to *a, R is not a single bond １０１ ~R １０８ Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R １１１ , R １１２ , R １１３ , R １１４ , R １１５ , R １１６ , R １１７ and R １１８ One of the groups consisting of is a single bond that connects to *b, R is not a single bond １１１ ~R １１８ Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R １２１ , R １２２ , R １２３ , R １２４ , R １２５ , R １２６ , R １２７ and R １２８ Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R is not a single bond, does not form a substituted or unsubstituted monoring, and does not form a substituted or unsubstituted fused ring. １ ~R ５ , R １０１ ~R １０８ , R １１１ ~R １１８ , and R １２１ ~R １２８ Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, Substituted or unsubstituted C1-C20 haloalkyl groups, Substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 20 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 20 carbon atoms, -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ ) a base represented by -O-(R ９０４ ) a base represented by -S-(R ９０５ ) a base represented by -N(R) ９０６ ) (Caution ９０７ ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, -C(=O)R ８０１ A base represented by - COOR ８０２ A base represented by halogen atom, Cyano group, Nitro group, -P (=O) (R ９３１ ) (Caution ９３２ ) a base represented by -Ge(R) ９３３ ) (Caution ９３４ ) (Caution ９３５ ) a base represented by -B(R) ９３６ ) (Caution ９３７ ) a base represented by -B (OR ９３８ ) ( OR ９３９ ) a base represented by -O-S (=O) ２ (R ９４０ ) a base represented by A substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or A heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms, However, R １ ~R ５ , R １０１ ~R １０８ , R １１１ ~R １１８ , and R １２１ ~R １２８ One or more atoms selected from the group consisting of are deuterium atoms, R ９０１ ~R ９０７ , R ８０１ ~R ８０２ , and R ９３１ ~R ９４０ Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 20 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or A heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms, R ９０１ If multiple R ９０１ They are either identical or different from one another. R ９０２ If multiple R ９０２ They are either identical or different from one another. R ９０３ If multiple R ９０３ They are either identical or different from one another. R ９０４ If multiple R ９０４ They are either identical or different from one another. R ９０５ If multiple R ９０５ They are either identical or different from one another. R ９０６ If multiple R ９０６ They are either identical or different from one another. R ９０７ If multiple R ９０７ They are either identical or different from one another. R ８０１ When there are a plurality of R's ８０１ they may be the same as or different from each other R ８０２ If multiple R ８０２ They are either identical or different from one another. R ９３１ If multiple R ９３１ They are either identical or different from one another. R ９３２ When there are a plurality of R's ９３２ they may be the same as or different from each other R ９３３ If multiple R ９３３ They are either identical or different from one another. R ９３４ If multiple R ９３４ They are either identical or different from one another. R ９３５ If multiple R ９３５ They are either identical or different from one another. R ９３６ If multiple R ９３６ They are either identical or different from one another. R ９３７ If multiple R ９３７ They are either identical or different from one another. R ９３８ If multiple R ９３８ They are either identical or different from one another. R ９３９ If multiple R ９３９ They are either identical or different from one another. R ９４０ If multiple R ９４０ (They are either identical or different to each other.) 　 In the compound represented by formula (1), R does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted fused ring. １ ~R ５ However, it is a deuterium atom, The compound according to claim 1. 　 In the compound represented by formula (1) above, R does not form a single bond, nor does it form a substituted or unsubstituted monoring, nor does it form a substituted or unsubstituted fused ring. １０１ ~R １０８ However, it is a deuterium atom, The compound according to claim 1 or claim 2. In the compound represented by formula (1) above, R does not form a single bond, nor does it form a substituted or unsubstituted monoring, nor does it form a substituted or unsubstituted fused ring. １１１ ~R １１８ However, it is a deuterium atom, The compound according to any one of claims 1 to 3. 　 In the compound represented by formula (1), R does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted fused ring. １２１ ~R １２８ However, it is a deuterium atom, The compound according to any one of claims 1 to 4. 　 In the compound represented by formula (1) above, L is a substituted or unsubstituted arylene group having 6 to 14 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 14 ring-forming atoms. The compound according to any one of claims 1 to 5. 　 In the compound represented by formula (1) above, L is a group represented by the following formulas (L1), (L2), or (L3): The compound according to any one of claims 1 to 6. (In formula (L1), formula (L2), or formula (L3), R １３１ , R １３２ , R １３３ , R １３４ and R １３５ Each of them operates independently. hydrogen atom, halogen atom, Substituted or unsubstituted alkyl groups having 1 to 18 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 18 carbon atoms, or A heterocyclic group having 5 to 18 substituted or unsubstituted ring-forming atoms, * indicates the bonding position. 　 In the compound represented by formula (1) above, all of the hydrogen atoms in L are deuterium atoms. The compound according to any one of claims 1 to 7. 　 All hydrogen atoms in the molecule of the compound represented by formula (1) are deuterium atoms. The compound according to any one of claims 1 to 8. R １０３ , R １０４ , R １０５ and R １０６ One of the groups consisting of is a single bond that connects to *a, R １１３ , R １１４ , R １１５ and R １１６ One of the groups selected is a single bond that connects to *b. The compound according to any one of claims 1 to 9. 　 The compound represented by formula (1) above is represented by the following formula (10), The compound according to any one of claims 1 to 10. (In formula (10) above, L, R １ ~R ５ , R １０１ ~R １０５ , R １０７ , R １０８ , R １１１ , R １１２ , R １１４ ~R １１８ , and R １２１ ~R １２８ These are L and R in formula (1) above, respectively. １ ~R ５ , R １０１ ~R １０５ , R １０７ , R １０８ , R １１１ , R １１２ , R １１４ ~R １１８ , and R １２１ ~R １２８ (This is synonymous with...) 　 In the compound represented by formula (1) above, R does not form a single bond, nor does it form a substituted or unsubstituted monoring, nor does it form a substituted or unsubstituted fused ring. １ ~R ５ , R １０１ ~R １０８ , R １１１ ~R １１８ and R １２１ ~R １２８ Each of them operates independently. hydrogen atom, halogen atom, Substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 14 carbon atoms, or These are heterocyclic groups with 5 to 14 substituted or unsubstituted ring-forming atoms. The compound according to any one of claims 1 to 11. 　 In the compound represented by formula (1) above, R does not form a single bond, nor does it form a substituted or unsubstituted monoring, nor does it form a substituted or unsubstituted fused ring. １ ~R ５ , R １０１ ~R １０８ , R １１１ ~R １１８ and R １２１ ~R １２８ Each of them operates independently. hydrogen atom, halogen atom, Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, or These are heterocyclic groups with 5 to 12 substituted or unsubstituted ring-forming atoms. The compound according to any one of claims 1 to 12. R １ ~R ５ Of these, any set of two or more adjacent items cannot be combined with each other. R １０１ ~R １０８ Of these, any set of two or more adjacent items cannot be combined with each other. R １１１ ~R １１８ Of these, any set of two or more adjacent items cannot be combined with each other. R １２１ ~R １２８ Of these, any set of two or more adjacent items cannot be combined with each other. The compound according to any one of claims 1 to 13. In the case of "substituted or unsubstituted," the substituent is an unsubstituted alkyl group having 1 to 18 carbon atoms, an unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 18 ring-forming atoms. The compound according to any one of claims 1 to 14. 　 A material for an organic electroluminescent device, comprising the compound described in any one of claims 1 to 15. 　 Cathode and, Anode and, It comprises a light-emitting unit disposed between the cathode and the anode, The light-emitting unit contains the compound described in any one of claims 1 to 16. Organic electroluminescent element. 　 The light-emitting unit has one or more light-emitting layers, At least one of the one or more light-emitting layers contains the compound as the first compound. The organic electroluminescent element according to claim 17. 　 At least one of the one or more light-emitting layers contains the first compound as the first host material. The organic electroluminescent element according to claim 18. 　 An electronic device equipped with an organic electroluminescent element according to any one of claims 17 to 19.

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