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

Abstract

Provided are a compound that further improves the performance of an organic EL element, an organic electroluminescent element with further improved element performance, and an electronic device comprising such an organic electroluminescent element, and provide a compound represented by the following formula (1), an organic electroluminescent element comprising the compound, and an electronic device comprising such an organic electroluminescent element. The molecular weight of the compound is 650 or more, wherein Cz, n, Y 1 , Y 2 ,Ar 1 ,Ar 2 , L 1 , L 2 , L 3 , L 4 and R 1 ~R 6 Same as the definition in the specification.

Description

Technical Field

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

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

[0003] Patent Documents 1 to 9 disclose compounds used as materials for organic electroluminescent devices.

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: WO2005 / 112519A1

[0007] Patent Document 2: KR2014-0006708A

[0008] Patent Document 3: WO2017 / 200210A1

[0009] Patent Document 4: WO2019 / 139419A1

[0010] Patent Document 5: US2014 / 361268A1

[0011] Patent Document 6: WO2018 / 105888A1

[0012] Patent document 7: CN107880031A

[0013] Patent Document 8: WO2018 / 056645A1

[0014] Patent Document 9: WO2012 / 108881A1 Summary of the invention

[0015] Problem that the invention aims to solve

[0016] Conventionally, a large number of compounds for organic EL devices have been reported, but compounds that further improve the performance of organic EL devices are still being sought.

[0017] The present invention has been made to solve the above-mentioned problems, and an object of the present invention is to provide a compound that further improves the performance of an organic EL element, an organic EL element with further improved element performance, and an electronic device including such an organic EL element.

[0018] Means used to solve problems

[0019] The present inventors have repeatedly conducted in-depth studies on the performance of organic EL devices containing the compounds described in Patent Documents 1 to 9, and found that naphthyl pyrimidine compounds with a molecular weight of 650 or more, having a structure in which a specific carbazole skeleton is bonded to a pyrimidine skeleton via a single bond or an aryl group and further via a naphthyl group, provide organic EL devices with further improved device performance.

[0020] In one embodiment, the present invention provides a compound represented by the following formula (1), wherein the molecular weight of the compound is 650 or more.

[0021] [Chemical formula 1]

[0022]

[0023] (Where,

[0024] Y 1 and Y 2 One of them is a nitrogen atom and the other one is CR.

[0025] R is selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a fluorine atom and a cyano group;

[0026] Ar 1 and Ar 2 Each is independently selected from 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;

[0027] 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.

[0028] R 1 ~R 6 Each is independently selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a fluorine atom and a cyano group, and R 1 ~R 6 Two adjacent ones of the amines are not bonded to each other to form a ring.

[0029] Cz is represented by the following formula (1-a) or formula (1-b);

[0030] [Chemical formula 2]

[0031]

[0032] In the formula,

[0033] R 21 ~R 28 and R 31 ~R 38 Each is independently a hydrogen atom or a substituent selected from a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms and not having a nitrogen-containing five-membered ring or a nitrogen-containing seven-membered ring, 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 fluorine atom and a cyano group,

[0034] Among them, selected from R 21 ~R 28 Two adjacent ones in R 31 ~R 38 The two adjacent ones in R 24 With R 25 , and R 34 With R 35 They are not bonded to each other to form a ring.

[0035] R a is selected from a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms;

[0036] Selected from R 21 ~R 28 One of them is connected to L via *a 3 Bonded single bonds;

[0037] *b means L 3 Bonding location.

[0038] n is an integer of 1 to 3. When n is an integer of 2 or 3, the two or three Cz are the same or different from each other;

[0039] L 3 and L 4 Each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms. 4 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0040] In another embodiment, the present invention provides a material for an organic EL device, comprising a compound represented by the above formula (1), wherein the molecular weight of the compound is 650 or more.

[0041] In another embodiment, the present invention provides an organic electroluminescent element, which is an organic electroluminescent element comprising an anode, a cathode, and an organic layer arranged between the anode and the cathode, the organic layer comprising a light-emitting layer, at least one layer of the organic layer comprises the compound represented by the above formula (1), and the molecular weight of the compound is greater than 650.

[0042] In yet another embodiment, the present invention provides an electronic device comprising the organic electroluminescent element.

[0043] Effects of the Invention

[0044] An organic EL device containing the compound represented by the above formula (1) having a molecular weight of 650 or more exhibits improved device performance. BRIEF DESCRIPTION OF THE DRAWINGS

[0045] 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.

[0046] Figure 2 It is a schematic diagram showing another example of the layer structure of the organic EL element according to one embodiment of the present invention. DETAILED DESCRIPTION

[0047] [definition]

[0048] In this specification, the hydrogen atom is meant to include isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0049] In the present specification, in chemical structural formulas, a bondable position that does not clearly show a symbol such as "R" or "D" representing a deuterium atom is assumed to be bonded with a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom.

[0050] In this specification, the ring carbon number refers to 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 in a ring shape. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the ring carbon number. The "ring carbon number" recorded below is set in the same manner unless otherwise stated. For example, the ring carbon number of the benzene ring is 6, the ring carbon number of the naphthalene ring is 10, the ring carbon number of the pyridine ring is 5, and the ring carbon number of the furan ring is 4. In addition, for example, the ring carbon number of 9,9-diphenylfluorenyl is 13, and the ring carbon number of 9,9'-spirobifluorenyl is 25.

[0051] 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.

[0052] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a bridged ring compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are bonded in a ring shape (e.g., a monocyclic compound, a condensed ring compound, a bridged ring compound, a carbocyclic compound, and a heterocyclic compound). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of atoms constituting the ring) and atoms contained in a substituent when the ring is substituted by a substituent are not included in the number of ring atoms. The "number of ring atoms" recorded below is set in the same manner as long as it is not recorded separately. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or atoms constituting a substituent is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring bonded with a hydrogen atom or a substituent is 6. In addition, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring. Therefore, the number of ring atoms of the quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

[0053] 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.

[0054] In this specification, "the number of atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having an atomic number of XX to YY" means the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituent when substituted. Here, "YY" is greater than "XX", "XX" means an integer greater than 1, and "YY" means an integer greater than 2.

[0055] 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".

[0056] 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.

[0057] In addition, in the present specification, "substituted" when expressing "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. "Substituted" when expressing "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0058] "Substituents described in this specification"

[0059] The substituents described in the present specification are described below.

[0060] 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.

[0061] 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.

[0062] The carbon number of the "unsubstituted alkyl group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise described in the present specification.

[0063] The carbon number of the "unsubstituted alkenyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise described in the present specification.

[0064] 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.

[0065] 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.

[0066] 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.

[0067] 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.

[0068] 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.

[0069] "Substituted or unsubstituted aryl"

[0070] As specific examples of "substituted or unsubstituted aryl" described in this specification (specific example group G1), the following unsubstituted aryl (specific example group G1A) and substituted aryl (specific example group G1B) can be cited. (Here, unsubstituted aryl refers to the case where "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl refers to the case where "substituted or unsubstituted aryl" is "substituted aryl".) In this specification, when only "aryl" is expressed, both "unsubstituted aryl" and "substituted aryl" are included.

[0071] "Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" are replaced by a substituent. Examples of "substituted aryl" include groups in which one or more hydrogen atoms of an "unsubstituted aryl" are replaced by a substituent in the following specific example group G1A, and examples of substituted aryl in the following specific example group G1B. It should be noted that the examples of "unsubstituted aryl" and "substituted aryl" listed here are only examples, and the "substituted aryl" described in this specification also includes groups in which the hydrogen atom bonded to the carbon atom of the aryl itself in the "substituted aryl" in the following specific example group G1B is further replaced by a substituent, and groups in which the hydrogen atom of the substituent in the "substituted aryl" in the following specific example group G1B is further replaced by a substituent.

[0072] Unsubstituted aryl (specific example group G1A):

[0073] Phenyl,

[0074] p-Biphenyl,

[0075] m-Biphenyl,

[0076] o-Biphenyl,

[0077] 4-terphenyl-4-yl,

[0078] 4-terphenyl-3-yl,

[0079] 4-terphenyl-2-yl,

[0080] m-terphenyl-4-yl,

[0081] m-terphenyl-3-yl,

[0082] m-terphenyl-2-yl,

[0083] o-terphenyl-4-yl,

[0084] o-terphenyl-3-yl,

[0085] o-terphenyl-2-yl,

[0086] 1-naphthyl,

[0087] 2-naphthyl,

[0088] Anthracene,

[0089] Benzanthryl,

[0090] Fiki,

[0091] Triphenylene,

[0092] Phenyl,

[0093] Pyrene

[0094] base,

[0095] Benzo base,

[0096] Triphenylene,

[0097] Benzotriphenylene,

[0098] Tetraphenylene,

[0099] Pentaphenyl,

[0100] Fluorene,

[0101] 9,9'-spirobifluorenyl,

[0102] Benzofluorenyl,

[0103] Dibenzofluorenyl,

[0104] Fluoranthene group,

[0105] Benzofluoranthene,

[0106] Base and

[0107] A monovalent aromatic group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[0108] [Chemical formula 3]

[0109]

[0110] [Chemical formula 4]

[0111]

[0112] Substituted aryl (specific example group G1B):

[0113] o-Toluyl,

[0114] m-Toluene

[0115] p-Tolyl,

[0116] p-Xylyl,

[0117] m-Xylyl,

[0118] o-Xylyl,

[0119] p-Isopropylphenyl,

[0120] m-isopropylphenyl,

[0121] o-isopropylphenyl,

[0122] 4-tert-Butylphenyl,

[0123] m-tert-butylphenyl,

[0124] o-tert-butylphenyl,

[0125] 3,4,5-Trimethylphenyl,

[0126] 9,9-dimethylfluorenyl,

[0127] 9,9-Diphenylfluorenyl

[0128] 9,9-bis(4-methylphenyl)fluorenyl,

[0129] 9,9-bis(4-isopropylphenyl)fluorenyl,

[0130] 9,9-bis(4-tert-butylphenyl)fluorenyl,

[0131] Cyanophenyl,

[0132] Triphenylsilylphenyl,

[0133] Trimethylsilylphenyl,

[0134] Phenyl naphthyl,

[0135] Naphthylphenyl and

[0136] 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.

[0137] "Substituted or unsubstituted heterocyclic group"

[0138] The "heterocyclic group" described in the present specification is a cyclic group containing at least one heteroatom among the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom and a boron atom.

[0139] The "heterocyclic group" described in the present specification is a monocyclic group or a condensed ring group.

[0140] The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0141] As specific examples of the "substituted or unsubstituted heterocyclic group" described in this specification (specific example group G2), the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B) can be cited. (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when only "heterocyclic group" is expressed, both "unsubstituted heterocyclic group" and "substituted heterocyclic group" are included.

[0142] "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.

[0143] 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).

[0144] Specific example group G2B includes, for example, the following heterocyclic groups containing nitrogen atom substitution (specific example group G2B1), oxygen atom substitution (specific example group G2B2), sulfur atom substitution (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formula (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4).

[0145] Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):

[0146] Pyrrolyl,

[0147] Imidazole,

[0148] Pyrazolyl,

[0149] Triazole,

[0150] Tetrazolyl,

[0151] Oxazolyl,

[0152] Isoxazolyl,

[0153] Oxadiazolyl,

[0154] Thiazolyl,

[0155] Isothiazolyl,

[0156] Thiadiazole,

[0157] Pyridyl,

[0158] Pyridazine

[0159] Pyrimidine,

[0160] Pyrazinyl,

[0161] Triazine,

[0162] Indolyl,

[0163] Isoindolyl,

[0164] Indolizine

[0165] Quinolizinyl,

[0166] Quinoline,

[0167] Isoquinolinyl,

[0168] Cinnoline,

[0169] Phthalocyanine

[0170] Quinazoline,

[0171] Quinoxaline,

[0172] Benzimidazolyl,

[0173] Indazolyl,

[0174] Phenanthroline,

[0175] Phenanthridinyl,

[0176] Acridinium,

[0177] Phenazine,

[0178] Carbazolyl,

[0179] Benzocarbazolyl,

[0180] Morpholinyl,

[0181] Phenoxazine,

[0182] Phenothiazine,

[0183] Azacarbazolyl and diazacarbazolyl.

[0184] Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):

[0185] Furanyl,

[0186] Oxazolyl,

[0187] Isoxazolyl,

[0188] Oxadiazolyl,

[0189] Xanthyl,

[0190] Benzofuranyl,

[0191] Isobenzofuranyl,

[0192] Dibenzofuranyl,

[0193] Naphthobenzofuranyl,

[0194] Benzoxazolyl,

[0195] Benzisoxazolyl,

[0196] Phenoxazine,

[0197] Morpholinyl,

[0198] dinaphthofuranyl,

[0199] Azadibenzofuranyl,

[0200] Diazadibenzofuranyl,

[0201] Azanaphthobenzofuranyl and

[0202] naphthyridinylbenzofuranyl.

[0203] Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3):

[0204] Thienyl,

[0205] Thiazolyl,

[0206] Isothiazolyl,

[0207] Thiadiazole,

[0208] benzothienyl,

[0209] Isobenzothienyl,

[0210] dibenzothienyl,

[0211] naphthobenzothienyl,

[0212] Benzothiazolyl,

[0213] Benzisothiazolyl,

[0214] Phenothiazine,

[0215] dinaphthothienyl,

[0216] azadibenzothienyl,

[0217] diazadibenzothienyl,

[0218] azanaphthobenzothienyl, and

[0219] diazanaphthobenzothienyl.

[0220] 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):

[0221] [Chemical formula 5]

[0222]

[0223] [Chemical formula 6]

[0224]

[0225] 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.

[0226] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A When at least any one of is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the above general formula (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0227] Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):

[0228] (9-phenyl)carbazolyl,

[0229] (9-biphenyl)carbazolyl,

[0230] (9-phenyl)phenylcarbazolyl,

[0231] (9-naphthyl)carbazolyl,

[0232] Diphenylcarbazole-9-yl,

[0233] Phenylcarbazol-9-yl,

[0234] Methylbenzimidazolyl,

[0235] Ethylbenzimidazolyl,

[0236] Phenyl triazine,

[0237] Biphenyl triazine,

[0238] Diphenyltriazine,

[0239] Phenylquinazolinyl and

[0240] Biphenylquinazolinyl.

[0241] Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0242] Phenyldibenzofuranyl,

[0243] Methyldibenzofuranyl,

[0244] tert-Butyldibenzofuranyl and

[0245] The monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0246] Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

[0247] Phenyldibenzothiophene,

[0248] Methyldibenzothiophene,

[0249] tert-Butyldibenzothienyl and

[0250] The monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0251] · Groups in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) are replaced with substituents (Specific example group G2B4):

[0252] The above-mentioned “one or more hydrogen atoms of the monovalent heterocyclic group” refers to one or more hydrogen atoms selected from the group consisting of hydrogen atoms bonded to ring-constituting carbon atoms of the monovalent heterocyclic group, hydrogen atoms bonded to nitrogen atoms when at least one of XA and YA is NH, and hydrogen atoms of a methylene group when one of XA and YA is CH2.

[0253] "Substituted or unsubstituted alkyl"

[0254] 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.

[0255] "Substituted alkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl" are replaced by a substituent. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl" (specific example group G3A) are replaced by a substituent, and examples of substituted alkyl (specific example group G3B) can be cited. In the present specification, the alkyl group in "unsubstituted alkyl" refers to a chain alkyl group. Therefore, "unsubstituted alkyl" includes "unsubstituted alkyl" as a straight chain and "unsubstituted alkyl" as a branched chain. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples, and the "substituted alkyl" recorded in the present specification also includes groups in which the hydrogen atoms of the alkyl group itself in the "substituted alkyl" of the specific example group G3B are further replaced by a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted alkyl" of the specific example group G3B are further replaced by a substituent.

[0256] Unsubstituted alkyl (specific example group G3A):

[0257] methyl,

[0258] Ethyl,

[0259] n-propyl,

[0260] Isopropyl,

[0261] n-Butyl,

[0262] Isobutyl,

[0263] sec-butyl, and

[0264] Tert-butyl.

[0265] Substituted alkyl (specific example group G3B):

[0266] Heptafluoropropyl (including isomers),

[0267] Pentafluoroethyl,

[0268] 2,2,2-trifluoroethyl and

[0269] Trifluoromethyl.

[0270] "Substituted or unsubstituted alkenyl"

[0271] As specific examples of "substituted or unsubstituted alkenyl" described in this specification (specific example group G4), the following unsubstituted alkenyl (specific example group G4A) and substituted alkenyl (specific example group G4B) can be cited. (Here, unsubstituted alkenyl refers to the case where "substituted or unsubstituted alkenyl" is "unsubstituted alkenyl", and "substituted alkenyl" refers to the case where "substituted or unsubstituted alkenyl" is "substituted alkenyl".) In this specification, when simply expressed as "alkenyl", both "unsubstituted alkenyl" and "substituted alkenyl" are included.

[0272] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" are replaced by a substituent. Specific examples of "substituted alkenyl" include the following "unsubstituted alkenyl" (specific example group G4A) groups with substituents and examples of substituted alkenyl (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples, and the "substituted alkenyl" recorded in this specification also includes groups in which the hydrogen atoms of the alkenyl itself in the "substituted alkenyl" of the specific example group G4B are further replaced by a substituent and groups in which the hydrogen atoms of the substituent in the "substituted alkenyl" of the specific example group G4B are further replaced by a substituent.

[0273] Unsubstituted alkenyl (specific example group G4A):

[0274] Vinyl,

[0275] Allyl,

[0276] 1-Butenyl,

[0277] 2-Butenyl and

[0278] 3-Butenyl.

[0279] Substituted alkenyl (specific example group G4B):

[0280] 1,3-Butadienyl,

[0281] 1-Methylvinyl,

[0282] 1-methylallyl,

[0283] 1,1-dimethylallyl,

[0284] 2-Methylallyl and

[0285] 1,2-Dimethylallyl.

[0286] "Substituted or unsubstituted alkynyl"

[0287] As specific examples of "substituted or unsubstituted alkynyl" described in this specification (specific example group G5), the following unsubstituted alkynyl (specific example group G5A) etc. can be cited. (Here, unsubstituted alkynyl refers to the case where "substituted or unsubstituted alkynyl" is "unsubstituted alkynyl".) When simply expressed as "alkynyl" below, both "unsubstituted alkynyl" and "substituted alkynyl" are included.

[0288] "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.

[0289] Unsubstituted alkynyl (specific example group G5A):

[0290] Ethylene

[0291] "Substituted or unsubstituted cycloalkyl"

[0292] As specific examples of "substituted or unsubstituted cycloalkyl" described in the present specification (specific example group G6), the following unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B) can be cited. (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl".) In the present specification, when only "cycloalkyl" is expressed, both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.

[0293] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" are replaced by a substituent. Specific examples of "substituted cycloalkyl" include the following "unsubstituted cycloalkyl" (specific example group G6A) in which one or more hydrogen atoms are replaced by a substituent, and examples of substituted cycloalkyl (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples, and the "substituted cycloalkyl" recorded in this specification also includes the group in which one or more hydrogen atoms bonded to the carbon atoms of the cycloalkyl itself in the "substituted cycloalkyl" of the specific example group G6B are replaced by a substituent, and the group in which the hydrogen atom of the substituent in the "substituted cycloalkyl" of the specific example group G6B is further replaced by a substituent.

[0294] Unsubstituted cycloalkyl (specific example group G6A):

[0295] Cyclopropyl,

[0296] Cyclobutyl,

[0297] Cyclopentyl,

[0298] Cyclohexyl,

[0299] 1-adamantyl,

[0300] 2-adamantyl,

[0301] 1-Norbornyl and

[0302] 2-Norborneol.

[0303] Substituted cycloalkyl (specific example group G6B):

[0304] 4-Methylcyclohexyl.

[0305] ·“-Si(R 901 )(R 902 )(R 903 )"

[0306] As described in this specification, -Si(R 901 )(R 902 )(R 903 ) as a specific example (specific example group G7), can be cited:

[0307] -Si(G1)(G1)(G1),

[0308] -Si(G1)(G2)(G2),

[0309] -Si(G1)(G1)(G2),

[0310] -Si(G2)(G2)(G2),

[0311] -Si(G3)(G3)(G3), and

[0312] -Si(G6)(G6)(G6)

[0313] Here,

[0314] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0315] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0316] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0317] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0318] A plurality of G1's in -Si(G1)(G1)(G1) are the same as or different from each other.

[0319] The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other.

[0320] A plurality of G1's in -Si(G1)(G1)(G2) are the same as or different from each other.

[0321] Multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other.

[0322] Multiple G3 in -Si(G3)(G3)(G3) are the same as or different from each other.

[0323] Multiple G6's in -Si(G6)(G6)(G6) are the same as or different from each other.

[0324] ·“-O-(R 904 )"

[0325] As described in this specification, -O-(R 904 ) as a specific example (specific example group G8), can be cited:

[0326] -O(G1),

[0327] -O(G2),

[0328] -O(G3) and

[0329] -O(G6).

[0330] Here,

[0331] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0332] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0333] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0334] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0335] ·“-S-(R 905 )"

[0336] As described in this specification, -S-(R 905 ) as a specific example (specific example group G9), can be cited:

[0337] -S(G1),

[0338] -S(G2),

[0339] -S(G3) and

[0340] -S(G6).

[0341] Here,

[0342] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0343] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0344] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0345] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0346] ·“-N(R 906 )(R 907 )"

[0347] As described in this specification, -N(R 906 )(R 907 ) are shown as specific examples (specific example group G10), and include

[0348] -N(G1)(G1),

[0349] -N(G2)(G2),

[0350] -N(G1)(G2),

[0351] -N(G3)(G3) and

[0352] -N(G6)(G6).

[0353] Here,

[0354] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0355] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0356] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0357] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0358] - A plurality of G1's in N(G1)(G1) are the same as or different from each other.

[0359] - The multiple G2s in N(G2)(G2) are the same as or different from each other.

[0360] - The multiple G3 in N(G3)(G3) are the same as or different from each other.

[0361] - The multiple G6's in N(G6)(G6) are the same as or different from each other.

[0362] "Halogen atoms"

[0363] 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.

[0364] "Substituted or unsubstituted fluoroalkyl"

[0365] The "substituted or unsubstituted fluoroalkyl group" described in the present specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in a "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). The carbon number of the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification. The "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. It should be noted that the "substituted fluoroalkyl group" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in a "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced with fluorine atoms.

[0366] "Substituted or unsubstituted haloalkyl"

[0367] The "substituted or unsubstituted haloalkyl group" described in the present specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in a "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The carbon number of the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification. The "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of a "haloalkyl group" are replaced with a substituent. It should be noted that the "substituted haloalkyl group" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in a "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in a "substituted haloalkyl group" are further replaced with a substituent. Specific examples of "unsubstituted haloalkyl" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (specific example group G3) are replaced with halogen atoms. A haloalkyl group is sometimes referred to as a halogenated alkyl group.

[0368] "Substituted or unsubstituted alkoxy"

[0369] 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.

[0370] "Substituted or unsubstituted alkylthio"

[0371] 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.

[0372] "Substituted or unsubstituted aryloxy group"

[0373] 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.

[0374] "Substituted or unsubstituted arylthio"

[0375] 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.

[0376] "Substituted or unsubstituted trialkylsilyl"

[0377] A specific example of a "trialkylsilyl group" described in the present specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. A plurality of G3's in -Si(G3)(G3)(G3) are the same or different from each other. The number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise described in the present specification.

[0378] "Substituted or unsubstituted aralkyl"

[0379] A specific example of the "substituted or unsubstituted aralkyl group" described in the present specification is a group represented by -(G3)-(G1), wherein G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. Therefore, the "aralkyl group" is a group in which the hydrogen atom of the "alkyl group" is replaced by the "aryl group" as a substituent, and is one embodiment of the "substituted alkyl group". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the carbon number of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise described in the present specification.

[0380] 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.

[0381] 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.

[0382] The substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidyl group, a triazine group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group or 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzofuranyl group benzothiophenyl, azadibenzothiophenyl, diazadibenzothiophenyl, (9-phenyl)carbazyl ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl or (9-phenyl)carbazol-4-yl), (9-biphenyl)carbazyl, (9-phenyl)phenylcarbazyl, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazine, biphenyltriazine, diphenyltriazine, phenyldibenzofuranyl and phenyldibenzothiophenyl, etc.

[0383] In the present specification, the carbazolyl group is specifically any of the following groups unless otherwise described in the present specification.

[0384] [Chemical formula 7]

[0385]

[0386] In the present specification, the (9-phenyl)carbazolyl group is specifically any of the following groups unless otherwise specified in the present specification.

[0387] [Chemical formula 8]

[0388]

[0389] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0390] 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.

[0391] [Chemical formula 9]

[0392]

[0393] In the above general formulas (TEMP-34) to (TEMP-41), * represents a bonding position.

[0394] 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.

[0395] "Substituted or unsubstituted arylene group"

[0396] Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted aryl group" by removing one hydrogen atom on the aromatic ring. Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in specific example group G1 by removing one hydrogen atom on the aromatic ring.

[0397] "Substituted or unsubstituted divalent heterocyclic group"

[0398] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom on the heterocyclic ring. Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in specific example group G2 by removing one hydrogen atom on the heterocyclic ring.

[0399] "Substituted or unsubstituted alkylene"

[0400] Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted alkyl group" by removing one hydrogen atom on the alkyl chain. Specific examples of the "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived from the "substituted or unsubstituted alkyl group" described in specific example group G3 by removing one hydrogen atom on the alkyl chain.

[0401] 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.

[0402] [Chemical formula 10]

[0403]

[0404] [Chemical formula 11]

[0405]

[0406] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0407] In the above general formulas (TEMP-42) to (TEMP-52), * represents a bonding position.

[0408] [Chemical formula 12]

[0409]

[0410] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0411] Formula Q9 and Q 10 They may be bonded to each other via a single bond to form a ring.

[0412] In the above general formulas (TEMP-53) to (TEMP-62), * represents a bonding position.

[0413] [Chemical formula 13]

[0414]

[0415] In the above general formulae (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0416] In the above general formulas (TEMP-63) to (TEMP-68), * represents a bonding position.

[0417] 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.

[0418] [Chemical formula 14]

[0419]

[0420] [Chemical formula 15]

[0421]

[0422] [Chemical formula 16]

[0423]

[0424] In the above general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0425] [Chemical formula 17]

[0426]

[0427] [Chemical formula 18]

[0428]

[0429] [Chemical formula 19]

[0430]

[0431] [Chemical formula 20]

[0432]

[0433] In the above general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0434] The above is the description of the “substituents described in the present specification”.

[0435] ・"When bonding to form a ring"

[0436] In the present specification, the expression "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, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other" means the case where "one or more of the groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring", the case where "one or more of the groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted condensed ring", and the case where "one or more of the groups consisting of two or more adjacent groups are not bonded to each other".

[0437] Hereinafter, 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 monocyclic 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" in this specification (hereinafter, these cases are sometimes collectively referred to as "cases of bonding to form a ring") are described. The case of an anthracene compound represented by the following general formula (TEMP-103) in which the mother skeleton is an anthracene ring is described as an example.

[0438] [Chemical formula 21]

[0439]

[0440] For example, in 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 as one group refers to R 921 With R 922 Group, R 922 With R 923 Group, R 923 With R 924 Group, R 924 With R 930 Group, R 930 With R 925 Group, R 925 With R 926 Group, R 926 With R 927 Group, R 927 With R 928 Group, R 928 With R 929 The group, and R 929 With R 921 group.

[0441] The above-mentioned "one or more groups" means that two or more groups of the above-mentioned two or more adjacent groups can simultaneously form a ring. 921 With R 922 Bonded to each other to form ring Q A And at the same time R 925 With R 926 Bonded to each other to form ring Q B When the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0442] [Chemical formula 22]

[0443]

[0444] 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 in the above example, but also the case where a group of "three or more" adjacent groups is bonded. For example, R 921 With R 922 Bonded to each other to form ring Q A , and R 922 With R 923 Bonded to each other to form ring Q C , consisting of three adjacent (R 921 , R 922 and R 923) are bonded to each other to form a ring and fused to the anthracene mother skeleton. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and Ring Q C Total R 922 .

[0445] [Chemical formula 23]

[0446]

[0447] In the "monocyclic ring" or "condensed ring" formed, the structure of the ring formed alone may be a saturated ring or an unsaturated ring. Even when "one of the two adjacent groups" forms a "monocyclic ring" or a "condensed ring", the "monocyclic ring" or "condensed ring" may form a saturated ring or an unsaturated ring. For example, in the above general formula (TEMP-104), the ring Q A and Ring Q B Each is a "single ring" or a "condensed ring". In addition, the ring Q formed in the above general formula (TEMP-105) A And Ring Q C The ring Q of the above general formula (TEMP-105) is A With Ring Q C By RingQ A With Ring Q C The ring Q of the above general formula (TMEP-104) is fused to form a fused ring. A If it is a benzene ring, then ring Q A The ring Q of the above general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a condensed ring.

[0448] 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.

[0449] 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.

[0450] 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.

[0451] 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.

[0452] "Forming a ring" means that a ring is formed only by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton and one or more other optional elements. For example, R 921 With R 922 The ring Q formed by mutual bonding A It refers to R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 The carbon atom of the anthracene skeleton to which the bonding occurs forms a ring with one or more optional elements. 921 With R 922 Ring Q A In the case of R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 When the carbon atom of the anthracene skeleton to which the carbon atom is bonded forms a monocyclic unsaturated ring with four carbon atoms, R 921 With R 922 The ring formed is a benzene ring.

[0453] Here, "optional element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur as long as it is not otherwise described in this specification. In the optional element (for example, in the case of carbon or nitrogen), the bond that does not form a ring can be terminated by hydrogen atoms or the like, or can be replaced by "optional substituents" described later. When an optional element other than carbon is included, the formed ring is a heterocycle.

[0454] 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.

[0455] Unless otherwise specified in the present specification, "monocyclic ring" is preferred among "monocyclic ring" and "condensed ring".

[0456] In the present specification, unless otherwise specified, among "saturated ring" and "unsaturated ring", "unsaturated ring" is preferred.

[0457] Unless otherwise specified in the present specification, a "monocyclic ring" is preferably a benzene ring.

[0458] Unless otherwise specified in the present specification, the "unsaturated ring" is preferably a benzene ring.

[0459] In the case of "one or more groups consisting of two or more adjacent atoms" "bonded to each other to form a substituted or unsubstituted single ring" or "bonded to each other to form a substituted or unsubstituted condensed ring", unless otherwise stated in the present specification, it is preferred that one or more groups consisting of two or more adjacent atoms bond 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.

[0460] 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".

[0461] When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above-mentioned "substituents described in the present specification".

[0462] 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").

[0463] ·Substituents when expressed as "substituted or unsubstituted"

[0464] 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 selected from, for example, unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0465] unsubstituted alkenyl having 2 to 50 carbon atoms,

[0466] unsubstituted alkynyl having 2 to 50 carbon atoms,

[0467] unsubstituted cycloalkyl having 3 to 50 ring carbon atoms,

[0468] -Si(R 901 )(R 902 )(R 903 ),

[0469] -O-(R 904 ),

[0470] -S-(R 905 ),

[0471] -N(R 906 )(R 907 ),

[0472] Halogen atoms, cyano, nitro,

[0473] unsubstituted aryl group having 6 to 50 ring carbon atoms and

[0474] Unsubstituted heterocyclic group having 5 to 50 ring atoms

[0475] The groups in the group etc.

[0476] Here, R 901 ~R 907 Each independently

[0477] Hydrogen atoms,

[0478] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0479] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0480] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0481] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0482] In R 901 When there are two or more R 901 Same or different from each other,

[0483] In R 902 When there are two or more R 902 Same or different from each other,

[0484] In R 903 When there are two or more R 903 Same or different from each other,

[0485] In R 904 When there are two or more R 904 Same or different from each other,

[0486] In R 905 When there are two or more R 905 Same or different from each other,

[0487] In R 906 When there are two or more R 906 Same or different from each other,

[0488] In R907 When there are two or more R 907 Same as or different from each other.

[0489] In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

[0490] an alkyl group having 1 to 50 carbon atoms,

[0491] An aryl group having 6 to 50 ring carbon atoms and

[0492] A heterocyclic group having 5 to 50 ring atoms

[0493] The groups in the group.

[0494] In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

[0495] an alkyl group having 1 to 18 carbon atoms,

[0496] An aryl group having 6 to 18 ring carbon atoms and

[0497] A heterocyclic group having 5 to 18 ring atoms

[0498] The groups in the group.

[0499] Specific examples of each group of the above-mentioned optional substituent are the specific examples of the substituent described in the above-mentioned section "substituent described in the present specification".

[0500] Unless otherwise stated in the present specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably a benzene ring.

[0501] Unless otherwise specified in the present specification, an optional substituent may further have a substituent. The substituent further possessed by the optional substituent is the same as the optional substituent described above.

[0502] 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.

[0503] The compounds of the present invention are described below.

[0504] The compound of the present invention is a compound represented by the following formula (1), and the molecular weight of the compound is 650 or more. Hereinafter, the compound of the present invention represented by formula (1) and each of the sub-formulas belonging to formula (1) described below may be simply referred to as "the compound of the present invention".

[0505] [Chemical formula 24]

[0506]

[0507] The molecular weight of the compound represented by formula (1) of the present invention is not less than 650. If the molecular weight of the inventive compound is less than 650, the glass transition temperature Tg is likely to decrease, and from the viewpoint of heat resistance to heat generated when the element is driven (hereinafter sometimes referred to as "driving heat"), the life of the element may be reduced.

[0508] The molecular weight of the inventive compound is preferably 650 to 5000, more preferably 650 to 3000, and further preferably 650 to 1000. When the molecular weight is within this range, a high glass transition temperature Tg can be maintained, so that the inventive compound is relatively stable to heat such as driving heat, and degradation and deformation of film properties are suppressed, thereby improving the life of the device.

[0509] The glass transition temperature of the compound of the invention is preferably 125° C. or higher, more preferably 130° C. or higher, and even more preferably 140° C. or higher.

[0510] Hereinafter, the symbols in the above formula and each of the formulas described below will be described. It should be noted that the same symbols have the same meaning unless otherwise specified.

[0511] Y 1 and Y 2 One of them is a nitrogen atom and the other one is CR. That is, Y 1 is a nitrogen atom and Y 2 CR, or Y 1 CR and Y 2 A nitrogen atom.

[0512] n is an integer of 1 to 3. When n is an integer of 2 or 3, two or three Cz are the same as or different from each other.

[0513] R is selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, 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 fluorine atom and a cyano group, preferably selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms and a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and more preferably a hydrogen atom.

[0514] The details of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms are the same as those described in the “substituents described in the present specification”, and more 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, fluorenyl, 9,9′-spirobifluorenyl, 9,9-dimethylfluorenyl, or 9,9-diphenylfluorenyl, and further preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, 1-naphthyl, 2-naphthyl, fluorenyl, 9,9′-spirobifluorenyl, 9,9-dimethylfluorenyl, or 9,9-diphenylfluorenyl.

[0515] The details of the above-mentioned substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms are the same as those described in the “Substituents described in the present specification”, and more preferably it is carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl or 9-carbazolyl), dibenzofuranyl, naphthiobenzofuranyl, dibenzothiophenyl, naphthiobenzothiophenyl, phenyldibenzofuranyl or phenyldibenzothiophenyl, and further preferably it is carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl or 9-carbazolyl), dibenzofuranyl or dibenzothiophenyl.

[0516] The details of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms are the same as those described in the "substituents described in the present specification", and are preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, and more preferably methyl, isopropyl, or tert-butyl.

[0517] The details of the substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms are the same as those described in "substituents described in the present specification", and is preferably cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and more preferably cyclopropyl, cyclopentyl or cyclohexyl.

[0518] R 1 ~R 6 Each is independently selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, 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 fluorine atom and a cyano group, preferably selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms and a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and more preferably a hydrogen atom.

[0519] Selected from R 1 ~R 6Two adjacent ones of the amines are not bonded to each other to form a ring.

[0520] The details of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, the substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, the substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, and the substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms are the same as the details of the corresponding groups described above for R.

[0521] L 3 and L 4 Each is independently selected from a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0522] When n is an integer of 2 or 3, L 4 It is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0523] As L 3 and L 4 A solution of L 3 and L 4 Preferably, each independently is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0524] As another embodiment, L 3 is a single bond and L 4 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or L 3 and L 4 For a single key.

[0525] The details of the substituted or unsubstituted arylene group having 6 to 50 carbon atoms are the same as those described in the "substituent described in the present specification", and examples thereof include a divalent group derived from the above-mentioned "substituted or unsubstituted aryl group having 6 to 50 carbon atoms" by removing one hydrogen atom on the aromatic ring.

[0526] L 3 and L 4 The unsubstituted arylene group of the substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms represented by is preferably each independently selected from phenylene, biphenylene, naphthylene, phenanthrylene and anthracene.

[0527] Ar 1 and Ar 2 Each is independently selected from 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.

[0528] The details of the above-mentioned substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms are the same as the details of the corresponding group described above with respect to R.

[0529] Ar 1and Ar 2 The unsubstituted aryl groups of the substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms are preferably each independently selected from phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, Base and pyrene base.

[0530] The details of the above-mentioned substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms are the same as the details of the corresponding group described above with respect to R.

[0531] Ar 1 and Ar 2 The unsubstituted heterocyclic group of the substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms represented by is preferably each independently selected from pyridyl, dibenzothienyl, dibenzofuranyl, azadibenzofuranyl, pyrimidinyl, quinolyl, isoquinolyl, benzothienyl and benzofuranyl.

[0532] L 1 and L 2 Each is independently selected from a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0533] As L 1 and L 2 A solution, preferably L 1 and L 2 One of them is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, and the remaining one is a single bond.

[0534] As L 1 and L 2 Another solution, L 1 and L 2 Preferably, each independently is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0535] As another alternative, it is preferred that L 1 and L 2 For a single key.

[0536] The details of the substituted or unsubstituted arylene group having 6 to 50 carbon atoms are the same as those described above for L 3 and L 4 The details of the arylene group described are the same.

[0537] L 1 and L 2 The unsubstituted arylene group of the substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms represented by is preferably each independently selected from phenylene, biphenylene, naphthylene, phenanthrenylene, fluorenylene and anthraceneylene.

[0538] Cz is a group represented by the following formula (1-a) or formula (1-b).

[0539] [Chemical formula 25]

[0540]

[0541] R 21 ~R 28 and R 31 ~R 38 Each is independently a hydrogen atom or a substituent.

[0542] The substituent is selected from a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms and not having a nitrogen-containing five-membered ring or a nitrogen-containing seven-membered ring, 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 fluorine atom, and a cyano group. Preferably, it is selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms and not having a nitrogen-containing five-membered ring or a nitrogen-containing seven-membered ring, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and a cyano group, and more preferably a hydrogen atom.

[0543] Among them, selected from R 21 ~R 28 Two adjacent ones in R 31 ~R 38 The two adjacent ones in R 24 With R 25 , and R 34 With R 35 They are not bonded to each other to form a ring.

[0544] In addition, selected from R 21 ~R 28 One of them is connected to L via *a 3 Single bond, *b indicates bonding with L 3 Bonding location.

[0545] The details of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, the substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, and the substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms are the same as those of the corresponding groups described above for R.

[0546] The details of the substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms and not having a nitrogen-containing five-membered ring or a nitrogen-containing seven-membered ring are the details of the heterocyclic group described above for R excluding the heterocyclic group having a nitrogen-containing five-membered ring or a nitrogen-containing seven-membered ring.

[0547] As one embodiment of the present invention, it is preferably selected from 3 R of the bonded single bond 21 ~R 28At least one of or selected from R 31 ~R 38 At least one of them is a substituent.

[0548] Preferably, it is not connected to L via *a. 3 R of the bonded single bond 21 ~R 28 and R 31 ~R 38 At least one of the substituents represented by is selected from a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms.

[0549] In not through *a and L 3 R of the bonded single bond 21 ~R 28 and R 31 ~R 38 Among the above-mentioned substituents represented by , it is preferred that at least one of the unsubstituted substituents is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, phenyl, biphenyl, naphthyl, phenanthryl and cyano.

[0550] R a It is selected from a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms.

[0551] The details of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and the substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms are the same as the details of the corresponding groups described above with respect to R.

[0552] R a The unsubstituted aryl group of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms represented by is preferably selected from phenyl, biphenyl, naphthyl and phenanthryl.

[0553] R a The unsubstituted alkyl group of the substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms represented by is preferably selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.

[0554] In a preferred embodiment of the present invention, the compound of the invention comprises a compound represented by formula (1-b-1) or (1-b-2).

[0555] [Chemical formula 26]

[0556]

[0557] Y 1 , Y 2 ,Ar 1 ,Ar 2 , L1 , L 2 , R 1 ~R 6 and R 31 ~R 38 Same as the definition above, R 41 ~R 42 , R 44 ~R 45 , R 51 ~R 52 and R 54 ~R 55 Each is independently selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0558] R 41 ~R 42 , R 44 ~R 45 , R 51 ~R 52 and R 54 ~R 55 The details of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and the substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms represented are the same as the details of the corresponding groups described above with respect to R.

[0559] Selected from R 41 ~R 42 , R 44 ~R 45 , R 51 ~R 52 and R 54 ~R 55 At least one set of two adjacent ones, namely selected from R 41 With R 42 , R 44 With R 45 , R 51 With R 52 , and R 54 With R 55 At least one group of adjacent two of them may be independently bonded to each other to form a substituted or unsubstituted benzene ring, or may not be bonded to each other and thus not form the above-mentioned benzene ring. In one embodiment of the present invention, it is preferred that the above-mentioned benzene ring is not formed. In another embodiment of the present invention, it is preferred that the above-mentioned benzene ring is formed.

[0560] In a preferred embodiment of the present invention, the compound of the invention includes a compound represented by any one of formulas (1-b-11) to (1-b-14).

[0561] [Chemical formula 27]

[0562]

[0563] Y 1 , Y 2 ,Ar 1 ,Ar 2 , L 1 , L 2 , R 1 ~R 6 , R 31 ~R 38 , R 41 and R 44 ~R 45 Each is the same as defined above. 43 It is selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0564] R 43 The details of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and the substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms represented are the same as the details of the corresponding groups described above with respect to R.

[0565] In a preferred embodiment of the present invention, the compound of the invention includes a compound represented by any one of formulae (1-a-1) to (1-a-4).

[0566] [Chemical formula 28]

[0567]

[0568] Y 1 , Y 2 ,Ar 1 ,Ar 2 , L 1 , L 2 , R a , R 1 ~R 6 , R 21 ~R 28 , R 41 ~R 42 and R 44 ~R 45 Same definition as above.

[0569] In one embodiment of the present invention,

[0570] (1) Can R 1 ~R 6 are hydrogen atoms,

[0571] (2) Can R 41 ~R 45 are hydrogen atoms,

[0572] (3) Can R51 ~R 52 and R 54 ~R 55 are hydrogen atoms,

[0573] (4) can be selected from L without *a 3 R of the bonded single bond 21 ~R 28 All groups except the substituents are hydrogen atoms.

[0574] (5) can be selected from R 31 ~R 38 All groups except the substituents are hydrogen atoms.

[0575] The compound of the invention may simultaneously satisfy two or more of the above conditions (1) to (5) depending on its constitution.

[0576] 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.

[0577] Alternatively, deuterium atoms may be deliberately introduced into the inventive compound by using a deuterated compound as part or all of the raw material compound. Therefore, in one embodiment of the present invention, the inventive compound contains at least one deuterium atom. That is, the inventive compound may 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.

[0578] In formula (1), R, R 1 ~R 6 、R that is not a single bond to *a 21 ~R 28 , R 31 ~R 38 , R 41 ~R 45 , R 51 ~R 52 and R 54 ~R 55 The hydrogen atoms, R, R 1 ~R 6 、R that is not a single bond to *a 21 ~R 28 , R 31 ~R 38 , R 41 ~R 45 , R 51 ~R 52 and R 54 ~R 55 The substituent represented by 1, L 2 , L 3 and L 4 The hydrogen atom of the arylene group represented by a At least one hydrogen atom among the hydrogen atoms possessed by the aryl group represented by 1 and Ar 2 At least one of the hydrogen atoms in the aryl group or heterocyclic group represented by may be a deuterium atom.

[0579] The deuteration rate of the invention compound (the ratio of the number of deuterium atoms in the invention compound to the total number of hydrogen atoms) depends on the deuteration rate of the raw material compound used. It is usually difficult to set the deuteration rate of all raw material compounds used to 100%, so the deuteration rate of the invention compound is lower than 100%.

[0580] 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.

[0581] The inventive compound may be a mixture of a deuterated compound (a compound into which deuterium atoms are intentionally introduced) and an undeuterated compound, or a mixture of two or more compounds having different deuteration rates. The deuteration rate of such a mixture (the ratio of the number of deuterium atoms in the inventive compound contained in the mixture to the total number of hydrogen atoms) is 1% or more, preferably 3% or more, more preferably 5% or more, and further preferably 10% or more, and less than 100%.

[0582] In the compound of the invention, at least one hydrogen atom selected from the hydrogen atom represented by R or the hydrogen atom possessed by the substituent represented by R 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 hydrogen atom represented by R or the substituent represented by R) is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and less than 100%.

[0583] In the compounds of the invention, R 1 ~R 6 A hydrogen atom or R 1 ~R 6 At least one of the hydrogen atoms in the substituent represented by may be a deuterium atom. 1 ~R 6 A hydrogen atom or R 1 ~R 6 The ratio of the total number of hydrogen atoms possessed by the substituent represented by is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and less than 100%.

[0584] In the inventive compound, R is selected from a single bond other than a bond to21 ~R 28 A hydrogen atom or an R that is not a single bond to *a 21 ~R 28 At least one of the hydrogen atoms in the substituent represented by may be a deuterium atom. The deuteration rate (the number of deuterium atoms relative to the number of R atoms not bonded to a single bond) is 21 ~R 28 A hydrogen atom or an R that is not a single bond to *a 21 ~R 28 The ratio of the total number of hydrogen atoms possessed by the substituent represented by is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and less than 100%.

[0585] In the compounds of the invention, R 31 ~R 38 A hydrogen atom or R 31 ~R 38 At least one of the hydrogen atoms in the substituent represented by may be a deuterium atom. 31 ~R 38 A hydrogen atom or R 31 ~R 38 The ratio of the total number of hydrogen atoms possessed by the substituent represented by is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and less than 100%.

[0586] In the inventive compound, selected from L 1 and L 2 At least one of the hydrogen atoms in the arylene group represented by may be a deuterium atom. 1 and L 2 The ratio of the total number of hydrogen atoms in the arylene group represented by is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and less than 100%.

[0587] In the inventive compound, selected from L 3 and L 4 At least one of the hydrogen atoms in the arylene group represented by may be a deuterium atom. 3 and L 4 The ratio of the total number of hydrogen atoms in the arylene group represented by is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and less than 100%.

[0588] In the compounds of the invention, R aAt least one of the hydrogen atoms in the aryl group represented by may be a deuterium atom. a The ratio of the total number of hydrogen atoms possessed by the aryl groups represented by is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and less than 100%.

[0589] In the inventive compound, selected from Ar 1 and Ar 2 At least one of the hydrogen atoms in the aryl or heterocyclic group represented by may be a deuterium atom. 1 and Ar 2 The ratio of the total number of hydrogen atoms possessed by the aryl or heterocyclic group represented by is 1% or more, preferably 3% or more, more preferably 5% or more, further preferably 10% or more, and less than 100%.

[0590] The details of the substituents (optional substituents) included in the definitions of the above formulae when expressed as "substituted or unsubstituted" are the same as those described in "Substituents when expressed as "substituted or unsubstituted"".

[0591] The compounds of the invention can be easily produced by those skilled in the art with reference to the following synthesis examples and known synthesis methods.

[0592] 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.

[0593] In the following specific examples, D represents a deuterium atom.

[0594] [Chemical formula 29]

[0595]

[0596] [Chemical formula 30]

[0597]

[0598] [Chemical formula 31]

[0599]

[0600] [Chemical formula 32]

[0601]

[0602] [Chemical formula 33]

[0603]

[0604] [Chemical formula 34]

[0605]

[0606] [Chemical formula 35]

[0607]

[0608] [Chemical formula 36]

[0609]

[0610] [Chemical formula 37]

[0611]

[0612] [Chemical formula 38]

[0613]

[0614] [Chemical formula 39]

[0615]

[0616] [Chemical formula 40]

[0617]

[0618] [Chemical formula 41]

[0619]

[0620] [Chemical formula 42]

[0621]

[0622] [Chemical formula 43]

[0623]

[0624] [Chemical formula 44]

[0625]

[0626] [Chemical formula 45]

[0627]

[0628] [Chemical formula 46]

[0629]

[0630] [Chemical formula 47]

[0631]

[0632] [Chemical formula 48]

[0633]

[0634] [Chemical formula 49]

[0635]

[0636] [Chemical formula 50]

[0637]

[0638] [Chemical formula 51]

[0639]

[0640] Materials for organic EL devices

[0641] 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%), more preferably 80% by mass or more (including 100%), more preferably 90% by mass or more (including 100%), more preferably 95% by mass or more (including 100%), particularly preferably 99% by mass or more (including 100%), and most preferably 99.9% by mass or more (including 100%). The material for an organic EL element of the present invention is useful for the manufacture of an organic EL element.

[0642] Organic EL elements

[0643] 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.

[0644] As examples of organic layers containing 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 a material for the electron transport region or the light-emitting layer of a fluorescent or phosphorescent EL element, more preferably a material for the electron transport region, further preferably a material for the electron injection layer, the electron transport layer, or the hole blocking layer, and particularly preferably a material for the hole blocking layer.

[0645] 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 a minimum unit that includes an organic layer, at least one of which is a light-emitting layer, and emits light by the recombination of injected holes and electrons.

[0646] For example, as a typical element structure of a simple organic EL element, the following element structure can be cited.

[0647] (1) Anode / light-emitting unit / cathode

[0648] 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 typical layer structure of a simplified light-emitting unit. The layers in parentheses are optional.

[0649] (a) (hole injection layer / ) hole transport layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[0650] (b) (hole injection layer / hole transport layer / phosphorescent light emitting layer / electron transport layer ( / electron injection layer)

[0651] (c) (hole injection layer / ) hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / electron transport layer ( / electron injection layer)

[0652] (d) (hole injection layer / ) hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer / electron transport layer ( / electron injection layer)

[0653] (e) (hole injection layer / ) hole transport layer / phosphorescent light emitting layer / spacer layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[0654] (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)

[0655] (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)

[0656] (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)

[0657] (i) (hole injection layer / ) hole transport layer / electron blocking layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[0658] (j) (hole injection layer / ) hole transport layer / electron blocking layer / phosphorescent light emitting layer / electron transport layer ( / electron injection layer)

[0659] (k) (hole injection layer / ) hole transport layer / exciton blocking layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[0660] (l) (hole injection layer / ) hole transport layer / exciton blocking layer / phosphorescent light emitting layer / electron transport layer ( / electron injection layer)

[0661] (m) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[0662] (n) (hole injection layer / ) first hole transport layer / second hole transport layer / phosphorescent light emitting layer / electron transport layer ( / electron injection layer)

[0663] (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)

[0664] (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)

[0665] (q) (hole injection layer / ) hole transport layer / fluorescent light emitting layer / hole blocking layer / electron transport layer ( / electron injection layer)

[0666] (r) (hole injection layer / ) hole transport layer / phosphorescent light emitting layer / hole blocking layer / electron transport layer ( / electron injection layer)

[0667] (s) (hole injection layer / ) hole transport layer / fluorescent light emitting layer / exciton blocking layer / electron transport layer ( / electron injection layer)

[0668] (t) (hole injection layer / ) hole transport layer / phosphorescent light emitting layer / exciton blocking layer / electron transport layer ( / electron injection layer)

[0669] Each of the phosphorescent or fluorescent light-emitting layers can be configured to emit light of different colors. Specifically, in the light-emitting unit (f), a layer structure such as (hole injection layer / ) hole transport layer / first phosphorescent light-emitting layer (red light emission) / second phosphorescent light-emitting layer (green light emission) / spacer layer / fluorescent light-emitting layer (blue light emission) / electron transport layer can be cited.

[0670] It should be noted that an electron blocking layer may be appropriately provided between each light-emitting layer and the hole transport layer or the spacer layer. In addition, a hole blocking layer may be appropriately provided between each light-emitting layer and the electron transport layer. By providing an electron blocking layer or a hole blocking layer, electrons or holes may be confined in the light-emitting layer to increase the recombination probability of charges in the light-emitting layer, thereby improving the luminous efficiency.

[0671] As a typical device structure of a tandem organic EL device, the following device structures can be mentioned.

[0672] (2) Anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode

[0673] 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.

[0674] The intermediate layer is also generally referred to as an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, or an intermediate insulating layer, and can be made of a known material that supplies electrons to the first light-emitting unit and holes to the second light-emitting unit.

[0675] Figure 1 Schematic diagram showing an example of the structure of the organic EL element of the present invention. The organic EL element 1 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10 arranged between the anode 3 and the cathode 4. The light-emitting unit 10 has a light-emitting layer 5. There is a hole transport region 6 (hole injection layer, hole transport layer, etc.) between the light-emitting layer 5 and the anode 3, and there is an electron transport region 7 (electron injection layer, electron transport layer, etc.) between the light-emitting layer 5 and the cathode 4. In addition, an electron blocking layer (not shown) can be provided on the anode 3 side of the light-emitting layer 5, and a hole blocking layer (not shown) can be provided on the cathode 4 side of the light-emitting layer 5, respectively. In this way, electrons and holes can be confined in the light-emitting layer 5 to further improve the generation efficiency of excitons in the light-emitting layer 5.

[0676] 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. In addition, there is a hole transport region 6 (hole injection layer, hole transport layer, etc.) disposed between the anode 3 and the light-emitting layer 5. In addition, there is an electron transport region disposed between the light-emitting layer 5 and the cathode 4, and the electron transport region is formed by a hole blocking layer 7a, an electron transport layer 7b, and an electron injection layer 7c.

[0677] It should be noted that in the present invention, the host combined with a fluorescent dopant (fluorescent luminescent material) is called a fluorescent host, and the host combined with a phosphorescent dopant is called a phosphorescent host. The fluorescent host and the phosphorescent host are not distinguished only by the molecular structure. That is, the phosphorescent host refers to the material that forms the phosphorescent luminescent layer containing the phosphorescent dopant, and does not mean that it cannot be used as a material for forming the fluorescent luminescent layer. The same is true for the fluorescent host.

[0678] substrate

[0679] 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.

[0680] anode

[0681] 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 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 cited.

[0682] These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target in which 1 to 10 wt% of zinc oxide is added to indium oxide, and indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5 to 5 wt% of tungsten oxide and 0.1 to 1 wt% of zinc oxide relative to indium oxide. In addition, it can also be produced by vacuum evaporation, coating, inkjet, spin coating, etc.

[0683] The hole injection layer formed adjacent to the anode is formed using a material that easily allows hole injection regardless of the work function of the anode. Therefore, materials commonly used as electrode materials (such as metals, alloys, conductive compounds and mixtures thereof, elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0684] It is also possible to use elements belonging to the first or second group of the periodic table as materials with a small work function, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing them. It should be noted that when using alkali metals, alkaline earth metals, and alloys containing them to form an anode, a vacuum evaporation method or a sputtering method can be used. In addition, when using silver paste, a coating method, an inkjet method, etc. can be used.

[0685] Hole injection layer

[0686] The hole injection layer is a layer containing a material with high hole injection properties (hole injection material), and is formed between the anode and the light-emitting layer, or, if a hole transport layer is present, between the hole transport layer and the anode.

[0687] As the hole injecting material, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide or the like can be used.

[0688] Examples of hole injection layer materials include low molecular weight organic compounds such as 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNT PD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) and other aromatic amine compounds.

[0689] High molecular weight compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, high molecular weight compounds such as poly(N-vinyl carbazole) (abbreviated as PVK), poly(4-vinyl triphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD) can be mentioned. In addition, high molecular weight compounds to which an acid is added, such as poly(3,4-ethylenedioxythiophene) / poly(styrene sulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrene sulfonic acid) (PAni / PSS), can also be used.

[0690] In addition, an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K) is also preferably used.

[0691] [Chemical formula 52]

[0692]

[0693] (In the above formula, R 21 ~R 26 Each 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-. )

[0694] As R 27 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl and the like can be mentioned.

[0695] Hole transport layer

[0696] The hole transport layer is a layer containing a material with a high hole transport property (hole transport material), and is formed between the anode and the light emitting layer, or, if a hole injection layer is present, between the hole injection layer and the light emitting layer.

[0697] The hole transport layer may be a single-layer structure or a multilayer structure comprising more than two layers. For example, the hole transport layer may be a two-layer structure comprising a first hole transport layer (anode side) and a second hole transport layer (cathode side). In one embodiment of the present invention, the hole transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, or 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 sandwiched between the hole transport layer of the single-layer structure and the light-emitting layer, or between the hole transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer.

[0698] As the hole transport layer material, for example, an aromatic amine compound, a carbazole derivative, an anthracene derivative or the like can be used.

[0699] 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-9-yl)triphenylamine (abbreviation: BAFLP), -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.

[0700] 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).

[0701] 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).

[0702] A polymer compound such as poly(N-vinylcarbazole) (abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation: PVTPA) may also be used.

[0703] However, any compound other than the above compounds may be used as long as the compound has a higher hole-transporting property than an electron-transporting property.

[0704] Dopant materials for the light-emitting layer

[0705] The light-emitting layer is a layer containing a material with high luminescence (dopant material), and various materials can be used. For example, fluorescent materials and phosphorescent materials can be used as dopant materials. Fluorescent materials are compounds that emit light using a singlet excited state, and phosphorescent materials are compounds that emit light using a triplet excited state.

[0706] As the blue fluorescent material that can be used for the light-emitting layer, pyrene derivatives, styrylamine derivatives, Derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. Specifically, N, N'-bis [4- (9H-carbazole-9-yl) phenyl] -N, N'-diphenylstilbene-4, 4'-diamine (abbreviation: YGA2S), 4- (9H-carbazole-9-yl) -4'- (10-phenyl-9-anthracenyl) triphenylamine (abbreviation: YGAPA), 4- (10-phenyl-9-anthracenyl) -4'- (9-phenyl-9H-carbazole-3-yl) triphenylamine (abbreviation: PCBAPA) and the like can be mentioned.

[0707] 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.

[0708] 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.

[0709] As a blue phosphorescent material that can be used for the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes can be used. Specifically, bis[2-(4',6'-difluorophenyl)pyridine-N, C2']iridium(III)tetrakis(1-pyrazolyl)borate (abbreviated as FIr6), bis[2-(4',6'-difluorophenyl)pyridine-N, C2']iridium(III)picolinate (abbreviated as FIrpic), bis[2-(3',5'bistrifluoromethylphenyl)pyridine-N, C2']iridium(III)picolinate (abbreviated as Ir(CF3ppy)2(pic)), bis[2-(4',6'-difluorophenyl)pyridine-N, C2']iridium(III)acetylacetonate (abbreviated as FIracac), etc. can be cited.

[0710] As green phosphorescent materials that can be used for the light-emitting layer, iridium complexes can be used, such as tris(2-phenylpyridine-N, C2')iridium(III) (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)), bis(benzo[h]quinoline)iridium(III)acetylacetonate (abbreviated as Ir(bzq)2(acac)), and the like.

[0711] As the red phosphorescent light-emitting material that can be used for the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes can be used. Specifically, organic metal complexes such as bis[2-(2'-benzo[4,5-α]thienyl)pyridine-N,C3']iridium(III)acetylacetonate (abbreviated as Ir(btp)2(acac)), bis(1-phenylisoquinoline-N,C2')iridium(III)acetylacetonate (abbreviated as Ir(piq)2(acac)), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviated as Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as PtOEP) can be cited.

[0712] In addition, rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviated as: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedione)(monophenanthroline)europium(III) (abbreviated as: Eu(DBM)3(Phen)), and tris[1-(2-thiophenoyl)-3,3,3-trifluoroacetone](monophenanthroline)europium(III) (abbreviated as: Eu(TTA)3(Phen)) can be used as phosphorescent materials because the luminescence comes from rare earth metal ions (electron transitions between different multiplicities).

[0713] Host material of the light-emitting layer

[0714] The light-emitting layer may be a structure in which the above-mentioned dopant material is dispersed in another material (host material). It is preferable to use a material having a higher lowest unoccupied molecular orbital level (LUMO level) and a lower highest occupied molecular orbital level (HOMO level) than the dopant material.

[0715] As the main material, for example,

[0716] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes,

[0717] (2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives,

[0718] (3) Carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or Derivatives and other condensed aromatic compounds,

[0719] (4) Aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives.

[0720] 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;

[0721] 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2',2"-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP) and other heterocyclic compounds;

[0722] 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviated as DPPA), 9,10-di(2-naphthyl)anthracene (abbreviated as DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviated as : t-BuDNA), 9,9'-bianthracene (abbreviated as: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviated as: DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviated as: DPNS2), 3,3',3"-(benzene-1,3,5-triyl)tripyrene (abbreviated as: TPB3), 9,10-diphenylanthracene (abbreviated as: DPAnth), 6,12-dimethoxy-5,11-diphenyl Equi-fused aromatic compounds; and

[0723] 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 -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), 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). Two or more types of the host material can be used.

[0724] In particular, in the case of a blue fluorescent element, it is preferable to use the anthracene compound described below as a host material.

[0725] [Chemical formula 53]

[0726]

[0727] [Chemical formula 54]

[0728]

[0729] [Chemical formula 55]

[0730]

[0731] Electron transport layer

[0732] The electron transport layer is a layer containing a material with a high electron transport property (electron transport material), and is formed between the light emitting layer and the cathode, or, if an electron injection layer exists, between the electron injection layer and the light emitting layer.

[0733] The compound of the invention is preferably used in an electron transport layer alone or in combination with the following compounds.

[0734] The electron transport layer may be a single-layer structure or a multilayer structure comprising more than two layers. For example, the electron transport layer may be a two-layer structure comprising a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one embodiment of the present invention, the electron transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, or the electron transport layer closest to the anode in the multilayer structure, such as the first electron transport layer of the two-layer structure, is preferably adjacent to the light-emitting layer. In another embodiment of the present invention, a hole blocking layer described later may be sandwiched between the electron transport layer of the single-layer structure and the light-emitting layer, or between the electron transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer.

[0735] In the electron transport layer having the above two-layer structure, the compound of the invention may be contained in one of the first electron transport layer and the second electron transport layer, or may be contained in both.

[0736] In one embodiment of the present invention, the inventive compound is preferably contained only in the first electron transport layer adjacent to the light-emitting layer. In another embodiment, the inventive compound is preferably contained only in the second electron transport layer. In still another embodiment, the inventive compound is preferably contained in both the first electron transport layer and the second electron transport layer.

[0737] In one embodiment of the present invention, the compound of the invention contained in one or both of the first electron transport layer and the second electron transport layer is preferably a protium body from the viewpoint of production cost.

[0738] The above-mentioned protium compound refers to a compound of the invention in which all hydrogen atoms in the formula (1) are protium atoms.

[0739] Therefore, the present invention includes an organic EL device in which one or both of the first electron transport layer and the second electron transport layer contain an invention compound substantially constituted via a protium body. "The invention compound substantially constituted via a 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 (each including 100%).

[0740] Electron transport layers other than the inventive compound can be used, for example

[0741] (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes,

[0742] (2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives,

[0743] (3)Polymer compounds.

[0744] Examples of the metal complex include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinolato)beryllium (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenol)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviation: ZnBTZ).

[0745] 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).

[0746] 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).

[0747] 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.

[0748] Electron injection layer

[0749] The electron injection layer is a layer containing a material with high electron injection properties (electron injection material), and is formed between the cathode and the light-emitting layer, or, when an electron transport layer is present, between the electron transport layer and the cathode. The compound of the invention can be used for the electron injection layer.

[0750] As electron injection materials other than the invention compound, 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 can be used. As such compounds, for example: alkali metal oxides, alkali metal halides, organic complexes containing alkali metals, alkaline earth metal oxides, alkaline earth metal halides, organic complexes containing alkaline earth metals, rare earth metal oxides, rare earth metal halides, and organic complexes containing rare earth metals can be cited. In addition, a variety of these compounds can also be used in combination.

[0751] Alternatively, a material having an electron transport property and containing an alkali metal, an alkaline earth metal or a compound thereof may be used, specifically, a material containing magnesium (Mg) in Alq, etc. In this case, electron injection from the cathode can be performed more efficiently.

[0752] Alternatively, the electron injection layer can use a composite material mixed with an organic compound and an electron donor (donor). Such a composite material has excellent electron injection and electron transport properties because the organic compound accepts electrons from the electron donor. At this time, as an organic compound, it is preferably a material with excellent transmission of the accepted electrons. Specifically, for example, the material (metal complex, heteroaromatic compound, etc.) constituting the electron transport layer mentioned above can be used. As an electron donor, it is a material that exhibits electron donation to the organic compound. Specifically, alkali metals, alkaline earth metals and rare earth metals are preferred, and lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. can be cited. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, and lithium oxide, calcium oxide, barium oxide, etc. can be cited. In addition, a Lewis base such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviated as: TTF) can also be used.

[0753] cathode

[0754] The cathode preferably uses a metal, alloy, conductive compound, and mixtures thereof with a small work function (specifically, less than 3.8 eV). Specific examples of such cathode materials include elements belonging to the first or second group of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys thereof (e.g., MgAg, AlLi), and rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys thereof.

[0755] It should be noted that when an alkali metal, an alkaline earth metal, or an alloy containing them is used to form the cathode, a vacuum deposition method or a sputtering method may be used. In addition, when a silver paste or the like is used, a coating method or an inkjet method may be used.

[0756] 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.

[0757] Insulation layer

[0758] Organic EL elements are prone to pixel defects due to leakage and short circuits due to the application of an electric field to ultra-thin films. To prevent this, an insulating layer formed of an insulating thin film layer may be inserted between a pair of electrodes.

[0759] Examples of materials that can be used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. It should be noted that mixtures and laminates thereof may also be used.

[0760] Spacer

[0761] For example, when a fluorescent light-emitting layer and a phosphorescent light-emitting layer are stacked, the spacer layer is a layer disposed between the fluorescent light-emitting layer and the phosphorescent light-emitting layer for the purpose of preventing the excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer or adjusting the carrier balance. In addition, the spacer layer may also be disposed between a plurality of phosphorescent light-emitting layers.

[0762] 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.

[0763] Barrier layer

[0764] Blocking layers such as electron blocking layers, hole blocking layers, and exciton blocking layers 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.

[0765] As an embodiment, the inventive compound is preferably used as the hole blocking layer.

[0766] The exciton blocking layer has a function of preventing excitons generated in the light-emitting layer from diffusing to the surrounding layers and confining the excitons in the light-emitting layer.

[0767] Each layer of the organic EL element can be formed by a conventionally known vapor deposition method, coating method, etc. For example, it can be formed by a vapor deposition method such as a vacuum vapor deposition method, a molecular beam vapor deposition method (MBE method), or a known method based on a coating method such as a dip coating method, a spin coating method, a casting method, a rod coating method, a roll coating method, etc. using a solution of a layer-forming compound.

[0768] The thickness of each layer is not particularly limited. Generally, if the thickness is too thin, defects such as pinholes are easily generated, while if it is too thick, a high driving voltage is required and the efficiency is deteriorated. Therefore, it is usually 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm.

[0769] The organic EL element can be used in display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and electronic devices such as lighting and light-emitting devices for vehicle lamps.

[0770] Example

[0771] Hereinafter, the present invention will be described in further detail using examples, but the present invention is not limited to the following examples.

[0772] The invention compounds used in the production of the organic EL devices of Examples 1 to 19 below

[0773] [Chemical formula 56]

[0774]

[0775] [Chemical formula 57]

[0776]

[0777] [Chemical formula 58]

[0778]

[0779] [Chemical formula 59]

[0780]

[0781] The comparative compounds used in the production of the organic EL devices of Comparative Examples 1 to 3 below

[0782] [Chemical formula 60]

[0783]

[0784] Other compounds used in the manufacture of the organic EL devices of Examples 1 to 19 and Comparative Examples 1 to 3 below

[0785] [Chemical formula 61]

[0786]

[0787] Each organic EL element was produced as described below, and the EL element performance of each element was evaluated.

[0788] Fabrication of organic EL elements

[0789] Example 1

[0790] A 25 mm×75 mm×1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.

[0791] The cleaned glass substrate with transparent electrode lines was mounted on a substrate holder of a vacuum evaporation device. First, compound HT-1 and compound HI-1 were co-evaporated on the surface of the side where the transparent electrode lines were formed so as to cover the transparent electrode to form a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-1 to compound HI-1 was 97:3.

[0792] 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.

[0793] Next, compound EBL-1 was vapor-deposited on the first hole transport layer to form a second hole transport layer (electron blocking layer) having a film thickness of 10 nm.

[0794] Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated on the second hole transport layer (electron blocking layer) to form a 25 nm thick light emitting layer. The mass ratio of compound BH-1 to compound BD-1 was 96:4.

[0795] Next, Compound 1 (HBL-1) was vapor-deposited on the light-emitting layer to form a hole-blocking layer having a thickness of 10 nm.

[0796] Compound ET-1 was evaporated to form an electron transport layer having a thickness of 15 nm.

[0797] Next, Yb was vapor-deposited on the electron transport layer to form an electron injecting electrode (cathode) having a film thickness of 1 nm.

[0798] Then, metal Al was vapor-deposited on the electron injecting electrode to form a metal cathode having a film thickness of 80 nm.

[0799] The layer structure of the organic EL device of Example 1 obtained in this manner is as follows.

[0800] ITO(130) / HT-1:HI-1=97:3(10) / HT-1(80) / EBL-1(10) / BH-1:BD-1=96:4(25) / HBL-1(10) / ET-1(15) / Yb(1) / Al(80)

[0801] In the above layer configuration, the numbers in parentheses are film thicknesses (nm), and the ratios of HT-1 to HI-1 and BH-1 to BD-1 are mass ratios.

[0802] Embodiments 2 to 19

[0803] Organic EL devices of Examples 2 to 19 were prepared in the same manner as in Example 1 except that Compound 2 (HBL-2) to Compound 19 (HBL-19) were used in this order instead of Compound 1 (HBL-1) in the hole blocking layer.

[0804] Comparative Examples 1 to 3

[0805] Organic EL elements of Comparative Examples 1 to 3 were prepared in the same manner as in Example 1 except that Comparative Compound 1 (HBL-A), Comparative Compound 2 (HBL-B) and Comparative Compound 3 (HBL-C) were used in this order instead of Compound 1 (HBL-1) of the hole blocking layer.

[0806] Evaluation of organic EL elements

[0807] The device life of each of the produced organic EL devices was evaluated. The evaluation results are shown in Table 1.

[0808] Component life (LT95)

[0809] The obtained organic EL device was heated at a current density of 50 mA / cm 2 The device was driven by direct current, and the time until the luminance decreased to 95% of the initial luminance was measured, and this time was defined as LT95 (95% life).

[0810] [Table 1]

[0811] Table 1

[0812]

[0813] Evaluation of glass transition temperature Tg

[0814] For the compound used as a hole blocking layer, the glass transition temperature Tg was evaluated.

[0815] The glass transition temperature was measured using a differential scanning calorimeter DSC7000X (Hitachi High-Tech Scientific Co., Ltd.) according to the method specified in JIS K7121 (1987).

[0816] [Table 2]

[0817] Table 2

[0818] Compound HBL Tg(℃) Compound 1 (HBL-1) 133 Compound 2 (HBL-2) 138 Compound 3 (HBL-3) 151 Compound 4 (HBL-4) 159 Compound 5 (HBL-5) 128 Compound 6 (HBL-6) 156 Compound 7 (HBL-7) 136 Compound 8 (HBL-8) 128 Compound 9 (HBL-9) 130 Compound 10 (HBL-10) 141 Compound 11 (HBL-11) 133 Compound 12 (HBL-12) 131 Compound 13 (HBL-13) 157 Compound 14 (HBL-14) 146 Compound 15 (HBL-15) 146 Compound 16 (HBL-16) 149 Compound 17 (HBL-17) 128 Compound 18 (HBL-18) 138 Compound 19 (HBL-19) 133 Comparative Compound 1 (HBL-A) 108 Comparative Compound 2 (HBL-B) 123 Comparative Compound 3 (HBL-C) 113

[0819] According to the results in Tables 1 and 2, the compounds of the present invention having a structure in which a specific carbazole skeleton is bonded to a pyrimidine skeleton via a single bond or an aryl group and further via a naphthyl group, having a molecular weight of 650 or more and a high glass transition temperature, show further improved device life compared to comparison compounds 1 to 3 that do not meet the structural conditions or molecular weight of the present invention.

[0820] <Synthesis of Compounds>

[0821] Synthesis of Intermediate A

[0822] [Chemical formula 62]

[0823]

[0824] 4-Bromo-1-naphthaldehyde (9.0 g), acetophenone (4.6 g), and sodium hydroxide (0.15 g) were added to 300 mL of ethanol and stirred at room temperature for 5 hours. Next, benzamidine hydrochloride (6.0 g) and sodium hydroxide (1.8 g) were added and stirred at 70° C. for 5 hours. After the reaction was completed, the precipitate was filtered out and purified by silica gel column chromatography (developing solvent: hexane / toluene) to obtain intermediate A as a white solid (7.6 g, yield 45%).

[0825] Synthesis Example 1: Synthesis of Compound 1

[0826] [Chemical formula 63]

[0827]

[0828] Intermediate A (5.0 g) and [4'-(carbazole-9-yl)-4-biphenyl]boronic acid (4.5 g) were added to 1,2-dimethoxyethane (80 mL), and argon was passed through the solution for 5 minutes. Pd(PPh3)4 (0.4 g) and aqueous sodium carbonate solution (2M, 12 mL) were added thereto, and the mixture was heated under reflux conditions for 7 hours while stirring under an argon atmosphere. The reaction solution was subjected to solvent distillation, and the obtained solid was purified by silica gel column chromatography (developing solvent: hexane / toluene), thereby obtaining HBL-1 as a white solid (6.6 g, yield 85%). As a result of mass spectrometry analysis, m / e=676 relative to the molecular weight of 675.84, and thus it was identified as compound 1 (HBL-1).

[0829] Synthesis of intermediate B

[0830] [Chemical formula 64]

[0831]

[0832] 4-Bromo-1-naphthaldehyde (8.0 g), 4-acetylbiphenyl (7.0 g), and sodium hydroxide (0.27 g) were added to 600 mL of ethanol and stirred at room temperature for 5 hours. Next, benzamidine hydrochloride (8.0 g) and sodium hydroxide (2.7 g) were added and stirred at 70° C. for 5 hours. After the reaction was completed, the precipitate was filtered out and purified by silica gel column chromatography (developing solvent: hexane / toluene) to obtain intermediate B as a white solid (5.0 g, yield 28%).

[0833] Synthesis Example 2: Synthesis of Compound 2

[0834] [Chemical formula 65]

[0835]

[0836] Intermediate B (5.0 g) was used to obtain HBL-2 ​​as a white solid (4.5 g, yield 68%) by the same method as in Synthesis Example 1. The mass spectrometry analysis showed that the molecular weight was 675.84 and m / e was 676, so it was identified as Compound 2 (HBL-2).

[0837] Synthesis of Intermediate C

[0838] [Chemical formula 66]

[0839]

[0840] Intermediate C was obtained as a white solid (9.0 g, yield 83%) by the same method as the synthesis method of Synthesis Example 1 using Intermediate A (10.0 g) and 4-fluorophenylboric acid (3.5 g).

[0841] Synthesis Example 3: Synthesis of Compound 3

[0842] [Chemical formula 67]

[0843]

[0844] Intermediate C (3.8 g), 3,6-diphenylcarbazole (4.0 g), cesium carbonate (8.2 g) were added to 30 mL of N-methylpyrrolidone (NMP) and stirred at 160°C for 24 hours. After the reaction solution was cooled to room temperature, 100 mL of methanol and 100 mL of water were added and stirred at room temperature for 1 hour. The precipitated solid was collected by filtration and purified by silica gel column chromatography (developing solvent: hexane / toluene) to obtain HBL-3 as a white solid (6.3 g, yield 94%). The results of mass spectrometry analysis showed that the molecular weight was 751.93 and m / e=752, so it was identified as compound 3 (HBL-3).

[0845] Synthesis of intermediate D

[0846] [Chemical formula 68]

[0847]

[0848] Intermediate A (5.0 g) and 3,5-difluorophenylboric acid (2.0 g) were used in the same manner as in Synthesis Example 1 to obtain Intermediate D as a white solid (4.2 g, yield 78%).

[0849] Synthesis Example 4: Synthesis of Compound 4

[0850] [Chemical formula 69]

[0851]

[0852] Intermediate D (4.2 g) and carbazole (4.5 g) were used to obtain HBL-4 as a white solid (4.1 g, yield 60%) by the same method as in Synthesis Example 3. The mass spectrometry analysis showed that the molecular weight was 764.93 and m / e = 765, and thus the compound was identified as Compound 4 (HBL-4).

[0853] Synthesis Example 5: Synthesis of Compound 5

[0854] [Chemical formula 70]

[0855]

[0856] Intermediate A (3.9 g) and 9-phenyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-9H-carbazole (4.0 g) were used to obtain HBL-5 as a white solid (4.7 g, yield 78%) by the same method as the synthesis method of Synthesis Example 1. The results of mass spectrometry showed that m / e=676 relative to the molecular weight of 675.84, and thus it was identified as Compound 5 (HBL-5).

[0857] Synthesis Example 6: Synthesis of Compound 6

[0858] [Chemical formula 71]

[0859]

[0860] Intermediate A (6.0 g), 3,6-diphenylcarbazole (4.2 g), palladium acetate (0.48 g), Amphos (1.3 g), t-BuONa (3.8 g) were added to 168 mL of dehydrated xylene and stirred for 36 hours under reflux conditions. After the reaction solution was cooled to room temperature, 100 mL of methanol and 100 mL of water were added and stirred at room temperature for 1 hour. The precipitated solid was collected by filtration and purified by silica gel column chromatography (developing solvent: hexane / toluene) to obtain HBL-6 as a white solid (4.8 g, yield 52%).

[0861] The result of mass spectrometry analysis showed that m / e=675 relative to the molecular weight of 675.84, and thus the compound was identified as Compound 6 (HBL-6).

[0862] Synthesis Example 7: Synthesis of Compound 7

[0863] [Chemical formula 72]

[0864]

[0865] Using Intermediate C (5.6 g), under the same conditions as described in Synthesis Example 3, HBL-7 was obtained as a white solid (5.9 g, yield 61%).

[0866] The result of mass spectrometry analysis showed that m / e=675 relative to the molecular weight of 675.84, and thus the compound was identified as Compound 7 (HBL-7).

[0867] Synthesis Example 8: Synthesis of Compound 8

[0868] [Chemical formula 73]

[0869]

[0870] Using Intermediate E (8.0 g) synthesized by the synthesis method of Intermediate B using 3-acetylbiphenyl as a starting material, HBL-8 was obtained as a white solid (10.3 g, yield 87%) under the same conditions as described in Synthesis Example 1.

[0871] The result of mass spectrometry analysis showed that m / e=675 relative to the molecular weight of 675.84, and thus the compound was identified as Compound 8 (HBL-8).

[0872] Synthesis Example 9: Synthesis of Compound 9

[0873] [Chemical formula 74]

[0874]

[0875] Using Intermediate E (5.0 g) and Intermediate F (3.6 g), under the same conditions as described in Synthesis Example 1, HBL-9 was obtained as a white solid (5.7 g, yield 78%).

[0876] The result of mass spectrometry analysis showed that m / e=751 relative to the molecular weight of 751.93, and thus the compound was identified as Compound 9 (HBL-9).

[0877] Synthesis Example 10: Synthesis of Compound 10

[0878] [Chemical formula 75]

[0879]

[0880] Using Intermediate B (4.0 g) and Intermediate F (2.8 g), under the same conditions as described in Synthesis Example 1, HBL-10 was obtained as a white solid (5.1 g, yield 87%).

[0881] The result of mass spectrometry analysis showed that m / e=751 relative to the molecular weight of 751.93, and thus the compound was identified as Compound 10 (HBL-10).

[0882] Synthesis of Intermediate G

[0883] [Chemical formula 76]

[0884]

[0885] Using Intermediate A (10.0 g) and 4-chlorophenylboronic acid (3.6 g), under the same conditions as described in Synthesis Example 1, Intermediate G was obtained as a white solid (9.8 g, yield 91%).

[0886] Synthesis Example 11: Synthesis of Compound 11

[0887] [Chemical formula 77]

[0888]

[0889] Intermediate G (4.5 g), N-phenylcarbazole-2-boric acid (4.1 g), and tripotassium phosphate (8.2 g) were added to 1,4-dioxane (100 mL), and argon was passed through the solution for 5 minutes. Pd2(dba)3 (0.18 g) and SPhos (0.32 g) were added thereto, and the mixture was heated under reflux conditions for 24 hours while stirring under an argon atmosphere. The reaction solution was subjected to solvent distillation, and the obtained solid was purified by silica gel column chromatography (developing solvent: hexane / toluene) to obtain HBL-11 as a white solid (5.8 g, yield 90%).

[0890] The result of mass spectrometry analysis showed that m / e=675 relative to the molecular weight of 675.84, and thus the compound was identified as Compound 11 (HBL-11).

[0891] Synthesis Example 12: Synthesis of Compound 12

[0892] [Chemical formula 78]

[0893]

[0894] Using Intermediate G (3.5 g) and N-phenylcarbazole-4-boronic acid (3.2 g), under the same conditions as described in Synthesis Example 11, HBL-12 was obtained as a white solid (3.1 g, yield 62%).

[0895] The result of mass spectrometry analysis showed that m / e=675 relative to the molecular weight of 675.84, and thus the compound was identified as Compound 12 (HBL-12).

[0896] Synthesis of intermediate H

[0897] [Chemical formula 79]

[0898]

[0899] Using Intermediate A (5.0 g) and 3,4-difluorophenylboric acid (2.5 g), under the same conditions as described in Synthesis Example 1, Intermediate H was obtained as a white solid (4.3 g, yield 80%).

[0900] Synthesis Example 13 Synthesis of Compound 13

[0901] [Chemical formula 80]

[0902]

[0903] Using Intermediate H (4.3 g), under the same conditions as described in Synthesis Example 3, HBL-13 was obtained as a white solid (5.5 g, yield 79%).

[0904] The result of mass spectrometry analysis showed that m / e=764 relative to the molecular weight of 764.93, and thus the compound was identified as Compound 13 (HBL-13).

[0905] Synthesis of Intermediate I

[0906] [Chemical formula 81]

[0907]

[0908] Using Intermediate A (5.0 g) and 3-fluorophenylboronic acid (2.2 g), under the same conditions as described in Synthesis Example 1, Intermediate I was obtained as a white solid (4.8 g, yield 92%).

[0909] Synthesis Example 14: Synthesis of Compound 14

[0910] [Chemical formula 82]

[0911]

[0912] Using Intermediate I (4.8 g) and 3,6-diphenylcarbazole (5.0 g), under the same conditions as described in Synthesis Example 3, HBL-14 was obtained as a white solid (7.2 g, yield 90%).

[0913] The result of mass spectrometry analysis showed that m / e=751 relative to the molecular weight of 751.93, and thus the compound was identified as Compound 14 (HBL-14).

[0914] Synthesis Example 15: Synthesis of Compound 15

[0915] [Chemical formula 83]

[0916]

[0917] Using Intermediate B (4.0 g) and [4′-(carbazol-9-yl)-4-biphenyl]boronic acid (3.4 g), under the same conditions as described in Synthesis Example 1, HBL-15 was obtained as a white solid (5.0 g, yield 76%).

[0918] The result of mass spectrometry analysis showed that m / e=751 relative to the molecular weight of 751.93, and thus the compound was identified as Compound 15 (HBL-15).

[0919] Synthesis Example 16: Synthesis of Compound 16

[0920] [Chemical formula 84]

[0921]

[0922] Using Intermediate B (4.5 g) and N-phenylcarbazole-4-boronic acid (3.0 g), under the same conditions as described in Synthesis Example 1, HBL-16 was obtained as a white solid (5.5 g, yield 92%).

[0923] The result of mass spectrometry analysis showed that m / e=675 relative to the molecular weight of 675.84, and thus the compound was identified as Compound 16 (HBL-16).

[0924] Synthesis Example 17: Synthesis of Compound 17

[0925] [Chemical formula 85]

[0926]

[0927] Using Intermediate B (5.0 g) and 3-(N-carbazolyl)phenylboronic acid (3.4 g), under the same conditions as described in Synthesis Example 1, HBL-17 was obtained as a white solid (5.6 g, yield 85%).

[0928] The result of mass spectrometry analysis showed that m / e=675 relative to the molecular weight of 675.84, and thus the compound was identified as Compound 17 (HBL-17).

[0929] Synthesis of Intermediate J

[0930] [Chemical formula 86]

[0931]

[0932] Using Intermediate B (5.0 g) and 4-fluorophenylboronic acid (1.6 g), under the same conditions as described in Synthesis Example 1, Intermediate J was obtained as a white solid (4.5 g, yield 87%).

[0933] Synthesis Example 18: Synthesis of Compound 18

[0934] [Chemical formula 87]

[0935]

[0936] Using Intermediate J (4.5 g) and carbazole-d8 (2.2 g), under the same conditions as described in Synthesis Example 3, HBL-18 was obtained as a white solid (3.8 g, yield 65%).

[0937] The result of mass spectrometry analysis showed that m / e=683 relative to the molecular weight of 683.88, and thus the compound was identified as Compound 18 (HBL-18).

[0938] Synthesis of intermediate K

[0939] [Chemical formula 88]

[0940]

[0941] Using acetophenone (phenyl-d5) (4.8 g) instead of acetophenone, according to the synthesis method of intermediate A, intermediate K was obtained as a white solid (5.1 g, yield 30%).

[0942] Synthesis Example 19: Synthesis of Compound 19

[0943] [Chemical formula 89]

[0944]

[0945] Using Intermediate K (3.0 g) and [4′-(carbazol-9-yl)-4-biphenyl]boronic acid (2.5 g), under the same conditions as described in Synthesis Example 1, HBL-19 was obtained as a white solid (2.0 g, yield 43%).

[0946] The result of mass spectrometry analysis showed that m / e=680 relative to the molecular weight of 680.87, and thus the compound was identified as Compound 19 (HBL-19).

[0947] In addition, the compound of the present invention can also be synthesized via the following synthetic intermediates according to the conditions described in the synthetic examples.

[0948] [Chemical formula 90]

[0949]

[0950] [Chemical formula 91]

[0951]

[0952] [Chemical formula 92]

[0953]

[0954] [Chemical formula 93]

[0955]

[0956] [Chemical formula 94]

[0957]

[0958] [Chemical formula 95]

[0959]

[0960] [Chemical formula 96]

[0961]

[0962] Explanation of symbols

[0963] 1.11 Organic EL elements

[0964] 2 substrate

[0965] 3 Anode

[0966] 4 Cathode

[0967] 5. Luminous layer

[0968] 6 Hole transport region (hole injection layer, hole transport layer, etc.)

[0969] 7 Electron transport region (electron injection layer, electron transport layer, etc.)

[0970] 7a Hole blocking layer

[0971] 7b Electron transport layer

[0972] 7c Electron injection layer

[0973] 10, 20 light units

Claims

1. A compound represented by the following formula (1): The molecular weight of the compound is 650 or more, In the formula, Y 1 and Y 2 One of them is a nitrogen atom, and the other one is CR. R is a hydrogen atom; Ar 1 and Ar 2 Each is independently selected from 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; Ar 1 and Ar 2 The unsubstituted aryl groups of the substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms are each independently selected from phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, Base and pyrene base, Ar 1 and Ar 2 The unsubstituted heterocyclic group of the substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms represented by is each independently selected from pyridyl, dibenzothienyl, dibenzofuranyl, azadibenzofuranyl, pyrimidinyl, quinolyl, isoquinolyl, benzothienyl and benzofuranyl, L 1 and L 2 1 of which is selected from unsubstituted phenylene, unsubstituted biphenylene and unsubstituted naphthylene and the remaining 1 is a single bond, or L 1 and L 2 are each independently selected from unsubstituted phenylene, unsubstituted biphenylene and unsubstituted naphthylene, R 1 ~R 6 are each independently selected from a hydrogen atom, a substituted or unsubstituted phenyl group and a substituted or unsubstituted methyl group, and selected from R 1 ~R 6 The two adjacent ones in are not bonded to each other to form a ring. Cz is represented by the following formula (1-a) or formula (1-b); In the formula, R 21 ~R 28 and R 31 ~R 38 are each independently a hydrogen atom or a substituent selected from a substituted or unsubstituted phenyl group and a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, in, Selected from R 21 ~R 28 Two adjacent ones in R 31 ~R 38 The two adjacent ones in R 24 With R 25 , and R 34 With R 35 They are not bonded to form a ring. R a is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl and substituted or unsubstituted naphthyl; Selected from R 21 ~R 28 One of them is connected to L via *a 3 Bonded single bonds; *b indicates the same as L 3 The bonding position, n is an integer of 1 to 2. When n is 2, the two Cz are the same or different from each other; L 3 is a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, L 4 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, When n is 2, L 4 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, L 3 and L 4 The unsubstituted arylene groups of the substituted or unsubstituted arylene groups having 6 to 50 ring carbon atoms represented by are each independently selected from phenylene, biphenylene, naphthylene, phenanthrylene and anthracene, When the term "substituted or unsubstituted" is used, the substituent is selected from unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, and A group in an unsubstituted aryl group having 6 to 18 ring carbon atoms.

2. The compound according to claim 1, wherein L 3 and L 4 are each independently a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, L 3 and L 4 The unsubstituted arylene groups of the substituted or unsubstituted arylene groups having 6 to 50 ring carbon atoms represented by are each independently selected from phenylene, biphenylene, naphthylene, phenanthrylene and anthracene.

3. The compound according to claim 1, wherein L 3 and L 4 The unsubstituted arylene groups of the substituted or unsubstituted arylene groups having 6 to 50 ring carbon atoms represented by are each independently selected from phenylene, biphenylene and naphthylene.

4. The compound according to claim 1, wherein L 3 For a single key.

5. The compound according to claim 1, wherein Selected from not via *a and L 3 R of the bonded single bond 21 ~R 28 At least one of or selected from R 31 ~R 38 At least one of them is a substituent.

6. The compound according to claim 5, wherein Not through *a and L 3 R of the bonded single bond 21 ~R 28 and R 31 ~R 38 At least one of the substituents represented by is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and phenyl.

7. The compound according to claim 1, which is represented by formula (1-b-1) or (1-b-2), Where Y 1 , Y 2 ,Ar 1 ,Ar 2 , L 1 , L 2 and R 1 ~R 6 Same as the definition in formula (1), R 31 ~R 38 Same as defined in formula (1-b), R 41 ~R 42 , R 44 ~R 45 , R 51 ~R 52 and R 54 ~R 55 Each is independently selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

8. The compound according to claim 1, which is represented by any one of formulas (1-b-11) to (1-b-14), Where Y 1 , Y 2 ,Ar 1 ,Ar 2 , L 1 , L 2 and R 1 ~R 6 Same as the definition in formula (1), R 31 ~R 38 Same as defined in formula (1-b), R 41 ~R 45 Each is independently selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

9. The compound according to claim 1, which is represented by any one of formulas (1-a-1) to (1-a-4), Where Y 1 , Y 2 ,Ar 1 ,Ar 2 , L 1 , L 2 and R 1 ~R 6 Same as the definition in formula (1), R a , R 21 ~R 28 Same as defined in formula (1-a), R 41 ~R 42 and R 44 ~R 45 Each is independently selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

10. The compound according to claim 1, wherein L 1 and L 2 Each is independently selected from unsubstituted phenylene, unsubstituted biphenylene and unsubstituted naphthylene.

11. The compound according to claim 1, wherein Ar 1 and Ar 2 The unsubstituted aryl groups of the substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms represented by are each independently selected from phenyl, biphenyl, naphthyl, phenanthrenyl and anthracenyl.

12. The compound according to claim 1, wherein Ar 1 and Ar 2 The unsubstituted heterocyclic group of the substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms represented by is each independently selected from a pyridyl group, a dibenzothienyl group, a dibenzofuranyl group, a pyrimidinyl group, a benzothienyl group and a benzofuranyl group.

13. The compound according to claim 1, wherein R a is substituted or unsubstituted phenyl.

14. The compound according to claim 1, wherein R 1 ~R 6 All are hydrogen atoms.

15. The compound according to any one of claims 7 to 9, wherein R 41 ~R 45 All are hydrogen atoms.

16. The compound according to claim 7, wherein R 51 ~R 52 and R 54 ~R 55 All are hydrogen atoms.

17. The compound according to claim 5, wherein Selected from not via *a and L 3 R of the bonded single bond 21 ~R 28 All groups except the substituents are hydrogen atoms.

18. The compound according to claim 5, wherein Selected from R 31 ~R 38 All groups except the substituents are hydrogen atoms.

19. The compound according to any one of claims 1 to 14 and 16 to 18, wherein Contains at least 1 deuterium atom.

20. The compound according to claim 1, wherein The molecular weight of the compound is 650-3000.

21. The compound according to claim 1, wherein The molecular weight of the compound is 650-1000.

22. The compound according to claim 7, which is represented by formula (1-b-1), Where Y 1 , Y 2 ,Ar 1 ,Ar 2 , L 1 , L 2 and R 1 ~R 6 Same as the definition in formula (1), R 31 ~R 38 Same as defined in formula (1-b), R 41 ~R 42 and R 44 ~R 45 Each is independently selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

23. The compound according to claim 7, which is represented by formula (1-b-2), Where Y 1 , Y 2 ,Ar 1 ,Ar 2 , L 1 , L 2 and R 1 ~R 6 Same as the definition in formula (1), R 31 ~R 38 Same as defined in formula (1-b), R 41 ~R 42 , R 44 ~R 45 , R 51 ~R 52 and R 54 ~R 55 Each is independently selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

24. The compound according to claim 8, which is represented by formula (1-b-11), Where Y 1 , Y 2 ,Ar 1 ,Ar 2 , L 1 , L 2 and R 1 ~R 6 Same as the definition in formula (1), R 31 ~R 38 Same as defined in formula (1-b), R 41 and R 43 ~R 45 Each is independently selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

25. The compound according to claim 8, which is represented by formula (1-b-12), Where Y 1 , Y 2 ,Ar 1 ,Ar 2 , L 1 , L 2 and R1~R 6 Same as the definition in formula (1), R 31 ~R 38 Same as defined in formula (1-b), R 41 and R 44 ~R 45 Each is independently selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

26. The compound according to claim 8, which is represented by formula (1-b-13), Where Y 1 , Y 2 ,Ar 1 ,Ar 2 , L 1 , L 2 and R 1 ~R 6 Same as the definition in formula (1), R 31 ~R 38 Same as defined in formula (1-b), R 41 , R 43 and R 45 Each is independently selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

27. The compound according to claim 8, which is represented by formula (1-b-14), Where Y 1 , Y 2 ,Ar 1 ,Ar 2 , L 1 , L 2 and R 1 ~R 6 Same as the definition in formula (1), R 31 ~R 38 Same as defined in formula (1-b), R 41 and R 45 Each is independently selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

28. The compound according to claim 9, which is represented by formula (1-a-1), Where Y 1 , Y 2 ,Ar 1 ,Ar 2 , L 1 , L 2 and R 1 ~R 6 Same as the definition in formula (1), R a , R 21 ~R 23 , R 25 ~R 28 Same as defined in formula (1-a), R 41 ~R 42 and R 44 ~R 45 Each is independently selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

29. The compound according to claim 9, which is represented by formula (1-a-2), Where Y 1 , Y 2 ,Ar 1 ,Ar 2 , L 1 , L 2 and R 1 ~R 6 Same as the definition in formula (1), R a , R 21 ~R 22 , R 24 ~R 28 Same as defined in formula (1-a), R 41 ~R 42 and R 44 ~R 45 Each is independently selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

30. The compound according to claim 9, which is represented by formula (1-a-3), Where Y 1 , Y 2 ,Ar 1 ,Ar 2 , L 1 , L 2 and R 1 ~R 6 Same as the definition in formula (1), R a , R 21 , R 23 ~R 28 Same as defined in formula (1-a), R 41 ~R 42 and R 44 ~R 45 Each is independently selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

31. The compound according to claim 9, which is represented by formula (1-a-4), Where Y 1 , Y 2 ,Ar 1 ,Ar 2 , L 1 , L 2 and R 1 ~R 6 Same as the definition in formula (1), R a , R 22 ~R 28 Same as defined in formula (1-a), R 41 ~R 42 and R 44 ~R 45 Each is independently selected from a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

32. A compound selected from the group consisting of the following compounds 1 to 19, 33. A material for an organic electroluminescent device, comprising the compound according to any one of claims 1 to 32.

34. An organic electroluminescent element comprising a cathode, an anode, and an organic layer located between the cathode and the anode, wherein the organic layer comprises a light-emitting layer, and at least one layer of the organic layer comprises the compound according to any one of claims 1 to 32.

35. The organic electroluminescent element according to claim 34, wherein The organic layer includes an electron transport region between the cathode and the light emitting layer, and the electron transport region includes the compound.

36. The organic electroluminescent element according to claim 35, wherein The electron transport region includes a first electron transport layer on the anode side and a second electron transport layer on the cathode side, the first electron transport layer includes the compound, the second electron transport layer includes the compound, or both the first electron transport layer and the second electron transport layer include the compound.

37. The organic electroluminescent element according to claim 35, wherein The electron transport region further comprises a hole blocking layer on the cathode side, and the hole blocking layer comprises the compound.

38. The organic electroluminescent element according to claim 37, wherein The hole blocking layer is adjacent to the light emitting layer.

39. The organic electroluminescent element according to any one of claims 34 to 38, wherein The light-emitting layer includes a fluorescent dopant material.

40. The organic electroluminescent element according to any one of claims 34 to 38, wherein The light-emitting layer includes a phosphorescent dopant material.

41. An electronic device comprising the organic electroluminescent element according to any one of claims 34 to 40.

Images