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

Abstract

A compound represented by formula (101). # imgabs0 #

Description

Technical Field

[0001] The present invention relates to novel compounds, materials for organic electroluminescent elements, organic electroluminescent elements and electronic equipment. Background Art

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

[0003] The device performance of conventional organic EL devices is still insufficient. In order to improve the device performance, the materials used in the organic EL devices are being improved, but further performance improvement is required.

[0004] Patent Documents 1 to 3 disclose using a compound having a specific structure in an organic EL element.

[0005] Prior art literature

[0006] Patent Literature

[0007] Patent Document 1: Japanese Patent Application Publication No. 2009-21336

[0008] Patent Document 2: International Publication No. 2005 / 112519

[0009] Patent Document 3: International Publication No. 2021 / 157636 Summary of the invention

[0010] An object of the present invention is to provide a high-performance organic EL element and a compound capable of realizing the organic EL element.

[0011] The present inventors have conducted intensive studies to achieve the above-mentioned object and have found that a compound having a specific structure contributes to the improvement of the performance of an organic EL element, thereby completing the present invention.

[0012] According to the present invention, the following compounds and the like are provided.

[0013] 1. A compound represented by the following formula (101).

[0014] [Chemistry 1]

[0015]

[0016] [In formula (101),

[0017] Either one of X1 and X2 is N, and the other is CH.

[0018] R1~R 10Each is independently a hydrogen atom or a substituent R. A group consisting of two or more adjacent R1 to R5 is not bonded to each other. 10 The adjacent groups of two or more are not bonded to each other.

[0019] n1 is an integer from 0 to 3.

[0020] When n1 is 0, the structure in the brackets involving n1 is a single bond.

[0021] When n1 is 2 or 3, the structures within the multiple brackets related to n1 may be the same or different.

[0022] R 11 is a hydrogen atom or a substituent R. 4 R 11 They can be the same or different from each other. 11 The adjacent groups of two or more are not bonded to each other.

[0023] n2 is an integer from 0 to 3.

[0024] When n2 is 0, the structure in the brackets involving n2 is a single bond.

[0025] When n2 is 2 or 3, the structures within the multiple brackets involving n2 may be the same or different.

[0026] R 21 is a hydrogen atom or a substituent R. 4 R 21 They can be the same or different from each other. 21 The adjacent groups of two or more are not bonded to each other.

[0027] n101 is 0 or 1.

[0028] When n101 is 0, the structure in the brackets related to n101 is a single bond.

[0029] L1 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.

[0030] R 101 ~R 108 1 in represents the same as (L1) n101 It does not represent the single bond of (L1) n101 The single bond R 101 ~R 108 One of them represents a single bond with the nitrogen atom of the carbazole structure.

[0031] R not representing the single bond 101 ~R 108 Each is independently a hydrogen atom or a substituent R. 101 ~R 108 The adjacent groups of two or more are not bonded to each other.

[0032] By R 201 ~R 208 One or more groups of two or more adjacent ones of the moieties may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring, or may not be bonded to each other.

[0033] R not bonded to each other 201 ~R 208 Each is independently a hydrogen atom or a substituent R.

[0034] The substituent R is selected from:

[0035] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0036] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0037] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

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

[0039] -Si(R 901 )(R 902 )(R 903 ),

[0040] -O-(R 904 ),

[0041] -S-(R 905 ),

[0042] -N(R 906 )(R 907 ),

[0043] Halogen atoms, cyano, nitro,

[0044] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0045] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0046] When there are two or more substituents R, the two or more substituents R may be the same as or different from each other.

[0047] R 901 ~R 907 Each independently

[0048] Hydrogen atoms,

[0049] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0050] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0051] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0052] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0053] R 901 ~R 907 When there are two or more of each, the two or more R 901 ~R 907 Can be the same or different. ].

[0054] 2. The compound according to 1 above, wherein the compound represented by formula (101) is a compound represented by the following formula (1),

[0055] [Chemistry 2]

[0056]

[0057] [In formula (1),

[0058] R1~R 10 Each is independently a hydrogen atom or a substituent R. A group consisting of two or more adjacent R1 to R5 is not bonded to each other. 10 The adjacent groups of two or more are not bonded to each other.

[0059] n1 is an integer from 0 to 3.

[0060] When n1 is 0, the structure in the brackets involving n1 is a single bond.

[0061] When n1 is 2 or 3, the structures within the multiple brackets related to n1 may be the same or different.

[0062] R 11 is a hydrogen atom or a substituent R. 4 R 11 They can be the same or different from each other. 11 The adjacent groups of two or more are not bonded to each other.

[0063] n2 is an integer from 0 to 3.

[0064] When n2 is 0, the structure in the brackets involving n2 is a single bond.

[0065] When n2 is 2 or 3, the structures within the multiple brackets involving n2 may be the same or different.

[0066] R 21 is a hydrogen atom or a substituent R. 4 R 21 They can be the same or different from each other. 21 The adjacent groups of two or more are not bonded to each other.

[0067] L1 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.

[0068] R 101 ~R 108 One of them represents a single bond with L1. R that does not represent a single bond with L1 101 ~R 108 One of them represents a single bond with the nitrogen atom of the carbazole structure.

[0069] R not representing the single bond 101 ~R 108 Each is independently a hydrogen atom or a substituent R. 101 ~R 108 The adjacent groups of two or more are not bonded to each other.

[0070] By R 201 ~R 208 One or more groups of two or more adjacent ones of the moieties may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring, or may not be bonded to each other.

[0071] R not bonded to each other 201 ~R 208 Each is independently a hydrogen atom or a substituent R.

[0072] The substituent R is selected from:

[0073] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0074] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0075] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0076] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0077] -Si(R 901 )(R 902 )(R 903 ),

[0078] -O-(R 904 ),

[0079] -S-(R 905 ),

[0080] -N(R 906 )(R 907 ),

[0081] Halogen atoms, cyano, nitro,

[0082] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0083] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0084] When there are two or more substituents R, the two or more substituents R may be the same as or different from each other.

[0085] R 901 ~R 907 Each independently

[0086] Hydrogen atoms,

[0087] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0088] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0089] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0090] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0091] R 901 ~R 907 When there are two or more of each, the two or more R 901 ~R 907 Can be the same or different. ].

[0092] 3. The compound according to 1 above, wherein the compound represented by formula (101) is a compound represented by the following formula (2):

[0093] [Chemistry 3]

[0094]

[0095] [In formula (2),

[0096] R1~R 10 Each is independently a hydrogen atom or a substituent R. A group consisting of two or more adjacent R1 to R5 is not bonded to each other. 10 The adjacent groups of two or more are not bonded to each other.

[0097] n1 is an integer from 0 to 3.

[0098] When n1 is 0, the structure in the brackets involving n1 is a single bond.

[0099] When n1 is 2 or 3, the structures within the multiple brackets related to n1 may be the same or different.

[0100] R 11 is a hydrogen atom or a substituent R. 4 R11 They can be the same or different from each other. 11 The adjacent groups of two or more R1 and R2 are not bonded to each other. 11 The groups of R5 and R 11 The groups are not bonded to each other.

[0101] n2 is an integer from 1 to 3.

[0102] When n2 is 2 or 3, the structures within the multiple brackets involving n2 may be the same or different.

[0103] R 21 is a hydrogen atom or a substituent R. 4 R 21 They can be the same or different from each other. 21 The adjacent groups of two or more R6 and R 21 The groups of R are not bonded to each other. 10 With R 21 The groups are not bonded to each other.

[0104] R 101 ~R 108 One of them represents a single bond to a carbon atom of a pyrimidine structure. R that does not represent a single bond to a carbon atom of a pyrimidine structure 101 ~R 108 One of them represents a single bond with the nitrogen atom of the carbazole structure.

[0105] R not representing the single bond 101 ~R 108 Each is independently a hydrogen atom or a substituent R. 101 ~R 108 The adjacent groups of two or more are not bonded to each other.

[0106] By R 201 ~R 208 One or more groups of two or more adjacent ones of the moieties may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring, or may not be bonded to each other.

[0107] R not bonded to each other 201 ~R 208 Each is independently a hydrogen atom or a substituent R.

[0108] The substituent R is selected from:

[0109] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

[0111] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0112] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0113] -Si(R 901 )(R 902 )(R 903 ),

[0114] -O-(R 904 ),

[0115] -S-(R 905 ),

[0116] -N(R 906 )(R 907 ),

[0117] Halogen atoms, cyano, nitro,

[0118] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0119] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0120] When there are two or more substituents R, the two or more substituents R may be the same as or different from each other.

[0121] R 901 ~R 907 Each independently

[0122] Hydrogen atoms,

[0123] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0124] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0125] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0126] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0127] R 901 ~R 907 When there are two or more of each, the two or more R 901 ~R 907 Can be the same or different. ].

[0128] According to the present invention, a high-performance organic EL element and a compound capable of realizing the organic EL element can be provided.

[0129] BRIEF DESCRIPTION OF THE DRAWINGS

[0130] Figure 1 This is a diagram showing a schematic configuration of an organic EL element according to one embodiment of the present invention. DETAILED DESCRIPTION

[0131] [definition]

[0132] In this specification, the hydrogen atom includes isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0133] In the present specification, in chemical structural formulas, a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is bonded to a position capable of bonding that is not explicitly indicated by symbols such as "R" or "D" representing a deuterium atom.

[0134] In this specification, the number of ring carbon atoms represents the number of carbon atoms among the atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are combined to form a ring structure. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. The "number of ring carbon atoms" recorded below is the same unless otherwise specified. For example, the number of ring carbon atoms of the benzene ring is 6, the number of ring carbon atoms of the naphthalene ring is 10, the number of ring carbon atoms of the pyridine ring is 5, and the number of ring carbon atoms of the furan ring is 4. In addition, for example, the number of ring carbon atoms of 9,9-diphenylfluorenyl is 13, and the number of ring carbon atoms of 9,9'-spirobifluorenyl is 25.

[0135] In addition, when the benzene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of the benzene ring substituted with an alkyl group is 6. In addition, when the naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.

[0136] In this specification, the number of ring atoms represents the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) whose atoms are combined into a cyclic structure (e.g., a monocyclic compound, a condensed ring compound, a bridged 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 also the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or the number of atoms constituting the 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.

[0137] In the present specification, "the number of carbon atoms XX to YY" in the expression "ZZ group having XX to YY carbon atoms which may be substituted or unsubstituted" means the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the group is substituted. Here, "YY" is greater than "XX", "XX" means an integer greater than 1, and "YY" means an integer greater than 2.

[0138] In the present specification, "the number of atoms XX to YY" in the expression "ZZ group having XX to YY atoms, which may be substituted or unsubstituted" means the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituent when the group is substituted. Here, "YY" is greater than "XX", "XX" means an integer greater than 1, and "YY" means an integer greater than 2.

[0139] 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".

[0140] In the present specification, "unsubstituted" in the case of "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.

[0141] In addition, in the present specification, "substituted" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. "Substituted" in the case of "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group are replaced by AA group.

[0142] "Substituents described in this specification"

[0143] Hereinafter, the substituents described in the present specification will be described.

[0144] Unless otherwise specified in the present specification, the “unsubstituted aryl group” described in the present specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms.

[0145] Unless otherwise specified in the present specification, the number of ring atoms in the "unsubstituted heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0146] Unless otherwise specified in the present specification, the “unsubstituted alkyl group” described in the present specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms.

[0147] Unless otherwise specified in the present specification, the “unsubstituted alkenyl group” described in the present specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0148] Unless otherwise specified in the present specification, the “unsubstituted alkynyl group” described in the present specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0149] Unless otherwise specified in the present specification, the “unsubstituted cycloalkyl group” described in the present specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6.

[0150] Unless otherwise specified in the present specification, the “unsubstituted arylene group” described in the present specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms.

[0151] Unless otherwise specified in the present specification, 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.

[0152] Unless otherwise specified in the present specification, the “unsubstituted alkylene group” described in the present specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms.

[0153] "Substituted or unsubstituted aryl"

[0154] Specific examples of the "substituted or unsubstituted aryl group" described in the present specification (specific example group G1) include the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B) (herein, the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group", and the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group"). In the present specification, when "aryl group" is mentioned alone, both "unsubstituted aryl group" and "substituted aryl group" are included.

[0155] "Substituted aryl" means 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 atoms bonded to the carbon atoms of the aryl itself in the "substituted aryl" in the following specific example group G1B are further replaced by a substituent, and groups in which the hydrogen atoms of the substituents in the "substituted aryl" in the following specific example group G1B are further replaced by substituents.

[0156] Unsubstituted aryl (specific example group G1A):

[0157] Phenyl,

[0158] p-Biphenyl,

[0159] m-Biphenyl,

[0160] o-Biphenyl,

[0161] 4-terphenyl-4-yl,

[0162] 4-terphenyl-3-yl,

[0163] 4-terphenyl-2-yl,

[0164] m-terphenyl-4-yl,

[0165] m-terphenyl-3-yl,

[0166] m-terphenyl-2-yl,

[0167] o-terphenyl-4-yl,

[0168] o-terphenyl-3-yl,

[0169] o-terphenyl-2-yl,

[0170] 1-naphthyl,

[0171] 2-naphthyl,

[0172] Anthracene,

[0173] Benzanthryl,

[0174] Fiki,

[0175] Triphenylene,

[0176] Phenyl,

[0177] Pyrene

[0178] base,

[0179] Benzo base,

[0180] Triphenylene,

[0181] Benzotriphenylene,

[0182] Tetraphenylene,

[0183] Pentaphenyl,

[0184] Fluorene,

[0185] 9,9'-Spirobifluorenyl,

[0186] Benzofluorenyl,

[0187] Dibenzofluorenyl,

[0188] Fluoranthene group,

[0189] Benzofluoranthene,

[0190] Perylene, and

[0191] A monovalent aromatic group derived by removing one hydrogen atom from the ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[0192] [Chemistry 4]

[0193]

[0194] [Chemistry 5]

[0195]

[0196] ·Substituted aryl (specific example group G1B): o-tolyl,

[0197] m-Toluene

[0198] p-Tolyl,

[0199] p-Xylyl,

[0200] m-Xylyl,

[0201] o-Xylyl,

[0202] p-Isopropylphenyl,

[0203] m-isopropylphenyl,

[0204] o-isopropylphenyl,

[0205] 4-tert-Butylphenyl,

[0206] m-tert-butylphenyl,

[0207] o-tert-butylphenyl,

[0208] 3,4,5-Trimethylphenyl,

[0209] 9,9-dimethylfluorenyl,

[0210] 9,9-Diphenylfluorenyl,

[0211] 9,9-bis(4-methylphenyl)fluorenyl,

[0212] 9,9-bis(4-isopropylphenyl)fluorenyl,

[0213] 9,9-bis(4-tert-butylphenyl)fluorenyl,

[0214] Cyanophenyl,

[0215] Triphenylsilylphenyl,

[0216] Trimethylsilylphenyl,

[0217] Phenyl naphthyl,

[0218] naphthylphenyl, and

[0219] A group in which one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the above-mentioned general formulae (TEMP-1) to (TEMP-15) are replaced by a substituent.

[0220] "Substituted or unsubstituted heterocyclic group"

[0221] 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.

[0222] The "heterocyclic group" described in the present specification is a monocyclic group or a condensed ring group.

[0223] The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0224] As specific examples of the "substituted or unsubstituted heterocyclic group" described in the present 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 (herein, 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 the present specification, when a "heterocyclic group" is mentioned alone, both "unsubstituted heterocyclic group" and "substituted heterocyclic group" are included.

[0225] “Substituted heterocyclic group” means 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 replaced, 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” described 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.

[0226] 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).

[0227] Specific example group G2B includes, for example: the following heterocyclic groups containing a nitrogen atom-substituted group (specific example group G2B1), heterocyclic groups containing an oxygen atom-substituted group (specific example group G2B2), heterocyclic groups containing a sulfur atom-substituted group (specific example group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced by a substituent (specific example group G2B4).

[0228] Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):

[0229] Pyrrolyl,

[0230] Imidazole,

[0231] Pyrazolyl,

[0232] Triazole,

[0233] Tetrazolyl,

[0234] Oxazolyl,

[0235] Isoxazolyl,

[0236] Oxadiazolyl,

[0237] Thiazolyl,

[0238] Isothiazolyl,

[0239] Thiadiazole,

[0240] Pyridyl,

[0241] Pyridazine

[0242] Pyrimidine,

[0243] Pyrazinyl,

[0244] Triazine,

[0245] Indolyl,

[0246] Isoindolyl,

[0247] Indolizinyl,

[0248] Quinolizinyl,

[0249] Quinoline,

[0250] Isoquinolinyl,

[0251] Cinnoline,

[0252] Phthalocyanine

[0253] Quinazoline,

[0254] Quinoxaline,

[0255] Benzimidazolyl,

[0256] Indazolyl,

[0257] Phenanthroline,

[0258] Phenanthridinyl,

[0259] Acridinium,

[0260] Phenolic acid,

[0261] Carbazolyl,

[0262] Benzocarbazolyl,

[0263] Morpholino,

[0264] Phenoxazine,

[0265] Phenothiazine,

[0266] azacarbazolyl, and diazacarbazolyl.

[0267] · Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): furyl,

[0268] Oxazolyl,

[0269] Isoxazolyl,

[0270] Oxadiazolyl,

[0271] Xanthyl,

[0272] Benzofuranyl,

[0273] Isobenzofuranyl,

[0274] Dibenzofuranyl,

[0275] Naphthobenzofuranyl,

[0276] Benzoxazolyl,

[0277] Benzisoxazolyl,

[0278] Phenoxazine,

[0279] Morpholino,

[0280] dinaphthofuranyl,

[0281] Azadibenzofuranyl,

[0282] Diazadibenzofuranyl,

[0283] azanaphthobenzofuranyl, and

[0284] naphthyridinylbenzofuranyl.

[0285] Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3):

[0286] Thienyl,

[0287] Thiazolyl,

[0288] Isothiazolyl,

[0289] Thiadiazole,

[0290] benzothienyl,

[0291] Isobenzothienyl,

[0292] dibenzothienyl,

[0293] naphthobenzothienyl,

[0294] Benzothiazolyl,

[0295] Benzisothiazolyl,

[0296] Phenothiazine,

[0297] dinaphthothiophenyl,

[0298] azadibenzothienyl,

[0299] diazadibenzothienyl,

[0300] azanaphthobenzothienyl,

[0301] diazanaphthobenzothienyl.

[0302] 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):

[0303] [Chemistry 6]

[0304]

[0305] [Chemistry 7]

[0306]

[0307] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each independently represents an oxygen atom, a sulfur atom, NH or CH2. A and Y A At least one of them is an oxygen atom, a sulfur atom or NH.

[0308] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A When at least one of is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the above-mentioned general formula (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0309] Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):

[0310] (9-phenyl)carbazolyl,

[0311] (9-biphenyl)carbazolyl,

[0312] (9-phenyl)phenylcarbazolyl,

[0313] (9-naphthyl)carbazolyl,

[0314] Diphenylcarbazole-9-yl,

[0315] Phenylcarbazol-9-yl,

[0316] Methylbenzimidazolyl,

[0317] Ethylbenzimidazolyl,

[0318] Phenyl triazine,

[0319] Biphenyl triazine,

[0320] Diphenyltriazine,

[0321] Phenylquinazolinyl, and

[0322] Biphenylquinazolinyl.

[0323] Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0324] Phenyldibenzofuranyl,

[0325] Methyldibenzofuranyl,

[0326] tert-Butyldibenzofuranyl, and

[0327] The monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0328] Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

[0329] Phenyldibenzothiophene,

[0330] Methyldibenzothiophene,

[0331] tert-Butyldibenzothienyl, and

[0332] The monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0333] A group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) are replaced by a substituent (specific example group G2B4):

[0334] The aforementioned "one or more hydrogen atoms of the monovalent heterocyclic group" refers to hydrogen atoms bonded to the ring-constituting carbon atoms of the monovalent heterocyclic group, X A and Y A when at least one of X is NH, a hydrogen atom bonded to a nitrogen atom, and X A and Y A When one side is CH2, one or more hydrogen atoms among the hydrogen atoms of the methylene group.

[0335] "Substituted or unsubstituted alkyl"

[0336] As specific examples of the "substituted or unsubstituted alkyl group" described in this specification (specific example group G3), the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B) can be cited (herein, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group", and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group"). Hereinafter, when "alkyl" is mentioned alone, both "unsubstituted alkyl group" and "substituted alkyl group" are included.

[0337] "Substituted alkyl" means 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 substituents, and examples of substituted alkyl (specific example group G3B) can be cited. In this specification, the alkyl group in "unsubstituted alkyl" means a chain alkyl group. Therefore, "unsubstituted alkyl" includes straight-chain "unsubstituted alkyl" and branched "unsubstituted alkyl". It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples, and the "substituted alkyl" recorded in this 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 substituents, and groups in which the hydrogen atoms of the substituents in the "substituted alkyl" of the specific example group G3B are further replaced by substituents.

[0338] Unsubstituted alkyl (specific example group G3A):

[0339] methyl,

[0340] Ethyl,

[0341] n-propyl,

[0342] Isopropyl,

[0343] n-Butyl,

[0344] Isobutyl,

[0345] sec-butyl, and

[0346] Tert-butyl.

[0347] Substituted alkyl (specific example group G3B):

[0348] Heptafluoropropyl (including isomers),

[0349] Pentafluoroethyl,

[0350] 2,2,2-trifluoroethyl, and

[0351] Trifluoromethyl.

[0352] "Substituted or unsubstituted alkenyl"

[0353] Specific examples of the "substituted or unsubstituted alkenyl group" described in the present specification (specific example group G4) include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B) (herein, the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group", and the "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group"). In the present specification, when "alkenyl group" is mentioned alone, both "unsubstituted alkenyl group" and "substituted alkenyl group" are included.

[0354] "Substituted alkenyl" means 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) having a substituent, 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 a group 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 a group in which the hydrogen atoms of the substituent in the "substituted alkenyl" of the specific example group G4B are further replaced by a substituent.

[0355] Unsubstituted alkenyl (specific example group G4A):

[0356] Vinyl,

[0357] Allyl,

[0358] 1-Butenyl,

[0359] 2-Butenyl, and

[0360] 3-Butenyl.

[0361] Substituted alkenyl (specific example group G4B):

[0362] 1,3-Butadienyl,

[0363] 1-Methylvinyl,

[0364] 1-methylallyl,

[0365] 1,1-dimethylallyl,

[0366] 2-methylallyl, and

[0367] 1,2-Dimethylallyl.

[0368] "Substituted or unsubstituted alkynyl"

[0369] As specific examples of the "substituted or unsubstituted alkynyl group" described in the present specification (specific example group G5), the following unsubstituted alkynyl group (specific example group G5A) and the like can be cited (herein, the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group"). Hereinafter, when "alkynyl group" is mentioned alone, both "unsubstituted alkynyl group" and "substituted alkynyl group" are included.

[0370] "Substituted alkynyl" means 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.

[0371] Unsubstituted alkynyl (specific example group G5A):

[0372] Ethylene

[0373] "Substituted or unsubstituted cycloalkyl"

[0374] Specific examples of the "substituted or unsubstituted cycloalkyl group" described in the present specification (specific example group G6) include the following unsubstituted cycloalkyl groups (specific example group G6A) and substituted cycloalkyl groups (specific example group G6B) (herein, unsubstituted cycloalkyl groups refer to the case where "substituted or unsubstituted cycloalkyl groups" are "unsubstituted cycloalkyl groups", and substituted cycloalkyl groups refer to the case where "substituted or unsubstituted cycloalkyl groups" are "substituted cycloalkyl groups"). In the present specification, when "cycloalkyl groups" are mentioned alone, both "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" are included.

[0375] "Substituted cycloalkyl" means 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 a 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 a 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.

[0376] Unsubstituted cycloalkyl (specific example group G6A):

[0377] Cyclopropyl,

[0378] Cyclobutyl,

[0379] Cyclopentyl,

[0380] Cyclohexyl,

[0381] 1-adamantyl,

[0382] 2-adamantyl,

[0383] 1-Norbornyl, and

[0384] 2-Norbornyl.

[0385] Substituted cycloalkyl (specific example group G6B):

[0386] 4-Methylcyclohexyl.

[0387] ·“-Si(R 901 )(R 902 )(R 903 )"

[0388] As described in this specification, -Si(R 901 )(R 902 )(R 903 ) Specific examples of the group represented by (specific example group G7) include:

[0389] -Si(G1)(G1)(G1),

[0390] -Si(G1)(G2)(G2),

[0391] -Si(G1)(G1)(G2),

[0392] -Si(G2)(G2)(G2),

[0393] -Si(G3)(G3)(G3), and

[0394] -Si(G6)(G6)(G6).

[0395] in,

[0396] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0397] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0398] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0399] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0400] A plurality of G1's in -Si(G1)(G1)(G1) are the same or different.

[0401] The multiple G2s in -Si(G1)(G2)(G2) are the same or different.

[0402] The plurality of G1's in -Si(G1)(G1)(G2) are the same or different.

[0403] Multiple G2s in -Si(G2)(G2)(G2) are the same or different.

[0404] Multiple G3 in -Si(G3)(G3)(G3) are the same or different.

[0405] Multiple G6's in -Si(G6)(G6)(G6) are the same or different.

[0406] ·“-O-(R 904 )"

[0407] As described in this specification, -O-(R 904 ) Specific examples of the group represented by (specific example group G8) include:

[0408] -O(G1),

[0409] -O(G2),

[0410] -O(G3), and

[0411] -O(G6).

[0412] in,

[0413] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0414] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0415] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0416] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0417] ·“-S-(R 905 )"

[0418] As described in this specification, -S-(R 905 ) are represented by (specific example group G9), and include:

[0419] -S(G1),

[0420] -S(G2),

[0421] -S(G3), and

[0422] -S(G6).

[0423] in,

[0424] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0425] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0426] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0427] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0428] ·“-N(R 906 )(R 907 )"

[0429] As described in this specification, -N(R 906 )(R 907 ) are represented by (specific example group G10):

[0430] -N(G1)(G1),

[0431] -N(G2)(G2),

[0432] -N(G1)(G2),

[0433] -N(G3)(G3), and

[0434] -N(G6)(G6).

[0435] in,

[0436] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0437] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0438] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0439] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0440] - The multiple G1s in N(G1)(G1) are the same or different.

[0441] - The multiple G2s in N(G2)(G2) are the same or different.

[0442] - The multiple G3 in N(G3)(G3) are the same or different.

[0443] Multiple G6's in -N(G6)(G6) are the same or different.

[0444] "Halogen atoms"

[0445] 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.

[0446] "Substituted or unsubstituted fluoroalkyl"

[0447] The "substituted or unsubstituted fluoroalkyl group" described in the present specification means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced by fluorine atoms (perfluoro group). The number of carbon atoms in 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" means a group in which one or more hydrogen atoms of the "fluoroalkyl group" are replaced by 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 the alkyl chain in the "substituted fluoroalkyl group" are further replaced by a substituent, and a group in which one or more hydrogen atoms of a substituent in the "substituted fluoroalkyl group" are further replaced by 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 by fluorine atoms.

[0448] "Substituted or unsubstituted haloalkyl"

[0449] The "substituted or unsubstituted haloalkyl" described in the present specification means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl" is replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl" are replaced by halogen atoms. The number of carbon atoms in the "unsubstituted haloalkyl" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification. The "substituted haloalkyl" means a group in which one or more hydrogen atoms of the "haloalkyl" are replaced by a substituent. It should be noted that the "substituted haloalkyl" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the "substituted haloalkyl" are further replaced by a substituent, and a group in which one or more hydrogen atoms of a substituent in the "substituted haloalkyl" are further replaced by a substituent. Specific examples of "unsubstituted haloalkyl" include groups in which one or more hydrogen atoms in the aforementioned "alkyl" (specific example group G3) are replaced by halogen atoms. A haloalkyl group may be referred to as a halogenated alkyl group.

[0450] "Substituted or unsubstituted alkoxy"

[0451] As a specific example of the "substituted or unsubstituted alkoxy group" described in the present specification, there is a group represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms in 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.

[0452] "Substituted or unsubstituted alkylthio"

[0453] 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 number of carbon atoms in 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.

[0454] "Substituted or unsubstituted aryloxy"

[0455] 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.

[0456] "Substituted or unsubstituted arylthio"

[0457] 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.

[0458] "Substituted or unsubstituted trialkylsilyl"

[0459] 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. Multiple G3s in -Si(G3)(G3)(G3) may be the same or different. The number of carbon atoms of 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.

[0460] "Substituted or unsubstituted aralkyl"

[0461] A specific example of the "substituted or unsubstituted aralkyl group" described in the present specification is a group represented by -(G3)-(G1), where 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 form of the "substituted alkyl group". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the number of carbon atoms 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.

[0462] 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.

[0463] 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, triphenylene, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl and 9,9-diphenylfluorenyl, etc.

[0464] 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 naphthiobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthiobenzofuranyl group, a benzothiophenyl ... benzothiophenyl, azadibenzothiophenyl, diazadibenzothiophenyl, (9-phenyl)carbazolyl ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl, or (9-phenyl)carbazol-4-yl), (9-biphenyl)carbazolyl, (9-phenyl)phenylcarbazolyl, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazine, biphenyltriazine, diphenyltriazine, phenyldibenzofuranyl, and phenyldibenzothiophenyl, etc.

[0465] In the present specification, the carbazolyl group is specifically any of the following groups unless otherwise described in the present specification.

[0466] [Chemistry 8]

[0467]

[0468] In the present specification, the (9-phenyl)carbazolyl group is specifically any of the following groups unless otherwise specified in the present specification.

[0469] [Chemistry 9]

[0470]

[0471] In the aforementioned general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding site.

[0472] 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.

[0473] [Chemistry 10]

[0474]

[0475] In the aforementioned general formulae (TEMP-34) to (TEMP-41), * represents a bonding site.

[0476] Unless otherwise specified in the present specification, 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.

[0477] "Substituted or unsubstituted arylene group"

[0478] The "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group" unless otherwise described. Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1.

[0479] "Substituted or unsubstituted divalent heterocyclic group"

[0480] 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.

[0481] "Substituted or unsubstituted alkylene"

[0482] Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group". Specific examples of the "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3.

[0483] 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.

[0484] [Chemistry 11]

[0485]

[0486] [Chemistry 12]

[0487]

[0488] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0489] In the aforementioned general formulae (TEMP-42) to (TEMP-52), * represents a bonding site.

[0490] [Chemistry 13]

[0491]

[0492] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0493] Formula Q9 and Q 10 They may be bonded to each other via a single bond to form a ring.

[0494] In the aforementioned general formulae (TEMP-53) to (TEMP-62), * represents a bonding site.

[0495] [Chemistry 14]

[0496]

[0497] In the aforementioned general formulae (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0498] In the aforementioned general formulae (TEMP-63) to (TEMP-68), * represents a bonding site.

[0499] 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.

[0500] [Chemistry 15]

[0501]

[0502] [Chemistry 16]

[0503]

[0504] [Chemistry 17]

[0505]

[0506] In the aforementioned general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0507] [Chemistry 18]

[0508]

[0509] [Chemistry 19]

[0510]

[0511] [Chemistry 20]

[0512]

[0513] [Chemistry 21]

[0514]

[0515] In the aforementioned general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0516] The above is the description of the “substituents described in the present specification”.

[0517] "Bonds forming a ring"

[0518] In the present specification, the situation that "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 situation that "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 situation that "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 situation that "one or more groups consisting of two or more adjacent groups are not bonded to each other".

[0519] 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.

[0520] [Chemistry 22]

[0521]

[0522] For example, R 921 ~R 930 In the case of "one or more groups consisting of two or more adjacent groups are bonded to each other to form a ring", one group consisting of two adjacent groups is 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.

[0523] The above “one or more groups” means that two or more 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 In the case of, the anthracene compound represented by the aforementioned general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0524] [Chemistry 23]

[0525]

[0526] The case where "a group of two or more adjacent members" forms a ring includes not only the case where the adjacent "two" members are bonded as in the above example, but also the case where the adjacent "three or more" members 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 form an 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 .

[0527] [Chemistry 24]

[0528]

[0529] The "monocyclic ring" or "condensed ring" formed as a structure of a ring formed alone may be a saturated ring or an unsaturated ring. Even when "a group consisting of two adjacent groups" forms a "monocyclic ring" or a "condensed ring", the "monocyclic ring" or "condensed ring" may form a saturated ring or an unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104) 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 (TMEP-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 (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a condensed ring.

[0530] The "unsaturated ring" includes, in addition to aromatic hydrocarbon rings and aromatic heterocyclic rings, aliphatic hydrocarbon rings having unsaturated bonds, i.e., double bonds and / or triple bonds in the ring structure (e.g., cyclohexene, cyclohexadiene, etc.), and non-aromatic heterocyclic rings having unsaturated bonds (e.g., dihydropyran, imidazoline, pyrazoline, quinolizine, indoline, isoindoline, etc.). The "saturated ring" includes aliphatic hydrocarbon rings without unsaturated bonds, or non-aromatic heterocyclic rings without unsaturated bonds.

[0531] Specific examples of the aromatic hydrocarbon ring include structures in which the groups listed as specific examples in Specific Example Group G1 are terminated with hydrogen atoms.

[0532] Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups listed as specific examples in Specific Example Group G2 are terminated with hydrogen atoms.

[0533] Specific examples of the aliphatic hydrocarbon ring include structures in which the groups listed as specific examples in Specific Example Group G6 are terminated with hydrogen atoms.

[0534] "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 arbitrary atoms. For example, R 921 With R 922 The ring Q formed by mutual bonding A Meaning by R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 As a specific example, in the case where R 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.

[0535] Here, "any atom" is preferably at least one atom selected from carbon atom, nitrogen atom, oxygen atom and sulfur atom unless otherwise described in this specification. For any atom (such as carbon atom or nitrogen atom), the bond that does not form a ring may be terminated by hydrogen atom or the like, or may be substituted by "any substituent" described later. When any atom other than carbon atom is included, the formed ring is a heterocycle.

[0536] Unless otherwise specified in the present specification, the number of "one or more arbitrary atoms" 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.

[0537] Unless otherwise specified in the present specification, "monocyclic ring" is preferred over "monocyclic ring" and "condensed ring".

[0538] In the present specification, unless otherwise specified, of "saturated ring" and "unsaturated ring", "unsaturated ring" is preferred.

[0539] Unless otherwise specified in the present specification, a "monocyclic ring" is preferably a benzene ring.

[0540] Unless otherwise specified in the present specification, the "unsaturated ring" is preferably a benzene ring.

[0541] 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 monocyclic ring", or "bonded to each other to form a substituted or unsubstituted condensed ring", unless otherwise stated in the present specification, it is preferred that one or more groups consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted "unsaturated ring" consisting of multiple atoms of the parent skeleton and one or more and fifteen or less atoms selected from carbon atoms, nitrogen atoms, oxygen atoms and sulfur atoms.

[0542] 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".

[0543] 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".

[0544] The above is an explanation of 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" and 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" ("the case where they are bonded to form a ring").

[0545] ·Substituents in the case of "substituted or unsubstituted"

[0546] In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituent" in the present specification) is, for example, a group selected from the following groups, etc.:

[0547] unsubstituted alkyl group having 1 to 50 carbon atoms,

[0548] unsubstituted alkenyl having 2 to 50 carbon atoms,

[0549] unsubstituted alkynyl having 2 to 50 carbon atoms,

[0550] unsubstituted cycloalkyl having 3 to 50 ring carbon atoms,

[0551] -Si(R 901 )(R 902 )(R 903 ),

[0552] -O-(R 904 ),

[0553] -S-(R 905 ),

[0554] -N(R 906 )(R 907 ),

[0555] Halogen atoms, cyano, nitro,

[0556] an unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0557] An unsubstituted heterocyclic group having 5 to 50 ring atoms;

[0558] Here, R 901 ~R 907 Each independently is:

[0559] Hydrogen atoms,

[0560] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0561] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0562] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0563] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0564] R 901 When there are two or more, two or more R 901 Same or different from each other,

[0565] R 902 When there are two or more, two or more R 902 Same or different from each other,

[0566] R 903 When there are two or more, two or more R 903 Same or different from each other,

[0567] R 904 When there are two or more, two or more R904 Same or different from each other,

[0568] R 905 When there are two or more, two or more R 905 Same or different from each other,

[0569] R 906 When there are two or more, two or more R 906 Same or different from each other,

[0570] R 907 When there are two or more, two or more R 907 Same as or different from each other.

[0571] In one embodiment, the substituent in the aforementioned "substituted or unsubstituted" case is selected from the following groups:

[0572] Alkyl groups having 1 to 50 carbon atoms,

[0573] an aryl group having 6 to 50 ring carbon atoms, and

[0574] A heterocyclic group having 5 to 50 ring atoms.

[0575] In one embodiment, the substituent in the aforementioned "substituted or unsubstituted" case is selected from the following groups:

[0576] Alkyl groups having 1 to 18 carbon atoms,

[0577] an aryl group having 6 to 18 ring carbon atoms, and

[0578] A heterocyclic group having 5 to 18 ring atoms.

[0579] Specific examples of each of the above-mentioned optional substituents are the same as the specific examples of the substituents described in the above section "Substituents described in the present specification".

[0580] Unless otherwise stated in this specification, any adjacent substituents may form a "saturated ring" or an "unsaturated ring" with each other, preferably forming a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably forming a benzene ring.

[0581] Unless otherwise specified in the present specification, an arbitrary substituent may further have a substituent. The substituent further possessed by the arbitrary substituent is the same as the above-mentioned arbitrary substituent.

[0582] 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.

[0583] [New Compounds]

[0584] The compound of one embodiment of the present invention is represented by the following formula (101).

[0585] [Chemistry 25]

[0586]

[0587] [In formula (101),

[0588] Either one of X1 and X2 is N, and the other is CH.

[0589] R1~R 10 Each is independently a hydrogen atom or a substituent R. A group consisting of two or more adjacent R1 to R5 is not bonded to each other. 10 The adjacent groups of two or more are not bonded to each other.

[0590] n1 is an integer from 0 to 3.

[0591] When n1 is 0, the structure in the brackets involving n1 is a single bond.

[0592] When n1 is 2 or 3, the structures within the multiple brackets related to n1 may be the same or different.

[0593] R 11 is a hydrogen atom or a substituent R. 4 R 11 They can be the same or different from each other. 11 The adjacent groups of two or more are not bonded to each other.

[0594] n2 is an integer from 0 to 3.

[0595] When n2 is 0, the structure in the brackets involving n2 is a single bond.

[0596] When n2 is 2 or 3, the structures within the multiple brackets involving n2 may be the same or different.

[0597] R 21 is a hydrogen atom or a substituent R. 4 R 21 They can be the same or different from each other. 21 The adjacent groups of two or more are not bonded to each other.

[0598] n101 is 0 or 1.

[0599] When n101 is 0, the structure in the brackets related to n101 is a single bond.

[0600] L1 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.

[0601] R 101 ~R 108 1 in represents the same as (L1) n101 It does not represent the single bond of (L1) n101 The single bond R 101 ~R 108 One of them represents a single bond with the nitrogen atom of the carbazole structure.

[0602] R not representing the single bond 101 ~R 108 Each is independently a hydrogen atom or a substituent R. 101 ~R 108 The adjacent groups of two or more are not bonded to each other.

[0603] By R 201 ~R 208 One or more groups of two or more adjacent ones of the moieties may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring, or may not be bonded to each other.

[0604] R not bonded to each other 201 ~R 208 Each is independently a hydrogen atom or a substituent R.

[0605] The substituent R is selected from

[0606] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0607] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0608] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0609] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0610] -Si(R 901 )(R 902 )(R 903 ),

[0611] -O-(R 904 ),

[0612] -S-(R 905 ),

[0613] -N(R 906 )(R 907 ),

[0614] Halogen atoms, cyano, nitro,

[0615] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0616] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0617] When there are two or more substituents R, the two or more substituents R may be the same as or different from each other.

[0618] R 901 ~R 907 Each independently

[0619] Hydrogen atoms,

[0620] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0621] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0622] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0623] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0624] R 901 ~R 907 When there are two or more of each, the two or more R 901 ~R 907 Can be the same or different. ].

[0625] The structure in the brackets regarding n1 in formula (101), that is, the structure represented by the following formula (111), will be described.

[0626] [Chemistry 26]

[0627]

[0628] The structure represented by formula (111) means that two of the six carbon atoms of the benzene ring are bonded to the adjacent structure by single bonds, and the remaining four carbon atoms are bonded to R 11 .

[0629] In other words, the structure represented by the above formula (111) can adopt three structures represented by the following formulas (111a) to (111c).

[0630] [Chemistry 27]

[0631]

[0632] (In formulae (111a) to (111c), *1 and *2 represent single bonds to adjacent structures. R 11 As defined in the above formula (101). ).

[0633] For example, when n1 is 3 and the order of the structure represented by formula (111c), the structure represented by formula (111b), and the structure represented by formula (111a) from the pyrimidine structure side in formula (101) is as follows, the overall structure is as follows.

[0634] [Chemistry 28]

[0635]

[0636] (In the above formula, *11 represents a single bond with the pyrimidine structure. *21 represents a single bond with the phenyl group. R 11 As defined in the above formula (101). ).

[0637] It should be noted that, as is obvious from the definition, when n1 is 0 in formula (101), the structure represented by formula (111) does not exist, and the pyrimidine structure and the phenyl group are directly bonded via a single bond.

[0638] The same applies to the structure in brackets involving n2 in formula (101), that is, the structure represented by the following formula (211).

[0639] [Chemistry 29]

[0640]

[0641] Specifically, the structure represented by formula (211) means that two of the six carbon atoms of the benzene ring are bonded to the adjacent structure by single bonds, and the remaining four carbon atoms are bonded to R 21 .

[0642] In other words, the structure represented by the above formula (211) can adopt three structures represented by the following formulas (211a) to (211c).

[0643] [Chemistry 30]

[0644]

[0645] [In formulae (211a) to (211c), *1 and *2 each represent a single bond with an adjacent structure. 21 As defined in formula (101) above. ].

[0646] It should be noted that, as is obvious from the definition, when n2 is 0 in formula (101), the structure represented by formula (211) does not exist, and the pyrimidine structure and the phenyl group are directly bonded via a single bond.

[0647] When n101 is 0, the structure in the brackets related to n101 is a single bond.

[0648] It should be noted that, as is obvious from the definition, when n101 is 0, the pyrimidine structure and the naphthalene structure are directly bonded to each other via a single bond.

[0649] In one embodiment, X1 is N and X2 is CH.

[0650] In one embodiment, X1 is CH and X2 is N.

[0651] In one embodiment, R 11 A hydrogen atom.

[0652] In one embodiment, R 21 A hydrogen atom.

[0653] In one embodiment, n1 and n2 are each independently 0 or 1.

[0654] In one embodiment, n1 and n2 are 0.

[0655] In one embodiment, n1 is 0 and n2 is 1.

[0656] In one embodiment, R1 to R 10 A hydrogen atom.

[0657] In one embodiment, L1 is substituted or unsubstituted phenylene.

[0658] In one embodiment, R 102 represents a single bond to L1.

[0659] In one embodiment, R 107 represents a single bond to the nitrogen atom of the carbazole structure.

[0660] In one embodiment, R not representing a single bond 101 ~R 108 A hydrogen atom.

[0661] It is obvious from the definition that R 101 ~R 108 One of them and R 201 ~R 208 That is, in formula (101), the naphthalene skeleton and the carbazole skeleton do not form a ring.

[0662] In one embodiment, R 201 ~R 208 One or more groups of two or more adjacent ones are not bonded to each other.

[0663] In one embodiment, R 201 ~R 208 A hydrogen atom.

[0664] In one embodiment, the compound represented by the above formula (101) is a compound represented by the following formula (1).

[0665] [Chemistry 31]

[0666]

[0667] [In formula (1),

[0668] R1~R 10 Each is independently a hydrogen atom or a substituent R. A group consisting of two or more adjacent R1 to R5 is not bonded to each other. 10 The adjacent groups of two or more are not bonded to each other.

[0669] n1 is an integer from 0 to 3.

[0670] When n1 is 0, the structure in the brackets involving n1 is a single bond.

[0671] When n1 is 2 or 3, the structures within the multiple brackets related to n1 may be the same or different.

[0672] R 11 is a hydrogen atom or a substituent R. 4 R 11 They can be the same or different from each other. 11 The adjacent groups of two or more are not bonded to each other.

[0673] n2 is an integer from 0 to 3.

[0674] When n2 is 0, the structure in the brackets involving n2 is a single bond.

[0675] When n2 is 2 or 3, the structures within the multiple brackets involving n2 may be the same or different.

[0676] R 21 is a hydrogen atom or a substituent R. 4 R 21 They can be the same or different from each other. 21 The adjacent groups of two or more are not bonded to each other.

[0677] L1 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.

[0678] R 101 ~R 108 One of them represents a single bond with L1. R that does not represent a single bond with L1 101 ~R 108One of them represents a single bond with the nitrogen atom of the carbazole structure.

[0679] R not representing the single bond 101 ~R 108 Each is independently a hydrogen atom or a substituent R. 101 ~R 108 The adjacent groups of two or more are not bonded to each other.

[0680] By R 201 ~R 208 One or more groups of two or more adjacent ones of the moieties may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring, or may not be bonded to each other.

[0681] R not bonded to each other 201 ~R 208 Each is independently a hydrogen atom or a substituent R.

[0682] The substituent R is selected from

[0683] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0684] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0685] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0686] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0687] -Si(R 901 )(R 902 )(R 903 ),

[0688] -O-(R 904 ),

[0689] -S-(R 905 ),

[0690] -N(R 906 )(R 907 ),

[0691] Halogen atoms, cyano, nitro,

[0692] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0693] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0694] When there are two or more substituents R, the two or more substituents R may be the same as or different from each other.

[0695] R 901 ~R907 Each independently

[0696] Hydrogen atoms,

[0697] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0698] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0699] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0700] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0701] R 901 ~R 907 When there are two or more of each, the two or more R 901 ~R 907 Can be the same or different. ].

[0702] In one embodiment, R in formula (1) 11 A hydrogen atom.

[0703] In one embodiment, R in formula (1) 21 A hydrogen atom.

[0704] In one embodiment, n1 and n2 in formula (1) are 0.

[0705] In one embodiment, R1 to R 10 A hydrogen atom.

[0706] In one embodiment, L1 in formula (1) is a substituted or unsubstituted phenylene group.

[0707] In one embodiment, R in formula (1) 102 represents a single bond to L1.

[0708] In one embodiment, R in formula (1) 107 represents a single bond to the nitrogen atom of the carbazole structure.

[0709] In one embodiment, R in formula (1) that does not represent a single bond 101 ~R 108 A hydrogen atom.

[0710] It is obvious from the definition that R 101 ~R 108 One of them and R 201 ~R 208 That is, in formula (1), the naphthalene skeleton and the carbazole skeleton do not form a ring.

[0711] In one embodiment, R in formula (1) 201 ~R 208 One or more groups of two or more adjacent ones are not bonded to each other.

[0712] In one embodiment, R in formula (1) 201 ~R 208 A hydrogen atom.

[0713] In one embodiment, the compound represented by formula (1) is a compound represented by the following formula (11).

[0714] [Chemistry 32]

[0715]

[0716] [In formula (11),

[0717] R1~R 10 , R 11 , R 21 , n1, n2 and R 201 ~R 208 As defined in formula (1).

[0718] R 31 is a hydrogen atom or a substituent R. 4 R 31 Can be the same or different. 31 The adjacent groups of two or more are not bonded to each other.

[0719] R 111 ~R 116 Each is independently a hydrogen atom or a substituent R. 111 ~R 116 The adjacent groups of two or more are not bonded to each other.

[0720] The substituent R is as defined in the formula (1). ]

[0721] For R in formula (11) 31 The bonded phenylene structure, that is, the structure represented by the following formula (311) will be described.

[0722] [Chemistry 33]

[0723]

[0724] The structure represented by the above formula (311) means that two of the six carbon atoms of the benzene ring are bonded to the adjacent structure by single bonds, and the remaining four carbon atoms are bonded to R 31 .

[0725] In other words, the structure represented by formula (311) can adopt three structures represented by the following formulas (311a) to (311c).

[0726] [Chemistry 34]

[0727]

[0728] (In formulae (311a) to (311c), *31 represents a single bond to an adjacent pyrimidine structure, and *32 represents a single bond to an adjacent naphthalene skeleton. R 31 As defined in the above formula (11).

[0729] For example, when the structure represented by formula (311) is the structure represented by formula (311c), the compound represented by formula (11) is represented by the following formula (11c).

[0730] [Chemistry 35]

[0731]

[0732] (In formula (11c), R1~R 10 , R 11 , R 21 , R 31 , R 111 ~R 116 , n1, n2, and R 201 ~R 208 As defined in the above formula (11).

[0733] In one embodiment, R 31 A hydrogen atom.

[0734] In one embodiment, R 111 ~R 116 A hydrogen atom.

[0735] In one embodiment, the compound represented by the above formula (101) is a compound represented by the following formula (2).

[0736] [Chemistry 36]

[0737]

[0738] [In formula (2),

[0739] R1~R 10 Each is independently a hydrogen atom or a substituent R. A group consisting of two or more adjacent R1 to R5 is not bonded to each other. 10 The adjacent groups of two or more are not bonded to each other.

[0740] n1 is an integer from 0 to 3.

[0741] When n1 is 0, the structure in the brackets involving n1 is a single bond.

[0742] When n1 is 2 or 3, the structures within the multiple brackets related to n1 may be the same or different.

[0743] R 11 is a hydrogen atom or a substituent R. 4 R 11 They can be the same or different from each other. 11 The adjacent groups of two or more are not bonded to each other.

[0744] n2 is an integer from 1 to 3.

[0745] When n2 is 2 or 3, the structures within the multiple brackets involving n2 may be the same or different.

[0746] R 21 is a hydrogen atom or a substituent R. 4 R 21 They can be the same or different from each other. 21 The adjacent groups of two or more are not bonded to each other.

[0747] R 101 ~R 108 One of them represents a single bond to a carbon atom of a pyrimidine structure. R that does not represent a single bond to a carbon atom of a pyrimidine structure 101 ~R 108 One of them represents a single bond with the nitrogen atom of the carbazole structure.

[0748] R not representing the single bond 101 ~R 108 Each is independently a hydrogen atom or a substituent R. 101 ~R 108 The adjacent groups of two or more are not bonded to each other.

[0749] By R 201 ~R 208 One or more groups of two or more adjacent ones of the moieties may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring, or may not be bonded to each other.

[0750] R not bonded to each other 201 ~R 208 Each is independently a hydrogen atom or a substituent R.

[0751] The substituent R is selected from:

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

[0757] -O-(R 904 ),

[0758] -S-(R 905 ),

[0759] -N(R 906 )(R 907 ),

[0760] Halogen atoms, cyano, nitro,

[0761] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0762] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0763] When there are two or more substituents R, the two or more substituents R may be the same as or different from each other.

[0764] R 901 ~R 907 Each independently

[0765] Hydrogen atoms,

[0766] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0767] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0768] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0769] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0770] R 901 ~R 907 When there are two or more of each, the two or more R 901 ~R 907 Can be the same or different. ].

[0771] In one embodiment, R in formula (2) 102 Represents a single bond to the carbon atom of the pyrimidine structure, R 107 represents a single bond to the nitrogen atom of the carbazole structure.

[0772] In one embodiment, R in formula (2) 201 ~R 208 One or more groups of two or more adjacent ones are not bonded to each other.

[0773] In one embodiment, the compound represented by the above formula (2) is a compound represented by the following formula (21).

[0774] [Chemistry 37]

[0775]

[0776] [In formula (21),

[0777] R1~R 10 , R 11 , R 21 , n1, n2 and R 201 ~R 208 As defined in formula (2).

[0778] R 211 ~R 216 Each is independently a hydrogen atom or a substituent R. 211 ~R 216 The adjacent groups of two or more are not bonded to each other.

[0779] The substituent R is as defined in the formula (2). ]

[0780] In one embodiment, n1 in formula (2) is 0.

[0781] In one embodiment, R1 to R 10 A hydrogen atom.

[0782] In one embodiment, R in formula (2) 201 ~R 208 Any one of is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0783] R 201 ~R 208 The rest are each independently selected from:

[0784] Hydrogen atoms,

[0785] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0786] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0787] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0788] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0789] -Si(R 901 )(R 902 )(R 903 ),

[0790] -O-(R 904 ),

[0791] -S-(R 905 ),

[0792] -N(R 906 )(R 907 ),

[0793] Halogen atoms, cyano, nitro, and

[0794] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0795] In one embodiment, R in formula (2) 203 It is a substituted or unsubstituted aryl group having 1 to 50 ring carbon atoms.

[0796] In one embodiment, R in formula (2) 203 is substituted or unsubstituted phenyl.

[0797] In one embodiment, R in formula (2) 201 ~R 202 and R 204 ~R 208 A hydrogen atom.

[0798] In one embodiment, R in formula (2) 211 ~R 216 A hydrogen atom.

[0799] In one embodiment, the "substituted or unsubstituted" substituent and the substituent R are each independently selected from an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and a monovalent heterocyclic group having 5 to 50 ring atoms.

[0800] In one embodiment, the "substituted or unsubstituted" substituent and the substituent R are each independently selected from an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a monovalent heterocyclic group having 5 to 18 ring atoms.

[0801] In one embodiment, the compound represented by formula (101) does not have a deuterium atom as a hydrogen atom in the molecule.

[0802] In this specification, "does not have deuterium atoms as hydrogen atoms" means that the ratio of deuterium atoms to the total of protium atoms and deuterium atoms in all hydrogen atoms in the molecule is less than the naturally occurring ratio. In other words, the compound of one embodiment of the present invention that does not have deuterium atoms as hydrogen atoms in the molecule may contain deuterium atoms at a ratio less than the naturally occurring ratio.

[0803] It can be confirmed by a nuclear magnetic resonance apparatus that the ratio of deuterium atoms to the total of protium atoms and deuterium atoms is lower than the naturally occurring ratio.

[0804] In one embodiment, the compound represented by formula (101) has at least one deuterium atom as a hydrogen atom in the molecule.

[0805] In one embodiment, R as a substituent R 201 ~R 208 Having at least one deuterium atom.

[0806] In this specification, "having deuterium atoms as hydrogen atoms" means that the ratio of deuterium atoms to the total of protium atoms and deuterium atoms in the hydrogen atoms is greater than that in nature. It can be confirmed by a nuclear magnetic resonance device that the ratio of deuterium atoms to the total of protium atoms and deuterium atoms is greater than that in nature.

[0807] The compound represented by formula (101) can be synthesized according to the examples using known substitution reactions and starting materials suitable for the target product.

[0808] Specific examples of the compound represented by formula (101) are described below, but these are merely examples and the compound represented by formula (101) is not limited to the following specific examples.

[0809] [Chemistry 38]

[0810]

[0811] [Chemistry 39]

[0812]

[0813] [Chemistry 40]

[0814]

[0815] [Chemistry 41]

[0816]

[0817] [Chemistry 42]

[0818]

[0819] [Chemistry 43]

[0820]

[0821] [Materials for organic electroluminescent devices]

[0822] The composition according to one embodiment of the present invention is useful as a material for an organic EL device, for example, as a material used in an electron transport region of an organic EL device.

[0823] [Organic EL element]

[0824] An organic EL element according to one embodiment of the present invention will be described.

[0825] The organic EL element according to one embodiment of the present invention comprises a cathode, an anode, and one or more organic layers arranged between the cathode and the anode, and at least one of the organic layers contains the compound according to one embodiment of the present invention (the compound represented by formula (1)).

[0826] In one embodiment, the organic EL device according to one embodiment of the present invention preferably comprises an anode, a light-emitting layer, an electron-transporting region, and a cathode in this order, and the electron-transporting region comprises the compound according to one embodiment of the present invention (the compound represented by formula (1)).

[0827] In one embodiment, the electron transport region has a first layer (also referred to as a "first electron transport layer" or a "hole blocking layer") and a second layer (also referred to as a "second electron transport layer") in order from the light-emitting layer side, and the first layer contains a compound represented by formula (1). As the second layer in this case, for example, the structure of the electron transport layer described later can be applied.

[0828] As a typical element structure of this organic EL element, a structure in which the following structure is stacked on a substrate can be exemplified.

[0829] (1) Anode / light-emitting layer / electron transport region / cathode

[0830] (2) Anode / hole transport region / light-emitting layer / electron transport region / cathode

[0831] (“ / ” indicates that the layers are adjacent and stacked.)

[0832] The electron transport region generally includes one or more layers selected from the group consisting of an electron injection layer and an electron transport layer. The hole transport region generally includes one or more layers selected from the group consisting of a hole injection layer and a hole transport layer.

[0833] Reference Figure 1 A schematic configuration of an organic EL element according to one embodiment of the present invention will be described.

[0834] An organic EL element 1 according to one embodiment of the present invention includes a substrate 2 , an anode 3 , a light-emitting layer 5 , a cathode 10 , a hole transport region 4 between the anode 3 and the light-emitting layer 5 , and an electron transport region 6 between the light-emitting layer 5 and the cathode 10 .

[0835] Hereinafter, members that can be used in the organic EL device of one embodiment of the present invention and materials other than the above-mentioned compounds constituting each layer will be described.

[0836] (Substrate)

[0837] The substrate is used as a support for the light-emitting element. As the substrate, for example, glass, quartz, plastic, etc. can be used. In addition, a flexible substrate can also be used. A flexible substrate refers to a (flexible) substrate that can be bent, and examples thereof include a plastic substrate formed of polycarbonate, polyvinyl chloride, etc.

[0838] (anode)

[0839] 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, examples include: indium oxide-tin oxide (ITO: Indium Tin Oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. In addition, gold (Au), platinum (Pt), or nitrides of metal materials (for example, titanium nitride) can also be mentioned.

[0840] (Hole Injection Layer)

[0841] The hole injection layer is a layer containing a substance with high hole injection properties. As substances with high hole injection properties, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compounds, or polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used.

[0842] (Hole Transport Layer)

[0843] The hole transport layer is a layer containing a substance with high hole transport properties. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used in the hole transport layer. Polymer compounds such as poly (N-vinyl carbazole) (abbreviated as: PVK) and poly (4-vinyl triphenylamine) (abbreviated as: PVTPA) can also be used. Among them, as long as the hole transport property is higher than the electron transport property, substances other than the above substances can be used. It should be noted that the layer containing a substance with high hole transport properties can be not only a single-layer layer, but also a layer formed by stacking two or more layers containing the above substances.

[0844] (Guest (dopant) material of light-emitting layer)

[0845] The light-emitting layer is a layer containing a highly luminescent substance, and various materials can be used. For example, as a highly luminescent substance, a fluorescent compound that emits fluorescence and a phosphorescent compound that emits phosphorescence can be used. A fluorescent compound is a compound that can emit light from a singlet excited state, and a phosphorescent compound is a compound that can emit light from a triplet excited state.

[0846] As the blue fluorescent material that can be used in the light-emitting layer, pyrene derivatives, styrylamine derivatives, Derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. As green fluorescent luminescent materials that can be used in the luminescent layer, aromatic amine derivatives, etc. can be used. As red fluorescent luminescent materials that can be used in the luminescent layer, butane derivatives, diamine derivatives, etc. can be used.

[0847] As the blue phosphorescent material that can be used in the light-emitting layer, metal complexes such as iridium complex, osmium complex, and platinum complex are used. As the green phosphorescent material that can be used in the light-emitting layer, iridium complex is used. As the red phosphorescent material that can be used in the light-emitting layer, metal complexes such as iridium complex, platinum complex, terbium complex, and europium complex are used.

[0848] (Host material of light-emitting layer)

[0849] As the light-emitting layer, the composition can be made by dispersing the above-mentioned high-luminescent substance (guest material) in other substances (host material). As the material for dispersing the high-luminescent substance, various substances can be used, preferably a substance having a high minimum unoccupied orbital energy level (LUMO energy level) and a low maximum occupied orbital energy level (HOMO energy level) compared with the high-luminescent substance.

[0850] As the substance (host material) for dispersing the highly luminescent substance, 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex; 2) a heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative; 3) a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or 4) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.

[0851] (Electron Transport Layer)

[0852] The electron transport layer is a layer containing a substance with high electron transport properties. The electron transport layer can use: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, oxazine derivatives, carbazole derivatives, and phenanthroline derivatives; 3) polymer compounds.

[0853] In one embodiment of the present invention, the electron transport layer may or may not contain the above-mentioned other substances in addition to the compound of one embodiment of the present invention (the compound represented by formula (1)).

[0854] (Electron Injection Layer)

[0855] The electron injection layer is a layer containing a substance with high electron injection properties. Metal complex compounds such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), 8-hydroxyquinoline-lithium (Liq), lithium oxide (LiO x ) or other alkali metals, alkaline earth metals, or compounds thereof.

[0856] (cathode)

[0857] The cathode preferably uses a metal, alloy, conductive compound, and mixture thereof with a small work function (specifically, less than 3.8 eV). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys thereof (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys thereof.

[0858] The cathode is usually formed by vacuum deposition or sputtering. When silver paste or the like is used, a coating method, an inkjet method, or the like can be used.

[0859] When an electron injection layer is provided, the cathode can be formed using various conductive materials such as aluminum, silver, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the size of the work function.

[0860] In the organic EL element of one embodiment of the present invention, the film thickness of each layer is not particularly limited, but is generally preferably in the range of several nm to 1 μm in order to suppress defects such as pinholes, keep the applied voltage low, and improve the luminous efficiency.

[0861] In the organic EL element described in one embodiment of the present invention, the method for forming each layer is not particularly limited. A conventionally known method for forming the layer based on vacuum evaporation, spin coating, etc. can be used. Each layer such as the light-emitting layer can be formed by a known method of coating such as vacuum evaporation, molecular beam evaporation (MBE), or immersion, spin coating, casting, rod coating, and roller coating based on a solution dissolved in a solvent.

[0862] [Electronic equipment]

[0863] An electronic device according to one embodiment of the present invention is characterized by including the organic EL element according to one embodiment of the present invention.

[0864] Specific examples of electronic devices include display components such as organic EL panel modules; display devices such as televisions, mobile phones, and personal computers; and light-emitting devices such as lighting or vehicle lamps.

[0865] Example

[0866] <Compound>

[0867] The compound represented by formula (101) used in the production of the organic EL device of the example is shown below.

[0868] [Chemistry 44]

[0869]

[0870] The following lists the comparative example compounds used in the production of the organic EL device of the comparative example.

[0871] [Chemistry 45]

[0872]

[0873] Other compounds used in the production of the organic EL devices of Examples and Comparative Examples are shown below.

[0874] [Chemistry 46]

[0875]

[0876] <Fabrication of organic EL element 1>

[0877] An organic EL element was produced as follows.

[0878] (Example 1)

[0879] A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Diomatique) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes to make the ITO film thickness 130 nm.

[0880] The cleaned glass substrate with a transparent electrode is mounted on a substrate holder of a vacuum evaporation device. First, compounds HT-1 and HI-1 are co-evaporated on the surface on which the transparent electrode is formed in a manner that covers the transparent electrode, so that the proportion of compound HI-1 reaches 3% by mass, forming a first hole transport layer with a film thickness of 10 nm.

[0881] Compound HT-1 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 80 nm.

[0882] Compound EBL-1 was deposited on the second hole transport layer to form a third hole transport layer (also referred to as “electron blocking layer”) with a film thickness of 5 nm.

[0883] Compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated on the third hole transport layer so that the proportion of compound BD-1 was 4 mass %, thereby forming a light-emitting layer with a thickness of 25 nm.

[0884] Compound 1-1 was evaporated on the light-emitting layer to form a first electron transport layer (also referred to as a “hole blocking layer”) with a thickness of 5 nm.

[0885] On the first electron transport layer, the compound ET-1 and Liq were co-evaporated so that the ratio of Liq became 50 mass % to form a second electron transport layer having a film thickness of 20 nm.

[0886] Metal Yb was evaporated on the second electron transport layer to form an electron injection layer with a film thickness of 1 nm.

[0887] Metal Al was evaporated on the electron injection layer to form a cathode with a film thickness of 50 nm.

[0888] The device structure of the organic EL device of Example 1 is briefly shown below.

[0889] ITO(130) / HT-1:HI-1(10:3%) / HT-1(80) / EBL-1(5) / BH-1:BD-1(25:4%) / Compound 1-1(5) / ET-1:Liq(20:50%) / Yb(1) / Al(50)

[0890] The numbers in parentheses indicate the film thickness (unit: nm). In addition, the numbers in parentheses expressed as percentages indicate the ratio (mass %) of the latter compound in the layer.

[0891] (Comparative Example 1)

[0892] An organic EL device was manufactured in the same manner as in Example 1, except that Compound Ref-1 was used instead of Compound 1-1 in forming the first electron transport layer.

[0893] <Evaluation of Organic EL Element 1>

[0894] The external quantum efficiency of the organic EL devices produced in Example 1 and Comparative Example 1 was evaluated as follows. The results are shown in Table 1.

[0895] External quantum efficiency

[0896] At a current density of 10 mA / cm 2 A voltage was applied to the organic EL element in a manner of , and the EL emission spectrum was measured using a spectroradiometer CS-2000 (manufactured by Conika Minolta Co., Ltd.). The external quantum efficiency EQE was calculated from the obtained spectroradiometric luminance spectrum. In Table 1, EQE represents a relative value when Comparative Example 1 is set to 100.

[0897] [Table 1]

[0898]

[0899] <Production of organic EL elements 2>

[0900] (Example 2)

[0901] An organic EL element was produced as follows.

[0902] A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Diomatique) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes to make the ITO film thickness 130 nm.

[0903] The cleaned glass substrate with a transparent electrode is mounted on a substrate holder of a vacuum evaporation device. First, compounds HT-2 and HI-1 are co-evaporated on the surface on which the transparent electrode is formed in a manner covering the transparent electrode so that the proportion of compound HI-1 reaches 3% by mass, forming a first hole transport layer with a film thickness of 10 nm.

[0904] Compound HT-2 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 80 nm.

[0905] Compound EBL-2 was deposited on the second hole transport layer to form a third hole transport layer (also referred to as “electron blocking layer”) with a film thickness of 5 nm.

[0906] Compound BH-1 (host material) and compound BD-2 (dopant material) were co-evaporated on the third hole transport layer so that the proportion of compound BD-2 was 4% by mass to form a light-emitting layer with a thickness of 25 nm.

[0907] Compound 2-1 was evaporated on the light-emitting layer to form a first electron transport layer (also referred to as a “hole blocking layer”) with a thickness of 5 nm.

[0908] On the first electron transport layer, the compound ET-1 and Liq were co-evaporated so that the ratio of Liq became 50 mass % to form a second electron transport layer having a film thickness of 20 nm.

[0909] Metal Yb was evaporated on the second electron transport layer to form an electron injection layer with a film thickness of 1 nm.

[0910] Metal Al was evaporated on the electron injection layer to form a cathode with a film thickness of 50 nm.

[0911] The device structure of the organic EL device of Example 2 is shown in a simplified form as follows.

[0912] ITO(130) / HT-2:HI-1(10:3%) / HT-2(80) / EBL-2(5) / BH-1:BD-2(25:4%) / Compound 2-1(5) / ET-1:Liq(20:50%) / Yb(1) / Al(50)

[0913] The numbers in parentheses indicate the film thickness (unit: nm). In addition, the numbers in parentheses indicating percentages indicate the ratio (mass %) of the latter compound in the layer.

[0914] (Example 3)

[0915] An organic EL device was produced in the same manner as in Example 2, except that the compound described in Table 2 was used instead of Compound 2-1 in forming the first electron transport layer.

[0916] <Evaluation of Organic EL Element 2>

[0917] The external quantum efficiency and device life of the organic EL devices produced in Examples 2 and 3 were evaluated as follows.

[0918] External quantum efficiency

[0919] At a current density of 10 mA / cm 2 A voltage was applied to the organic EL element in a manner of , and the EL emission spectrum was measured using a spectroradiometer CS-2000 (manufactured by Conika Minolta Co., Ltd.). The external quantum efficiency EQE was calculated from the obtained spectroradiometric brightness spectrum.

[0920] Component life

[0921] At room temperature, the current density reaches 50mA / cm 2A voltage was applied to the organic EL element in a manner of , and the time until the luminance reached 95% of the initial luminance (LT95 (unit: h)) was measured.

[0922] [Table 2]

[0923]

[0924] It was confirmed that the elements of Examples 2 and 3 were excellent in both EQE and LT95.

[0925] It was confirmed that the element of Example 4 was excellent in LT95. In addition, in Example 4, EQE was not measured.

[0926] <Synthesis of Compounds>

[0927] (Synthesis Example 1) Synthesis of Compound 1-1

[0928] Compound 1-1 was synthesized by the following synthetic route.

[0929] [Chemistry 47]

[0930]

[0931] Under argon atmosphere, dioxane (30 mL) and water (5 mL) were added to intermediate 1 (3.00 g), intermediate 2 (3.10 g), Pd2(dba)3 (160 mg), SPhos (287 mg) and potassium carbonate (2.42 g), and refluxed for 6 hours. After the reaction was completed, the solvent was concentrated by short-path silica gel column chromatography. The obtained oil was recrystallized with hexane / toluene solvent to recover a white solid (4.6 g). The solid was purified by column chromatography to obtain the target compound 1-1 (3.7 g, yield 71%). As a result of mass spectrometry analysis, m / e=600 relative to the molecular weight 599.74.

[0932] (Synthesis Example 2) Synthesis of Compound 2-1

[0933] Compound 2-1 was synthesized by the following synthetic route.

[0934] [Chemistry 48]

[0935]

[0936] Under argon atmosphere, 30 mL of xylene was added to intermediate 3 (1.46 g), intermediate 4 (3.00 g), Pd2(dba)3 (165 mg), Xantphos (406 mg), and NaOtBu (1.28 g), and the mixture was heated for 5 hours while refluxed. After the reaction was completed, column chromatography was used for purification to obtain the target compound 2-1 (2.4 g, yield 61%). As a result of mass spectrometry analysis, m / e=676 relative to the molecular weight of 675.84.

[0937] (Synthesis Example 3) Synthesis of Compound 2-2

[0938] Compound 2-2 was synthesized by the following synthetic route.

[0939] [Chemistry 49]

[0940]

[0941] Compound 2-2 was synthesized in the same manner as in the synthesis of compound 2-1, except that intermediate 5 was used instead of intermediate 4, to obtain compound 2-2 as a white solid (9.0 g, yield 76%). As a result of mass spectrometry, the molecular weight was 675.84, m / e=676, and it was identified as the target compound.

[0942] (Synthesis Example 4) Synthesis of Compound 2-3

[0943] Compound 2-3 was synthesized by the following synthetic route.

[0944] [Chemistry 50]

[0945]

[0946] Under argon atmosphere, 20 mL of xylene was added to intermediate 6 (1.00 g), intermediate 4 (2.00 g), Pd2(dba)3 (110 mg), Xantphos (271 mg), and NaOtBu (853 mg), and the mixture was heated for 5 hours and refluxed. After the reaction, the mixture was purified by column chromatography to obtain the target compound 2-3 (1.7 g, yield 65%). As a result of mass spectrometry, m / e=681 relative to the molecular weight of 680.9.

[0947] Several embodiments and / or examples of the present invention are described in detail above, but it is easy for those skilled in the art to make many changes to these illustrative embodiments and / or examples without actually departing from the new teachings and effects of the present invention. Therefore, these many changes are also included in the scope of the present invention.

[0948] The contents of the documents described in this specification and the applications serving as the basis for the Paris Convention priority claim of the present application are incorporated herein by reference in their entirety.

Claims

1. A compound represented by the following formula (101), [Chemistry 51] In formula (101), Either one of X1 and X2 is N, and the other is CH, R1~R 10 Each is independently a hydrogen atom or a substituent R, a group consisting of two or more adjacent groups of R1 to R5 are not bonded to each other, and R6 to R 10 The adjacent groups of two or more are not bonded to each other. n1 is an integer from 0 to 3, When n1 is 0, the structure in the brackets involving n1 is a single bond. When n1 is 2 or 3, the structures in the brackets of n1 may be the same or different. R 11 is a hydrogen atom or a substituent R, 4 R 11 They can be the same or different from each other and consist of 4 R 11 The adjacent groups of two or more are not bonded to each other. n2 is an integer from 0 to 3, When n2 is 0, the structure in the brackets involving n2 is a single bond. When n2 is 2 or 3, the structures in the brackets of n2 may be the same or different. R 21 is a hydrogen atom or a substituent R, 4 R 21 They can be the same or different from each other and consist of 4 R 21 The adjacent groups of two or more are not bonded to each other. n1 01 is 0 or 1, When n101 is 0, the structure in the brackets involving n101 is a single bond. L1 is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group, R 101 ~R 108 1 in the representation is the same as (L1) n101 The single bond of (L1) n101 The single bond R 101 ~R 108 One of them represents a single bond to the nitrogen atom of the carbazole structure, R not representing the single bond 101 ~R 108 Each independently is a hydrogen atom or a substituent R, wherein R 101 ~R 108 The adjacent groups of two or more are not bonded to each other. By R 201 ~R 208 One or more groups of two or more adjacent ones of the rings are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring, or are not bonded to each other, R not bonded to each other 201 ~R 208 are each independently a hydrogen atom or a substituent R, The substituent R is selected from: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 )、 -O-(R 904 )、 -S-(R 905 )、 -N(R 906 )(R 907 )、 Halogen atoms, cyano, nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, When there are two or more substituents R, the two or more substituents R may be the same or different. R 901 ~R 907 Each independently is: 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 monovalent heterocyclic group having 5 to 50 ring atoms, R 901 ~R 907 When there are two or more of each, the two or more R 901 ~R 907 Can be the same or different.

2. The compound according to claim 1, wherein The compound represented by the formula (101) is a compound represented by the following formula (1), [Chemistry 52] In formula (1), R1~R 10 Each is independently a hydrogen atom or a substituent R, a group consisting of two or more adjacent groups of R1 to R5 are not bonded to each other, and R6 to R 10 The adjacent groups of two or more are not bonded to each other. n1 is an integer from 0 to 3, When n1 is 0, the structure in the brackets involving n1 is a single bond. When n1 is 2 or 3, the structures in the brackets of n1 may be the same or different. R 11 is a hydrogen atom or a substituent R, 4 R 11 They can be the same or different from each other and consist of 4 R 11 The adjacent groups of two or more are not bonded to each other. n2 is an integer from 0 to 3, When n2 is 0, the structure in the brackets involving n2 is a single bond. When n2 is 2 or 3, the structures in the brackets of n2 may be the same or different. R 21 is a hydrogen atom or a substituent R, 4 R 21 They can be the same or different from each other and consist of 4 R 21 The adjacent groups of two or more are not bonded to each other. L1 is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group, R 101 ~R 108 One of them represents a single bond with L1, and R that does not represent a single bond with L1 101 ~R 108 One of them represents a single bond to the nitrogen atom of the carbazole structure, R not representing the single bond 101 ~R 108 Each independently is a hydrogen atom or a substituent R, wherein R 101 ~R 108 The adjacent groups of two or more are not bonded to each other. By R 201 ~R 208 One or more groups of two or more adjacent ones of the rings are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring, or are not bonded to each other, R not bonded to each other 201 ~R 208 are each independently a hydrogen atom or a substituent R, The substituent R is selected from: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 )、 -O-(R 904 )、 -S-(R 905 )、 -N(R 906 )(R 907 )、 Halogen atoms, cyano, nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, When there are two or more substituents R, the two or more substituents R may be the same or different. R 901 ~R 907 Each independently is: 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 monovalent heterocyclic group having 5 to 50 ring atoms, R 901 ~R 907 When there are two or more of each, the two or more R 901 ~R 907 Can be the same or different.

3. The compound according to claim 1 or 2, wherein R 102 represents a single bond with L1, R 107 represents a single bond to the nitrogen atom of the carbazole structure.

4. The compound according to any one of claims 1 to 3, wherein By R 201 ~R 208 One or more groups of two or more adjacent ones are not bonded to each other.

5. The compound according to any one of claims 1 to 4, wherein L1 is a substituted or unsubstituted phenylene group.

6. The compound according to any one of claims 2 to 5, wherein The compound represented by the formula (1) is a compound represented by the following formula (11), [Chemistry 53] In formula (11), R1~R 10 , R 11 , R 21 , n1, n2 and R 201 ~R 208 As defined in formula (1), R 31 is a hydrogen atom or a substituent R, 4 R 31 Can be the same or different, consisting of 4 R 31 The adjacent groups of two or more are not bonded to each other. R 111 ~R 116 Each independently is a hydrogen atom or a substituent R, wherein R 111 ~R 116 The adjacent groups of two or more are not bonded to each other. The substituent R is as defined in the above formula (1).

7. The compound according to any one of claims 1 to 6, wherein n1 and n2 are 0.

8. The compound according to any one of claims 1 to 7, wherein R1~R 10 A hydrogen atom.

9. The compound according to any one of claims 1 to 9, wherein R 201 ~R 208 A hydrogen atom.

10. The compound according to any one of claims 2 to 9, wherein In the formula (1), R not representing a single bond 101 ~R 108 or R in the formula (11) 111 ~R 116 A hydrogen atom.

11. The compound according to claim 1, wherein The compound represented by the formula (101) is a compound represented by the following formula (2), [Chemistry 54] In formula (2), R1~R 10 Each is independently a hydrogen atom or a substituent R, a group consisting of two or more adjacent groups of R1 to R5 are not bonded to each other, and R6 to R 10 The adjacent groups of two or more are not bonded to each other. n1 is an integer from 0 to 3, When n1 is 0, the structure in the brackets involving n1 is a single bond. When n1 is 2 or 3, the structures in the brackets of n1 may be the same or different. R 11 is a hydrogen atom or a substituent R, 4 R 11 They can be the same or different from each other and consist of 4 R 11 The adjacent groups of two or more are not bonded to each other, and R1 and R 11 The groups are not bonded to each other, R5 and R 11 The groups are not bonded to each other, n2 is an integer from 1 to 3, When n2 is 2 or 3, the structures in the brackets of n2 may be the same or different. R 21 is a hydrogen atom or a substituent R, 4 R 21 They can be the same or different from each other and consist of 4 R 21 The adjacent groups of two or more are not bonded to each other, and R6 and R 21 The groups are not bonded to each other, R 10 With R 21 The groups are not bonded to each other, R 101 ~R 108 One of them represents a single bond with a carbon atom of the pyrimidine structure, and R that does not represent a single bond with a carbon atom of the pyrimidine structure 101 ~R 108 One of them represents a single bond to the nitrogen atom of the carbazole structure, R not representing the single bond 101 ~R 108 Each independently is a hydrogen atom or a substituent R, wherein R 101 ~R 108 The adjacent groups of two or more are not bonded to each other. By R 201 ~R 208 One or more groups of two or more adjacent ones of the rings are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring, or are not bonded to each other, R not bonded to each other 201 ~R 208 are each independently a hydrogen atom or a substituent R, The substituent R is selected from: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 )、 -O-(R 904 )、 -S-(R 905 )、 -N(R 906 )(R 907 )、 Halogen atoms, cyano, nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, When there are two or more substituents R, the two or more substituents R may be the same or different. R 901 ~R 907 Each independently is: 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 monovalent heterocyclic group having 5 to 50 ring atoms, R 901 ~R 907 When there are two or more of each, the two or more R 901 ~R 907 Can be the same or different.

12. The compound according to claim 11, wherein R 102 Represents a single bond to the carbon atom of the pyrimidine structure, R 107 represents a single bond to the nitrogen atom of the carbazole structure.

13. The compound according to claim 11 or 12, wherein By R 201 ~R 208 One or more groups of two or more adjacent ones are not bonded to each other.

14. The compound according to any one of claims 11 to 13, wherein The compound represented by the formula (2) is a compound represented by the following formula (21), [Chemistry 55] In formula (21), R1~R 10 , R 11 , R 21 , n1, n2 and R 201 ~R 208 As defined in formula (2), R 211 ~R 216 Each independently is a hydrogen atom or a substituent R, wherein R 211 ~R 216 The adjacent groups of two or more are not bonded to each other. The substituent R is as defined in the above formula (2).

15. The compound according to any one of claims 11 to 14, wherein n1 is 0.

16. The compound according to any one of claims 11 to 15, wherein R1~R 10 A hydrogen atom.

17. The compound according to any one of claims 11 to 16, wherein R 201 ~R 208 Any one of is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 201 ~R 208 The rest are each independently selected from: Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 )、 -O-(R 904 )、 -S-(R 905 )、 -N(R 906 )(R 907 )、 Halogen atoms, cyano, nitro, and A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

18. The compound according to any one of claims 11 to 17, wherein R 203 It is a substituted or unsubstituted aryl group having 1 to 50 ring carbon atoms.

19. The compound according to any one of claims 11 to 18, wherein R 203 is substituted or unsubstituted phenyl.

20. The compound according to any one of claims 11 to 19, wherein R 201 ~R 202 and R 204 ~R 208 A hydrogen atom.

21. The compound according to any one of claims 11 to 20, wherein R 211 ~R 216 A hydrogen atom.

22. The compound according to any one of claims 1 to 21, wherein In the case of "substituted or unsubstituted", the substituent and the substituent R are each independently selected from an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and a monovalent heterocyclic group having 5 to 50 ring atoms.

23. The compound according to any one of claims 1 to 22, wherein In the case of "substituted or unsubstituted", the substituent and the substituent R are each independently selected from an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a monovalent heterocyclic group having 5 to 18 ring atoms. 24 . The compound according to claim 1 , which is a material for an organic electroluminescent device.

25. An organic electroluminescent element, comprising: cathode, Anode, and One or more organic layers are disposed between the cathode and the anode, At least one of the organic layers contains the compound according to any one of claims 1 to 24.

26. The organic electroluminescent element according to claim 25, comprising an anode, a light-emitting layer, an electron transport region and a cathode in sequence, The electron transport region includes the compound.

27. The organic electroluminescent element according to claim 26, wherein: The electron transport region has a first layer and a second layer in order from the light emitting layer side, The first layer includes the compound.

28. An electronic device comprising the organic electroluminescent element according to any one of claims 24 to 27.

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