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

Abstract

A compound represented by formula (1) (wherein each symbol is as defined in the description) provides an organic electroluminescent element having further improved element performance. # imgabs0 #

Description

[0001] This application is a divisional application of an application with a filing date of September 23, 2020, application number 202080066366.2, and invention name “Compounds, materials for organic electroluminescent elements, organic electroluminescent elements and electronic devices”. Technical Field

[0002] The present invention relates to a compound, a material for an organic electroluminescent element, an organic electroluminescent element, and an electronic device comprising the organic electroluminescent element. Background Art

[0003] Generally speaking, an organic electroluminescent element (hereinafter, sometimes also described as an "organic EL element") is composed of an anode, a cathode, and an organic layer sandwiched between the anode and the cathode. If a voltage is applied between the two electrodes, electrons are injected from the cathode side and holes are injected from the anode side into the luminescent region, and the injected electrons and holes recombine in the luminescent region to produce an excited state, which emits light when the excited state returns to the ground state. Therefore, from the perspective of obtaining a high-performance organic EL element, it is important to develop materials that efficiently transfer electrons or holes to the luminescent region and facilitate the recombination of electrons and holes.

[0004] Patent Documents 1 to 27 disclose compounds used as materials for organic electroluminescent devices.

[0005] Prior art literature

[0006] Patent Literature

[0007] Patent document 1: US10,388,900B2

[0008] Patent document 2: US10,270,041B2

[0009] Patent Document 3: US10,134,999B2

[0010] Patent Document 4: US9,525,009B2

[0011] Patent Document 5: KR10-1961346

[0012] Patent Document 6: WO2019 / 146781A1

[0013] Patent Document 7: US10,079,34882

[0014] Patent Document 8: KR10-2019-0039905

[0015] Patent Document 9: KR10-2018-0082124

[0016] Patent Document 10: US2018 / 0026199A1

[0017] Patent Document 11: US2019 / 0039996A1

[0018] Patent Document 12: KR10-2018-0102362

[0019] Patent Document 13: KR10-2018-0102367

[0020] Patent Document 14: US2019 / 0237668A1

[0021] Patent Document 15: WO2018 / 168991A1

[0022] Patent document 16: CN106632185B

[0023] Patent document 17: CN106831313A

[0024] Patent Document 18: KR10-2017-0094665

[0025] Patent Document 19: US2017 / 0244047A1

[0026] Patent Document 20: KR10-2018-0053121

[0027] Patent Document 21: KR10-2017-0136391

[0028] Patent document 22: CN108250083A

[0029] Patent Document 23: US2018 / 0123042A1

[0030] Patent Document 24: US2017 / 0194569A1

[0031] Patent Document 25: US2017 / 0186969A1

[0032] Patent Document 26: US2017 / 0186978A1

[0033] Patent Document 27: WO2019 / 044542A1 Summary of the invention

[0034] Problems to be solved by the invention

[0035] Conventionally, many compounds for organic EL devices have been reported, but compounds that further improve the performance of organic EL devices are still being sought.

[0036] The present invention has been made to solve the above-mentioned problems, and an object of the present invention is to provide a compound that further improves the performance of an organic EL element, an organic EL element that further improves the performance of the element, and an electronic device including the organic EL element.

[0037] Means for solving problems

[0038] The present inventors have conducted intensive studies on the performance of organic EL devices containing the compounds described in Patent Documents 1 to 27 and other compounds, and have found that a monoamine having a group having a meta-(2-naphthyl)phenyl group at the terminal bonded to a central nitrogen atom provides an organic EL device with further improved device performance.

[0039] In one embodiment, the present invention provides a compound represented by the following formula (1).

[0040] [Chemical formula 1]

[0041]

[0042] (Where,

[0043] m is 0 or 1;

[0044] n is 0 or 1;

[0045] When m is 0 and n is 0, *b is bonded to carbon atom *1;

[0046] When m is 1 and n is 0, R 5 ~R 9 One of them is a single bond bonded to *b;

[0047] When m is 0 and n is 1, *a is bonded to the carbon atom *1 and is selected from R 10 ~R 14 One of them is a single bond bonded to *b;

[0048] When m is 1 and n is 1, R 5 ~R 9 One of them is a single bond bonded to *a, selected from R 10 ~R 14 One of them is a single bond bonded to *b;

[0049] R 1 ~R 4 , R is not a single bond to *a or *b 5 ~R 9 、R that is not a single bond to *b 10 ~R 14 , R 15 ~R 18 and R 20~R 26 Each independently

[0050] Hydrogen atoms,

[0051] Halogen atoms,

[0052] Nitro,

[0053] Cyano,

[0054] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0055] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0056] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0057] a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms,

[0058] a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,

[0059] a substituted or unsubstituted halogenated alkoxy group having 1 to 50 carbon atoms,

[0060] a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,

[0061] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or

[0062] A monosubstituted silyl group, a disubstituted silyl group or a trisubstituted silyl group having a substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 ring 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, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;

[0063] One or more pairs of two mutually bonded benzene rings selected from benzene rings A to D can be bonded by CR x R y Cross-linking to form a substituted or unsubstituted fluorene structure, or not cross-linking to form a fluorene structure;

[0064] R x and R y are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R x With R y Can be bonded via a single bond;

[0065] L 1 and L 2 Each is independently a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms;

[0066] Ar 1 and Ar 2 Each is independently a substituted or unsubstituted non-condensed aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted condensed aryl group containing a 5-membered ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0067] In another embodiment, the present invention provides a material for an organic EL device, comprising the compound represented by the above formula (1).

[0068] In another embodiment, the present invention provides an organic electroluminescent element comprising an anode, a cathode and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a light-emitting layer, and at least one layer of the organic layer comprises the compound represented by the above formula (1).

[0069] In another embodiment, the present invention provides an electronic device comprising the organic electroluminescent element.

[0070] Effects of the Invention

[0071] An organic EL device containing the compound represented by the above formula (1) shows improved device performance. BRIEF DESCRIPTION OF THE DRAWINGS

[0072] Figure 1 It is a schematic diagram showing an example of the layer structure of the organic EL element according to one embodiment of the present invention.

[0073] Figure 2 It is a schematic diagram showing an example of the layer structure of another organic EL element according to one embodiment of the present invention. DETAILED DESCRIPTION

[0074] [definition]

[0075] In this specification, the hydrogen atom includes isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0076] 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 bondable position of "D" representing a deuterium atom, where a symbol such as "R" is not explicitly indicated.

[0077] In this specification, the number of ring carbons 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 bridged ring compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are bonded 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 carbons. For the "number of ring carbons" described below, it is the same unless otherwise specified. For example, the number of ring carbons of a benzene ring is 6, the number of ring carbons of a naphthalene ring is 10, the number of ring carbons of a pyridine ring is 5, and the number of ring carbons of a furan ring is 4. In addition, for example, the number of ring carbons of 9,9-diphenylfluorenyl is 13, and the number of ring carbons of 9,9'-spirobifluorenyl is 25.

[0078] In addition, when a substituent such as an alkyl group is substituted on a benzene ring, the carbon number of the alkyl group is not included in the ring carbon number of the benzene ring. Therefore, the ring carbon number of the benzene ring substituted with an alkyl group is 6. In addition, when a substituent such as an alkyl group is substituted on a naphthalene ring, the carbon number of the alkyl group is not included in the ring carbon number of the naphthalene ring. Therefore, the ring carbon number of the naphthalene ring substituted with an alkyl group is 10.

[0079] 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 ring compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are bonded to form a cyclic structure (e.g., a monocyclic ring, a condensed ring, and a ring set). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of atoms constituting the ring) and atoms contained in substituents when the ring is substituted by substituents are not included in the number of ring atoms. For the "number of ring atoms" described below, it is the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms 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.

[0080] In this specification, "carbon number XX to YY" in the expression "substituted or unsubstituted ZZ group with carbon number XX to YY" means the carbon number of the ZZ group when it is unsubstituted, and does not include the carbon number of the substituent when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer greater than 1, and "YY" means an integer greater than 2.

[0081] In this specification, "the number of atoms XX to YY" in the expression "ZZ group having XX to YY atoms, which may be substituted or unsubstituted" means the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituent when substituted. Here, "YY" is greater than "XX", "XX" means an integer greater than 1, and "YY" means an integer greater than 2.

[0082] 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".

[0083] In the present specification, "unsubstituted" in the expression "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom or a tritium atom.

[0084] In addition, in the present specification, "substituted" in the expression "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. "Substituted" in the expression "BB group substituted by an AA group" also means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0085] "Substituents described in this specification"

[0086] The substituents described in the present specification are described below. Unless otherwise specified, the substituents described in the present specification are defined as follows.

[0087] The number of ring carbon atoms of the "unsubstituted aryl group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise described in the present specification.

[0088] The number of ring atoms of the "unsubstituted heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise described in the present specification.

[0089] The number of carbon atoms in the "unsubstituted alkyl group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise described in the present specification.

[0090] The number of carbon atoms in the "unsubstituted alkenyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise described in the present specification.

[0091] The number of carbon atoms in the "unsubstituted alkynyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise described in the present specification.

[0092] The number of ring carbon atoms of the "unsubstituted cycloalkyl group" described in the present specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise described in the present specification.

[0093] The number of ring carbon atoms of the "unsubstituted arylene group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise described in the present specification.

[0094] The number of ring atoms of the "unsubstituted divalent heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise described in the present specification.

[0095] The carbon number of the "unsubstituted alkylene group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise described in the present specification.

[0096] "Substituted or unsubstituted aryl"

[0097] As specific examples of "substituted or unsubstituted aryl" described in this specification (specific example group G1), the following unsubstituted aryl (specific example group G1A) and substituted aryl (specific example group G1B) can be cited. (Here, unsubstituted aryl refers to the case where "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl refers to the case where "substituted or unsubstituted aryl" is "substituted aryl".) In the present specification, when it is expressed as "aryl", both "unsubstituted aryl" and "substituted aryl" are included.

[0098] "Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" are replaced by a substituent. Examples of "substituted aryl" include groups in which one or more hydrogen atoms of an "unsubstituted aryl" in the following specific example group G1A are replaced by a substituent, and examples of substituted aryl in the following specific example group G1B can be cited. It should be noted that the examples of "unsubstituted aryl" and "substituted aryl" listed here are for illustrative purposes only, 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 substituent in the "substituted aryl" in the following specific example group G1B are further replaced by a substituent.

[0099] Unsubstituted aryl (specific example group G1A):

[0100] Phenyl,

[0101] p-Biphenyl,

[0102] m-Biphenyl,

[0103] o-Biphenyl,

[0104] 4-terphenyl-4-yl,

[0105] 4-terphenyl-3-yl,

[0106] 4-terphenyl-2-yl,

[0107] m-terphenyl-4-yl,

[0108] m-terphenyl-3-yl,

[0109] m-terphenyl-2-yl,

[0110] o-terphenyl-4-yl,

[0111] o-terphenyl-3-yl,

[0112] o-terphenyl-2-yl,

[0113] 1-naphthyl,

[0114] 2-naphthyl,

[0115] Anthracene,

[0116] Benzanthryl,

[0117] Fiki,

[0118] Triphenylene,

[0119] Phenyl,

[0120] Pyrene

[0121] base,

[0122] Benzo base,

[0123] Triphenylene,

[0124] Benzotriphenylene,

[0125] Tetraphenylene,

[0126] Pentaphenyl,

[0127] Fluorene,

[0128] 9,9'-spirobifluorenyl,

[0129] Benzofluorenyl,

[0130] Dibenzofluorenyl,

[0131] Fluoranthene group,

[0132] Benzofluoranthene,

[0133] Perylene, and

[0134] 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).

[0135] [Chemical formula 2]

[0136]

[0137] [Chemical formula 3]

[0138]

[0139] Substituted aryl (specific example group G1B):

[0140] o-Toluyl,

[0141] m-Toluene

[0142] p-Tolyl,

[0143] p-Xylyl,

[0144] m-Xylyl,

[0145] o-Xylyl,

[0146] p-Isopropylphenyl,

[0147] m-isopropylphenyl,

[0148] o-isopropylphenyl,

[0149] 4-tert-Butylphenyl,

[0150] m-tert-butylphenyl,

[0151] o-tert-butylphenyl,

[0152] 3,4,5-Trimethylphenyl,

[0153] 9,9-dimethylfluorenyl,

[0154] 9,9-Diphenylfluorenyl

[0155] 9,9-di(4-methylphenyl)fluorenyl,

[0156] 9,9-di(4-isopropylphenyl)fluorenyl,

[0157] 9,9-di(4-tert-butylphenyl)fluorenyl,

[0158] Cyanophenyl,

[0159] Triphenylsilylphenyl,

[0160] Trimethylsilylphenyl,

[0161] Phenyl naphthyl,

[0162] Naphthylphenyl, and

[0163] A group in which one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the above general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0164] "Substituted or unsubstituted heterocyclic group"

[0165] The "heterocyclic group" described in this specification is a cyclic group containing at least one heteroatom in the ring atoms. Specific examples of heteroatoms include nitrogen atoms, oxygen atoms, sulfur atoms, silicon atoms, phosphorus atoms and boron atoms. The "heterocyclic group" described in this specification is a monocyclic group or a condensed ring group.

[0166] The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0167] 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. (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In the present specification, when only "heterocyclic group" is expressed, both "unsubstituted heterocyclic group" and "substituted heterocyclic group" are included.

[0168] "Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by a substituent. Specific examples of "substituted heterocyclic group" include groups in which hydrogen atoms of the "unsubstituted heterocyclic group" of the following specific example group G2A are substituted, and examples of substituted heterocyclic groups of the following specific example group G2B are mentioned. It should be noted that the examples of "unsubstituted heterocyclic group" and "substituted heterocyclic group" listed here are only examples, and the "substituted heterocyclic group" recorded in this specification also includes groups in which hydrogen atoms bonded to ring atoms of the heterocyclic group itself in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents, and groups in which hydrogen atoms of substituents in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents.

[0169] 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).

[0170] Specific example group G2B includes, for example, the following heterocyclic groups containing nitrogen atom substitution (specific example group G2B1), oxygen atom substitution heterocyclic groups (specific example group G2B2), sulfur atom substitution heterocyclic groups (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 formula (TEMP-16) to (TEMP-33) are replaced by substituents (specific example group G2B4).

[0171] Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):

[0172] Pyrrolyl,

[0173] Imidazole,

[0174] Pyrazolyl,

[0175] Triazole,

[0176] Tetrazolyl,

[0177] Oxazolyl,

[0178] Isoxazolyl,

[0179] Oxadiazolyl,

[0180] Thiazolyl,

[0181] Isothiazolyl,

[0182] Thiadiazole,

[0183] Pyridyl,

[0184] Pyridazine

[0185] Pyrimidine,

[0186] Pyrazinyl,

[0187] Triazine,

[0188] Indolyl,

[0189] Isoindolyl,

[0190] Indolizine

[0191] Quinolizinyl,

[0192] Quinoline,

[0193] Isoquinolinyl,

[0194] Cinnoline,

[0195] Phthalocyanine

[0196] Quinazoline,

[0197] Quinoxaline,

[0198] Benzimidazolyl,

[0199] Indazolyl,

[0200] Phenanthroline,

[0201] Phenanthridinyl,

[0202] Acridinium,

[0203] Phenazine,

[0204] Carbazolyl,

[0205] Benzocarbazolyl,

[0206] Morpholinyl,

[0207] Phenoxazine,

[0208] Phenothiazine,

[0209] azacarbazolyl, and diazacarbazolyl.

[0210] · Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): furyl,

[0211] Oxazolyl,

[0212] Isoxazolyl,

[0213] Oxadiazolyl,

[0214] Cuckoo ton base,

[0215] Benzofuranyl,

[0216] Isobenzofuranyl,

[0217] Dibenzofuranyl,

[0218] Naphthobenzofuranyl,

[0219] Benzoxazolyl,

[0220] Benzisoxazolyl,

[0221] Phenoxazine,

[0222] Morpholinyl,

[0223] dinaphthofuranyl,

[0224] Azadibenzofuranyl,

[0225] Diazadibenzofuranyl,

[0226] azanaphthobenzofuranyl, and

[0227] naphthyridinylbenzofuranyl.

[0228] Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3):

[0229] Thienyl,

[0230] Thiazolyl,

[0231] Isothiazolyl,

[0232] Thiadiazole,

[0233] benzothienyl,

[0234] Isobenzothienyl,

[0235] dibenzothienyl,

[0236] naphthobenzothienyl,

[0237] Benzothiazolyl,

[0238] Benzisothiazolyl,

[0239] Phenothiazine,

[0240] dinaphthothienyl,

[0241] azadibenzothienyl,

[0242] diazadibenzothienyl,

[0243] azanaphthobenzothienyl, and

[0244] diazanaphthobenzothienyl.

[0245] 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)

[0246] [Chemical formula 4]

[0247]

[0248] [Chemical formula 5]

[0249]

[0250] 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.

[0251] In the above general formulas (TEMP-16) to (TEMP-33), in X A and Y A When at least one of them is NH or CH2, the above general formula (TEMP-16) to

[0252] The monovalent heterocyclic group derived from the ring structure represented by (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from NH or CH2.

[0253] Substituted heterocyclic group containing a nitrogen atom (specific example group G2B 1):

[0254] (9-phenyl)carbazolyl,

[0255] (9-biphenyl)carbazolyl,

[0256] (9-phenyl)phenylcarbazolyl,

[0257] (9-naphthyl)carbazolyl,

[0258] Diphenylcarbazole-9-yl,

[0259] Phenylcarbazol-9-yl,

[0260] Methylbenzimidazolyl,

[0261] Ethylbenzimidazolyl,

[0262] Phenyl triazine,

[0263] Biphenyl triazine,

[0264] Diphenyltriazine,

[0265] Phenylquinazolinyl, and

[0266] Biphenylquinazolinyl.

[0267] Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0268] Phenyldibenzofuranyl,

[0269] Methyldibenzofuranyl,

[0270] tert-Butyldibenzofuranyl, and

[0271] The monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0272] Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

[0273] Phenyldibenzothiophene,

[0274] Methyldibenzothiophene,

[0275] tert-Butyldibenzothienyl, and

[0276] The monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0277] · Groups in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structure represented by the above general formula (TEMP-16) to (TEMP-33) are replaced with substituents (specific example group G2B4):

[0278] The above-mentioned "one or more hydrogen atoms of the monovalent heterocyclic group" refers to hydrogen atoms bonded to carbon atoms forming a ring selected from the monovalent heterocyclic group, A and Y A When at least one of the X atoms is NH, the hydrogen atoms bonded to the nitrogen atom and the A and Y A When one of them is CH2, one or more hydrogen atoms among the hydrogen atoms of the methylene group.

[0279] "Substituted or unsubstituted alkyl"

[0280] As specific examples of "substituted or unsubstituted alkyl" described in this specification (specific example group G3), the following unsubstituted alkyl (specific example group G3A) and substituted alkyl (specific example group G3B) can be cited. (Here, unsubstituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when only "alkyl" is expressed, both "unsubstituted alkyl" and "substituted alkyl" are included.

[0281] "Substituted alkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl" are replaced with 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 with a substituent, and examples of substituted alkyl (specific example group G3B) can be cited. In this specification, the alkyl in "unsubstituted alkyl" refers to a chain alkyl. Therefore,

[0282] “Unsubstituted alkyl” includes linear “unsubstituted alkyl” and branched “unsubstituted alkyl”. It should be noted that the examples of “unsubstituted alkyl” and “substituted alkyl” listed here are for illustrative purposes only, and the “substituted alkyl” described in this specification also includes groups in which the hydrogen atoms of the alkyl 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.

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

[0284] methyl,

[0285] Ethyl,

[0286] n-propyl,

[0287] Isopropyl,

[0288] n-Butyl,

[0289] Isobutyl,

[0290] sec-butyl, and

[0291] Tert-butyl.

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

[0293] Heptafluoropropyl (including isomers),

[0294] Pentafluoroethyl,

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

[0296] Trifluoromethyl.

[0297] "Substituted or unsubstituted alkenyl"

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

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

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

[0301] Vinyl,

[0302] Allyl,

[0303] 1-Butenyl,

[0304] 2-Butenyl, and

[0305] 3-Butenyl.

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

[0307] 1,3-Butadienyl,

[0308] 1-Methylvinyl,

[0309] 1-methylallyl,

[0310] 1,1-dimethylallyl,

[0311] 2-methylallyl, and

[0312] 1,2-Dimethylallyl.

[0313] "Substituted or unsubstituted alkynyl"

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

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

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

[0317] Ethylene

[0318] "Substituted or unsubstituted cycloalkyl"

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

[0320] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" are replaced with 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 with 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 for illustrative purposes only, and the "substituted cycloalkyl" described in this specification also includes the group in which one or more hydrogen atoms bonded to the carbon atoms of the cycloalkyl itself in the "substituted cycloalkyl" of the specific example group G6B are replaced with a substituent, and the group in which the hydrogen atoms of the substituent in the "substituted cycloalkyl" of the specific example group G6B are further replaced with a substituent.

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

[0322] Cyclopropyl,

[0323] Cyclobutyl,

[0324] Cyclopentyl,

[0325] Cyclohexyl,

[0326] 1-adamantyl,

[0327] 2-adamantyl,

[0328] 1-Norbornyl, and

[0329] 2-Norborneol.

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

[0331] 4-Methylcyclohexyl.

[0332] ·“-Si(R 901 )(R 902 )(R 903 )"

[0333] As described in this specification, -Si(R 901 )(R 902 )(R 903 ) are shown as follows (specific example group G7):

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

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

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

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

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

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

[0340] Here,

[0341] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0342] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0343] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0344] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0345] A plurality of G1's in -Si(G1)(G1)(G1) are the same as or different from each other.

[0346] Multiple G2 in -Si(G1)(G2)(G2) are the same as or different from each other.

[0347] A plurality of G1's in -Si(G1)(G1)(G2) are the same as or different from each other.

[0348] Multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other.

[0349] Multiple G3 in -Si(G3)(G3)(G3) are the same as or different from each other.

[0350] Multiple G6's in -Si(G6)(G6)(G6) are the same as or different from each other.

[0351] ·“-O-(R 904 )"

[0352] As described in this specification, -O-(R 904 ) are shown as specific examples (specific example group G8), and include

[0353] -O(G1),

[0354] -O(G2),

[0355] -O(G3), and

[0356] -O(G6).

[0357] Here,

[0358] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0359] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0360] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0361] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0362] ·“-S-(R 905 )"

[0363] As described in this specification, -S-(R 905 ) are shown as specific examples (specific example group G9), and include

[0364] -S(G1),

[0365] -S(G2),

[0366] -S(G3), and

[0367] -S(G6).

[0368] Here,

[0369] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0370] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0371] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0372] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0373] ·“-N(R 906 )(R 907 )"

[0374] As described in this specification, -N(R 906 )(R 907 ) are shown as specific examples (specific example group G10), and include

[0375] -N(G1)(G1),

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

[0377] -N(G1)(G2),

[0378] -N(G3)(G3), and

[0379] -N(G6)(G6).

[0380] Here,

[0381] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0382] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0383] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0384] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0385] - A plurality of G1's in N(G1)(G1) are the same as or different from each other.

[0386] - Multiple G2 in N(G2)(G2) are the same as or different from each other.

[0387] - The multiple G3 in N(G3)(G3) are the same as or different from each other.

[0388] - A plurality of G6's in N(G6)(G6) are the same as or different from each other.

[0389] "Halogen atoms"

[0390] 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.

[0391] "Substituted or unsubstituted fluorinated alkyl"

[0392] The "substituted or unsubstituted fluoroalkyl group" described in the present specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in the "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). The carbon number of the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification. The "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. It should be noted that the "substituted fluoroalkyl group" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in the "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in the "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluorinated alkyl group" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced with fluorine atoms.

[0393] "Substituted or unsubstituted haloalkyl"

[0394] The "substituted or unsubstituted haloalkyl" described in the present specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in the "substituted or unsubstituted alkyl" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in the "substituted or unsubstituted alkyl" are replaced with halogen atoms. The carbon number of 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" refers to a group in which one or more hydrogen atoms of a "haloalkyl" are replaced with 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 an alkyl chain in the "substituted haloalkyl" are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in the "substituted haloalkyl" are further replaced with a substituent. Specific examples of the "unsubstituted haloalkyl group" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced with halogen atoms. A haloalkyl group may also be referred to as a haloalkyl group.

[0395] "Substituted or unsubstituted alkoxy"

[0396] A specific example of the "substituted or unsubstituted alkoxy group" described in the present specification is a group represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification.

[0397] "Substituted or unsubstituted alkylthio"

[0398] A specific example of the "substituted or unsubstituted alkylthio group" described in the present specification is a group represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification.

[0399] "Substituted or unsubstituted aryloxy group"

[0400] 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.

[0401] "Substituted or unsubstituted arylthio"

[0402] 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.

[0403] "Substituted or unsubstituted trialkylsilyl"

[0404] A specific example of a "trialkylsilyl group" described in the present specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. A plurality of G3's in -Si(G3)(G3)(G3) may be identical to or different from each other. The number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise described in the present specification.

[0405] "Substituted or unsubstituted aralkyl"

[0406] 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 obtained by replacing the hydrogen atom of the "alkyl group" with an "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 carbon number of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise described in the present specification.

[0407] 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.

[0408] The substituted or unsubstituted aryl group described in the present specification is preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl, etc.

[0409] The substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidyl group, a triazine group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzofuranyl group The invention also includes but is not limited to benzothiophene, azadibenzothiophene, diazadibenzothiophene, (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 phenyldibenzothiophene, etc.

[0410] In the present specification, the carbazolyl group is specifically any of the following groups unless otherwise described in the present specification.

[0411] [Chemical formula 6]

[0412]

[0413] In the present specification, the (9-phenyl)carbazolyl group is specifically any of the following groups unless otherwise specified in the present specification.

[0414] [Chemical formula 7]

[0415]

[0416] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0417] 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.

[0418] [Chemical formula 8]

[0419]

[0420] In the above general formulas (TEMP-34) to (TEMP-41), * represents a bonding position.

[0421] The substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, or the like, unless otherwise described in the present specification.

[0422] "Substituted or unsubstituted arylene group"

[0423] Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group". Specific examples 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.

[0424] "Substituted or unsubstituted divalent heterocyclic group"

[0425] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom on the heterocyclic ring from the above-mentioned "substituted or unsubstituted heterocyclic group". Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include divalent groups derived by removing one hydrogen atom on the heterocyclic ring from the "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0426] "Substituted or unsubstituted alkylene"

[0427] 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.

[0428] 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.

[0429] [Chemical formula 9]

[0430]

[0431] [Chemical formula 10]

[0432]

[0433] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q10 Each is independently a hydrogen atom or a substituent.

[0434] In the above general formulas (TEMP-42) to (TEMP-52), * represents a bonding position.

[0435] [Chemical formula 11]

[0436]

[0437] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0438] Formula Q9 and Q 10 They may be bonded to each other via a single bond to form a ring.

[0439] In the above general formulas (TEMP-53) to (TEMP-62), * represents a bonding position.

[0440] [Chemical formula 12]

[0441]

[0442] In the above general formulae (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0443] In the above general formulas (TEMP-63) to (TEMP-68), * represents a bonding position.

[0444] 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.

[0445] [Chemical formula 13]

[0446]

[0447] [Chemical formula 14]

[0448]

[0449] In the above general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0450] [Chemical formula 16]

[0451]

[0452] [Chemical formula 18]

[0453]

[0454] In the above general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0455] The above is the description of the “substituents described in the present specification”.

[0456] "When bonding to form a ring"

[0457] In the present specification, when it is expressed that "one or more of the adjacent groups of two or more 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", it means the case where "one or more of the adjacent groups of two or more are bonded to each other to form a substituted or unsubstituted monocyclic ring", the case where "one or more of the adjacent groups of two or more are bonded to each other to form a substituted or unsubstituted condensed ring", and the case where "one or more of the adjacent groups of two or more are not bonded to each other".

[0458] The case of "one or more of the groups consisting 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 of the groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted condensed ring" (hereinafter, these cases are sometimes collectively referred to as "bonded to form a ring") in this specification are explained below. The case of an anthracene compound represented by the following general formula (TEMP-103) in which the mother skeleton is an anthracene ring is explained as an example.

[0459] [Chemical formula 20]

[0460]

[0461] For example, R 921 ~R 930 In the case of "one or more groups of two or more adjacent groups are bonded to each other to form a ring", the group of two adjacent groups forming one group means that R 921 and R 922 Group, R 922 and R 923 Group, R 923 and R 924 Group, R 924 and R 930 Group, R 930 and R 925 Group, R 925 and R 926 Group, R 926 and R 927 Group, R 927 and R928 Group, R 928 and R 929 The group, and R 929 and R 921 group.

[0462] The above-mentioned "one or more groups" means that the above-mentioned two or more adjacent groups can form a ring at the same time. 921 and R 922 Bonded to each other to form ring Q A , while R 925 and R 926 Bonded to each other to form ring Q B When the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0463] [Chemical formula 21]

[0464]

[0465] The case where "a group of two or more adjacent groups" forms a ring includes not only the case where a group of "two" adjacent groups is bonded as shown in the above example, but also the case where a group of "three or more" adjacent groups is bonded. For example, R 921 and R 922 Bonded to each other to form ring Q A And R 922 and R 923 Bonded to each other to form ring Q C , consisting of three adjacent (R 921 , R 922 and R 923 ) are bonded to each other to form a ring and fused to the anthracene mother skeleton, in this case, the anthracene compound represented by the above 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 .

[0466] [Chemical formula 22]

[0467]

[0468] The formed "monocyclic ring" or "condensed ring" may be a saturated ring or an unsaturated ring based only on the structure of the formed ring. When "one of the two adjacent groups" forms a "monocyclic ring" or "condensed ring", the "monocyclic ring" or "condensed ring" may form a saturated ring or an unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104) Aand 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 and Ring Q C If the ring Q of the above general formula (TMEP-104) A is a benzene ring, then ring Q A If the ring Q of the above general formula (TMEP-104) A is a naphthalene ring, then ring Q A It is a condensed ring.

[0469] The "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.

[0470] Specific examples of the aromatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G1 are terminated with hydrogen atoms.

[0471] Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in Specific Example Group G2 are terminated with hydrogen atoms.

[0472] Specific examples of the aliphatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G6 are terminated with hydrogen atoms.

[0473] "Forming a ring" means that a ring is formed only by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton and one or more other optional elements. For example, R 921 and R 922 The ring Q formed by mutual bonding A It means that R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 The carbon atoms of the anthracene skeleton bonded to one or more optional elements form a ring. 921 and 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 bonded to the four carbon atoms forms a monocyclic unsaturated ring, R 921 and R 922 The ring formed is a benzene ring.

[0474] Here, "optional element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur, unless otherwise specified in this specification. In the optional element (e.g., carbon or nitrogen), the bond that does not form a ring may be terminated by a hydrogen atom or the like, or may be substituted by an "optional substituent" described later. When an optional element other than carbon is included, the formed ring is a heterocycle.

[0475] Unless otherwise specified in the present specification, the number of "one or more optional elements" constituting a monocyclic or condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.

[0476] Unless otherwise specified in the present specification, "monocyclic ring" is preferred among "monocyclic ring" and "condensed ring".

[0477] Unless otherwise specified in the present specification, the "unsaturated ring" is preferred among the "saturated ring" and the "unsaturated ring".

[0478] Unless otherwise specified in the present specification, the "monocyclic ring" is preferably a benzene ring.

[0479] Unless otherwise specified in the present specification, the "unsaturated ring" is preferably a benzene ring.

[0480] When "one or more of the adjacent two or more groups" "are bonded to each other to form a substituted or unsubstituted single ring", or "are 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 of the adjacent two or more groups are bonded to each other to form a substituted or unsubstituted "unsaturated ring" formed by multiple atoms of the parent skeleton and one or more and fifteen or less elements selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0481] 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".

[0482] When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of the substituent when the above-mentioned "saturated ring" or "unsaturated ring" has a substituent are the substituents described in the above-mentioned "substituents described in the present specification".

[0483] The above is an explanation of the case where "one or more of the groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted single ring" and the case where "one or more of the 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").

[0484] ·Substituents when expressed as "substituted or unsubstituted"

[0485] In one embodiment of the present specification, the substituent described as "substituted or unsubstituted" (sometimes referred to as "optional substituent" in the present specification) is, for example, selected from

[0486] unsubstituted alkyl having 1 to 50 carbon atoms,

[0487] unsubstituted alkenyl having 2 to 50 carbon atoms,

[0488] unsubstituted alkynyl having 2 to 50 carbon atoms,

[0489] unsubstituted cycloalkyl having 3 to 50 ring carbon atoms,

[0490] -Si(R 901 )(R 902 )(R 903 ),

[0491] -O-(R 904 ),

[0492] -S-(R 905 ),

[0493] -N(R 906 )(R 907 ),

[0494] Halogen atoms, cyano, nitro,

[0495] unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0496] Unsubstituted heterocyclic group having 5 to 50 ring atoms

[0497] The groups in the group etc.

[0498] Here, R 901 ~R 907 , each independently

[0499] Hydrogen atoms,

[0500] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0501] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0502] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0503] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0504] In R 901 When there are two or more, two or more R 901 Same or different from each other,

[0505] In R 902 When there are two or more, two or more R 902 Same or different from each other,

[0506] In R 903 When there are two or more, two or more R 903 Same or different from each other,

[0507] In R 904 When there are two or more, two or more R 904 Same or different from each other,

[0508] In R 905 When there are two or more, two or more R 905 Same or different from each other,

[0509] In R 906 When there are two or more, two or more R 906 Same or different from each other,

[0510] In R 907 When there are two or more, two or more R 907 Same as or different from each other.

[0511] In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

[0512] an alkyl group having 1 to 50 carbon atoms,

[0513] an aryl group having 6 to 50 ring carbon atoms, and

[0514] A heterocyclic group having 5 to 50 ring atoms

[0515] The groups in the group.

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

[0517] an alkyl group having 1 to 18 carbon atoms,

[0518] an aryl group having 6 to 18 ring carbon atoms, and

[0519] A heterocyclic group having 5 to 18 ring atoms

[0520] The groups in the group.

[0521] Specific examples of each of the above optional substituents are the same as those described in the above section "substituents described in the present specification".

[0522] In the present specification, unless otherwise stated, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring" with each other, preferably forming a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably forming a benzene ring.

[0523] In the present specification, unless otherwise specified, an optional substituent may further have a substituent. The substituent further possessed by the optional substituent is the same as the optional substituent described above.

[0524] 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.

[0525] Hereinafter, the compound of the present invention will be described.

[0526] The compound of the present invention is represented by the following formula (1). Hereinafter, the compound of the present invention represented by formula (1) and formulas included in formula (1) described later may be simply referred to as "compound of the present invention".

[0527] [Chemical formula 23]

[0528]

[0529] Hereinafter, symbols in formula (1) and formula (1) described later will be described. Unless otherwise specified, the same symbols have the same meanings.

[0530] m is 0 or 1, and n is 0 or 1.

[0531] When m is 0 and n is 0, *b is bonded to the carbon atom *1.

[0532] When m is 1 and n is 0, R 5 ~R 9 One of them is a single bond bonded to *b.

[0533] When m is 0 and n is 1, *a is bonded to the carbon atom *1 and is selected from R 10 ~R 14 One of them is a single bond bonded to *b.

[0534] When m is 1 and n is 1, R 5 ~R 9 One of them is a single bond bonded to *a, selected from R 10 ~R 1 One of them is a single bond bonded to *b.

[0535] Therefore, the compound of the invention represented by formula (1) includes a compound represented by any of the following formulae (1a) to (1d).

[0536] [Chemical formula 24]

[0537]

[0538] [Chemical formula 25]

[0539]

[0540] [Chemical formula 26]

[0541]

[0542] [Chemical formula 27]

[0543]

[0544] R 1 ~R 4 , R is not a single bond to *a or *b 5 ~R 9 、R that is not a single bond to *b 10 ~R 14 , R 15 ~R 18 and R 20 ~R 26 Each of them is independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, 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 heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms, or a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from 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, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0545] Preferably, each independently represents a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and more preferably each independently represents a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0546] The details of the halogen atom are as described in the "substituents described in the present specification", and a fluorine atom is preferred.

[0547] The details of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms are as described in the section "Substituents described in the present specification".

[0548] The unsubstituted alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl, more preferably methyl, ethyl, isopropyl or tert-butyl, further preferably methyl or tert-butyl.

[0549] The details of the substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms are as described in the section "Substituents described in the present specification".

[0550] The unsubstituted cycloalkyl group is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group, and more preferably a cyclopropyl group, a cyclopentyl group or a cyclohexyl group.

[0551] The details of the substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms are as described in the "Substituents described in the present specification".

[0552] The unsubstituted heterocyclic group 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, a dibenzofuranyl group, a naphthiobenzofuranyl group, a dibenzothiophenyl group or a naphthiobenzothiophenyl group, more preferably a pyridyl group, a pyrimidyl group, a carbazolyl group, a dibenzofuranyl group, a naphthiobenzofuranyl group or a dibenzothiophenyl group, further preferably a 1-, 2-, 3-, 4- or 9-carbazolyl group, a 1-, 2-, 3- or 4-dibenzofuranyl group, or a 1-, 2-, 3- or 4-dibenzothiophenyl group.

[0553] The substituted heterocyclic group is preferably a 9-phenylcarbazolyl group (9-phenylcarbazolyl-1-yl, 9-phenylcarbazolyl-2-yl, 9-phenylcarbazolyl-3-yl, or 9-phenylcarbazolyl-4-yl), a diphenylcarbazolyl-9-yl, or a phenylcarbazolyl-9-yl, a 6-phenyldibenzofuran-4-yl, or a 7-phenyldibenzofuran-3-yl.

[0554] The details of the substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms are as described in the "substituents described in the present specification", and it is preferably a substituted or unsubstituted fluoroalkyl group having 1 to 50 carbon atoms.

[0555] The unsubstituted fluoroalkyl group is preferably a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, or a heptafluoropropyl group, and more preferably a trifluoromethyl group.

[0556] The details of the substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms are as described in the "Substituents described in the present specification".

[0557] The unsubstituted alkoxy group is preferably a methoxy group, an ethoxy group, a propoxy group or a tert-butoxy group, more preferably a methoxy group or an ethoxy group, and further preferably a methoxy group.

[0558] The above-mentioned substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms is a group represented by -O(G12), and G12 is the above-mentioned substituted or unsubstituted haloalkyl group.

[0559] The substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms is preferably a substituted or unsubstituted fluoroalkoxy group having 1 to 50 carbon atoms.

[0560] The unsubstituted fluoroalkoxy group is preferably a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, a pentafluoroethoxy group, or a heptafluoropropoxy group, more preferably a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, or a pentafluoroethoxy group, and further preferably a trifluoromethoxy group.

[0561] The details of the substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms are as described in the "Substituents described in the present specification".

[0562] The unsubstituted aryloxy group is preferably a phenoxy group, a biphenyloxy group, or a terphenyloxy group, and more preferably a phenoxy group or a biphenyloxy group.

[0563] The details of the substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms are as described in the "Substituents described in the present specification".

[0564] The unsubstituted aralkyl group is preferably benzyl, phenyl-tert-butyl, α-naphthylmethyl, β-naphthylmethyl, 1-β-naphthylisopropyl, or 2-β-naphthylisopropyl, and more preferably benzyl, phenyl-tert-butyl, α-naphthylmethyl, or β-naphthylmethyl.

[0565] The substituents of the monosubstituted silyl group, disubstituted silyl group or trisubstituted silyl group are each independently selected from 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, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. The details of these groups are as described in "Substituents described in the present specification".

[0566] The monosubstituted silyl group, disubstituted silyl group or trisubstituted silyl group is preferably trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, isopropyldimethylsilyl, triphenylsilyl, phenyldimethylsilyl, tert-butyldiphenylsilyl, or tritolylsilyl, and more preferably trimethylsilyl or triphenylsilyl.

[0567] Selected from R 1 With R 2 and R 3 With R 4 At least one group of adjacent two of the can be independently bonded to each other to form a ring structure selected from a substituted or unsubstituted heterocycle and a substituted or unsubstituted hydrocarbon ring, or can be non-bonded to each other, so that the above-mentioned ring structure is not formed. In one embodiment of the present invention, it is preferred that the above-mentioned ring structure is not formed. In other embodiments of the present invention, it is preferred to form the above-mentioned ring structure.

[0568] In one embodiment of the present invention, R 1 ~R 4 All may be hydrogen atoms.

[0569] R is selected from R which is not a single bond to *a or *b 5 ~R 9 At least one set of two adjacent ones, i.e. selected from R 5 With R 6 , R 6 With R 7 , R 7 With R 8 , and R 8 With R 9 At least one group of adjacent two of them may be bonded to each other independently to form a ring structure selected from a substituted or unsubstituted heterocycle and a substituted or unsubstituted hydrocarbon ring, or may not be bonded to each other, so that the above-mentioned ring structure is not formed. In one embodiment of the present invention, it is preferred that the above-mentioned ring structure is not formed. In other embodiments of the present invention, it is preferred that the above-mentioned ring structure is formed.

[0570] In one embodiment of the present invention, R which is not a single bond to *a or *b 5 ~R 9 All may be hydrogen atoms.

[0571] R selected from the group consisting of R which is not a single bond to *b 10 ~R 14 At least one set of two adjacent ones, i.e. selected from R 10 With R 11 , R 11 With R 12 , R 12 With R 13 , and R 13 With R 14 At least one group of adjacent two of them may be bonded to each other independently to form a ring structure selected from a substituted or unsubstituted heterocycle and a substituted or unsubstituted hydrocarbon ring, or may not be bonded to each other, so that the above-mentioned ring structure is not formed. In one embodiment of the present invention, it is preferred that the above-mentioned ring structure is not formed. In other embodiments of the present invention, it is preferred that the above-mentioned ring structure is formed.

[0572] In one embodiment of the present invention, R which is not a single bond bonded to *b 10 ~R 1 All may be hydrogen atoms.

[0573] Selected from R 15 ~R 18 and R 20 ~R 26 At least one set of two adjacent ones, i.e. selected from R 15 With R 16 , R 16 With R 17 , R 21 With R 22 , R 23 With R 24 , R 24 With R 25 , and R 25 With R 26 At least one group of adjacent two of them may be bonded to each other independently to form a ring structure selected from a substituted or unsubstituted heterocycle and a substituted or unsubstituted hydrocarbon ring, or may not be bonded to each other, so that the above-mentioned ring structure is not formed. In one embodiment of the present invention, it is preferred that the above-mentioned ring structure is not formed. In other embodiments of the present invention, it is preferred that the above-mentioned ring structure is formed.

[0574] In one embodiment of the present invention, R 15 ~R 18 All can be hydrogen atoms, R 20 ~R 26 All may be hydrogen atoms.

[0575] The heterocyclic ring is selected from aromatic heterocyclic rings and non-aromatic heterocyclic rings.

[0576] The above-mentioned aromatic heterocyclic ring is, for example, a pyrrole ring, a furan ring, a thiophene ring, a pyridine ring, an imidazole ring, a pyrazole ring, an indole ring, an isoindole ring, a benzofuran ring, an isobenzofuran ring, a benzothiophene ring, a benzimidazole ring, an indazole ring, a dibenzofuran ring, a naphthiobenzofuran ring, a dibenzothiophene ring, a naphthiobenzothiophene ring, a carbazole ring or a benzocarbazole ring.

[0577] The non-aromatic heterocycle is, for example, a heterocycle obtained by partially hydrogenating the aromatic heterocycle.

[0578] The hydrocarbon ring is selected from an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.

[0579] The aromatic hydrocarbon rings include, for example, a benzene ring, a biphenyl ring, a naphthalene ring, an anthracene ring, a benzanthracene ring, a phenanthrene ring, a triphenylene ring, a phenanthene ring, a pyrene ring, It is a 1,1-dimethylindene ring, a 1,1-dimethylindene ring, or a triphenylene ring, preferably a benzene ring or a naphthalene ring, more preferably a benzene ring.

[0580] The aliphatic hydrocarbon ring is, for example, a cyclopentene ring, a cyclopentadiene ring, a cyclohexene ring, a cyclohexadiene ring, or a hydrocarbon ring obtained by partially hydrogenating the aromatic hydrocarbon ring.

[0581] In formula (1), formulas included in the above formula (1), and formulas included in the formula (1) described later, one or more pairs of two mutually bonded benzene rings selected from benzene rings A to D may be bonded by CR x R y The fluorene structure may be formed by cross-linking or a substituted or unsubstituted fluorene structure may be formed without cross-linking.

[0582] That is, in formula (1):

[0583] [Chemical formula 28]

[0584]

[0585] When m is 0 and n is 0, the benzene ring A and the benzene ring D bonded to each other may or may not form the above-mentioned substituted or unsubstituted fluorene structure.

[0586] When m is 1 and n is 0, one or both of the mutually bonded benzene rings A and B and the mutually bonded benzene rings B and D may or may not form the above-mentioned substituted or unsubstituted fluorene structure.

[0587] When m is 0 and n is 1, one or both of the mutually bonded benzene ring A and benzene ring C and the mutually bonded benzene ring C and benzene ring D may or may not form the above-mentioned substituted or unsubstituted fluorene structure.

[0588] When m is 1 and n is 1, the two mutually bonded benzene rings selected from at least one of the mutually bonded benzene rings A and B, the mutually bonded benzene rings B and C, and the mutually bonded benzene rings C and D may form the above-mentioned substituted or unsubstituted fluorene structure, or may not form the above-mentioned substituted or unsubstituted fluorene structure.

[0589] In other words, when m is 0 and n is 0,

[0590] R 2 and R 3 One of them can be combined with R 15 and R 18 One of them together forms a cross-linking group CR x R y , or no cross-linking group CR may be formed x R y .

[0591] When m is 1 and n is 0,

[0592] R 2 and R 3 One of them can be combined with R 5 and R 9 One of them together forms a cross-linking group CR x R y , or no cross-linking group CR may be formed x R y ;

[0593] is present on a carbon atom adjacent to the carbon atom bonded to the benzene ring D and is selected from R 5 ~R 9 One of them can be combined with R 15 and R 18 One of them together forms a cross-linking group CR x R y , or no CR is formed x R y .

[0594] When m is 0 and n is 1,

[0595] R 2 and R 3 One of them can be combined with R 10 and R 14 One of them together forms a cross-linking group CR x Ry , or no cross-linking group CR may be formed x R y ;

[0596] is present on a carbon atom adjacent to the carbon atom bonded to the benzene ring D and is selected from R 10 ~R 14 One of them can be combined with R 15 and R 19 One of them together forms a cross-linking group CR x R y , or no cross-linking group CR may be formed x R y .

[0597] When m is 1 and n is 1,

[0598] R 2 and R 3 One of them can be combined with R 5 and R 9 One of them together forms a cross-linking group CR x R y , or no cross-linking group CR may be formed x R y ;

[0599] is present on a carbon atom adjacent to the carbon atom bonded to the benzene ring C and is selected from R 5 ~R 9 One of them can be combined with R 10 and R 14 One of them together forms a cross-linking group CR x R y , or no cross-linking group CR may be formed x R y ;

[0600] is present on a carbon atom adjacent to the carbon atom bonded to the benzene ring D and is selected from R 10 ~R 14 One of them can be combined with R 15 and R 19 One of them together forms a cross-linking group CR x R y , or no cross-linking group CR may be formed x R y .

[0601] In one embodiment of the present invention, it is preferred that the two mutually bonded benzene rings are not cross-linked to form the substituted or unsubstituted fluorene structure. In another embodiment of the present invention, it is preferred that one or more groups of the two mutually bonded benzene rings are cross-linked by CR. x R yCross-linking to form substituted or unsubstituted fluorene structure.

[0602] R x and R y are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R x With R y Bonding may be via a single bond.

[0603] The details of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms are as described in relation to R 1 ~R 4 , R is not a single bond to *a or *b 5 ~R 9 、R that is not a single bond to *b 10 ~R 14 , R 15 ~R 18 and R 20 ~R 26 As described in the records.

[0604] The details of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms are as described in "Substituents described in the present specification". The unsubstituted aryl group having 6 to 50 ring carbon atoms is preferably phenyl, 1-naphthyl, 2-naphthyl, p-biphenyl, m-biphenyl, or o-biphenyl, and more preferably phenyl.

[0605] As R x With R y CR bonded by a single bond x R y , for example, the following groups can be mentioned.

[0606] [Chemical formula 29]

[0607]

[0608] (In the formula, *g is bonded to one of the two benzene rings cross-linked with each other, and *h is bonded to the other benzene ring.)

[0609] L 1 and L 2 Each is independently a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0610] In one embodiment of the present invention, preferably L 1 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, L 2 It is a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0611] In another embodiment of the present invention, preferably L 1is a single bond, L 2 It is a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0612] The details of the substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms are as described in "Substituents described in the present specification", and it is preferably a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group, and more preferably an arylene group selected from the following.

[0613] [Chemical formula 30]

[0614]

[0615] (In the formula, one of the two free valences is bonded to the central nitrogen atom, and the other is bonded to Ar 1 or Ar 2 Optional substituents are omitted for simplicity.)

[0616] Ar 1 and Ar 2 Each is independently a substituted or unsubstituted non-condensed aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted condensed aryl group containing a 5-membered ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0617] The substituted or unsubstituted non-condensed aryl group having 6 to 50 ring carbon atoms is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group, more preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, a m-terphenyl-3′-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, or a 5′-phenyl-m-terphenyl group, further preferably a phenyl group, a p-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, or a p-terphenyl-2-yl group, and particularly preferably a phenyl group, a p-biphenyl group, or a p-terphenyl-4-yl group.

[0618] The above-mentioned substituted or unsubstituted 5-membered ring-containing condensed aromatic group having 6 to 50 ring carbon atoms is preferably a substituted or unsubstituted fluorenyl group, more preferably a 1-, 2-, 3- or 4-9,9-dimethylfluorenyl group, a 1-, 2-, 3- or 4-9,9-diphenylfluorenyl group, or a 1-, 2-, 3- or 4-9,9'-spirobifluorenyl group, and further preferably a 1- or 2-9,9-dimethylfluorenyl group, a 2- or 4-9,9-diphenylfluorenyl group, or a 2- or 4-9,9'-spirobifluorenyl group.

[0619] The details of the substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms are as described in the “Substituents described in the present specification”, preferably a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group, more preferably a 1-, 2-, 3-, or 4-dibenzofuranyl group, a 1-, 2-, 3-, or 4-dibenzothienyl group, a 9-carbazolyl group, or a 9-phenyl-1-, 2-, 3-, or 4-carbazolyl group, further preferably a 3- or 4-dibenzofuranyl group, a 9-carbazolyl group, a 3-, or 4-carbazolyl group.

[0620] In Ar 1 or Ar 2 In the case of a carbazolyl group, it is preferred that a benzene ring or the like is not fused to the carbazolyl group.

[0621] In Ar 1 or Ar 2 is a 9-carbazolyl group and the L to which the 9-carbazolyl group is bonded 1 or L 2 When Ar is phenylene, biphenylene, or terphenylene, 1 -L 1 - or Ar 2 -L 2 - The following structure is preferred.

[0622] [Chemical formula 31]

[0623]

[0624] (In the formula, optional substituents are omitted for simplicity.)

[0625] In one embodiment of the present invention, preferably L of formula (1) 1 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, Ar 1 It is a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0626] Therefore, the formula (1) includes the compound represented by the following formula (2).

[0627] [Chemical formula 32]

[0628]

[0629] (Where,

[0630] m, n, R 1 ~R 4 , R 5 ~R 9 , R 10 ~R14 , R 15 ~R 18 , R 20 ~R 26 , *a, *b, L 2 and Ar 2 As defined in formula (1);

[0631] L 11 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms;

[0632] X 1 Is with O, S, CR c R d NR e or a nitrogen atom bonded to *c;

[0633] R c and R d Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;

[0634] R e is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;

[0635] In X 1 O, S, CR c R d or NR e In the case of R 31 ~R 34 One of them is a single bond to *c;

[0636] R that is not a single bond to *c 31 ~R 34 and R 35 ~R 38 Each independently

[0637] Hydrogen atoms,

[0638] Halogen atoms,

[0639] Nitro,

[0640] Cyano,

[0641] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0642] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0643] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0644] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

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

[0646] a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,

[0647] a substituted or unsubstituted halogenated alkoxy group having 1 to 50 carbon atoms,

[0648] a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,

[0649] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or

[0650] A monosubstituted silyl group, a disubstituted silyl group, or a trisubstituted silyl group having a substituent selected from 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, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0651] L 11 The details of the substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms are as described for L 1 and L 2 As described in the records.

[0652] R c and R d The details of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and the details of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms are the same as those for R x and R y As shown in the records.

[0653] R e The details of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms are as described for R x and R y As described in the records.

[0654] R is not a single bond to *c 31 ~R 34 and R 35 ~R 38 The details of each group shown (excluding substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms) are the same as those for R 1 ~R 4 , R is not a single bond to *a or *b 5 ~R 9 、R that is not a single bond to *b 10 ~R 1 , R 15 ~R 18 and R 20 ~R26 The details of the corresponding groups described are the same.

[0655] R that is not a single bond to *c 31 ~R 34 and R 35 ~R 38 The details of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms are as described for R x and R y As described in the records.

[0656] R is selected from R which is not a single bond to *c 31 ~R 34 and R 35 ~R 38 At least one set of two adjacent ones, i.e. selected from R 31 With R 32 , R 32 With R 33 , R 33 With R 34 , R 35 With R 36 , R 36 With R 37 and R 37 and R 38 At least one set of adjacent two of the X may be independently bonded to each other to form a ring structure selected from a substituted or unsubstituted heterocyclic ring and a substituted or unsubstituted hydrocarbon ring, or may not be bonded to each other, thus not forming the above ring structure. In one embodiment of the present invention, it is preferred to form the above ring structure. In other embodiments of the present invention, it is preferred not to form the above ring structure, especially in X 1 NR e In the case of a nitrogen atom bonded to *c, it is preferred that the above-mentioned ring structure is not formed.

[0657] The details of the above heterocyclic ring and hydrocarbon ring are as described above.

[0658] R that is not a single bond to *c 31 ~R 34 and R 35 ~R 38 All may be hydrogen atoms.

[0659] Formula (2) includes compounds represented by any of the following formulae (2a) to (2d).

[0660] [Chemical formula 33]

[0661]

[0662] [Chemical formula 34]

[0663]

[0664] [Chemical formula 35]

[0665]

[0666] [Chemical formula 36]

[0667]

[0668] In one embodiment of the present invention, preferably L of formula (1) 1 is a single bond, Ar 1 It is a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0669] Therefore, the formula (1) includes the compound represented by the following formula (3).

[0670] [Chemical formula 37]

[0671]

[0672] (Where,

[0673] m, n, R 1 ~R 4 , R 5 ~R 9 , R 10 ~R 14 , R 15 ~R 18 , R 20 ~R 26 , *a, *b, L 2 and Ar 2 As defined in formula (1);

[0674] X 2 O, S, CR c R d or NR e ;

[0675] Selected from R 31 ~R 34 One of them is a single bond to *c;

[0676] R c , R d , R e 、R that is not a single bond to *c 31 ~R 34 , and R 35 ~R 38 As defined in formula (2).

[0677] Formula (3) includes compounds represented by any of the following formulae (3a) to (3d).

[0678] [Chemical formula 38]

[0679]

[0680] [Chemical formula 39]

[0681]

[0682] [Chemical formula 40]

[0683]

[0684] [Chemical formula 41]

[0685]

[0686] In one embodiment of the present invention, Ar of formula (1) 1 and Ar 2 Each of them is independently preferably a substituted or unsubstituted non-condensed aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted condensed aryl group having 6 to 50 ring carbon atoms and containing a 5-membered ring.

[0687] Therefore, the formula (1) includes the compound represented by the following formula (4).

[0688] [Chemical formula 42]

[0689]

[0690] (Where,

[0691] m, n, R 1 ~R 4 , R 5 ~R 9 , R 10 ~R 14 , R 15 ~R 18 , R 20 ~R 26 , *a, *b, L 1 , and L 2 As defined in formula (1):

[0692] Ar 11 and Ar 22 Each is independently a substituted or unsubstituted non-condensed aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted condensed aryl group having 6 to 50 ring carbon atoms and containing a 5-membered ring.

[0693] Ar 1 and Ar 22The details of the substituted or unsubstituted non-condensed aryl group having 6 to 50 ring carbon atoms and the details of the substituted or unsubstituted condensed aryl group having 6 to 50 ring carbon atoms and containing a 5-membered ring are as described in the description of Ar 1 and Ar 2 As shown in the records.

[0694] Formula (4) includes compounds represented by any of the following formulae (4a) to (4d).

[0695] [Chemical formula 43]

[0696]

[0697] [Chemical formula 44]

[0698]

[0699] [Chemical formula 45]

[0700]

[0701] [Chemical formula 46]

[0702]

[0703] In one embodiment of the present invention, preferably X of formula (2) 1 is a nitrogen atom bonded to *c. Therefore, the compound of the invention includes a compound represented by the following formula (5).

[0704] [Chemical formula 47]

[0705]

[0706] L 11 It is preferably a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group, and more preferably an arylene group selected from the following.

[0707] [Chemical formula 48]

[0708]

[0709] (In the formula, * is bonded to the central nitrogen atom, and ** is bonded to the nitrogen atom of the 9-carbazolyl group. For simplicity, the optional substituents are omitted.)

[0710] As mentioned above, the "hydrogen atom" used in this specification includes protium atoms, deuterium atoms and tritium atoms. Therefore, the inventive compound may contain deuterium atoms of natural origin.

[0711] In addition, by using a compound in which a part or all of the raw material compound is deuterated, a deuterium atom can be intentionally introduced into the invention compound. Therefore, in one embodiment of the present invention, the invention compound contains at least one deuterium atom. That is, the invention compound can be a compound represented by formula (1) or the above formula contained in formula (1), and at least one of the hydrogen atoms contained in the compound is a deuterium atom.

[0712] In formula (1), R 1 ~R 4 , R is not a single bond to *a or *b 5 ~R 9 、R that is not a single bond to *b 10 ~R 14 , R 15 ~R 18 and R 20 ~R 26 The hydrogen atoms shown, L 1 and L 2 The hydrogen atoms, Ar 1 and Ar 2 At least one of the hydrogen atoms contained in the non-condensed aryl group, the condensed aryl group containing a 5-membered ring, or the heterocyclic group may be a deuterium atom.

[0713] The deuteration rate of the invention compound (the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the invention compound) depends on the deuteration rate of the raw material compound used. It is usually difficult to make the deuteration rate of all raw material compounds used 100%, so the deuteration rate of the invention compound is less than 100%, preferably 95% or less, more preferably 90% or less, and further preferably 80% or less.

[0714] The deuteration rate of the compound of the invention is 1% or more, preferably 3% or more, more preferably 5% or more, and further preferably 10% or more.

[0715] The invention compound may be a mixture of a deuterated compound (a compound into which deuterium atoms are intentionally introduced) and a non-deuterated compound, or a mixture of two or more compounds having different deuteration rates. The deuteration rate (ratio of the number of deuterium atoms to the total number of hydrogen atoms in the invention compound contained in the mixture) of such a mixture is 1% or more, preferably 3% or more, more preferably 5% or more, and further preferably 10% or more, and is less than 100%, preferably 95% or less, and more preferably 90% or less.

[0716] In the inventive compound, selected from R 1 ~R 4 , R is not a single bond to *a or *b 5 ~R 9、R that is not a single bond to *b 10 ~R 14 , and R 15 ~R 18 At least one of the hydrogen atoms shown may be a deuterium atom. The deuteration rate (the number of deuterium atoms relative to R 1 ~R 4 , R is not a single bond to *a or *b 5 ~R 9 、R that is not a single bond to *b 10 ~R 14 , and R 15 ~R 18 The ratio of the total number of hydrogen atoms shown in FIG. 1 is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and is less than 100%, preferably 95% or less, more preferably 90% or less.

[0717] In the compounds of the invention, R 20 ~R 26 At least one of the hydrogen atoms shown may be a deuterium atom. The deuteration rate (the number of deuterium atoms relative to R 20 ~R 26 The ratio of the total number of hydrogen atoms shown in FIG. 1 is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and is less than 100%, preferably 95% or less, more preferably 90% or less.

[0718] In the inventive compound, selected from L 1 and L 2 At least one of the hydrogen atoms possessed by the arylene group shown may be a deuterium atom. The deuteration rate (the ratio of the number of deuterium atoms to the total number of hydrogen atoms possessed by the arylene group) is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and is less than 100%, preferably 95% or less, more preferably 90% or less.

[0719] In the inventive compound, selected from Ar 1 and Ar 2 At least one of the hydrogen atoms possessed by the non-fused aryl group, the fused aryl group containing a 5-membered ring, or the heterocyclic group shown may be a deuterium atom. The deuteration rate (the ratio of the number of deuterium atoms to the total number of hydrogen atoms possessed by the non-fused aryl group, the fused aryl group containing a 5-membered ring, or the heterocyclic group) is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and is less than 100%, preferably 95% or less, and more preferably 90% or less.

[0720] Details of the substituents (optional substituents) in the case of "substituted or unsubstituted" included in the definitions of the above formulae are as described in "Substituents in the case of 'substituted or unsubstituted'".

[0721] Those skilled in the art can easily produce the compounds of the invention by referring to the following synthesis examples and known synthesis methods.

[0722] Specific examples of the compounds of the invention are shown below, but the compounds of the invention are not limited to the following exemplary compounds.

[0723] [Chemical formula 49]

[0724]

[0725] [Chemical formula 50]

[0726]

[0727] [Chemical formula 51]

[0728]

[0729] [Chemical formula 52]

[0730]

[0731] [Chemical formula 53]

[0732]

[0733] [Chemical formula 54]

[0734]

[0735] [Chemical formula 55]

[0736]

[0737] [Chemical formula 56]

[0738]

[0739] [Chemical formula 57]

[0740]

[0741] [Chemical formula 58]

[0742]

[0743] [Chemical formula 59]

[0744]

[0745] [Chemical formula 60]

[0746]

[0747] [Chemical formula 61]

[0748]

[0749] [Chemical formula 62]

[0750]

[0751] [Chemical formula 63]

[0752]

[0753] [Chemical formula 64]

[0754]

[0755] [Chemical formula 65]

[0756]

[0757] [Chemical formula 66]

[0758]

[0759] [Chemical formula 67]

[0760]

[0761] [Chemical formula 68]

[0762]

[0763] [Chemical formula 69]

[0764]

[0765] [Chemical formula 70]

[0766]

[0767] [Chemical formula 71]

[0768]

[0769] [Chemical formula 72]

[0770]

[0771] [Chemical formula 73]

[0772]

[0773] [Chemical formula 74]

[0774]

[0775] [Chemical formula 75]

[0776]

[0777] [Chemical formula 76]

[0778]

[0779] [Chemical formula 77]

[0780]

[0781] [Chemical formula 78]

[0782]

[0783] [Chemical formula 79]

[0784]

[0785] [Chemical formula 80]

[0786]

[0787] [Chemical formula 81]

[0788]

[0789] [Chemical formula 82]

[0790]

[0791] [Chemical formula 83]

[0792]

[0793] [Chemical formula 84]

[0794]

[0795] [Chemical formula 85]

[0796]

[0797] [Chemical formula 86]

[0798]

[0799] [Chemical formula 87]

[0800]

[0801] [Chemical formula 88]

[0802]

[0803] [Chemical formula 89]

[0804]

[0805] [Chemical formula 90]

[0806]

[0807] [Chemical formula 91]

[0808]

[0809] [Chemical formula 92]

[0810]

[0811] [Chemical formula 93]

[0812]

[0813] [Chemical formula 94]

[0814]

[0815] [Chemical formula 95]

[0816]

[0817] [Chemical formula 96]

[0818]

[0819] [Chemical formula 97]

[0820]

[0821] [Chemical formula 98]

[0822]

[0823] [Chemical formula 99]

[0824]

[0825] [Chemical formula 100]

[0826]

[0827] [Chemical Formula 101]

[0828]

[0829] [Chemical formula 102]

[0830]

[0831] [Chemical formula 103]

[0832]

[0833] [Chemical formula 104]

[0834]

[0835] [Chemical formula 105]

[0836]

[0837] [Chemical formula 106]

[0838]

[0839] [Chemical formula 107]

[0840]

[0841] [Chemical formula 108]

[0842]

[0843] [Chemical formula 109]

[0844]

[0845] [Chemical formula 110]

[0846]

[0847] [Chemical formula 111]

[0848]

[0849] [Chemical formula 112]

[0850]

[0851] [Chemical formula 113]

[0852]

[0853] [Chemical formula 114]

[0854]

[0855] [Chemical formula 115]

[0856]

[0857] [Chemical formula 116]

[0858]

[0859] [Chemical formula 117]

[0860]

[0861] [Chemical formula 118]

[0862]

[0863] [Chemical formula 119]

[0864]

[0865] [Chemical formula 120]

[0866]

[0867] [Chemical formula 121]

[0868]

[0869] [Chemical formula 122]

[0870]

[0871] [Chemical formula 123]

[0872]

[0873] [Chemical formula 124]

[0874]

[0875] [Chemical formula 125]

[0876]

[0877] [Chemical formula 126]

[0878]

[0879] [Chemical formula 127]

[0880]

[0881] [Chemical formula 128]

[0882]

[0883] [Chemical formula 129]

[0884]

[0885] [Chemical formula 130]

[0886]

[0887] [Chemical formula 131]

[0888]

[0889] [Chemical formula 132]

[0890]

[0891] [Chemical formula 133]

[0892]

[0893] [Chemical formula 134]

[0894]

[0895] [Chemical formula 135]

[0896]

[0897] [Chemical formula 136]

[0898]

[0899] [Chemical formula 137]

[0900]

[0901] [Chemical formula 138]

[0902]

[0903] [Chemical formula 139]

[0904]

[0905] [Chemical formula 140]

[0906]

[0907] [Chemical formula 141]

[0908]

[0909] [Chemical formula 142]

[0910]

[0911] [Chemical formula 143]

[0912]

[0913] [Chemical formula 144]

[0914]

[0915] [Chemical formula 145]

[0916]

[0917] [Chemical formula 146]

[0918]

[0919] [Chemical formula 147]

[0920]

[0921] [Chemical formula 148]

[0922]

[0923] [Chemical formula 149]

[0924]

[0925] [Chemical formula 150]

[0926]

[0927] [Chemical formula 151]

[0928]

[0929] [Chemical formula 152]

[0930]

[0931] [Chemical formula 153]

[0932]

[0933] [Chemical formula 154]

[0934]

[0935] [Chemical formula 155]

[0936]

[0937] [Chemical formula 156]

[0938]

[0939] [Chemical formula 157]

[0940]

[0941] [Chemical formula 158]

[0942]

[0943] [Chemical formula 159]

[0944]

[0945] [Chemical formula 160]

[0946]

[0947] [Chemical formula 161]

[0948]

[0949] [Chemical formula 162]

[0950]

[0951] [Chemical formula 163]

[0952]

[0953] [Chemical formula 164]

[0954]

[0955] [Chemical formula 165]

[0956]

[0957] [Chemical formula 166]

[0958]

[0959] [Chemical formula 167]

[0960]

[0961] [Chemical formula 168]

[0962]

[0963] [Chemical formula 169]

[0964]

[0965] [Chemical formula 170]

[0966]

[0967] [Chemical formula 171]

[0968]

[0969] [Chemical formula 172]

[0970]

[0971] [Chemical formula 173]

[0972]

[0973] [Chemical formula 174]

[0974]

[0975] [Chemical formula 175]

[0976]

[0977] [Chemical formula 176]

[0978]

[0979] [Chemical formula 177]

[0980]

[0981] [Chemical formula 178]

[0982]

[0983] [Chemical formula 179]

[0984]

[0985] [Chemical formula 180]

[0986]

[0987] [Chemical formula 181]

[0988]

[0989] [Chemical formula 182]

[0990]

[0991] [Chemical formula 183]

[0992]

[0993] [Chemical formula 184]

[0994]

[0995] [Chemical formula 185]

[0996]

[0997] [Chemical formula 186]

[0998]

[0999] [Chemical formula 187]

[1000]

[1001] [Chemical formula 188]

[1002]

[1003] [Chemical formula 189]

[1004]

[1005] [Chemical formula 190]

[1006]

[1007] [Chemical formula 191]

[1008]

[1009] [Chemical formula 192]

[1010]

[1011] [Chemical formula 193]

[1012]

[1013] [Chemical formula 194]

[1014]

[1015] [Chemical formula 195]

[1016]

[1017] [Chemical formula 196]

[1018]

[1019] [Chemical formula 197]

[1020]

[1021] [Chemical formula 198]

[1022]

[1023] [Chemical formula 199]

[1024]

[1025] [Chemical formula 200]

[1026]

[1027] [Chemical formula 201]

[1028]

[1029] [Chemical formula 202]

[1030]

[1031] [Chemical formula 203]

[1032]

[1033] [Chemical formula 204]

[1034]

[1035] [Chemical formula 205]

[1036]

[1037] [Chemical formula 206]

[1038]

[1039] [Chemical formula 207]

[1040]

[1041] [Chemical formula 208]

[1042]

[1043] [Chemical formula 209]

[1044]

[1045] [Chemical formula 210]

[1046]

[1047] [Chemical formula 211]

[1048]

[1049] [Chemical formula 212]

[1050]

[1051] [Chemical formula 213]

[1052]

[1053] [Chemical formula 214]

[1054]

[1055] [Chemical formula 215]

[1056]

[1057] [Chemical formula 216]

[1058]

[1059] [Chemical formula 217]

[1060]

[1061] [Chemical formula 218]

[1062]

[1063] [Chemical formula 219]

[1064]

[1065] [Chemical formula 220]

[1066]

[1067] [Chemical formula 221]

[1068]

[1069] [Chemical formula 222]

[1070]

[1071] [Chemical formula 223]

[1072]

[1073] [Chemical formula 224]

[1074]

[1075] [Chemical formula 225]

[1076]

[1077] [Chemical formula 226]

[1078]

[1079] [Chemical formula 227]

[1080]

[1081] [Chemical formula 228]

[1082]

[1083] [Chemical formula 229]

[1084]

[1085] [Chemical formula 230]

[1086]

[1087] [Chemical formula 231]

[1088]

[1089] [Chemical formula 232]

[1090]

[1091] [Chemical formula 233]

[1092]

[1093] [Chemical formula 234]

[1094]

[1095] [Chemical formula 235]

[1096]

[1097] [Chemical formula 236]

[1098]

[1099] [Chemical formula 237]

[1100]

[1101] [Chemical formula 238]

[1102]

[1103] [Chemical formula 239]

[1104]

[1105] [Chemical formula 240]

[1106]

[1107] [Chemical formula 241]

[1108]

[1109] [Chemical formula 242]

[1110]

[1111] [Chemical formula 243]

[1112]

[1113] [Chemical formula 244]

[1114]

[1115] [Chemical formula 245]

[1116]

[1117] [Chemical formula 246]

[1118]

[1119] [Chemical formula 247]

[1120]

[1121] [Chemical formula 248]

[1122]

[1123] [Chemical formula 249]

[1124]

[1125] [Chemical formula 250]

[1126]

[1127] [Chemical formula 251]

[1128]

[1129] [Chemical formula 252]

[1130]

[1131] [Chemical formula 253]

[1132]

[1133] [Chemical formula 254]

[1134]

[1135] [Chemical formula 255]

[1136]

[1137] [Chemical formula 256]

[1138]

[1139] [Chemical formula 257]

[1140]

[1141] [Chemical formula 258]

[1142]

[1143] [Chemical formula 259]

[1144]

[1145] [Chemical formula 260]

[1146]

[1147] [Chemical formula 261]

[1148]

[1149] [Chemical formula 262]

[1150]

[1151] [Chemical formula 263]

[1152]

[1153] [Chemical formula 264]

[1154]

[1155] [Chemical formula 265]

[1156]

[1157] [Chemical formula 266]

[1158]

[1159] [Chemical formula 267]

[1160]

[1161] [Chemical formula 268]

[1162]

[1163] [Chemical formula 269]

[1164]

[1165] [Chemical formula 270]

[1166]

[1167] [Chemical formula 271]

[1168]

[1169] [Chemical formula 272]

[1170]

[1171] [Chemical formula 273]

[1172]

[1173] [Chemical formula 274]

[1174]

[1175] [Chemical formula 275]

[1176]

[1177] [Chemical formula 276]

[1178]

[1179] [Chemical formula 277]

[1180]

[1181] [Chemical formula 278]

[1182]

[1183] [Chemical formula 279]

[1184]

[1185] [Chemical formula 280]

[1186]

[1187] [Chemical formula 281]

[1188]

[1189] [Chemical formula 282]

[1190]

[1191] [Chemical formula 283]

[1192]

[1193] [Chemical formula 284]

[1194]

[1195] [Chemical formula 285]

[1196]

[1197] [Chemical formula 286]

[1198]

[1199] [Chemical formula 287]

[1200]

[1201] [Chemical formula 288]

[1202]

[1203] [Chemical formula 289]

[1204]

[1205] [Chemical formula 290]

[1206]

[1207] [Chemical formula 291]

[1208]

[1209] [Chemical formula 292]

[1210]

[1211] [Chemical formula 293]

[1212]

[1213] [Chemical formula 294]

[1214]

[1215] [Chemical formula 295]

[1216]

[1217] [Chemical formula 296]

[1218]

[1219] [Chemical formula 297]

[1220]

[1221] [Chemical formula 298]

[1222]

[1223] [Chemical formula 299]

[1224]

[1225] [Chemical formula 300]

[1226]

[1227] [Chemical formula 301]

[1228]

[1229] [Chemical formula 302]

[1230]

[1231] [Chemical formula 303]

[1232]

[1233] [Chemical formula 304]

[1234]

[1235] [Chemical formula 305]

[1236]

[1237] [Chemical formula 306]

[1238]

[1239] [Chemical formula 307]

[1240]

[1241] Materials for organic EL devices

[1242] The material for an organic EL element of the present invention comprises the compound of the invention. The content of the compound of the invention in the material for an organic EL element is 1% by mass or more (including 100%), preferably 10% by mass or more (including 100%), more preferably 50% by mass or more (including 100%), further preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). The material for an organic EL element of the present invention is useful in the manufacture of an organic EL element.

[1243] Organic EL elements

[1244] The organic EL device of the present invention comprises an anode, a cathode and an organic layer disposed between the anode and the cathode. The organic layer comprises a light-emitting layer, and at least one layer of the organic layer comprises the compound of the present invention.

[1245] As examples of organic layers included in the invention compound, a hole transport region (hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer, etc.) disposed between the anode and the light-emitting layer, a light-emitting layer, a spacer layer, an electron transport region (electron injection layer, electron transport layer, hole blocking layer, etc.) disposed between the cathode and the light-emitting layer, etc., can be cited, but are not limited thereto. The invention compound is preferably used as a material for the hole transport region or the light-emitting layer of a fluorescent or phosphorescent EL element, more preferably as a material for the hole transport region, further preferably as a material for a hole injection layer, a hole transport layer, an electron blocking layer, or an exciton blocking layer, and particularly preferably as a material for a hole injection layer or a hole transport layer.

[1246] The organic EL element of the present invention may be a single-color light-emitting element of a fluorescent or phosphorescent light-emitting type, or a white light-emitting element of a fluorescent / phosphorescent mixed type, or a simple type having a single light-emitting unit, or a series type having a plurality of light-emitting units, wherein a fluorescent light-emitting element is preferred. Here, "light-emitting unit" refers to the smallest unit that includes an organic layer, at least one of which is a light-emitting layer, and emits light by recombination of injected holes and electrons.

[1247] For example, as a representative element structure of a simple organic EL element, the following element structures can be cited.

[1248] (1) Anode / light-emitting unit / cathode

[1249] In addition, the above-mentioned light-emitting unit may also be a multilayer type having a plurality of phosphorescent light-emitting layers and fluorescent light-emitting layers. In this case, a spacer layer may be provided between each light-emitting layer for the purpose of preventing the excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer. The following shows a representative layer structure of a simplified light-emitting unit. The layers in parentheses are optional.

[1250] (a) (hole injection layer / ) hole transport layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[1251] (b) (hole injection layer / hole transport layer / phosphorescent light emitting layer / electron transport layer ( / electron injection layer)

[1252] (c) (hole injection layer / ) hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / electron transport layer ( / electron injection layer)

[1253] (d) (hole injection layer / ) hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer / electron transport layer ( / electron injection layer)

[1254] (e) (hole injection layer / ) hole transport layer / phosphorescent light emitting layer / spacer layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[1255] (f) (hole injection layer / hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer / spacer layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[1256] (g) (hole injection layer / ) hole transport layer / first phosphorescent emitting layer / spacer layer / second phosphorescent emitting layer / spacer layer / fluorescent emitting layer / electron transport layer ( / electron injection layer)

[1257] (h) (hole injection layer / ) hole transport layer / phosphorescent emitting layer / spacer layer / first fluorescent emitting layer / second fluorescent emitting layer / electron transport layer ( / electron injection layer)

[1258] (i) (hole injection layer / ) hole transport layer / electron blocking layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[1259] (j) (hole injection layer / ) hole transport layer / electron blocking layer / phosphorescent light emitting layer / electron transport layer ( / electron injection layer)

[1260] (k) (hole injection layer / ) hole transport layer / exciton blocking layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[1261] (l) (hole injection layer / ) hole transport layer / exciton blocking layer / phosphorescent light emitting layer / electron transport layer ( / electron injection layer)

[1262] (m) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[1263] (n) (hole injection layer / ) first hole transport layer / second hole transport layer / phosphorescent light emitting layer / electron transport layer ( / electron injection layer)

[1264] (o) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer)

[1265] (p) (hole injection layer / ) first hole transport layer / second hole transport layer / phosphorescent light emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer)

[1266] (q) (hole injection layer / ) hole transport layer / fluorescent light emitting layer / hole blocking layer / electron transport layer ( / electron injection layer)

[1267] (r) (hole injection layer / ) hole transport layer / phosphorescent light emitting layer / hole blocking layer / electron transport layer ( / electron injection layer)

[1268] (s) (hole injection layer / ) hole transport layer / fluorescent light emitting layer / exciton blocking layer / electron transport layer ( / electron injection layer)

[1269] (t) (hole injection layer / ) hole transport layer / phosphorescent light emitting layer / exciton blocking layer / electron transport layer ( / electron injection layer)

[1270] Each of the above-mentioned phosphorescent or fluorescent light-emitting layers can be set as a layer showing a different light color from each other. Specifically, in the above-mentioned light-emitting unit (f), there can be mentioned a layer structure such as (hole injection layer / ) hole transport layer / first phosphorescent light-emitting layer (red light emission) / second phosphorescent light-emitting layer (green light emission) / spacer layer / fluorescent light-emitting layer (blue light emission) / electron transport layer.

[1271] It should be noted that an electron blocking layer may be appropriately provided between each light-emitting layer and the hole transport layer or the spacer layer. In addition, a hole blocking layer may be appropriately provided between each light-emitting layer and the electron transport layer. By providing an electron blocking layer or a hole blocking layer, electrons or holes may be enclosed in the light-emitting layer, thereby increasing the recombination probability of the charges in the light-emitting layer and improving the luminous efficiency.

[1272] As a typical element structure of a tandem organic EL element, the following element structures can be mentioned.

[1273] (2) Anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode

[1274] Here, the first light-emitting unit and the second light-emitting unit may be independently selected from the light-emitting units described above, for example.

[1275] The intermediate layer is generally also called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, and an intermediate insulating layer. The intermediate layer supplies electrons to the first light-emitting unit and holes to the second light-emitting unit, and can be composed of known materials.

[1276] Figure 1 : is a schematic diagram showing an example of the structure of the organic EL element of the present invention. The organic EL element 1 has a substrate 2, an anode 3, a cathode 4 and a light-emitting unit 10 arranged between the anode 3 and the cathode 4. The light-emitting unit 10 has a light-emitting layer 5. There is a hole transport region 6 (hole injection layer, hole transport layer, etc.) between the light-emitting layer 5 and the anode 3, and there is an electron transport region 7 (electron injection layer, electron transport layer, etc.) between the light-emitting layer 5 and the cathode 4. In addition, an electron blocking layer (not shown) may be provided on the anode 3 side of the light-emitting layer 5, and a hole blocking layer (not shown) may be provided on the cathode 4 side of the light-emitting layer 5. In this way, electrons and holes can be confined in the light-emitting layer 5, thereby further improving the generation efficiency of excitons in the light-emitting layer 5.

[1277] Figure 2 Schematic diagram showing another structure of the organic EL element of the present invention. The organic EL element 11 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 20 disposed between the anode 3 and the cathode 4. The light-emitting unit 20 has a light-emitting layer 5. The hole transport region disposed between the anode 3 and the light-emitting layer 5 is formed by a hole injection layer 6a, a first hole transport layer 6b, and a second hole transport layer 6c. In addition, the electron transport region disposed between the light-emitting layer 5 and the cathode 4 is formed by a first electron transport layer 7a and a second electron transport layer 7b.

[1278] It should be noted that in the present invention, a host combined with a fluorescent dopant (fluorescent luminescent material) is referred to as a fluorescent host, and a host combined with a phosphorescent dopant is referred to as a phosphorescent host. The fluorescent host and the phosphorescent host are not distinguished only by the molecular structure. That is, the phosphorescent host refers to a material that forms a phosphorescent luminescent layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material for forming a fluorescent luminescent layer. The same is true for the fluorescent host.

[1279] substrate

[1280] The substrate is used as a support of the organic EL element. As the substrate, for example, a plate of glass, quartz, plastic, etc. can be used. In addition, a flexible substrate can also be used. As the flexible substrate, for example, a plastic substrate formed of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, etc. can be cited. In addition, an inorganic vapor-deposited film can also be used.

[1281] anode

[1282] The anode formed on the substrate preferably uses a metal, alloy, conductive compound, and a mixture thereof with a large work function (specifically, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO: Indium Tin Oxide, indium tin oxide); indium oxide-tin oxide containing silicon or silicon oxide; indium oxide-zinc oxide; indium oxide containing tungsten oxide and zinc oxide; graphene, etc. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the above metals (such as titanium nitride) can be mentioned.

[1283] These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering a target containing 1 to 10 wt% zinc oxide relative to indium oxide; indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering a target containing 0.5 to 5 wt% tungsten oxide and 0.1 to 1 wt% zinc oxide relative to indium oxide. In addition, it can also be produced by vacuum evaporation, coating, inkjet, spin coating, etc.

[1284] The hole injection layer formed adjacent to the anode is formed using a material that is easy to inject holes and is independent of the work function of the anode. Therefore, as the electrode material, generally used materials (such as metals, alloys, conductive compounds, and mixtures thereof, elements belonging to the first or second group of the periodic table) can be used.

[1285] It is also possible to use elements belonging to the first or second group of the periodic table as materials with a small work function, i.e., alkali metals such as lithium (Li), cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing them. It should be noted that when using alkali metals, alkaline earth metals, and alloys containing them to form anodes, vacuum evaporation methods and sputtering methods can be used. In addition, when using silver pastes, coating methods, inkjet methods, etc. can be used.

[1286] Hole injection layer

[1287] The hole injection layer is a layer containing a material with high hole injection properties (hole injection material), and is formed between the anode and the light-emitting layer, or, if present, between the hole transport layer and the anode.

[1288] As hole injecting materials other than the invention compound, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. can be used.

[1289] Examples of hole injection layer materials include low molecular weight organic compounds such as 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNAB). TPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) and other aromatic amine compounds.

[1290] High molecular weight compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, there can be mentioned high molecular weight compounds such as poly(N-vinyl carbazole) (abbreviated as PVK), poly(4-vinyl triphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD). In addition, high molecular weight compounds to which an acid is added, such as poly(3,4-ethylenedioxythiophene) / poly(styrene sulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrene sulfonic acid) (PAni / PSS), can also be used.

[1291] Furthermore, an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K) is also preferably used.

[1292] [Chemical formula 308]

[1293]

[1294] (In the above formula, R 21 ~R 26Each independently represents a cyano group, -CONH2, a carboxyl group, or a -COOR 27 (R 27 represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms). In addition, R 21 and R 22 , R 23 and R 24 and R 25 and R 26 Two adjacent ones of can be bonded to each other to form a group represented by -CO-O-CO-. )

[1295] As R 27 , examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, and cyclohexyl.

[1296] Hole transport layer

[1297] The hole transport layer is a layer containing a material with high hole transport properties (hole transport material) and is formed between the anode and the light emitting layer, or, if present, between the hole injection layer and the light emitting layer. The inventive compound can be used alone or in combination with the following compounds for the hole transport layer.

[1298] The hole transport layer may be a single-layer structure or a multilayer structure including more than two layers. For example, the hole transport layer may be a two-layer structure including a first hole transport layer (anode side) and a second hole transport layer (cathode side). In one embodiment of the present invention, the hole transport layer of the single-layer structure is preferably adjacent to the light-emitting layer. In addition, the hole transport layer closest to the cathode in the multilayer structure, such as the second hole transport layer of the two-layer structure, is preferably adjacent to the light-emitting layer. In another embodiment of the present invention, an electron blocking layer described later may be interposed between the hole transport layer of the single-layer structure and the light-emitting layer, or between the hole transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer.

[1299] In the above-mentioned two-layer hole transport layer, the compound of the invention may be contained in one of the first hole transport layer and the second hole transport layer, or may be contained in both.

[1300] In one embodiment of the present invention, the inventive compound is preferably contained only in the first hole transport layer. In another embodiment, the inventive compound is preferably contained only in the second hole transport layer. In another embodiment, the inventive compound is preferably contained in both the first hole transport layer and the second hole transport layer.

[1301] In one embodiment of the present invention, from the viewpoint of production cost, the compound of the invention contained in one or both of the first hole transport layer and the second hole transport layer is preferably a protium body.

[1302] The above-mentioned protium compound refers to a compound of the invention in which all hydrogen atoms in the formula (1) are protium atoms.

[1303] Therefore, the present invention includes an organic EL element, wherein one or both of the first hole transport layer and the second hole transport layer contain the invention compound substantially composed of only the protium body. "The invention compound substantially composed of only the protium body" means that the content ratio of the protium body relative to the total amount of the compound represented by formula (1) is 90 mol% or more, preferably 95 mol% or more, and more preferably 99 mol% or more (including 100%).

[1304] As hole transport layer materials other than the inventive compound, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used.

[1305] Examples of the aromatic amine compound include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluorene]-1,1'-biphenyl]-1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), -2-yl)-N-phenylamino]biphenyl (abbreviated as DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB). The above compounds have 10 -6 cm 2 / Vs and above hole mobility.

[1306] Examples of the carbazole derivative include 4,4′-di(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: PCzPA).

[1307] Examples of the anthracene derivative include 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth).

[1308] A polymer compound such as poly(N-vinylcarbazole) (abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation: PVTPA) may also be used.

[1309] However, any compound other than the above-mentioned compounds may be used as long as the compound has a higher hole-transporting property than an electron-transporting property.

[1310] Dopant materials for the light-emitting layer

[1311] The light-emitting layer is a layer containing a material with high luminescence (dopant material), and various materials can be used. For example, fluorescent materials and phosphorescent materials can be used as dopant materials. Fluorescent materials are compounds that emit light in a singlet excited state, and phosphorescent materials are compounds that emit light in a triplet excited state.

[1312] As the blue fluorescent material that can be used for the light-emitting layer, pyrene derivatives, styrylamine derivatives, Derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. Specifically, N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2 S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthracenyl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthracenyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBAPA), etc. can be mentioned.

[1313] As green fluorescent light-emitting materials that can be used for the light-emitting layer, aromatic amine derivatives can be used. Specifically, N-(9,10-diphenyl-2-anthracenyl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCABPhA), N-(9,10-diphenyl-2-anthracenyl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPAPhA), PA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviated as 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviated as DPhAPhA), etc.

[1314] As the red fluorescent luminescent material that can be used for the light-emitting layer, there can be used tetracene derivatives, diamine derivatives, etc. Specifically, there can be mentioned N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviated as: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviated as: p-mPhAFD), etc.

[1315] As a blue phosphorescent material that can be used for the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used. Specifically, bis[2-(4',6'-difluorophenyl)pyridine-N, C2']iridium(III)tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridine-N, C2']iridium(III)picolinate (abbreviation: FIrpic), bis[2-(3',5'bistrifluoromethylphenyl)pyridine-N, C2']iridium(III)picolinate (abbreviation: Ir(CF3ppy)2(pic)), bis[2-(4',6'-difluorophenyl)pyridine-N, C2']iridium(III)acetylacetonate (abbreviation: FIracac), etc. are mentioned.

[1316] As green phosphorescent materials that can be used for the light-emitting layer, iridium complexes are used, such as tris(2-phenylpyridine-N, C2')iridium(III) (abbreviated as Ir(ppy)3), bis(2-phenylpyridine-N, C2')iridium(III)acetylacetonate (abbreviated as Ir(PPy)2(acac)), bis(1,2-diphenyl-1H-benzimidazole)iridium(III)acetylacetonate (abbreviated as Ir(pbi)2(acac)), and bis(benzo[h]quinoline)iridium(III)acetylacetonate (abbreviated as Ir(bzq)2(acac)).

[1317] As a red phosphorescent material that can be used for the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used. Specifically, organic metal complexes such as bis[2-(2'-benzo[4,5-α]thienyl)pyridine-N,C3']iridium(III)acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinoline-N,C2')iridium(III)acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrinplatinum(II) (abbreviation: PtOEP) can be cited.

[1318] In addition, tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviated as Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedione)(monophenanthroline)europium(III)

[1319] Rare earth metal complexes such as Eu(DBM)3(Phen) and tris[1-(2-thiophenoyl)-3,3,3-trifluoroacetone](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3(Phen)) can be used as phosphorescent materials because the luminescence comes from rare earth metal ions (electron transitions between different multiplicities).

[1320] Host material of the light-emitting layer

[1321] The light-emitting layer may be formed by dispersing the above-mentioned dopant material in another material (host material). It is preferable to use a material having a higher lowest unoccupied molecular orbital level (LUMO level) than the dopant material and a lower highest occupied molecular orbital level (HOMO level) than the dopant material.

[1322] As main materials, for example:

[1323] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes,

[1324] (2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives,

[1325] (3) Carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or Derivatives and other condensed aromatic compounds,

[1326] (4) Aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives.

[1327] For example, metal complexes such as tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-hydroxyquinoline)aluminum(III) (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium(II) (abbreviated as BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO), and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ) can be used;

[1328] 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (OXD-7), 3-(4-biphenyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ), 2,2',2"-(1,3,5-phenyltriyl)tris(1-phenyl-1H-benzimidazole) (TPBI), bathophenanthroline (BPhen), bathocuproin (BCP), and other heterocyclic compounds; 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (CzPA), 3,6-diphenyl-9-[4-(10 9,10-bis(3,5-diphenylphenyl)anthracene (DPPA), 9,10-di(2-naphthyl)anthracene (DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (t-BuDNA), 9,9'-bianthracene (BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (DPNS2), 3,3',3"-(benzene-1,3,5-triyl)tripyrene (TPB3), 9,10-diphenylanthracene (DPAnth), 6,12-dimethoxy-5,11-diphenyl Equi-fused aromatic compounds; and

[1329] N,N-diphenyl-9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole-3-amine (abbreviated as: CzA1PA), 4-(10-phenyl-9-anthracenyl)triphenylamine (abbreviated as: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole-3-amine (abbreviated as: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthracenyl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviated as: PCAPBA), N-(9,10-diphenyl-2-anthracenyl)-N,9-diphenyl- Aromatic amine compounds such as 9H-carbazole-3-amine (abbreviation: 2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), and 4,4'-bis[N-(spiro-9,9'-difluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). Two or more types of the host material can be used.

[1330] In particular, in the case of a blue fluorescent element, it is preferable to use the following anthracene compound as a host material.

[1331] [Chemical formula 309]

[1332]

[1333] [Chemical formula 310]

[1334]

[1335] [Chemical formula 311]

[1336]

[1337] Electron transport layer

[1338] The electron transport layer is a layer containing a material with a high electron transport property (electron transport material), and is formed between the light emitting layer and the cathode, or, if present, between the electron injection layer and the light emitting layer.

[1339] The electron transport layer may be a single-layer structure or a multilayer structure comprising more than two layers. For example, the electron transport layer may be a two-layer structure comprising a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one embodiment of the present invention, the electron transport layer of the single-layer structure is preferably adjacent to the light-emitting layer. In addition, the electron transport layer closest to the anode in the multilayer structure, such as the first electron transport layer of the two-layer structure, is preferably adjacent to the light-emitting layer. In another embodiment of the present invention, a hole blocking layer described later may be provided between the electron transport layer of the single-layer structure and the light-emitting layer, or between the electron transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer.

[1340] For example, the electron transport layer may be

[1341] (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes,

[1342] (2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives,

[1343] (3)Polymer compounds.

[1344] Examples of the metal complex include tris(8-hydroxyquinoline)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-hydroxyquinoline)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (abbreviation: BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviation: BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviation: ZnBTZ).

[1345] Examples of the heteroaromatic compound include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ)), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), and 4,4′-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs).

[1346] Examples of the polymer compound include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).

[1347] The above materials are 10 -6 cm 2 It should be noted that materials other than the above may be used for the electron transport layer as long as the electron transport property is higher than the hole transport property.

[1348] Electron injection layer

[1349] The electron injection layer is a layer containing a material with high electron injection. The electron injection layer can use alkali metals such as lithium (Li), cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), strontium (Sr), rare earth metals such as europium (Eu), ytterbium (Yb) and compounds containing these metals. As such compounds, for example, alkali metal oxides, alkali metal halides, organic complexes containing alkali metals, alkaline earth metal oxides, alkaline earth metal halides, organic complexes containing alkaline earth metals, rare earth metal oxides, rare earth metal halides and organic complexes containing rare earth metals can be cited. In addition, a variety of these compounds can also be mixed for use.

[1350] Alternatively, a material containing an alkali metal, an alkaline earth metal, or a compound thereof in a material having an electron transport property, specifically, a material containing magnesium (Mg) in Alq, etc. In this case, electrons can be injected more efficiently from the cathode.

[1351] Alternatively, a composite material formed by mixing an organic compound and an electron donor (donor) can also be used for the electron injection layer. Since the organic compound accepts electrons from the electron donor, the electron injection and electron transport properties of such a composite material are excellent. At this time, as an organic compound, it is preferably a material with excellent transmission of the accepted electrons. Specifically, for example, the above-mentioned materials (metal complexes, heteroaromatic compounds, etc.) constituting the electron transport layer can be used. As an electron donor, any material that exhibits electron donating properties to organic compounds can be used. Specifically, alkali metals, alkaline earth metals and rare earth metals are preferred, and lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. can be cited. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, and lithium oxide, calcium oxide, barium oxide, etc. can be cited. In addition, Lewis bases such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviated as: TTF) can also be used.

[1352] cathode

[1353] The cathode preferably utilizes metals, alloys, conductive compounds, and mixtures thereof with a small work function (specifically, less than 3.8 eV). Specific examples of such cathode materials include elements belonging to the first or second group of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys thereof (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), and ytterbium (Yb), and alloys thereof.

[1354] It should be noted that when an alkali metal, an alkaline earth metal, or an alloy thereof is used to form the cathode, a vacuum deposition method or a sputtering method may be used. In addition, when a silver paste or the like is used, a coating method or an inkjet method may be used.

[1355] It should be noted that, by providing an electron injection layer, a cathode can be formed using various conductive materials such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the size of the work function. These conductive materials can be formed into films using sputtering, inkjet, spin coating, etc.

[1356] Insulation layer

[1357] Organic EL elements are prone to pixel defects due to leakage and short circuits due to the application of an electric field to an ultra-thin film. In order to prevent such pixel defects, an insulating layer including an insulating thin film layer may be inserted between a pair of electrodes.

[1358] Examples of the material used in the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. It should be noted that mixtures and laminates thereof may be used.

[1359] Spacer

[1360] The above-mentioned spacer layer refers to a layer provided between the fluorescent emitting layer and the phosphorescent emitting layer, for example, in order to prevent the excitons generated in the phosphorescent emitting layer from diffusing to the fluorescent emitting layer or to adjust the carrier balance when the fluorescent emitting layer and the phosphorescent emitting layer are stacked. In addition, the spacer layer may also be provided between a plurality of phosphorescent emitting layers.

[1361] Since the spacer layer is disposed between the light-emitting layers, it is preferably a material having both electron transport and hole transport properties. In addition, in order to prevent the diffusion of triplet energy in the adjacent phosphorescent light-emitting layer, the triplet energy is preferably above 2.6 eV. As the material for the spacer layer, the same material as the material for the hole transport layer mentioned above can be cited.

[1362] Barrier layer

[1363] Blocking layers such as an electron blocking layer, a hole blocking layer, and an exciton blocking layer may be provided adjacent to the light-emitting layer. The electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer, and the hole blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron transport layer. The exciton blocking layer has the function of preventing excitons generated in the light-emitting layer from diffusing to surrounding layers and sealing the excitons in the light-emitting layer.

[1364] Each layer of the organic EL element can be formed by a conventionally known vapor deposition method, coating method, etc. For example, it can be formed by a known method based on a vapor deposition method such as a vacuum vapor deposition method, a molecular beam vapor deposition method (MBE method), or a coating method such as a dip coating method, a spin coating method, a casting method, a rod coating method, a roll coating method, etc. using a solution of a compound forming a layer.

[1365] The thickness of each layer is not particularly limited. Generally, if the thickness is too thin, defects such as pinholes are likely to occur, whereas if it is too thick, a high driving voltage is required and the efficiency deteriorates. Therefore, it is usually 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm.

[1366] The organic EL element can be used in electronic devices such as display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and light-emitting devices for lighting and vehicle lamps.

[1367] Example

[1368] Hereinafter, the present invention will be described in further detail using examples, but the present invention is not limited to the following examples.

[1369] Invention compounds used in the manufacture of organic EL devices of Examples 1 to 13

[1370] [Chemical formula 312]

[1371]

[1372] [Chemical formula 314]

[1373]

[1374] Comparative compounds used in the manufacture of organic EL devices of Comparative Examples 1 and 2

[1375] [Chemical formula 315]

[1376]

[1377] Comparative compound Ref-1 is a compound described in prior art documents 1 to 3.

[1378] Other compounds used in the manufacture of organic EL devices of Examples 1 to 13 and Comparative Examples 1 to 2

[1379] [Chemical formula 316]

[1380]

[1381] Fabrication of organic EL elements

[1382] Example 1

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

[1384] The cleaned glass substrate with a transparent electrode was mounted on a substrate holder of a vacuum evaporation device, and compound HT-1 and compound HI-1 were co-evaporated on the surface of the side where the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-1 to compound HI-1 (HT-1: HI-1) was 97:3.

[1385] Next, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a film thickness of 80 nm.

[1386] Next, compound Inv-1 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 10 nm.

[1387] Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated on the second hole transport layer to form a 25 nm thick light emitting layer. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 96:4.

[1388] Next, compound ET-1 was vapor-deposited on the light-emitting layer to form a first electron transport layer having a film thickness of 10 nm.

[1389] Next, compound ET-2 was vapor-deposited on the first electron transport layer to form a second electron transport layer having a film thickness of 15 nm.

[1390] Next, LiF was vapor-deposited on the second electron transport layer to form an electron injecting electrode with a film thickness of 1 nm.

[1391] Then, metal Al was vapor-deposited on the electron injecting electrode to form a metal cathode with a film thickness of 50 nm.

[1392] The layer structure of the organic EL device of Example 1 obtained in this manner is shown below.

[1393] ITO(130) / HT-1:HI-1=97:3(10) / HT--1(80) / Inv-1(10) / BH-1:BD-1=96:4(25) / ET-1(10) / ET-2(15) / LiF(1) / Al(50)

[1394] In the above layer configuration, the numbers in parentheses are film thicknesses (nm), and the ratios are mass ratios.

[1395] Determination of component life (LT95)

[1396] The obtained organic EL device was heated at a current density of 50 mA / cm 2The battery was driven by direct current, and the time required for the luminance to decrease to 95% of the initial luminance was measured, and this time was defined as the 95% lifespan (LT95).

[1397] Examples 2 to 13 and Comparative Examples 1 to 2

[1398] Each organic EL device was produced in the same manner as in Example 1 except that the second hole transport layer material was changed to each compound described in Table 1, and LT95 was measured. The results are shown in Table 1.

[1399] [Table 1]

[1400] Table 1

[1401]

[1402] It is clear from the results in Table 1 that, compared with the amine compound having a p-(2-naphthyl)phenyl group bonded to the central nitrogen atom at the terminal (comparison compound Ref-1), the inventive compounds having a m-(2-naphthyl)phenyl group bonded to the central nitrogen atom at the terminal (compounds Inv-1 to Inv-13) provide organic EL elements with significantly improved element life.

[1403] Compounds Inv-1 to Inv-13 synthesized in Synthesis Examples 1 to 13 [Chemical Formula 317]

[1404]

[1405] [Chemical formula 319]

[1406]

[1407] Compound Inv-13

[1408] Intermediate Synthesis Example 1: Synthesis of Intermediate A

[1409] [Chemical formula 320]

[1410]

[1411] Under argon atmosphere, a mixture of 4-chlorophenylboric acid (11.66 g, 74.6 mmol), 2-(3-bromophenyl)naphthalene (19.2 g, 67.8 mmol), tetrakis(triphenylphosphine)palladium(0) (2.35 g, 2.03 mmol), sodium carbonate (21.5 g, 203 mmol), dimethoxyethane (DME) (271 mL) and water (67.8 mL) was stirred at 80°C for 7 hours. The reaction solution was cooled to room temperature, and filtered after adding water. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (15.78 g). The yield was 73%.

[1412] Intermediate Synthesis Example 2: Synthesis of Intermediate B

[1413] [Chemical formula 321]

[1414]

[1415] Under argon atmosphere, a mixture of (4'-chloro[1,1'-biphenyl]-4-yl)boric acid (2.32 g, 10.0 mmol), 2-(3-bromophenyl)naphthalene (3.11 g, 11.0 mmol), tetrakis(triphenylphosphine)palladium(0) (0.346 g, 0.2 mmol), sodium carbonate (3.18 g, 30 mmol), DME (40 mL) and water (10 mL) was stirred at 80°C for 7 hours. The reaction solution was cooled to room temperature, and filtered after adding water. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (3.05 g). The yield was 78%.

[1416] Intermediate Synthesis Example 3: Synthesis of Intermediate C

[1417] [Chemical formula 322]

[1418]

[1419] Synthesis of intermediate C-1

[1420] Under argon atmosphere, 4,4,5,5-tetramethyl-2-(2-naphthyl-1,3,4,5,6,7,8-d7)-1,3,2-dioxaborolane (2.61 g, 10.0 mmol), 1-bromo-3-iodobenzene (3.11 g, 11.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.183 g, 0.20 mmol), XantPhos (0.462 g, 0.80 mmol), sodium carbonate (3.18 g, 30 mmol), DME

[1421] A mixture of 40 mL of 1,2-dihydro-2-nitropropene (40 mL) and water (10 mL) was stirred at 80°C for 7 hours. The reaction solution was cooled to room temperature, and filtered after adding water. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (2.50 g). The yield was 86%.

[1422] Synthesis of Intermediate C

[1423] Under argon atmosphere, a mixture of 4-chlorophenylboronic acid (1.34 g, 8.55 mmol), intermediate C-1 (2.50 g, 7.77 mmol), tetrakis(triphenylphosphine)palladium(0) (0.266 g, 0.23 mmol), sodium carbonate (2.47 g, 23.3 mmol), DME (31 mL) and water (8 mL) was stirred at 80°C for 7 hours. The reaction solution was cooled to room temperature, and filtered after adding water. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (1.98 g). The yield was 79%.

[1424] Synthesis Example 1: Synthesis of Compound Inv-1

[1425] [Chemical formula 323]

[1426]

[1427] Under argon atmosphere, a mixture of N-[1,1'-biphenyl]-4-yl-[1,1'-biphenyl]-4-amine (1.93 g, 6.00 mmol), intermediate A (2.08 g, 6.60 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.110 g, 0.120 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.139 g, 0.480 mmol), sodium tert-butoxide (0.865 g, 9.00 mmol) and xylene (30 mL) was stirred at 110° C. for 3.5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (1.45 g). The yield was 40%.

[1428] The obtained compound was analyzed by mass spectrometry (m / e=600 with respect to molecular weight 599.78) and was identified as Compound Inv-1.

[1429] Synthesis Example 2: Synthesis of Compound Inv-2

[1430] [Chemical formula 324]

[1431]

[1432] Under argon atmosphere, a mixture of N-[4-(4-dibenzofuranyl)phenyl][1,1'-biphenyl]-4-amine (8.00 g, 19.4 mmol), intermediate A (6.73 g, 21.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.356 g, 0.389 mmoL), tri-tert-butylphosphonium tetrafluoroborate (0.451 g, 1.56 mmoL), sodium tert-butoxide (2.80 g, 29.20 mmoL) and xylene (97 mL) synthesized in the same manner as described in International Publication No. 2007 / 125714 was stirred at 110° C. for 4 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (7.43 g). The yield was 55%.

[1433] The obtained compound was subjected to mass spectrometry analysis (m / e=690 relative to molecular weight 689.86), and was identified as Compound Inv-2.

[1434] Synthesis Example 3: Synthesis of Compound Inv-3

[1435] [Chemical formula 325]

[1436]

[1437] Under argon atmosphere, a mixture of N-[4-(4-dibenzofuranyl)phenyl][1,1'-biphenyl]-4-amine (2.80 g, 6.81 mmoL), intermediate B (2.93 g, 7.49 mmoL), tris(dibenzylideneacetone)dipalladium(0) (0.124 g, 0.136 mmoL), tri-tert-butylphosphonium tetrafluoroborate (0.158 g, 0.545 mmoL), sodium tert-butoxide (0.98 g, 10.2 mmoL) and xylene (34 mL) synthesized in the same manner as described in International Publication No. 2007 / 125714 was stirred at 110° C. for 4 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (3.29 g). The yield was 63%.

[1438] The obtained compound was analyzed by mass spectrometry (m / e=766, relative molecular weight: 765.96) and was identified as Compound Inv-3.

[1439] Synthesis Example 4: Synthesis of Compound Inv-4

[1440] [Chemical formula 326]

[1441]

[1442] Under argon atmosphere, a mixture of N-[4-(4-dibenzofuranyl)phenyl][1,1'-biphenyl]-4-amine (2.30 g, 5.59 mmol), intermediate C (1.98 g, 6.15 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.103 g, 0.112 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.130 g, 0.448 mmol), sodium tert-butoxide (0.806 g, 8.39 mmol) and xylene (28 mL) synthesized in the same manner as described in International Publication No. 2007 / 125714 was stirred at 110° C. for 4 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (2.38 g). The yield was 61%.

[1443] The obtained compound was analyzed by mass spectrometry (m / e=697 relative to molecular weight 696.90), and was identified as Compound Inv-4.

[1444] Synthesis Example 5: Synthesis of Compound Inv-5

[1445] [Chemical formula 327]

[1446]

[1447] Under argon atmosphere, a mixture of N-[4-(3-dibenzofuranyl)phenyl][1,1'-biphenyl]-4-amine (4.11 g, 10.0 mmol), intermediate A (2.08 g, 11.0 mmol), tri(dibenzylideneacetone)dipalladium(0) (0.110 g, 0.20 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.139 g, 0.80 mmol), sodium tert-butoxide (0.865 g, 15.0 mmol) and xylene (50 mL) was stirred at 110° C. for 3.5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (3.55 g). The yield was 59%.

[1448] The obtained compound was analyzed by mass spectrometry (m / e=690 with respect to molecular weight 689.86) and was identified as compound Inv-5.

[1449] Synthesis Example 6: Synthesis of Compound Inv-6

[1450] [Chemical formula 328]

[1451]

[1452] Under argon atmosphere, a mixture of N-[4-(4-dibenzothienyl)phenyl][1,1'-biphenyl]-4-amine (4.28 g, 10.0 mmol), intermediate A (2.08 g, 11.0 mmol), tri(dibenzylideneacetone)dipalladium(0) (0.110 g, 0.20 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.139 g, 0.80 mmol), sodium tert-butoxide (0.865 g, 15.0 mmol) and xylene (50 mL) was stirred at 110° C. for 3.5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (3.09 g). The yield was 44%.

[1453] The obtained compound was analyzed by mass spectrometry (m / e=706 with respect to molecular weight 705.92), and was identified as compound Inv-6.

[1454] Synthesis Example 7: Synthesis of Compound Inv-7

[1455] [Chemical formula 329]

[1456]

[1457] Under argon atmosphere, a mixture of N-[1,1'-biphenyl]-4-yl-9,9-diphenyl-9H-fluorene-2-amine (4.86g, 10.0mmoL), intermediate A (2.08g, 11.0mmol), tris(dibenzylideneacetone)dipalladium(0) (0.110g, 0.20mmoL), tri-tert-butylphosphonium tetrafluoroborate (0.139g, 0.80mmoL), sodium tert-butoxide (0.865g, 15.0mmoL) and xylene (50mL) was stirred at 110°C for 3.5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (3.62g). The yield was 47%.

[1458] The obtained compound was analyzed by mass spectrometry (m / e=764, relative molecular weight: 763.98) and was identified as Compound Inv-7.

[1459] Synthesis Example 8: Synthesis of Compound Inv-8

[1460] [Chemical formula 330]

[1461]

[1462] Under argon atmosphere, a mixture of N-[3-(4-dibenzofuranyl)phenyl][1,1'-biphenyl]-4-amine (4.11 g, 10.0 mmol), intermediate A (2.08 g, 11.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.110 g, 0.20 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.139 g, 0.80 mmol), sodium tert-butoxide (0.865 g, 15.0 mmol) and xylene (50 mL) was stirred at 110° C. for 3.5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (3.89 g). The yield was 56%.

[1463] The obtained compound was analyzed by mass spectrometry (m / e=690 with respect to molecular weight 689.86) and was identified as compound Inv-8.

[1464] Synthesis Example 9: Synthesis of Compound Inv-9

[1465] [Chemical formula 331]

[1466]

[1467] Under an argon atmosphere, a mixture of [1,1'-biphenyl]-4-yl-[1,1':4'1"-triphenyl]-4-amine (4.11 g, 10.0 mmol), intermediate A (2.08 g, 11.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.110 g, 0.20 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.139 g, 0.80 mmol), sodium tert-butoxide (0.865 g, 15.0 mmol) and xylene (50 mL) was stirred at 110°C for 3.5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (4.07 g). The yield was 60%.

[1468] The obtained compound was analyzed by mass spectrometry (m / e=676 with respect to molecular weight 675.88) and was identified as compound Inv-9.

[1469] Synthesis Example 10: Synthesis of Compound Inv-10

[1470] [Chemical formula 332]

[1471]

[1472] Under argon atmosphere, a mixture of [1,1'-biphenyl]-4-yl-1-dibenzofuranamine (3.35 g, 10.0 mmol), intermediate A (2.08 g, 11.0 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.110 g, 0.20 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.139 g, 0.80 mmol), sodium tert-butoxide (0.865 g, 15.0 mmol) and xylene (50 mL) was stirred at 110° C. for 3.5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (2.60 g). The yield was 42%.

[1473] The obtained compound was analyzed by mass spectrometry (m / e=614 ​​with respect to molecular weight 613.76) and was identified as compound Inv-10.

[1474] Synthesis Example 11: Synthesis of Compound Inv-11

[1475] [Chemical formula 333]

[1476]

[1477] Under argon atmosphere, a mixture of N-[3-(9H-carbazole-9-yl)phenyl][1,1'-biphenyl]-4-amine (4.11 g, 10.0 mmol), intermediate A (2.08 g, 11.0 mmol), tri(dibenzylideneacetone)dipalladium(0) (0.110 g, 0.20 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.139 g, 0.80 mmol), sodium tert-butoxide (0.865 g, 15.0 mmol) and xylene (50 mL) was stirred at 110° C. for 3.5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (2.95 g). The yield was 43%.

[1478] The obtained compound was analyzed by mass spectrometry (m / e=689 with respect to molecular weight 688.87), and was identified as compound Inv-11.

[1479] Synthesis Example 12: Synthesis of Compound Inv-12

[1480] [Chemical formula 334]

[1481]

[1482] Under argon atmosphere, a mixture of N-[4-(4-dibenzofuranyl)phenyl]-1-dibenzofuranamine (3.35 g, 10.0 mmol), intermediate A (2.08 g, 11.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.110 g, 0.20 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.139 g, 0.80 mmol), sodium tert-butoxide (0.865 g, 15.0 mmol) and xylene (50 mL) was stirred at 110° C. for 3.5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (2.46 g). The yield was 35%.

[1483] The obtained compound was identified as Compound Inv-12 by mass spectrometry analysis (m / e=704, relative molecular weight: 703.84).

[1484] Synthesis Example 13: Synthesis of Compound Inv-13

[1485] [Chemical formula 335]

[1486]

[1487] Under argon atmosphere, a mixture of [1,1'-biphenyl]-4-yl-[1,1'-biphenyl]-2-amine (3.21 g, 10.0 mmol), intermediate A (2.08 g, 11.0 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.110 g, 0.20 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.139 g, 0.80 mmol), sodium tert-butoxide (0.865 g, 15.0 mmol) and xylene (50 mL) was stirred at 110° C. for 3.5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (2.77 g). The yield was 46%.

[1488] The obtained compound was analyzed by mass spectrometry (m / e=600 with respect to molecular weight 599.78) and was identified as compound Inv-13.

[1489] Description of Reference Numerals

[1490] 1.11: Organic EL components

[1491] 2: Substrate

[1492] 3: Anode

[1493] 4: Cathode

[1494] 5: Luminous layer

[1495] 6: Hole transport region (hole transport layer)

[1496] 6a: Hole injection layer

[1497] 6b: 1st hole transport layer

[1498] 6c: Second hole transport layer

[1499] 7: Electron transport region (electron transport layer)

[1500] 7a: 1st electron transport layer

[1501] 7b: Second electron transport layer

[1502] 10, 20: Light-emitting unit

Claims

1. A compound represented by the following formula (1), In formula (1), m is 0 or 1, n is 0 or 1, When m is 0 and n is 0, *b is bonded to carbon atom *1. When m is 1 and n is 0, R 5 ~R 9 One of them is a single bond to *b, When m is 0 and n is 1, *a is bonded to the carbon atom *1 and is selected from R 10 ~R 14 One of them is a single bond to *b, When m is 1 and n is 1, R 5 ~R 9 One of them is a single bond bonded to *a, selected from R 10 ~R 14 One of them is a single bond to *b, R 1 ~R 4 , R is not a single bond to *a or *b 5 ~R 9 、R that is not a single bond to *b 10 ~R 14 , R 15 ~R 18 and R 20 ~R 26 Each independently Hydrogen atoms, Halogen atoms, Nitro, Cyano, unsubstituted alkyl having 1 to 50 carbon atoms, unsubstituted cycloalkyl having 3 to 50 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 50 ring atoms, unsubstituted halogenated alkyl having 1 to 50 carbon atoms, unsubstituted alkoxy group having 1 to 50 carbon atoms, unsubstituted halogenated alkoxy group having 1 to 50 carbon atoms, unsubstituted aryloxy group having 6 to 50 ring carbon atoms, unsubstituted aralkyl having 7 to 50 carbon atoms, or a monosubstituted silyl group, a disubstituted silyl group, or a trisubstituted silyl group having a substituent selected from an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and an unsubstituted heterocyclic group having 5 to 50 ring atoms, One or more pairs of two mutually bonded benzene rings selected from benzene rings A to D are optionally connected by CR x R y Crosslinking to form a fluorene structure, or not crosslinking to form a fluorene structure, R x and R y are each independently an unsubstituted alkyl group having 1 to 50 carbon atoms or an unsubstituted aryl group having 6 to 50 ring carbon atoms, R x With R y optionally via a single bond, L 1 and L 2 are each independently a single bond or an unsubstituted phenylene group, Ar 1 and Ar 2 Each is independently an unsubstituted non-condensed aryl group having 6 to 50 ring carbon atoms.

2. The compound according to claim 1, which is represented by any one of the following formulas (1a) to (1d): In formulas (1a) to (1d), R 1 ~R 4 , R 5 ~R 9 , R 10 ~R 14 , R 15 ~R 18 , R 20 ~R 26 , *a, *b, L 1 , L 2 ,Ar 1 and Ar 2 As defined in formula (1).

3. The compound according to claim 1 or 2, wherein Ar 1 , or Ar 2 The unsubstituted non-condensed aryl group having 6 to 50 ring carbon atoms is phenyl, biphenyl or terphenyl.

4. The compound according to any one of claims 1 to 3, wherein One or more sets of the two mutually bonded benzene rings are cross-linked.

5. The compound according to any one of claims 1 to 3, wherein The two benzene rings bonded to each other are not cross-linked.

6. The compound according to any one of claims 1 to 3 and 5, wherein R 1 ~R 4 All are hydrogen atoms.

7. The compound according to any one of claims 1 to 3, 5 and 6, wherein R is not a single bond to *a or *b 5 ~R 9 All are hydrogen atoms.

8. The compound according to any one of claims 1 to 3 and 5 to 7, wherein R is not a single bond to *b 10 ~R 14 All are hydrogen atoms.

9. The compound according to any one of claims 1 to 3 and 5 to 8, wherein R 15 ~R 18 All are hydrogen atoms.

10. The compound according to any one of claims 1 to 9, wherein R 20 ~R 26 All are hydrogen atoms.

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

14. The organic electroluminescent element according to claim 13, wherein The organic layer includes a hole transport region between the anode and the light emitting layer, and the hole transport region includes the compound.

15. The organic electroluminescent element according to claim 14, wherein The hole transport region includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side, and the first hole transport layer, the second hole transport layer, or the first hole transport layer and the second hole transport layer include the compound.

16. The organic electroluminescent element according to any one of claims 13 to 15, wherein The light-emitting layer includes a fluorescent dopant material.

17. The organic electroluminescent element according to any one of claims 13 to 15, wherein The light-emitting layer includes a phosphorescent dopant material. 18 . An electronic device comprising the organic electroluminescent element according to claim 13 .

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