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

Abstract

Provided is a compound represented by formula (1). (The symbols in formula (1) are as defined in the specification.) Also provided are an organic electroluminescent element that contains the compound and an electronic device that includes 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, in order to obtain a high-performance organic EL device, it is important to find a combination of materials that efficiently transport electrons or holes to the light-emitting region, facilitate the recombination of electrons and holes, and efficiently emit excitons.

[0003] Patent Documents 1 to 13 disclose compounds used as materials for organic electroluminescence devices.

[0004] Chinese Patent Publication No. 111675701 Chinese Patent Publication No. 109096179 Korean Patent Publication No. 10-2019-0035567 Korean Patent Publication No. 10-2018-0066855 U.S. Patent Application Publication No. 2016 / 0293843 U.S. Patent Application Publication No. 2015 / 0179953 U.S. Patent Application Publication No. 2016 / 0301005 specification Korean Patent Publication No. 10-2018-0116740 specification U.S. Patent Application Publication No. 2017 / 0194569 specification U.S. Patent Application Publication No. 2017 / 0186978 specification U.S. Patent Application Publication No. 2017 / 0186969 specification Korean Patent Publication No. 10-2019-0005522 specification International Publication No. 2021 / 045590

[0005] Although many compounds for organic EL devices have been reported, there is still a demand for further improvement in 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 that further improves the performance of an organic EL element, an organic EL element having further improved element performance, and an electronic device including such an organic EL element.

[0007] The present inventors have conducted extensive research into the performance of organic EL devices containing the compounds described in Patent Documents 1 to 13, and as a result have found that an organic EL device containing a compound represented by the following formula (1) has improved performance:

[0008] In one aspect, the present invention provides a compound represented by the following formula (1): (In formula (1), N ＊ is the central nitrogen atom. ａ and R ｂ One of the groups is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and the other is 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. ａ and R ｂ may be bonded to each other to form a substituted or unsubstituted ring. ２ , R ３ , R ６ and R ７ is a single bond bonded to *1, and R １ , R ４ , R ５ , R ８ , and R that is not a single bond bonded to *1 ２ , R ３ , R ６ and R ７ 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 15 ring 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. １ , R ４ , R ５ , R ８ and the R ２ , R ３ , R ６ and R ７Adjacent two selected from R are not bonded to each other and therefore do not form a ring. １１ ~R １４ 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 18 ring carbon atoms. １１ ~R １４ Adjacent two selected from are not bonded to each other and therefore do not form a ring. １ ~L ４ are each independently a single bond or an arylene group having 6 to 30 ring carbon atoms. １ and Ar ２ is a group represented by any one of the following formulas (1a) to (1g): (In formula (1a), *21 is L １ or L ２ is the bonding position to R 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, and R １１１ ~R １１５ One selected from is a single bond bonded to *24. １０１ ~R １１５ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. １０１ ~R １０５ adjacent two selected from are not bonded to each other and therefore do not form a ring, １０６ ~R １１０ adjacent two selected from are not bonded to each other and therefore do not form a ring, １１１ ~R １１５ Two adjacent groups selected from are not bonded to each other and therefore do not form a ring. m is 0 or 1, n is 0 or 1, and l is 0 or 1. R １１６ ~R １２０are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 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. １１６ ~R １２０ Adjacent two selected from are not bonded to each other and therefore do not form a ring. (In formula (1b), *25 is L １ or L ２ is the bonding position to R １２１ ~R １２８ One selected from is a single bond bonded to *26. １２１ ~R １２８ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. １２１ ~R １２８ adjacent two selected from are not bonded to each other and therefore do not form a ring. １ is a p-phenylene group, and Ar １ is represented by formula (1b), R in the group represented by formula (1b) bonded to the p-phenylene group １２１ , R １２４ , R １２５ , and R １２８ one selected from is a single bond bonded to *26, ２ is a p-phenylene group, and Ar ２ is represented by formula (1b), R in the group represented by formula (1b) bonded to the p-phenylene group １２１ , R １２４ , R １２５ , and R １２８ One selected from is a single bond bonded to *26.) (In formula (1c), *27 is L １ or L ２ is the bonding position to R １３１ ~R １４０ One selected from is a single bond bonded to *28. １３１ ~R １４０are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. １３１ ~R １４０ Adjacent two selected from are not bonded to each other and therefore do not form a ring. (In formula (1d), *29 is L １ or L ２ is the bonding position to R １４１ ~R １５２ One selected from is a single bond bonded to *30. １４１ ~R １５２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. １４１ ~R １５２ Adjacent two selected from are not bonded to each other and therefore do not form a ring structure. (In formula (1e), *31 is L １ or L ２ is the bonding position to R １６１ ~R １６５ is a single bond bonded to *32, and R １６１ ~R １６５ The other one selected from is a single bond bonded to *33. R which is not a single bond bonded to said *32 and is not a single bond bonded to said *33 １６１ ~R １６５ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group. R is not a single bond bonded to *32, nor is it a single bond bonded to *33. １６１ ~R １６５ Adjacent two selected from R are not bonded to each other and therefore do not form a ring. １７１ ~R １７５ and R １８１ ~R １８５ are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms. １７１ ~R １７５adjacent two 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; １８１ ~R １８５ 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 not form a ring. (In formula (1f), *34 is L １ or L ２ X is an oxygen atom, a sulfur atom, or an NR Ａ It is. １９１ ~R １９８ and R Ａ One selected from is a single bond bonded to *35. 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. １９１ ~R １９８ 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. １９１ ~R １９８ 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 not form a ring. (In formula (1g), *36 is L １ or L ２ is the bonding position to R B , R C , and R ２０１ ~R ２０８ One selected from is a single bond bonded to *37. B and R C are each independently 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. B and RC may be bonded to each other to form a substituted or unsubstituted ring. ２０１ ~R ２０８ 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. ２０１ ~R ２０８ Adjacent two selected from are not bonded to each other and therefore do not form a ring.

[0009] In another aspect, the present invention provides a material for an organic EL device, which comprises a compound represented by the formula (1).

[0010] In still another aspect, the present invention provides an organic electroluminescence device comprising a cathode, an anode, and organic layers between the cathode and the anode, wherein the organic layers comprise an emitting layer, and at least one layer of the organic layers comprises a compound represented by formula (1).

[0011] In still another aspect, the present invention provides an electronic device including the organic electroluminescence device.

[0012] An organic EL device containing the compound represented by formula (1) exhibits improved device performance.

[0013] 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 another example of a layer structure of an organic EL element according to one embodiment of the present invention, and FIG. 3 is a schematic diagram showing yet another example of a layer structure of an organic EL element according to one embodiment of the present invention.

[0014] [Definitions] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0015] In this specification, in a chemical structural formula, a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded to a possible bonding position that is not explicitly indicated with a symbol such as "R" or "D" representing a deuterium atom.

[0016] 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.

[0017] 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.

[0018] 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.

[0019] 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.

[0020] 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.

[0021] "Substituents Described in This Specification" The substituents described in this specification are explained below.

[0022] 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.

[0023] "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.

[0024] 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).

[0025]

[0026]

[0027] 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.

[0028] "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.

[0029] 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).

[0030] 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).

[0031] 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.

[0032] 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.

[0033] 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).

[0034] 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):

[0035]

[0036]

[0037] 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:

[0038] 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.

[0039] 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].

[0040] 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].

[0041] 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):

[0042] 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.

[0043] "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.

[0044] 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.

[0045] 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.

[0046] "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.

[0047] 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.

[0048] 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.

[0049] - "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.

[0050] Unsubstituted alkynyl groups (specific example group G5A): ethynyl group

[0051] "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.

[0052] 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.

[0053] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.

[0054] -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.

[0055] ・「-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.

[0056] ・"-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.

[0057] ・「-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.

[0058] "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.

[0059] "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.

[0060] "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.

[0061] - "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.

[0062] - "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.

[0063] - "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.

[0064] - "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.

[0065] - "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.

[0066] "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.

[0067] 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.

[0068] 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.

[0069] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.

[0070]

[0071] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically any of the following groups:

[0072]

[0073] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0074] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0075]

[0076] In the general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.

[0077] 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.

[0078] "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.

[0079] "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.

[0080] "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.

[0081] 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).

[0082]

[0083]

[0084] 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.

[0085]

[0086] 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.

[0087]

[0088] 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.

[0089] 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).

[0090]

[0091]

[0092]

[0093] In the general formulae (TEMP-69) to (TEMP-82), Q １ ~Q ９ are each independently a hydrogen atom or a substituent.

[0094]

[0095]

[0096]

[0097]

[0098] In the general formulae (TEMP-83) to (TEMP-102), Q １ ~Q ８ are each independently a hydrogen atom or a substituent.

[0099] The above is the explanation of "substituents described in this specification."

[0100] "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.

[0101]

[0102] 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.

[0103] 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).

[0104]

[0105] 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.

[0106]

[0107] 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.

[0108] 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

[0109] 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.

[0110] 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").

[0111] 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.

[0112] 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.

[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 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heterocyclic group having 5 to 18 ring atoms.

[0114] 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."

[0115] 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.

[0116] 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.

[0117] The compound of the present invention will be described below. The compound of the present invention is represented by the above formula (1). The symbols in formula (1) and each formula contained in formula (1) described below will be described below. Unless otherwise specified, the same symbols have the same meaning. The compound of the present invention represented by formula (1) and each formula contained in formula (1) described below will sometimes be referred to as an "invention compound."

[0118]

[0119] N ＊ is the central nitrogen atom.

[0120] R ａ and R ｂ One of the groups is a substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 18, more preferably 1 to 10, and even more preferably 1 to 6, carbon atoms, and the other is a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 25, and more preferably 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30, preferably 5 to 18, and more preferably 5 to 13 ring atoms. ａ and R ｂ may be bonded to each other to form a substituted or unsubstituted ring.

[0121] In one embodiment of the present invention, R ａ and R ｂPreferably, one of R is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and the other is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms; ａ and R ｂ It is more preferable that one of the groups is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and the other is a substituted or unsubstituted phenyl group.

[0122] The R ａ and R ｂ The unsubstituted alkyl group having 1 to 30 carbon atoms represented by is, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, or a dodecyl group, 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, a t-butyl group, or a pentyl group, more 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, and even more preferably a methyl group or a t-butyl group.

[0123] The R ａ and R ｂ The unsubstituted aryl group having 6 to 30 ring carbon atoms represented by the formula (I) is, for example, a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, an anthryl group, a benzanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a picenyl group, a pentaphenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a fluorenyl group, a fluoranthenyl group, a perylenyl group, or a triphenylenyl group, and preferably a phenyl group, a biphenylyl group, The alkyl group is preferably a phenyl group, a terphenylyl group, or a naphthyl group, more preferably a phenyl group, a 2-, 3-, or 4-biphenylyl group, a 2-, 3-, or 4-o-terphenylyl group, a 2-, 3-, or 4-m-terphenylyl group, a 2-, 3-, or 4-p-terphenylyl group, or a 1- or 2-naphthyl group, still more preferably a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group, and particularly preferably a phenyl group.

[0124] The R ａ and R ｂ Examples of the unsubstituted aromatic heterocyclic group having 5 to 30 ring atoms represented by the formula (I) include a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, an imidazopyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, an isoxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a tetrazolyl 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, a benzoxazolyl group, a benzothiazolyl group, an indazolyl group, a benzisoxazolyl group, a benzisothiazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, The alkyl group is a phenazinyl group, a phenothiazinyl group, a phenoxazinyl group, a xanthenyl group, a benzofuranyl group, an isobenzofuranyl group, a naphthobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group (a benzothienyl group, the same applies hereinafter), an isobenzothiophenyl group (an isobenzothienyl group, the same applies hereinafter), a naphthobenzothiophenyl group (a naphthobenzothienyl group, the same applies hereinafter), a dibenzothiophenyl group (a dibenzothienyl group, the same applies hereinafter), or a carbazolyl group, and is preferably a benzofuranyl group, an isobenzofuranyl group, a naphthobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, a naphthobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group (a 9-carbazolyl group, or a 1-, 2-, 3-, or 4-carbazolyl group).

[0125] The R ａ and R ｂ The unsubstituted monocyclic ring formed by R is, for example, a benzene ring, a cyclopentane ring, or a cyclohexane ring. ａ and R ｂ The unsubstituted fused ring formed by R is, for example, a naphthalene ring or an anthracene ring. ａ and R ｂare bonded to each other to form an unsubstituted monocyclic ring or an unsubstituted fused ring, R ａ and R ｂ may form a ring together with the fluorene skeleton to which they are bonded to form a spiro ring. The spiro ring is a hydrocarbon ring or a heterocyclic ring, and is selected from a monocyclic ring, a fused ring, a bridged bicyclic ring, and a bridged tricyclic ring. Examples of substituted or unsubstituted spiro rings are shown below, but are not limited to these. * indicates the bonding position of the fluorene skeleton to the benzene ring.

[0126]

[0127] In one embodiment of the present invention, R ａ and R ｂ are preferably not bonded to each other to form a substituted or unsubstituted ring.

[0128] R ２ , R ３ , R ６ and R ７ is a single bond bonded to *1, and R １ , R ４ , R ５ , R ８ , and R that is not a single bond bonded to *1 ２ , R ３ , R ６ and R ７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 18, more preferably 1 to 10, and even more preferably 1 to 6, carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 15, preferably 3 to 10, and more preferably 3 to 6 ring 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. １ , R ４ , R ５ , R ８ and the R which is not a single bond. ２ , R ３ , R ６ and R ７ Adjacent two selected from are not bonded to each other and therefore do not form a ring.

[0129] In one embodiment of the present invention, R ２ or R ７ is preferably a single bond bonded to *1.

[0130] The R １ , R ４ , R ５ , R ８ , and R that is not a single bond bonded to *1 ２ , R ３ , R ６ and R ７ The details of the unsubstituted alkyl group having 1 to 30 carbon atoms represented by R ａ and R ｂ As described above.

[0131] The R １ , R ４ , R ５ , R ８ , and R that is not a single bond bonded to *1 ２ , R ３ , R ６ and R ７ The unsubstituted cycloalkyl group having 3 to 15 ring carbon atoms represented by the formula (I) is, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, or a cyclooctyl group, and preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group.

[0132] The R １ , R ４ , R ５ , R ８ , and R that is not a single bond bonded to *1 ２ , R ３ , R ６ and R ７ The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ａ and R ｂ As described above.

[0133] The R １ , R ４ , R ５ , R ８ , and R that is not a single bond bonded to *1 ２ , R ３, R ６ and R ７ The details of the unsubstituted heterocyclic group having 5 to 13 ring atoms represented by R ａ and R ｂ As described above.

[0134] The R １ , R ４ , R ５ , R ８ , and R that is not a single bond bonded to *1 ２ , R ３ , R ６ and R ７ may all be hydrogen atoms.

[0135] R １１ ~R １４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 18, more preferably 1 to 10, and even more preferably 1 to 6, carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18, preferably 6 to 12, ring carbon atoms. １１ ~R １４ Adjacent two selected from are not bonded to each other and therefore do not form a ring.

[0136] The R １１ ~R １４ The details of the unsubstituted alkyl group having 1 to 30 carbon atoms represented by R ａ and R ｂ As described above.

[0137] The R １１ ~R １４ The details of the unsubstituted aryl group having 6 to 18 ring carbon atoms represented by R ａ and R ｂ As described above.

[0138] The R １１ ~R １４ may all be hydrogen atoms.

[0139] L １ ~L ４are each independently a single bond or an arylene group having 6 to 30, preferably 6 to 25, and more preferably 6 to 12 ring carbon atoms.

[0140] In one embodiment of the present invention, L １ and L ２ are preferably each independently a single bond or an arylene group having 6 to 12 ring carbon atoms. １ may be a single bond, L ２ may be a single bond.

[0141] In one embodiment of the present invention, L ３ is preferably a single bond. ４ is preferably a single bond. ３ and L ４ is preferably a single bond.

[0142] Said L １ ~L ４ The unsubstituted arylene group having 6 to 30 ring carbon atoms represented by the formula (I) is a divalent group obtained by removing one hydrogen atom from an unsubstituted aryl group having 6 to 30 ring carbon atoms. ａ and R ｂ As described above.

[0143] Ar １ and Ar ２ is a group represented by any one of the following formulas (1a) to (1g):

[0144]

[0145] In formula (1a), *21 is L １ or L ２ is the bonding position to R 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, and R １１１ ~R １１５ One selected from is a single bond bonded to *24.１０１ ~R １１５ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. １０１ ~R １０５ adjacent two selected from are not bonded to each other and therefore do not form a ring, １０６ ~R １１０ adjacent two selected from are not bonded to each other and therefore do not form a ring, １１１ ~R １１５ Adjacent two selected from are not bonded to each other and therefore do not form a ring.

[0146] L １ When is a single bond, Ar １ *21 in the group represented by formula (1a) is the central nitrogen atom N ＊ represents the bonding position to ２ When is a single bond, Ar ２ *21 in the group represented by formula (1a) is the central nitrogen atom N ＊ represents the binding position to

[0147] The R that is not a single bond １０１ ~R １１５ The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R ａ and R ｂ As described above.

[0148] The R １０１ ~R １１５ The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ａ and R ｂ As described above.

[0149] * R that is not a single bond bonded to 22 １０１ ~R １０５ may all be hydrogen atoms, and R １０６ ~R １１０ may all be hydrogen atoms, and R １１１ ~R１１５ may all be hydrogen atoms.

[0150] m is 0 or 1, n is 0 or 1, and l is 0 or 1. When m is 0, n is 1, and l is 0 or 1, *22 is L １ or L ２ (*22 represents *21), and when m is 0, n is 0, and l is 1, *23 represents L １ or L ２ (*23 represents *21), and when m is 0, n is 0, and l is 0, *24 represents L １ or L ２ represents the bonding position to (*24 represents *21).

[0151] In one embodiment of the present invention, m is 0, n is 0, and 1 is 0. In this case, *24 represents *21, and formula (1a) is represented by the following formula.

[0152] In another embodiment of the present invention, m is 1, n is 0, and l is 0. In this case, *24 represents *22, and formula (1a) is represented by the following formula:

[0153] In yet another embodiment of the present invention, m is 0, n is 1, and l is 0. In this case, *22 represents *21, *24 represents *23, and formula (1a) is represented by the following formula:

[0154] In yet another embodiment of the present invention, m is 0, n is 0, and 1 is 1. In this case, *23 represents *21, and formula (1a) is represented by the following formula:

[0155] In yet another embodiment of the present invention, m is 1, n is 1, and l is 0. In this case, *24 represents *23, and formula (1a) is represented by the following formula:

[0156] In yet another embodiment of the present invention, m is 1, n is 0, and l is 1. In this case, *23 represents *22, and formula (1a) is represented by the following formula:

[0157] In yet another embodiment of the present invention, m is 0, n is 1, and l is 1. In this case, *22 represents *21, and formula (1a) is represented by the following formula:

[0158] In yet another embodiment of the present invention, m is 1, n is 1, and l is 1. In this case, formula (1a) is represented by the following formula:

[0159] The group represented by formula (1a) preferably satisfies at least one of the following conditions (i) to (iii): (i) R １０１ or R １０５ is a single bond bonded to *22 (ii) R １０６ or R １１０ is a single bond bonded to *23 (iii) R １１１ or R １１５ is a single bond that bonds to *24

[0160] R １１６ ~R １２０ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 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. １１６ ~R １２０ Adjacent two selected from are not bonded to each other and therefore do not form a ring.

[0161] The R １１６ ~R １２０ The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R ａ and R ｂ As described above.

[0162] The R １１６ ~R １２０ The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ａ and R ｂ As described above.

[0163] The R １１６ ~R １２０The details of the unsubstituted aryl group having 5 to 13 ring carbon atoms represented by R ａ and R ｂ As described above.

[0164] The R １１６ ~R １２０ may all be hydrogen atoms.

[0165] The group represented by formula (1a) is preferably represented by the following formula: In the following formula, R has been omitted for simplicity.

[0166] Formula (1b) is expressed by the following formula.

[0167]

[0168] In formula (1b), *25 is L １ or L ２ is the bonding position to R １２１ ~R １２８ One selected from is a single bond bonded to *26. １２１ ~R １２８ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. １２１ ~R １２８ adjacent two selected from are not bonded to each other and therefore do not form a ring. １ is a p-phenylene group, and Ar １ is represented by formula (1b), R in the group represented by formula (1b) bonded to the p-phenylene group １２１ , R １２４ , R １２５ , and R １２８ one selected from is a single bond bonded to *26, ２ is a p-phenylene group, and Ar ２ is represented by formula (1b), R in the group represented by formula (1b) bonded to the p-phenylene group １２１ , R １２４ , R １２５ , and R １２８One selected from is a single bond bonded to *26.

[0169] L １ When is a single bond, Ar １ *25 in the group represented by formula (1b) is the central nitrogen atom N ＊ represents the bonding position to ２ When is a single bond, Ar ２ *25 in the group represented by formula (1b) is the central nitrogen atom N ＊ represents the binding position to

[0170] The R １２１ ~R １２８ The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R ａ and R ｂ 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 ａ and R ｂ As described above.

[0171] In one embodiment of the present invention, R １２１ is preferably a single bond attached to *26, and in another embodiment, R １２２ is preferably a single bond bonded to *26. R that is not a single bond bonded to *26 １２１ ~R １２８ may all be hydrogen atoms.

[0172] Formula (1c) is expressed by the following formula.

[0173]

[0174] In formula (1c), *27 is L １ or L ２ is the bonding position to R １３１ ~R １４０ One selected from is a single bond bonded to *28. １３１ ~R １４０are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 6, carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. １３１ ~R １４０ Adjacent two selected from are not bonded to each other and therefore do not form a ring.

[0175] L １ When is a single bond, Ar １ *27 in the group represented by formula (1c) is the central nitrogen atom N ＊ represents the bonding position to ２ When is a single bond, Ar ２ *27 in the group represented by formula (1c) is the central nitrogen atom N ＊ represents the binding position to

[0176] The R １３１ ~R １４０ The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R ａ and R ｂ 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 ａ and R ｂ In one aspect of the present invention, R １３１ However, in other embodiments, R １３２ However, in still another embodiment, R １４０ is preferably a single bond bonded to *28. R that is not a single bond bonded to *28 １３１ ~R １４０ may all be hydrogen atoms.

[0177] Formula (1d) is expressed by the following formula.

[0178]

[0179] In formula (1d), *29 is L １ or L ２ is the bonding position to R １４１ ~R １５２One selected from is a single bond bonded to *30. １４１ ~R １５２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 6, carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. １４１ ~R １５２ Adjacent two selected from are not bonded to each other and therefore do not form a ring structure.

[0180] L １ When is a single bond, Ar １ *29 in the group represented by formula (1d) is the central nitrogen atom N ＊ represents the bonding position to ２ When is a single bond, Ar ２ *29 in the group represented by formula (1d) is the central nitrogen atom N ＊ represents the binding position to

[0181] The R １４１ ~R １５２ The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R ａ and R ｂ As described above with respect to the R １４１ ~R １５２ The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ａ and R ｂ * R that is not a single bond bonded to 30 １４１ ~R １５２ may all be hydrogen atoms.

[0182] Formula (1e) is expressed by the following formula.

[0183]

[0184] In formula (1e), *31 is L １ or L ２ is the bonding position to R １６１ ~R １６５ is a single bond bonded to *32, and R １６１ ~R１６５ The other one selected from is a single bond bonded to *33. R which is not a single bond bonded to said *32 and is not a single bond bonded to said *33 １６１ ~R １６５ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, or an unsubstituted phenyl group. R is not a single bond bonded to *32, and is not a single bond bonded to *33. １６１ ~R １６５ Adjacent two selected from are not bonded to each other and therefore do not form a ring.

[0185] L １ When is a single bond, Ar １ *31 in the group represented by formula (1e) is the central nitrogen atom N ＊ represents the bonding position to ２ When is a single bond, Ar ２ *31 in the group represented by formula (1e) is the central nitrogen atom N ＊ represents the binding position to

[0186] R that is not a single bond bonded to the *32 and is not a single bond bonded to the *33 １６１ ~R １６５ The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R ａ and R ｂ As described above with respect to the R １４１ ~R １５２ The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ａ and R ｂ It is the same as described above with respect to *32 and *33. １６１ ~R １６５ may all be hydrogen atoms.

[0187] R １７１ ~R １７５ and R １８１ ~R １８５ are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms. １７１ ~R１７５ adjacent two 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; １８１ ~R １８５ 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 not form a ring.

[0188] The R １７１ ~R １７５ and R １８１ ~R １８５ The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R ａ and R ｂ As described above with respect to the R １７１ ~R １７５ and R １８１ ~R １８５ may all be hydrogen atoms.

[0189] 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.

[0190]

[0191] Formula (1f) is expressed by the following formula.

[0192]

[0193] In formula (1f), *34 is L １ or L ２ X is an oxygen atom, a sulfur atom, or an NR Ａ X is preferably an oxygen atom or NR Ａ is.

[0194] R １９１ ~R １９８ and R Ａ One selected from is a single bond bonded to *35. 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.

[0195] L １ When is a single bond, Ar １ *34 of the group represented by formula (1f) is the central nitrogen atom N ＊ represents the bonding position to ２ When is a single bond, Ar ２ *34 of the group represented by formula (1f) is the central nitrogen atom N ＊ represents the binding position to

[0196] The R Ａ The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R ａ and R ｂ 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 ａ and R ｂ As described above.

[0197] The R that is not a single bond １９１ ~R １９８ 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. １９１ ~R １９８ 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 not form a ring.

[0198] The R that is not a single bond １９１ ~R １９８ The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R ａ and R ｂ The R that is not a single bond is as described above. １９１ ~R １９８ The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ａ and R ｂ The R that is not a single bond is as described above.１９１ ~R １９８ The details of the unsubstituted heterocyclic group having 5 to 13 ring atoms represented by R ａ and R ｂ As described above.

[0199] * Not a single bond bonded to 35, R １９１ ~R １９８ may all be hydrogen atoms.

[0200] When X is an oxygen atom or a sulfur atom, it is preferably R １９１ ~R １９４ One selected from the above is a single bond bonded to *35. X is NR Ａ When R １９１ ~R １９４ and R Ａ One selected from is a single bond bonded to *35. Ａ is particularly preferably a single bond or an unsubstituted phenyl group bonded to *35.

[0201] Formula (1g) is represented by the following formula.

[0202]

[0203] In formula (1g), *36 is L １ or L ２ is the bonding position to R B , R C , and R ２０１ ~R ２０８ One selected from is a single bond bonded to *37. B and R C are each independently 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. B and R C may be bonded to each other to form a substituted or unsubstituted ring.

[0204] L １ When is a single bond, Ar １*36 in the group represented by formula (1g) is the central nitrogen atom N ＊ represents the bonding position to ２ When is a single bond, Ar ２ *36 in the group represented by formula (1g) is the central nitrogen atom N ＊ represents the binding position to

[0205] In one embodiment of the present invention, R B and R C are preferably each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a phenyl group.

[0206] The R that is not a single bond B and R C The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R ａ and R ｂ The R that is not a single bond is as described above. B and R C The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ａ and R ｂ The R that is not a single bond is as described above. B and R C The details of the unsubstituted heterocyclic group having 5 to 13 ring atoms represented by R ａ and R ｂ The R that is not a single bond is as described above. B and R C The details of the unsubstituted ring formed by bonding together are as follows: ａ and R ｂ As described above.

[0207] The R that is not a single bond ２０１ ~R ２０８ 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. ２０１ ~R ２０８Adjacent two selected from are not bonded to each other and therefore do not form a ring.

[0208] The R that is not a single bond ２０１ ~R ２０８ The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R ａ and R ｂ The R that is not a single bond is as described above. ２０１ ~R ２０８ The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ａ and R ｂ The R that is not a single bond is as described above. ２０１ ~R ２０８ The details of the unsubstituted heterocyclic group having 5 to 13 ring atoms represented by R ａ and R ｂ As described above.

[0209] In one embodiment of the present invention, R ２０２ or R ２０７ is preferably a single bond bonded to *37.

[0210] In one embodiment of the present invention, Ar １ and Ar ２ At least one of the above is preferably a group represented by formula (1a) or (1g).

[0211] In one embodiment of the present invention, Ar １ or Ar ２ is a group represented by the formula (1a), and the group represented by the formula (1a) preferably satisfies at least one of the following (i) to (iii): (i) R １０１ or R １０５ is a single bond bonded to *22 (ii) R １０６ or R １１０ is a single bond bonded to *23 (iii) R １１１ or R １１５ is a single bond that bonds to *24

[0212] In one embodiment of the present invention, Ar １or Ar ２ is a group represented by the formula (1g), and in the group represented by the formula (1g), R B and R C are preferably each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted phenyl group.

[0213] In one embodiment of the present invention, Ar １ or Ar ２ is a group represented by the formula (1g), and in the group represented by the formula (1g), R ２０２ or R ２０７ is preferably a single bond bonded to *37.

[0214] 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 compound (1) by using partially or entirely deuterated starting compounds. Therefore, in one embodiment of the present invention, compound (1) 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.

[0215] At least one hydrogen atom selected from the following hydrogen atoms may be a deuterium atom. In the following, "substituted or unsubstituted", the number of carbon atoms and the number of atoms are omitted. ａ and R ｂ When R is an alkyl group, an aryl group, or a heterocyclic group, a hydrogen atom contained therein; １ ~R ５ , R ８ , and R that is not a single bond bonded to *1 ６ and R ７ a hydrogen atom represented by R in formula (1); １ ~R ５ , R ８ , and R that is not a single bond bonded to *1 ６ and R ７When R is an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group, a hydrogen atom contained therein; １１ ~R １４ a hydrogen atom represented by R in formula (1); １１ ~R １４ When L is an alkyl group or an aryl group, a hydrogen atom contained therein; １ ~L ４ is an arylene group, a hydrogen atom thereof; R which is not a single bond bonded to *22 in formula (1a) １０１ ~R １０５ , *23 is not a single bond R １０６ ~R １１０ , * R that is not a single bond bonded to 24 １１１ ~R １１５ a hydrogen atom represented by R which is not a single bond bonded to *22 in formula (1a); １０１ ~R １０５ , *23 is not a single bond R １０６ ~R １１０ , * R that is not a single bond bonded to 24 １１１ ~R １１５ When R is an alkyl group or an aryl group, a hydrogen atom contained therein; １１６ ~R １２０ a hydrogen atom represented by R in formula (1a); １１６ ~R １２０ is an alkyl group, an aryl group, or a heterocyclic group, a hydrogen atom contained therein; R which is not a single bond bonded to *26 in formula (1b) １２１ ~R １２８ a hydrogen atom represented by R which is not a single bond bonded to *26 in formula (1b); １２１ ~R １２８ is an alkyl group or an aryl group, a hydrogen atom thereof; R which is not a single bond bonded to *28 in formula (1c) １３１ ~R １４０ a hydrogen atom represented by R which is not a single bond bonded to *28 in formula (1c); １３１ ~R １４０ is an alkyl group or an aryl group, a hydrogen atom thereof; R which is not a single bond bonded to *30 in formula (1d) １４１ ~R １５２a hydrogen atom represented by R which is not a single bond bonded to *30 in formula (1d); １４１ ~R １５２ is an alkyl group or an aryl group, a hydrogen atom thereof; R which is not a single bond bonded to *32 in formula (1e) and is not a single bond bonded to *33 １６１ ~R １６５ a hydrogen atom represented by the formula (1e) １６１ ~R １６５ When R is an alkyl group or a phenyl group, a hydrogen atom contained therein; １７１ ~R １７５ and R １８１ ~R １８５ a hydrogen atom represented by R in formula (1e); １７１ ~R １７５ and R １８１ ~R １８５ is an alkyl group, the hydrogen atom thereof; R which is not a single bond bonded to *35 in formula (1f) Ａ is an alkyl group or an aryl group, a hydrogen atom thereof; R which is not a single bond bonded to *35 in formula (1f) １９１ ~R １９８ a hydrogen atom represented by R which is not a single bond bonded to *35 in formula (1f); １９１ ~R １９８ When R is an alkyl group, an aryl group, or a heterocyclic group, a hydrogen atom contained therein; B and R C is an alkyl group, an aryl group, or a heterocyclic group, a hydrogen atom contained therein; R which is not a single bond bonded to *37 in formula (1g) ２０１ ~R ２０８ a hydrogen atom represented by R which is not a single bond bonded to *37 in formula (1g); ２０１ ~R ２０８ When is an alkyl group, an aryl group, or a heterocyclic group, a hydrogen atom contained therein.

[0216] The deuteration rate of the invention compound depends on the deuteration rate of the raw material compound used. Even when a raw material with a predetermined deuteration rate is used, a certain proportion of naturally occurring proton isotopes may be contained. Therefore, the deuteration rate of the invention compound shown below includes a ratio that takes 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 rate 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.

[0217] 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%.

[0218] When the "substituted or unsubstituted XX group" included in the definition of each formula above is a substituted XX group, the details of the substituent are as described in "Substituents when "substituted or unsubstituted" is used", and is preferably an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring carbon atoms, or an aromatic heterocyclic group having 5 to 13 ring atoms, more preferably an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 12 ring carbon atoms. The details of each group are as described above.

[0219] 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.

[0220] 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.

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352] Material for Organic EL Device The material for organic EL devices of the present invention contains an invention compound. The content of the invention compound in the material for organic EL devices 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 devices of the present invention is useful for producing organic EL devices.

[0353] Organic EL device The organic EL device of the present invention comprises 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.

[0354] The organic EL device 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.

[0355] 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 / first fluorescent-emitting layer / second fluorescent-emitting layer / electron transport layer ( / electron injection layer) (c) (hole injection layer / ) hole transport layer / phosphorescent-emitting layer / space layer / fluorescent-emitting layer / electron transport layer ( / electron injection layer) (d) (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) (e) (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) (f) (hole injection layer / ) hole transport layer / electron blocking layer / fluorescent-emitting layer / electron transport layer ( / electron injection layer) (g) (hole injection layer / ) hole transport layer / exciton blocking layer / fluorescent-emitting layer / electron transport layer ( / electron injection layer) (h) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent-emitting layer / electron transport layer ( / electron injection layer) (i) (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) (j) (hole injection layer / ) hole transport layer / fluorescent-emitting layer / hole blocking layer / electron transport layer ( / electron injection layer) (k) (hole injection layer / ) hole transport layer / fluorescent-emitting layer / exciton blocking layer / electron transport layer ( / electron injection layer) (l) (hole injection layer / ) first hole transport layer / second hole transport layer / first fluorescent-emitting layer / second fluorescent-emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer) (m) (hole injection layer / ) first hole transport layer / second hole transport layer / third hole transport layer / first fluorescent-emitting layer / second fluorescent-emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer) (n) (hole injection layer / ) first hole transport layer / second hole transport layer / third hole transport layer / fluorescent-emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer)

[0356] 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.

[0357] 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.

[0358] FIG. 1 is a schematic diagram showing an example of the configuration of an organic EL element of the present invention. The organic EL element 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 exciton generation efficiency in the emitting layer 5.

[0359] 2 is a schematic diagram showing another configuration of an organic EL element 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 transporting region disposed between the anode 3 and the emitting layer 5 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 emitting layer 5 and the cathode 4 is formed of a first electron transporting layer 7a and a second electron transporting layer 7b.

[0360] 3 is a schematic diagram showing another configuration of an organic EL element 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 an emitting layer 5. The hole transporting region disposed between the anode 3 and the emitting layer 5 is formed of a hole injection layer 6a, a first hole transporting layer 6b, a second hole transporting layer 6c, and a third hole transporting layer 6d. The electron transporting region disposed between the emitting layer 5 and the cathode 4 is formed of a first electron transporting layer 7a and a second electron transporting layer 7b.

[0361] In the present invention, a host combined with a fluorescent dopant material (fluorescent-emitting material) is referred to as a fluorescent host, and a host combined with a phosphorescent dopant material 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.

[0362] 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.

[0363] 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).

[0364] 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.

[0365] Hole Transporting Zone As described above, the organic layer may include a hole transporting zone between the anode and the light emitting layer. The hole transporting zone is composed of a hole injection layer, a hole transporting layer, an electron blocking layer, etc. It is preferable that the hole transporting zone contains the compound of the invention. It is preferable that at least one of these layers constituting the hole transporting layer contains the compound of the invention, and it is particularly preferable that the compound of the invention be contained in the hole transporting layer.

[0366] 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.

[0367] 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.

[0368] 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.

[0369] 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).

[0370] 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.

[0371] Furthermore, it is also preferable to use an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K).

[0372]

[0373] (In the above formula, R ２２１ ~R ２２６ each independently represents a cyano group, —CONH ２ , a carboxyl group, or -COOR ２２７ (R ２２７ represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms). ２２１ and R ２２２ , R ２２３ and R ２２４ , and R ２２５ and R ２２６ Two adjacent groups selected from the following may be bonded to each other to form a group represented by —CO—O—CO—. ２２７ 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.

[0374] 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.

[0375] 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 in the two-layer structure or the third hole transport layer in the three-layer structure, is preferably adjacent to 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 and the light-emitting layer in the multilayer structure. When the hole transport layer has a two-layer structure, at least one of the first hole transport layer and the second hole transport layer contains the invention compound. That is, the invention compound is contained only in the first hole transport layer, only in the second hole transport layer, or in both the first and second hole transport layers. In one embodiment of the present invention, the invention compound is preferably contained in the second hole transport layer. That is, the invention compound is preferably contained only in the second hole transport layer, or in both the first and second hole transport layers. When the hole transport layer has a three-layer structure, at least one of the first to third hole transport layers contains the invention compound. That is, the invention compound is contained in only one layer selected from the first to third hole transport layers (only the first hole transport layer, only the second hole transport layer, or only the third hole transport layer), only two layers selected from the first to third hole transport layers (only the first hole transport layer and the second hole transport layer, only the first hole transport layer and the third hole transport layer, or only the second hole transport layer and the third hole transport layer), or all of the first to third hole transport layers. In one embodiment of the present invention, the invention compound is preferably contained in the third hole transport layer. That is, it is preferable that the invention compound is contained only in the third hole transport layer, or that the invention compound is contained in the third hole transport layer and one or both of the first hole transport layer and the second hole transport layer.In one embodiment of the present invention, the invention compound contained in each of the hole transport layers is preferably a proteasome, from the viewpoint of production costs. The proteasome refers to an invention compound in which all hydrogen atoms are proteasomes. Accordingly, the present invention encompasses an organic EL device in which one or both of the first hole transport layer and the second hole transport layer (in the case of a two-layer structure), and at least one of the first to third hole transport layers, contain an invention compound substantially consisting of a proteasome. The phrase "an invention compound substantially consisting of a proteasome" means that the content of the proteasome 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 including 100%).

[0376] 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.

[0377] 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.

[0378] In the organic EL element of the present invention having a hole transport layer with a two-layer structure, the first hole transport layer preferably contains one or more compounds represented by the following formula (11) or formula (12). In the organic EL element of the present invention having a hole transport layer with a three-layer structure, one or both of the first hole transport layer and the second hole transport layer preferably contain one or more compounds represented by the following formula (11) or (12). In the organic EL element of the present invention having a hole transport layer with an n-layer structure (n is an integer of 4 or more), at least one of the first hole transport layer to the (n-1)th hole transport layer preferably contains one or more compounds represented by the following formula (11) or formula (12).

[0379] [In the formula (11) and the formula (12), L Ａ１ , L Ｂ１ , L Ｃ１ , L Ａ２ , L Ｂ２ , L Ｃ２ and L Ｄ２ are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, k is 1, 2, 3, or 4, and when k is 1, L Ｅ２is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, and when k is 2, 3, or 4, there are 2, 3, or 4 L Ｅ２ are the same or different from each other, and when k is 2, 3, or 4, a plurality of L Ｅ２ are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, Ｅ２ A is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, １ , B １ , C １ , A ２ , B ２ , C ２ , and D ２ each independently represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or —Si(R′ ９０１ ) (R' ９０２ ) (R' ９０３ ) and R' ９０１ , R' ９０２ and R' ９０３ R' are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; ９０１ When there are a plurality of R' ９０１ are the same or different from each other, and R' ９０２ When there are a plurality of R' ９０２ are the same or different from each other, and R' ９０３ When there are a plurality of R' ９０３ are the same as or different from each other.

[0380] In formula (11) and formula (12), A1, B1, C1, A2, B2, C2, and D2 are preferably each independently selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group. More preferably, at least one of A1, B1, and C1 in formula (11), and at least one of A2, B2, C2, and D2 in formula (12) are a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0381] The fluorenyl group which can be represented by A1, B1, C1, A2, B2, C2, and D2 may have a substituent at the 9-position, such as a 9,9-dimethylfluorenyl group or a 9,9-diphenylfluorenyl group. Furthermore, the substituents at the 9-position may be bonded together to form a ring, such as a fluorene skeleton or a xanthene skeleton.

[0382] L Ａ１ , L Ｂ１ , L Ｃ１ , L Ａ２ , L Ｂ２ , L Ｃ２ and L Ｄ２ are preferably each independently a single bond or a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.

[0383] Specific examples of the compounds represented by formula (11) and formula (12) include the following compounds.

[0384]

[0385] 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 organic EL element according to the present invention, the light-emitting layer is a single layer. In another embodiment of the organic EL element according to the present invention, the light-emitting layer includes a first light-emitting layer and a second light-emitting layer.

[0386] 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.

[0387] 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.

[0388] Red fluorescent materials that can be used in the light-emitting layer include tetracene derivatives, diamine derivatives, etc. 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).

[0389] In one embodiment of the present invention, the light-emitting layer preferably contains a fluorescent light-emitting material (fluorescent dopant material).

[0390] 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).

[0391] 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)).

[0392] 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).

[0393] 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).

[0394] 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.

[0395] 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.

[0396] 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.

[0397] In particular, in the case of a blue fluorescent element, it is preferable to use the following anthracene compound as the host material.

[0398]

[0399]

[0400]

[0401] In one embodiment of the organic EL device according to the present invention, when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, at least one of the components constituting the first light-emitting layer is different from the components constituting the second light-emitting layer. For example, the dopant material contained in the first light-emitting layer may be different from the dopant material contained in the second light-emitting layer, or the host material contained in the first light-emitting layer may be different from the host material contained in the second light-emitting layer.

[0402] In the organic EL device of the present invention, the light-emitting layer may contain a light-emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less (hereinafter, sometimes simply referred to as a "fluorescent compound").

[0403] The method for measuring the main peak wavelength of a compound is as follows. A 5 μmol / L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K). The emission spectrum can be measured using a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measuring device is not limited to the device used here. The peak wavelength of the emission spectrum at which the emission intensity is maximum is defined as the main peak wavelength. Note that in this specification, the main peak wavelength may also be referred to as the fluorescence emission main peak wavelength (FL-peak).

[0404] The fluorescent compound may be the dopant material or the host material.

[0405] When the light-emitting layer is a single layer, only one of the dopant material and the host material may be the fluorescent compound, or both may be the fluorescent compound. When the light-emitting layer includes a first light-emitting layer (anode side) and a second light-emitting layer (cathode side), only one of the first light-emitting layer and the second light-emitting layer may contain the fluorescent compound, or both may contain the fluorescent compound. When the first light-emitting layer includes the fluorescent compound, only one of the dopant material and the host material included in the first light-emitting layer may be the fluorescent compound, or both may be the fluorescent compound. When the second light-emitting layer includes the fluorescent compound, only one of the dopant material and the host material included in the second light-emitting layer may be the fluorescent compound, or both may be the fluorescent compound.

[0406] 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, and 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.

[0407] 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.

[0408] 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).

[0409] 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).

[0410] 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).

[0411] 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.

[0412] 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.

[0413] 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.

[0414] 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.

[0415] 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.

[0416] 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.

[0417] 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.

[0418] 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.

[0419] In the organic EL device of the present invention having a hole transport layer of a two-layer or three-layer structure, the total thickness of the first hole transport layer and the second hole transport layer is preferably 30 nm or more and 150 nm or less, more preferably 40 nm or more and 130 nm or less. In one embodiment of the present invention, the thickness of the second hole transport layer of the two-layer or three-layer structure is preferably 5 nm or more, more preferably 20 nm or more, even more preferably 25 nm or more, particularly preferably 35 nm or more, and preferably 100 nm or less. In another embodiment of the present invention, the thickness of the hole transport layer adjacent to the light-emitting layer is preferably 5 nm or more, more preferably 20 nm or more, even more preferably 25 nm or more, particularly preferably 30 nm or more, and preferably 100 nm or less. In the organic EL element of the present invention having a hole transport layer of a two-layer structure or a three-layer structure, the ratio of the thickness D2 of the second hole transport layer to the thickness D1 of the first hole transport layer is preferably 0.3 < D2 / D1 < 4.0, more preferably 0.5 < D2 / D1 < 3.5, and even more preferably 0.75 < D2 / D1 < 3.0.

[0420] Preferred embodiments of the organic EL device of the present invention include, for example, (1) an organic EL device having a two-layer hole transport layer: - a first embodiment in which the second hole transport layer contains the compound of the invention, and the first hole transport layer does not contain the compound of the invention; - a second embodiment in which both the first hole transport layer and the second hole transport layer contain the compound of the invention; - a third embodiment in which the first hole transport layer contains the compound of the invention, and the second hole transport layer does not contain the compound of the invention; (2) an organic EL device having a three-layer hole transport layer: - a fourth embodiment in which the first hole transport layer contains the compound of the invention, and the second and third hole transport layers do not contain the compound of the invention; - a fifth embodiment in which the second hole transport layer contains the compound of the invention, and the first and third hole transport layers do not contain the compound of the invention; - a sixth embodiment in which the third hole transport layer contains the compound of the invention, and the first and second hole transport layers do not contain the compound of the invention; - a seventh embodiment in which the first and second hole transport layers contain the compound of the invention, and the third hole transport layer does not contain the compound of the invention; - An eighth embodiment in which the first and third hole transport layers contain the compound of the invention, and the second hole transport layer does not contain the compound of the invention; - A tenth embodiment in which the second and third hole transport layers contain the compound of the invention, and the first hole transport layer does not contain the compound of the invention; - A tenth embodiment in which all of the first to third hole transport layers contain the compound of the invention.

[0421] The organic EL element according to one embodiment of the present invention can be used in electronic devices such as display devices and light-emitting devices. Examples of display devices include display components such as organic EL panel modules, televisions, mobile phones, tablets, and personal computers. Examples of light-emitting devices include lighting fixtures and vehicle lamps.

[0422] The organic EL element can be used in display components such as organic EL panel modules, display devices for televisions, mobile phones, personal computers, etc., and electronic devices such as light-emitting devices for lighting and vehicle lamps.

[0423] The present invention will be described in more detail below using examples, but the present invention is not limited to the following examples.

[0424] Invention compounds used in the production of organic EL devices (I) in Examples 1 to 3

[0425] Comparative compounds used in the production of organic EL devices (I) of Comparative Examples 1 and 2

[0426] Other compounds used in the production of organic EL devices (I) in Examples 1 to 3 and Comparative Examples 1 and 2

[0427] Preparation of Organic EL Device (I) Example 1 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, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was 130 nm. The cleaned glass substrate with the ITO transparent electrode was attached to a substrate holder in a vacuum deposition apparatus, and first, compound HT-1 and compound HA were co-deposited on the surface on which the transparent electrode was formed, covering the transparent electrode, to form a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-1 to compound HA (HT-1:HA) 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 40 nm. Next, compound Inv-1 was vapor-deposited on this first hole transport layer to form a second hole transport layer with a thickness of 40 nm. Next, compound HT-2 was vapor-deposited on this second hole-transporting layer to form a third hole-transporting layer with a thickness of 5 nm. Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited on this third hole-transporting layer to form a first light-emitting layer with a thickness of 20 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 99:1. Next, compound ET-1 was vapor-deposited on this light-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 25 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50. Next, Yb was vapor-deposited on this second electron-transporting layer to form an electron-injecting electrode with a thickness of 1 nm. Then, metal Al was vapor-deposited onto the electron-injecting electrode to form a metal cathode with a thickness of 50 nm. The layer structure of the organic EL device of Example 1 obtained in this manner is shown below: ITO (130) / HT-1:HA=97:3 (10) / HT-1 (40) / Inv-1 (40) / HT-2 (5) / BH-1:BD-1=99:1 (20) / ET-1 (5) / ET-2:Liq=50:50 (25) / Yb (1) / Al (50). In the above layer structure, the numbers in parentheses indicate the film thickness (nm), and the ratios are mass ratios.

[0428] Examples 2 and 3 Organic EL devices (I) were fabricated in the same manner as in Example 1, except that in Example 2, compound Inv-4 was used instead of compound Inv-1, and in Example 3, compound Inv-5 was used instead.

[0429] Comparative Examples 1 and 2 Organic E(I)L elements were fabricated in the same manner as in Example 1, except that in Comparative Example 1, comparative compound Ref-1 was used instead of compound Inv-1, and in Comparative Example 2, comparative compound Ref-2 was used instead.

[0430] Evaluation of Organic EL Element (I) The driving voltage and external quantum efficiency of the obtained organic EL element (I) were measured. (1) Measurement of driving voltage ２ The voltage (unit: V) was measured when a voltage was applied to the organic EL element (I) so that the voltage was 10 mA / cm at room temperature. The results are shown in Table 1. (2) Measurement of external quantum efficiency (EQE) The obtained organic EL element (I) was ２ The 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.

[0431]

[0432] Invention compounds used in the production of organic EL devices (II) in Examples 4 to 7

[0433] Comparative compounds used in the production of organic EL device (II) of Comparative Example 2

[0434] Other compounds used in the production of organic EL devices (II) in Examples 4 to 7 and Comparative Example 3

[0435] Preparation of Organic EL Element (II) Example 4 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, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was 130 nm. The cleaned glass substrate with the ITO transparent electrode was attached to a substrate holder in a vacuum deposition apparatus, and first, compound Inv-1 and compound HA were co-deposited on the surface on which the transparent electrode was formed, covering the transparent electrode, to form a hole injection layer with a thickness of 10 nm. The mass ratio of compound Inv-1 to compound HA (Inv-1:HA) was 97:3. Next, compound Inv-1 was vapor-deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, compound HT-4 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 25 nm. The mass ratio of compound BH-2 to compound BD-2 (BH-2:BD-2) was 96:4. Next, compound ET-3 was deposited on this emitting layer to form a first electron-transporting layer with a thickness of 10 nm. Next, compound ET-4 was deposited on this first electron-transporting layer to form a second electron-transporting layer with a thickness of 15 nm. 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 structure of the organic EL device (II) of Example 4 obtained in this manner is shown below. ITO (130) / Inv-1:HA=97:3 (10) / Inv-1 (80) / HT-4 (10) / BH-2:BD-2=96:4 (25) / ET-3 (10) / ET-4 (15) / LiF (1) / Al (50) In the above layer structure, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

[0436] Examples 5 to 7 Organic EL devices (II) were prepared in the same manner as in Example 4, except that in Example 5, compound Inv-6, compound Inv-7, and compound Inv-8 were used instead of compound Inv-1, respectively.

[0437] Comparative Example 3 Organic EL devices (II) were fabricated in the same manner as in Example 4, except that the comparative compound Ref-2 was used instead of the invention compound Inv-1.

[0438] Evaluation of Organic EL Element (II) The driving voltage and external quantum efficiency of the obtained organic EL element (II) were measured in the same manner as for the organic EL element (I). The results are shown in Table 2.

[0439]

[0440] Invention compounds used in the production of organic EL devices (III) in Examples 8 to 17

[0441] Comparative compounds used in the production of organic EL devices (III) of Comparative Examples 4 and 5

[0442] Other compounds used in the production of organic EL devices in Examples 8 to 17 and Comparative Examples 4 and 5

[0443]

[0444] Preparation of Organic EL Element (III) Example 8 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, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was 130 nm. The cleaned glass substrate with the ITO transparent electrode was attached to a substrate holder in a vacuum deposition apparatus, and first, compound HT-1 and compound HA were co-deposited on the surface on which the transparent electrode was formed, covering the transparent electrode, to form a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-1 to compound HA (HT-1:HA) 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 40 nm. Next, compound Inv-2 was vapor-deposited on this first hole transport layer to form a second hole transport layer with a thickness of 45 nm. Next, compound HT-6 was vapor-deposited on this second hole-transporting layer to form a third hole-transporting layer with a thickness of 5 nm. Next, compound BH-1 (host material) and compound BD-3 (dopant material) were co-deposited on this third hole-transporting layer to form a first light-emitting layer with a thickness of 5 nm. The mass ratio of compound BH-1 to compound BD-3 (BH-1:BD-3) was 99:1. Next, compound BH-5 (host material) and compound BD-3 (dopant material) were co-deposited on this first light-emitting layer to form a second light-emitting layer with a thickness of 20 nm. The mass ratio of compound BH-5 to compound BD-3 (BH-5:BD-3) was 99:1. Next, compound ET-1 was vapor-deposited on this second light-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 transport layer to form a second electron transport layer with a film thickness of 31 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50. Next, Liq was deposited on this second electron transport layer to form an electron injection electrode with a film thickness of 1 nm. Then, metal Al was deposited on this electron injection electrode to form a metal cathode with a film thickness of 80 nm. The layer structure of the organic EL device (III) of Example 8 obtained in this manner is shown below.ITO (130) / HT-1:HA=97:3 (10) / HT-1 (40) / Inv-2 (45) / HT-6 (5) / BH-1:BD-3=99:1 (5) / BH-5:BD-3=99:1 (20) / ET-1 (5) / ET-2:Liq=50:50 (31) / Liq (1) / Al (80) In the above layer structure, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

[0445] Example 9 An organic EL device (III) was produced in the same manner as in Example 8, except that compound Inv-3 was used instead of compound Inv-2.

[0446] Example 10 An organic EL device (III) was prepared in the same manner as in Example 8, except that the compound Inv-9 was used instead of the compound Inv-2.

[0447] Example 11 An organic EL device (III) was produced in the same manner as in Example 8, except that the compound BD-4 was used instead of the compound BD-3.

[0448] Example 12 An organic EL device (III) was prepared in the same manner as in Example 8, except that instead of forming a 20 nm-thick second emitting layer by co-depositing compound BH-5 (host material) and compound BD-3 (dopant material) on the first emitting layer, a 20 nm-thick second emitting layer was formed by co-depositing compound BH-4 (host material), compound BH-7 (host material), and compound BD-3 (dopant material). The mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 70:30, and the concentration of compound BD-3 was 1 mass % with respect to the entire second emitting layer.

[0449] Example 13 An organic EL element (III) was produced in the same manner as in Example 12, except that the mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 50:50.

[0450] Example 14 An organic EL element (III) was prepared in the same manner as in Example 12, except that the mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 30:70.

[0451] Example 15 An organic EL element (III) was produced in the same manner as in Example 12, except that the mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 20:80.

[0452] Example 16 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 ITO transparent electrode was attached to a substrate holder in a vacuum deposition apparatus, and first, compound HT-1 and compound HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, forming a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-1 to compound HA (HT-1:HA) 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 40 nm. Next, compound Inv-2 was vapor-deposited on this first hole transport layer to form a second hole transport layer with a thickness of 45 nm. Next, compound HT-2 was vapor-deposited on this second hole-transporting layer to form a third hole-transporting layer with a thickness of 5 nm. Next, compound BH-3 (host material) and compound BD-5 (dopant material) were co-deposited on this third hole-transporting layer to form a first light-emitting layer with a thickness of 5 nm. The mass ratio of compound BH-3 to compound BD-5 (BH-3:BD-5) was 99:1. Next, compound BH-6 (host material) and compound BD-5 (dopant material) were co-deposited on this first light-emitting layer to form a second light-emitting layer with a thickness of 20 nm. The mass ratio of compound BH-6 to compound BD-5 (BH-6:BD-5) was 99:1. Next, compound ET-3 was vapor-deposited on this second light-emitting layer to form a first electron-transporting layer with a thickness of 10 nm. Next, compound ET-4 was vapor-deposited on the first electron-transporting layer to form a second electron-transporting layer with a thickness of 15 nm. Then, metal Al was vapor-deposited on the electron-injecting electrode to form a metal cathode with a thickness of 80 nm. The layer structure of the organic EL device (III) of Example 16 obtained in this manner is shown below: ITO (130) / HT-1:HA=97:3 (10) / HT-1 (40) / Inv-2 (45) / HT-2 (5) / BH-3:BD-5=99:1 (5) / BH-6:BD-5=99:1 (20) / ET-3 (10) / ET-4 (15) / Al (80) In the above layer structure, the numbers in parentheses indicate the film thickness (nm), and the ratios are mass ratios.

[0453] Example 17 An organic EL device (III) was produced in the same manner as in Example 8, except that compound HT-5 was used instead of compound HT-1 and compound Inv-1 was used instead of compound Inv-2.

[0454] Comparative Examples 4 and 5 Organic EL devices (III) were prepared in the same manner as in Example 8, except that the comparative compound Ref-3 or Ref-4 was used instead of the compound Inv-2.

[0455] Evaluation of Organic EL Element (III) The external quantum efficiency of the obtained organic EL element (III) was measured in the same manner as for the organic EL element (I). The results are shown in Table 3. (3) 95% Lifetime (LT95) The obtained organic EL element (III) was applied with a current density of 50 mA / cm. ２ The time until the luminance decreased to 95% of the initial luminance was measured, and this was taken as the 95% lifespan (LT95). The results are shown in Table 3.

[0456]

[0457] Invention compounds used in the production of organic EL devices (IV) in Examples 18 to 34

[0458] Comparative compounds used in the production of organic EL device (IV) of Comparative Example 6

[0459] Other compounds used in the production of organic EL devices in Examples 18 to 34 and Comparative Example 6

[0460]

[0461] Preparation of Organic EL Device (IV) Example 18 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, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was 130 nm. The cleaned glass substrate with the ITO transparent electrode was attached to a substrate holder in a vacuum deposition apparatus, and first, compound Inv-2 and compound HA were co-deposited on the surface on which the transparent electrode was formed, covering the transparent electrode, to form a hole injection layer with a thickness of 10 nm. The mass ratio of compound Inv-2 to compound HA (Inv-2:HA) was 97:3. Next, compound Inv-2 was vapor-deposited on the hole injection layer to form a first hole transport layer with a thickness of 85 nm. Next, compound HT-6 was vapor-deposited on this first hole transport layer to form a second hole transport layer with a thickness of 5 nm. Next, compound BH-1 (host material) and compound BD-3 (dopant material) were co-deposited on this second hole-transporting layer to form a first light-emitting layer with a thickness of 5 nm. The mass ratio of compound BH-1 to compound BD-3 (BH-1:BD-3) was 99:1. Next, compound BH-5 (host material) and compound BD-3 (dopant material) were co-deposited on this first light-emitting layer to form a second light-emitting layer with a thickness of 15 nm. The mass ratio of compound BH-5 to compound BD-3 (BH-5:BD-3) was 99:1. Next, compound ET-1 was deposited on this second light-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 31 nm. The mass ratio of the compound ET-2 to Liq (ET-2:Liq) was 50:50. Next, Liq was vapor-deposited on this second electron-transporting layer to form an electron-injecting electrode with a film thickness of 1 nm. Then, metal Al was vapor-deposited on this electron-injecting electrode to form a metal cathode with a film thickness of 80 nm. The layer structure of the organic EL element (IV) of Example 18 obtained in this manner is shown below.ITO (130) / Inv-2:HA=97:3 (10) / Inv-2 (85) / HT-6 (5) / BH-1:BD-3=99:1 (5) / BH-5:BD-3=99:1 (15) / ET-1 (5) / ET-2:Liq=50:50 (31) / Liq (1) / Al (80) In the above layer structure, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

[0462] Examples 19 to 21 Organic EL devices (IV) were prepared in the same manner as in Example 18, except that, instead of compound Inv-2, compound Inv-4 was used in Example 19, compound Inv-3 was used in Example 20, and compound Inv-9 was used in Example 21.

[0463] Example 22 An organic EL device (IV) was produced in the same manner as in Example 18, except that the compound HT-7 was used instead of the compound HT-6.

[0464] Example 23 An organic EL device (IV) was produced in the same manner as in Example 18, except that compound BH-9 was used instead of compound BH-5.

[0465] Example 24 An organic EL device (IV) was produced in the same manner as in Example 18, except that compound BH-3 was used instead of compound BH-1, compound BH-6 was used instead of compound BH-5, and compound BD-4 was used instead of compound BD-3.

[0466] Example 25 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 ITO transparent electrode was attached to a substrate holder in a vacuum deposition apparatus, and first, compound Inv-2 and compound HA were co-deposited on the surface on which the transparent electrode was formed, covering the transparent electrode, to form a hole injection layer with a thickness of 10 nm. The mass ratio of compound Inv-2 to compound HA (Inv-2:HA) was 97:3. Next, invention compound Inv-2 was vapor-deposited on the hole injection layer to form a first hole transport layer with a thickness of 85 nm. Next, compound HT-8 was vapor-deposited on this first hole transport layer to form a second hole transport layer with a thickness of 5 nm. Next, compound BH-3 (host material) and compound BD-5 (dopant material) were co-deposited on this second hole-transporting layer to form a first light-emitting layer with a thickness of 5 nm. The mass ratio of compound BH-3 to compound BD-5 (BH-3:BD-5) was 99:1. Next, compound BH-6 (host material) and compound BD-5 (dopant material) were co-deposited on this first light-emitting layer to form a second light-emitting layer with a thickness of 15 nm. The mass ratio of compound BH-6 to compound BD-5 (BH-6:BD-5) was 99:1. Next, compound ET-3 was deposited on this second light-emitting layer to form a first electron-transporting layer with a thickness of 10 nm. Next, compound ET-4 was deposited on this first electron-transporting layer to form a second electron-transporting layer with a thickness of 15 nm. Finally, metal Al was deposited on this second electron-transporting layer to form a metal cathode with a thickness of 80 nm. The layer structure of the organic EL device (IV) of Example 25 thus obtained is shown below: ITO (130) / Inv-2:HA=97:3 (10) / Inv-2 (85) / HT-8 (5) / BH-3:BD-5=99:1 (5) / BH-6:BD-5=99:1 (15) / ET-3 (10) / ET-4 (15) / Al (80) In the above layer structure, the numbers in parentheses are film thicknesses (nm), and the ratios are mass ratios.

[0467] Example 26 An organic EL device (IV) was produced in the same manner as in Example 18, except that the compound HT-9 was used instead of the compound HT-6.

[0468] Example 27 An organic EL device (IV) was produced in the same manner as in Example 18, except that the compound HT-10 was used instead of the compound HT-6.

[0469] Example 28 An organic EL device (IV) was prepared in the same manner as in Example 18, except that instead of forming a 15 nm-thick second emitting layer by co-depositing compound BH-5 (host material) and compound BD-3 (dopant material) on the first emitting layer, a 20 nm-thick second emitting layer was formed by co-depositing compound BH-4 (host material), compound BH-7 (host material), and compound BD-3 (dopant material). The mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 70:30, and the concentration of compound BD-3 was 1 mass % with respect to the entire second emitting layer.

[0470] Example 29 An organic EL element (IV) was prepared in the same manner as in Example 28, except that compound HT-7 was used instead of compound HT-6 and the mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 60:40.

[0471] Example 30 An organic EL device (IV) was prepared in the same manner as in Example 18, except that instead of forming a 15 nm-thick second emitting layer by co-depositing compound BH-5 (host material) and compound BD-3 (dopant material) on the first emitting layer, a 20 nm-thick second emitting layer was formed by co-depositing compound BH-8 (host material), compound BH-5 (host material), and compound BD-3 (dopant material). The mass ratio of compound BH-8 to compound BH-5 (BH-8:BH-5) was 70:30, and the concentration of compound BD-3 was 1 mass% with respect to the entire second emitting layer.

[0472] Examples 31 to 34 Organic EL devices (IV) were prepared in the same manner as in Example 18, except that, instead of compound HT-6, compound HT-11 was used in Example 31, compound HT-4 in Example 32, compound HT-12 in Example 33, and compound HT-13 in Example 34.

[0473] Comparative Example 6 An organic EL device (IV) was produced in the same manner as in Example 17, except that the compound Ref-5 was used instead of the compound Inv-2 and the compound HT-13 was used instead of the compound HT-6.

[0474] Evaluation of Organic EL Element (IV) The external quantum efficiency of the obtained organic EL element (IV) was measured in the same manner as for the organic EL element (I), and the 95% lifetime was measured in the same manner as for the organic EL element (III). The results are shown in Table 4.

[0475]

[0476] As is clear from the results in Tables 1 to 4, the compounds Inv-1 to Inv-9 provide organic EL devices with lower driving voltages and higher external quantum efficiencies than the comparative compounds Ref-1 to Ref-5.

[0477] Invention compounds Inv-1 to Inv-9 synthesized in the synthesis examples

[0478] Intermediate Synthesis Example 1: Synthesis of Intermediate A

[0479] Under an argon atmosphere, a mixture of 7.40 g (22.1 mmol) of 2-bromo9-phenyl-9-methyl-9H-fluorene, 5.08 g (23.2 mmol) of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, 0.404 g (0.441 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.845 g (1.77 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos), 33 ml of 2 M aqueous potassium phosphate solution, and 110 mL of 1,4-dioxane was stirred at 80°C for 7 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography to obtain 7.67 g of a white solid (Intermediate A-1). The yield was 99%.

[0480] Under an argon atmosphere, a mixture of 7.67 g (22.1 mmol) of Intermediate A-1, 5.15 g (22.1 mmol) of 2-bromobiphenyl, 0.406 g (0.443 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.552 g (0.886 mmol) of BINAP, 2.343 g (24.4 mmol) of sodium t-butoxide, and 111 mL of toluene was stirred at 100°C for 30 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography to obtain 6.93 g of a white solid. The yield was 63%.

[0481] Intermediate Synthesis Example 2: Synthesis of Intermediate B

[0482] Under an argon atmosphere, a mixture of 9.05 g (27.0 mmol) of 2-bromo9-phenyl-9-methyl-9H-fluorene, 5.07 g (32.4 mmol) of 2-chlorophenylboronic acid, 0.395 g (0.540 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, 40.5 mL of 2 M aqueous sodium carbonate, and 135 mL of DME was refluxed at the boiling point for 7 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography to obtain 9.82 g of a white solid. The yield was 99%.

[0483] Intermediate Synthesis Example 3: Synthesis of Intermediate C

[0484] A white solid was obtained in 75% yield by the same procedure as in the synthesis of Intermediate A, except that bromobenzene was used instead of 2-bromobiphenyl.

[0485] Synthesis Example 1: Synthesis of Compound Inv-1

[0486] Under an argon atmosphere, a mixture of 5.93 g (11.9 mmol) of intermediate A, 3.89 g (14.2 mmol) of 2-bromo-9,9-dimethyl-9H-fluorene, 0.217 g (0.237 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.275 g (0.949 mmol) of tri-tert-butylphosphonium tetrafluoroborate, 23.7 mL of lithium bis(trimethylsilyl)amide (1 M toluene solution), and 119 mL of xylene was refluxed at the boiling point for 7 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 3.29 g of a white solid. The yield was 40%. Mass spectrometry analysis of the resulting product indicated that it was compound Inv-1, with a molecular weight of 691.92 and an m / e of 692.

[0487] Synthesis Example 2: Synthesis of Compound Inv-2

[0488] Under an argon atmosphere, a mixture of 3.47 g (10.0 mmol) of Intermediate A-1, 6.28 g (23.0 mmol) of 2-bromo-9,9-dimethyl-9H-fluorene, 0.366 g (0.400 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.464 g (1.60 mmol) of tri-tert-butylphosphonium tetrafluoroborate, 2.69 g (28.0 mmol) of sodium t-butoxide, and 100 mL of xylene was stirred at 110°C for 7 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography to obtain 1.88 g of a white solid. The yield was 26%. Mass spectrometry analysis of the resulting product identified compound Inv-2, which had a molecular weight of 731.98 with an m / e of 732.

[0489] Synthesis Example 3: Synthesis of Compound Inv-3

[0490] The same procedure as in Synthesis Example 2 was carried out, except that 4-bromobiphenyl was used instead of 2-bromo-9,9-dimethyl-9H-fluorene, to obtain 3.51 g of a white solid. The yield was 54%. Mass spectrometry analysis of the obtained product showed that it was compound Inv-3, with a molecular weight of 651.85 and an m / e of 652.

[0491] Synthesis Example 4: Synthesis of Compound Inv-4

[0492] Under an argon atmosphere, a mixture of 2.43 g (8.51 mmol) of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, 3.44 g (9.37 mmol) of Intermediate B, 0.156 g (0.170 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.280 g (0.681 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos), 1.15 g (11.9 mmol) of sodium t-butoxide, and 85 mL of xylene was stirred at 110°C for 7 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography to obtain 1.88 g of a white solid. The yield was 35%. Mass spectrometry analysis of the resulting product identified compound Inv-4, which had a molecular weight of 615.82 with an m / e of 616.

[0493] Synthesis Example 5: Synthesis of Compound Inv-5

[0494] A white solid was obtained in the same manner as in Synthesis Example 4, except that Intermediate D was used instead of Intermediate B and Intermediate C was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine. The yield was 62%. Mass spectrometry analysis of the obtained product showed that it was Compound Inv-5, with a molecular weight of 691.92 and an m / e of 692.

[0495] Synthesis Example 6: Synthesis of Compound Inv-6

[0496] A white solid was obtained in the same manner as in Synthesis Example 4, except that N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-9H-fluoren-2-amine was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine. The yield was 48%. Mass spectrometry analysis of the obtained product revealed that it was compound Inv-6, with a molecular weight of 691.92 and an m / e of 692.

[0497] Synthesis Example 7: Synthesis of Compound Inv-7

[0498] A white solid was obtained in the same manner as in Synthesis Example 4, except that Intermediate E was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine. The yield was 47%. Mass spectrometry analysis of the obtained product revealed that it was compound Inv-7, with a molecular weight of 753.99 and an m / e ratio of 754.

[0499] Synthesis Example 8: Synthesis of Compound Inv-8

[0500] A white solid was obtained in the same manner as in Synthesis Example 4, except that Intermediate F was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine. The yield was 55%. Mass spectrometry analysis of the obtained product showed that it was compound Inv-8, with a molecular weight of 767.97 and an m / e of 768.

[0501] Synthesis Example 9: Synthesis of Compound Inv-9

[0502] A white solid was obtained in the same manner as in Synthesis Example 4, except that bis([1,1'-biphenyl]-4-yl-d9)amine was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine. The yield was 65%. Mass spectrometry analysis of the obtained product revealed that it was compound Inv-9, with a molecular weight of 669.96 and an m / e of 670.

[0503] 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 6d third 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): 【Chemistry 1】 (In formula (1), N ＊ is the central nitrogen atom. R ａ and R ｂ One of the groups is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and the other is 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. However, R ａ and R ｂ may be bonded to each other to form a substituted or unsubstituted ring. R ２ , R ３ , R ６ and R ７ is a single bond bonded to *1, and R １ , R ４ , R ５ , R ８ , and R that is not a single bond bonded to *1 ２ , R ３ , R ６ and R ７ 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 15 ring 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. R １ , R ４ , R ５ , R ８ and R which is not a single bond ２ , R ３ , R ６ and R ７ Adjacent two selected from are not bonded to each other and therefore do not form a ring. R １１ ~R １４ each independently represents 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 18 ring carbon atoms. R １１ ~R １４ Adjacent two selected from are not bonded to each other and therefore do not form a ring. L １ ~L ４ are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms. Ar １ and Ar ２ is a group represented by any one of the following formulas (1a) to (1g), and at least one of Ar 1 and Ar 2 is a group represented by the above formula (1a) or (1g). 【Chemistry 2】 (In formula (1a), *21 is L １ Or L ２ is the binding site to R １０１ ~R １０５ is a single bond bonded to *22, and R １０６ ~R １１０ is a single bond bonded to *23, and R １１１ ~R １１５ One selected from is a single bond bonding to *24. The R that is not a single bond １０１ ~R １１５ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. The R that is not a single bond １０１ ~R １０５ adjacent two selected from are not bonded to each other and therefore do not form a ring, The R that is not a single bond １０６ ~R １１０ adjacent two selected from are not bonded to each other and therefore do not form a ring, The R that is not a single bond １１１ ~R １１５ Adjacent two selected from are not bonded to each other and therefore do not form a ring. m is 0 or 1, n is 0 or 1, and l is 0 or 1. R １１６ ~R １２０ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 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. R １１６ ~R １２０ Adjacent two selected from are not bonded to each other and therefore do not form a ring. 【Chemistry 3】 (In formula (1b), *25 is L １ Or L ２ is the binding site to R １２１ ~R １２８ One selected from is a single bond bonding to *26. The R that is not a single bond １２１ ~R １２８ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms. The R that is not a single bond １２１ ~R １２８ Adjacent two selected from are not bonded to each other and therefore do not form a ring. However, L １ is a p-phenylene group, and Ar １ is represented by formula (1b), R in the group represented by formula (1b) bonded to the p-phenylene group １２１ , R １２４ , R １２５ , and R １２８ one selected from is a single bond bonded to *26, L ２ is a p-phenylene group, and Ar ２ is represented by formula (1b), R in the group represented by formula (1b) bonded to the p-phenylene group １２１ , R １２４ , R １２５ , and R １２８ One selected from is a single bond bonded to *26. 【Chemistry 4】 (In formula (1c), *27 is L １ Or L ２ is the binding site to R １３１ ~R １４０ One selected from is a single bond bonded to *28. The R that is not a single bond １３１ ~R １４０ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. The R that is not a single bond １３１ ~R １４０ Adjacent two selected from are not bonded to each other and therefore do not form a ring. 【Chemistry 5】 (In formula (1d), *29 is L １ Or L ２ is the binding site to R １４１ ~R １５２ One selected from is a single bond bonding to *30. The R that is not a single bond １４１ ~R １５２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. The R that is not a single bond １４１ ~R １５２ Adjacent two selected from are not bonded to each other and therefore do not form a ring structure. 【Chemistry 6】 (In formula (1e), *31 is L １ Or L ２ is the binding site to R １６１ ~R １６５ is a single bond bonded to *32, and R １６１ ~R １６５ The other one selected from is a single bond bonded to *33. R which is not a single bond bonded to the *32 and is not a single bond bonded to the *33 １６１ ~R １６５ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group. R that is not a single bond bonded to *32 and is not a single bond bonded to *33 １６１ ~R １６５ Adjacent two selected from are not bonded to each other and therefore do not form a ring. R １７１ ~R １７５ and R １８１ ~R １８５ are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms. R １７１ ~R １７５ adjacent two 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 １８１ ~R １８５ 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 not form a ring. 【Chemistry 7】 (In formula (1f), *34 is L １ Or L ２ is the binding site to X is an oxygen atom, a sulfur atom, or NR Ａ It is. R １９１ ~R １９８ and R Ａ One selected from is a single bond bonded to *35. The R that is not a single bond Ａ represents 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. The R that is not a single bond １９１ ~R １９８ 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. The R that is not a single bond １９１ ~R １９８ 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 not form a ring. 【Chemistry 8】 (In formula (1g), *36 is L １ Or L ２ is the binding site to R B , R C , and R ２０１ ~R ２０８ One selected from is a single bond bonded to *37. The R that is not a single bond B and R C are each independently 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. The R that is not a single bond B and R C do not combine with each other to form a substituted or unsubstituted ring. The R that is not a single bond ２０１ ~R ２０８ 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. The R that is not a single bond ２０１ ~R ２０８ Adjacent two selected from are not bonded to each other and therefore do not form a ring.

2. R ａ and R ｂ 2. The compound according to claim 1, wherein one of said alkyl groups is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and the other is a substituted or unsubstituted phenyl group.

3. R ２ Or R ７ The compound according to claim 1 or 2, wherein is a single bond bonded to *1.

4. L ３ The compound according to claim 1 or 2, wherein is a single bond.

5. L ４ The compound according to claim 1 or 2, wherein is a single bond.

6. Ar １ Or Ar ２ is a group represented by formula (1a), and the group represented by formula (1a) satisfies at least one of the following (i) to (iii): (i) R １０１ Or R １０５ is a single bond that bonds to *22 (ii) R １０６ Or R １１０ is a single bond that bonds to *23 (iii) R １１１ Or R １１５ is a single bond that bonds to *24

7. Ar １ Or Ar ２ is a group represented by the formula (1g), and in the group represented by the formula (1g), R B and R C and each independently represent a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group.

8. Ar １ Or Ar ２ is a group represented by the formula (1g), and in the group represented by the formula (1g), R ２０２ Or R ２０７ The compound according to claim 1 or 2, wherein is a single bond attached to *37.

9. L １ and L ２ and each independently represent a single bond or an arylene group having 6 to 12 ring carbon atoms.

10. The compound according to claim 1 or 2, wherein L 1 and L 2 are single bonds.

11. The compound according to claim 1 or 2, wherein R 11 to R 14 are all hydrogen atoms.

12. 3. The compound according to claim 1 or 2, which contains at least one deuterium atom.

13. A material for an organic electroluminescence device, comprising the compound according to claim 1 or 2.

14. A hole transport layer material comprising the compound according to claim 1 or 2.

15. 3. 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 layer of the organic layer including the compound according to claim 1 or 2.

16. 16. The organic electroluminescence device according to claim 15, wherein the organic layer comprises a hole transporting zone between the anode and the light emitting layer, the hole transporting zone comprising the compound.

17. 17. The organic electroluminescence device according to claim 16, wherein the hole transport region includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side, and one or both of the first hole transport layer and the second hole transport layer contain the compound.

18. 18. The organic electroluminescence device according to claim 17, wherein the light emitting layer and the second hole transport layer are in direct contact with each other.

19. 18. The organic electroluminescence device according to claim 17, wherein the sum of the thickness of the first hole transport layer and the thickness of the second hole transport layer is 30 nm or more and 150 nm or less.

20. 16. The organic electroluminescence device according to claim 15, wherein the light-emitting layer is a single layer.

21. 16. The organic electroluminescence device according to claim 15, wherein the light-emitting layer contains a light-emitting compound that exhibits fluorescent emission having a main peak wavelength of 500 nm or less.

22. 16. The organic electroluminescence device according to claim 15, wherein the light-emitting layer comprises a fluorescent dopant material.

23. An electronic device comprising the organic electroluminescence device according to claim 15.

Images