Compound, organic electroluminescent element, and electronic device

Abstract

This compound is represented by formula (1). In formula (1), any one of R9, R10 and R11 is a group represented by formula (1A), R1 to R8 and the other moieties among R9 to R11 are each a hydrogen atom, a substituent group, or the like. R13a to R13h form a ring represented by formula (1B-1) or a ring represented by formula (1B-2), or are each a hydrogen atom, a substituent group, or the like. If m and n are both 0, then (L1)m and (L2)n are both single bonds. If m and n are both between 1 and 3, then L1 and L2 are both divalent groups. Y is a group represented by formula (1C), a substituent group, or the like. In a group represented by formula (1A), Ak1 and Ak2 are both substituent groups. R13a to R13h are hydrogen atoms, substituent groups, or the like.

Description

Compound, organic electroluminescence element and electronic device

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

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

[0003] For example, Patent Document 1 discloses a fused ring compound containing a nitrogen atom and a boron atom as a compound that can be used in an organic electroluminescence device.

[0004] International Publication No. 2023 / 042574

[0005] Further improvements in the performance of organic EL elements are desired to improve the performance of electronic devices such as displays, etc. Examples of the performance of organic EL elements include luminance, emission wavelength, half-width, chromaticity, luminous efficiency, driving voltage, and lifespan.

[0006] An object of the present invention is to provide a compound capable of extending the life of an organic electroluminescent device. Another object of the present invention is to provide an organic electroluminescent device that emits light with a long life, and to provide an electronic device equipped with the organic electroluminescent device.

[0007] According to one aspect of the present invention, there is provided a compound represented by the following formula (1):

[0008]

[0009] [(in the formula (1), R１ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , and R ８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ９ , R １０ , and R １１ any one of R is a single bond bonding to *2 in the group represented by formula (1A), and R is not a single bond bonding to *2 in the group represented by formula (1A). ９ ~R １１ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １３ａ , R １３ｂ , R １３ｃ , R １３ｄ , R １３ｅ , R １３ｆ , R １３ｇ , and R １３ｈ Any one of R is a single bond bonded to *1, and R is not a single bond bonded to *1 １３ａ ~R １３ｈ one or more pairs of adjacent R groups bond to each other to form a ring represented by formula (1B-1), bond to each other to form a ring represented by formula (1B-2), or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring １ ~R ８ R is not a group represented by formula (1A), does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring. ９ ~R １１ and R which is not a single bond bonded to *1, does not form a ring represented by formula (1B-1), and does not form a ring represented by formula (1B-2).１３ａ ~R １３ｈ , each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ a group represented by —O—(R １３６ ), a group represented by —S—(R １３７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, １ is an oxygen atom, a sulfur atom, or C(R １３８ ) (R １３９ ) and L １ and L ２ are each independently a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, or a substituted or unsubstituted divalent aralkyl group having 7 or more carbon atoms, m and n are each independently 0, 1, 2, or 3, provided that when m is 0, (L １ ) m represents a single bond, and when n is 0, (L ２ ) n represents a single bond, and when m is 2 or 3, a plurality of L １ are the same or different from each other, and when n is 2 or 3, a plurality of L ２ are the same or different, Y is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ a group represented by —Si(R１３３ ) (R １３４ ) (R １３５ a group represented by —O—(R １３６ ), a group represented by —S—(R １３７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (1C). ｋ１ and A ｋ２ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; R １２ａ , R １２ｂ , and R １２ｃ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused ring １２ａ ~R １２ｃ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ a group represented by —O—(R １３６ ), a group represented by —S—(R １３７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.) (In the formulae (1B-1) and (1B-2), R １４ａ , R １４ｂ , R１４ｃ , and R １４ｄ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring １４ａ ~R １４ｄ , and R １５ａ , R １５ｂ , R １５ｃ , and R １５ｄ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ a group represented by —O—(R １３６ ), a group represented by —S—(R １３７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ２ is an oxygen atom, a sulfur atom, or C(R １３８ ) (R １３９ ) wherein *3, *4, *5, and *6 each independently represent a bonding position.) (In the formula (1C), R １６ａ , R １６ｂ , R １６ｃ , R １６ｄ , R １６ｅ , R １６ｆ , R １６ｇ , and R １６ｈ Any one of the １ is a single bond that bonds to L １ R that is not a single bond １６ａ ~R １６ｈone or more pairs of adjacent two or more of the following are bonded to each other to form a ring represented by formula (1B-1), bonded to each other to form a ring represented by formula (1B-2), or are not bonded to each other, and L １ is not a single bond bonded to R, which does not form a ring represented by formula (1B-1) and does not form a ring represented by formula (1B-2) １６ａ ~R １６ｈ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ a group represented by —O—(R １３６ ), a group represented by —S—(R １３７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ３ is an oxygen atom, a sulfur atom, or C(R １３８ ) (R １３９ (In the compound represented by the formula (1), R １３１ ~R １３７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted hydrocarbon ring group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and R １３８ and R １３９are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the substituted or unsubstituted monocycle or the substituted or unsubstituted fused ring. １３８ and R １３９ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, １３１ If there are multiple R １３１ are the same or different from each other, R １３２ If there are multiple R １３２ are the same or different from each other, R １３３ If there are multiple R １３３ are the same or different from each other, R １３４ If there are multiple R １３４ are the same or different from each other, R １３５ If there are multiple R １３５ are the same or different from each other, R １３６ If there are multiple R １３６ are the same or different from each other, R １３７ If there are multiple R １３７ are the same or different from each other, R １３８ If there are multiple R １３８ are the same or different from each other, R １３９ If there are multiple R １３９ are the same or different from each other.) (However, among the compounds represented by formula (1), the compounds represented by the following formulas (10A) and (10B) are excluded.)

[0010]

[0011] According to one aspect of the present invention, there is provided an organic electroluminescence device comprising a cathode, an anode, and an organic layer between the cathode and the anode, wherein at least one layer included in the organic layer contains the compound according to one aspect of the present invention as a first compound.

[0012] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescence element according to one aspect of the present invention.

[0013] According to one embodiment of the present invention, it is possible to provide a compound capable of extending the lifetime of an organic electroluminescence device, an organic electroluminescence device that emits light with a long lifetime, and an electronic device equipped with the organic electroluminescence device.

[0014] 1 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a third embodiment of the present invention; FIG. 2 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a fourth embodiment of the present invention; and FIG. 3 is a diagram showing a schematic configuration of another example of an organic electroluminescence element according to the fourth embodiment of the present invention.

[0015] [Definitions] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0016] In this specification, in a chemical structural formula, a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded to a possible bonding position that is not explicitly marked with a symbol such as "R" or "D" representing a deuterium atom.

[0017] As used herein, the term "number of ring carbon atoms" refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. For example, a 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and a 9,9'-spirobifluorenyl group has 25 ring carbon atoms. When a benzene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of a benzene ring substituted with an alkyl group is 6. Furthermore, when the naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.

[0018] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, and a ring assembly). Atoms that do not constitute the ring (e.g., hydrogen atoms terminating the bonds of atoms constituting the ring) and atoms contained in the substituent when the ring is substituted with a substituent are not included in the number of ring atoms. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms or atoms constituting a substituent bonded to the pyridine ring is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. Furthermore, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring, so the number of ring atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

[0019] In this specification, the "number of carbon atoms XX to YY" in the expression "substituted or unsubstituted ZZ group having carbon atoms XX to YY" represents the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0020] In this specification, the "number of atoms XX to YY" in the expression "substituted or unsubstituted ZZ group having number of atoms XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of substituents when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0021] In this specification, an unsubstituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group". In this specification, "unsubstituted" in the case of a "substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protist atom, a deuterium atom, or a tritium atom. Furthermore, in this specification, "substituted" in the case of a "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. Similarly, "substituted" in the case of a "BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced with an AA group.

[0022] "Substituents Described in This Specification" The substituents described in this specification are explained below.

[0023] The number of ring carbon atoms of an "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring atoms of an "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms of an "unsubstituted alkyl group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein. The number of carbon atoms of an "unsubstituted alkenyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of carbon atoms of an "unsubstituted alkynyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of ring carbon atoms of an "unsubstituted cycloalkyl group" described herein is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified herein. Unless otherwise specified herein, the number of ring carbon atoms of an "unsubstituted arylene group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18. Unless otherwise specified herein, the number of ring atoms of an "unsubstituted divalent heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18. Unless otherwise specified herein, the number of carbon atoms of an "unsubstituted alkylene group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0024] "Substituted or Unsubstituted Aryl Group" Specific examples (Specific Example Group G1) of the "substituted or unsubstituted aryl group" described herein include the following unsubstituted aryl group (Specific Example Group G1A) and substituted aryl group (Specific Example Group G1B). (Here, an unsubstituted aryl group refers to a case where a "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and a substituted aryl group refers to a case where a "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" simply refers to both an "unsubstituted aryl group" and a "substituted aryl group." A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with substituents. Examples of the "substituted aryl group" include a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with substituents in the "unsubstituted aryl group" of the following Specific Example Group G1A, and examples of the substituted aryl group of the following Specific Example Group G1B. It should be noted that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl groups" described in this specification also include groups in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl groups" of the following specific example group G1B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted aryl groups" of the following specific example group G1B is further replaced with a substituent.

[0025] Unsubstituted aryl groups (specific example group G1A): a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a benzanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a triphenylenyl group, a benzotriphenylenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, A 9,9'-spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a fluoranthenyl group, a benzofluoranthenyl group, a perylenyl group, and a monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0026]

[0027]

[0028] Substituted aryl groups (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, cyanophenyl group, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl group, and A group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by the above general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0029] "Substituted or Unsubstituted Heterocyclic Group" The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom among the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom. The "heterocyclic group" described herein is a monocyclic group or a fused ring group. The "heterocyclic group" described herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described herein include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, an unsubstituted heterocyclic group refers to when a "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and a substituted heterocyclic group refers to when a "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when simply referring to a "heterocyclic group", it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group". A "substituted heterocyclic group" means a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with substituents. Specific examples of the "substituted heterocyclic group" include groups in which hydrogen atoms of an "unsubstituted heterocyclic group" in the following specific example group G2A are replaced, and examples of substituted heterocyclic groups in the following specific example group G2B. The examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic groups" described in this specification also include groups in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic groups" of specific example group G2B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted heterocyclic groups" of specific example group G2B is further replaced with a substituent.

[0030] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0031] Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced with substituents (specific example group G2B4).

[0032] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolidinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, an indazolyl group, a phenanthrolinyl group, a phenanthridinyl group, an acridinyl group, a phenazinyl group, a carbazolyl group, Benzocarbazolyl group, morpholino group, phenoxazinyl group, phenothiazinyl group, azacarbazolyl group, and diazacarbazolyl group.

[0033] Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): a furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a xanthenyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a benzoxazolyl group, a benzisoxazolyl group, a phenoxazinyl group, a morpholino group, a dinaphthofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, an azanaphthobenzofuranyl group, and a diazanaphthobenzofuranyl group.

[0034] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a benzothiophenyl group (benzothienyl group), an isobenzothiophenyl group (isobenzothienyl group), a dibenzothiophenyl group (dibenzothienyl group), a naphthobenzothiophenyl group (naphthobenzothienyl group), a benzothiazolyl group, a benzisothiazolyl group, a phenothiazinyl group, a dinaphthothiophenyl group (dinaphthothienyl group), an azadibenzothiophenyl group (azadibenzothienyl group), a diazadibenzothiophenyl group (diazadibenzothienyl group), an azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and a diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0035] Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0036]

[0037]

[0038] In the general formulae (TEMP-16) to (TEMP-33), X Ａ and Y Ａ are each independently an oxygen atom, a sulfur atom, NH, or CH ２ However, X Ａ and Y Ａ At least one of X is an oxygen atom, a sulfur atom, or NH. Ａ and Y Ａ At least one of the groups is NH or CH ２ In this case, the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) may contain any of these NH, CH ２ and monovalent groups obtained by removing one hydrogen atom from the group consisting of:

[0039] Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): a (9-phenyl)carbazolyl group, a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a (9-naphthyl)carbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a methylbenzimidazolyl group, an ethylbenzimidazolyl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenylquinazolinyl group, and a biphenylylquinazolinyl group.

[0040] Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): a phenyldibenzofuranyl group, a methyldibenzofuranyl group, a t-butyldibenzofuranyl group, and a monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0041] Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3): a phenyldibenzothiophenyl group, a methyldibenzothiophenyl group, a t-butyldibenzothiophenyl group, and a monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0042] Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4):

[0043] The "one or more hydrogen atoms of the monovalent heterocyclic group" refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, X Ａ and Y Ａ a hydrogen atom bonded to a nitrogen atom when at least one of Ａ and Y Ａ One of them is CH ２ and n is 0 or more. The methylene group in the formula (I) is one or more hydrogen atoms selected from the hydrogen atoms of the methylene group in the formula (I).

[0044] "Substituted or Unsubstituted Alkyl Group" Specific examples (Specific Example Group G3) of the "substituted or unsubstituted alkyl group" described herein include the following unsubstituted alkyl group (Specific Example Group G3A) and substituted alkyl group (Specific Example Group G3B). (Here, the term "unsubstituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and the term "substituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereinafter, the term "alkyl group" includes both an "unsubstituted alkyl group" and a "substituted alkyl group." A "substituted alkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced with substituents. Specific examples of the "substituted alkyl group" include the following "unsubstituted alkyl group" (Specific Example Group G3A) in which one or more hydrogen atoms are replaced with substituents, and the examples of the substituted alkyl group (Specific Example Group G3B). In this specification, the alkyl group in an "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the term "unsubstituted alkyl group" includes a straight-chain "unsubstituted alkyl group" and a branched "unsubstituted alkyl group." The examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes groups in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" of specific example group G3B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted alkyl group" of specific example group G3B is further replaced with a substituent.

[0045] Unsubstituted alkyl groups (specific example group G3A): a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, and a t-butyl group.

[0046] Substituted alkyl groups (specific example group G3B): a heptafluoropropyl group (including isomers), a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, and a trifluoromethyl group.

[0047] "Substituted or Unsubstituted Alkenyl Group" Specific examples (Specific Example Group G4) of the "substituted or unsubstituted alkenyl group" described herein include the following unsubstituted alkenyl group (Specific Example Group G4A) and substituted alkenyl group (Specific Example Group G4B). (Here, an unsubstituted alkenyl group refers to a case where a "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and a "substituted alkenyl group" refers to a case where a "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply refers to both an "unsubstituted alkenyl group" and a "substituted alkenyl group." A "substituted alkenyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced with substituents. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl groups" (specific example group G4A) having a substituent, and examples of substituted alkenyl groups (specific example group G4B). The examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl group" described in this specification also includes groups in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl groups" of specific example group G4B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted alkenyl groups" of specific example group G4B is further replaced with a substituent.

[0048] Unsubstituted alkenyl groups (specific example group G4A): a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, and a 3-butenyl group.

[0049] Substituted alkenyl groups (specific example group G4B): a 1,3-butadienyl group, a 1-methylvinyl group, a 1-methylallyl group, a 1,1-dimethylallyl group, a 2-methylallyl group, and a 1,2-dimethylallyl group.

[0050] - "Substituted or Unsubstituted Alkynyl Group" Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl group (specific example group G5A). (Here, an unsubstituted alkynyl group refers to a case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, the term "alkynyl group" includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group." A "substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" have been replaced with a substituent. Specific examples of the "substituted alkynyl group" include a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" (specific example group G5A) have been replaced with a substituent.

[0051] Unsubstituted alkynyl groups (specific example group G5A): ethynyl group.

[0052] "Substituted or Unsubstituted Cycloalkyl Group" Specific examples (Specific Example Group G6) of the "substituted or unsubstituted cycloalkyl group" described herein include the following unsubstituted cycloalkyl group (Specific Example Group G6A) and substituted cycloalkyl group (Specific Example Group G6B). (Here, the term "unsubstituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group," and the term "substituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group.") In this specification, the term "cycloalkyl group" simply refers to both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group." A "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced with substituents. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (Specific Example Group G6A) in which one or more hydrogen atoms are replaced with substituents, and the examples of the substituted cycloalkyl group (Specific Example Group G6B). The examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed here are merely examples, and the "substituted cycloalkyl groups" described in this specification also include groups in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl groups" of specific example group G6B are replaced with substituents, and groups in which a hydrogen atom of a substituent in the "substituted cycloalkyl groups" of specific example group G6B is further replaced with a substituent.

[0053] Unsubstituted cycloalkyl groups (specific example group G6A): a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a 2-norbornyl group.

[0054] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.

[0055] -Si(R ９０１ ) (R ９０２ ) (R ９０３ A group represented by —Si(R ９０１ ) (R ９０２) (R ９０３ Specific examples (specific example group G7) of the group represented by the formula (G1) include -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. The multiple G1s in -Si(G1)(G1)(G1) may be the same or different. - Multiple G2 in Si(G1)(G2)(G2) are the same as or different from each other. - Multiple G1 in Si(G1)(G1)(G2) are the same as or different from each other. - Multiple G2 in Si(G2)(G2)(G2) are the same as or different from each other. - Multiple G3 in Si(G3)(G3)(G3) are the same as or different from each other. - Multiple G6 in Si(G6)(G6)(G6) are the same as or different from each other.

[0056] ・「-O-(R ９０４ A group represented by —O—(R ９０４ ) (Specific example group G8) includes -O(G1), -O(G2), -O(G3), and -O(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0057] ・"-S-(R ９０５ A group represented by —S—(R ９０５) (Specific example group G9) includes -S(G1), -S(G2), -S(G3), and -S(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0058] ・「-N(R ９０６ ) (R ９０７ A group represented by —N(R ９０６ ) (R ９０７ Specific examples (specific example group G10) of groups represented by the formula (G1) include -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. Multiple G1s in -N(G1)(G1) may be the same as or different from one another. Multiple G2s in -N(G2)(G2) may be the same as or different from one another. Multiple G3s in -N(G3)(G3) may be the same as or different from one another. The multiple G6s in -N(G6)(G6) are the same as or different from each other.

[0059] "Halogen Atom" Specific examples (specific example group G11) of the "halogen atom" described in this specification include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0060] "Substituted or unsubstituted fluoroalkyl group" As used herein, a "substituted or unsubstituted fluoroalkyl group" refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). Unless otherwise specified herein, the number of carbon atoms in an "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. A "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. Note that the "substituted fluoroalkyl group" described herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in a "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include the examples of the above-mentioned "alkyl group" (specific example group G3) in which one or more hydrogen atoms have been replaced with fluorine atoms.

[0061] "Substituted or unsubstituted haloalkyl group" As used herein, a "substituted or unsubstituted haloalkyl group" refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The number of carbon atoms in an "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. A "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of a "haloalkyl group" are replaced with a substituent. Note that the "substituted haloalkyl group" described herein also includes a "substituted haloalkyl group" in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain are further replaced with a substituent, and a "substituted haloalkyl group" in which one or more hydrogen atoms of the substituent are further replaced with a substituent. Specific examples of the "unsubstituted haloalkyl group" include the examples of the above-mentioned "alkyl group" (specific example group G3) in which one or more hydrogen atoms are replaced with halogen atoms. A haloalkyl group may also be referred to as a halogenated alkyl group.

[0062] - "Substituted or unsubstituted alkoxy group" A specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0063] - "Substituted or unsubstituted alkylthio group" A specific example of the "substituted or unsubstituted alkylthio group" described in this specification is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0064] - "Substituted or unsubstituted aryloxy group" A specific example of the "substituted or unsubstituted aryloxy group" described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. Unless otherwise specified in this specification, the number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0065] - "Substituted or unsubstituted arylthio group" A specific example of the "substituted or unsubstituted arylthio group" described in this specification is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. Unless otherwise specified in this specification, the number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0066] - "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Multiple G3s in -Si(G3)(G3)(G3) are the same as or different from one another. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0067] "Substituted or unsubstituted aralkyl group" A specific example of the "substituted or unsubstituted aralkyl group" described in this specification is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. Therefore, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one embodiment of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group," and the number of carbon atoms in the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification. Specific examples of the "substituted or unsubstituted aralkyl group" include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group, an α-naphthylmethyl group, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group, a 1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, a β-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethyl group, a 1-β-naphthylisopropyl group, and a 2-β-naphthylisopropyl group.

[0068] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described in this specification is preferably a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, or the like.

[0069] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic group described in this specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an aza Examples of such groups include a dibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group (a (9-phenyl)carbazol-1-yl group, a (9-phenyl)carbazol-2-yl group, a (9-phenyl)carbazol-3-yl group, or a (9-phenyl)carbazol-4-yl group), a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group.

[0070] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.

[0071]

[0072] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically any of the following groups:

[0073]

[0074] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0075] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0076]

[0077] In the general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.

[0078] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like.

[0079] "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group". Specific examples (specific example group G12) of the "substituted or unsubstituted arylene group" include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1.

[0080] "Substituted or unsubstituted divalent heterocyclic group" Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom on the heterocycle from the above-mentioned "substituted or unsubstituted heterocyclic group". Specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group" include divalent groups derived by removing one hydrogen atom on the heterocycle from the "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0081] "Substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group". Specific examples (specific example group G14) of the "substituted or unsubstituted alkylene group" include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3.

[0082] Unless otherwise specified in the present specification, the substituted or unsubstituted arylene group described in the present specification is preferably any one of the groups represented by the following general formulae (TEMP-42) to (TEMP-68).

[0083]

[0084]

[0085] In the general formulae (TEMP-42) to (TEMP-52), Q １ ~Q １０ are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-42) to (TEMP-52), * represents a bonding position.

[0086]

[0087] In the general formulae (TEMP-53) to (TEMP-62), Q １ ~Q １０ are each independently a hydrogen atom or a substituent. ９ and Q １０ may be bonded to each other via a single bond to form a ring. In the general formulae (TEMP-53) to (TEMP-62), * represents the bonding position.

[0088]

[0089] In the general formulae (TEMP-63) to (TEMP-68), Q １ ~Q ８ are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-63) to (TEMP-68), * represents a bonding position.

[0090] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any one of the groups represented by the following general formulae (TEMP-69) to (TEMP-102).

[0091]

[0092]

[0093]

[0094] In the general formulae (TEMP-69) to (TEMP-82), Q １ ~Q ９ are each independently a hydrogen atom or a substituent.

[0095]

[0096]

[0097]

[0098]

[0099] In the general formulae (TEMP-83) to (TEMP-102), Q １ ~Q ８ are each independently a hydrogen atom or a substituent.

[0100] The above is the explanation of "substituents described in this specification."

[0101] "When bonded to form a ring" In this specification, when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle, bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other," it means when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle," when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring," and when "one or more pairs of adjacent groups do not bond to each other." In this specification, the cases when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle" and "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "when bonded to form a ring") will be explained below. An anthracene compound represented by the following general formula (TEMP-103), in which the main skeleton is an anthracene ring, will be described as an example.

[0102]

[0103] For example, R ９２１~R ９３０ In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," the pair of adjacent two groups is R ９２１ and R ９２２ Paired with R ９２２ and R ９２３ Paired with R ９２３ and R ９２４ Paired with R ９２４ and R ９３０ Paired with R ９３０ and R ９２５ Paired with R ９２５ and R ９２６ Paired with R ９２６ and R ９２７ Paired with R ９２７ and R ９２８ Paired with R ９２８ and R ９２９ and R ９２９ and R ９２１ It is paired with.

[0104] The above-mentioned "one or more pairs" means that two or more pairs of adjacent two or more groups may simultaneously form a ring. For example, R ９２１ and R ９２２ and are bonded to each other to form ring Q Ａ and simultaneously form R ９２５ and R ９２６ and are bonded to each other to form ring Q Ｂ When the anthracene compound represented by the general formula (TEMP-103) is formed, the anthracene compound represented by the general formula (TEMP-104) is represented by the following general formula (TEMP-104).

[0105]

[0106] The case where a "set of two or more adjacent groups" forms a ring includes not only the case where a set of "two" adjacent groups is bonded as in the above example, but also the case where a set of "three or more" adjacent groups is bonded. For example, R ９２１ and R ９２２ and are bonded to each other to form ring Q Ａ and R ９２２ and R ９２３ and are bonded to each other to form ring Q Ｃ and three adjacent (R ９２１ , R ９２２ and R９２３ In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105): Ａ and Ring Q Ｃ is R ９２２ Share.

[0107]

[0108] The "monocyclic ring" or "fused ring" formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when "one pair of adjacent two" forms a "monocyclic ring" or a "fused ring", the "monocyclic ring" or the "fused ring" may form a saturated ring or an unsaturated ring. For example, in the case of the ring Q formed in the general formula (TEMP-104), Ａ and Ring Q Ｂ are "monocyclic rings" or "fused rings". Ａ , and ring Q Ｃ is a "fused ring". Ａ and Tamaki Q Ｃ That is, Ring Q Ａ and Tamaki Q Ｃ The ring Q in the general formula (TMEP-104) is fused to form a fused ring. Ａ is a benzene ring, then ring Q Ａ The ring Q in the general formula (TMEP-104) is a monocyclic ring. Ａ is a naphthalene ring, then ring Q Ａ is a fused ring.

[0109] The term "unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The term "saturated ring" means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of aromatic hydrocarbon rings include structures in which the groups given as specific examples in the specific example group G1 are terminated with a hydrogen atom. Specific examples of aromatic heterocyclic rings include structures in which the aromatic heterocyclic groups given as specific examples in the specific example group G2 are terminated with a hydrogen atom. Specific examples of aliphatic hydrocarbon rings include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom. "Forming a ring" means forming a ring only with a plurality of atoms of the main skeleton, or with a plurality of atoms of the main skeleton and one or more optional elements. For example, R ９２１ and R ９２２ and a ring Q formed by bonding together Ａ is R ９２１ and the carbon atom of the anthracene skeleton to which R ９２２ It means a ring formed by the carbon atom of the anthracene skeleton to which R is bonded and one or more arbitrary elements. ９２１ and R ９２２ Todekan Q Ａ In the case where R ９２１ and the carbon atom of the anthracene skeleton to which R ９２２ When a monocyclic unsaturated ring is formed by the carbon atom of the anthracene skeleton to which R is bonded and four carbon atoms, R ９２１ and R ９２２ The ring formed by

[0110] Here, unless otherwise specified herein, the "arbitrary element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur. In any element (for example, in the case of carbon or nitrogen), a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below. When any element other than a carbon element is included, the formed ring is a heterocycle. Unless otherwise specified herein, the "one or more arbitrary elements" constituting the monocycle or fused ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5. Unless otherwise specified herein, of the "monocycle" and the "fused ring," the "monocycle" is preferred. Unless otherwise specified herein, of the "saturated ring" and the "unsaturated ring," the "unsaturated ring" is preferred. Unless otherwise specified herein, the "monocycle" is preferably a benzene ring. Unless otherwise specified herein, the "unsaturated ring" is preferably a benzene ring. When "one or more pairs of adjacent two or more rings" "combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring," unless otherwise specified in this specification, preferably, one or more pairs of adjacent two or more rings combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0111] When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents Described Herein." When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents Described Herein." The above is an explanation of the case where "one or more pairs of adjacent two or more rings are bonded to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent two or more rings are bonded to form a substituted or unsubstituted fused ring" ("when bonded to form a ring").

[0112] Substituents in the case of "substituted or unsubstituted" In one embodiment of the present specification, the substituents in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituents" in the present specification) include, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ), -O-(R ９０４ ), -S-(R ９０５ ), -N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and an unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ ~R ９０７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. ９０１ When there are two or more R９０１ are the same or different from each other, R ９０２ When there are two or more R ９０２ are the same or different from each other, R ９０３ When there are two or more R ９０３ are the same or different from each other, R ９０４ When there are two or more R ９０４ are the same or different from each other, R ９０５ When there are two or more R ９０５ are the same or different from each other, R ９０６ When there are two or more R ９０６ are the same or different from each other, R ９０７ When there are two or more R ９０７ are the same or different from each other.

[0113] In one embodiment, the substituent in the "substituted or unsubstituted" is a group selected from the group consisting of an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and a heterocyclic group having 5 to 50 ring atoms.

[0114] In one embodiment, the substituent in the "substituted or unsubstituted" is a group selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heterocyclic group having 5 to 18 ring atoms.

[0115] Specific examples of each group of the above optional substituents are the specific examples of the substituents described above in the section "Substituents described in this specification."

[0116] Unless otherwise specified in this specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring. Unless otherwise specified in this specification, any optional substituent may further have a substituent. The substituents further possessed by the optional substituent are the same as those of the optional substituents described above.

[0117] In this specification, a numerical range expressed using "AA to BB" means a range that includes the number AA written before "AA to BB" as the lower limit and the number BB written after "AA to BB" as the upper limit.

[0118] [First Embodiment] (Compound) The compound according to the first embodiment is a compound represented by the following formula (1).

[0119]

[0120] [(in the formula (1), R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , and R ８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ９ , R １０ , and R １１ any one of R is a single bond bonding to *2 in the group represented by formula (1A), and R is not a single bond bonding to *2 in the group represented by formula (1A). ９ ~R １１ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １３ａ, R １３ｂ , R １３ｃ , R １３ｄ , R １３ｅ , R １３ｆ , R １３ｇ , and R １３ｈ Any one of R is a single bond bonded to *1, and R is not a single bond bonded to *1 １３ａ ~R １３ｈ one or more pairs of adjacent R groups bond to each other to form a ring represented by formula (1B-1), bond to each other to form a ring represented by formula (1B-2), or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring １ ~R ８ R is not a group represented by formula (1A), does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring. ９ ~R １１ and R which is not a single bond bonded to *1, does not form a ring represented by formula (1B-1), and does not form a ring represented by formula (1B-2). １３ａ ~R １３ｈ , each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ a group represented by —O—(R １３６ ), a group represented by —S—(R １３７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, １ is an oxygen atom, a sulfur atom, or C(R １３８ ) (R １３９) and L １ and L ２ are each independently a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, or a substituted or unsubstituted divalent aralkyl group having 7 or more carbon atoms, m and n are each independently 0, 1, 2, or 3, provided that when m is 0, (L １ ) m represents a single bond, and when n is 0, (L ２ ) n represents a single bond, and when m is 2 or 3, a plurality of L １ are the same or different from each other, and when n is 2 or 3, a plurality of L ２ are the same or different, Y is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ a group represented by —O—(R １３６ ), a group represented by —S—(R １３７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (1C). ｋ１ and A ｋ２ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; R １２ａ , R １２ｂ , and R １２ｃone or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused ring １２ａ ~R １２ｃ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ a group represented by —O—(R １３６ ), a group represented by —S—(R １３７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.) (In the formulae (1B-1) and (1B-2), R １４ａ , R １４ｂ , R １４ｃ , and R １４ｄ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring １４ａ ~R １４ｄ , and R １５ａ , R １５ｂ , R １５ｃ , and R １５ｄare each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ a group represented by —O—(R １３６ ), a group represented by —S—(R １３７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ２ is an oxygen atom, a sulfur atom, or C(R １３８ ) (R １３９ ) wherein *3, *4, *5, and *6 each independently represent a bonding position.) (In the formula (1C), R １６ａ , R １６ｂ , R １６ｃ , R １６ｄ , R １６ｅ , R １６ｆ , R １６ｇ , and R １６ｈ Any one of the １ is a single bond that bonds to L １ R that is not a single bond １６ａ ~R １６ｈ one or more pairs of adjacent two or more of the following are bonded to each other to form a ring represented by formula (1B-1), bonded to each other to form a ring represented by formula (1B-2), or are not bonded to each other, and L １ is not a single bond bonded to R, which does not form a ring represented by formula (1B-1) and does not form a ring represented by formula (1B-2) １６ａ ~R １６ｈare each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ a group represented by —O—(R １３６ ), a group represented by —S—(R １３７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ３ is an oxygen atom, a sulfur atom, or C(R １３８ ) (R １３９ (In the compound represented by the formula (1), R １３１ ~R １３７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted hydrocarbon ring group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and R １３８ and R １３９ are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the substituted or unsubstituted monocycle or the substituted or unsubstituted fused ring. １３８ and R １３９ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, １３１ If there are multiple R １３１are the same or different from each other, R １３２ If there are multiple R １３２ are the same or different from each other, R １３３ If there are multiple R １３３ are the same or different from each other, R １３４ If there are multiple R １３４ are the same or different from each other, R １３５ If there are multiple R １３５ are the same or different from each other, R １３６ If there are multiple R １３６ are the same or different from each other, R １３７ If there are multiple R １３７ are the same or different from each other, R １３８ If there are multiple R １３８ are the same or different from each other, R １３９ If there are multiple R １３９ are the same or different from each other.) (However, among the compounds represented by formula (1), the compounds represented by the following formulas (10A) and (10B) are excluded.)

[0121]

[0122] In the compound represented by the formula (1), A in the group represented by the formula (1A) ｋ１ and A ｋ２ In the compound represented by formula (1), it is preferable that at least one selected from the group consisting of: is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. ｋ１ and A ｋ２ It is preferred that both of the above groups are substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms.

[0123] In the compound represented by the formula (1), A in the group represented by the formula (1A) ｋ１ and A ｋ２ It is preferable that at least one selected from the group consisting of is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms.

[0124] In the compound represented by the formula (1), A in the group represented by the formula (1A) ｋ１ and A ｋ２ It is preferred that both of the above groups are substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms.

[0125] In the compound represented by formula (1), it is preferable that m and n are each independently 0 or 1.

[0126] In the compound represented by the formula (1), X １ is an oxygen atom or C(R １３８ ) (R １３９ ) is preferred.

[0127] In the compound represented by the formula (1), X １ is C(R １３８ ) (R １３９ ) is preferred.

[0128] In the compound represented by the formula (1), X in the group represented by the formula (1C) ３ is an oxygen atom or C(R １３８ ) (R １３９ ) is preferred.

[0129] In the compound represented by the formula (1), X in the group represented by the formula (1C) ３ is C(R １３８ ) (R １３９ ) is preferred.

[0130] In the compound represented by the formula (1), Y is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the formula (1C).

[0131] In the compound represented by formula (1), R １ ~R １１ It is preferable that the above-mentioned substituted or unsubstituted monocyclic ring and the above-mentioned substituted or unsubstituted fused ring are not formed.

[0132] In the compound represented by the formula (1), R in the group represented by the formula (1A) １２ａ ~R １２ｃIt is preferable that the above-mentioned substituted or unsubstituted monocyclic ring and the above-mentioned substituted or unsubstituted fused ring are not formed.

[0133] In the compound represented by the formula (1), R １３ａ ~R １３ｈ It is preferable that the ring represented by the formula (1B-1) does not form a ring represented by the formula (1B-2).

[0134] In the compound represented by the formula (1), L in the group represented by the formula (1C) １ R that is not a single bond １６ａ ~R １６ｈ It is preferable that the ring represented by the formula (1B-1) does not form a ring represented by the formula (1B-2).

[0135] In the compound represented by formula (1), R １ ~R ８ At least one selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or —N(R １３１ ) (R １３２ ) is preferably a group represented by the formula (I).

[0136] The compound represented by the formula (1) preferably contains at least one deuterium atom.

[0137] In the compound represented by the formula (1), A in the formula (1A) ｋ１ and A ｋ２ and n is 0 or 1. Preferably, at least one selected from the group consisting of is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and containing at least one deuterium atom, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and containing at least one deuterium atom.

[0138] In the compound represented by formula (1), R １ ~R ８ At least one selected from the group consisting of —N(R １３１ ) (R １３２ ) is preferably a group represented by the formula (I).

[0139] In the compound represented by formula (1), n ​​is preferably 0 and m is preferably 1. In the compound represented by formula (1), n ​​is preferably 1 and m is preferably 0.

[0140] In the compound represented by the formula (1), it is also preferable that n is 1 and m is 1. In the compound represented by the formula (1), it is also preferable that n is 0 and m is 0.

[0141] In the compound represented by formula (1), R ７ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or —N(R １３１ ) (R １３２ ) is preferably a group represented by the formula (I).

[0142] In the compound represented by formula (1), R ２ and R ３ Preferably, any one of the groups is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0143] In the compound represented by formula (1), R ２ and R ３ any one of R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; ６ is also preferably a group represented by a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. ２ and R ３ any one of R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; ７ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or —N(R １３１ ) (R １３２ In the compound represented by formula (1), R ２ and R ３ any one of the groups is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and containing at least one deuterium atom, and R ７is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and containing at least one deuterium atom, or —N(R １３１ ) (R １３２ In the compound represented by formula (1), R ２ and R ３ any one of R is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms; ７ is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or —N(R １３１ ) (R １３２ In the compound represented by formula (1), R ２ and R ３ any one of R is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms and containing at least one deuterium atom; ７ is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms containing at least one deuterium atom, or —N(R １３１ ) (R １３２ ) is also preferred.

[0144] The compound represented by the formula (1) is preferably a compound represented by the following formula (10):

[0145]

[0146] (In the formula (10), R １ ~R ９ , R １１ , R １３ａ ~R １３ｈ , X １ , L １ , L ２ , m, n, Y, A ｋ１ , A ｋ２ , and R １２ａ ~R １２ｃ are R in the formula (1), respectively. １ ~R ９ , R １１ , R １３ａ ~R １３ｈ , X １ , L １ , L ２, m, n, Y, A ｋ１ , A ｋ２ , and R １２ａ ~R １２ｃ is synonymous with

[0147] In the compound represented by the formula (10), A ｋ１ and A ｋ２ In the compound represented by formula (10), it is preferable that at least one selected from the group consisting of A is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. ｋ１ and A ｋ２ It is preferred that both of the above groups are substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms.

[0148] In the compound represented by the formula (10), A ｋ１ and A ｋ２ In the compound represented by formula (10), it is preferable that at least one selected from the group consisting of A is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. ｋ１ and A ｋ２ It is preferred that both of the above groups are substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms.

[0149] In the compound represented by the formula (10), it is preferable that m and n are each independently 0 or 1.

[0150] In the compound represented by the formula (10), X １ is an oxygen atom or C(R １３８ ) (R １３９ ) is preferred.

[0151] In the compound represented by the formula (10), X １ is C(R １３８ ) (R １３９ ) is preferred.

[0152] In the compound represented by the formula (10), X in the group represented by the formula (1C) ３ is an oxygen atom or C(R １３８ ) (R １３９ ) is preferred.

[0153] In the compound represented by the formula (10), X in the group represented by the formula (1C) ３ is C(R １３８ ) (R １３９ ) is preferred.

[0154] In the compound represented by the formula (10), Y is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the formula (1C).

[0155] In the compound represented by the formula (10), R １ ~R ９ , and R １１ It is preferable that the above-mentioned substituted or unsubstituted monocyclic ring and the above-mentioned substituted or unsubstituted fused ring are not formed.

[0156] In the compound represented by the formula (10), R １２ａ ~R １２ｃ It is preferable that the above-mentioned substituted or unsubstituted monocyclic ring and the above-mentioned substituted or unsubstituted fused ring are not formed.

[0157] In the compound represented by the formula (10), R １３ａ ~R １３ｈ It is preferable that the ring represented by the formula (1B-1) does not form a ring represented by the formula (1B-2).

[0158] In the compound represented by the formula (10), L in the group represented by the formula (1C) １ R that is not a single bond １６ａ ~R １６ｈ It is preferable that the ring represented by the formula (1B-1) does not form a ring represented by the formula (1B-2).

[0159] In the compound represented by the formula (10), R １ ~R ８ At least one selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or —N(R １３１ ) (R １３２ ) is preferably a group represented by the formula (I).

[0160] The compound represented by the formula (10) preferably contains at least one deuterium atom.

[0161] In the compound represented by the formula (10), A ｋ１ and A ｋ２ and n is 0 or 1. Preferably, at least one selected from the group consisting of is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and containing at least one deuterium atom, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and containing at least one deuterium atom.

[0162] In the compound represented by the formula (10), R １ ~R ８ At least one selected from the group consisting of —N(R １３１ ) (R １３２ ) is preferably a group represented by the formula (I).

[0163] In the compound represented by the formula (10), n is preferably 0 and m is preferably 1. In the compound represented by the formula (10), n is preferably 1 and m is preferably 0.

[0164] In the compound represented by the formula (10), it is also preferable that n is 1 and m is 1. In the compound represented by the formula (10), it is also preferable that n is 0 and m is 0.

[0165] In the compound represented by the formula (10), R ７ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or —N(R １３１ ) (R １３２ ) is preferably a group represented by the formula (I).

[0166] In the compound represented by the formula (10), R ２ and R ３ Preferably, any one of the groups is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0167] In the compound represented by the formula (10), R ２ and R ３any one of R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; ６ is also preferably a group represented by a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. ２ and R ３ any one of R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; ７ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or —N(R １３１ ) (R １３２ In the compound represented by formula (10), R ２ and R ３ any one of the groups is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and containing at least one deuterium atom, and R ７ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and containing at least one deuterium atom, or —N(R １３１ ) (R １３２ In the compound represented by formula (10), R ２ and R ３ any one of R is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms; ７ is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or —N(R １３１ ) (R １３２ In the compound represented by formula (10), R ２ and R ３ any one of R is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms and containing at least one deuterium atom; ７ is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms containing at least one deuterium atom, or —N(R １３１ ) (R １３２ ) is also preferred.

[0168] In the compound according to this embodiment, the substituent in the term "substituted or unsubstituted" is preferably an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 13 ring atoms.

[0169] In the compounds according to this embodiment, all groups described as "substituted or unsubstituted" are preferably "unsubstituted".

[0170] In the compound according to this embodiment, R １ ~R ８ Any pair of adjacent two or more of R ９ ~R １１ Any pair of two or more adjacent groups of R １２ａ ~R １２ｃ Any pair of adjacent two or more of R is not bonded to each other, and is not a single bond bonded to *1. １３ａ ~R １３ｈ Any pair of two or more adjacent groups of R １４ａ ~R １４ｄ Any pair of two or more adjacent groups of L １ R that is not a single bond １６ａ ~R １６ｈ It is preferable that any pair of two or more adjacent groups of the above do not bond to each other.

[0171] (Maximum Fluorescence Emission Peak Wavelength) In this specification, the maximum peak wavelength of fluorescence emission may be referred to as the maximum fluorescence emission peak wavelength. In the compound according to this embodiment, the maximum fluorescence emission peak wavelength of the compound according to this embodiment is preferably 440 nm or more, and preferably 445 nm or more. In the compound according to this embodiment, the maximum fluorescence emission peak wavelength of the compound according to this embodiment is preferably 480 nm or less, and more preferably 470 nm or less. When the maximum fluorescence emission peak wavelength of the compound according to this embodiment is 440 nm or more, electronic devices such as displays equipped with an organic EL element containing the compound according to this embodiment can easily emit the desired moderate blue light. When the maximum fluorescence emission peak wavelength of the compound according to this embodiment is 480 nm or less, electronic devices such as displays equipped with an organic EL element containing the compound according to this embodiment can easily emit the desired moderate blue light.

[0172] In this specification, the maximum fluorescence emission peak wavelength is the wavelength at which the compound to be measured is 10 －６ moles / liter or more, 10 －５ The maximum peak wavelength of the fluorescence spectrum at which the emission intensity is maximum in a fluorescence spectrum measured for a toluene solution in which the compound is dissolved at a concentration of 1 mole / liter or less. The measurement device may be a fluorescence spectrum measurement device (device name: FP-8300, manufactured by JASCO Corporation). Note that the fluorescence spectrum measurement device is not limited to the device exemplified here.

[0173] (Method for Producing Compound According to This Embodiment) The compound according to this embodiment can be produced according to the synthesis method described in the Examples below, or by imitating the synthesis method and using known alternative reactions and raw materials suited to the target compound.

[0174] (Specific Examples of Compounds According to This Embodiment) Specific examples of compounds according to this embodiment include the following compounds, however, the present invention is not limited to these specific examples.

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

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[0200]

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[0251]

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[0264]

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[0267]

[0268] [Second Embodiment] (Material for Organic Electroluminescence Device) The material for organic electroluminescence devices according to this embodiment contains the compound according to the first embodiment. One embodiment includes a material for organic electroluminescence devices containing only the compound according to the first embodiment, and another embodiment includes a material for organic electroluminescence devices containing the compound according to the first embodiment and another compound different from the compound according to the first embodiment. In the material for organic electroluminescence devices according to this embodiment, it is preferable that the compound according to the first embodiment is a dopant material. In this case, the material for organic electroluminescence devices may contain the compound according to the first embodiment as a dopant material and another compound such as, for example, a host material.

[0269] The compound according to the first embodiment can be used as a material for an organic EL device, can be used as a material for the light-emitting layer of an organic EL device, and can be used in particular as a blue-emitting material for the light-emitting layer.

[0270] One aspect of the compound different from the compound in the first embodiment is a compound that can be used as a blue light-emitting material in the light-emitting layer.

[0271] (Specific Examples of Other Compounds That Can Be Used as Blue Light-Emitting Materials in the Light-Emitting Layer) Specific examples of compounds that are different from the compounds in the first embodiment and can be used as blue light-emitting materials in the light-emitting layer include the following compounds.

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281] Third Embodiment (Organic Electroluminescence Element) An organic EL element according to this embodiment will be described. The organic EL element according to this embodiment includes an organic layer between an anode and a cathode. This organic layer includes at least one layer made of an organic compound. Alternatively, this organic layer is formed by stacking multiple layers made of organic compounds. The organic layer may further include an inorganic compound.

[0282] In the organic EL element according to this embodiment, the organic layer contains the compound according to the first embodiment. That is, the organic EL element according to this embodiment has a cathode, an anode, and an organic layer between the cathode and the anode, and at least one layer included in the organic layer contains the compound according to the first embodiment as a first compound.

[0283] According to this embodiment, the life of the organic electroluminescence element can be extended.

[0284] In the organic EL device according to this embodiment, at least one of the organic layers may contain the compound according to the first embodiment (first compound).

[0285] In the organic EL device according to this embodiment, the organic layer preferably includes an emitting layer, and the emitting layer preferably contains a first compound (the compound according to the first embodiment).

[0286] The organic EL device according to this embodiment includes a cathode, an anode, and one or more light-emitting layers disposed between the cathode and the anode, and at least one of the one or more light-emitting layers contains a first compound (the compound according to the first embodiment).

[0287] The organic EL element according to this embodiment may be an organic EL element having a single light-emitting layer as a third embodiment.

[0288] The schematic configuration of an organic EL element according to one aspect of the present embodiment will be described with reference to FIG. 1 . FIG. 1 shows a schematic configuration of an example of an organic EL element according to a third embodiment. The organic EL element 1 according to one aspect of the present embodiment includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is configured by stacking, in this order from the anode 3 side, a first organic layer 67, an emitting layer 5, and a second organic layer 89. The first organic layer 67 and the second organic layer 89 may each be a single layer or may be composed of multiple layers. The first organic layer 67 may include a hole transport region. The hole transport region may include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, and the like. The second organic layer 89 may include an electron transport region. The electron transport region may include at least one layer selected from the group consisting of an electron injection layer, an electron transport layer, a hole blocking layer, and the like. For example, the first organic layer 67 may be configured by stacking a hole injection layer and a hole transport layer in this order from the anode 3 side. The second organic layer 89 may be configured by stacking an electron transport layer and an electron injection layer in this order from the anode 3 side. The organic EL element 1 may be configured by stacking a hole injection layer, a hole transport layer, the light-emitting layer 5, an electron transport layer, and an electron injection layer in this order from the anode 3 side. Furthermore, for example, the first organic layer 67 may be configured by stacking a hole injection layer, a hole transport layer, and an electron blocking layer in this order from the anode 3 side. Furthermore, for example, the second organic layer 89 may be configured by stacking a hole blocking layer, an electron transport layer, and an electron injection layer in this order from the anode 3 side. The present invention is not limited to the organic EL element having the configuration shown in Fig. 1. The compound according to the first embodiment is contained in the first organic layer 67, the light-emitting layer 5, or the second organic layer 89. In one embodiment, the compound according to the first embodiment is contained in the light-emitting layer 5. The compound according to the first embodiment can function as a light-emitting compound in the light-emitting layer 5.

[0289] In the organic EL device according to the third embodiment, the light-emitting layer preferably contains the compound according to the first embodiment (first compound) as a light-emitting compound and also contains a host material. The host material is not particularly limited, but is preferably, for example, a compound that can be used together with the fluorescent compound.

[0290] (First Compound and Second Compound) In the organic EL device according to the third embodiment, the light-emitting layer preferably contains a second compound represented by the following formula (H10).

[0291] In the organic EL element according to this embodiment, it is also preferable that the light-emitting layer does not contain a metal complex.It is also preferable that the light-emitting layer does not contain a boron-containing complex.

[0292] In the organic EL element according to this embodiment, the light-emitting layer preferably does not contain a phosphorescent material (dopant material) and preferably does not contain a heavy metal complex or a phosphorescent rare earth metal complex.

[0293] In the organic EL element according to the third embodiment, the light-emitting layer of the organic EL element preferably contains a combination of the compound according to the first embodiment (first compound) and a compound represented by the following formula (H10) (second compound):

[0294] <Compound Represented by Formula (H10)> The compound represented by formula (H10) (second compound) will be described.

[0295]

[0296] [(in the formula (H10), R １０１ ~R １１０ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused ring １０１ ~R １１０are each independently a hydrogen atom, a substituent R, or a group represented by the following formula (H10A), provided that R does not form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring. １０１ ~R １１０ is a group represented by the following formula (H10A), and when two or more groups represented by the following formula (H10A) are present, the two or more groups represented by the following formula (H10A) are the same or different from each other. １０１ -Ar １０１ (H10A)) (wherein, L １０１ represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, １０１ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and the substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and when two or more substituents R are present, the two or more substituents R are the same or different from each other, and R ９０１ ~R ９０７are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ９０６ If there are multiple R ９０６ are the same or different from each other, R ９０７ If there are multiple R ９０７ are the same or different from each other.)

[0297] The compound represented by the formula (H10) may have a deuterium atom in place of a hydrogen atom.

[0298] In one embodiment, Ar in formula (H10) １０１ At least one of the groups is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0299] In one embodiment, Ar in formula (H10) １０１ At least one of the groups is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0300] In one embodiment, all of Ar in formula (H10) １０１ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. １０１ may be the same as or different from each other.

[0301] In one embodiment, Ar in formula (H10) １０１ one of Ar is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and the remaining Ar １０１ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. １０１ may be the same as or different from each other.

[0302] In one embodiment, L in formula (H10) １０１ In one embodiment, at least one of L in formula (H10) is a single bond. １０１ In one embodiment, all of L in formula (H10) are single bonds. １０１ In one embodiment, at least one of L in formula (H10) is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms. １０１ At least one of the groups is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.

[0303] In one embodiment, -L in formula (H10) １０１ -Ar １０１ is selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.

[0304] In one embodiment, the substituents R in the formula (H10) each independently represent a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or —Si(R ９０１ ) (R ９０２ ) (R ９０３a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a halogen atom, a cyano group, a nitro group, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, ９０１ ~R ９０７ is as defined in the above formula (H10).

[0305] In one embodiment, the substituents in the case of "substituted or unsubstituted" in formula (H10) 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 carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ ~R ９０７ is as defined in the above formula (H10).

[0306] In one embodiment, the substituents in the case of "substituted or unsubstituted" in formula (H10) are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R９０７ a halogen atom, a cyano group, a nitro group, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, ９０１ ~R ９０７ is as defined in the above formula (H10).

[0307] In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (H10) is selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heterocyclic group having 5 to 18 ring atoms.

[0308] In one embodiment, the substituent in the "substituted or unsubstituted" in formula (H10) is an alkyl group having 1 to 5 carbon atoms.

[0309] In one embodiment, the compound represented by formula (H10) is a compound represented by formula (H20) below.

[0310]

[0311] (In the formula (H20), R １０１ ~R １０８ , L １０１ and Ar １０１ is as defined in the formula (H10).

[0312] That is, in one embodiment, the compound represented by formula (H10) or formula (H20) has at least two groups represented by formula (H10A). In one embodiment, the compound represented by formula (H10) or formula (H20) has two or three groups represented by formula (H10A).

[0313] The compound represented by the formula (H20) may have a deuterium atom in place of a hydrogen atom.

[0314] In one embodiment, R in formula (H10) １０１ ~R １１０ and R in formula (H20) １０１ ~R １０８In one embodiment, any pair of adjacent groups of R １０１ ~R １１０ and R in formula (H20) １０１ ~R １０８ is a hydrogen atom.

[0315] In one embodiment, the compound represented by formula (H20) is a compound represented by formula (H30):

[0316]

[0317] (In the above formula (H30), L １０１ and Ar １０１ is as defined in formula (H10), １０１Ａ ~R １０８Ａ Any pair of two or more adjacent groups of R １０１Ａ ~R １０８Ａ are each independently a hydrogen atom or a substituent R, and the substituent R is as defined in formula (H10).

[0318] That is, the compound represented by the formula (H30) is a compound having two groups represented by the formula (H10A).

[0319] In one embodiment, the compound represented by formula (H30) is a compound represented by formula (H31) below.

[0320]

[0321] (In the above formula (H31), L １０１ and Ar １０１ is as defined in formula (H10), １０１Ａ ~R １０８Ａ is as defined in the formula (H30), ｂ is an oxygen atom, a sulfur atom, N(R ３３１ ), or C(R ３３２ ) (R ３３３ ) and R １２１ ~R １２８ , and R ３３１ ~R ３３３ One of them is L １０１is a single bond bonding to L １０１ R that is not a single bond １２１ ~R １２８ one or more pairs of adjacent two or more of L are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １０１ and R is not a single bond bonding to R, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring. １２１ ~R １２８ are each independently a hydrogen atom or a substituent R, the substituent R is as defined in formula (H10), and L １０１ R that is not a single bond ３３１ ~R ３３３ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ３３１ If there are multiple R ３３１ are the same or different from each other, R ３３２ If there are multiple R ３３２ are the same or different from each other, R ３３３ If there are multiple R ３３３ are the same or different from each other.)

[0322] In one embodiment, the compound represented by formula (H31) is a compound represented by formula (H32) below.

[0323]

[0324] (In the formula (H32), R １０１Ａ ~R １０８Ａ , L １０１ , Ar １０１ , R １２１ ~R １２８ , R ３３２ and R ３３３is as defined in the formula (H31).

[0325] In one embodiment, the compound represented by formula (H31) is a compound represented by formula (H33) below.

[0326]

[0327] (In the formula (H33), R １０１Ａ ~R １０８Ａ , L １０１ , Ar １０１ , and R １２１ ~R １２８ is as defined in the formula (H31), ｃ is an oxygen atom, a sulfur atom, or N(R ３３１ ) and R ３３１ is as defined in the formula (H31).

[0328] In one embodiment, the compound represented by formula (H31) is a compound represented by formula (H34) below.

[0329]

[0330] (In the formula (H34), R １０１Ａ ~R １０８Ａ , L １０１ and Ar １０１ is as defined in the formula (H31), ｃ is an oxygen atom, a sulfur atom, or N(R ３３１ ) and R ３３１ is as defined in the formula (H31), １２１Ａ ~R １２８Ａ One of them is L １０１ is a single bond bonding to L １０１ R that is not a single bond １２１Ａ ~R １２８Ａ Any pair of adjacent two or more of L １０１ R that is not a single bond １２１Ａ ~R １２８Ａ are each independently a hydrogen atom or a substituent R, and the substituent R is as defined in formula (H10).

[0331] In one embodiment, the compound represented by formula (H31) is a compound represented by formula (H35) below.

[0332]

[0333] [In the formula (H35), R １０１Ａ ~R １０８Ａ , L １０１ , Ar １０１ and X ｂ is as defined in the formula (H31). １２１Ａ ~R １２４Ａ Any pair of two or more adjacent groups of R １２５Ａ and R １２６Ａ , R １２６Ａ and R １２７Ａ , and R １２７Ａ and R １２８Ａ Any one pair of these is bonded to each other to form a ring represented by the following formula (H35a) or (H35b).

[0334]

[0335] (In the formula (H35a) and formula (H35b), two * represent R １２５Ａ and R １２６Ａ , R １２６Ａ and R １２７Ａ , and R １２７Ａ and R １２８Ａ and R ３４１ ~R ３４４ are each independently a hydrogen atom or a substituent R, the substituent R is as defined in formula (H10), ｄ is an oxygen atom or a sulfur atom. １２１Ａ ~R １２４Ａ R that does not form a ring represented by formula (H35a) or (H35b) １２５Ａ ~R １２８Ａ , and R ３４１ ~R ３４４ One of them is L １０１ is a single bond bonding to L １０１ R that is not a single bond １２１Ａ ~R １２４Ａ , and L １０１and R which is not a single bond bonding to the ring represented by formula (H35a) or (H35b) １２５Ａ ~R １２８Ａ are each independently a hydrogen atom or a substituent R, and the substituent R is as defined in formula (H10).

[0336] In one embodiment, the compound represented by formula (H35) is a compound represented by formula (H36) below.

[0337]

[0338] (In the formula (H36), R １０１Ａ ~R １０８Ａ , L １０１ , and Ar １０１ is as defined in formula (H35), and R １２５Ｂ ~R １２８Ｂ are each independently R in formula (H35). １２５Ａ ~R １２８Ａ is synonymous with

[0339] In one embodiment, the compound represented by formula (H34) is a compound represented by formula (H37) below.

[0340]

[0341] (In the formula (H37), R １０１Ａ ~R １０８Ａ , R １２５Ａ ~R １２８Ａ , L １０１ and Ar １０１ is as defined in the above formula (H34).

[0342] In one embodiment, R in formulas (H30) to (H37) １０１Ａ ~R １０８Ａ is a hydrogen atom.

[0343] In one embodiment, the compound represented by formula (H10) is a compound represented by formula (H40) below.

[0344]

[0345] (In the formula (H40), L １０１ and Ar １０１is as defined in formula (H10), １０１Ａ , and R １０３Ａ ~R １０８Ａ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused ring １０１Ａ , and R １０３Ａ ~R １０８Ａ are each independently a hydrogen atom or a substituent R, and the substituent R is as defined in formula (H10). That is, the compound represented by formula (H40) is a compound having three groups represented by formula (H10A).

[0346] In one embodiment, the compound represented by formula (H40) is represented by formula (H41) below.

[0347]

[0348] (In the above formula (H41), L １０１ and Ar １０１ is as defined in the formula (H40).

[0349] In one embodiment, the compound represented by formula (H40) is a compound represented by any one of the following formulas (H42-1) to (H42-3).

[0350]

[0351] (In the formulas (H42-1) to (H42-3), R １０１Ａ , R １０３Ａ ~R １０８Ａ , L １０１ and Ar １０１ is as defined in the formula (H40).

[0352] In one embodiment, the compounds represented by formulae (H42-1) to (H42-3) are compounds represented by any of formulae (H43-1) to (H43-3) below.

[0353]

[0354] (In the formulas (H43-1) to (H43-3), L １０１ and Ar １０１ is as defined in the formula (H40).

[0355] In one embodiment, -L in the formula (H40), the formula (H41), the formula (H42-1) to the formula (H42-3), and the formula (H43-1) to the formula (H43-3) １０１ -Ar １０１ is selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.

[0356] In one embodiment, the compounds represented by formula (H10) or (H20) include compounds in which at least one of the hydrogen atoms contained in these compounds is a deuterium atom.

[0357] In one embodiment, in the formula (H20), R is a hydrogen atom. １０１ ~R １０８ , R, which is the substituent R １０１ ~R １０８ a hydrogen atom possessed by L １０１ a hydrogen atom possessed by L １０１ a hydrogen atom of the substituent of Ar １０１ a hydrogen atom of Ar １０１ At least one of the hydrogen atoms of the substituent is a deuterium atom.

[0358] The compounds represented by the formulae (H30) to (H37) include compounds in which at least one of the hydrogen atoms contained in these compounds is a deuterium atom. In one embodiment, at least one of the hydrogen atoms bonded to a carbon atom constituting the anthracene skeleton in the compounds represented by the formulae (H30) to (H37) is a deuterium atom.

[0359] In one embodiment, the compound represented by formula (H30) is a compound represented by formula (H30D) below.

[0360]

[0361] (In the formula (H30D), R １０１Ａ ~R １０８Ａ , L １０１ and Ar １０１ is as defined in the formula (H30) above, provided that R is a hydrogen atom. １０１Ａ ~R １０８Ａ , R, which is the substituent R １０１Ａ ~R １０８Ａ a hydrogen atom possessed by L １０１ a hydrogen atom possessed by L １０１ a hydrogen atom of the substituent of Ar １０１ a hydrogen atom of Ar １０１ At least one of the hydrogen atoms possessed by the substituent of formula (H30) is a deuterium atom. That is, the compound represented by formula (H30D) is a compound in which at least one of the hydrogen atoms possessed by the compound represented by formula (H30) is a deuterium atom.

[0362] In one embodiment, R which is a hydrogen atom in formula (H30D) １０１Ａ ~R １０８Ａ At least one of the atoms is a deuterium atom.

[0363] In one embodiment, the compound represented by formula (H30D) is a compound represented by formula (H31D) below.

[0364]

[0365] (In the formula (H31D), R １０１Ａ ~R １０８Ａ , L１０１ and Ar １０１ is as defined in the formula (H30D), ｄ is an oxygen atom or a sulfur atom, R １２１ ~R １２８ One of them is L １０１ is a single bond bonding to L １０１ R that is not a single bond １２１ ~R １２８ one or more pairs of adjacent two or more of L are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １０１ and R is not a single bond bonding to R, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring. １２１ ~R １２８ are each independently a hydrogen atom or a substituent R, and the substituent R is as defined in formula (H10). １０１Ａ ~R １０８Ａ , R, which is the substituent R １０１Ａ ~R １０８Ａ a hydrogen atom possessed by L １０１ a hydrogen atom possessed by L １０１ a hydrogen atom of the substituent of Ar １０１ a hydrogen atom of Ar １０１ A hydrogen atom possessed by the substituent of R １２１ ~R １２８ and R, which is the substituent R １２１ ~R １２８ At least one of the hydrogen atoms is a deuterium atom.

[0366] In one embodiment, the compound represented by formula (H31D) is a compound represented by formula (H32D) below.

[0367]

[0368] (In the formula (H32D), R １０１Ａ ~R １０８Ａ , L １０１ and Ar１０１ is as defined in formula (H31D), and R １２５Ａ ~R １２８Ａ each independently represents R in formula (H31D). １２５ ~R １２８ However, when R is a hydrogen atom, １０１Ａ ~R １０８Ａ , R, which is the substituent R １０１Ａ ~R １０８Ａ a hydrogen atom possessed by R １２５Ａ ~R １２８Ａ , R, which is the substituent R １２５Ａ ~R １２８Ａ a hydrogen atom bonded to a carbon atom of the dibenzofuran skeleton in formula (H32D), L １０１ a hydrogen atom possessed by L １０１ a hydrogen atom of the substituent of Ar １０１ a hydrogen atom of Ar １０１ At least one of the hydrogen atoms of the substituent is a deuterium atom.

[0369] In one embodiment, the compound represented by formula (H32D) is a compound represented by formula (H32D-1) or (H32D-2) below.

[0370]

[0371] (In the formulas (H32D-1) and (H32D-2), R １０１Ａ ~R １０８Ａ , R １２５Ａ ~R １２８Ａ , L １０１ and Ar １０１ is as defined in the formula (H32D) above, provided that R is a hydrogen atom. １０１Ａ ~R １０８Ａ , R, which is the substituent R １０１Ａ ~R １０８Ａ a hydrogen atom possessed by R １２５Ａ ~R １２８Ａ , R, which is the substituent R １２５Ａ ~R １２８Ａa hydrogen atom bonded to a carbon atom of the dibenzofuran skeleton in formulae (H32D-1) and (H32D-2); L １０１ a hydrogen atom possessed by L １０１ a hydrogen atom of the substituent of Ar １０１ a hydrogen atom of Ar １０１ At least one of the hydrogen atoms of the substituent is a deuterium atom.

[0372] In one embodiment, at least one of the hydrogen atoms possessed by the compound represented by formula (H40), formula (H41), formula (H42-1) to formula (H42-3), or formula (H43-1) to formula (H43-3) is a deuterium atom.

[0373] In one embodiment, at least one of the hydrogen atoms bonded to the carbon atoms constituting the anthracene skeleton in the compound represented by formula (H41) is a deuterium atom.

[0374] In one embodiment, the compound represented by formula (H40) is a compound represented by formula (H40D) below.

[0375]

[0376] (In the formula (H40D), L １０１ and Ar １０１ is as defined in formula (H10), １０１Ａ , and R １０３Ａ ~R １０８Ａ Any pair of two or more adjacent R １０１Ａ , and R １０３Ａ ~R １０８Ａ are each independently a hydrogen atom or a substituent R, and the substituent R is as defined in formula (H10). １０１Ａ , and R １０３Ａ ~R １０８Ａ , R, which is the substituent R １０１Ａ , and R １０３Ａ ~R １０８Ａ a hydrogen atom possessed by L １０１ a hydrogen atom possessed by L １０１a hydrogen atom of the substituent of Ar １０１ a hydrogen atom of Ar １０１ At least one of the hydrogen atoms of the substituent is a deuterium atom.

[0377] In one embodiment, R in formula (H40D) １０１Ａ , and R １０３Ａ ~R １０８Ａ At least one of the atoms is a deuterium atom.

[0378] In one embodiment, the compound represented by formula (H40D) is a compound represented by formula (H41D) below.

[0379]

[0380] (In the formula (H41D), L １０１ and Ar １０１ is as defined in the formula (H40D) above, provided that in the formula (H41D), a hydrogen atom bonded to a carbon atom constituting an anthracene skeleton, L １０１ a hydrogen atom possessed by L １０１ a hydrogen atom of the substituent of Ar １０１ a hydrogen atom of Ar １０１ At least one of the hydrogen atoms of the substituent is a deuterium atom.

[0381] In one embodiment, the compound represented by formula (H40D) is a compound represented by any one of formulas (H42D-1) to (H42D-3) below.

[0382]

[0383] (In the formulas (H42D-1) to (H42D-3), R １０１Ａ , R １０３Ａ ~R １０８Ａ , L １０１ and Ar １０１ is as defined in the formula (H40D) above, provided that R in the formula (H42D-1) is a hydrogen atom. １０１Ａ , and R １０３Ａ ~R １０８Ａ , R, which is the substituent R １０１Ａ , and R１０３Ａ ~R １０８Ａ a hydrogen atom possessed by L １０１ a hydrogen atom possessed by L １０１ a hydrogen atom of the substituent of Ar １０１ a hydrogen atom of Ar １０１ and at least one of the hydrogen atoms of the substituents of formula (H42D-1) and the hydrogen atoms bonded to the carbon atoms constituting the phenyl group in formula (H42D-1) is a deuterium atom, and １０１Ａ , and R １０３Ａ ~R １０８Ａ , R, which is the substituent R １０１Ａ , and R １０３Ａ ~R １０８Ａ a hydrogen atom possessed by L １０１ a hydrogen atom possessed by L １０１ a hydrogen atom of the substituent of Ar １０１ a hydrogen atom of Ar １０１ and at least one of the hydrogen atoms of the substituents of formula (H42D-2) and the hydrogen atoms bonded to the carbon atoms constituting the naphthyl group in formula (H42D-2) is a deuterium atom, and １０１Ａ , and R １０３Ａ ~R １０８Ａ , R, which is the substituent R １０１Ａ , and R １０３Ａ ~R １０８Ａ a hydrogen atom possessed by L １０１ a hydrogen atom possessed by L １０１ a hydrogen atom of the substituent of Ar １０１ a hydrogen atom of Ar １０１ and at least one of the hydrogen atoms bonded to the carbon atoms constituting the naphthyl group in formula (H42D-3) is a deuterium atom.

[0384] In one embodiment, the compounds represented by formulae (H42D-1) to (H42D-3) are compounds represented by any of formulae (H43D-1) to (H43D-3) below.

[0385]

[0386] (In the formulas (H43D-1) to (H43D-3), L １０１ and Ar １０１ is as defined in the formula (H40D) above, provided that: a hydrogen atom bonded to a carbon atom constituting the anthracene skeleton in the formula (H43D-1) above; L １０１ a hydrogen atom possessed by L １０１ a hydrogen atom of the substituent of Ar １０１ a hydrogen atom of Ar １０１ and a hydrogen atom bonded to a carbon atom constituting the phenyl group in formula (H43D-1) is a deuterium atom, and at least one of the hydrogen atoms bonded to a carbon atom constituting the anthracene skeleton in formula (H43D-2), L １０１ a hydrogen atom possessed by L １０１ a hydrogen atom of the substituent of Ar １０１ a hydrogen atom of Ar １０１ and a hydrogen atom bonded to a carbon atom constituting the naphthyl group in formula (H43D-2) is a deuterium atom, and at least one of the hydrogen atoms bonded to a carbon atom constituting the anthracene skeleton in formula (H43D-3), L １０１ a hydrogen atom possessed by L １０１ a hydrogen atom of the substituent of Ar １０１ a hydrogen atom of Ar １０１ and at least one of the hydrogen atoms bonded to the carbon atoms constituting the naphthyl group in formula (H43D-3) is a deuterium atom.

[0387] In one embodiment, in the compound represented by formula (H20), Ar １０１ At least one of the groups is a monovalent group having a structure represented by the following formula (H50):

[0388]

[0389] (In the above formula (H50), X １５１ is an oxygen atom, a sulfur atom, or C(R１６１ ) (R １６２ ) and R １５１ ~R １６０ One of them is L １０１ is a single bond bonding to L １０１ R is not a single bond bonded to １５１ ~R １５４ and R １５５ ~R １６０ one or more pairs of adjacent pairs of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １６１ and R １６２ are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the substituted or unsubstituted monocycle or the substituted or unsubstituted fused ring. １６１ and R １６２ , and L １０１ and R is not a single bond bonding to R, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring. １５１ ~R １６０ are each independently a hydrogen atom or a substituent R, the substituent R is as defined in formula (H10), and Ar is not a monovalent group having a structure represented by formula (H50). １０１ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0390] L in the formula (H50) １０１ In one embodiment, the position of the single bond with R １５１ ~R １５４ or R １５５ ~R １６０ One of them is L １０１ It is a single bond that bonds to

[0391] In one embodiment, Ar１０１ is expressed by the following formula (H50-R １５２ ), formula (H50-R １５３ ), formula (H50-R １５４ ), formula (H50-R １５７ ) or formula (H50-R １５８ ) is a monovalent group represented by the formula:

[0392]

[0393] (Formula (H50-R １５２ ), formula (H50-R １５３ ), formula (H50-R １５４ ), formula (H50-R １５７ ) and the formula (H50-R １５８ ) Medium, X １５１ , R １５１ ~R １６０ is as defined in the formula (H50), and * represents L １０１ Combine with

[0394] (Specific examples of compounds represented by formula (H10)) Specific examples of compounds represented by formula (H10) include the compounds shown below. The compounds represented by formula (H10) are not limited to these specific examples. In the following specific examples, D represents a deuterium atom.

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409] Specific examples of the above groups are as described in the [Definitions] section of this specification.

[0410] As described above, the organic EL element according to one aspect of the present invention has a cathode, an anode, and an emitting layer between the cathode and the anode. Except for the fact that the emitting layer contains the compound according to the first embodiment, conventionally known materials and element configurations can be applied as long as the effects of the present invention are not impaired.

[0411] The organic EL element of this embodiment preferably emits light having a maximum peak wavelength of 445 nm or more and 470 nm or less when the element is driven. The maximum peak wavelength of the light emitted from the organic EL element when the element is driven is measured as follows. ２ A voltage is applied to the organic EL element so that the spectral radiance spectrum obtained is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is measured, and this is defined as the maximum peak wavelength (unit: nm).

[0412] The content of the compound according to the first embodiment in the light-emitting layer is preferably 1% by mass or more and 20% by mass or less with respect to the entire light-emitting layer. The compound according to the first embodiment is preferably a dopant material.

[0413] In the organic EL device according to this embodiment, when the light-emitting layer contains the second compound, the light-emitting layer preferably contains the second compound in an amount of 60% by mass or more, more preferably 70% by mass or more, and even more preferably 80% by mass or more of the total mass of the light-emitting layer. The second compound is preferably a host material. When the light-emitting layer contains the second compound as a host material and the compound according to the first embodiment as a dopant material, the upper limit of the total content of the host material and the dopant material is 100% by mass.

[0414] [Fourth Embodiment] (Organic Electroluminescence Element) An organic EL element according to this embodiment will be described. The organic EL element according to this embodiment may be an organic EL element having two or more light-emitting layers as a fourth embodiment. The organic EL element of the fourth embodiment differs from the organic EL element of the third embodiment in that it has at least two or more light-emitting layers. In other respects, it is the same as the third embodiment. In the description of the fourth embodiment, components that are the same as those of the third embodiment are given the same reference numerals or names, and descriptions thereof will be omitted or simplified. Furthermore, in the fourth embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the first, second, and third embodiments can be used.

[0415] The organic electroluminescent device according to this embodiment has an anode, a cathode, and an emission band disposed between the anode and the cathode. The emission band includes a first emission layer and a second emission layer. The first emission layer contains a first host material and a first emission compound. The second emission layer contains a second host material and a second emission compound. The first host material and the second host material are different from each other, and the first emission compound and the second emission compound are the same as or different from each other.

[0416] The organic EL element according to this embodiment includes at least two light-emitting layers (a first light-emitting layer and a second light-emitting layer). The following mainly describes differences from the third embodiment, and redundant descriptions will be omitted or simplified.

[0417] (Emission Zone) The emission zone is disposed between the anode and the cathode. In the organic EL device according to this embodiment, the emission zone includes a first emission layer and a second emission layer.

[0418] In the organic EL element according to this embodiment, the first light-emitting layer may be disposed between the anode and the second light-emitting layer, or the first light-emitting layer may be disposed between the cathode and the second light-emitting layer. In the organic EL element according to this embodiment, the first light-emitting layer is preferably disposed between the anode and the second light-emitting layer.

[0419] In one aspect of the organic EL element according to the present embodiment, among the multiple layers included in the emission band, one of the first emission layer and the second emission layer is the layer located closest to the anode in the emission band, and the other of the first emission layer and the second emission layer is the layer located closest to the cathode in the emission band.

[0420] According to this embodiment, the life of the organic electroluminescence element can be extended.

[0421] Conventionally, triplet-triplet-annihilation (sometimes referred to as TTA) has been known as a technique for improving the luminous efficiency of organic electroluminescence elements. TTA is a mechanism in which triplet excitons collide with each other to generate singlet excitons. Note that the TTA mechanism is also sometimes referred to as the TTF (triplet-triplet fusion) mechanism, as described in International Publication No. 2010 / 134350.

[0422] In the organic EL device according to this embodiment, from the viewpoint of realizing the TTF mechanism, the triplet energy T １ (H1) and the triplet energy T of the second host material １ (H2) preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 1), and more preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 1A): T １ (H1)>T １ (H2) ...(Math. 1) T １ (H1)-T １(H2)>0.03 eV... (Equation 1A)

[0423] The TTF phenomenon will be explained. Holes injected from the anode and electrons injected from the cathode recombine in the light-emitting layer to generate excitons. As has been conventionally known, the spin state of these excitons is 25% singlet excitons and 75% triplet excitons. In conventional fluorescent elements, 25% of the singlet excitons emit light when they relax to the ground state, while the remaining 75% of the triplet excitons return to the ground state through a thermal deactivation process without emitting light. Therefore, the theoretical limit of the internal quantum efficiency of conventional fluorescent elements was said to be 25%. Meanwhile, the behavior of triplet excitons generated within organic materials has been theoretically investigated. According to S. M. Bachilo et al. (J. Phys. Chem. A, 104, 7711 (2000)), assuming that higher-order excitons such as quintets immediately return to triplets, triplet excitons (hereinafter referred to as triplet excitons) can be calculated as follows: ３ A ＊ When the density of triplet excitons (hereinafter referred to as triplet excitons) increases, the triplet excitons collide with each other, causing the reaction shown in the following formula: １ A represents the ground state, １ A ＊ represents the lowest excited singlet exciton. ３ A ＊ + ３ A ＊ → (4 / 9) １ A+ (1 / 9) １ A ＊ + (13 / 9) ３ A ＊ That is, 5 ３ A ＊ →4 １ A+1A ＊It is predicted that 1 / 5, or 20%, of the 75% of triplet excitons initially generated will convert to singlet excitons. Therefore, the singlet excitons contributing to light are 40%, calculated by adding 75% × (1 / 5) = 15% to the 25% initially generated. In this case, the TTF-derived emission ratio (TTF ratio) of the total luminescence intensity is 15 / 40, or 37.5%. Furthermore, if we assume that singlet excitons are generated by collisions between the 75% of the initially generated triplet excitons (one singlet exciton is generated from two triplet excitons), a very high internal quantum efficiency of 62.5% is obtained by adding 75% × (1 / 2) = 37.5% to the 25% of the initially generated singlet excitons. In this case, the TTF ratio is 37.5 / 62.5 = 60%.

[0424] According to the organic electroluminescent device of this embodiment, triplet excitons generated by the recombination of holes and electrons in the first emitting layer are thought to be less likely to be quenched at the interface between the first emitting layer and the organic layer, even if excess carriers are present at the interface between the first emitting layer and the organic layer directly in contact with the first emitting layer. For example, when the recombination region is locally present at the interface between the first emitting layer and the hole transport layer or the electron blocking layer, quenching by excess electrons is thought to occur. On the other hand, when the recombination region is locally present at the interface between the first emitting layer and the electron transport layer or the hole blocking layer, quenching by excess holes is thought to occur. The organic electroluminescent device of this embodiment includes at least two emitting layers (i.e., a first emitting layer and a second emitting layer) that satisfy a predetermined relationship, and the triplet energy T of the first host material in the first emitting layer is １ (H1) and the triplet energy T of the second host material in the second emitting layer １(H2) satisfies the relationship of the above mathematical formula (1). By providing the first emitting layer and the second emitting layer so as to satisfy the relationship of the above mathematical formula (1), triplet excitons generated in the first emitting layer can migrate to the second emitting layer without being quenched by excess carriers, and reverse migration from the second emitting layer to the first emitting layer can be suppressed. As a result, the TTF mechanism is exhibited in the second emitting layer, singlet excitons are efficiently generated, and luminous efficiency is improved. In this way, an organic electroluminescent device has a first emitting layer that mainly generates triplet excitons and a second emitting layer that mainly exhibits the TTF mechanism by utilizing triplet excitons transferred from the first emitting layer, as distinct regions, and a compound having a lower triplet energy than the first host material in the first emitting layer is used as the second host material in the second emitting layer to provide a difference in triplet energy, thereby improving luminous efficiency.

[0425] In this specification, the term "host material" refers to a material that is contained in, for example, "50% by mass or more of the layer." Thus, for example, the first emitting layer contains the first host material in an amount of 50% by mass or more of the total mass of the first emitting layer. The second emitting layer contains, for example, the second host material in an amount of 50% by mass or more of the total mass of the second emitting layer.

[0426] In the organic EL device according to this embodiment, at least one of the first luminescent compound and the second luminescent compound is the compound according to embodiment 1. In the organic EL device according to this embodiment, when one of the first luminescent compound and the second luminescent compound is the compound according to embodiment 1 and the other is not the compound according to embodiment 1, the other luminescent compound is not particularly limited.

[0427] In the organic EL device according to this embodiment, the first light-emitting compound is preferably the compound according to the first embodiment.

[0428] In one aspect of the organic EL device according to this embodiment, both the first light-emitting compound and the second light-emitting compound are the compound according to the first embodiment.

[0429] (First Light-Emitting Layer) The first light-emitting layer contains a first host material and a first light-emitting compound. The first host material is a compound different from the second host material contained in the second light-emitting layer.

[0430] In the organic EL device according to this embodiment, the first light-emitting compound is preferably a compound that does not contain an azine ring structure in the molecule.

[0431] In the organic EL device according to this embodiment, the first light-emitting compound is preferably not a boron-containing complex, and more preferably not a complex.

[0432] In the organic EL element according to this embodiment, the first light-emitting layer preferably does not contain a metal complex. Also, in the organic EL element according to this embodiment, the first light-emitting layer preferably does not contain a boron-containing complex.

[0433] In the organic EL device according to this embodiment, the first light-emitting layer preferably does not contain a phosphorescent material (dopant material). Furthermore, the first light-emitting layer preferably does not contain a heavy metal complex or a phosphorescent rare earth metal complex. Examples of heavy metal complexes include an iridium complex, an osmium complex, and a platinum complex.

[0434] In one aspect of the organic EL element according to this embodiment, the triplet energy T １ (H1) and the triplet energy T １ (D1) preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 3): T １ (D1)>T １ (H1) ...(Math 3)

[0435] When the first host material and the first light-emitting compound satisfy the relationship of the above mathematical formula (Mathematical Formula 3), triplet excitons generated in the first light-emitting layer move over the first host material rather than the first light-emitting compound having a higher triplet energy, and therefore are more likely to move to the second light-emitting layer.

[0436] In one aspect of the organic EL element according to this embodiment, when the relationship of the above formula (Formula 3) is satisfied, the triplet energy T １ (H1) and the triplet energy T １ (D1) and the triplet energy T of the second host material １ (H2) preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 3B): １ (D1)>T １ (H1)>T １ (H2) ...(Math 3B)

[0437] In one aspect of the organic EL element according to this embodiment, when the relationship of the above formula (Formula 3) is satisfied, the triplet energy T １ (H1) and the triplet energy T １ (D1) and the triplet energy T of the second host material １ (H2) preferably satisfy the relationship of the following formula (Formula 3C): 2.6 eV>T １ (D1)>T １ (H1)>T １ (H2) ...(Math 3C)

[0438] In one aspect of the organic EL element according to this embodiment, when the relationship of the above mathematical formula (Mathematical Formula 3) is satisfied, the triplet energy T １ It is preferable that (D1) satisfies the relationship of the following formula (Formula 11A): 0 eV<T １ (D1)-T １ (H1)<0.6 eV... (Equation 11A)

[0439] In one aspect of the organic EL element according to this embodiment, the singlet energy S １ (H1) and the singlet energy S of the first luminescent compound １ It is preferable that the singlet energy S １ means the energy difference between the lowest excited singlet state and the ground state. １ (H1)>S １ (D1) ... (Equation 4)

[0440] When the first host material and the first light-emitting compound satisfy the relationship of the above-mentioned mathematical formula (Mathematical Formula 4), singlet excitons generated on the first host material can easily transfer energy from the first host material to the first light-emitting compound, contributing to the fluorescent emission of the first light-emitting compound.

[0441] In the organic EL device according to this embodiment, the triplet energy T １ It is preferable that (H1) satisfies the relationship of the following mathematical formula (Mathematical Formula 12): T １ (H1)>2.0 eV (Equation 12)

[0442] In the organic EL device according to this embodiment, the triplet energy T １ It is also preferable that (H1) satisfies the relationship of the following mathematical formula (12A), and it is also preferable that (H1) satisfies the relationship of the following mathematical formula (12B). １ (H1)>2.10 eV ... (Equation 12A) T １ (H1)>2.15 eV (Equation 12B)

[0443] In the organic EL device according to this embodiment, the triplet energy T １ When (H1) satisfies the relationship of the above-mentioned formula (12A) or (12B), triplet excitons generated in the first emitting layer are easily transferred to the second emitting layer, and reverse transfer from the second emitting layer to the first emitting layer is easily suppressed. As a result, singlet excitons are efficiently generated in the second emitting layer, and luminous efficiency is improved.

[0444] In the organic EL device according to this embodiment, the triplet energy T １ It is also preferable that (H1) satisfies the relationship of the following mathematical formula (12C), and it is also preferable that (H1) satisfies the relationship of the following mathematical formula (12D): 2.08 eV>T １ (H1)>1.87eV...(Math. 12C) 2.05eV>T １ (H1)>1.90 eV (Equation 12D)

[0445] In the organic EL device according to this embodiment, the triplet energy T １When (H1) satisfies the relationship of the above-mentioned formula (12C) or (12D), the energy of triplet excitons generated in the first light-emitting layer becomes small, and an extension of the life of the organic EL element can be expected.

[0446] In the organic EL device according to this embodiment, the triplet energy T １ It is also preferable that (D1) satisfies the relationship of the following mathematical formula (14A), and it is also preferable that (D1) satisfies the relationship of the following mathematical formula (14B): 2.60 eV>T １ (D1) ... (Equation 14A) 2.50 eV > T １ (D1) (Equation 14B) When the first light-emitting layer contains a compound that satisfies the relationship of the above-mentioned equation (Equation 14A) or (Equation 14B), the life of the organic EL element is extended.

[0447] In the organic EL device according to this embodiment, the triplet energy T １ It is also preferable that (D1) satisfies the relationship of the following mathematical formula (14C), and it is also preferable that (D1) satisfies the relationship of the following mathematical formula (14D): 2.20 eV>T １ (D1) ... (Equation 14C) 2.10 eV > T １ (D1) ... (Equation 14D)

[0448] (triplet energy T １ ) Triplet energy T １ The following method can be used to measure the compound to be measured: －５ mol / L or more 10 －４ The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this measurement sample was measured at low temperature (77 [K]), and a tangent line was drawn to the rising edge of the phosphorescence spectrum on the short wavelength side, and the wavelength value λ at the intersection of the tangent line and the horizontal axis was determined. ｅｄｇｅ Based on [nm], the amount of energy calculated from the following conversion formula (F1) is the triplet energy T １ Conversion formula (F1): T １[eV]=1239.85 / λ ｅｄｇｅ

[0449] The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows: When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum among the spectral maxima, consider the tangent at each point on the curve toward the long wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope is at its maximum (i.e., the tangent at the inflection point) is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that maximum points with peak intensities of 15% or less of the maximum peak intensity of the spectrum are not included in the shortest wavelength maximum, and the tangent drawn at the point where the slope is closest to the shortest wavelength maximum is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Phosphorescence can be measured using an F-4500 spectrofluorophotometer manufactured by Hitachi High-Technologies Corporation. However, the measuring device is not limited to this, and measurements may be performed by combining a cooling device, a cryogenic container, an excitation light source, and a light receiving device.

[0450] (singlet energy S １ ) Singlet energy S using solution １ The following methods can be used to measure the compound to be measured (sometimes referred to as the solution method). －５ mol / L or more 10 －４ A toluene solution of 1000 mol / L or less is prepared and placed in a quartz cell, and the absorption spectrum (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K). A tangent line is drawn to the falling edge of the long wavelength side of this absorption spectrum, and the wavelength value λ at the intersection of this tangent line and the horizontal axis is determined. ｅｄｇｅ [nm] is substituted into the following conversion formula (F2) to calculate the singlet energy. Conversion formula (F2): S １ [eV]=1239.85 / λ ｅｄｇｅ An example of an absorption spectrum measuring device is a spectrophotometer (device name: U3310) manufactured by Hitachi, Ltd., but is not limited to this.

[0451] A tangent to the fall of the absorption spectrum on the long wavelength side is drawn as follows: When moving along the spectral curve from the longest maximum value on the longest wavelength side among the maximum values ​​of the absorption spectrum in the direction of longer wavelengths, consider the tangent at each point on the curve. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the slope is minimum on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is considered to be the tangent to the fall of the absorption spectrum on the long wavelength side. Note that maximum points with absorbance values ​​of 0.2 or less are not included in the maximum value on the longest wavelength side.

[0452] (Content) In the organic EL device according to this embodiment, the first light-emitting compound is preferably contained in the first light-emitting layer in an amount of 0.5% by mass or more. That is, the first light-emitting layer preferably contains the first light-emitting compound in an amount of 0.5% by mass or more of the total mass of the first light-emitting layer, more preferably 1.0% by mass or more of the total mass of the first light-emitting layer, even more preferably 1.2% by mass or more of the total mass of the first light-emitting layer, and even more preferably 1.5% by mass or more of the total mass of the first light-emitting layer. The first light-emitting layer preferably contains the first light-emitting compound in an amount of 10% by mass or less of the total mass of the first light-emitting layer, more preferably 7% by mass or less of the total mass of the first light-emitting layer, and even more preferably 5% by mass or less of the total mass of the first light-emitting layer.

[0453] In the organic EL device according to this embodiment, the first emitting layer preferably contains the first compound as the first host material in an amount of 60% by mass or more, more preferably 70% by mass or more, even more preferably 80% by mass or more, even more preferably 90% by mass or more, and even more preferably 95% by mass or more. The first emitting layer preferably contains the first host material in an amount of 99% by mass or less, based on the total mass of the first emitting layer. However, when the first emitting layer contains both the first host material and the first emitting compound, the upper limit of the total content of the first host material and the first emitting compound is 100% by mass.

[0454] Note that this embodiment does not exclude the case where the first light-emitting layer contains a material other than the first host material and the first light-emitting compound. The first light-emitting layer may contain only one type of first host material, or may contain two or more types of first light-emitting compounds.

[0455] (First Host Material) In the organic EL device according to this embodiment, the first host material is not particularly limited.

[0456] In one aspect of the organic EL element of this embodiment, the first host material contains at least one of a structure satisfying the following condition (i) and a structure satisfying the following condition (ii) in the molecule:

[0457] Condition (i) The compound has a biphenyl structure in which a first benzene ring and a second benzene ring are connected by a single bond, and the first benzene ring and the second benzene ring in the biphenyl structure are further connected by a bridge at at least one portion other than the single bond.

[0458] Condition (ii) The compound has a first connecting structure including a benzene ring and a naphthalene ring connected by a single bond, and the benzene ring and the naphthalene ring in the first connecting structure are each independently fused with a further single ring or a fused ring, or are not fused with a further single ring or a fused ring, and the benzene ring and the naphthalene ring in the first connecting structure are further connected by a bridge at at least one portion other than the single bond.

[0459] In one aspect of the organic EL element of this embodiment, the first host material contains a structure that satisfies the above condition (i) in the molecule.

[0460] In one aspect of the organic EL element of the present embodiment, the first benzene ring and the second benzene ring in the biphenyl structure of the condition (i) are further linked by the bridge of the condition (i) at a portion other than the single bond. When the first host material has a biphenyl structure including such a bridge, it is expected that deterioration in chromaticity can be suppressed when the first host material is used in an emitting layer of an organic EL element.

[0461] In one aspect of the organic EL element of the present embodiment, the first benzene ring and the second benzene ring in the biphenyl structure of the condition (i) are further connected by the bridge of the condition (i) at two portions other than the single bond.

[0462] In one aspect of the organic EL element of the present embodiment, the crosslink in the condition (i) contains a double bond.

[0463] In one aspect of the organic EL element of the present embodiment, the crosslink in the condition (i) does not contain a double bond.

[0464] In one aspect of the organic EL element of this embodiment, the first host material has a structure satisfying the above condition (i) in its molecule, the first benzene ring and the second benzene ring in the biphenyl structure are further connected to each other by the bridge satisfying the above condition (i) at two portions other than the single bond, and the bridge satisfying the above condition (i) does not contain a double bond. When the first host material has a biphenyl structure containing such a bridge, it is expected that deterioration in chromaticity can be suppressed when the first host material is used in an emitting layer of an organic EL element.

[0465] For example, when the first benzene ring and the second benzene ring in the biphenyl structure represented by the following formula (BP1) are further linked by a bridge at at least one moiety other than a single bond, the biphenyl structure becomes a linked structure (fused ring) of the following formulae (BP11) to (BP15), etc.

[0466]

[0467] The formula (BP11) is a structure in which one moiety other than the single bond is linked by a bridge containing no double bond. The formula (BP12) is a structure in which one moiety other than the single bond is linked by a bridge containing a double bond. The formula (BP13) is a structure in which two moieties other than the single bond are linked by a bridge containing no double bond. The formula (BP14) is a structure in which one of the two moieties other than the single bond is linked by a bridge containing no double bond, and the other of the two moieties other than the single bond is linked by a bridge containing a double bond. The formula (BP15) is a structure in which two moieties other than the single bond are linked by a bridge containing a double bond.

[0468] In one aspect of the organic EL element of this embodiment, the first host material contains a structure that satisfies the above condition (ii) in the molecule.

[0469] When the first host material has such a linking structure containing a bridge, it is expected that deterioration in chromaticity can be suppressed when the first host material is used in the light-emitting layer of an organic EL device. In this case, the first host material only needs to have, as a minimum unit, a first linking structure (sometimes referred to as a benzene-naphthalene linking structure) containing a benzene ring and a naphthalene ring linked by a single bond, as represented by the following formula (X1) or (X2), in the molecule. A single ring or a fused ring may be further fused to the benzene ring, or a single ring or a fused ring may be further fused to the naphthalene ring. For example, even when the first host material has, in the molecule, a second linking structure (sometimes referred to as a naphthalene-naphthalene linking structure) containing a naphthalene ring and a naphthalene ring linked by a single bond, as represented by the following formula (X3), (X4), or (X5), one of the naphthalene rings contains a benzene ring, and therefore the first host material contains a benzene-naphthalene linking structure.

[0470]

[0471] In one aspect of the organic EL element of the present embodiment, the crosslink in the condition (ii) preferably includes a double bond. That is, it is also preferable that the benzene ring and the naphthalene ring have a structure in which they are further connected by a crosslinked structure including a double bond at a portion other than a single bond.

[0472] When the benzene ring and the naphthalene ring in the first linked structure (benzene-naphthalene linked structure) are further linked by a bridge at at least one moiety other than a single bond, for example, in the case of the formula (X1), the linked structure (fused ring) is represented by the following formula (X11), and in the case of the formula (X3), the linked structure (fused ring) is represented by the following formula (X31). When the benzene ring and the naphthalene ring in the benzene-naphthalene linked structure are further linked by a bridge containing a double bond at a moiety other than a single bond, for example, in the case of the formula (X1), the linked structure (fused ring) is represented by the following formula (X12), in the case of the formula (X2), the linked structure (fused ring) is represented by the following formula (X21), formula (X22), or formula (X23), in the case of the formula (X4), the linked structure (fused ring) is represented by the following formula (X41), and in the case of the formula (X5), the linked structure (fused ring) is represented by the following formula (X51). When the benzene ring and the naphthalene ring in the benzene-naphthalene linked structure are further linked by a bridge containing a heteroatom (for example, an oxygen atom) in at least one portion other than the single bond, for example, in the case of the above formula (X1), the linked structure (fused ring) is represented by the following formula (X13).

[0473]

[0474] In the organic EL element of the present embodiment, for example, it is also preferable that the compound is any one compound selected from the group consisting of a compound represented by the following formula (H11), a compound represented by the formula (H12), a compound represented by the formula (H13), a compound represented by the formula (H14), a compound represented by the formula (H15), and a compound represented by the formula (H16).

[0475] (Compound Represented by Formula (H11)) The compound represented by formula (H11) will be described.

[0476]

[0477] (In the formula (H11), R １０１ ~R １１０ , and R １１１ ~R １２０are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, with the proviso that R １０１ ~R １１０ One of them is L １０１ indicates the bonding position with R １１１ ~R １２０ One of them is L １０１ indicates the bonding position with L １０１ represents a single bond, a substituted or unsubstituted arylene group having 6 to 24 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 24 ring atoms, mx is 0, 1, 2, 3, 4, or 5, and L １０１ When there are two or more, there are two or more L １０１ are the same or different from each other.)

[0478] (In the first host material, R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ , R ９０７ , R ８０１ and R ８０２are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ９０６ If there are multiple R ９０６ are the same or different from each other, R ９０７ If there are multiple R ９０７ are the same or different from each other, R ８０１ If there are multiple R ８０１ are the same or different from each other, R ８０２ If there are multiple R ８０２ are the same or different from each other.)

[0479] In one aspect of the organic EL element according to this embodiment, the compound represented by formula (H11) is a compound represented by the following formula (H111).

[0480]

[0481] (In the formula (H111), R １０１ , R １０２ , R １０４ ~R １１０ , and R １１１ ~R １１９are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and L １０１ and mx are L in the formula (H11), respectively. １０１ and mx.)

[0482] In one aspect of the organic EL element according to this embodiment, mx is 1 or 2.

[0483] In one aspect of the organic EL element according to this embodiment, L １０１ represents a substituted or unsubstituted arylene group having 6 to 24 ring carbon atoms.

[0484] In one aspect of the organic EL element according to this embodiment, the first compound is a compound having only two pyrene rings in the molecule (sometimes referred to as a bispyrene compound). In one aspect of the organic EL element according to this embodiment, the compound represented by formula (H11) is a bispyrene compound.

[0485] (Compound Represented by Formula (H12)) The compound represented by formula (H12) will be described.

[0486]

[0487] (In the formula (H12), Xa is an oxygen atom, a sulfur atom, or C(R １２０１ ) (R １２０２ ), or Si(R １２０３ ) (R １２０４ ) and R １２０１ ~R １２０４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, １２１ ~R １３０ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused ring １２１ ~R １３０ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (H121), wherein R １２１ ~R １３０ is a group represented by the formula (H121), and when a plurality of groups represented by the formula (H121) are present, the plurality of groups represented by the formula (H121) are the same or different from each other, and L １２ represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, ma is 0, 1, 2, or 3, and L １２ When there are two or more, there are two or more L １２ are the same or different from each other, Ar １２ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, １２ When two or more are present, two or more Ar １２ are the same or different, and * in formula (H121) indicates the bonding position.

[0488] In one aspect of the organic EL element of this embodiment, L １２ represents a single bond, a substituted or unsubstituted arylene group having 6 to 15 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 15 ring atoms.

[0489] In one aspect of the organic EL element according to this embodiment, Ar １２ is a substituted or unsubstituted aryl group containing four or more rings or a substituted or unsubstituted heterocyclic group containing four or more rings.

[0490] In one aspect of the organic EL element according to this embodiment, Ar １２ is a substituted or unsubstituted aryl group containing four or more rings.

[0491] In one aspect of the organic EL element according to this embodiment, R １２９ is a group represented by the formula (H121).

[0492] In one aspect of the organic EL element according to this embodiment, Xa is an oxygen atom.

[0493] In one aspect of the organic EL element according to this embodiment, the compound represented by formula (H12) is a compound represented by formula (H122) below.

[0494]

[0495] (In the formula (H122), R １２１ ~R １２８ and R １３０ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, １２ , L １２ and ma respectively represent Ar in the formula (H121).１２ , L １２ and ma.)

[0496] In one aspect of the organic EL element according to this embodiment, ma is 1 or 2.

[0497] (Compound Represented by Formula (H13)) The compound represented by formula (H13) will be described.

[0498]

[0499] (In the formula (H13), R １３１ ~R １４０ , Ar １３１ and Ar １３２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (H131), wherein R １３１ ~R １４０ , Ar １３１ and Ar １３２ is a group represented by the formula (H131), and when a plurality of groups represented by the formula (H131) are present, the plurality of groups represented by the formula (H131) are the same or different from each other, and L １３represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, １３ represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mb is 0, 1, 2, 3, 4, or 5, and L １３ When there are two or more, there are two or more L １３ are the same or different from each other, Ar １３ When two or more are present, two or more Ar １３ are the same or different, and * in formula (H131) indicates the bonding position to the benz[a]anthracene ring in formula (H13).

[0500] In one aspect of the organic EL element according to this embodiment, Ar １３１ and Ar １３２ At least one of the above is a group represented by formula (H131).

[0501] In one aspect of the organic EL element according to this embodiment, the compound represented by formula (H13) is a compound represented by formula (H132) or (H133) below.

[0502]

[0503] (In the formulas (H132) and (H133), R １３１ ~R １４０ , Ar １３１ and Ar １３２ are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and L １３ , Ar １３ and mb respectively represent L in the formula (H131). １３ , Ar １３ and mb.)

[0504] In one aspect of the organic EL element according to this embodiment, mb is 0, 1, or 2.

[0505] (Compound Represented by Formula (H14)) The compound represented by formula (H14) will be explained.

[0506]

[0507] (In the formula (H14), R １Ａ and R １Ｂ are each independently a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 17 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 17 ring atoms, with the proviso that R １Ａ and R １Ｂ at least one of R is a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms; １４１ ~R １４４ and a set of two or more adjacent １４５ ~R １４８ at least one pair of adjacent two or more of these is bonded to each other to form a substituted or unsubstituted monocycle, or is bonded to each other to form a substituted or unsubstituted fused ring, and in the case where a substituted or unsubstituted monocycle or a substituted or unsubstituted fused ring is formed on the ring A side of the group represented by formula (H141), R １４２or the carbon atom C on the ring B side among the carbon atoms constituting the monocyclic ring on the ring A side and the fused ring on the ring A side ２ Carbon atom C of ring A bonded to １ When a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring is not formed on the ring A side but is formed on the ring B side, R １４２ and R is not a group represented by formula (H141), １４２ R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring １４１ , R １４３ , R １４４ and R １４５ ~R １４８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 17 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 17 ring atoms, １４ is a substituted or unsubstituted aryl group having four or more fused rings or a substituted or unsubstituted heterocyclic group having four or more fused rings, １４represents a single bond, a substituted or unsubstituted arylene group having 6 to 17 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 17 ring atoms, mc is 0, 1, or 2, * represents the bonding position to an atom constituting the ring of formula (H14), with the proviso that the compound represented by formula (H14) does not contain three or more substituted or unsubstituted aryl groups having four or more fused rings and three or more substituted or unsubstituted heterocyclic groups having four or more fused rings in the molecule of the compound represented by formula (H14).

[0508] In one aspect of the organic EL element according to this embodiment, R １４２ is a group represented by the formula (H141).

[0509] In one aspect of the organic EL element according to this embodiment, in the compound represented by formula (H14), R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ , R ９０７ , R ８０１ and R ８０２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 17 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 17 ring atoms.

[0510] In one aspect of the organic EL element according to this embodiment, the compound represented by formula (H14) is a compound represented by formula (H142), formula (H143), or formula (H144) below.

[0511]

[0512]

[0513] (In the formula (H142), formula (H143) or formula (H144), R １Ａ , R １Ｂ , R １４１ , R １４３ , R １４４ , R １４５ , R１４６ , R １４７ and R １４８ respectively represent R in the formula (H14). １Ａ , R １Ｂ , R １４１ , R １４３ , R １４４ , R １４５ , R １４６ , R １４７ and R １４８ Ar １４ , L １４ and mc are the Ar groups in the formula (H141), respectively. １４ , L １４ and mc, R １４０１ ~R １４０４ one or more pairs of adjacent two or more of R １４０１ ~R １４０４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 17 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 17 ring atoms.

[0514] In one aspect of the organic EL element according to this embodiment, mc is 0, 1, or 2.

[0515] (Compound Represented by Formula (H15)) The compound represented by formula (H15) will be described.

[0516]

[0517] (In the formula (H15), R １５０ ~R １５９ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (H150), wherein R １５０ ~R １５９ is a group represented by the formula (H150), and when a plurality of groups represented by the formula (H150) are present, the plurality of groups represented by the formula (H150) are the same or different from each other, and L １５１ represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, １５１ represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mg represents 0, 1, 2, 3, 4, or 5, and L １５１ When there are two or more, there are two or more L １５１are the same or different from each other, Ar １５１ When two or more are present, two or more Ar １５１ are the same or different, and * in formula (H150) indicates the bonding position to the pyrene ring in formula (H15).

[0518] In one aspect of the organic EL element according to this embodiment, R １５３ is a group represented by the formula (H150).

[0519] In one aspect of the organic EL element according to this embodiment, L １５１ is a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, and Ar １５１ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0520] In one aspect of the organic EL element according to this embodiment, L １５１ is a single bond or a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms, and Ar １５１ is a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms.

[0521] In one aspect of the organic EL element according to this embodiment, the group represented by formula (H150) is a group represented by formula (H151) below.

[0522]

[0523] (In the formula (H151), X １５ is an oxygen atom or a sulfur atom, L １５ represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, md is 0, 1, 2, 3, 4, or 5, and L １５ When there are two or more, there are two or more L １５ are the same or different from each other, R １５００ ~R １５０４one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring １５００ ~R １５０４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, １５００ are the same or different from each other, when a plurality of groups represented by the formula (H151) are present, the plurality of groups represented by the formula (H151) are the same or different from each other, and * in the formula (H151) indicates the bonding position with the pyrene ring in the formula (H15).

[0524] In one aspect of the organic EL element according to this embodiment, the compound represented by formula (H15) is a compound represented by formula (H152): １５３ is a group represented by formula (H151), it is represented by formula (H152) below.

[0525]

[0526] (In the formula (H152), R １５０ ~R １５２ and R １５４ ~R １５９ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and X １５ , L １５ and md are the X in the formula (H151), respectively. １５ , L １５ and md, R １５００ ~R １５０４ each independently represents R in formula (H151). １５００ ~R １５０４ is synonymous with

[0527] In one aspect of the organic EL element according to this embodiment, md is 0, 1, or 2. In one aspect of the organic EL element according to this embodiment, when md is 0, the compound represented by formula (H152) is represented by the following formula (H153):

[0528]

[0529] (In the formula (H153), R １５０ ~R １５２ , R １５４ ~R １５９, R １５００ ~R １５０４ , and X １５ are R in the formula (H152), respectively. １５０ ~R １５２ , R １５４ ~R １５９ , R １５００ ~R １５０４ , and X １５ is synonymous with

[0530] In one aspect of the organic EL element according to this embodiment, the first compound is a compound having only one pyrene ring in the molecule (sometimes referred to as a monopyrene compound). In one aspect of the organic EL element according to this embodiment, the compound represented by formula (H15) is a monopyrene compound.

[0531] (Compound Represented by Formula (H16)) The compound represented by formula (H16) will be described.

[0532]

[0533] (In the formula (H16), R １６０ ~R １６９ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring １６０ ~R １６９ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by formula (H161), provided that when the substituted or unsubstituted monocycle has a substituent, the substituent when the substituted or unsubstituted fused ring has a substituent, and R １６０ ~R １６９ is a group represented by the formula (H161), and when a plurality of groups represented by the formula (H161) are present, the plurality of groups represented by the formula (H161) are the same or different from each other, and L １６ represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, １６ represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mf represents 0, 1, 2, 3, 4, or 5, and L １６ When there are two or more, there are two or more L １６ are the same or different from each other, Ar １６ When two or more are present, two or more Ar １６ are the same or different, and * in formula (H161) indicates the bonding position to the ring represented by formula (H16).

[0534] In one aspect of the organic EL element according to this embodiment, the first compound is a compound represented by the following formula (H162).

[0535]

[0536] (In the formula (H162), R １６１ ~R １６７ and R １６０１ ~R １６０４are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, １６ , L １６ and mf are Ar in the formula (H16), respectively. １６ , L １６ and mf.)

[0537] In one aspect of the organic EL element according to this embodiment, mf is 0, 1, or 2.

[0538] In one aspect of the organic EL element according to this embodiment, it is preferable that the first host materials are each independently any compound selected from the group consisting of a compound represented by formula (H111), a compound represented by formula (H122), a compound represented by formula (H132), and a compound represented by formula (H133).

[0539] In one aspect of the organic EL element according to this embodiment, it is preferable that the first host material does not have a bis-carbazole structure or an amine structure in the molecule.

[0540] In one aspect of the organic EL element according to this embodiment, the first host material does not contain a compound having a bis-carbazole structure or a compound having an amine structure.

[0541] In the first host material and the second host material, it is preferable that the groups described as "substituted or unsubstituted" are both "unsubstituted" groups.

[0542] (Method for Producing First Host Material) The first host material can be produced by a known method. Alternatively, the first host material can be produced by following a known method and using known alternative reactions and raw materials suited to the target material.

[0543] (Specific Examples of First Host Material) Specific examples of the first host material include the following compounds. However, the present invention is not limited to these specific examples of the first host material. In this specification, among the specific examples of the compounds, D represents a deuterium atom, Me represents a methyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0544]

[0545]

[0546]

[0547]

[0548]

[0549]

[0550]

[0551]

[0552]

[0553]

[0554]

[0555]

[0556]

[0557]

[0558]

[0559]

[0560]

[0561]

[0562]

[0563]

[0564]

[0565]

[0566]

[0567]

[0568] (Film Thickness) In the organic EL element according to this embodiment, the film thickness of the first light-emitting layer is preferably 3 nm or more, and more preferably 5 nm or more. If the film thickness of the first light-emitting layer is 3 nm or more, the film thickness is sufficient to cause recombination of holes and electrons in the first light-emitting layer. In the organic EL element according to this embodiment, the film thickness of the first light-emitting layer is preferably 15 nm or less, and more preferably 10 nm or less. If the film thickness of the first light-emitting layer is 15 nm or less, the film thickness is thin enough to allow triplet excitons to migrate to the second light-emitting layer. In the organic EL element according to this embodiment, the film thickness of the first light-emitting layer is more preferably 3 nm or more and 15 nm or less.

[0569] (Second Light-Emitting Layer) In the organic EL device according to this embodiment, the second light-emitting layer contains a second host material and a second light-emitting compound. The second host material is a compound different from the first host material contained in the first light-emitting layer. In the organic EL device according to this embodiment, the first light-emitting compound and the second light-emitting compound may be the same or different from each other.

[0570] In the organic EL device according to this embodiment, the second light-emitting compound is preferably a compound that does not contain an azine ring structure in the molecule.

[0571] In the organic EL device according to this embodiment, the second light-emitting compound is preferably not a boron-containing complex, and more preferably not a complex.

[0572] In the organic EL element according to this embodiment, the second light-emitting layer preferably does not contain a metal complex. Also, in the organic EL element according to this embodiment, the second light-emitting layer preferably does not contain a boron-containing complex.

[0573] In the organic EL device according to this embodiment, the second light-emitting layer preferably does not contain a phosphorescent material (dopant material). Furthermore, the second light-emitting layer preferably does not contain a heavy metal complex or a phosphorescent rare earth metal complex. Examples of heavy metal complexes include an iridium complex, an osmium complex, and a platinum complex.

[0574] In the organic EL device according to this embodiment, the triplet energy T １ (D2) and the triplet energy T of the second host material １ It is preferable that (H2) satisfies the relationship of the following formula (Formula 5): T １ (D2)>T １ (H2) ... (Equation 5)

[0575] In the organic EL device according to this embodiment, the second light-emitting compound and the second host material satisfy the relationship of the above mathematical formula (Mathematical Formula 5), ​​so that triplet excitons generated in the first light-emitting layer transfer energy to molecules of the second host material, rather than to the second light-emitting compound having a higher triplet energy, when they move to the second light-emitting layer. Furthermore, triplet excitons generated by recombination of holes and electrons on the second host material do not transfer to the second light-emitting compound having a higher triplet energy. Triplet excitons generated by recombination on molecules of the second light-emitting compound quickly transfer energy to molecules of the second host material. Triplet excitons from the second host material efficiently collide with each other on the second host material due to the TTF phenomenon, generating singlet excitons, without transferring to the second light-emitting compound.

[0576] In the organic EL device according to this embodiment, the singlet energy S １ (H2) and the singlet energy S of the second luminescent compound １ (D2) preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 6): １ (H2)>S １ (D2) ... (Equation 6)

[0577] In the organic EL element according to this embodiment, the second light-emitting compound and the second host material satisfy the relationship of the above mathematical formula (Mathematical Formula 6), and therefore the singlet energy of the second light-emitting compound is smaller than the singlet energy of the second host material. Therefore, the singlet excitons generated by the TTF phenomenon transfer energy from the second host material to the second light-emitting compound, and contribute to the fluorescent emission of the second light-emitting compound.

[0578] In one aspect of the organic EL element according to this embodiment, the triplet energy T １ (H1) and the triplet energy T of the second luminescent compound １ (D2) and the triplet energy T of the second host material １ (H2) satisfies the relationship of the following formula (Formula 5A): T １ (H1) ≧ T １ (D2)>T １ (H2) ...(Number 5A)

[0579] In one aspect of the organic EL element according to this embodiment, the triplet energy T １ (H1) and the triplet energy T of the second host material １ (H2) and the triplet energy T of the second luminescent compound １ (D2) may satisfy the relationship of the following formula (5B) instead of the formula (5A): T １ (D2)>T １ (H1)>T １ (H2) ... (Math 5B)

[0580] In the organic EL element according to this embodiment, when the relationship of the above formula (Formula 5B) is satisfied, the triplet energy T １ (H1) and the triplet energy T of the second host material１ (H2) and the triplet energy T of the second luminescent compound １ (D2) preferably satisfy the relationship of the following formula (Formula 5C): 2.6 eV>T １ (D2)>T １ (H1)>T １ (H2) ... (Math 5C)

[0581] The triplet energy T of the second emissive compound １ It is preferable that (D2) satisfies the relationship of the following mathematical formula (Mathematical Formula 11B): 0 eV<T １ (D2)-T １ (H2)<0.8 eV (Equation 11B)

[0582] In the organic EL device according to this embodiment, the triplet energy T １ It is also preferable that (D2) satisfies the relationship of the following mathematical formula (15A), and it is also preferable that (D2) satisfies the relationship of the following mathematical formula (15B): 2.60 eV>T １ (D2) ...(Math. 15A) 2.50eV>T １ (D2) (Equation 15B) When the second light-emitting layer contains a compound that satisfies the relationship of the above-mentioned equation (Equation 15A) or (Equation 15B), the life of the organic EL element is extended.

[0583] In the organic EL device according to this embodiment, the triplet energy T １ It is also preferable that (D2) satisfies the relationship of the following mathematical formula (15C), and it is also preferable that (D2) satisfies the relationship of the following mathematical formula (15D): 2.20 eV>T １ (D2) ...(Math. 15C) 2.10eV>T １ (D2) ...(Math. 15D)

[0584] In the organic EL device according to this embodiment, the triplet energy T １ It is also preferable that (H2) satisfies the relationship of the following mathematical formula (Mathematical Formula 13): T １ (H2) ≧ 1.9 eV (Equation 13)

[0585] In one aspect of the organic EL element according to this embodiment, the second emitting layer may have the same configuration as the emitting layer according to the third embodiment. The second emitting compound is preferably the compound according to the first embodiment (the compound represented by formula (1)). The second host material is preferably the compound represented by formula (H10) (the second compound). In the organic EL element according to the fourth embodiment, the compound according to the first embodiment and the compound represented by formula (H10) (the second compound) can be used in combination in the second emitting layer of the organic EL element.

[0586] In the organic EL device according to this embodiment, the second light-emitting compound is preferably contained in the second light-emitting layer in an amount of 0.5% by mass or more. That is, the second light-emitting layer preferably contains the second light-emitting compound in an amount of 0.5% by mass or more of the total mass of the second light-emitting layer, more preferably 1.0% by mass or more of the total mass of the second light-emitting layer, even more preferably 1.2% by mass or more of the total mass of the second light-emitting layer, and even more preferably 1.5% by mass or more of the total mass of the second light-emitting layer. The second light-emitting layer preferably contains the second light-emitting compound in an amount of 10% by mass or less of the total mass of the second light-emitting layer, more preferably 7% by mass or less of the total mass of the second light-emitting layer, and even more preferably 5% by mass or less of the total mass of the second light-emitting layer.

[0587] The second light-emitting layer preferably contains the second compound as the second host material in an amount of 60 mass% or more of the total mass of the second light-emitting layer, more preferably 70 mass% or more of the total mass of the second light-emitting layer, even more preferably 80 mass% or more of the total mass of the second light-emitting layer, even more preferably 90 mass% or more of the total mass of the second light-emitting layer, and even more preferably 95 mass% or more of the total mass of the second light-emitting layer. The second light-emitting layer preferably contains the second host material in an amount of 99 mass% or less of the total mass of the second light-emitting layer. When the second light-emitting layer contains a second host material and a second light-emitting compound, the upper limit of the total content of the second host material and the second light-emitting compound is 100 mass%.

[0588] Note that this embodiment does not exclude the case where the second light-emitting layer contains a material other than the second host material and the second light-emitting compound. The second light-emitting layer may contain only one type of second host material, or may contain two or more types of second light-emitting compounds.

[0589] (Second Host Material) In the organic EL element according to this embodiment, the second host material is not particularly limited. For example, the second host material is preferably a compound (second compound) represented by formula (H10).

[0590] (Film Thickness) In the organic EL element according to this embodiment, the film thickness of the second emitting layer is preferably 5 nm or more, and more preferably 15 nm or more. When the film thickness of the second emitting layer is 5 nm or more, triplet excitons that have migrated from the first emitting layer to the second emitting layer can be easily prevented from returning to the first emitting layer. Furthermore, when the film thickness of the second emitting layer is 5 nm or more, triplet excitons can be sufficiently separated from the recombination site in the first emitting layer. In the organic EL element according to this embodiment, the film thickness of the second emitting layer is preferably 20 nm or less. When the film thickness of the second emitting layer is 20 nm or less, the density of triplet excitons in the second emitting layer can be increased, making the TTF phenomenon more likely to occur. In the organic EL element according to this embodiment, the film thickness of the second emitting layer is preferably 5 nm or more and 20 nm or less.

[0591] The organic EL element according to this embodiment may have an anode, a first light-emitting layer, a second light-emitting layer, and a cathode in this order, or the order of the first light-emitting layer and the second light-emitting layer may be reversed. That is, the organic EL element may have an anode, a second light-emitting layer, a first light-emitting layer, and a cathode in this order. Regardless of the order of the first light-emitting layer and the second light-emitting layer, by selecting a combination of host materials that satisfies the relationship of the above mathematical formula (Mathematical Formula 1), the effect of forming the light-emitting layer into a stacked structure can be expected.

[0592] In the organic EL element according to this embodiment, when the first emitting layer and the second emitting layer are stacked in the order of the first emitting layer and the second emitting layer from the anode side, the electron mobility μe(H1) of the first host material and the electron mobility μe(H2) of the second host material satisfy the relationship of the following mathematical formula (30): μe(H2)>μe(H1) (Mathematical Formula 30) When the first host material and the second host material satisfy the relationship of the mathematical formula (30), the recombination ability of holes and electrons in the first emitting layer is improved.

[0593] In the organic EL element according to this embodiment, when the first emitting layer and the second emitting layer are stacked in the order of the first emitting layer and the second emitting layer from the anode side, it is also preferable that the hole mobility μh(H1) of the first host material and the hole mobility μh(H2) of the second host material satisfy the relationship of the following mathematical formula (31): μh(H1)>μh(H2) (Mathematical Formula 31).

[0594] In the organic EL element according to this embodiment, when the first light-emitting layer and the second light-emitting layer are stacked in the order of the first light-emitting layer and the second light-emitting layer from the anode side, it is also preferable that the hole mobility μh(H1) of the first host material, the electron mobility μe(H1) of the first host material, the hole mobility μh(H2) of the second host material, and the electron mobility μe(H2) of the second host material satisfy the relationship of the following formula (Formula 32): (μe(H2) / μh(H2))>(μe(H1) / μh(H1)) (Formula 32)

[0595] Electron mobility can be measured by performing impedance measurements using a mobility evaluation element fabricated according to the following procedure. The mobility evaluation element is fabricated, for example, according to the following procedure. A compound Target, the electron mobility of which is to be measured, is vapor-deposited on a glass substrate with an aluminum electrode (anode) so as to cover the aluminum electrode, to form a measurement target layer. An electron transport layer is formed on this measurement target layer by vapor-depositing the following compound ET-A. An electron injection layer is formed on this electron transport layer by vapor-depositing LiF. A metal cathode is formed on this electron injection layer by vapor-depositing metallic aluminum (Al). The configuration of the mobility evaluation element described above can be summarized as follows: glass / Al(50) / Target(200) / ET-A(10) / LiF(1) / Al(50). The numbers in parentheses indicate film thickness (nm).

[0596]

[0597] The electron mobility evaluation element is placed in an impedance measurement device, and impedance measurement is performed. The impedance measurement is performed by sweeping the measurement frequency from 1 Hz to 1 MHz. At this time, a DC voltage V is applied to the element simultaneously with an AC amplitude of 0.1 V. From the measured impedance Z, the modulus M is calculated using the relationship in the following calculation formula (C1). Calculation formula (C1): M = jωZ. In the above calculation formula (C1), j is an imaginary unit whose square is -1, and ω is the angular frequency [rad / s]. In a Bode plot with the imaginary part of the modulus M on the vertical axis and frequency [Hz] on the horizontal axis, the electrical time constant τ of the mobility evaluation element is calculated from the frequency fmax showing the peak using the following calculation formula (C2): Calculation formula (C2): τ = 1 / (2πfmax). π in the above calculation formula (C2) is the symbol representing pi. Using the above τ, the electron mobility μe is calculated from the relationship in the following calculation formula (C3-1). Calculation formula (C3-1): μe=d ２ / (Vτ) In the above formula (C3-1), d is the total film thickness of the organic thin films that constitute the device, and in the case of the device configuration for evaluating the electron mobility, d=210 [nm].

[0598] Hole mobility can be measured by performing impedance measurements using a mobility evaluation element fabricated according to the following procedure. The mobility evaluation element is fabricated, for example, according to the following procedure. On a glass substrate with an ITO transparent electrode (anode), the following compound HA-2 is vapor-deposited to form a hole injection layer so as to cover the transparent electrode. On this hole injection layer, the following compound HT-A is vapor-deposited to form a hole transport layer. Subsequently, a compound Target, whose hole mobility is to be measured, is vapor-deposited to form a measurement target layer. On this measurement target layer, metal aluminum (Al) is vapor-deposited to form a metal cathode. The configuration of the mobility evaluation element described above is shown in simplified form as follows: ITO(130) / HA-2(5) / HT-A(10) / Target(200) / Al(80). Note that the numbers in parentheses indicate the film thickness (nm).

[0599]

[0600] The element for evaluating hole mobility is placed in an impedance measurement device, and impedance measurement is performed. The impedance measurement is performed by sweeping the measurement frequency from 1 Hz to 1 MHz. At this time, a DC voltage V is applied to the element simultaneously with an AC amplitude of 0.1 V. From the measured impedance Z, the modulus M is calculated using the relationship of the above-mentioned calculation formula (C1). In a Bode plot with the imaginary part of the modulus M on the vertical axis and frequency [Hz] on the horizontal axis, the electrical time constant τ of the element for evaluating mobility is calculated from the frequency fmax showing the peak using the above-mentioned calculation formula (C2). Using the τ calculated from the above-mentioned calculation formula (C2), the hole mobility μh is calculated from the relationship of the following calculation formula (C3-2). Calculation formula (C3-2): μh = d ２ / (Vτ) In the above formula (C3-2), d is the total film thickness of the organic thin films that constitute the device, and in the case of the device configuration for evaluating hole mobility, d=215 [nm].

[0601] The electron and hole mobilities herein are expressed as the square root of the electric field strength, E １／２ = 500 [V １／２ / cm １／２ The square root of the electric field strength E １／２can be calculated from the relationship of the following calculation formula (C4): １／２ =V １／２ / d １／２ The impedance measurement is performed using a Solartron Model 1260 impedance measuring device, and for higher accuracy, a Solartron Model 1296 dielectric constant measurement interface can also be used.

[0602] (Third Light-Emitting Layer) The organic EL device according to this embodiment may further include a third light-emitting layer. The third light-emitting layer includes a third host material, and the first host material, the second host material, and the third host material are different from one another. The third light-emitting layer includes at least a third light-emitting compound, and the first light-emitting compound, the second light-emitting compound, and the third light-emitting compound are the same as or different from one another. The triplet energy T １ (H2) and the triplet energy T of the third host material １ (H3) preferably satisfy the relationship of the following formula (Formula 7): T １ (H2)>T １ (H3) …(Number 7)

[0603] The third light-emitting compound is preferably a compound that emits light having a maximum peak wavelength of 500 nm or less, and more preferably a compound that emits fluorescent light having a maximum peak wavelength of 500 nm or less.

[0604] When the organic EL device according to this embodiment includes a third emitting layer, the triplet energy T １ (H1) and the triplet energy T of the third host material １ (H3) preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 8): T １ (H1)>T １ (H3) ...(Math. 8)

[0605] The third host material is not particularly limited, and for example, the host materials exemplified as the first host material and the second host material in this embodiment can be used. The third light-emitting compound is not particularly limited, and for example, the light-emitting compounds exemplified as the first light-emitting compound and the second light-emitting compound can be used.

[0606] In the organic EL element according to this embodiment, it is preferable that the first light-emitting layer and the second light-emitting layer are in direct contact with each other.

[0607] In this specification, a layer structure in which "the first emitting layer and the second emitting layer are in direct contact" may include, for example, any of the following embodiments (LS1), (LS2), and (LS3): (LS1) An embodiment in which a region in which both the first host material and the second host material are mixed is generated during the process of vapor-depositing the compound for the first emitting layer and the compound for the second emitting layer, and this region is present at the interface between the first emitting layer and the second emitting layer; (LS2) An embodiment in which, when the first emitting layer and the second emitting layer contain a light-emitting compound (dopant material), a region in which the first host material, the second host material, and the light-emitting compound are mixed is generated during the process of vapor-depositing the compound for the first emitting layer and the compound for the second emitting layer, and this region is present at the interface between the first emitting layer and the second emitting layer. (LS3) When the first emitting layer and the second emitting layer contain a light-emitting compound, a region composed of the light-emitting compound, a region composed of the first host material, or a region composed of the second host material is generated during the process of vapor-depositing the compound for the first emitting layer and the compound for the second emitting layer, and the region is present at the interface between the first emitting layer and the second emitting layer.

[0608] When the organic EL element according to this embodiment includes a third light-emitting layer, it is preferable that the first light-emitting layer and the second light-emitting layer are in direct contact with each other, and that the first light-emitting layer and the third light-emitting layer are in direct contact with each other.

[0609] In this specification, a layer structure in which "the first emitting layer and the third emitting layer are in direct contact" may include, for example, any of the following embodiments (LS4), (LS5), and (LS6): (LS4) An embodiment in which a region in which both the first host material and the third host material are mixed is generated during the process of vapor-depositing the compound for the first emitting layer and the compound for the third emitting layer, and this region is present at the interface between the first emitting layer and the third emitting layer; (LS5) An embodiment in which, when the first emitting layer and the third emitting layer contain a light-emitting compound (dopant material), a region in which the first host material, the third host material, and the light-emitting compound are mixed is generated during the process of vapor-depositing the compound for the first emitting layer and the compound for the third emitting layer, and this region is present at the interface between the first emitting layer and the third emitting layer. (LS6) When the first emitting layer and the third emitting layer contain a light-emitting compound, a region composed of the light-emitting compound, a region composed of the first host material, or a region composed of the third host material is generated during the process of vapor-depositing the compound for the first emitting layer and the compound for the third emitting layer, and the region is present at the interface between the first emitting layer and the third emitting layer.

[0610] When the organic EL device according to this embodiment has an intervening layer, the intervening layer is preferably disposed between the first light-emitting layer and the second light-emitting layer.

[0611] The intervening layer is preferably a non-doped layer. The intervening layer is preferably a layer that does not contain a light-emitting compound (dopant material). The intervening layer preferably does not contain metal atoms. The intervening layer includes an intervening layer material. The intervening layer material is preferably not a light-emitting compound. The intervening layer material is not particularly limited, but is preferably a material other than a light-emitting compound. Examples of the intervening layer material include: 1) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives; 2) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and chrysene derivatives; and 3) aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives.

[0612] The intervening layer material may be one or both of the first host material contained in the first emitting layer and the second host material contained in the second emitting layer.

[0613] When the intervening layer contains multiple intervening layer materials, the content of each intervening layer material is preferably 10% by mass or more of the total mass of the intervening layer. The intervening layer preferably contains the intervening layer material in an amount of 60% by mass or more of the total mass of the intervening layer, more preferably 70% by mass or more of the total mass of the intervening layer, even more preferably 80% by mass or more of the total mass of the intervening layer, even more preferably 90% by mass or more of the total mass of the intervening layer, and even more preferably 95% by mass or more of the total mass of the intervening layer. The intervening layer may contain only one intervening layer material, or two or more intervening layer materials. When the intervening layer contains two or more intervening layer materials, the upper limit of the total content of the two or more intervening layer materials is 100% by mass. The organic EL element according to the fourth embodiment does not exclude the inclusion of materials other than the intervening layer material in the intervening layer.

[0614] The intervening layer may be composed of a single layer or may be composed of two or more layers laminated together.

[0615] The thickness of the intervening layer is not particularly limited, but is preferably 3 nm to 15 nm, more preferably 5 nm to 10 nm, per layer.

[0616] (Other Layers of Organic EL Element) The organic EL element according to this embodiment may have, in addition to the first light-emitting layer and the second light-emitting layer, one or more layers formed of an organic compound. Examples of the layer formed of an organic compound include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, an electron transport layer, a hole blocking layer, and an electron blocking layer.

[0617] The organic EL element according to this embodiment may have, for example, an anode, a second light-emitting layer, a first light-emitting layer, and a cathode in this order, or the order of the second light-emitting layer and the first light-emitting layer may be reversed, and the organic EL element may have an anode, a first light-emitting layer, a second light-emitting layer, and a cathode in this order. Regardless of the order of the first light-emitting layer and the second light-emitting layer, by selecting a combination of host materials that satisfies the relationship of the above-mentioned mathematical formula (Mathematical Formula 1), the effect of forming the light-emitting layer into a stacked structure can be expected.

[0618] In the organic EL element according to this embodiment, the organic layer may be composed of only the first light-emitting layer and the second light-emitting layer. Alternatively, for example, the organic layer may further 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, a hole blocking layer, an electron blocking layer, and the like.

[0619] The organic EL device according to this embodiment preferably includes a first light-emitting layer between the anode and the cathode, and a second light-emitting layer between the first light-emitting layer and the anode. The organic EL device according to this embodiment also preferably includes a first light-emitting layer between the anode and the cathode, and a second light-emitting layer between the first light-emitting layer and the cathode.

[0620] In the organic EL device according to this embodiment, it is preferable that a hole transport layer is included between the light-emitting region and the anode. In the organic EL device according to this embodiment, it is preferable that a hole transport layer is disposed between the anode and the light-emitting layer.

[0621] In the organic EL device according to this embodiment, it is preferable that an electron transport layer is included between the light-emitting region and the cathode. In the organic EL device according to this embodiment, it is preferable that an electron transport layer is disposed between the cathode and the light-emitting layer.

[0622] 2 shows a schematic configuration of another example of an organic EL element according to the fourth embodiment. The organic EL element 1A includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10A disposed between the anode 3 and the cathode 4. The organic layer 10A includes a hole injection layer 6, a hole transport layer 7, a first light-emitting layer 51, a second light-emitting layer 52, an electron transport layer 8, and an electron injection layer 9, stacked in this order from the anode 3 side. The organic EL element 1A has an emission zone 50A, which includes a first light-emitting layer 51 and a second light-emitting layer 52. The first light-emitting layer 51 is the layer disposed closest to the anode 3 within the emission zone 50A, and the second light-emitting layer 52 is the layer disposed closest to the cathode 4 within the emission zone 50A.

[0623] FIG. 3 shows a schematic configuration of another example of an organic EL element according to the fourth embodiment. The organic EL element 1B includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10B disposed between the anode 3 and the cathode 4. The organic layer 10B includes a hole injection layer 6, a hole transport layer 7, a second light-emitting layer 52, a first light-emitting layer 51, an electron transport layer 8, and an electron injection layer 9, stacked in this order from the anode 3 side. The organic EL element 1B has an emission zone 50B, which includes a first light-emitting layer 51 and a second light-emitting layer 52. The second light-emitting layer 52 is the layer disposed closest to the anode 3 within the emission zone 50B, and the first light-emitting layer 51 is the layer disposed closest to the cathode 4 within the emission zone 50B. The present invention is not limited to the configuration of the organic EL element shown in FIGS. 2 and 3 .

[0624] The configuration of the organic EL element will be further described. This configuration is common to the organic EL elements of the third and fourth embodiments. Hereinafter, the reference numerals may be omitted.

[0625] (Substrate) The substrate is used as a support for the organic EL element. For example, glass, quartz, plastic, etc. can be used as the substrate. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate. Examples of materials for forming the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Inorganic vapor deposition films can also be used.

[0626] (Anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, etc. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metal materials (e.g., titanium nitride).

[0627] These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1 mass % to 10 mass % of zinc oxide added to indium oxide. Furthermore, for example, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5 mass % to 5 mass % of tungsten oxide and 0.1 mass % to 1 mass % of zinc oxide relative to indium oxide. Alternatively, the films may be formed by vacuum deposition, coating, inkjet printing, spin coating, or the like.

[0628] Of the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that facilitates hole injection regardless of the work function of the anode, and therefore materials that can be used as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures thereof, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0629] Materials with low work functions, such as elements belonging to Group 1 or 2 of the periodic table, can also be used, including alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these. When forming an anode using alkali metals, alkaline earth metals, and alloys containing these, vacuum deposition or sputtering can be used. Furthermore, when using silver paste or the like, coating or inkjet printing can be used.

[0630] (Cathode) For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such a cathode material include elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.

[0631] When an alkali metal, an alkaline earth metal, or an alloy containing these is used to form a cathode, a vacuum deposition method or a sputtering method can be used. When a silver paste or the like is used, a coating method or an inkjet method can be used.

[0632] By providing an electron injection layer, the cathode can be formed using various conductive materials, regardless of the magnitude of the work function, such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, etc. These conductive materials can be formed into films by a sputtering method, an inkjet method, a spin coating method, or the like.

[0633] (Hole Injection Layer) The hole injection layer is a layer containing a substance with high hole injection properties, such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, or manganese oxide.

[0634] Furthermore, examples of the substance with high hole injection properties include low-molecular-weight organic compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DNTPD). [N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and other aromatic amine compounds, such as dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).

[0635] Furthermore, as a substance with high hole injection properties, a polymer compound (oligomer, dendrimer, polymer, etc.) can also be used. Examples of such polymer compounds include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD). Furthermore, a polymer compound to which an acid has been added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) or polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[0636] (Hole Transport Layer) The hole transport layer is a layer containing a substance with high hole transport properties. For the hole transport layer, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: NPB), Examples of aromatic amine compounds that can be used include 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The substances mentioned here are mainly 10 －６ cm ２ The material has a hole mobility of 1 / (V·s) or more.

[0637] The hole transport layer may be formed using carbazole derivatives such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (PCzPA), or anthracene derivatives such as t-BuDNA, DNA, and DPAnth. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) may also be used.

[0638] However, other substances may be used as long as they have a higher hole-transporting property than an electron-transporting property. Note that the layer containing the substance having a high hole-transporting property may be not only a single layer, but also a stack of two or more layers containing the above-mentioned substances.

[0639] (Electron Transport Layer) In the organic EL device according to the above embodiment, it is preferable to include an electron transport layer between the light-emitting layer and the cathode. The electron transport layer is a layer containing a substance with high electron transport properties. For the electron transport layer, 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds can be used. Specifically, examples of low-molecular organic compounds include Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq), and the like. ３ ), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq ２), BAlq, Znq, ZnPBO, ZnBTZ, and other metal complexes can be used. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: OXD-8), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-9 ... Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) can also be used. In the above embodiment, benzimidazole compounds can be preferably used. The substances mentioned here are mainly 10 －６ cm ２ The electron-transport layer is a substance having an electron mobility of 1 / (V·s) or more. Note that any substance other than those mentioned above may be used as the electron-transport layer as long as it has a higher electron-transporting property than a hole-transporting property. The electron-transport layer may be formed as a single layer or as a stack of two or more layers made of the above-mentioned substances.

[0640] The electron transport layer can also be made of a polymer compound, such as poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) or poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy).

[0641] (Electron Injection Layer) The electron injection layer is a layer containing a substance with high electron injection properties. Examples of the electron injection layer include lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), and calcium fluoride (CaF ２For example, alkali metals, alkaline earth metals, or compounds thereof, such as lithium oxide (LiOx), can be used. Alternatively, a substance having electron transport properties containing an alkali metal, alkaline earth metal, or a compound thereof, such as Alq containing magnesium (Mg), can be used. In this case, electron injection from the cathode can be performed more efficiently.

[0642] Alternatively, the electron injection layer may be formed using a composite material obtained by mixing an organic compound and an electron donor (donor). Such composite materials have excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material that is excellent at transporting the generated electrons. Specifically, for example, the substances constituting the electron transport layer described above (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor may be any substance that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides and alkaline earth metal oxides are also preferred, such as lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (abbreviated as TTF) can also be used.

[0643] (Layer Formation Method) The method for forming each layer of the organic EL element is not limited to those specifically mentioned above, but known methods can be used, such as dry film formation methods such as vacuum deposition, sputtering, plasma deposition, and ion plating, and wet film formation methods such as spin coating, dipping, flow coating, and inkjet deposition.

[0644] (Film Thickness) The film thickness of each organic layer of the organic EL element is not limited unless specifically mentioned above. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and if the film thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the film thickness of each organic layer of the organic EL element is usually preferably in the range of several nm to 1 μm.

[0645] Fifth Embodiment Electronic Device An electronic device according to this embodiment is equipped with the organic electroluminescence element according to any one of the above-described embodiments. Examples of the electronic device include a display device and a light-emitting device. Examples of the display device include display components (e.g., an organic EL panel module), a television, a mobile phone, a tablet, and a personal computer. Examples of the light-emitting device include lighting and vehicle lighting. The light-emitting device can be used in a display device, and can also be used as a backlight for a display device, for example.

[0646] [Modifications of the Embodiment] The present invention is not limited to the above-described embodiment, and any modifications, improvements, etc. that can achieve the object of the present invention are included in the present invention.

[0647] For example, the light-emitting layer is not limited to one layer, and multiple light-emitting layers may be stacked. When the organic EL element has multiple light-emitting layers, it is sufficient that at least one organic layer satisfies the conditions described in the above embodiment, and it is preferable that at least one light-emitting layer contains the compound of the first embodiment. When one light-emitting layer of the multiple light-emitting layers contains the compound of the first embodiment, for example, the other light-emitting layers may be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize light emission by electron transition from a triplet excited state directly to the ground state. Furthermore, when the organic EL element has multiple light-emitting layers, these light-emitting layers may be provided adjacent to each other, or the organic EL element may be a so-called tandem organic EL element in which multiple light-emitting units are stacked via an intermediate layer.

[0648] Furthermore, for example, a barrier layer may be provided adjacent to at least one of the anode side and the cathode side of the light-emitting layer. The barrier layer is preferably disposed in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons. For example, when a barrier layer is disposed in contact with the cathode side of the light-emitting layer, the barrier layer transports electrons and blocks holes from reaching a layer (e.g., an electron transport layer) closer to the cathode than the barrier layer. When the organic EL device includes an electron transport layer, the barrier layer is preferably provided between the light-emitting layer and the electron transport layer. When a barrier layer is disposed in contact with the anode side of the light-emitting layer, the barrier layer transports holes and blocks electrons from reaching a layer (e.g., a hole transport layer) closer to the anode than the barrier layer. When the organic EL device includes a hole transport layer, the barrier layer is preferably provided between the light-emitting layer and the hole transport layer. Furthermore, the barrier layer may be provided adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to its surrounding layers. The blocking layer prevents excitons generated in the light-emitting layer from migrating to layers closer to the electrode than the blocking layer (for example, the electron transport layer and the hole transport layer).The light-emitting layer and the blocking layer are preferably in contact with each other.

[0649] In addition, the specific structure and shape in carrying out the present invention may be other structures within the scope that the object of the present invention can be achieved.

[0650] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples in any way.

[0651] <Compounds> The structures of the compounds represented by formula (1) used in the production of the organic EL devices according to Examples 1 to 4 are shown below.

[0652]

[0653] The structure of the comparative compound used in the production of the organic EL device according to Comparative Example 1 is shown below.

[0654]

[0655] The structures of other compounds used in the production of the organic EL devices according to Examples 1 to 4 and Comparative Example 1 are shown below.

[0656]

[0657] <Fabrication of Organic EL Device> [Example 1] A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO (Indium Tin Oxide) transparent electrode (anode) measuring 25 mm x 75 mm x 1.1 mm was placed on a N ２The substrate was treated with plasma for 100 seconds. The film thickness of the ITO transparent electrode was 130 nm. The cleaned glass substrate with transparent electrode lines was mounted on a substrate holder of a vacuum deposition apparatus. First, compound HT-1 and compound HA were co-deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, thereby forming a hole injection layer with a film thickness of 10 nm. The proportion of compound HT-1 in this hole injection layer was 97% by mass, and the proportion of compound HA was 3% by mass. Compound HT-1 was deposited on the hole injection layer to form a first hole transport layer with a film thickness of 80 nm. Next, compound HT-2 was deposited on the first hole transport layer to form an electron blocking layer (sometimes referred to as a second hole transport layer) with a film thickness of 10 nm. Compound BH-1 (second compound) as a host material and compound BD-1 (first compound) as a light-emitting compound were co-deposited on the electron blocking layer to form a light-emitting layer with a film thickness of 25 nm. The proportion of compound BH-1 in this emitting layer was 98% by mass, and the proportion of compound BD-1 was 2% by mass. Compound ET-1 was vapor-deposited on the emitting layer to form a first electron transport layer (sometimes referred to as a hole blocking layer) with a thickness of 10 nm. Compound ET-2 was vapor-deposited on the first electron transport layer to form a second electron transport layer with a thickness of 15 nm. LiF was vapor-deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm. Metallic Al was vapor-deposited on the electron injection layer to form a cathode with a thickness of 50 nm. The organic EL device of Example 1 was fabricated in this manner. The device configuration of the organic EL device of Example 1 is schematically shown as follows. ITO(130) / HT-1:HA(10,97%:3%) / HT-1(80) / HT-2(10) / BH-1:BD-1(25,98%:2%) / ET-1(10) / ET-2(15) / LiF(1) / Al(50). Note that the numbers in parentheses indicate film thickness (unit: nm). With respect to the element configuration of the organic EL element according to Example 1, the percentages (97%:3%) in parentheses indicate the proportions (unit: mass%) of Compound HT-1 and Compound HA in the hole injection layer, and the percentages (98%:2%) indicate the proportions (unit: mass%) of the second compound (Compound BH-1) and the first compound (Compound BD-1) in the emitting layer. The same notation is used hereinafter.

[0658] [Examples 2 to 4] The organic EL devices of Examples 2 to 4 were fabricated in the same manner as the organic EL device of Example 1, except that the first compound (compound BD-1) used in forming the light-emitting layer was changed to the first compound shown in Table 1.

[0659] [Comparative Example 1] The organic EL element of Comparative Example 1 was produced in the same manner as the organic EL element of Example 1, except that the first compound (compound BD-1) used in forming the light-emitting layer was changed to the comparative compound shown in Table 1.

[0660] <Evaluation of Organic EL Device> The fabricated organic EL device was evaluated as follows. The evaluation results are shown in Table 1.

[0661] (External quantum efficiency EQE, maximum peak wavelength λ ＥＬ , and FWHM) when the current density is 10 mA / cm ２ The spectral radiance spectrum when a voltage was applied to the element so that the maximum peak wavelength λ was obtained was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming that Lambertian radiation was performed. In addition, from the obtained spectral radiance spectrum, the maximum peak wavelength λ ＥＬ The full width at half maximum (FWHM) (unit: nm) and the full width at half maximum (FWHM) were determined.

[0662] (Lifespan LT95) The fabricated organic EL element was subjected to a current density of 50 mA / cm ２ The time required for the luminance to reach 95% of the initial luminance (LT95 (unit: hours)) was measured as the lifetime. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.).

[0663]

[0664] The organic EL elements according to Examples 1 to 4 were improved in all of FWHM, EQE, and LT95 compared to the organic EL element according to Comparative Example 1. The compounds represented by formula (1), such as Compounds BD-1 to BD-4, were able to extend the element life of the organic EL element.

[0665] <Synthesis Examples> Synthesis examples of compounds BD-1 to BD-5 are shown below.

[0666]

[0667] The percentages and ratios stated in the following examples are percentages and ratios by weight unless otherwise specified.

[0668] [Synthesis of Compound BD-1] The synthesis method of compound BD-1 is described below.

[0669] (Synthesis of Intermediate 1-2) First, Intermediate 1-2 was synthesized.

[0670]

[0671] To a 500 mL degassed three-neck round-bottom flask was added 4-(dibenzo[b,d]furan-4-yl)aniline (7.00 g, 27.0 mmol), 1-bromo-4-(tert-butyl)-2-iodobenzene (9.73 g, 28.3 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.382 g, 1.5 mol%), 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (0.52 g, 3 mol%), and sodium tert-butoxide (3.21 g, 32.4 mmol). Toluene (270 mL) was then added, and the reaction was heated under a nitrogen atmosphere at an oil bath temperature of 95° C. for 6 hours. The reaction was then cooled to room temperature, and the mixture was washed with water, saturated aqueous sodium chloride, and dried over magnesium sulfate. The solution was then filtered through a pad of silica, flushed with toluene, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography using heptane / dichloromethane as the eluent (dichloromethane gradient: 0-35%) to give intermediate 1-2 (12.4 g, 97% yield) as a beige solid, which was characterized by electrospray ionization mass spectrometry (ESI-MS). The results are shown below. ESI-MS: C ２８ H ２４ Calculated mass of BrNO = 469, Measured mass = 470 (M + 1)

[0672] (Synthesis of Intermediate 1-3) Next, Intermediate 1-3 was synthesized.

[0673]

[0674] To a 500 mL degassed three-neck round-bottom flask was added Intermediate 1-2 (6.65 g, 14.1 mmol), 1-bromo-4-chloro-2,6-diiodobenzene (9.69 g, 21.2 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.267 g, 2 mol%), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.668 g, 8 mol%), and sodium tert-butoxide (2.80 g, 28.3 mmol). Toluene (140 mL) was then added, and the reaction was heated under a nitrogen atmosphere at an oil bath temperature of 120° C. for 20 hours. The reaction was then cooled to room temperature, and the mixture was washed with water, saturated aqueous sodium chloride, and dried over magnesium sulfate. The solution was then filtered through a pad of silica, flushed with toluene, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography using heptane / dichloromethane as the eluent (dichloromethane gradient: 0-15%) to give intermediate 1-3 (8.25 g, 73% yield) as a yellow foam, which was characterized by electrospray ionization mass spectrometry (ESI-MS). The results are shown below. ESI-MS: C ３４ H ２５ Br ２ Calculated mass for ClINO = 782, observed mass = 783 (M+1)

[0675] (Synthesis of Intermediate 1-4) Next, intermediate 1-4 was synthesized.

[0676]

[0677] To a 250 mL degassed three-neck round-bottom flask was added Intermediate 1-3 (8.25 g, 10.5 mmol), 9,9-dimethylfluoren-2-amine (2.58 g, 12.1 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.297 g, 3 mol%), 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (0.404 g, 6 mol%), and sodium tert-butoxide (2.08 g, 21.0 mmol). Toluene (100 mL) was then added, and the reaction was heated under a nitrogen atmosphere at an oil bath temperature of 95° C. for 6 hours. The reaction was then cooled to room temperature, and the mixture was washed with water, saturated aqueous sodium chloride, and dried over magnesium sulfate. The solution was then filtered through a pad of silica, flushed with toluene, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography using heptane / dichloromethane as the eluent (dichloromethane gradient: 5-20%) to give intermediate 1-4 (7.61 g, 83% yield) as a yellow foam, which was characterized by electrospray ionization mass spectrometry (ESI-MS). The results are shown below. ESI-MS: C ４９ H ３９ Br ２ ClN ２ Calculated value of O = 864, Measured mass = 865 (M + 1)

[0678] (Synthesis of Intermediate 1-5) Next, intermediate 1-5 was synthesized.

[0679]

[0680] To a 250 mL degassed three-neck round-bottom flask was added Intermediate 1-4 (7.60 g, 8.76 mmol), 1-bromo-4-(tert-butyl)-2-iodobenzene (5.13 g, 14.9 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.165 g, 2 mol%), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.414 g, 8 mol%), and sodium tert-butoxide (1.74 g, 17.5 mmol). Toluene (100 mL) was then added, and the reaction was heated under a nitrogen atmosphere at an oil bath temperature of 120° C. for 18 hours. The reaction was then cooled to room temperature, and the mixture was washed with water, saturated aqueous sodium chloride, and dried over magnesium sulfate. The solution was then filtered through a pad of silica, flushed with toluene, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography using heptane / dichloromethane as the eluent (dichloromethane gradient: 0-30%) to give intermediate 1-5 (8.55 g, 89% yield) as a beige foam, which was characterized by electrospray ionization mass spectrometry (ESI-MS). The results are shown below. ESI-MS: C ５９ H ５０ Br ３ ClN ２ Calculated mass of O = 1074, Measured mass = 1075 (M + 1)

[0681] (Synthesis of Intermediate 1-6) Next, intermediate 1-6 was synthesized.

[0682]

[0683] To a 500 mL degassed three-neck round-bottom flask was added Intermediate 1-5 (7.86 g, 7.29 mmol) and tert-butylbenzene (250 mL), and the solution was degassed under nitrogen. The solution was cooled to 0°C in an ice bath. 1.4 M sec-butyllithium in cyclohexane (16.4 mL, 23.0 mmol) was added via syringe to keep the reaction below 3°C. After the addition was complete, the reaction was stirred at room temperature for 1 hour and then cooled to 0°C. Trimethyl borate (3.18 g, 30.6 mmol) was added, and the reaction was heated under a nitrogen atmosphere at an oil bath temperature of 90°C for 18 hours. The reaction was then cooled to room temperature, and the mixture was washed with water, saturated aqueous sodium chloride, and dried over magnesium sulfate. The solution was filtered through a pad of silica, flushed with toluene, and the solvent removed under reduced pressure. The crude product was purified by column chromatography using heptane / toluene (ratio 9:1) as the eluent to give intermediate 1-6 (3.72 g, 60% yield) as a yellow solid, which was characterized by electrospray ionization mass spectrometry (ESI-MS). The results are shown below. ESI-MS: ５９ H ５０ BClN ２ Calculated value of O = 848, Measured mass = 849 (M + 1)

[0684] (Synthesis of Compound BD-1) Next, compound BD-1 was synthesized.

[0685]

[0686] To a 250 mL degassed three-neck round-bottom flask was added Intermediate 1-6 (0.840 g, 0.989 mmol), 2,6-dimethylphenylboronic acid (0.378 g, 2.947 mmol), palladium(II) acetate (11 mg, 5 mol%), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-3-yl)phosphane (96 mg, 20 mol%), cesium carbonate (0.806 g, 2.47 mmol), toluene (21 mL), ethanol (7 mL), and water (7 mL). The reaction was heated under a nitrogen atmosphere at an oil bath temperature of 75°C for 1 hour. The reaction was then cooled to room temperature, and 10% ammonium chloride solution was added to quench the reaction. The mixture was washed with water, saturated aqueous sodium chloride, and dried over magnesium sulfate. The solution was then filtered through a pad of silica, flushed with toluene, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography using hexane / dichloromethane (ratio 8:1) as the eluent to obtain compound BD-1 (0.855 g, yield 94%) as a yellow solid, which was characterized by electrospray ionization mass spectrometry (ESI-MS). The results are shown below. ESI-MS: ６７ H ５９ BN ２ Calculated value of O = 918, Measured mass = 919 (M + 1)

[0687] [Synthesis of Compound BD-2] The synthesis method of compound BD-2 is described below.

[0688] (Synthesis of Compound BD-2) Compound BD-2 was synthesized.

[0689]

[0690] To a 250 mL degassed three-neck round-bottom flask was added intermediate 1-6 (0.830 g, 0.977 mmol), (2,6-bis(methyl-d3)phenyl)boronic acid (0.381 g, 2.44 mmol), palladium(II) acetate (11 mg, 5 mol%), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-3-yl)phosphane (47 mg, 10 mol%), cesium carbonate (0.796 g, 2.44 mmol), toluene (21 mL), ethanol (7 mL), and water (7 mL). The reaction was heated under a nitrogen atmosphere at an oil bath temperature of 75°C for 1 hour. The reaction was then cooled to room temperature, and 10% ammonium chloride solution was added to quench the reaction. The mixture was washed with water, saturated aqueous sodium chloride, and dried over magnesium sulfate. The solution was then filtered through a pad of silica, flushed with toluene, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography using hexane / dichloromethane (ratio 8:1) as the eluent to obtain compound BD-2 (0.780 g, 86% yield) as a yellow solid, which was characterized by electrospray ionization mass spectrometry (ESI-MS). The results are shown below. ESI-MS: ６７ H ５３ D ６ BN ２ Calculated value of O = 924, Measured mass = 925 (M + 1)

[0691] [Synthesis of Compound BD-3] The synthesis method of compound BD-3 is described below.

[0692] (Synthesis of Intermediate 3-1) First, intermediate 3-1 was synthesized.

[0693]

[0694] To a 750 mL degassed three-neck round-bottom flask was added 1-bromo-4-tertbutyl-2,6-dimethylbenzene (39.2 g, 163 mmol). ６ (205 g, 2.438 mol) was added followed by potassium tert-butoxide (9.12 g, 81 mmol). The reaction was heated at 50° C. for 24 hours and then cooled to room temperature. The mixture was treated with D ２The mixture was quenched with 0, diluted with heptane, washed with water, saturated aqueous sodium chloride, and dried over magnesium sulfate. The solvent was removed under reduced pressure to give Intermediate 3-1 (36.9 g, 92% yield) as a colorless oil, which was used directly without further purification. ６ indicates a deuterium compound in which all six hydrogen atoms of dimethyl sulfoxide have been replaced with deuterium atoms.

[0695] (Synthesis of Intermediate 3-2) Next, intermediate 3-2 was synthesized.

[0696]

[0697] To a 250 mL degassed three-neck round-bottom flask was added Intermediate 3-1 (12.5 g, 50.6 mmol), 4-aminobiphenyl (12.2 g, 70.8 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.70 g, 1.5 mol%), tri-tert-butylphosphonium tetrafluoroborate (0.88 g, 6 mol%), and sodium tert-butoxide (10.7 g, 111 mmol). Toluene (170 mL) was then added, and the reaction was heated under a nitrogen atmosphere at an oil bath temperature of 110° C. for 5 hours. The reaction was then cooled to room temperature, and the mixture was washed with water, saturated aqueous sodium chloride, and dried over magnesium sulfate. The solution was then filtered through a pad of silica and flushed with toluene. The solvent was removed under reduced pressure, and the crude product was purified by column chromatography using hexane / dichloromethane (ratio 9:1) as the eluent to give intermediate 3-2 (14.5 g, 85% yield) as orange crystals, which were characterized by electrospray ionization mass spectrometry (ESI-MS). The results are shown below. ESI-MS: ２４ H ２１ D ６ Calculated value of N = 335, measured mass = 335 (M + 1)

[0698] (Synthesis of Intermediate 3-3) Next, intermediate 3-3 was synthesized.

[0699]

[0700] To a 250 mL degassed three-neck round-bottom flask was added Intermediate 3-2 (7.00 g, 20.9 mmol), 1-bromo-3-iodobenzene (8.85 g, 31.3 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.191 g, 1 mol%), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.483 g, 4 mol%), and sodium tert-butoxide (4.01 g, 41.7 mmol). Xylene (100 mL) was then added, and the reaction was heated under a nitrogen atmosphere at an oil bath temperature of 120° C. for 2.5 hours. The reaction was then cooled to room temperature, and the mixture was washed with water, saturated aqueous sodium chloride, and dried over magnesium sulfate. The solution was then filtered through a pad of silica, flushed with toluene, and the solvent was removed under reduced pressure. The crude product was suspended in hot ethanol, followed by filtration to give intermediate 3-3 (9.60 g, 73% yield) as a brown solid, which was characterized by electrospray ionization mass spectrometry (ESI-MS). The results are shown below. ESI-MS: C ３０ H ２４ D ６ Calculated mass of BrN = 489, Measured mass = 490 (M + 1)

[0701] (Synthesis of Intermediate 3-4) Next, intermediate 3-4 was synthesized.

[0702]

[0703] The synthesis procedure for intermediate 1-4 was followed, except that intermediate 3-3 was used instead of intermediate 1-3. Intermediate 3-4 was obtained as a colorless foam in 26% yield. It was characterized by electrospray ionization mass spectrometry (ESI-MS). The results are shown below. ESI-MS: C ４５ H ３８ D ６ N ２ Calculated value = 618, measured mass = 619 (M + 1)

[0704] (Synthesis of Intermediate 3-5) Next, intermediate 3-5 was synthesized.

[0705]

[0706] To a 250 mL degassed three-neck round-bottom flask was added 2,3-dibromo-5-chloro-N,N-bis[4-(1,1-dimethylethyl)phenyl]benzenamine (2.75 g, 5.01 mmol), Intermediate 3-4 (3.10 g, 5.01 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.046 g, 1 mol%), tri-tert-butylphosphonium tetrafluoroborate (0.058 g, 4 mol%), and sodium tert-butoxide (1.20 g, 12.5 mmol). Toluene (100 mL) was then added, and the reaction was heated under a nitrogen atmosphere at an oil bath temperature of 120°C for 1 hour. The reaction was then cooled to room temperature, and the mixture was washed with water, saturated aqueous sodium chloride, and dried over magnesium sulfate. The solution was filtered through a pad of silica, flushed with toluene, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography using hexane / dichloromethane (dichloromethane gradient: 0-40%) as the eluent to give intermediate 3-5 (1.80 g, 32% yield) as a yellow foam, which was characterized by electrospray ionization mass spectrometry (ESI-MS). The results are shown below. ESI-MS: C ７１ H ６５ D ６ BrClN ３ Calculated value = 1085, measured mass = 1086 (M + 1)

[0707] (Synthesis of Intermediate 3-6) Next, intermediate 3-6 was synthesized.

[0708]

[0709] To a 250 mL degassed three-neck round-bottom flask was added intermediate 3-5 (5.00 g, 4.60 mmol) and tert-butylbenzene (150 mL), and the solution was degassed under nitrogen. The solution was cooled to -10 °C in an ethanol-ice bath. 1.4 M sec-butyllithium in cyclohexane (3.67 mL, 5.23 mmol) was added via syringe to keep the reaction below 0 °C. After 30 minutes, trimethyl borate (1.43 g, 13.8 mmol) was added, and the reaction was stirred at room temperature for 30 minutes. The reaction was cooled to 0 °C in an ice bath, and 1 M boron tribromide in heptane (27.6 mL, 27.6 mmol) was added. The reaction was then heated at 60 °C for 2 hours and cooled to room temperature. N,N-Diisopropylethylamine (7.13 g, 55.2 mmol) was added, and the resulting reaction mixture was stirred at room temperature for 30 minutes. The reaction was quenched with methanol (10 mL) and then poured into 700 mL of methanol. The resulting solid was filtered off and dissolved in toluene / dichloromethane (150 mL, 1:1 ratio), and the solution was filtered through a pad of silica and flushed with toluene. Acetonitrile (500 mL) was then added and the dichloromethane was removed under reduced pressure. The resulting yellow precipitate was filtered and the solid was washed with methanol to give intermediate 3-6 (3.2 g, 69% yield) as a yellow solid, which was characterized by electrospray ionization mass spectrometry (ESI-MS). The results are shown below. ESI-MS: C ７１ H ６３ D ６ BClN ３ Calculated value = 1091, measured mass = 1092 (M + 1)

[0710] (Synthesis of Compound BD-3) Next, compound BD-3 was synthesized.

[0711]

[0712] The synthesis procedure for compound BD-2 was followed, except that intermediate 3-6 was used instead of intermediate 1-6. Compound BD-3 was obtained as a yellow solid in 24% yield. It was characterized by electrospray ionization mass spectrometry (ESI-MS). The results are shown below. ESI-MS: C ７９ H ６６ D１２ BN ３ Calculated value = 1091, measured mass = 1092 (M + 1)

[0713] [Synthesis of Compound BD-4] The synthesis method of compound BD-4 is described below.

[0714] (Synthesis of Intermediate 4-1) First, intermediate 4-1 was synthesized.

[0715]

[0716] The synthesis procedure for intermediate 1-4 was followed, except that N-(3-bromophenyl)-5-(1,1-dimethylethyl)-N-[4-(1,1-dimethylethyl)phenyl][1,1'-biphenyl]-2-amine was used instead of intermediate 1-3. Intermediate 4-1 was obtained as a colorless foam in 91% yield. It was characterized by electrospray ionization mass spectrometry (ESI-MS). The results are shown below. ESI-MS: C ４７ H ４８ N ２ Calculated value = 640, measured mass = 641 (M + 1)

[0717] (Synthesis of Intermediate 4-2) Next, intermediate 4-2 was synthesized.

[0718]

[0719] The synthesis procedure for intermediate 3-5 was followed, except that intermediate 4-1 was used instead of intermediate 3-4. Intermediate 4-2 was obtained as a colorless foam in 77% yield. It was characterized by electrospray ionization mass spectrometry (ESI-MS). The results are shown below. ESI-MS: C ７３ H ７５ BrClN ３ Calculated value = 1107, measured mass = 1108 (M + 1)

[0720] (Synthesis of Intermediate 4-3) Next, intermediate 4-3 was synthesized.

[0721]

[0722] The synthetic procedure for intermediate 3-6 was followed, except that intermediate 4-2 was used instead of intermediate 3-5. Intermediate 4-3 was obtained as a yellow solid in 62% yield. It was characterized by electrospray ionization mass spectrometry (ESI-MS). The results are shown below. ESI-MS: C ７３ H ７３ BClN ３ Calculated value = 1037, measured mass = 1038 (M + 1)

[0723] (Synthesis of Compound BD-4) Next, compound BD-4 was synthesized.

[0724]

[0725] The synthesis procedure for compound BD-2 was followed, except that intermediate 4-3 was used instead of intermediate 1-6. Compound BD-4 was obtained as a yellow solid in 87% yield. It was characterized by electrospray ionization mass spectrometry (ESI-MS). The results are shown below. ESI-MS: C ８１ H ７６ D ６ BN ３ Calculated value = 1113, measured mass = 1114 (M + 1)

[0726] [Synthesis of Compound BD-5] The synthesis method of compound BD-5 is described below.

[0727] (Synthesis of Compound BD-5) Compound BD-5 was synthesized.

[0728]

[0729] The synthesis procedure for compound BD-1 was followed, except that B-[1,1':3',1''terphenyl]-2'-ylboronic acid was used instead of 2,6-dimethylphenylboronic acid. Compound BD-5 was obtained as a yellow solid in 23% yield. It was characterized by electrospray ionization mass spectrometry (ESI-MS). The results are shown below. ESI-MS: C ７７ H ６３ BN ２ Calculated value of O = 1042, measured mass = 1043 (M + 1)

[0730] 1, 1A, 1B... organic EL element, 2... substrate, 3... anode, 4... cathode, 5... light-emitting layer, 51... first light-emitting layer, 52... second light-emitting layer, 6... hole injection layer, 7... hole transport layer, 8... electron transport layer, 9... electron injection layer, 10, 10A, 10B... organic layer, 50A, 50B... light-emitting zone, 67... first organic layer, 89... second organic layer.

Claims

1. A compound represented by the following formula (1): [In the above formula (1), R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , and R ８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ９ , R １０ , and R １１ any one of R is a single bond bonded to *2 in the group represented by formula (1A), and R is not a single bond bonded to *2 in the group represented by formula (1A). ９ ~R １１ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, １３ａ , R １３ｂ , R １３ｃ , R １３ｄ , R １３ｅ , R １３ｆ , R １３ｇ , and R １３ｈ Any one of R is a single bond bonded to *1, and R is not a single bond bonded to *1 １３ａ ~R １３ｈ Among these, one or more pairs of adjacent two or more R are bonded to each other to form a ring represented by formula (1B-1), bonded to each other to form a ring represented by formula (1B-2), or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring. １ ~R ８ R is not a group represented by formula (1A), does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring. ９ ~R １１ and R which is not a single bond bonded to *1, does not form a ring represented by formula (1B-1), and does not form a ring represented by formula (1B-2). １３ａ ~R １３ｈ , each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ ), a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ ) group represented by -O-(R １３６ ) group represented by -S-(R １３７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, １ is an oxygen atom, a sulfur atom, or C(R １３８ ) (R １３９ ) and L １ and L ２ are each independently a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, or a substituted or unsubstituted divalent aralkyl group having 7 or more carbon atoms, m and n are each independently 0, 1, 2, or 3, with the proviso that when m is 0, (L １ ) m represents a single bond, and when n is 0, (L ２ ) n represents a single bond; when m is 2 or 3, a plurality of L １ are the same or different from each other, and when n is 2 or 3, a plurality of L ２ are the same or different, Y is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ ), a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ ) group represented by -O-(R １３６ ) group represented by -S-(R １３７ A) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (1C). ｋ１ and A ｋ２ each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; R １２ａ , R １２ｂ , and R １２ｃ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring. １２ａ ~R １２ｃ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ ), a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ ) group represented by -O-(R １３６ ) group represented by -S-(R １３７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. １４ａ , R １４ｂ , R １４ｃ , and R １４ｄ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring. １４ａ ~R １４ｄ , and R １５ａ , R １５ｂ , R １５ｃ , and R １５ｄ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ ), a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ ) group represented by -O-(R １３６ ) group represented by -S-(R １３７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ２ is an oxygen atom, a sulfur atom, or C(R １３８ ) (R １３９ (In the formula (1C), R １６ａ , R １６ｂ , R １６ｃ , R １６ｄ , R １６ｅ , R １６ｆ , R １６ｇ , and R １６ｈ Any one of the following is L １ is a single bond bonded to L １ R that is not a single bond bonded to １６ａ ~R １６ｈ one or more pairs of adjacent two or more of the groups are bonded to each other to form a ring represented by the formula (1B-1), bonded to each other to form a ring represented by the formula (1B-2), or are not bonded to each other, and １ R which does not form a ring represented by formula (1B-1) and does not form a ring represented by formula (1B-2) １６ａ ~R １６ｈ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ ), a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ ) group represented by -O-(R １３６ ) group represented by -S-(R １３７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ３ is an oxygen atom, a sulfur atom, or C(R １３８ ) (R １３９ In the compound represented by the formula (1), R １３１ ~R １３７ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted hydrocarbon ring group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; R １３８ and R １３９ are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring. １３８ and R １３９ each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; R １３１ When there are multiple R １３１ are the same or different from each other, R １３２ When there are multiple R １３２ are the same or different from each other, R １３３ When there are multiple R １３３ are the same or different from each other, R １３４ When there are multiple R １３４ are the same or different from each other, R １３５ When there are multiple R １３５ are the same or different from each other, R １３６ When there are multiple R １３６ are the same or different from each other, R １３７ When there are multiple R １３７ are the same or different from each other, R １３８ When there are multiple R １３８ are the same or different from each other, R １３９ When there are multiple R １３９ are the same or different from each other. (However, among the compounds represented by formula (1), the compounds represented by the following formulas (10A) and (10B) are excluded.) 2. The compound according to claim 1, wherein the compound represented by formula (1) is a compound represented by the following formula (10): (In the formula (10), R １ ~R ９ , R １１ , R １３ａ ~R １３ｈ , X １ , L １ , L ２ , m, n, Y, A ｋ１ , A ｋ２ , and R １２ａ ~R １２ｃ are R in the formula (1), １ ~R ９ , R １１ , R １３ａ ~R １３ｈ , X １ , L １ , L ２ , m, n, Y, A ｋ１ , A ｋ２ , and R １２ａ ~R １２ｃ (Same meaning as above.) 3. In the compound represented by the formula (10), A ｋ１ and A ｋ２ and each of the formula (1) and (2) are a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

4. In the compound represented by the formula (1), A in the group represented by the formula (1A) ｋ１ and A ｋ２ and each of the formula (1) and (2) is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms.

5. The compound according to any one of claims 1 to 4, wherein in the compound represented by formula (1), m and n are each independently 0 or 1.

6. In the compound represented by the formula (1), X １ is an oxygen atom or C(R １３８ ) (R １３９ 6. The compound according to claim 1 , wherein 7. In the compound represented by the formula (1), X １ is C(R １３８ ) (R １３９ 7. The compound according to claim 1 , wherein 8. In the compound represented by the formula (1), X in the group represented by the formula (1C) ３ is an oxygen atom or C(R １３８ ) (R １３９ 8. The compound according to claim 1 , wherein 9. In the compound represented by the formula (1), X in the group represented by the formula (1C) ３ is C(R １３８ ) (R １３９ 9. The compound according to claim 1 , wherein 10. The compound according to any one of claims 1 to 9, wherein, in the compound represented by formula (1), Y is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by formula (1C).

11. In the compound represented by the formula (1), R １ ~R １１ does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. The compound according to any one of claims 1 to 10.

12. In the compound represented by the formula (1), R in the group represented by the formula (1A) １２ａ ~R １２ｃ does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring.

13. In the compound represented by formula (1), R which is not a single bond bonded to *1 １３ａ ~R １３ｈ does not form a ring represented by formula (1B-1) and does not form a ring represented by formula (1B-2).

14. In the compound represented by the formula (1), L in the group represented by the formula (1C) １ R that is not a single bond bonded to １６ａ ~R １６ｈ does not form a ring represented by formula (1B-1) and does not form a ring represented by formula (1B-2).

15. In the compound represented by the formula (1), R １ ~R ８ At least one selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or -N(R １３１ ) (R １３２ The compound according to any one of claims 1 to 14, wherein:

16. The compound according to any one of claims 1 to 15, wherein the compound represented by formula (1) contains at least one deuterium atom.

17. In the compound represented by the formula (1), A in the formula (1A) ｋ１ and A ｋ２ wherein at least one selected from the group consisting of is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and containing at least one deuterium atom, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and containing at least one deuterium atom.

18. In the compound represented by the formula (1), R １ ~R ８ At least one selected from the group consisting of -N(R １３１ ) (R １３２ The compound according to any one of claims 1 to 17, wherein:

19. The compound according to any one of claims 1 to 18, wherein in the compound represented by formula (1), n ​​is 0 and m is 1.

20. In the compound represented by the formula (1), R ７ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or -N(R １３１ ) (R １３２ The compound according to any one of claims 1 to 19, wherein:

21. In the compound represented by the formula (1), R ２ and R ３ The compound according to any one of claims 1 to 20, wherein any one of the above is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

22. The compound according to any one of claims 1 to 21, wherein the substituent in the term "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 13 ring atoms.

23. A compound according to any one of claims 1 to 22, wherein any group described as "substituted or unsubstituted" is an "unsubstituted" group.

24. R １ ~R ８ Any pair of adjacent two or more of R ９ ~R １１ Any pair of adjacent two or more of R １２ａ ~R １２ｃ Among these, adjacent pairs of two or more are not bonded to each other, and * is not a single bond bonded to 1. １３ａ ~R １３ｈ Any pair of adjacent two or more of these is not bonded to each other, １４ａ ~R １４ｄ Any pair of adjacent two or more of L １ R that is not a single bond bonded to １６ａ ~R １６ｈ The compound according to any one of claims 1 to 23, wherein any adjacent pairs of two or more of:

25. An organic electroluminescence element comprising a cathode, an anode, and an organic layer between the cathode and the anode, wherein at least one layer included in the organic layer contains the compound according to any one of claims 1 to 24 as a first compound.

26. The organic electroluminescence device according to claim 25, wherein the organic layer includes an emitting layer, and the emitting layer contains the first compound.

27. The organic electroluminescence device according to claim 26, wherein the light-emitting layer contains a second compound represented by the following formula (H10): [(In the above formula (H10), R １０１ ~R １１０ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring. １０１ ~R １１０ are each independently a hydrogen atom, a substituent R, or a group represented by the following formula (H10A), provided that R does not form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted condensed ring. １０１ ~R １１０ At least one of the groups represented by formula (H10A) is a group represented by the following formula (H10A), and when two or more groups represented by formula (H10A) are present, the two or more groups represented by formula (H10A) are the same or different from each other. １０１ -Ar １０１ (H10A)) (In the above formula (H10A), L １０１ represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, １０１ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and the substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ) group represented by -O-(R ９０４ ) group represented by -S-(R ９０５ ), a group represented by -N(R ９０６ ) (R ９０７ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, when two or more of the substituents R are present, the two or more substituents R are the same or different, ９０１ ~R ９０７ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; R ９０１ When there are multiple R ９０１ are the same or different from each other, R ９０２ When there are multiple R ９０２ are the same or different from each other, R ９０３ When there are multiple R ９０３ are the same or different from each other, R ９０４ When there are multiple R ９０４ are the same or different from each other, R ９０５ When there are multiple R ９０５ are the same or different from each other, R ９０６ When there are multiple R ９０６ are the same or different from each other, R ９０７ When there are multiple R ９０７ are the same or different from each other.

28. The organic electroluminescence device according to claim 26 or 27, wherein a hole transport layer is disposed between the anode and the light emitting layer.

29. The organic electroluminescence device according to any one of claims 26 to 28, wherein an electron transport layer is disposed between the cathode and the light-emitting layer.

30. An electronic device equipped with the organic electroluminescence element according to any one of claims 25 to 29.

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