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

Abstract

[Problem] A compound that further improves the performance of an organic EL device, a material for an organic electroluminescent device that further improves the performance of an organic EL device, an organic electroluminescent device with improved device performance, and an electronic device including such an organic electroluminescent device. [Solution] Compound represented by the following formula (1): (Each symbol in the formula is as defined in the specification.), a material for an organic electroluminescent device comprising said compound, an organic electroluminescent device comprising said compound, and an electronic device comprising said organic electroluminescent device.

Description

Technology Field

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

[0002] Generally, an organic electroluminescent device (hereinafter referred to as an "organic EL device") is composed of an anode, a cathode, and an organic layer sandwiched between the anode and the cathode. When a voltage is applied between the two electrodes, electrons from the cathode side and holes from the anode side are injected into the light-emitting region. The injected electrons and holes recombine in the light-emitting region to create an excited state, and light is emitted when the excited state returns to the ground state. Therefore, the development of materials that efficiently transport electrons or holes to the light-emitting region and facilitate the recombination of electrons and holes is important for obtaining high-performance organic EL devices.

[0003] Patent documents 1 to 10 disclose compounds used as materials for organic electroluminescent devices (hereinafter referred to as "materials for organic EL devices"). Prior art literature

[0004] Specification of U.S. Patent Application Publication No. 2020 / 0235297 Specification of U.S. Patent Application Publication No. 2024 / 0237528 Specification of U.S. Patent Application Publication No. 2019 / 0140177 Specification of U.S. Patent Application Publication No. 2021 / 0376241 Specification of U.S. Patent Application Publication No. 2020 / 0119282 Specification of U.S. Patent Application Publication No. 2023 / 0013038 Specification of U.S. Patent Application Publication No. 2019 / 0237676 International Publication No. 2023 / 013575 International Publication No. 2024 / 071332 Chinese Published Patent No. 118271266 The problem to be solved

[0005] Conventionally, many compounds for organic EL devices have been reported, but there is still a need for compounds that further improve the performance of organic EL devices.

[0006] The present invention is made to solve the above-mentioned problem and aims to provide a compound that further improves the performance of an organic EL device, an organic EL device with further improved device performance, and an electronic device including such an organic EL device. means of solving the problem

[0007] As a result of repeated research on the performance of organic EL devices containing compounds described in patent documents 1 to 4, the inventors discovered that organic EL devices containing compounds represented by the following formula (1) have improved performance.

[0008] In one aspect, the present invention provides a compound represented by the following formula (1).

[0009] [Chemical Formula 1]

[0010]

[0011] [Essence (1),

[0012] N * is the central nitrogen atom.

[0013] R 5 ~R 8 One selected from is a single bond that combines with *1.

[0014] R 1 ~R 4 Two of the selected groups are substituted or unsubstituted phenyl groups.

[0015] R that is not a substituted or unsubstituted phenyl group 1 ~R 4 , and R that is not a single bond 5 ~R 8 Two adjacent items selected from do not combine with each other and do not form a ring.

[0016] Ar 1 and Ar 2Each is independently a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 5 to 30 atoms.

[0017] L 1 , L 2 , and L 3 Each is independently a single bond, a substituted or unsubstituted cyclic arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroarylene group having 5 to 30 atoms.

[0018] R that is not a substituted or unsubstituted phenyl group 1 ~R 4 , R that is not a single bond 5 ~R 8 , and any substituent in the phenyl group is each independently a hydrogen atom, a substituted or unsubstituted C1-50 alkyl group, a substituted or unsubstituted C2-50 alkenyl group, a substituted or unsubstituted C2-50 alkynyl group, a substituted or unsubstituted cyclic C3-50 cycloalkyl group, -Si(R 901 ')(R 902 ')(R 903 '), -O-(R 904 '), -S-(R 905 It is a halogen atom, a cyano group, or a nitro group. R 901 '~R 905 ' is, each independently, a hydrogen atom, a substituted or unsubstituted C1-50 alkyl group, a substituted or unsubstituted cyclic C3-50 cycloalkyl group, or a substituted or unsubstituted cyclic C6-50 aryl group. R 901 '~R 905 If there are 2 or more ', 2 or more R 901 '~R 905 ' may be the same or different.]

[0019] In another aspect, the present invention provides a material for an organic EL device comprising a compound represented by the above formula (1).

[0020] In another aspect, the present invention provides an organic electroluminescent device having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer comprises a single or multiple layers including a light-emitting layer, and at least one layer selected from the group consisting of a single layer and multiple layers constituting the organic layer comprises said compound.

[0021] In another aspect, the present invention provides an electronic device comprising the organic electroluminescent element. Effects of the invention

[0022] An organic EL device containing a compound represented by the above formula (1) exhibits improved device performance. Brief explanation of the drawing

[0023] FIG. 1 is a schematic diagram showing an example of a layer configuration of an organic EL device according to one aspect of the present invention. FIG. 2 is a schematic diagram showing another example of the layer configuration of an organic EL device according to one aspect of the present invention. FIG. 3 is a schematic diagram showing another example of the layer configuration of an organic EL device according to one aspect of the present invention. Specific details for implementing the invention

[0024] [definition]

[0025] In this specification, the term hydrogen atom includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0026] In this specification, in the chemical structural formula, hydrogen atoms, i.e., light hydrogen atoms, deuterium atoms, or tritium atoms, are bonded to the bondable positions where symbols such as "R" or "D" representing a deuterium atom are not specified.

[0027] In this specification, the term "cyclic carbon number" refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, condensed ring compounds, crosslinked compounds, carbon-ring compounds, and heterocyclic compounds). When the ring is substituted by a substituent, the carbons included in the substituent are not included in the cyclic carbon number. The "cyclic carbon number" described below shall be treated as such unless otherwise noted. For example, the benzene ring has a cyclic carbon number of 6, the naphthalene ring has a cyclic carbon number of 10, the pyridine ring has a cyclic carbon number of 5, and the furan ring has a cyclic carbon number of 4. Also, for example, the cyclic carbon number of the 9,9-diphenylfluorenyl group is 13, and the cyclic carbon number of the 9,9'-spirobifluorenyl group is 25.

[0028] In addition, when a benzene ring is substituted with, for example, an alkyl group, the number of carbons of the said alkyl group is not included in the number of carbons forming the ring of the benzene ring. Therefore, the number of carbons forming the ring of the benzene ring substituted with an alkyl group is 6. In addition, when a naphthalene ring is substituted with, for example, an alkyl group, the number of carbons of the said alkyl group is not included in the number of carbons forming the ring of the naphthalene ring. Therefore, the number of carbons forming the ring of the naphthalene ring substituted with an alkyl group is 10.

[0029] In this specification, the number of ring-forming atoms refers to the number of atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., a single ring, a condensed ring, and a ring assembly) (e.g., a single ring compound, a condensed ring compound, a crosslinked compound, a carbon ring compound, and a heteroring compound). Atoms that do not constitute a ring (e.g., hydrogen atoms terminating the bonds of atoms constituting the ring) or atoms included in the substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. The same shall apply to the "number of ring-forming atoms" described below unless otherwise noted. For example, the number of ring-forming atoms of a pyridine ring is 6, the number of ring-forming atoms of a quinazoline ring is 10, and the number of ring-forming atoms of a furan ring is 5. For example, hydrogen atoms bonded to the pyridine ring or the number of atoms constituting the substituents are not included in the number of pyridine ring-forming atoms. For this reason, the number of cyclic atoms of the pyridine ring to which hydrogen atoms or substituents are bonded is 6. Also, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of cyclic atoms of the quinazoline ring. For this reason, the number of cyclic atoms of the quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

[0030] In the present specification, in the expression “substituted or unsubstituted ZZ group having XX to YY carbons,” “XX to YY carbons” indicates the number of carbons when the ZZ group is unsubstituted and does not include the number of carbons of the substituent when it is substituted. Here, “YY” is greater than “XX,” “XX” means an integer of 1 or more, and “YY” means an integer of 2 or more.

[0031] In the present specification, in the expression “ZZ group having a number of atoms XX to YY that are substituted or unsubstituted,” “number of atoms XX to YY” represents the number of atoms when the ZZ group is unsubstituted and does not include the number of atoms of the substituent when it is substituted. Here, “YY” is greater than “XX,” “XX” means an integer greater than or equal to 1, and “YY” means an integer greater than or equal to 2.

[0032] In this specification, the term "unsubstituted ZZ group" indicates the case where the "substituted or unsubstituted ZZ group" is the "unsubstituted ZZ group," and the term "substituted ZZ group" indicates the case where the "substituted or unsubstituted ZZ group" is the "substituted ZZ group."

[0033] In this specification, "non-substituted" in the case of "substituted or non-substituted ZZ group" means that the hydrogen atoms in the ZZ group are not substituted with substituents. The hydrogen atoms in the "non-substituted ZZ group" are light hydrogen atoms, deuterium atoms, or tritium atoms.

[0034] In addition, in the present specification, "substitution" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are substituted with a substituent. Likewise, "substitution" in the case of "BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are substituted with an AA group.

[0035] "Substituents described in this specification"

[0036] The substituents described in this specification are described below. Unless otherwise noted, each substituent described in this specification is defined as follows.

[0037] The number of ring-forming carbons of the “unsubstituted aryl group” described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0038] The number of cyclic atoms of the “unsubstituted heterocyclic group” described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified in this specification.

[0039] The number of carbon atoms of the “unsubstituted alkyl group” described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified in this specification.

[0040] The number of carbon atoms of the “unsubstituted alkenyl group” described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified in this specification.

[0041] The number of carbon atoms of the “unsubstituted alkyne group” described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified in this specification.

[0042] The number of cyclic carbon atoms of the “unsubstituted cycloalkyl group” described in this specification is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified in this specification.

[0043] The number of cyclic carbon atoms of the “unsubstituted arylene group” described in this specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified in this specification.

[0044] The number of ring-forming atoms of the “unsubstituted divalent heterocyclic group” described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified in this specification.

[0045] The number of carbon atoms of the “unsubstituted alkylene group” described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified in this specification.

[0046] · "Substituted or non-substituted aryl group"

[0047] Specific examples (Group of Specific Examples G1) of the “substituted or unsubstituted aryl group” described in this specification include the following unsubstituted aryl group (Group of Specific Examples G1A) and substituted aryl group (Group of Specific Examples G1B). (Here, “unsubstituted aryl group” refers to the case where the “substituted or unsubstituted aryl group” is an “unsubstituted aryl group,” and “substituted aryl group” refers to the case where the “substituted or unsubstituted aryl group” is a “substituted aryl group.”) In this specification, when simply referred to as an “aryl group,” both the “unsubstituted aryl group” and the “substituted aryl group” are included.

[0048] "Substituted aryl group" means a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are substituted with a substituent. Examples of "substituted aryl groups" include a group in which one or more hydrogen atoms of an "unsubstituted aryl group" of the following specific example group G1A are substituted with a substituent, and examples of substituted aryl groups of the following specific example group G1B. Meanwhile, the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed herein are merely examples, and the "substituted aryl groups" described in this specification include a group in which a hydrogen atom bonded to the carbon atom of the aryl group itself in the "substituted aryl group" of the following specific example group G1B is further substituted with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted aryl group" of the following specific example group G1B is further substituted with a substituent.

[0049] · Unsubstituted Arylgi (Specific Example Group G1A):

[0050] phenyl group,

[0051] p-biphenyl group,

[0052] m-biphenyl group,

[0053] o-biphenyl group,

[0054] p-terphenyl-4-diary,

[0055] p-terphenyl-3-diary,

[0056] p-terphenyl-2-diary,

[0057] m-terphenyl-4-diary,

[0058] m-terphenyl-3-diary,

[0059] m-terphenyl-2-diary,

[0060] o-terphenyl-4-diary,

[0061] o-terphenyl-3-diary,

[0062] o-terphenyl-2-diyl,

[0063] 1-Naphthyl group,

[0064] 2-Naphthyl group,

[0065] Anthrill,

[0066] benzoaterillic group,

[0067] phenanthril group,

[0068] Benzophenanthrile group,

[0069] Penalen Diary,

[0070] Firen's Diary

[0071] Krysen's Diary

[0072] Benzokrysen Diary

[0073] triphenyleneyl group,

[0074] Benzotriphenyleneyl group,

[0075] Tetracen Diary,

[0076] Pentasen Diary,

[0077] Fluorene Diary,

[0078] 9,9'-Spyrobluorene Diary,

[0079] Benzofluorene Diary,

[0080] Dibenzofluoren Diary,

[0081] Fluoranthene Diary

[0082] Benzofluoranthene Diary

[0083] Perillen Diary, and

[0084] A monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0085] [Chemical Formula 2]

[0086]

[0087] [Chemical Formula 3]

[0088]

[0089] · Substituted aryl group (Specific example group G1B):

[0090] o-tollil group,

[0091] m-tolyl group,

[0092] p-tolyl group,

[0093] Para-xylyl,

[0094] meta-xylyl group,

[0095] Ortho-xylyl group,

[0096] para-isopropylphenyl group,

[0097] meta-isopropylphenyl group,

[0098] Ortho-isopropylphenyl group,

[0099] para-t-butylphenyl group,

[0100] meta-t-butylphenyl group,

[0101] Ortho-t-butylphenyl group,

[0102] 3,4,5-trimethylphenyl group,

[0103] 9,9-dimethylfluorene yl group,

[0104] 9,9-diphenylfluorene digroup

[0105] 9,9-bis(4-methylphenyl)fluorenyl group,

[0106] 9,9-bis(4-isopropylphenyl)fluoreneyl group,

[0107] 9,9-bis(4-t-butylphenyl)fluorenyl group,

[0108] cyanophenyl group,

[0109] triphenylsilylphenyl group,

[0110] trimethylsilylphenyl group,

[0111] phenylnaphthyl group,

[0112] Naphthylphenyl group, and

[0113] A group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by the above general formulas (TEMP-1) to (TEMP-15) are substituted with substituents.

[0114] · "Substituted or unsubstituted heterovents"

[0115] The “heterocyclic group” described in this specification is a cyclic group comprising at least one heteroatom in a cyclic atom. Specific examples of heteroatoms include nitrogen atoms, oxygen atoms, sulfur atoms, silicon atoms, phosphorus atoms, and boron atoms.

[0116] The “heterocyclic group” described in this specification is a single-ring group or a condensed-ring group.

[0117] The "heteroventilation" described in this specification is an aromatic heteroventilation or a non-aromatic heteroventilation.

[0118] Examples of specific examples (Group of Specific Examples G2) of the “substituted or unsubstituted heterovent” described in this specification include the following unsubstituted heterovent (Group of Specific Examples G2A) and substituted heterovent (Group of Specific Examples G2B). (Here, “unsubstituted heterovent” refers to the case where the “substituted or unsubstituted heterovent” is the “unsubstituted heterovent,” and “substituted heterovent” refers to the case where the “substituted or unsubstituted heterovent” is the “substituted heterovent.”) In this specification, when simply referred to as “heterovent,” both the “unsubstituted heterovent” and the “substituted heterovent” are included.

[0119] "Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are substituted with a substituent. Specific examples of "substituted heterocyclic groups" include a group in which a hydrogen atom of an "unsubstituted heterocyclic group" of the following group of examples G2A is substituted, and an example of a substituted heterocyclic group of the following group of examples G2B. Meanwhile, the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed herein are merely examples, and the "substituted heterocyclic group" described in this specification includes a group in which a hydrogen atom bonded to the cyclic atom of the heterocyclic group itself in the "substituted heterocyclic group" of the following group of examples G2B is further substituted with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted heterocyclic group" of the following group of examples G2B is further substituted with a substituent.

[0120] Specific example group G2A includes, for example, an unsubstituted heterocyclic group containing a nitrogen atom (Specific example group G2A1), an unsubstituted heterocyclic group containing an oxygen atom (Specific example group G2A2), an unsubstituted heterocyclic group containing a sulfur atom (Specific example group G2A3), and a monovalent heterocyclic group (Specific example group G2A4) derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33).

[0121] Specific example group G2B comprises, for example, a substituted heterocyclic group containing a nitrogen atom (Specific example group G2B1), a substituted heterocyclic group containing an oxygen atom (Specific example group G2B2), a substituted heterocyclic group containing a sulfur atom (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 formulas (TEMP-16) to (TEMP-33) are substituted with a substituent (Specific example group G2B4).

[0122] · Unsubstituted heterocyclic group containing a nitrogen atom (Specific example group G2A1):

[0123] pyrrolyl group,

[0124] Imidajorilgi,

[0125] pyrazolyl group,

[0126] triazolyl group,

[0127] tetrazolyl group,

[0128] Oxazoligi,

[0129] Child's sleepiness

[0130] oxadiazolyl group,

[0131] Thiazolidin,

[0132] isothiazolyl group,

[0133] Cydiadiazolyl,

[0134] Piridilgi,

[0135] Piridajin Diary,

[0136] Pyrimidin Diary,

[0137] Pirajin Diary,

[0138] Triazine Diary

[0139] Indolil,

[0140] Iso-in-drill,

[0141] Indollijin Diary,

[0142] Quinoligin Diary,

[0143] Quinolyl group,

[0144] isoquinolyl group,

[0145] Sinnolilgi,

[0146] Phtalazine Diary,

[0147] Quinazolin Diary,

[0148] Quinoxalin Diary

[0149] Benzimidazoliyl group,

[0150] Indazolillgi,

[0151] Penantrollin Diary

[0152] Phenanthridine Diary,

[0153] Acridin Diary,

[0154] Penazine Diary

[0155] Carbazolyl group,

[0156] benzocarbazolyl group,

[0157] Morpolinogi,

[0158] Phenox Photo Diary

[0159] Phenothiazine Diary

[0160] Azacarbazolyl group, and

[0161] Diazacarbazolyl group.

[0162] · Unsubstituted heterocyclic group containing an oxygen atom (Specific example group G2A2):

[0163] Furyl group,

[0164] Oxazoligi,

[0165] Child's sleepiness

[0166] oxadiazolyl group,

[0167] Zanten Diary,

[0168] Benzofuran Diary,

[0169] Isobenzofuran Diary,

[0170] Divenzofuran Diary,

[0171] Naftobenzopyran Diary,

[0172] benzoxazolyl group,

[0173] Benz-Eye Soksajolilgi,

[0174] Phenox Photo Diary

[0175] Morpolinogi,

[0176] Dynaphtofuran Diary

[0177] Azada Benzopyun Diary,

[0178] Diary of Diazadaibenzofuran

[0179] Azanaptobenzopyran Diary, and

[0180] Diary of Diazanaptobenzopyran

[0181] · Unsubstituted heterocyclic groups containing sulfur atoms (Specific example group G2A3):

[0182] Cyworld Diary,

[0183] Thiazolidin,

[0184] isothiazolyl group,

[0185] Cydiadiazolyl,

[0186] Benzothiophene Diary (Benzothien Diary),

[0187] Isobenzothiophene Diary (Isobenzothiene Diary),

[0188] Dibenzothiophen Diary (Dibenzothiophen Diary),

[0189] Naphthobenzothiophen Diary (Naphthobenzothiophen Diary),

[0190] Benzothiazolyl group,

[0191] Benzisothiazolyl group,

[0192] Phenothiazine Diary

[0193] Dynaphthothiophene Diary (Dynapthothien Diary),

[0194] Azada benzothiophen Diary (Aza benzothiophen Diary),

[0195] Diazadiabenzothiophen Diary (Diazadiabenzothiophen Diary),

[0196] Azanaptobenzothiophen Diary (Azanaptobenzothien Diary), and

[0197] Diazanapthobenzothiophen Diary (Diazanapthobenzothiophen Diary).

[0198] · A monovalent heterocyclic group induced by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (Specific example group G2A4):

[0199] [Chemical Formula 4]

[0200]

[0201] [Chemical Formula 5]

[0202]

[0203] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A is, each independently, an oxygen atom, a sulfur atom, NH, or CH2. provided that X A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH.

[0204] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Where at least one of them is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0205] · Substituted heterocyclic group containing a nitrogen atom (Specific example group G2B1):

[0206] (9-phenyl)carbazolyl group,

[0207] (9-biphenylyl)carbazolyl group,

[0208] (9-phenyl)phenylcarbazolyl group,

[0209] (9-naphthyl)carbazolyl group,

[0210] Diphenylcarbazole-9-diary,

[0211] Phenylcarbazole-9-diary,

[0212] methylbenzimidazolyl group,

[0213] Ethylbenzimidazolyl group,

[0214] Phenyltriazine diary,

[0215] Biphenylyltriazine Diary,

[0216] Diphenyltriazine Diary

[0217] Phenylquinazolin diary, and

[0218] Biphenylylquinazolin Diary

[0219] · Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0220] Phenyldibenzofuran diary,

[0221] Methyldibenzofuran group,

[0222] t-butyldibenzofuran group, and

[0223] The monovalent residue of spiro[9H-xanthen-9,9'-[9H]fluorene].

[0224] · Substituted heterocyclic groups containing sulfur atoms (specific example group G2B3):

[0225] Phenyldibenzothiophene Diary,

[0226] Methyl dibenzothiophene diary,

[0227] t-butyldibenzothiophenyl group, and

[0228] The monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0229] · A group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structures represented by the above general formulas (TEMP-16) to (TEMP-33) are substituted with a substituent (Specific Example Group G2B4):

[0230] The above "one or more hydrogen atoms of a monovalent heterocyclic group" refers to a hydrogen atom, X, bonded to a cyclic carbon atom of the said monovalent heterocyclic group. A and Y A A hydrogen atom bonded to a nitrogen atom in the case where at least one of them is NH, and X A and Y A It means one or more hydrogen atoms selected from the hydrogen atoms of the methylene group when one side is CH2.

[0231] · Substituted or unsubstituted alkyl group

[0232] Examples of specific examples (Group of Specific Examples G3) of the “substituted or unsubstituted alkyl group” described in this specification include the following unsubstituted alkyl group (Group of Specific Examples G3A) and substituted alkyl group (Group of Specific Examples G3B). (Here, the term “unsubstituted alkyl group” refers to the case where the “substituted or unsubstituted alkyl group” is an “unsubstituted alkyl group,” and the term “substituted alkyl group” refers to the case where the “substituted or unsubstituted alkyl group” is a “substituted alkyl group.”) Hereinafter, when simply referred to as “alkyl group,” both the “unsubstituted alkyl group” and the “substituted alkyl group” are included.

[0233] "Substituted alkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are substituted with substituents. Specific examples of "substituted alkyl group" include a group in which one or more hydrogen atoms in the following "unsubstituted alkyl group" (Specific Example Group G3A) are substituted with substituents, and examples of a substituted alkyl group (Specific Example Group G3B). In this specification, the alkyl group in "unsubstituted alkyl group" refers to a chain-like alkyl group. Accordingly, "unsubstituted alkyl group" includes straight-chain "unsubstituted alkyl groups" and branched "unsubstituted alkyl groups." Meanwhile, the examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed herein are merely examples, and the "substituted alkyl groups" described in this specification include a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" of Specific Example Group G3B is further substituted with a substituent, and a group in which a hydrogen atom of the substituent in the "substituted alkyl group" of Specific Example Group G3B is further substituted with a substituent.

[0234] · Unsubstituted alkyl group (Specific Example Group G3A):

[0235] methyl group,

[0236] ethyl group,

[0237] n-Profilter,

[0238] isopropyl group,

[0239] n-butyl group,

[0240] isobutyl group,

[0241] s-butyl group, and

[0242] t-butyl group.

[0243] · Substituted alkyl group (Specific Example Group G3B):

[0244] heptafluoropropyl group (including isomers),

[0245] pentafluoroethyl group,

[0246] 2,2,2-trifluoroethyl group, and

[0247] Trifluoromethyl group.

[0248] · "Substituted or Unsubstituted Alkenes"

[0249] Specific examples (Group of Specific Examples G4) of the “substituted or unsubstituted alkenyl group” described in this specification include the following unsubstituted alkenyl group (Group of Specific Examples G4A) and substituted alkenyl group (Group of Specific Examples G4B). (Here, “unsubstituted alkenyl group” refers to the case where the “substituted or unsubstituted alkenyl group” is an “unsubstituted alkenyl group,” and “substituted alkenyl group” refers to the case where the “substituted or unsubstituted alkenyl group” is a “substituted alkenyl group.”) In this specification, when simply referred to as an “alkenyl group,” both the “unsubstituted alkenyl group” and the “substituted alkenyl group” are included.

[0250] "Substituted alkenyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are substituted with substituents. Specific examples of "substituted alkenyl group" include the following "unsubstituted alkenyl group" (Group of Specific Examples G4A) having substituents, and examples of a substituted alkenyl group (Group of Specific Examples G4B). Meanwhile, the examples of "unsubstituted alkenyl group" and "substituted alkenyl group" listed herein are merely examples, and the "substituted alkenyl group" described in this specification includes a group in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl group" of Group of Specific Examples G4B is further substituted with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkenyl group" of Group of Specific Examples G4B is further substituted with a substituent.

[0251] · Unsubstituted Alkene Diary (Special Example Group G4A):

[0252] vinyl recorder

[0253] Alilgi,

[0254] 1-Beauten Diary,

[0255] 2-Beauten Diary, and

[0256] 3-Beauten Diary.

[0257] · Substituted Alken Diary (Specific Example Group G4B):

[0258] 1,3-Butanedienne's Diary,

[0259] 1-methylvinyl group,

[0260] 1-methylallyl group,

[0261] 1,1-dimethylallyl group,

[0262] 2-methylallyl group, and

[0263] 1,2-dimethylallyl group.

[0264] · "Substitution or Non-Substitutional Alkin Diary"

[0265] Examples of specific examples (group of examples G5) of the “substituted or unsubstituted alkyne group” described in this specification include the following unsubstituted alkyne group (group of examples G5A). (Here, “unsubstituted alkyne group” refers to the case where the “substituted or unsubstituted alkyne group” is an “unsubstituted alkyne group.”) Hereinafter, when simply referred to as an “alkyne group,” both “unsubstituted alkyne groups” and “substituted alkyne groups” are included.

[0266] "Substituted alkyne group" means a group in which one or more hydrogen atoms in an "unsubstituted alkyne group" are substituted with substituents. Specific examples of "substituted alkyne group" include a group in which one or more hydrogen atoms in an "unsubstituted alkyne group" (specific example group G5A) are substituted with substituents.

[0267] · Unsubstituted Alkin Diary (Special Example Group G5A):

[0268] Etin Diary

[0269] · Substituted or unsubstituted cycloalkyl group

[0270] Examples of specific examples (Group of Examples G6) of the “substituted or unsubstituted cycloalkyl group” described in this specification include the following unsubstituted cycloalkyl group (Group of Examples G6A) and substituted cycloalkyl group (Group of Examples G6B). (Here, “unsubstituted cycloalkyl group” refers to the case where the “substituted or unsubstituted cycloalkyl group” is an “unsubstituted cycloalkyl group,” and “substituted cycloalkyl group” refers to the case where the “substituted or unsubstituted cycloalkyl group” is a “substituted cycloalkyl group.”) In this specification, when simply referred to as “cycloalkyl group,” both “unsubstituted cycloalkyl group” and “substituted cycloalkyl group” are included.

[0271] "Substituted cycloalkyl group" means a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are substituted with substituents. Specific examples of "substituted cycloalkyl group" include a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" (Specific Example Group G6A) are substituted with substituents, and examples of a substituted cycloalkyl group (Specific Example Group G6B). Meanwhile, the examples of "unsubstituted cycloalkyl group" and "substituted cycloalkyl group" listed herein are merely examples, and the "substituted cycloalkyl group" described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the cycloalkyl group itself in the "substituted cycloalkyl group" of Specific Example Group G6B are substituted with substituents, and a group in which a hydrogen atom of a substituent in the "substituted cycloalkyl group" of Specific Example Group G6B is further substituted with a substituent.

[0272] · Unsubstituted cycloalkyl group (Specific Example Group G6A):

[0273] Cyclopropyl group,

[0274] cyclobutyl group,

[0275] cyclopentyl group,

[0276] cyclohexyl group,

[0277] 1-adamantyl group,

[0278] 2-adamantyl group,

[0279] 1-norbonyl group, and

[0280] 2-Novonyl group.

[0281] · Substituted cycloalkyl group (Specific Example Group G6B):

[0282] 4-methylcyclohexyl group.

[0283] · -Si(R 901 )(R 902 )(R 903 The device indicated by )

[0284] -Si(R as described in this specification 901 )(R 902 )(R903 As for a specific example of the device indicated by ) (specific example group G7),

[0285] -Si(G1)(G1)(G1),

[0286] -Si(G1)(G2)(G2),

[0287] -Si(G1)(G1)(G2),

[0288] -Si(G2)(G2)(G2),

[0289] -Si(G3)(G3)(G3), and

[0290] -Si(G6)(G6)(G6)

[0291] ...can be cited. Here,

[0292] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.

[0293] G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0294] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

[0295] G6 is a “substituted or unsubstituted cycloalkyl group” as described in Specific Example Group G6.

[0296] In -Si(G1)(G1)(G1), the multiple G1s are either identical or different from each other.

[0297] In Si(G1)(G2)(G2), the multiple G2s are either identical or different from each other.

[0298] In -Si(G1)(G1)(G2), the multiple G1s are either identical or different from each other.

[0299] In -Si(G2)(G2)(G2), the multiple G2s are either identical or different from each other.

[0300] In -Si(G3)(G3)(G3), the multiple G3s are either identical or different from each other.

[0301] In -Si(G6)(G6)(G6), the multiple G6s are either identical or different from each other.

[0302] · 「-O-(R 904 The unit indicated by )

[0303] -O-(R as described in this specification 904 As for a specific example of the device indicated by ) (specific example group G8),

[0304] -O(G1),

[0305] -O(G2),

[0306] -O(G3), and

[0307] -O(G6)

[0308] ...can be cited.

[0309] Here,

[0310] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.

[0311] G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0312] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

[0313] G6 is a “substituted or unsubstituted cycloalkyl group” as described in Specific Example Group G6.

[0314] · 「-S-(R 905 The unit indicated by )

[0315] -S-(R as described in this specification 905 As for a specific example of the device indicated by ) (specific example group G9),

[0316] -S(G1),

[0317] -S(G2),

[0318] -S(G3), and

[0319] -S(G6)

[0320] ...can be cited.

[0321] Here,

[0322] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.

[0323] G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0324] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

[0325] G6 is a “substituted or unsubstituted cycloalkyl group” as described in Specific Example Group G6.

[0326] · 「-N(R 906 )(R 907 The unit indicated by )

[0327] -N(R as described in this specification 906 )(R 907 As for a specific example of the device indicated by ) (specific example group G10),

[0328] -N(G1)(G1),

[0329] -N(G2)(G2),

[0330] -N(G1)(G2),

[0331] -N(G3)(G3), and

[0332] -N(G6)(G6)

[0333] ...can be cited.

[0334] Here,

[0335] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.

[0336] G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0337] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

[0338] G6 is a “substituted or unsubstituted cycloalkyl group” as described in Specific Example Group G6.

[0339] In -N(G1)(G1), multiple G1s are either identical or different from each other.

[0340] In -N(G2)(G2), the multiple G2s are either identical or different from each other.

[0341] In -N(G3)(G3), the multiple G3s are either identical or different from each other.

[0342] In -N(G6)(G6), the multiple G6s are either identical or different from each other.

[0343] · Halogen atoms

[0344] Specific examples of the “halogen atoms” described in this specification (Specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0345] · Substituted or unsubstituted fluoroalkyl group

[0346] The "substituted or unsubstituted fluoroalkyl group" described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is substituted with a fluorine atom, and also includes a group (perfluoro group) in which all hydrogen atoms bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" are substituted with fluorine atoms. Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of the "fluoroalkyl group" are substituted with a substituent. Meanwhile, the “substituted fluoroalkyl group” described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the “substituted fluoroalkyl group” are further substituted with a substituent, and a group in which one or more hydrogen atoms of the substituent in the “substituted fluoroalkyl group” are further substituted with a substituent. Specific examples of the “unsubstituted fluoroalkyl group” include a group in which one or more hydrogen atoms in the “alkyl group” (specific example group G3) are substituted with a fluorine atom.

[0347] · Substituted or unsubstituted haloalkyl group

[0348] The "substituted or unsubstituted haloalkyl group" described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is substituted with a halogen atom, and also includes a group in which all hydrogen atoms bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" are substituted with halogen atoms. Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of the "haloalkyl group" are substituted with a substituent. Meanwhile, the “substituted haloalkyl group” described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the “substituted haloalkyl group” are further substituted with a substituent, and a group in which one or more hydrogen atoms of the substituent in the “substituted haloalkyl group” are further substituted with a substituent. Specific examples of the “unsubstituted haloalkyl group” include a group in which one or more hydrogen atoms in the “alkyl group” (specific example group G3) are substituted with a halogen atom. A haloalkyl group may be referred to as an alkyl halide group.

[0349] · "Substituted or unsubstituted alkoxy groups"

[0350] A specific example of the “substituted or unsubstituted alkoxy group” described in this specification is a group represented by -O(G3), wherein G3 is the “substituted or unsubstituted alkyl group” described in the group of specific examples G3. Unless otherwise specified in this specification, the number of carbon atoms of the “unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0351] · Substituted or unsubstituted alkylthio groups

[0352] A specific example of the “substituted or unsubstituted alkylthio group” described in this specification is a group represented by -S(G3), wherein G3 is the “substituted or unsubstituted alkyl group” described in the group of specific examples G3. Unless otherwise specified in this specification, the number of carbon atoms of the “unsubstituted alkylthio group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0353] · "Substituted or unsubstituted aryloxy group"

[0354] A specific example of the “substituted or unsubstituted aryloxy group” described in this specification is a group represented by -O(G1), wherein G1 is the “substituted or unsubstituted aryl group” described in the group of specific examples G1. Unless otherwise specified in this specification, the number of ring-forming carbons of the “unsubstituted aryloxy group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0355] · "Substituted or unsubstituted arylcyogi"

[0356] A specific example of the “substituted or unsubstituted arylthio group” described in this specification is a group represented by -S(G1), wherein G1 is the “substituted or unsubstituted aryl group” described in the group of specific examples G1. Unless otherwise specified in this specification, the number of ring-forming carbons of the “unsubstituted arylthio group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0357] · Substituted or unsubstituted trialkylsilyl group

[0358] A specific example of the “trialkylsilyl group” described in this specification is a group represented by -Si(G3)(G3)(G3), wherein G3 is a “substituted or unsubstituted alkyl group” described in the group of specific examples G3. The plurality of G3s in -Si(G3)(G3)(G3) are identical or different from each other. Unless otherwise specified in this specification, 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.

[0359] · Substituted or unsubstituted aralkyl group

[0360] A specific example of the “substituted or unsubstituted aralkyl group” described in this specification is a group represented by -(G3)-(G1), wherein G3 is the “substituted or unsubstituted alkyl group” described in the group of specific examples G3, and G1 is the “substituted or unsubstituted aryl group” described in the group of specific examples G1. Accordingly, the “aralkyl group” is a group in which a hydrogen atom of the “alkyl group” is substituted with an “aryl group” as a substituent, and is one aspect of the “substituted alkyl group.” The “unsubstituted aralkyl group” is an “unsubstituted alkyl group” substituted with an “unsubstituted aryl group,” and the number of carbon atoms of the “unsubstituted aralkyl group” is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.

[0361] Specific examples of the “substituted or unsubstituted aralkyl group” include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.

[0362] The substituted or unsubstituted aryl groups described in this specification are, unless otherwise specified in this specification, preferably phenyl groups, p-biphenyl groups, m-biphenyl groups, o-biphenyl groups, p-terphenyl-4-yl groups, p-terphenyl-3-yl groups, p-terphenyl-2-yl groups, m-terphenyl-4-yl groups, m-terphenyl-3-yl groups, m-terphenyl-2-yl groups, o-terphenyl-4-yl groups, o-terphenyl-3-yl groups, o-terphenyl-2-yl groups, 1-naphthyl groups, 2-naphthyl groups, anthryl groups, phenanthryl groups, pyrene-yl groups, chrysen-yl groups, triphenylene-yl groups, fluorene-yl groups, 9,9'-spirobifluorene-yl groups, 9,9-dimethylfluorene-yl groups, and 9,9-diphenylfluorene-yl groups, etc.

[0363] The substituted or unsubstituted heterocyclic groups described herein, unless otherwise specified herein, are preferably pyridyl groups, pyrimidinyl groups, triazineyl groups, quinolyl groups, isoquinolyl groups, quinazolinyl groups, benzimidazolyl groups, phenanthrolineyl groups, carbazolyl groups (1-carbazolyl groups, 2-carbazolyl groups, 3-carbazolyl groups, 4-carbazolyl groups, or 9-carbazolyl groups), benzocarbazolyl groups, azacarbazolyl groups, diazacarbazolyl groups, dibenzofuranyl groups, naphthobenzofuranyl groups, azadibenzofuranyl groups, diazadibenzofuranyl groups, dibenzothiophenyl groups, naphthobenzothiophenyl groups, azadibenzothiophenyl groups, These include diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazol-4-yl group), (9-biphenyllyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazine yl group, biphenyllyltriazine yl group, diphenyltriazine yl group, phenyldibenzofuran yl group, and phenyldibenzothiophenyl group, etc.

[0364] In this specification, the carbazolyl group is, specifically, any of the following, unless otherwise specified in this specification.

[0365] [Chemical Formula 6]

[0366]

[0367] In this specification, the (9-phenyl)carbazolyl group is, specifically, any of the following groups, unless otherwise specified in this specification.

[0368] [Chemical Formula 7]

[0369]

[0370] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates a bonding position.

[0371] In this specification, the dibenzofuranyl group and the dibenzothiophenyl group are, specifically, any of the following, unless otherwise specified in this specification.

[0372] [Chemical Formula 8]

[0373]

[0374] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

[0375] The substituted or unsubstituted alkyl groups described in this specification are, unless otherwise specified in this specification, preferably methyl groups, ethyl groups, propyl groups, isopropyl groups, n-butyl groups, isobutyl groups, and t-butyl groups, etc.

[0376] · "Substituted or unsubstituted arylene group"

[0377] The “substituted or unsubstituted arylene group” described in this specification is a divalent group derived by removing one hydrogen atom from the aryl ring from the “substituted or unsubstituted aryl group” unless otherwise noted. Specific examples of the “substituted or unsubstituted arylene group” (Specific Example Group G12) include a divalent group derived by removing one hydrogen atom from the aryl ring from the “substituted or unsubstituted aryl group” described in Specific Example Group G1.

[0378] · "Substituted or unsubstituted divalent heterocyclic"

[0379] The “substituted or unsubstituted divalent heterocyclic group” described in this specification is a divalent group induced by removing one hydrogen atom from the heterocyclic group from the “substituted or unsubstituted heterocyclic group” unless otherwise noted. Specific examples of the “substituted or unsubstituted divalent heterocyclic group” (Specific Example Group G13) include a divalent group induced by removing one hydrogen atom from the heterocyclic group from the “substituted or unsubstituted heterocyclic group” described in Specific Example Group G2.

[0380] · Substituted or unsubstituted alkylene group

[0381] The “substituted or unsubstituted alkylene group” described in this specification is a divalent group derived by removing one hydrogen atom from the alkyl chain of the “substituted or unsubstituted alkyl group” unless otherwise specified. Specific examples of the “substituted or unsubstituted alkylene group” (Specific Example Group G14) include a divalent group derived by removing one hydrogen atom from the alkyl chain of the “substituted or unsubstituted alkyl group” described in Specific Example Group G3.

[0382] The substituted or unsubstituted arylene groups described in this specification are preferably any of the following general formulas (TEMP-42) to (TEMP-68), unless otherwise specified in this specification.

[0383] [Chemical Formula 9]

[0384]

[0385] [Chemical Formula 10]

[0386]

[0387] Among the above general formulas (TEMP-42) to (TEMP-52), Q 1~ Q 10 Each is independently a hydrogen atom or a substituent.

[0388] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0389] [Chemical Formula 11]

[0390]

[0391] Among the above general formulas (TEMP-53) to (TEMP-62), Q 1~ Q 10 Each is independently a hydrogen atom or a substituent.

[0392] Formula Q9 and Q 10 Silver may also form rings by joining together with a single bond.

[0393] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.

[0394] [Chemical Formula 12]

[0395]

[0396] Among the above general formulas (TEMP-63) to (TEMP-68), Q 1~ Q8 is, independently, a hydrogen atom or a substituent.

[0397] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.

[0398] The substituted or unsubstituted divalent heterocyclic groups described in this specification are preferably any of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise noted in this specification.

[0399] [Chemical Formula 13]

[0400]

[0401] [Chemical Formula 14]

[0402]

[0403] [Chemical Formula 15]

[0404]

[0405] Among the above general formulas (TEMP-69) to (TEMP-82), Q 1~Q9 is, independently, a hydrogen atom or a substituent.

[0406] [Chemical Formula 16]

[0407]

[0408] [Chemical Formula 17]

[0409]

[0410] [Chemical Formula 18]

[0411]

[0412] [Chemical Formula 19]

[0413]

[0414] Among the above general formulas (TEMP-83) to (TEMP-102), Q 1~ Q8 is, independently, a hydrogen atom or a substituent.

[0415] The above is an explanation of the “substituents described in this specification.”

[0416] · "When combining to form a ring"

[0417] In the present specification, the phrase “one or more of two or more adjacent groups combine to form a substituted or unsubstituted single ring, combine to form a substituted or unsubstituted condensed ring, or do not combine to each other” means the case where “one or more of two or more adjacent groups combine to form a substituted or unsubstituted single ring,” the case where “one or more of two or more adjacent groups combine to form a substituted or unsubstituted condensed ring,” and the case where “one or more of two or more adjacent groups do not combine to each other.”

[0418] In this specification, the cases in which "one or more sets of two or more adjacent groups combine to form a substituted or unsubstituted single ring" and "one or more sets of two or more adjacent groups combine to form a substituted or unsubstituted condensed ring" (hereinafter, these cases are collectively referred to as "combining to form a ring") will be explained below. The case of an anthracene compound represented by the following general formula (TEMP-103), in which the matrix is ​​an anthracene ring, will be explained as an example.

[0419] [Chemical Formula 20]

[0420]

[0421] For example, R 921~ R 930 In the case where "one or more sets of two or more adjacent elements combine to form a ring," the two adjacent elements forming one set refer to R 921 and R 922 of, R 922 and R 923 of, R 923 and R 924 of, R 924 and R 930 of, R 930 and R 925 of, R 925 and R 926 of, R 926 and R 927 of, R 927 and R 928 of, R 928 and R 929 of, and R 929 and R 921 It is the group of.

[0422] The above "one or more sets" means that two or more sets of the above two or more adjacent sets may simultaneously form a ring. For example, R 921 and R 922 A combines with another to form a ring Q AForms, and simultaneously R 925 and R 926 These combine with each other to form the ring Q B In the case where it is formed, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0423] [Chemical Formula 21]

[0424]

[0425] The case where "a group consisting of two or more adjacent units" forms a ring includes not only the case where a group consisting of "two" adjacent units combines as in the example above, but also the case where a group consisting of "three or more" adjacent units combines. For example, R 921 and R 922 A combines with another to form a ring Q A It forms, and also R 922 and R 923 These combine with each other to form the ring Q C Forming, three adjacent (R 921 , R 922 and R 923 This refers to the case where groups consisting of ) combine with each other to form a ring and condense onto the anthracene matrix, and in this case, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and Q C is, R 922 Share.

[0426] [Chemical Formula 22]

[0427]

[0428] The formed "single ring" or "condensed ring" may be a saturated ring or an unsaturated ring, as it is a structure consisting solely of the formed ring. Even if "a set of two adjacent rings" forms a "single ring" or a "condensed ring," said "single ring" or "condensed ring" may form a saturated ring or an unsaturated ring. For example, ring Q formed in the above general formula (TEMP-104). A and Q B are, respectively, a "single ring" or a "condensed ring." In addition, the ring Q formed in the above general formula (TEMP-105) A , and Hwan Q C is a "condensed ring". The ring Q of the above general formula (TEMP-105) A Wa Hwan Q C ne, hwan Q A Wa Hwan Q C It becomes a condensed ring through condensation. The ring Q of the above general formula (TEMP-104) A If α is a benzene ring, then ring Q A is a simple ring. The ring Q of the above general formula (TEMP-104) A If ga is a naphthalene ring, then ring Q A is a condensed ring.

[0429] "Unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. "Saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.

[0430] As a specific example of an aromatic hydrocarbon ring, a structure in which the group of examples in group G1 is terminated by a hydrogen atom can be cited.

[0431] As a specific example of an aromatic heterocyclic group, a structure in which an aromatic heterocyclic group is terminated by a hydrogen atom, as specified in the specific example group G2, can be cited.

[0432] As a specific example of an aliphatic hydrocarbon ring, a structure in which the group of specific examples in group G6 is terminated by a hydrogen atom can be cited.

[0433] "Forming a ring" means forming a ring with only a plurality of atoms of the matrix, or with a plurality of atoms of the matrix and one or more additional arbitrary elements. For example, R as shown in the general formula (TEMP-104) above. 921 and R 922 A ring Q formed by the combination of each other A is, R 921 The carbon atom of the anthracene skeleton that bonds with this, and R 922 It refers to a ring formed by a carbon atom of the anthracene skeleton to which it bonds, and one or more arbitrary elements. As a specific example, R 921 and R 922 Rohwan Q A In the case where it forms, R 921 The carbon atom of the anthracene skeleton that bonds with this, and R 922 In the case where the carbon atoms of the anthracene skeleton to which it bonds form a monocyclic unsaturated ring of four carbon atoms, R 921 and R 922 The ring formed by is a benzene ring.

[0434] Here, "any element" is, unless otherwise specified in this specification, preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur. In any element (e.g., carbon or nitrogen), bonds that do not form a ring may be terminated by hydrogen atoms, etc., or substituted by "any substituent" described below. When any element other than carbon is included, the ring formed is a heteroring.

[0435] Unless otherwise specified in this specification, “one or more of any elements” constituting a single ring or a condensed ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5.

[0436] Unless otherwise specified in this specification, among “single ring” and “condensed ring,” it is preferably “single ring”.

[0437] Unless otherwise specified in this specification, among "saturated ring" and "unsaturated ring," it is preferably "unsaturated ring".

[0438] Unless otherwise specified in this specification, "single ring" is preferably a benzene ring.

[0439] Unless otherwise specified in this specification, the “unsaturated ring” is preferably a benzene ring.

[0440] In the case where “one or more sets of two or more adjacent elements” combine with each other to form a substituted or unsubstituted single ring, or “combine with each other to form a substituted or unsubstituted condensed ring,” unless otherwise stated in this specification, preferably, one or more sets of two or more adjacent elements combine with each other to form a substituted or unsubstituted “unsaturated ring” consisting of a plurality of atoms of the matrix and at least one element selected from the group consisting of 1 to 15 carbon elements, nitrogen elements, oxygen elements, and sulfur elements.

[0441] The substituents in the case where the above "single ring" or "condensed ring" has substituents are, for example, "any substituent" described below. Specific examples of the substituents in the case where the above "single ring" or "condensed ring" has substituents are the substituents described in the aforementioned section "Substituents described in this specification."

[0442] When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, an "optional substituent" described below. When the above-mentioned "single ring" or "condensed ring" has a substituent, specific examples of substituents are the substituents described in the aforementioned section "Substituents described in this specification."

[0443] The above is an explanation of the case where “one or more of two or more adjacent groups combine to form a substituted or unsubstituted single ring” and the case where “one or more of two or more adjacent groups combine to form a substituted or unsubstituted condensed ring” (the case where they combine to form a ring).

[0444] · Substituents in the case of "substituted or unsubstituted"

[0445] In one embodiment of this specification, the substituent in the case of "substituted or unsubstituted" (which may be referred to as "optional substituent" in this specification) is, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms,

[0446] Unsubstituted alkene group having 2 to 50 carbon atoms,

[0447] Unsubstituted alkyne groups having 2 to 50 carbon atoms,

[0448] Unsubstituted cyclic cycloalkyl groups having 3 to 50 carbon atoms,

[0449] -Si(R 901 )(R 902 )(R 903 ),

[0450] -O-(R 904 ),

[0451] -S-(R 905 ),

[0452] -N(R 906 )(R 907 ),

[0453] Halogen atoms, cyano-type, nitro-type,

[0454] Unsubstituted cyclic aryl groups having 6 to 50 carbon atoms, and

[0455] Unsubstituted heterocyclic atoms with 5 to 50 atoms

[0456] It is a group selected from the group consisting of, and

[0457] Here, R 901~ R 907Each independently,

[0458] hydrogen atom,

[0459] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0460] Substituted or unsubstituted cyclic cycloalkyl groups having 3 to 50 carbon atoms,

[0461] A substituted or unsubstituted cyclic aryl group having 6 to 50 carbon atoms, or

[0462] It is a heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms.

[0463] R 901 If there are 2 or more of these, 2 or more R 901 are identical to each other, or different,

[0464] R 902 If there are 2 or more, 2 or more R 902 are identical to each other, or different,

[0465] R 903 If there are 2 or more of these, 2 or more R 903 are identical to each other, or different,

[0466] R 904 If there are 2 or more, 2 or more R 904 are identical to each other, or different,

[0467] R 905 If there are 2 or more, 2 or more R 905 are identical to each other, or different,

[0468] R 906 If there are 2 or more of these, 2 or more R 906 are identical or different from each other,

[0469] R 907 If there are 2 or more of these, 2 or more R 907 They are identical or different from each other.

[0470] In one embodiment, the substituent in the case of "substituted or unsubstituted" is,

[0471] alkyl group having 1 to 50 carbon atoms,

[0472] Cyclic aryl groups having 6 to 50 carbon atoms, and

[0473] Heterocyclic with 5 to 50 cyclic atoms

[0474] It is a group selected from the group consisting of

[0475] In one embodiment, the substituent in the case of "substituted or unsubstituted" is,

[0476] alkyl group having 1 to 18 carbon atoms,

[0477] Cyclic aryl groups having 6 to 18 carbon atoms, and

[0478] Heterocyclic cyclic atoms with 5 to 18 atoms

[0479] It is a group selected from the group consisting of

[0480] Specific examples of each of the above-mentioned arbitrary substituents are specific examples of substituents described in the aforementioned section “Substituents described in this specification”.

[0481] Unless otherwise specified in this specification, any adjacent 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, and more preferably, a benzene ring.

[0482] Unless otherwise stated in this specification, any substituent may have additional substituents. The additional substituents that any substituent has are the same as the said arbitrary substituent.

[0483] In the present specification, the numerical range indicated using “AA~BB” means a range that includes the numerical value AA listed before “AA~BB” as the lower limit and the numerical value BB listed after “AA~BB” as the upper limit.

[0484] The compounds of the present invention will be described below.

[0485] The compound of the present invention is represented by the following formula (1). However, the compound of the present invention represented by the formula included in formula (1), formulas (11) to (13) described later, and formula (21) described later may be simply referred to as the “inventive compound.”

[0486] [Chemical Formula 23]

[0487]

[0488] Hereinafter, symbols included in Equation (1), Equations (11) to (13) described later, and Equation (21) are explained. Meanwhile, identical symbols have identical meanings.

[0489] In equation (1), N * is the central nitrogen atom.

[0490] In Equation (1), R 5 ~R 8 One selected from is not particularly limited, as long as it is a single bond bonded to *1, but preferably R 6 or R 7 This is a single bond that combines with *1.

[0491] In Equation (1), R 1 ~R 4 The two selected from are not particularly limited, as long as they are substituted or unsubstituted phenyl groups, but preferably, R 1 and R 3 This, R 1 and R 2 Ga, or R 2 and R 3This is a substituted or unsubstituted phenyl group (a compound represented by Formula (11), a compound represented by Formula (12), or a compound represented by Formula (13) described below), and more preferably, R 1 and R 3 This, or R 1 and R 2 a, a substituted or unsubstituted phenyl group (a compound represented by formula (11) described below, or a compound represented by formula (12)), particularly preferably, R 1 and R 2 is a substituted or unsubstituted phenyl group (a compound represented by formula (12) described later).

[0492] R 1 ~R 4 There is no particular limitation on the number of unsubstituted phenyl groups in the two substituted or unsubstituted phenyl groups represented by, but preferably one or more, more preferably all are unsubstituted phenyl groups.

[0493] Meanwhile, R 1 ~R 4 The two substituted or unsubstituted phenyl groups represented by may be the same or different.

[0494] In formula (1), R that is not a substituted or unsubstituted phenyl group 1 ~R 4 , and R that is not a single bond 5 ~R 8 Two adjacent items selected from do not combine with each other and do not form a ring.

[0495] In formula (1), Ar 1 and Ar 2Each is, independently, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 atoms, and is not particularly limited but preferably represented by the following formulas (2A), (2B), (2C), (2D), (2E), or (2F), more preferably represented by the following formulas (2A), (2B), or (2D), and particularly preferably a substituted or unsubstituted phenyl group (based on formula (2A)), a substituted or unsubstituted biphenyl group (based on formula (2A)), a substituted or unsubstituted naphthyl group (based on formula (2B)), a substituted or unsubstituted dibenzofuranyl group (based on formula (2D)), or a substituted or unsubstituted naphthyl group (based on formula (2D)).

[0496] [Chemical Formula 24]

[0497]

[0498] In equation (2A), *21 is L 1 or L 2 It indicates the combination with.

[0499] In Equation (2A), R 101 ~R 105 One selected from is a single bond that joins to *22, and R 106 ~R 110 One selected from is a single bond that combines with *23.

[0500] R, which is not the above single bond 101 ~R 105 and R 106 ~R 110 Each is independently a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, or a substituted or unsubstituted cyclic C3-15 cycloalkyl group.

[0501] R that is not a single bond 101 ~R 105 and R 106 ~R 110In the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms shown here, the unsubstituted alkyl group having 1 to 10 carbon atoms is not particularly limited and examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, etc. Among these, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, or a hexyl group is preferred, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group is more preferred, a methyl group or a t-butyl group is more preferred, and a t-butyl group is particularly preferred.

[0502] R that is not a single bond 101 ~R 105 and R 106 ~R 110 In the substituted or unsubstituted cyclic cycloalkyl group having 3 to 15 carbon atoms shown herein, there are no particular limitations on the unsubstituted cyclic cycloalkyl group having 3 to 15 carbon atoms, and examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, a 2-norbornyl group, etc. Among these, a cyclopropyl group, a cyclobutyl group, a cyclohexyl group, a 1-adamantyl group, and a 1-norbornyl group are preferred.

[0503] In formula (2A), R, which is not a single combination 101 ~R 105 Two adjacent items selected from do not combine with each other and do not form a ring.

[0504] In formula (2A), R, which is not a single combination 106 ~R 110 Two adjacent items selected from do not combine with each other and do not form a ring.

[0505] In Equation (2A), R 111 ~R115 Each is independently a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, a substituted or unsubstituted C3-15 cycloalkyl group, a substituted or unsubstituted C6-12 aryl group, or a substituted or unsubstituted C5-13 heteroaryl group.

[0506] R 111 ~R 115 Two adjacent items selected from do not combine with each other and do not form a ring.

[0507] R 111 ~R 115 Details of the substituted or unsubstituted C1-10 alkyl group and preferred examples thereof are R 101 ~R 105 As stated regarding.

[0508] R 111 ~R 115 Details of the substituted or unsubstituted cyclic cycloalkyl group having 3 to 15 carbon atoms and preferred examples thereof are R 101 ~R 105 As stated regarding.

[0509] R 111 ~R 115 In the substituted or unsubstituted cyclic aryl group having 6 to 12 carbon atoms represented by, there are no particular limitations on the unsubstituted cyclic aryl group having 6 to 12 carbon atoms, and examples include a phenyl group, a biphenyl group, a naphthyl group, etc. Among these, a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group is preferred, a phenyl group, a 1- or 2-naphthyl group is more preferred, and a phenyl group is particularly preferred.

[0510] R 111 ~R 115In the substituted or unsubstituted heteroaryl group having 5 to 13 cyclic atoms represented by, the said unsubstituted heteroaryl group having 5 to 13 cyclic atoms is not particularly limited and, for example, pyrrolyl group, furyl group, thienyl group, pyridyl group, imidazopyridyl group, pyridazineyl group, pyrimidineyl group, pyrazineyl group, triazineyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyrazolyl group, isoxazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, indolyl group, isoindolyl group, indolyzineyl group, quinolyzineyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazineyl group, quinazolinyl group, Examples include quinoxalin group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, benzisosoxazolyl group, benzisothiazolyl group, benzofuran group, isobenzofuran group, dibenzofuran group, benzothiophen group (benzothien group, hereinafter the same), isobenzothiophen group (isobenzothien group, hereinafter the same), dibenzothiophen group (dibenzothien group, hereinafter the same), carbazolyl group, etc. Among these, a furyl group, a thienyl group, a pyridyl group, a pyrimidineyl group, a triazineyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group is preferred, and a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group (9-carbazolyl group, 1-, 2-, 3-, or 4-carbazolyl group) is more preferred.

[0511] R 111 ~R 115There are no particular limitations on the heteroaryl group having 5 to 13 substituted cyclic atoms represented by, and examples include 9-phenylcarbazolyl group, 9-biphenylcarbazolyl group, 9-phenylphenylcarbazolyl group, 9-naphthylcarbazolyl group, phenyldibenzofuranyl group, phenyldibenzothiophenyl group (phenyldibenzothienyl group, hereinafter the same).

[0512] The above-mentioned substituted or unsubstituted cyclic heteroaryl group having 5 to 13 atoms includes an isomer group if present.

[0513] In Equation (2A), j is 0, 1, or 2, and k is 0 or 1. The case where j is 2 and k is 0 is excluded.

[0514] In the case of j=0, k=0, *23 represents *21.

[0515] In the case of j=0, k=1, *22 represents *21.

[0516] In the case of j=1, k=0, *23 represents *22.

[0517] In one aspect of the present invention, j is 0 and k is 0. In this case, *23 represents *21, and Equation (2A) is expressed as the following equation.

[0518] [Chemical Formula 25]

[0519]

[0520] In another aspect of the present invention, j is 0 and k is 1. In this case, *22 represents *21, and Equation (2A) is expressed as the following equation.

[0521] [Chemical Formula 26]

[0522]

[0523] In another aspect of the present invention, j is 1 and k is 0. In this case, *23 represents *22, and Equation (2A) is expressed as the following equation.

[0524] [Chemical Formula 27]

[0525]

[0526] In another aspect of the present invention, j is 1 and k is 1. In this case, Equation (2A) is expressed as follows.

[0527] [Chemical Formula 28]

[0528]

[0529] In another aspect of the present invention, j is 2 and k is 1. In this case, Equation (2A) is expressed as follows.

[0530] [Chemical Formula 29]

[0531]

[0532] The unit represented by Equation (2A) is preferably represented by the following equation. In the following equation, R has been omitted for simplification.

[0533] [Chemical Formula 30]

[0534]

[0535] R that is not a single bond bonding to *22 101 ~R 105 R that is not a single bond bonding to , *23 106 ~R 110 , and R 111 ~R 115 It is okay if all of them are hydrogen atoms.

[0536] [Chemical Formula 31]

[0537]

[0538] In equation (2B), *24 is L 1 or L 2 It indicates the combination with.

[0539] In equation (2B), R 121 ~R 128 One selected from is a single combination that combines with *25.

[0540] Among formula (2B), R, which is not a single combination 121 ~R 128Each is independently a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, a substituted or unsubstituted cyclic C3-15 cycloalkyl group, or a substituted or unsubstituted cyclic C6-12 aryl group.

[0541] R, which is not the above single bond 121 ~R 128 Two adjacent items selected from do not combine with each other and do not form a ring.

[0542] R 121 ~R 128 Details of the substituted or unsubstituted C1-10 alkyl group and preferred examples thereof are as follows: R 101 ~R 105 As stated regarding.

[0543] R 121 ~R 128 Details and preferred examples of the substituted or unsubstituted cyclic cycloalkyl group having 3 to 15 carbon atoms shown herein are, above R 101 ~R 105 As stated regarding.

[0544] R 121 ~R 128 The substituted or unsubstituted cyclic aryl group having 6 to 12 carbon atoms represented by this is the above R 111 ~R 115 As stated regarding.

[0545] In one aspect of the present invention, preferably R 121 , R 124 , R 125 , and R 128 It is preferable that one selected from is a single bond that combines with *25.

[0546] R that is not a single bond bonding to *25 121 ~R 128 It is okay if all of them are hydrogen atoms.

[0547] [Chemical Formula 32]

[0548]

[0549] In equation (2C), *26 is L 1 or L 2 It indicates the combination with.

[0550] In Equation (2C), R 131 ~R 140 One selected from is a single bond that combines with *27.

[0551] R, which is not the above single bond 131 ~R 140 Each is independently a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, a substituted or unsubstituted cyclic C3-15 cycloalkyl group, or a substituted or unsubstituted cyclic C6-12 aryl group.

[0552] R, which is not the above single bond 131 ~R 140 Two adjacent items selected from do not combine with each other and do not form a ring.

[0553] R 131 ~R 140 Details of the substituted or unsubstituted C1-10 alkyl group and preferred examples thereof are as follows: R 101 ~R 105 As stated regarding.

[0554] R 131 ~R 140 Details and preferred examples of the substituted or unsubstituted cyclic cycloalkyl group having 3 to 15 carbon atoms shown herein are, above R 101 ~R 105 As stated regarding.

[0555] R 131 ~R 140 Details of the substituted or unsubstituted cyclic aryl group having 6 to 12 carbon atoms and preferred examples thereof are as follows: the above R 111 ~R 115 As stated regarding.

[0556] In one aspect of the present invention, preferably R 137and R 138 One selected from is a single bond that bonds to *27, and more preferably R 137 It is a single bond that combines with *27.

[0557] R that is not a single bond bonding to *27 131 ~R 140 These can all be hydrogen atoms.

[0558] [Chemical Formula 33]

[0559]

[0560] In equation (2D), *28 is L 1 or L 2 It indicates the combination with.

[0561] Among equation (2D), X 1 Silver, oxygen atom, sulfur atom, -CR a R b , or -NR c It is. Among these, the oxygen atom, -CR a R b , -NR c It is desirable.

[0562] In equation (2D), *29 is R 141 ~R 148 , R 200 ~R 203 , R a , R b , or R c Combines with one of the

[0563] *29 is R a , R b , and R c If bonding to either of them, R a , R b , and R c Either one is a single bond that binds to *29 or a divalent bond that binds to *29.

[0564] R a , R b , or R cThere are no particular limitations on the divalent groups that can be taken, and examples include unsubstituted phenylene groups, unsubstituted biphenylene groups, and unsubstituted naphthylene groups. Among these, unsubstituted phenylene groups are preferred, and unsubstituted m-phenylene groups and unsubstituted p-phenylene groups are more preferred.

[0565] In equation (2D), p is 0 or 1.

[0566] p is 0, and X 1 This, oxygen atom, sulfur atom, -CR a R b , or -NR c When, R a , R b , R c , and R 141 ~R 148 One selected from is a single combination that combines with *29.

[0567] p is 1, and X 1 This -CR a R b or -NR c When, R 145 and R 146 , R 146 and R 147 , R 141 and R 148 , or R 147 and R 148 R, where one side is a single bond bonding to *e and the other side is a single bond bonding to *f, and not a single bond bonding to *e or *f. 141 and R 145 ~R 148 , R 142 ~R 144 , R 200 ~R 203 , R a , R b , and R c One selected from is a single combination that combines with *29.

[0568] p is 1, and X 1 When this is an oxygen atom or a sulfur atom, R 145and R 146 , R 146 and R 147 , R 141 and R 148 , or R 147 and R 148 R, where one side is a single bond bonding to *e and the other side is a single bond bonding to *f, and not a single bond bonding to *e or *f. 141 and R 145 ~R 148 , R 142 ~R 144 , and R 200 ~R 203 One selected from is a single combination that combines with *29.

[0569] Among equation (2D), R, which is not a single combination, 141 ~R 148 , R which is not the above single bond 200 ~R 203 , R which is not the above single bond and is not the above divalent group a and R b , and R c Each is independently a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, a substituted or unsubstituted C3-15 cycloalkyl group, a substituted or unsubstituted C6-12 aryl group, or a substituted or unsubstituted C5-13 heteroaryl group.

[0570] However, R a and R b It is preferable that the hydrogen atoms of the unsubstituted alkyl group represented by are not deuterated.

[0571] R, which is not the above single bond 141 ~R 148 and the above single bond is not R 200 ~R 203 Two adjacent items selected from do not combine with each other and do not form a ring.

[0572] R that is not a single bond 141 ~R 148, R that is not a single bond 200 ~R 203 , not a single bond and not the above divalent group R a and R b , and R c Details of the substituted or unsubstituted C1-10 alkyl group and preferred examples thereof are as follows: R 101 ~R 105 As stated regarding.

[0573] R that is not a single bond 141 ~R 148 , R that is not a single bond 200 ~R 203 , not a single bond and not the above divalent group R a and R b , and R c Details of the substituted or unsubstituted cyclic cycloalkyl group having 3 to 15 carbon atoms and preferred examples thereof are as follows: the above R 101 ~R 105 As stated regarding.

[0574] R that is not a single bond 141 ~R 148 , R that is not a single bond 200 ~R 203 , not a single bond and not the above divalent group R a and R b , and R c Details of the substituted or unsubstituted cyclic aryl group having 6 to 12 carbon atoms and preferred examples thereof are as follows: the above R 111 ~R 115 As stated regarding.

[0575] R that is not a single bond 141 ~R 148 , R that is not a single bond 200 ~R 203 , not a single bond and not the above divalent group R a and R b , and R cDetails of a heteroaryl group having 5 to 13 substituted or unsubstituted cyclic atoms represented by and preferred examples thereof are, above R 111 ~R 115 As stated regarding.

[0576] R that is not a single bond 141 ~R 148 , R that is not a single bond 200 ~R 203 , not a single bond and not the above divalent group R a and R b , and R c They can all be hydrogen atoms.

[0577] [Chemical Formula 34]

[0578]

[0579] In equation (2E), *30 is L 1 or L 2 It indicates the combination with.

[0580] In Equation (2E), R 151 ~R 155 One selected from is a single bond that joins to *31, and R 151 ~R 155 The other one selected from is a single bond that combines with *32.

[0581] In formula (2E), R, which is not a single combination, 151 ~R 155 Each is independently a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, a substituted or unsubstituted cyclic C3-15 cycloalkyl group, or an unsubstituted phenyl group.

[0582] R, which is not the above single bond 151 ~R 155 Two adjacent items selected from do not combine with each other and do not form a ring.

[0583] In Equation (2E), R 161 ~R 165 and R 171 ~R 175Each is independently a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, or a substituted or unsubstituted cyclic C3-15 cycloalkyl group.

[0584] R, which is not a hydrogen atom 161 ~R 165 At least one adjacent two selected from combine to form one or more unsubstituted benzene rings, or do not combine to form rings.

[0585] R, which is not a hydrogen atom 171 ~R 175 At least one adjacent two selected from combine to form one or more unsubstituted benzene rings, or do not combine to form rings.

[0586] R 151 ~R 155 , R 161 ~R 165 , and R 171 ~R 175 Details of the substituted or unsubstituted C1-10 alkyl group and preferred examples thereof are as follows: R 101 ~R 105 As stated regarding.

[0587] R 151 ~R 155 , R 161 ~R 165 , and R 171 ~R 175 Details of the substituted or unsubstituted cyclic cycloalkyl group having 3 to 15 carbon atoms and preferred examples thereof are as follows: the above R 101 ~R 105 As stated regarding.

[0588] In one aspect of the present invention, R 161 ~R 165 Two adjacent rings selected from combine with each other to form one or more unsubstituted benzene rings. In another aspect of the present invention, R 161 ~R165 Two adjacent items selected from do not combine with each other and therefore do not form a ring structure.

[0589] In one aspect of the present invention, R 171 ~R 175 Two adjacent rings selected from combine with each other to form one or more unsubstituted benzene rings. In another aspect of the present invention, R 171 ~R 175 Two adjacent items selected from do not combine with each other and therefore do not form a ring structure.

[0590] R that is not a single bond 151 ~R 155 , can all be hydrogen atoms, and R 161 ~R 165 They can all be hydrogen atoms, and R 171 ~R 175 All of them can be hydrogen atoms.

[0591] [Chemical Formula 35]

[0592]

[0593] In equation (2F), *33 is L 1 or L 2 It indicates the combination with.

[0594] In equation (2F), R 181 ~R 192 One selected from is a single combination that combines with *34.

[0595] In formula (2F), R, which is not a single combination, 181 ~R 192 Each is independently a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, a substituted or unsubstituted cyclic C3-15 cycloalkyl group, or a substituted or unsubstituted cyclic C6-12 aryl group.

[0596] R, which is not the above single bond 181 ~R 192Two adjacent items selected from do not combine with each other and do not form a ring.

[0597] R 181 ~R 192 Details of the substituted or unsubstituted C1-10 alkyl group and preferred examples thereof are as follows: R 101 ~R 105 As stated regarding.

[0598] R 181 ~R 192 Details of the substituted or unsubstituted cyclic cycloalkyl group having 3 to 15 carbon atoms and preferred examples thereof are as follows: the above R 101 ~R 105 As stated regarding.

[0599] R 181 ~R 192 Details of the substituted or unsubstituted cyclic aryl group having 6 to 12 carbon atoms and preferred examples thereof are as follows: the above R 111 ~R 115 As stated regarding.

[0600] In one aspect of the present invention, R 181 This is a single bond that binds to *33, and for other suns, R 182 It is a single bond that combines with *33.

[0601] R that is not a single bond 181 ~R 192 A, all may be hydrogen atoms.

[0602] In formula (1), L 1 , L 2 , and L 3 ...is not particularly limited, provided that each is independently a single-bonded, substituted or unsubstituted cyclic arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms, but preferably a single-bonded, substituted or unsubstituted cyclic arylene group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 13 carbon atoms. Also, L3 As long as it is a single bond, substituted or unsubstituted cyclic arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms, there are no particular limitations, but preferably, it is a single bond, substituted or unsubstituted cyclic arylene group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 13 carbon atoms, more preferably, a substituted or unsubstituted cyclic arylene group having 6 to 12 carbon atoms, even more preferably, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group, more preferably a substituted or unsubstituted phenylene group, particularly preferably an unsubstituted phenylene group.

[0603] However, L 1 , L 2 , and L 3 In the case of the substituted or unsubstituted cyclic arylene group having 6 to 30 carbon atoms, the substituted or unsubstituted cyclic heteroarylene group having 5 to 30 carbon atoms, the substituted or unsubstituted cyclic arylene group having 6 to 12 carbon atoms, and the substituted or unsubstituted heteroarylene group having 5 to 13 carbon atoms, the substituent in the case of “substituted or unsubstituted” is, respectively, an unsubstituted alkyl group having 1 to 18 carbon atoms, an unsubstituted cyclic aryl group having 6 to 18 carbon atoms, or an unsubstituted heteroaryl group having 5 to 18 carbon atoms.

[0604] Meanwhile, L 1 or L 2 If is a single bond, Ar 1 or Ar 2 means directly binding to the central nitrogen, for example, Ar 1 or Ar 2 The formula is (2A), (2B), (2C), (2D), (2E), or (2F), and L 1 or L 2In the case where is a single bond, *21, *24, *26, *28, *30, and *33 in formulas (2A), (2B), (2C), (2D), (2E), or (2F) are directly bonded to the central nitrogen.

[0605] L 1 , L 2 , and L 3 In the substituted or unsubstituted cyclic arylene group having 6 to 30 carbon atoms shown here, the unsubstituted cyclic arylene group having 6 to 30 carbon atoms is not particularly limited and examples include a phenylene group, a biphenylylene group, a terphenylylene group, a naphthylene group, anthrylene group, a benzanthrylene group, a phenanthrylene group, a benzophenanthrylene group, a phenyleneylene group, a pyreneylene group, a pyreneylene group, a benzochrysenylene group, a triphenyleneylene group, etc. Among these, a phenylene group, a biphenylylene group, and a naphthylene group are preferred.

[0606] L 1 , L 2 , and L 3In the heteroarylene group having 5 to 30 substituted or unsubstituted cyclic atoms represented by this, the heteroarylene group having 5 to 30 unsubstituted cyclic atoms is not particularly limited and, for example, pyrrolylene group, furylene group, thienyllene group, pyridylene group, imidazopyridylene group, pyridazineylene group, pyrimidineylene group, pyrazineylene group, triazineylene group, imidazolylene group, oxazolilene group, thiazolilene group, pyrazolilene group, isooxazolilene group, isothiazolylene group, oxadiazolilene group, thiazolilene group, triazolilene group, tetrazolylene group, indolylene group, isoindolilene group, benzofuranylene group, isobenzofuranylene group, Examples include benzothiophenylene group, isobenzothiophenylene group, indolezylene group, quinolizylene group, quinolilene group, isoquinolilene group, cinolilene group, phthalazinylene group, quinazolinylene group, quinoxalinylene group, benzimidazolilene group, benzoxazolilene group, benzothiazolylene group, indazolilene group, benzisothiazolilene group, benzisothiazolilene group, phenanthridineylene group, acridineylene group, phenanthrolineylene group, phenazineylene group, phenothiazolylene group, phenoxazineylene group, xanthenylene group, etc.

[0607] L 1 , L 2 , and L 3In the substituted or unsubstituted cyclic arylene group having 6 to 30 carbon atoms (preferably 6 to 12) and the substituted or unsubstituted heteroarylene group having 5 to 30 atoms (preferably 5 to 13) as indicated by this, the unsubstituted alkyl group having 1 to 18 carbon atoms as a substituent in the case of "substituted or unsubstituted" is not particularly limited, and examples include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, Examples include n-octadecyl groups, neopentyl groups, amyl groups, isoamyl groups, 1-methylpentyl groups, 2-methylpentyl groups, 1-pentylhexyl groups, 1-butylpentyl groups, 1-heptyloctyl groups, 3-methylpentyl groups, etc. Among these, methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, isobutyl groups, s-butyl groups, and t-butyl groups are preferred, methyl groups, ethyl groups, isopropyl groups, and t-butyl groups are more preferred, and methyl groups and t-butyl groups are particularly preferred.

[0608] L 1 , L 2 , and L 3 In the case of the substituted or unsubstituted arylene group having 6 to 30 carbon atoms (preferably 6 to 12) and the substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms (preferably 5 to 13) represented by this, the unsubstituted aryl group having 6 to 18 carbon atoms as the substituent in the case of "substituted or unsubstituted" is not particularly limited, and examples include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, anthryl group, a phenanthryl group, a phenylenyl group, a pentaphenyl group, a pyreneyl group, a chrysenyl group, a fluoreneyl group, a triphenyleneyl group, etc. Among these, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, anthryl group, a fluoreneyl group, or a triphenyleneyl group is preferred.

[0609] L 1 , L 2 , and L 3 In the case of the substituted or unsubstituted arylene group having 6 to 30 carbon atoms (preferably 6 to 12) and the substituted or unsubstituted heteroarylene group having 5 to 30 (preferably 5 to 13) cyclic atoms, the unsubstituted heteroaryl group having 5 to 18 cyclic atoms as a substituent in the case of "substituted or unsubstituted" is not particularly limited and, for example, pyrrolyl group, furyl group, thienyl group, pyridyl group, imidazopyridyl group, pyridazineyl group, pyrimidineyl group, pyrazineyl group, triazineyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyrazolyl group, isoxazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, Examples include indolyl group, isoindolyl group, indolizine group, quinolizine group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazine group, quinazolin group, quinoxalin group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, benzisoxazolyl group, benzisothiazolyl group, benzofuran group, isobenzofuran group, dibenzofuran group, benzothiophen group (benzothien group, hereinafter the same), isobenzothiophen group (isobenzothien group, hereinafter the same), dibenzothiophen group (dibenzothien group, hereinafter the same), carbazolyl group, etc. Among these, a furyl group, a thienyl group, a pyridyl group, a pyrimidineyl group, a triazineyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group is preferred, and a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group (9-carbazolyl group, 1-, 2-, 3-, or 4-carbazolyl group) is more preferred.

[0610] In formula (1), R that is not a substituted or unsubstituted phenyl group 1~R 4 , R that is not a single bond 5 ~R 8 , and any substituent in the phenyl group is each independently a hydrogen atom, a substituted or unsubstituted C1-50 alkyl group, a substituted or unsubstituted C2-50 alkenyl group, a substituted or unsubstituted C2-50 alkynyl group, a substituted or unsubstituted cyclic C3-50 cycloalkyl group, -Si(R 901 ')(R 902 ')(R 903 '), -O-(R 904 '), -S-(R 905 It is a halogen atom, a cyano group, or a nitro group. Among these, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cyclic cycloalkyl group having 3 to 50 carbon atoms is preferred, and a hydrogen atom is more preferred.

[0611] R 901 '~R 905 Each is independently a hydrogen atom, a substituted or unsubstituted C1-50 alkyl group, a substituted or unsubstituted cyclic C3-50 cycloalkyl group, or a substituted or unsubstituted cyclic C6-50 aryl group. Among these, a hydrogen atom, a substituted or unsubstituted C1-50 alkyl group, or a substituted or unsubstituted cyclic C3-50 cycloalkyl group is preferred, and a hydrogen atom, or a substituted or unsubstituted C1-50 alkyl group is more preferred.

[0612] R 901 '~R 905 If there are 2 or more ', 2 or more R 901 '~R 905 ' can be the same or different.

[0613] R that is not a substituted or unsubstituted phenyl group 1 ~R 4 , R that is not a single bond 5 ~R 8The substituted or unsubstituted alkyl group having 1 to 50 carbon atoms represented by any substituent in the phenyl group is not particularly limited, but is preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, more preferably a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, and particularly preferably a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms.

[0614] R that is not a substituted or unsubstituted phenyl group 1 ~R 4 , R that is not a single bond 5 ~R 8 , and in the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms represented by any substituent in the phenyl group, the unsubstituted alkyl group having 1 to 50 carbon atoms is not particularly limited and examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, etc. Among these, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, and pentyl groups are preferred, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, and t-butyl groups are more preferred, and methyl and t-butyl groups are particularly preferred.

[0615] R that is not a substituted or unsubstituted phenyl group 1 ~R 4 , R that is not a single bond 5 ~R 8 The substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms represented by any substituent in the phenyl group is not particularly limited, but is preferably a substituted or unsubstituted alkenyl group having 1 to 30 carbon atoms, more preferably a substituted or unsubstituted alkenyl group having 1 to 15 carbon atoms, and particularly preferably a substituted or unsubstituted alkenyl group having 1 to 5 carbon atoms.

[0616] R that is not a substituted or unsubstituted phenyl group 1 ~R 4 , R that is not a single bond 5 ~R 8 ..., and in the substituted or unsubstituted alkeneyl group having 2 to 50 carbon atoms represented by any substituent in the phenyl group, the unsubstituted alkeneyl group having 2 to 50 carbon atoms is not particularly limited and examples include a vinyl group, a 2-propeneyl group, a 1-buteneyl group, a 2-buteneyl group, a 3-buteneyl group, a 4-penteneyl group, a 5-hexeneyl group, a 1-methyl-2-propeneyl group, a 1-methyl-2-buteneyl group, a 1,1-dimethyl-2-propeneyl group, etc. Among these, a vinyl group, a 2-propeneyl group, a 1-buteneyl group, a 2-buteneyl group, and a 3-buteneyl group are preferred, and a vinyl group and a 2-propeneyl group are more preferred.

[0617] R that is not a substituted or unsubstituted phenyl group 1 ~R 4 , R that is not a single bond 5 ~R 8 The substituted or unsubstituted alkyne group having 2 to 50 carbon atoms represented by any substituent in the phenyl group is not particularly limited, but is preferably a substituted or unsubstituted alkyne group having 1 to 30 carbon atoms, more preferably a substituted or unsubstituted alkyne group having 1 to 15 carbon atoms, and particularly preferably a substituted or unsubstituted alkyne group having 1 to 5 carbon atoms.

[0618] R that is not a substituted or unsubstituted phenyl group 1 ~R 4 , R that is not a single bond 5 ~R 8..., and in the substituted or unsubstituted alkyne group having 2 to 50 carbon atoms represented by any substituent in the phenyl group, the unsubstituted alkyne group having 2 to 50 carbon atoms is not particularly limited and examples include an etyne group, 2-propinyl group, 2-butinyl group, 3-butinyl group, 4-pentyneyl group, 5-hexyneyl group, 1-methyl-2-propinyl group, 1-methyl-2-butinyl group, 1,1-dimethyl-2-propinyl group, etc. Among these, an etyne group, 2-propinyl group, and 2-butinyl group are preferred, and an etyne group and 2-propinyl group are more preferred.

[0619] R that is not a substituted or unsubstituted phenyl group 1 ~R 4 , R that is not a single bond 5 ~R 8 The substituted or unsubstituted cyclic cycloalkyl group having 3 to 50 carbon atoms represented by any substituent in the phenyl group is not particularly limited, but is preferably a substituted or unsubstituted cyclic cycloalkyl group having 1 to 30 carbon atoms, more preferably a substituted or unsubstituted cyclic cycloalkyl group having 1 to 15 carbon atoms, and particularly preferably a substituted or unsubstituted cyclic cycloalkyl group having 1 to 10 carbon atoms.

[0620] R that is not a substituted or unsubstituted phenyl group 1 ~R 4 , R that is not a single bond 5 ~R 8..., and in the substituted or unsubstituted cyclic cycloalkyl group having 3 to 50 carbon atoms represented by any substituent in the phenyl group, the unsubstituted cyclic cycloalkyl group having 3 to 50 carbon atoms is not particularly limited and examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a 2-norbornyl group. Among these, a cyclopropyl group, a cyclobutyl group, a cyclohexyl group, a 1-adamantyl group, and a 1-norbornyl group are preferred, and a cyclohexyl group and a 1-adamantyl group are more preferred.

[0621] R that is not a substituted or unsubstituted phenyl group 1 ~R 4 , R that is not a single bond 5 ~R 8 , and -Si(R that any substituent in the phenyl group can represent 901 ')(R 902 ')(R 903 '), -O-(R 904 '), and -S-(R 905 R of ') 901 '~R 905 Each is independently a hydrogen atom, a substituted or unsubstituted C1-50 alkyl group, a substituted or unsubstituted cyclic C3-50 cycloalkyl group, or a substituted or unsubstituted cyclic C6-50 aryl group.

[0622] The above R 901 '~R 905 As for the substituted or unsubstituted C1 to C50 alkyl group represented by ', there are no particular limitations, and for example, R which is not the aforementioned substituted or unsubstituted phenyl group 1 ~R 4 , R that is not a single bond 5 ~R 8 , and details and preferred examples thereof of a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms represented by any substituent in the phenyl group may be referenced.

[0623] The above R 901 '~R 905 As for the substituted or unsubstituted cyclic cycloalkyl group having 3 to 50 carbon atoms represented by ', there are no particular limitations, and for example, R which is not the aforementioned substituted or unsubstituted phenyl group 1 ~R 4 , R that is not a single bond 5 ~R 8 , and details and preferred examples thereof of a substituted or unsubstituted cyclic cycloalkyl group having 3 to 50 carbon atoms represented by any substituent in the phenyl group may be referenced.

[0624] The above R 901 '~R 905 In the substituted or unsubstituted cyclic aryl group having 6 to 50 carbon atoms represented by ', there are no particular limitations on the unsubstituted cyclic aryl group having 6 to 50 carbon atoms, and examples include a phenyl group, a biphenylyl group, a terphenylyl group, a biphenyleneyl group, a naphthyl group, anthryl group, a benzanthyl group, a phenanthyl group, a benzophenanthyl group, a phenaleneyl group, a physenyl group, a pentaphenyl group, a pyreneyl group, a chrysenyl group, a benzochrysenyl group, a fluoreneyl group, a fluorantheneyl group, a peryleneyl group, or a triphenyleneyl group. Among these, a phenyl group, a biphenylyl group, or a naphthyl group is preferred.

[0625] R that is not a substituted or unsubstituted phenyl group 1 ~R 4 , R that is not a single bond 5 ~R 8 There are no particular limitations on the halogen atoms that can be represented by any substituent in the phenyl group, and examples include fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, astatine atoms, tennessine atoms, etc. Among these, fluorine atoms and chlorine atoms are preferred.

[0626] There are no particular limitations on the compound represented by formula (1), but as described above, it is preferable to have a compound represented by the following formula (11), a compound represented by the following formula (12), or a compound represented by the following formula (13). From the perspective of improving the lifespan of the organic EL device, it is more preferable to have a compound represented by the following formula (11) or a compound represented by the following formula (12), and it is particularly preferable to have a compound represented by the following formula (12).

[0627] [Chemical Formula 36]

[0628]

[0629] [Chemical Formula 37]

[0630]

[0631] [Chemical Formula 38]

[0632]

[0633] Among equations (11) to (13), N * , R 1 ~R 8 , *1, Ar 1 , Ar 2 , L 1 , L 2 , and L 3 It is as defined in the above formula (1).

[0634] Among equations (11) to (13), R 11 ~R 15 and R 21 ~R 25 are, each independently, a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted C2–50 alkenyl group, a substituted or unsubstituted C2–50 alkynyl group, a substituted or unsubstituted cyclic C3–50 cycloalkyl group, -Si(R 901 ')(R 902 ')(R 903 '), -O-(R 904 '), -S-(R 905It is a halogen atom, a cyano group, or a nitro group. R 901 '~R 905 ' is, each independently, a hydrogen atom, a substituted or unsubstituted C1-50 alkyl group, a substituted or unsubstituted cyclic C3-50 cycloalkyl group, or a substituted or unsubstituted cyclic C6-50 aryl group. R 901 '~R 905 If there are 2 or more ', 2 or more R 901 '~R 905 ' can be the same or different.

[0635] R 11 ~R 15 and R 21 ~R 25 Two adjacent items selected from do not combine with each other and do not form a ring.

[0636] R 11 ~R 15 and R 21 ~R 25 As for the substituted or unsubstituted C1 to C50 alkyl group represented by, there are no particular limitations, and for example, R which is not the aforementioned substituted or unsubstituted phenyl group 1 ~R 4 , R that is not a single bond 5 ~R 8 , and details and preferred examples thereof of a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms represented by any substituent in the phenyl group may be referenced.

[0637] R 11 ~R 15 and R 21 ~R 25 As for the substituted or unsubstituted alkeneyl group having 2 to 50 carbon atoms represented by, there are no particular restrictions, and for example, R which is not the aforementioned substituted or unsubstituted phenyl group 1 ~R 4 , R that is not a single bond 5 ~R 8Refer to the details and preferred examples of the substituted or unsubstituted alkeneyl group having 2 to 50 carbon atoms represented by any substituent in the phenyl group.

[0638] R 11 ~R 15 and R 21 ~R 25 As for the substituted or unsubstituted alkyne group having 2 to 50 carbon atoms represented by, there are no particular restrictions, and for example, R which is not the aforementioned substituted or unsubstituted phenyl group 1 ~R 4 , R that is not a single bond 5 ~R 8 , and details and preferred examples thereof of a substituted or unsubstituted alkyne group having 2 to 50 carbon atoms represented by any substituent in the phenyl group may be referenced.

[0639] R 11 ~R 15 and R 21 ~R 25 As for the substituted or unsubstituted cyclic cycloalkyl group having 3 to 50 carbon atoms represented by, there are no particular limitations, and for example, R which is not the aforementioned substituted or unsubstituted phenyl group 1 ~R 4 , R that is not a single bond 5 ~R 8 , and details and preferred examples thereof of a substituted or unsubstituted cyclic cycloalkyl group having 3 to 50 carbon atoms represented by any substituent in the phenyl group may be referenced.

[0640] R 11 ~R 15 and R 21 ~R 25 -Si(R 901 ')(R 902 ')(R 903 '), -O-(R 904 '), and -S-(R 905 As for '), R 901 '~R 905Includes substituted or unsubstituted C1-50 alkyl groups, substituted or unsubstituted cyclic C3-50 cycloalkyl groups, and substituted or unsubstituted cyclic C6-50 aryl groups, without particular limitation, for example, R other than the aforementioned substituted or unsubstituted phenyl group. 1 ~R 4 , R that is not a single bond 5 ~R 8 , and -Si(R 901 ')(R 902 ')(R 903 '), -O-(R 904 '), -S-(R 905 '), and that R 901 '~R 905 You can refer to the details of ' and its desirable examples.

[0641] R 11 ~R 15 and R 21 ~R 25 As for the halogen atom represented by , there are no particular restrictions, and for example, R that is not the aforementioned substituted or unsubstituted phenyl group 1 ~R 4 , R that is not a single bond 5 ~R 8 , and details of the halogen atom represented by any substituent in the phenyl group and preferred examples thereof may be referred to.

[0642] As for the compound represented by formula (1), there are no particular limitations, but as mentioned above, L 3 It is preferable that this be an unsubstituted phenylene group, and from the perspective of improving the lifespan of the organic EL device, it is more preferable that it be a compound represented by the following formula (21).

[0643] [Chemical Formula 39]

[0644]

[0645] In equation (21), N * , R 1 ~R8 , *1, Ar 1 , Ar 2 , L 1 , and L 2 is as defined in the above formula (1).

[0646] As stated above, the "hydrogen atom" used in this specification includes light hydrogen atoms, deuterium atoms, and tritium atoms. Accordingly, the compound of the invention may include naturally occurring deuterium atoms.

[0647] In addition, deuterium atoms may be intentionally introduced into the inventive compound by using a deuteriumized compound in part or all of the raw material compound. Accordingly, in one aspect of the present invention, the inventive compound may contain at least one deuterium atom. That is, the inventive compound may be a compound represented by formula (1), and may be a compound in which at least one of the hydrogen atoms included in the compound is a deuterium atom.

[0648] In one aspect of the present invention, L 1 , L 2 , and L 3 In the case where all of these are unsubstituted phenylene groups, each of these unsubstituted phenylene groups may independently contain at least one deuterium atom.

[0649] In one aspect of the present invention, L 1 , L 2 , and L 3 In the case where all of these are unsubstituted phenylene groups, the hydrogen atoms included in one of the unsubstituted phenylene groups may all be deuterium atoms.

[0650] In one aspect of the present invention, L 1 , L 2 , and L 3 In the case where all of these are unsubstituted phenylene groups, the hydrogen atoms included in two of the unsubstituted phenylene groups may all be deuterium atoms.

[0651] In one aspect of the present invention, L 1 , L 2 , and L 3 In the case where all of these are unsubstituted phenylene groups, the hydrogen atoms included in these unsubstituted phenylene groups may all be deuterium atoms.

[0652] The deuterium content of the inventive compound depends on the deuterium content of the raw material compound used. Even if a raw material with a predetermined deuterium content is used, a certain proportion of naturally derived light hydrogen isotopes may be included. Therefore, the deuterium content of the inventive compound shown below includes a ratio that takes into account trace amounts of naturally derived isotopes, in addition to the ratio obtained by simply counting the number of deuterium atoms represented by the chemical formula.

[0653] The deuterium content of the inventive compound is not particularly limited, but is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, and particularly preferably 20% or more. In addition, the deuterium content may be 1 to 100%, 2 to 90%, 3 to 80%, 5 to 60%, 10 to 50%, or 20 to 30%.

[0654] The inventive compound may be a mixture comprising a deuterated compound and a non-deuterated compound, or a mixture of two or more compounds having different deuteration rates. The deuteration rate of such a mixture is not particularly limited, but is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, and particularly preferably 20% or more. In addition, the deuteration rate may be 1 to 100%, 3 to 80%, 5 to 60%, 10 to 50%, or 20 to 30%.

[0655] Except in exceptional cases, the details of the substituents (optional substituents) referred to as "substituted or unsubstituted" included in the definitions of each of the above formulas are as described in the section titled "Substituents referred to as 'substituted or unsubstituted'".

[0656] The compound of the invention can be easily prepared by a person skilled in the art by referring to the following synthesis examples and known synthesis methods.

[0657] Specific examples of the inventive compounds are shown below, but are not limited to the following exemplary compounds. In addition to the compounds described in the following exemplary compounds, the inventive compounds also include compounds in which, due to the synthesis technique, some hydrogen is not deuteriumized.

[0658] In the following specific examples, D represents a deuterium atom.

[0659] [Chemical Formula 40]

[0660]

[0661] [Chemical Formula 41]

[0662]

[0663] [Chemical Formula 42]

[0664]

[0665] [Chemical Formula 43]

[0666]

[0667] [Chemical Formula 44]

[0668]

[0669] [Chemical Formula 45]

[0670]

[0671] [Chemical Formula 46]

[0672]

[0673] [Chemical Formula 47]

[0674]

[0675] [Chemical Formula 48]

[0676]

[0677] [Chemical Formula 49]

[0678]

[0679] [Chemical Formula 50]

[0680]

[0681] [Chemical Formula 51]

[0682]

[0683] [Chemical Formula 52]

[0684]

[0685] [Chemical Formula 53]

[0686]

[0687] [Chemical Formula 54]

[0688]

[0689] [Chemical Formula 55]

[0690]

[0691] [Chemical Formula 56]

[0692]

[0693] [Chemical Formula 57]

[0694]

[0695] [Chemical Formula 58]

[0696]

[0697] [Chemical Formula 59]

[0698]

[0699] [Chemical Formula 60]

[0700]

[0701] [Chemical Formula 61]

[0702]

[0703] [Chemical Formula 62]

[0704]

[0705] [Chemical Formula 63]

[0706]

[0707] [Chemical Formula 64]

[0708]

[0709] [Chemical Formula 65]

[0710]

[0711] [Chemical Formula 66]

[0712]

[0713] [Chemical Formula 67]

[0714]

[0715] [Chemical Formula 68]

[0716]

[0717] [Chemical Formula 69]

[0718]

[0719] [Chemical Formula 70]

[0720]

[0721] [Chemical Formula 71]

[0722]

[0723] [Chemical Formula 72]

[0724]

[0725] [Chemical Formula 73]

[0726]

[0727] [Chemical Formula 74]

[0728]

[0729] [Chemical Formula 75]

[0730]

[0731] [Chemical Formula 76]

[0732]

[0733] [Chemical Formula 77]

[0734]

[0735] [Chemical Formula 78]

[0736]

[0737] [Chemical Formula 79]

[0738]

[0739] [Chemical Formula 80]

[0740]

[0741] [Chemical Formula 81]

[0742]

[0743] [Chemical Formula 82]

[0744]

[0745] [Chemical Formula 83]

[0746]

[0747] [Chemical Formula 84]

[0748]

[0749] [Chemical Formula 85]

[0750]

[0751] [Chemical Formula 86]

[0752]

[0753] [Chemical Formula 87]

[0754]

[0755] [Chemical Formula 88]

[0756]

[0757] [Chemical Formula 89]

[0758]

[0759] [Chemical Formula 90]

[0760]

[0761] [Chemical Formula 91]

[0762]

[0763] [Chemical Formula 92]

[0764]

[0765] [Chemical Formula 93]

[0766]

[0767] [Chemical Formula 94]

[0768]

[0769] [Chemical Formula 95]

[0770]

[0771] [Chemical Formula 96]

[0772]

[0773] [Chemical Formula 97]

[0774]

[0775] [Chemical Formula 98]

[0776]

[0777] [Chemical Formula 99]

[0778]

[0779] [Chemical Formula 100]

[0780]

[0781] [Chemical Formula 101]

[0782]

[0783] [Chemical Formula 102]

[0784]

[0785] [Chemical Formula 103]

[0786]

[0787] [Chemical Formula 104]

[0788]

[0789] [Chemical Formula 105]

[0790]

[0791] [Chemical Formula 106]

[0792]

[0793] [Chemical Formula 107]

[0794]

[0795] [Chemical Formula 108]

[0796]

[0797] [Chemical Formula 109]

[0798]

[0799] [Chemical Formula 110]

[0800]

[0801] Materials for Organic EL Devices

[0802] A material for an organic EL device of one aspect 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 device is 1 mass% or more (including 100%), and although there are no particular limitations, preferably 10 mass% or more (including 100%), more preferably 50 mass% or more (including 100%), even more preferably 80 mass% or more (including 100%), and particularly preferably 90 mass% or more (including 100%). The material for an organic EL device of one aspect of the present invention is useful for manufacturing an organic EL device.

[0803] In one aspect of the present invention, it is preferable that the inventive compound is a hole transport layer material.

[0804] A material for an organic electroluminescent device according to one aspect of the present invention is a hole transport layer material.

[0805] The content of the inventive compound in the material for organic electroluminescent devices is not particularly limited, but preferably 1 mass% or more (including 100%), more preferably 10 mass% or more (including 100%), even more preferably 50 mass% or more (including 100%), even more preferably 80 mass% or more (including 100%), and particularly preferably 90 mass% or more (including 100%).

[0806] Organic EL device

[0807] An organic EL device of one aspect of the present invention comprises an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer is composed of a single or multiple layers including a light-emitting layer, and at least one layer selected from the group consisting of a single layer and multiple layers constituting the organic layer comprises the compound of the invention.

[0808] Examples of organic layers containing the inventive compound include a hole transport band (hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer, etc.) provided between an anode and a light-emitting layer, a light-emitting layer, a space layer, and an electron transport band (electron injection layer, electron transport layer, hole blocking layer, etc.) provided between a cathode and a light-emitting layer, but are not limited thereto. The inventive compound is not particularly limited, but is preferably used as a material for the hole transport band or the light-emitting layer of a fluorescent or phosphorescent EL device, more preferably as a material for the hole transport band, even more preferably as a material for the hole injection layer, the hole transport layer, the electron blocking layer, the exciton blocking layer, and particularly preferably as a material for the hole injection layer and the hole transport layer.

[0809] An organic EL device of one aspect of the present invention may be a monochromatic light-emitting device of the fluorescent or phosphorescent emission type, a white light-emitting device of the fluorescent / phosphorescent hybrid type, a simple type having a single light-emitting unit, or a tandem type having a plurality of light-emitting units. Among these, it is preferable that it be a fluorescent light-emitting type device. Here, "light-emitting unit" refers to a minimum unit that includes an organic layer, is composed of a single or multiple layers formed by the organic layer, and at least one layer selected from the group consisting of said single layer and multiple layers is a light-emitting layer, and emits light by the recombination of injected holes and electrons.

[0810] For example, the following device configurations can be cited as representative device configurations of simple organic EL devices.

[0811] (1) Anode / Light-emitting unit / Cathode

[0812] In addition, the above-mentioned light-emitting unit may be a multilayer type having multiple phosphorescent light-emitting layers or fluorescent light-emitting layers, and in that case, a space layer may be provided between each light-emitting layer for the purpose of preventing excitons generated in the phosphorescent light-emitting layer from diffusing into the fluorescent light-emitting layer. A representative layer configuration of a simple light-emitting unit is shown below. The layers in parentheses are optional.

[0813] (a) (hole injection layer / )hole transport layer / fluorescent emitting layer / electron transport layer( / electron injection layer)

[0814] (b) (hole injection layer / )hole transport layer / first fluorescent emitting layer / second fluorescent emitting layer / electron transport layer( / electron injection layer)

[0815] (c) (hole injection layer / )hole transport layer / phosphorescent emitting layer / space layer / fluorescent emitting layer / electron transport layer( / electron injection layer)

[0816] (d) (hole injection layer / )hole transport layer / first phosphorescent emitting layer / second phosphorescent emitting layer / space layer / fluorescent emitting layer / electron transport layer( / electron injection layer)

[0817] (e) (hole injection layer / )hole transport layer / phosphorescent emitting layer / space layer / first fluorescent emitting layer / second fluorescent emitting layer / electron transport layer( / electron injection layer)

[0818] (f) (hole injection layer / )hole transport layer / electron blocking layer / fluorescent emitting layer / electron transport layer( / electron injection layer)

[0819] (g) (hole injection layer / )hole transport layer / exciton blocking layer / fluorescent emitting layer / electron transport layer( / electron injection layer)

[0820] (h) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent emitting layer / electron transport layer( / electron injection layer)

[0821] (h1) (hole injection layer / ) first hole transport layer / second hole transport layer / third hole transport layer / fluorescent emitting layer / electron transport layer( / electron injection layer)

[0822] (i) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer)

[0823] (i1) (hole injection layer / ) first hole transport layer / second hole transport layer / third hole transport layer / fluorescent emitting layer / first electron transport layer / second electron transport layer( / electron injection layer)

[0824] (j) (hole injection layer / )hole transport layer / fluorescent emitting layer / hole blocking layer / electron transport layer( / electron injection layer)

[0825] (k) (hole injection layer / )hole transport layer / fluorescent emission layer / exciton blocking layer / electron transport layer( / electron injection layer)

[0826] Each of the above phosphorescent or fluorescent emitting layers may exhibit a different emission color. Specifically, the emitting unit (d) may include a layer configuration such as a (hole injection layer) hole transport layer, a first phosphorescent emitting layer (red emission) and a second phosphorescent emitting layer (green emission) and a space layer, a fluorescent emitting layer (blue emission) and an electron transport layer.

[0827] Meanwhile, an electron blocking layer may be appropriately provided between each light-emitting layer and a hole transport layer or a space layer. Additionally, a hole blocking layer may be appropriately provided between each light-emitting layer and an electron transport layer. By providing an electron blocking layer or a hole blocking layer, electrons or holes can be trapped within the light-emitting layer, thereby increasing the probability of charge recombination in the light-emitting layer and improving luminous efficiency.

[0828] Representative device configurations of tandem organic EL devices include the following device configurations.

[0829] (2) Anode / First light-emitting unit / Intermediate layer / Second light-emitting unit / Cathode

[0830] Here, the first light-emitting unit and the second light-emitting unit are not particularly limited and, for example, can each be independently selected from the light-emitting units described above.

[0831] The above intermediate layer may utilize a known material composition that is generally referred to as an intermediate electrode, intermediate conductive layer, charge generating layer, electron drawing layer, connection layer, or intermediate insulating layer, and supplies electrons to the first light-emitting unit and holes to the second light-emitting unit.

[0832] In addition, when the hole transport layer is a multilayer structure including two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer in the multilayer structure, for example, the second hole transport layer of the two-layer structure or the third hole transport layer of the three-layer structure, may function as an electron blocking layer. That is, when the hole transport layer is a multilayer structure including two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer in the multilayer structure may be used as an electron blocking layer.

[0833] FIG. 1 is a schematic diagram showing an example of the configuration of an organic EL device according to one aspect of the present invention. The organic EL device (1) shown in FIG. 1 has a substrate (2), an anode (3), a cathode (4), and a light-emitting unit (10) disposed between the anode (3) and the cathode (4). The light-emitting unit (10) has a light-emitting layer (5). Between the light-emitting layer (5) and the anode (3), there is a hole transport band (6) (hole injection layer, hole transport layer, etc.), and between the light-emitting layer (5) and the cathode (4), there is an electron transport band (7) (electron injection layer, electron transport layer, etc.). Additionally, an electron blocking layer (not shown) may be provided on the anode (3) side of the light-emitting layer (5), and a hole blocking layer (not shown) may be provided on the cathode (4) side of the light-emitting layer (5). By doing so, electrons or holes can be trapped in the light-emitting layer (5), thereby increasing the generation efficiency of excitons in the light-emitting layer (5).

[0834] FIG. 2 is a schematic diagram showing another configuration of an organic EL device according to one aspect of the present invention. The organic EL device (11) shown in FIG. 2 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). A hole transport band disposed between the anode (3) and the light-emitting layer (5) is formed by a hole injection layer (6a), a first hole transport layer (6b), and a second hole transport layer (6c). Additionally, an electron transport band disposed between the light-emitting layer (5) and the cathode (4) is formed by a first electron transport layer (7a) and a second electron transport layer (7b).

[0835] FIG. 3 is a schematic diagram showing another configuration of an organic EL device according to one aspect of the present invention. The organic EL device (12) has a substrate (2), an anode (3), a cathode (4), and a light-emitting unit (30) disposed between the anode (3) and the cathode (4). The light-emitting unit (30) has a light-emitting layer (5). A hole transport band disposed between the anode (3) and the light-emitting layer (5) is formed by a hole injection layer (6a), a first hole transport layer (6b), a second hole transport layer (6c), and a third hole transport layer (6d). Additionally, an electron transport band disposed between the light-emitting layer (5) and the cathode (4) is formed by a first electron transport layer (7a) and a second electron transport layer (7b).

[0836] In FIGS. 1 to 3, the light-emitting layer (5) comprises at least one light-emitting layer. The light-emitting layer (5) may be a single layer or may comprise a plurality of layers (e.g., a plurality of light-emitting layers, a plurality of light-emitting layers and a space layer). Among these, it is preferable that it be stacked in a plurality of layers as one embodiment.

[0837] Meanwhile, in the present invention, a host combined with a fluorescent dopant material (fluorescent emitting material) is referred to as a fluorescent host, and a host combined with a phosphorescent dopant material is referred to as a phosphorescent host. Fluorescent hosts and phosphorescent hosts are not distinguished solely by their molecular structures. That is, a phosphorescent host refers to a material that forms a phosphorescent emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material that forms a fluorescent emitting layer. The same applies to fluorescent hosts.

[0838] substrate

[0839] The substrate is used as a support for the organic EL device. There are no particular restrictions on the substrate, and for example, plates such as glass, quartz, and plastic can be used. Additionally, a flexible substrate may be used. There are no particular restrictions on the flexible substrate, and examples include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. In addition, an inorganic deposition film may be used.

[0840] anode

[0841] As for the anode formed on the substrate, there are no particular limitations, but preferably, a metal, alloy, electrically conductive compound, or mixture thereof having a large work function (specifically 4.0 eV or more) is used. Specifically, examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. In addition, examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), and nitrides of the above metals (e.g., titanium nitride).

[0842] These materials are typically formed by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering by using a target containing 1 to 10 wt% zinc oxide relative to indium oxide, and indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering by using a target containing 0.5 to 5 wt% tungsten oxide and 0.1 to 1 wt% zinc oxide relative to indium oxide. In addition, they may be produced by vacuum deposition, coating, inkjet, spin coating, etc.

[0843] Precision transport band

[0844] As described above, the organic layer may include a hole transport band between the anode and the light-emitting layer. The hole transport band is composed of a hole injection layer, a hole transport layer, an electron blocking layer, etc. It is preferable that the hole transport band includes the compound of the invention. It is preferable that the compound of the invention be included in at least one layer selected from the group consisting of these layers (hole injection layer, hole transport layer, electron blocking layer, etc.) constituting the hole transport band, and it is particularly more preferable that the compound of the invention be included in the hole transport layer.

[0845] Since the hole injection layer formed in contact with the anode is formed using a material that facilitates hole injection regardless of the work function of the anode, materials generally used as electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, and elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0846] Materials with a small work function, such as elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals like lithium (Li) and cesium (Cs); alkaline earth metals like magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi); rare earth metals like europium (Eu) and ytterbium (Yb), and alloys containing them, may also be used. Meanwhile, when forming an anode using alkali metals, alkaline earth metals, and alloys containing them, vacuum deposition or sputtering methods may be used. Also, when using silver paste, etc., coating methods or inkjet methods may be used.

[0847] Hole injection layer

[0848] The hole injection layer is a layer containing a material with high hole injection properties (hole injection material), and is formed between the anode and the light-emitting layer, or, if present, between the hole transport layer and the anode.

[0849] There are no particular limitations on hole-injecting materials other than the compound of invention, and examples include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc.

[0850] Low molecular weight organic compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviated: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviated: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviated: DPA3B), and 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated: PCzPCA1), Aromatic amine compounds such as 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated: PCzPCA2) and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviated: PCzPCN1) can also be used as hole injection layer materials.

[0851] Polymeric compounds (oligomers, dendrimers, polymers, etc.) may also be used. Examples include poly(N-vinylcarbazole) (abbreviated: PVK), poly(4-vinyltriphenylamine) (abbreviated: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated: Poly-TPD). Additionally, polymeric compounds with added acids, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), may also be used.

[0852] In addition, it is also desirable to use an acceptor material such as a hexa-azatriphenylene (HAT) compound represented by the following formula (K).

[0853] [Chemical Formula 111]

[0854]

[0855] (Among the above formulas, R 221 ~R 226 Each independently consists of a cyano group, -CONH2, carboxyl group, or -COOR 227 (R 227 ... represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms. Also, R 221 and R 222 , R 223 and R 224 , and R 225 and R 226 Two adjacent groups selected from may combine to form a group represented as -CO-O-CO-.)

[0856] R 227 There are no particular limitations on the group, and examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, cyclopentyl group, cyclohexyl group, etc.

[0857] In one aspect of an organic EL device according to the present invention, the hole transport band comprises a hole injection layer between the anode and a first hole transport layer on the anode side, and the hole injection layer comprises a first organic material and a second organic material, wherein the first organic material and the second organic material are different from each other. The content of the second organic material in the hole injection layer is not particularly limited, but is preferably 0.01 mass% or more and less than 50 mass%, more preferably 0.05 to 30 mass%, even more preferably 0.10 mass to 10 mass%, even more preferably 0.50 to 5 mass%, and particularly preferably 1.0 mass% to 3 mass%.

[0858] As a first organic material, the inventive compound or the aforementioned hole-injecting material other than the inventive compound may be cited.

[0859] In one aspect of the organic EL device of the present embodiment, the second organic material is not particularly limited and, for example, is a compound comprising at least one of a first ring structure represented by the following general formula (P11) and a second ring structure represented by the following general formula (P12).

[0860] [Chemical Formula 112]

[0861]

[0862] (The first ring structure represented by the above general formula (P11) condenses with at least one ring structure among a substituted or unsubstituted cyclic aromatic hydrocarbon ring having 6 to 50 carbon atoms and a substituted or unsubstituted cyclic heterocyclic ring having 5 to 50 atoms in the molecule of the second organic material, and

[0863] =Z 10 The structure represented by is expressed by the following general formulas (11a), (11b), (11c), (11d), (11e), (11f), (11g), (11h), (11i), (11j), (11k) or (11m).

[0864] [Chemical Formula 113]

[0865]

[0866] [Chemical Formula 114]

[0867]

[0868] (among the above general formulas (11a), (11b), (11c), (11d), (11e), (11f), (11g), (11h), (11i), (11j), (11k) or (11m), R 11 ~R 14 and R 1101 ~R 1110 Each independently,

[0869] hydrogen atom,

[0870] Halogen atoms,

[0871] hydroxyl group,

[0872] Cyanog,

[0873] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0874] Substituted or unsubstituted alkyl halides having 1 to 50 carbon atoms,

[0875] Substituted or unsubstituted cyclic cycloalkyl groups having 3 to 50 carbon atoms,

[0876] -Si(R 901 )(R 902 )(R 903 The one indicated by ),

[0877] -O-(R 904 The one indicated by ),

[0878] -S-(R 905 The one indicated by ),

[0879] -N(R 906 )(R 907 The one indicated by ),

[0880] A substituted or unsubstituted cyclic aryl group having 6 to 50 carbon atoms, or

[0881] It is a heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms.

[0882] (In the above general formula (P12), Z1 to Z5 are each independently,

[0883] nitrogen atoms,

[0884] R 15 A carbon atom that bonds with, or

[0885] It is a carbon atom that bonds with other atoms in the molecule of the second organic material, and

[0886] Among Z1 to Z5, at least one is a carbon atom that bonds with another atom in the molecule of the second organic material, and

[0887] R 15 Is,

[0888] hydrogen atom,

[0889] Halogen atoms,

[0890] Cyanog,

[0891] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0892] Substituted or unsubstituted alkyl halides having 1 to 50 carbon atoms,

[0893] Substituted or unsubstituted cyclic cycloalkyl groups having 3 to 50 carbon atoms,

[0894] Substituted or unsubstituted cyclic aryl groups having 6 to 50 carbon atoms,

[0895] Substituted or unsubstituted heterocyclic groups having 5 to 50 cyclic atoms,

[0896] -Si(R 901 )(R 902 )(R 903 The one indicated by ),

[0897] -O-(R 904 The one indicated by ),

[0898] -S-(R 905 The one indicated by ),

[0899] -N(R 906 )(R 907The one indicated by ),

[0900] Substituted or unsubstituted alkeneyl groups having 2 to 50 carbon atoms,

[0901] Substituted or unsubstituted aralkyl groups having 7 to 50 carbon atoms,

[0902] Carboxy

[0903] Substituted or unsubstituted ester group,

[0904] Substituted or non-substituted Kabamo diary,

[0905] Nitrogy, and

[0906] Selected from a group consisting of substituted or non-substituted Siloksan Ilgi, and

[0907] R 15 If there are multiple instances of , multiple R 15 They are identical or different from each other.)

[0908] (Among the above second organic materials, R 901 ~R 907 Each independently,

[0909] hydrogen atom,

[0910] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0911] Substituted or unsubstituted cyclic cycloalkyl groups having 3 to 50 carbon atoms,

[0912] A substituted or unsubstituted cyclic aryl group having 6 to 50 carbon atoms, or

[0913] It is a heterocyclic group having 5 to 50 substituted or unsubstituted cyclic atoms, and

[0914] R 901 In this case, multiple Rs 901 are identical to each other, or different,

[0915] R 902 If there are multiple cases, multiple R 902 are identical to each other, or different,

[0916] R 903 In this case, multiple Rs903 are identical to each other, or different,

[0917] R 904 If there are multiple cases, multiple R 904 are identical to each other, or different,

[0918] R 905 If there are multiple cases, multiple R 905 are identical to each other, or different,

[0919] R 906 In this case, multiple Rs 906 are identical to each other, or different,

[0920] R 907 In this case, multiple Rs 907 ...is either identical to or different from each other.)

[0921] In this specification, the ester group is at least one group selected from the group consisting of alkyl ester groups and aryl ester groups.

[0922] As for the alkyl ester group in this specification, there are no particular limitations, and for example, -C(=O)OR E It is indicated as. R E There are no particular limitations, and examples include substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms (preferably 1 to 10 carbon atoms).

[0923] As for the aryl ester group in this specification, there are no particular limitations, and for example, -C(=O)OR Ar It is indicated as. R Ar There are no particular restrictions on the type, and examples include substituted or unsubstituted cyclic aryl groups having 6 to 30 carbon atoms.

[0924] The siloxane group in this specification is a silicon compound group having an ether bond interposed therein. There are no particular limitations on the siloxane group, and examples include trimethylsiloxane group.

[0925] In this specification, the carbamoyl group is denoted as -CONH2.

[0926] As for the substituted carbamoyl group in this specification, there are no particular limitations, and for example, -CONH-Ar C , -CONH-R C It is indicated as, etc. Ar C There are no particular limitations on the group, and examples include substituted or unsubstituted aryl groups having 6 to 50 carbon atoms (preferably 6 to 10 carbon atoms) and heterocyclic groups having 5 to 50 (preferably 5 to 14) carbon atoms. In addition, Ar C It is a contribution formed by the combination of a substituted or unsubstituted cyclic aryl group having 6 to 50 carbon atoms and a substituted or unsubstituted cyclic heterocyclic group having 5 to 50 atoms.

[0927] R C There are no particular limitations on the group, and examples include substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms (preferably 1 to 6 carbon atoms).

[0928] In the above second organic material, it is preferable that all groups described as "substituted or non-substituted" are "non-substituted" groups.

[0929] There are no particular limitations on the second organic material, and examples include the following compounds. However, the present invention is not limited to specific examples of these second organic materials.

[0930] [Chemical Formula 115]

[0931]

[0932] [Chemical Formula 116]

[0933]

[0934] Precision transport layer

[0935] The hole transport layer is a layer comprising a material with high hole transportability (hole transportable material) and is formed between the anode and the emissive layer, or, if present, between the hole injection layer and the emissive layer. The compound of the invention may be used in the hole transport layer alone or in combination with the following compounds.

[0936] The hole transport layer may be a single-layer structure or a multi-layer structure including two or more layers. For example, the hole transport layer may be a two-layer structure including a first hole transport layer (anode side) and a second hole transport layer (cathode side). That is, the hole transport band may include a first hole transport layer on the anode side and a second hole transport layer on the cathode side. In addition, the hole transport layer may be a three-layer structure including a first hole transport layer, a second hole transport layer, and a third hole transport layer in order from the anode side. That is, a third hole transport layer may be disposed between the second hole transport layer and the light-emitting layer.

[0937] In one aspect of the present invention, it is preferable that the hole transport layer of the single-layer structure be adjacent to the light-emitting layer, and it is also preferable that the hole transport layer closest to the cathode among the multilayer structures, for example, the second hole transport layer of the two-layer structure or the third hole transport layer of the three-layer structure, be adjacent to the light-emitting layer. In particular, it is preferable that the light-emitting layer and the second hole transport layer are in direct contact. In another aspect of the present invention, an electron blocking layer, etc., described below may be interposed between the hole transport layer of the single-layer structure and the light-emitting layer, or between the hole transport layer closest to the light-emitting layer among the multilayer structures and the light-emitting layer. Furthermore, as described above, when the hole transport layer is a multilayer structure comprising two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer among the multilayer structures may be used as an electron blocking layer.

[0938] In one aspect of an organic electroluminescent device according to the present invention, at least one selected from the group consisting of the first hole transport layer and the second hole transport layer comprises the inventive compound. Specifically, in the hole transport layer having a two-layer structure, the inventive compound may be included in either the first hole transport layer or the second hole transport layer, or in both. In addition, in another aspect, at least one selected from the group consisting of the first to third hole transport layers comprises the inventive compound. Specifically, in the hole transport layer having a three-layer structure, the inventive compound may be included in only at least one of the first to third hole transport layers, in only two of them, or in all of them.

[0939] In one aspect of the present invention, it is preferable that the inventive compound be included in the second hole transport layer, and specifically, it is preferable that the inventive compound be included only in the second hole transport layer, or that the inventive compound be included in both the first hole transport layer and the second hole transport layer.

[0940] There are no particular limitations on hole transport layer materials other than the inventive compound, and examples include aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc.

[0941] As for aromatic amine compounds, there are no particular limitations, and examples include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated: TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated: BAFLP), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (abbreviated: DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviated: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated: MTDATA), and Examples include 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviated: BSPB), etc. The above compound is, 10 -6 cm 2 It has a positive mobility of / Vs or higher.

[0942] There are no particular limitations on carbazole derivatives, and examples include 4,4'-di(9-carbazolyl)biphenyl (abbreviated: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviated: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthyl)phenyl]-9H-carbazole (abbreviated: PCzPA).

[0943] Examples of anthracene derivatives include 2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviated: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviated: DNA), and 9,10-diphenylanthracene (abbreviated: DPAnth), among others.

[0944] Polymeric compounds such as poly(N-vinylcarbazole) (abbreviated: PVK) and poly(4-vinyltriphenylamine) (abbreviated: PVTPA) may also be used.

[0945] However, if the hole transport capacity is higher than the electron transport capacity, compounds other than the above may be used.

[0946] In one aspect of the organic EL device according to the present invention, the first hole transport layer comprises a compound represented by the following formula (21) or formula (22).

[0947] [Chemical Formula 117]

[0948]

[0949] [Among the above formulas (21) and (22),

[0950] L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 Each is independently a single bond, a substituted or unsubstituted cyclic arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted cyclic divalent heterocyclic group having 5 to 50 atoms, and

[0951] k is 1, 2, 3, or 4, and

[0952] When k is 1, L E2 is a substituted or unsubstituted cyclic arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted cyclic divalent heterocyclic group having 5 to 50 atoms, and

[0953] If k is 2, 3, or 4, multiple L E2 are identical to each other, or different,

[0954] If k is 2, 3, or 4, multiple L E2 ...combined with each other to form substituted or unsubstituted single rings, combined with each other to form substituted or unsubstituted condensed rings, or not combined with each other,

[0955] L that does not form the above-mentioned single ring and also does not form the above-mentioned condensed ring E2 is a substituted or unsubstituted cyclic arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted cyclic divalent heterocyclic group having 5 to 50 atoms, and

[0956] A1 , B 1 , C 1 , A 2 , B 2 , C 2 , and D 2 is, respectively, a substituted or unsubstituted cyclic aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cyclic heterocyclic group having 5 to 50 atoms, or -Si(R' 901 )(R' 902 )(R' 903 ) and,

[0957] R' 901 , R' 902 and R' 903 Each is independently a substituted or unsubstituted cyclic aryl group having 6 to 50 carbon atoms, and

[0958] R' 901 If this plural exists, the plural R' 901 are identical to each other, or different,

[0959] R' 902 If there are multiple instances of R' 902 are identical to each other, or different,

[0960] R' 903 If this plural exists, the plural R' 903 [They are identical or different from each other.]

[0961] Meanwhile, the first hole transport layer may contain one type of compound represented by formulas (21) and (22), or may contain multiple types of compounds represented by formulas (21) and (22).

[0962] In equations (21) and (22), A 1 , B 1 , C 1 , A 2 , B 2 , C 2 , and D 2As for the group, there are no particular limitations, but preferably, each independently is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.

[0963] Also, more preferably, in formula (21), A 1 , B 1 and C 1 At least one selected from the group consisting of, and in Equation (22), A 2 , B 2 , C 2 and D 2 At least one selected from the group consisting of is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.

[0964] A 1 , B 1 , C 1 , A 2 , B 2 , C 2 , and D 2 The fluorene group that can be taken may have a substituent at the 9th position, for example, 9,9-dimethylfluorene group or 9,9-diphenylfluorene group. In addition, the substituents at the 9th position may form a ring together, for example, a fluorene skeleton or a xanthen skeleton may be formed together.

[0965] L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2As for the group, there are no particular restrictions, but preferably, each independently, is a single bond, substituted or unsubstituted cyclic arylene group having 6 to 12 carbon atoms.

[0966] Specific examples of compounds represented by formulas (21) and (22) include, for instance, the following compounds.

[0967] [Chemical Formula 118]

[0968]

[0969] dopant material of the light-emitting layer

[0970] The emissive layer is a layer containing a material with high luminescence (dopant material), and various materials can be used. For example, fluorescent emitting materials and phosphorescent emitting materials can be used as dopant materials. A fluorescent emitting material is a compound that emits light from a singlet excited state, and a phosphorescent emitting material is a compound that emits light from a triplet excited state.

[0971] In one aspect of the organic EL device according to the present invention, it is preferable that the light-emitting layer is a single layer.

[0972] In addition, in one aspect of the organic EL device according to the present invention, it is preferable that the light-emitting layer be stacked in a plurality of layers.

[0973] There are no particular limitations on blue fluorescent light-emitting materials that can be used in the light-emitting layer, and examples include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, azaborin derivatives, arylborain derivatives, etc. Specifically, examples include N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviated: YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviated: YGAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated: PCBAPA), etc.

[0974] There are no particular limitations on green fluorescent light-emitting materials that can be used in the light-emitting layer, and examples include aromatic amine derivatives. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviated: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated: 2DPABPhA), Examples include N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviated: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviated: DPhAPhA), etc.

[0975] There are no particular limitations on red fluorescent light-emitting materials that can be used in the light-emitting layer, and examples include tetracene derivatives and diamine derivatives. Specifically, examples include N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviated: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviated: p-mPhAFD).

[0976] In one aspect of the present invention, it is preferable that the light-emitting layer comprises a fluorescent light-emitting material (fluorescent dopant material).

[0977] There are no particular limitations on the blue phosphorescent materials that can be used in the light-emitting layer, and examples include metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Specifically, examples include bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) tetrakis(1-pyrazolyl)borate (abbreviated: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviated: FIrpic), bis[2-(3',5'-bistrifluoromethylphenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviated: Ir(CF3ppy)2(pic)), and bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) acetylacetonate (abbreviated: FIracac).

[0978] There are no particular limitations on green phosphorescent materials that can be used in the light-emitting layer, and examples include iridium complexes. Examples include tris(2-phenylpyridinato-N,C2')iridium(III) (abbreviated: Ir(ppy)3), bis(2-phenylpyridinato-N,C2')iridium(III) acetylacetonate (abbreviated: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazoleate)iridium(III) acetylacetonate (abbreviated: Ir(pbi)2(acac)), and bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviated: Ir(bzq)2(acac)).

[0979] There are no particular restrictions on the red phosphorescent material that can be used in the emissive layer, and for example, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used. Specifically, examples include organometallic complexes such as bis[2-(2'-benzo[4,5-α]thienyl)pyridinato-N,C3']iridium(III) acetylacetonate (abbreviated: Ir(btp)2(acac)), bis(1-phenylisoquinolinato-N,C2')iridium(III) acetylacetonate (abbreviated: Ir(piq)2(acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviated: Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated: PtOEP).

[0980] In addition, rare earth metal complexes such as tris(acetylacetonate)(monophenantroline)terbium(III) (abbreviated: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedioto)(monophenantroline)europium(III) (abbreviated: Eu(DBM)3(Phen)), and tris[1-(2-tenoyl)-3,3,3-trifluoroacetonato](monophenantroline)europium(III) (abbreviated: Eu(TTA)3(Phen)) can be used as phosphorescent light-emitting materials because the emission is from rare earth metal ions (electron transition between different multiplicity).

[0981] Host material of the light-emitting layer

[0982] The light-emitting layer may be configured such that the aforementioned dopant material is dispersed in another material (host material). It is preferable to use a material that has a lower empty orbit level (LUMO level) and a lower highest occupied orbit level (HOMO level) than the dopant material.

[0983] As for the host material, there are no particular restrictions, for example,

[0984] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes;

[0985] (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives;

[0986] (3) Condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives;

[0987] (4) Aromatic amine compounds such as triarylamine derivatives, condensed polycyclic aromatic amine derivatives, etc.

[0988] In the present invention, as one aspect, the light-emitting layer comprises an anthracene derivative, and it is preferable that a hydrogen atom present on at least one benzene ring of the anthracene derivative is deuteriumized.

[0989] Specific examples of anthracene derivatives will be described later.

[0990] Specific examples of anthracene derivatives include, for example, metal complexes such as tris(8-quinolinoleto)aluminum(III) (abbreviated: Alq), tris(4-methyl-8-quinolinoleto)aluminum(III) (abbreviated: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviated: BeBq2), bis(2-methyl-8-quinolinoleto)(4-phenylphenolato)aluminum(III) (abbreviated: BAlq), bis(8-quinolinoleto)zinc(II) (abbreviated: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviated: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviated: ZnBTZ);

[0991] Heterocyclic compounds such as 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-biphenylyl)-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), vasophenanthroline (abbreviation: BPhen), and vasocuproin (abbreviation: BCP);

[0992] 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9'-bianthrile (abbreviation: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviation: DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation: Condensed aromatic compounds such as DPNS2), 3,3',3''-(benzene-1,3,5-triyl)tripyrene (abbreviated: TPB3), 9,10-diphenylanthracene (abbreviated: DPAnth), 6,12-dimethoxy-5,11-diphenylchrysene; and

[0993] N,N-Diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), N,9-Diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), N,9-Diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviation: PCAPBA), N-(9,10-Diphenyl-2-anthryl)-N,9-Diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), Examples include aromatic amine compounds such as 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated: TPD), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (abbreviated: DFLDPBi), and 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviated: BSPB). Multiple types of host materials may be used.

[0994] In particular, for blue fluorescent devices, it is preferable to use the following anthracene derivative as a host material.

[0995] [Chemical Formula 119]

[0996]

[0997] [Chemical Formula 120]

[0998]

[0999] [Chemical Formula 121]

[1000]

[1001] [Chemical Formula 122]

[1002]

[1003] In one aspect of an organic EL device according to the present invention, it is preferable that the light-emitting layer is stacked in a plurality of layers. When the light-emitting layer stacked in a plurality of layers is composed of, for example, a first light-emitting layer and a second light-emitting layer, at least one of the components constituting the first light-emitting layer is different from the component constituting the second light-emitting layer. For example, there may be an example in which the dopant material included in the first light-emitting layer is different from the dopant material included in the second light-emitting layer, or an example in which the host material included in the first light-emitting layer is different from the host material included in the second light-emitting layer.

[1004] In the organic EL device according to the present embodiment, the light-emitting layer may include a layer containing a light-emitting compound that exhibits fluorescent light emission with a main peak wavelength of 500 nm or less.

[1005] The method for measuring the main peak wavelength of a compound is as follows. A 5 μmol / L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the emission spectrum of the sample is measured at room temperature (300K) (longitudinal axis: emission intensity, horizontal axis: wavelength). The emission spectrum can be measured using a spectrofluorescence photometer manufactured by Hitachi High-Tech Science Inc. (device name: F-7000). Meanwhile, the emission spectrum measuring device is not limited to the device used herein.

[1006] In the emission spectrum, the peak wavelength of the emission spectrum where the emission intensity is maximum is designated as the main peak wavelength. Meanwhile, in this specification, the main peak wavelength may be referred to as the fluorescence emission main peak wavelength (FL-peak).

[1007] A luminescent compound exhibiting fluorescent emission with a main peak wavelength of 500 nm or less may be the dopant material or the host material.

[1008] In the case where the emitting layer is a single layer, only one of the dopant material and the host material may be a emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less, or both materials may be emitting compounds that exhibit fluorescent emission with a main peak wavelength of 500 nm or less.

[1009] In addition, when the emitting layer includes a first emitting layer and a second emitting layer, only one of the first emitting layer and the second emitting layer may include a emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less, and both emitting layers may include a emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less. Furthermore, when the first emitting layer includes a emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less, only one of the dopant material and the host material included in the first emitting layer may be a emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less, and both materials may be emitting compounds that exhibit fluorescent emission with a main peak wavelength of 500 nm or less. In addition, when the second emitting layer includes a emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less, only one of the dopant material and the host material included in the second emitting layer may be a emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less, and both materials may be emitting compounds that exhibit fluorescent emission with a main peak wavelength of 500 nm or less.

[1010] Electron transport layer

[1011] The electron transport layer is a layer containing a material with high electron transportability (electron transportable material), and is formed between the light-emitting layer and the cathode, or, if present, between the electron injection layer and the light-emitting layer.

[1012] The electron transport layer may be a single-layer structure or a multilayer structure including two or more layers. For example, the electron transport layer may be a two-layer structure including a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one aspect of the present invention, it is preferable that the electron transport layer of the single-layer structure be adjacent to the light-emitting layer, and it is also preferable that the electron transport layer closest to the anode among the multilayer structures, for example, the first electron transport layer of the two-layer structure, be adjacent to the light-emitting layer. In another aspect of the present invention, a hole blocking layer described later may be interposed 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 among the multilayer structures and the light-emitting layer.

[1013] As for the electron transport layer, there are no particular restrictions, for example,

[1014] (1) Metal complexes such as aluminum complexes, beryllium complexes, zinc complexes, etc.;

[1015] (2) Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives, etc.;

[1016] (3) Polymer compounds; etc.

[1017] As for the metal complex, there are no particular limitations, and examples include tris(8-quinolinoleto)aluminum(III) (abbreviated: Alq), tris(4-methyl-8-quinolinoleto)aluminum (abbreviated: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviated: BeBq2), bis(2-methyl-8-quinolinoleto)(4-phenylphenolato)aluminum(III) (abbreviated: BAlq), bis(8-quinolinoleto)zinc(II) (abbreviated: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviated: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviated: ZnBTZ). Examples include (8-quinolinolenate)lithium (abbreviation: Liq).

[1018] As heteroaromatic compounds, there are no particular limitations, and examples 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), vasophenanthroline (abbreviation: BPhen), and vasocuproin (abbreviation: BCP). Examples include 4,4'-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviated: BzOs).

[1019] As for polymer compounds, there are no particular limitations, and examples include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated: PF-BPy), etc.

[1020] The above material is 10 -6 cm 2 It is a material having an electron mobility of / Vs or higher. Meanwhile, if the material has higher electron transport than hole transport, other materials may be used in the electron transport layer. In addition, the electron transport layer may be a single layer, or a stack of two or more layers, each containing the above material. When the electron transport layer has a two-layer structure, the layer on the anode side is called the first electron transport layer, and the layer on the cathode side is called the second electron transport layer.

[1021] electron injection layer

[1022] The electron injection layer is a layer containing a material with high electron injection properties. In the electron injection layer, alkali metals such as lithium (Li) and cesium (Cs); alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr); rare earth metals such as europium (Eu) and ytterbium (Yb); and compounds containing these metals may be used. There are no particular limitations on such compounds, and examples include alkali metal oxides; alkali metal halides; alkali metal-containing organic complexes such as (8-quinolinoleto)lithium (abbreviated as Liq); alkaline earth metal oxides; alkaline earth metal halides; alkaline earth metal-containing organic complexes; rare earth metal oxides; rare earth metal halides; and rare earth metal-containing organic complexes. In addition, a mixture of these compounds may be used.

[1023] In addition, a material having electron transport properties may be used that contains an alkali metal, an alkaline earth metal, or a compound thereof, specifically a material that contains magnesium (Mg) in Alq. Meanwhile, in this case, electron injection from the cathode can be performed more efficiently.

[1024] Alternatively, a composite material formed by mixing an organic compound and an electron donor (donor) may be used in the electron injection layer. Since the organic compound receives electrons from the electron donor, such a composite material exhibits excellent electron injection and electron transport properties. In this case, there are no particular restrictions on the organic compound, but preferably, it is a material that exhibits excellent transport of received electrons. Specifically, for example, a material constituting the aforementioned electron transport layer (such as a metal complex or a heteroaromatic compound) may be used. As for the electron donor, any material that exhibits electron-donating properties with respect to the organic compound is sufficient. As for the electron donor, there are no particular restrictions, but preferably, it is an alkali metal, an alkaline earth metal, a rare earth metal, and more preferably, an alkali metal oxide or an alkaline earth metal oxide. There are no particular restrictions on the alkali metal, alkaline earth metal, or rare earth metal, and examples include lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. There are no particular limitations on alkali metal oxides or alkaline earth metal oxides, and examples include lithium oxide, calcium oxide, and barium oxide. In addition, Lewis bases such as magnesium oxide may be used. In addition, organic compounds such as tetrathiafulvalene (abbreviated: TTF) may also be used.

[1025] cathode

[1026] As for the cathode, there are no particular limitations, but preferably, a metal, alloy, electrically conductive compound, or mixture thereof with a small work function (specifically 3.8 eV or less) is used. Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) or 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) and ytterbium (Yb), and alloys containing them.

[1027] Meanwhile, when forming a cathode using alkali metals, alkaline earth metals, or alloys containing them, vacuum deposition or sputtering methods may be used. In addition, when using silver paste, coating methods or inkjet methods may be used.

[1028] Meanwhile, by providing an electron injection layer, a cathode can be formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium-tin oxide containing silicon oxide, regardless of the magnitude of the work function. These conductive materials can be deposited using sputtering, inkjet, spin coating, etc.

[1029] insulating layer

[1030] Since organic EL devices apply an electric field to an ultrathin film, pixel defects caused by leakage or short circuits are likely to occur. To prevent this, an insulating layer consisting of an insulating thin film may be inserted between a pair of electrodes.

[1031] There are no particular restrictions on the materials used for the insulating layer, and examples 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, vanadium oxide, etc. Meanwhile, mixtures or laminates thereof may also be used.

[1032] Space layer

[1033] The above space layer is a layer provided between a fluorescent emitting layer and a phosphorescent emitting layer for the purpose of preventing excitons generated in the phosphorescent emitting layer from diffusing into the fluorescent emitting layer, or for the purpose of adjusting the carrier balance, for example, when a fluorescent emitting layer and a phosphorescent emitting layer are stacked. Additionally, the space layer may be provided between a plurality of phosphorescent emitting layers.

[1034] Since the space layer is provided between the emitting layers, it is desirable for it to be a material that possesses both electron transport and hole transport properties. In addition, to prevent the diffusion of triplet energy within the adjacent phosphorescent emitting layer, it is desirable for the triplet energy to be 2.6 eV or higher. The same material used for the space layer as that used for the hole transport layer described above may be used.

[1035] low-lying area

[1036] Blocking layers, such as an electron blocking layer, a hole blocking layer, and an exciton blocking layer, may be provided adjacent to the emitting layer. An electron blocking layer is a layer that prevents electrons from leaking from the emitting layer to the hole transport layer, and a hole blocking layer is a layer that prevents holes from leaking from the emitting layer to the electron transport layer. The exciton blocking layer prevents excitons generated in the emitting layer from diffusing into surrounding layers, thereby having the function of trapping excitons within the emitting layer.

[1037] Each layer of the above organic EL device can be formed by conventionally known deposition methods, coating methods, etc. There are no particular limitations on the deposition method, and examples include known methods such as vacuum deposition and molecular beam deposition (MBE). There are no particular limitations on the coating method, and examples include known methods such as dipping, spin coating, casting, bar coating, and roll coating using a solution of a compound that forms a layer.

[1038] There are no particular limitations on the film thickness of each layer, but generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and conversely, if it is too thick, a high driving voltage is required and efficiency is poor, so it is preferably 5 nm to 10 μm, more preferably 10 nm to 0.2 μm.

[1039] In one aspect of the organic EL device of the present invention, the sum of the thickness of the first hole transport layer and the thickness of the second hole transport layer is 30 nm or more and 150 nm or less, preferably 40 nm or more and 130 nm or less.

[1040] In addition, in one aspect of the organic EL device of the present invention, the thickness of the second hole transport layer is 20 nm or more, preferably 25 nm or more, more preferably 35 nm or more, and also preferably 100 nm or less.

[1041] In addition, in one aspect of the organic EL device of the present invention, the hole transport layer adjacent to the light-emitting layer is 20 nm or more, preferably 25 nm or more, more preferably 30 nm or more, and also preferably 100 nm or less.

[1042] In addition, in one aspect of the organic EL device of the present invention, the film thickness D1 of the first hole transport layer and the film thickness D2 of the second hole transport layer are 0.3 <D2 / D1<4.0의 관계를 만족시키고, 바람직하게는 0.5<D2 / D1<3.5의 관계를 만족시키고, 보다 바람직하게는 0.75<D2 / D1<3.0의 관계를 만족시킨다.

[1043] As an embodiment of the organic EL device of the present invention, for example,

[1044] As an organic EL device having a hole transport layer with the above two-layer configuration,

[1045] · A first embodiment in which the second hole transport layer comprises a compound of the present invention, and the first hole transport layer does not comprise a compound of the present invention;

[1046] · A second embodiment in which both the first hole transport layer and the second hole transport layer comprise a compound of the present invention;

[1047] · A third embodiment in which the first hole transport layer comprises a compound of the present invention and the second hole transport layer does not comprise a compound of the present invention;

[1048] As an organic EL device having a hole transport layer with the above-mentioned three-layer configuration,

[1049] · A fourth embodiment in which the first hole transport layer comprises a compound of the present invention, and the second and third hole transport layers do not comprise a compound of the present invention;

[1050] · A fifth embodiment in which the second hole transport layer comprises a compound of the present invention, and the first and third hole transport layers do not comprise a compound of the present invention;

[1051] · A sixth embodiment in which the third hole transport layer comprises a compound of the present invention, and the first and second hole transport layers do not comprise a compound of the present invention;

[1052] · A seventh embodiment in which the first and second hole transport layers comprise the compound of the present invention, and the third hole transport layer does not comprise the compound of the present invention;

[1053] · An eighth embodiment in which the first and third hole transport layers comprise a compound of the present invention, and the second hole transport layer does not comprise a compound of the present invention;

[1054] · A ninth embodiment in which the second and third hole transport layers comprise the compound of the present invention, and the first hole transport layer does not comprise the compound of the present invention;

[1055] · A 10th embodiment in which all of the first to third hole transport layers comprise the compound of the present invention; etc. may be cited.

[1056] electronic devices

[1057] The above 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, light-emitting devices for vehicles, etc.

[1058] In one aspect of the present invention, it is preferable that the electronic device includes an organic electroluminescent element.

[1059] Examples

[1060] The present invention will be explained in more detail below using examples, but the present invention is not limited to the following examples.

[1061] Inventive compounds used in the manufacture of the organic EL devices of Examples 1 to 18

[1062] [Chemical Formula 123]

[1063]

[1064] [Chemical Formula 124]

[1065]

[1066] Comparative compounds used in the manufacture of the organic EL devices of Comparative Examples 1 to 6

[1067] [Chemical Formula 125]

[1068]

[1069] [Chemical Formula 126]

[1070]

[1071] Other compounds used in the manufacture of the organic EL devices of Examples 1 to 18 and Comparative Examples 1 to 6

[1072] [Chemical Formula 127]

[1073]

[1074] [Chemical Formula 128]

[1075]

[1076] Fabrication of Organic EL Devices

[1077] Example 1

[1078] A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The thickness of the ITO film was set to 130 nm.

[1079] After cleaning, the glass substrate with the ITO transparent electrode attached was mounted in the substrate holder of a vacuum deposition apparatus, and the transparent electrode was first placed over the side on which the transparent electrode was formed, so that compound HT-1 and compound HI-1 were co-deposited to form a hole injection layer with a film thickness of 10 nm. The mass ratio of compound HT-1 and compound HI-1 (HT-1:HI-1) was 97:3.

[1080] Next, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer with a film thickness of 85 nm.

[1081] Next, compound HT-2 (compound Inv-1) was deposited on this first hole transport layer to form a second hole transport layer with a film thickness of 5 nm.

[1082] Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited on this second hole transport layer to form an emissive layer with a film thickness of 5 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 98:2.

[1083] Next, compound aET-1 was deposited on this light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[1084] Next, compound bET-1 and Liq were co-deposited on this first electron transport layer to form a second electron transport layer with a film thickness of 31 nm. The mass ratio of compound bET-1 and Liq (bET-1:Liq) was 50:50.

[1085] Next, Liq was deposited on this second electron transport layer to form an electron injection electrode with a film thickness of 1 nm.

[1086] Then, metallic Al was deposited on this electron-injectable electrode to form a metallic cathode with a film thickness of 80 nm.

[1087] The layer composition of the organic EL device of Example 1 obtained in this way is shown below.

[1088] ITO(130) / HT-1:HI-1=97:3(10) / HT-1(85) / HT-2(5) / BH-1:BD-1=98:2(5) / aET-1(5) / bET-1:Liq=50:50(31) / Liq(1) / Al(80)

[1089] In the above layer composition, the number in parentheses is the film thickness (nm), and the ratio is the mass ratio.

[1090] Examples 2–10 and Comparative Examples 1–2

[1091] Organic EL devices of Examples 2 to 10 and Comparative Examples 1 to 2 were fabricated in the same manner as in Example 1, except that the compound listed in Table 1 was used instead of compound Inv-1.

[1092] Example 11

[1093] A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The thickness of the ITO film was set to 130 nm.

[1094] After cleaning, the glass substrate with the ITO transparent electrode attached was mounted in the substrate holder of a vacuum deposition apparatus, and the transparent electrode was first placed over the side on which the transparent electrode was formed, so that compound HT-3 and compound HI-1 were co-deposited to form a hole injection layer with a film thickness of 10 nm. The mass ratio of compound HT-3 and compound HI-1 (HT-3:HI-1) was 97:3.

[1095] Next, compound HT-3 was deposited on the hole injection layer to form a first hole transport layer with a film thickness of 85 nm.

[1096] Next, compound HT-2 (compound Inv-9) was deposited on this first hole transport layer to form a second hole transport layer with a film thickness of 5 nm.

[1097] Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited on this second hole transport layer to form an emissive layer with a film thickness of 5 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 98:2.

[1098] Next, compound aET-2 was deposited on this light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[1099] Next, compound bET-2 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer with a film thickness of 31 nm. The mass ratio of compound bET-2 and Liq (bET-2:Liq) was 50:50.

[1100] Next, Liq was deposited on this second electron transport layer to form an electron injection electrode with a film thickness of 1 nm.

[1101] Then, metallic Al was deposited on this electron-injectable electrode to form a metallic cathode with a film thickness of 80 nm.

[1102] The layer composition of the organic EL device of Example 11 obtained in this way is shown below.

[1103] ITO(130) / HT-3:HI-1=97:3(10) / HT-3(85) / HT-2(5) / BH-1:BD-1=98:2(5) / aET-2(5) / bET-2:Liq=50:50(31) / Liq(1) / Al(80)

[1104] In the above layer composition, the number in parentheses is the film thickness (nm), and the ratio is the mass ratio.

[1105] Examples 12–18 and Comparative Examples 3–6

[1106] Organic EL devices of Examples 12 to 18 and Comparative Examples 3 to 6 were fabricated in the same manner as in Example 11, except that the compound listed in Table 2 was used instead of compound Inv-9.

[1107] Evaluation of organic EL devices

[1108] Measurement of Device Lifetime (LT95)

[1109] The obtained organic EL device at a current density of 30 mA / cm² 2 The DC drive was operated, and the time (h) until the brightness dropped to 95% of the initial brightness was measured and this was set as the 95% lifespan (LT95).

[1110] The results are shown in Tables 1 and 2, according to the layer configuration of the organic EL device.

[1111]

[1112] As is evident from the results of Table 1, compounds satisfying the specifications of the present invention (compounds Inv-1 to Inv-8 and compounds Inv-17 to Inv-18) provide an organic EL device with significantly improved device lifespan compared to compounds not satisfying the specifications of the present invention (compounds Ref-1 and Ref-2).

[1113]

[1114] As is evident from the results of Table 2, compounds satisfying the specifications of the present invention (compounds Inv-9 to Inv-16) provide an organic EL device with significantly improved device lifespan compared to compounds not satisfying the specifications of the present invention (compounds Ref-3 to Ref-6).

[1115] Inventive compound synthesized in the synthesis example

[1116] [Chemical Formula 129]

[1117]

[1118] [Chemical Formula 130]

[1119]

[1120] Intermediate Synthesis Example 1: Synthesis of Intermediate A-1 and Intermediate A

[1121] [Chemical Formula 131]

[1122]

[1123] (Synthesis of intermediate A-1)

[1124] Under an argon atmosphere, 3.3 mL of trifluoromethanesulfonic acid was added to a mixture of 2-(3-bromophenyl)-1-phenylethanol (3.40 g, 12.4 mmol), acetophenone (2.2 mL, 18.5 mmol), and toluene (50 mL), and the mixture was stirred at 80°C for 3.5 hours. After cooling the reaction mixture to room temperature, water was added and the mixture was separated. The organic layer was dehydrated with sodium sulfate and then concentrated. The resulting residue was purified by silica gel column chromatography to obtain 2.78 g of intermediate A-1 as a pale yellow solid (yield 63%).

[1125] (Synthesis of Intermediate A)

[1126] Under an argon atmosphere, a mixture of raw material 1 (intermediate A-1, 2.70 g, 7.52 mmol), raw material 2 (4-chlorophenylboronic acid, 1.23 g, 7.89 mmol), tetrakis(triphenylphosphine)palladium (0.174 g, 0.15 mmol), potassium carbonate (2.08 g, 15.0 mmol), toluene (18 mL), ethanol (6 mL), and water (6 mL) was refluxed at boiling point for 4 hours. After cooling the reaction mixture to room temperature, water was added and fractionation was performed. The organic layer was dehydrated with sodium sulfate and then concentrated. The resulting residue was purified by silica gel column chromatography to obtain 2.49 g of intermediate A as a white solid (yield 85%).

[1127] Intermediate Synthesis Example 2: Synthesis of Intermediate C-1 and Intermediate C

[1128] [Chemical Formula 132]

[1129]

[1130] (Synthesis of intermediate C-1)

[1131] Intermediate C-1 was obtained by performing the same operation except that 2-(2-bromophenyl)-1-phenylethanol was used instead of 2-(3-bromophenyl)-1-phenylethanol in the synthesis of intermediate A-1 in intermediate synthesis Example 1.

[1132] (Synthesis of intermediate C)

[1133] In the synthesis of intermediate A in Example 1 of intermediate synthesis, intermediate C was obtained by performing the same operation except that intermediate C-1 was used instead of intermediate A-1 and (4'-chloro-[1,1'-biphenyl]-3-yl)boronic acid was used instead of 4-chlorophenylboronic acid.

[1134] Intermediate Synthesis Examples 3–8: Synthesis of Intermediates D–I

[1135] Intermediates D to I were synthesized by performing the same operation as Intermediate A in Intermediate Synthesis Example 1, except that Intermediate A-1 and 4-chlorophenylboronic acid were replaced with Raw Material 1 and Raw Material 2 shown in Table 3 below.

[1136]

[1137] Synthesis Example 1: Synthesis of Compound Inv-1

[1138] [Chemical Formula 133]

[1139]

[1140] Under an argon atmosphere, a mixture of raw material I (intermediate A, 1.09 g, 2.78 mmol), raw material II (intermediate B, 0.85 g, 2.64 mmol), tris(dibenzylideneacetone)dipalladium(0)(0.048 g, 0.053 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl(SPhos)(0.087 g, 0.212 mmol), sodium-tert-butoxide (0.381 g, 3.97 mmol), and xylene (26 mL) was refluxed to the boiling point for 3 hours. After cooling the reaction mixture to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 1.58 g of compound Inv-1 as a white solid. The result obtained was, as a result of mass spectrum analysis, compound Inv-1, with a molecular weight of 675.86 and m / z=676.

[1141] Synthesis Examples 2–18: Synthesis of Compounds Inv-2–18

[1142] Compounds Inv-2 to Inv-18 were synthesized in the same manner as in Synthesis Example 1, except that intermediates A and B in Synthesis Example 1 were replaced with raw material I and raw material II shown in Table 4 below.

[1143] Explanation of the symbols

[1144] 1, 11, 12 Organic EL devices 2 substrates 3 bipolar poles 4 cathodes 5 light-emitting layer 6. Precision transport zone (precision transport layer) 6a Hole injection layer 6b First hole transport layer 6c Second hole transport layer 6d Third hole transport layer 7 Electron transport band (electron transport layer) 7a First electron transport layer 7b Second electron transport layer 10, 20, 30 light-emitting units

Claims

Claim 1 A compound represented by the following formula (1). [Equation (1), N * is the central nitrogen atom.R 5 ~R 8 One selected from is a single bond that combines with *1.R 1 ~R 4 Two of the selected groups are substituted or unsubstituted phenyl groups. R that is not a substituted or unsubstituted phenyl group 1 ~R 4 , and R that is not a single bond 5 ~R 8 Two adjacent elements selected from do not combine with each other and do not form a ring. 1 and Ar 2 Each is independently a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 5 to 30 atoms. 1 , L 2 , and L 3 R is, respectively, a single bond, a substituted or unsubstituted cyclic arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroarylene group having 5 to 30 atoms. R is not a substituted or unsubstituted phenyl group. 1 ~R 4 , R that is not a single bond 5 ~R 8 , and any substituent in the phenyl group is each independently a hydrogen atom, a substituted or unsubstituted C1-50 alkyl group, a substituted or unsubstituted C2-50 alkenyl group, a substituted or unsubstituted C2-50 alkynyl group, a substituted or unsubstituted cyclic C3-50 cycloalkyl group, -Si(R 901 ')(R 902 ')(R 903 '), -O-(R 904 '), -S-(R 905 It is a halogen atom, a cyano group, or a nitro group. R 901 '~R 905 ' is, each independently, a hydrogen atom, a substituted or unsubstituted C1-50 alkyl group, a substituted or unsubstituted cyclic C3-50 cycloalkyl group, or a substituted or unsubstituted cyclic C6-50 aryl group. R 901 '~R 905 If there are 2 or more ', 2 or more R 901 '~R 905 ' can be the same or different.] Claim 2 A compound represented by the following formula (11) or formula (12) in paragraph 1. [Among Equations (11) and (12), N * , R 2 ~R 8 , *1, Ar 1 , Ar 2 , L 1 , L 2 , and L 3 is as defined in the above equation (1). 11 ~R 15 and R 21 ~R 25 are, each independently, a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted C2–50 alkenyl group, a substituted or unsubstituted C2–50 alkynyl group, a substituted or unsubstituted cyclic C3–50 cycloalkyl group, -Si(R 901 ')(R 902 ')(R 903 '), -O-(R 904 '), -S-(R 905 It is a halogen atom, a cyano group, or a nitro group. R 901 '~R 905 ' is, each independently, a hydrogen atom, a substituted or unsubstituted C1-50 alkyl group, a substituted or unsubstituted cyclic C3-50 cycloalkyl group, or a substituted or unsubstituted cyclic C6-50 aryl group. R 901 '~R 905 If there are 2 or more ', 2 or more R 901 '~R 905 ' can be the same or different. 11 ~R 15 and R 21 ~R 25 Two adjacent items selected from do not combine with each other and do not form a ring. Claim 3 In paragraph 2, a compound represented by the above formula (12). Claim 4 In any one of paragraphs 1 to 3, L 1 , L 2 , and L 3 A compound, each independently comprising a single bond, a substituted or unsubstituted cyclic arylene group having 6 to 12 carbon atoms, or a substituted or unsubstituted cyclic heteroarylene group having 5 to 13 atoms. Claim 5 In any one of paragraphs 1 to 4, L 3 A compound that is a substituted or unsubstituted cyclic arylene group having 6 to 12 carbon atoms. Claim 6 In any one of paragraphs 1 to 5, L 3 A compound that is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group. Claim 7 In any one of paragraphs 1 through 6, L 3 A compound, which is an unsubstituted phenylene group. Claim 8 In any one of paragraphs 1 through 7, Ar 1 and Ar 2 Compounds, each independently represented by the following formulas (2A), (2B), (2C), (2D), (2E), or (2F). [Equation (2A), *21 is, L 1 or L 2 Represents the binding to R 101 ~R 105 One selected from is a single bond that joins to *22, and R 106 ~R 110 One selected from is a single bond that combines with *23. The above single bond is not R 101 ~R 105 and R 106 ~R 110 Each is independently a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, or a substituted or unsubstituted cyclic C3-15 cycloalkyl group. The above single bond is not R 101 ~R 105 Two adjacent items selected from do not combine with each other and do not form a ring. The above single bond is not R 106 ~R 110 Two adjacent items selected from do not combine with each other and do not form a ring.R 111 ~R 115 R is, each independently, a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, a substituted or unsubstituted cyclic C3-15 cycloalkyl group, a substituted or unsubstituted cyclic C6-12 aryl group, or a substituted or unsubstituted cyclic C5-13 heteroaryl group. 111 ~R 115 Two adjacent elements selected from do not combine to form a ring. j is 0, 1, or 2, and k is 0 or 1. Exclude the case where j is 2 and k is 0. If j=0 and k=0, *23 represents *21. If j=0 and k=1, *22 represents *21. If j=1 and k=0, *23 represents *22.] [Equation (2B), *24 is, L 1 or L 2 Represents the binding to R 121 ~R 128 One selected from is a single bond that combines with *25. The above single bond is not R 121 ~R 128 Each is independently a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, a substituted or unsubstituted cyclic C3-15 cycloalkyl group, or a substituted or unsubstituted cyclic C6-12 aryl group. The above single bond is R that is not 121 ~R 128 Two adjacent items selected from do not combine with each other and do not form a ring. [In Equation (2C), *26 is L 1 or L 2 Represents the binding to R 131 ~R 140 One selected from is a single bond that combines with *27. The above single bond is not R 131 ~R 140 Each is independently a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, a substituted or unsubstituted cyclic C3-15 cycloalkyl group, or a substituted or unsubstituted cyclic C6-12 aryl group. The above single bond is R that is not 131 ~R 140 Two adjacent items selected from do not combine with each other and do not form a ring. [Equation (2D), *28 is L 1 or L 2 Represents the combination to.X 1 Silver, oxygen atom, sulfur atom, -CR a R b , or -NR c is.*29 is, R 141 ~R 148 , R 200 ~R 203 , R a , R b , or R c Combines to one of the.*29 is R a , R b , and R c If bonding to either of them, R a , R b , and R c Either one is a single bond bonded to *29 or a divalent group bonded to *29. p is 0 or 1. p is 0 and X 1 This, oxygen atom, sulfur atom, -CR a R b , or -NR c When, R a , R b , R c , and R 141 ~R 148 One selected from is a single bond that joins to *29. p is 1, and X 1 This -CR a R b or -NR c When, R 145 and R 146 , R 146 and R 147 , R 141 and R 148 , or R 147 and R 148 R, where one side is a single bond bonding to *e and the other side is a single bond bonding to *f, and not a single bond bonding to *e or *f. 141 and R 145 ~R 148 , R 142 ~R 144 , R 200 ~R 203 , R a , R b , and R c One selected from is a single bond that joins to *29. p is 1, and X 1 When this is an oxygen atom or a sulfur atom, R 145 and R 146 , R 146 and R 147 , R 141 and R 148 , or R 147 and R 148 R, where one side is a single bond bonding to *e and the other side is a single bond bonding to *f, and not a single bond bonding to *e or *f. 141 and R 145 ~R 148 , R 142 ~R 144 , and R 200 ~R 203 One selected from is a single bond that combines with *29. The above single bond is not R 141 ~R 148 , R which is not the above single bond 200 ~R 203 , R which is not the above single bond and is not the above divalent group a and R b , and R c Each is independently a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, a substituted or unsubstituted cyclic C3-15 cycloalkyl group, a substituted or unsubstituted cyclic C6-12 aryl group, or a substituted or unsubstituted cyclic C5-13 heteroaryl group. The above single bond is R that is not 141 ~R 148 and the above single bond is not R 200 ~R 203 Two adjacent items selected from do not combine with each other and do not form a ring. [Equation (2E), *30 is, L 1 or L 2 Represents the binding to R 151 ~R 155 One selected from is a single bond that joins to *31, and R 151 ~R 155 The other one selected from is a single bond that combines with *32. The above single bond is not R 151 ~R 155 is, each independently, a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, a substituted or unsubstituted cyclic C3-15 cycloalkyl group, or an unsubstituted phenyl group. The above single bond is not R 151 ~R 155 Two adjacent items selected from do not combine with each other and do not form a ring.R 161 ~R 165 and R 171 ~R 175 is, each independently, a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, or a substituted or unsubstituted cyclic C3-15 cycloalkyl group. R is not a hydrogen atom. 161 ~R 165 At least one adjacent pair selected from combines to form one or more unsubstituted benzene rings, or does not combine to form a ring. R is not a hydrogen atom. 171 ~R 175 At least one adjacent two selected from combine to form one or more unsubstituted benzene rings, or do not combine to form rings and thus do not form rings. [Equation (2F), *33 is, L 1 or L 2 Represents the binding to R 181 ~R 192 One selected from is a single bond that combines with *34. The above single bond is not R 181 ~R 192 Each is independently a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, a substituted or unsubstituted cyclic C3-15 cycloalkyl group, or a substituted or unsubstituted cyclic C6-12 aryl group. The above single bond is R which is not 181 ~R 192 Two adjacent items selected from do not combine with each other and do not form a ring. Claim 9 In paragraph 8, Ar 1 and Ar 2 A compound, each independently represented by the above formula (2A), (2B), or (2D). Claim 10 In any one of paragraphs 1 through 9, Ar 1 and Ar 2 A compound, each independently comprising a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted naphthobenzofuranyl group. Claim 11 A compound according to any one of claims 1 to 10, comprising at least one deuterium atom in the molecule. Claim 12 A material for an organic electroluminescent device comprising a compound described in any one of claims 1 to 11. Claim 13 A material for an organic electroluminescent device, wherein, in claim 12, the compound described in any one of claims 1 to 11 is a hole transport layer material. Claim 14 An organic electroluminescent device having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer comprises a single or multiple layers including a light-emitting layer, and at least one layer selected from the group consisting of a single layer and multiple layers constituting the organic layer comprises a compound described in any one of claims 1 to 11. Claim 15 An organic electroluminescent device according to claim 14, wherein the organic layer comprises a hole transport band between the anode and the light-emitting layer, and the hole transport band comprises a compound described in any one of claims 1 to 9. Claim 16 An organic electroluminescent device according to claim 15, wherein the hole transport band comprises a first hole transport layer on the anode side and a second hole transport layer on the cathode side, and at least one of the first hole transport layer and the second hole transport layer comprises a compound described in any one of claims 1 to 11. Claim 17 An organic electroluminescent device according to claim 16, wherein the second hole transport layer comprises a compound described in any one of claims 1 to 11. Claim 18 An organic electroluminescent device according to claim 15 or 16, wherein the hole transport band comprises a hole injection layer between the anode and a first hole transport layer on the anode side, the hole injection layer comprises a first organic material and a second organic material, the first organic material and the second organic material are different from each other, and the content of the second organic material in the hole injection layer is 0.01 mass% or more and less than 50 mass%. Claim 19 An organic electroluminescent device according to any one of claims 16 to 18, wherein the light-emitting layer and the second hole transport layer are in direct contact. Claim 20 An organic electroluminescent device according to any one of claims 16 to 19, wherein the sum of the thickness of the first hole transport layer and the thickness of the second hole transport layer is 30 nm or more and 150 nm or less. Claim 21 An organic electroluminescent device according to any one of claims 14 to 20, wherein the light-emitting layer comprises a layer containing a light-emitting compound that exhibits fluorescent light emission having a main peak wavelength of 500 nm or less. Claim 22 An organic electroluminescent device according to any one of claims 14 to 21, wherein the light-emitting layer is stacked in a plurality of layers. Claim 23 An organic electroluminescent device according to any one of claims 14 to 22, wherein the light-emitting layer comprises an anthracene derivative, and a hydrogen atom present on at least one benzene ring of the anthracene derivative is deuterated. Claim 24 An electronic device comprising an organic electroluminescent element as described in any one of paragraphs 14 to 23.

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