Organic electroluminescent element and electronic device

Abstract

Provided are an organic electroluminescent element having further improved element performance, and an electronic device comprising such an organic electroluminescent element. Specifically, provided are: a compound represented by formula (1); an organic electroluminescent element comprising the compound; and an electronic device comprising such an organic electroluminescent element. Each symbol in the formula is the same as the definition in the description. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to 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. The injected electrons and holes recombine 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 crucial to develop compounds and element structures that can efficiently transfer electrons or holes to the luminescent region and facilitate recombination of electrons and holes in order to obtain high-performance organic EL elements.

[0003] Patent Documents 1 to 7 disclose compounds useful as materials for organic electroluminescent devices.

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: KR10-2374470B1

[0007] Patent document 2: WO2021 / 134820A1

[0008] Patent Document 3: WO2015 / 014435A1

[0009] Patent Document 4: KR2021-0120526A

[0010] Patent Document 5: KR2021-0096954A

[0011] Patent document 6: CN110577510A

[0012] Patent document 7: CN105906547A Summary of the invention

[0013] Problem that the invention aims to solve

[0014] Conventionally, a large number of compounds and device structures for organic EL devices have been reported, but a device structure that further improves the performance of organic EL devices is still being sought.

[0015] The present invention has been made to solve the above-mentioned problems, and an object of the present invention is to provide an organic EL element with further improved element performance, and an electronic device including such an organic EL element.

[0016] Means used to solve problems

[0017] The present inventors have conducted intensive studies on the performance of organic EL devices containing the compounds described in Patent Documents 1 to 7 and have found that an organic EL device containing a compound represented by the following formula (1) has further improved performance.

[0018] In one embodiment, the present invention provides a compound represented by the following formula (1) [hereinafter sometimes referred to as compound (1)].

[0019] [Chemical formula 1]

[0020]

[0021] [In formula (1),

[0022] R a1 ~R a4 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, and R a1 With R a2 and R a3 With R a4 They may be bonded to each other to form a ring, or may not be bonded to each other.

[0023] R 1 , R 2 and R b1 ~R b12 Each independently

[0024] Hydrogen atom, halogen atom, nitro group, cyano group,

[0025] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0026] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0027] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0028] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0029] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0030] a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms,

[0031] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0032] -O-(R 904 ) shown in the group,

[0033] -S-(R 905 ) or

[0034] -N(R 906 )(R 907 ) shown in the following;

[0035] The above R 901 ~R 907 Each independently

[0036] Hydrogen atoms,

[0037] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0038] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0039] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0040] a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;

[0041] Among them, R b1 ~R b12 Two adjacent groups in may be bonded to each other to form a ring, or may not be bonded to each other.

[0042] Ar 1 It is a group represented by any one of the following formulae (i) to (iii).]

[0043] [Chemical formula 2]

[0044]

[0045] [In formula (i),

[0046] R b13 ~R b16 Each independently

[0047] Hydrogen atom, halogen atom, nitro group, cyano group,

[0048] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0049] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0050] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0051] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0052] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0053] a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms,

[0054] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0055] -O-(R 904 ) shown in the group,

[0056] -S-(R 905 ) or

[0057] -N(R 906 )(R 907 ) shown in the following;

[0058] The above R 901 ~R 907 Each independently

[0059] Hydrogen atoms,

[0060] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0061] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0062] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0063] a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;

[0064] Among them, R b13 ~R b16 The two adjacent groups in may be bonded to each other to form a benzene ring, or may not be bonded to each other.

[0065] Ar 2 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.

[0066] In the above R b13 ~R b16 When two adjacent groups in Ar are not bonded to each other, 3 is a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group, in the above R b13 ~R b16 When two adjacent groups in Ar are bonded to each other to form a benzene ring, 3 is a hydrogen atom, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0067] n1 is 0, 1 or 2.

[0068] *1 represents the bonding position to the nitrogen atom represented in formula (1).

[0069] n2 is an integer greater than or equal to 1.

[0070] When n2 is 1, R x is a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms (excluding adamantyl),

[0071] When n2 is an integer greater than 2, R x It is an alkyl group having 1 to 30 carbon atoms or a cycloalkyl group having 3 to 30 ring carbon atoms.

[0072] *2 indicates R x The bonding position of (a) R x Replace selected from R b13 ~R b16 At least one of the following is bonded to the benzene ring, or (b) R x Bonded to a b13 ~R b16 or (c) R x Bonded to a selected from Ar 2 and Ar 3 At least one group in x Satisfies two or more of the above-mentioned (a) to (c).

[0073] [Chemical formula 3]

[0074]

[0075] [In formula (ii),

[0076] X is -O-, -S- or -N(-R 3 )-[R 3 It is an alkyl group having 1 to 50 carbon atoms or an aryl group having 6 to 50 ring carbon atoms. ].

[0077] R c1 , R c2 , R b17 ~R b22 and R d1 ~R d6 Each independently

[0078] Hydrogen atom, halogen atom, nitro group, cyano group,

[0079] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0080] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0081] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0082] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0083] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0084] a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms,

[0085] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0086] -O-(R 904 ) shown in the group,

[0087] -S-(R 905 ) or

[0088] -N(R 906 )(R 907 ) shown in the following;

[0089] The above R 901 ~R 907 Each independently

[0090] Hydrogen atoms,

[0091] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0092] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0093] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0094] a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;

[0095] Among them, R c1 , R c2 and R b17 ~R b22 Two adjacent groups in may be bonded to each other to form a ring, or may not be bonded to each other.

[0096] n3 is 0 or 1.

[0097] *3 represents the bonding position to the nitrogen atom represented in formula (1).

[0098] *4 and *5 represent replacement of R d1 ~R d6 In the embodiment of the present invention, any one of the above is bonded to the benzene ring, and each is bonded to a different position. When n3 is 0, *3 and *6 are directly connected without passing through *4 and *5.

[0099] *6 means replace Rb17 ~R b19 Any one of them is bonded to the benzene ring.

[0100] R y1 It is an alkyl group having 1 to 30 carbon atoms or a cycloalkyl group having 3 to 30 ring carbon atoms.

[0101] n4 is an integer greater than or equal to 1.

[0102] *7 means R y1 The bonding position of (d)R y1 Replace selected from R c1 , R c2 and R b17 ~R b22 At least one of the following is bonded to the benzene ring, (e) R y1 Bonded to a c1 , R c2 , R 3 and R b17 ~R b22 At least one group in y1 Satisfies both the above solutions (d) and (e).]

[0103] [Chemical formula 4]

[0104]

[0105] [In formula (iii),

[0106] R b23 ~R b30 and R e1 ~R e5 Each independently

[0107] Hydrogen atom, halogen atom, nitro group, cyano group,

[0108] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0109] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0110] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0111] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0112] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0113] a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms,

[0114] -Si(R 901 )(R 902 )(R903 ) shown in the group,

[0115] -O-(R 904 ) shown in the group,

[0116] -S-(R 905 ) or

[0117] -N(R 906 )(R 907 ) shown in the following;

[0118] The above R 901 ~R 907 Each independently

[0119] Hydrogen atoms,

[0120] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0121] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0122] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0123] a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;

[0124] Among them, R b23 ~R b30 Two adjacent groups in may be bonded to each other to form a ring, or may not be bonded to each other.

[0125] *8 represents the bonding position to the nitrogen atom represented in formula (1).

[0126] *9 represents a nitrogen atom in place of R in formula (iii) e1 ~R e5 Any one of them is bonded to the benzene ring.

[0127] R y2 It is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms.

[0128] n5 is an integer greater than or equal to 1.

[0129] *10 means R y2 The bonding position of (f)R y2 Replace selected from R b23 ~R b30 At least one of the following is bonded to the benzene ring, (g) R y2 Bonded to a b23 ~R b30 At least one group in y2Satisfies both (f) and (g) above.]

[0130] In another embodiment, the present invention provides an organic electroluminescent device comprising the above compound (1).

[0131] In still another embodiment, the present invention provides an electronic device comprising the organic electroluminescent element.

[0132] Effects of the Invention

[0133] An organic EL device containing the compound represented by the above formula (1) exhibits improved device performance. BRIEF DESCRIPTION OF THE DRAWINGS

[0134] 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.

[0135] 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.

[0136] Figure 3 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. DETAILED DESCRIPTION

[0137] [definition]

[0138] In this specification, the hydrogen atom means isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0139] 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.

[0140] 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.

[0141] 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.

[0142] 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.

[0143] 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.

[0144] In this specification, "the number of atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having an atomic number of XX to YY" 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.

[0145] 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".

[0146] 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.

[0147] 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.

[0148] "Substituents described in this specification"

[0149] The substituents described in the present specification are described below. Unless otherwise specified, the substituents described in the present specification are defined as follows.

[0150] 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.

[0151] 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.

[0152] 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.

[0153] 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.

[0154] 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.

[0155] 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.

[0156] 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.

[0157] 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.

[0158] 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.

[0159] "Substituted or unsubstituted aryl"

[0160] As specific examples of "substituted or unsubstituted aryl" described in this specification (specific example group G1), the following unsubstituted aryl (specific example group G1A) 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 only "aryl" is expressed, both "unsubstituted aryl" and "substituted aryl" are included.

[0161] "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.

[0162] Unsubstituted aryl (specific example group G1A):

[0163] Phenyl,

[0164] p-Biphenyl,

[0165] m-Biphenyl,

[0166] o-Biphenyl,

[0167] 4-terphenyl-4-yl,

[0168] 4-terphenyl-3-yl,

[0169] 4-terphenyl-2-yl,

[0170] m-terphenyl-4-yl,

[0171] m-terphenyl-3-yl,

[0172] m-terphenyl-2-yl,

[0173] m-terphenyl-3′-yl,

[0174] o-terphenyl-4-yl,

[0175] o-terphenyl-3-yl,

[0176] o-terphenyl-2-yl,

[0177] 1-naphthyl,

[0178] 2-naphthyl,

[0179] Anthracene,

[0180] Benzanthryl,

[0181] Fiki,

[0182] Triphenylene,

[0183] Phenyl,

[0184] Pyrene

[0185] base,

[0186] Benzo base,

[0187] Triphenylene,

[0188] Benzotriphenylene,

[0189] Tetraphenylene,

[0190] Pentaphenyl,

[0191] Fluorene,

[0192] 9,9'-spirobifluorenyl,

[0193] Benzofluorenyl,

[0194] Dibenzofluorenyl,

[0195] Fluoranthene group,

[0196] Benzofluoranthene,

[0197] Perylene, and

[0198] 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).

[0199] [Chemical formula 5]

[0200]

[0201] [Chemical formula 6]

[0202]

[0203] Substituted aryl (specific example group G1B):

[0204] o-Toluyl,

[0205] m-Toluene

[0206] p-Tolyl,

[0207] p-Xylyl,

[0208] m-Xylyl,

[0209] o-Xylyl,

[0210] p-Isopropylphenyl,

[0211] m-isopropylphenyl,

[0212] o-isopropylphenyl,

[0213] 4-tert-Butylphenyl,

[0214] m-tert-butylphenyl,

[0215] o-tert-butylphenyl,

[0216] 3,4,5-Trimethylphenyl,

[0217] 9,9-dimethylfluorenyl,

[0218] 9,9-Diphenylfluorenyl

[0219] 9,9-bis(4-methylphenyl)fluorenyl,

[0220] 9,9-bis(4-isopropylphenyl)fluorenyl,

[0221] 9,9-bis(4-tert-butylphenyl)fluorenyl,

[0222] Cyanophenyl,

[0223] Triphenylsilylphenyl,

[0224] Trimethylsilylphenyl,

[0225] Phenyl naphthyl,

[0226] naphthylphenyl, and

[0227] 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.

[0228] "Substituted or unsubstituted heterocyclic group"

[0229] 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.

[0230] The "heterocyclic group" described in the present specification is a monocyclic group or a condensed ring group.

[0231] The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0232] 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.

[0233] "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.

[0234] 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).

[0235] 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).

[0236] Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):

[0237] Pyrrolyl,

[0238] Imidazole,

[0239] Pyrazolyl,

[0240] Triazole,

[0241] Tetrazolyl,

[0242] Oxazolyl,

[0243] Isoxazolyl,

[0244] Oxadiazolyl,

[0245] Thiazolyl,

[0246] Isothiazolyl,

[0247] Thiadiazole,

[0248] Pyridyl,

[0249] Pyridazine

[0250] Pyrimidine,

[0251] Pyrazinyl,

[0252] Triazine,

[0253] Indolyl,

[0254] Isoindolyl,

[0255] Indolizine

[0256] Quinolizinyl,

[0257] Quinoline,

[0258] Isoquinolinyl,

[0259] Cinnoline,

[0260] Phthalocyanine

[0261] Quinazoline,

[0262] Quinoxaline,

[0263] Benzimidazolyl,

[0264] Indazolyl,

[0265] Phenanthroline,

[0266] Phenanthridinyl,

[0267] Acridinium,

[0268] Phenazine,

[0269] Carbazolyl,

[0270] Benzocarbazolyl,

[0271] Morpholinyl,

[0272] Phenoxazine,

[0273] Phenothiazine,

[0274] azacarbazolyl, and diazacarbazolyl.

[0275] Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):

[0276] Furanyl,

[0277] Oxazolyl,

[0278] Isoxazolyl,

[0279] Oxadiazolyl,

[0280] Cuckoo ton base,

[0281] Benzofuranyl,

[0282] Isobenzofuranyl,

[0283] Dibenzofuranyl,

[0284] Naphthobenzofuranyl,

[0285] Benzoxazolyl,

[0286] Benzisoxazolyl,

[0287] Phenoxazine,

[0288] Morpholinyl,

[0289] dinaphthofuranyl,

[0290] Azadibenzofuranyl,

[0291] Diazadibenzofuranyl,

[0292] azanaphthobenzofuranyl, and

[0293] naphthyridinylbenzofuranyl.

[0294] Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3):

[0295] Thienyl,

[0296] Thiazolyl,

[0297] Isothiazolyl,

[0298] Thiadiazole,

[0299] benzothienyl,

[0300] Isobenzothienyl,

[0301] dibenzothienyl,

[0302] naphthobenzothienyl,

[0303] Benzothiazolyl,

[0304] Benzisothiazolyl,

[0305] Phenothiazine,

[0306] dinaphthothienyl,

[0307] azadibenzothienyl,

[0308] diazadibenzothienyl,

[0309] azanaphthobenzothienyl and

[0310] diazanaphthobenzothienyl.

[0311] 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):

[0312] [Chemical formula 7]

[0313]

[0314] [Chemical formula 8]

[0315]

[0316] In the above general formulas (TEMP-16) to (TEMP-33), X A and YA are each independently 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.

[0317] 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.

[0318] Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):

[0319] (9-phenyl)carbazolyl,

[0320] (9-biphenyl)carbazolyl,

[0321] (9-phenyl)phenylcarbazolyl,

[0322] (9-naphthyl)carbazolyl,

[0323] Diphenylcarbazole-9-yl,

[0324] Phenylcarbazol-9-yl,

[0325] Methylbenzimidazolyl,

[0326] Ethylbenzimidazolyl,

[0327] Phenyl triazine,

[0328] Biphenyl triazine,

[0329] Diphenyltriazine,

[0330] Phenylquinazolinyl, and

[0331] Biphenylquinazolinyl.

[0332] Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0333] Phenyldibenzofuranyl,

[0334] Methyldibenzofuranyl,

[0335] tert-Butyldibenzofuranyl, and

[0336] The monovalent residue of spiro[9H-xanthen-9,9'-[9H]fluorene].

[0337] Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

[0338] Phenyldibenzothiophene,

[0339] Methyldibenzothiophene,

[0340] tert-Butyldibenzothienyl, and

[0341] The monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0342] · 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):

[0343] 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 the hydrogen atom bonded to the nitrogen atom when at least one of YA is NH, 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.

[0344] "Substituted or unsubstituted alkyl"

[0345] 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.

[0346] "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.

[0347] Unsubstituted alkyl (specific example group G3A):

[0348] methyl,

[0349] Ethyl,

[0350] n-propyl,

[0351] Isopropyl,

[0352] n-Butyl,

[0353] Isobutyl

[0354] sec-butyl, and

[0355] Tert-butyl.

[0356] Substituted alkyl (specific example group G3B):

[0357] Heptafluoropropyl (including isomers),

[0358] Pentafluoroethyl,

[0359] 2,2,2-trifluoroethyl, and

[0360] Trifluoromethyl.

[0361] "Substituted or unsubstituted alkenyl"

[0362] 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.

[0363] "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.

[0364] Unsubstituted alkenyl (specific example group G4A):

[0365] Vinyl,

[0366] Allyl,

[0367] 1-Butenyl,

[0368] 2-Butenyl, and

[0369] 3-Butenyl.

[0370] Substituted alkenyl (specific example group G4B):

[0371] 1,3-Butadienyl,

[0372] 1-Methylvinyl,

[0373] 1-methylallyl,

[0374] 1,1-dimethylallyl,

[0375] 2-methylallyl, and

[0376] 1,2-Dimethylallyl.

[0377] "Substituted or unsubstituted alkynyl"

[0378] 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.

[0379] "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.

[0380] Unsubstituted alkynyl (specific example group G5A):

[0381] Ethylene

[0382] "Substituted or unsubstituted cycloalkyl"

[0383] 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.

[0384] "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.

[0385] Unsubstituted cycloalkyl (specific example group G6A):

[0386] Cyclopropyl,

[0387] Cyclobutyl,

[0388] Cyclopentyl,

[0389] Cyclohexyl,

[0390] 1-adamantyl,

[0391] 2-adamantyl,

[0392] 1-Norbornyl, and

[0393] 2-Norborneol.

[0394] Substituted cycloalkyl (specific example group G6B):

[0395] 4-Methylcyclohexyl.

[0396] ·“-Si(R 901 )(R 902 )(R 903 )"

[0397] As described in this specification, -Si(R 901 )(R 902 )(R 903 ) as a specific example (specific example group G7), can be cited:

[0398] -Si(G1)(G1)(G1),

[0399] -Si(G1)(G2)(G2),

[0400] -Si(G1)(G1)(G2),

[0401] -Si(G2)(G2)(G2),

[0402] -Si(G3)(G3)(G3) and

[0403] -Si(G6)(G6)(G6). Here,

[0404] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0405] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0406] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0407] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0408] A plurality of G1's in -Si(G1)(G1)(G1) are the same as or different from each other.

[0409] The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other.

[0410] A plurality of G1's in -Si(G1)(G1)(G2) are the same as or different from each other.

[0411] Multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other.

[0412] Multiple G3 in -Si(G3)(G3)(G3) are the same as or different from each other.

[0413] Multiple G6's in -Si(G6)(G6)(G6) are the same as or different from each other.

[0414] ·“-O-(R 904 )"

[0415] As described in this specification, -O-(R 904 ) as a specific example (specific example group G8), can be cited:

[0416] -O(G1),

[0417] -O(G2),

[0418] -O(G3) and

[0419] -O(G6).

[0420] Here,

[0421] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0422] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0423] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0424] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0425] ·“-S-(R 905 )"

[0426] As described in this specification, -S-(R 905 ) as a specific example (specific example group G9), can be cited:

[0427] -S(G1),

[0428] -S(G2),

[0429] -S(G3) and

[0430] -S(G6).

[0431] Here,

[0432] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0433] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0434] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0435] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0436] ·“-N(R 906 )(R 907 )"

[0437] As described in this specification, -N(R 906 )(R 907 ) are shown as specific examples (specific example group G10), and include

[0438] -N(G1)(G1),

[0439] -N(G2)(G2),

[0440] -N(G1)(G2),

[0441] -N(G3)(G3) and

[0442] -N(G6)(G6).

[0443] Here,

[0444] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0445] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0446] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0447] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0448] - A plurality of G1's in N(G1)(G1) are the same as or different from each other.

[0449] - The multiple G2s in N(G2)(G2) are the same as or different from each other.

[0450] - The multiple G3 in N(G3)(G3) are the same as or different from each other.

[0451] - The multiple G6's in N(G6)(G6) are the same as or different from each other.

[0452] "Halogen atoms"

[0453] 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.

[0454] "Substituted or unsubstituted fluoroalkyl"

[0455] 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.

[0456] "Substituted or unsubstituted haloalkyl"

[0457] 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.

[0458] "Substituted or unsubstituted alkoxy"

[0459] 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.

[0460] "Substituted or unsubstituted alkylthio"

[0461] 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.

[0462] "Substituted or unsubstituted aryloxy group"

[0463] 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.

[0464] "Substituted or unsubstituted arylthio"

[0465] 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.

[0466] "Substituted or unsubstituted trialkylsilyl"

[0467] 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.

[0468] "Substituted or unsubstituted aralkyl"

[0469] 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.

[0470] 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.

[0471] 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.

[0472] 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.

[0473] In the present specification, the carbazolyl group is specifically any of the following groups unless otherwise described in the present specification.

[0474] [Chemical formula 9]

[0475]

[0476] In the present specification, the (9-phenyl)carbazolyl group is specifically any of the following groups unless otherwise specified in the present specification.

[0477] [Chemical formula 10]

[0478]

[0479] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0480] 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.

[0481] [Chemical formula 11]

[0482]

[0483] In the above general formulas (TEMP-34) to (TEMP-41), * represents a bonding position.

[0484] 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.

[0485] "Substituted or unsubstituted arylene group"

[0486] 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.

[0487] "Substituted or unsubstituted divalent heterocyclic group"

[0488] 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.

[0489] "Substituted or unsubstituted alkylene"

[0490] 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.

[0491] 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.

[0492] [Chemical formula 12]

[0493]

[0494] [Chemical formula 13]

[0495]

[0496] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0497] In the above general formulas (TEMP-42) to (TEMP-52), * represents a bonding position.

[0498] [Chemical formula 14]

[0499]

[0500] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0501] Formula Q9 and Q 10 They may be bonded to each other via a single bond to form a ring.

[0502] In the above general formulas (TEMP-53) to (TEMP-62), * represents a bonding position.

[0503] [Chemical formula 15]

[0504]

[0505] In the above general formulae (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0506] In the above general formulas (TEMP-63) to (TEMP-68), * represents a bonding position.

[0507] 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.

[0508] [Chemical formula 16]

[0509]

[0510] [Chemical formula 17]

[0511]

[0512] [Chemical formula 18]

[0513]

[0514] In the above general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0515] [Chemical formula 19]

[0516]

[0517] [Chemical formula 20]

[0518]

[0519] [Chemical formula 21]

[0520]

[0521] [Chemical formula 22]

[0522]

[0523] In the above general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0524] The above is the description of the “substituents described in the present specification”.

[0525] ・"When bonding to form a ring"

[0526] 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".

[0527] 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.

[0528] [Chemical formula 23]

[0529]

[0530] 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 930 Group, 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.

[0531] The above-mentioned "one or more groups" means that two or more groups of the above-mentioned groups consisting of 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).

[0532] [Chemical formula 24]

[0533]

[0534] 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 .

[0535] [Chemical formula 25]

[0536]

[0537] 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.

[0538] 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.

[0539] 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.

[0540] 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.

[0541] 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.

[0542] "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 R 921 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.

[0543] 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.

[0544] 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.

[0545] Unless otherwise specified in the present specification, "monocyclic ring" is preferred among "monocyclic ring" and "condensed ring".

[0546] In the present specification, unless otherwise specified, among "saturated ring" and "unsaturated ring", "unsaturated ring" is preferred.

[0547] Unless otherwise specified in the present specification, a "monocyclic ring" is preferably a benzene ring.

[0548] Unless otherwise specified in the present specification, the "unsaturated ring" is preferably a benzene ring.

[0549] 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.

[0550] 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".

[0551] 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".

[0552] 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").

[0553] ·Substituents when expressed as "substituted or unsubstituted"

[0554] 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

[0555] unsubstituted alkyl having 1 to 50 carbon atoms,

[0556] unsubstituted alkenyl having 2 to 50 carbon atoms,

[0557] unsubstituted alkynyl having 2 to 50 carbon atoms,

[0558] unsubstituted cycloalkyl having 3 to 50 ring carbon atoms,

[0559] -Si(R 901 )(R 902 )(R 903 ),

[0560] -O-(R 904 ),

[0561] -S-(R905 ),

[0562] -N(R 906) (R 907 ),

[0563] Halogen atoms, cyano, nitro,

[0564] unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0565] Unsubstituted heterocyclic group having 5 to 50 ring atoms

[0566] The groups in the group etc.

[0567] Here, R 901 ~R 907 Each independently

[0568] Hydrogen atoms,

[0569] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0570] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0571] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0572] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0573] In R 901 If there are two or more, two or more R 901 Same or different from each other,

[0574] In R 902 If there are two or more, two or more R 902 Same or different from each other,

[0575] In R 903 If there are two or more, two or more R 903 Same or different from each other,

[0576] In R 904 If there are two or more, two or more R 904 Same or different from each other,

[0577] In R 905 If there are two or more, two or more R 905 Same or different from each other,

[0578] In R 906 If there are two or more, two or more R 906 Same or different from each other,

[0579] In R 907 If there are two or more, two or more R 907 Same as or different from each other.

[0580] In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

[0581] an alkyl group having 1 to 50 carbon atoms,

[0582] an aryl group having 6 to 50 ring carbon atoms, and

[0583] A heterocyclic group having 5 to 50 ring atoms

[0584] The groups in the group.

[0585] In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

[0586] an alkyl group having 1 to 18 carbon atoms,

[0587] an aryl group having 6 to 18 ring carbon atoms, and

[0588] A heterocyclic group having 5 to 18 ring atoms

[0589] The groups in the group.

[0590] 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".

[0591] 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.

[0592] 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.

[0593] 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.

[0594] Hereinafter, the compound of the present invention will be described.

[0595] The compound (1) according to one embodiment of the present invention is represented by the following formula (1).

[0596] Hereinafter, the symbols in formula (1) and each formula included in formula (1) will be described. It should be noted that the same symbols have the same meanings unless otherwise specified.

[0597] [Chemical formula 26]

[0598]

[0599] In formula (1), R a1 ~R a4 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, and R a1 With R a2 and R a3 With R a4 They may be bonded to each other to form a ring, or may not be bonded to each other.

[0600] About R a1 ~R a4 For details of the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, see the description of "substituted or unsubstituted alkyl group" in the item "Substituents described in the present specification" which is limited to the range of 1 to 30 carbon atoms. The unsubstituted alkyl group having 1 to 30 carbon atoms is preferably methyl.

[0601] About R a1 ~R a4 For details of the substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, reference can be made to the description of "substituted or unsubstituted cycloalkyl group" in the section "substituents described in the present specification" which is limited to the range of 3 to 30 ring carbon atoms.

[0602] In R a1 With R a2 and R a3 With R a4 When the two groups are bonded to form a ring, a spiro ring is formed. The 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. Examples of substituted or unsubstituted spiro rings are shown below, but are not limited thereto. * indicates the bonding position to the benzene ring of the fluorene skeleton.

[0603] [Chemical formula 27]

[0604]

[0605] The spiro ring is preferably the following spiro ring.

[0606] [Chemical formula 28]

[0607]

[0608] The spiro ring is more preferably the following spiro ring.

[0609] [Chemical formula 29]

[0610]

[0611] R 1 , R 2 and R b1 ~R b12 Each independently

[0612] Hydrogen atom, halogen atom, nitro group, cyano group,

[0613] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0614] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0615] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0616] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0617] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0618] a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms,

[0619] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0620] -O-(R 904 ) shown in the group,

[0621] -S-(R 905 ) or

[0622] -N(R 906 )(R 907 ) and R b1 ~R b12 Two adjacent groups in may be bonded to each other to form a ring, or may not be bonded to each other.

[0623] R 1 , R 2 and R b1 ~R b12The hydrogen atom, halogen atom, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, -Si(R 901 )(R 902 )(R 903 ) represented by -O-(R 904 ) represented by the group, -S-(R 905 ) and -N(R 906 )(R 907 ) are the same as those described in the item "Substituents described in the present specification".

[0624] R 1 , R 2 Each independently is preferably a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and more preferably a hydrogen atom.

[0625] R b1 ~R b12 Each independently is preferably a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, more preferably a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, further preferably a hydrogen atom or an unsubstituted alkyl group having 1 to 6 carbon atoms, and particularly preferably a hydrogen atom, a methyl group, an isopropyl group, or a tert-butyl group.

[0626] It should be noted that Rb1~R b12 The two adjacent groups in the fluorene skeleton may be bonded to each other to form a ring or may not be bonded to each other. As the above ring, a benzene ring, a naphthalene ring, etc. can be cited. In this case, a condensed ring is formed together with the benzene ring of the fluorene skeleton, that is, a naphthalene ring and an anthracene ring are formed respectively. The above ring is preferably a benzene ring.

[0627] As specific examples of preferred embodiments of the above formula (1), the following formulas (1-1) to (1-9) can be cited, but are not particularly limited thereto. It should be noted that each group in the following formulas (1-1) to (1-9) is the same as the group with the same symbol in formula (1). Hereinafter, each description in formula (1) also applies to the following formulas (1-1) to (1-9).

[0628] [Chemical formula 30]

[0629]

[0630] [Chemical formula 31]

[0631]

[0632] [Chemical formula 32]

[0633]

[0634] [Chemical formula 33]

[0635]

[0636] [Chemical formula 34]

[0637]

[0638] In addition, in formula (1), Ar 1 It is a group represented by any one of the following formulae (i) to (iii). 1 There are no particular restrictions, but the group represented by formula (i) or the group represented by formula (ii) is preferred.

[0639] Hereinafter, formula (i), formula (ii), and formula (iii) will be described in detail in sequence.

[0640] (Regarding formula (i))

[0641] [Chemical formula 35]

[0642]

[0643] In formula (i), R b13 ~R b16 Each independently

[0644] Hydrogen atom, halogen atom, nitro group, cyano group,

[0645] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0646] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0647] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0648] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0649] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0650] a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms,

[0651] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0652] -O-(R 904 ) shown in the group,

[0653] -S-(R 905 ) or

[0654] -N(R 906 )(R 907 ),

[0655] Among them, R b13 ~R b16 The two adjacent groups in may be bonded to each other to form a benzene ring, or may not be bonded to each other.

[0656] Ar 2 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.

[0657] In the above R b13 ~R b16 When two adjacent groups in Ar are not bonded to each other, 3 is a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group, in the above R b13 ~R b16 When two adjacent groups in Ar are bonded to each other to form a benzene ring, 3 is a hydrogen atom, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0658] n1 is 0, 1 or 2.

[0659] *1 represents the bonding position to the nitrogen atom represented in formula (1).

[0660] n2 is an integer greater than or equal to 1.

[0661] When n2 is 1, R x is a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms (excluding adamantyl),

[0662] When n2 is an integer greater than 2, R x It is an alkyl group having 1 to 30 carbon atoms or a cycloalkyl group having 3 to 30 ring carbon atoms.

[0663] *2 indicates R x The bonding position, R x (a) Substitute the selected b13 ~R b16 and (b) bonded to a benzene ring, and (c) bonded to a b13 ~R b16 At least one group selected from Ar 2 and Ar 3 or satisfies at least one group selected from the above (a) to (c).

[0664] R b13 ~R b16 The hydrogen atom, halogen atom, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, -Si(R 901 )(R 902 )(R 903 ) represented by -O-(R 904 ) represented by the group, -S-(R 905 ) and -N(R 906 )(R 907 ) are the same as those described in the item "Substituents described in the present specification".

[0665] R b13 ~R b16 Each of the above groups is independently preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; more preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms; further preferably a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms; particularly preferably a hydrogen atom, a methyl group, an isopropyl group, a tert-butyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, a 2-norbornyl group, or a substituted or unsubstituted phenyl group.

[0666] It should be noted that R b13 ~R b16 The two adjacent groups in R may be bonded to each other to form a benzene ring, or they may not be bonded to each other. b13 ~R b16 When two adjacent groups in the b13 ~R b16 The bonded benzene rings together form a condensed ring, that is, a naphthalene ring.

[0667] In Ar 2In the substituted or unsubstituted phenylene group and substituted or unsubstituted naphthylene group represented by , the substituent is the same as described in the item "Substituents recorded in the present specification". The substituent is preferably an unsubstituted alkyl group having 1 to 50 carbon atoms or an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, more preferably an unsubstituted alkyl group having 1 to 6 carbon atoms or an unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, further preferably an unsubstituted alkyl group having 1 to 6 carbon atoms or an unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, and particularly preferably a methyl group, isopropyl group, tert-butyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.

[0668] n1 is 0, 1 or 2, preferably 0 or 1, and can be either 0 or 1.

[0669] In Ar 3 In the substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl represented by , the substituent is the same as described in the item "Substituents recorded in the present specification". The substituent is preferably an unsubstituted alkyl group having 1 to 50 carbon atoms or an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, more preferably an unsubstituted alkyl group having 1 to 6 carbon atoms or an unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, further preferably an unsubstituted alkyl group having 1 to 6 carbon atoms or an unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, and particularly preferably a methyl group, isopropyl group, tert-butyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.

[0670] Represents R x The number of substitution n2 is an integer greater than or equal to 1, and may be 1 or an integer greater than or equal to 2. It is preferably an integer of 1-6, more preferably an integer of 1-4, and even more preferably an integer of 1-3.

[0671] When n2 is 1, about R x The substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, and the substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms (excluding adamantyl group) represented by the above-mentioned group can refer to the description of "substituted or unsubstituted alkyl group" in the item of "substituents described in the present specification" being limited to the range of 3 to 30 carbon atoms, and can refer to the description of "substituted or unsubstituted cycloalkyl group" being limited to the range of 3 to 30 ring carbon atoms.

[0672] R when n2 is 1 xPreferred are substituted or unsubstituted alkyl groups having 3 to 10 carbon atoms, or substituted or unsubstituted cycloalkyl groups having 3 to 9 ring carbon atoms, more preferred are unsubstituted alkyl groups having 3 to 10 carbon atoms, or unsubstituted cycloalkyl groups having 3 to 9 ring carbon atoms, further preferred are unsubstituted alkyl groups having 3 to 6 carbon atoms, or unsubstituted cycloalkyl groups having 3 to 9 ring carbon atoms, and particularly preferred are isopropyl, tert-butyl, cyclopentyl, cyclohexyl, 1-norbornyl, and 2-norbornyl.

[0673] When n2 is an integer greater than 2, x With regard to the alkyl group having 1 to 30 carbon atoms and the cycloalkyl group having 3 to 30 ring carbon atoms, the description of “substituted or unsubstituted alkyl group” in the item “substituents described in the present specification” can be limited to the range of 1 to 30 carbon atoms, and the description of “substituted or unsubstituted cycloalkyl group” can be limited to the range of 3 to 30 ring carbon atoms.

[0674] R when n2 is an integer greater than or equal to 2 x Preferred are substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, or substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, more preferred are unsubstituted alkyl groups having 1 to 10 carbon atoms, or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, further preferred are unsubstituted alkyl groups having 1 to 6 carbon atoms, or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, and particularly preferred are methyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl.

[0675] As mentioned above, *2 means R x The bonding position, R x (a) Substitute the selected b13 ~R b16 and (b) bonded to a benzene ring, and (c) bonded to a b13 ~R b16 At least one group selected from Ar 2 and Ar 3 or satisfies at least one group selected from the above (a) to (c).

[0676] The above-mentioned solution (b) can be bonded to a b13 ~R b16 Any position of at least one group in x Bonded to R b13 As an example, if R b13 When it is a substituted aryl group having 6 to 50 ring carbon atoms, R x It may be bonded to the aryl group or may be bonded to a substituent of the aryl group.

[0677] Similarly, the above-mentioned solution (c) can be bonded to a compound selected from Ar 2 and Ar 3 Any position of at least one group in.

[0678] As specific examples of preferred embodiments of the above formula (i), the following formulas (i-1) to (i-5) can be cited, but are not particularly limited to these. It should be noted that each group in the following formula is the same as the group with the same symbol in formula (i). Each description in the above formula (i) also applies to the following formulas (i-1) to (i-5). The above formula (i) can be the following formula (i-1) or the following formula (i-5), or it can be any one of the following formulas (i-2) to (i-4).

[0679] [Chemical formula 36]

[0680]

[0681] In formula (i-1), Ar is described 2 The benzene ring represents Ar 2 is a benzene ring. That is, Ar 2 The benzene ring may have a substituent or may be bonded to R x The substituent on the benzene ring may also be bonded with R x .

[0682] Records Ar 2 The substituents that the benzene ring may have are the same as the “substituents when described as “substituted or unsubstituted”” in the item “substituents recorded in the present specification”. The substituent is preferably an alkyl group having 1 to 50 carbon atoms or a cycloalkyl group having 3 to 50 ring carbon atoms, more preferably an alkyl group having 1 to 18 carbon atoms or a cycloalkyl group having 3 to 10 ring carbon atoms, further preferably an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 5 to 10 ring carbon atoms, and particularly preferably a methyl group, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl.

[0683] It should be noted that in Ar 2 In, not with Ar 3 A hydrogen atom is bonded to the site that is bonded and does not have a substituent.

[0684] [Chemical formula 37]

[0685]

[0686] In the naphthalene ring described in the above formulae (i-2) to (i-4), the site where no substituent is described may be bonded to a hydrogen atom or may be bonded to R x , and a substituent may be bonded to it. In addition, R x.

[0687] The above-mentioned substituents are the same as the “substituents when described as “substituted or unsubstituted”” in the item “substituents recorded in the present specification”. The substituent is preferably an alkyl group having 1 to 50 carbon atoms or a cycloalkyl group having 3 to 50 ring carbon atoms, more preferably an alkyl group having 1 to 18 carbon atoms or a cycloalkyl group having 3 to 10 ring carbon atoms, further preferably an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 5 to 10 ring carbon atoms, and particularly preferably a methyl group, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl.

[0688] [Chemical formula 38]

[0689]

[0690] In formula (i-5), Ar is recorded 2 The benzene ring represents Ar 2 is a benzene ring. That is, Ar 2 The benzene ring may have a substituent or may be bonded to R x The substituent on the benzene ring may be bonded with R x .

[0691] Records Ar 2 The substituents that the benzene ring may have are the same as the “substituents when described as “substituted or unsubstituted”” in the item “substituents recorded in the present specification”. The substituent is preferably an alkyl group having 1 to 50 carbon atoms or a cycloalkyl group having 3 to 50 ring carbon atoms, more preferably an alkyl group having 1 to 18 carbon atoms or a cycloalkyl group having 3 to 10 ring carbon atoms, further preferably an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 5 to 10 ring carbon atoms, and particularly preferably a methyl group, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl.

[0692] It should be noted that in Ar 2 In, not with another Ar 2 Bonded or not with Ar 3 A hydrogen atom is bonded to the site which is not substituted.

[0693] Although not particularly limited, in formula (i-5), Ar 3 Preferred is a substituted or unsubstituted phenyl group.

[0694] (Regarding formula (ii))

[0695] [Chemical formula 39]

[0696]

[0697] In formula (ii),

[0698] X is -O-, -S- or -N(-R 3 )-[R 3 It is an alkyl group having 1 to 50 carbon atoms or an aryl group having 6 to 50 ring carbon atoms. ].

[0699] R c1 , R c2 , R b17 ~R b22 and R d1 ~R d6 Each independently

[0700] Hydrogen atom, halogen atom, nitro group, cyano group,

[0701] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0702] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0703] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0704] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0705] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0706] a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms,

[0707] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0708] -O-(R 904 ) shown in the group,

[0709] -S-(R 905 ) or

[0710] -N(R 906) (R 907 ),

[0711] Among them, R c1 , R c2 and R b17 ~R b22 Two adjacent groups in may be bonded to each other to form a ring, or may not be bonded to each other.

[0712] n3 is 0 or 1.

[0713] *3 represents the bonding position to the nitrogen atom represented in formula (1).

[0714] *4 and *5 represent replacement of R d1 ~R d6 In the embodiment of the present invention, any one of the above is bonded to the benzene ring, and each is bonded to a different position. When n3 is 0, *3 and *6 are directly connected without passing through *4 and *5.

[0715] *6 means replace R b17 ~R b19 Any one of them is bonded to the benzene ring.

[0716] R y1 It is an alkyl group having 1 to 30 carbon atoms or a cycloalkyl group having 3 to 30 ring carbon atoms.

[0717] n4 is an integer greater than or equal to 1.

[0718] *7 means R y1 The bonding position, R y1 (d) is replaced by R c1 , R c2 and R b17 ~R b22 and (e) bonded to a benzene ring, and (e) bonded to a c1 , R c2 , R 3 and R b17 ~R b22 or satisfies both of the above-mentioned (d) and (e).

[0719] In the X-denoted -N(-R 3 )-middle, R 3 For the alkyl group having 1 to 50 carbon atoms represented, see the description of the unsubstituted alkyl group in the "substituted or unsubstituted alkyl group" in the section of "substituents described in the present specification".

[0720] In the X-denoted -N(-R 3 )-middle, R 3 For the aryl group having 6 to 50 ring carbon atoms, see the description of the unsubstituted alkyl group in the "substituted or unsubstituted aryl group" in the section of "substituents described in the present specification".

[0721] X is preferably -O-.

[0722] R c1 , R c2 , R b17 ~R b22 and R d1 ~R d6The hydrogen atom, halogen atom, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, -Si(R 901 )(R 902 )(R 903 ) represented by -O-(R 904 ) represented by the group, -S-(R 905 ) and -N(R 906 )(R 907 ) are the same as those described in the item "Substituents described in the present specification".

[0723] R c1 , R c2 , R b17 ~R b22 and R d1 ~R d6 Each of the above groups is independently preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; more preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms; further preferably a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms; particularly preferably a hydrogen atom, a methyl group, an isopropyl group, a tert-butyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, a 2-norbornyl group, or a substituted or unsubstituted phenyl group.

[0724] It should be noted that R c1 , R c2 and R b17 ~R b22 The two adjacent groups in R may be bonded to each other to form a ring, or may not be bonded to each other. c1 , R c2 and R b17 ~R b22 When two adjacent groups in are bonded to each other to form a ring, c1 , R c2 and R b17 ~R b22 The bonded benzene rings together form a fused ring.

[0725] n3 is 0 or 1, preferably 0.

[0726] About R y1 The alkyl group having 1 to 30 carbon atoms and the cycloalkyl group having 3 to 30 ring carbon atoms represented by the above-mentioned group can refer to the description of “substituted or unsubstituted alkyl group” in the item of “substituents described in the present specification” to limit the range of the carbon atoms to 1 to 30, and can refer to the description of “substituted or unsubstituted cycloalkyl group” to limit the range of the ring carbon atoms to 3 to 30.

[0727] R y1 Preferred are substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, or substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, more preferred are unsubstituted alkyl groups having 1 to 10 carbon atoms, or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, further preferred are unsubstituted alkyl groups having 1 to 6 carbon atoms, or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, and particularly preferred are methyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl.

[0728] n4 is an integer greater than or equal to 1, preferably an integer of 1 to 6, more preferably an integer of 1 to 4, further preferably an integer of 1 to 3, and may be 1, 2, or 3.

[0729] *7 means R y1 The bonding position, R y1 (d) is replaced by R c1 , R c2 and R b17 ~R b22 and (e) bonded to a benzene ring, and (e) bonded to a c1 , R c2 , R 3 and R b17 ~R b22 or satisfies both of the above-mentioned (d) and (e).

[0730] The above-mentioned solution (e) may be bonded to a c1 , R c2 , R 3 and R b17 ~R b22 Any position of at least one group in y1 Bonded to R b20 As an example, if R b20 is a substituted aryl group having 6 to 50 ring carbon atoms, then R y1 It may be bonded to the aryl group or may be bonded to a substituent of the aryl group.

[0731] As specific examples of preferred embodiments of the above formula (ii), the following formulas (ii-1) to (ii-7) can be cited, but are not particularly limited thereto. It should be noted that each group in the following formula is the same as the group with the same symbol in formula (ii). Each description in the above formula (ii) also applies to the following formulas (ii-1) to (ii-7).

[0732] [Chemical formula 40]

[0733]

[0734] [Chemical formula 41]

[0735]

[0736] [Chemical formula 42]

[0737]

[0738] [Chemical formula 43]

[0739]

[0740] [Chemical formula 44]

[0741]

[0742] [Chemical formula 45]

[0743]

[0744] [Chemical formula 46]

[0745]

[0746] (Regarding formula (iii))

[0747] [Chemical formula 47]

[0748]

[0749] In formula (iii),

[0750] R b23 ~R b30 and R e1 ~R e5 Each independently

[0751] Hydrogen atom, halogen atom, nitro group, cyano group,

[0752] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0753] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0754] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0755] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0756] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0757] a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms,

[0758] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0759] -O-(R 904 ) shown in the group,

[0760] -S-(R 905 ) or

[0761] -N(R 906 )(R 907 ) shown in the following;

[0762] R 901 ~R 907 Each independently

[0763] Hydrogen atoms,

[0764] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0765] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0766] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0767] a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;

[0768] Among them, R b23 ~R b30 Two adjacent groups in may be bonded to each other to form a ring, or may not be bonded to each other.

[0769] *8 represents the bonding position to the nitrogen atom represented in formula (1).

[0770] *9 represents a nitrogen atom in place of R in formula (iii). e1 ~R e5 Any one of them is bonded to the benzene ring.

[0771] R y2 It is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms.

[0772] n5 is an integer greater than or equal to 1.

[0773] *10 means R y2 The bonding position, R y2 (f) is replaced by R b23 ~R b30 and (g) is bonded to a benzene ring, and (g) is bonded to a b23 ~R b30 or satisfies both of the above-mentioned (f) and (g).

[0774] R b23 ~R b30 and R e1 ~R e5 The hydrogen atom, halogen atom, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, -Si(R 901 )(R 902 )(R 903 ) represented by -O-(R 904 ) represented by the group, -S-(R 905 ) and -N(R 906 )(R 907 ) are the same as those described in the item "Substituents described in the present specification".

[0775] R b23 ~R b30 and R e1 ~R e5 Each of the above groups is independently preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; more preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms; further preferably a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms; particularly preferably a hydrogen atom, a methyl group, an isopropyl group, a tert-butyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, a 2-norbornyl group, or a substituted or unsubstituted phenyl group.

[0776] It should be noted that R b23 ~R b30The two adjacent groups in R may be bonded to each other to form a ring, or may not be bonded to each other. b23 ~R b30 When two adjacent groups in the formula (R) are bonded to each other to form a ring, b23 ~R b30 The bonded benzene rings together form a condensed ring, that is, a naphthalene ring.

[0777] About R y2 The alkyl group having 1 to 30 carbon atoms and the cycloalkyl group having 3 to 30 ring carbon atoms represented by the present invention can refer to the description of "substituted or unsubstituted alkyl group" in the item of "substituents described in the present specification" to limit the range of carbon atoms to 1 to 30, and can refer to the description of "substituted or unsubstituted cycloalkyl group" to limit the range of carbon atoms to 3 to 30.

[0778] R y2 Preferred are substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, or substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, more preferred are unsubstituted alkyl groups having 1 to 10 carbon atoms, or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, further preferred are unsubstituted alkyl groups having 1 to 6 carbon atoms, or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, and particularly preferred are methyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl.

[0779] n5 is an integer greater than or equal to 1, preferably an integer of 1 to 6, more preferably an integer of 1 to 4, further preferably an integer of 1 to 3, and may be 1, 2, or 3.

[0780] *10 means R y2 The bonding position, R y2 (f) is replaced by R b23 ~R b30 and (g) is bonded to a benzene ring, and (g) is bonded to a b23 ~R b30 or satisfies both of the above-mentioned (f) and (g).

[0781] The above-mentioned embodiment (g) may be bonded to a b23 ~R b30 Any position of at least one group in y2 Bonded to R b23 As an example, if R b23 is a substituted aryl group having 6 to 50 ring carbon atoms, then R y2 It may be bonded to the aryl group or may be bonded to a substituent of the aryl group.

[0782] As specific examples of preferred embodiments of the above formula (iii), the following formulas (iii-1) to (iii-3) can be cited, but are not particularly limited thereto. It should be noted that each group in the following formula is the same as the group with the same symbol in formula (iii). Each description in the above formula (iii) also applies to the following formulas (iii-1) to (iii-3).

[0783] [Chemical formula 48]

[0784]

[0785] [Chemical formula 49]

[0786]

[0787] [Chemical formula 50]

[0788]

[0789] As described above, in the present specification, "hydrogen atom" may be any of protium atom, deuterium atom and tritium atom. Therefore, compound (1) may contain a deuterium atom of natural origin.

[0790] In addition, deuterium atoms can be intentionally introduced into compound (1) by using a deuterated compound as part or all of the raw material compound. That is, compound (1) can also be a compound represented by the above formula (1), in which at least one of the hydrogen atoms contained in the compound is a deuterium atom. That is, compound (1) can be a solution containing one or more deuterium atoms in the molecule.

[0791] The deuteration rate of compound (1) 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 that protium isotopes are contained in a certain ratio of natural origin. Therefore, for the scheme of the deuteration rate of compound (1) shown below, the ratio obtained 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.

[0792] The deuteration rate of compound (1) 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.

[0793] Compound (1) 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%.

[0794] The ratio of the number of deuterium atoms to the total number of hydrogen atoms in compound (1) 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.

[0795] In one embodiment of the present invention, from the viewpoint of production cost, the compound (1) is preferably a protium form. The protium form means that the content of the protium form is 90 mol% or more, preferably 95 mol% or more, and more preferably 99 mol% or more (each including 100%) relative to the total amount of the compound (1).

[0796] A person skilled in the art can easily produce compound (1) by referring to known synthesis methods and the synthesis examples described below.

[0797] Specific examples of compound (1) are shown below, but the compound (1) is not limited to the following exemplary compounds.

[0798] In the following specific examples, when unsubstituted, it means that a protium atom is bonded, and D is a deuterium atom. In addition, when there is nothing at the beginning of the bonding group, it means a methyl group according to the chemical convention.

[0799] <Examples of compounds represented by formula (1) having a group represented by formula (i)>

[0800] [Chemical formula 51]

[0801]

[0802] [Chemical formula 52]

[0803]

[0804] [Chemical formula 53]

[0805]

[0806] [Chemical formula 54]

[0807]

[0808] [Chemical formula 55]

[0809]

[0810] [Chemical formula 56]

[0811]

[0812] [Chemical formula 57]

[0813]

[0814] [Chemical formula 58]

[0815]

[0816] [Chemical formula 59]

[0817]

[0818] [Chemical formula 60]

[0819]

[0820] [Chemical formula 61]

[0821]

[0822] [Chemical formula 62]

[0823]

[0824] [Chemical formula 63]

[0825]

[0826] [Chemical formula 64]

[0827]

[0828] [Chemical formula 65]

[0829]

[0830] [Chemical formula 66]

[0831]

[0832] [Chemical formula 67]

[0833]

[0834] [Chemical formula 68]

[0835]

[0836] [Chemical formula 69]

[0837]

[0838] [Chemical formula 70]

[0839]

[0840] [Chemical formula 71]

[0841]

[0842] [Chemical formula 72]

[0843]

[0844] [Chemical formula 73]

[0845]

[0846] [Chemical formula 74]

[0847]

[0848] [Chemical formula 75]

[0849]

[0850] [Chemical formula 76]

[0851]

[0852] [Chemical formula 77]

[0853]

[0854] [Chemical formula 78]

[0855]

[0856] [Chemical formula 79]

[0857]

[0858] [Chemical formula 80]

[0859]

[0860] [Chemical formula 81]

[0861]

[0862] [Chemical formula 82]

[0863]

[0864] [Chemical formula 83]

[0865]

[0866] [Chemical formula 84]

[0867]

[0868] [Chemical formula 85]

[0869]

[0870] [Chemical formula 86]

[0871]

[0872] [Chemical formula 87]

[0873]

[0874] [Chemical formula 88]

[0875]

[0876] [Chemical formula 89]

[0877]

[0878] [Chemical formula 90]

[0879]

[0880] [Chemical formula 91]

[0881]

[0882] [Chemical formula 92]

[0883]

[0884] [Chemical formula 93]

[0885]

[0886] [Chemical formula 94]

[0887]

[0888] [Chemical formula 95]

[0889]

[0890] [Chemical formula 96]

[0891]

[0892] [Chemical formula 97]

[0893]

[0894] [Chemical formula 98]

[0895]

[0896] [Chemical formula 99]

[0897]

[0898] [Chemical formula 100]

[0899]

[0900] [Chemical Formula 101]

[0901]

[0902] [Chemical formula 102]

[0903]

[0904] [Chemical formula 103]

[0905]

[0906] <Examples of compounds represented by formula (1) having a group represented by formula (ii) or (iii)>

[0907] [Chemical formula 104]

[0908]

[0909] [Chemical formula 105]

[0910]

[0911] [Chemical formula 106]

[0912]

[0913] [Chemical formula 107]

[0914]

[0915] [Chemical formula 108]

[0916]

[0917] [Chemical formula 109]

[0918]

[0919] [Chemical formula 110]

[0920]

[0921] [Chemical formula 111]

[0922]

[0923] [Chemical formula 112]

[0924]

[0925] [Chemical formula 113]

[0926]

[0927] [Chemical formula 114]

[0928]

[0929] [Chemical formula 115]

[0930]

[0931] [Chemical formula 116]

[0932]

[0933] [Chemical formula 117]

[0934]

[0935] [Chemical formula 118]

[0936]

[0937] [Chemical formula 119]

[0938]

[0939] [Chemical formula 120]

[0940]

[0941] [Chemical formula 121]

[0942]

[0943] [Chemical formula 122]

[0944]

[0945] [Chemical formula 123]

[0946]

[0947] [Chemical formula 124]

[0948]

[0949] [Chemical formula 125]

[0950]

[0951] [Chemical formula 126]

[0952]

[0953] [Chemical formula 127]

[0954]

[0955] [Chemical formula 128]

[0956]

[0957] [Chemical formula 129]

[0958]

[0959] [Chemical formula 130]

[0960]

[0961] [Chemical formula 131]

[0962]

[0963] [Chemical formula 132]

[0964]

[0965] [Chemical formula 133]

[0966]

[0967] [Chemical formula 134]

[0968]

[0969] [Chemical formula 135]

[0970]

[0971] [Chemical formula 136]

[0972]

[0973] [Chemical formula 137]

[0974]

[0975] [Chemical formula 138]

[0976]

[0977] [Chemical formula 139]

[0978]

[0979] [Chemical formula 140]

[0980]

[0981] [Chemical formula 141]

[0982]

[0983] [Chemical formula 142]

[0984]

[0985] [Chemical formula 143]

[0986]

[0987] [Chemical formula 144]

[0988]

[0989] [Chemical formula 145]

[0990]

[0991] [Chemical formula 146]

[0992]

[0993] [Chemical formula 147]

[0994]

[0995] [Chemical formula 148]

[0996]

[0997] [Chemical formula 149]

[0998]

[0999] [Chemical formula 150]

[1000]

[1001] [Chemical formula 151]

[1002]

[1003] [Chemical formula 152]

[1004]

[1005] [Chemical formula 153]

[1006]

[1007] [Chemical formula 154]

[1008]

[1009] [Chemical formula 155]

[1010]

[1011] [Chemical formula 156]

[1012]

[1013] [Chemical formula 157]

[1014]

[1015] [Chemical formula 158]

[1016]

[1017] [Chemical formula 159]

[1018]

[1019] [Chemical formula 160]

[1020]

[1021] [Chemical formula 161]

[1022]

[1023] [Chemical formula 162]

[1024]

[1025] [Chemical formula 163]

[1026]

[1027] [Chemical formula 164]

[1028]

[1029] [Chemical formula 165]

[1030]

[1031] [Chemical formula 166]

[1032]

[1033] [Chemical formula 167]

[1034]

[1035] [Chemical formula 168]

[1036]

[1037] [Chemical formula 169]

[1038]

[1039] [Chemical formula 170]

[1040]

[1041] [Chemical formula 171]

[1042]

[1043] [Chemical formula 172]

[1044]

[1045] [Chemical formula 173]

[1046]

[1047] [Chemical formula 174]

[1048]

[1049] [Chemical formula 175]

[1050]

[1051] [Chemical formula 176]

[1052]

[1053] [Chemical formula 177]

[1054]

[1055] [Chemical formula 178]

[1056]

[1057] [Chemical formula 179]

[1058]

[1059] [Chemical formula 180]

[1060]

[1061] [Chemical formula 181]

[1062]

[1063] [Chemical formula 182]

[1064]

[1065] [Chemical formula 183]

[1066]

[1067] [Chemical formula 184]

[1068]

[1069] [Chemical formula 185]

[1070]

[1071] [Chemical formula 186]

[1072]

[1073] [Chemical formula 187]

[1074]

[1075] [Chemical formula 188]

[1076]

[1077] [Chemical formula 189]

[1078]

[1079] [Chemical formula 190]

[1080]

[1081] [Chemical formula 191]

[1082]

[1083] [Chemical formula 192]

[1084]

[1085] [Chemical formula 193]

[1086]

[1087] [Chemical formula 194]

[1088]

[1089] [Chemical formula 195]

[1090]

[1091] [Chemical formula 196]

[1092]

[1093] [Chemical formula 197]

[1094]

[1095] [Chemical formula 198]

[1096]

[1097] [Chemical formula 199]

[1098]

[1099] [Chemical formula 200]

[1100]

[1101] [Chemical formula 201]

[1102]

[1103] [Chemical formula 202]

[1104]

[1105] [Chemical formula 203]

[1106]

[1107] [Chemical formula 204]

[1108]

[1109] [Chemical formula 205]

[1110]

[1111] [Chemical formula 206]

[1112]

[1113] [Chemical formula 207]

[1114]

[1115] [Chemical formula 208]

[1116]

[1117] [Chemical formula 209]

[1118]

[1119] [Chemical formula 210]

[1120]

[1121] [Chemical formula 211]

[1122]

[1123] [Chemical formula 212]

[1124]

[1125] [Chemical formula 213]

[1126]

[1127] [Chemical formula 214]

[1128]

[1129] [Chemical formula 215]

[1130]

[1131] [Chemical formula 216]

[1132]

[1133] [Chemical formula 217]

[1134]

[1135] [Chemical formula 218]

[1136]

[1137] [Chemical formula 219]

[1138]

[1139] [Chemical formula 220]

[1140]

[1141] [Chemical formula 221]

[1142]

[1143] [Chemical formula 222]

[1144]

[1145] Organic EL elements

[1146] 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 compound (1).

[1147] Examples of organic layers containing compound (1) include at least one layer selected from 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, and an electron transport region (electron injection layer, electron transport layer, hole blocking layer, etc.) disposed between the cathode and the light-emitting layer.

[1148] In one embodiment of the present invention, the organic layer comprises a hole transport region located between the anode and the light-emitting layer. Preferably, the hole transport region comprises compound (1). More preferably, the hole injection layer and the hole transport layer comprise compound (1). Further preferably, the hole transport layer comprises compound (1).

[1149] The hole transport layer may be formed of two or more layers, and any one of the two or more hole transport layers, preferably the hole transport layer closest to the anode (far from the light-emitting layer), may contain compound (1). For example, when the hole transport layer contains compound (1) and the hole transport layer is formed of a first hole transport layer on the anode side and a second hole transport layer on the cathode side, preferably at least one of the first hole transport layer and the second hole transport layer contains compound (1), and more preferably at least the first hole transport layer contains compound (1).

[1150] The light-emitting layer may be formed of one layer or two or more layers. The electron transport layer may be formed of one layer or two or more layers.

[1151] Hereinafter, each layer (including an optional layer) included in the organic EL device of the present invention and materials other than the compound (1) for forming each layer will be described.

[1152] 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.

[1153] For example, as a typical element structure of a simple organic EL element, the following element structure can be cited.

[1154] (1) Anode / light-emitting unit / cathode

[1155] 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 presence or absence of the layers in parentheses is optional.

[1156] (a) (hole injection layer / ) hole transport layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[1157] (b) (hole injection layer / ) hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / electron transport layer ( / electron injection layer)

[1158] (c) (hole injection layer / ) hole transport layer / phosphorescent light emitting layer / spacer layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[1159] (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)

[1160] (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)

[1161] (f) (hole injection layer / ) hole transport layer / electron blocking layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[1162] (g) (hole injection layer / ) hole transport layer / exciton blocking layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[1163] (h) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[1164] (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)

[1165] (j) (hole injection layer / ) hole transport layer / fluorescent light emitting layer / hole blocking layer / electron transport layer ( / electron injection layer)

[1166] (k) (hole injection layer / ) hole transport layer / fluorescent light emitting layer / exciton blocking layer / electron transport layer ( / electron injection layer)

[1167] (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)

[1168] (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)

[1169] (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)

[1170] Each of the above-mentioned phosphorescent or fluorescent light-emitting layers can be set as a light-emitting layer that respectively displays a different light-emitting color. Specifically, in the above-mentioned light-emitting unit (d), 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.

[1171] 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.

[1172] As a typical device structure of a tandem organic EL device, the following device structures can be mentioned.

[1173] (2) Anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode

[1174] 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.

[1175] 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.

[1176] Figure 1 Schematic 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.

[1177] 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.

[1178] 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 first light-emitting layer 5a and a second light-emitting layer 5b. The hole transport region disposed between the anode 3 and the first light-emitting layer 5a 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 second light-emitting layer 5b and the cathode 4 is formed by a first electron transport layer 7a and a second electron transport layer 7b.

[1179] 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.

[1180] substrate

[1181] 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 polyimide, polycarbonate, polyarylate, polyether sulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, etc. can be cited. In addition, an inorganic vapor-deposited film can also be used.

[1182] anode

[1183] 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.

[1184] 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.

[1185] Hole transport region

[1186] 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.

[1187] 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.

[1188] 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.

[1189] Hole injection layer

[1190] 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.

[1191] As hole injection layer 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.

[1192] 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.

[1193] 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.

[1194] In addition, an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K) is also preferably used.

[1195] [Chemical formula 223]

[1196]

[1197] (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-. )

[1198] As R2 27 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl and the like can be mentioned.

[1199] Hole transport layer

[1200] 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. Compound (1) can be used alone or in combination with the following compounds for the hole transport layer.

[1201] 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.

[1202] 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.

[1203] In one embodiment of the organic electroluminescent element of the present invention, at least one of the first hole transport layer and the second hole transport layer contains the invention compound. Specifically, in the hole transport layer of the two-layer structure, the invention compound may be contained in one of the first hole transport layer and the second hole transport layer, or in both. In addition, in another embodiment, at least one of the first to third hole transport layers contains the invention compound. Specifically, in the hole transport layer of the three-layer structure, the invention compound may be contained in only one of the first to third hole transport layers, or in only any two layers, or in all layers.

[1204] In one embodiment of the present invention, the inventive compound is preferably contained in the second hole transport layer. Specifically, 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.

[1205] As hole transport layer materials other than compound (1), for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used.

[1206] 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.

[1207] 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).

[1208] 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).

[1209] A polymer compound such as poly(N-vinylcarbazole) (abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation: PVTPA) may also be used.

[1210] 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.

[1211] In one embodiment of the organic EL device according to the present invention, the first hole transport layer includes a compound represented by the following formula (11) or (12).

[1212] [Chemical formula 224]

[1213]

[1214] [In the above formula (11) and formula (12),

[1215] L A1 , L B1 , LC1 , 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,

[1216] k is 1, 2, 3 or 4,

[1217] 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,

[1218] When k is 2, 3 or 4, 2, 3 or 4 L E2 Same or different from each other,

[1219] 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,

[1220] 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,

[1221] 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 ),

[1222] R' 901 , R' 902 and R' 903 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1223] In R' 901 When there are multiple R' 901 Same or different from each other,

[1224] In R' 902 When there are multiple R' 902Same or different from each other,

[1225] In R' 903 When there are multiple R' 903 The same as or different from each other.]

[1226] It should be noted that the first hole transport layer may contain one compound represented by formula (11) or formula (12), or may contain two or more compounds represented by formula (11) or formula (12).

[1227] 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.

[1228] In addition, it is more preferred that A in formula (11) 1 , B 1 and C 1 At least one of the above, and A in formula (12) 2 , B 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.

[1229] 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.

[1230] L A1 , L B1 , L C1 , L A2 , L B2 , LC2 and L D2 Preferably, each independently is a single bond, a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.

[1231] Specific examples of the compounds represented by formula (11) and formula (12) include the following compounds.

[1232] [Chemical formula 225]

[1233]

[1234] Dopant materials for the light-emitting layer

[1235] 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.

[1236] In one embodiment of the present invention, the light-emitting layer is a single layer. In another embodiment of the present invention, the light-emitting layer includes a first light-emitting layer on the anode side and a second light-emitting layer on the cathode side.

[1237] 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.

[1238] 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.

[1239] 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.

[1240] In one embodiment of the present invention, the light-emitting layer preferably contains a fluorescent light-emitting material (fluorescent dopant material).

[1241] 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.

[1242] 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.

[1243] 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 (abbreviated as: Ir(bto)2(acac)), bis(1-phenylisoquinoline-N,C2')iridium(III)acetylacetonate (abbreviated as: Ir(piq)2(acac)), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviated as: Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as: PtOEP) can be cited.

[1244] 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).

[1245] Host material of the light-emitting layer

[1246] 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.

[1247] As the host material, use e.g.

[1248] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes,

[1249] (2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives,

[1250] (3) Carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or Derivatives and other condensed aromatic compounds,

[1251] (4) Aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives.

[1252] 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;

[1253] 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;

[1254] 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

[1255] 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.

[1256] In particular, in the case of a blue fluorescent element, it is preferable to use the anthracene compound described below as a host material.

[1257] [Chemical formula 226]

[1258]

[1259] [Chemical formula 227]

[1260]

[1261] [Chemical formula 228]

[1262]

[1263] 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.

[1264] 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").

[1265] The method for determining the peak wavelength of the main peak is as follows. A 5 μmol / L toluene solution of the compound to be determined 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.

[1266] 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).

[1267] The fluorescent compound may be the dopant material or the host material.

[1268] 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.

[1269] 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.

[1270] Electron transport layer

[1271] 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.

[1272] 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.

[1273] The electron transport layer may be, for example,

[1274] (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes,

[1275] (2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives,

[1276] (3)Polymer compounds.

[1277] 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).

[1278] 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).

[1279] 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).

[1280] 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.

[1281] Electron injection layer

[1282] 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.

[1283] Alternatively, a material having an electron transport property and containing an alkali metal, an alkaline earth metal or a compound thereof may be used, specifically, a material containing magnesium (Mg) in Alq, etc. In this case, electron injection from the cathode can be performed more efficiently.

[1284] Alternatively, the electron injection layer may 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 material (metal complex, heteroaromatic compound, etc.) constituting the electron transport layer described above can be used. As an electron donor, it is a material that exhibits electron donating properties to the 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. In addition, organic compounds such as tetrathiafulvalene (abbreviated as: TTF) can also be used.

[1285] cathode

[1286] 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, AILi), and rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys thereof.

[1287] 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.

[1288] 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.

[1289] Insulation layer

[1290] 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.

[1291] 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.

[1292] Spacer

[1293] 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.

[1294] 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.

[1295] Barrier layer

[1296] Blocking layers such as an electron blocking layer, a hole blocking layer, and an exciton blocking layer may also be provided adjacent to the light-emitting layer. An electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer, and a hole blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron transport layer. An exciton blocking layer has the function of preventing excitons generated in the light-emitting layer from diffusing to the surrounding layers, thereby confining the excitons in the light-emitting layer.

[1297] Each layer of the organic EL element can be formed by a conventionally known vapor deposition method, coating method, etc. For example, it can be formed by a vapor deposition method such as a vacuum vapor deposition method, a molecular beam vapor deposition method (MBE method), or a known method based on a coating method such as a dip coating method, a spin coating method, a casting method, a rod coating method, a roll coating method, etc. using a solution of a layer-forming compound.

[1298] The thickness of each layer is not particularly limited. Generally, if the thickness is too thin, defects such as pinholes are easily generated, while if it is too thick, a high driving voltage is required and the efficiency is deteriorated. Therefore, it is usually 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm.

[1299] In one embodiment of the organic EL element of the present invention, without particular limitation, the total thickness of the first hole transport layer (anode side) and the second hole transport layer (cathode side) is preferably greater than 30 nm and less than 150 nm, more preferably greater than 40 nm and less than 130 nm.

[1300] In one embodiment of the organic EL element of the present invention, the thickness of the second hole transport 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, most preferably 35 nm or more, and preferably 100 nm or less.

[1301] In one embodiment of the organic EL element of the present invention, 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, most preferably 35 nm or more, and preferably 100 nm or less.

[1302] In addition, in one embodiment of the organic EL element of the present invention, there is no particular limitation, and the film thickness D1 of the first hole transport layer and the film thickness D2 of the second hole transport layer preferably satisfy the relationship of 0.3<D2 / D1<4.0. It is more preferred to satisfy the relationship of 0.5<D2 / D1<3.5, and it is further preferred to satisfy the relationship of 0.75<D2 / D1<3.0. In addition, in another embodiment of the organic EL element of the present invention, there is no particular limitation, and the above-mentioned D2 / D1 may satisfy the relationship of 0.05<D2 / D1<0.5, may satisfy the relationship of 0.05<D2 / D1<0.3, and may satisfy the relationship of 0.08<D2 / D1<0.25.

[1303] As an embodiment of the organic EL device of the present invention, for example, an organic EL device having a hole transport layer of the above two-layer structure and

[1304] The first embodiment in which the second hole transport layer contains the compound (1) of the present invention and the first hole transport layer does not contain the compound (1) of the present invention;

[1305] The first hole transport layer and the second hole transport layer both contain the second embodiment of the compound (1) of the present invention; or

[1306] A third embodiment in which the first hole transport layer contains the compound (1) of the present invention, and the second hole transport layer does not contain the compound (1) of the present invention;

[1307] As an organic EL element having a hole transport layer of the above three-layer structure, and

[1308] A fourth embodiment in which the first hole transport layer contains the compound (1) of the present invention, and the second hole transport layer and the third hole transport layer do not contain the compound (1) of the present invention;

[1309] A fifth embodiment in which the second hole transport layer contains the compound (1) of the present invention, and the first hole transport layer and the third hole transport layer do not contain the compound (1) of the present invention;

[1310] A sixth embodiment in which the third hole transport layer contains the compound (1) of the present invention, and the first hole transport layer and the second hole transport layer do not contain the compound (1) of the present invention;

[1311] The seventh embodiment in which the first hole transport layer and the second hole transport layer contain the compound (1) of the present invention, and the third hole transport layer does not contain the compound (1) of the present invention;

[1312] The eighth embodiment in which the first hole transport layer and the third hole transport layer contain the compound (1) of the present invention, and the second hole transport layer does not contain the compound (1) of the present invention;

[1313] The ninth embodiment in which the second hole transport layer and the third hole transport layer contain the compound (1) of the present invention, and the first hole transport layer does not contain the compound (1) of the present invention; or

[1314] The first to third hole transport layers all contain the tenth embodiment of the compound (1) of the present invention; and so on.

[1315] Electronic devices

[1316] 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.

[1317] Example

[1318] Hereinafter, the present invention will be described in further detail using examples, but the present invention is not limited to the following examples.

[1319] The compounds represented by formula (1) used in the production of the organic EL devices of Examples are shown below.

[1320] [Chemical formula 229]

[1321]

[1322] Comparative compounds used in the production of organic EL devices of Comparative Examples are shown below.

[1323] [Chemical formula 230]

[1324]

[1325] Other compounds used in the production of the organic EL devices of Examples and Comparative Examples are shown below.

[1326] [Chemical formula 231]

[1327]

[1328] [Production of organic EL elements]

[1329] Example 1

[1330] 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.

[1331] The cleaned glass substrate with a transparent electrode was mounted on a substrate holder of a vacuum evaporation device, and compound HT-1 and 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. It should be noted that the mass ratio of compound HT-1 to compound HA (HT-1:HA) was 97:3.

[1332] Next, Compound 1 as Compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a film thickness of 80 nm.

[1333] Next, compound HT-2 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 10 nm.

[1334] Next, compound BH-1 (host material) and compound BD-1 (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-1 to compound BD-1 (BH-1:BD-1) was 96:4.

[1335] Next, compound ET-1 was deposited on the light-emitting layer to form a first electron transport layer with a thickness of 5 nm.

[1336] 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 20 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50.

[1337] Next, LiF was vapor-deposited on the second electron transport layer to form an electron injection layer having a film thickness of 1 nm.

[1338] Next, metal Al was deposited on the electron injection layer to form a metal cathode with a film thickness of 50 nm.

[1339] The layer structure of the organic EL device of Example 1 obtained in this manner is shown below.

[1340] ITO(130) / HT-1:HA=97:3(10) / HT-1(80) / HT-2(10) / BH-1:BD-1=96:4(25) / ET-1(5) / ET-2:Liq=50:50(20) / LiF(1) / Al(50)

[1341] In addition, in the above-mentioned layer structure, the number in a parenthesis is a film thickness (nm), and the ratio is a mass ratio.

[1342] <Evaluation of Organic EL Devices>

[1343] (1) Determination of external quantum efficiency (EQE)

[1344] A voltage was applied to the organic EL element at room temperature so that the current density was 10 mA / cm 2 The brightness was measured using a brightness meter (CS-1000, a spectrophotometer manufactured by Minolta Corporation), and the external quantum efficiency (%) was evaluated based on the results.

[1345] The results are shown in Table 1.

[1346] Embodiments 2 to 5

[1347] In Example 1, an organic EL device was produced in the same manner as in Example 1 except that any one of Compounds 2 to 5 was used instead of Compound 1 as Compound HT-1, and the external quantum efficiency (EQE) was evaluated.

[1348] The results are shown in Table 1.

[1349] Comparative Examples 1 to 4

[1350] In Example 1, an organic EL device was produced in the same manner as in Example 1 except that any one of Comparative Compounds 1 to 4 was used instead of Compound 1 as Compound HT-1, and the external quantum efficiency (EQE) was evaluated.

[1351] The results are shown in Table 1.

[1352] [Table 1]

[1353] Table 1

[1354]

[1355] As is clear from the results in Table 1, the organic EL devices of Examples 1 to 5 containing the compound (1) showed significantly improved external quantum efficiency compared to the organic EL devices of Comparative Examples 1 to 4 not containing the compound (1).

[1356] <Synthesis of Compounds>

[1357] Synthesis Example 1: Synthesis of Compound 1

[1358] [Chemical formula 232]

[1359]

[1360] Under an argon atmosphere, a mixture of 4.02 g (10.0 mmol) of N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine, 3.03 g (10.0 mmol) of 4-bromo-6-(tert-butyl)dibenzo[b,d]furan, 0.183 g (0.20 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.232 g (0.80 mmol) of tri-tert-butylphosphonium tetrafluoroborate, 1.35 g (14.0 mmol) of sodium tert-butoxide and 100 mL of xylene was stirred at 110° C. for 7 hours.

[1361] The obtained reaction solution was cooled to room temperature and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 4.41 g of a white solid. The yield was 71%.

[1362] The result of mass spectrometry analysis was m / e=624, based on which the obtained white solid was identified as Compound 1 (molecular weight 623.84).

[1363] Synthesis Example 2: Synthesis of Compound 2

[1364] [Chemical formula 233]

[1365]

[1366] In Synthesis Example 1, 3.58 g of a white solid was obtained by performing the same operation except that 6-bromo-2,4-di(tert-butyl)dibenzo[b,d]furan was used instead of 4-bromo-6-(tert-butyl)dibenzo[b,d]furan. The yield was 52%.

[1367] The result of mass spectrometry analysis was m / e=680, based on which the obtained white solid was identified as Compound 2 (molecular weight 679.95).

[1368] Synthesis Example 3: Synthesis of Compound 3

[1369] [Chemical formula 234]

[1370]

[1371] In Synthesis Example 1, 3.12 g of a white solid was obtained by performing the same operation except that 4'-(tert-butyl)-2-chloro-1,1'-biphenyl was used instead of 4-bromo-6-(tert-butyl)dibenzo[b,d]furan. The yield was 51%.

[1372] The result of mass spectrometry analysis was m / e=610, based on which the obtained white solid was identified as Compound 3 (molecular weight 609.86).

[1373] Synthesis Example 4: Synthesis of Compound 4

[1374] [Chemical formula 235]

[1375]

[1376] In Synthesis Example 1, 5.36 g of a white solid was obtained by carrying out the same operation except that 4"',5"-di-tert-butyl-2-chloro-1,1':2',1":2",1"'-quaterphenyl was used instead of 4-bromo-6-(tert-butyl)dibenzo[b,d]furan. The yield was 65%.

[1377] The result of mass spectrometry analysis was m / e=818, based on which the obtained white solid was identified as compound 4 (molecular weight 818.16).

[1378] Synthesis Example 5: Synthesis of Compound 5

[1379] [Chemical formula 236]

[1380]

[1381] In Synthesis Example 1, 5.11 g of a white solid was obtained by performing the same operation except that 4",5'-di-tert-butyl-2-chloro-1,1':2',1"-terphenyl was used instead of 4-bromo-6-(tert-butyl)dibenzo[b,d]furan. The yield was 69%.

[1382] The result of mass spectrometry analysis was m / e=743, based on which the obtained white solid was identified as Compound 5 (molecular weight 742.06).

[1383] Synthesis Example 6: Synthesis of Compound 6

[1384] [Chemical formula 237]

[1385]

[1386] Under argon atmosphere, a mixture of 4.02 g (10.0 mmol) of N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9-dimethyl-9H-fluorene-2-amine, 3.90 g (10.0 mmol) of 3,6-di-tert-butyl-9-(3-chlorophenyl)-9H-carbazole, 0.183 g (0.20 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.232 g (0.80 mmol) of tri-tert-butylphosphonium tetrafluoroborate, 1.35 g (14.0 mmol) of sodium tert-butoxide and 100 mL of xylene was stirred at 110° C. for 17 hours.

[1387] The obtained reaction solution was cooled to room temperature and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 6.23 g of a white solid. The yield was 69%.

[1388] The result of mass spectrometry analysis was m / e=755, based on which the obtained white solid was identified as Compound 6 (molecular weight 755.06).

[1389] Explanation of symbols

[1390] 1, 11, 12 Organic EL elements

[1391] 2 substrate

[1392] 3 Anode

[1393] 4 Cathode

[1394] 5. Luminous layer

[1395] 5a 1st light emitting layer

[1396] 5b Second light-emitting layer

[1397] 6 Hole transport region (hole transport layer)

[1398] 6a Hole injection layer

[1399] 6b 1st hole transport layer

[1400] 6c Second hole transport layer

[1401] 6d Third hole transport layer

[1402] 7 Electron transport region (electron transport layer)

[1403] 7a 1st electron transport layer

[1404] 7b Second electron transport layer

[1405] 10, 20, 30 light units

Claims

1. A compound represented by the following formula (1), In formula (1), R a1 ~R a4 Each is independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, wherein: R a1 With R a2 They may be bonded to each other to form a ring, or may not be bonded to each other, R a3 With R a4 They may be bonded to each other to form a ring, or may not be bonded to each other, R 1 , R 2 and R b1 ~R b12 Each independently Hydrogen atom, halogen atom, nitro group, cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, -S-(R 905 ) or -N(R 906 )(R 907 ) shown in the following; The R 901 ~R 907 Each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms; Among them, R b1 ~R b12 The two adjacent groups in the group may be bonded to each other to form a ring, or may not be bonded to each other, Ar 1 is a group represented by any one of the following formulae (i) to (iii), In formula (i), R b13 ~R b16 Each independently Hydrogen atom, halogen atom, nitro group, cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, -S-(R 905 ) or -N(R 906 )(R 907 ) shown in the following; The R 901 ~R 907 Each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms; Among them, R b13 ~R b16 The two adjacent groups in may be bonded to each other to form a benzene ring, or may not be bonded to each other, Ar 2 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group, In the R b13 ~R b16 When two adjacent groups in Ar are not bonded to each other, 3 is a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group, wherein R b13 ~R b16 When two adjacent groups in Ar are bonded to each other to form a benzene ring, 3 is a hydrogen atom, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group, n1 is 0, 1, or 2, *1 represents the bonding position to the nitrogen atom represented in formula (1), n2 is an integer greater than 1, When n2 is 1, R x is a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, excluding adamantyl, When n2 is an integer greater than 2, R x is an alkyl group having 1 to 30 carbon atoms or a cycloalkyl group having 3 to 30 ring carbon atoms, *2 indicates R x The bonding position of (a) R x Replace selected from R b13 ~R b16 At least one of the following is bonded to the benzene ring, or (b) R x Bonded to a b13 ~R b16 or (c) R x Bonded to a selected from Ar 2 and Ar 3 or satisfying at least one of the bonding modes selected from (a) to (c), In formula (ii), X is -O-, -S- or -N(-R 3 )-, where R 3 is an alkyl group having 1 to 50 carbon atoms or an aryl group having 6 to 50 ring carbon atoms, R c1 , R c2 , R b17 ~R b22 and R d1 ~R d6 Each independently Hydrogen atom, halogen atom, nitro group, cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, -S-(R 905 ) or -N(R 906 )(R 907 ) shown in the following; The R 901 ~R 907 Each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms; Among them, R c1 , R c2 and R b17 ~R b22 Two adjacent groups in may be bonded to each other to form a ring, or may not be bonded to each other. n3 is 0 or 1, *3 represents the bonding position to the nitrogen atom represented in formula (1). *4 and *5 represent replacement of R d1 ~R d6 and bonded to the benzene ring at different positions, wherein when n3 is 0, *3 and *6 are directly connected without passing through *4 and *5, *6 means replace R b17 ~R b19 Any one of them is bonded to the benzene ring, R y1 is an alkyl group having 1 to 30 carbon atoms or a cycloalkyl group having 3 to 30 ring carbon atoms, n4 is an integer greater than or equal to 1, *7 means R y1 The bonding position of (d)R y1 Replace selected from R c1 , R c2 and R b17 ~R b22 At least one of the following is bonded to the benzene ring, or (e) R y1 Bonded to a c1 , R c2 , R 3 and R b17 ~R b22 or satisfying both bonding modes (d) and (e), In formula (iii), R b23 ~R b30 and R e1 ~R e5 Each independently Hydrogen atom, halogen atom, nitro group, cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, -S-(R 905 ) or -N(R 906 )(R 907 ) shown in the following; The R 901 ~R 907 Each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms; Among them, R b23 ~R b30 The two adjacent groups in the group may be bonded to each other to form a ring, or may not be bonded to each other, *8 represents the bonding position to the nitrogen atom represented in formula (1), *9 represents a nitrogen atom in place of R in formula (iii). e1 ~R e5 Any one of them is bonded to the benzene ring, R y2 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, n5 is an integer greater than or equal to 1, *10 means R y2 The bonding position of (f)R y2 Replace selected from R b23 ~R b30 At least one of the following is bonded to the benzene ring, or (g) R y2 Bonded to a b23 ~R b30 or satisfies both bonding modes (f) and (g).

2. The compound according to claim 1, which is represented by the following formula (1-1) or (1-2), The definitions of the groups in formula (1-1) and formula (1-2) are the same as those in formula (1).

3. The compound according to claim 1, which is represented by the following formula (1-3) or (1-4), The definitions of the groups in formula (1-3) and formula (1-4) are the same as those in the above formula (1).

4. The compound according to claim 1, which is represented by the following formula (1-5) or (1-6), The definitions of the groups in formula (1-5) and formula (1-6) are the same as those in formula (1).

5. The compound according to claim 1, which is represented by the following formula (1-7), (1-8) or (1-9), The definitions of the groups in formula (1-7), formula (1-8) and formula (1-9) are the same as those in the above formula (1).

6. The compound according to any one of claims 1 to 5, wherein R 1 , R 2 Each is independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

7. The compound according to any one of claims 1 to 6, wherein R b1 ~R b12 are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R b1 ~R b12 Two adjacent groups in the group may be bonded to each other to form a ring, or may not be bonded to each other.

8. The compound according to any one of claims 1 to 7, wherein Ar 1 is a group represented by the formula (i).

9. The compound according to any one of claims 1 to 7, wherein Ar 1 is the group represented by the formula (ii).

10. The compound according to any one of claims 1 to 8, wherein The group represented by the formula (i) is a group represented by the following formula (i-1) or (i-5), The definitions of the groups in formula (i-1) and (i-5) are the same as those in formula (i), wherein Ar 2 The benzene ring represents Ar 2 It is a benzene ring.

11. The compound according to any one of claims 1 to 8, wherein The group represented by the formula (i) is a group represented by any one of the following formulae (i-2) to (i-4), The definitions of the groups in formulas (i-2) to (i-4) are the same as those in formula (i). In the naphthalene ring described in the above formulae (i-2) to (i-4), the site where no substituent is described may be bonded to a hydrogen atom, R x or a substituent is bonded, and the substituent is optionally bonded to R x .

12. The compound according to any one of claims 1 to 11, wherein When n2 is 1, R x It is a substituted or unsubstituted alkyl group having 3 to 10 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 9 ring carbon atoms.

13. The compound according to any one of claims 1 to 7 and 9, wherein The group represented by the formula (ii) is a group represented by the following formula (ii-1), The definitions of the groups in formula (ii-1) are the same as those in formula (ii).

14. The compound according to any one of claims 1 to 7 and 9, wherein The group represented by the formula (ii) is a group represented by the following formula (ii-2), The definitions of the groups in formula (ii-2) are the same as those in formula (ii).

15. The compound according to any one of claims 1 to 7 and 9, wherein The group represented by the formula (ii) is a group represented by any one of the following formulae (ii-3) to (ii-5), The definitions of the groups in formula (ii-3) and formula (ii-4) are the same as those in formula (ii). The definitions of the groups in formula (ii-5) are the same as those in the above formula (ii).

16. The compound according to any one of claims 1 to 7 and 9, wherein The group represented by the formula (ii) is a group represented by the following formula (ii-6), The definitions of the groups in formula (ii-6) are the same as those in the above formula (ii).

17. The compound according to any one of claims 1 to 7 and 9, wherein The group represented by the formula (ii) is a group represented by the following formula (ii-7), The definitions of the groups in formula (ii-7) are the same as those in the above formula (ii).

18. The compound according to any one of claims 1 to 7, wherein The group represented by the formula (iii) is a group represented by any one of the following formulae (iii-1) to (iii-3), The definitions of the groups in formula (iii-1) and formula (iii-2) are the same as those in formula (iii). The definitions of the groups in formula (iii-3) are the same as those in the above formula (iii).

19. The compound according to any one of claims 1 to 18, wherein Contains one or more deuterium atoms in a molecule.

20. The compound according to claim 1, which is any one of the following compounds 1 to 6, 21 . An organic electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a light-emitting layer, and at least one layer of the organic layer comprises the compound according to claim 1 .

22. The organic electroluminescent element according to claim 21, wherein The organic layer comprises a hole transport region between the anode and the light emitting layer, and the hole transport region comprises compound (1).

23. The organic electroluminescent element according to claim 22, 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. At least one of the first hole transport layer and the second hole transport layer contains the compound according to any one of claims 1 to 20.

24. The organic electroluminescent element according to claim 23, wherein At least the first hole transport layer contains the compound according to any one of claims 1 to 20.

25. The organic electroluminescent element according to claim 23 or 24, 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.

26. The organic electroluminescent element according to any one of claims 21 to 25, wherein The light-emitting layer is a single layer. 27 . An electronic device comprising the organic electroluminescent element according to claim 21 .

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