Compound, organic electroluminescent element, and electronic device

Abstract

Compounds represented by formula (1).

Description

Compound, organic electroluminescent element, and electronic device

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

[0002] When a voltage is applied to an organic electroluminescence element (hereinafter also referred to as an organic EL element), holes are injected from the anode and electrons are injected from the cathode into the light-emitting layer, where they recombine to form excitons.

[0003] Conventional organic EL elements have not yet achieved sufficient element performance. Although improvements to organic EL elements have been made gradually to enhance element performance, further improvements in performance are still required. Patent Document 1 discloses a compound having a specific structure for use in an organic EL element.

[0004] Korean Patent Publication No. 2011-103819

[0005] An object of the present invention is to provide an organic EL device with higher performance.

[0006] As a result of extensive research to achieve the above object, the present inventors have discovered that a high-performance organic EL element can be obtained by using a compound having a specific structure in at least one of the organic layers of the organic EL element, and have completed the present invention.

[0007] According to the present invention, the following compounds are provided: 1. A compound represented by formula (1): [In formula (1), R ７ and R １２ One of the two is (L １ ) ｎ１ represents a single bond with R ７ and R １２ The other of (L ２ ) ｎ２ represents a single bond with １ ~R ６ , R ８ ~R １１ , and R ２２ ~R ２５ are each independently a hydrogen atom or a substituent R. ２１is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. １ is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 18 ring atoms, or a substituted or unsubstituted monovalent sulfur-containing heterocyclic group having 5 to 18 ring atoms. １ and L ２ are each independently a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 14 ring atoms. n1 is an integer of 0 to 3. n2 is an integer of 0 to 3. When n1 is 0, (L １ ) ｎ１ When n1 is 2 or more, two or more L １ are connected in series with each other. When n1 is 2 or more, two or more L １ may be the same or different. When n2 is 0, (L ２ ) ｎ２ When n2 is 2 or more, two or more L ２ are connected in series with each other. When n2 is 2 or more, two or more L ２ may be the same or different. The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ), -O-(R ９０４ ), -S-(R ９０５ ), -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 monovalent heterocyclic group having 5 to 50 ring atoms. ９０１ ~R ９０７are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. ９０１ ~R ９０７ When there are two or more R ９０１ ~R ９０７ may be the same or different. When two or more substituents R are present, the two or more substituents R may be the same or different. 2. An organic electroluminescence element comprising: a cathode; an anode; and one or more organic layers disposed between the cathode and the anode, wherein at least one of the organic layers contains the compound described in 1 above. 3. An electronic device comprising the organic electroluminescence element described in 2 above.

[0008] According to the present invention, an organic EL device with higher performance can be provided.

[0009] 1 is a diagram showing a schematic configuration of an organic EL element according to one embodiment of the present invention.

[0010] [Definitions] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0011] 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.

[0012] 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.

[0013] 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.

[0014] 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.

[0015] 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.

[0016] 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.

[0017] "Substituents Described in This Specification" The substituents described in this specification are explained below.

[0018] 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.

[0019] "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.

[0020] 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).

[0021]

[0022]

[0023] 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.

[0024] "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.

[0025] 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).

[0026] 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).

[0027] 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.

[0028] 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.

[0029] 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).

[0030] 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):

[0031]

[0032]

[0033] 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:

[0034] 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.

[0035] 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].

[0036] 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].

[0037] 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):

[0038] 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).

[0039] "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.

[0040] 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.

[0041] 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.

[0042] "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.

[0043] 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.

[0044] 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.

[0045] - "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.

[0046] Unsubstituted alkynyl groups (specific example group G5A): ethynyl group

[0047] "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.

[0048] 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.

[0049] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.

[0050] -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.

[0051] ・「-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.

[0052] ・"-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.

[0053] ・「-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.

[0054] "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.

[0055] "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.

[0056] "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.

[0057] - "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.

[0058] - "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.

[0059] - "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.

[0060] - "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.

[0061] - "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.

[0062] "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.

[0063] 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.

[0064] 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.

[0065] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.

[0066]

[0067] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically any of the following groups:

[0068]

[0069] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a binding site.

[0070] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0071]

[0072] In the general formulae (TEMP-34) to (TEMP-41), * represents a binding site.

[0073] 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.

[0074] "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.

[0075] "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.

[0076] "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.

[0077] 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).

[0078]

[0079]

[0080] 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 binding site.

[0081]

[0082] 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 a bonding site.

[0083]

[0084] 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 binding site.

[0085] 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).

[0086]

[0087]

[0088]

[0089] In the general formulae (TEMP-69) to (TEMP-82), Q １ ~Q ９ are each independently a hydrogen atom or a substituent.

[0090]

[0091]

[0092]

[0093]

[0094] In the general formulae (TEMP-83) to (TEMP-102), Q １ ~Q ８ are each independently a hydrogen atom or a substituent.

[0095] The above is the explanation of "substituents described in this specification."

[0096] "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.

[0097]

[0098] For example, R ９２１~R ９３０ In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," the pair of adjacent two groups is R ９２１ and R ９２２ With the pair, R ９２２ and R ９２３ With the pair, R ９２３ and R ９２４ With the pair, R ９２４ and R ９３０ With the pair, R ９３０ and R ９２５ With the pair, R ９２５ and R ９２６ With the pair, R ９２６ and R ９２７ With the pair, R ９２７ and R ９２８ With the pair, R ９２８ and R ９２９ and R ９２９ and R ９２１ It is paired with.

[0099] 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).

[0100]

[0101] 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.

[0102]

[0103] 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.

[0104] "Unsaturated rings" include aromatic hydrocarbon rings and aromatic heterocycles, as well as aliphatic hydrocarbon rings having an unsaturated bond, i.e., a double bond and / or a triple bond, in the ring structure (e.g., cyclohexene, cyclohexadiene, etc.), and non-aromatic heterocycles having an unsaturated bond (e.g., dihydropyran, imidazoline, pyrazoline, quinolizine, indoline, isoindoline, etc.). "Saturated rings" include aliphatic hydrocarbon rings having no unsaturated bonds, or non-aromatic heterocycles having no unsaturated bonds. Specific examples of aromatic hydrocarbon rings include structures in which the groups listed as specific examples in Specific Example Group G1 are terminated with a hydrogen atom. Specific examples of aromatic heterocycles include structures in which the aromatic heterocyclic groups listed as specific examples in Specific Example Group G2 are terminated with a hydrogen atom. Specific examples of aliphatic hydrocarbon rings include structures in which the groups listed as specific examples in Specific Example Group G6 are terminated with a hydrogen atom. "Forming a ring" means forming a ring with only multiple atoms of the parent skeleton, or with multiple atoms of the parent skeleton and one or more optional atoms. 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 atoms. 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

[0105] Here, unless otherwise specified herein, the "any atom" is preferably at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. In any atom (for example, in the case of a carbon atom or a nitrogen atom), a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "any substituent" described below. When any atom other than a carbon atom is included, the formed ring is a heterocycle. Unless otherwise specified herein, the "one or more any atoms" 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 atom selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0106] 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").

[0107] 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.

[0108] 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.

[0109] 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.

[0110] 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."

[0111] 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.

[0112] 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.

[0113] [Novel Compound] A compound according to one aspect of the present invention is a compound represented by the following formula (1). [In formula (1), R ７ and R １２ One of the two is (L １ ) ｎ１ represents a single bond with R ７ and R １２ The other of (L ２ ) ｎ２ represents a single bond with １ ~R ６ , R ８ ~R １１ , and R ２２ ~R ２５ are each independently a hydrogen atom or a substituent R. ２１ is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. １ is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 18 ring atoms, or a substituted or unsubstituted monovalent sulfur-containing heterocyclic group having 5 to 18 ring atoms. １ and L ２are each independently a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 14 ring atoms. n1 is an integer of 0 to 3. n2 is an integer of 0 to 3. When n1 is 0, (L １ ) ｎ１ When n1 is 2 or more, two or more L １ are connected in series with each other. When n1 is 2 or more, two or more L １ may be the same or different. When n2 is 0, (L ２ ) ｎ２ When n2 is 2 or more, two or more L ２ are connected in series with each other. When n2 is 2 or more, two or more L ２ may be the same or different. The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ), -O-(R ９０４ ), -S-(R ９０５ ), -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 monovalent 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 monovalent heterocyclic group having 5 to 50 ring atoms. ９０１ ~R ９０７ When there are two or more R ９０１ ~R ９０７may be the same or different. When two or more substituents R are present, the two or more substituents R may be the same or different.

[0114] In formula (1), when n1 is 0, (L １ ) ｎ１ is a single bond, and the carbon atom of the benzanthracene ring and Ar １ and are directly bonded.

[0115] In formula (1), when n2 is 0, (L ２ ) ｎ２ is a single bond, which directly bonds the benzanthracene ring to the nitrogen atom of the benzimidazole ring.

[0116] In formula (1), when n1 is 2 or more, 2 or more L １ are connected in series with each other. It is obvious from the definition, for example, when n1 is 2, two L １ is a benzoanthracene ring and Ar １ and "(benzoanthracene ring)-L" is connected in series between １ -L １ -Ar １ In other words, the benzanthracene ring is formed by two L １ and Ar １ is two L １ When n1 is 3, three L １ is a benzoanthracene ring and Ar １ and "(benzoanthracene ring)-L" is connected in series between １ -L １ -L １ -Ar １ " structure is formed.

[0117] In formula (1), when n2 is 2 or more, 2 or more L ２ are connected in series with each other. １ " to "L ２ " to "Ar １" is replaced with "a nitrogen atom of a benzimidazole ring", and the same explanation as in "when n1 is 2 or more" can be applied.

[0118] In formula (1), R ７ and R １２ One of the two is (L １ ) ｎ１ represents a single bond with R ７ and R １２ The other of (L ２ ) ｎ２ In one embodiment, R ７ (L １ ) ｎ１ represents a single bond with R １２ (L ２ ) ｎ２ In one embodiment, R １２ (L １ ) ｎ１ represents a single bond with R ７ (L ２ ) ｎ２ represents a single bond with

[0119] In formula (1), R １ ~R ６ , R ８ ~R １１ , and R ２２ ~R ２５ At least one pair of adjacent two or more of the above are not bonded to each other and do not form a substituted or unsubstituted monocyclic or condensed ring.

[0120] In one embodiment, R １ ~R ６ and R ８ ~R １１ is a hydrogen atom.

[0121] In one embodiment, R ２１ is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. ２１ is an unsubstituted alkyl group having 1 to 6 carbon atoms. ２１ is a methyl group, an ethyl group, a propyl group, or an isopropyl group.

[0122] In one embodiment, R２２ ~R ２５ is a hydrogen atom.

[0123] In one embodiment, Ar １ represents a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0124] In one embodiment, Ar １ is a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted dibenzofuranyl group.

[0125] In one embodiment, Ar １ is a hydrogen atom, an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, or an unsubstituted dibenzofuranyl group.

[0126] In one embodiment, L １ is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenediyl group, or a substituted or unsubstituted pyridinediyl group.

[0127] In one embodiment, L ２ is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenediyl group, or a substituted or unsubstituted pyridinediyl group.

[0128] In one embodiment, n1 is 0. In one embodiment, n2 is 1 or 2. In one embodiment, n1 is 0 and n2 is 1 or 2.

[0129] In one embodiment, the compound represented by formula (1) is a compound represented by any one of formulas (11) to (14) below. [In formulas (11) to (14), R １ ~R ６ , R ８ ~R １１, R ２１ ~R ２５ , n1, n2, L １ , and L ２ is as defined in the formula (1). In the formulas (11) and (12), H is a hydrogen atom. In the formulas (13) and (14), Ar １１ is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 18 ring atoms, or a substituted or unsubstituted monovalent sulfur-containing heterocyclic group having 5 to 18 ring atoms.]

[0130] In one embodiment, the compound represented by formula (1) is a compound represented by any one of formulas (111) to (114) below. [In formulas (111) to (114), R ２１ , n1, n2, L １ , and L ２ is as defined in the formula (1). １１ is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 18 ring atoms, or a substituted or unsubstituted monovalent sulfur-containing heterocyclic group having 5 to 18 ring atoms.]

[0131] In one embodiment, Ar １１ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0132] In one embodiment, Ar １１ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted dibenzofuranyl group.

[0133] In one embodiment, Ar １１ is an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, or an unsubstituted dibenzofuranyl group.

[0134] In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (1) is an alkyl group having 1 to 50 carbon atoms, an alkenyl group having 2 to 50 carbon atoms, an alkynyl group having 2 to 50 carbon atoms, a 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 ), an aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９０８ , -COOR ９０９ , -S(=O) ２ R ９４１ a group represented by -P(=O)(R ９４２ ) (R ９４３ ), -Ge(R ９４４ ) (R ９４５ ) (R ９４６ ), a halogen atom, a cyano group, a nitro group, an aryl group having 6 to 50 ring carbon atoms, or a heterocyclic group having 5 to 50 ring atoms. ９０１ ~R ９０９ and R ９４１ ~R ９４６ 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 monovalent heterocyclic group having 5 to 50 ring atoms.

[0135] In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (1) is an alkyl group having 1 to 50 carbon atoms, an alkenyl group having 2 to 50 carbon atoms, an alkynyl group having 2 to 50 carbon atoms, a 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 aryl group having 6 to 50 ring carbon atoms, or a 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 monovalent heterocyclic group having 5 to 50 ring atoms.

[0136] In one embodiment, the substituent in the "substituted or unsubstituted" in formula (1) 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.

[0137] In one embodiment, the substituent in the "substituted or unsubstituted" in formula (1) 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.

[0138] In one embodiment, the compound according to one aspect of the present invention does not have a deuterium atom in the molecule as a hydrogen atom.

[0139] As used herein, the phrase "having no deuterium atoms as hydrogen atoms" means that, among all hydrogen atoms in the molecule, the ratio of deuterium atoms to the total of protons and deuterium atoms is equal to or less than the natural abundance. In other words, a compound according to one embodiment of the present invention that does not have deuterium atoms as hydrogen atoms in the molecule may contain deuterium atoms at a ratio equal to or less than the natural abundance. Whether the ratio of deuterium atoms to the total of protons and deuterium atoms is equal to or less than the natural abundance can be confirmed using a nuclear magnetic resonance spectrometer.

[0140] In one embodiment, the compound according to one aspect of the present invention has at least one deuterium atom in the molecule as a hydrogen atom.

[0141] In one embodiment, R in formula (1) is a hydrogen atom. １ ~R ６, R is a substituent R １ ~R ６ a hydrogen atom possessed by R ８ ~R １１ , R is a substituent R ８ ~R １１ a hydrogen atom possessed by R ２１ a hydrogen atom possessed by R ２２ ~R ２５ , R is a substituent R ２２ ~R ２５ a hydrogen atom contained in Ar １ , Ar １ a hydrogen atom possessed by L １ a hydrogen atom possessed by L ２ At least one of the hydrogen atoms contained in

[0142] In one embodiment, R in formula (1) is a hydrogen atom. １ ~R ６ , R is a substituent R １ ~R ６ a hydrogen atom possessed by R ８ ~R １１ , R is a substituent R ８ ~R １１ a hydrogen atom contained in Ar １ At least one of the groups is a deuterium atom.

[0143] In one embodiment, n1 in formula (1) is 0, and R is a hydrogen atom. １ ~R ６ , R is a substituent R １ ~R ６ a hydrogen atom possessed by R ８ ~R １１ , R is a substituent R ８ ~R １１ a hydrogen atom contained in Ar １ is a deuterium atom.

[0144] In one embodiment, R in formula (1) ２１ At least one of the hydrogen atoms contained in the aryl group is a deuterium atom.

[0145] In one embodiment, R in formula (1) ２１ The hydrogen atom contained in is a deuterium atom.

[0146] As used herein, "having deuterium atoms as hydrogen atoms" or "hydrogen atoms are deuterium atoms" means that, in the hydrogen atoms, the ratio of deuterium atoms to the total of protium atoms and deuterium atoms is higher than the natural abundance. The fact that the ratio of deuterium atoms to the total of protium atoms and deuterium atoms is higher than the natural abundance can be confirmed by a nuclear magnetic resonance spectrometer.

[0147] The compound represented by formula (1) can be synthesized by following the examples and using known alternative reactions and raw materials suited to the target compound.

[0148] Specific examples of the compound represented by formula (1) are listed below, but these are merely illustrative and the compound represented by formula (1) is not limited to the following specific examples.

[0149]

[0150] [Material for Organic Electroluminescence Device] The compound according to one embodiment of the present invention is useful as a material for an organic EL device, for example, as a material used in the electron transport region of an organic EL device.

[0151] [Organic EL element] An organic EL element according to one embodiment of the present invention (hereinafter also referred to as "organic EL element of the present invention") has a cathode, an anode, and one or more organic layers disposed between the cathode and the anode, and at least one of the organic layers contains the compound according to one embodiment of the present invention (compound represented by formula (1)).

[0152] The organic EL element according to one aspect of the present invention has the above-described configuration, and thus can improve its performance.

[0153] The organic EL device according to one aspect of the present invention has one or more organic layers disposed between a cathode and the anode. At least one of the organic layers contains a compound according to one aspect of the present invention (a compound represented by formula (1)). Conventionally known materials and device configurations can be used in the organic EL device according to one aspect of the present invention, as long as the effects of the present invention are not impaired.

[0154] In one embodiment, the organic EL device of the present invention includes an anode, an emitting layer, an electron transporting region, and a cathode, in this order, and at least one of the organic layers in the electron transporting region includes a compound according to one aspect of the present invention (a compound represented by formula (1)).

[0155] In one embodiment, the electron-transporting region has at least a first layer and a second layer in this order from the light-emitting layer side, and the first layer contains the compound according to one aspect of the present invention (the compound represented by Formula (1)).

[0156] In one embodiment, the electron-transporting region has at least a first layer and a second layer in this order from the light-emitting layer side, and the second layer contains the compound according to one aspect of the present invention (the compound represented by Formula (1)).

[0157] In one embodiment, no other layers are included between the first layer and the light-emitting layer.

[0158] The electron-transporting region may further include a third layer, or may not include a third layer. In one embodiment, the electron-transporting region has a first layer, a second layer, and a third layer in this order from the light-emitting layer side.

[0159] In one embodiment, the organic EL device according to one aspect of the present invention has a hole transporting region between the anode and the light-emitting layer.

[0160] The schematic configuration of an organic EL element according to one aspect of the present invention will be described with reference to Fig. 1. In one embodiment, an organic EL element 1 according to one aspect of the present invention includes a substrate 2, an anode 3, an emitting layer 5, a cathode 10, a hole transporting region 4 between the anode 3 and the emitting layer 5, and an electron transporting region 6 between the emitting layer 5 and the cathode 10.

[0161] A typical example of the device configuration of the organic EL device of the present invention is a structure in which the following structures are laminated on a substrate: (1) anode / light-emitting layer / electron-transporting region / cathode (2) anode / hole-transporting region / light-emitting layer / electron-transporting region / cathode (" / " indicates that each layer is laminated adjacent to each other).

[0162] The hole transport region is a general term for one or more layers disposed between the anode and the light-emitting layer. The hole transport region is composed of, for example, layers called an electron blocking layer, a hole transport layer, and a hole injection layer, which will be described later from the light-emitting layer side. The hole transport region may have a laminated structure including all of these layers, or may have a layered structure including only some of these layers. Furthermore, two or more types of layers may be used for each of the above layers. For example, two types of hole transport layers with different compositions may be laminated. Each layer may be formed using only one type of material, or may be formed using two or more types of materials in combination.

[0163] The electron transport region is a general term for one or more layers disposed between the cathode and the light-emitting layer. The electron transport region is composed of, for example, layers called a hole-blocking layer, an exciton-blocking layer, an electron-transporting layer, and an electron-injection layer, which will be described later, from the light-emitting layer side. The electron transport region may have a laminated structure including all of these layers, or may have a layered structure including only some of these layers. Furthermore, two or more types of layers may be used for each of the above layers. For example, two types of electron-transporting layers with different compositions may be laminated. Each layer may be formed using only one type of material, or two or more types of materials in combination.

[0164] Each layer of the organic EL element according to one embodiment of the present invention will be described below. (Substrate) The substrate is used as a support for the light-emitting 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 plastic substrates made of polycarbonate or polyvinyl chloride.

[0165] (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, and graphene. Other examples include gold (Au), platinum (Pt), or nitrides of metal materials (e.g., titanium nitride).

[0166] (Hole Injection Layer) The hole injection layer is a layer containing a substance with high hole injection properties. Examples of the substance with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compounds, and polymer compounds (oligomers, dendrimers, polymers, etc.).

[0167] (Hole Transport Layer) The hole transport layer is a layer containing a substance with high hole transport properties. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, and the like can be used for the hole transport layer. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used. However, other substances may be used as long as they have a higher hole transport property than electron transport property. The layer containing the substance with high hole transport properties may be a single layer or may be a stack of two or more layers made of the above substances.

[0168] (Guest (dopant) material of the light-emitting layer) The light-emitting layer is a layer containing a highly light-emitting substance, and various materials can be used. For example, as the highly light-emitting substance, a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used. A fluorescent compound is a compound that can emit light from a singlet excited state, and a phosphorescent compound is a compound that can emit light from a triplet excited state. Examples of blue fluorescent light-emitting materials that can be used in the light-emitting layer include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, and triarylamine derivatives. Examples of green fluorescent light-emitting materials that can be used in the light-emitting layer include aromatic amine derivatives. Examples of red fluorescent light-emitting materials that can be used in the light-emitting layer include tetracene derivatives and diamine derivatives. Examples of blue phosphorescent light-emitting materials that can be used in the light-emitting layer include metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Examples of green phosphorescent light-emitting materials that can be used in the light-emitting layer include iridium complexes. As the red phosphorescent material that can be used in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used.

[0169] (Host Material of the Light-Emitting Layer) The light-emitting layer may be configured by dispersing the highly light-emitting substance (guest material) described above in another substance (host material). Various substances can be used as the substance for dispersing the highly light-emitting substance, and it is preferable to use a substance having a higher lowest unoccupied molecular orbital (LUMO) level and a lower highest occupied molecular orbital (HOMO) level than the highly light-emitting substance. Examples of substances (host materials) for dispersing the highly light-emitting substance include: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives; 3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and chrysene derivatives; and 4) aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives. A delayed fluorescent (thermally activated delayed fluorescent) compound can also be used as the host material. It is also preferable that the light-emitting layer contains the material used in the present invention described above and a delayed fluorescent host compound.

[0170] (Electron Blocking Layer, Hole Blocking Layer, Exciton Blocking Layer) An electron blocking layer, hole blocking layer, exciton (triplet) blocking layer, or the like may be provided adjacent to the light-emitting layer. The electron blocking layer is a layer that has the function of blocking electrons from leaking from the light-emitting layer to the hole transport layer. The hole blocking layer is a layer that has the function of blocking holes from leaking from the light-emitting layer to the electron transport layer. The exciton blocking layer is a layer that has the function of blocking excitons generated in the light-emitting layer from diffusing to adjacent layers and confining the excitons within the light-emitting layer.

[0171] (Electron Transport Layer) The electron transport layer is a layer containing a substance with high electron transport properties. For the electron transport layer, 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex, 2) a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative, or a phenanthroline derivative, or 3) a polymer compound can be used.

[0172] (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), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ２ ), metal complex compounds such as 8-hydroxyquinolinolato-lithium (Liq), lithium oxide (LiO ｘ ), alkaline metals such as Cr, alkaline earth metals, or compounds thereof can be used.

[0173] (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.

[0174] In the organic EL element according to one embodiment of the present invention, the thickness of each layer is not particularly limited, but in order to generally suppress defects such as pinholes, keep the applied voltage low, and improve the luminous efficiency, it is usually preferable that the thickness be in the range of several nm to 1 μm.

[0175] In the organic EL element according to one embodiment of the present invention, the method for forming each layer is not particularly limited. Conventionally known methods such as vacuum deposition and spin coating can be used. Each layer, such as the light-emitting layer, can be formed by a known method such as vacuum deposition, molecular beam deposition (MBE), or a coating method such as dipping a solution in a solvent, spin coating, casting, bar coating, or roll coating.

[0176] [Electronic Device] An electronic device according to an aspect of the present invention is characterized by comprising the organic EL element according to an aspect of the present invention. Specific examples of the electronic device include display components such as organic EL panel modules, display devices for televisions, mobile phones, and personal computers, and light-emitting devices such as lighting and vehicle lamps.

[0177] <Compounds> The compounds represented by formula (1) used in the production of the organic EL devices of the examples are shown below.

[0178] The comparative compounds used in the production of the organic EL devices of the comparative examples are shown below.

[0179] The structures of other compounds used in the production of the organic EL devices of the Examples and Comparative Examples are shown below.

[0180] Example 1 <Preparation of Organic EL Device> An organic EL device was prepared as follows. A 25 mm × 75 mm × 1.1 mm thick glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was 130 nm. The cleaned glass substrate with the transparent electrode was attached to a substrate holder in a vacuum deposition apparatus. First, compounds HTL-1 and HI-1 were co-deposited on the surface on which the transparent electrode was formed, so that the proportion of compound HI-1 was 15% by mass, to form a first hole transport layer with a thickness of 10 nm, covering the transparent electrode. Compound HTL-1 was vapor-deposited on the first hole transport layer to form a second hole transport layer with a thickness of 80 nm. Compound EBL-1 was vapor-deposited on the second hole transport layer to form a third hole transport layer with a thickness of 10 nm. On the third hole transport layer, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited so that the proportion of compound BD-1 was 2% by mass, thereby forming a light-emitting layer with a thickness of 25 nm. Compound ET-1 was deposited on the light-emitting layer to form an electron transport layer with a thickness of 20 nm. LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 1 nm. Metallic Al was deposited on the electron injection layer to form a cathode with a thickness of 50 nm.

[0181] The device configuration of the organic EL device of Example 1 is shown in outline as follows: ITO(130) / HTL-1:HI-1(10:15%) / HTL-1(80) / EBL-1(10) / BH-1:BD-1(25:2%) / ET-1(20) / LiF(1) / Al(50), where the numbers in parentheses indicate the film thickness (unit: nm). The percentage numbers in parentheses indicate the proportion (mass %) of the latter compound in the corresponding layer.

[0182] <Evaluation of Organic EL Device> The fabricated organic EL device was evaluated as follows. The results are shown in Table 1. Driving voltage The initial characteristics of the organic EL device were measured at room temperature with a DC (direct current) constant current of 10 mA / cm ２ Measured with driving.

[0183] Examples 2 to 8 and Comparative Example 1 Organic EL devices were prepared and evaluated in the same manner as in Example 1, except that in forming the electron transport layer, the compound ET-1 was replaced with a compound shown in Table 1. The results are shown in Table 1.

[0184]

[0185] <Synthesis of Compounds> (Synthesis Example 1) Synthesis of Compound ET-1 Compound ET-1 was synthesized according to the following synthetic route. 12-Bromo-7-phenyltetraphene (5.26 g), 2-ethyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazole (4.54 g), Pd ２ (dba) ３ (0.25 g), SPhos (0.45 g), and cesium carbonate (8.94 g) were placed in a flask, and the flask was purged with argon gas. Then, 1,4-dioxane (59 mL) and H ２ 0 (9.8 mL) was added, and the mixture was heated and stirred under reflux conditions for 4 hours. The solvent was distilled off, and the resulting crude product was purified by silica gel chromatography and washed with toluene to obtain compound ET-1 as a white solid (4.26 g, yield 59%). Mass spectrometry analysis showed that the molecular weight was 524.67 with an m / e of 525, and the compound was identified as the target product.

[0186] (Synthesis Example 2) Synthesis of Compound ET-2 Compound ET-2 was synthesized according to the following synthesis route. 1-(6-bromonaphthalen-2-yl)-2-ethyl-1H-benzo[d]imidazole (6.35 g), (4-chlorophenyl)boronic acid (5.08 g), and (PPh) ３ PdCl ２ (0.51 g) was placed in a flask and purged with argon gas. Toluene (180 mL) and aqueous sodium carbonate solution (2 M, 23 mL) were added, and the mixture was heated and stirred under reflux for 4 hours. The solvent was evaporated, and the resulting crude product was purified by silica gel chromatography to obtain Intermediate A as a white solid (6.09 g, yield 85%). Intermediate A (5.59 g), tetraphen-7-ylboronic acid (4.37 g), Pd ２ (dba) ３ (0.27 g), SPhos (0.48 g), and potassium carbonate (4.03 g) were placed in a flask, and the air was replaced with argon gas. Then, 1,4-dioxane (90 mL) and H ２ 0 (15 mL) was added, and the mixture was heated and stirred under reflux conditions for 12 hours. The solvent was distilled off, and the resulting crude product was purified by silica gel chromatography and washed with toluene to obtain compound ET-2 as a white solid (4.37 g, yield 48%). Mass spectrometry analysis showed a molecular weight of 574.73 with an m / e of 575, and the compound was identified as the target product.

[0187] (Synthesis Example 3) Synthesis of Compound ET-3 Compound ET-3 was synthesized according to the following synthesis route. 7-Bromotetraphene (7.00 g), (6-chloropyridin-3-yl)boronic acid (3.66 g), Pd ２ (dba) ３(0.42 g), and tricyclohexylphosphane (0.31 g) were placed in a flask, and the inside of the flask was replaced with argon gas. Then, 1,4-dioxane (59 mL) and an aqueous potassium phosphate solution (1.3 M, 39 mL) were added, and the mixture was heated and stirred under reflux for 4 hours. The solvent was evaporated, and the resulting crude product was purified by silica gel chromatography and washed with methanol to obtain Intermediate B as a white solid (5.49 g, 74% yield). Intermediate B (5.09 g), 2-ethyl-1-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)-1H-benzo[d]imidazole (6.27 g), Pd ２ (dba) ３ (0.34 g) and XPhos (0.72 g) were placed in a flask, and the atmosphere was replaced with argon gas. Then, 1,4-dioxane (107 mL) and an aqueous solution of sodium carbonate (2 M, 38 mL) were added, and the mixture was heated and stirred under reflux for 7 hours. The solvent was distilled off, and the resulting crude product was purified by silica gel chromatography and washed with toluene to obtain compound ET-3 as a white solid (8.01 g, yield 86%). Mass spectrometry analysis showed a molecular weight of 575.72 with an m / e of 576, identifying the compound as the target product.

[0188] (Synthesis Example 4) Synthesis of Compound ET-4 Compound ET-4 was synthesized according to the following synthesis route. 12-Bromo-7-phenyltetraphene (2.28 g), 2-(ethyl-d5)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazole (2.10 g), Pd ２ (dba) ３ (0.11 g), SPhos (0.20 g), and cesium carbonate (3.89 g) were placed in a flask, and the flask was purged with argon gas. Then, 1,4-dioxane (25 mL) and H ２0 (4.3 mL) was added, and the mixture was heated and stirred under reflux conditions for 5 hours. The solvent was distilled off, and the resulting crude product was purified by silica gel chromatography and washed with toluene to obtain ET-4 as a white solid (1.64 g, yield 52%). Mass spectrometry analysis showed that the molecular weight was 529.70 with an m / e of 530, and the product was identified as the target product.

[0189] (Synthesis Example 5) Synthesis of Compound ET-5 Compound ET-5 was synthesized according to the following synthesis route. Intermediate A (3.31 g), (tetraphen-7-yl-d11)boronic acid (2.69 g), Pd ２ (dba) ３ (0.16 g), SPhos (0.28 g), and potassium carbonate (2.39 g) were placed in a flask, and the air was replaced with argon gas. Then, 1,4-dioxane (50 mL) and H ２ 0 (9 mL) was added, and the mixture was heated and stirred under reflux conditions for 12 hours. The solvent was distilled off, and the resulting crude product was purified by silica gel chromatography and washed with toluene to obtain ET-5 as a white solid (2.13 g, yield 42%). Mass spectrometry analysis showed a molecular weight of 585.79 with an m / e of 586, identifying it as the target product.

[0190] Although several embodiments and / or examples of the present invention have been described in detail above, those skilled in the art will readily be able to make numerous modifications to these exemplary embodiments and / or examples without substantially departing from the novel teachings and advantages of the present invention. Accordingly, these numerous modifications are within the scope of the present invention. The contents of all documents cited in this specification and of the applications from which this application claims priority under the Paris Convention are incorporated by reference in their entirety.

Claims

1. A compound represented by formula (1). [In formula (1), R ７ and R １２ One of the two is (L １ ) ｎ１ represents a single bond with ７ and R １２ The other of (L ２ ) ｎ２ R represents a single bond with １ ~R ６ , R ８ ~R １１ , and R ２２ ~R ２５ are each independently a hydrogen atom or a substituent R. ２１ is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms. １ is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 18 ring atoms, or a substituted or unsubstituted monovalent sulfur-containing heterocyclic group having 5 to 18 ring atoms. １ and L ２ are each independently a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 14 ring atoms. n1 is an integer of 0 to 3. n2 is an integer of 0 to 3. When n1 is 0, (L １ ) ｎ１ is a single bond. When n1 is 2 or more, L is 2 or more. １ are connected in series to each other. When n1 is 2 or more, L is 2 or more. １ may be the same or different. When n2 is 0, (L ２ ) ｎ２ is a single bond. When n2 is 2 or more, L is 2 or more. ２ are connected in series to each other. When n2 is 2 or more, L is 2 or more. ２ may be the same or different. The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ), -O-(R ９０４ ), -S-(R ９０５ ), -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 monovalent 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 monovalent heterocyclic group having 5 to 50 ring atoms. ９０１ ~R ９０７ When there are two or more R ９０１ ~R ９０７ may be the same or different. When two or more substituents R are present, the two or more substituents R may be the same or different.

2. The compound according to claim 1, wherein the compound represented by formula (1) is a compound represented by any one of the following formulas (11) to (14): [In the formulas (11) to (14), R １ ~R ６ , R ８ ~R １１ , R ２１ ~R ２５ , n1, n2, L １ , and L ２ is as defined in formula (1). In formulas (11) and (12), H is a hydrogen atom. In formulas (13) and (14), Ar １１ represents a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 18 ring atoms, or a substituted or unsubstituted monovalent sulfur-containing heterocyclic group having 5 to 18 ring atoms.

3. Ar １ The compound according to claim 1 , wherein is a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted dibenzofuranyl group.

4. The compound according to any one of claims 1 to 3, wherein n1 is 0.

5. L ２ The compound according to any one of claims 1 to 4, wherein is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenediyl group, or a substituted or unsubstituted pyridinediyl group.

6. The compound according to any one of claims 1 to 5, wherein n2 is 1 or 2.

7. R １ ~R ６ and R ８ ~R １１ The compound according to any one of claims 1 to 6, wherein is a hydrogen atom.

8. R ２１ The compound according to any one of claims 1 to 7, wherein is an unsubstituted alkyl group having 1 to 6 carbon atoms.

9. R ２１ The compound according to any one of claims 1 to 8, wherein is a methyl group, an ethyl group, a propyl group, or an isopropyl group.

10. R ２２ ~R ２５ The compound according to any one of claims 1 to 9, wherein is a hydrogen atom.

11. The compound according to any one of claims 1 to 10, wherein the compound represented by formula (1) is a compound represented by any one of the following formulas (111) to (114): [In formulas (111) to (114), R ２１ , n1, n2, L １ , and L ２ is as defined in formula (1). １１ represents a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 18 ring atoms, or a substituted or unsubstituted monovalent sulfur-containing heterocyclic group having 5 to 18 ring atoms.

12. A compound according to any one of claims 1 to 11, having at least one deuterium atom in the molecule as a hydrogen atom.

13. The compound according to any one of claims 1 to 12, which is a material for an organic electroluminescence device.

14. An organic electroluminescence device comprising: a cathode; an anode; and one or more organic layers disposed between the cathode and the anode, wherein at least one of the organic layers contains a compound according to any one of claims 1 to 13.

15. The organic electroluminescence device according to claim 14, comprising an anode, a light-emitting layer, an electron-transporting zone, and a cathode, in that order, and at least one of the organic layers in the electron-transporting zone contains the compound.

16. The organic electroluminescence device according to claim 15, wherein the electron transporting zone has at least a first layer and a second layer in this order from the light emitting layer side, and the first layer contains the compound.

17. The organic electroluminescence device according to claim 15 or 16, wherein the electron transporting zone has at least a first layer and a second layer in this order from the light emitting layer side, and the second layer contains the compound.

18. The organic electroluminescence device according to any one of claims 15 to 17, further comprising a hole transporting region between said anode and said light emitting layer.

19. An electronic device comprising the organic electroluminescence element according to any one of claims 14 to 18.

Images