Compound, organic electroluminescent element, and electronic device

Abstract

This compound is represented by general formula (1). R1-R14 each independently represent a hydrogen atom, a substituted or unsubstituted aryl group having 6-19 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5-50 ring-forming atoms, a group represented by general formula (12), or the like. At least one among R1-R14 is a group represented by general formula (12). L1 represents a substituted or unsubstituted arylene group having 6-30 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5-30 ring-forming atoms. Ar1 represents a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted heterocyclic group having 5-30 ring-forming atoms, or the like. When L1 represents a heterocyclic group, the ring of that heterocyclic group, and, when Ar1 represents a heterocyclic group, the ring of that heterocyclic group do not include a nitrogen atom or a sulfur atom.

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] Organic electroluminescence elements (hereinafter sometimes referred to as "organic EL elements") are applied to full-color displays such as mobile phones and televisions. When a voltage is applied to an organic EL element, holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical law of electron spin, singlet excitons are generated at a rate of 25% and triplet excitons are generated at a rate of 75%. Performance characteristics of organic EL elements include, for example, brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan. For example, Patent Document 1 discusses ways to improve the performance of organic EL elements.

[0003] US Patent Application Publication No. 2017 / 062735

[0004] An object of the present invention is to provide a compound capable of improving the performance of an organic electroluminescence device, to provide an organic electroluminescence device containing the compound, and to provide an electronic device equipped with the organic electroluminescence device.

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

[0006]

[0007] (In the general formula (1), R １ ~R １４ one or more pairs of adjacent R groups bond to each other to form a substituted or unsubstituted monocycle, or bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other, １ ~R １４are 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 19 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the general formula (12), １ ~R １４ At least one of R is a group represented by the general formula (12), １ ~R １４ When any of R is a heterocyclic group, the ring of the heterocyclic group does not contain a nitrogen atom or a sulfur atom, ９ and R １４ and R are hydrogen atoms. ９ and R １４ are different from each other, and R ２ , R ４ , R ５ , R ７ , R １１ and R １２ When one or two of the groups are the group represented by the general formula (12), R １ , R ３ , R ６ , R ８ , R ９ , R １０ , R １３ and R １４ At least one of the following is not a hydrogen atom: １is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, １ When L is a heterocyclic group, the ring of the heterocyclic group does not contain a nitrogen atom or a sulfur atom, n is 0, 1, 2 or 3, and when n is 0, -(L １ ) ０ - is a single bond, and when n is 2 or 3, two or three L １ are the same or different from each other, Ar １ is a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted dibenz[a,c]anthracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, a substituted or unsubstituted indenofluorenyl group, a substituted or unsubstituted fluoranthenyl group, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and Ar １ When Ar is a heterocyclic group, the ring of the heterocyclic group does not contain a nitrogen atom or a sulfur atom, １ is not a benzoxanthenyl group, and Ar １ When Ar is a heterocyclic group having a substituent, the substituent is not a substituted or unsubstituted anthracenyl group, and １is a group having a substituent, the substituent does not include a group represented by the following general formula (PO1); when a plurality of groups represented by the general formula (12) are present, the plurality of groups represented by the general formula (12) are the same or different from one another; in the compound represented by the general formula (1), when the substituent in the case of "substituted or unsubstituted" is a heterocyclic group, the ring of the heterocyclic group does not include a nitrogen atom or a sulfur atom; in the compound represented by the general formula (1), when the substituent in the case of "substituted or unsubstituted" is an aryl group, the number of ring carbon atoms of the aryl group is 6 to 19; * indicates the bonding position to the dibenz[a,c]anthracene ring represented by the general formula (1).

[0008]

[0009] (In the general formula (PO1), Rp １ and Rp ２ are each independently 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 * indicates the bonding position.

[0010] (In the compound represented by the general formula (1), R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , 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 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, R９０４ 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 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.)

[0011] According to one aspect of the present invention, there is provided an organic electroluminescence device containing 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 aspect of the present invention, it is possible to provide a compound capable of improving the performance of an organic electroluminescence device, an organic electroluminescence device containing the compound, 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, and 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.

[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 indicated 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 the present specification, the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the groups represented by the following general formulae (TEMP-69) to (TEMP-102).

[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 With the pair, R ９２５ and R ９２６ Paired with R ９２６ and R ９２７ Paired with R ９２７ and R ９２８ 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 general formula (1).

[0119]

[0120] (In the general formula (1), R １ ~R １４ one or more pairs of adjacent R groups bond to each other to form a substituted or unsubstituted monocycle, or bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other, １ ~R １４ 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 19 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the general formula (12), １ ~R １４ At least one of R is a group represented by the general formula (12), １ ~R １４ When any of R is a heterocyclic group, the ring of the heterocyclic group does not contain a nitrogen atom or a sulfur atom, ９ and R １４ and R are hydrogen atoms. ９ and R １４ are different from each other, and R ２ , R ４ , R ５ , R ７ , R １１ and R １２ When one or two of the groups are the group represented by the general formula (12), R １ , R ３ , R ６ , R ８ , R ９ , R １０ , R １３ and R １４ At least one of the following is not a hydrogen atom: １ is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, １ When L is a heterocyclic group, the ring of the heterocyclic group does not contain a nitrogen atom or a sulfur atom, n is 0, 1, 2 or 3, and when n is 0, -(L １ ) ０ - is a single bond, and when n is 2 or 3, two or three L １ are the same or different from each other, Ar １is a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted dibenz[a,c]anthracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, a substituted or unsubstituted indenofluorenyl group, a substituted or unsubstituted fluoranthenyl group, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and Ar １ When Ar is a heterocyclic group, the ring of the heterocyclic group does not contain a nitrogen atom or a sulfur atom, １ is not a benzoxanthenyl group, and Ar １ When Ar is a heterocyclic group having a substituent, the substituent is not a substituted or unsubstituted anthracenyl group, and １ is a group having a substituent, the substituent does not include a group represented by the following general formula (PO1); when a plurality of groups represented by the general formula (12) are present, the plurality of groups represented by the general formula (12) are the same or different from one another; in the compound represented by the general formula (1), when the substituent in the case of "substituted or unsubstituted" is a heterocyclic group, the ring of the heterocyclic group does not include a nitrogen atom or a sulfur atom; in the compound represented by the general formula (1), when the substituent in the case of "substituted or unsubstituted" is an aryl group, the number of ring carbon atoms of the aryl group is 6 to 19; * indicates the bonding position to the dibenz[a,c]anthracene ring represented by the general formula (1).

[0121]

[0122] (In the general formula (PO1), Rp １ and Rp ２are each independently 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 * indicates the bonding position.

[0123] (In the compound represented by the general formula (1), R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , 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 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 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.)

[0124] Regarding the bonding position of the dibenz[a,c]anthracene ring indicated by * in the group represented by the general formula (12), the dibenz[a,c]anthracene ring in the general formula (1) is R １ ~R １４ means the dibenz[a,c]anthracene ring itself to which R is bonded, １ ~R １４has a dibenz[a,c]anthracene ring, but is not a dibenz[a,c]anthracene ring.

[0125] The compound according to this embodiment has a dibenz[a,c]anthracene ring containing Ar １ Directly or L １ and Ar １ is an aryl group or heterocyclic group having a specific fused ring structure as described above. The compound according to this embodiment having such a structure can improve the device performance of the organic electroluminescence device (e.g., one or more properties selected from the group consisting of luminance, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan). One aspect of the compound according to this embodiment can extend the lifespan of the organic electroluminescence device.

[0126] In the compound according to this embodiment, R １ ~R １４ 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 19 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by general formula (12).

[0127] In the compound according to this embodiment, R １ ~R １４ are preferably each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 19 ring carbon atoms, or a group represented by the general formula (12).

[0128] In the compound according to this embodiment, R １ , R ３ , R ６ , R ８ , R ９ , R １０ , R １３ and R １４At least one of the above is preferably a group represented by the general formula (12).

[0129] In the compound according to this embodiment, R １ ~R １４ is preferably a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 19 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0130] In the compound according to this embodiment, R １ ~R １４ are preferably each independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 19 ring carbon atoms.

[0131] In the compound according to this embodiment, R １ ~R １４ is also preferably a hydrogen atom.

[0132] In this embodiment, the compound represented by the general formula (1) is preferably represented by the following general formula (10).

[0133]

[0134] (In the general formula (10), R １ , R ３ , R ６ , R ８ , R ９ , R １０ , R １３ and R １４ are R in the general formula (1), respectively. １ , R ３ , R ６ , R ８ , R ９ , R １０ , R １３ and R １４ is synonymous with

[0135] In this embodiment, the compound represented by the general formula (1) is preferably represented by the following general formula (11).

[0136]

[0137] (In the general formula (11), R １４ is R in the general formula (1). １４ and n, L １ and Ar １ respectively represent n and L in the general formula (12). １ and Ar １ is synonymous with

[0138] In the compound according to this embodiment, R １４ and "*-(L １ ) ｎ -Ar １ " (the group represented by the general formula (12)) are different from each other.

[0139] In the compound according to this embodiment, R １４ is preferably a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 19 ring carbon atoms.

[0140] In the compound according to this embodiment, R １ and R ８ It is also preferable that at least one of the above is a group represented by the general formula (12).

[0141] In the compound according to this embodiment, R ９ and R １４ may both be hydrogen atoms.

[0142] In this embodiment, the compound represented by the general formula (1) is also preferably a compound represented by the following general formula (13), (14), or (15).

[0143]

[0144] (In the general formula (13), R １３ is R in the general formula (1). １３ and in the general formula (14), R １ is R in the general formula (1). １ and in the general formula (15), R ３ is R in the general formula (1). ３In the general formulae (13), (14) and (15), n, L １ and Ar １ respectively represent n and L in the general formula (12). １ and Ar １ is synonymous with

[0145] In the compound according to this embodiment, R in the general formula (13) １３ and "*-(L １ ) ｎ -Ar １ and the groups represented by " may be the same groups or different groups.

[0146] In the compound according to this embodiment, R in the general formula (14) １ and "*-(L １ ) ｎ -Ar １ and the groups represented by " may be the same groups or different groups.

[0147] In the compound according to this embodiment, R in the general formula (15) ３ and "*-(L １ ) ｎ -Ar １ and the groups represented by " may be the same groups or different groups.

[0148] In this embodiment, n in the compound represented by the general formula (1) is preferably 0 or 1.

[0149] In the compound according to this embodiment, n in the general formula (12) is preferably 0. When n is 0, -(L) ０ - is a single bond, i.e., Ar １ is directly bonded to the dibenz[a,c]anthracene ring. For example, when n in the general formula (12) is 0, the compounds represented by the general formulae (11), (13), (14), and (15) are represented by the following general formulae (11A), (13A), (14A), and (15A), respectively.

[0150]

[0151] (In the general formulae (11A), (13A), (14A) and (15A), R １ , R ３ , R １３ and R １４ are R in the general formula (1), respectively. １ , R ３ , R １３ and R １４ and Ar １ represents Ar in the general formula (12). １ is synonymous with

[0152] In the compound according to this embodiment, R １４ and Ar １ and are different groups.

[0153] In the compound according to this embodiment, R in the general formula (13A) １３ and Ar １ and may be the same group or different groups.

[0154] In the compound according to this embodiment, R in the general formula (14A) １ and Ar １ and may be the same group or different groups.

[0155] In the compound according to this embodiment, R in the general formula (15A) ３ and Ar １ and may be the same group or different groups.

[0156] In the compound according to this embodiment, R in the general formulas (11) and (11A) １４ , R in the general formulas (13) and (13A) １３ , R in the general formulas (14) and (14A) １ and R in the general formulas (15) and (15A) ３are 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 19 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by general formula (12).

[0157] In the compound according to this embodiment, R in the general formulas (11) and (11A) １４ , R in the general formulas (13) and (13A) １３ , R in the general formulas (14) and (14A) １ and R in the general formulas (15) and (15A) ３ are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 19 ring carbon atoms, or a group represented by the general formula (12).

[0158] The compound according to this embodiment preferably has one or two groups represented by the general formula (12) in the molecule, and more preferably has only one group.

[0159] In this embodiment, when n is 1, 2, or 3, L in the compound represented by the general formula (1) １ is preferably a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, and more preferably a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms.

[0160] In this embodiment, when n is 1, 2, or 3, L in the compound represented by the general formula (1) １ is also preferably a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.

[0161] In this embodiment, when n is 1, 2, or 3, L in the compound represented by the general formula (1) １ is also preferably a substituted or unsubstituted m-phenylene group or a substituted or unsubstituted p-phenylene group.

[0162] In the compound according to this embodiment, L １is also preferably any group selected from the group consisting of groups represented by the following general formulas (L1) to (L23).

[0163]

[0164]

[0165]

[0166] In the general formulae (L1) to (L23), * indicates a bonding position. The groups represented by the general formulae (L1) to (L23) may or may not each independently have one or more of the above-mentioned "optional substituents." The groups represented by the general formulae (L1) to (L23) may each independently have one or more deuterium atoms.

[0167] Ar in the compound represented by the general formula (1) １ When is a heterocyclic group, the ring of the heterocyclic group preferably contains an oxygen atom.

[0168] In this embodiment, Ar in the compound represented by the general formula (1) １ is a heterocyclic group, Ar as a heterocyclic group １ is preferably a substituted or unsubstituted furanyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzo[b]naphtho[2,1-d]furanyl group, a substituted or unsubstituted benzo[b]naphtho[2,3-d]furanyl group, a substituted or unsubstituted benzo[b]naphtho[1,2-d]furanyl group, a substituted or unsubstituted dinaphthofuranyl group, a substituted or unsubstituted benzobisbenzofuranyl group, a substituted or unsubstituted benzo[b]phenanthrofuranyl group, or a substituted or unsubstituted xanthenyl group.

[0169] In this embodiment, Ar in the compound represented by the general formula (1) １is also preferably a substituted or unsubstituted furanyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzo[b]naphtho[2,1-d]furanyl group, a substituted or unsubstituted benzo[b]naphtho[2,3-d]furanyl group, a substituted or unsubstituted benzo[b]naphtho[1,2-d]furanyl group, a substituted or unsubstituted dinaphthofuranyl group, a substituted or unsubstituted benzobisbenzofuranyl group, a substituted or unsubstituted benzo[b]phenanthrofuranyl group, or a substituted or unsubstituted xanthenyl group.

[0170] In this embodiment, Ar in the compound represented by the general formula (1) １ is also preferably a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted dibenz[a,c]anthracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, a substituted or unsubstituted indenofluorenyl group, or a substituted or unsubstituted fluoranthenyl group.

[0171] In this embodiment, Ar in the compound represented by the general formula (1) １is also preferably a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, a substituted or unsubstituted indenofluorenyl group, or a substituted or unsubstituted fluoranthenyl group.

[0172] In this embodiment, Ar in the compound represented by the general formula (1) １ is also preferably any of the groups represented by the following general formulas (101) to (112).

[0173]

[0174]

[0175]

[0176]

[0177] (R in the general formulas (101) to (112) １０１ ~R １０９ , R １１１ ~R １６５ and R １６６ ~R １８７ 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 19 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and * indicates the bonding position.

[0178] In this embodiment, Ar in the compound represented by the general formula (1) １ is also preferably any of the groups represented by the general formulae (101) to (110).

[0179] In this embodiment, Ar in the compound represented by the general formula (1) １ is also preferably a group represented by the general formula (101), (103), (106), (111) or (112).

[0180] In this embodiment, Ar in the compound represented by the general formula (1) １ is also preferably a group represented by the general formula (101).

[0181] In this embodiment, Ar in the compound represented by the general formula (1) １ is also preferably a group represented by the general formula (111).

[0182] In this embodiment, Ar in the compound represented by the general formula (1) １ is also preferably any of the groups represented by the following general formulae (AR101) to (AR224).

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191] In the general formulae (AR101) to (AR224), * indicates a bonding position. The groups represented by the general formulae (AR101) to (AR224) may each independently have one or more of the above-mentioned "optional substituents", or may not have any of them. The groups represented by the general formulae (AR101) to (AR224) may each independently have one or more deuterium atoms. The "optional substituents" possessed by the groups represented by the general formulae (AR101) to (AR224) are 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 12 ring atoms, and more preferably an unsubstituted aryl group having 6 to 12 ring carbon atoms.

[0192] In this embodiment, Ar in the compound represented by the general formula (1) １ is also preferably any of the groups represented by the general formulae (AR101) to (AR222).

[0193] In this embodiment, Ar in the compound represented by the general formula (1) １ is also preferably a group represented by the general formula (AR101), (AR104), (AR147), (AR152), (AR169) or (AR223).

[0194] In this embodiment, Ar in the compound represented by the general formula (1) １ is also preferably a group represented by the general formula (AR101) or (AR104).

[0195] In this embodiment, Ar in the compound represented by the general formula (1) １ is also preferably a group represented by the general formula (AR147) or (AR152).

[0196] In this embodiment, Ar in the compound represented by the general formula (1) １ is also preferably a group represented by (AR223).

[0197] In this embodiment, the substituted or unsubstituted benzobisbenzofuranyl group is preferably a group represented by any of the general formulae (AR199) to (AR209).

[0198] In this embodiment, Ar in the compound represented by the general formula (1) １ It is also preferred that is not a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0199] In the compound according to this embodiment, R １ ~R １４ It is preferable that any pair of two or more adjacent groups of the above do not bond to each other.

[0200] In this embodiment, it is preferable that the compound represented by the general formula (1) does not have an anthracene structure in the molecule. Note that the "anthracene structure" here refers to the structure of an anthracene ring itself in which three benzene rings are fused, and structures in which one or more rings are further fused to an anthracene ring are not included in the "anthracene structure" here. Therefore, for example, a structure in which four benzene rings are fused, such as benz[a]anthracene, and a structure in which five benzene rings are fused, such as dibenz[a,c]anthracene, are not included in the "anthracene structure" here.

[0201] In this embodiment, the compound represented by the general formula (1) preferably does not have a benzoxanthene structure in the molecule. Here, the "benzoxanthene structure" refers to the following benzo[kl]xanthene structure:

[0202]

[0203] In the compound according to this embodiment, R ９ and R １４ is preferably not a phenanthryl group.

[0204] In this embodiment, the compound represented by the general formula (1) preferably does not contain a phosphorus atom in the molecule.

[0205] In this embodiment, it is preferable that the compound represented by the general formula (1) does not contain a heterocyclic group containing at least one of a nitrogen atom and a sulfur atom as a ring-forming atom in the molecule.

[0206] In this embodiment, it is preferable that the compound represented by the general formula (1) does not contain an aryl group having 20 or more ring carbon atoms in the molecule.

[0207] In this embodiment, it is also preferable that the compound represented by formula (1) contains at least one deuterium atom.

[0208] In the compound according to this embodiment, R １ ~R １４ It is also preferred that one or more of the above be a deuterium atom.

[0209] In the compound according to this embodiment, L １ It is also preferred that contains one or more deuterium atoms.

[0210] In the compound according to this embodiment, Ar １ It is also preferred that contains one or more deuterium atoms.

[0211] In the compound according to this embodiment, Ar １ It is also preferred that all of the hydrogen atoms contained in are deuterium atoms.

[0212] In the compound according to this embodiment, R １ ~R １４ It is also preferable that at least one of the groups is a deuterium atom.

[0213] In the compound according to this embodiment, R １ ~R １４ It is also preferable that the hydrogen atom in is a deuterium atom.

[0214] In the compound according to this embodiment, R １ ~R １４ is also preferably a deuterium atom.

[0215] 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 12 ring atoms.

[0216] In the compounds according to this embodiment, all groups described as "substituted or unsubstituted" are preferably "unsubstituted".

[0217] (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.

[0218] (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.

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320] [Second Embodiment] (Material for Organic Electroluminescence Device) The material for an organic EL device according to this embodiment contains the compound according to the first embodiment. One aspect includes a material for an organic EL device containing only the compound according to the first embodiment. Another aspect includes a material for an organic EL device containing the compound according to the first embodiment and another compound different from the compound in the first embodiment. In the material for an organic EL device according to this embodiment, it is preferable that the compound according to the first embodiment is a host material. In this case, the material for an organic EL device may contain the compound according to the first embodiment as a host material and another compound such as a dopant material.

[0321] The compound according to the first embodiment is useful as a material for an organic EL device, and is useful as a material for the light-emitting layer of an organic EL device, and is particularly useful as a host material for the blue light-emitting layer.

[0322] Third Embodiment Organic Electroluminescence Element An organic EL element according to the third embodiment will be described. The organic EL element according to this embodiment contains the compound according to the first embodiment as a first compound.

[0323] One aspect of the organic EL element according to this embodiment includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer includes at least one layer containing an organic compound. Alternatively, the organic layer is configured by stacking multiple layers containing organic compounds. Each of the organic compound-containing layers constituting the organic layer may independently further include an inorganic compound.

[0324] In one aspect of the organic EL element according to this embodiment, at least one of the organic layers contains a first compound (the compound according to the first embodiment).

[0325] (Light-emitting region) In the organic EL element of this embodiment, the organic layer preferably has a light-emitting region. In the organic EL element of this embodiment, the light-emitting region preferably includes at least one light-emitting layer. In one embodiment, the at least one light-emitting layer contains the first compound (the compound according to the first embodiment).

[0326] (Emission Wavelength of Organic EL Element) The organic EL element according to this embodiment preferably emits light having a maximum peak wavelength of 500 nm or less when driven, and more preferably emits light of 430 nm or more and 480 nm or less. The organic EL element according to this embodiment more preferably emits light having a maximum peak wavelength of 470 nm or less when driven, and even more preferably emits light of 465 nm or less when driven. The organic EL element according to this embodiment more preferably emits light having a maximum peak wavelength of 440 nm or more when driven, and even more preferably emits light of 445 nm or more when driven. The maximum peak wavelength of light emitted by the organic EL element when driven is measured as follows. When the current density is 10 mA / cm 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).

[0327] In the organic EL element according to this embodiment, the organic layer may be composed of only the light-emitting layer, or 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, and an electron blocking layer.

[0328] Fig. 1 shows a schematic configuration of an example of an organic EL element according to this embodiment. The organic EL element 1A shown in Fig. 1 includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10A disposed between the anode 3 and the cathode 4. The organic layer 10A includes, in order from the anode 3 side, a hole transport region 6, an emissive region 5A, and an electron transport region 7. The hole transport region 6 includes, in order from the anode 3 side, a hole injection layer 61 and a hole transport layer 62. The emissive region 5A includes one emissive layer 5. The electron transport region 7 includes, in order from the emissive region 5A side, an electron transport layer 71 and an electron injection layer 72.

[0329] (Light-emitting layer) In one aspect of the organic EL element according to this embodiment, the light-emitting layer contains the compound according to the first embodiment. The compound contained in the light-emitting layer is preferably the first compound (the compound according to the first embodiment).

[0330] (Light-emitting compound) In one aspect of the organic EL element according to this embodiment, the light-emitting layer preferably contains the first compound (the compound according to the first embodiment) and a light-emitting compound. The light-emitting compound contained in the light-emitting layer is preferably a fluorescent compound.

[0331] (Compound Represented by General Formula (5)) In one aspect of the organic EL element according to this embodiment, the light-emitting compound contained in the light-emitting layer is a compound represented by the following general formula (5).

[0332]

[0333] (In the general formula (5), R ５０１ ~R ５０７ and R ５１１ ~R ５１７one 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 ５０１ ~R ５０７ and R ５１１ ~R ５１７ 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, ５２１ and R ５２２ 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.

[0334] In the luminescent compound, R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ and R ９０７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, preferably 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 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.

[0335] "R ５０１ ~R ５０７ and R ５１１ ~R ５１７ "One set of two or more adjacent pairs of R ５０１and R ５０２ A set consisting of R ５０２ and R ５０３ A set consisting of R ５０３ and R ５０４ A set consisting of R ５０５ and R ５０６ A set consisting of R ５０６ and R ５０７ A set consisting of R ５０１ and R ５０２ and R ５０３ It is a combination of a set consisting of:

[0336] In one embodiment, the compound represented by the general formula (5) is a compound represented by the following general formula (52):

[0337]

[0338] (In the general formula (52), R ５３１ ~R ５３４ and R ５４１ ~R ５４４ 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 ５３１ ~R ５３４ , R ５４１ ~R ５４４ , and R ５５１ and R ５５２ are each independently a hydrogen atom, 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 ５６１ ~R ５６４ are each independently 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.

[0339] (Compound Represented by General Formula (6)) In one aspect of the organic EL element according to this embodiment, the light-emitting compound contained in the light-emitting layer is a compound represented by the following general formula (6).

[0340]

[0341] (In the general formula (6), the ring a, the ring b, and the ring c are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, and R ６０１ and R ６０２ each independently bond to the ring a, ring b or ring c to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle, ６０１ and R ６０２ 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, 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.

[0342] In one aspect of the organic EL element according to this embodiment, ring a, ring b, and ring c are rings (substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring carbon atoms, or substituted or unsubstituted heterocycles having 5 to 50 ring atoms) fused to the central fused bicyclic structure of general formula (6) composed of a boron atom and two nitrogen atoms.

[0343] The "aromatic hydrocarbon rings" of rings a, b, and c have the same structure as a compound in which a hydrogen atom is introduced into an "aryl group." The "aromatic hydrocarbon ring" of ring a includes three carbon atoms on the central fused bicyclic structure of general formula (6) as ring-forming atoms. The "aromatic hydrocarbon rings" of rings b and c include two carbon atoms on the central fused bicyclic structure of general formula (6) as ring-forming atoms.

[0344] Specific examples of "substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring carbon atoms" include compounds in which a hydrogen atom has been introduced into the "aryl group" described in specific example group G1. The "heterocyclic rings" of ring a, ring b, and ring c have the same structure as the compounds in which a hydrogen atom has been introduced into the above-mentioned "heterocyclic group". The "heterocyclic ring" of ring a includes three carbon atoms on the central fused bicyclic structure of general formula (6) as ring-forming atoms. The "heterocyclic rings" of ring b and ring c include two carbon atoms on the central fused bicyclic structure of general formula (6) as ring-forming atoms. Specific examples of "substituted or unsubstituted heterocyclic rings having 5 to 50 ring atoms" include compounds in which a hydrogen atom has been introduced into the "heterocyclic group" described in specific example group G2.

[0345] R ６０１ and R ６０２ may each independently bond to ring a, ring b, or ring c to form a substituted or unsubstituted heterocyclic ring. In this case, the heterocyclic ring contains the nitrogen atom on the central fused bicyclic structure of the general formula (6). In this case, the heterocyclic ring may contain a heteroatom other than the nitrogen atom. ６０１ and R ６０２ is bonded to ring a, ring b, or ring c specifically means that an atom constituting ring a, ring b, or ring c is bonded to R ６０１ and R ６０２ It means that the atoms constituting R are bonded together. ６０１ is bonded to ring a, and R ６０１ A two-ring (or three- or more-ring) nitrogen-containing heterocyclic ring may be formed by condensing a ring containing R with ring a. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing two- or more-ring condensed heterocyclic groups in specific example group G2. ６０１ When is bonded to ring b, R ６０２ When R is bonded to ring a, ６０２ The same applies when R is bonded to ring c. ６０１ and R ６０２ may each independently not be bonded to ring a, ring b, or ring c.

[0346] In one embodiment, the ring a, ring b, and ring c in the general formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having ring carbon atoms of 6 to 50. In one embodiment, the ring a, ring b, and ring c in the general formula (6) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.

[0347] In one embodiment, R in the general formula (6) ６０１ and R ６０２ are each independently 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, preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0348] In one embodiment, the compound represented by the general formula (6) is a compound represented by the following general formula (62):

[0349]

[0350] (In the general formula (62), R ６０１Ａ is R ６１１ and R ６２１ R ６０２Ａ is R ６１３ and R ６１４ or a substituted or unsubstituted heterocyclic ring, or a substituted or unsubstituted heterocyclic ring is not formed by bonding to one or more selected from the group consisting of ６０１Ａ and R ６０２Ａ 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, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and R ６１１ ~R ６２１one 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 heterocycle, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring; ６１１ ~R ６２１ 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. ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ and 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, 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 R９０３ 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.)

[0351] R in the general formula (62) ６０１Ａ and R ６０２Ａ are R in the general formula (6), respectively. ６０１ and R ６０２ For example, R ６０１Ａ and R ６１１ may be bonded to form a two-ring (or three- or more-ring) fused nitrogen-containing heterocycle in which a ring containing the ring is fused with a benzene ring corresponding to ring a. Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing two- or more-ring fused heterocyclic groups in specific example group G2. ６０１Ａ and R ６２１ When R ６０２Ａ and R ６１３ is bonded, and R ６０２Ａ and R ６１４ The same applies when the two are combined.

[0352] R ６１１ ~R ６２１ One or more pairs of adjacent two or more of R may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or may be bonded to each other to form a substituted or unsubstituted fused ring. ６１１ and R ６１２ may be bonded to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like is fused to the six-membered ring to which they are bonded, and the fused ring formed is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring.

[0353] In one embodiment, the compound represented by the general formula (6) is a compound represented by the following general formula (63):

[0354]

[0355] (In the general formula (63), R ６１１ ~R ６１７ , R ６０１Ａ and R ６０２Ａ are each independently R in the general formula (62). ６１１ ~R ６１７ , R ６０１Ａ and R ６０２Ａ is synonymous with X ４ is an oxygen atom or a sulfur atom, R ７０１ ~R ７０４ 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 ７０１ ~R ７０４ 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, ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R９０６ and R ９０７ are each independently R in the general formula (62). ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ and R ９０７ is synonymous with

[0356] (Compound Represented by General Formula (3A)) In one aspect of the organic EL element according to this embodiment, the light-emitting compound contained in the light-emitting layer is a compound represented by the following general formula (3A).

[0357]

[0358] (In the general formula (3A), Ra ３０１ , Ra ３０２ , Ra ３０３ , Ra ３０４ , Ra ３０５ , Ra ３０６ , Ra ３０７ , Ra ３０８ , Ra ３０９ and Ra ３１０ one or more pairs of adjacent two or more of Ra 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, ３０１ ~Ra ３１０ at least one of Ra is a monovalent group represented by the following general formula (31A), which does not form the monocycle, does not form the condensed ring, and is not a monovalent group represented by the following general formula (31A): ３０１ ~Ra ３１０ 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 ９０５a 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.

[0359]

[0360] (In the general formula (31A), Ara ３０１ and Ara ３０２ are each independently 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, ３０１ , La ３０２ and La ３０３ are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, and * indicates a bonding position on the pyrene ring in general formula (3A).

[0361] (Specific Examples of Light-Emitting Compounds) Specific examples of light-emitting compounds are listed below, but these are merely illustrative and the light-emitting compounds are not limited to the following specific examples.

[0362]

[0363] (Maximum Peak Wavelength of Compound) In the organic EL device according to this embodiment, the light-emitting compound contained in the light-emitting layer is preferably a compound that exhibits light emission (preferably fluorescent emission) with a maximum peak wavelength of 500 nm or less. The maximum peak wavelength of the light emission (preferably fluorescent emission) exhibited by the light-emitting compound is preferably 480 nm or less, more preferably 460 nm or less, and even more preferably 455 nm or less. The maximum peak wavelength of the light emission (preferably fluorescent emission) exhibited by the light-emitting compound is preferably 430 nm or more, more preferably 440 nm or more, and even more preferably 445 nm or more.

[0364] The method for measuring the maximum peak wavelength of a compound in this specification is as follows. －６ mol / L or more, 10 －５ A toluene solution of 0.01 mol / L or less is prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K). The emission spectrum can be measured using a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measuring device is not limited to the device used here. The peak wavelength of the emission spectrum at which the emission intensity is maximum is defined as the maximum emission peak wavelength. Note that in this specification, the maximum peak wavelength may also be referred to as the maximum fluorescence emission peak wavelength (FL-peak).

[0365] In the organic EL element according to this embodiment, when the light-emitting layer contains a first compound (the compound according to the first embodiment) and a light-emitting compound, it is preferable that the first compound (the compound according to the first embodiment) is a host material (which may also be referred to as a matrix material), and the light-emitting compound is a dopant material (which may also be referred to as a guest material, an emitter, or a light-emitting material).

[0366] 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." Therefore, for example, in the case of the organic EL element according to this embodiment, the light-emitting layer contains the first compound (the compound according to the first embodiment) in an amount of 50% by mass or more of the total mass of the light-emitting layer.

[0367] (Thickness of the Light-Emitting Layer) In the organic EL element according to this embodiment, the thickness of the light-emitting layer is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less. When the thickness of the light-emitting layer is 5 nm or more, it is easy to form the light-emitting layer and adjust the chromaticity. When the thickness of the light-emitting layer is 50 nm or less, it is easy to suppress an increase in driving voltage.

[0368] (Compound Content in Light-Emitting Layer) In the organic EL device according to this embodiment, when the light-emitting layer contains a first compound (compound according to the first embodiment) and a light-emitting compound, the contents of the first compound (compound according to the first embodiment) and the light-emitting compound in the light-emitting layer are preferably, for example, in the following ranges. The content of the first compound (compound according to the first embodiment) is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less. The content of the light-emitting compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less. However, the upper limit of the total content of the first compound (compound according to the first embodiment) and the light-emitting compound in the light-emitting layer is 100% by mass.

[0369] Note that this embodiment does not exclude the case where the light-emitting layer contains a material other than the first compound (the compound according to the first embodiment) and the light-emitting compound. In one aspect of the organic EL element according to this embodiment, the light-emitting layer may contain only one type of the first compound (the compound according to the first embodiment), or may contain two or more types. In one aspect of the organic EL element according to this embodiment, the light-emitting layer may contain only one type of the light-emitting compound, or may contain two or more types.

[0370] Each of the components that can be included in the organic EL element according to this embodiment will be described.

[0371] (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.

[0372] (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).

[0373] 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.

[0374] 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.

[0375] 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.

[0376] (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.

[0377] 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.

[0378] 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.

[0379] (Hole Transport Region) In one aspect of the organic EL element according to this embodiment, the hole transport region is disposed between the anode and the light emitting region. In one aspect of the organic EL element according to this embodiment, the hole transport region includes, in order from the anode side, a hole injection layer and a hole transport layer. In one aspect of the organic EL element according to this embodiment, the hole transport region includes, in order from the light emitting region side, a hole injection layer, a hole transport layer, and an electron blocking layer.

[0380] (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.

[0381] 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).

[0382] 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.

[0383] (Hole Transport Layer) The organic EL device according to this embodiment preferably has a hole transport layer between the anode and the light-emitting region. The hole transport layer is a layer containing a substance with high hole transport properties. For the hole transport layer, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. 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.

[0384] 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.

[0385] 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.

[0386] (Specific Examples of Hole Transporting Region Materials) Specific examples of materials (hole transporting region materials) used in each layer of the hole transporting region include the following compounds. However, the present invention is not limited to these specific examples of the hole transporting region materials.

[0387]

[0388] (Electron Transporting Zone) In one aspect of the organic EL element according to this embodiment, the electron transporting zone is disposed between the light-emitting zone and the cathode. In one aspect of the organic EL element according to this embodiment, the electron transporting zone includes, in order from the light-emitting zone side, an electron transporting layer and an electron injection layer. In one aspect of the organic EL element according to this embodiment, the electron transporting zone includes, in order from the light-emitting zone side, a hole blocking layer, an electron transporting layer, and an electron injection layer.

[0389] (Electron Transport Layer) The organic EL device according to this embodiment preferably has an electron transport layer between the cathode and the light-emitting region. The electron transport layer is a layer containing a substance with high electron transport properties. For the electron transport layer, 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds can be used. Specifically, low-molecular organic compounds such as Alq and tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq) can be used. ３ ), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq ２ ), BAlq, Znq, ZnPBO, ZnBTZ, and other metal complexes can be used. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: OXD-8), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-9 ... Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) can also be used. In this embodiment, benzimidazole compounds can also 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.

[0390] 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).

[0391] (Specific Examples of Electron Transporting Materials) Specific examples of electron transporting materials that can be used in the electron transporting layer include the following compounds, however, the present invention is not limited to these specific examples of electron transporting materials.

[0392]

[0393]

[0394] (Electron Injection Layer) The electron injection layer is a layer containing a substance with high electron injection properties. Examples of the electron injection layer include lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), and calcium fluoride (CaF ２ For 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.

[0395] 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.

[0396] (Layer Formation Method) The method for forming each layer of the organic EL element of this embodiment is not limited to those specifically mentioned above, but may be any known method such as a dry film formation method such as a vacuum deposition method, a sputtering method, a plasma method, or an ion plating method, or a wet film formation method such as a spin coating method, a dipping method, a flow coating method, or an inkjet method.

[0397] (Film Thickness) The film thickness of each organic layer in the organic EL element of this embodiment is not limited unless specifically mentioned above. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and if the film thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the film thickness of each organic layer in the organic EL element is usually preferably in the range of several nm to 1 μm.

[0398] The organic electroluminescent device according to this embodiment contains the compound according to the first embodiment (first compound), and therefore the device performance is improved. According to one aspect of the organic electroluminescent device according to this embodiment, the life span is extended.

[0399] [Fourth Embodiment] <Organic Electroluminescence Element> The organic EL element according to the fourth embodiment differs from the organic EL element according to the third embodiment in that the light-emitting region includes at least two light-emitting layers. The organic EL element according to the fourth embodiment is similar to the organic EL element according to the third embodiment in all respects except for the light-emitting region. In the description of the fourth embodiment, components that are the same as those in the third embodiment are given the same reference numerals or names, and descriptions thereof are 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 third embodiment can be used.

[0400] Fig. 2 shows a schematic configuration of an example of an organic EL element according to this embodiment. The organic EL element 1B shown in Fig. 2 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, in order from the anode 3 side, a hole transport region 6, a first light-emitting region 5B, and an electron transport region 7. The hole transport region 6 includes, in order from the anode 3 side, a hole injection layer 61 and a hole transport layer 62. The first light-emitting region 5B includes, in order from the anode 3 side, a first light-emitting layer 51 and a second light-emitting layer 52. The electron transport region 7 includes, in order from the light-emitting region 5A side, an electron transport layer 71 and an electron injection layer 72.

[0401] (Light-emitting region) In the organic EL element according to this embodiment, the organic layer has a light-emitting region, and the light-emitting region includes a first light-emitting layer and a second light-emitting layer, and the first light-emitting layer contains a first compound. In the organic EL element according to this embodiment, it is preferable that the second light-emitting layer contains a second compound.

[0402] (Emission Wavelength of Organic EL Element) The organic EL element according to this embodiment preferably emits light having a maximum peak wavelength of 500 nm or less when driven, and more preferably emits light of 430 nm or more and 480 nm or less. The organic EL element according to this embodiment more preferably emits light having a maximum peak wavelength of 470 nm or less when driven, and even more preferably emits light of 465 nm or less. The organic EL element according to this embodiment more preferably emits light having a maximum peak wavelength of 440 nm or more when driven, and even more preferably emits light of 445 nm or more.

[0403] (First Light-Emitting Layer and Second Light-Emitting Layer) In the organic EL element according to this embodiment, it is also preferable that the second light-emitting layer is disposed between the anode and the cathode, and the first light-emitting layer is disposed between the anode and the second light-emitting layer. That is, 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.

[0404] In the organic EL element according to this embodiment, it is also preferable that a first light-emitting layer is disposed between the anode and the cathode, and a second light-emitting layer is disposed between the anode and the first light-emitting layer. That is, the organic EL element according to this embodiment may have an anode, a second light-emitting layer, a first light-emitting layer, and a cathode in this order.

[0405] (First Compound) In the organic EL device according to this embodiment, the first compound is preferably the compound according to the first embodiment.

[0406] (Second Compound) In the organic EL element according to this embodiment, the second compound is not particularly limited, and examples thereof include a second compound represented by the following general formula (2): In one aspect of the organic EL element according to this embodiment, the second compound is a compound represented by the following general formula (2):

[0407]

[0408] (In the general formula (2), R ２０１ ~R ２０８are 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 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and L ２０１ and L ２０２ each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, ２０１ and Ar ２０２ are each independently 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.

[0409] (In the second compound, 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.)

[0410] In one aspect of the organic EL element according to this embodiment, the second compound is a compound having at least one group represented by the following general formula (HY1) in the molecule.

[0411]

[0412] (In the general formula (HY1), R Ｙ１ ~R Ｙ８ and R Ｙ１１ ~R Ｙ１４are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, 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 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, ny is 0 or 1, provided that when ny is 0, R Ｙ１ ~R Ｙ８ is a single bond bonded to *ey, and when ny is 1, R Ｙ１ and R Ｙ２ , R Ｙ２ and R Ｙ３ or R Ｙ３ and R Ｙ４ is a single bond that binds to *cy, and R Ｙ１ and R Ｙ２ , R Ｙ２ and R Ｙ３ or R Ｙ３ and R Ｙ４ The other is a single bond bonding to *dy, and R Ｙ５ ~R Ｙ８ , R Ｙ１１ ~R Ｙ１４ and *cy and *dy are bonded to R that is not a single bond. Ｙ１ ~R Ｙ４ is a single bond bonded to *ey, ２ is an oxygen atom or a sulfur atom, and *fy indicates the bonding position to an atom in the second compound.

[0413] In one aspect of the organic EL element according to this embodiment, when ny in general formula (HY1) is 0, the group represented by general formula (HY1) is represented by the following general formula (HY10): In one aspect of the organic EL element according to this embodiment, the second compound is a compound having at least one group represented by the following general formula (HY10) in the molecule.

[0414]

[0415] (In the general formula (HY10), R Ｙ１ ~R Ｙ８ , and Z ２ are R in the general formula (HY1), respectively. Ｙ１ ~R Ｙ８ , and Z ２ However, R Ｙ１ ~R Ｙ８ is a single bond bonded to *ey, and *fy indicates the bonding position to an atom in the second compound.

[0416] In one aspect of the organic EL element according to this embodiment, the second compound is a compound having at least one group represented by the general formula (HY1) in the molecule, and ny is 1.

[0417] In one aspect of the organic EL element according to this embodiment, the second compound is a compound having, in the molecule thereof, at least one group selected from the group consisting of groups represented by the following general formulae (HY11), (HY12), and (HY13):

[0418]

[0419]

[0420]

[0421] (In the general formulae (HY11), (HY12) and (HY13), R Ｙ１ ~R Ｙ８ , R Ｙ１１ ~R Ｙ１４ , and Z ２ are R in the general formula (HY1), respectively. Ｙ１ ~R Ｙ８ , R Ｙ１１ ~RＹ１４ , and Z ２ However, R Ｙ１ ~R Ｙ８ and R Ｙ１１ ~R Ｙ１４ One of these is a single bond that binds to *ey, and *fy indicates the bonding position to an atom in the second compound.

[0422] In one aspect of the organic EL element according to this embodiment, the second compound is a compound represented by the general formula (2), and the compound represented by the general formula (2) has at least one group represented by the general formula (HY1) in the molecule thereof.

[0423] In one aspect of the organic EL element according to this embodiment, Ar in the general formula (2) ２０１ and Ar ２０２ At least one of the above is a group represented by general formula (HY1).

[0424] In one aspect of the organic EL element according to this embodiment, Ar in the general formula (2) ２０１ or Ar ２０２ is a group represented by the general formula (HY1).

[0425] In one aspect of the organic EL element according to this embodiment, the second compound is a compound represented by the general formula (2), and the compound represented by the general formula (2) has in its molecule at least one group selected from the group consisting of the groups represented by the general formulas (HY11), (HY12), and (HY13).

[0426] In one aspect of the organic EL element according to this embodiment, Ar in the general formula (2) ２０１ and Ar ２０２ At least one of the above is a group selected from the group consisting of groups represented by the general formulae (HY11), (HY12) and (HY13).

[0427] In one aspect of the organic EL element according to this embodiment, Ar in the general formula (2) ２０１ or Ar ２０２ is any group selected from the group consisting of groups represented by the general formulae (HY11), (HY12) and (HY13).

[0428] In one aspect of the organic EL element according to this embodiment, the second compound has, in the molecule thereof, at least one group selected from the group consisting of groups represented by general formula (HY1), general formula (HY10), general formula (HY11), (HY12), and (HY13), thereby improving the excitation resistance of the second compound. By using such a second compound in the second emitting layer, the lifetime of the organic EL element is likely to be extended.

[0429] In one aspect of the organic EL element according to this embodiment, all of the groups described as "substituted or unsubstituted" in the second compound are "unsubstituted" groups.

[0430] (Method for Producing Second Compound) The second compound according to this embodiment can be produced by a known method, or can be produced by following the method and using known alternative reactions and raw materials suited to the target compound.

[0431] (Specific Examples of the Second Compound) Specific examples of the second compound according to this embodiment include the following compounds. However, the present invention is not limited to these specific examples. In this specification, a deuterium atom is represented as D in a chemical formula, and a protium atom is represented as H or is not represented at all.

[0432]

[0433]

[0434]

[0435]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441]

[0442]

[0443]

[0444]

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463]

[0464]

[0465]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474]

[0475]

[0476]

[0477]

[0478]

[0479]

[0480]

[0481]

[0482]

[0483]

[0484]

[0485]

[0486]

[0487]

[0488]

[0489]

[0490]

[0491]

[0492]

[0493]

[0494]

[0495] In the specific examples of the compounds below, D represents a deuterium atom, z, z1, z4, z5, and z6 each represent the number of deuterium atoms bonded to the ring, z is an integer of 1 or more and 8 or less, z1 is an integer of 1 or more and 9 or less, z4 and z5 are each an integer of 1 or more and 5 or less, and z6 is an integer of 1 or more and 7 or less.

[0496]

[0497]

[0498]

[0499]

[0500]

[0501]

[0502]

[0503]

[0504] (First Light-Emitting Compound and Second Light-Emitting Compound) In the organic EL element according to this embodiment, it is also preferable that the first light-emitting layer contains a first light-emitting compound. The first light-emitting compound is preferably a fluorescent compound. In the organic EL element according to this embodiment, it is also preferable that the second light-emitting layer contains a second light-emitting compound. The second light-emitting compound is preferably a fluorescent compound. When the first light-emitting layer contains a first light-emitting compound and the second light-emitting layer contains a second light-emitting compound, the first light-emitting compound and the second light-emitting compound are the same as or different from each other. In the organic EL element according to this embodiment, it is preferable that the first light-emitting compound and the second light-emitting compound are each independently the light-emitting compound described in the third embodiment. In the organic EL element according to this embodiment, it is preferable that the first light-emitting compound and the second light-emitting compound are each independently a compound that exhibits light emission having a maximum peak wavelength of 500 nm or less.

[0505] In the organic EL device according to this embodiment, the first light-emitting compound is preferably a compound that exhibits light emission (preferably fluorescent emission) with a maximum peak wavelength of 500 nm or less. The maximum peak wavelength of the light emission (preferably fluorescent emission) exhibited by the first light-emitting compound is preferably 480 nm or less, more preferably 460 nm or less, and even more preferably 455 nm or less. The maximum peak wavelength of the light emission (preferably fluorescent emission) exhibited by the first light-emitting compound is preferably 430 nm or more, more preferably 440 nm or more, and even more preferably 445 nm or more.

[0506] In the organic EL device according to this embodiment, the second light-emitting compound is preferably a compound that exhibits light emission (preferably fluorescent emission) with a maximum peak wavelength of 500 nm or less. The maximum peak wavelength of the light emission (preferably fluorescent emission) exhibited by the second light-emitting compound is preferably 480 nm or less, more preferably 460 nm or less, and even more preferably 455 nm or less. The maximum peak wavelength of the light emission (preferably fluorescent emission) exhibited by the second light-emitting compound is preferably 430 nm or more, more preferably 440 nm or more, and even more preferably 445 nm or more.

[0507] In the organic EL element according to this embodiment, when the first emitting layer contains a first compound and a first light-emitting compound, the first compound is preferably a first host material, and the first light-emitting compound is preferably a first dopant material.

[0508] In the organic EL element according to this embodiment, when the second emitting layer contains a second compound and a second emitting compound, the second compound is preferably a second host material, and the second emitting compound is preferably a second dopant material.

[0509] In the organic EL device according to this embodiment, the triplet energy T １ (H1) and the triplet energy T of the second compound １ (H2) preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 1): T １ (H1)>T １ (H2) ... (Equation 1)

[0510] In the organic EL element according to this embodiment, the first compound in the first emitting layer and the second compound in the second emitting layer satisfy the relationship of the mathematical formula (Mathematical Formula 1), thereby improving the luminous efficiency of the organic EL element. Conventionally, triplet-triplet-annihilation (sometimes referred to as TTA) has been known as a technique for improving the luminous efficiency of organic EL elements. TTA is a mechanism in which triplet excitons collide with each other to generate singlet excitons. The TTA mechanism is also sometimes referred to as the TTF mechanism, as described in International Publication No. WO 2010 / 134350.

[0511] 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 １A+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%.

[0512] According to the organic EL device of this embodiment, triplet excitons generated by 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 that is in direct 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 EL 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 compound in the first emitting layer is １ (H1) and the triplet energy T of the second compound in the second emitting layer １By providing the first emitting layer and the second emitting layer such that (H2) satisfies the relationship of mathematical formula (Mathematical Formula 1), triplet excitons generated in the first emitting layer 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. As such, the organic EL device according to this embodiment includes, as distinct regions, 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, and the second compound in the second emitting layer is used as a compound having a lower triplet energy than the first compound in the first emitting layer, thereby providing a difference in triplet energy, and thereby improving luminous efficiency.

[0513] In the organic EL device according to this embodiment, the triplet energy T １ (H1) and the triplet energy T of the second compound １ (H2) preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 1A): T １ (H1)-T １ (H2)>0.03 eV... (Equation 1A)

[0514] In the organic EL device 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 (D1) and (D2) satisfy the relationship of the following mathematical formula (Mathematical Formula 2): １ (H1)>S １ (D1) ... (Equation 2)

[0515] When the first compound and the first light-emitting compound in the first light-emitting layer satisfy the relationship of the mathematical formula (Mathematical Formula 2), singlet excitons generated on the molecules of the first compound can easily transfer energy from the first compound to the first light-emitting compound, contributing to the fluorescent emission of the first light-emitting compound.

[0516] In the organic EL device according to this embodiment, the triplet energy T １(H1) and the triplet energy T １ It is preferable that (D1) satisfies the relationship of the following mathematical formula (Mathematical Formula 2A): T １ (D1)>T １ (H1) ...(Math 2A)

[0517] When the first compound and the first light-emitting compound in the first light-emitting layer satisfy the relationship of the mathematical formula (Mathematical Formula 2A), triplet excitons generated in the first light-emitting layer move on the molecules of the first compound rather than on the molecules of the first light-emitting compound having a higher triplet energy, and therefore are more likely to move to the second light-emitting layer.

[0518] 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 3): １ (H2)>S １ (D2) ... (Equation 3)

[0519] In the organic EL element according to this embodiment, the second compound and the second light-emitting compound in the second light-emitting layer satisfy the relationship of the mathematical formula (Mathematical Formula 3), and therefore the singlet energy of the second light-emitting compound is smaller than the singlet energy of the second compound. Therefore, the singlet excitons generated by the TTF phenomenon transfer energy from the second compound to the second light-emitting compound, and contribute to the fluorescent emission of the second light-emitting compound.

[0520] In the organic EL device according to this embodiment, the triplet energy T １ (D2) and the triplet energy T of the second compound １ (H2) preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 3A): T １ (D2)>T １ (H2) ...(Math 3A)

[0521] In the organic EL device according to this embodiment, the second compound and the second light-emitting compound in the second light-emitting layer satisfy the relationship of mathematical formula (Mathematical Formula 3A), so that triplet excitons generated in the first light-emitting layer transfer energy to molecules of the second compound, 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 molecules of the second compound 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 compound. Triplet excitons of the second compound do not transfer to the second light-emitting compound, but instead efficiently collide with each other on molecules of the second compound due to the TTF phenomenon, generating singlet excitons.

[0522] (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

[0523] 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.

[0524] (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 on the long wavelength side of this absorption spectrum, and the wavelength value λedge [nm] at the intersection of this tangent line and the horizontal axis is substituted into the following conversion formula (F2) to obtain the singlet energy S １ Calculate the conversion formula (F2): S １ [eV]=1239.85 / λedge. The absorption spectrum measuring device may be, for example, a spectrophotometer manufactured by Hitachi (device name: U3310), but is not limited to this.

[0525] 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.

[0526] The first and second light-emitting layers preferably do not contain a phosphorescent material (dopant material). Furthermore, the first and second light-emitting layers preferably do not contain a heavy metal complex or a phosphorescent rare earth metal complex. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes. Furthermore, the first and second light-emitting layers preferably do not contain a metal complex.

[0527] (Thickness of the Light-Emitting Layer) The thicknesses of the first light-emitting layer and the second light-emitting layer in the organic EL element according to this embodiment are each independently preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less. When the thickness of the light-emitting layer is 5 nm or more, it is easy to form the light-emitting layer and adjust the chromaticity. When the thickness of the light-emitting layer is 50 nm or less, it is easy to suppress an increase in driving voltage.

[0528] (Compound Content in Light-Emitting Layer) When the first light-emitting layer contains a first compound and a first light-emitting compound, the contents of the first compound and the first light-emitting compound in the first light-emitting layer are preferably, for example, in the following ranges. The content of the first compound is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less. The content of the first light-emitting compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less. However, the upper limit of the total content of the first compound and the first light-emitting compound in the first light-emitting layer is 100% by mass.

[0529] Note that this embodiment does not exclude the case where the first light-emitting layer contains a material other than the first compound and the first light-emitting compound. The first light-emitting layer may contain only one type of first compound, or may contain two or more types of first light-emitting compounds. The first light-emitting layer may contain only one type of first light-emitting compound, or may contain two or more types of first light-emitting compounds.

[0530] When the second light-emitting layer contains a second compound and a second light-emitting compound, the contents of the second compound and the second light-emitting compound in the second light-emitting layer are preferably, for example, in the following ranges. The content of the second compound is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less. The content of the second light-emitting compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less. However, the upper limit of the total content of the second compound and the second light-emitting compound in the second light-emitting layer is 100% by mass.

[0531] Note that this embodiment does not exclude the case where the second light-emitting layer contains a material other than the second compound and the second light-emitting compound. The second light-emitting layer may contain only one type of second compound, or may contain two or more types of second compounds. The second light-emitting layer may contain only one type of second light-emitting compound, or may contain two or more types of second light-emitting compounds.

[0532] In the organic EL element according to this embodiment, it is also preferable that the first light-emitting layer and the second light-emitting layer are in direct contact with each other.

[0533] In the organic EL element according to this embodiment, when "the first emitting layer and the second emitting layer are in direct contact with each other," the layer structure "where the first emitting layer and the second emitting layer are in direct contact with each other" may include, for example, any of the following modes (LS1), (LS2), and (LS3): (LS1) A mode in which a region where both the first compound as a host material (hereinafter sometimes referred to as the "first host material") and the second compound as a host material (hereinafter sometimes referred to as 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, 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 process of vapor-depositing 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) An embodiment in which, when the first emitting layer and the second emitting layer contain a light-emitting compound, a region consisting of the light-emitting compound, a region consisting of the first host material, or a region consisting of the second host material is generated during the process of vapor-depositing the compound for the first emitting layer and the process of vapor-depositing 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.

[0534] 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 second light-emitting layer and the third light-emitting layer are in direct contact with each other.

[0535] In the organic EL element according to this embodiment, when "the second emitting layer and the third emitting layer are in direct contact," the layer structure "in which the second emitting layer and the third emitting layer are in direct contact" may include, for example, any of the following aspects (LS4), (LS5), and (LS6). (LS4) An aspect in which a region in which both the second host material and the third host material (the host material contained in the third emitting layer) are mixed is generated during the process of vapor-depositing the compound for the second emitting layer and the compound for the third emitting layer, and this region is present at the interface between the second emitting layer and the third emitting layer. (LS5) An aspect in which, when the second emitting layer and the third emitting layer contain a light-emitting compound, a region in which the second 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 second emitting layer and the compound for the third emitting layer, and this region is present at the interface between the second emitting layer and the third emitting layer. (LS6) When the second 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 second host material, or a region composed of the third host material is generated during the process of vapor-depositing the compound for the second emitting layer and the compound for the third emitting layer, and the region is present at the interface between the second emitting layer and the third emitting layer.

[0536] The organic EL element according to this embodiment may further include an intervening layer as an organic layer. When the organic EL element according to this embodiment includes an intervening layer, the intervening layer is preferably disposed between the first light-emitting layer and the second light-emitting layer.

[0537] (Intervening Layer) The intervening layer is preferably a non-doped layer. The intervening layer preferably does not contain metal atoms. The intervening layer contains 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.

[0538] The intervening layer material may be one or both of the first compound contained in the first light-emitting layer and the second compound contained in the second light-emitting layer.

[0539] When the intermediate layer contains multiple intermediate layer materials, the content of each intermediate layer material is preferably 10% by mass or more of the total mass of the intermediate layer. The intermediate layer preferably contains 60% by mass or more of the intermediate layer material, more preferably 70% by mass or more of the total mass of the intermediate layer, even more preferably 80% by mass or more of the intermediate layer material, even more preferably 90% by mass or more of the total mass of the intermediate layer, and even more preferably 95% by mass or more of the total mass of the intermediate layer. The intermediate layer may contain only one type of intermediate layer material, or two or more types. When the intermediate layer contains two or more types of intermediate layer materials, the upper limit of the total content of the two or more intermediate layer materials is 100% by mass. Note that this embodiment does not exclude the intermediate layer containing materials other than the intermediate layer material.

[0540] The intervening layer may be composed of a single layer or may be composed of two or more layers laminated together.

[0541] 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.

[0542] (Hole Transport Layer) In the organic EL device according to this embodiment, when the light-emitting region includes a first light-emitting layer and a second light-emitting layer, and the stacking order of the first light-emitting layer and the second light-emitting layer is, from the anode side, the first light-emitting layer and the second light-emitting layer, it is preferable to have a hole transport layer between the anode and the first light-emitting layer. Furthermore, when the stacking order of the first light-emitting layer and the second light-emitting layer is, from the anode side, the second light-emitting layer and the first light-emitting layer, it is preferable to have a hole transport layer between the anode and the second light-emitting layer.

[0543] (Electron Transport Layer) In the organic EL device according to this embodiment, when the light-emitting region includes a first light-emitting layer and a second light-emitting layer, and the stacking order of the first light-emitting layer and the second light-emitting layer is, from the anode side, the first light-emitting layer and the second light-emitting layer, it is preferable to have an electron transport layer between the cathode and the second light-emitting layer. Furthermore, when the stacking order of the first light-emitting layer and the second light-emitting layer is, from the anode side, the second light-emitting layer and the first light-emitting layer, it is preferable to have an electron transport layer between the cathode and the first light-emitting layer.

[0544] In the organic electroluminescent element according to this embodiment, the light-emitting region includes a first light-emitting layer and a second light-emitting layer, and the first light-emitting layer contains the compound according to the first embodiment (first compound). Therefore, the organic electroluminescent element according to this embodiment has improved device performance. According to one aspect of the organic electroluminescent element according to this embodiment, the life span is extended.

[0545] Fifth Embodiment (Electronic Device) An electronic device according to this embodiment is equipped with an organic electroluminescence element according to the above-described embodiment. 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), televisions, mobile phones, tablets, and personal computers. Examples of the light-emitting device include lighting and vehicle lighting fixtures. The light-emitting device can be used in a display device, and can also be used, for example, as a backlight for a display device.

[0546] [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.

[0547] For example, the number of light-emitting layers in the organic EL element is not limited to one or two, and three or more light-emitting layers may be stacked. When the organic EL element has two or more light-emitting layers, it is sufficient that at least two of the light-emitting layers (the first light-emitting layer and the second light-emitting layer) satisfy the conditions described in the above embodiment. For example, the other light-emitting layer may be a fluorescent light-emitting layer or a phosphorescent light-emitting layer that utilizes light emission by electron transition from a triplet excited state directly to the ground state.

[0548] Furthermore, when the organic EL element has a plurality of light-emitting layers, these light-emitting layers may be provided adjacent to each other, or the organic EL element may be a so-called tandem type organic EL element in which a plurality of light-emitting units are stacked via an intermediate layer.

[0549] 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.

[0550] 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.

[0551] 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.

[0552] <Compounds> The structures of the compounds represented by general formula (1) used in the production of the organic EL devices according to Examples 1-1 to 1-10 and Examples 2-1 to 2-10 are shown below.

[0553]

[0554]

[0555]

[0556]

[0557] The structures of the comparative compounds used in the production of the organic EL devices according to Comparative Example 1-1 and Comparative Example 2-1 are shown below.

[0558]

[0559] The structures of other compounds used in the production of the organic EL devices according to Examples 1-1 to 1-10, Examples 2-1 to 2-10, Comparative Example 1-1, and Comparative Example 2-1 are shown below.

[0560]

[0561]

[0562] <Preparation of Organic EL Device (1)> An organic EL device was prepared as follows.

[0563] Example 1-1 A 25 mm x 75 mm x 1.1 mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO (indium tin oxide) transparent electrode (anode) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was 130 nm. The cleaned glass substrate with transparent electrode lines was attached to a substrate holder in a vacuum deposition apparatus, and compound HA-1 was first vapor-deposited on the surface on which the transparent electrode lines were formed, covering the transparent electrode, to form a hole injection layer with a film thickness of 5 nm. Compound HT-1 was vapor-deposited on the hole injection layer to form a hole transport layer with a film thickness of 80 nm. Compound EBL-1 was then vapor-deposited on the hole transport layer to form an electron blocking layer with a film thickness of 10 nm. On the electron blocking layer, compound BH1-1 (first compound) and compound BD-1 (first light-emitting compound) were co-deposited to form an emitting layer with a thickness of 25 nm. The proportion of compound BH1-1 in this emitting layer was 98 mass %, and the proportion of compound BD-1 was 2 mass %. On the emitting layer, compound HBL-1 was deposited by vapor deposition to form a first electron transport layer with a thickness of 10 nm. The first electron transport layer may also be referred to as a hole blocking layer. On the first electron transport layer, compound ET-1 was deposited by vapor deposition to form a second electron transport layer with a thickness of 15 nm. On the second electron transport layer, LiF was deposited by vapor deposition to form an electron injection layer with a thickness of 1 nm. On the electron injection layer, metal Al was deposited by vapor deposition to form a cathode with a thickness of 80 nm. In this manner, the organic EL device of Example 1-1 was fabricated. The device configuration of the organic EL device of Example 1-1 is schematically shown as follows. ITO(130) / HA-1(5) / HT-1(80) / EBL-1(10) / BH1-1:BD-1(25,98%:2%) / HBL-1(10) / ET-1(15) / LiF(1) / Al(80) The numbers in parentheses indicate film thickness (unit: nm). With respect to the element configuration of the organic EL element according to Example 1-1, the numbers expressed in percentage (98%:2%) in parentheses indicate the proportions (mass %) of the first compound (compound BH1-1) and the first light-emitting compound (compound BD-1) in the emitting layer. The same notation is used hereinafter.

[0564] [Examples 1-2 to 1-10] The organic EL devices of Examples 1-2 to 1-10 were fabricated in the same manner as the organic EL device of Example 1-1, except that the first compound (compound BH1-1) used in forming the light-emitting layer was changed to the first compound shown in Table 1.

[0565] [Comparative Example 1-1] The organic EL element of Comparative Example 1-1 was produced in the same manner as the organic EL element of Example 1-1, except that the first compound (compound BH1-1) used in forming the light-emitting layer was changed to the comparative compound shown in Table 1.

[0566] <Evaluation of Organic EL Devices (1)> The following evaluations were carried out on the prepared organic EL devices. The evaluation results are shown in Table 1. For the sake of convenience, the comparative compound used in preparing the organic EL device of Comparative Example 1-1 is also listed in the column for the first compound. In addition, the singlet energy S １ and triplet energy T １ are also shown in Table 1.

[0567] (Lifespan LT95) The fabricated organic EL element was subjected to a current density of 50 mA / cm ２ A voltage was applied so that the voltage was such that the voltage was 0.01 V, and the time (LT95 (unit: hour)) until the luminance reached 95% of the initial luminance was measured as the lifespan. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). Table 1 shows the relative LT95 values. The relative LT95 values ​​were calculated based on the measured LT95 values ​​of each example of Examples 1-1 to 1-10 and Comparative Example 1-1, and the following mathematical formula (Math 1X): LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 1-1) × 100 (Math 1X)

[0568] (Maximum peak wavelength λ ＥＬ ) Current density is 10mA / cm ２ The spectral radiance spectrum when a voltage was applied to the organic EL element was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). From the obtained spectral radiance spectrum, the maximum peak wavelength λ ＥＬ (unit: nm) was determined.

[0569]

[0570] In the organic EL elements of Examples 1-1 to 1-10 and Comparative Example 1-1, the light-emitting region includes one light-emitting layer. The organic EL elements of Examples 1-1 to 1-10 include the compound represented by general formula (1) as the host material of the light-emitting layer, and have a longer life than the organic EL element of Comparative Example 1-1.

[0571] <Preparation of Organic EL Device (2)> An organic EL device was prepared as follows.

[0572] Example 2-1 A 25 mm x 75 mm x 1.1 mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO (indium tin oxide) transparent electrode (anode) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was 130 nm. The cleaned glass substrate with transparent electrode lines was attached to a substrate holder in a vacuum deposition apparatus, and compound HA-1 was first vapor-deposited on the surface on which the transparent electrode lines were formed, covering the transparent electrode, to form a 5 nm thick hole injection layer. Compound HT-1 was vapor-deposited on the hole injection layer to form an 80 nm thick hole transport layer. Compound EBL-1 was then vapor-deposited on the hole transport layer to form a 10 nm thick electron blocking layer. On the electron blocking layer, compound BH1-1 (first compound) and compound BD-1 (first luminescent compound) were co-deposited to form a first luminescent layer with a thickness of 5 nm. The proportion of compound BH1-1 in this first luminescent layer was 98% by mass, and the proportion of compound BD-1 was 2% by mass. On the first luminescent layer, compound BH2 (second compound) and compound BD-1 (second luminescent compound) were co-deposited to form a second luminescent layer with a thickness of 20 nm. The proportion of compound BH2 in this second luminescent layer was 98% by mass, and the proportion of compound BD-1 was 2% by mass. On the second luminescent layer, compound HBL-1 was deposited by vapor deposition to form a first electron transport layer with a thickness of 10 nm. The first electron transport layer may be referred to as a hole blocking layer. On the first electron transport layer, compound ET-1 was deposited by vapor deposition 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 80 nm. In this manner, an organic EL device according to Example 2-1 was fabricated. The device configuration of the organic EL device according to Example 2-1 is summarized as follows: ITO(130) / HA-1(5) / HT-1(80) / EBL-1(10) / BH1-1:BD-1(5,98%:2%) / BH2:BD-1(20,98%:2%) / HBL-1(10) / ET-1(15) / LiF(1) / Al(80). The numbers in parentheses indicate the film thickness (unit: nm).Regarding the element configuration of the organic EL element according to Example 2-1, the figures expressed as percentages in parentheses (98%:2%) also indicate the proportions (mass %) of the first compound (compound BH1-1) or the second compound (BH2), and the light-emitting compound (compound BD-1) in the first light-emitting layer or the second light-emitting layer.

[0573] [Examples 2-2 to 2-10] The organic EL devices of Examples 2-2 to 2-10 were fabricated in the same manner as the organic EL device of Example 2-1, except that the first compound (compound BH1-1) used in forming the light-emitting layer was changed to the first compound shown in Table 2.

[0574] [Comparative Example 2-1] The organic EL element of Comparative Example 2-1 was produced in the same manner as the organic EL element of Example 2-1, except that the first compound (compound BH1-1) used in forming the first emitting layer was changed to the comparative compound shown in Table 2.

[0575] <Evaluation of Organic EL Devices (2)> The following evaluations were carried out on the prepared organic EL devices. The evaluation results are shown in Table 2. For the sake of convenience, the comparative compound used in preparing the organic EL device of Comparative Example 2-1 is also listed in the column for the first compound. In addition, the singlet energies S １ and triplet energy T １ are also shown in Table 2.

[0576] (Lifetime LT95) LT95 was measured in the same manner as in the above-mentioned <Evaluation of Organic EL Elements (1)>. Table 2 shows the relative values ​​of LT95. The relative values ​​of LT95 were calculated based on the measured values ​​of LT95 for each example of Examples 2-1 to 2-10 and Comparative Example 2-1, and the following mathematical formula (Math 2X). LT95 (relative value) = (LT95 for each example / LT95 for Comparative Example 2-1) × 100 (Math 2X)

[0577] (Maximum peak wavelength λ ＥＬ ) As in the above-mentioned <Evaluation of Organic EL Device (1)>, the maximum peak wavelength λ ＥＬ was measured.

[0578]

[0579] In the organic EL elements of Examples 2-1 to 2-10 and Comparative Example 2-1, the light-emitting region includes two light-emitting layers. The organic EL elements of Examples 2-1 to 2-10 include the compound represented by general formula (1) as the first host material of the first light-emitting layer, and have a longer lifetime than the organic EL element of Comparative Example 2-1.

[0580] <Evaluation of Compounds> The compounds used in the production of the organic EL devices were evaluated by the following methods.

[0581] (triplet energy T １ The compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol / L, and this solution was placed in a quartz cell to prepare a measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this measurement sample was measured at low temperature (77 [K]), and a tangent was drawn to the rising edge of the short wavelength side of this phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent 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 The triplet energy T １ Depending on the measurement conditions, an error of about 0.02 eV may occur. １ [eV]=1239.85 / λ ｅｄｇｅ

[0582] 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 was measured using an F-4500 spectrofluorometer manufactured by Hitachi High-Technologies Corporation.

[0583] (singlet energy S １ A 10 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell. The absorption spectrum of this sample (vertical axis: absorption intensity, horizontal axis: wavelength) was measured at room temperature (300 K). A tangent was 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 and the horizontal axis was determined. ｅｄｇｅ The singlet energy was calculated by substituting [nm] into the following conversion formula (F2): Conversion formula (F2): S １ [eV]=1239.85 / λ ｅｄｇｅ The absorption spectrum measuring device used was a spectrophotometer manufactured by Hitachi (device name: U3310).

[0584] 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.

[0585] (Maximum peak wavelength of compound) Maximum peak wavelength λ of compound ＳＯＬ was measured by the following method. A 5 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample was measured at room temperature (300 K). In this example, the emission spectrum was measured using a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength at which the emission intensity is maximum is referred to as the maximum peak wavelength λ ＳＯＬ The maximum peak wavelength λ of compound BD-1 ＳＯＬ was 452 nm.

[0586] Synthesis Examples The synthesis methods of the compounds BH1-1 to BH1-10 used in the production of organic EL devices are shown below.

[0587] (Synthesis Example 1) Synthesis of BH1-1

[0588]

[0589] 1-bromonaphthalen-2-ol (intermediate M1) (25.1 g), pyren-1-ylboronic acid (intermediate M2) (27.7 g), and PdCl ２ (Amphos) ２(2.39 g) was placed in a flask and purged with argon gas. DME (564 mL) and 2 M aqueous sodium carbonate solution (169 mL) were then added and the mixture was heated and stirred under reflux conditions for 3 hours. After heating and stirring, the solvent was distilled off, water was added, and the precipitated solid was collected by filtration. The resulting crude product was purified by silica gel chromatography to obtain 1-(pyren-1-yl)naphthalen-2-ol (intermediate M3) as a white solid (31.4 g, yield 81%). Mass spectrometry analysis of the white solid showed an m / e of 345 for a molecular weight of 344.41, identifying the white solid as the target intermediate M3.

[0590]

[0591] 1-(pyren-1-yl)naphthalen-2-ol (intermediate M3) (25.4 g) was placed in a flask and the atmosphere was replaced with argon gas. ２ Cl ２ (369 mL) was added, and pyridine (23.8 mL) was added while stirring at 0°C. ２ 0 (14.9 mL) was added dropwise. After completion of the addition, the reaction solution was returned to room temperature and stirred for 3 hours. After stirring, water was added to terminate the reaction, and the solvent was distilled off to obtain a crude product, which was purified by silica gel chromatography to obtain 1-(pyren-1-yl)naphthalen-2-yl trifluoromethanesulfonate (intermediate M4) as a white solid (26.1 g, yield 74%). Mass spectrometry analysis of the white solid showed that m / e = 477 for a molecular weight of 476.46, and the white solid was identified as the target intermediate M4.

[0592]

[0593] 1-(pyren-1-yl)naphthalen-2-yl trifluoromethanesulfonate (intermediate M4) (10.7 g), 2-(2'-chloro-[1,1'-biphen yl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (intermediate M5) (6.45 g), Pd ２(dba) ３ (0.37 g) and SPhos (0.67 g) were placed in a flask, and the atmosphere was replaced with argon gas. Then, 1,4-dioxane (205 mL) and 2 M aqueous potassium phosphate solution (41 mL) were added, and the mixture was heated and stirred under reflux conditions for 7 hours. After heating and stirring, the solvent was distilled off, and the resulting crude product was purified by silica gel chromatography and washed with DME to obtain 1-(2-(2'-chloro-[1,1'-biphenyl]-2-yl)naphthalen-1-yl)pyrene (Intermediate M6) as a white solid (6.81 g, yield 65%). Mass spectrometry analysis of the white solid revealed an m / e of 516 for a molecular weight of 515.05, and the white solid was identified as the target intermediate M6.

[0594]

[0595] 1-(2-(2'-chloro-[1,1'-biphenyl]-2-yl)naphthalen-1-yl)pyrene (Intermediate M6) (6.81 g), Pd(OAc) ２ (0.59g), PCy ３ (1.48 g) and cesium carbonate (8.62 g) were placed in a flask, and after purging with argon gas, xylene (132 mL) was added and the mixture was heated and stirred under reflux conditions for 7 hours. After completion of the reaction, toluene was added to the resulting precipitate, which was heated to dissolve, and the mixture was passed through silica gel. The crude product obtained by distilling off the solvent was washed with DME and recrystallized with toluene to obtain compound BH1-1 as a white solid (5.34 g, yield 84%). Mass spectrometry analysis of the white solid showed an m / e of 479 for a molecular weight of 478.59, and the white solid was identified as the target compound BH1-1.

[0596] (Synthesis Example 2) Synthesis of BH1-2 Compound BH1-2 was obtained as a white solid by the method described in Synthesis Example 1, except that 6-phenyl-pyren-1-ylboronic acid (intermediate M7) was used instead of pyren-1-ylboronic acid (intermediate M2) used in Synthesis Example 1. Mass spectrometry analysis of the white solid showed that m / e = 555 for a molecular weight of 554.69, and the white solid was identified as the target compound BH1-2.

[0597]

[0598] (Synthesis Example 3) Synthesis of BH1-3 In Synthesis Example 3, compound BH1-3 was obtained as a white solid by the same method as in Synthesis Example 1, except that B-benzo[b]naphtho[2,1-d]furan-7-yl-boronic acid (intermediate M8) was used instead of pyren-1-ylboronic acid (intermediate M2) used in Synthesis Example 1. Mass spectrometry analysis of the white solid showed that m / e = 495 for a molecular weight of 494.59, and the white solid was identified as the target compound BH1-3.

[0599]

[0600] (Synthesis Example 4) Synthesis of BH1-4

[0601]

[0602] In Synthesis Example 4, first, intermediate M11 was synthesized using 1,4-dibromonaphthalen-2-ol (intermediate M9) and intermediate M10 as shown in the above reaction scheme.

[0603] Thereafter, compound BH1-4 was obtained as a white solid by the method described in Synthesis Example 1, except that intermediate M11 was used instead of 1-bromonaphthalen-2-ol (intermediate M1) used in Synthesis Example 1. Mass spectrometry analysis of the white solid showed that m / e = 555 for a molecular weight of 554.69, and the white solid was identified as the target compound BH1-4.

[0604] In the explanation of the synthesis examples, DME is an abbreviation for 1,2-dimethoxyethane, and Tf ２ O is the abbreviation for trifluoromethanesulfonic anhydride, and PdCl ２ (Amphos) ２ is the abbreviation for bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium(II), and Pd ２ (dba) ３ is the abbreviation for tris(dibenzylideneacetone)dipalladium(0), SPhos is the abbreviation for 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, and Pd(OAc) ２ is the abbreviation for palladium(II) acetate, and PCy ３ is the abbreviation for tricyclohexylphosphine.

[0605] (Synthesis Example 5) Synthesis of BH1-5 Compound BH1-5 was obtained as a white solid by the method described in Synthesis Example 1, except that (11,11-dimethyl-11H-benzo[b]fluoren-2-yl)boronic acid (intermediate M12) was used instead of pyren-1-ylboronic acid (intermediate M2) used in Synthesis Example 1. Mass spectrometry analysis of the white solid showed that m / e = 521 for a molecular weight of 520.68, and the white solid was identified as the target compound BH1-5.

[0606]

[0607] (Synthesis Example 6) Synthesis of BH1-6 Compound BH1-6 was obtained as a white solid by the method described in Synthesis Example 1, except that (7,7-dimethyl-7H-benzo[c]fluoren-9-yl)boronic acid (intermediate M13) was used instead of pyren-1-ylboronic acid (intermediate M2) used in Synthesis Example 1. Mass spectrometry analysis of the white solid showed that m / e = 521 for a molecular weight of 520.68, and the white solid was identified as the target compound BH1-6.

[0608]

[0609] (Synthesis Example 7) Synthesis of BH1-7 Compound BH1-7 was obtained as a white solid by the method described in Synthesis Example 1, except that 7-[2-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzo[b]naphtho[2,1-d]furan (Intermediate M14) was used instead of pyren-1-ylboronic acid (Intermediate M2) used in Synthesis Example 1. Mass spectrometry analysis of the white solid showed an m / e of 571 for a molecular weight of 570.69, and the white solid was identified as the target compound BH1-7.

[0610]

[0611] (Synthesis Example 8) Synthesis of BH1-8 Compound BH1-8 was obtained as a white solid by the method described in Synthesis Example 1, except that (benzo[b]triphenylen-9-yl)boronic acid (intermediate M15) was used instead of pyren-1-ylboronic acid (intermediate M2) used in Synthesis Example 1. Mass spectrometry analysis of the white solid showed that m / e = 555 for a molecular weight of 554.69, and the white solid was identified as the target compound BH1-8.

[0612]

[0613] (Synthesis Example 9) Synthesis of BH1-9 Instead of pyren-1-ylboronic acid (intermediate M2) used in Synthesis Example 1, (1-pyrenyl-2,3,4,5,6,7,8,9,10-d ９ Compound BH1-9 was obtained as a white solid by the method described in Synthesis Example 1, except that boronic acid (Intermediate M16) was used. Mass spectrometry analysis of the white solid revealed that m / e was 488 for a molecular weight of 487.65, and the white solid was identified as the target compound BH1-9.

[0614]

[0615] (Synthesis Example 10) Synthesis of BH1-10

[0616]

[0617] Compound BH1-3 (5.00 g) and aluminum chloride (0.40 g) were placed in a flask, and the flask was purged with argon gas. ６ (100 mL) was added and the mixture was stirred at 10°C for 24 hours. Heavy water (100 mL) was added to the reaction mixture after stirring and the mixture was returned to room temperature. The organic layer was then concentrated, and the resulting residue was purified by silica gel chromatography. Further, recrystallization using toluene was repeated to obtain compound BH1-10 as a white solid (2.10 g, yield 40%). Mass spectrometry analysis of the white solid showed that m / e = 517 for a molecular weight of 516.73, and the white solid was identified as the target compound BH1-10.

[0618] Reference Signs List 1A, 1B... organic EL element, 2... substrate, 3... anode, 4... cathode, 5A... light-emitting region, 5B... first light-emitting region, 5... light-emitting layer, 51... first light-emitting layer, 52... second light-emitting layer, 6... hole-transporting region, 61... hole-injecting layer, 62... hole-transporting layer, 7... electron-transporting region, 71... electron-transporting layer, 72... electron-injecting layer.

Claims

1. A compound represented by the following general formula (1): (In the general formula (1), R １ ~R １４ 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 condensed ring, or are not bonded to each other, １ ~R １４ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ), a group represented by —O—(R ９０４ ) group, -S-(R ９０５ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ A group represented by the formula: ８０２ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 19 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the general formula (12) above, R １ ~R １４ At least one of R is a group represented by the general formula (12), １ ~R １４ When any of R is a heterocyclic group, the ring of the heterocyclic group does not contain a nitrogen atom or a sulfur atom, ９ and R １４ Unless both are hydrogen atoms, R ９ and R １４ are different from each other, R ２ , R ４ , R ５ , R ７ , R １１ and R １２ When one or two of the above are a group represented by the general formula (12), R １ , R ３ , R ６ , R ８ , R ９ , R １０ , R １３ and R １４ At least one of L is not a hydrogen atom, １ is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, L １ When L is a heterocyclic group, the ring of the heterocyclic group does not contain a nitrogen atom or a sulfur atom, n is 0, 1, 2 or 3, and when n is 0, -(L １ ) ０ - is a single bond, and when n is 2 or 3, two or three L １ are the same or different, Ar １ is a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted dibenz[a,c]anthracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, a substituted or unsubstituted indenofluorenyl group, a substituted or unsubstituted fluoranthenyl group, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, Ar １ When Ar is a heterocyclic group, the ring of the heterocyclic group does not contain a nitrogen atom or a sulfur atom, １ is not a benzoxanthenyl group, Ar １ When Ar is a heterocyclic group having a substituent, the substituent is not a substituted or unsubstituted anthracenyl group, １ is a group having a substituent, the substituent does not include a group represented by the following general formula (PO1); when there are a plurality of groups represented by the general formula (12), the plurality of groups represented by the general formula (12) are the same or different from each other; in the compound represented by the general formula (1), when the substituent in the case of "substituted or unsubstituted" is a heterocyclic group, the ring of the heterocyclic group does not include a nitrogen atom or a sulfur atom; in the compound represented by the general formula (1), when the substituent in the case of "substituted or unsubstituted" is an aryl group, the number of ring carbon atoms of the aryl group is 6 to 19; * indicates the bonding position with the dibenz[a,c]anthracene ring represented by the general formula (1). (In the general formula (PO1), Rp １ and Rp ２ are each independently 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 * indicates a bonding position. ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ８０１ , and R ８０２ 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 ８０１ When there are multiple R ８０１ are the same or different from each other, R ８０２ When there are multiple R ８０２ are the same or different from each other.) 2. R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. １ ~R １４ 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 19 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by general formula (12).

3. R ​​does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. １ ~R １４ are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 19 ring carbon atoms, or a group represented by general formula (12).

4. R １ , R ３ , R ６ , R ８ , R ９ , R １０ , R １３ and R １４ The compound according to claim 1 , wherein at least one of the following is a group represented by general formula (12):

5. The compound according to any one of claims 1 to 4, wherein the compound represented by the general formula (1) is represented by the following general formula (10): (In the general formula (10), R １ , R ３ , R ６ , R ８ , R ９ , R １０ , R １３ and R １４ are R in the general formula (1), １ , R ３ , R ６ , R ８ , R ９ , R １０ , R １３ and R １４ (Same meaning as above.) 6. The compound according to any one of claims 1 to 5, wherein the compound represented by the general formula (1) is represented by the following general formula (11): (In the general formula (11), R １４ is R in the general formula (1). １４ and n, L １ and Ar １ respectively represent n and L in the general formula (12). １ and Ar １ (Same meaning as above.) 7. R １４ is a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 19 ring carbon atoms.

8. R １ and R ８ The compound according to any one of claims 1 to 5, wherein at least one of the following is a group represented by general formula (12):

9. The compound according to any one of claims 1 to 8, wherein n in the compound represented by the general formula (1) is 0 or 1.

10. L in the compound represented by the general formula (1) １ is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.

11. L in the compound represented by the general formula (1) １ The compound according to any one of claims 1 to 10, wherein: is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.

12. Ar in the compound represented by the general formula (1) １ is a substituted or unsubstituted furanyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzo[b]naphtho[2,1-d]furanyl group, a substituted or unsubstituted benzo[b]naphtho[2,3-d]furanyl group, a substituted or unsubstituted benzo[b]naphtho[1,2-d]furanyl group, a substituted or unsubstituted dinaphthofuranyl group, a substituted or unsubstituted benzobisbenzofuranyl group, a substituted or unsubstituted benzo[b]phenanthrofuranyl group, or a substituted or unsubstituted xanthenyl group.

13. Ar in the compound represented by the general formula (1) １ is any one of groups represented by the following general formulas (101) to (112): The compound according to any one of claims 1 to 11. (R in the above general formulae (101) to (112) １０１ ~R １０９ , R １１１ ~R １６５ and R １６６ ~R １８７ 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 19 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and * indicates the bonding position.

14. Ar in the compound represented by the general formula (1) １ is a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted dibenz[a,c]anthracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, a substituted or unsubstituted indenofluorenyl group, or a substituted or unsubstituted fluoranthenyl group. The compound according to any one of claims 1 to 11, 15. R １ ~R １４ The compound according to any one of claims 1 to 14, wherein any pair of adjacent groups of:

16. The compound according to any one of claims 1 to 15, wherein the compound represented by the general formula (1) does not have an anthracene structure in the molecule.

17. The compound according to any one of claims 1 to 16, wherein the compound represented by the general formula (1) does not have a benzoxanthene structure in the molecule.

18. R ９ and R １４ is not a phenanthryl group.

19. The compound according to any one of claims 1 to 18, wherein the compound represented by the general formula (1) does not contain a phosphorus atom in the molecule.

20. The compound according to any one of claims 1 to 19, wherein the compound represented by formula (1) contains at least one deuterium atom.

21. The compound according to any one of claims 1 to 20, 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 12 ring atoms.

22. A compound according to any one of claims 1 to 20, wherein any group described as "substituted or unsubstituted" is an "unsubstituted" group.

23. An organic electroluminescence device comprising a compound according to any one of claims 1 to 22 as a first compound.

24. The organic electroluminescence device according to claim 23, comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, at least one of the organic layers containing the first compound.

25. The organic electroluminescence device according to claim 24, wherein the organic layer has a light-emitting region, the light-emitting region includes at least one light-emitting layer, and the at least one light-emitting layer contains the first compound.

26. The organic electroluminescence device according to claim 25, wherein the light-emitting region includes a first light-emitting layer and a second light-emitting layer, the first light-emitting layer contains the first compound, and the second light-emitting layer contains a second compound.

27. The triplet energy T of the first compound １ (H1) and the triplet energy T of the second compound １ The organic electroluminescence element according to claim 26, wherein (H1) and (H2) satisfy the relationship of the following formula (Formula 1). １ (H1)>T １ (H2) ... (Equation 1) 28. The organic electroluminescence device according to claim 26 or 27, wherein the first light-emitting layer and the second light-emitting layer are in direct contact with each other.

29. The organic electroluminescence device according to any one of claims 26 to 28, wherein the first light-emitting layer is disposed between the anode and the second light-emitting layer.

30. An organic electroluminescent element described in any one of claims 26 to 29, wherein the first light-emitting layer contains a first light-emitting compound, the second light-emitting layer contains a second light-emitting compound, and the first light-emitting compound and the second light-emitting compound are each independently a compound that exhibits light emission having a maximum peak wavelength of 500 nm or less.

31. The organic electroluminescence device according to any one of claims 25 to 30, further comprising a hole transport layer between the anode and the light emitting region.

32. The organic electroluminescence device according to any one of claims 25 to 31, further comprising an electron transport layer between the cathode and the light-emitting region.

33. An electronic device equipped with the organic electroluminescence element according to any one of claims 23 to 32.

Images