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

Abstract

A compound represented by formula (1), an organic electroluminescent element containing the compound, and an electronic device containing the organic electroluminescent element. Each symbol in formula (1) is as defined in the description. # imgabs0 #

Description

Technical Field

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

[0002] Generally speaking, an organic electroluminescent element (hereinafter sometimes referred to as an "organic EL element") is composed of an anode, a cathode, and an organic layer sandwiched between the anode and the cathode. If a voltage is applied between the two electrodes, electrons are injected from the cathode side into the luminescent region, and holes are injected from the anode side into the luminescent region, and the injected electrons and holes are recombined in the luminescent region to generate an excited state, and light is emitted when the excited state returns to the ground state. Therefore, it is important to find a combination of materials that efficiently transfer electrons or holes to the luminescent region and make it easy for electrons and holes to recombine so that excitons emit light efficiently in order to obtain high-performance organic EL elements.

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

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: China Publication Patent No. 111675701

[0007] Patent Document 2: China Publication Patent No. 109096179

[0008] Patent Document 3: Korean Patent Publication No. 10-2019-0035567

[0009] Patent Document 4: Korean Patent Publication No. 10-2018-0066855

[0010] Patent Document 5: U.S. Patent Application Publication No. 2016 / 0293843

[0011] Patent Document 6: U.S. Patent Application Publication No. 2015 / 0179953

[0012] Patent Document 7: U.S. Patent Application Publication No. 2016 / 0301005

[0013] Patent Document 8: Korean Patent Publication No. 10-2018-0116740

[0014] Patent Document 9: U.S. Patent Application Publication No. 2017 / 0194569

[0015] Patent Document 10: U.S. Patent Application Publication No. 2017 / 0186978

[0016] Patent Document 11: U.S. Patent Application Publication No. 2017 / 0186969

[0017] Patent Document 12: Korean Patent Publication No. 10-2019-0005522

[0018] Patent Document 13: International Publication No. 2021 / 045590 Summary of the invention

[0019] Problem that the invention aims to solve

[0020] Conventionally, a large number of compounds for organic EL devices have been reported, but further improvement in the performance of organic EL devices is still being sought.

[0021] 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 with further improved element performance, and an electronic device including such an organic EL element.

[0022] Means used to solve problems

[0023] The present inventors have conducted intensive studies on the performance of organic EL devices containing the compounds described in Patent Documents 1 to 13 and have found that the performance of an organic EL device containing a compound represented by the following formula (1) is further improved.

[0024] In one embodiment, the present invention provides a compound represented by the following formula (1).

[0025] [Chemical formula 1]

[0026]

[0027] (In formula (1),

[0028] N* is the central nitrogen atom.

[0029] R a and R b One of them 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.

[0030] Among them, R a and R b They may be bonded to each other to form a substituted or unsubstituted ring.

[0031] Selected from R 2 , R 3 , R 6 and R7 One of them is a single bond to *1, R 1 , R 4 , R 5 , R 8 and R which is not a single bond bonded to *1 2 , R 3 , R 6 and R 7 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 ring 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.

[0032] Selected from R 1 , R 4 , R 5 , R 8 and R other than the above single bond 2 , R 3 , R 6 and R 7 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring.

[0033] R 11 ~R 14 Each is 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.

[0034] Selected from R 11 ~R 14 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring.

[0035] L 1 ~L 4 Each is independently a single bond or an arylene group having 6 to 30 ring carbon atoms.

[0036] Ar 1 and Ar 2 It is a group represented by any one of the following formulae (1a) to (1g).

[0037] [Chemical formula 2]

[0038]

[0039] (In formula (1a),

[0040] *21 is with L 1 or L 2 bonding position.

[0041] Selected from R 101 ~R 105 One of them is a single bond bonded to *22, selected from R106 ~R 110 One of them is a single bond bonded to *23, selected from R 111 ~R 115 One of them is a single bond to *24.

[0042] R is not a single bond as above 101 ~R 115 Each is 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.

[0043] R is selected from the group consisting of 101 ~R 105 The two adjacent ones in are not bonded to each other and thus do not form a ring.

[0044] R is selected from the group consisting of 106 ~R 110 The two adjacent ones in are not bonded to each other and thus do not form a ring.

[0045] R is selected from the group consisting of 111 ~R 115 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring.

[0046] m is 0 or 1, n is 0 or 1, and 1 is 0 or 1.

[0047] R 116 ~R 120 Each is 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.

[0048] Selected from R 116 ~R 120 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring.)

[0049] [Chemical formula 3]

[0050]

[0051] (In formula (1b),

[0052] *25 is the same as L 1 or L 2 bonding position.

[0053] Selected from R 121 ~R 128 One of them is a single bond to *26.

[0054] R is not a single bond as above 121 ~R 128Each is 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.

[0055] R is selected from the group consisting of 121 ~R 128 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring.

[0056] Among them, in L 1 is p-phenylene, Ar 1 When represented by formula (1b), the group represented by formula (1b) bonded to the p-phenylene group is selected from R 121 , R 124 , R 125 and R 128 One of them is a single bond to *26,

[0057] In L 2 is p-phenylene, Ar 2 When represented by formula (1b), the group represented by formula (1b) bonded to the p-phenylene group is selected from R 121 , R 124 , R 125 and R 128 One of them is a single bond to *26. )

[0058] [Chemical formula 4]

[0059]

[0060] (In formula (1c),

[0061] *27 is with L 1 or L 2 bonding position.

[0062] Selected from R 131 ~R 140 One of them is a single bond to *28.

[0063] R is not a single bond as above 131 ~R 140 Each is 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.

[0064] R is selected from the group consisting of 131 ~R 140 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring.)

[0065] [Chemical formula 5]

[0066]

[0067] (In formula (1d),

[0068] *29 is with L 1 or L 2 bonding position.

[0069] Selected from R 141 ~R 152 One of them is a single bond bonded to *30.

[0070] R is not a single bond as above 141 ~R 152 Each is 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.

[0071] R is selected from the group consisting of 141 ~R 152 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring structure.)

[0072] [Chemical formula 6]

[0073]

[0074] (In formula (1e),

[0075] *31 is with L 1 or L 2 bonding position.

[0076] Selected from R 161 ~R 165 One of them is a single bond bonded to *32, selected from R 161 ~R 165 The other one in is a single bond to *33.

[0077] R which is neither the single bond bonded to *32 nor the single bond bonded to *33 161 ~R 165 Each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group.

[0078] R is selected from a single bond that is neither bonded to *32 nor bonded to *33 161 ~R 165 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring.

[0079] R 171 ~R 175 and R 181 ~R 185 Each independently represents a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.

[0080] Selected from R 171 ~R175 Two adjacent ones of the alkyl groups may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form no ring.

[0081] Selected from R 181 ~R 185 Two adjacent ones of the alkyl groups may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form no ring.

[0082] [Chemical formula 7]

[0083]

[0084] (In formula (1f),

[0085] *34 is with L 1 or L 2 bonding position.

[0086] X is an oxygen atom, a sulfur atom or NR A .

[0087] Selected from R 191 ~R 198 and R A One of them is a single bond to *35.

[0088] R is not a single bond as above A It 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.

[0089] R is not a single bond as above 191 ~R 198 Each is 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.

[0090] R is selected from the group consisting of 191 ~R 198 Two adjacent ones of the alkyl groups may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form no ring.

[0091] [Chemical formula 8]

[0092]

[0093] (In formula (1g),

[0094] *36 is with L 1 or L 2 bonding position.

[0095] Selected from R B , RC and R 201 ~R 208 One of them is a single bond to *37.

[0096] RB and R are not single bonds. C Each is 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.

[0097] RB and R are not the single bonds mentioned above. C They may be bonded to each other to form a substituted or unsubstituted ring.

[0098] R is not a single bond as above 201 ~R 208 Each is 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.

[0099] R is selected from the group consisting of 201 ~R 208 The two adjacent ones in the formula are not bonded to each other and thus do not form a ring.

[0100] In another embodiment, the present invention provides a material for an organic EL device comprising the compound represented by the above formula (1).

[0101] In another embodiment, the present invention provides an organic electroluminescent element comprising a cathode, an anode and an organic layer located between the cathode and the anode, wherein the organic layer comprises a light-emitting layer, and at least one layer of the organic layer comprises the compound represented by the above formula (1).

[0102] In still another embodiment, the present invention provides an electronic device comprising the organic electroluminescent element.

[0103] Effects of the Invention

[0104] An organic EL device containing the compound represented by the above formula (1) exhibits improved device performance. BRIEF DESCRIPTION OF THE DRAWINGS

[0105] Figure 1 It is a schematic diagram showing an example of the layer structure of the organic EL element according to one embodiment of the present invention.

[0106] Figure 2 It is a schematic diagram showing another example of the layer structure of the organic EL element according to one embodiment of the present invention.

[0107] Figure 3This is a schematic diagram showing still another example of the layer structure of the organic EL element according to one embodiment of the present invention. DETAILED DESCRIPTION

[0108] [definition]

[0109] In this specification, the hydrogen atom is meant to include isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0110] In the present specification, in chemical structural formulas, a bondable position that does not clearly show a symbol such as "R" or "D" representing a deuterium atom is assumed to be bonded with a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom.

[0111] In this specification, the number of ring carbons refers to the number of carbon atoms among the atoms constituting the ring itself of a compound (such as a monocyclic compound, a condensed ring compound, a bridged ring compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are bonded in a ring shape. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring carbons. The "number of ring carbons" recorded below is set in the same manner unless otherwise stated. For example, the number of ring carbons of a benzene ring is 6, the number of ring carbons of a naphthalene ring is 10, the number of ring carbons of a pyridine ring is 5, and the number of ring carbons of a furan ring is 4. In addition, for example, the number of ring carbons of 9,9-diphenylfluorenyl is 13, and the number of ring carbons of 9,9'-spirobifluorenyl is 25.

[0112] In addition, when a substituent such as an alkyl group is substituted on a benzene ring, the carbon number of the alkyl group is not included in the ring carbon number of the benzene ring. Therefore, the ring carbon number of the benzene ring substituted with an alkyl group is 6. In addition, when a substituent such as an alkyl group is substituted on a naphthalene ring, the carbon number of the alkyl group is not included in the ring carbon number of the naphthalene ring. Therefore, the ring carbon number of the naphthalene ring substituted with an alkyl group is 10.

[0113] 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 condensed ring compound, a bridged ring compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are bonded in a ring shape (e.g., a monocyclic compound, a condensed ring compound, a bridged ring compound, a carbocyclic compound, and a heterocyclic compound). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of atoms constituting the ring) and atoms contained in a substituent when the ring is substituted by a substituent are not included in the number of ring atoms. The "number of ring atoms" recorded below is set in the same manner as long as it is not recorded separately. 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 bonded to a pyridine ring or atoms constituting a substituent is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring bonded with a hydrogen atom or a substituent is 6. In addition, 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. Therefore, the number of ring atoms of the quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

[0114] In this specification, "carbon number XX to YY" in the expression "substituted or unsubstituted ZZ group with carbon number XX to YY" means the carbon number of the ZZ group when it is unsubstituted, and does not include the carbon number of the substituent when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer greater than 1, and "YY" means an integer greater than 2.

[0115] In this specification, "the number of atoms XX to YY" in the expression "ZZ group having XX to YY atoms which may be substituted or unsubstituted" means the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituent when substituted. Here, "YY" is greater than "XX", "XX" means an integer greater than 1, and "YY" means an integer greater than 2.

[0116] In the present specification, an unsubstituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group".

[0117] In the present specification, "unsubstituted" in the expression "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom or a tritium atom.

[0118] In addition, in the present specification, "substituted" when expressing "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. "Substituted" when expressing "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0119] "Substituents described in this specification"

[0120] The substituents described in the present specification are described below.

[0121] The number of ring carbon atoms of the "unsubstituted aryl group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise described in the present specification.

[0122] The number of ring atoms of the "unsubstituted heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise described in the present specification.

[0123] The carbon number of the "unsubstituted alkyl group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise described in the present specification.

[0124] The carbon number of the "unsubstituted alkenyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise described in the present specification.

[0125] The number of carbon atoms in the "unsubstituted alkynyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise described in the present specification.

[0126] The number of ring carbon atoms of the "unsubstituted cycloalkyl group" described in the present specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise described in the present specification.

[0127] The number of ring carbon atoms of the "unsubstituted arylene group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise described in the present specification.

[0128] The number of ring atoms of the "unsubstituted divalent heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise described in the present specification.

[0129] The carbon number of the "unsubstituted alkylene group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise described in the present specification.

[0130] "Substituted or unsubstituted aryl"

[0131] As specific examples of "substituted or unsubstituted aryl" described in this specification (specific example group G1), the following unsubstituted aryl (specific example group G1 A) and substituted aryl (specific example group G1B) can be cited. (Here, unsubstituted aryl refers to the case where "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl refers to the case where "substituted or unsubstituted aryl" is "substituted aryl".) In this specification, when simply expressed as "aryl", both "unsubstituted aryl" and "substituted aryl" are included.

[0132] "Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" are replaced by a substituent. Examples of "substituted aryl" include groups in which one or more hydrogen atoms of an "unsubstituted aryl" are replaced by a substituent in the following specific example group G1A, and examples of substituted aryl in the following specific example group G1B. It should be noted that the examples of "unsubstituted aryl" and "substituted aryl" listed here are only examples, and the "substituted aryl" described in this specification also includes groups in which the hydrogen atom bonded to the carbon atom of the aryl itself in the "substituted aryl" in the following specific example group G1B is further replaced by a substituent, and groups in which the hydrogen atom of the substituent in the "substituted aryl" in the following specific example group G1B is further replaced by a substituent.

[0133] Unsubstituted aryl (specific example group G1 A):

[0134] Phenyl,

[0135] p-Biphenyl,

[0136] m-Biphenyl,

[0137] o-Biphenyl,

[0138] 4-terphenyl-4-yl,

[0139] 4-terphenyl-3-yl,

[0140] 4-terphenyl-2-yl,

[0141] m-terphenyl-4-yl,

[0142] m-terphenyl-3-yl,

[0143] m-terphenyl-2-yl,

[0144] o-terphenyl-4-yl,

[0145] o-terphenyl-3-yl,

[0146] o-terphenyl-2-yl,

[0147] 1-naphthyl,

[0148] 2-naphthyl,

[0149] Anthracene,

[0150] Benzanthryl,

[0151] Fiki,

[0152] Triphenylene,

[0153] Phenyl,

[0154] Pyrene

[0155] base,

[0156] Benzo base,

[0157] Triphenylene,

[0158] Benzotriphenylene,

[0159] Tetraphenylene,

[0160] Pentaphenyl,

[0161] Fluorene,

[0162] 9,9'-spirobifluorenyl,

[0163] Benzofluorenyl,

[0164] Dibenzofluorenyl,

[0165] Fluoranthene group,

[0166] Benzofluoranthene,

[0167] Perylene, and

[0168] A monovalent aromatic group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[0169] [Chemical formula 9]

[0170]

[0171] [Chemical formula 10]

[0172]

[0173] ·Substituted aryl (specific example group G1B): o-tolyl,

[0174] m-Toluene

[0175] p-Tolyl,

[0176] p-Xylyl,

[0177] m-Xylyl,

[0178] o-Xylyl,

[0179] p-Isopropylphenyl,

[0180] m-isopropylphenyl,

[0181] o-isopropylphenyl,

[0182] 4-tert-Butylphenyl,

[0183] m-tert-butylphenyl,

[0184] o-tert-butylphenyl,

[0185] 3,4,5-Trimethylphenyl,

[0186] 9,9-dimethylfluorenyl,

[0187] 9,9-Diphenylfluorenyl

[0188] 9,9-bis(4-methylphenyl)fluorenyl,

[0189] 9,9-bis(4-isopropylphenyl)fluorenyl,

[0190] 9,9-bis(4-tert-butylphenyl)fluorenyl,

[0191] Cyanophenyl,

[0192] Triphenylsilylphenyl,

[0193] Trimethylsilylphenyl,

[0194] Phenyl naphthyl,

[0195] naphthylphenyl, and

[0196] A group in which one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the above general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0197] "Substituted or unsubstituted heterocyclic group"

[0198] The "heterocyclic group" described in the present specification 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.

[0199] The "heterocyclic group" described in the present specification is a monocyclic group or a condensed ring group.

[0200] The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0201] As specific examples of the "substituted or unsubstituted heterocyclic group" described in this specification (specific example group G2), the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B) can be cited. (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when only "heterocyclic group" is expressed, both "unsubstituted heterocyclic group" and "substituted heterocyclic group" are included.

[0202] "Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by a substituent. Specific examples of "substituted heterocyclic group" include groups in which hydrogen atoms of the "unsubstituted heterocyclic group" of the following specific example group G2A are substituted, and examples of substituted heterocyclic groups of the following specific example group G2B are mentioned. It should be noted that the examples of "unsubstituted heterocyclic group" and "substituted heterocyclic group" listed here are only examples, and the "substituted heterocyclic group" recorded in this specification also includes groups in which hydrogen atoms bonded to ring atoms of the heterocyclic group itself in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents, and groups in which hydrogen atoms of substituents in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents.

[0203] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1), unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2), unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0204] Specific example group G2B includes, for example, the following heterocyclic groups containing nitrogen atom substitution (specific example group G2B1), oxygen atom substitution (specific example group G2B2), sulfur atom substitution (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formula (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4).

[0205] Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):

[0206] Pyrrolyl,

[0207] Imidazole,

[0208] Pyrazolyl,

[0209] Triazole,

[0210] Tetrazolyl,

[0211] oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, indolizinyl, quinolizinyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, indazolyl, phenanthrolinyl, phenanthridinyl, acridinyl, phenazinyl, carbazolyl, benzocarbazolyl, morpholinyl, phenoxazinyl,

[0212] Phenothiazine,

[0213] azacarbazolyl, and diazacarbazolyl.

[0214] · Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): furyl,

[0215] Oxazolyl,

[0216] Isoxazolyl,

[0217] Oxadiazolyl,

[0218] Cuckoo ton base,

[0219] Benzofuranyl,

[0220] Isobenzofuranyl,

[0221] Dibenzofuranyl,

[0222] Naphthobenzofuranyl,

[0223] Benzoxazolyl,

[0224] Benzisoxazolyl,

[0225] Phenoxazine,

[0226] Morpholinyl,

[0227] dinaphthofuranyl,

[0228] Azadibenzofuranyl,

[0229] Diazadibenzofuranyl,

[0230] azanaphthobenzofuranyl, and

[0231] naphthyridinylbenzofuranyl.

[0232] Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3): thienyl,

[0233] Thiazolyl,

[0234] Isothiazolyl,

[0235] Thiadiazole,

[0236] benzothienyl,

[0237] isobenzothienyl, dibenzothienyl,

[0238] naphthobenzothienyl,

[0239] Benzothiazolyl,

[0240] Benzisothiazolyl,

[0241] Phenothiazine,

[0242] dinaphthothienyl,

[0243] azadibenzothienyl,

[0244] diazadibenzothienyl,

[0245] azanaphthobenzothienyl and

[0246] diazanaphthobenzothienyl.

[0247] A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formula (TEMP-16) to (TEMP-33) (Specific example group G2A4):

[0248] [Chemical formula 11]

[0249]

[0250] [Chemical formula 12]

[0251]

[0252] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each independently represents an oxygen atom, a sulfur atom, NH or CH2. A and Y A At least one of them is an oxygen atom, a sulfur atom or NH.

[0253] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A When at least any one of is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the above general formula (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0254] Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):

[0255] (9-phenyl)carbazolyl,

[0256] (9-biphenyl)carbazolyl,

[0257] (9-phenyl)phenylcarbazolyl,

[0258] (9-naphthyl)carbazolyl,

[0259] Diphenylcarbazole-9-yl,

[0260] Phenylcarbazol-9-yl,

[0261] Methylbenzimidazolyl,

[0262] Ethylbenzimidazolyl,

[0263] Phenyl triazine,

[0264] Biphenyl triazine,

[0265] Diphenyltriazine,

[0266] Phenylquinazolinyl, and

[0267] Biphenylquinazolinyl.

[0268] Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0269] Phenyldibenzofuranyl,

[0270] Methyldibenzofuranyl,

[0271] tert-Butyldibenzofuranyl, and

[0272] The monovalent residue of spiro[9H-xanthen-9,9'-[9H]fluorene].

[0273] Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

[0274] Phenyldibenzothiophene,

[0275] Methyldibenzothiophene,

[0276] tert-Butyldibenzothienyl, and

[0277] The monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0278] · Groups in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) are replaced with substituents (Specific example group G2B4):

[0279] The above-mentioned "one or more hydrogen atoms of the monovalent heterocyclic group" refers to hydrogen atoms bonded to carbon atoms constituting the ring of the monovalent heterocyclic group, A and Y A When at least one of the is NH, the hydrogen atom bonded to the nitrogen atom and X A and Y A When one of them is CH2, one or more hydrogen atoms among the hydrogen atoms of the methylene group.

[0280] "Substituted or unsubstituted alkyl"

[0281] As specific examples of "substituted or unsubstituted alkyl" described in this specification (specific example group G3), the following unsubstituted alkyl (specific example group G3A) and substituted alkyl (specific example group G3B) can be cited. (Here, unsubstituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when only "alkyl" is expressed, both "unsubstituted alkyl" and "substituted alkyl" are included.

[0282] "Substituted alkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl" are replaced by a substituent. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl" (specific example group G3A) are replaced by a substituent, and examples of substituted alkyl (specific example group G3B) can be cited. In the present specification, the alkyl group in "unsubstituted alkyl" refers to a chain alkyl group. Therefore, "unsubstituted alkyl" includes "unsubstituted alkyl" as a straight chain and "unsubstituted alkyl" as a branched chain. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples, and the "substituted alkyl" recorded in the present specification also includes groups in which the hydrogen atoms of the alkyl group itself in the "substituted alkyl" of the specific example group G3B are further replaced by a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted alkyl" of the specific example group G3B are further replaced by a substituent.

[0283] Unsubstituted alkyl (specific example group G3A):

[0284] methyl,

[0285] Ethyl,

[0286] n-propyl,

[0287] Isopropyl,

[0288] n-Butyl,

[0289] Isobutyl,

[0290] sec-butyl, and

[0291] Tert-butyl.

[0292] Substituted alkyl (specific example group G3B):

[0293] Heptafluoropropyl (including isomers),

[0294] Pentafluoroethyl,

[0295] 2,2,2-trifluoroethyl, and

[0296] Trifluoromethyl.

[0297] "Substituted or unsubstituted alkenyl"

[0298] As specific examples of "substituted or unsubstituted alkenyl" described in this specification (specific example group G4), the following unsubstituted alkenyl (specific example group G4A) and substituted alkenyl (specific example group G4B) can be cited. (Here, unsubstituted alkenyl refers to the case where "substituted or unsubstituted alkenyl" is "unsubstituted alkenyl", and "substituted alkenyl" refers to the case where "substituted or unsubstituted alkenyl" is "substituted alkenyl".) In this specification, when simply expressed as "alkenyl", both "unsubstituted alkenyl" and "substituted alkenyl" are included.

[0299] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" are replaced by a substituent. Specific examples of "substituted alkenyl" include the following "unsubstituted alkenyl" (specific example group G4A) groups with substituents and examples of substituted alkenyl (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples, and the "substituted alkenyl" recorded in this specification also includes groups in which the hydrogen atoms of the alkenyl itself in the "substituted alkenyl" of the specific example group G4B are further replaced by a substituent and groups in which the hydrogen atoms of the substituent in the "substituted alkenyl" of the specific example group G4B are further replaced by a substituent.

[0300] Unsubstituted alkenyl (specific example group G4A):

[0301] Vinyl,

[0302] Allyl,

[0303] 1-Butenyl,

[0304] 2-Butenyl, and

[0305] 3-Butenyl.

[0306] Substituted alkenyl (specific example group G4B):

[0307] 1,3-Butadienyl,

[0308] 1-Methylvinyl,

[0309] 1-methylallyl,

[0310] 1,1-dimethylallyl,

[0311] 2-methylallyl, and

[0312] 1,2-Dimethylallyl.

[0313] "Substituted or unsubstituted alkynyl"

[0314] As specific examples of "substituted or unsubstituted alkynyl" described in this specification (specific example group G5), the following unsubstituted alkynyl (specific example group G5A) etc. can be cited. (Here, unsubstituted alkynyl refers to the case where "substituted or unsubstituted alkynyl" is "unsubstituted alkynyl".) When simply expressed as "alkynyl" below, both "unsubstituted alkynyl" and "substituted alkynyl" are included.

[0315] "Substituted alkynyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl" are replaced by a substituent. Specific examples of "substituted alkynyl" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl" (specific example group G5A) are replaced by a substituent.

[0316] Unsubstituted alkynyl (specific example group G5A):

[0317] Ethylene

[0318] "Substituted or unsubstituted cycloalkyl"

[0319] As specific examples of "substituted or unsubstituted cycloalkyl" described in the present specification (specific example group G6), the following unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B) can be cited. (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl".) In the present specification, when only "cycloalkyl" is expressed, both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.

[0320] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" are replaced by a substituent. Specific examples of "substituted cycloalkyl" include the following "unsubstituted cycloalkyl" (specific example group G6A) in which one or more hydrogen atoms are replaced by a substituent, and examples of substituted cycloalkyl (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples, and the "substituted cycloalkyl" recorded in this specification also includes the group in which one or more hydrogen atoms bonded to the carbon atoms of the cycloalkyl itself in the "substituted cycloalkyl" of the specific example group G6B are replaced by a substituent, and the group in which the hydrogen atom of the substituent in the "substituted cycloalkyl" of the specific example group G6B is further replaced by a substituent.

[0321] Unsubstituted cycloalkyl (specific example group G6A):

[0322] Cyclopropyl,

[0323] Cyclobutyl,

[0324] Cyclopentyl,

[0325] Cyclohexyl,

[0326] 1-adamantyl,

[0327] 2-adamantyl,

[0328] 1-Norbornyl, and

[0329] 2-Norborneol.

[0330] Substituted cycloalkyl (specific example group G6B):

[0331] 4-Methylcyclohexyl.

[0332] ·“-Si(R 901 )(R 902 )(R 903 )"

[0333] As described in this specification, -Si(R 901 )(R 902 )(R 903 ) as a specific example (specific example group G7), can be cited:

[0334] -Si(G1)(G1)(G1),

[0335] -Si(G1)(G2)(G2),

[0336] -Si(G1)(G1)(G2),

[0337] -Si(G2)(G2)(G2),

[0338] -Si(G3)(G3)(G3) and

[0339] -Si(G6)(G6)(G6). Here,

[0340] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0341] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0342] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0343] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0344] A plurality of G1's in -Si(G1)(G1)(G1) are the same as or different from each other.

[0345] The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other.

[0346] A plurality of G1's in -Si(G1)(G1)(G2) are the same as or different from each other.

[0347] Multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other.

[0348] Multiple G3 in -Si(G3)(G3)(G3) are the same as or different from each other.

[0349] Multiple G6's in -Si(G6)(G6)(G6) are the same as or different from each other.

[0350] ·“-O-(R 904 )"

[0351] As described in this specification, -O-(R 904) as a specific example (specific example group G8), can be cited:

[0352] -O(G1),

[0353] -O(G2),

[0354] -O(G3) and

[0355] -O(G6).

[0356] Here,

[0357] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0358] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0359] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0360] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0361] ·“-S-(R 905 )"

[0362] As described in this specification, -S-(R 905 ) as a specific example (specific example group G9), can be cited:

[0363] -S(G1),

[0364] -S(G2),

[0365] -S(G3) and

[0366] -S(G6).

[0367] Here,

[0368] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0369] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0370] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0371] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0372] ·“-N(R 906 )(R 907 )"

[0373] As described in this specification, -N(R906 )(R 907 ) are shown as specific examples (specific example group G10), and include

[0374] -N(G1)(G1),

[0375] -N(G2)(G2),

[0376] -N(G1)(G2),

[0377] -N(G3)(G3) and

[0378] -N(G6)(G6).

[0379] Here,

[0380] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0381] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0382] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0383] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0384] - A plurality of G1's in N(G1)(G1) are the same as or different from each other.

[0385] - The multiple G2s in N(G2)(G2) are the same as or different from each other.

[0386] - The multiple G3 in N(G3)(G3) are the same as or different from each other.

[0387] - The multiple G6's in N(G6)(G6) are the same as or different from each other.

[0388] "Halogen atoms"

[0389] Specific examples of the "halogen atom" described in the present specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0390] "Substituted or unsubstituted fluoroalkyl"

[0391] The "substituted or unsubstituted fluoroalkyl group" described in the present specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting an 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 an alkyl group in a "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). The carbon number of the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification. The "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. It should be noted that the "substituted fluoroalkyl group" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of an 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 groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced with fluorine atoms.

[0392] "Substituted or unsubstituted haloalkyl"

[0393] The "substituted or unsubstituted haloalkyl group" described in the present specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting an 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 an alkyl group in a "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The carbon number of the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification. The "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of a "haloalkyl group" are replaced with a substituent. It should be noted that the "substituted haloalkyl group" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in a "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in a "substituted haloalkyl group" are further replaced with a substituent. Specific examples of "unsubstituted haloalkyl" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (specific example group G3) are replaced with halogen atoms. A haloalkyl group is sometimes referred to as a halogenated alkyl group.

[0394] "Substituted or unsubstituted alkoxy"

[0395] A specific example of the "substituted or unsubstituted alkoxy group" described in the present specification is a group represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification.

[0396] "Substituted or unsubstituted alkylthio"

[0397] A specific example of the "substituted or unsubstituted alkylthio group" described in the present specification is a group represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification.

[0398] "Substituted or unsubstituted aryloxy group"

[0399] A specific example of the "substituted or unsubstituted aryloxy group" described in the present specification is a group represented by -O(G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. 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, unless otherwise described in the present specification.

[0400] "Substituted or unsubstituted arylthio"

[0401] A specific example of the "substituted or unsubstituted arylthio group" described in the present specification is a group represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. 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, unless otherwise described in the present specification.

[0402] "Substituted or unsubstituted trialkylsilyl"

[0403] A specific example of a "trialkylsilyl group" described in the present specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. A plurality of G3's in -Si(G3)(G3)(G3) are the same or different from each other. 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, unless otherwise described in the present specification.

[0404] "Substituted or unsubstituted aralkyl"

[0405] A specific example of the "substituted or unsubstituted aralkyl group" described in the present specification is a group represented by -(G3)-(G1), wherein G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. Therefore, the "aralkyl group" is a group in which the hydrogen atom of the "alkyl group" is replaced by the "aryl group" as a substituent, and is one embodiment of the "substituted alkyl group". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the carbon number of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise described in the present specification.

[0406] Specific examples of the “substituted or unsubstituted aralkyl group” include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl and 2-β-naphthylisopropyl.

[0407] The substituted or unsubstituted aryl group described in the present specification is preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl and 9,9-diphenylfluorenyl, etc.

[0408] The substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidyl group, a triazine group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group or 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 naphthobenzofuranyl group benzothiophenyl, azadibenzothiophenyl, diazadibenzothiophenyl, (9-phenyl)carbazyl ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl or (9-phenyl)carbazol-4-yl), (9-biphenyl)carbazyl, (9-phenyl)phenylcarbazyl, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazine, biphenyltriazine, diphenyltriazine, phenyldibenzofuranyl and phenyldibenzothiophenyl, etc.

[0409] In the present specification, the carbazolyl group is specifically any of the following groups unless otherwise described in the present specification.

[0410] [Chemical formula 13]

[0411]

[0412] In the present specification, the (9-phenyl)carbazolyl group is specifically any of the following groups unless otherwise specified in the present specification.

[0413] [Chemical formula 14]

[0414]

[0415] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0416] In the present specification, the dibenzofuranyl group and the dibenzothienyl group are specifically any of the following groups unless otherwise specified in the present specification.

[0417] [Chemical formula 15]

[0418]

[0419] In the above general formulas (TEMP-34) to (TEMP-41), * represents a bonding position.

[0420] The substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, or the like, unless otherwise described in the present specification.

[0421] "Substituted or unsubstituted arylene group"

[0422] Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted aryl group" by removing one hydrogen atom on the aryl ring. Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in specific example group G1 by removing one hydrogen atom on the aryl ring.

[0423] "Substituted or unsubstituted divalent heterocyclic group"

[0424] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom on the heterocyclic ring. Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in specific example group G2 by removing one hydrogen atom on the heterocyclic ring.

[0425] "Substituted or unsubstituted alkylene"

[0426] Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted alkyl group" by removing one hydrogen atom on the alkyl chain. Specific examples of the "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived from the "substituted or unsubstituted alkyl group" described in specific example group G3 by removing one hydrogen atom on the alkyl chain.

[0427] The substituted or unsubstituted arylene group described in the present specification is preferably any one of the following general formulae (TEMP-42) to (TEMP-68) unless otherwise described in the present specification.

[0428] [Chemical formula 16]

[0429]

[0430] [Chemical formula 17]

[0431]

[0432] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0433] In the above general formulas (TEMP-42) to (TEMP-52), * represents a bonding position.

[0434] [Chemical formula 18]

[0435]

[0436] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0437] Formula Q9 and Q 10 They may be bonded to each other via a single bond to form a ring.

[0438] In the above general formulas (TEMP-53) to (TEMP-62), * represents a bonding position.

[0439] [Chemical formula 19]

[0440]

[0441] In the above general formulae (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0442] In the above general formulas (TEMP-63) to (TEMP-68), * represents a bonding position.

[0443] The substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the following general formulae (TEMP-69) to (TEMP-102) unless otherwise described in the present specification.

[0444] [Chemical formula 20]

[0445]

[0446] [Chemical formula 21]

[0447]

[0448] [Chemical formula 22]

[0449]

[0450] In the above general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0451] [Chemical formula 23]

[0452]

[0453] [Chemical formula 24]

[0454]

[0455] [Chemical formula 25]

[0456]

[0457] [Chemical formula 26]

[0458]

[0459] In the above general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0460] The above is the description of the “substituents described in the present specification”.

[0461] ・"When bonding to form a ring"

[0462] In the present specification, the expression "one or more groups consisting of two or more adjacent groups ... 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 condensed ring, or are not bonded to each other" means the case where "one or more groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted monocyclic ring", the case where "one or more groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted condensed ring" and the case where "one or more groups consisting of two or more adjacent groups ... are not bonded to each other".

[0463] Hereinafter, the case of "one or more groups of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case of "one or more groups of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted condensed ring" in this specification (hereinafter, these cases are sometimes collectively referred to as "cases of bonding to form a ring.") are described. The case of an anthracene compound represented by the following general formula (TEMP-103) in which the mother skeleton is an anthracene ring is described as an example.

[0464] [Chemical formula 27]

[0465]

[0466] For example, in the 921 ~R 930 In the case of "one or more groups of two or more adjacent groups are bonded to each other to form a ring", the group of two adjacent groups forming one group means that R 921 With R 922 Group, R 922 With R 923 Group, R 923 With R 924 Group, R 924 With R 930Group, R 930 With R 925 Group, R 925 With R 926 Group, R 926 With R 927 Group, R 927 With R 928 Group, R 928 With R 929 The group, and R 929 With R 921 group.

[0467] The above-mentioned "one or more groups" means that two or more groups of the above-mentioned two or more adjacent groups can simultaneously form a ring. 921 With R 922 Bonded to each other to form ring Q A And at the same time R 925 With R 926 Bonded to each other to form ring Q B When the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0468] [Chemical formula 28]

[0469]

[0470] The case where "a group of two or more adjacent groups" forms a ring includes not only the case where a group of "two" adjacent groups are bonded as in the above example, but also the case where a group of "three or more" adjacent groups are bonded. For example, R 921 With R 922 Bonded to each other to form ring Q A , and R 922 With R 923 Bonded to each other to form ring Q C , consisting of three adjacent (R 921 , R 922 and R 923 ) are bonded to each other to form a ring and fused to the anthracene mother skeleton. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP.105), ring Q A and Ring Q C Total R 922 .

[0471] [Chemical formula 29]

[0472]

[0473] In the formed "monocyclic ring" or "condensed ring", the structure of the formed ring itself may be a saturated ring or an unsaturated ring. Even when "one of the two adjacent groups" forms a "monocyclic ring" or "condensed ring", the "monocyclic ring" or "condensed ring" may form a saturated ring or an unsaturated ring. For example, in the above general formula (TEMP-104), the ring Q A and Ring Q B Each is a "single ring" or a "condensed ring". In addition, the ring Q formed in the above general formula (TEMP-105) A And Ring Q C The ring Q of the above general formula (TEMP-105) is A With Ring Q C By RingQ A With Ring Q C The ring Q of the above general formula (TEMP-104) is fused to form a fused ring. A If it is a benzene ring, then ring Q A The ring Q of the above general formula (TEMP-104) A If it is a naphthalene ring, then ring Q A It is a condensed ring.

[0474] The "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.

[0475] Specific examples of the aromatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G1 are terminated with hydrogen atoms.

[0476] Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in Specific Example Group G2 are terminated with hydrogen atoms.

[0477] Specific examples of the aliphatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G6 are terminated with hydrogen atoms.

[0478] "Forming a ring" means that a ring is formed only by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton and one or more other optional elements. For example, R 921 With R 922 The ring Q formed by mutual bonding A It refers to R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 The carbon atom of the anthracene skeleton to which the bonding occurs forms a ring with one or more optional elements. 921 With R 922 Ring Q A In the case of R921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 When the carbon atom of the anthracene skeleton to which the carbon atom is bonded forms a monocyclic unsaturated ring with four carbon atoms, R 921 With R 922 The ring formed is a benzene ring.

[0479] Here, "optional element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur as long as it is not otherwise described in this specification. In the optional element (for example, in the case of carbon or nitrogen), the bond that does not form a ring can be terminated by hydrogen atoms or the like, or can be replaced by "optional substituents" described later. When an optional element other than carbon is included, the formed ring is a heterocycle.

[0480] Unless otherwise specified in the present specification, the number of "one or more optional elements" constituting a monocyclic or condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.

[0481] Unless otherwise specified in the present specification, "monocyclic ring" is preferred among "monocyclic ring" and "condensed ring".

[0482] In the present specification, unless otherwise specified, among "saturated ring" and "unsaturated ring", "unsaturated ring" is preferred.

[0483] Unless otherwise specified in the present specification, a "monocyclic ring" is preferably a benzene ring.

[0484] Unless otherwise specified in the present specification, the "unsaturated ring" is preferably a benzene ring.

[0485] In the case of "one or more groups consisting of two or more adjacent groups" "bonded to each other to form a substituted or unsubstituted single ring" or "bonded to each other to form a substituted or unsubstituted condensed ring", unless otherwise stated in the present specification, it is preferably one or more groups consisting of two or more adjacent groups bonded to each other to form a substituted or unsubstituted "unsaturated ring" formed by multiple atoms of the parent skeleton and one or more and fifteen or less elements selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0486] When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the above-mentioned "substituents described in the present specification".

[0487] When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above-mentioned "substituents described in the present specification".

[0488] The above is an explanation of the case where "one or more groups of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted single ring" and the case where "one or more groups of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted condensed ring" ("the case where they are bonded to form a ring").

[0489] ·Substituents when expressed as "substituted or unsubstituted"

[0490] In one embodiment of the present specification, the substituent group described as "substituted or unsubstituted" (in the present specification, sometimes referred to as "optional substituent group") is, for example, selected from

[0491] unsubstituted alkyl having 1 to 50 carbon atoms,

[0492] unsubstituted alkenyl having 2 to 50 carbon atoms,

[0493] unsubstituted alkynyl having 2 to 50 carbon atoms,

[0494] unsubstituted cycloalkyl having 3 to 50 ring carbon atoms,

[0495] -Si(R 901 )(R 902 )(R 903 ),

[0496] -O-(R 904 ),

[0497] -S-(R 905 ),

[0498] -N(R 906 )(R 907 ),

[0499] Halogen atoms, cyano, nitro,

[0500] unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0501] Unsubstituted heterocyclic group having 5 to 50 ring atoms

[0502] The groups in the group etc.

[0503] Here, R 901 ~R 907 Each independently

[0504] Hydrogen atoms,

[0505] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0506] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0507] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0508] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0509] In R 901 If there are two or more, two or more R 901 Same or different from each other,

[0510] In R 902 If there are two or more, two or more R 902 Same or different from each other,

[0511] In R 903 If there are two or more, two or more R 903 Same or different from each other,

[0512] In R 904 If there are two or more, two or more R 904 Same or different from each other,

[0513] In R 905 If there are two or more, two or more R 905 Same or different from each other,

[0514] In R 906 If there are two or more, two or more R 906 Same or different from each other,

[0515] In R 907 If there are two or more, two or more R 907 Same as or different from each other.

[0516] In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

[0517] an alkyl group having 1 to 50 carbon atoms,

[0518] an aryl group having 6 to 50 ring carbon atoms, and

[0519] A heterocyclic group having 5 to 50 ring atoms

[0520] The groups in the group.

[0521] In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

[0522] an alkyl group having 1 to 18 carbon atoms,

[0523] an aryl group having 6 to 18 ring carbon atoms, and

[0524] A heterocyclic group having 5 to 18 ring atoms

[0525] The groups in the group.

[0526] Specific examples of each group of the above-mentioned optional substituent are the specific examples of the substituent described in the above-mentioned section "substituent described in the present specification".

[0527] Unless otherwise stated in the present specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably a benzene ring.

[0528] Unless otherwise specified in the present specification, an optional substituent may further have a substituent. The substituent further possessed by the optional substituent is the same as the optional substituent described above.

[0529] In this specification, the numerical range expressed using "AA to BB" means a range including the numerical value AA described before "AA to BB" as the lower limit value and the numerical value BB described after "AA to BB" as the upper limit value.

[0530] Hereinafter, the compound of the present invention will be described.

[0531] The compound of the present invention is represented by the above formula (1). The symbols in formula (1) and the subsequent formulas contained in formula (1) are explained below. Unless otherwise specified, the same symbols have the same meanings.

[0532] The compound of the present invention represented by formula (1) and the formula described below included in formula (1) may be referred to as an "invention compound".

[0533] [Chemical formula 30]

[0534]

[0535] N* is the central nitrogen atom.

[0536] R a and R bOne of them 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 even more preferably 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30, preferably 5 to 18, and even more preferably 5 to 13 ring atoms.

[0537] Among them, R a and R b They may be bonded to each other to form a substituted or unsubstituted ring.

[0538] In one embodiment of the present invention, preferably R a and R b One of them 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, and more preferably R a and R b One of them is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and the other is a substituted or unsubstituted phenyl group.

[0539] The above R a and R b The unsubstituted alkyl group having 1 to 30 carbon atoms represented by the above-mentioned group is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl or dodecyl, preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or pentyl, more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, further preferably methyl or tert-butyl.

[0540] The above R a and R b The unsubstituted aryl group having 6 to 30 ring carbon atoms represented by is exemplified by phenyl, biphenyl, terphenyl, biphenylalkenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, triphenylenyl, phenanthrenyl, benzophenanthren ... Benzo The invention relates to an aryl group, a fluorenyl group, a fluorenyl group, a peryl group or a triphenylenyl group, preferably a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group, more preferably a phenyl group, a 2-biphenyl group, a 3-biphenyl group or a 4-biphenyl group, a 2-o-terphenyl group, a 3-o-terphenyl group or a 4-o-terphenyl group, a 2-m-terphenyl group, a 3-m-terphenyl group or a 4-m-terphenyl group, a 2-p-terphenyl group, a 3-p-terphenyl group or a 4-p-terphenyl group, or a 1-naphthyl group or a 2-naphthyl group, further preferably a phenyl group, a 2-biphenyl group, a 3-biphenyl group or a 4-biphenyl group, or a 1-naphthyl group or a 2-naphthyl group, and particularly preferably a phenyl group.

[0541] The above Ra and R b The unsubstituted aromatic heterocyclic group having 5 to 30 ring atoms represented by the present invention is exemplified by pyrrolyl, furanyl, thienyl, pyridyl, imidazopyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, indolyl, isoindolyl, indolizinyl, quinolizinyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, indazolyl, benzisoxazolyl, benzisothiazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, xanthenyl, benzofuranyl, isobenzo The benzothienyl group is preferably a furanyl group, a naphthobenzofuranyl group, a dibenzofuranyl group, a benzothienyl group (benzothienyl, the same below), an isobenzothienyl group (isobenzothienyl, the same below), a naphthobenzothienyl group (naphthobenzothienyl, the same below), a dibenzothienyl group (dibenzothienyl, the same below) or a carbazolyl group, preferably a benzofuranyl group, an isobenzofuranyl group, a naphthobenzofuranyl group, a dibenzofuranyl group, a benzothienyl group, an isobenzothienyl group, a naphthobenzothienyl group, a dibenzothienyl group or a carbazolyl group (9-carbazolyl group, or 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group or 4-carbazolyl group).

[0542] From the above R a and R b The unsubstituted monocyclic ring formed is, for example, a benzene ring, a cyclopentane ring, or a cyclohexane ring.

[0543] From the above R a and R b The unsubstituted condensed ring formed is, for example, a naphthalene ring or an anthracene ring.

[0544] In addition, in R a With R b When they are bonded to each other to form an unsubstituted monocyclic ring or an unsubstituted condensed ring, R a and R b It can form a ring with the fluorene skeleton to which these groups are bonded to form a spiro ring. The above spiro ring is a hydrocarbon ring or a heterocyclic ring selected from a monocyclic ring, a condensed ring, a bicyclic bridged ring, and a tricyclic bridged ring. The following are examples of substituted or unsubstituted spiro rings, but are not limited thereto. * indicates the bonding position to the benzene ring of the fluorene skeleton.

[0545] [Chemical formula 31]

[0546]

[0547] In one embodiment of the present invention, R a and R bPreferably, they do not bond to each other to form a substituted or unsubstituted ring.

[0548] Selected from R 2 , R 3 , R 6 and R 7 One of them is a single bond to *1, R 1 , R 4 , R 5 , R 8 and R which is not a single bond bonded to *1 2 , R 3 , R 6 and R 7 Each is 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 even 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.

[0549] Selected from R 1 , R 4 , R 5 , R 8 and R other than the above single bond 2 , R 3 , R 6 and R 7 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring.

[0550] In one embodiment of the present invention, R 2 or R 7 It is preferably a single bond bonded to *1.

[0551] The above R 1 , R 4 , R 5 , R 8 and R which is not a single bond bonded to *1 2 , R 3 , R 6 and R 7 The details of the unsubstituted alkyl radical having 1 to 30 carbon atoms are the same as those for R a and R b The records are the same.

[0552] The above R 1 , R 4 , R 5 , R 8 and R which is not a single bond bonded to *1 2 , R 3 , R 6 and R7 The unsubstituted cycloalkyl group having 3 to 15 ring carbon atoms represented by is, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl, and preferably cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

[0553] The above R 1 , R 4 , R 5 , R 8 and R which 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 are the same as those for R except that the number of ring carbon atoms is 6 to 12. a and R b The records are the same.

[0554] The above R 1 , R 4 , R 5 , R 8 and R which 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 are the same as those for R except that the number of ring atoms is 5 to 13. a and R b The records are the same.

[0555] The above R 1 , R 4 , R 5 , R 8 and R which is not a single bond bonded to *1 2 , R 3 , R 6 and R 7 They may all be hydrogen atoms.

[0556] R 11 ~R 14 Each is 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.

[0557] Selected from R 11 ~R 14 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring.

[0558] The above R 11 ~R 14The details of the unsubstituted alkyl radical having 1 to 30 carbon atoms are the same as those for R a and R b The records are the same.

[0559] The above R 11 ~R 14 The details of the unsubstituted aryl group having 6 to 18 ring carbon atoms are the same as those for R except that the number of ring carbon atoms is 6 to 18. a and R b The records are the same.

[0560] The above R 11 ~R 14 They may all be hydrogen atoms.

[0561] L 1 ~L 4 Each independently represents a single bond or an arylene group having 6 to 30, preferably 6 to 25, more preferably 6 to 12 ring carbon atoms.

[0562] In one embodiment of the present invention, L 1 and L 2 Each independently is preferably a single bond or an arylene group having 6 to 12 ring carbon atoms.

[0563] L 1 Can be a single bond, L 2 Can be a single key.

[0564] In one embodiment of the present invention, L 3 Preferred is a single bond.

[0565] In addition, in one embodiment of the present invention, L 4 Preferred is a single bond.

[0566] In addition, in one embodiment of the present invention, L 3 and L 4 Preferred is a single bond.

[0567] The above L 1 ~L 4 The unsubstituted arylene group having 6 to 30 ring carbon atoms represented by means of a divalent group obtained by removing one hydrogen atom from an unsubstituted aryl group having 6 to 30 ring carbon atoms. The details of the unsubstituted aryl group having 6 to 30 ring carbon atoms are the same as those for R a and R b The records are the same.

[0568] Ar 1 and Ar 2 It is a group represented by any one of the following formulae (1a) to (1g).

[0569] [Chemical formula 32]

[0570]

[0571] In formula (1a),

[0572] *21 is with L 1 or L 2 bonding position.

[0573] Selected from R 101 ~R 105 One of them is a single bond bonded to *22, selected from R 106 ~R 110 One of them is a single bond bonded to *23, selected from R 111 ~R 115 One of them is a single bond to *24.

[0574] R is not a single bond as above 101 ~R 115 Each is 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.

[0575] R is selected from the group consisting of 101 ~R 105 The two adjacent ones in are not bonded to each other and thus do not form a ring.

[0576] R is selected from the group consisting of 106 ~R 110 The two adjacent ones in are not bonded to each other and thus do not form a ring.

[0577] R is selected from the group consisting of 111 ~R 115 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring.

[0578] In L 1 When it is a single bond, it is Ar 1 *21 of the group represented by formula (1a) represents the bonding position to the central nitrogen atom N*,

[0579] In L 2 When it is a single bond, it is Ar 2 *21 of the group represented by the formula (1a) represents a bonding position to the central nitrogen atom N*.

[0580] R is not a single bond as above 101 ~R 115 The details of the unsubstituted alkyl radical having 1 to 10 carbon atoms are the same as those for R except that the number of carbon atoms is 1 to 10. a and R b The records are the same.

[0581] The above R 101~R 115 The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms are the same as those for R except that the number of ring carbon atoms is 6 to 12. a and R b The records are the same.

[0582] R that is not a single bond to *22 101 ~R 105 R may be a hydrogen atom, not a single bond to *23 106 ~R 110 R may be a hydrogen atom, not a single bond to *24 111 ~R 115 They may all be hydrogen atoms.

[0583] m is 0 or 1, n is 0 or 1, and 1 is 0 or 1.

[0584] When m is 0, n is 1 and 1 is 0 or 1, *22 means L 1 or L 2 The bonding position of (*22 indicates *21), when m is 0, n is 0 and 1 is 1, *23 indicates the bonding position with L 1 or L 2 The bonding position (*23 represents *21), when m is 0, n is 0 and 1 is 0, *24 represents the bonding position with L 1 or L 2 The bonding position of (*24 indicates *21).

[0585] 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.

[0586] [Chemical formula 33]

[0587]

[0588] In another embodiment of the present invention, m is 1, n is 0, and 1 is 0. In this case, *24 represents *22, and formula (1a) is represented by the following formula.

[0589] [Chemical formula 34]

[0590]

[0591] In another embodiment of the present invention, m is 0, n is 1, and 1 is 0. In this case, *22 represents *21, *24 represents *23, and formula (1a) is represented by the following formula.

[0592] [Chemical formula 35]

[0593]

[0594] In 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.

[0595] [Chemical formula 36]

[0596]

[0597] In another embodiment of the present invention, m is 1, n is 1, and 1 is 0. In this case, *24 represents *23, and formula (1a) is represented by the following formula.

[0598] [Chemical formula 37]

[0599]

[0600] In another embodiment of the present invention, m is 1, n is 0, and 1 is 1. In this case, *23 represents *22, and formula (1a) is represented by the following formula.

[0601] [Chemical formula 38]

[0602]

[0603] In another embodiment of the present invention, m is 0, n is 1, and 1 is 1. In this case, *22 represents *21, and formula (1a) is represented by the following formula.

[0604] [Chemical formula 39]

[0605]

[0606] In another embodiment of the present invention, m is 1, n is 1, and 1 is 1. In this case, formula (1a) is represented by the following formula.

[0607] [Chemical formula 40]

[0608]

[0609] The group represented by the above formula (1a) preferably satisfies at least one of the following (i) to (iii).

[0610] (i)R 101 or R 105 is a single bond bonded to *22

[0611] (ii) R 106 or R 110 is a single bond to *23

[0612] (iii) R 111 or R 115 is a single bond to *24

[0613] R 116 ~R 120 Each is 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.

[0614] Selected from R 116 ~R 120 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring.

[0615] The above R 116 ~R 120 The details of the unsubstituted alkyl radical having 1 to 10 carbon atoms are the same as those for R except that the number of carbon atoms is 1 to 10. a and R b The records are the same.

[0616] The above R 116 ~R 120 The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms are the same as those for R except that the number of ring carbon atoms is 6 to 12. a and R b The records are the same.

[0617] The above R 116 ~R 120 The details of the unsubstituted aryl group having 5 to 13 ring carbon atoms are the same as those for R except that the number of ring atoms is 5 to 13. a and R b The records are the same.

[0618] The above R 116 ~R 120 They may all be hydrogen atoms.

[0619] The group represented by formula (1a) is preferably represented by the following formula: In the following formula, R is omitted for simplicity.

[0620] [Chemical formula 41]

[0621]

[0622] Formula (1b) is represented by the following formula.

[0623] [Chemical formula 42]

[0624]

[0625] In formula (1b),

[0626] *25 is the same as L 1 or L 2 bonding position.

[0627] Selected from R 121 ~R 128 One of them is a single bond to *26.

[0628] R is not a single bond as above 121 ~R 128 Each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10, preferably 1 to 6, carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms.

[0629] R is selected from the group consisting of 121 ~R 128 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring.

[0630] Among them, in L 1 is p-phenylene, Ar 1 When represented by formula (1b), the group represented by formula (1b) bonded to the p-phenylene group is selected from R 121 , R 124 , R 125 and R 128 One of them is a single bond to *26,

[0631] In L 2 is p-phenylene, Ar 2 When represented by formula (1b), the group represented by formula (1b) bonded to the p-phenylene group is selected from R 121 , R 124 , R 125 and R 128 One of them is a single bond to *26.

[0632] In L 1 When it is a single bond, it is Ar 1 *25 of the group represented by formula (1b) represents the bonding position to the central nitrogen atom N*,

[0633] In L 2 When it is a single bond, it is Ar 2 *25 of the group represented by the formula (1b) represents a bonding position to the central nitrogen atom N*.

[0634] The above R 121 ~R 128 The details of the unsubstituted alkyl radical having 1 to 10 carbon atoms are the same as those for R except that the number of carbon atoms is 1 to 10. a and R b The records are the same.

[0635] The above R 121 ~R 128The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms are the same as those for R except that the number of ring carbon atoms is 6 to 12. a and R b The records are the same.

[0636] In one embodiment of the present invention, preferably R 121 is a single bond bonded to *26. In another embodiment, preferably R 122 It is a single bond bonded to *26.

[0637] R that is not a single bond to *26 121 ~R 128 They may all be hydrogen atoms.

[0638] Formula (1c) is represented by the following formula.

[0639] [Chemical formula 43]

[0640]

[0641] In formula (1c),

[0642] *27 is with L 1 or L 2 bonding position.

[0643] Selected from R 131 ~R 140 One of them is a single bond to *28.

[0644] R is not a single bond as above 131 ~R 140 Each is 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.

[0645] R is selected from the group consisting of 131 ~R 140 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring.

[0646] In L 1 When it is a single bond, it is Ar 1 *27 of the group represented by formula (1c) represents the bonding position to the central nitrogen atom N*,

[0647] In L 2 When it is a single bond, it is Ar 2 *27 of the group represented by the formula (1c) represents a bonding position to the central nitrogen atom N*.

[0648] The above R 131 ~R 140The details of the unsubstituted alkyl radical having 1 to 6 carbon atoms are the same as those for R except that the number of carbon atoms is 1 to 6. a and R b The records are the same.

[0649] The above R 131 ~R 140 The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms are the same as those for R except that the number of ring carbon atoms is 6 to 12. a and R b The records are the same.

[0650] In one embodiment of the present invention, preferably R 131 is a single bond bonded to *28. In another embodiment, preferably R 132 is a single bond bonded to *28. In another embodiment, preferably R 140 It is a single bond bonded to *28.

[0651] R that is not a single bond to *28 131 ~R 140 They may all be hydrogen atoms.

[0652] Formula (1d) is represented by the following formula.

[0653] [Chemical formula 44]

[0654]

[0655] In formula (1d),

[0656] *29 is with L 1 or L 2 bonding position.

[0657] Selected from R 141 ~R 152 One of them is a single bond bonded to *30.

[0658] R is not a single bond as above 141 ~R 152 Each is 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.

[0659] R is selected from the group consisting of 141 ~R 152 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring structure.

[0660] In L 1 When it is a single bond, it is Ar 1 *29 of the group represented by formula (1d) represents the bonding position to the central nitrogen atom N*,

[0661] In L 2 When it is a single bond, it is Ar 2 *29 of the group represented by the formula (1d) represents a bonding position to the central nitrogen atom N*.

[0662] The above R 141 ~R 152 The details of the unsubstituted alkyl radical having 1 to 10 carbon atoms are the same as those for R except that the number of carbon atoms is 1 to 10. a and R b The records are the same.

[0663] The above R 141 ~R 152 The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms are the same as those for R except that the number of ring carbon atoms is 6 to 12. a and R b The records are the same.

[0664] R that is not a single bond to *30 141 ~R 152 They may all be hydrogen atoms.

[0665] Formula (1e) is represented by the following formula.

[0666] [Chemical formula 45]

[0667]

[0668] In formula (1e),

[0669] *31 is with L 1 or L 2 bonding position.

[0670] Selected from R 161 ~R 165 One of them is a single bond bonded to *32, selected from R 161 ~R 165 The other one in is a single bond to *33.

[0671] R which is neither the single bond bonded to *32 nor the single bond bonded to *33 161 ~R 165 Each is 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.

[0672] R is selected from a single bond that is neither bonded to *32 nor bonded to *33 161 ~R 165 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring.

[0673] In L 1When it is a single bond, it is Ar 1 *31 of the group represented by formula (1e) represents the bonding position to the central nitrogen atom N*,

[0674] In L 2 When it is a single bond, it is Ar 2 *31 of the group represented by the formula (1e) represents a bonding position to the central nitrogen atom N*.

[0675] R which is neither the single bond bonded to *32 nor the single bond bonded to *33 161 ~R 165 The details of the unsubstituted alkyl radical having 1 to 10 carbon atoms are the same as those for R except that the number of carbon atoms is 1 to 10. a and R b The records are the same.

[0676] The above R 141 ~R 152 The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms are the same as those for R except that the number of ring carbon atoms is 6 to 12. a and R b The records are the same.

[0677] R is not a single bond bonded to *32 nor a single bond bonded to *33 161 ~R 165 They may all be hydrogen atoms.

[0678] R 171 ~R 175 and R 181 ~R 185 Each independently represents a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms.

[0679] Selected from R 171 ~R 175 Two adjacent ones of the alkyl groups may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form no ring.

[0680] Selected from R 181 ~R 185 Two adjacent ones of the alkyl groups may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form no ring.

[0681] The above R 171 ~R 175 and R 181 ~R 185 The details of the unsubstituted alkyl radical having 1 to 10 carbon atoms are the same as those for R except that the number of carbon atoms is 1 to 10. a and R b The records are the same.

[0682] The above R 171 ~R 175 and R 181 ~R 185 They may all be hydrogen atoms.

[0683] The formula (1e) includes groups represented by the following formulae (1e-1) to (1e-5), and preferably the formula (1e-1), (1e-2) or (1e-4).

[0684] [Chemical formula 46]

[0685]

[0686] Formula (1f) is represented by the following formula.

[0687] [Chemical formula 47]

[0688]

[0689] In formula (1f),

[0690] *34 is with L 1 or L 2 bonding position.

[0691] X is an oxygen atom, a sulfur atom or NR A .

[0692] X is preferably an oxygen atom or NR A .

[0693] Selected from R 191 ~R 198 and R A One of them is a single bond to *35.

[0694] R is not a single bond as above A It 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.

[0695] In L 1 When it is a single bond, it is Ar 1 *34 of the group represented by formula (1f) represents the bonding position to the central nitrogen atom N*,

[0696] In L 2 When it is a single bond, it is Ar 2 *34 of the group represented by the formula (1f) represents a bonding position to the central nitrogen atom N*.

[0697] The above R A The details of the unsubstituted alkyl radical having 1 to 6 carbon atoms are the same as those for R except that the number of carbon atoms is 1 to 6.a and R b The records are the same.

[0698] The above R A The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms are the same as those for R except that the number of ring carbon atoms is 6 to 12. a and R b The records are the same.

[0699] R is not a single bond as above 191 ~R 198 Each is 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.

[0700] R is selected from the group consisting of 191 ~R 198 Two adjacent ones of the alkyl groups may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form no ring.

[0701] R is not a single bond as above 191 ~R 198 The details of the unsubstituted alkyl radical having 1 to 6 carbon atoms are the same as those for R except that the number of carbon atoms is 1 to 6. a and R b The records are the same.

[0702] R is not a single bond as above 191 ~R 198 The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms are the same as those for R except that the number of ring carbon atoms is 6 to 12. a and R b The records are the same.

[0703] R is not a single bond as above 191 ~R 198 The details of the unsubstituted heterocyclic group having 5 to 13 ring atoms are the same as those for R except that the number of ring atoms is 5 to 13. a and R b The records are the same.

[0704] R that is not a single bond to *35 191 ~R 198 They may all be hydrogen atoms.

[0705] When X is an oxygen atom or a sulfur atom, it is preferably selected from R 191 ~R 194 One of them is a single bond to *35.

[0706] In X is NR A When, preferably selected from R191 ~R 194 and R A One of them is a single bond to *35.

[0707] R A A single bond or unsubstituted phenyl group bonded to *35 is particularly preferred.

[0708] Formula (1g) is represented by the following formula.

[0709] [Chemical formula 48]

[0710]

[0711] In formula (1g),

[0712] *36 is with L 1 or L 2 bonding position.

[0713] Selected from R B , R C and R 201 ~R 208 One of them is a single bond to *37.

[0714] RB and R are not single bonds. C Each is 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.

[0715] RB and R are not the single bonds mentioned above. C They may be bonded to each other to form a substituted or unsubstituted ring.

[0716] In L 1 When it is a single bond, it is Ar 1 *36 of the group represented by the formula (1g) represents the bonding position to the central nitrogen atom N*,

[0717] In L 2 When it is a single bond, it is Ar 2 *36 of the group represented by the formula (1g) represents a bonding position to the central nitrogen atom N*.

[0718] In one embodiment of the present invention, RB and R C Each independently is preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a phenyl group.

[0719] RB and R are not single bonds. C The details of the unsubstituted alkyl radical having 1 to 6 carbon atoms are the same as those for R except that the number of carbon atoms is 1 to 6. a and R b The records are the same.

[0720] R is not a single bond as above B and R C The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms are the same as those for R except that the number of ring carbon atoms is 6 to 12. a and R b The records are the same.

[0721] R is not a single bond as above B and R C The details of the unsubstituted heterocyclic group having 5 to 13 ring atoms are the same as those for R except that the number of ring atoms is 5 to 13. a and R b The records are the same.

[0722] R is not a single bond as above B With R C The details of the unsubstituted ring formed by bonding to each other are the same as for R a and R b The records are the same.

[0723] R is not a single bond as above 201 ~R 208 Each is 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.

[0724] Among them, R is selected from the group consisting of 201 ~R 208 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring.

[0725] R is not a single bond as above 201 ~R 208 The details of the unsubstituted alkyl radical having 1 to 6 carbon atoms are the same as those for R except that the number of carbon atoms is 1 to 6. a and R b The records are the same.

[0726] R is not a single bond as above 201 ~R 208 The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms are the same as those for R except that the number of ring carbon atoms is 6 to 12. a and R b The records are the same.

[0727] R is not a single bond as above 201 ~R 208 The details of the unsubstituted heterocyclic group having 5 to 13 ring atoms are the same as those for R except that the number of ring atoms is 5 to 13. a and R bThe records are the same.

[0728] In one embodiment of the present invention, preferably R 202 or R 207 It is a single bond bonded to *37.

[0729] In one embodiment of the present invention, preferably Ar 1 and Ar 2 At least one of them is a group represented by the above formula (1a) or (1g).

[0730] In one embodiment of the present invention, preferably, Ar 1 or Ar 2 It is a group represented by the above formula (1a), and the group represented by the above formula (1a) satisfies at least one of the following (i) to (iii).

[0731] (i)R 101 or R 105 is a single bond bonded to *22

[0732] (ii) R 106 or R 110 is a single bond to *23

[0733] (iii) R 111 or R 115 is a single bond to *24

[0734] In one embodiment of the present invention, preferably, Ar 1 or Ar 2 is a group represented by the above formula (1g) and RB and R in the group represented by the above formula (1g) C Each is independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted phenyl group.

[0735] In one embodiment of the present invention, preferably, Ar 1 or Ar 2 is a group represented by the above formula (1g) and R 202 or R 207 It is a single bond bonded to *37.

[0736] As mentioned above, the "hydrogen atom" used in this specification includes protium atoms, deuterium atoms and tritium atoms. Therefore, the inventive compound may contain deuterium atoms of natural origin.

[0737] In addition, deuterium atoms can be intentionally introduced into compound (1) by using deuterated compounds as part or all of the raw material compounds. Therefore, in one embodiment of the present invention, compound (1) contains at least one deuterium atom. That is, the inventive compound can also be a compound represented by formula (1), in which at least one of the hydrogen atoms contained in the compound is a deuterium atom.

[0738] At least one hydrogen atom selected from the following hydrogen atoms may be a deuterium atom. It should be noted that, in the following, "substituted or unsubstituted", the number of carbon atoms and the number of atoms are omitted for simplicity.

[0739] In formula (1), R a and R b When it is an alkyl group, an aryl group or a heterocyclic group, the hydrogen atoms possessed by these groups;

[0740] R in formula (1) 1 ~R 5 , R 8 and R which is not a single bond bonded to *1 6 and R 7 The hydrogen atom represented by

[0741] In formula (1), R 1 ~R 5 , R 8 and R which is not a single bond bonded to *1 6 and R 7 When it is an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group, the hydrogen atoms possessed by these groups;

[0742] R in formula (1) 11 ~R 14 The hydrogen atom represented by

[0743] In formula (1), R 11 ~R 14 When it is an alkyl group or an aryl group, the hydrogen atoms possessed by these groups;

[0744] In formula (1), L 1 ~L 4 In the case of arylene groups, the hydrogen atoms possessed by these groups;

[0745] R of formula (1a) which is not a single bond bonded to *22 101 ~R 105 、R that is not a single bond to *23 106 ~R 110 、R that is not a single bond to *24 111 ~R 115 The hydrogen atom represented by

[0746] In formula (1a), R which is not a single bond bonded to *22 101 ~R 105 、R that is not a single bond to *23 106 ~R 110 、R that is not a single bond to *24 111 ~R 115 When it is an alkyl group or an aryl group, the hydrogen atoms possessed by these groups;

[0747] R in formula (1a) 116 ~R 120 The hydrogen atom represented by

[0748] In formula (1a), R 116 ~R 120 When it is an alkyl group, an aryl group or a heterocyclic group, the hydrogen atoms possessed by these groups;

[0749] R of formula (1b) which is not a single bond bonded to *26 121 ~R 128 The hydrogen atom represented by

[0750] In formula (1b), R which is not a single bond bonded to *26 121 ~R 128 When it is an alkyl group or an aryl group, the hydrogen atoms possessed by these groups;

[0751] R of formula (1c) which is not a single bond bonded to *28 131 ~R 140 The hydrogen atom represented by

[0752] In formula (1c), R which is not a single bond bonded to *28 131 ~R 140 When it is an alkyl group or an aryl group, the hydrogen atoms possessed by these groups;

[0753] R of formula (1d) which is not a single bond bonded to *30 141 ~R 152 The hydrogen atom represented by

[0754] In formula (1d), R which is not a single bond bonded to *30 141 ~R 152 When it is an alkyl group or an aryl group, the hydrogen atoms possessed by these groups;

[0755] R of formula (1e) which is not a single bond bonded to *32 and is not a single bond bonded to *33 161 ~R 165 The hydrogen atom represented by

[0756] In formula (1e), R which is not a single bond bonded to *32 and is not a single bond bonded to *33 described above 161~R 165 When it is an alkyl group or a phenyl group, the hydrogen atoms possessed by these groups;

[0757] R in formula (1e) 171 ~R 175 and R 181 ~R 185 The hydrogen atom represented by

[0758] In formula (1e), R 171 ~R 175 and R 181 ~R 185 When they are alkyl groups, the hydrogen atoms possessed by these groups;

[0759] In formula (1f), R which is not a single bond bonded to *35 A When it is an alkyl group or an aryl group, the hydrogen atoms possessed by these groups;

[0760] R of formula (1f) which is not a single bond bonded to *35 191 ~R 198 The hydrogen atom represented by

[0761] In formula (1f), R which is not a single bond bonded to *35 191 ~R 198 When it is an alkyl group, an aryl group or a heterocyclic group, the hydrogen atoms possessed by these groups;

[0762] In formula (1g), R B and R C When it is an alkyl group, an aryl group or a heterocyclic group, the hydrogen atoms possessed by these groups;

[0763] R of formula (1g) which is not a single bond bonded to *37 201 ~R 208 The hydrogen atom represented by

[0764] In formula (1g), R which is not a single bond bonded to *37 201 ~R 208 In the case of an alkyl group, an aryl group or a heterocyclic group, the hydrogen atoms possessed by these groups.

[0765] The deuteration rate of the invention compound depends on the deuteration rate of the raw material compound used. Even if a raw material with a specified deuteration rate is used, it is possible to contain protium isotopes at a certain ratio of natural origin. Therefore, for the scheme of the deuteration rate of the invention compound shown below, the ratio calculated by counting only the number of deuterium atoms represented in the chemical formula includes a ratio that takes into account trace amounts of isotopes of natural origin.

[0766] The deuteration rate of the compound of the invention is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, further preferably 10% or more, further preferably 50% or more.

[0767] The compound of the invention may be a mixture of 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, further preferably 5% or more, further preferably 10% or more, further preferably 50% or more, and less than 100%.

[0768] The ratio of the number of deuterium atoms to the total number of hydrogen atoms in the compound of the invention is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, further preferably 10% or more, and is 100% or less.

[0769] When the "substituted or unsubstituted XX group" included in the definitions of the above formulae is a substituted XX group, the details of the substituent are the same as those described in "Substituents when expressed as "substituted or unsubstituted", 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, and 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.

[0770] The compounds of the invention can be easily produced by those skilled in the art with reference to the following synthesis examples and known synthesis methods.

[0771] Specific examples of the compounds of the invention are shown below, but the compounds of the invention are not limited to the following exemplified compounds.

[0772] In the following specific examples, D represents a deuterium atom.

[0773] [Chemical formula 49]

[0774]

[0775] [Chemical formula 50]

[0776]

[0777] [Chemical formula 51]

[0778]

[0779] [Chemical formula 52]

[0780]

[0781] [Chemical formula 53]

[0782]

[0783] [Chemical formula 54]

[0784]

[0785] [Chemical formula 55]

[0786]

[0787] [Chemical formula 56]

[0788]

[0789] [Chemical formula 57]

[0790]

[0791] [Chemical formula 58]

[0792]

[0793] [Chemical formula 59]

[0794]

[0795] [Chemical formula 60]

[0796]

[0797] [Chemical formula 61]

[0798]

[0799] [Chemical formula 62]

[0800]

[0801] [Chemical formula 63]

[0802]

[0803] [Chemical formula 64]

[0804]

[0805] [Chemical formula 65]

[0806]

[0807] [Chemical formula 66]

[0808]

[0809] [Chemical formula 67]

[0810]

[0811] [Chemical formula 68]

[0812]

[0813] [Chemical formula 69]

[0814]

[0815] [Chemical formula 70]

[0816]

[0817] [Chemical formula 71]

[0818]

[0819] [Chemical formula 72]

[0820]

[0821] [Chemical formula 73]

[0822]

[0823] [Chemical formula 74]

[0824]

[0825] [Chemical formula 75]

[0826]

[0827] [Chemical formula 76]

[0828]

[0829] [Chemical formula 77]

[0830]

[0831] [Chemical formula 78]

[0832]

[0833] [Chemical formula 79]

[0834]

[0835] [Chemical formula 80]

[0836]

[0837] [Chemical formula 81]

[0838]

[0839] [Chemical formula 82]

[0840]

[0841] [Chemical formula 83]

[0842]

[0843] [Chemical formula 84]

[0844]

[0845] [Chemical formula 85]

[0846]

[0847] [Chemical formula 86]

[0848]

[0849] [Chemical formula 87]

[0850]

[0851] [Chemical formula 88]

[0852]

[0853] [Chemical formula 89]

[0854]

[0855] [Chemical formula 90]

[0856]

[0857] [Chemical formula 91]

[0858]

[0859] [Chemical formula 92]

[0860]

[0861] [Chemical formula 93]

[0862]

[0863] [Chemical formula 94]

[0864]

[0865] [Chemical formula 95]

[0866]

[0867] [Chemical formula 96]

[0868]

[0869] [Chemical formula 97]

[0870]

[0871] [Chemical formula 98]

[0872]

[0873] [Chemical formula 99]

[0874]

[0875] [Chemical formula 100]

[0876]

[0877] [Chemical Formula 101]

[0878]

[0879] [Chemical formula 102]

[0880]

[0881] [Chemical formula 103]

[0882]

[0883] [Chemical formula 104]

[0884]

[0885] [Chemical formula 105]

[0886]

[0887] [Chemical formula 106]

[0888]

[0889] [Chemical formula 107]

[0890]

[0891] [Chemical formula 108]

[0892]

[0893] [Chemical formula 109]

[0894]

[0895] [Chemical formula 110]

[0896]

[0897] [Chemical formula 111]

[0898]

[0899] [Chemical formula 112]

[0900]

[0901] [Chemical formula 113]

[0902]

[0903] [Chemical formula 114]

[0904]

[0905] [Chemical formula 115]

[0906]

[0907] [Chemical formula 116]

[0908]

[0909] [Chemical formula 117]

[0910]

[0911] [Chemical formula 118]

[0912]

[0913] [Chemical formula 119]

[0914]

[0915] [Chemical formula 120]

[0916]

[0917] [Chemical formula 121]

[0918]

[0919] [Chemical formula 122]

[0920]

[0921] [Chemical formula 123]

[0922]

[0923] [Chemical formula 124]

[0924]

[0925] [Chemical formula 125]

[0926]

[0927] [Chemical formula 126]

[0928]

[0929] [Chemical formula 127]

[0930]

[0931] [Chemical formula 128]

[0932]

[0933] [Chemical formula 129]

[0934]

[0935] [Chemical formula 130]

[0936]

[0937] [Chemical formula 131]

[0938]

[0939] [Chemical formula 132]

[0940]

[0941] [Chemical formula 133]

[0942]

[0943] [Chemical formula 134]

[0944]

[0945] [Chemical formula 135]

[0946]

[0947] [Chemical formula 136]

[0948]

[0949] [Chemical formula 137]

[0950]

[0951] [Chemical formula 138]

[0952]

[0953] [Chemical formula 139]

[0954]

[0955] [Chemical formula 140]

[0956]

[0957] [Chemical formula 141]

[0958]

[0959] [Chemical formula 142]

[0960]

[0961] [Chemical formula 143]

[0962]

[0963] [Chemical formula 144]

[0964]

[0965] [Chemical formula 145]

[0966]

[0967] [Chemical formula 146]

[0968]

[0969] [Chemical formula 147]

[0970]

[0971] [Chemical formula 148]

[0972]

[0973] [Chemical formula 149]

[0974]

[0975] [Chemical formula 150]

[0976]

[0977] [Chemical formula 151]

[0978]

[0979] [Chemical formula 152]

[0980]

[0981] [Chemical formula 153]

[0982]

[0983] [Chemical formula 154]

[0984]

[0985] [Chemical formula 155]

[0986]

[0987] [Chemical formula 156]

[0988]

[0989] [Chemical formula 157]

[0990]

[0991] [Chemical formula 158]

[0992]

[0993] [Chemical formula 159]

[0994]

[0995] [Chemical formula 160]

[0996]

[0997] [Chemical formula 161]

[0998]

[0999] [Chemical formula 162]

[1000]

[1001] [Chemical formula 163]

[1002]

[1003] [Chemical formula 164]

[1004]

[1005] [Chemical formula 165]

[1006]

[1007] [Chemical formula 166]

[1008]

[1009] [Chemical formula 167]

[1010]

[1011] [Chemical formula 168]

[1012]

[1013] [Chemical formula 169]

[1014]

[1015] [Chemical formula 170]

[1016]

[1017] [Chemical formula 171]

[1018]

[1019] [Chemical formula 172]

[1020]

[1021] [Chemical formula 173]

[1022]

[1023] [Chemical formula 174]

[1024]

[1025] [Chemical formula 175]

[1026]

[1027] [Chemical formula 176]

[1028]

[1029] [Chemical formula 177]

[1030]

[1031] [Chemical formula 178]

[1032]

[1033] [Chemical formula 179]

[1034]

[1035] Materials for organic EL devices

[1036] The material for an organic EL element of the present invention comprises the compound of the invention. The content of the compound of the invention in the material for an organic EL element 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%), further preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). The material for an organic EL element of the present invention is useful for the manufacture of an organic EL element.

[1037] Organic EL elements

[1038] 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 comprises a light-emitting layer, and at least one layer of the organic layer comprises the compound of the present invention.

[1039] As examples of organic layers containing the invention compound, there can be cited a hole transport region (hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer, etc.) disposed between the anode and the light-emitting layer, a light-emitting layer, a spacer layer, an electron transport region (electron injection layer, electron transport layer, hole blocking layer, etc.) disposed between the cathode and the light-emitting layer, etc., but are not limited thereto. The invention compound is preferably used as a material for the hole transport region or the light-emitting layer of a fluorescent or phosphorescent EL element, more preferably as a material for the hole transport region, further preferably as a material for a hole injection layer, a hole transport layer, an electron blocking layer, or an exciton blocking layer, and particularly preferably as a material for a hole injection layer or a hole transport layer.

[1040] The organic EL element of the present invention can be a single-color light-emitting element of fluorescent or phosphorescent light-emitting type, or a white light-emitting element of fluorescent / phosphorescent mixed type, and can be a simple type having a single light-emitting unit, or a tandem type (Tandem) having multiple light-emitting units, wherein a fluorescent light-emitting element is preferred. Here, "light-emitting unit" refers to: a minimum unit that includes an organic layer, at least one of which is a light-emitting layer, and the injected holes and electrons recombine to emit light.

[1041] For example, as a typical element structure of a simple organic EL element, the following element structure can be cited.

[1042] (1) Anode / light-emitting unit / cathode

[1043] In addition, the above-mentioned light-emitting unit may also be a multilayer type having a plurality of phosphorescent light-emitting layers or fluorescent light-emitting layers. In this case, a spacer layer may be provided between each light-emitting layer for the purpose of preventing the excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer. The following shows a typical layer structure of a simplified light-emitting unit. The layers in parentheses are optional.

[1044] (a) (hole injection layer / ) hole transport layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[1045] (b) (hole injection layer / ) hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / electron transport layer ( / electron injection layer)

[1046] (c) (hole injection layer / ) hole transport layer / phosphorescent light emitting layer / spacer layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[1047] (d) (hole injection layer / ) hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer / spacer layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[1048] (e) (hole injection layer / ) hole transport layer / phosphorescent emitting layer / spacer layer / first fluorescent emitting layer / second fluorescent emitting layer / electron transport layer ( / electron injection layer)

[1049] (f) (hole injection layer / ) hole transport layer / electron blocking layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[1050] (g) (hole injection layer / ) hole transport layer / exciton blocking layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[1051] (h) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[1052] (i) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer)

[1053] (j) (hole injection layer / ) hole transport layer / fluorescent light emitting layer / hole blocking layer / electron transport layer ( / electron injection layer)

[1054] (k) (hole injection layer / ) hole transport layer / fluorescent light emitting layer / exciton blocking layer / electron transport layer ( / electron injection layer)

[1055] (1) (hole injection layer / ) first hole transport layer / second hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer)

[1056] (m) (hole injection layer / ) first hole transport layer / second hole transport layer / third hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer)

[1057] (n) (hole injection layer / ) first hole transport layer / second hole transport layer / third hole transport layer / fluorescent light emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer)

[1058] Each of the phosphorescent or fluorescent light-emitting layers can be configured to emit light of different colors. Specifically, in the light-emitting unit (f), a layer structure such as (hole injection layer / ) hole transport layer / first phosphorescent light-emitting layer (red light emission) / second phosphorescent light-emitting layer (green light emission) / spacer layer / fluorescent light-emitting layer (blue light emission) / electron transport layer can be cited.

[1059] It should be noted that an electron blocking layer may be appropriately provided between each light-emitting layer and the hole transport layer or the spacer layer. In addition, a hole blocking layer may be appropriately provided between each light-emitting layer and the electron transport layer. By providing an electron blocking layer or a hole blocking layer, electrons or holes may be confined in the light-emitting layer to increase the recombination probability of charges in the light-emitting layer, thereby improving the luminous efficiency.

[1060] As a typical device structure of a tandem organic EL device, the following device structures can be mentioned.

[1061] (2) Anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode

[1062] Here, the first light emitting unit and the second light emitting unit may be independently selected from the light emitting units described above, for example.

[1063] The intermediate layer is generally referred to as an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, or an intermediate insulating layer, and can be made of a known material that supplies electrons to the first light-emitting unit and holes to the second light-emitting unit.

[1064] Figure 1Schematic diagram showing an example of the structure of the organic EL element of the present invention. The organic EL element 1 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10 arranged between the anode 3 and the cathode 4. The light-emitting unit 10 has a light-emitting layer 5. There is a hole transport region 6 (hole injection layer, hole transport layer, etc.) between the light-emitting layer 5 and the anode 3, and there is an electron transport region 7 (electron injection layer, electron transport layer, etc.) between the light-emitting layer 5 and the cathode 4. In addition, an electron blocking layer (not shown) can be provided on the anode 3 side of the light-emitting layer 5, and a hole blocking layer (not shown) can be provided on the cathode 4 side of the light-emitting layer 5, respectively. In this way, electrons and holes can be confined in the light-emitting layer 5 to further improve the generation efficiency of excitons in the light-emitting layer 5.

[1065] Figure 2 Schematic diagram showing another structure of the organic EL element of the present invention. The organic EL element 11 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 20 disposed between the anode 3 and the cathode 4. The light-emitting unit 20 has a light-emitting layer 5. The hole transport region disposed between the anode 3 and the light-emitting layer 5 is formed by a hole injection layer 6a, a first hole transport layer 6b, and a second hole transport layer 6c. In addition, the electron transport region disposed between the light-emitting layer 5 and the cathode 4 is formed by a first electron transport layer 7a and a second electron transport layer 7b.

[1066] Figure 3 Schematic diagram showing another structure of the organic EL element of the present invention. The organic EL element 12 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 30 disposed between the anode 3 and the cathode 4. The light-emitting unit 30 has a light-emitting layer 5. The hole transport region disposed between the anode 3 and the light-emitting layer 5 is formed by a hole injection layer 6a, a first hole transport layer 6b, a second hole transport layer 6c, and a third hole transport layer 6d. In addition, the electron transport region disposed between the light-emitting layer 5 and the cathode 4 is formed by a first electron transport layer 7a and a second electron transport layer 7b.

[1067] It should be noted that in the present invention, the host combined with the fluorescent dopant material (fluorescent luminescent material) is called a fluorescent host, and the host combined with the phosphorescent dopant material is called a phosphorescent host. The fluorescent host and the phosphorescent host are not distinguished only by the molecular structure. That is, the phosphorescent host refers to the material that forms the phosphorescent luminescent layer containing the phosphorescent dopant, and does not mean that it cannot be used as a material for forming the fluorescent luminescent layer. The same is true for the fluorescent host.

[1068] substrate

[1069] The substrate is used as a support of the organic EL element. As the substrate, for example, a plate of glass, quartz, plastic, etc. can be used. In addition, a flexible substrate can also be used. As the flexible substrate, for example, a plastic substrate formed of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, etc. can be cited. In addition, an inorganic vapor-deposited film can also be used.

[1070] anode

[1071] The anode formed on the substrate preferably uses a metal, alloy, conductive compound, and a mixture thereof with a large work function (specifically, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO: Indium Tin Oxide, indium tin oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, graphene, etc. In addition, 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 (such as titanium nitride), etc. can be mentioned.

[1072] These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering 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 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. In addition, it can also be produced by vacuum evaporation, coating, inkjet, spin coating, etc.

[1073] Hole transport region

[1074] As described above, the organic layer may include a hole transport region between the anode and the light-emitting layer. The hole transport region is composed of a hole injection layer, a hole transport layer, an electron blocking layer, etc. The hole transport region preferably contains the invention compound. It is preferred that at least one of the layers constituting the hole transport layer contains the invention compound, and it is particularly preferred that the hole transport layer contains the invention compound.

[1075] The hole injection layer formed adjacent to the anode is formed using a material that easily allows hole injection regardless of the work function of the anode. Therefore, materials commonly used as electrode materials (such as metals, alloys, conductive compounds and mixtures thereof, elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[1076] It is also possible to use elements belonging to the first or second group of the periodic table as materials with a small work function, 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 them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing them. It should be noted that when using alkali metals, alkaline earth metals, and alloys containing them to form an anode, a vacuum evaporation method or a sputtering method can be used. In addition, when using silver paste, a coating method, an inkjet method, etc. can be used.

[1077] Hole injection layer

[1078] 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 a hole transport layer is present, between the hole transport layer and the anode.

[1079] As hole injecting materials other than the invention compound, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. can be used.

[1080] Examples of hole injection layer materials include low molecular weight organic compounds such as 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNT PD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) and other aromatic amine compounds.

[1081] High molecular weight compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, high molecular weight compounds such as poly(N-vinyl carbazole) (abbreviated as PVK), poly(4-vinyl triphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD) can be mentioned. In addition, high molecular weight compounds to which an acid is added, such as poly(3,4-ethylenedioxythiophene) / poly(styrene sulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrene sulfonic acid) (PAni / PSS), can also be used.

[1082] In addition, an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K) is also preferably used.

[1083] [Chemical formula 180]

[1084]

[1085] (In the above formula, R 221 ~R 226 Each independently represents a cyano group, -CONH2, a carboxyl group, or a -COOR 227 (R 227 represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms). In addition, R 221 and R 222 , R 223 and R 224 and R 225 and R 226 Two adjacent ones of can be bonded to each other to form a group represented by -CO-O-CO-. )

[1086] As R2 27 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl and the like can be mentioned.

[1087] Hole transport layer

[1088] 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 a hole injection layer is present, between the hole injection layer and the light-emitting layer. The inventive compound can be used alone or in combination with the following compounds for the hole transport layer.

[1089] The hole transport layer may be a single-layer structure or a multilayer structure comprising more than two layers. For example, the hole transport layer may be a two-layer structure comprising a first hole transport layer (anode side) and a second hole transport layer (cathode side). That is, the hole transport region may include a first hole transport layer on the anode side and a second hole transport layer on the cathode side. In addition, the hole transport layer may be a three-layer structure comprising a first hole transport layer, a second hole transport layer and a third hole transport layer in sequence from the anode side. That is, a third hole transport layer may be configured between the second hole transport layer and the light-emitting layer.

[1090] In one embodiment of the present invention, the hole transport layer of the single-layer structure is preferably adjacent to the light-emitting layer. In addition, the hole transport layer closest to the cathode in the multi-layer structure, such as the second hole transport layer of the two-layer structure or the third hole transport layer of the three-layer structure, is preferably adjacent to the light-emitting layer. In another embodiment of the present invention, an electron blocking layer described later may be sandwiched between the hole transport layer of the single-layer structure and the light-emitting layer, or between the hole transport layer closest to the light-emitting layer in the multi-layer structure and the light-emitting layer.

[1091] 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 hole transport layer and the second hole transport layer.

[1092] In one embodiment of the present invention, the inventive compound is preferably contained in the second hole transport layer. That is, it is preferred that the inventive compound is contained only in the second hole transport layer, or that the inventive compound is contained in both the first hole transport layer and the second hole transport layer.

[1093] 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 layers of the first to third hole transport layers.

[1094] In one embodiment of the present invention, the inventive compound is preferably contained in the third hole transport layer. That is, the inventive compound is preferably contained only in the third hole transport layer, or in the third hole transport layer and one or both selected from the first hole transport layer and the second hole transport layer.

[1095] In one embodiment of the present invention, the inventive compound contained in each hole transport layer is preferably a protium compound from the viewpoint of production cost. The protium compound refers to an inventive compound in which all hydrogen atoms in the inventive compound are protium atoms.

[1096] Therefore, the present invention includes 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) contain an invention compound substantially composed of a protium body, and an organic EL device in which at least one of the first to third hole transport layers contains an invention compound substantially composed of a protium body. The meaning of "the invention compound substantially composed of a protium body" is that the content ratio of the protium body 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 (including 100%).

[1097] As hole transport layer materials other than the inventive compound, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used.

[1098] Examples of the aromatic amine compound include: 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated as BAFLP), 4,4'-bis[N-(9,9-dimethylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), The above compounds have 10 -6 cm 2 / Vs and above hole mobility.

[1099] Examples of the carbazole derivative 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-anthracenyl)phenyl]-9H-carbazole (abbreviation: PCzPA).

[1100] Examples of the anthracene derivative include 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth).

[1101] A polymer compound such as poly(N-vinylcarbazole) (abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation: PVTPA) may also be used.

[1102] However, any compound other than the above compounds may be used as long as the compound has a higher hole-transporting property than an electron-transporting property.

[1103] In the organic EL device having a two-layer hole transport layer of the present invention, it is preferred that the first hole transport layer contains one or more compounds represented by the following formula (11) or formula (12).

[1104] In the organic EL device having a three-layer hole transport layer of the present invention, it is preferred that one or both of the first hole transport layer and the second hole transport layer contain one or more compounds represented by the following formula (11) or (12).

[1105] In the organic EL element having a hole transport layer having an n-layer structure (n is an integer greater than or equal to 4) of the present invention, it is preferred that at least one of the first to (n-1)th hole transport layers contains one or more compounds represented by the following formula (11) or (12).

[1106] [Chemical formula 181]

[1107]

[1108] [In the above formula (11) and formula (12),

[1109] 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,

[1110] k is 1, 2, 3 or 4,

[1111] When k is 1, L E2 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,

[1112] When k is 2, 3 or 4, 2, 3 or 4 L E2 Same or different from each other,

[1113] When k is 2, 3 or 4, multiple L E2 are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,

[1114] L which does not form the above-mentioned monocyclic ring and does not form the above-mentioned condensed ring E2 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,

[1115] A 1 , B 1 , C 1 , A 2 , B 2 , C 2 and D 2 Each is independently 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 ),

[1116] R' 901 , R' 902 and R' 903 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1117] In R' 901 When there are multiple R' 901 Same or different from each other,

[1118] In R' 902 When there are multiple R' 902 Same or different from each other,

[1119] In R' 903 When there are multiple R' 903 The same as or different from each other.]

[1120] In formula (11) and formula (12), preferably, A 1 , B 1 , C 1 , A 2 , B 2 , C 2 and D 2 Each is 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 dibenzothienyl group and a substituted or unsubstituted carbazolyl group.

[1121] In addition, it is more preferred that A in formula (11) 1 , B 1 and C 1 At least one of them, and A2, B in formula (12) 2 , C 2 and D 2 At least one of them is 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.

[1122] A 1 , B 1 , C 1 , A 2 , B 2 , C 2 and D 2 The selectable fluorenyl group may have a substituent at position 9, for example, 9,9-dimethylfluorenyl group or 9,9-diphenylfluorenyl group. In addition, the substituents at position 9 may form a ring, for example, the substituents at position 9 may form a fluorene skeleton or a xanthene skeleton.

[1123] L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 Preferably, each independently is a single bond, a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.

[1124] Specific examples of the compounds represented by formula (11) and formula (12) include the following compounds.

[1125] [Chemical formula 182]

[1126]

[1127] Dopant materials for the light-emitting layer

[1128] The light-emitting layer is a layer containing a material with high luminescence (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 using a singlet excited state, and phosphorescent materials are compounds that emit light using a triplet excited state.

[1129] In one embodiment of the organic EL device according to the present invention, the light-emitting layer is a single layer.

[1130] In another embodiment of the organic EL device according to the present invention, the light-emitting layer includes a first light-emitting layer and a second light-emitting layer.

[1131] As the blue fluorescent material that can be used for the light-emitting layer, pyrene derivatives, styrylamine derivatives, Derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. Specifically, N, N'-bis [4- (9H-carbazole-9-yl) phenyl] -N, N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4- (9H-carbazole-9-yl) -4'- (10-phenyl-9-anthracenyl) triphenylamine (abbreviation: YGAPA), 4- (10-phenyl-9-anthracenyl) -4'- (9-phenyl-9H-carbazole-3-yl) triphenylamine (abbreviation: PCBAPA), etc. can be mentioned.

[1132] As green fluorescent light-emitting materials that can be used for the light-emitting layer, aromatic amine derivatives can be used. Specifically, N-(9,10-diphenyl-2-anthracenyl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCABPhA), N-(9,10-diphenyl-2-anthracenyl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPAPhA), PA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviated as 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviated as DPhAPhA), etc.

[1133] As the red fluorescent luminescent material that can be used for the light-emitting layer, tetracene derivatives, diamine derivatives, etc. can be used. Specifically, N, N, N', N'-tetrakis (4-methylphenyl) tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N, N, N', N'-tetrakis (4-methylphenyl) acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), etc. can be mentioned.

[1134] In one embodiment of the present invention, the light-emitting layer preferably contains a fluorescent light-emitting material (fluorescent dopant material).

[1135] As a blue phosphorescent material that can be used for the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes can be used. Specifically, bis[2-(4', 6'-difluorophenyl)pyridine-N, C2']iridium(III)tetrakis(1-pyrazolyl)borate (abbreviated as FIr6), bis[2-(4', 6'-difluorophenyl)pyridine-N, C2']iridium(III)picolinate (abbreviated as FIrpic), bis[2-(3', 5'bistrifluoromethylphenyl)pyridine-N, C2']iridium(III)picolinate (abbreviated as Ir(CF3ppy)2(pic)), bis[2-(4', 6'-difluorophenyl)pyridine-N, C2']iridium(III)acetylacetonate (abbreviated as FIracac), etc. can be cited.

[1136] As green phosphorescent materials that can be used for the light-emitting layer, iridium complexes can be used, such as tris(2-phenylpyridine-N,C2')iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridine-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazole)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), bis(benzo[h]quinoline)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)), and the like.

[1137] As the red phosphorescent light-emitting material that can be used for the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes can be used. Specifically, organic metal complexes such as bis[2-(2'-benzo[4,5-α]thienyl)pyridine-N,C3']iridium(III)acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinoline-N,C2')iridium(III)acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrinplatinum(II) (abbreviation: PtOEP) can be cited.

[1138] In addition, rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviated as: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedione)(monophenanthroline)europium(III) (abbreviated as: Eu(DBM)3(Phen)), and tris[1-(2-thiophenoyl)-3,3,3-trifluoroacetonate](monophenanthroline)europium(III) (abbreviated as: Eu(TTA)3(Phen)) can be used as phosphorescent materials because the luminescence comes from rare earth metal ions (electron transitions between different multiplicities).

[1139] Host material of the light-emitting layer

[1140] The light-emitting layer may be a structure in which the above-mentioned dopant material is dispersed in another material (host material). It is preferable to use a material having a higher lowest unoccupied molecular orbital level (LUMO level) and a lower highest occupied molecular orbital level (HOMO level) than the dopant material.

[1141] As the host material, use e.g.

[1142] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes,

[1143] (2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives,

[1144] (3) Carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or Derivatives and other condensed aromatic compounds,

[1145] (4) Aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives.

[1146] For example, metal complexes such as tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-hydroxyquinoline)aluminum(III) (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium(II) (abbreviated as BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO), and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ) can be used;

[1147] 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenyl)-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), bathocuproin (abbreviation: BCP) and other heterocyclic compounds;

[1148] 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviated as DPPA), 9,10-di(2-naphthyl)anthracene (abbreviated as DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviated as : t-BuDNA), 9,9'-bianthracene (abbreviated as: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviated as: DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviated as: DPNS2), 3,3',3"-(benzene-1,3,5-triyl)tripyrene (abbreviated as: TPB3), 9,10-diphenylanthracene (abbreviated as: DPAnth), 6,12-dimethoxy-5,11-diphenyl Equi-fused aromatic compounds; and

[1149] N,N-diphenyl-9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole-3-amine (abbreviated as: CzA1PA), 4-(10-phenyl-9-anthracenyl)triphenylamine (abbreviated as: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole-3-amine (abbreviated as: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthracenyl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviated as: PCAPBA), N-(9,10-diphenyl-2-anthracenyl)-N,9-diphenyl- Aromatic amine compounds such as 9H-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). Two or more types of the host material may be used.

[1150] In particular, in the case of a blue fluorescent element, it is preferable to use the anthracene compound described below as a host material.

[1151] [Chemical formula 183]

[1152]

[1153] [Chemical formula 184]

[1154]

[1155] [Chemical formula 185]

[1156]

[1157] In one embodiment of the organic EL element 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 embodiment in which the dopant material contained in the first light-emitting layer is different from the dopant material contained in the second light-emitting layer, and the embodiment in which the host material contained in the first light-emitting layer is different from the host material contained in the second light-emitting layer can be cited.

[1158] In the organic EL device of the present invention, the light-emitting layer may contain a light-emitting compound that emits fluorescence having a main peak wavelength of 500 nm or less (hereinafter, sometimes simply referred to as a "fluorescent compound").

[1159] The method for determining the peak wavelength of the main peak of a compound is as follows. A 5 μmol / L toluene solution of the compound to be measured is prepared and added to a quartz colorimetric cell, and the luminescence spectrum of the sample is measured at room temperature (300K) (the vertical axis is set as the luminescence intensity and the horizontal axis is set as the wavelength). The luminescence spectrum can be measured by a spectrofluorophotometer (device name: F-7000) manufactured by Hitachi High-Tech Scientific Co., Ltd. It should be noted that the luminescence spectrum measuring device is not limited to the device used here.

[1160] In the emission spectrum, the peak wavelength of the emission spectrum where the emission intensity reaches the maximum is defined as the main peak wavelength. In this specification, the main peak wavelength is sometimes referred to as the fluorescence emission main peak wavelength (FL-peak).

[1161] The fluorescent compound may be the dopant material or the host material.

[1162] When the light-emitting layer is a single layer, only one of the dopant material and the host material may be the above-mentioned fluorescent compound, or both of them may be the above-mentioned fluorescent compound.

[1163] In addition, 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 include the above-mentioned fluorescent compound, or both light-emitting layers may include the above-mentioned fluorescent compound. In the case where the first light-emitting layer includes the above-mentioned fluorescent compound, only one of the dopant material and the host material included in the first light-emitting layer may be the above-mentioned fluorescent compound, or both may be the above-mentioned fluorescent compound. In addition, when the second light-emitting layer includes the above-mentioned fluorescent compound, only one of the dopant material and the host material included in the second light-emitting layer may be the above-mentioned fluorescent compound, or both may be the above-mentioned fluorescent compound.

[1164] Electron transport layer

[1165] The electron transport layer is a layer containing a material with a high electron transport property (electron transport material), and is formed between the light emitting layer and the cathode, or, if an electron injection layer exists, between the electron injection layer and the light emitting layer.

[1166] The electron transport layer may be a single-layer structure or a multilayer structure comprising more than two layers. For example, the electron transport layer may be a two-layer structure comprising 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, or the electron transport layer closest to the anode in the multilayer structure, such as the first electron transport layer of the two-layer structure, is preferably adjacent to the light-emitting layer. In another embodiment of the present invention, a hole blocking layer described later may be sandwiched between the electron transport layer of the single-layer structure and the light-emitting layer, or between the electron transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer.

[1167] The electron transport layer may be, for example,

[1168] (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes,

[1169] (2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives,

[1170] (3)Polymer compounds.

[1171] Examples of the metal complex include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinolato)beryllium (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenol)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviation: ZnBTZ).

[1172] Examples of the heteroaromatic compound include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), and 4,4′-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs).

[1173] 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).

[1174] The above materials are 10 -6 cm 2 It should be noted that materials other than the above may be used for the electron transport layer as long as the electron transport property is higher than the hole transport property.

[1175] Electron injection layer

[1176] The electron injection layer is a layer containing a material with high electron injection property. The electron injection layer can use alkali metals such as lithium (Li), cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), strontium (Sr), rare earth metals such as europium (Eu), ytterbium (Yb) and compounds containing these metals. As such compounds, for example: alkali metal oxides, alkali metal halides, organic complexes containing alkali metals, alkaline earth metal oxides, alkaline earth metal halides, organic complexes containing alkaline earth metals, rare earth metal oxides, rare earth metal halides and organic complexes containing rare earth metals can be cited. In addition, a variety of these compounds can also be used in combination.

[1177] In addition, materials containing alkali metals, alkaline earth metals or their compounds in materials with electron transport properties can be used. Specifically, materials containing magnesium (Mg) in Alq can be used. It should be noted that at this time, electron injection from the cathode can be performed more efficiently. Alternatively, the electron injection layer can also use a composite material mixed with an organic compound and an electron donor (donor). Such a composite material has excellent electron injection and electron transport properties because the organic compound accepts electrons from the electron donor. At this time, as an organic compound, it is preferably a material excellent in the transmission of the accepted electrons. Specifically, for example, the materials (metal complexes, heteroaromatic compounds, etc.) constituting the electron transport layer described above can be used. As an electron donor, it is as long as it is a material that exhibits electron donation to an organic compound. Specifically, alkali metals, alkaline earth metals and rare earth metals are preferred, and lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. can be cited. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, and lithium oxide, calcium oxide, barium oxide, etc. can be cited. In addition, a Lewis base such as magnesium oxide can also be used. Alternatively, organic compounds such as tetrathiafulvalene (abbreviation: TTF) may be used.

[1178] cathode

[1179] The cathode preferably uses a metal, alloy, conductive compound, and mixtures thereof with a small work function (specifically, less than 3.8 eV). Specific examples of such cathode materials include elements belonging to the first or second group of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys thereof (e.g., MgAg, AlLi), and rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys thereof.

[1180] It should be noted that when an alkali metal, an alkaline earth metal, or an alloy containing them is used to form the cathode, a vacuum deposition method or a sputtering method may be used. In addition, when a silver paste or the like is used, a coating method or an inkjet method may be used.

[1181] It should be noted that, by providing an electron injection layer, a cathode can be formed using various conductive materials such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the size of the work function. These conductive materials can be formed into films using sputtering, inkjet, spin coating, etc.

[1182] Insulation layer

[1183] Organic EL elements are prone to pixel defects due to leakage and short circuits due to the application of an electric field to ultra-thin films. To prevent this, an insulating layer formed of an insulating thin film layer may be inserted between a pair of electrodes.

[1184] Examples of materials that can be used for the insulating layer include 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. It should be noted that mixtures and laminates thereof may also be used.

[1185] Spacer

[1186] For example, when a fluorescent light-emitting layer and a phosphorescent light-emitting layer are stacked, the spacer layer is a layer disposed between the fluorescent light-emitting layer and the phosphorescent light-emitting layer for the purpose of preventing the excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer or adjusting the carrier balance. In addition, the spacer layer may also be disposed between a plurality of phosphorescent light-emitting layers.

[1187] Since the spacer layer is disposed between the light-emitting layers, it is preferably a material having both electron transport and hole transport properties. In addition, in order to prevent the diffusion of triplet energy in the adjacent phosphorescent light-emitting layer, the triplet energy is preferably above 2.6 eV. As the material for the spacer layer, the same material as the material for the hole transport layer mentioned above can be cited.

[1188] Barrier layer

[1189] It is also possible to dispose a blocking layer such as an electron blocking layer, a hole blocking layer, and an exciton blocking layer adjacent to the light-emitting layer. The electron blocking layer refers to a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer, and the hole blocking layer refers to a layer that prevents holes from leaking from the light-emitting layer to the electron transport layer. The exciton blocking layer has a function of preventing excitons generated in the light-emitting layer from diffusing to the periphery and thus confining the excitons within the light-emitting layer.

[1190] Each layer of the above organic EL element can be formed by a conventionally known vapor deposition method, coating method, or the like. For example, vapor deposition methods such as vacuum vapor deposition method and molecular beam epitaxy (MBE) method can be used, or a known method based on a coating method such as dip coating method, spin coating method, casting method, bar coating method, roll coating method, etc. using a solution of a compound forming the layer can be used.

[1191] The film thickness of each layer is not particularly limited. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur. On the contrary, if it is too thick, a high driving voltage is required and the efficiency deteriorates. Therefore, it is usually 5 nm to 10 μm, more preferably 10 nm to 0.2 μm.

[1192] In the organic EL element having a hole transport layer with a two-layer structure or a three-layer structure of the present invention, the total thickness of the thickness of the first hole transport layer and the thickness of 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.

[1193] In addition, in one aspect of the present invention, the thickness of the second hole transport layer of the two-layer structure or the three-layer structure is preferably 5 nm or more, more preferably 20 nm or more, further preferably 25 nm or more, particularly preferably 35 nm or more, and preferably 100 nm or less.

[1194] In addition, in one aspect 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, further preferably 25 nm or more, particularly preferably 30 nm or more, and preferably 100 nm or less.

[1195] In addition, in the organic EL element having a hole transport layer with a two-layer structure or a three-layer structure of the present invention, the ratio of the film thickness D2 of the second hole transport layer to the film thickness D1 of the first hole transport layer is preferably 0.3 < D2 / D1 < 4.0, more preferably 0.5 < D2 / D1 < 3.5, further preferably 0.75 < D2 / D1 < 3.0.

[1196] As a preferred embodiment of the organic EL element of the present invention, for example, the following can be cited:

[1197] (1) An organic EL element having a hole transport layer with a two-layer structure

[1198] The first embodiment in which the second hole transport layer comprises the inventive compound and the first hole transport layer does not comprise the inventive compound;

[1199] The second embodiment wherein both the first hole transport layer and the second hole transport layer comprise the inventive compound;

[1200] A third embodiment in which the first hole transport layer contains the invention compound and the second hole transport layer does not contain the invention compound;

[1201] (2) Organic EL element having a three-layer hole transport layer

[1202] A fourth embodiment in which the first hole transport layer comprises the invention compound, and the second hole transport layer and the third hole transport layer do not comprise the invention compound;

[1203] A fifth embodiment in which the second hole transport layer comprises the invention compound, and the first hole transport layer and the third hole transport layer do not comprise the invention compound;

[1204] A sixth embodiment in which the third hole transport layer comprises the invention compound, and the first hole transport layer and the second hole transport layer do not comprise the invention compound;

[1205] A seventh embodiment in which the first hole transport layer and the second hole transport layer contain the invention compound, and the third hole transport layer does not contain the invention compound;

[1206] An eighth embodiment in which the first hole transport layer and the third hole transport layer contain the invention compound, and the second hole transport layer does not contain the invention compound;

[1207] A tenth embodiment in which the second hole transport layer and the third hole transport layer contain the invention compound, and the first hole transport layer does not contain the invention compound;

[1208] The tenth embodiment in which the first to third hole transport layers all contain the inventive compound; and so on.

[1209] Electronic devices

[1210] An organic EL element according to an 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, tablet computers, and personal computers. Examples of light-emitting devices include lighting or vehicle lamps.

[1211] The organic EL element can be used in display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and electronic devices such as lighting and light-emitting devices for vehicle lamps.

[1212] Example

[1213] Hereinafter, the present invention will be described in further detail using examples, but the present invention is not limited to the following examples.

[1214] Invention compounds used in the production of organic EL devices (I) of Examples 1 to 3

[1215] [Chemical formula 186]

[1216]

[1217] Comparative compounds used in the manufacture of organic EL devices (I) of Comparative Examples 1 and 2

[1218] [Chemical formula 187]

[1219]

[1220] Other compounds used in the manufacture of the organic EL devices (I) of Examples 1 to 3 and Comparative Examples 1 and 2

[1221] [Chemical formula 188]

[1222]

[1223] Fabrication of organic EL elements (I)

[1224] <Example 1>

[1225] A 25 mm×75 mm×1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.

[1226] The cleaned glass substrate with the ITO transparent electrode was mounted on a substrate holder of a vacuum evaporation device, and the compound HT-1 and the compound HA were co-evaporated on the surface of the side where the transparent electrode was formed so as to cover the transparent electrode to form a hole injection layer with a thickness of 10 nm. The mass ratio of the compound HT-1 to the compound HA (HT-1:HA) was 97:3.

[1227] Next, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a film thickness of 40 nm.

[1228] Next, compound Inv-1 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 40 nm.

[1229] Next, compound HT-2 was vapor-deposited on the second hole transport layer to form a third hole transport layer with a film thickness of 5 nm.

[1230] Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated on the third hole transport 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.

[1231] Next, compound ET-1 was deposited on the light-emitting layer to form a first electron transport layer with a thickness of 5 nm.

[1232] Next, compound ET-2 and Liq were co-evaporated on the first electron transport layer to form a second electron transport layer with a film thickness of 25 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50.

[1233] Next, Yb was vapor-deposited on the second electron transport layer to form an electron injecting electrode having a film thickness of 1 nm.

[1234] Then, metal Al was vapor-deposited on the electron injecting electrode to form a metal cathode having a film thickness of 50 nm.

[1235] The layer structure of the organic EL device of Example 1 obtained in this manner is shown below.

[1236] 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)

[1237] In the above-mentioned layer constitution, the numbers in parentheses are film thickness (nm), and the ratios are mass ratios.

[1238] <Examples 2 and 3>

[1239] Each organic EL device (I) was produced in the same manner as in Example 1, except that the compound Inv-4 was used in place of the compound Inv-1 in Example 2, and the compound Inv-5 was used in place of the compound Inv-1 in Example 3.

[1240] <Comparative Examples 1 and 2>

[1241] Each organic EL device (I) was produced in the same manner as in Example 1, except that the comparative compound Ref-1 was used in Comparative Example 1 instead of the compound Inv-1, and the comparative compound Ref-2 was used in Comparative Example 2 instead of the compound Inv-1.

[1242] Evaluation of organic EL devices (I)

[1243] The driving voltage and external quantum efficiency of the obtained organic EL device (I) were measured.

[1244] (1) Determination of driving voltage

[1245] A voltage was applied to the organic EL element (I) so that the current density was 10 mA / cm 2 The voltage at this time was measured (unit: V). The results are shown in Table 1.

[1246] (2) Determination of external quantum efficiency (EQE)

[1247] The obtained organic EL device (I) was subjected to a current density of 10 mA / cm at room temperature. 2 The device was driven with a direct current constant current. The brightness was measured using a brightness meter (CS-1000, a spectroradiometer manufactured by Minolta Corporation), and the external quantum efficiency (%) was measured based on the results. The results are shown in Table 1.

[1248] [Table 1]

[1249] Table 1

[1250]

[1251] Invention compounds used in the production of organic EL devices (II) of Examples 4 to 7

[1252] [Chemical formula 189]

[1253]

[1254] Comparative compound used in the preparation of the organic EL device (II) of Comparative Example 2

[1255] [Chemical formula 190]

[1256]

[1257] Other compounds used in the manufacture of the organic EL device (II) of Examples 4 to 7 and Comparative Example 3

[1258] [Chemical formula 191]

[1259]

[1260] Fabrication of organic EL elements (II)

[1261] <Example 4>

[1262] A 25 mm×75 mm×1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.

[1263] The cleaned glass substrate with the ITO transparent electrode was mounted on a substrate holder of a vacuum evaporation device, and compound Inv-1 and compound HA were co-evaporated on the surface of the side where the transparent electrode was formed in a manner 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.

[1264] Next, compound Inv-1 was deposited on the hole injection layer to form a first hole transport layer having a film thickness of 80 nm.

[1265] Next, compound HT-4 was deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 10 nm.

[1266] Next, compound BH-2 (host material) and compound BD-2 (dopant material) were co-evaporated on the second hole transport layer to form a 25 nm thick light emitting layer. The mass ratio of compound BH-2 to compound BD-2 (BH-2:BD-2) was 96:4.

[1267] Next, compound ET-3 was deposited on the light-emitting layer to form a first electron transport layer having a film thickness of 10 nm.

[1268] Next, compound ET-4 was vapor-deposited on the first electron transport layer to form a second electron transport layer with a film thickness of 15 nm.

[1269] Next, LiF was vapor-deposited on the second electron transport layer to form an electron injecting electrode having a film thickness of 1 nm.

[1270] Then, metal Al was vapor-deposited on the electron injecting electrode to form a metal cathode having a film thickness of 50 nm.

[1271] The layer structure of the organic EL device (II) of Example 4 obtained in this manner is shown below.

[1272] 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)

[1273] In the above-mentioned layer constitution, the numbers in parentheses are film thickness (nm), and the ratios are mass ratios.

[1274] <Examples 5 to 7>

[1275] An organic EL element (II) was produced in the same manner as in Example 4, except that Compound Inv-6 was used instead of Compound Inv-1 in Example 5, Compound Inv-7 was used instead of Compound Inv-1 in Example 6, and Compound Inv-8 was used instead of Compound Inv-1 in Example 7.

[1276] <Comparative Example 3>

[1277] Each organic EL device (II) was produced in the same manner as in Example 4 except that the comparative compound Ref-2 was used instead of the inventive compound Inv-1.

[1278] Evaluation of organic EL elements (II)

[1279] The driving voltage and external quantum efficiency of the obtained organic EL device (II) were measured by the same method as that of the organic EL device (I).

[1280] [Table 2]

[1281] Table 2

[1282]

[1283] Invention compounds used in the production of organic EL devices (III) of Examples 8 to 17

[1284] [Chemical formula 192]

[1285]

[1286] Comparative compounds used in the preparation of organic EL devices (III) of Comparative Examples 4 and 5

[1287] [Chemical formula 193]

[1288]

[1289] Other compounds used in the manufacture of organic EL devices of Examples 8 to 17 and Comparative Examples 4 and 5

[1290] [Chemical formula 194]

[1291]

[1292] [Chemical formula 195]

[1293]

[1294] Fabrication of organic EL elements (III)

[1295] <Example 8>

[1296] A 25 mm×75 mm×1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.

[1297] The cleaned glass substrate with the ITO transparent electrode was mounted on a substrate holder of a vacuum evaporation device, and the compound HT-1 and the compound HA were co-evaporated on the surface of the side where the transparent electrode was formed so as to cover the transparent electrode to form a hole injection layer with a thickness of 10 nm. The mass ratio of the compound HT-1 to the compound HA (HT-1:HA) was 97:3.

[1298] Next, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a film thickness of 40 nm.

[1299] Next, compound Inv-2 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 45 nm.

[1300] Next, compound HT-6 was vapor-deposited on the second hole transport layer to form a third hole transport layer with a film thickness of 5 nm.

[1301] Next, compound BH-1 (host material) and compound BD-3 (dopant material) were co-evaporated on the third hole transport 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.

[1302] Next, compound BH-5 (host material) and compound BD-3 (dopant material) were co-evaporated on the first emitting layer to form a second 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.

[1303] Next, compound ET-1 was vapor-deposited on the second light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[1304] Next, compound ET-2 and Liq were co-evaporated on the 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.

[1305] Next, Liq was vapor-deposited on the second electron transport layer to form an electron injecting electrode having a film thickness of 1 nm.

[1306] Then, metal Al was vapor-deposited on the electron injecting electrode to form a metal cathode having a film thickness of 80 nm.

[1307] The layer structure of the organic EL device (IH) of Example 8 obtained in this manner is shown below.

[1308] 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)

[1309] In the above-mentioned layer constitution, the numbers in parentheses are film thickness (nm), and the ratios are mass ratios.

[1310] <Example 9>

[1311] An organic EL device (III) was produced in the same manner as in Example 8, except that the compound Inv-3 was used instead of the compound Inv-2.

[1312] <Example 10>

[1313] An organic EL device (III) was produced in the same manner as in Example 8, except that the compound Inv-9 was used instead of the compound Inv-2.

[1314] <Example 11>

[1315] 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.

[1316] <Example 12>

[1317] In Example 8, an organic EL device (III) was prepared in the same manner except that a second emitting layer with a thickness of 20 nm was formed by co-evaporating compound BH-4 (host material), compound BH-7 (host material) and compound BD-3 (dopant material) on the first emitting layer instead of co-evaporating compound BH-5 (host material) and compound BD-3 (dopant material) to form a second emitting layer with a thickness of 20 nm. 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 % relative to the entire second emitting layer.

[1318] <Example 13>

[1319] In Example 12, an organic EL device (III) was produced in the same manner except that the mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 50:50.

[1320] <Example 14>

[1321] In Example 12, an organic EL device (III) was produced in the same manner except that the mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 30:70.

[1322] <Example 15>

[1323] In Example 12, an organic EL device (IH) was produced in the same manner except that the mass ratio of the compound BH-4 to the compound BH-7 (BH-4:BH-7) was 20:80.

[1324] <Example 16>

[1325] A 25 mm×75 mm×1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.

[1326] The cleaned glass substrate with the ITO transparent electrode was mounted on a substrate holder of a vacuum evaporation device, and the compound HT-1 and the compound HA were co-evaporated on the surface of the side where the transparent electrode was formed so as to cover the transparent electrode to form a hole injection layer with a thickness of 10 nm. The mass ratio of the compound HT-1 to the compound HA (HT-1:HA) was 97:3.

[1327] Next, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a film thickness of 40 nm.

[1328] Next, compound Inv-2 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 45 nm.

[1329] Next, compound HT-2 was vapor-deposited on the second hole transport layer to form a third hole transport layer with a film thickness of 5 nm.

[1330] Next, compound BH-3 (host material) and compound BD-5 (dopant material) were co-evaporated on the third hole transport 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.

[1331] Next, compound BH-6 (host material) and compound BD-5 (dopant material) were co-evaporated on the first emitting layer to form a second 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.

[1332] Next, compound ET-3 was deposited on the second light-emitting layer to form a first electron transport layer with a film thickness of 10 nm.

[1333] Next, compound ET-4 was vapor-deposited on the first electron transport layer to form a second electron transport layer with a film thickness of 15 nm.

[1334] Then, metal Al was vapor-deposited on the electron injecting electrode to form a metal cathode having a film thickness of 80 nm.

[1335] The layer structure of the organic EL device (III) of Example 16 obtained in this manner is shown below.

[1336] 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)

[1337] In the above-mentioned layer constitution, the numbers in parentheses are film thickness (nm), and the ratios are mass ratios.

[1338] <Example 17>

[1339] An organic EL device (III) was produced in the same manner as in Example 8, except that the compound HT-5 was used instead of the compound HT-1, and the compound Inv-1 was used instead of the compound Inv-2.

[1340] <Comparative Examples 4 and 5>

[1341] An organic EL device (III) was prepared in the same manner as in Example 8 except that the comparative compound Ref-3 or the comparative compound Ref-4 was used instead of the compound Inv-2.

[1342] Evaluation of organic EL elements (III)

[1343] The external quantum efficiency of the obtained organic EL device (III) was measured by the same method as that of the organic EL device (I).

[1344] (3) 95% life (LT95)

[1345] The obtained organic EL device (III) was subjected to a current density of 50 mA / cm 2 The battery was driven by a direct current constant current, and the time until the luminance decreased to 95% of the initial luminance was measured, and this time was defined as the 95% life (LT95).

[1346] [Table 3]

[1347]

[1348] Invention compounds used in the production of organic EL devices (IV) of Examples 18 to 34

[1349] [Chemical formula 196]

[1350]

[1351] Comparative compound used in the preparation of the organic EL device (IV) of Comparative Example 6

[1352] [Chemical formula 197]

[1353]

[1354] Other compounds used in the manufacture of organic EL devices of Examples 18 to 34 and Comparative Example 6

[1355] [Chemical formula 198]

[1356]

[1357] [Chemical formula 199]

[1358]

[1359] Fabrication of organic EL elements (IV)

[1360] <Example 18>

[1361] A 25 mm×75 mm×1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.

[1362] The cleaned glass substrate with the ITO transparent electrode was mounted on a substrate rack of a vacuum evaporation device, and the compound Inv-2 and the compound HA were co-evaporated on the surface of the side where the transparent electrode was formed so as to cover the transparent electrode to form a hole injection layer with a thickness of 10 nm. The mass ratio of the compound Inv-2 to the compound HA (Inv-2:HA) was 97:3.

[1363] Next, compound Inv-2 was deposited on the hole injection layer to form a first hole transport layer having a film thickness of 85 nm.

[1364] Next, compound HT-6 was vapor-deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 5 nm.

[1365] Next, compound BH-1 (host material) and compound BD-3 (dopant material) were co-evaporated on the second hole transport 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.

[1366] Next, compound BH-5 (host material) and compound BD-3 (dopant material) were co-evaporated on the first emitting layer to form a second 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.

[1367] Next, compound ET-1 was vapor-deposited on the second light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[1368] Next, compound ET-2 and Liq were co-evaporated on the 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.

[1369] Next, Liq was vapor-deposited on the second electron transport layer to form an electron injecting electrode having a film thickness of 1 nm.

[1370] Then, metal Al was vapor-deposited on the electron injecting electrode to form a metal cathode having a film thickness of 80 nm.

[1371] The layer structure of the organic EL device (IV) of Example 18 obtained in this manner is shown below.

[1372] 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)

[1373] In the above-mentioned layer constitution, the numbers in parentheses are film thickness (nm), and the ratios are mass ratios.

[1374] <Examples 19 to 21>

[1375] An organic EL element (IV) was prepared in the same manner as in Example 18, except that compound Inv-4 was used instead of compound Inv-2 in Example 19, compound Inv-3 was used instead of compound Inv-2 in Example 20, and compound Inv-9 was used instead of compound Inv-2 in Example 21.

[1376] <Example 22>

[1377] 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.

[1378] <Example 23>

[1379] 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.

[1380] <Example 24>

[1381] 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.

[1382] <Example 25>

[1383] A 25 mm×75 mm×1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.

[1384] The cleaned glass substrate with the ITO transparent electrode was mounted on a substrate rack of a vacuum evaporation device, and compound Inv-2 and compound HA were co-evaporated on the surface of the side where the transparent electrode was formed in a manner covering the transparent electrode, forming a hole injection layer with a film thickness of 10 nm. The mass ratio of compound Inv-2 to compound HA (Inv-2:HA) was 97:3.

[1385] Next, the inventive compound Inv-2 was deposited on the hole injection layer to form a first hole transport layer having a film thickness of 85 nm.

[1386] Next, compound HT-8 was vapor-deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 5 nm.

[1387] Next, compound BH-3 (host material) and compound BD-5 (dopant material) were co-evaporated on the second hole transport 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.

[1388] Next, compound BH-6 (host material) and compound BD-5 (dopant material) were co-evaporated on the first emitting layer to form a second 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.

[1389] Next, compound ET-3 was vapor-deposited on the second light-emitting layer to form a first electron transport layer with a film thickness of 10 nm.

[1390] Next, compound ET-4 was vapor-deposited on the first electron transport layer to form a second electron transport layer with a film thickness of 15 nm.

[1391] Then, metal Al was vapor-deposited on the second electron transport layer to form a metal cathode with a film thickness of 80 nm.

[1392] The layer structure of the organic EL device (IV) of Example 25 obtained in this manner is shown below.

[1393] 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)

[1394] In the above-mentioned layer constitution, the numbers in parentheses are film thickness (nm), and the ratios are mass ratios.

[1395] <Example 26>

[1396] 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.

[1397] <Example 27>

[1398] 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.

[1399] <Example 28>

[1400] In Example 18, an organic EL device (IV) was prepared in the same manner except that a second emitting layer with a thickness of 20 nm was formed by co-evaporating compound BH-4 (host material), compound BH-7 (host material) and compound BD-3 (dopant material) on the first emitting layer instead of forming a second emitting layer with a thickness of 15 nm by co-evaporating compound BH-5 (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 % relative to the entire second emitting layer.

[1401] <Example 29>

[1402] In Example 28, an organic EL device (IV) was produced in the same manner except that the compound HT-7 was used instead of the compound HT-6 and the mass ratio of the compound BH-4 to the compound BH-7 (BH-4:BH-7) was 60:40.

[1403] <Example 30>

[1404] In Example 18, an organic EL device (IV) was prepared in the same manner except that a second emitting layer with a thickness of 20 nm was formed by co-evaporating compound BH-8 (host material), compound BH-5 (host material) and compound BD-3 (dopant material) on the first emitting layer instead of forming a second emitting layer with a thickness of 15 nm by co-evaporating 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 % relative to the entire second emitting layer.

[1405] <Examples 31 to 34>

[1406] An organic EL element (IV) was prepared in the same manner as in Example 18, except that compound HT-11 was used instead of compound HT-6 in Example 31, compound HT-4 was used instead of compound HT-6 in Example 32, compound HT-12 was used instead of compound HT-6 in Example 33, and compound HT-13 was used instead of compound HT-6 in Example 34.

[1407] <Comparative Example 6>

[1408] 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.

[1409] Evaluation of organic EL devices (IV)

[1410] The external quantum efficiency of the obtained organic EL device (IV) was measured by the same method as that of the organic EL device (I), and the 95% lifetime was measured by the same method as that of the organic EL device (III).

[1411] [Table 4]

[1412]

[1413] As is clear from the results of Tables 1 to 4, compounds Inv-1 to Inv-9 provide organic EL devices with low driving voltage and high external quantum efficiency, compared with comparative compounds Ref-1 to Ref-5.

[1414] Inventive compounds Inv-1 to Inv-9 synthesized in the synthesis examples

[1415] [Chemical formula 200]

[1416]

[1417] Intermediate Synthesis Example 1: Synthesis of Intermediate A

[1418] [Chemical formula 201]

[1419]

[1420] Under argon atmosphere, a mixture of 7.40 g (22.1 mmol) of 2-bromo-9-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 2M potassium phosphate aqueous 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 concentrated under reduced pressure. The obtained solid was purified by silica gel column chromatography to obtain 7.67 g of a white solid (intermediate A-1). The yield was 99%.

[1421] Under 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 tert-butoxide, and 111 mL of toluene was stirred at 100° C. for 30 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The obtained solid was purified by silica gel column chromatography to obtain 6.93 g of a white solid. The yield was 63%.

[1422] Intermediate Synthesis Example 2: Synthesis of Intermediate B

[1423] [Chemical formula 202]

[1424]

[1425] Under an argon atmosphere, a mixture of 9.05 g (27.0 mmol) of 2-bromo-9-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]dichloropalladium(II) dichloromethane adduct, 40.5 mL of 2M sodium carbonate aqueous solution, and 135 mL of DME was subjected to boiling point reflux for 7 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained solid was purified by silica gel column chromatography to obtain 9.82 g of a white solid. The yield was 99%.

[1426] Intermediate Synthesis Example 3: Synthesis of Intermediate C

[1427] [Chemical formula 203]

[1428]

[1429] In the synthesis of Intermediate A, the same operation was carried out except that bromobenzene was used instead of 2-bromobiphenyl to obtain a white solid with a yield of 75%.

[1430] Synthesis Example 1: Synthesis of Compound Inv-1

[1431] [Chemical formula 204]

[1432]

[1433] Under 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 bis(trimethylsilyl)amide lithium (1 M toluene solution), and 119 mL of xylene was subjected to boiling point reflux for 7 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 3.29 g of a white solid. The yield was 40%.

[1434] The obtained substance was subjected to mass spectrometry analysis, which revealed that it was compound Inv-1 with a molecular weight of 691.92 and m / e=692.

[1435] Synthesis Example 2: Synthesis of Compound Inv-2

[1436] [Chemical formula 205]

[1437]

[1438] Under argon atmosphere, a mixture of intermediate A-1 3.47 g (10.0 mmol), 2-bromo-9,9-dimethyl-9H-fluorene 6.28 g (23.0 mmol), tri(dibenzylideneacetone)dipalladium (0) 0.366 g, (0.400 mmol), tri-tert-butylphosphonium tetrafluoroborate 0.464 g (1.60 mmol), sodium tert-butoxide 2.69 g (28.0 mmol), and xylene 100 mL was stirred at 110° C. for 7 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained solid was purified by silica gel column chromatography to obtain 1.88 g of a white solid. The yield was 26%.

[1439] The obtained substance was subjected to mass spectrometry analysis, which revealed that it was compound Inv-2 with a relative molecular weight of 731.98 and m / e=732.

[1440] Synthesis Example 3: Synthesis of Compound Inv-3

[1441] [Chemical formula 206]

[1442]

[1443] The same operation was carried out as in Synthesis Example 2 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%.

[1444] The obtained substance was subjected to mass spectrometry analysis, which revealed that it was compound Inv-3 with a molecular weight of 651.85 and m / e=652.

[1445] Synthesis Example 4: Synthesis of Compound Inv-4

[1446] [Chemical formula 207]

[1447]

[1448] Under argon atmosphere, a mixture of 2.43 g (8.51 mmol) of 9,9-dimethyl-N-phenyl-9H-fluorene-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 tert-butoxide, and 85 mL of xylene was stirred at 110°C for 7 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained solid was purified by silica gel column chromatography to obtain 1.88 g of a white solid. The yield was 35%.

[1449] The obtained substance was subjected to mass spectrometry analysis, and the result was compound Inv-4, with a relative molecular weight of 615.82 and m / e=616.

[1450] Synthesis Example 5: Synthesis of Compound Inv-5

[1451] [Chemical formula 208]

[1452]

[1453] A white solid was obtained by the same operation 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%.

[1454] The obtained substance was subjected to mass spectrometry analysis, which revealed that it was compound Inv-5 with a relative molecular weight of 691.92 and m / e=692.

[1455] Synthesis Example 6: Synthesis of Compound Inv-6

[1456] [Chemical formula 209]

[1457]

[1458] A white solid was obtained by the same operation 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%.

[1459] The obtained substance was subjected to mass spectrometry analysis, and the result was compound Inv-6, with a relative molecular weight of 691.92 and m / e=692.

[1460] Synthesis Example 7: Synthesis of Compound Inv-7

[1461] [Chemical formula 210]

[1462]

[1463] A white solid was obtained by the same operation 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%.

[1464] The obtained substance was subjected to mass spectrometry analysis, and the result was compound Inv-7, with a relative molecular weight of 753.99 and m / e=754.

[1465] Synthesis Example 8: Synthesis of Compound Inv-8

[1466] [Chemical formula 211]

[1467]

[1468] A white solid was obtained by the same operation 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%.

[1469] The obtained substance was subjected to mass spectrometry analysis, and the result was compound Inv-8, with a relative molecular weight of 767.97 and m / e=768.

[1470] Synthesis Example 9: Synthesis of Compound Inv-9

[1471] [Chemical formula 212]

[1472]

[1473] A white solid was obtained by the same operation 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%.

[1474] The obtained substance was subjected to mass spectrometry analysis, which revealed that it was compound Inv-9 with a relative molecular weight of 669.96 and m / e=670.

[1475] Explanation of symbols

[1476] 1, 11, 12 Organic EL elements

[1477] 2 substrate

[1478] 3 Anode

[1479] 4 Cathode

[1480] 5. Luminous layer

[1481] 5a 1st light emitting layer

[1482] 5b Second light-emitting layer

[1483] 6 Hole transport region (hole transport layer)

[1484] 6a Hole injection layer

[1485] 6b 1st hole transport layer

[1486] 6c Second hole transport layer

[1487] 6d Third hole transport layer

[1488] 7 Electron transport region (electron transport layer)

[1489] 7a 1st electron transport layer

[1490] 7b Second electron transport layer

[1491] 10, 20, 30 light units

Claims

1. A compound represented by the following formula (1), In formula (1), N ＊ is the central nitrogen atom, R a and R b One of them 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, in, R a With R b are optionally bonded to each other to form a substituted or unsubstituted ring, Selected from R 2 , R 3 , R 6 and R 7 One of them is a single bond to *1, R 1 , R 4 , R 5 , R 8 and R which is not a single bond bonded to *1 2 , R 3 , R 6 and R 7 each independently represents 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, Selected from R 1 , R 4 , R 5 , R 8 and R other than said single bond 2 , R 3 , R 6 and R 7 The two adjacent ones in are not bonded to each other and thus do not form a ring. R 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, Selected from R 11 ~R 14 The two adjacent ones in are not bonded to each other and thus 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 formulae (1a) to (1g), In formula (1a), *21 is the same as L 1 or L 2 The bonding position of Selected from R 101 ~R 105 One of them is a single bond to *22, selected from R 106 ~R 110 One of them is a single bond to *23, selected from R 111 ~R 115 One of them is a single bond to *24, R other than the 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, is selected from R which is not a single bond 101 ~R 105 The two adjacent ones in are not bonded to each other and thus do not form a ring. is selected from R which is not a single bond 106 ~R 110 The two adjacent ones in are not bonded to each other and thus do not form a ring. is selected from R which is not a single bond 111 ~R 115 The two adjacent ones in are not bonded to each other and thus do not form a ring. m is 0 or 1, n is 0 or 1, 1 is 0 or 1, R 116 ~R 120 each independently represents 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, Selected from R 116 ~R 120 The two adjacent ones in are not bonded to each other and thus do not form a ring. In formula (1b), *25 is with L 1 or L 2 The bonding position of Selected from R 121 ~R 128 One of them is a single bond to *26, R other than the 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, is selected from R which is not a single bond 121 ~R 128 The two adjacent ones in are not bonded to each other and thus do not form a ring. Among them, in L 1 is p-phenylene, Ar 1 When represented by formula (1b), the group represented by formula (1b) bonded to the p-phenylene group is selected from R 121 , R 124 , R 125 and R 128 One of them is a single bond to *26, In L 2 is p-phenylene, Ar 2 When represented by formula (1b), the group represented by formula (1b) bonded to the p-phenylene group is selected from R 121 , R 124 , R 125 and R 128 One of them is a single bond to *26, In formula (1c), *27 is the same as L 1 or L 2 The bonding position of Selected from R 131 ~R 140 One of them is a single bond to *28, R other than the 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, is selected from R which is not a single bond 131 ~R 140 The two adjacent ones in are not bonded to each other and thus do not form a ring. In formula (1d), *29 is with L 1 or L 2 The bonding position of Selected from R 141 ~R 152 One of them is a single bond to *30, R other than the 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, is selected from R which is not a single bond 141 ~R 152 The two adjacent ones in are not bonded to each other and thus do not form a ring structure. In formula (1e), *31 is the same as L 1 or L 2 The bonding position of Selected from R 161 ~R 165 One of them is a single bond to *32, selected from R 161 ~R 165 The other one in is a single bond to *33, R is not the single bond bonded to *32 nor the single bond bonded to *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 selected from a single bond that is neither bonded to *32 nor bonded to *33 161 ~R 165 The two adjacent ones in are not bonded to each other and thus 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, Selected from R 171 ~R 175 The adjacent two of them may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form no ring, Selected from R 181 ~R 185 The adjacent two of them may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form no ring, In formula (1f), *34 is with L 1 or L 2 The bonding position of X is an oxygen atom, a sulfur atom or NR A , Selected from R 191 ~R 198 One of RA is a single bond to *35, R other than the single bond 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, R other than the single bond 191 ~R 198 each independently represents 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, is selected from R which is not a single bond 191 ~R 198 The adjacent two of them may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form no ring, In formula (1g), *36 is with L 1 or L 2 The bonding position of Selected from R B , R C and R 201 ~R 208 One of them is a single bond to *37, R other than the single bond B and R C each independently represents 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, RB and RC which are not the single bond are optionally bonded to each other to form a substituted or unsubstituted ring, R other than the single bond 201 ~R 208 each independently represents 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, is selected from R which is not a single bond 201 ~R 208 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring.

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

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

4. The compound according to any one of claims 1 to 3, wherein L 3 For a single key.

5. The compound according to any one of claims 1 to 4, wherein L 4 For a single key.

6. The compound according to any one of claims 1 to 5, wherein Ar 1 and Ar 2 At least one of them is a group represented by the formula (1a) or (1g).

7. The compound according to any one of claims 1 to 6, wherein Ar 1 or Ar 2 is a group represented by the formula (1a), and the group represented by the formula (1a) satisfies at least one of the following (i) to (iii), (i)R 101 or R 105 is a single bond to *22 (ii) R 106 or R 110 is a single bond to *23 (iii) R 111 or R 115 is a single bond to *24.

8. The compound according to any one of claims 1 to 7, wherein Ar 1 or Ar 2 is a group represented by the formula (1g), and in the group represented by the formula (1g), RB and R C Each is independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted phenyl group.

9. The compound according to any one of claims 1 to 8, wherein Ar 1 or Ar 2 is a group represented by the formula (1g), and in the group represented by the formula (1g), R2 02 or R2 07 is a single bond to *37.

10. The compound according to any one of claims 1 to 9, wherein L 1 and L 2 Each is independently a single bond or an arylene group having 6 to 12 ring carbon atoms.

11. The compound according to any one of claims 1 to 10, comprising at least one deuterium atom. 12 . A material for an organic electroluminescent device, comprising the compound according to claim 1 . 13 . A hole transport layer material comprising the compound according to claim 1 . 14 . An organic electroluminescent device comprising a cathode, an anode, and an organic layer located between the cathode and the anode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer includes the compound according to claim 1 .

15. The organic electroluminescent element according to claim 14, wherein The organic layer includes a hole transport region between the anode and the light emitting layer, and the hole transport region includes the compound.

16. The organic electroluminescent element according to claim 15, 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 include the compound.

17. The organic electroluminescent element according to claim 16, wherein: The light-emitting layer is directly in contact with the second hole transport layer.

18. The organic electroluminescent element according to claim 16 or 17, wherein: The total thickness of the first hole transport layer and the second hole transport layer is greater than or equal to 30 nm and less than or equal to 150 nm.

19. The organic electroluminescent element according to any one of claims 14 to 18, wherein The light-emitting layer is a single layer.

20. The organic electroluminescent element according to any one of claims 14 to 19, wherein The light-emitting layer contains a light-emitting compound that emits fluorescence with a main peak wavelength of 500 nm or less.

21. The organic electroluminescent element according to any one of claims 14 to 20, wherein The light-emitting layer includes a fluorescent dopant material. 22 . An electronic device comprising the organic electroluminescent element according to claim 14 .

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