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

Abstract

The present invention provides a compound represented by formula (I) or (II) which further improves the performance of an organic EL device, a material for an organic electroluminescent device, comprising the compound, an organic electroluminescent device having further improved device performance which comprises the compound, 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 the compound, an organic electroluminescent device, and an electronic device comprising the organic electroluminescent device.

[0002] In general, an organic electroluminescence device (hereinafter sometimes 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 are injected from the cathode side and holes are injected from the anode side into the light-emitting region. The injected electrons and holes recombine in the light-emitting region to generate an excited state, and light is emitted when the excited state returns to the ground state. Therefore, the development of a material that efficiently transports electrons or holes to the light-emitting region and facilitates the recombination of electrons and holes is important for obtaining a high-performance organic EL device.

[0003] Patent documents 1 to 8 disclose compounds used as materials for organic electroluminescent devices.

[0004] [Prior Art Literature]

[0005] (Patent Document 1) PCT Publication No. 2010 / 140617 (WO2010140617A1)

[0006] (Patent Document 2) PCT Publication No. 2022 / 035097 (WO2022035097A1)

[0007] (Patent Document 3) PCT Publication No. 2020 / 226298 (WO2020226298A1)

[0008] (Patent Document 4) PCT Publication No. 2023 / 140529 (WO2023140529A1)

[0009] (Patent Document 5) Japanese Patent Publication No. 2010-150167 (JP2010150167A)

[0010] (Patent Document 6) Japanese Patent Publication No. 2010-064963 (JP2010064963A)

[0011] (Patent Document 7) Japanese Patent Publication No. 2014-047197 (JP2014047197A)

[0012] (Patent Document 8) Korean Patent Publication No. 2023-0056865 (KR20230056865A)

[0013] Although many compounds for organic EL devices have been reported, compounds that further improve the performance of organic EL devices are still in demand.

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

[0015] The present inventors have repeatedly conducted extensive research on the performance of organic EL devices containing novel compounds, and have found that organic EL devices containing a compound represented by the following formula (I) and organic EL devices containing a compound represented by the following formula (II) have improved performance.

[0016] In one aspect, the present invention provides a compound represented by the following formula (I).

[0017]

[0018] In formula (I),

[0019] R1 and R2 are each independently a methyl group or a phenyl group, but not both are phenyl groups;

[0020] Two adjacent ones selected from R3 to R6 are bonded to a and b, respectively;

[0021] R3 to R6, which are not bonded to the above a and b, are hydrogen atoms;

[0022] L is a single bond or a phenylene group;

[0023] L1 is a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms;

[0024] Ar1 is substituted or unsubstituted , substituted or unsubstituted , or substituted or unsubstituted and;

[0025] A is a substituted or unsubstituted aryl group having 12 to 17 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 12 to 17 ring atoms;

[0026] X is an oxygen atom or -CR 7 R 8 and R 7 and R 8 are each independently a methyl group or a phenyl group, or R 7 and R 8 combine with each other to form a spiro ring;

[0027] Ar2 is represented by the following formula (1-a), (1-b), (1-c), (1-d) or (1-e).

[0028]

[0029] (In equation (1-a),

[0030] *21 is a single bond bonding to L1, and when L1 is a single bond, *21 is bonded to the central nitrogen atom;

[0031] R 101 ~R 105 One selected from is a single bond binding to *22, and R 106 ~R 110 One selected from is a single bond binding to *23;

[0032] R, which is not a single bond 101 ~R 105 and R 106 ~R 110are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms;

[0033] R 111 ~R 115 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 13 ring atoms;

[0034] u is 0 to 2, v is 0 or 1, but at least one of u and v is not 0)

[0035]

[0036] (In equation (1-b),

[0037] *24 is a single bond bonding to L1, and when L1 is a single bond, *24 is bonded to the central nitrogen atom;

[0038] R 121 ~R 128 One selected from is a single bond binding to *25;

[0039] R, which is not a single bond 121 ~R 128 are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms)

[0040]

[0041] (In equation (1-c),

[0042] *26 is a single bond bonding to L1, and when L1 is a single bond, *26 is bonded to the central nitrogen atom;

[0043] R 131 ~R 140 One selected from is a single bond binding to *27;

[0044] R, which is not a single bond 131 ~R 140are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.

[0045]

[0046] (In equation (1-d),

[0047] *28 is a single bond bonding to L1, and when L1 is a single bond, *28 is bonded to the central nitrogen atom;

[0048] X 1 Silver oxygen atom, sulfur atom, -CR E R F or -NR G and;

[0049] p is 0 or 1;

[0050] p is 0, X 1 This oxygen atom, sulfur atom, -CR E R F or -NR G When, R 141 ~R 148 and R G One selected from is a single bond binding to *29;

[0051] p is 1, and X 1 This -CR E R F or -NR G If , R 145 Wow R 146 , R 146 and R 147 , or R 147 and R 148 R is a single bond where one side is bonded to *d, the other side is bonded to *e, and is not a single bond bonded to *d or *e. 145 ~R 148 , R 141 ~R 144 , and R 200 ~R 203 One selected from is a single bond binding to *29;

[0052] p is 1, and X 1 If this is an oxygen atom or a sulfur atom, R 145 Wow R 146 , R 146 and R 147 , or R 147 and R 148 One side of R is a single bond bonded to *d, the other side is a single bond bonded to *e, and R 141 Inland R 144 One selected from is a single bond binding to *29;

[0053] R, which is not a single bond 141 ~R 148 , R, which is not a single bond 200 ~R 203 , and R which is not a single bond G , the above R E , and the above R F are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 13 ring atoms;

[0054] Just p is 0 and X 1 This -CR E R F If R E is a methyl group and R F is a methyl group or a phenyl group)

[0055]

[0056] (In equation (1-e),

[0057] *30 is a single bond bonding to L1, and if L1 is a single bond, *30 is bonded to the central nitrogen atom;

[0058] R 151 ~R 155 One selected from is a single bond binding to *31, and R 151 ~R 155 Another one selected from is a single bond binding to *32;

[0059] R, which is not a single bond 151 ~R 155 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group;

[0060] R 161 ~R 165 and R 171 ~R 175 are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms;

[0061] R, not a hydrogen atom 161 Inland R 165 At least two adjacent ones selected from can combine with each other to form one or more unsubstituted benzene rings;

[0062] R, not a hydrogen atom 171 Inland R 175 At least two adjacent ones selected from can combine with each other to form one or more unsubstituted benzene rings)

[0063] In another aspect, the present invention provides a compound represented by the following formula (II).

[0064]

[0065] In formula (II),

[0066] R1, R2, R7 and R8 are each independently a methyl group or a phenyl group, or R1 and R2, or R7 and R8 are combined with each other to form a spiro ring;

[0067] Two adjacent ones selected from R3 to R6 are bonded to a and b, respectively;

[0068] R9~R 12 Two adjacent ones selected from are bonded to c and d respectively;

[0069] R3 to R6 that do not bind to the above a and b, and R9 to R that do not bind to the above c and d 12 is a hydrogen atom;

[0070] L is each independently a single bond or a phenylene group;

[0071] Ar1 is substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , or substituted or unsubstituted However, when the above Ar1 has two or more substituents, the substituents can combine with each other to form a condensed ring (provided that X is -CR 13 R 14 (except in this case)

[0072] A is a substituted or unsubstituted aryl group having 5 or more ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 or more ring atoms;

[0073] X is an oxygen atom, a sulfur atom, or -CR 13 R 14 and;

[0074] R 13 and R 14 are each independently a methyl group or a phenyl group, or R 13 and R 14 They combine with each other to form spirocycles.

[0075] In another aspect, the present invention provides a material for an organic electroluminescent device comprising a compound represented by the above formula (I) or a compound represented by the above formula (II).

[0076] In another aspect, the present invention provides an organic electroluminescent device 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 includes a light-emitting layer, and at least one of the organic layers includes a compound represented by the formula (I) or a compound represented by the formula (II).

[0077] In another aspect, the present invention provides an electronic device including the organic electroluminescent device.

[0078] An organic EL device comprising a compound represented by the above formula (I) or a compound represented by the above formula (II) exhibits improved device performance.

[0079]

[0080] FIG. 1 is a schematic diagram showing an example of the layer configuration of an organic EL device according to one aspect of the present invention.

[0081] FIG. 2 is a schematic diagram showing another example of the layer configuration of an organic EL device according to another aspect of the present invention.

[0082] FIG. 3 is a schematic diagram showing another example of the layer configuration of an organic EL device according to another aspect of the present invention.

[0083]

[0084] [definition]

[0085] In this specification, the term "hydrogen atom" includes isotopes having different numbers of neutrons, i.e., protium, deuterium, and tritium.

[0086] In this specification, in the chemical structural formula, a hydrogen atom, i.e., a light hydrogen atom, a deuterium atom, or a tritium atom, is bonded to a bondable position where a symbol such as “R” or “D” representing a deuterium atom is not specified.

[0087] In this specification, the number of ring carbon atoms 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., a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted by a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below shall be the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. In addition, for example, a 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and a 9,9'-spirobifluorenyl group has 25 ring carbon atoms.

[0088] In addition, when a benzene ring is substituted with, for example, an alkyl group as a substituent, the carbon number of the alkyl group is not included in the number of ring-forming carbon atoms of the benzene ring. Therefore, the number of ring-forming carbon atoms 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 as a substituent, the carbon number of the alkyl group is not included in the number of ring-forming carbon atoms of the naphthalene ring. Therefore, the number of ring-forming carbon atoms of the naphthalene ring substituted with an alkyl group is 10.

[0089] In this specification, the number of ring-forming atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a condensed ring, and a ring set). Atoms that do not constitute a ring (e.g., a hydrogen atom terminating a bond of atoms constituting a ring) or atoms contained in a substituent when the ring is substituted by a substituent are not included in the number of ring-forming atoms. The same applies to the “number of ring-forming atoms” described below unless otherwise specified. 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, the number of hydrogen atoms bonded to a pyridine ring or the number of atoms constituting a substituent are not included in the number of pyridine ring-forming atoms. Therefore, the number of ring atoms of the pyridine ring to which the hydrogen atom or substituent is bonded is 6. In addition, for example, the hydrogen atom bonded to the carbon atom of the quinazoline ring or the atoms forming the substituent are not included in the number of ring atoms of the quinazoline ring. Therefore, the number of ring atoms of the quinazoline ring to which the hydrogen atom or substituent is bonded is 10.

[0090] In this specification, in the expression "ZZ group having XX to YY carbon atoms, substituted or unsubstituted", "carbon atoms XX to YY" indicates the carbon number when the ZZ group is unsubstituted, and does not include the carbon number of the substituent when substituted. Here, "YY" is larger than "XX", "XX" means an integer greater than or equal to 1, and "YY" means an integer greater than or equal to 2.

[0091] In this specification, in the expression "ZZ group having a substituted or unsubstituted atomic number XX to YY", "atom number XX to YY" indicates the atomic number of the ZZ group when it is unsubstituted, and does not include the atomic number 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.

[0092] In this specification, an unsubstituted ZZ group refers to a case where a “substituted or unsubstituted ZZ group” is an “unsubstituted ZZ group,” and a substituted ZZ group refers to a case where a “substituted or unsubstituted ZZ group” is a “substituted ZZ group.”

[0093] In the present specification, "unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not substituted with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a light hydrogen atom, a deuterium atom, or a tritium atom.

[0094] 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 replaced with a substituent. Similarly, "substitution" in the case of "BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced with an AA group.

[0095] "Substituents described in this specification"

[0096] Hereinafter, the substituents described in this specification are described.

[0097] The number of ring carbon atoms 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.

[0098] The number of ring-forming atoms of the “unsubstituted heterocyclic group” described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in this specification.

[0099] The carbon number of the “unsubstituted alkyl group” described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.

[0100] The carbon number of the “unsubstituted alkenyl group” described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in this specification.

[0101] The carbon number of the “unsubstituted alkynyl group” described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in this specification.

[0102] The number of ring-forming carbon atoms of the “unsubstituted cycloalkyl group” described in this specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified in this specification.

[0103] The number of ring-forming carbon atoms of the “unsubstituted arylene 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.

[0104] The number of ring-forming atoms of the “unsubstituted divalent heterocyclic group” described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in this specification.

[0105] The carbon number of the “unsubstituted alkylene group” described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.

[0106] · “Substituted or unsubstituted aryl group”

[0107] Specific examples (specific example group G1) of the “substituted or unsubstituted aryl group” described in this specification include the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B). (Here, the unsubstituted aryl group refers to a case where the “substituted or unsubstituted aryl group” is an “unsubstituted aryl group,” and the substituted aryl group refers to a case where the “substituted or unsubstituted aryl group” is a “substituted aryl group.”) In this specification, when simply referred to as “aryl group,” both an “unsubstituted aryl group” and a “substituted aryl group” are included.

[0108] A "substituted aryl group" means a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent. Examples of the "substituted aryl group" include groups in which one or more hydrogen atoms of the "unsubstituted aryl group" of the following specific example group G1A are replaced with a substituent, and examples of substituted aryl groups of the following specific example group G1B, etc. In addition, the examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed herein are merely examples, and the "substituted aryl group" described in the present specification also includes groups in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group" of the following specific example group G1B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted aryl group" of the following specific example group G1B is further replaced with a substituent.

[0109] · Unsubstituted aryl group (specific example group G1A):

[0110] phenyl group,

[0111] p-biphenyl group,

[0112] m-biphenyl group,

[0113] o-biphenyl group,

[0114] p-terphenyl-4-yl group,

[0115] p-terphenyl-3-yl group,

[0116] p-terphenyl-2-yl group,

[0117] m-terphenyl-4-yl group,

[0118] m-terphenyl-3-yl,

[0119] m-terphenyl-2-yl,

[0120] o-terphenyl-4-yl,

[0121] o-terphenyl-3-yl,

[0122] o-terphenyl-2-yl,

[0123] 1-naphthyl group,

[0124] 2-naphthyl group,

[0125] Anthryl group,

[0126] Benzanthryl group,

[0127] Phenanthryl group,

[0128] Benzophenanthryl group,

[0129] Penalen Diary,

[0130] Florence Diary,

[0131] Chrysen's Diary,

[0132] Benzochreisen Diary,

[0133] Triphenylene group,

[0134] Benzotriphenylene group,

[0135] Tetracen Diary,

[0136] Pentacen Diary,

[0137] Fluorene diary,

[0138] 9,9'-spirobifluorene diaryl,

[0139] Benzofluorene diary,

[0140] Dibenzofluorene diary,

[0141] Fluoranthene diary,

[0142] Benzofluoranthene diary,

[0143] Perylene diary, and

[0144] 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).

[0145]

[0146]

[0147] · Substituted aryl group (specific example group G1B):

[0148] o-tolyl group,

[0149] m-tolyl group,

[0150] p-tolyl group,

[0151] para-xylyl group,

[0152] meta-xylyl group,

[0153] ortho-xylyl group,

[0154] para-isopropylphenyl group,

[0155] meta-isopropylphenyl group,

[0156] ortho-isopropylphenyl group,

[0157] para-t-butylphenyl group,

[0158] meta-t-butylphenyl group,

[0159] ortho-t-butylphenyl group,

[0160] 3,4,5-trimethylphenyl group,

[0161] 9,9-dimethylfluorenyl group,

[0162] 9,9-diphenylfluorenyl group

[0163] 9,9-bis(4-methylphenyl)fluorenyl group,

[0164] 9,9-bis(4-isopropylphenyl)fluorenyl group,

[0165] 9,9-bis(4-t-butylphenyl)fluorenyl group,

[0166] cyanophenyl group,

[0167] Triphenylsilylphenyl group,

[0168] Trimethylsilylphenyl group,

[0169] phenylnaphthyl group,

[0170] naphthylphenyl group, and

[0171] A group in which at least one hydrogen atom of a monovalent group derived from a ring structure represented by the above general formula (TEMP-1) to (TEMP-15) is substituted with a substituent.

[0172] · “Substituted or unsubstituted heterocyclic group”

[0173] The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom in the ring-forming atom. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.

[0174] The “heterocyclic group” described in this specification is a monocyclic group or a condensed ring group.

[0175] The “heterocyclic group” described in this specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0176] Specific examples of the “substituted or unsubstituted heterocyclic group” described in this specification (specific examples group G2) include the following unsubstituted heterocyclic groups (specific examples group G2A) and substituted heterocyclic groups (specific examples group G2B). (Here, the unsubstituted heterocyclic group refers to a case where the “substituted or unsubstituted heterocyclic group” is an “unsubstituted heterocyclic group,” and the substituted heterocyclic group refers to a case where the “substituted or unsubstituted heterocyclic group” is a “substituted heterocyclic group.”) In this specification, when simply referred to as “heterocyclic group,” it includes both an “unsubstituted heterocyclic group” and a “substituted heterocyclic group.”

[0177] A “substituted heterocyclic group” means a group in which at least one hydrogen atom of an “unsubstituted heterocyclic group” is replaced with a substituent. Specific examples of the “substituted heterocyclic group” include groups in which the hydrogen atoms of the “unsubstituted heterocyclic group” of the following specific example group G2A are substituted, and examples of substituted heterocyclic groups of the following specific example group G2B are examples. In addition, the examples of the “unsubstituted heterocyclic group” and the examples of the “substituted heterocyclic group” listed herein are merely examples, and the “substituted heterocyclic group” described in the present specification also includes groups in which the hydrogen atom bonded to the ring-forming atom of the heterocyclic group itself in the “substituted heterocyclic group” of the specific example group G2B is further substituted with a substituent, and groups in which the hydrogen atom of the substituent in the “substituted heterocyclic group” of the specific example group G2B is further substituted with a substituent.

[0178] 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 derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0179] Specific example group G2B includes, 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 at least one hydrogen atom of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) is substituted with a substituent (specific example group G2B4).

[0180] · Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):

[0181] pyrrolyl group,

[0182] imidazolyl group,

[0183] Pyrazolyl group,

[0184] Triazolyl group,

[0185] tetrazolyl group,

[0186] Oxazolyl group,

[0187] Isoxazolyl group,

[0188] Oxadiazolyl group,

[0189] Thiazolyl group,

[0190] isothiazolyl group,

[0191] Cyadiazolyl group,

[0192] Pyridyl group,

[0193] Pyridazin Diary,

[0194] Pyrimidine Diary,

[0195] The Pirazin Diary,

[0196] Triazine Diary,

[0197] Indolyl group,

[0198] Isoindole group,

[0199] Indolizine Diary,

[0200] Quinolizine Diary,

[0201] quinolyl group,

[0202] Isoquinolyl group,

[0203] Shinnolgi,

[0204] Phthalazine Diary,

[0205] Quinazoline diary,

[0206] Quinoxaline Diary,

[0207] Benzimidazolyl group,

[0208] Indazolyl group,

[0209] Phenanthroline Diary,

[0210] Phenanthridine diary,

[0211] Acridin Diary,

[0212] Phenazine Diary,

[0213] Carbazolyl group,

[0214] Benzocarbazolyl group,

[0215] Morpholino period,

[0216] Penok Photo Diary,

[0217] Phenothiazine Diary,

[0218] azacarbazolyl group, and

[0219] Diazacabazolyl group.

[0220] · Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):

[0221] furyl group,

[0222] Oxazolyl group,

[0223] Isoxazolyl group,

[0224] Oxadiazolyl group,

[0225] Zanten Diary,

[0226] Benzofuran diary,

[0227] Isobenzofuran diary,

[0228] Dibenzofuran diary,

[0229] Naphthobenzofuran diary,

[0230] Benzoxazolyl group,

[0231] Benzisoxazolyl group,

[0232] Penok Photo Diary,

[0233] Morpholino period,

[0234] Dynaptofuran diary,

[0235] Azadibenzofuran diary,

[0236] Diazadibenzofuran diary,

[0237] Azanaphthobenzofuran diary, and

[0238] Diazanaphthobenzofuran diary.

[0239] · Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3):

[0240] Cyworld Diary,

[0241] Thiazolyl group,

[0242] isothiazolyl group,

[0243] Cyadiazolyl group,

[0244] Benzothiophene diary (benzothiene diary),

[0245] Isobenzothiophene diary (isobenzothiene diary),

[0246] Dibenzothiophene diary (dibenzothiene diary),

[0247] Naphthobenzothiophene diary (naphthobenzothiene diary),

[0248] Benzothiazolyl group,

[0249] Benzisothiazolyl group,

[0250] Phenothiazine Diary,

[0251] Dynaptothiophene Diary (Dynaptothiene Diary),

[0252] Azadibenzothiophene diary (azadibenzothiene diary),

[0253] Diazadibenzothiophene diaryl (diazadibenzothiene diaryl),

[0254] Azanaphthobenzothiophene dihydrate (azanaphthobenzothien dihydrate), and

[0255] Diazanaphthobenzothiophene diary (diazanaphthobenzothien diary).

[0256] 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):

[0257]

[0258]

[0259] In the above general formula (TEMP-16) to (TEMP-33), X A and Y Aare, 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.

[0260] In the above general formula (TEMP-16) to (TEMP-33), X A and Y A When at least one of them is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from NH or CH2.

[0261] · Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):

[0262] (9-phenyl)carbazolyl group,

[0263] (9-biphenylyl)carbazolyl group,

[0264] (9-phenyl)phenylcarbazolyl group,

[0265] (9-naphthyl)carbazolyl group,

[0266] Diphenylcarbazol-9-yl group,

[0267] phenylcarbazol-9-yl group,

[0268] Methylbenzimidazolyl group,

[0269] Ethylbenzimidazolyl group,

[0270] Phenyltriazine dihydrate,

[0271] Biphenylyltriazine diary,

[0272] Diphenyltriazinyl group,

[0273] Phenylquinazolinyl group, and

[0274] Biphenylylquinazoline diary.

[0275] · Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0276] Phenyldibenzofuran dibasic group,

[0277] Methyldibenzofuran dibasic group,

[0278] t-butyldibenzofuran diaryl, and

[0279] A monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0280] · Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

[0281] Phenyldibenzothiophene diary,

[0282] Methyldibenzothiophene diary,

[0283] t-butyldibenzothiophene diary, and

[0284] A monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0285] · A group in which at least one hydrogen atom of a monovalent heterocyclic group derived from a ring structure represented by the above general formula (TEMP-16) to (TEMP-33) is substituted with a substituent (specific example group G2B4):

[0286] The above “one or more hydrogen atoms of a monovalent heterocyclic group” refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, X A and Y A A hydrogen atom bonded to a nitrogen atom, at least one of which is NH, and X A and Y A It means one or more hydrogen atoms selected from the hydrogen atoms of a methylene group when one side is CH2.

[0287] · “Substituted or unsubstituted alkyl group”

[0288] Specific examples of the “substituted or unsubstituted alkyl group” described in this specification (specific example group G3) include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B). (Here, the unsubstituted alkyl group refers to a case where the “substituted or unsubstituted alkyl group” is an “unsubstituted alkyl group,” and the substituted alkyl group refers to a case where the “substituted or unsubstituted alkyl group” is a “substituted alkyl group.”) Hereinafter, when simply referred to as “alkyl group,” both an “unsubstituted alkyl group” and a “substituted alkyl group” are included.

[0289] A "substituted alkyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced with a substituent. Specific examples of the "substituted alkyl group" include a group in which one or more hydrogen atoms in the following "unsubstituted alkyl group" (specific example group G3A) are replaced with a substituent, and examples of a substituted alkyl group (specific example group G3B). In the present specification, the alkyl group in the "unsubstituted alkyl group" means a chain alkyl group. Therefore, the "unsubstituted alkyl group" includes a straight-chain "unsubstituted alkyl group" and a branched "unsubstituted alkyl group." Meanwhile, the examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" listed here are only examples, and the "substituted alkyl group" described in this specification also includes a group in which the hydrogen atom of the alkyl group itself in the "substituted alkyl group" of the specific example group G3B is further substituted with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl group" of the specific example group G3B is further substituted with a substituent.

[0290] · Unsubstituted alkyl group (specific example group G3A):

[0291] methyl group,

[0292] Ethyl group,

[0293] n-profiler,

[0294] Isopropyl group,

[0295] n-butyl group,

[0296] Isobutyl group,

[0297] s-butyl group, and

[0298] t-butyl group.

[0299] · Substituted alkyl group (specific example group G3B):

[0300] Heptafluoropropyl group (including isomers),

[0301] pentafluoroethyl group,

[0302] 2,2,2-trifluoroethyl group, and

[0303] Trifluoromethyl group.

[0304] · “Substituted or unsubstituted alkenyl group”

[0305] Specific examples of the “substituted or unsubstituted alkenyl group” described in this specification (specific example group G4) include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B). (Here, the unsubstituted alkenyl group refers to a case where the “substituted or unsubstituted alkenyl group” is an “unsubstituted alkenyl group,” and the “substituted alkenyl group” refers to a case where the “substituted or unsubstituted alkenyl group” is a “substituted alkenyl group.”) In this specification, when simply referred to as “alkenyl group,” both an “unsubstituted alkenyl group” and a “substituted alkenyl group” are included.

[0306] A “substituted alkenyl group” means a group in which one or more hydrogen atoms in an “unsubstituted alkenyl group” are replaced with a substituent. Specific examples of the “substituted alkenyl group” include groups in which the “unsubstituted alkenyl group” (specific example group G4A) below has a substituent, and examples of substituted alkenyl groups (specific example group G4B). In addition, the examples of the “unsubstituted alkenyl group” and the examples of the “substituted alkenyl group” listed here are merely examples, and the “substituted alkenyl group” described in the present specification also includes groups in which the hydrogen atoms of the alkenyl group itself in the “substituted alkenyl group” of the specific example group G4B are further replaced with substituents, and groups in which the hydrogen atoms of the substituent in the “substituted alkenyl group” of the specific example group G4B are further replaced with substituents.

[0307] · Unsubstituted alkenyl group (specific example group G4A):

[0308] Vinyl machine,

[0309] Announcement,

[0310] 1-Viewten Diary,

[0311] 2-Viewten Diary, and

[0312] 3-Viewten Diary.

[0313] · Substituted alkenyl group (specific example group G4B):

[0314] 1,3-butanediene diary,

[0315] 1-methylvinyl group,

[0316] 1-methylallyl group,

[0317] 1,1-dimethylallyl group,

[0318] 2-methylallyl group, and

[0319] 1,2-Dimethylallyl group.

[0320] · “Substituted or unsubstituted alkyne group”

[0321] Specific examples of the “substituted or unsubstituted alkynyl group” described in this specification (specific examples G5) include the following unsubstituted alkynyl groups (specific examples G5A). (Here, the unsubstituted alkynyl group refers to a case where the “substituted or unsubstituted alkynyl group” is an “unsubstituted alkynyl group.”) Hereinafter, when simply referred to as “alkynyl group,” both an “unsubstituted alkynyl group” and a “substituted alkynyl group” are included.

[0322] A "substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced with a substituent. Specific examples of a "substituted alkynyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl group" (specific example group G5A) are replaced with a substituent.

[0323] · Unsubstituted alkynylidene group (specific example group G5A):

[0324] Etin Diary

[0325] · “Substituted or unsubstituted cycloalkyl group”

[0326] Specific examples of the “substituted or unsubstituted cycloalkyl group” described in this specification (specific examples G6) include the following unsubstituted cycloalkyl groups (specific examples G6A) and substituted cycloalkyl groups (specific examples G6B). (Here, the unsubstituted cycloalkyl group refers to a case where the “substituted or unsubstituted cycloalkyl group” is an “unsubstituted cycloalkyl group,” and the substituted cycloalkyl group refers to a case where the “substituted or unsubstituted cycloalkyl group” is a “substituted cycloalkyl group.”) In this specification, when simply referred to as “cycloalkyl group,” both an “unsubstituted cycloalkyl group” and a “substituted cycloalkyl group” are included.

[0327] A “substituted cycloalkyl group” means a group in which one or more hydrogen atoms in an “unsubstituted cycloalkyl group” are replaced with a substituent. Specific examples of the “substituted cycloalkyl group” include groups in which one or more hydrogen atoms in the “unsubstituted cycloalkyl group” (specific example group G6A) below are replaced with a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). In addition, the examples of the “unsubstituted cycloalkyl group” and the examples of the “substituted cycloalkyl group” listed herein are merely examples, and the “substituted cycloalkyl group” described in the present specification also includes groups in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the “substituted cycloalkyl group” of specific example group G6B are replaced with a substituent, and groups in which the hydrogen atoms of the substituent in the “substituted cycloalkyl group” of specific example group G6B are further replaced with a substituent.

[0328] · Unsubstituted cycloalkyl group (specific example group G6A):

[0329] Cyclopropyl group,

[0330] Cyclobutyl group,

[0331] Cyclopentyl group,

[0332] Cyclohexyl group,

[0333] 1-adamantyl group,

[0334] 2-adamantyl group,

[0335] 1-norbornyl group, and

[0336] 2-Norbornyl group.

[0337] · Substituted cycloalkyl group (specific example group G6B):

[0338] 4-methylcyclohexyl group.

[0339] · 「-Si(R 901 )(R 902 )(R 903 ) is indicated by

[0340] -Si(R) described in this specification 901 )(R 902 )(R903 ) as a specific example (specific example group G7) of the flag,

[0341] -Si(G1)(G1)(G1),

[0342] -Si(G1)(G2)(G2),

[0343] -Si(G1)(G1)(G2),

[0344] -Si(G2)(G2)(G2),

[0345] -Si(G3)(G3)(G3), and

[0346] -Si(G6)(G6)(G6)

[0347] can be heard. Here,

[0348] G1 is a “substituted or unsubstituted aryl group” described in the specific example group G1.

[0349] G2 is a “substituted or unsubstituted heterocyclic group” described in the specific example group G2.

[0350] G3 is a “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0351] G6 is a “substituted or unsubstituted cycloalkyl group” described in specific example group G6.

[0352] - In Si(G1)(G1)(G1), multiple G1s are the same or different from each other.

[0353] - In Si(G1)(G2)(G2), multiple G2s are the same or different from each other.

[0354] - In Si(G1)(G1)(G2), multiple G1s are the same or different from each other.

[0355] - In Si(G2)(G2)(G2), multiple G2s are the same or different from each other.

[0356] - In Si(G3)(G3)(G3), plural G3s are the same or different from each other.

[0357] - In Si(G6)(G6)(G6), plural G6s are the same or different.

[0358] · 「-O-(R 904 ) is indicated by

[0359] -O-(R as described herein 904 ) as a specific example (specific example group G8) of the flag,

[0360] -O(G1),

[0361] -O(G2),

[0362] -O(G3), and

[0363] -O(G6)

[0364] can be heard.

[0365] Here,

[0366] G1 is a “substituted or unsubstituted aryl group” described in the specific example group G1.

[0367] G2 is a “substituted or unsubstituted heterocyclic group” described in the specific example group G2.

[0368] G3 is a “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0369] G6 is a “substituted or unsubstituted cycloalkyl group” described in specific example group G6.

[0370] · 「-S-(R 905 ) is indicated by

[0371] -S-(R as described in this specification 905 ) as a specific example (specific example group G9) of the flag,

[0372] -S(G1),

[0373] -S(G2),

[0374] -S(G3), and

[0375] -S(G6)

[0376] can be heard.

[0377] Here,

[0378] G1 is a “substituted or unsubstituted aryl group” described in the specific example group G1.

[0379] G2 is a “substituted or unsubstituted heterocyclic group” described in the specific example group G2.

[0380] G3 is a “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0381] G6 is a “substituted or unsubstituted cycloalkyl group” described in specific example group G6.

[0382] · 「-N(R 906 )(R 907 ) is indicated by

[0383] -N(R) described in this specification 906 )(R 907 ) as a specific example (specific example group G10) of the flag,

[0384] -N(G1)(G1),

[0385] -N(G2)(G2),

[0386] -N(G1)(G2),

[0387] -N(G3)(G3), and

[0388] -N(G6)(G6)

[0389] can be heard.

[0390] Here,

[0391] G1 is a “substituted or unsubstituted aryl group” described in the specific example group G1.

[0392] G2 is a “substituted or unsubstituted heterocyclic group” described in the specific example group G2.

[0393] G3 is a “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0394] G6 is a “substituted or unsubstituted cycloalkyl group” described in specific example group G6.

[0395] - In N(G1)(G1), plural G1s are identical or different.

[0396] - In N(G2)(G2), plural G2s are identical or different.

[0397] - In N(G3)(G3), plural G3s are identical or different.

[0398] - In N(G6)(G6), plural G6s are identical or different.

[0399] · "Halogen atom"

[0400] Specific examples of the “halogen atom” described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0401] · “Substituted or unsubstituted fluoroalkyl group”

[0402] The “substituted or unsubstituted fluoroalkyl group” described herein means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the “substituted or unsubstituted alkyl group” is replaced with a fluorine atom, and also includes a group (perfluoro group) in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the “substituted or unsubstituted alkyl group” are replaced with fluorine atoms. Unless otherwise specified in this specification, the carbon number of the “unsubstituted fluoroalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The “substituted fluoroalkyl group” means a group in which one or more hydrogen atoms of the “fluoroalkyl group” are replaced with a substituent. Meanwhile, the "substituted fluoroalkyl group" described herein includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in the "substituted fluoroalkyl group" are further substituted with a substituent, and a group in which one or more hydrogen atoms of a substituent in the "substituted fluoroalkyl group" are further substituted with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include examples of a group in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced with a fluorine atom.

[0403] · “Substituted or unsubstituted haloalkyl group”

[0404] The “substituted or unsubstituted haloalkyl group” described herein means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the “substituted or unsubstituted alkyl group” is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the “substituted or unsubstituted alkyl group” are replaced with halogen atoms. Unless otherwise specified in this specification, the carbon number of the “unsubstituted haloalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The “substituted haloalkyl group” means a group in which one or more hydrogen atoms of the “haloalkyl group” are replaced with a substituent. Meanwhile, the "substituted haloalkyl group" described herein includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in the "substituted haloalkyl group" are further substituted with a substituent, and a group in which one or more hydrogen atoms of a substituent in the "substituted haloalkyl group" are further substituted with a substituent. Specific examples of the "unsubstituted haloalkyl group" include examples of a group in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced with a halogen atom. A haloalkyl group is sometimes referred to as a halogenated alkyl group.

[0405] · “Substituted or unsubstituted alkoxy group”

[0406] A specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), wherein G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0407] · “Substituted or unsubstituted alkylthio group”

[0408] A specific example of the "substituted or unsubstituted alkylthio group" described in this specification is a group represented by -S(G3), wherein G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0409] · “Substituted or unsubstituted aryloxy group”

[0410] A specific example of the "substituted or unsubstituted aryloxy group" described in this specification is a group represented by -O(G1), wherein G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0411] · “Substituted or unsubstituted arylthio group”

[0412] A specific example of the "substituted or unsubstituted arylthio group" described in this specification is a group represented by -S(G1), wherein G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0413] · “Substituted or unsubstituted trialkylsilyl group”

[0414] 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 specific example group G3. Multiple G3s in -Si(G3)(G3)(G3) are the same as 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.

[0415] · “Substituted or unsubstituted aralkyl group”

[0416] A specific example of the “substituted or unsubstituted aralkyl group” described in the present specification is a group represented by -(G3)-(G1), wherein G3 is a “substituted or unsubstituted alkyl group” described in the specific example group G3, and G1 is a “substituted or unsubstituted aryl group” described in the specific example group G1. Therefore, 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 embodiment of the “substituted alkyl group.” The “unsubstituted aralkyl group” is an “unsubstituted alkyl group” in which an “unsubstituted aryl group” is substituted, and the carbon number of the “unsubstituted aralkyl group” is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in the present specification.

[0417] Specific examples of the “substituted or unsubstituted aralkyl group” include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group, an α-naphthylmethyl group, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group, a 1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, a β-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethyl group, a 1-β-naphthylisopropyl group, and a 2-β-naphthylisopropyl group.

[0418] The substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, and a 9,9-diphenylfluorenyl group.

[0419] The substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an azadibenzothiophenyl group, 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-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group, etc.

[0420] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.

[0421]

[0422] In this specification, the (9-phenyl)carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.

[0423]

[0424] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates a bonding position.

[0425] In this specification, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0426]

[0427] In the above general formulas (TEMP-34) to (TEMP-41), * indicates a bonding position.

[0428] The substituted or unsubstituted alkyl group described in this specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, and a t-butyl group, unless otherwise specified in this specification.

[0429] · “Substituted or unsubstituted arylene group”

[0430] The "substituted or unsubstituted arylene group" described herein, unless otherwise specified, is a divalent group derived from the "substituted or unsubstituted aryl group" by removing one hydrogen atom on the aryl ring. Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in specific example group G1 by removing one hydrogen atom on the aryl ring.

[0431] · “Substituted or unsubstituted divalent heterocyclic group”

[0432] The “substituted or unsubstituted divalent heterocyclic group” described herein, unless otherwise specified, is a divalent group derived from the “substituted or unsubstituted heterocyclic group” by removing one hydrogen atom on the heterocycle. Specific examples of the “substituted or unsubstituted divalent heterocyclic group” (specific example group G13) include divalent groups derived from the “substituted or unsubstituted heterocyclic group” described in specific example group G2 by removing one hydrogen atom on the heterocycle.

[0433] · “Substituted or unsubstituted alkylene group”

[0434] The “substituted or unsubstituted alkylene group” described herein, unless otherwise specified, is a divalent group derived from the “substituted or unsubstituted alkyl group” by removing one hydrogen atom on the alkyl chain. Specific examples of the “substituted or unsubstituted alkylene group” (specific example group G14) include divalent groups derived from the “substituted or unsubstituted alkyl group” described in specific example group G3 by removing one hydrogen atom on the alkyl chain.

[0435] The substituted or unsubstituted arylene group described in this specification is preferably one of the groups of the following general formulae (TEMP-42) to (TEMP-68), unless otherwise specified in this specification.

[0436]

[0437]

[0438] Among the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 are, each independently, a hydrogen atom or a substituent.

[0439] In the above general formulas (TEMP-42) to (TEMP-52), * indicates a bonding position.

[0440]

[0441] Among the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 are, each independently, a hydrogen atom or a substituent.

[0442] Formula Q9 and Q 10 Silver can be combined with each other via single bonds to form a ring.

[0443] In the above general formulas (TEMP-53) to (TEMP-62), * indicates a bonding position.

[0444]

[0445] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0446] In the above general formulas (TEMP-63) to (TEMP-68), * indicates a bonding position.

[0447] The substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any group of the following general formulae (TEMP-69) to (TEMP-102), unless otherwise specified in this specification.

[0448]

[0449]

[0450]

[0451] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0452]

[0453]

[0454]

[0455]

[0456] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0457] The above is a description of the “substituents described in this specification.”

[0458] · "When combined to form a ring"

[0459] In the present specification, when it is said that “one or more groups of two or more adjacent groups are combined with each other to form a substituted or unsubstituted monocyclic ring, or are combined with each other to form a substituted or unsubstituted condensed ring, or are not combined with each other”, it means that “one or more groups of two or more adjacent groups are combined with each other to form a substituted or unsubstituted monocyclic ring,” “one or more groups of two or more adjacent groups are combined with each other to form a substituted or unsubstituted condensed ring,” and “one or more groups of two or more adjacent groups are not combined with each other.”

[0460] In the present specification, the case where "one or more groups consisting of two or more adjacent groups are combined with each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more groups consisting of two or more adjacent groups are combined with each other to form a substituted or unsubstituted condensed ring" (hereinafter, these cases may be collectively referred to as "the case of combining to form a ring") are described below. The case of an anthracene compound represented by the following general formula (TEMP-103) in which the parent skeleton is an anthracene ring is described as an example.

[0461]

[0462] For example, R 921 ∼R 930 In the case where "one or more groups of two or more adjacent groups are combined to form a ring", a group consisting of two adjacent groups that form a group, R921 and R 922 Joe, R 922 Wow R 923 Joe, R 923 and R 924 Joe, R 924 Wow R 930 Joe, R 930 and R 925 Joe, R 925 Wow R 926 Joe, R 926 and R 927 Joe, R 927 and R 928 Joe, R 928 and R 929 of the group, and R 929 Wow R 921 It is a group of people.

[0463] The above "1 or more groups" means that two or more groups of two or more adjacent groups can form a ring at the same time. For example, R 921 and R 922 are combined with each other to form a ring Q A , and at the same time R 925 Wow R 926 These are combined to form a ring Q B In the case where it is formed, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0464]

[0465] The case where "a group consisting of two or more adjacent elements" forms a ring includes not only the case where groups consisting of "two" adjacent elements are combined as in the example described above, but also the case where groups consisting of "three or more" adjacent elements are combined. For example, R 921 and R 922 are combined with each other to form a ring Q A , and also R 922 Wow R 923 These are combined to form a ring Q C , forming three adjacent (R 921 , R922 and R 923 ) are combined with each other to form a ring and condense on the anthracene parent skeleton. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C is, R 922 Share.

[0466]

[0467] The formed "single ring" or "fused ring" has a structure of only the formed ring, and may be a saturated ring or an unsaturated ring. Even in the case where "a group of two adjacent groups" forms a "single ring" or a "fused ring", the "single ring" or "fused ring" may form a saturated ring or an unsaturated ring. For example, in the general formula (TEMP-104), the formed ring Q A and ring Q B are, respectively, "single ring" or "condensed ring". In addition, the ring Q formed in the general formula (TEMP-105) A , and ring Q C is a "condensed ring". Ring Q of the above general formula (TEMP-105) A Wow, Hwan Q C is, ring Q A Wow, Hwan Q C A condensed ring is formed by condensation. Ring Q of the above general formula (TEMP-104) A If it is a benzene ring, then ring Q A is a single ring. The ring Q of the above general formula (TEMP-104) A If it is a naphthalene ring, then ring Q A is a condensed ring.

[0468] “Unsaturated ring” means an aromatic hydrocarbon ring or an aromatic heterocycle. “Saturated ring” means an aliphatic hydrocarbon ring or a non-aromatic heterocycle.

[0469] As a specific example of an aromatic hydrocarbon ring, a structure in which the group listed as a specific example in the specific example group G1 is terminated by a hydrogen atom can be mentioned.

[0470] As a specific example of an aromatic heterocyclic ring, a structure in which the aromatic heterocyclic ring group listed as a specific example in the specific example group G2 is terminated by a hydrogen atom can be mentioned.

[0471] As a specific example of an aliphatic hydrocarbon ring, a structure in which the group listed as a specific example in the specific example group G6 is terminated by a hydrogen atom can be mentioned.

[0472] "Forming a ring" means forming a ring with only a plurality of atoms of the parent skeleton, or with a plurality of atoms of the parent skeleton and one or more additional arbitrary elements. For example, R shown in the general formula (TEMP-104) above 921 and R 922 Ring Q formed by combining with each other A is, R 921 The carbon atoms of the anthracene skeleton to which this bond is made, and R 922 It means a ring formed by a carbon atom of the anthracene skeleton to which R is bonded and one or more arbitrary elements. As a specific example, R 921 and R 922 Rohwan Q A In the case of forming R 921 The carbon atoms of the anthracene skeleton to which this bond is made, and R 922 When the carbon atom of the anthracene skeleton to which R is bonded forms a monocyclic unsaturated ring with four carbon atoms, R 921 and R 922 The ring formed by is a benzene ring.

[0473] Here, "any element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur, unless otherwise specified in the present specification. In any element (for example, in the case of carbon or nitrogen), a bond that does not form a ring may be terminated with a hydrogen atom or the like, and may be substituted with an "arbitrary substituent" described below. When any element other than a carbon element is included, the ring formed is a heterocycle.

[0474] Unless otherwise specified in this specification, “one or more arbitrary elements” constituting a single ring or condensed ring are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.

[0475] Unless otherwise specified in this specification, among “single ring” and “condensed ring”, “single ring” is preferred.

[0476] Unless otherwise specified in this specification, among “saturated ring” and “unsaturated ring”, “unsaturated ring” is preferred.

[0477] Unless otherwise specified in this specification, “monocyclic” is preferably a benzene ring.

[0478] Unless otherwise specified in this specification, the “unsaturated ring” is preferably a benzene ring.

[0479] In the case where “one or more groups consisting of two or more adjacent groups” are “combined with each other to form a substituted or unsubstituted monocyclic ring” or “combined with each other to form a substituted or unsubstituted condensed ring”, unless otherwise stated in the present specification, preferably, one or more groups consisting of two or more adjacent groups are combined with each other to form a substituted or unsubstituted “unsaturated ring” consisting of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of one or more and 15 or fewer carbon elements, nitrogen elements, oxygen elements, and sulfur elements.

[0480] In the case where the above "single ring" or "fused ring" has a substituent, the substituent is, for example, an "arbitrary substituent" described below. Specific examples of the substituent in the case where the above "single ring" or "fused ring" has a substituent are the substituents described in the above-mentioned "substituent described in the present specification."

[0481] When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, an "arbitrary substituent" described below. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, a specific example of the substituent is the substituent described in the above-mentioned "substituent described in the present specification."

[0482] The above is an explanation of the case where “one or more groups of two or more adjacent groups combine with each other to form a substituted or unsubstituted monocyclic ring” and the case where “one or more groups of two or more adjacent groups combine with each other to form a substituted or unsubstituted condensed ring” (“when combined to form a ring”).

[0483] · Substituents in cases where it is said to be “substituted or unsubstituted”

[0484] In one embodiment of the present specification, the substituent in the case of “substituted or unsubstituted” (in the present specification, sometimes referred to as “optional substituent”) is, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms,

[0485] Unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0486] Unsubstituted alkyne group having 2 to 50 carbon atoms,

[0487] Unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0488] -Si(R 901 )(R 902 )(R 903 ),

[0489] -O-(R 904 ),

[0490] -S-(R 905 ),

[0491] -N(R 906 )(R 907 ),

[0492] Halogen atom, cyano group, nitro group,

[0493] An unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0494] Heterocyclic group having 5 to 50 unsubstituted ring atoms

[0495] A group selected from the group consisting of, etc.,

[0496] Here, R 901 ∼R 907 , each independently,

[0497] hydrogen atoms,

[0498] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0499] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0500] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0501] It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0502] R 901 If there are two or more of these, two or more R 901 are identical to each other, or different,

[0503] R 902 If there are two or more R's, two or more R's 902 are identical to each other, or different,

[0504] R 903 If there are two or more of these, two or more R 903 are identical to each other, or different,

[0505] R 904 If there are two or more R's, two or more R's 904 are identical to each other, or different,

[0506] R 905 If there are two or more R's, two or more R's 905 are identical to each other, or different,

[0507] R 906 If there are two or more of these, two or more R 906 are identical to each other, or different,

[0508] R 907 If there are two or more of these, two or more R 907 are identical or different from each other.

[0509] In one embodiment, the substituent in the case of “substituted or unsubstituted” is

[0510] Alkyl group having 1 to 50 carbon atoms,

[0511] An aryl group having 6 to 50 ring carbon atoms, and

[0512] Heterocyclic ring with 5 to 50 ring atoms

[0513] A group selected from the group consisting of .

[0514] In one embodiment, the substituent in the case of “substituted or unsubstituted” is

[0515] Alkyl group having 1 to 18 carbon atoms,

[0516] An aryl group having 6 to 18 ring carbon atoms, and

[0517] Heterocyclic ring with 5 to 18 ring atoms

[0518] A group selected from the group consisting of .

[0519] Specific examples of each of the above arbitrary substituents are specific examples of the substituents described in the above-mentioned “substituents described in the present specification.”

[0520] Unless otherwise stated herein, adjacent arbitrary substituents may form a “saturated ring” or an “unsaturated ring”, preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, and more preferably a benzene ring.

[0521] Unless otherwise specified herein, any substituent may additionally have a substituent. The substituent additionally possessed by any substituent is the same as the above-mentioned optional substituent.

[0522] In this specification, the numerical range indicated using “AA∼BB” means a range including the numerical value AA described before “AA∼BB” as the lower limit and the numerical value BB described after “AA∼BB” as the upper limit.

[0523]

[0524] Hereinafter, the compound of the present invention is described.

[0525] The compound of the present invention is represented by the above formula (I) or (II). Hereinafter, symbols in formulas (I) and (II) and each formula described below will be described. Unless otherwise specified, the same symbols have the same meaning.

[0526] Hereinafter, the compound of the present invention represented by the formula (I) and the formula included in the formula (I) described below is sometimes simply referred to as “inventive compound (I).”

[0527] In addition, there are cases where the compound of the present invention represented by the formula (II) and the formula included in the formula (II) described below is simply referred to as “inventive compound (II).”

[0528] Additionally, the above-described invention compounds (I) and (II) are sometimes referred to simply as “invention compounds.”

[0529]

[0530] The first compound of the present invention (inventive compound (I)) is represented by the following formula (I).

[0531]

[0532] In formula (I),

[0533] R1 and R2 are each independently a methyl group or a phenyl group, but not both are phenyl groups;

[0534] Two adjacent ones selected from R3 to R6 are bonded to a and b, respectively;

[0535] R3 to R6, which are not bonded to the above a and b, are hydrogen atoms;

[0536] L is a single bond or a phenylene group;

[0537] L1 is a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms;

[0538] Ar1 is substituted or unsubstituted , substituted or unsubstituted , or substituted or unsubstituted and;

[0539] A is a substituted or unsubstituted aryl group having 12 to 17 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 12 to 17 ring atoms;

[0540] X is an oxygen atom or -CR 7 R 8 and R 7 and R 8 are each independently a methyl group or a phenyl group, or R 7 and R 8 combine with each other to form a spiro ring;

[0541] Ar2 is represented by the formula (1-a), (1-b), (1-c), (1-d) or (1-e) described below.

[0542]

[0543] In this specification, the structure of a group (e.g., R group) connected to a parent structure is or It is displayed as follows.

[0544] In one specific example, in the above formula (I), silver , , or , wherein R1 and R2 are each independently a methyl group or a phenyl group, but not both are phenyl groups.

[0545]

[0546] In one specific example, in the formula (I), R1 and R2 are methyl groups. In another specific example, in the formula (I), one of R1 and R2 is a methyl group and the other is a phenyl group.

[0547] In one specific example, in the formula (I), R3 and R4 are bonded to a and b, respectively, and R5 and R6 are hydrogen atoms. In another specific example, R4 and R5 are bonded to a and b, respectively, and R3 and R6 are hydrogen atoms. In yet another specific example, R5 and R6 are bonded to a and b, respectively, and R3 and R4 are hydrogen atoms.

[0548] In the above formula (I), L is a single bond or a phenylene group; L1 is a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0549] In the above formula (I), at least one of L and L1 may be a deuterated group. For example, in the above formula (I), L is a single bond or a phenylene group substituted with a deuterium atom; L1 is a single bond or an arylene group having 6 to 12 carbon atoms substituted or unsubstituted with a deuterium atom.

[0550] For example, the unsubstituted arylene group having 6 to 12 carbon atoms in L1 may be a phenylene group, a biphenylene group, or a naphthylene group. Specifically, the unsubstituted arylene group having 6 to 12 carbon atoms in L1 may be, for example, a phenylene group.

[0551] In the above formula (I), L is a single bond; L1 may be a single bond or a phenylene group.

[0552] Among Ar1 in the above formula (I), A may be a substituted or unsubstituted aryl group having 12 to 17 ring carbon atoms.

[0553] In one example, A in Ar1 of the above formula (I) may be an unsubstituted aryl group having 12 to 15 ring carbon atoms. Specifically, A in Ar1 of the above formula (I) may be a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a fluorenyl group, or a 9,9-dimethylfluorenyl group.

[0554] In one specific example, the substituted or unsubstituted aryl group having 12 to 17 ring carbon atoms may be an unsubstituted biphenyl group.

[0555] Among Ar1 in the above formula (I), A may be a substituted or unsubstituted aromatic heterocyclic group having 12 to 17 ring atoms. The aromatic heterocyclic group having 12 to 17 ring atoms includes at least one heteroatom selected from a nitrogen (N) atom, an oxygen (O) atom, and a sulfur (S) atom among the ring atoms. For example, the aromatic heterocyclic group having 12 to 17 ring atoms is a phenanthroline group, a phenanthridinyl group, an acridinyl group, a phenazinyl group, a carbazolyl group, a benzocarbazolyl group, a phenoxazinyl group, a phenothiazinyl group, an azacarbazolyl group, a diazacabazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, an azanaphthobenzofuranyl group, a diazanaphthobenzofuranyl group, a dibenzothiophenyl group (dibenzothienyl group), a naphthobenzothiophenyl group (naphthobenzothienyl group), an azadibenzothiophenyl group (azadibenzothienyl group), It can be diazadibenzothiophenyl group (diazadibenzothienyl group), azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), or diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0556] In the above formula (I), X in Ar1 is an oxygen atom or -CR 7 R 8 and R 7 and R 8 may be a phenyl group.

[0557] Ar1 of the above formula (I) is substituted or unsubstituted For example, it can be 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, or 9-phenanthrenyl.

[0558] Ar1 of the above formula (I) is substituted or unsubstituted Silver substituted or unsubstituted , or substituted or unsubstituted It can be. Among the Ar1 of the above formula (I), substituted or unsubstituted Silver substituted or unsubstituted , or substituted or unsubstituted It can be. Among the Ar1 of the above formula (I), substituted or unsubstituted Silver substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , or substituted or unsubstituted It could be.

[0559] Ar1 of the above formula (I) is substituted or unsubstituted Silver substituted or unsubstituted It can be. Among the Ar1 of the above formula (I), substituted or unsubstituted Silver substituted or unsubstituted It can be. Among the Ar1 of the above formula (I), substituted or unsubstituted Silver substituted or unsubstituted , or substituted or unsubstituted It could be.

[0560] In one example, in the above formula (I), Ar1 is substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , or substituted or unsubstituted It could be.

[0561]

[0562] In one embodiment, Ar2 of the above formula (I) is represented by the following formula (1-a).

[0563]

[0564] (In equation (1-a),

[0565] *21 is a single bond bonding to L1, and when L1 is a single bond, *21 is bonded to the central nitrogen atom;

[0566] R 101 ~R 105 One selected from is a single bond binding to *22, and R 106 ~R 110One selected from is a single bond binding to *23;

[0567] R, which is not a single bond 101 ~R 105 and R 106 ~R 110 are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms;

[0568] R 111 ~R 115 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 13 ring atoms;

[0569] u is 0 to 2, v is 0 or 1, but at least one of u and v is not 0)

[0570] R in the above formula (1-a) 102 ~R 104 One selected from may be a single bond binding to *22. In one example, R in the above formula (Ia) 103 may be a single bond that binds to *22.

[0571] R, which is not a single bond 101 ~R 105 All of them can be hydrogen atoms.

[0572] R in the above formula (1-a) 107 ~R 109 One selected from may be a single bond binding to *23. In one example, R in the above formula (Ia) 108 * may be a single bond that binds to 23.

[0573] R, which is not a single bond 106 ~R 110 All of them can be hydrogen atoms.

[0574] R in the above formula (1-a) 111 ~R 115 can all be hydrogen atoms.

[0575] The above u and v may be either 0 or both may be non-zero.

[0576] In one specific example, in the formula (I), L1 is a single bond; Ar2 is represented by the formula (1-a), and in the formula (1-a), R 103 is a single bond that binds to *22, and R 108 is a single bond that binds to *23, and R 111 ~R 115 is a hydrogen atom, and u or v can be 0.

[0577]

[0578] In another embodiment, Ar2 of the above formula (I) is represented by the following formula (1-b).

[0579]

[0580] (In equation (1-b),

[0581] *24 is a single bond bonding to L1, and when L1 is a single bond, *24 is bonded to the central nitrogen atom;

[0582] R 121 ~R 128 One selected from is a single bond binding to *25;

[0583] R, which is not a single bond 121 ~R 128 are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms)

[0584] R in the above formula (1-b) 122 , R 123 , R 127 and R 128 One selected from may be a single bond binding to *25.

[0585] Among the above formula (1-b), R is not a single bond. 121 ~R 128 All of them can be hydrogen atoms.

[0586] In one specific example, in the formula (I), L1 is a single bond or a phenylene group; Ar2 is represented by the formula (1-b), and in the formula (1-b), R 122 , R 123 , R 127 and R 128 One selected from is a single bond bonding to *25, and R is not the single bond 121 ~R 128 can be a hydrogen atom.

[0587]

[0588] In another embodiment, Ar2 of the above formula (I) is represented by the following formula (1-c).

[0589]

[0590] (In equation (1-c),

[0591] *26 is a single bond bonding to L1, and when L1 is a single bond, *26 is bonded to the central nitrogen atom;

[0592] R 131 ~R 140 One selected from is a single bond binding to *27;

[0593] R, which is not a single bond 131 ~R 140 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.

[0594] In one specific example, in the above formula (I), L1 is a single bond; Ar2 is represented by the above formula (1-c), and in the formula (1-c), R is not a single bond. 131 ~R 140 can be a hydrogen atom.

[0595] In another embodiment, Ar2 of the above formula (I) is represented by the following formula (1-d).

[0596]

[0597] (In equation (1-d),

[0598] *28 is a single bond bonding to L1, and when L1 is a single bond, *28 is bonded to the central nitrogen atom;

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

[0600] p is 0 or 1;

[0601] p is 0, X 1 This oxygen atom, sulfur atom, -CR E R F or -NR G When, R 141 ~R 148 and R G One selected from is a single bond binding to *29;

[0602] p is 1, and X 1 This -CR E R F or -NR G If , R 145 Wow R 146 , R 146 and R 147 , or R 147 and R 148 R is a single bond where one side is bonded to *d, the other side is bonded to *e, and is not a single bond bonded to *d or *e. 145 ~R 148 , R 141 ~R 144 , and R 200 ~R 203 One selected from is a single bond binding to *29;

[0603] p is 1, and X 1 If this is an oxygen atom or a sulfur atom, R 145 Wow R 146 , R 146 and R 147 , or R147 and R 148 One side of R is a single bond bonded to *d, the other side is a single bond bonded to *e, and R 141 Inland R 144 One selected from is a single bond binding to *29;

[0604] R, which is not a single bond 141 ~R 148 , R, which is not a single bond 200 ~R 203 , and R which is not a single bond G , the above R E , and the above R F are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 13 ring atoms;

[0605] Just p is 0 and X 1 This -CR E R F If R E is a methyl group and R F is a methyl group or a phenyl group)

[0606] X in the above formula (1-d) 1 Silver -CR E R F and R E is a methyl group, and R F may be a methyl group or a phenyl group. In one example, X in the above formula (1-d) 1 Silver -CR E R F and R E and R F can all be methyl groups.

[0607] In the above formula (I), L1 is a single bond; Ar2 is represented by the above formula (1-d), and in the formula (1-d), p is 0, and X 1 Silver -CR E R F and R E is a methyl group, and RF can be a methyl group or a phenyl group.

[0608]

[0609] In another embodiment, Ar2 of the above formula (I) is represented by the following formula (1-e).

[0610]

[0611] (In equation (1-e),

[0612] *30 is a single bond bonding to L1, and if L1 is a single bond, *30 is bonded to the central nitrogen atom;

[0613] R 151 ~R 155 One selected from is a single bond binding to *31, and R 151 ~R 155 Another one selected from is a single bond binding to *32;

[0614] R, which is not a single bond 151 ~R 155 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group;

[0615] R 161 ~R 165 and R 171 ~R 175 are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms;

[0616] R, not a hydrogen atom 161 Inland R 165 At least two adjacent ones selected from can combine with each other to form one or more unsubstituted benzene rings;

[0617] R, not a hydrogen atom 171 Inland R 175 At least two adjacent ones selected from may combine with each other to form one or more unsubstituted benzene rings).

[0618] In one specific example, in the above formula (I), L1 is a single bond; Ar2 is represented by the above formula (1-e), and in the formula (1-e), R is not a single bond. 151 ~R 155 , R 161 ~R 165 and R 171 ~R 175 can be a hydrogen atom.

[0619] In one specific example, in the formula (I), R1 and R2 are methyl groups; L is a single bond; L1 is a single bond or a phenylene group; in Ar1, A is a substituted or unsubstituted aryl group having 12 to 17 ring carbon atoms, and X is an oxygen atom or -CR 7 R 8 and R 7 and R 8 is a phenyl group; in formula (1-a), R 103 is a single bond that binds to *22, and R 108 is a single bond that binds to *23, and R 111 ~R 115 is a hydrogen atom, u or v is 0; in formula (1-b), R 122 , R 123 , R 127 and R 128 One selected from is a single bond bonding to *25, and R is not the single bond 121 ~R 128 is a hydrogen atom; in formula (1-c), R is not a single bond 131 ~R 140 is a hydrogen atom; in formula (1-d), p is 0, and X 1 Silver -CR E R F and R E is a methyl group, and R F is a methyl group or a phenyl group; in formula (1-e), R is not a single bond 151 ~R 155 , R 161 ~R 165 and R 171 ~R 175can be a hydrogen atom.

[0620] Among the substituent definitions of the above formulas (1-a) to (1-e), the alkyl group having 1 to 10 carbon atoms mentioned 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, or a t-butyl group. Among the substituent definitions of the above formulas (1-a) to (1-e), the aryl group having 6 to 12 ring-forming carbon atoms mentioned may be a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, or a naphthyl group. Among the substituent definitions of the above formulas (1-a) to (1-e), the aromatic heterocyclic group having 5 to 13 ring atoms is selected from the group consisting of a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolizinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, an indazolyl group, a phenazinyl group, a carbazolyl group, Benzocarbazolyl group, azacarbazolyl group, diazacabazolyl group, furyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzoxazolyl group, benzisoxazolyl group, azadibenzofuranyl group, diazadibenzofuranyl group, thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), dibenzothiophenyl group (dibenzothienyl group), benzothiazolyl group, benzisothiazolyl group, It can be azadibenzothiophenyl group (azadibenzothienyl group) or diazadibenzothiphenyl group (diazadibenzothienyl group).

[0621]

[0622] The second compound of the present invention (inventive compound (B)) is represented by the following formula (II).

[0623]

[0624] In formula (II),

[0625] R1, R2, R7 and R8 are each independently a methyl group or a phenyl group, or R1 and R2, or R7 and R8 are combined with each other to form a spiro ring;

[0626] Two adjacent ones selected from R3 to R6 are bonded to a and b, respectively;

[0627] R9~R 12 Two adjacent ones selected from are bonded to c and d respectively;

[0628] R3 to R6 that do not bind to the above a and b, and R9 to R that do not bind to the above c and d 12 is a hydrogen atom;

[0629] L is each independently a single bond or a phenylene group;

[0630] Ar1 is substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , or substituted or unsubstituted However, when the above Ar1 has two or more substituents, the substituents can combine with each other to form a condensed ring (provided that X is -CR 13 R 14 (except in this case)

[0631] A is a substituted or unsubstituted aryl group having 5 or more ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 or more ring atoms;

[0632] X is an oxygen atom, a sulfur atom, or -CR 13 R 14 and;

[0633] R 13 and R 14 are each independently a methyl group or a phenyl group, or R13 and R 14 They combine with each other to form spirocycles.

[0634] In one specific example, in the above formula (II), silver , , or , wherein R1 and R2 are each independently a methyl group or a phenyl group, or R1 and R2 are combined with each other to form a spiro ring.

[0635] In another specific example, in the above formula (II), silver , , or , wherein R7 and R8 are each independently a methyl group or a phenyl group, or R7 and R8 are combined with each other to form a spiro ring.

[0636]

[0637] In one specific example, in the above formula (II), R1, R2, R7 and R8 may be methyl groups.

[0638] In another specific example, in the above formula (II), any one of R1, R2, R7 and R8 may be a methyl group and the others may be phenyl groups.

[0639] In another specific example, in the above formula (II), any two of R1, R2, R7 and R8 may be methyl groups and the remainder may be phenyl groups.

[0640] In another specific example, in the above formula (II), R1 and R2 are methyl groups and R7 and R8 can be combined with each other to form a spiro ring.

[0641] In another specific example, in the above formula (II), R1 and R2 may be combined with each other to form a spiro ring, and R7 and R8 may be methyl groups.

[0642] In the above formula (II), two adjacent ones selected from R3 to R5 are bonded to a and b, respectively; R9 to R11 Two adjacent ones selected from can be bonded to c and d respectively.

[0643] For example, in formula (II), R3 and R4 can be bonded to a and b, respectively, or R4 and R5 can be bonded to a and b, respectively. Also, in formula (II), R9 and R 10 These are respectively bound to c and d, or R 10 and R 11 These can be combined with c and d respectively.

[0644] In one specific example, in formula (II), R3 and R4 are bonded to a and b, respectively, and R9 and R 10 These can be bonded to c and d respectively. In another specific example, in formula (II), R4 and R5 are bonded to a and b respectively, and R9 and R 10 These can be bonded to c and d respectively. In another specific example, in formula (II), R3 and R4 are bonded to a and b respectively, and R 10 and R 11 These can be bonded to c and d respectively. In another specific example, in formula (II), R4 and R5 are bonded to a and b respectively, and R 10 and R 11 These can be combined with c and d respectively.

[0645] In the above formula (II), R3 to R6 that do not bind to a and b, and R9 to R that do not bind to c and d 12 is a hydrogen atom.

[0646] In one specific example, in formula (II), all Ls are single bonds.

[0647] In another specific example, in formula (II), one L is a single bond and the other L is a phenylene group.

[0648] In another specific example, in formula (II), all Ls are phenylene groups.

[0649] In the above formula (II), at least one L may be a deuterated group. For example, in the above formula (II), each L may independently be a single bond or a phenylene group substituted with a deuterium atom. Specifically, in the above formula (II), at least one L may be a phenylene group substituted with a deuterium atom.

[0650] In the above formula (II), Ar1 is unsubstituted or has two substituents, and the substituents can combine with each other to form a condensed ring having 5 to 20 ring-forming carbon atoms.

[0651] In one example, in the above formula (II), Ar1 has a substituent at each of two adjacent carbon positions, and the substituents can be combined with each other to form a condensed ring having 5 to 20 ring carbon atoms. The condensed ring having 5 to 20 ring carbon atoms can be, for example, a benzene ring. In one specific example, Ar1 is substituted or unsubstituted. Silver has a substituent at each of two adjacent carbon positions, and the substituents can combine with each other to form a benzene ring, and when X is O, Ar1 is substituted or unsubstituted. It could be.

[0652] Among Ar1 in the above formula (II), A may be a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms. For example, the aryl group having 6 to 20 carbon atoms may be a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, or a 9,9-diphenylfluorenyl group.

[0653] Among Ar1 in the above formula (II), A may be an aromatic heterocyclic group having 5 to 20 ring atoms, which is substituted or unsubstituted.

[0654] The aromatic heterocyclic group having 5 to 20 ring-forming atoms includes at least one heteroatom selected from among nitrogen (N) atoms, oxygen (O) atoms, and sulfur (S) atoms among the ring-forming atoms. For example, the aromatic heterocyclic group having 5 to 20 ring atoms is a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolizinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, an indazolyl group, a phenanthrolinyl group, a phenanthridinyl group, an acridinyl group, a phenazinyl group, Carbazolyl group, benzocarbazolyl group, morpholino group, phenoxazinyl group, phenothiazinyl group, azacarbazolyl group, diazacabazolyl group, furyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzisoxazolyl group, phenoxazinyl group, morpholino group, dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, azanapthobenzofuranyl group, diazanaphthobenzofuranyl group, thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, Benzothiophene group (benzothienyl group), isobenzothiophene group (isobenzothiophene group), dibenzothiophene group (dibenzothiophene group), naphthobenzothiophene group (naphthobenzothiophene group), benzothiazolyl group, benzisothiazolyl group, phenothiazinyl group, dinaphthothiophene group (dinaphthothiophene group), azadibenzothiophene group (azadibenzothiophene group), diazadibenzothiophene group (diazadibenzothiophene group), azanaphthobenzothiophene group (azanaphthobenzothiophene group), or diazanaphthobenzothiophene group (diazanaphthobenzothiophene group).

[0655] In one specific example, in the above formula (II), A may be an aromatic heterocyclic group having 5 to 20 ring atoms and a substituted or unsubstituted ring containing an oxygen (O) atom, and more specifically, may be an aromatic heterocyclic group having 10 to 20 ring atoms and an unsubstituted ring containing an oxygen (O) atom.

[0656] In the above formula (II), Ar1, X is an oxygen atom or -CR 13 R 14 and; R 13 and R 14 are each independently a methyl group or a phenyl group, or R 13 and R 14 are combined with each other to form a spiro ring having 5 to 20 ring-forming carbon atoms.

[0657] In one example, among Ar1 of the above formula (II), R 13 and R 14 One of them can be a methyl group and the other can be a phenyl group. In another example, R 13 and R 14 can combine with each other to form an aromatic spiro ring having 5 to 20 ring carbon atoms. In one specific example, R 13 and R 14 can combine with each other to form fluorene, and thus Ar1 can become 9,9'-spirofluorene.

[0658] Ar1 of the above formula (II) is substituted or unsubstituted For example, it can be 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, or 9-phenanthrenyl.

[0659] Ar1 of the above formula (II) is substituted or unsubstituted Silver substituted or unsubstituted , or substituted or unsubstituted It can be. Among the Ar1 of the above formula (II), substituted or unsubstituted Silver substituted or unsubstituted , or substituted or unsubstituted It can be. Among the Ar1 of the above formula (II), substituted or unsubstituted Silver substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , or substituted or unsubstituted It could be.

[0660] Ar1 of the above formula (II) is substituted or unsubstituted Silver substituted or unsubstituted It can be. Among the Ar1 of the above formula (II), substituted or unsubstituted Silver substituted or unsubstituted It can be. Among the Ar1 of the above formula (II), substituted or unsubstituted Silver substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , or substituted or unsubstituted It can be. Among the Ar1 of the above formula (II), substituted or unsubstituted Silver substituted or unsubstituted It could be.

[0661]

[0662] In one example, Ar1 in the above formula (II) is substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , or substituted or unsubstituted am.

[0663]

[0664] In one specific example, in the formula (II), R1, R2, R7 and R8 are methyl groups; two adjacent groups selected from R3 to R5 are bonded to a and b, respectively; and R9 to R 11 Two adjacent ones selected from are bonded to c and d respectively; L is a single bond; Ar1 ​​is unsubstituted or has two substituents, and the substituents are bonded to each other to form a condensed ring having 5 to 20 ring carbon atoms; A is a substituted or unsubstituted aromatic heterocyclic group having 5 to 20 ring atoms; X is an oxygen atom or -CR 13 R 14 and; R 13 and R 14 are each independently a methyl group or a phenyl group, or R 13 and R 14 are combined with each other to form a spiro ring having 5 to 20 ring-forming carbon atoms.

[0665]

[0666] As described above, the term "hydrogen atom" used herein includes light hydrogen atoms, deuterium atoms, and tritium atoms. Therefore, the inventive compound may contain naturally occurring deuterium atoms.

[0667] In addition, deuterium atoms may be intentionally introduced into the inventive compound by using a deuterated compound in part or in whole of the raw material compound. Therefore, in one embodiment of the present invention, the inventive compound contains at least one deuterium atom. That is, the inventive compound may be a compound represented by Formula (I) or Formula (II), wherein at least one of the hydrogen atoms contained in the compound is a deuterium atom.

[0668] The deuteration rate of the inventive compound depends on the deuteration rate of the raw material compound used. Even if a raw material with a predetermined deuteration rate is used, a certain proportion of naturally occurring deuterium isotopes may be included. Therefore, the deuteration rate of the inventive compound shown below includes a proportion that takes into account trace amounts of naturally occurring isotopes, compared to the proportion calculated by simply counting the number of deuterium atoms represented by the chemical formula.

[0669] The deuteration rate 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.

[0670] The invention compound may be a deuterium compound in which all hydrogen atoms are deuterium atoms (i.e., the deuteration rate of the invention compound is 100%).

[0671] The inventive compound may be a mixture comprising a deuterated compound and a non-deuterated compound, or a mixture of two or more compounds having different deuteration rates. The deuteration rate of such a mixture is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, still more preferably 10% or more, still more preferably 50% or more, and further less than 100%.

[0672] In addition, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the inventive compound is preferably 1% or more, more preferably 3% or more, more preferably 5% or more, even more preferably 10% or more, and also 100% or less.

[0673] Details of the substituent (any substituent) in the case of “substituted or unsubstituted” included in the definition of each of the above formulas are as described in “Substituent in the case of “substituted or unsubstituted”” unless otherwise specified.

[0674] The method for producing the inventive compound is not particularly limited, and a person skilled in the art can easily produce the compound by the method described in the examples below, or by a method modified by referring to a known synthetic method.

[0675] Specific examples of the invention compounds are shown below, but the invention compounds are not limited to the following exemplary compounds.

[0676] In the following specific examples, D represents a deuterium atom.

[0677] Example compounds of formula (I)

[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] Example compounds of formula (II)

[0726]

[0727]

[0728]

[0729]

[0730]

[0731]

[0732]

[0733]

[0734]

[0735]

[0736]

[0737]

[0738]

[0739]

[0740]

[0741]

[0742]

[0743]

[0744]

[0745] Materials for organic EL devices

[0746] A material for an organic EL device, which is one aspect of the present invention, includes the invention compound.

[0747] The content of the inventive compound in the material for an organic EL device is 1 mass% or more (including 100%), preferably 10 mass% or more (including 100%), more preferably 50 mass% or more (including 100%), still more preferably 80 mass% or more (including 100%), and particularly preferably 90 mass% or more (including 100%). The material for an organic EL device, which is one aspect of the present invention, is useful for manufacturing an organic EL device.

[0748] In one aspect of the present invention, it is preferable that the compound of the present invention is a hole transport layer material.

[0749] In one aspect of the present invention, the compound of the present invention can also be used as a hole injection layer material.

[0750] In one embodiment of the present invention, the material for an organic EL device preferably further comprises a hydrogen-containing compound of the present invention. The hydrogen-containing compound is a compound in which all hydrogen atoms in the compound of the present invention are hydrogen atoms.

[0751] The molar ratio of the invention compound and the hydrophobic substance of the invention compound (invention compound: hydrophobic substance) is preferably 10:90 to 90:10, more preferably 20:80 to 80:20, still more preferably 30:70 to 70:30, and particularly preferably 40:60 to 60:40.

[0752] A material for an organic electroluminescent device according to one embodiment of the present invention preferably includes the invention compound.

[0753] In the material for an organic electroluminescent device, the content of the inventive compound is preferably 1 mass% or more (including 100%), more preferably 10 mass% or more (including 100%), further preferably 50 mass% or more (including 100%), still more preferably 80 mass% or more (including 100%), and particularly preferably 90 mass% or more (including 100%).

[0754]

[0755] Organic EL devices

[0756] An organic EL device according to one aspect of the present invention has an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer is composed of a single or multiple layers including a light-emitting layer, and at least one of the organic layers includes the invention compound.

[0757] Examples of organic layers containing the inventive compound include, but are not limited to, a hole transport zone (hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer, etc.) provided between the anode and the light-emitting layer, a light-emitting layer, a spacer layer, an electron transport zone (electron injection layer, electron transport layer, hole blocking layer, etc.) provided between the cathode and the light-emitting layer, and the like. The inventive compound is preferably used as a material for a hole transport zone or a light-emitting layer of a fluorescent or phosphorescent EL device, more preferably as a material for a hole transport zone, 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.

[0758] The organic EL device, which is one embodiment of the present invention, may be a single-color light-emitting device of a fluorescent or phosphorescent type, a white light-emitting device of a fluorescent / phosphorescent hybrid type, a simple type having a single light-emitting unit, or a tandem type having multiple light-emitting units, and among these, a fluorescent light-emitting device is preferable. Here, the "light-emitting unit" refers to the smallest unit that includes an organic layer, at least one of which is a light-emitting layer, and emits light by the recombination of injected holes and electrons.

[0759] For example, as a representative device configuration of a simple organic EL device, the following device configuration can be mentioned.

[0760] (1) Anode / luminescent unit / cathode

[0761] 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 spacer layer may be provided between each light-emitting layer for the purpose of preventing excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer. A representative layer configuration of a simple light-emitting unit is shown below. The layers in parentheses are arbitrary.

[0762] (a) (hole injection layer / ) hole transport layer / fluorescent emitting layer / electron transport layer( / electron injection layer)

[0763] (b) (hole injection layer / ) hole transport layer / first fluorescent emitting layer / second fluorescent emitting layer / electron transport layer ( / electron injection layer)

[0764] (c) (hole injection layer / ) hole transport layer / phosphorescent emitting layer / space layer / fluorescent emitting layer / electron transport layer ( / electron injection layer)

[0765] (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)

[0766] (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)

[0767] (f) (hole injection layer / ) hole transport layer / electron blocking layer / fluorescent emitting layer / electron transport layer( / electron injection layer)

[0768] (g) (hole injection layer / ) hole transport layer / exciton blocking layer / fluorescent emitting layer / electron transport layer( / electron injection layer)

[0769] (h) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent emitting layer / electron transport layer ( / electron injection layer)

[0770] (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).

[0771] (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)

[0772] (i1) (hole injection layer / ) first hole transport layer / second hole transport layer / third hole transport layer / fluorescent emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer)

[0773] (j) (hole injection layer / ) hole transport layer / fluorescent emitting layer / hole blocking layer / electron transport layer( / electron injection layer)

[0774] (k) (hole injection layer / ) hole transport layer / fluorescent emitting layer / exciton blocking layer / electron transport layer( / electron injection layer)

[0775] Each of the above phosphorescent or fluorescent emitting layers may exhibit different emission colors. Specifically, in the above emitting unit (d), a layer configuration 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 mentioned.

[0776] Meanwhile, an electron-blocking layer may be provided between each light-emitting layer and the hole-transporting layer or spacer layer, as appropriate. Furthermore, a hole-blocking layer may be provided between each light-emitting layer and the electron-transporting layer, as appropriate. By providing an electron-blocking layer or a hole-blocking layer, electrons or holes can be confined within the light-emitting layer, increasing the probability of charge recombination in the light-emitting layer and improving luminous efficiency.

[0777] As representative device configurations of tandem organic EL devices, the following device configurations can be cited.

[0778] (2) Anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode

[0779] Here, the first light emitting unit and the second light emitting unit can be independently selected from the light emitting units described above, for example.

[0780] The above intermediate layer is generally also called an intermediate electrode, an intermediate conductive layer, a charge generating layer, an electron extraction layer, a connection layer, or an intermediate insulating layer, and may utilize a known material composition that supplies electrons to the first light emitting unit and holes to the second light emitting unit.

[0781] 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.

[0782] 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). A hole transport zone (6) (hole injection layer, hole transport layer, etc.) is disposed between the light-emitting layer (5) and the anode (3), and an electron transport zone (7) (electron injection layer, electron transport layer, etc.) is disposed between the light-emitting layer (5) and the cathode (4). In addition, an electron-blocking layer (not shown) may be provided on the anode (3) side of the light-emitting layer (5), and a hole-blocking layer (not shown) may be provided on the cathode (4) side of the light-emitting layer (5). Thereby, electrons and holes can be confined in the light-emitting layer (5), and the efficiency of generating excitons in the light-emitting layer (5) can be further increased.

[0783] Fig. 2 is a schematic diagram showing another configuration of an 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 zone disposed between the anode (3) and the light-emitting layer (5) is formed by a hole injection layer (6a), a first hole transport layer (6b), and a second hole transport layer (6c). In addition, an electron transport zone 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).

[0784] Fig. 3 is a schematic diagram showing another configuration of an 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 zone 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). In addition, an electron transport zone 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).

[0785] In FIGS. 1 to 3, the light-emitting layer (5) includes at least one light-emitting layer. The light-emitting layer (5) may be a single layer or may include multiple layers (e.g., multiple light-emitting layers, multiple light-emitting layers and a space layer).

[0786] Meanwhile, in the present invention, a host combined with a fluorescent dopant material (fluorescent emitting material) is called a fluorescent host, and a host combined with a phosphorescent dopant material is called a phosphorescent host. A fluorescent host and a phosphorescent host 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 a fluorescent host.

[0787]

[0788] substrate

[0789] The substrate is used as a support for the organic EL element. Examples of substrates that can be used include plates made of glass, quartz, plastic, and the like. Furthermore, 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. Furthermore, an inorganic deposition film may also be used.

[0790]

[0791] anode

[0792] 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 thereof include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, graphene, etc. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the above metals (e.g., titanium nitride), etc.

[0793] These materials are typically formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1 to 10 wt% of zinc oxide relative to indium oxide, and indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5 to 5 wt% of tungsten oxide and 0.1 to 1 wt% of zinc oxide relative to indium oxide. In addition, they can be formed by vacuum deposition, coating, inkjet, spin coating, etc.

[0794]

[0795] hole transport band

[0796] As described above, the organic layer may include a hole transport zone between the anode and the light-emitting layer. The hole transport zone is composed of a hole injection layer, a hole transport layer, an electron blocking layer, etc. It is preferable that the hole transport zone includes the inventive compound. It is preferable that at least one of these layers constituting the hole transport zone includes the inventive compound, and it is particularly more preferable that the hole transport layer includes the inventive compound.

[0797] 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 of elements) can be used.

[0798] Materials with a small work function, such as elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) or cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), and ytterbium (Yb), and alloys containing them, etc. can also be used. Meanwhile, when forming an anode using an alkali metal, an alkaline earth metal, and an alloy containing them, a vacuum deposition method or a sputtering method can be used. In addition, when using silver paste or the like, a coating method or an inkjet method can be used.

[0799]

[0800] hole injection layer

[0801] The hole injection layer is a layer containing a material having 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.

[0802] 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.

[0803] Low molecular weight organic compounds 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), Aromatic amine compounds such as 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2) and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) can also be used as hole injection layer materials.

[0804] Polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used. Examples thereof include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD). In addition, polymer compounds to which acids are added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[0805] Additionally, it is also preferable to use an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K).

[0806]

[0807] (In the above formula, R 221 ∼R 226 Silver, each independently a cyano group, -CONH2, a 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). In addition, R 221 and R 222 , R 223 and R 224 , and R 225 and R 226 Two adjacent groups selected from may combine with each other to form a group represented by -CO-O-CO-.)

[0808] R 227 Examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.

[0809]

[0810] hole transport layer

[0811] The hole transport layer is a layer containing a material with high hole transport properties (hole transport material) and is formed between the anode and the light-emitting layer, or, if present, between the hole injection layer and the light-emitting layer. The inventive compound may be used alone or in combination with the compounds described below in the hole transport layer.

[0812] The hole transport layer may have a single-layer structure or a multi-layer structure including two or more layers. For example, the hole transport layer may have 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 region may include a first hole transport layer on the anode side and a second hole transport layer on the cathode side. Furthermore, the hole transport layer may have a three-layer structure including a first hole transport layer, a second hole transport layer, and a third hole transport layer in sequence from the anode side. That is, the third hole transport layer may be arranged between the second hole transport layer and the light-emitting layer.

[0813] In one aspect of the present invention, it is preferable that the hole transport layer of the single-layer structure is adjacent to the light-emitting layer, and furthermore, it is preferable that the hole transport layer closest to the cathode in the multi-layer structure, for example, the second hole transport layer of the two-layer structure or the third hole transport layer of the three-layer structure, is adjacent to the light-emitting layer. In one example, the light-emitting layer and the second hole transport layer may be in direct contact.

[0814] In another aspect of the present invention, an electron blocking layer, etc., described later, 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 in the multilayer structure and the light-emitting layer. In addition, as described above, when the hole transport layer is a multilayer structure including two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer in the multilayer structure may be used as an electron blocking layer.

[0815] In one embodiment of the organic electroluminescence device according to the present invention, at least one of the first hole transport layer and the second hole transport layer comprises the invention compound. Specifically, in the hole transport layer having a two-layer structure, the invention 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 invention compound. Specifically, when the hole transport layer has a three-layer structure, the invention 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.

[0816] In one aspect of the present invention, it is preferable that the invention compound is included in the second hole transport layer, and specifically, it is preferable that the invention compound is included only in the second hole transport layer, or that the invention compound is included in the first hole transport layer and the second hole transport layer.

[0817] 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, is preferably a hydrogen body from the viewpoint of manufacturing cost.

[0818] The above-mentioned hydrogen compound is an invention compound in which all hydrogen atoms in the invention compound are hydrogen atoms.

[0819] Accordingly, the present invention includes 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 solely of a hydrophobic substance. The term "inventive compound substantially composed solely of a hydrophobic substance" means that the content ratio of the hydrophobic substance relative to the total amount of the inventive compound is 90 mol% or more, preferably 95 mol% or more, and more preferably 99 mol% or more (each including 100%).

[0820] As hole transport layer materials other than the invention compound, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used.

[0821] As aromatic amine compounds, for example, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) can be mentioned. The compound is 10 -6 cm 2 / It has a hole mobility of Vs or more.

[0822] Examples of carbazole derivatives include 4,4'-di(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA).

[0823] Examples of anthracene derivatives include 2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth).

[0824] Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.

[0825] However, compounds other than those mentioned above may be used if they have a higher hole transport property than electron transport property.

[0826] In one embodiment of the organic EL device according to the present invention, the first hole transport layer includes a compound represented by the following formula (21) or formula (22).

[0827]

[0828] [Among the above equations (21) and (22),

[0829] L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[0830] k is 1, 2, 3, or 4,

[0831] If k is 1, L E2 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[0832] If k is 2, 3 or 4, then plural L E2 are identical to each other, or different,

[0833] If k is 2, 3 or 4, then plural L E2 are combined with each other to form a substituted or unsubstituted monocyclic ring, or are combined with each other to form a substituted or unsubstituted condensed ring, or are not combined with each other,

[0834] L which does not form the above-mentioned single ring and also does not form the above-mentioned condensed ring E2 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[0835] A 1 , B 1 , C 1 , A 2 , B 2 , C 2 , and D 2 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or -Si(R' 901 )(R' 902 )(R' 903 ) and,

[0836] R' 901 , R' 902 and R' 903 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0837] R' 901 If this plural exists, then plural R' 901 are identical to each other, or different,

[0838] R' 902 If there are multiple R's, then multiple R's 902 are identical to each other, or different,

[0839] R' 903 If this plural exists, then plural R' 903 are identical or different from each other.]

[0840] In addition, the first hole transport layer may contain one type of compound represented by formula (21) and formula (22), or may contain multiple types of compounds represented by formula (21) and formula (22).

[0841] In equations (21) and (22), A 1 , B 1 , C 1 , A 2 , B 2 , C 2 , and D 2 is 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.

[0842] Also, more preferably, in equation (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 the groups 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.

[0843] A 1 , B 1 , C 1 , A 2 , B 2 , C 2 , and D 2The fluorenyl group that can be formed may have a substituent at the 9-position, for example, a 9,9-dimethylfluorenyl group or a 9,9-diphenylfluorenyl group. In addition, the substituents at the 9-position may form a ring, for example, the substituents at the 9-position may form a fluorene skeleton or a xanthene skeleton.

[0844] L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 are, preferably, each independently, a single bond, a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.

[0845] Specific examples of compounds represented by formulas (21) and (22) include, for example, the following compounds.

[0846]

[0847]

[0848] Dopant material of the light-emitting layer

[0849] The light-emitting layer is a layer containing a highly luminescent material (dopant material), and various materials can be used. For example, fluorescent or phosphorescent materials can be used as dopant materials. Fluorescent materials are compounds that emit light from a singlet excited state, and phosphorescent materials are compounds that emit light from a triplet excited state.

[0850] In one embodiment of the organic EL device according to the present invention, the light-emitting layer is a single layer.

[0851] In addition, in another aspect of the organic EL device according to the present invention, the light-emitting layer includes a first light-emitting layer and a second light-emitting layer.

[0852] 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-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), etc. can be mentioned.

[0853] As a green fluorescent emitting material that can be used in the light-emitting layer, aromatic amine derivatives, etc. can be used. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), Examples include N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), etc.

[0854] As a red fluorescent emitting material that can be used in the emitting layer, tetracene derivatives, diamine derivatives, etc. can be used. Specifically, N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), etc. can be mentioned.

[0855] In one aspect of the present invention, it is preferable that the light-emitting layer includes a fluorescent light-emitting material (fluorescent dopant material).

[0856] As a blue phosphorescent material that can be used in the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used. Specifically, bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviation: FIrpic), bis[2-(3',5'-bistrifluoromethylphenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviation: Ir(CF3ppy)2(pic)), bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) acetylacetonate (abbreviation: FIracac), etc. can be mentioned.

[0857] As a green phosphorescent material that can be used in the light-emitting layer, iridium complexes, etc. are used. Examples thereof include tris(2-phenylpyridinato-N,C2')iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazolato)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), and bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)).

[0858] As a red-based phosphorescent material that can be used in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used. Specifically, organometallic complexes such as bis[2-(2'-benzo[4,5-α]thienyl)pyridinato-N,C3']iridium(III) acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinolinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP) can be mentioned.

[0859] In addition, rare earth metal complexes such as tris(acetylacetonate)(monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: Eu(DBM)3(Phen)), and tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3(Phen)) can be used as phosphorescent materials because the emission is from the rare earth metal ion (electron transition between different multiplicities).

[0860]

[0861] Host material of the light-emitting layer

[0862] The light-emitting layer may be configured by dispersing the aforementioned dopant material in another material (host material). It is preferable to use a material with a lower unoccupied orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) than the dopant material.

[0863] As a host material, for example,

[0864] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes,

[0865] (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives,

[0866] (3) Condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives,

[0867] (4) An aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative is used.

[0868] For example, metal complexes such as tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ);

[0869] 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-oxadiazol-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), bathophenanthroline (abbreviation: BPhen), and bathocuproine (abbreviation: BCP);

[0870] 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), Condensed aromatic compounds such as 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 3,3',3"-(benzene-1,3,5-triyl)tripyrene (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenylchrysene, and the like; and

[0871] N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), Aromatic amine compounds such as 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) can be used. Multiple types of host materials may be used.

[0872] In particular, in the case of a blue fluorescent element, it is preferable to use the following anthracene compound as a host material.

[0873]

[0874]

[0875]

[0876]

[0877]

[0878] In one embodiment of the organic EL device according to the present invention, when the light-emitting layer includes 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 components constituting the second light-emitting layer. For example, an embodiment in which a dopant material included in the first light-emitting layer is different from a dopant material included in the second light-emitting layer, or an embodiment in which a host material included in the first light-emitting layer is different from a host material included in the second light-emitting layer, may be mentioned.

[0879] In the organic EL device of the present invention, the light-emitting layer may contain a light-emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less.

[0880] 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, placed in a quartz cell, and the emission spectrum of this sample (vertical axis: emission intensity, horizontal axis: wavelength) is measured at room temperature (300 K). The emission spectrum can be measured using a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Science Co., Ltd. In addition, the emission spectrum measuring device is not limited to the device used herein.

[0881] In the luminescence spectrum, the peak wavelength of the luminescence spectrum at which the luminescence intensity is maximum is referred to as the main peak wavelength. Meanwhile, in this specification, the main peak wavelength is sometimes referred to as the fluorescence emission main peak wavelength (FL-peak).

[0882] The luminescent compound exhibiting fluorescence with a main peak wavelength of 500 nm or less may be the dopant material or the host material.

[0883] When the light-emitting layer is a single layer, only one of the dopant material and the host material may be a light-emitting compound exhibiting fluorescence emission with a main peak wavelength of 500 nm or less, or both may be light-emitting compounds exhibiting fluorescence emission with a main peak wavelength of 500 nm or less.

[0884] In addition, when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, only one of the first light-emitting layer and the second light-emitting layer may include a light-emitting compound that exhibits fluorescent emission having a main peak wavelength of 500 nm or less, or both light-emitting layers may include light-emitting compounds that exhibit fluorescent emission having a main peak wavelength of 500 nm or less. When the first light-emitting layer includes a light-emitting compound that exhibits fluorescent emission having a main peak wavelength of 500 nm or less, only one of the dopant material and the host material included in the first light-emitting layer may be a light-emitting compound that exhibits fluorescent emission having a main peak wavelength of 500 nm or less, or both may be light-emitting compounds that exhibit fluorescent emission having a main peak wavelength of 500 nm or less. In addition, when the second light-emitting layer includes a light-emitting compound that exhibits fluorescence 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 light-emitting layer may be a light-emitting compound that exhibits fluorescence emission with a main peak wavelength of 500 nm or less, or both materials may be light-emitting compounds that exhibit fluorescence emission with a main peak wavelength of 500 nm or less.

[0885]

[0886] electron transport layer

[0887] The electron transport layer is a layer containing a material with high electron transport properties (electron transport material), and is formed between the light-emitting layer and the cathode, or, if present, between the electron injection layer and the light-emitting layer.

[0888] The electron transport layer may have a single-layer structure or a multi-layer structure including two or more layers. For example, the electron transport layer may have 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, the electron transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, and furthermore, the electron transport layer closest to the anode in the multi-layer structure, for example, the first electron transport layer of the two-layer structure, is preferably adjacent to the light-emitting layer. In another aspect of the present invention, a hole-blocking layer or the like described below 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 in the multi-layer structure and the light-emitting layer.

[0889] In the electron transport layer, for example,

[0890] (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes,

[0891] (2) Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives,

[0892] (3) Polymer compounds can be used.

[0893] As metal complexes, for example, tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), (8-quinolinolate)lithium (abbreviation: Liq) can be mentioned.

[0894] Examples of heteroaromatic compounds include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) can be mentioned.

[0895] As polymer compounds, examples thereof include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).

[0896] The above materials are 10 -6 cm 2 / Vs or higher electron mobility. On the other hand, if it is a material with a higher electron transport property than a hole transport property, a material other than the above may be used for the electron transport layer. Furthermore, the electron transport layer may be a single layer or a laminate 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.

[0897]

[0898] electron injection layer

[0899] The electron injection layer is a layer containing a material with high electron injection properties. The electron injection layer can be formed using 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. Examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes such as lithium (8-quinolinolate) (abbreviation: 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. Furthermore, a plurality of these compounds can be mixed and used.

[0900] In addition, a material having electron transport properties containing an alkali metal, alkaline earth metal, or a compound thereof, specifically, a material containing magnesium (Mg) in Alq, may be used. In this case, electron injection from the cathode can be performed more efficiently.

[0901] 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 has excellent electron injection and electron transport properties because the organic compound receives electrons from the electron donor. In this case, the organic compound is preferably a material that is excellent in transporting the received electrons. Specifically, for example, a material constituting the electron transport layer described above (such as a metal complex or a heteroaromatic compound) can be used. The electron donor may be a material that exhibits electron donating properties toward the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and examples thereof include lithium, cesium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides and alkaline earth metal oxides are also preferable, and examples thereof include lithium oxide, calcium oxide, and barium oxide. A Lewis base such as magnesium oxide may also be used. Furthermore, an organic compound such as tetrathiafulvalene (abbreviation: TTF) may also be used.

[0902]

[0903] cathode

[0904] For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having 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, i.e., alkali metals such as lithium (Li) or cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), and ytterbium (Yb), and alloys containing these.

[0905] Meanwhile, when forming a cathode using an alkali metal, alkaline earth metal, or an alloy containing them, vacuum deposition or sputtering can be used. Furthermore, when using silver paste or the like, coating or inkjet methods can be used.

[0906] 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 work function. These conductive materials can be deposited into a film using a sputtering method, an inkjet method, a spin coating method, or the like.

[0907]

[0908] Insulating layer

[0909] Organic EL devices are prone to pixel defects due to leakage or short-circuiting because an electric field is applied to an ultra-thin film. To prevent this, an insulating layer consisting of an insulating thin film may be inserted between a pair of electrodes.

[0910] Examples of materials used in the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. Alternatively, mixtures or laminates thereof may be used.

[0911]

[0912] space layer

[0913] The above space layer is, for example, a layer provided between a fluorescent light-emitting layer and a phosphorescent light-emitting layer for the purpose of preventing excitons generated in the phosphorescent light-emitting layer from diffusing into the fluorescent light-emitting layer or adjusting the carrier balance when laminating a fluorescent light-emitting layer and a phosphorescent light-emitting layer. In addition, the space layer may be provided between a plurality of phosphorescent light-emitting layers.

[0914] Since the spacer layer is provided between the light-emitting layers, it is preferably a material that possesses both electron-transport and hole-transport properties. Furthermore, to prevent triplet energy diffusion within the adjacent phosphorescent light-emitting layer, a triplet energy of 2.6 eV or higher is preferred. Examples of materials used in the spacer layer include those similar to those used in the aforementioned hole-transport layer.

[0915]

[0916] low-rise

[0917] A blocking layer such as an electron blocking layer, a hole blocking layer, or an exciton blocking layer may be provided adjacent to the light-emitting layer. The electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer, and the hole blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron transport layer. The exciton blocking layer has the function of confining excitons within the light-emitting layer by preventing excitons generated in the light-emitting layer from diffusing to surrounding layers.

[0918]

[0919] Each layer of the above organic EL device can be formed by a conventionally known deposition method, coating method, etc. For example, it can be formed by a known method such as a vacuum deposition method, molecular beam deposition (MBE) method, or a coating method such as a dipping method, spin coating method, casting method, bar coating method, or roll coating method using a solution of a compound that forms the layer.

[0920] The film thickness of each layer is not particularly limited, but in general, if the film thickness is too thin, defects such as pinholes are likely to occur, and conversely, if the film thickness is too thick, a high driving voltage is required, resulting in poor efficiency. Therefore, it is usually 5 nm to 10 μm, and 10 nm to 0.2 μm is more preferable.

[0921] In the organic EL device having the 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 or more and 150 nm or less, and more preferably 40 nm or more and 130 nm or less.

[0922] In addition, in one embodiment of the organic EL device of the present invention, the thickness of the second hole transport layer is preferably 5 nm or more, and further preferably 100 nm or less.

[0923] In addition, in one embodiment 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 further preferably 100 nm or less.

[0924] In addition, in one embodiment 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.

[0925] Preferred embodiments of the organic EL device of the present invention include, for example,

[0926] As an organic EL device having a two-layer hole transport layer,

[0927] · A first embodiment wherein the second hole transport layer comprises the invention compound and the first hole transport layer does not comprise the invention compound;

[0928] · A second embodiment in which both the first hole transport layer and the second hole transport layer comprise the inventive compound;

[0929] · A third embodiment, wherein the first hole transport layer comprises the invention compound and the second hole transport layer does not comprise the invention compound;

[0930] As an organic EL device having a three-layer hole transport layer structure,

[0931] · A fourth embodiment, wherein the first hole transport layer comprises the invention compound, and the second and third hole transport layers do not comprise the invention compound;

[0932] · A fifth embodiment, wherein the second hole transport layer comprises the invention compound, and the first and third hole transport layers do not comprise the invention compound;

[0933] · A sixth embodiment, wherein the third hole transport layer comprises the invention compound, and the first and second hole transport layers do not comprise the invention compound;

[0934] · A seventh embodiment, wherein the first and second hole transport layers comprise the invention compound, and the third hole transport layer does not comprise the invention compound;

[0935] · An eighth embodiment, wherein the first and third hole transport layers comprise the invention compound, and the second hole transport layer does not comprise the invention compound;

[0936] · A ninth embodiment, wherein the second and third hole transport layers comprise the invention compound, and the first hole transport layer does not comprise the invention compound;

[0937] · A tenth embodiment, wherein all of the first to third hole transport layers comprise the inventive compound; etc.

[0938]

[0939] electronic devices

[0940] The above organic EL element can be used in electronic devices such as display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and light-emitting devices such as lighting and vehicle lighting.

[0941]

[0942] Example

[0943] Hereinafter, the present invention will be described in more detail using examples, but the present invention is not limited to the following examples.

[0944]

[0945] The compounds represented by formula (I) or formula (II) used in the production of organic EL devices of Examples 1 to 11 are shown below.

[0946]

[0947]

[0948]

[0949]

[0950] The comparative compounds used in the manufacture of the organic EL device of Comparative Example 1 are shown below.

[0951]

[0952]

[0953] Other compounds used in the manufacture of the organic EL devices of Examples 1 to 11 and Comparative Example 1 are shown below.

[0954]

[0955]

[0956] The compounds represented by formula (I) or formula (II) used in the production of organic EL devices of Examples 12 to 14 are shown below.

[0957]

[0958] The comparative compounds used in the manufacture of the organic EL device of Comparative Example 2 are shown below.

[0959]

[0960]

[0961] Other compounds used in the manufacture of the organic EL devices of Examples 12 to 14 and Comparative Example 2 are shown below.

[0962]

[0963]

[0964] <Fabrication of organic EL devices>

[0965] Organic EL devices were manufactured and evaluated as follows.

[0966]

[0967] Example 1

[0968] A 25 mm × 75 mm × 1.1 mm ITO transparent electrode (anode) attached glass substrate (manufactured by Geomatech Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was 130 nm.

[0969] After cleaning, the glass substrate with an ITO transparent electrode attached was mounted on the substrate holder of a vacuum deposition device, and the compound Inv-1 and compound HA were co-deposited by first covering the transparent electrode on the side where the transparent electrode was formed, thereby forming a hole injection layer with a film thickness of 10 nm. The mass ratio of compound Inv-1 to compound HA (Inv-1:HA) was 97:3.

[0970] Next, compound Inv-1 was deposited on the hole injection layer to form a first hole transport layer with a film thickness of 77.5 nm.

[0971] Next, compound HT-2 was deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 7.5 nm.

[0972] Next, compound BH-1, compound BH-2, and compound BD were co-deposited on the second hole transport layer to form a light-emitting layer having a film thickness of 20 nm. The mass ratio of compound BH-1, compound BH-2, and compound BD (BH-1:BH-2:BD) was 58.8:39.2:2.

[0973] Next, compound ET-1 was deposited on the above-mentioned light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[0974] 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 25 nm. The mass ratio of compound ET-2 and Liq (ET-2:Liq) was 67:33.

[0975] Next, Yb was deposited on the second electron transport layer to form an electron injection electrode with a film thickness of 1 nm.

[0976] Then, metal Al was deposited on the electron injection electrode to form a metal cathode with a film thickness of 80 nm.

[0977] The device configuration of the organic EL device of Example 1 is briefly described below.

[0978] ITO(130) / Inv-1:HA(10, 97:3) / Inv-1(77.5) / HT-2(7.5) / BH-1:BH-2:BD(20, 58.8:39.2:2) / ET-1(5) / ET-2:Liq(25, 67:33) / Yb(1) / Al(80)

[0979] In the above device configuration, the number in parentheses is the film thickness (nm), and the ratio is the mass ratio of the compound used.

[0980]

[0981] Examples 2 to 11

[0982] Organic EL devices of Examples 2 to 11 were manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of the compound Inv-1 in Example 1.

[0983]

[0984] Comparative Example 1

[0985] The organic EL device of Comparative Example 1 was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 below was used instead of the compound Inv-1 in Example 1.

[0986]

[0987] Example 12

[0988] A 25 mm × 75 mm × 1.1 mm ITO transparent electrode (anode) attached glass substrate (manufactured by Geomatech Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was 130 nm.

[0989] After cleaning, the glass substrate with an ITO transparent electrode attached was mounted on the substrate holder of a vacuum deposition device, and the compound HT-1 and compound HA were co-deposited by first covering the transparent electrode on the side where the transparent electrode was formed, thereby forming 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.

[0990] Next, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer with a film thickness of 77.5 nm.

[0991] Next, compound Inv-12 was deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 7.5 nm.

[0992] Next, compound BH-1, compound BH-2, and compound BD were co-deposited on the second hole transport layer to form a light-emitting layer having a film thickness of 20 nm. The mass ratio of compound BH-1, compound BH-2, and compound BD (BH-1:BH-2:BD) was 58.8:39.2:2.

[0993] Next, compound ET-1 was deposited on the above-mentioned light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[0994] 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 25 nm. The mass ratio of compound ET-2 and Liq (ET-2:Liq) was 67:33.

[0995] Next, Yb was deposited on the second electron transport layer to form an electron injection electrode with a film thickness of 1 nm.

[0996] Then, metal Al was deposited on the electron injection electrode to form a metal cathode with a film thickness of 80 nm.

[0997] The device configuration of the organic EL device of Example 1 is briefly described below.

[0998] ITO(130) / HT-1:HA(10, 97:3) / HT-1(77.5) / Inv-12(7.5) / BH-1:BH-2:BD(20, 58.8:39.2:2) / ET-1(5) / ET-2:Liq(25, 67:33) / Yb(1) / Al(80)

[0999] In the above device configuration, the number in parentheses is the film thickness (nm), and the ratio is the mass ratio of the compound used.

[1000]

[1001] Examples 13 and 14

[1002] Organic EL devices of Examples 13 and 14 were manufactured in the same manner as in Example 12, except that the compounds shown in Table 2 below were used instead of the compound Inv-12 in Example 12.

[1003]

[1004] Comparative Example 2

[1005] The organic EL device of Comparative Example 2 was manufactured in the same manner as in Example 12, except that the compound shown in Table 2 below was used instead of the compound Inv-12 in Example 12.

[1006]

[1007] Evaluation of Organic EL Devices

[1008] The following evaluation was performed on the fabricated organic EL device. The evaluation results are shown in Tables 1 and 2.

[1009]

[1010] Measurement of external quantum efficiency (EQE)

[1011] The organic EL device obtained as described above was subjected to a current density of 10 mA / cm at room temperature. 2 When voltage was applied to the device, the spectral radiance spectrum was measured using a spectral radiance meter (CS-1000 manufactured by Konica Minolta). From the obtained spectral radiance spectrum, the external quantum efficiency EQE (%) was obtained assuming that Lambertian reflection occurred.

[1012]

[1013] Measurement of driving voltage

[1014] Current density is 10mA / cm 2 The voltage (unit: V) when voltage was applied to the organic EL element was measured.

[1015] Hole injection layer and first hole transport layer material EQE(%)@10mA / cm 2 Driving voltage (V) @ 10 mA / cm 2Example 1 lnv-110.82 3.50 Example 2 lnv-210.99 3.53 Example 3 lnv-310.95 3.48 Example 4 Inv-411.12 3.48 Example 6 Inv-611.01 3.48 Example 7 Inv-711.04 3.55 Example 8 Inv-810.91 3.49 Example 9 Inv-910.94 3.53 Example 10 Inv-1011.10 3.47 Example 11 Inv-1111.01 3.51 Comparative Example 1 Ref-110.21 3.65

[1016]

[1017] As is clear from the results in Table 1, the organic EL device comprising the inventive compound Inv-1, Inv-2, Inv-3, Inv-4, Inv-6, Imv-7, Inv-8, Inv-9, Inv-10 or Inv-11 has a higher external quantum efficiency and a lower driving voltage than the organic EL device comprising the comparative compound Ref-1.

[1018] Second hole transport layer material EQE(%)@10mA / cm 2 Driving voltage (V) @ 10 mA / cm 2 Example 12lnv-1211.333.55 Example 13lnv-1311.123.39 Example 14lnv-1411.133.47 Comparative Example 2Ref-210.563.66

[1019]

[1020] As is clear from the results in Table 2, the organic EL device comprising the inventive compound Inv-12, Inv-13, or Inv-14 has a higher external quantum efficiency and a lower driving voltage than the organic EL device comprising the comparative compound Ref-2.

[1021]

[1022] Synthesis of compounds

[1023] Intermediate Synthesis Example 1: Synthesis of Intermediate A-1

[1024]

[1025] Under a nitrogen gas atmosphere, a mixture of the following components was refluxed at the boiling point for 3 hours.

[1026] Raw material 1: 11,11-dimethyl-11H-benzo[a]fluoren-9-amine (3.89 g, 15 mmol)

[1027] Raw material 2: 2-bromophenanthrene (3.86 g, 15 mmol)

[1028] Catalyst: Tris(dibenzylideneacetone)dipalladium(0)(Pd2(dba)3)(0.275g, 0.3mmol)

[1029] Ligand: 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) (0.374 g, 0.6 mmol)

[1030] Base: Sodium t-butoxide (t-BuONa) (1.586 g, 16.5 mmol)

[1031] Solvent: Toluene (75 mL)

[1032] The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain a white solid (4.51 g). The yield was 69%.

[1033]

[1034] Intermediate Synthesis Example 2: Synthesis of Intermediates A-2 to A-8

[1035] Intermediates A-2 to A-8 were synthesized in the same manner as the synthesis of intermediate A-1, except that raw materials 1 and 2 were changed to the compounds shown in Table 3 below.

[1036] Intermediates A-1 to A-8 are shown in Table 3 along with raw materials 1 and 2 and yields.

[1037]

[1038]

[1039] Synthesis Example 1: Synthesis of Compound 1 (Inv-1)

[1040]

[1041] Under a nitrogen gas atmosphere, a mixture of the following components was stirred at 110°C for 3 hours.

[1042] Intermediate 1: Intermediate A-1 (4.36 g, 10 mmol)

[1043] Intermediate 2: Intermediate B-1 (2.73 g, 10 mmol)

[1044] Catalyst: Tris(dibenzylideneacetone)dipalladium(0) (0.183 g, 0.2 mmol)

[1045] Ligand: tri-tert-butylphosphonium tetrafluoroborate (0.232 g, 0.8 mmol)

[1046] Base: Sodium-t-butoxide (1.44 g, 15 mmol)

[1047] Solvent: Xylene (50 mL)

[1048] After cooling the reaction mixture to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain 4.77 g of a white solid. The yield was 76%. The result of mass spectral analysis was compound 1, with a molecular weight of 627.83 and m / e = 628.

[1049]

[1050] Synthetic Examples 2 to 14: Synthesis of Compounds 2 to 14

[1051] Compounds 2 to 14 were synthesized in the same manner as in Synthesis Example 1, except that the compounds shown in Table 4 below were used as intermediates 1 and 2.

[1052] Compounds 2 to 14 are shown in Table 4 along with the raw materials, intermediates 1 and 2, and yields.

[1053]

[1054]

[1055]

[1056] [Explanation of symbols]

[1057] 1, 11, 12: Organic EL devices

[1058] 2: Substrate

[1059] 3: Anode

[1060] 4: Cathode

[1061] 5: Emissive layer

[1062] 6: Hole transport band (hole transport layer)

[1063] 6a: Hole injection layer

[1064] 6b: First hole transport layer

[1065] 6c: Second hole transport layer

[1066] 6d: Third hole transport layer

[1067] 7: Electron transport band (electron transport layer)

[1068] 7a: First electron transport layer

[1069] 7b: Second electron transport layer

[1070] 10, 20, 30: Light-emitting units

Claims

A compound represented by the following formula (I): In formula (I), R1 and R2 are each independently a methyl group or a phenyl group, but not both are phenyl groups; Two adjacent ones selected from R3 to R6 are bonded to a and b, respectively; R3 to R6, which are not bonded to the above a and b, are hydrogen atoms; L is a single bond or a phenylene group; L1 is a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms; Ar1 is substituted or unsubstituted , substituted or unsubstituted , or substituted or unsubstituted and; A is a substituted or unsubstituted aryl group having 12 to 17 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 12 to 17 ring atoms; X is an oxygen atom or -CR 7 R 8 and R 7 and R 8 are each independently a methyl group or a phenyl group, or R 7 and R 8 combine with each other to form a spiro ring; Ar2 is represented by the following formula (1-a), (1-b), (1-c), (1-d) or (1-e). (In Equation (1-a), *21 is a single bond bonding to L1, and when L1 is a single bond, *21 is bonded to the central nitrogen atom; R 101 ~R 105 One selected from is a single bond binding to *22, and R 106 ~R 110 One selected from is a single bond binding to *23; R, which is not a single bond 101 ~R 105 and R 106 ~R 110 are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms; R 111 ~R 115 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 13 ring atoms; u is 0 to 2, v is 0 or 1, but at least one of u and v is not 0) (In equation (1-b), *24 is a single bond bonding to L1, and when L1 is a single bond, *24 is bonded to the central nitrogen atom; R 121 ~R 128 One selected from is a single bond binding to *25; R, which is not a single bond 121 ~R 128 are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms) (In equation (1-c), *26 is a single bond bonding to L1, and when L1 is a single bond, *26 is bonded to the central nitrogen atom; R 131 ~R 140 One selected from is a single bond binding to *27; R, which is not a single bond 131 ~R 140 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. (In equation (1-d), *28 is a single bond bonding to L1, and when L1 is a single bond, *28 is bonded 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; p is 0, X 1 This oxygen atom, sulfur atom, -CR E R F or -NR G When, R 141 ~R 148 and R G One selected from is a single bond binding to *29; p is 1, and X 1 This -CR E R F or -NR G If , R 145 Wow R 146 , R 146 and R 147 , or R 147 and R 148 R is a single bond where one side is bonded to *d, the other side is bonded to *e, and is not a single bond bonded to *d or *e. 145 ~R 148 , R 141 ~R 144 , and R 200 ~R 203 One selected from is a single bond binding to *29; p is 1, and X 1 If this is an oxygen atom or a sulfur atom, R 145 Wow R 146 , R 146 and R 147 , or R 147 and R 148 One side of R is a single bond bonded to *d, the other side is a single bond bonded to *e, and R 141 Inland R 144 One selected from is a single bond binding to *29; R, which is not a single bond 141 ~R 148 , R, which is not a single bond 200 ~R 203 , and R which is not a single bond G , the above R E , and the above R F are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 13 ring atoms; Just p is 0 and X 1 This -CR E R F If R E is a methyl group and R F is a methyl group or a phenyl group) (In Equation (1-e), *30 is a single bond bonding to L1, and if L1 is a single bond, *30 is bonded to the central nitrogen atom; R 151 ~R 155 One selected from is a single bond binding to *31, and R 151 ~R 155 Another one selected from is a single bond binding to *32; R, which is not a single bond 151 ~R 155 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group; R 161 ~R 165 and R 171 ~R 175 are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms; R, not a hydrogen atom 161 Inland R 165 At least two adjacent ones selected from can combine with each other to form one or more unsubstituted benzene rings; R, not a hydrogen atom 171 Inland R 175 At least two adjacent ones selected from can combine with each other to form one or more unsubstituted benzene rings) 　 In the first paragraph, A compound in which R1 and R2 are methyl groups. 　 In the first paragraph, L is a single bond; A compound in which L1 is a single bond or a phenylene group. 　 In the first paragraph, A compound in which A is a substituted or unsubstituted aryl group having 12 to 17 ring carbon atoms. 　 In the first paragraph, Among Ar1, X is an oxygen atom or -CR 7 R 8 and R 7 and R 8 A compound containing a silver phenyl group. 　 In the first paragraph, Ar1 is substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , or substituted or unsubstituted Phosphorus compounds. 　 In the first paragraph, L1 is a single bond; Ar2 is represented by the above formula (1-a), In equation (1-a), R 103 is a single bond that binds to *22, and R 108 is a single bond that binds to *23, and R 111 ~R 115 A compound in which is a hydrogen atom and u or v is 0. 　 In the first paragraph, L1 is a single bond or a phenylene group; Ar2 is represented by the above formula (1-b), In equation (1-b), R 122 , R 123 , R 127 and R 128 One selected from is a single bond bonding to *25, and R is not the single bond 121 ~R 128 A compound containing hydrogen atoms. In the first paragraph, L1 is a single bond; Ar2 is represented by the above formula (1-c), In formula (1-c), R is not a single bond 131 ~R 140 A compound containing hydrogen atoms. 　 In the first paragraph, L1 is a single bond; Ar2 is represented by the above formula (1-d), In equation (1-d), p is 0 and X 1 Silver -CR E R F and R E is a methyl group, and R F A compound containing a methyl group or a phenyl group. 　 In the first paragraph, L1 is a single bond; Ar2 is represented by the above formula (1-e), In formula (1-e), R is not a single bond 151 ~R 155 , R 161 ~R 165 and R 171 ~R 175 is a compound containing hydrogen atoms. 　 In the first paragraph, R1 and R2 are methyl groups; L is a single bond; L1 is a single bond or a phenylene group; Among Ar1, A is a substituted or unsubstituted aryl group having 12 to 17 ring carbon atoms, and X is an oxygen atom or -CR 7 R 8 and R 7 and R 8 is a phenyl group; In equation (1-a), R 103 is a single bond that binds to *22, and R 108 is a single bond that binds to *23, and R 111 ~R 115 is a hydrogen atom, and u or v is 0; In equation (1-b), R 122 , R 123 , R 127 and R 128 One selected from is a single bond bonding to *25, and R is not the single bond 121 ~R 128 is a hydrogen atom; In formula (1-c), R is not a single bond 131 ~R 140 is a hydrogen atom; In equation (1-d), p is 0 and X 1 Silver -CR E R F and R E is a methyl group, and R F is a methyl group or a phenyl group; In formula (1-e), R is not a single bond 151 ~R 155 , R 161 ~R 165 and R 171 ~R 175 is a compound containing hydrogen atoms. 　 A compound represented by the following formula (II): In formula (II), R1, R2, R7 and R8 are each independently a methyl group or a phenyl group, or R1 and R2, or R7 and R8 are combined with each other to form a spiro ring; Two adjacent ones selected from R3 to R6 are bonded to a and b, respectively; R9~R 12 Two adjacent ones selected from are bonded to c and d respectively; R3 to R6 that do not bind to the above a and b, and R9 to R that do not bind to the above c and d 12 is a hydrogen atom; L is each independently a single bond or a phenylene group; Ar1 is substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , or substituted or unsubstituted However, when the above Ar1 has two or more substituents, the substituents can combine with each other to form a condensed ring (provided that X is -CR 13 R 14 (except in this case) A is a substituted or unsubstituted aryl group having 5 or more ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 or more ring atoms; X is an oxygen atom, a sulfur atom, or -CR 13 R 14 and; R 13 and R 14 are each independently a methyl group or a phenyl group, or R 13 and R 14 They combine with each other to form spirocycles. 　 In paragraph 13, A compound wherein R1, R2, R7 and R8 are methyl groups. 　 In paragraph 13, Two adjacent ones selected from R3 to R5 are bonded to a and b, respectively; R9~R 11 Two adjacent compounds selected from are bonded to c and d, respectively. 　 In paragraph 13, L is a compound in which all bonds are single. 　 In paragraph 13, A compound in which Ar1 is unsubstituted or has two substituents, and the substituents are combined with each other to form a condensed ring having 5 to 20 ring carbon atoms. 　 In paragraph 13, A compound is an aromatic heterocyclic group having 5 to 20 substituted or unsubstituted ring atoms. 　 In paragraph 13, X is an oxygen atom or -CR 13 R 14 and; R 13 and R 14 are each independently a methyl group or a phenyl group, or R 13 and R 14 are compounds that combine with each other to form a spiro ring having 5 to 20 ring-forming carbon atoms. 　 In paragraph 13, Ar1 is substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , substituted or unsubstituted , or substituted or unsubstituted Phosphorus compounds. 　 In paragraph 13, R1, R2, R7 and R8 are methyl groups; Two adjacent ones selected from R3 to R5 are bonded to a and b, respectively; R9~R 11 Two adjacent ones selected from are bonded to c and d respectively; L is all single bonds; Ar1 is unsubstituted or has two substituents, and the substituents are combined with each other to form a condensed ring having 5 to 20 ring carbon atoms; A is an aromatic heterocyclic group having 5 to 20 substituted or unsubstituted ring atoms; X is an oxygen atom or -CR 13 R 14 and; R 13 and R 14 are each independently a methyl group or a phenyl group, or R 13 and R 14 are compounds that combine with each other to form a spiro ring having 5 to 20 ring-forming carbon atoms. 　 A material for an organic electroluminescent device comprising a compound according to any one of claims 1 to 21. 　 An organic electroluminescent device comprising an anode, a cathode, and an organic layer formed of a single or multiple layers between the anode and the cathode, The above organic layer includes a light-emitting layer, An organic electroluminescent device, wherein at least one of the organic layers comprises a compound as described in any one of claims 1 to 21. 　 In paragraph 23, An organic electroluminescent device wherein 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 paragraph 24, An organic electroluminescent device wherein the hole transport band comprises a first hole transport layer on the anode side and a second hole transport layer on the cathode side, and one or both of the first hole transport layer and the second hole transport layer comprises the compound. 　 In paragraph 25, An organic electroluminescent device in which the above-mentioned light-emitting layer and the above-mentioned second hole transport layer are in direct contact. 　 In paragraph 25, 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 or more and 150 nm or less. 　 An electronic device comprising the organic electroluminescent device described in claim 23.

Images