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

Abstract

Provided are: a compound represented by formula (1) (the symbols in the formula being as defined in the specification); a material, comprising the compound, for an organic electroluminescent element; an organic electroluminescent element comprising the compound; and an electronic device comprising the organic electroluminescent element.

Description

Compound, material for organic electroluminescence device, organic electroluminescence device, and electronic device

[0001] The present invention relates to a compound, a material for an organic electroluminescent device, an organic electroluminescent device, and an electronic device including the organic electroluminescent device.

[0002] Generally, an organic electroluminescent device (hereinafter sometimes referred to as "organic EL device") is composed of an anode, a cathode, and an organic layer sandwiched between the anode and cathode. When a voltage is applied between the two electrodes, electrons are injected from the cathode side and holes are injected from the anode side into the light-emitting region. The injected electrons and holes recombine in the light-emitting region to generate an excited state, and light is emitted when the excited state returns to the ground state. Therefore, the development of a material that efficiently transports electrons or holes to the light-emitting region and facilitates the recombination of electrons and holes is important for obtaining high-performance organic EL devices.

[0003] Patent Documents 1 to 10 disclose compounds used as materials for organic electroluminescence devices.

[0004] International Publication No. WO 2023 / 096225 International Publication No. WO 2022 / 065745 International Publication No. WO 2022 / 108068 European Patent Application Publication No. 4019505 Korean Registered Patent No. 10-2076958 International Publication No. WO 2022 / 260236 International Publication No. WO 2022 / 009999 Korean Registered Patent No. 10-2169568 Chinese Patent No. 111689889 Chinese Published Patent No. 114933577 Chinese Published Patent No. 114853701

[0005] Although many compounds for organic EL devices have been reported, there is still a demand for compounds that further improve the performance of organic EL devices.

[0006] The present invention has been made to solve the above-mentioned problems, and an object of the present invention is to provide a compound and a material for an organic electroluminescence device that further improve the performance of an organic EL device, an organic EL device with further improved device performance, and an electronic device including such an organic EL device.

[0007] The present inventors have conducted extensive research into the performance of organic EL devices containing the compounds described in the above patent documents and other compounds, and as a result have found that a monoamine represented by the following formula (1) provides an organic EL device with improved device performance.

[0008] In one aspect, the present invention provides a compound represented by the following formula (1):

[0009] In formula (1), Ar １ and Ar ２ are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. １ ~L ３ are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms. ７ ~R １０ is a single bond bonded to *a. １ is a single bond, R ８ ~R １０ One selected from is a single bond bonded to *a. １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. １ and R ３ ~R ６ At least one of R is not a hydrogen atom. ２ is a hydrogen atom.

[0010] In another aspect, the present invention provides a material for an organic EL device, which comprises a compound represented by the formula (1).

[0011] In still another aspect, the present invention provides an organic electroluminescence device having an anode, a cathode, and organic layers disposed between the anode and the cathode, the organic layers including an emitting layer, and at least one layer of the organic layers including a compound represented by formula (1).

[0012] In still another aspect, the present invention provides an electronic device including the organic electroluminescence device.

[0013] An organic EL device containing the compound represented by formula (1) exhibits improved device performance.

[0014] 1 is a schematic diagram showing an example of a layer structure of an organic EL element according to one embodiment of the present invention, FIG. 2 is a schematic diagram showing an example of a layer structure of another organic EL element according to one embodiment of the present invention, and FIG. 3 is a schematic diagram showing an example of a layer structure of yet another organic EL element according to one embodiment of the present invention.

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

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

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

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

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

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

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

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

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

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

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

[0026]

[0027]

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

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

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

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

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

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

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

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

[0036]

[0037]

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

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

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

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

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

[0043] The "one or more hydrogen atoms of a monovalent heterocyclic group" means one or more hydrogen atoms selected from a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, a hydrogen atom bonded to a nitrogen atom when at least one of XA and YA is NH, and a hydrogen atom of a methylene group when one of XA and YA is CH.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[0071]

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

[0073]

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

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

[0076]

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

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

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

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

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

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

[0083]

[0084]

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

[0086]

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

[0088]

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

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

[0091]

[0092]

[0093]

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

[0095]

[0096]

[0097]

[0098]

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

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

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

[0102]

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

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

[0105]

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

[0107]

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

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

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

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

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

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

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

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

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

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

[0118] The compound of the present invention is described below. The compound of the present invention is represented by the following formula (1). Hereinafter, the compounds of the present invention represented by formula (1) and each formula described below may be simply referred to as "invention compounds."

[0119]

[0120] The symbols in formula (1) and each formula described below will be explained below. Unless otherwise specified, the same symbols have the same meaning in the following formulas.

[0121] In formula (1), R ７ ~R １０ One selected from is a single bond bonded to *a. １ is a single bond, R ８ ~R １０ One selected from is a single bond bonded to *a. １０ is preferably a single bond bonded to *a. １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. １ and R ３ ~R ６ At least one of R is not a hydrogen atom. ２ is a hydrogen atom.

[0122] R is not a hydrogen atom １ and R ３ ~R ６ is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0123] R ３ ~R ６ It is preferable that at least one of the groups is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0124] R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ The details of the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms represented by are as described above in the section "Substituents described in this specification." The unsubstituted alkyl group is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group, more preferably a methyl group, an ethyl group, an isopropyl group, or a t-butyl group, and even more preferably a methyl group or a t-butyl group. R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０The details of the substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms represented by are as described above in the section "Substituents described in this specification." The unsubstituted cycloalkyl group is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, or a 2-norbornyl group, more preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and even more preferably a cyclopentyl group or a cyclohexyl group.

[0125] R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ The details of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms represented by are as described above in the section "Substituents Described in the Specification." The unsubstituted aryl group having 6 to 30 ring carbon atoms is preferably a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9-methyl-9-phenylfluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, or a 9,9-diphenylfluorenyl group.

[0126] R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ The details of the substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms represented by are as described above in the section "Substituents Described in the Present Description." The unsubstituted heterocyclic group having 5 to 50 ring carbon atoms is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), a dibenzofuranyl group, a naphthobenzofuranyl group, a dibenzothiophenyl group, or a naphthobenzothiophenyl group.

[0127] R１ ~R １０ Adjacent two selected from are not bonded to each other and therefore do not form a ring structure.

[0128] L １ ~L ３ are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.

[0129] L １ is preferably a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, more preferably a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group, and still more preferably a substituted or unsubstituted phenylene group.

[0130] L １ ~L ３ The details of the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms represented by are as described above in the section "Substituents Described in this Specification." The unsubstituted arylene group having 6 to 30 ring carbon atoms is preferably a phenylene group, a biphenylene group, a terphenylene group, or a naphthylene group, and more preferably a phenylene group.

[0131] In one embodiment of the present invention, L ２ and L ３ are preferably each independently a single bond or a group represented by the following formulas (i) to (iii):

[0132] In formulas (i) to (iii), *a is bonded to one selected from carbon atoms *1 to *3, *b is bonded to one selected from carbon atoms *4 to *6, *c is bonded to one selected from carbon atoms *7 to *9, *d is bonded to one selected from carbon atoms *10 to *17, *e is bonded to another selected from carbon atoms *10 to *17, * represents the bonding position to the central nitrogen atom, ** represents Ar １ or Ar ２ represents the binding position to

[0133] In one embodiment of the present invention, *a is preferably bonded to carbon atom *3. In another embodiment of the present invention, *b is preferably bonded to carbon atom *6. In yet another embodiment of the present invention, *c is preferably bonded to carbon atom *7.

[0134] Ar １ and Ar ２ are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0135] Ar １ and Ar ２ are each independently preferably a group represented by any one of the following formulae (1a) to (1e), and more preferably a group represented by any one of the following formulae (1a), (1b), and (1d):

[0136]

[0137] In formula (1a), *21 is L １ or L ２ is the binding site to

[0138] R １０１ ~R １１０ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. １０１ ~R １０５ one selected from is a single bond bonded to *22, and R １０６ ~R １１０ One selected from is a single bond bonded to *23. １０１ ~R １０５ adjacent two selected from are not bonded to each other and therefore do not form a ring, １０６ ~R １１０ Any two adjacent groups selected from the above are not bonded to each other and therefore do not form a ring.

[0139] The R １０１ ~R １１０ The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R １ , R３ ~R ６ , and R that is not a single bond ７ ~R １０ is as described above.

[0140] The R １０１ ~R １１０ The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ As described above.

[0141] * R that is not a single bond bonded to 22 and is not a single bond bonded to 23 １０１ ~R １１０ may all be hydrogen atoms.

[0142] k is 0 or 1, l is 0 or 1, and k+l is an integer of 0 to 2.

[0143] In one embodiment of the present invention, k is 0 and l is 0. In this case, *23 represents *21, and formula (1a) is represented by the following formula.

[0144] In another embodiment of the present invention, k is 1 and l is 0. In this case, *23 represents *22, and formula (1a) is represented by the following formula:

[0145] In another embodiment of the present invention, k is 0 and l is 1. In this case, *22 represents *21, and formula (1a) is represented by the following formula:

[0146] In another embodiment of the present invention, k is 1 and l is 1. In this case, formula (1a) is represented by the following formula:

[0147] In one embodiment of the present invention, k+l is preferably 1.

[0148] R １１１ ~R １１５are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. １１１ ~R １１５ Adjacent two selected from the above may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore may not form a ring.

[0149] The R １１１ ~R １１５ The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ As described above with respect to the R １１１ ~R １１５ The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ As described above with respect to the R １１１ ~R １１５ The details of the unsubstituted heterocyclic group having 5 to 13 ring atoms represented by R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ As described above.

[0150] R １１１ ~R １１５ may all be hydrogen atoms.

[0151] The group represented by formula (1a) is preferably represented by the following formula: In the following formula, R has been omitted for simplicity.

[0152] Formula (1b) is expressed by the following formula.

[0153]

[0154] In formula (1b), *24 is L １ or L ２ is the binding site to

[0155] R １２１ ~R １２８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. １２１ ~R １２８ one selected from is a single bond bonded to *25, and R １２１ ~R １２８ Adjacent two selected from are not bonded to each other and therefore do not form a ring.

[0156] The R １２１ ~R １２８ The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ As described above with respect to the R １２１ ~R １２８ The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ As described above.

[0157] In one embodiment of the present invention, R １２１ is preferably a single bond bonded to *25, and in another embodiment, R １２２ is preferably a single bond bonded to *25. R that is not a single bond bonded to *25 １２１ ~R １２８ may all be hydrogen atoms.

[0158] Formula (1c) is expressed by the following formula.

[0159]

[0160] In formula (1c), *26 is L １ or L ２ is the binding site to

[0161] R １３１ ~R １４０ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. １３１ ~R １４０ is a single bond bonded to *27, and R １３１ ~R １４０ Adjacent two selected from are not bonded to each other and therefore do not form a ring.

[0162] The R １３１ ~R １４０ The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ As described above with respect to the R １３１ ~R １４０ The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ As described above. １３１ , R １３２ and R １４０ Preferably, one selected from is a single bond bonded to *27. １３１ However, in other embodiments, R １３２ However, in still another embodiment, R １４０ is a single bond bonded to *27. R that is not a single bond bonded to *27 １３１ ~R １４０ may all be hydrogen atoms.

[0163] Formula (1d) is expressed by the following formula.

[0164]

[0165] In formula (1d), *28 is L １ or L ２ is the binding site to

[0166] X ２ is an oxygen atom, a sulfur atom, NR Ａ , or CR ａ R ｂ X ２ is preferably an oxygen atom or NR Ａ is.

[0167] R Ａ is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.

[0168] The R Ａ The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ As described above with respect to the R Ａ The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ As described above.

[0169] R ａ and R ｂ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or are bonded to each other to form a substituted or unsubstituted ring structure.

[0170] The R ａ and R ｂ The details of the unsubstituted alkyl group having 1 to 30 carbon atoms represented by R １ , R ３ ~R ６ , and R that is not a single bond７ ~R １０ As described above with respect to the R ａ and R ｂ The details of the unsubstituted aryl group having 6 to 30 ring carbon atoms represented by R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ As described above.

[0171] R １４１ ~R １４８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. １４１ ~R １４８ , R Ａ , R ａ , and R ｂ One selected from is a single bond bonded to *29. １４１ ~R １４８ At least two adjacent ones selected from the following may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore not form a ring.

[0172] The R １４１ ~R １４８ The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ As described above with respect to the R １４１ ~R １４８ The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ As described above with respect to the R １４１ ~R １４８The details of the unsubstituted heterocyclic group having 5 to 13 ring atoms represented by R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ As described above.

[0173] * Not a single bond bonded to 29, R １４１ ~R １４８ , R Ａ , R ａ , and R ｂ may all be hydrogen atoms.

[0174] X ２ is an oxygen atom or a sulfur atom, preferably R １４１ ~R １４４ One selected from is a single bond bonded to *29. X ２ NR Ａ When R １４１ ~R １４４ and R Ａ One selected from is a single bond bonded to *29. Ａ is particularly preferably a single bond bonded to *29, an unsubstituted phenyl group, or a naphthyl group. ２ is CR ａ R ｂ When R １４１ ~R １４４ , R ａ , and R ｂ One selected from is a single bond bonded to *29. ａ and R ｂ are particularly preferably each independently a single bond bonded to *29, an unsubstituted phenyl group, or a naphthyl group.

[0175] Formula (1e) is expressed by the following formula.

[0176]

[0177] In formula (1e), *30 is L １ or L ２ is the binding site to

[0178] R １５１~R １５５ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted phenyl group. １５１ ~R １５５ is a single bond bonded to *31, and R １５１ ~R １５５ Another one selected from is a single bond bonded to *32. R that is not a single bond bonded to *31 and is not a single bond bonded to *32 １５１ ~R １５５ Adjacent two selected from are not bonded to each other and therefore do not form a ring.

[0179] The R １５１ ~R １５５ The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ R that is not a single bond bonded to *31 and is not a single bond bonded to *32 １５１ ~R １５５ may all be hydrogen atoms.

[0180] R １６１ ~R １６５ and R １７１ ~R １７５ are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms. １６１ ~R １６５ At least two adjacent ones selected from may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore not form a ring, １７１ ~R １７５ At least two adjacent ones selected from the following may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore not form a ring.

[0181] The R １６１ ~R １６５ and R １７１ ~R １７５The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R １ , R ３ ~R ６ , and R that is not a single bond ７ ~R １０ As described above. １６１ ~R １６５ and R １７１ ~R １７５ may all be hydrogen atoms.

[0182] Formula (1e) includes groups represented by the following formulae (1e-1) to (1e-5), and formula (1e-1), (1e-2) or (1e-4) is preferred.

[0183]

[0184] As described above, the term "hydrogen atom" used herein encompasses protium, deuterium, and tritium atoms. Therefore, the compound of the invention may contain naturally occurring deuterium atoms. Alternatively, deuterium atoms may be intentionally introduced into the compound of the invention by using partially or entirely deuterated starting compounds. Therefore, in one embodiment of the present invention, the compound of the invention contains at least one deuterium atom. That is, the compound of the invention may be a compound represented by formula (1), in which at least one of the hydrogen atoms contained in the compound is a deuterium atom.

[0185] R １ ~R １０ a hydrogen atom represented by any one of the following: １ , R ３ ~R １０ a hydrogen atom of a substituted or unsubstituted alkyl group, aryl group, or heterocyclic group represented by any one of the following: １ ~L ３ a hydrogen atom possessed by a substituted or unsubstituted arylene group represented by any one of the following: １ and Ar ２ At least one hydrogen atom selected from the group consisting of a hydrogen atom possessed by a substituted or unsubstituted aryl group or heterocyclic group represented by any one of the following may be a deuterium atom:

[0186] The deuteration ratio of an invention compound (the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the compound) depends on the deuteration ratio of the raw material compound used. Even if a raw material with a predetermined deuteration ratio is used, a certain proportion of naturally occurring protium isotopes may be contained. Therefore, the deuteration ratios of the invention compounds shown below include ratios that take into account trace amounts of naturally occurring isotopes, in addition to the proportion determined simply by counting the number of deuterium atoms represented by the chemical formula. The deuteration ratio of the invention compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, still more preferably 10% or more, and even more preferably 50% or more.

[0187] The invention compound may be a mixture containing a deuterated compound and a non-deuterated compound, or a mixture of two or more compounds having different deuteration rates. The deuteration rate of such a mixture is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, still more preferably 10% or more, even more preferably 50% or more, and less than 100%. Furthermore, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the invention compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, and still more preferably 10% or more, and less than 100%.

[0188] Those skilled in the art can easily prepare the compounds of the present invention by referring to the synthesis examples below and known synthesis methods.

[0189] Specific examples of the compound of the invention are shown below, but the invention is not limited to these exemplary compounds. In the specific examples below, D represents a deuterium atom.

[0190]

[0191]

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[0283] Material for Organic EL Device The material for organic EL device, which is one embodiment of the present invention, contains the compound of the present invention. The content of the compound of the present invention in the material for organic EL device is 1% by mass or more (including 100%), preferably 10% by mass or more (including 100%), more preferably 50% by mass or more (including 100%), even more preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). The material for organic EL device, which is one embodiment of the present invention, is useful for producing organic EL devices.

[0284] Organic EL Device An organic EL device according to one embodiment of the present invention has an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer includes an emitting layer, and at least one layer of the organic layer contains the compound of the present invention. Examples of organic layers containing the compound of the present invention include, but are not limited to, a hole transporting region (e.g., hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer) disposed between the anode and the emitting layer, the emitting layer, a spacer layer, and an electron transporting region (e.g., electron injection layer, electron transport layer, hole blocking layer) disposed between the cathode and the emitting layer. The compound of the present invention is preferably used as a material for the hole transporting region or the emitting layer of a fluorescent or phosphorescent EL device, more preferably as a material for the hole transporting region, even more preferably as a material for the hole injection layer, hole transport layer, electron blocking layer, or exciton blocking layer, and particularly preferably as a material for the hole injection layer or hole transport layer.

[0285] The organic EL device according to one embodiment of the present invention may be a fluorescent or phosphorescent monochromatic light-emitting device, a fluorescent / phosphorescent hybrid white light-emitting device, a simple type having a single light-emitting unit, or a tandem type having multiple light-emitting units, and is preferably a fluorescent light-emitting device. Here, the term "light-emitting unit" refers to a minimum unit that includes organic layers, at least one of which is a light-emitting layer, and that emits light by recombination of injected holes and electrons.

[0286] For example, a typical element configuration of a simple-type organic EL element can be the following: (1) Anode / Light-emitting unit / Cathode The light-emitting unit may also be a multi-layer type having a plurality of phosphorescent or fluorescent light-emitting layers, in which case a spacer layer may be provided between each light-emitting layer to prevent excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer. A typical layer configuration of a simple-type light-emitting unit is shown below. The layers in parentheses are optional.(a) (hole injection layer / ) hole transport layer / fluorescent-emitting layer / electron transport layer ( / electron injection layer) (b) (hole injection layer / ) hole transport layer / phosphorescent-emitting layer / electron transport layer ( / electron injection layer) (c) (hole injection layer / ) hole transport layer / first fluorescent-emitting layer / second fluorescent-emitting layer / electron transport layer ( / electron injection layer) (d) (hole injection layer / ) hole transport layer / first phosphorescent-emitting layer / second phosphorescent-emitting layer / electron transport layer ( / electron injection layer) (e) (hole injection layer / ) hole transport layer / phosphorescent-emitting layer / space layer / fluorescent-emitting layer / electron transport layer ( / electron injection layer) (f) (hole injection layer / ) hole transport layer / first phosphorescent-emitting layer / second phosphorescent-emitting layer / space layer / fluorescent-emitting layer / electron transport layer ( / electron injection layer) (g) (hole injection layer / ) hole transport layer / first phosphorescent-emitting layer / space layer / second phosphorescent-emitting layer / space layer / fluorescent-emitting layer / electron transport layer ( / electron injection layer) (h) (hole injection layer / ) hole transport layer / phosphorescent-emitting layer / space layer / first fluorescent-emitting layer / second fluorescent-emitting layer / electron transport layer ( / electron injection layer) (i) (hole injection layer / ) hole transport layer / electron blocking layer / fluorescent-emitting layer / electron transport layer ( / electron injection layer) (j) (hole injection layer / ) hole transport layer / electron blocking layer / phosphorescent-emitting layer / electron transport layer ( / electron injection layer) (k) (hole injection layer / ) hole transport layer / exciton blocking layer / fluorescent-emitting layer / electron transport layer ( / electron injection layer) (l) (hole injection layer / ) hole transport layer / exciton blocking layer / phosphorescent-emitting layer / electron transport layer ( / electron injection layer) (m) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent-emitting layer / electron transport layer ( / electron injection layer) (n) (hole injection layer / ) first hole transport layer / second hole transport layer / phosphorescent-emitting layer / electron transport layer ( / electron injection layer) (o) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent-emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer) (p) (hole injection layer / ) first hole transport layer / second hole transport layer / phosphorescent-emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer) (q) (hole injection layer / ) hole transport layer / fluorescent-emitting layer / hole blocking layer / electron transport layer ( / electron injection layer) (r) (hole injection layer / ) hole transport layer / phosphorescent-emitting layer / hole blocking layer / electron transport layer ( / electron injection layer) (s) (hole injection layer / ) hole transport layer / fluorescent emitting layer / exciton blocking layer / electron transport layer ( / electron injection layer) (t) (hole injection layer / ) hole transport layer / phosphorescent emitting layer / exciton blocking layer / electron transport layer ( / electron injection layer).

[0287] The phosphorescent or fluorescent-emitting layers may each emit a different light color. Specifically, the light-emitting unit (f) may have a layer structure such as (hole injection layer / ) hole transport layer / first phosphorescent-emitting layer (red-emitting) / second phosphorescent-emitting layer (green-emitting) / spacer layer / fluorescent-emitting layer (blue-emitting) / electron transport layer. An electron-blocking layer may be provided between each light-emitting layer and the hole transport layer or the spacer layer, as appropriate. A hole-blocking layer may also be provided between each light-emitting layer and the electron transport layer, as appropriate. By providing an electron-blocking layer or a hole-blocking layer, electrons or holes can be confined within the light-emitting layer, increasing the probability of charge recombination in the light-emitting layer and improving luminous efficiency.

[0288] A typical element configuration of a tandem organic EL element can be as follows: (2) anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode Here, the first light-emitting unit and the second light-emitting unit can be, for example, independently selected from the light-emitting units described above. The intermediate layer is generally also called an intermediate electrode, intermediate conductive layer, charge generation layer, electron extraction layer, connection layer, or intermediate insulating layer, and can be made of known materials that supply electrons to the first light-emitting unit and holes to the second light-emitting unit.

[0289] 1 is a schematic diagram showing an example of the layer structure of an organic EL device according to one embodiment of the present invention. The organic EL device 1 includes a substrate 2, an anode 3, a cathode 4, and an emitting unit 10 disposed between the anode 3 and the cathode 4. The emitting unit 10 includes an emitting layer 5. A hole transport zone 6 (e.g., a hole injection layer, a hole transport layer) is disposed between the emitting layer 5 and the anode 3, and an electron transport zone 7 (e.g., an electron injection layer, an electron transport layer) is disposed between the emitting layer 5 and the cathode 4. An electron blocking layer (not shown) may be disposed on the anode 3 side of the emitting layer 5, and a hole blocking layer (not shown) may be disposed on the cathode 4 side of the emitting layer 5. This allows electrons and holes to be trapped in the emitting layer 5, further increasing the efficiency of exciton generation in the emitting layer 5.

[0290] 2 is a schematic diagram showing the layer structure of another organic EL element according to one embodiment of the present invention. The organic EL element 11 includes a substrate 2, an anode 3, a cathode 4, and an emitting unit 20 disposed between the anode 3 and the cathode 4. The emitting unit 20 includes an emitting layer 5. The hole transport region disposed between the anode 3 and the emitting layer 5 is formed of a hole injection layer 6a, a first hole transport layer 6b, and a second hole transport layer 6c. The electron transport region disposed between the emitting layer 5 and the cathode 4 is formed of a first electron transport layer 7a and a second electron transport layer 7b.

[0291] 3 is a schematic diagram showing an example of the layer structure of yet another organic EL element according to one embodiment of the present invention. The organic EL element 12 includes a substrate 2, an anode 3, a cathode 4, and an emitting unit 30 disposed between the anode 3 and the cathode 4. The emitting unit 30 includes a first emitting layer 5a and a second emitting layer 5b. The hole transporting region disposed between the anode 3 and the first emitting layer 5a is formed of a hole injection layer 6a, a first hole transporting layer 6b, and a second hole transporting layer 6c. The electron transporting region disposed between the second emitting layer 5b and the cathode 4 is formed of a first electron transporting layer 7a and a second electron transporting layer 7b.

[0292] In the present invention, a host combined with a fluorescent dopant (fluorescent-emitting material) is referred to as a fluorescent host, and a host combined with a phosphorescent dopant is referred to as a phosphorescent host. The fluorescent host and the phosphorescent host are not distinguished solely by molecular structure. That is, the phosphorescent host refers to a material that forms a phosphorescent-emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material that forms a fluorescent-emitting layer. The same applies to the fluorescent host.

[0293] Substrate The substrate is used as a support for the organic EL element. For example, a glass, quartz, or plastic plate can be used as the substrate. Flexible substrates may also be used. Examples of flexible substrates include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Inorganic vapor-deposited films can also be used.

[0294] 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, indium oxide containing tungsten oxide and zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the above metals (e.g., titanium nitride).

[0295] These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target in which 1 to 10 wt % of zinc oxide is added to indium oxide, and indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target in which 0.5 to 5 wt % of tungsten oxide and 0.1 to 1 wt % of zinc oxide are added to indium oxide. Other methods that may be used for production include vacuum deposition, coating, inkjet printing, and spin coating.

[0296] The hole injection layer formed in contact with the anode is formed using a material that easily injects holes regardless of the work function of the anode, and therefore materials commonly used as electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, elements belonging to Group 1 or Group 2 of the periodic table) can be used. Materials with small work functions, such as elements belonging to Group 1 or Group 2 of the periodic table, can also be used, including alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these. When forming an anode using alkali metals, alkaline earth metals, and alloys containing these, vacuum deposition or sputtering can be used. Furthermore, when using silver paste or the like, coating or inkjet printing can be used.

[0297] Hole Injection Layer The hole injection layer is a layer containing a material with high hole injection properties (hole injection material), and is formed between the anode and the light-emitting layer, or, if present, between the hole transport layer and the anode.

[0298] Examples of hole injection materials that can be used other than the compound of the present invention include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.

[0299] The low molecular weight organic compounds 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DNTPD). Examples of the hole injection layer material include aromatic amine compounds such as 3-[N-(9-phenylcarbazol-3-yl)-N-phenylaminophenyl]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1).

[0300] Polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used. Examples include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD). Furthermore, polymer compounds to which an acid has been added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[0301] Furthermore, it is also preferable to use an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K).

[0302] (In the above formula, R ２０１ ~R ２０６ each independently represents a cyano group, —CONH ２ , a carboxyl group, or -COOR ２０７ (R ２０７ represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms). ２０１ and R ２０２ , R ２０３ and R ２０４ , and R ２０５ and R ２０６ Two adjacent groups selected from the following may be bonded to each other to form a group represented by —CO—O—CO—. ２０７ Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.

[0303] Hole Transport Layer The hole transport layer is a layer containing a material with high hole transport properties (hole transport material), and is formed between the anode and the light-emitting layer, or, if present, between the hole injection layer and the light-emitting layer. The invention compound may be used alone or in combination with the following compounds in the hole transport layer.

[0304] The hole transport layer may have a single-layer structure or a multilayer structure including two or more layers. For example, the hole transport layer may have a two-layer structure including a first hole transport layer (anode side) and a second hole transport layer (cathode side). That is, the hole transport zone may include a first hole transport layer on the anode side and a second hole transport layer on the cathode side. The hole transport layer may also have a three-layer structure including, in order from the anode side, a first hole transport layer, a second hole transport layer, and a third hole transport layer. That is, the third hole transport layer may be disposed between the second hole transport layer and the light-emitting layer. In one embodiment of the present invention, the hole transport layer of the single-layer structure is preferably adjacent to the light-emitting layer. Furthermore, the hole transport layer closest to the cathode in the multilayer structure, for example, the second hole transport layer of the two-layer structure, is preferably adjacent to (directly contacts) the light-emitting layer. In another embodiment of the present invention, an electron blocking layer, as described below, may be interposed between the hole transport layer and the light-emitting layer in the single-layer structure, or between the hole transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer. In the hole transport layer of the two-layer structure, the invention compound may be contained in either the first hole transport layer or the second hole transport layer, or may be contained in both. In one embodiment of the present invention, the invention compound is preferably contained only in the first hole transport layer, while in another embodiment, the invention compound is preferably contained only in the second hole transport layer. In yet another embodiment, the invention compound is preferably contained in both the first hole transport layer and the second hole transport layer.

[0305] In one embodiment of the present invention, the invention compound contained in one or both of the first hole transport layer and the second hole transport layer is preferably a protonated form from the viewpoint of production costs. The protonated form refers to an invention compound in which all hydrogen atoms are protonated. Therefore, an organic EL device according to one embodiment of the present invention is preferably an organic EL device in which one or both of the first hole transport layer and the second hole transport layer contain an invention compound consisting essentially of a protonated form. The term "invention compound consisting essentially of a protonated form" means that the content of the protonated form relative to the total amount of the invention compound is 90 mol % or more, preferably 95 mol % or more, and more preferably 99 mol % or more (all of which include 100%).

[0306] Examples of materials that can be used for the hole transport layer other than the compound of the present invention include aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. Examples of aromatic amine compounds include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl) )-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). －６ cm ２ / Vs or more.

[0307] Examples of carbazole derivatives include 4,4'-di(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA). Examples of anthracene derivatives include 2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth). Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. However, compounds other than those mentioned above may be used as long as they have a higher hole transporting property than an electron transporting property.

[0308] Dopant Material of the Light-Emitting Layer The light-emitting layer is a layer containing a highly light-emitting material (dopant material), and various materials can be used. For example, fluorescent materials and phosphorescent materials can be used as dopant materials. Fluorescent materials are compounds that emit light from a singlet excited state, and phosphorescent materials are compounds that emit light from a triplet excited state. In one embodiment of the present invention, the light-emitting layer is a single layer. In another embodiment of the present invention, the light-emitting layer includes a first light-emitting layer on the anode side and a second light-emitting layer on the cathode side.

[0309] Examples of blue fluorescent materials that can be used in the light-emitting layer include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. Specific examples include N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), etc.

[0310] As a green fluorescent material that can be used in the light-emitting layer, aromatic amine derivatives and the like can be used. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[ 9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), and the like.

[0311] Examples of red fluorescent materials that can be used in the light-emitting layer include tetracene derivatives and diamine derivatives. Specific examples include N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD) and 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD). In one embodiment of the present invention, the light-emitting layer preferably contains a fluorescent material (fluorescent dopant material).

[0312] As blue phosphorescent materials that can be used in the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used. Specific examples include bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviation: FIrpic), bis[2-(3',5'bistrifluoromethylphenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviation: Ir(CF3ppy)2(pic)), and bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) acetylacetonate (abbreviation: FIracac).

[0313] Green phosphorescent materials that can be used in the light-emitting layer include iridium complexes, such as tris(2-phenylpyridinato-N,C2')iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazolato)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), and bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)).

[0314] 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. Specific examples include organometallic complexes such as bis[2-(2'-benzo[4,5-α]thienyl)pyridinato-N,C3']iridium(III) acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinolinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP).

[0315] Furthermore, rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: Eu(DBM)3(Phen)), and tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3(Phen)) can be used as phosphorescent materials because they emit light from rare earth metal ions (electron transition between different multiplicities).

[0316] The light-emitting layer may have a structure in which the above-described dopant material is dispersed in another material (host material). It is preferable to use a material having a lower lowest unoccupied molecular orbital (LUMO) level and a lower highest occupied molecular orbital (HOMO) level than the dopant material.

[0317] Examples of host materials that can be used 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.

[0318] For example, metal complexes such as tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ); Heterocyclic compounds such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), and bathocuproine (abbreviation: BCP); 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-B uDNA), 9,9'-bianthryl (abbreviation: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviation: DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 3,3',3''-(benzene-1,3,5-triyl)tripylene (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenylchrysene, and other condensed aromatic compounds;and N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H Examples of the aromatic amine compounds that can be used include N,N'-carbazole-3-amine (abbreviation: 2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). Multiple types of host materials may be used.

[0319] In particular, in the case of a blue fluorescent element, it is preferable to use the following anthracene compound as the host material.

[0320]

[0321]

[0322]

[0323] Electron Transport Layer The electron transport layer is a layer containing a material with high electron transport properties (electron transport material) and is formed between the light-emitting layer and the cathode, or, if present, between the electron injection layer and the light-emitting layer. The electron transport layer may have a single-layer structure or a multilayer structure containing two or more layers. For example, the electron transport layer may have a two-layer structure containing a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one embodiment of the present invention, the electron transport layer of the single-layer structure is preferably adjacent to the light-emitting layer. Furthermore, the electron transport layer closest to the anode in the multilayer structure, such as the first electron transport layer in the two-layer structure, is preferably adjacent to the light-emitting layer. In another embodiment of the present invention, a hole-blocking layer, as described below, may be interposed between the electron transport layer and the light-emitting layer of the single-layer structure, or between the electron transport layer closest to the light-emitting layer and the light-emitting layer in the multilayer structure. In one embodiment of the organic EL device according to the present invention, the electron transport layer may contain compound (1).

[0324] The electron transport layer may be made of, for example: (1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; (2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; or (3) polymer compounds.

[0325] Examples of metal complexes include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).

[0326] Examples of heteroaromatic compounds include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2, Examples of such benzophenanthroline include 4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4′-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs).

[0327] Examples of the polymer compound include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy).

[0328] The above material is 10 －６ cm ２ A material having an electron mobility of 1 / Vs or more may be used for the electron transport layer, as long as the material has a higher electron transport property than a hole transport property.

[0329] Electron Injection Layer The electron injection layer is a layer containing a material with high electron injection properties. For the electron injection layer, alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), rare earth metals such as europium (Eu) and ytterbium (Yb), and compounds containing these metals can be used. Examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, rare earth metal halides, and rare earth metal-containing organic complexes. Mixtures of these compounds can also be used. Alternatively, materials with electron transport properties containing alkali metals, alkaline earth metals, or compounds thereof, such as Alq containing magnesium (Mg), can be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, the electron injection layer may be formed using a composite material comprising a mixture of an organic compound and an electron donor (donor). Such composite materials have excellent electron injection and transport properties because the organic compound accepts electrons from the electron donor. In this case, the organic compound is preferably a material that is excellent at transporting the accepted electrons. Specifically, for example, the materials constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) described above can be used. The electron donor may be any material that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, including lithium, cesium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides and alkaline earth metal oxides are also preferred, including lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (abbreviated as TTF) can also be used.

[0330] Cathode For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof with a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), and ytterbium (Yb), and alloys containing these. When forming a cathode using alkali metals, alkaline earth metals, or alloys containing these, vacuum deposition or sputtering can be used. When using silver paste or the like, coating or inkjet printing can be used. By providing an electron injection layer, the cathode can be formed using various conductive materials, regardless of the magnitude of the work function, such as Al, Ag, ITO, graphene, and indium oxide-tin oxide containing silicon or silicon oxide. These conductive materials can be formed into films by sputtering, ink jetting, spin coating, or the like.

[0331] Insulating Layer Organic EL elements are prone to pixel defects due to leakage and short circuits because an electric field is applied to an ultra-thin film. To prevent this, an insulating layer made of an insulating thin film may be inserted between a pair of electrodes. Materials used for the insulating layer include, for example, aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. Mixtures or laminates of these materials may also be used.

[0332] Spacer Layer The spacer layer is a layer provided between a fluorescent-emitting layer and a phosphorescent-emitting layer, for example, when the fluorescent-emitting layer and the phosphorescent-emitting layer are stacked, for the purpose of preventing excitons generated in the phosphorescent-emitting layer from diffusing into the fluorescent-emitting layer or for the purpose of adjusting the carrier balance. Spacer layers can also be provided between multiple phosphorescent-emitting layers. Because the spacer layer is provided between the light-emitting layers, it is preferable that the spacer layer be made of a material that has both electron transport and hole transport properties. Furthermore, in order to prevent the diffusion of triplet energy in adjacent phosphorescent-emitting layers, it is preferable that the triplet energy be 2.6 eV or more. Materials used for the spacer layer include those similar to those used for the hole transport layer described above.

[0333] Blocking Layer A blocking layer such as an electron blocking layer, hole blocking layer, or exciton blocking layer may be provided adjacent to the light-emitting layer. An electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer, and a hole blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron transport layer. An exciton blocking layer has the function of preventing excitons generated in the light-emitting layer from diffusing to surrounding layers and confining the excitons within the light-emitting layer.

[0334] Each layer of the organic EL element can be formed by a conventionally known vapor deposition method, coating method, etc. For example, the layers can be formed by a conventionally known vapor deposition method such as vacuum vapor deposition or molecular beam deposition (MBE), or by a coating method using a solution of a compound that forms the layer, such as dipping, spin coating, casting, bar coating, or roll coating.

[0335] The thickness of each layer is not particularly limited, but generally, if the thickness is too thin, defects such as pinholes are likely to occur, whereas if the thickness is too thick, a high driving voltage is required, resulting in poor efficiency. Therefore, the thickness is usually 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm.

[0336] Electronic Equipment The organic EL element can be suitably used in electronic equipment such as display components such as organic EL panel modules, display devices for televisions, mobile phones, personal computers, etc., and light-emitting devices for lighting and vehicle lamps.

[0337] The present invention will be described in more detail below using examples, but the present invention is not limited to the following examples.

[0338] Invention compound (Compound 1) used in the production of the organic EL device of Example 1

[0339] Invention compound (Compound 2) used in the production of the organic EL device of Example 2

[0340] Invention compound (Compound 3) used in the production of the organic EL device of Example 3

[0341] Invention compound (Compound 4) used in the production of the organic EL device of Example 4

[0342] Invention compound (Compound 5) used in the production of the organic EL device of Example 5

[0343] Invention compound (Compound 6) used in the production of the organic EL device of Example 6

[0344] Invention compound (Compound 7) used in the production of the organic EL device of Example 7

[0345] Invention compound (Compound 8) used in the production of the organic EL device of Example 8

[0346] Invention compound (Compound 9) used in the production of the organic EL device of Example 9

[0347] Invention compound (Compound 10) used in the production of the organic EL device of Example 10

[0348] Invention compound (Compound 11) used in the production of the organic EL device of Example 11

[0349] Invention compound (Compound 12) used in the production of the organic EL device of Example 12

[0350] Invention compound (Compound 13) used in the production of the organic EL device of Example 13

[0351] Invention compound (Compound 14) used in the production of the organic EL device of Example 14

[0352] Invention compound (Compound 15) used in the production of the organic EL device of Example 15

[0353] Invention compound (Compound 16) used in the production of the organic EL device of Example 16

[0354] Invention compound (Compound 17) used in the production of the organic EL device of Example 17

[0355] Comparative Compound 1 used in the production of the organic EL device of Comparative Example 1

[0356] Comparative Compound 2 used in the production of the organic EL device of Comparative Example 2

[0357] Comparative Compound 3 used in the production of the organic EL device of Comparative Example 3

[0358] Other compounds used in the production of organic EL devices in Examples 1 to 13 and Comparative Examples 1 and 2

[0359] Other compounds used in the production of organic EL devices in Examples 14 to 17 and Comparative Example 3

[0360] Preparation of First Organic EL Device Example 1 A 25 mm × 75 mm × 1.1 mm glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then 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, and first, compound HT-1 and compound HI-1 were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-1 to compound HI-1 (HT-1:HI-1) was 97:3. Next, compound HT-1 was vapor-deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, compound 1 was vapor-deposited on this first hole transport layer to form a second hole transport layer with a thickness of 10 nm. Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited on this second hole-transporting layer to form an emitting layer with a thickness of 25 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 96:4. Next, compound ET-1 was deposited on this emitting layer to form a first electron-transporting layer with a thickness of 5 nm. Next, compound ET-2 and Liq were co-deposited on this first electron-transporting layer to form a second electron-transporting layer with a thickness of 20 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50. Next, LiF was deposited on this second electron-transporting layer to form an electron-injecting electrode with a thickness of 1 nm. Then, metal Al was deposited on this electron-injecting electrode to form a metal cathode with a thickness of 50 nm. The layer configuration of the first organic EL device of Example 1 obtained in this manner is shown below. ITO (130) / HT-1:HI-1 = 97:3 (10) / HT-1 (80) / Compound 1 (10) / BH-1:BD-1 = 96:4 (25) / ET-1 (5) / ET-2:Liq = 50:50 (20) / LiF (1) / Al (50) In the above layer structure, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

[0361] Measurement of External Quantum Efficiency (EQE) The obtained first organic EL device was subjected to a current density of 10 mA / cm at room temperature. ２The device was driven with a constant DC current at 1000 V. The luminance was measured using a luminance meter (Spectroradiometer CS-1000 manufactured by Minolta Co., Ltd.), and the external quantum efficiency (%) was calculated from the results. The results are shown in Table 1.

[0362] A first organic EL device was fabricated in the same manner as in Example 1, except that the material of the second hole transport layer was changed from Compound 1 to Compound 2, and the external quantum efficiency (EQE) was measured. The results are shown in Table 1.

[0363] Example 3 A first organic EL device was fabricated in the same manner as in Example 1, except that the material of the second hole transport layer was changed from Compound 1 to Compound 3, and the external quantum efficiency (EQE) was measured. The results are shown in Table 1.

[0364] Example 4 A first organic EL device was fabricated in the same manner as in Example 1, except that the material of the second hole transport layer was changed from Compound 1 to Compound 4, and the external quantum efficiency (EQE) was measured. The results are shown in Table 1.

[0365] Example 5 A first organic EL device was fabricated in the same manner as in Example 1, except that the material of the second hole transport layer was changed from Compound 1 to Compound 5, and the external quantum efficiency (EQE) was measured. The results are shown in Table 1.

[0366] Example 6 A first organic EL device was fabricated in the same manner as in Example 1, except that the material of the second hole transport layer was changed from Compound 1 to Compound 6, and the external quantum efficiency (EQE) was measured. The results are shown in Table 1.

[0367] Example 7 A first organic EL device was fabricated in the same manner as in Example 1, except that the material of the second hole transport layer was changed from Compound 1 to Compound 7, and the external quantum efficiency (EQE) was measured. The results are shown in Table 1.

[0368] Example 8 A first organic EL device was fabricated in the same manner as in Example 1, except that the material of the second hole transport layer was changed from Compound 1 to Compound 8, and the external quantum efficiency (EQE) was measured. The results are shown in Table 1.

[0369] Example 9 A first organic EL device was fabricated in the same manner as in Example 1, except that the material of the second hole transport layer was changed from Compound 1 to Compound 9, and the external quantum efficiency (EQE) was measured. The results are shown in Table 1.

[0370] Example 10 A first organic EL device was fabricated in the same manner as in Example 1, except that the material of the second hole transport layer was changed from Compound 1 to Compound 10, and the external quantum efficiency (EQE) was measured. The results are shown in Table 1.

[0371] Example 11 A first organic EL device was fabricated in the same manner as in Example 1, except that the material of the second hole transport layer was changed from Compound 1 to Compound 11, and the external quantum efficiency (EQE) was measured. The results are shown in Table 1.

[0372] Example 12 A first organic EL device was fabricated in the same manner as in Example 1, except that the material of the second hole transport layer was changed from Compound 1 to Compound 12, and the external quantum efficiency (EQE) was measured. The results are shown in Table 1.

[0373] Example 13 A first organic EL device was fabricated in the same manner as in Example 1, except that the material of the second hole transport layer was changed from Compound 1 to Compound 13, and the external quantum efficiency (EQE) was measured. The results are shown in Table 1.

[0374] Comparative Example 1 A first organic EL device was fabricated in the same manner as in Example 1, except that the second hole transport layer material was changed from Compound 1 to Comparative Compound 1, and the external quantum efficiency (EQE) was measured. The results are shown in Table 1.

[0375] Comparative Example 2 A first organic EL device was fabricated in the same manner as in Example 1, except that the material of the second hole transport layer was changed from Compound 1 to Comparative Compound 2, and the external quantum efficiency (EQE) was measured. The results are shown in Table 1.

[0376] Preparation of a Second Organic EL Device Example 14 A 25 mm x 75 mm x 1.1 mm glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then 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, and first, compound HT-2 and compound HI-1 were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-2 to compound HI-1 (HT-2:HI-1) was 97:3. Next, compound HT-2 was vapor-deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, compound 14 was vapor-deposited on this first hole transport layer to form a second hole transport layer with a thickness of 10 nm. Next, compound BH-2 (host material) and compound BD-2 (dopant material) were co-deposited on this second hole-transporting layer to form an emitting layer with a thickness of 20 nm. The mass ratio of compound BH-2 to compound BD-2 (BH-2:BD-2) was 99:1. Next, compound ET-1 was deposited on this emitting layer to form a first electron-transporting layer with a thickness of 5 nm. Next, compound ET-3 and Liq were co-deposited on this first electron-transporting layer to form a second electron-transporting layer with a thickness of 25 nm. The mass ratio of compound ET-3 to Liq (ET-3:Liq) was 50:50. Next, Yb was deposited on this second electron-transporting layer to form an electron-injecting electrode with a thickness of 1 nm. Then, metal Al was deposited on this electron-injecting electrode to form a metal cathode with a thickness of 50 nm. The layer structure of the second organic EL device of Example 14 obtained in this manner is shown below. ITO (130) / HT-2:HI-1 = 97:3 (10) / HT-2 (80) / Compound 14 (10) / BH-2:BD-2 = 99:1 (20) / ET-1 (5) / ET-3:Liq = 50:50 (25) / Yb (1) / Al (50) In the above layer structure, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

[0377] Measurement of External Quantum Efficiency (EQE) The obtained second organic EL device was subjected to a current density of 10 mA / cm at room temperature. ２The device was driven with a constant DC current at 1000 V. The luminance was measured using a luminance meter (Spectroradiometer CS-1000 manufactured by Minolta Co., Ltd.), and the external quantum efficiency (%) was calculated from the results. The results are shown in Table 2.

[0378] Example 15 A second organic EL device was fabricated in the same manner as in Example 14, except that the material of the second hole transport layer was changed from Compound 14 to Compound 15, and the external quantum efficiency (EQE) was measured. The results are shown in Table 2.

[0379] A second organic EL device was fabricated in the same manner as in Example 14, except that the material of the second hole transport layer was changed from Compound 14 to Compound 16, and the external quantum efficiency (EQE) was measured. The results are shown in Table 2.

[0380] Example 17 A second organic EL device was fabricated in the same manner as in Example 14, except that the material of the second hole transport layer was changed from Compound 14 to Compound 17, and the external quantum efficiency (EQE) was measured. The results are shown in Table 2.

[0381] A second organic EL device was fabricated in the same manner as in Example 14, except that the material of the second hole transport layer was changed from Compound 14 to Comparative Compound 3, and the external quantum efficiency (EQE) was measured. The results are shown in Table 2.

[0382]

[0383]

[0384] As is clear from the results in Table 1, the organic EL devices containing the invention compounds (compounds 1 to 13) have significantly improved external quantum efficiency (EQE) compared to the organic EL devices containing comparative compounds 1 and 2. As is clear from the results in Table 2, the organic EL devices containing the invention compounds (compounds 14 to 17) have significantly improved external quantum efficiency (EQE) compared to the organic EL device containing comparative compound 3.

[0385] Compounds 1 to 17 synthesized in Synthesis Examples 1 to 17

[0386] Intermediate Synthesis Example 1: Synthesis of Intermediate A

[0387] (1) Synthesis of Intermediate A Under an argon atmosphere, a mixture of 7-chloro-4-phenylnaphtho[1,2-b]benzofuran (13.15 g, 40.0 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (8.76 g, 40.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.733 g, 0.8 mmol), Xphos (1.359 g, 3.2 mmol), tripotassium phosphate (25.5 g, 120 mmol), 1,4-dioxane (200 mL), and water (60 mL) was stirred at 100°C for 5 hours. The reaction solution was cooled to room temperature, water was added, and the mixture was filtered. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain 6.2 g of a yellow solid (Intermediate A). The yield was 40%.

[0388] Intermediate Synthesis Example 2: Synthesis of Intermediate B

[0389] Intermediate B was obtained in a 91% yield by the same procedure as in Intermediate Synthesis Example 1, except that 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline was used instead of the boron compound used in Intermediate Synthesis Example 1.

[0390] Intermediate Synthesis Example 3: Synthesis of Intermediate C

[0391] The same operations as in Intermediate Synthesis Example 1 were carried out except that 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline was used instead of the boron compound used in Intermediate Synthesis Example 1, thereby obtaining Compound C. The yield was 83%.

[0392] Intermediate Synthesis Example 4: Synthesis of Intermediate D

[0393] Intermediate D was obtained in a 78% yield by the same procedure as in Intermediate Synthesis Example 1, except that 10-chloro-4-phenylnaphtho[1,2-b]benzofuran was used instead of 7-chloro-4-phenylnaphtho[1,2-b]benzofuran used in Intermediate Synthesis Example 1.

[0394] Intermediate Synthesis Example 5: Synthesis of Intermediate E

[0395] Intermediate E was obtained in a yield of 85% by the same procedure as in Intermediate Synthesis Example 1, except that 7-chloro-1-phenylnaphtho[1,2-b]benzofuran was used instead of 7-chloro-4-phenylnaphtho[1,2-b]benzofuran used in Intermediate Synthesis Example 1.

[0396] Intermediate Synthesis Example 6: Synthesis of Intermediate F

[0397] Intermediate F was obtained in a yield of 84% by the same procedure as in Intermediate Synthesis Example 1, except that 7-chloro-2-phenylnaphtho[1,2-b]benzofuran was used instead of 7-chloro-4-phenylnaphtho[1,2-b]benzofuran used in Intermediate Synthesis Example 1.

[0398] Intermediate Synthesis Example 7: Synthesis of Intermediate G

[0399] Intermediate G was obtained in a 91% yield by the same procedure as in Intermediate Synthesis Example 1, except that 7-chloro-3-phenylnaphtho[1,2-b]benzofuran was used instead of 7-chloro-4-phenylnaphtho[1,2-b]benzofuran used in Intermediate Synthesis Example 1.

[0400] Intermediate Synthesis Example 8: Synthesis of Intermediate H

[0401] Intermediate H was obtained in a yield of 71% by the same procedure as in Intermediate Synthesis Example 1, except that 7-bromo-4-phenylnaphtho[1,2-b]benzofuran was used instead of 7-chloro-4-phenylnaphtho[1,2-b]benzofuran and 2-(2-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane were used instead of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline.

[0402] Intermediate Synthesis Example 9: Synthesis of Intermediate I

[0403] Intermediate I was obtained in a yield of 81% by the same procedure as in Intermediate Synthesis Example 1, except that 10-bromo-4-phenylnaphtho[1,2-b]benzofuran was used instead of 7-chloro-4-phenylnaphtho[1,2-b]benzofuran and 4-chlorophenylboronic acid was used instead of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline.

[0404] Intermediate Synthesis Example 10: Synthesis of Intermediate J

[0405] Intermediate J was obtained in a yield of 88% by the same procedure as in Intermediate Synthesis Example 1, except that 7-bromo-4-phenylnaphtho[1,2-b]benzofuran was used instead of 7-chloro-4-phenylnaphtho[1,2-b]benzofuran and 3-chlorophenylboronic acid was used instead of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline used in Intermediate Synthesis Example 1.

[0406] Synthesis Example 1: Synthesis of Compound 1

[0407] Under an argon atmosphere, a mixture of intermediate A (3.00 g, 7.78 mmol), 4-bromobiphenyl (3.72 g, 15.95 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.143 g, 0.156 mmol), tri-t-butylphosphonium tetrafluoroborate (0.181 g, 0.623 mmol), sodium t-butoxide (2.09 g, 21.79 mmol), and 51.9 mL of xylene was stirred at 140°C for 3 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain 3.00 g of a white solid. The yield was 56%. Mass spectrometry analysis of the resulting product identified Compound 1, which had a molecular weight of 689.85 with an m / e of 690.

[0408] Synthesis Example 2: Synthesis of Compound 2

[0409] Compound 2 was obtained by the same procedure as in Synthesis Example 1, except that Intermediate B was used instead of Intermediate A used in Synthesis Example 1. Mass spectrometry analysis of the obtained product showed that it was Compound 2, with a molecular weight of 689.85 and an m / e of 690.

[0410] Synthesis Example 3: Synthesis of Compound 3

[0411] Compound 3 was obtained by the same procedure as in Synthesis Example 1, except that Intermediate C was used instead of Intermediate A used in Synthesis Example 1. Mass spectrometry analysis of the obtained product showed that it was Compound 3, with a molecular weight of 689.85 and an m / e of 690.

[0412] Synthesis Example 4: Synthesis of Compound 4

[0413] Under an argon atmosphere, a mixture of 7-chloro-4-phenylnaphtho[1,2-b]benzofuran (3.00 g, 9.12 mmol), di([1,1'-biphenyl]-4-yl)amine (2.93 g, 9.12 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.167 g, 0.182 mmol), tri-t-butylphosphonium tetrafluoroborate (0.222 g, 0.729 mmol), sodium t-butoxide (1.228 g, 12.77 mmol), and xylene (60.8 mL) was stirred at 140°C for 3 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain 2.74 g of a white solid. The yield was 49%. Mass spectrometry analysis of the resulting product identified Compound 4, which had a molecular weight of 613.76 and an m / e of 614.

[0414] Synthesis Example 5: Synthesis of Compound 5

[0415] The same procedure as in Synthesis Example 1 was carried out, except that 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-D9 was used instead of 4-bromobiphenyl used in Synthesis Example 1, to obtain 2.2 g of a white solid. The yield was 55%. Mass spectrometry analysis of the obtained product showed that it was Compound 5, with a molecular weight of 707.96 and an m / e of 708.

[0416] Synthesis Example 6: Synthesis of Compound 6

[0417] The same procedure as in Synthesis Example 1 was carried out, except that 2-(4-bromophenyl-2,3,5,6-d4)naphthalene was used instead of 4-bromobiphenyl used in Synthesis Example 1, to obtain 3.72 g of a white solid. The yield was 46%. Mass spectrometry analysis of the obtained product showed that it was Compound 6, with a molecular weight of 798.03 and an m / e of 798.

[0418] Synthesis Example 7: Synthesis of Compound 7

[0419] The same procedure as in Synthesis Example 1 was carried out, except that Intermediate D was used instead of Intermediate A used in Synthesis Example 1, to obtain 4.55 g of a white solid. The yield was 66%. Mass spectrometry analysis of the obtained product showed that it was Compound 7, with a molecular weight of 689.85 and an m / e of 690.

[0420] Synthesis Example 8: Synthesis of Compound 8

[0421] The same procedure as in Synthesis Example 1 was carried out, except that Intermediate E was used instead of Intermediate A used in Synthesis Example 1, to obtain 3.39 g of a white solid. The yield was 49%. Mass spectrometry analysis of the obtained product showed that it was Compound 8, with a molecular weight of 689.85 and an m / e of 690.

[0422] Synthesis Example 9: Synthesis of Compound 9

[0423] The same procedure as in Synthesis Example 1 was carried out, except that Intermediate F was used instead of Intermediate A used in Synthesis Example 1, to obtain 5.09 g of a white solid. The yield was 74%. Mass spectrometry analysis of the obtained product showed that it was Compound 9, with a molecular weight of 689.85 and an m / e of 690.

[0424] Synthesis Example 10: Synthesis of Compound 10

[0425] The same procedure as in Synthesis Example 1 was carried out, except that Intermediate G was used instead of Intermediate A used in Synthesis Example 1, to obtain 4.77 g of a white solid. The yield was 69%. Mass spectrometry analysis of the obtained product showed that it was Compound 10, with a molecular weight of 689.85 and an m / e of 690.

[0426] Synthesis Example 11: Synthesis of Compound 11

[0427] The same procedure as in Synthesis Example 1 was carried out, except that Intermediate H was used instead of Intermediate A used in Synthesis Example 1, and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1''-terphenyl]-4-amine was used instead of 4-bromobiphenyl, to obtain 4.82 g of a white solid. The yield was 63%. Mass spectrometry analysis of the obtained product identified it as Compound 11, which had a molecular weight of 765.96 and an m / e of 766.

[0428] Synthesis Example 12: Synthesis of Compound 12

[0429] The same procedure as in Synthesis Example 11 was carried out, except that N-(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1'-biphenyl]-4-amine was used instead of N-([1,1'-biphenyl]-4-yl)-[1,1':4',1''-terphenyl]-4-amine used in Synthesis Example 11, to obtain 3.67 g of a white solid. The yield was 47%. Mass spectrometry analysis of the obtained product identified it as Compound 12, which had a molecular weight of 779.94 and an m / e of 780.

[0430] Synthesis Example 13: Synthesis of Compound 13

[0431] The same procedure as in Synthesis Example 11 was carried out, except that N-([1,1'-biphenyl]-4-yl)-9,9-diphenyl-9H-fluoren-2-amine was used instead of N-([1,1'-biphenyl]-4-yl)-[1,1':4',1''-terphenyl]-4-amine used in Synthesis Example 11, to obtain 5.11 g of a white solid. The yield was 60%. Mass spectrometry analysis of the obtained product identified it as Compound 13, which had a molecular weight of 854.06 and an m / e of 854.

[0432] Synthesis Example 14: Synthesis of Compound 14

[0433] The same procedure as in Synthesis Example 4 was carried out, except that Intermediate I was used instead of 7-chloro-4-phenylnaphtho[1,2-b]benzofuran, and N-[4-(1-naphthalenyl)phenyl][1,1'-biphenyl]-4-amine was used instead of N-[1,1'-biphenyl]-4-yl-[1,1'-biphenyl]-4-amine in Synthesis Example 4, to obtain 4.25 g of a white solid. The yield was 63%. Mass spectrometry analysis of the obtained product identified it as Compound 14, which had a molecular weight of 739.92 and an m / e of 740.

[0434] Synthesis Example 15: Synthesis of Compound 15

[0435] The same procedure as in Synthesis Example 4 was carried out, except that Intermediate I was used instead of 7-chloro-4-phenylnaphtho[1,2-b]benzofuran, and N-[4-(9H-carbazol-9-yl)phenyl][1,1'-biphenyl]-2-amine was used instead of N-[1,1'-biphenyl]-4-yl-[1,1'-biphenyl]-4-amine, to obtain 3.48 g of a white solid. The yield was 49%. Mass spectrometry analysis of the obtained product identified it as Compound 15, which had a molecular weight of 778.96 and an m / e of 779.

[0436] Synthesis Example 16: Synthesis of Compound 16

[0437] The same procedure as in Synthesis Example 4 was carried out, except that Intermediate J was used instead of 7-chloro-4-phenylnaphtho[1,2-b]benzofuran and N-[4-(1-naphthalenyl)phenyl]-1-naphthalenamine was used instead of N-[1,1'-biphenyl]-4-yl-[1,1'-biphenyl]-4-amine, to obtain 2.34 g of a white solid. The yield was 36%. Mass spectrometry analysis of the obtained product identified it as Compound 16, which had a molecular weight of 713.88 and an m / e of 714.

[0438] Synthesis Example 17: Synthesis of Compound 17

[0439] The same procedure as in Synthesis Example 4 was carried out, except that N-[1,1'-biphenyl]-4-yl-[4'-phenyl-1,1':3',1"-terphenyl]-4-amine was used instead of N-[1,1'-biphenyl]-4-yl-[1,1'-biphenyl]-4-amine in Synthesis Example 4, to obtain 4.82 g of a white solid. The yield was 69%. Mass spectrometry analysis of the obtained product identified it as Compound 17, which had a molecular weight of 765.96 and an m / e value of 766.

[0440] REFERENCE SIGNS LIST 1, 11, 12 organic EL element 2 substrate 3 anode 4 cathode 5 emitting layer 5a first emitting layer 5b second emitting layer 6 hole transporting zone (hole transporting layer) 6a hole injection layer 6b first hole transporting layer 6c second hole transporting layer 7 electron transporting zone (electron transporting layer) 7a first electron transporting layer 7b second electron transporting layer 10, 20, 30 emitting unit

Claims

1. A compound represented by the following formula (1): (In formula (1), Ar １ and Ar ２ are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. １ ~L ３ R are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms. ７ ~R １０ is a single bond bonded to *a. １ When is a single bond, R ８ ~R １０ One selected from is a single bond bonded to *a. １ , R ３ ~R ６ and R which is not a single bond ７ ~R １０ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. １ and R ３ ~R ６ At least one of R is not a hydrogen atom. ２ is a hydrogen atom.) 2. R is not a hydrogen atom １ and R ３ ~R ６ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

3. L １ is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.

4. L １ The compound according to claim 3 , wherein is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.

5. L １ The compound according to claim 4 , wherein is a substituted or unsubstituted phenylene group.

6. R ３ ~R ６ The compound according to any one of claims 1 to 5, wherein at least one of is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

7. Ar １ and Ar ２ Each of the groups independently represents a group represented by any one of the following formulas (1a) to (1e): (In formula (1a), *21 is L １ Or L ２ is the bond position to １０１ ~R １０５ and R １０６ ~R １１０ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. １０１ ~R １０５ is a single bond bonded to *22, and R １０６ ~R １１０ One selected from is a single bond bonded to *23. １０１ ~R １０５ adjacent two selected from are not bonded to each other and therefore do not form a ring, １０６ ~R １１０ Two adjacent ones selected from the above are not bonded to each other and therefore do not form a ring. k is 0 or 1, l is 0 or 1, and k+l is an integer of 0 to 2. R １１１ ~R １１５ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. １１１ ~R １１５ Any two adjacent groups selected from may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore may not form a ring. (In formula (1b), *24 is L １ Or L ２ is the bond position to １２１ ~R １２８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. １２１ ~R １２８ is a single bond bonded to *25, and R １２１ ~R １２８ Adjacent two selected from are not bonded to each other and therefore do not form a ring. (In formula (1c), *26 is L １ Or L ２ is the bond position to １３１ ~R １４０ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. １３１ ~R １４０ is a single bond bonded to *27, and R １３１ ~R １４０ Adjacent two selected from are not bonded to each other and therefore do not form a ring. (In formula (1d), *28 is L １ Or L ２ is the bond position to X ２ is an oxygen atom, a sulfur atom, NR Ａ , or C.R. ａ R ｂ It is. Ａ R is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. ａ and R ｂ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or are bonded to each other to form a substituted or unsubstituted ring structure, R １４１ ~R １４８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms. １４１ ~R １４８ , R Ａ , R ａ , and R ｂ One selected from is a single bond bonded to *29. １４１ ~R １４８ At least two adjacent ones selected from may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore may not form a ring. (In formula (1e), *30 is L １ Or L ２ is the bond position to １５１ ~R １５５ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted phenyl group. １５１ ~R １５５ is a single bond bonded to *31, and R １５１ ~R １５５ Another one selected from is a single bond bonded to *32. R that is not a single bond bonded to *31 and is not a single bond bonded to *32 １５１ ~R １５５ Two adjacent groups selected from are not bonded to each other and therefore do not form a ring. １６１ ~R １６５ and R １７１ ~R １７５ are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms. １６１ ~R １６５ At least two adjacent ones selected from may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore not form a ring; R １７１ ~R １７５ At least two adjacent ones selected from may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore may not form a ring.

8. The compound according to any one of claims 1 to 7, wherein the compound represented by formula (1) contains at least one deuterium atom.

9. A material for an organic electroluminescence device comprising the compound according to any one of claims 1 to 8.

10. An organic electroluminescence device having a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer including a light-emitting layer, and at least one of the organic layers including a compound according to any one of claims 1 to 8.

11. The organic electroluminescence device according to claim 10, wherein the organic layer comprises a hole transporting zone between the anode and the light emitting layer, the hole transporting zone comprising the compound.

12. The organic electroluminescent device according to claim 11, wherein the hole transport zone comprises a first hole transport layer on the anode side and a second hole transport layer on the cathode side, and the first hole transport layer, the second hole transport layer, or both contain the compound.

13. The organic electroluminescence device according to claim 12, wherein the second hole transport layer comprises the compound.

14. The organic electroluminescence device according to claim 12 or 13, wherein the second hole transport layer is adjacent to the light emitting layer.

15. The organic electroluminescence device according to any one of claims 10 to 14, wherein the light-emitting layer contains a fluorescent dopant material.

16. The organic electroluminescence device according to any one of claims 10 to 14, wherein the light-emitting layer contains a phosphorescent dopant material.

17. An electronic device comprising the organic electroluminescence element according to any one of claims 10 to 16.

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