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

Abstract

The present invention provides: a compound represented by formula (I), the compound further improving the performance of an organic EL device; a material for an organic electroluminescent device, the material comprising the compound; an organic electroluminescent device comprising the compound and having further improved device performance; and an electronic device comprising the organic electroluminescent device. (Each symbol in each formula is as defined in the specification.)

Description

Compounds, materials for organic electroluminescent devices, organic electroluminescent devices, and electronic devices

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

[0002]

[0003] 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.

[0004] Patent documents 1 to 6 disclose organic electroluminescent devices and compounds used as materials thereof.

[0005] [Prior Art Literature]

[0006] (Patent Document 1) PCT Publication No. 2022 / 071350 (WO2022071350A1)

[0007] (Patent Document 2) PCT Publication No. 2017 / 052261 (WO2017052261A1)

[0008] (Patent Document 3) PCT Publication No. 2022 / 009999 (WO2022009999A2)

[0009] (Patent Document 4) U.S. Publication No. 2023 / 0329025 (US20230329025A1)

[0010] (Patent Document 5) PCT Publication No. 2023 / 199832 (WO2023199832A1)

[0011] (Patent Document 6) PCT Publication No. 2022 / 181711 (WO2022181711A1)

[0012]

[0013] 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.

[0014] The present invention is made to solve the above problems and aims to provide a compound and a material for an organic electroluminescent device that further improves the performance of an organic EL device, an organic electroluminescent device with further improved device performance, and an electronic device including said organic electroluminescent device.

[0015]

[0016] According to one aspect of the present invention, a compound represented by the following formula (I) is provided:

[0017]

[0018] Among the formula (I),

[0019] L1 is an unsubstituted cyclic arylene group having 6 to 12 carbon atoms;

[0020] L2 is a single bond, or a substituted or unsubstituted cyclic arylene group having 6 to 12 carbon atoms;

[0021] R a and R e Each is independently a hydrogen atom;

[0022] R b , R c and R d One of them is a group represented by the following formula (1) or (2), and the other two are each independently hydrogen atoms;

[0023]

[0024]

[0025] (of Equations (1) and (2),

[0026] One selected from R1~R4 is a single bond connected to *, and the other three are each independently hydrogen atoms;

[0027] R5~R 10 Each is independently a hydrogen atom;

[0028] R1~R4 and R5~R, which are not the single combination mentioned above 10 Each of them does not combine with each other and therefore does not form a ring.

[0029] Ar1 is a device represented by the following formula (3) or (4);

[0030]

[0031] (Essence (3),

[0032] R 11 ~R 18 Each is independently a hydrogen atom, and R 11 ~R 18 Each of them does not combine with each other and therefore does not form a ring.

[0033]

[0034] (Equation (4),

[0035] X is O or S and;

[0036] R 21 ~R 24 Each is independently a hydrogen atom;

[0037] R 21 ~R 24 Two adjacent atoms selected from can combine with each other to form a cyclic condensed ring having 6 to 10 carbon atoms;

[0038] R 25 ~R 28 One selected from is a single bond connected to *, and the other three are each independently hydrogen atoms)

[0039] However, if Ar1 is represented by the above equation (4), R b , R c and R dOne of them is a device represented by the above equation (2), and in the above equation (2), R4 is a single connection connected to *, and

[0040] Ar2 is a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms (excluding pyreneyl groups), or a substituted or unsubstituted cyclic heterocyclic group having 5 to 30 atoms (excluding carbazole-9-yl groups and naphthobenzofuranyl groups), and

[0041] In the definition of each substituent in Formula (I), "non-substituent" means that the hydrogen atom is not substituted with a substituent, and the hydrogen atom is a light hydrogen atom, a deuterium atom, or a tritium atom.

[0042] According to another aspect of the present invention, a material for an organic electroluminescent device comprising a compound represented by the formula (I) is provided.

[0043] According to another aspect of the present invention, a hole transport layer material comprising a compound represented by the formula (I) is provided.

[0044] An organic electroluminescent device is provided comprising an anode, a cathode, and an organic layer formed of a single or multiple layers between the anode and the cathode, wherein the organic layer comprises a light-emitting layer, and at least one of the organic layers comprises a compound represented by the formula (I).

[0045] According to another aspect of the present invention, an electronic device comprising the organic electroluminescent element is provided.

[0046]

[0047] An organic EL device containing a compound represented by the above formula (I) exhibits improved device performance.

[0048]

[0049] 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.

[0050] 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.

[0051] 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.

[0052] <Explanation of Symbols> 1, 11, 12: Organic EL device, 2: Substrate, 3: Anode, 4: Cathode, 5: Emitting layer, 6: Hole transport band (hole 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: Emitting unit

[0053]

[0054] [definition]

[0055] In this specification, the term hydrogen atom includes isotopes with different numbers of neutrons, namely, protium atoms, deuterium atoms, and tritium atoms.

[0056] 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.

[0057] 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 9,9-diphenylfluorenyl group has a cyclic carbon number of 13, and the 9,9'-spirobifluorenyl group has a cyclic carbon number of 25.

[0058] 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.

[0059] 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 "number of ring-forming atoms" described below shall be treated in the same way 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.

[0060] 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.

[0061] In the present specification, in the expression “ZZ group having a number of atoms XX to YY that is 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.

[0062] 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."

[0063] 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.

[0064] 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.

[0065] "Substituents described in this specification"

[0066] The substituents described in this specification will be explained below.

[0067] 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.

[0068] 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.

[0069] 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.

[0070] 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.

[0071] 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.

[0072] 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.

[0073] 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.

[0074] 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.

[0075] 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.

[0076] · "Substituted or unsubstituted aryl group"

[0077] 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.

[0078] "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.

[0079] · Unsubstituted Arylgi (Specific Example Group G1A):

[0080] phenyl group,

[0081] p-biphenyl group,

[0082] m-biphenyl group,

[0083] o-biphenyl group,

[0084] p-terphenyl-4-diary,

[0085] p-terphenyl-3-diary,

[0086] p-terphenyl-2-diary,

[0087] m-terphenyl-4-diary,

[0088] m-terphenyl-3-diary,

[0089] m-terphenyl-2-diary,

[0090] o-terphenyl-4-diary,

[0091] o-terphenyl-3-diary,

[0092] o-terphenyl-2-diyl,

[0093] 1-Naphthyl group,

[0094] 2-Naphthyl group,

[0095] Anthrill,

[0096] benzoaterillic group,

[0097] phenanthril group,

[0098] Benzophenanthrile group,

[0099] Penalen Diary,

[0100] Firen's Diary

[0101] Krysen's Diary

[0102] Benzokrysen Diary

[0103] triphenyleneyl group,

[0104] Benzotriphenyleneyl group,

[0105] Tetracen Diary,

[0106] Pentasen Diary,

[0107] Fluorene Diary,

[0108] 9,9'-Spyrobluorene Diary,

[0109] Benzofluorene Diary,

[0110] Dibenzofluoren Diary,

[0111] Fluoranthene Diary

[0112] Benzofluoranthene Diary

[0113] Perillen Diary, and

[0114] 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).

[0115]

[0116]

[0117] · Substituted aryl group (Specific example group G1B):

[0118] o-tollil group,

[0119] m-tolyl group,

[0120] p-tolyl group,

[0121] Para-xylyl,

[0122] meta-xylyl group,

[0123] Ortho-xylyl group,

[0124] para-isopropylphenyl group,

[0125] meta-isopropylphenyl group,

[0126] Ortho-isopropylphenyl group,

[0127] para-t-butylphenyl group,

[0128] meta-t-butylphenyl group,

[0129] Ortho-t-butylphenyl group,

[0130] 3,4,5-trimethylphenyl group,

[0131] 9,9-dimethylfluorene yl group,

[0132] 9,9-diphenylfluorene digroup

[0133] 9,9-bis(4-methylphenyl)fluorenyl group,

[0134] 9,9-bis(4-isopropylphenyl)fluoreneyl group,

[0135] 9,9-bis(4-t-butylphenyl)fluorenyl group,

[0136] cyanophenyl group,

[0137] triphenylsilylphenyl group,

[0138] trimethylsilylphenyl group,

[0139] phenylnaphthyl group,

[0140] Naphthylphenyl group, and

[0141] 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.

[0142] · "Substituted or unsubstituted heterovents"

[0143] 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.

[0144] The “heterocyclic group” described in this specification is a single-ring group or a condensed-ring group.

[0145] The "heteroventilation" described in this specification is an aromatic heteroventilation or a non-aromatic heteroventilation.

[0146] Examples of specific examples (Group of Examples G2) of the “substituted or unsubstituted heterovent” described in this specification include the following unsubstituted heterovent (Group of Examples G2A) and substituted heterovent (Group of 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.

[0147] "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.

[0148] 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).

[0149] 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).

[0150] · Unsubstituted heterocyclic group containing a nitrogen atom (Specific example group G2A1):

[0151] pyrrolyl group,

[0152] Imidajorilgi,

[0153] pyrazolyl group,

[0154] triazolyl group,

[0155] tetrazolyl group,

[0156] Oxazoligi,

[0157] Child's sleepiness

[0158] oxadiazolyl group,

[0159] Thiazolidin,

[0160] isothiazolyl group,

[0161] Cydiadiazolyl,

[0162] Piridilgi,

[0163] Piridajin Diary,

[0164] Pyrimidin Diary,

[0165] Pirajin Diary,

[0166] Triazine Diary

[0167] Indolil,

[0168] Iso-in-drill,

[0169] Indollijin Diary,

[0170] Quinoligin Diary,

[0171] Quinolyl group,

[0172] isoquinolyl group,

[0173] Sinnolilgi,

[0174] Phtalazine Diary,

[0175] Quinazolin Diary,

[0176] Quinoxalin Diary

[0177] Benzimidazoliyl group,

[0178] Indazolillgi,

[0179] Penantrollin Diary

[0180] Phenanthridine Diary,

[0181] Acridin Diary,

[0182] Penazine Diary

[0183] Carbazolyl group,

[0184] benzocarbazolyl group,

[0185] Morpolinogi,

[0186] Phenox Photo Diary

[0187] Phenothiazine Diary

[0188] Azacarbazolyl group, and

[0189] Diazacarbazolyl group.

[0190] · Unsubstituted heterocyclic group containing an oxygen atom (Specific example group G2A2):

[0191] Furyl group,

[0192] Oxazoligi,

[0193] Child's sleepiness

[0194] oxadiazolyl group,

[0195] Zanten Diary,

[0196] Benzofuran Diary,

[0197] Isobenzofuran Diary,

[0198] Divenzofuran Diary,

[0199] Naftobenzopyran Diary,

[0200] benzoxazolyl group,

[0201] Benz-Eye Soksajolilgi,

[0202] Phenox Photo Diary

[0203] Morpolinogi,

[0204] Dynaphtofuran Diary

[0205] Azada Benzopyun Diary,

[0206] Diary of Diazadaibenzofuran

[0207] Azanaptobenzopyran Diary, and

[0208] Diary of Diazanaptobenzopyran

[0209] · Unsubstituted heterocyclic groups containing sulfur atoms (Specific example group G2A3):

[0210] Cyworld Diary,

[0211] Thiazolidin,

[0212] isothiazolyl group,

[0213] Cydiadiazolyl,

[0214] Benzothiophene Diary (Benzothien Diary),

[0215] Isobenzothiophene Diary (Isobenzothiene Diary),

[0216] Dibenzothiophen Diary (Dibenzothiophen Diary),

[0217] Naphthobenzothiophen Diary (Naphthobenzothiophen Diary),

[0218] Benzothiazolyl group,

[0219] Benzisothiazolyl group,

[0220] Phenothiazine Diary

[0221] Dynaphthothiophene Diary (Dynapthothien Diary),

[0222] Azada benzothiophen Diary (Aza benzothiophen Diary),

[0223] Diazadiabenzothiophen Diary (Diazadiabenzothiophen Diary),

[0224] Azanaptobenzothiophen Diary (Azanaptobenzothien Diary), and

[0225] Diazanapthobenzothiophen Diary (Diazanapthobenzothiophen Diary).

[0226] A monovalent heterocyclic group (specific example group G2A4) induced by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33):

[0227]

[0228]

[0229] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y Ais, 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.

[0230] 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 above general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0231] · Substituted heterocyclic group containing a nitrogen atom (Specific example group G2B1):

[0232] (9-phenyl)carbazolyl group,

[0233] (9-biphenylyl)carbazolyl group,

[0234] (9-phenyl)phenylcarbazolyl group,

[0235] (9-naphthyl)carbazolyl group,

[0236] Diphenylcarbazole-9-diary,

[0237] Phenylcarbazole-9-diary,

[0238] methylbenzimidazolyl group,

[0239] Ethylbenzimidazolyl group,

[0240] Phenyltriazine diary,

[0241] Biphenylyltriazine Diary,

[0242] Diphenyltriazine Diary

[0243] Phenylquinazolin diary, and

[0244] Biphenylylquinazolin Diary

[0245] · Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0246] Phenyldibenzofuran diary,

[0247] Methyldibenzofuran group,

[0248] t-butyldibenzofuran group, and

[0249] The monovalent residue of spiro[9H-xanthen-9,9'-[9H]fluorene].

[0250] · Substituted heterocyclic groups containing sulfur atoms (specific example group G2B3):

[0251] Phenyldibenzothiophene Diary,

[0252] Methyl dibenzothiophene diary,

[0253] t-butyldibenzothiophenyl group, and

[0254] The monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0255] · 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):

[0256] 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.

[0257] · "Substituted or unsubstituted alkyl group"

[0258] Examples of specific examples (Group of Examples G3) of the “substituted or unsubstituted alkyl group” described in this specification include the following unsubstituted alkyl group (Group of Examples G3A) and substituted alkyl group (Group of 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.

[0259] "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.

[0260] · Unsubstituted alkyl group (Specific Example Group G3A):

[0261] methyl group,

[0262] ethyl group,

[0263] n-Profilter,

[0264] isopropyl group,

[0265] n-butyl group,

[0266] isobutyl group,

[0267] s-butyl group, and

[0268] t-butyl group.

[0269] · Substituted alkyl group (Specific Example Group G3B):

[0270] heptafluoropropyl group (including isomers),

[0271] pentafluoroethyl group,

[0272] 2,2,2-trifluoroethyl group, and

[0273] Trifluoromethyl group.

[0274] · "Substituted or unsubstituted alkenes"

[0275] Examples of specific examples (Group of Examples G4) of the “substituted or unsubstituted alkenyl group” described in this specification include the following unsubstituted alkenyl group (Group of Examples G4A) and substituted alkenyl group (Group of 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.

[0276] "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.

[0277] · Unsubstituted Alkene Diary (Special Example Group G4A):

[0278] vinyl recorder

[0279] Alilgi,

[0280] 1-Beauten Diary,

[0281] 2-Beauten Diary, and

[0282] 3-Beauten Diary.

[0283] · Substituted Alken Diary (Specific Example Group G4B):

[0284] 1,3-Butanedienne's Diary,

[0285] 1-methylvinyl group,

[0286] 1-methylallyl group,

[0287] 1,1-dimethylallyl group,

[0288] 2-methylallyl group, and

[0289] 1,2-dimethylallyl group.

[0290] · "Substituted or Non-substituted Alkin Diary"

[0291] 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.

[0292] "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.

[0293] · Unsubstituted Alkin Diary (Special Example Group G5A):

[0294] Etin Diary

[0295] · Substituted or unsubstituted cycloalkyl group

[0296] Specific examples of the “substituted or unsubstituted cycloalkyl group” described in this specification (Specific Example Group G6) include the following unsubstituted cycloalkyl group (Specific Example Group G6A) and substituted cycloalkyl group (Specific Example Group 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.

[0297] "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.

[0298] · Unsubstituted cycloalkyl group (Specific Example Group G6A):

[0299] Cyclopropyl group,

[0300] cyclobutyl group,

[0301] cyclopentyl group,

[0302] cyclohexyl group,

[0303] 1-adamantyl group,

[0304] 2-adamantyl group,

[0305] 1-norbonyl group, and

[0306] 2-Novonyl group.

[0307] · Substituted cycloalkyl group (Specific Example Group G6B):

[0308] 4-methylcyclohexyl group.

[0309] · -Si(R 901 )(R 902 )(R 903 The device indicated by )

[0310] -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),

[0311] -Si(G1)(G1)(G1),

[0312] -Si(G1)(G2)(G2),

[0313] -Si(G1)(G1)(G2),

[0314] -Si(G2)(G2)(G2),

[0315] -Si(G3)(G3)(G3), and

[0316] -Si(G6)(G6)(G6)

[0317] ...can be cited. Here,

[0318] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.

[0319] G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2.

[0320] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

[0321] G6 is a “substituted or unsubstituted cycloalkyl group” as described in Specific Example Group G6.

[0322] In -Si(G1)(G1)(G1), the multiple G1s are either identical or different from each other.

[0323] In Si(G1)(G2)(G2), the multiple G2s are either identical or different from each other.

[0324] In -Si(G1)(G1)(G2), the multiple G1s are either identical or different from each other.

[0325] In -Si(G2)(G2)(G2), the multiple G2s are either identical or different from each other.

[0326] In -Si(G3)(G3)(G3), the multiple G3s are either identical or different from each other.

[0327] In -Si(G6)(G6)(G6), the multiple G6s are either identical or different from each other.

[0328] · 「-O-(R 904 The unit indicated by )

[0329] -O-(R as described in this specification 904 As for a specific example of the device indicated by ) (specific example group G8),

[0330] -O(G1),

[0331] -O(G2),

[0332] -O(G3), and

[0333] -O(G6)

[0334] ...can be cited.

[0335] Here,

[0336] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.

[0337] G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2.

[0338] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

[0339] G6 is a “substituted or unsubstituted cycloalkyl group” as described in Specific Example Group G6.

[0340] · 「-S-(R 905 The unit indicated by )

[0341] -S-(R as described in this specification 905 As for a specific example of the device indicated by ) (specific example group G9),

[0342] -S(G1),

[0343] -S(G2),

[0344] -S(G3), and

[0345] -S(G6)

[0346] ...can be cited.

[0347] Here,

[0348] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.

[0349] G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2.

[0350] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

[0351] G6 is a “substituted or unsubstituted cycloalkyl group” as described in Specific Example Group G6.

[0352] · 「-N(R 906 )(R 907 The unit indicated by )

[0353] -N(R as described in this specification 906 )(R 907 As for a specific example of the device indicated by ) (specific example group G10),

[0354] -N(G1)(G1),

[0355] -N(G2)(G2),

[0356] -N(G1)(G2),

[0357] -N(G3)(G3), and

[0358] -N(G6)(G6)

[0359] ...can be cited.

[0360] Here,

[0361] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.

[0362] G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2.

[0363] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

[0364] G6 is a “substituted or unsubstituted cycloalkyl group” as described in Specific Example Group G6.

[0365] In -N(G1)(G1), multiple G1s are either identical or different from each other.

[0366] In -N(G2)(G2), the multiple G2s are either identical or different from each other.

[0367] In -N(G3)(G3), the multiple G3s are either identical or different from each other.

[0368] In -N(G6)(G6), the multiple G6s are either identical or different from each other.

[0369] · Halogen atoms

[0370] Specific examples of the “halogen atoms” described in this specification (Specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0371] · Substituted or unsubstituted fluoroalkyl group

[0372] 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.

[0373] · Substituted or unsubstituted haloalkyl group

[0374] 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.

[0375] · "Substituted or unsubstituted alkoxy groups"

[0376] 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.

[0377] · "Substituted or unsubstituted alkylthio groups"

[0378] 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.

[0379] · "Substituted or unsubstituted aryloxy group"

[0380] 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 cyclic carbon atoms of the “unsubstituted aryloxy group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0381] · "Substituted or unsubstituted aryl-thiologic"

[0382] 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.

[0383] · "Substituted or unsubstituted trialkylsilyl group"

[0384] 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.

[0385] · Substituted or unsubstituted aralkyl group

[0386] 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.

[0387] Specific examples of “substituted or unsubstituted aralkyl groups” include benzyl groups, 1-phenylethyl groups, 2-phenylethyl groups, 1-phenylisopropyl groups, 2-phenylisopropyl groups, phenyl-t-butyl groups, α-naphthylmethyl groups, 1-α-naphthylethyl groups, 2-α-naphthylethyl groups, 1-α-naphthylisopropyl groups, 2-α-naphthylisopropyl groups, β-naphthylmethyl groups, 1-β-naphthylethyl groups, 2-β-naphthylethyl groups, 1-β-naphthylisopropyl groups, and 2-β-naphthylisopropyl groups.

[0388] 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.

[0389] 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.

[0390] In this specification, the carbazolyl group is, specifically, any one of the following, unless otherwise specified in this specification.

[0391]

[0392] In this specification, the (9-phenyl)carbazolyl group is, specifically, any one of the following groups, unless otherwise specified in this specification.

[0393]

[0394] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates a bonding position.

[0395] In this specification, the dibenzofuranyl group and the dibenzothiophenyl group are, specifically, any one of the following, unless otherwise specified in this specification.

[0396]

[0397] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

[0398] 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.

[0399] · "Substituted or unsubstituted arylene group"

[0400] 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.

[0401] · "Substituted or unsubstituted divalent heterocyclic"

[0402] The “substituted or unsubstituted divalent heterocyclic group” described in this specification is a divalent group induced by removing one hydrogen atom from the “substituted or unsubstituted heterocyclic group” above. 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 “substituted or unsubstituted heterocyclic group” described in Specific Example Group G2.

[0403] · "Substituted or unsubstituted alkylene group"

[0404] 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.

[0405] The substituted or unsubstituted arylene groups described in this specification are, unless otherwise specified in this specification, preferably any one of the following general formulas (TEMP-42) to (TEMP-68).

[0406]

[0407]

[0408] Among the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0409] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0410]

[0411] Among the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0412] Formula Q9 and Q 10 Silver may also form rings by joining together with a single bond.

[0413] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.

[0414]

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

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

[0417] 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.

[0418]

[0419]

[0420]

[0421] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently hydrogen atoms or substituents.

[0422]

[0423]

[0424]

[0425]

[0426] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently hydrogen atoms or substituents.

[0427] The above is an explanation of the “substituents described in this specification.”

[0428] · "When combining to form a ring"

[0429] 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.”

[0430] 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. An example will be explained for an anthracene compound represented by the following general formula (TEMP-103), in which the matrix is ​​an anthracene ring.

[0431]

[0432] 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 R921 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.

[0433] 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 A Forms, 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).

[0434]

[0435] 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 , R922 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.

[0436]

[0437] 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.

[0438] "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.

[0439] 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.

[0440] 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.

[0441] 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.

[0442] "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.

[0443] 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.

[0444] 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.

[0445] Unless otherwise specified in this specification, among “single ring” and “condensed ring,” it is preferably “single ring”.

[0446] Unless otherwise specified in this specification, among "saturated ring" and "unsaturated ring," it is preferably "unsaturated ring".

[0447] Unless otherwise specified in this specification, "single ring" is preferably a benzene ring.

[0448] Unless otherwise specified in this specification, the “unsaturated ring” is preferably a benzene ring.

[0449] 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.

[0450] 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."

[0451] 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."

[0452] 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 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).

[0453] · Substituents in the case of "substituted or unsubstituted"

[0454] 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,

[0455] Unsubstituted alkene group having 2 to 50 carbon atoms,

[0456] Unsubstituted alkyne groups having 2 to 50 carbon atoms,

[0457] Unsubstituted cyclic cycloalkyl groups having 3 to 50 carbon atoms,

[0458] -Si(R 901 )(R 902 )(R 903 ),

[0459] -O-(R 904 ),

[0460] -S-(R 905 ),

[0461] -N(R 906 )(R 907 ),

[0462] Halogen atoms, cyano-type, nitro-type,

[0463] Unsubstituted cyclic aryl groups having 6 to 50 carbon atoms, and

[0464] Unsubstituted heterocyclic atoms with 5 to 50 atoms

[0465] It is a group selected from the group consisting of, and

[0466] Here, R 901 ~R 907 Each independently,

[0467] hydrogen atom,

[0468] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0469] Substituted or unsubstituted cyclic cycloalkyl groups having 3 to 50 carbon atoms,

[0470] A substituted or unsubstituted cyclic aryl group having 6 to 50 carbon atoms, or

[0471] It is a heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms.

[0472] R 901 If there are 2 or more of these, 2 or more R 901 are identical to each other, or different,

[0473] R 902 If there are 2 or more, 2 or more R 902 are identical to each other, or different,

[0474] R 903 If there are 2 or more of these, 2 or more R 903 are identical to each other, or different,

[0475] R 904 If there are 2 or more, 2 or more R 904 are identical to each other, or different,

[0476] R 905 If there are 2 or more, 2 or more R 905 are identical to each other, or different,

[0477] R 906 If there are 2 or more of these, 2 or more R 906 are identical to each other, or different,

[0478] R 907 If there are 2 or more of these, 2 or more R 907 They are identical or different from each other.

[0479] In one embodiment, the substituent in the case of "substituted or unsubstituted" is,

[0480] alkyl group having 1 to 50 carbon atoms,

[0481] Cyclic aryl groups having 6 to 50 carbon atoms, and

[0482] Heterocyclic with 5 to 50 cyclic atoms

[0483] It is a group selected from the group consisting of

[0484] In one embodiment, the substituent in the case of "substituted or unsubstituted" is,

[0485] alkyl group having 1 to 18 carbon atoms,

[0486] Cyclic aryl groups having 6 to 18 carbon atoms, and

[0487] Heterocyclic cyclic atoms with 5 to 18 atoms

[0488] It is a group selected from the group consisting of

[0489] 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”.

[0490] 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.

[0491] 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.

[0492] 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.

[0493]

[0494] Compound of Formula (I)

[0495] The compounds of the present invention will be described below.

[0496] A compound according to one aspect of the present invention is represented by the following formula (I). Hereinafter, a compound of the present invention represented by formula (I) and a formula included in formula (I) described below may be simply referred to as the “inventive compound.”

[0497]

[0498] Among the formula (I),

[0499] L1 is an unsubstituted cyclic arylene group having 6 to 12 carbon atoms;

[0500] L2 is a single bond, or a substituted or unsubstituted cyclic arylene group having 6 to 12 carbon atoms;

[0501] R a and R e Each is independently a hydrogen atom;

[0502] R b , R c and R d One of them is a group represented by the following formula (1) or (2), and the other two are each independently hydrogen atoms;

[0503]

[0504]

[0505] (of Equations (1) and (2),

[0506] One selected from R1~R4 is a single bond connected to *, and the other three are each independently hydrogen atoms;

[0507] R5~R 10 Each is independently a hydrogen atom;

[0508] R1~R4 and R5~R, which are not the single combination mentioned above 10 Each of them does not combine with each other and therefore does not form a ring.

[0509] Ar1 is a device represented by the following formula (3) or (4);

[0510]

[0511] (Essence (3),

[0512] R 11 ~R 18 Each is independently a hydrogen atom, and R 11 ~R 18 Each of them does not combine with each other and therefore does not form a ring.

[0513]

[0514] (Equation (4),

[0515] X is O or S and;

[0516] R 21 ~R 24 Each is independently a hydrogen atom;

[0517] R 21 ~R 24 Two adjacent atoms selected from can combine with each other to form a cyclic condensed ring having 6 to 10 carbon atoms;

[0518] R 25 ~R 28 One selected from is a single bond connected to *, and the other three are each independently hydrogen atoms)

[0519] However, if Ar1 is represented by the above equation (4), R b , R c and R d One of them is a device represented by the above equation (2), and in the above equation (2), R4 is a single connection connected to *, and

[0520] Ar2 is a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms (excluding pyreneyl groups), or a substituted or unsubstituted cyclic heterocyclic group having 5 to 30 atoms (excluding carbazole-9-yl groups and naphthobenzofuranyl groups), and

[0521] In the definition of each substituent in Formula (I), "non-substituent" means that the hydrogen atom is not substituted with a substituent, and the hydrogen atom is a light hydrogen atom, a deuterium atom, or a tritium atom.

[0522] In one embodiment, R in the above formula (4) 21 ~R 24 When two adjacent selected from combine to form a cyclic condensed ring having 6 to 10 carbon atoms, it may be represented by any one of the following formulas (4-1) to (4-6), but is not limited thereto.

[0523]

[0524] (In Equation (4-1), X, R 23 ~R 28 and * are as defined in Equation (4)

[0525]

[0526] (In Equation (4-2), X, R 21 and R 24 ~R 28 and * are as defined in Equation (4)

[0527]

[0528] (In Equation (4-3), X, R 21 , R 22 and R 25 ~R 28 and * are as defined in Equation (4)

[0529]

[0530] (In Equation (4-4), X, R 23 ~R 28 and * are as defined in Equation (4)

[0531]

[0532] (In Equation (4-5), X, R 21 and R 24 ~R 28 and * are as defined in Equation (4)

[0533]

[0534] (In Equation (4-6), X, R 21 , R 22 and R25 ~R 28 and * are as defined in Equation (4)

[0535] In another embodiment, Ar2 may be a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms. The above substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms may preferably be a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group, chrysenyl group, triphenyleneyl group, fluoreneyl group, 9,9'-spirobifluoreneyl group, 9,9-dimethylfluoreneyl group, or 9,9-diphenylfluoreneyl group, but is not limited thereto.

[0536] In another specific example, Ar2 may be a heterocyclic group having 5 to 30 substituted or unsubstituted cyclic atoms. The above-mentioned substituted or unsubstituted heterocyclic group having 5 to 30 cyclic atoms is preferably a pyridyl group, a pyrimidineyl group, a triazineyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolineyl group, a carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, or 4-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an azadibenzothiophenyl group, a 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, or phenyldibenzothiophen yl group, but is not limited thereto.

[0537] In another embodiment, Ar2 is a substituted or unsubstituted cyclic aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted cyclic heterocyclic group having 5 to 20 atoms.

[0538] In another embodiment, Ar2 is a substituted or unsubstituted cyclic aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted cyclic heterocyclic group having 5 to 15 atoms.

[0539] In another specific example, among the above formula (I), Ar2 is represented by the following formulas (1-a), (1-b), (1-c), (1-d) or (1-e).

[0540]

[0541] (of Equation (1-a),

[0542] *21 is a single bond that bonds to L2, and if L2 is a single bond, *21 bonds to the central nitrogen atom;

[0543] 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 combination that combines to *23;

[0544] R other than the above single bond 101 ~R 110 Each is independently a hydrogen atom or an unsubstituted C1- to C10 alkyl group;

[0545] R 111 ~R 115 Each is independently a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, a substituted or unsubstituted cyclic C6-12 aryl group, or a substituted or unsubstituted cyclic 5-13 heterocyclic group;

[0546] u is 0 to 2, and v is 0 or 1;

[0547] When u is 0, *22 is a single bond bonded to L2, and when u is 0 and L2 is a single bond, *22 is bonded to the central nitrogen atom;

[0548] When both u and v are 0, *23 is a single bond bonded to L2, and when both u and v are 0 and L2 is a single bond, *23 is bonded to the central nitrogen atom.

[0549]

[0550] (of Equation (1-b),

[0551] *24 is a single bond that bonds to L2, and if L2 is a single bond, *24 bonds to the central nitrogen atom;

[0552] R 121 ~R 128 One selected from is a single combination that combines to *25;

[0553] R other than the above single bond 121 ~R 128 Each is independently a hydrogen atom, a substituted or unsubstituted C1- to C10 alkyl group, or a substituted or unsubstituted cyclic C6- to C12 aryl group)

[0554]

[0555] (of Equation (1-c),

[0556] *26 is a single bond that bonds to L2, and if L2 is a single bond, *26 bonds to the central nitrogen atom;

[0557] R 131 ~R 140 One selected from is a single combination that combines to *27;

[0558] R other than the above single bond 131 ~R 140 Each is independently a hydrogen atom, a substituted or unsubstituted C1- to C10 alkyl group, or a substituted or unsubstituted cyclic C6- to C12 aryl group)

[0559]

[0560] (of Equation (1-d),

[0561] *28 is a single bond that bonds to L2, and if L2 is a single bond, *28 bonds to the central nitrogen atom;

[0562] X 1 Silver oxygen atom, sulfur atom, -CR E R F or -NR G And;

[0563] p is 0 or 1 and;

[0564] When p is 0, R 141 ~R 148 , R E , R F and R G One selected from is a single combination that combines to *29;

[0565] p is 1, and X 1 This -CR E R F or -NR G In the case of, R 145 and R 146 , R 146 and R 147 , or R 147 and R 148 One of them is a single bond binding to *d, the other is a single bond binding to *e, and R is not a single bond binding to *d or *e. 145 ~R 148 , R 141 ~R 144 , R 200 ~R 203 , R E , R F and R G One selected from is a single combination that combines to *29;

[0566] p is 1, and X 1 If this is an oxygen atom or a sulfur atom, R 145 and R 146 , R 146 and R 147 , or R 147 and R 148 One side is a single bond bonding to *d, the other side is a single bond bonding to *e, and R 141 to R 144 One selected from is a single combination that combines to *29;

[0567] R other than the above single bond 141 ~R 148 , R other than the above single bond 200 ~R 203 , and R that is not the single bond mentioned above E ~R G Each is independently a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, a substituted or unsubstituted C6-12 aryl group, or a substituted or unsubstituted C5-13 heterocyclic group)

[0568]

[0569] (of Equation (1-e),

[0570] *30 is a single bond that bonds to L2, and if L2 is a single bond, *30 bonds to the central nitrogen atom;

[0571] R 151 ~R 155 One selected from is a single bond that combines to *31, and the other is a single bond that combines to *32;

[0572] R other than the above single bond 151 ~R 155 Each is independently a hydrogen atom, an unsubstituted C1- to C10 alkyl group, or an unsubstituted phenyl group;

[0573] R 161 ~R 165 and R 171 ~R 175 Each is independently a hydrogen atom or an unsubstituted C1- to C10 alkyl group;

[0574] R, not a hydrogen atom 161 to R 165 At least one pair of adjacent 2 selected from can combine with each other to form one or more unsubstituted benzene rings;

[0575] R, not a hydrogen atom 171 to R 175 At least one pair of adjacent two selected from can combine with each other to form one or more unsubstituted benzene rings.)

[0576] In another embodiment, among the above formula (I), Ar1 is the group represented by formula (3), and Ar2 is the group represented by formula (1-a). In another embodiment, among the above formula (I), Ar1 is the group represented by formula (3), and Ar2 is the group represented by formula (1-b). In another embodiment, among the above formula (I), Ar1 is the group represented by formula (3), and Ar2 is the group represented by formula (1-c). In another embodiment, among the above formula (I), Ar1 is the group represented by formula (3), and Ar2 is the group represented by formula (1-d). In another embodiment, among the above formula (I), Ar1 is the group represented by formula (3), and Ar2 is the group represented by formula (1-e).

[0577] In another embodiment, among the above formula (I), Ar1 is the group represented by formula (4), and Ar2 is the group represented by formula (1-a). In another embodiment, among the above formula (I), Ar1 is the group represented by formula (4), and Ar2 is the group represented by formula (1-b). In another embodiment, among the above formula (I), Ar1 is the group represented by formula (4), and Ar2 is the group represented by formula (1-c). In another embodiment, among the above formula (I), Ar1 is the group represented by formula (4), and Ar2 is the group represented by formula (1-d). In another embodiment, among the above formula (I), Ar1 is the group represented by formula (4), and Ar2 is the group represented by formula (1-e).

[0578] In another specific example, R b , R c and R d One of them is a group represented by Equation (1), Ar1 is a group represented by Equation (3), and Ar2 is a group represented by Equation (1-a). In another specific example, R b , R c and R dOne of them is a group represented by Equation (1), Ar1 is a group represented by Equation (3), and Ar2 is a group represented by Equation (1-b). In another specific example, R b , R c and R d One of them is a group represented by Equation (1), Ar1 is a group represented by Equation (3), and Ar2 is a group represented by Equation (1-c). In another specific example, R b , R c and R d One of them is a group represented by Equation (1), Ar1 is a group represented by Equation (3), and Ar2 is a group represented by Equation (1-d). In another specific example, R b , R c and R d One of them is a group represented by Equation (1), Ar1 is a group represented by Equation (3), and Ar2 is a group represented by Equation (1-e).

[0579] In another specific example, R b , R c and R d One of them is a group represented by Equation (2), Ar1 is a group represented by Equation (3), and Ar2 is a group represented by Equation (1-a). In another specific example, R b , R c and R d One of them is a group represented by Equation (2), Ar1 is a group represented by Equation (3), and Ar2 is a group represented by Equation (1-b). In another specific example, R b , R c and R d One of them is a group represented by Equation (2), Ar1 is a group represented by Equation (3), and Ar2 is a group represented by Equation (1-c). In another specific example, R b , R c and R dOne of them is a group represented by Equation (2), Ar1 is a group represented by Equation (3), and Ar2 is a group represented by Equation (1-d). In another specific example, R b , R c and R d One of them is a group represented by Equation (2), Ar1 is a group represented by Equation (3), and Ar2 is a group represented by Equation (1-e).

[0580] In another specific example, R b , R c and R d One of them is a group represented by Equation (2), Ar1 is a group represented by Equation (4), and Ar2 is a group represented by Equation (1-a). In another specific example, R b , R c and R d One of them is a group represented by Equation (2), Ar1 is a group represented by Equation (4), and Ar2 is a group represented by Equation (1-b). In another specific example, R b , R c and R d One of them is a group represented by Equation (2), Ar1 is a group represented by Equation (4), and Ar2 is a group represented by Equation (1-c). In another specific example, R b , R c and R d One of them is a group represented by Equation (2), Ar1 is a group represented by Equation (4), and Ar2 is a group represented by Equation (1-d). In another specific example, R b , R c and R d One of them is a group represented by Equation (2), Ar1 is a group represented by Equation (4), and Ar2 is a group represented by Equation (1-e).

[0581] In one embodiment, the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms mentioned in the substituent definitions of formulas (1-a) to (1-e) may be 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, or a heptafluoropropyl group, a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, or a trifluoromethyl group.

[0582] In other embodiments, the substituted or unsubstituted cyclic aryl group having 6 to 12 carbon atoms mentioned in the substituent definitions of formulas (1-a) to (1-e) above may be a phenyl group, a biphenyl group, or a naphthyl group.

[0583] In another specific example, the heterocyclic group having 5 to 13 substituted or unsubstituted cyclic atoms mentioned in the substituent definitions of formulas (1-a) to (1-e) may be a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.

[0584] In another specific example, the base of the above formula (1-a) may be represented by any one of the following formulas (1-a-1) to (1-a-4).

[0585]

[0586]

[0587]

[0588]

[0589] In equations (1-a-1) through (1-a-4), each symbol is as defined in equation (1-a).

[0590] In another specific embodiment, the base of the above-mentioned formula (1-a) may be represented by any one selected from the group consisting of the following formulas (in the following formulas, for simplification, R 101 ~R 115 The notation is omitted).

[0591]

[0592] In another specific embodiment, in formula (1-a), R that is not a single bond 101 ~R 110 , and R 111 ~R 115 It can be a hydrogen atom.

[0593] In another specific embodiment, in formula (1-b), R that is not a single bond is 121 ~R 128 It can be a hydrogen atom.

[0594] In another specific embodiment, in formula (1-c), R that is not a single bond 131 ~R 140 It can be a hydrogen atom.

[0595] In another specific example, in Equation (1-d), when p is 0, R 141 ~R 148 , R E and R F One selected from is a single bond that joins to *29; and if p is 1, X 1 Silver is a sulfur atom, -CR E R F , or -NR G am.

[0596] In another specific example, the group represented by the above formula (1-d) is a group represented by any one of the following formulas (1-d-1) to (1-d-4).

[0597]

[0598] (of Equation (1-d-1),

[0599] X 1 Silver oxygen atom, sulfur atom, -CR E R F or -NR G And;

[0600] R 141 ~R 148 , R E and R FOne selected from is a single combination that combines to *29;

[0601] *28, R 141 ~R 148 , R E , R F and R G As defined in Equation (1-d)

[0602]

[0603] (of Equation (1-d-2),

[0604] X 1 Silver is a sulfur atom, -CR E R F or -NR G And;

[0605] *28, *29, R 141 ~R 144 , R 147 , R 148 , R 200 ~R 203 , R E , R F and R G is as defined in Equation (1-d)

[0606]

[0607] (Equation (1-d-3),

[0608] X 1 Silver is a sulfur atom, -CR E R F or -NR G And;

[0609] *28, *29, R 141 ~R 144 , R 145 , R 148 , R 200 ~R 203 , R E , R F and R G is as defined in Equation (1-d)

[0610]

[0611] (of Equation (1-d-4),

[0612] X 1 Silver is a sulfur atom, -CR E R F or -NR G And;

[0613] *28, *29, R 141 ~R 144 , R 145 , R 146 , R 200 ~R 203 , R E , R F and R G is as defined in Equation (1-d)

[0614] In another specific embodiment, in formula (1-d), R that is not a single bond 141 ~R 148 , and R that is not the single bond mentioned above 200 ~R 203 It can be a hydrogen atom.

[0615] In another specific example, X in Equation (1-d) 1 It can be an oxygen atom or a sulfur atom.

[0616] In another specific embodiment, in formula (1-d), R that is not a single bond E ~R G It can be a hydrogen atom, a methyl group, or a phenyl group.

[0617] In another specific embodiment, the apparatus represented by the above formula (1-e) may be represented by any one of the following formulas (1-e-1) to (1-e-5).

[0618]

[0619]

[0620]

[0621]

[0622]

[0623] In equations (1-e-1) through (1-e-5), each symbol is as defined in equation (1-e).

[0624] In another specific embodiment, in formula (1-e), R that is not a single bond 151 ~R 155 , R 161 ~R 165 and R 171 ~R 175 It can be a hydrogen atom.

[0625] In another embodiment, L1 is an unsubstituted phenylene group, an unsubstituted biphenylylene group, or an unsubstituted naphthylene group.

[0626] In another embodiment, L1 is an unsubstituted phenylene group or an unsubstituted biphenylylene group.

[0627] In another embodiment, L2 is a single bond or an unsubstituted cyclic arylene group having 6 to 12 carbon atoms.

[0628] In another embodiment, L2 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylylene group, or a substituted or unsubstituted naphthylene group.

[0629] In another embodiment, L2 is a single bond, an unsubstituted phenylene group, an unsubstituted biphenylylene group, or an unsubstituted naphthylene group.

[0630] In another embodiment, L2 is a single bond or an unsubstituted phenylene group.

[0631] In another embodiment, L1 is an unsubstituted phenylene group or an unsubstituted biphenylylene group; and L2 is a single bond or an unsubstituted phenylene group.

[0632] 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.

[0633] In addition, deuterium atoms may be intentionally introduced into the inventive compound by using a compound that has been deuterinized in part or all of the raw material compound. Accordingly, in one aspect of the present invention, the inventive compound comprises at least one deuterium atom. That is, the inventive compound may be a compound represented by formula (I), wherein at least one of the hydrogen atoms included in the compound is a deuterium atom.

[0634] 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 described below includes a ratio that takes into account trace amounts of naturally derived isotopes, relative to the ratio obtained by simply counting the number of deuterium atoms represented by the chemical formula.

[0635] The deuterium content of the inventive compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, and even more preferably 50% or more.

[0636] The compound of invention may be a deuterium in which all hydrogen atoms are deuterium atoms (i.e., the deuteriumization rate of the compound of invention is 100%).

[0637] The compound of the invention 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 preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, even more preferably 50% or more, and also less than 100%.

[0638] In addition, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the compound of invention is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, and also 100% or less.

[0639] The details of the substituents (any substituents) in the case of being "substituted or unsubstituted" included in the definition of each of the above formulas are, unless otherwise specifically stated, as described in "substituents in the case of being 'substituted or unsubstituted'."

[0640] The method of manufacturing the compound of the invention is not particularly limited, and a person skilled in the art can easily manufacture it by the method described in the following examples, or by a method modified by referring to known synthesis methods.

[0641] Specific examples of the inventive compound are shown below, but the inventive compound is not limited to the following example compounds.

[0642] In the following specific examples, D represents a deuterium atom.

[0643]

[0644] Example compounds of Formula (I)

[0645]

[0646]

[0647]

[0648]

[0649]

[0650]

[0651]

[0652]

[0653]

[0654]

[0655]

[0656]

[0657]

[0658]

[0659]

[0660]

[0661]

[0662]

[0663]

[0664]

[0665]

[0666]

[0667]

[0668]

[0669]

[0670]

[0671]

[0672]

[0673]

[0674]

[0675]

[0676]

[0677]

[0678]

[0679]

[0680]

[0681]

[0682]

[0683]

[0684]

[0685]

[0686]

[0687]

[0688]

[0689]

[0690]

[0691]

[0692]

[0693]

[0694]

[0695]

[0696]

[0697]

[0698]

[0699]

[0700]

[0701]

[0702]

[0703]

[0704]

[0705]

[0706]

[0707]

[0708]

[0709]

[0710]

[0711]

[0712]

[0713]

[0714]

[0715]

[0716]

[0717]

[0718]

[0719]

[0720]

[0721]

[0722]

[0723]

[0724]

[0725]

[0726]

[0727]

[0728]

[0729]

[0730]

[0731]

[0732]

[0733]

[0734]

[0735]

[0736]

[0737]

[0738]

[0739]

[0740]

[0741]

[0742]

[0743]

[0744]

[0745]

[0746]

[0747]

[0748]

[0749]

[0750] Materials for Organic EL Devices

[0751] A material for an organic EL device according to one embodiment of the present invention preferably comprises the compound of the invention.

[0752] The content of the inventive compound in the organic EL device material is 1 mass% or more (including 100%), preferably 10 mass% or more (including 100%), more preferably 50 mass% or more (including 100%), more preferably 80 mass% or more (including 100%), and particularly preferably 90 mass% or more (including 100%). The organic EL device material of one aspect of the present invention is useful for manufacturing an organic EL device.

[0753] A hole transport layer material according to one embodiment of the present invention preferably comprises the compound of the invention.

[0754] In one aspect of the present invention, the compound of the present invention can also be used as a hole injection layer material.

[0755] In one embodiment of the present invention, the material for an organic EL device preferably further comprises a light hydrogen body of the compound of the present invention. The light hydrogen body is a compound in which all hydrogen atoms in the compound of the present invention are light hydrogen atoms.

[0756] The molar ratio of the inventive compound and the light hydrogen of the inventive compound (inventive compound: light hydrogen) is preferably 10:90 to 90:10, more preferably 20:80 to 80:20, even more preferably 30:70 to 70:30, and particularly preferably 40:60 to 60:40.

[0757]

[0758] Organic EL device

[0759] An organic EL device of one aspect of the present invention comprises an anode, a cathode, and an organic layer formed in a single or multiple layers between the anode and the cathode, wherein the organic layer comprises a light-emitting layer, and at least one of the organic layers comprises the compound of the invention.

[0760] 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 preferably used as a material for a hole transport band or a light-emitting layer of a fluorescent or phosphorescent EL device, more preferably as a material for a hole transport band, even more preferably as a material for a hole injection layer, a hole transport layer, an electron blocking layer, or an exciton blocking layer, and particularly preferably as a material for a hole injection layer or a hole transport layer.

[0761] An organic EL device, which is one embodiment 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, and among these, it is preferable to be a fluorescent light-emitting type device. Here, "light-emitting unit" refers to a minimum unit that includes an organic layer, wherein at least one of the organic layers is a light-emitting layer, and emits light by the recombination of injected holes and electrons.

[0762] For example, the following device configurations can be cited as representative device configurations of simple organic EL devices.

[0763] (1) Anode / Light-emitting unit / Cathode

[0764] 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.

[0765] (a) (hole injection layer / )hole transport layer / fluorescent emitting layer / electron transport layer( / electron injection layer)

[0766] (b) (hole injection layer / )hole transport layer / first fluorescent emitting layer / second fluorescent emitting layer / electron transport layer( / electron injection layer)

[0767] (c) (hole injection layer / )hole transport layer / phosphorescent emitting layer / space layer / fluorescent emitting layer / electron transport layer( / electron injection layer)

[0768] (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)

[0769] (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)

[0770] (f) (hole injection layer / )hole transport layer / electron blocking layer / fluorescent emitting layer / electron transport layer( / electron injection layer)

[0771] (g) (hole injection layer / )hole transport layer / exciton blocking layer / fluorescent emitting layer / electron transport layer( / electron injection layer)

[0772] (h) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent emitting layer / electron transport layer( / electron injection layer)

[0773] (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).

[0774] (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)

[0775] (i1) (hole injection layer / ) 1st hole transport layer / 2nd hole transport layer / 3rd hole transport layer / fluorescent emitting layer / 1st electron transport layer / 2nd electron transport layer( / electron injection layer)

[0776] (j) (hole injection layer / )hole transport layer / fluorescent emitting layer / hole blocking layer / electron transport layer( / electron injection layer)

[0777] (k) (hole injection layer / )hole transport layer / fluorescent emission layer / exciton blocking layer / electron transport layer( / electron injection layer)

[0778] Each of the above phosphorescent or fluorescent emitting layers may exhibit different emission colors. Specifically, in the above-mentioned emitting unit (d), layer configurations such as (hole injection layer / ) hole transport layer / first phosphorescent emitting layer (red emission) / second phosphorescent emitting layer (green emission) / space layer / fluorescent emitting layer (blue emission) / electron transport layer may be used.

[0779] 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.

[0780] Representative device configurations of tandem organic EL devices include the following device configurations.

[0781] (2) Anode / 1st light-emitting unit / intermediate layer / 2nd light-emitting unit / cathode

[0782] Here, the first light-emitting unit and the second light-emitting unit can be selected independently from the light-emitting units described above, for example.

[0783] 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.

[0784] 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 also be used as an electron blocking layer.

[0785] FIG. 1 is a schematic diagram showing an example of the configuration of an organic EL device of the present invention. The organic EL device (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).

[0786] FIG. 2 is a schematic diagram showing another configuration of the organic EL device of the present invention. The organic EL device (11) has a substrate (2), an anode (3), a cathode (4), and a light-emitting unit (20) disposed between the anode (3) and the cathode (4). The light-emitting unit (20) has a light-emitting layer (5). 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).

[0787] FIG. 3 is a schematic diagram showing another configuration of the organic EL device 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).

[0788] 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).

[0789] 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.

[0790]

[0791] substrate

[0792] The substrate is used as a support for the organic EL device. As a substrate, for example, a plate made of glass, quartz, plastic, etc., may be used. In addition, a flexible substrate may be used. Examples of flexible substrates include plastic substrates selected from the group consisting of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. In addition, an inorganic deposition film may be used.

[0793]

[0794] anode

[0795] For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a large work function (specifically 4.0 eV or more). 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), or nitrides of the above metals (e.g., titanium nitride).

[0796] 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.

[0797]

[0798] Precision transport band

[0799] 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 inventive compound. It is preferable that at least one of these layers constituting the hole transport band includes the inventive compound, and it is particularly more preferable that the hole transport layer includes the inventive compound.

[0800] 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 commonly used as electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0801] 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) or cesium (Cs), alkaline earth metals like magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals like europium (Eu) and ytterbium (Yb), and alloys containing these may also be used. Meanwhile, when forming an anode using alkali metals, alkaline earth metals, and alloys containing these, vacuum deposition or sputtering methods may be used. Also, when using silver paste, etc., coating methods or inkjet methods may be used.

[0802]

[0803] Hole injection layer

[0804] 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.

[0805] As hole-injecting materials other than the inventive compound, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. can be used.

[0806] 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.

[0807] 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.

[0808] In addition, it is also desirable to use an acceptor material such as a hexa-azatriphenylene (HAT) compound represented by the following formula (K).

[0809]

[0810] (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 selected from may combine to form a group represented as -CO-O-CO-.)

[0811] R 227 Examples include methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, isobutyl groups, t-butyl groups, cyclopentyl groups, cyclohexyl groups, etc.

[0812]

[0813] Precision transport layer

[0814] 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.

[0815] 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 sequentially 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.

[0816] In one aspect of the present invention, the hole transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, and 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, is preferably adjacent to the light-emitting layer. In one example, the light-emitting layer and the second hole transport layer may be in direct contact.

[0817] In another aspect of the present invention, an electron blocking layer described below may be interposed between the hole transport layer and the light-emitting layer of the single-layer structure, or between the hole transport layer closest to the light-emitting layer among the multilayer structures. Additionally, 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.

[0818] In one embodiment of an organic electroluminescent device according to the present invention, one or both of the first hole transport layer and the second hole transport layer comprise 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 another embodiment, at least one of the first to third hole transport layers comprises the inventive compound. Specifically, when the hole transport layer has a three-layer structure, the inventive compound may be included in only one of the first to third hole transport layers, in only two of them, or in all of them.

[0819] In one aspect of the present invention, it is preferable that the second hole transport layer comprises the inventive compound. Specifically, it is preferable that the inventive compound is included only in the second hole transport layer, or that the inventive compound is included in both the first hole transport layer and the second hole transport layer.

[0820] In one aspect of the present invention, the inventive compound included in one or both of the first hole transport layer and the second hole transport layer, or included in at least one of the first to third hole transport layers, may be a light hydrogen body from the perspective of manufacturing cost.

[0821] The above light hydrogen body is an inventive compound in which all hydrogen atoms in the inventive compound are light hydrogen atoms.

[0822] Accordingly, the present invention comprises an organic EL device comprising an inventive compound in which one or both of the first hole transport layer and the second hole transport layer, or at least one of the first to third hole transport layers, is substantially composed only of a light hydrogen. "Inventive compound substantially composed only of a light hydrogen" means that the content ratio of the light hydrogen to the total amount of the inventive compound is 90 mol% or more, preferably 95 mol% or more, more preferably 99 mol% or more (each including 100%).

[0823] As hole transport layer materials other than the inventive compound, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used.

[0824] As aromatic amine compounds, for example, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated: NPB) or 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). The above compound is 10 -6 cm 2 It has a positive mobility of / Vs or higher.

[0825] Examples of carbazole derivatives 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-anthryl)phenyl]-9H-carbazole (abbreviated: PCzPA).

[0826] 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).

[0827] Polymeric compounds such as poly(N-vinylcarbazole) (abbreviated: PVK) or poly(4-vinyltriphenylamine) (abbreviated: PVTPA) may also be used.

[0828] However, if the compound has higher hole transport than electron transport, compounds other than the above may be used.

[0829] In one form of an 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).

[0830]

[0831] [Among the above formulas (21) and (22),

[0832] 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

[0833] k is 1, 2, 3, or 4, and

[0834] 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

[0835] If k is 2, 3, or 4, multiple L E2 are identical to each other, or different,

[0836] 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,

[0837] 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

[0838] A 1 , B 1 , C 1 , A 2 , B 2 , C 2 , and D 2 is, each independently, 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,

[0839] R' 901 , R' 902 and R' 903 Each is independently a substituted or unsubstituted cyclic aryl group having 6 to 50 carbon atoms, and

[0840] R' 901 If this plural exists, the plural R' 901 are identical to each other, or different,

[0841] R' 902 If there are multiple instances of R' 902 are identical to each other, or different,

[0842] R' 903 If this plural exists, the plural R' 903 [They are identical or different from each other.]

[0843] Additionally, 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).

[0844] In Equations (21) and (22), A 1 , B 1 , C 1 , A 2 , B 2 , C 2 , and D 2 Preferably, each independently selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.

[0845] Also, more preferably, in formula (21), A 1 , B 1 and C 1 At least one of, and, in Equation (22), A 2 , B 2 , C 2 and D 2 At least one of them is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0846] A 1 , B 1 , C 1 , A 2 , B 2 , C 2 , and D 2The fluorene group that can be taken may have a substituent at the 9 position, for example, a 9,9-dimethylfluorene group or a 9,9-diphenylfluorene group. In addition, the substituents at the 9 position may form a ring with each other, for example, the substituents at the 9 position may form a fluorene backbone or a xanthen backbone with each other.

[0847] L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 The group is, preferably, independently, a single bond, substituted or unsubstituted cyclic arylene group having 6 to 12 carbon atoms.

[0848] Specific examples of compounds represented by formulas (21) and (22) include, for instance, the following compounds.

[0849]

[0850]

[0851] dopant material of the light-emitting layer

[0852] 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 or phosphorescent emitting materials can be used as dopant materials. Fluorescent emitting materials are compounds that emit light from a singlet excited state, and phosphorescent emitting materials are compounds that emit light from a triplet excited state.

[0853] In one aspect of the organic EL device according to the present invention, the light-emitting layer is a single layer.

[0854] In addition, in another aspect of the organic EL device according to the present invention, the light-emitting layer comprises a first light-emitting layer and a second light-emitting layer.

[0855] As blue fluorescent light-emitting materials that can be used in the light-emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc., can be used. Specifically, 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., can be used.

[0856] As a green fluorescent light-emitting material usable in the light-emitting layer, aromatic amine derivatives, etc., may be used. 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.

[0857] As red fluorescent light-emitting materials that can be used in the light-emitting layer, tetracene derivatives, diamine derivatives, etc. may be used. Specifically, 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), etc. may be used.

[0858] In one aspect of the present invention, it is preferable that the light-emitting layer comprises a fluorescent light-emitting material (fluorescent dopant material).

[0859] Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used as blue phosphorescent materials that can be used in the light-emitting layer. 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).

[0860] Iridium complexes are used as green phosphorescent materials that can be used in the light-emitting layer. 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)).

[0861] Metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used as red phosphorescent materials that can be used in the emissive layer. 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).

[0862] 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).

[0863]

[0864] Host material of the light-emitting layer

[0865] 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.

[0866] As a host material, for example

[0867] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes,

[0868] (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives,

[0869] (3) Condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives,

[0870] (4) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives are used.

[0871] 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);

[0872] 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);

[0873] 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

[0874] 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), 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) may be used. Multiple types of host materials may be used.

[0875] In particular, for blue fluorescent devices, it is preferable to use the following anthracene compound as a host material.

[0876]

[0877]

[0878]

[0879]

[0880]

[0881] In one aspect of an organic EL device according to the present invention, when the light-emitting layer comprises 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, a dopant material included in the first light-emitting layer may be different from the dopant material included in the second light-emitting layer, or a host material included in the first light-emitting layer may be different from the host material included in the second light-emitting layer.

[0882] In the organic EL device of the present invention, the light-emitting layer may contain a light-emitting compound that exhibits fluorescent light emission with a main peak wavelength of 500 nm or less.

[0883] 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.

[0884] 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).

[0885] 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.

[0886] 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 may be emitting compounds that exhibit fluorescent emission with a main peak wavelength of 500 nm or less.

[0887] 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, or both emitting layers may include emitting compounds that exhibit fluorescent emission with a main peak wavelength of 500 nm or less. 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, or both 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, or both materials may be emitting compounds that exhibit fluorescent emission with a main peak wavelength of 500 nm or less.

[0888]

[0889] Electron transport layer

[0890] 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.

[0891] 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.

[0892] In the electron transport layer, for example,

[0893] (1) Metal complexes such as aluminum complexes, beryllium complexes, zinc complexes, etc.

[0894] (2) Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, etc.

[0895] (3) Polymer compounds can be used.

[0896] As metal complexes, for example, 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), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviated: ZnBTZ), (8-quinolinoleate)lithium (abbreviated: Liq) can be cited.

[0897] As heteroaromatic compounds, for example, 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), vasocuproin (abbreviation: BCP), Examples include 4,4'-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviated: BzOs).

[0898] Examples of polymer compounds include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated: PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated: PF-BPy).

[0899] The above material is 10 -6 cm 2It 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 materials. 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.

[0900]

[0901] electron injection layer

[0902] 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. Examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes such as (8-quinolinoleate) 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.

[0903] 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.

[0904] Alternatively, a composite material formed by mixing an organic compound and an electron donor (donor) may be used in the electron injection layer. Such a composite material exhibits excellent electron injection and electron transport properties because the organic compound receives electrons from the electron donor. In this case, it is preferable that the organic compound be a material with 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 toward the organic compound is sufficient. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples include lithium, cesium, magnesium, calcium, erbium, and ytterbium. Additionally, alkali metal oxides or alkaline earth metal oxides are preferred, and examples include lithium oxide, calcium oxide, and barium oxide. Furthermore, Lewis bases such as magnesium oxide may be used. Additionally, organic compounds such as tetrathiafulvalene (abbreviated as TTF) may be used.

[0905]

[0906] cathode

[0907] For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof that have a small work function (specifically 3.8 eV or less). 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), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.

[0908] 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.

[0909] 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.

[0910]

[0911] insulating layer

[0912] 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.

[0913] Examples of materials used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, etc. Meanwhile, mixtures or laminates of these may also be used.

[0914]

[0915] Space layer

[0916] 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.

[0917] Since the space layer is provided between the emitting layers, it is desirable that the material 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 that the triplet energy 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.

[0918]

[0919] low-lying area

[0920] 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. An exciton blocking layer has the function of trapping excitons within the emitting layer by preventing excitons generated in the emitting layer from diffusing into surrounding layers.

[0921]

[0922] Each layer of the above organic EL device can be formed by conventionally known deposition methods, coating methods, etc. For example, it can be formed by known methods such as deposition methods including vacuum deposition and molecular beam deposition (MBE), or coating methods including dipping, spin coating, casting, bar coating, and roll coating using a solution of a compound that forms the layer.

[0923] The film thickness of each layer is not particularly limited, 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, which reduces efficiency, so it is typically 5 nm to 10 μm, and 10 nm to 0.2 μm is more preferable.

[0924] In the organic EL device having a hole transport layer 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 preferably 30 nm to 150 nm, more preferably 40 nm to 130 nm.

[0925] In addition, in one aspect of the organic EL device of the present invention, the thickness of the second hole transport layer is preferably 5 nm or more, and also preferably 100 nm or less.

[0926] In addition, in one aspect of the organic EL device of the present invention, the thickness of the hole transport layer adjacent to the light-emitting layer is preferably 5 nm or more, and also preferably 100 nm or less.

[0927] 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 만족시킨다. 바람직하게는 0.5<D2 / D1<3.5의 관계를 만족시키고, 보다 바람직하게는 0.75<D2 / D1<3.0의 관계를 만족시킨다.

[0928] As a preferred embodiment of the organic EL device of the present invention, for example,

[0929] As an organic EL device having a two-layer hole transport layer,

[0930] · A first embodiment in which the second hole transport layer comprises the inventive compound and the first hole transport layer does not comprise the inventive compound;

[0931] · A second embodiment in which both the first hole transport layer and the second hole transport layer comprise the inventive compound;

[0932] · A third embodiment in which the first hole transport layer comprises the inventive compound and the second hole transport layer does not comprise the inventive compound;

[0933] As an organic EL device having a hole transport layer with a three-layer structure,

[0934] · A fourth embodiment in which the first hole transport layer comprises the inventive compound, and the second and third hole transport layers do not comprise the inventive compound;

[0935] · A fifth embodiment in which the second hole transport layer comprises the inventive compound, and the first and third hole transport layers do not comprise the inventive compound;

[0936] · A sixth embodiment in which the third hole transport layer comprises the inventive compound, and the first and second hole transport layers do not comprise the inventive compound;

[0937] · A seventh embodiment in which the first and second hole transport layers comprise the inventive compound, and the third hole transport layer does not comprise the inventive compound;

[0938] · Eighth embodiment in which the first and third hole transport layers comprise the inventive compound, and the second hole transport layer does not comprise the inventive compound;

[0939] · A ninth embodiment in which the second and third hole transport layers comprise the inventive compound, and the first hole transport layer does not comprise the inventive compound;

[0940] · A 10th embodiment in which all of the first to third hole transport layers comprise the inventive compound; etc.

[0941]

[0942] electronic devices

[0943] 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 and light-emitting devices for vehicle lighting fixtures.

[0944] Accordingly, an electronic device according to one embodiment includes the organic electroluminescent element.

[0945]

[0946] The present invention will be explained in more detail below using examples, but the present invention is not limited to the following examples.

[0947]

[0948] The compound represented by formula (I) used in the manufacture of the organic EL devices of Examples 1 to 9 is shown below.

[0949]

[0950]

[0951]

[0952]

[0953] The comparative compounds used in the manufacture of the organic EL device of Comparative Example 1 are shown below.

[0954]

[0955]

[0956] Other compounds used in the manufacture of the organic EL devices of Examples 1 to 9 and Comparative Example 1 are shown below.

[0957]

[0958]

[0959]

[0960]

[0961] Fabrication of Organic EL Devices

[0962] An organic EL device was fabricated and evaluated as follows.

[0963]

[0964] Example 1

[0965] 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.

[0966] After cleaning, the glass substrate with the ITO transparent electrode attached was mounted in the substrate holder of the vacuum deposition apparatus, and the transparent electrode was placed over the side on which the transparent electrode was formed first, so that compound HT-1 and compound HA 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 HA (HT-1:HA) was 97:3.

[0967] Next, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer with a film thickness of 80 nm.

[0968] Next, compound Inv-1 was deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 10 nm.

[0969] Next, compound BH-1 and compound BD-1 were co-deposited on the second hole transport layer to form an emissive layer with a film thickness of 25 nm. The mass ratio of compound BH-1 and compound BD-1 (BH-1:BD-1) was 96:4.

[0970] Next, compound ET-1 was deposited on the light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[0971] Next, compound ET-2 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer with a film thickness of 20 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50. Liq is an abbreviation for (8-quinolinolato)lithium.

[0972] Next, LiF was deposited on the second electron transport layer to form an electron injection electrode with a film thickness of 1 nm.

[0973] Then, metal Al was deposited on the electron injection electrode to form a metal cathode with a film thickness of 50 nm.

[0974] The device configuration of the organic EL device of Example 1 is briefly shown as follows.

[0975] ITO(130) / HT-1:HA=97:3(10) / HT-1(80) / Inv-1(10) / BH-1:BD-1=96:4(25) / ET-1(5) / ET-2:Liq=50:50(20) / LiF(1) / Al(50)

[0976] In the above device configuration, the number in parentheses is the film thickness (nm), and the ratio is the mass ratio of the compounds used.

[0977]

[0978] Examples 2 to 9

[0979] The organic EL devices of Examples 2 to 9 were fabricated in the same manner as Example 1, except that the compounds shown in Table 1 below were used instead of the compound Inv-1 in Example 1.

[0980]

[0981] Comparative Example 1

[0982] The organic EL device of Comparative Example 1 was fabricated in the same manner as Example 1, except that the compound shown in Table 1 below was used instead of the compound Inv-1 in Example 1.

[0983]

[0984] Evaluation of Organic EL Devices

[0985] The following evaluations were performed on the fabricated organic EL device. The evaluation results are shown in Table 1.

[0986]

[0987] Measurement of 95% lifespan (LT95)

[0988] Current density is 50 mA / cm² 2 A voltage was applied to the organic EL device to achieve this, and a 95% lifespan (LT95) evaluation was performed. Here, LT95 refers to the time (hr) until the brightness drops to 95% of the initial brightness when driven by a constant current.

[0989]

[0990]

[0991]

[0992] As is evident from the results of Table 1, it can be seen that an organic EL device containing any one of the inventive compounds Inv-1 to Inv-9 has a 95% higher lifetime than an organic EL device containing the comparative compound Ref-1.

[0993]

[0994] Synthesis of Intermediate Compounds

[0995]

[0996] Intermediate Synthesis Example 1: Synthesis of Intermediate A-1

[0997]

[0998] Ingredient 1: Naphtho[2,1-b]benzofuran-11-yl trifluoromethanesulfonic acid (3.66 g, 10 mmol)

[0999] Ingredient 2: (4-Bromophenyl)boronic acid (2.01g, 10mmol)

[1000] Catalyst: Bis(triphenylphosphine)palladium(II) dichloride (0.14 g, 0.2 mmol)

[1001] Base: 2M aqueous potassium carbonate solution (15mL)

[1002] Solvent: 1,2-Dimethoxyethane (DME) (50 mL)

[1003] The mixture of the above components was refluxed at the boiling point for 3 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 2.65 g of a white solid. The yield was 71%.

[1004]

[1005] Intermediate Synthesis Examples 2 to 7: Synthesis of Intermediates A-2 to A-7

[1006] Intermediates A-2 to A-7 were each synthesized in the same manner as intermediate A-1, except that raw materials 1 and 2 were changed to those shown in Table 2 below.

[1007]

[1008] Intermediates A-1 to A-7 are shown in Table 2 along with raw materials 1, 2 and yields.

[1009]

[1010]

[1011] Synthesis of Second Hole Transport Layer Compounds

[1012]

[1013] Synthesis Example 1: Synthesis of Compound 1 (Inv-1)

[1014]

[1015] Intermediate A: Intermediate A-1 (3.73g, 10mmol)

[1016] Intermediate B: N-([1,1'-biphenyl]-4-yl)-2'-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine (4.87 g, 10 mmol)

[1017] Catalyst: Tris(dibenzylideneacetone)dipalladium(0) (0.183g, 0.2mmol)

[1018] Ligand: Tri-tert-butylphosphonium tetrafluoroborate (0.232 g, 0.8 mmol)

[1019] Base: Sodium-t-butoxide (1.44 g, 15 mmol)

[1020] Solvent: Xylene (50mL)

[1021] The mixture of the above components was refluxed at the boiling point for 3 hours. After cooling the reaction solution to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain 5.73 g of a white solid. The yield was 69%. Mass spectrum analysis of the obtained substance revealed it to be Compound 1, with a molecular weight of 778.96 and m / e = 779.

[1022]

[1023] Synthesis Examples 2 to 9: Synthesis of Compounds 2 (Inv-2) to Compound 9 (Inv-9)

[1024] Compounds 2 to 9 (Inv-2 to Inv-9) were each synthesized in the same manner as in Synthesis Example 1, except that intermediates A and B of Synthesis Example 1 were changed to those shown in Table 3 below.

[1025]

[1026] Compounds 1 to 9 are shown in Table 3 along with the raw materials intermediates A and B and their yields.

[1027]

[1028]

Claims

Compound represented by the following formula (I): Among the formula (I), L1 is an unsubstituted cyclic arylene group having 6 to 12 carbon atoms; L2 is a single bond, or a substituted or unsubstituted cyclic arylene group having 6 to 12 carbon atoms; R a and R e Each is independently a hydrogen atom; R b , R c and R d One of them is a group represented by the following formula (1) or (2), and the other two are each independently hydrogen atoms; (of Equations (1) and (2), One selected from R1~R4 is a single bond connected to *, and the other three are each independently hydrogen atoms; R5~R 10 Each is independently a hydrogen atom; R1~R4 and R5~R, which are not the single combination mentioned above 10 Each of them does not combine with each other and therefore does not form a ring. Ar1 is a device represented by the following formula (3) or (4); (Essence (3), R 11 ~R 18 Each is independently a hydrogen atom, and R 11 ~R 18 Each of them does not combine with each other and therefore does not form a ring. (Equation (4), X is O or S and; R 21 ~R 24 Each is independently a hydrogen atom; R 21 ~R 24 Two adjacent atoms selected from can combine with each other to form a cyclic condensed ring having 6 to 10 carbon atoms; R 25 ~R 28 One selected from is a single bond connected to *, and the other three are each independently hydrogen atoms) However, if Ar1 is represented by the above equation (4), R b , R c and R d One of them is a device represented by the above equation (2), and in the above equation (2), R4 is a single connection connected to *, and Ar2 is a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms (excluding pyreneyl groups), or a substituted or unsubstituted cyclic heterocyclic group having 5 to 30 atoms (excluding carbazole-9-yl groups and naphthobenzofuranyl groups), and In the definition of each substituent in Formula (I), "non-substituent" means that the hydrogen atom is not substituted with a substituent, and the hydrogen atom is a light hydrogen atom, a deuterium atom, or a tritium atom. 　 In Article 1, L1 is a compound in which the unsubstituted phenylene group or unsubstituted biphenyllylene group. 　 In Article 1, L2 is a compound in which the bond is a single bond or an unsubstituted phenylene group. 　 In Article 1, Ar2 is a compound represented by the following formulas (1-a), (1-b), (1-c), (1-d) or (1-e): (of Equation (1-a), *21 is a single bond that bonds to L2, and if L2 is a single bond, *21 bonds to the central nitrogen atom; 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 combination that combines to *23; R other than the above single bond 101 ~R 110 Each is independently a hydrogen atom or an unsubstituted C1- to C10 alkyl group; R 111 ~R 115 Each is independently a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, a substituted or unsubstituted cyclic C6-12 aryl group, or a substituted or unsubstituted cyclic 5-13 heterocyclic group; u is 0 to 2, and v is 0 or 1; When u is 0, *22 is a single bond bonded to L2, and when u is 0 and L2 is a single bond, *22 is bonded to the central nitrogen atom; When both u and v are 0, *23 is a single bond bonded to L2, and when both u and v are 0 and L2 is a single bond, *23 is bonded to the central nitrogen atom. (of Equation (1-b), *24 is a single bond that bonds to L2, and if L2 is a single bond, *24 bonds to the central nitrogen atom; R 121 ~R 128 One selected from is a single combination that combines to *25; R other than the above single bond 121 ~R 128 Each is independently a hydrogen atom, a substituted or unsubstituted C1- to C10 alkyl group, or a substituted or unsubstituted cyclic C6- to C12 aryl group) (of Equation (1-c), *26 is a single bond that bonds to L2, and if L2 is a single bond, *26 bonds to the central nitrogen atom; R 131 ~R 140 One selected from is a single combination that combines to *27; R other than the above single bond 131 ~R 140 Each is independently a hydrogen atom, a substituted or unsubstituted C1- to C10 alkyl group, or a substituted or unsubstituted cyclic C6- to C12 aryl group) (of Equation (1-d), *28 is a single bond that bonds to L2, and if L2 is a single bond, *28 bonds to the central nitrogen atom; X 1 Silver oxygen atom, sulfur atom, -CR E R F or -NR G And; p is 0 or 1 and; When p is 0, R 141 ~R 148 , R E , R F and R G One selected from is a single combination that combines to *29; p is 1, and X 1 This -CR E R F or -NR G In the case of, R 145 and R 146 , R 146 and R 147 , or R 147 and R 148 One of them is a single bond binding to *d, the other is a single bond binding to *e, and R is not a single bond binding to *d or *e. 145 ~R 148 , R 141 ~R 144 , R 200 ~R 203 , R E , R F and R G One selected from is a single combination that combines to *29; p is 1, and X 1 If this is an oxygen atom or a sulfur atom, R 145 and R 146 , R 146 and R 147 , or R 147 and R 148 One side is a single bond bonding to *d, the other side is a single bond bonding to *e, and R 141 to R 144 One selected from is a single combination that combines to *29; R other than the above single bond 141 ~R 148 , R other than the above single bond 200 ~R 203 , and R that is not the single bond mentioned above E ~R G Each is independently a hydrogen atom, a substituted or unsubstituted C1-10 alkyl group, a substituted or unsubstituted C6-12 aryl group, or a substituted or unsubstituted C5-13 heterocyclic group) (of Equation (1-e), *30 is a single bond that bonds to L2, and if L2 is a single bond, *30 bonds to the central nitrogen atom; R 151 ~R 155 One selected from is a single bond that combines to *31, and the other is a single bond that combines to *32; R other than the above single bond 151 ~R 155 Each is independently a hydrogen atom, an unsubstituted C1- to C10 alkyl group, or an unsubstituted phenyl group; R 161 ~R 165 and R 171 ~R 175 Each is independently a hydrogen atom or an unsubstituted C1- to C10 alkyl group; R, not a hydrogen atom 161 to R 165 At least one pair of adjacent 2 selected from can combine with each other to form one or more unsubstituted benzene rings; R, not a hydrogen atom 171 to R 175 At least one pair of adjacent two selected from can combine with each other to form one or more unsubstituted benzene rings.) 　 In Article 4, Among Equation (1-d), When p is 0, R 141 ~R 148 , R E and R F One selected from is a single combination that combines to *29; When p is 1, X 1 Silver is a sulfur atom, -CR E R F , or -NR G Phosphorus compound. 　 A material for an organic electroluminescent device comprising a compound described in any one of claims 1 to 5. 　 A hole transport layer material comprising a compound described in any one of claims 1 to 5. 　 An organic electroluminescent device comprising an anode, a cathode, and an organic layer formed as a single or multiple layers between the anode and the cathode, The above organic layer includes a light-emitting layer, and An organic electroluminescent device comprising at least one of the above organic layers, the compound described in any one of claims 1 to 5. 　 In Article 8, The organic layer comprises a hole transport band between the anode and the light-emitting layer, and the hole transport band comprises the compound in an organic electroluminescent device. 　 In Article 9, The above hole transport band includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side, and one or both of the first hole transport layer and the second hole transport layer include the compound, forming an organic electroluminescent device. 　 In Article 10, An organic electroluminescent device in which the second hole transport layer comprises the compound. 　 In Article 10, An organic electroluminescent device in which the light-emitting layer and the second hole transport layer are in direct contact. 　 In Article 10, An organic electroluminescent device in which the sum of the thickness of the first hole transport layer and the thickness of the second hole transport layer is 30 nm to 150 nm. 　 In Article 8, The above-mentioned light-emitting layer is a single layer organic electroluminescent device. 　 In Article 8, The above-described light-emitting layer is an organic electroluminescent device containing a light-emitting compound that exhibits fluorescent light emission with a main peak wavelength of 500 nm or less. 　 In Article 8, An organic electroluminescent device in which the above-mentioned light-emitting layer comprises a fluorescent dopant material. 　 An electronic device comprising an organic electroluminescent element as described in claim 8.

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