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

Abstract

The present application relates to a compound, a material for an organic electroluminescent element, an organic electroluminescent element, and an electronic device. The present application provides a compound represented by formula (1) or (2), an organic electroluminescent element comprising the compound, and an electronic device comprising the organic electroluminescent element. The symbols in the formula are as defined in the specification. # imgabs0 #

Description

[0001] This application is a divisional application of an application with a filing date of March 30, 2022, application number 202280007471.8, and invention name “Compounds, materials for organic electroluminescent elements, organic electroluminescent elements and electronic devices”. Technical Field

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

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

[0004] Patent Documents 1 to 4 disclose compounds useful as materials for organic electroluminescent devices.

[0005] Prior art literature

[0006] Patent Literature

[0007] Patent Document 1: U.S. Patent No. 10840455

[0008] Patent Document 2: U.S. Patent Application Publication No. 2019 / 0148650

[0009] Patent Document 3: International Publication No. 2019 / 139419

[0010] Patent Document 4: International Publication No. 2014 / 034795 Summary of the invention

[0011] Problem that the invention aims to solve

[0012] Conventionally, a large number of compounds for organic EL devices have been reported, but compounds that further improve the performance of organic EL devices are still being sought.

[0013] The present invention has been made to solve the above-mentioned problems, and an object of the present invention is to provide a compound that further improves the performance of an organic EL element, an organic EL element with further improved element performance, and an electronic device including such an organic EL element.

[0014] Means used to solve problems

[0015] The present inventors have repeatedly conducted in-depth studies on the performance of organic EL devices containing the compounds described in Patent Documents 1 to 4, and found that the performance of organic EL devices containing the compound represented by the following formula (1) and the organic EL devices containing the compound represented by the following formula (2) are further improved.

[0016] In one embodiment, the present invention provides a compound represented by the following formula (1).

[0017] [Chemical formula 1]

[0018]

[0019] In formula (1),

[0020] R 1 and R 2 One of them is methyl and the other is unsubstituted phenyl,

[0021] R 1 With R 2 They are not bonded to each other and thus do not form a ring structure.

[0022] R 3 and R 4 One of them is methyl and the other is unsubstituted phenyl,

[0023] R 3 With R 4 They are not bonded to each other and thus do not form a ring structure.

[0024] R 11 ~R 18 and R 21 ~R 28 A hydrogen atom.

[0025] in,

[0026] Selected from R 11 ~R 18 One of them is a single bond to *a,

[0027] Selected from R 21 ~R 28 One of them is a single bond bonded to *b.

[0028] L 1 and L 2 Each is independently a single bond, or a substituted or unsubstituted phenylene group.

[0029] Ar 1 It is a group represented by any one of formulae (1-1) to (1-6).

[0030] [Chemical formula 2]

[0031]

[0032] In formulas (1-1) to (1-6),

[0033] R 31 ~R 35 , R 41 ~R 46 , R 51 ~R 55 , R 61 ~R 68 , R 71 ~R 82 , R 91 ~R 100 , R 101 ~R 108 , R 111 ~R 116 , R 121 ~R 125 and R 131 ~R 135 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0034] X 1 is an oxygen atom, a sulfur atom, or CRaRb,

[0035] R a and R b are each independently a hydrogen atom, a methyl group, or a substituted or unsubstituted phenyl group, R a With R b They may be bonded to each other to form a substituted or unsubstituted ring.

[0036] in,

[0037] Selected from R 31 ~R 35 One of them is a single bond to *c,

[0038] Selected from R 41 ~R 46 One of them is a single bond bonded to *d, selected from R 41 ~R 46 The other one in is a single bond bonded to *e,

[0039] Selected from R 65 ~R 68 One of them is a single bond to *f,

[0040] Selected from R 79 ~R 82 One of them is a single bond to *g,

[0041] Selected from R 91 and R 97 ~R 100 One of them is a single bond to *h,

[0042] Selected from R 105 ~R 108 One of them is a single bond bonded to *i,

[0043] Selected from R 111 ~R 116 One of them is a single bond bonded to *i, selected from R 111 ~R 116 The other one of them is a single bond bonded to *k, selected from R 11 1~R 116 The other one in is a single bond bonded to *1,

[0044] R is selected from the group consisting of 31 ~R 35 Two adjacent R selected from R which are not any of the above single bonds 41 ~R 46 Two adjacent ones in R 51 ~R 55 Two adjacent R selected from the group consisting of R which are not the above single bonds 61 ~R 68 Two adjacent R selected from the group consisting of R which are not the above single bonds 71 ~R 82 Two adjacent R selected from the group consisting of R which are not the above single bonds 91 ~R 100 Two adjacent R selected from the group consisting of R which are not the above single bonds 101 ~R 108 Two adjacent R selected from R which are not any of the above single bonds 111 ~R 116 Two adjacent ones in R 121 ~R 125 Two adjacent ones in R 131 ~R 135 The two adjacent ones in are not bonded to each other and thus do not form a ring structure.

[0045] The benzene ring A1 and the benzene ring B1, the benzene ring A1 and the benzene ring C1, the benzene ring A1 and the benzene ring D1, the benzene ring A1 and the benzene ring E1, the benzene ring A1 and the benzene ring F1, the benzene ring B1 and the benzene ring C1, the benzene ring D1 and the benzene ring E1, and the benzene ring D1 and the benzene ring F1 are not cross-linked,

[0046] ** indicates the bonding position with the central nitrogen atom N,

[0047] m is 0 or 1, n is 0 or 1,

[0048] In formula (1-1) and (1-2), when m is 0 and n is 0, *e is bonded to the central nitrogen atom N, when m is 0 and n is 1, *c is bonded to the central nitrogen atom N, and when m is 1 and n is 0, *e is bonded to a member selected from R 31 ~R 35 1 bond in

[0049] In formulas (1-3) to (1-6), when m is 0, *c is bonded to the central nitrogen atom N,

[0050] In R 12 or R 17 is a single bond bonded to *a, R 22 or R 27 When it is a single bond bonding to *b, the formula (1-1) excludes the p-biphenyl group.

[0051] In another embodiment, the present invention provides a compound represented by the following formula (2).

[0052] [Chemical formula 3]

[0053]

[0054] In formula (2),

[0055] Selected from R 201 ~R 204 One of them is methyl, selected from R 201 ~R 204 The other three are unsubstituted phenyl groups,

[0056] R 201 With R 202 do not bond to each other and thus do not form a ring structure,

[0057] R 203 With R 204 They are not bonded to each other and thus do not form a ring structure.

[0058] R 211 ~R 218 and R 221 ~R 228 A hydrogen atom.

[0059] in,

[0060] Selected from R 211 ~R 218 One of them is a single bond to *m,

[0061] Selected from R221 ~R 228 One of them is a single bond bonded to *n.

[0062] L 11 and L 12 Each is independently a single bond, or a substituted or unsubstituted phenylene group.

[0063] Ar 11 It is a group represented by any one of formulae (2-1) to (2-6).

[0064] [Chemical formula 4]

[0065]

[0066] In formulas (2-1) to (2-6),

[0067] R 231 ~R 235 , R 241 ~R 246 , R 251 ~R 255 , R 261 ~R 268 , R 271 ~R 282 , R 291 ~R 300 , R 301 ~R 308 , R 311 ~R 316 , R 321 ~R 325 and R 331 ~R 335 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0068] X 2 is an oxygen atom, a sulfur atom, or CR c R d ,

[0069] R c and R d are each independently a hydrogen atom or a methyl group, R c With R d They are not bonded to each other and thus do not form a ring structure.

[0070] in,

[0071] Selected from R 231 ~R 235One of them is a single bond bonded to *o,

[0072] Selected from R 241 ~R 246 One of them is a single bond bonded to *p, selected from R 241 ~R 246 The other one in is a single bond bonded to *q,

[0073] Selected from R 265 ~R 268 One of them is a single bond to *r,

[0074] Selected from R 279 ~R 282 One of them is a single bond to *s,

[0075] Selected from R 291 and R 297 ~R 300 One of them is a single bond to *t,

[0076] Selected from R 305 ~R 308 One of them is a single bond to *u,

[0077] Selected from R 311 ~R 316 One of them is a single bond bonded to *v, selected from R 311 ~R 316 The other one of them is a single bond bonded to *w, selected from R 311 ~R 316 The other one in is a single bond bonded to *x,

[0078] R is selected from the group consisting of 231 ~R 235 Two adjacent R selected from R which are not any of the above single bonds 241 ~R 246 Two adjacent ones in R 251 ~R 255 Two adjacent R selected from the group consisting of R which are not the above single bonds 261 ~R 268 Two adjacent R selected from the group consisting of R which are not the above single bonds 271 ~R 282 Two adjacent R selected from the group consisting of R which are not the above single bonds 291 ~R 300 Two adjacent R selected from the group consisting of R which are not the above single bonds 301 ~R 308 Two adjacent R selected from R which are not any of the above single bonds 311 ~R 316 Two adjacent ones in R 321~R 325 Two adjacent ones in R 331 ~R 335 The two adjacent ones in are not bonded to each other and thus do not form a ring structure.

[0079] The benzene ring A2 and the benzene ring B2, the benzene ring A2 and the benzene ring C2, the benzene ring A2 and the benzene ring D2, the benzene ring A2 and the benzene ring E2, the benzene ring A2 and the benzene ring F2, the benzene ring B2 and the benzene ring C2, the benzene ring D2 and the benzene ring E2, and the benzene ring D2 and the benzene ring F2 are not cross-linked,

[0080] *** indicates the bonding position with the central nitrogen atom N,

[0081] p is 0 or 1, q is 0 or 1,

[0082] In formulas (2-1) and (2-2), when p is 0 and q is 0, *q is bonded to the central nitrogen atom N, when p is 0 and q is 1, *o is bonded to the central nitrogen atom N, and when p is 1 and q is 0, *q is bonded to one selected from R231 to R235,

[0083] In formulas (2-3) to (2-6), when p is 0, *o is bonded to the central nitrogen atom N,

[0084] In formula (2-5), in X 2 CR c R d When p is 0, select L 11 and L 12 At least one of them is a substituted or unsubstituted phenylene group,

[0085] In formula (2-5), in X 2 When it is an oxygen atom and p is 1, it is selected from R 306 ~R 308 One of them is a single bond to *u,

[0086] In R 212 or R 217 is a single bond bonded to *m, R 222 or R 227 In the case of a single bond bonding to *n, the formula (2-1) excludes the p-biphenyl group.

[0087] In still another embodiment, the present invention provides an organic electroluminescent device material comprising at least one selected from the group consisting of the compound represented by the above formula (1) and the compound represented by the above formula (2).

[0088] In another embodiment, the present invention provides an organic electroluminescent element, which has a cathode, an anode, and an organic layer located between the cathode and the anode, the organic layer includes a light-emitting layer, and at least one layer of the organic layer includes at least one selected from the compound represented by the above formula (1) and the compound represented by the above formula (2).

[0089] In yet another embodiment, the present invention provides an electronic device including the organic electroluminescent element.

[0090] Effects of the Invention

[0091] An organic EL device containing the compound represented by the above formula (1) exhibits improved device performance. In addition, an organic EL device containing the compound represented by the above formula (2) exhibits improved device performance. BRIEF DESCRIPTION OF THE DRAWINGS

[0092] Figure 1 It is a schematic diagram showing an example of the layer structure of the organic EL element according to one embodiment of the present invention.

[0093] Figure 2 It is a schematic diagram showing another example of the layer structure of the organic EL element according to one embodiment of the present invention.

[0094] Figure 3 It is a schematic diagram showing still another example of the layer structure of the organic EL element according to one embodiment of the present invention. DETAILED DESCRIPTION

[0095] [definition]

[0096] In this specification, the hydrogen atom is meant to include isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0097] In the present specification, in chemical structural formulas, a bondable position that does not clearly show a symbol such as "R" or "D" representing a deuterium atom is assumed to be bonded with a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom.

[0098] In this specification, the number of ring carbons refers to the number of carbon atoms among the atoms constituting the ring itself of a compound (such as a monocyclic compound, a condensed ring compound, a bridged ring compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are bonded in a ring shape. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring carbons. The "number of ring carbons" recorded below is set in the same manner unless otherwise stated. For example, the number of ring carbons of a benzene ring is 6, the number of ring carbons of a naphthalene ring is 10, the number of ring carbons of a pyridine ring is 5, and the number of ring carbons of a furan ring is 4. In addition, for example, the number of ring carbons of 9,9-diphenylfluorenyl is 13, and the number of ring carbons of 9,9'-spirobifluorenyl is 25.

[0099] In addition, when a substituent such as an alkyl group is substituted on a benzene ring, the carbon number of the alkyl group is not included in the ring carbon number of the benzene ring. Therefore, the ring carbon number of the benzene ring substituted with an alkyl group is 6. In addition, when a substituent such as an alkyl group is substituted on a naphthalene ring, the carbon number of the alkyl group is not included in the ring carbon number of the naphthalene ring. Therefore, the ring carbon number of the naphthalene ring substituted with an alkyl group is 10.

[0100] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a bridged ring compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are bonded in a ring shape (e.g., a monocyclic compound, a condensed ring compound, a bridged ring compound, a carbocyclic compound, and a heterocyclic compound). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of atoms constituting the ring) and atoms contained in a substituent when the ring is substituted by a substituent are not included in the number of ring atoms. The "number of ring atoms" recorded below is set in the same manner as long as it is not recorded separately. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or atoms constituting a substituent is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring bonded with a hydrogen atom or a substituent is 6. In addition, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring. Therefore, the number of ring atoms of the quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

[0101] In this specification, "carbon number XX to YY" in the expression "substituted or unsubstituted ZZ group with carbon number XX to YY" means the carbon number of the ZZ group when it is unsubstituted, and does not include the carbon number of the substituent when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer greater than 1, and "YY" means an integer greater than 2.

[0102] In this specification, "the number of atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having an atomic number of XX to YY" means the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituent when substituted. Here, "YY" is greater than "XX", "XX" means an integer greater than 1, and "YY" means an integer greater than 2.

[0103] In the present specification, an unsubstituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group".

[0104] In the present specification, "unsubstituted" in the expression "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom or a tritium atom.

[0105] In addition, in the present specification, "substituted" when expressing "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. "Substituted" when expressing "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0106] "Substituents described in this specification"

[0107] The substituents described in the present specification are described below. Unless otherwise specified, each substituent described in the present specification is defined as follows.

[0108] The number of ring carbon atoms of the "unsubstituted aryl group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise described in the present specification.

[0109] The number of ring atoms of the "unsubstituted heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise described in the present specification.

[0110] The carbon number of the "unsubstituted alkyl group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise described in the present specification.

[0111] The carbon number of the "unsubstituted alkenyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise described in the present specification.

[0112] The number of carbon atoms in the "unsubstituted alkynyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise described in the present specification.

[0113] The number of ring carbon atoms of the "unsubstituted cycloalkyl group" described in the present specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise described in the present specification.

[0114] The number of ring carbon atoms of the "unsubstituted arylene group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise described in the present specification.

[0115] The number of ring atoms of the "unsubstituted divalent heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise described in the present specification.

[0116] The carbon number of the "unsubstituted alkylene group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise described in the present specification.

[0117] "Substituted or unsubstituted aryl"

[0118] As specific examples of "substituted or unsubstituted aryl" described in this specification (specific example group G1), the following unsubstituted aryl (specific example group G1A) and substituted aryl (specific example group G1B) can be cited. (Here, unsubstituted aryl refers to the case where "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl refers to the case where "substituted or unsubstituted aryl" is "substituted aryl".) In this specification, when only "aryl" is expressed, both "unsubstituted aryl" and "substituted aryl" are included.

[0119] "Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" are replaced by a substituent. Examples of "substituted aryl" include groups in which one or more hydrogen atoms of an "unsubstituted aryl" are replaced by a substituent in the following specific example group G1A, and examples of substituted aryl in the following specific example group G1B. It should be noted that the examples of "unsubstituted aryl" and "substituted aryl" listed here are only examples, and the "substituted aryl" described in this specification also includes groups in which the hydrogen atom bonded to the carbon atom of the aryl itself in the "substituted aryl" in the following specific example group G1B is further replaced by a substituent, and groups in which the hydrogen atom of the substituent in the "substituted aryl" in the following specific example group G1B is further replaced by a substituent.

[0120] Unsubstituted aryl (specific example group G1A):

[0121] Phenyl,

[0122] p-Biphenyl,

[0123] m-Biphenyl,

[0124] o-Biphenyl,

[0125] 4-terphenyl-4-yl,

[0126] 4-terphenyl-3-yl,

[0127] 4-terphenyl-2-yl,

[0128] m-terphenyl-4-yl,

[0129] m-terphenyl-3-yl,

[0130] m-terphenyl-2-yl,

[0131] m-terphenyl-3'-yl,

[0132] o-terphenyl-4-yl,

[0133] o-terphenyl-3-yl,

[0134] o-terphenyl-2-yl,

[0135] 1-naphthyl,

[0136] 2-naphthyl,

[0137] Anthracene,

[0138] Benzanthryl,

[0139] Fiki,

[0140] Triphenylene, phenanthrenyl,

[0141] Pyrene

[0142] base,

[0143] Benzo base,

[0144] Triphenylene,

[0145] Benzotriphenylene,

[0146] Tetraphenylene,

[0147] Pentaphenyl,

[0148] Fluorene,

[0149] 9,9'-spirobifluorenyl,

[0150] Benzofluorenyl,

[0151] Dibenzofluorenyl,

[0152] Fluoranthene base,

[0153] Benzofluoranthene,

[0154] Perylene, and

[0155] A monovalent aromatic group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[0156] [Chemical formula 5]

[0157]

[0158] [Chemical formula 6]

[0159]

[0160] Substituted aryl (specific example group G1B):

[0161] o-Toluyl,

[0162] m-Toluene

[0163] p-Tolyl,

[0164] p-Xylyl,

[0165] m-Xylyl,

[0166] o-Xylyl,

[0167] p-Isopropylphenyl,

[0168] m-isopropylphenyl,

[0169] o-isopropylphenyl,

[0170] 4-tert-Butylphenyl,

[0171] m-tert-butylphenyl,

[0172] o-tert-butylphenyl,

[0173] 3,4,5-Trimethylphenyl,

[0174] 9,9-dimethylfluorenyl,

[0175] 9,9-Diphenylfluorenyl

[0176] 9,9-bis(4-methylphenyl)fluorenyl,

[0177] 9,9-bis(4-isopropylphenyl)fluorenyl,

[0178] 9,9-bis(4-tert-butylphenyl)fluorenyl,

[0179] Cyanophenyl,

[0180] Triphenylsilylphenyl,

[0181] Trimethylsilylphenyl,

[0182] Phenyl naphthyl,

[0183] Naphthylphenyl and

[0184] A group in which one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the above general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0185] "Substituted or unsubstituted heterocyclic group"

[0186] The "heterocyclic group" described in the present specification is a cyclic group containing at least one heteroatom among the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom and a boron atom.

[0187] The "heterocyclic group" described in the present specification is a monocyclic group or a condensed ring group.

[0188] The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0189] As specific examples of the "substituted or unsubstituted heterocyclic group" described in this specification (specific example group G2), the following unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B) can be cited. (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when only "heterocyclic group" is expressed, both "unsubstituted heterocyclic group" and "substituted heterocyclic group" are included.

[0190] "Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by a substituent. Specific examples of "substituted heterocyclic group" include groups in which hydrogen atoms of the "unsubstituted heterocyclic group" of the following specific example group G2A are substituted, and examples of substituted heterocyclic groups of the following specific example group G2B are mentioned. It should be noted that the examples of "unsubstituted heterocyclic group" and "substituted heterocyclic group" listed here are only examples, and the "substituted heterocyclic group" recorded in this specification also includes groups in which hydrogen atoms bonded to ring atoms of the heterocyclic group itself in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents, and groups in which hydrogen atoms of substituents in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents.

[0191] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1), unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2), unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0192] Specific example group G2B includes, for example, the following heterocyclic groups containing nitrogen atom substitution (specific example group G2B1), oxygen atom substitution (specific example group G2B2), sulfur atom substitution (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formula (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4).

[0193] Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):

[0194] Pyrrolyl,

[0195] Imidazole,

[0196] Pyrazolyl,

[0197] Triazole,

[0198] Tetrazolyl,

[0199] Oxazolyl,

[0200] Isoxazolyl,

[0201] Oxadiazolyl,

[0202] Thiazolyl,

[0203] Isothiazolyl,

[0204] Thiadiazole,

[0205] Pyridyl,

[0206] Pyridazine

[0207] Pyrimidine,

[0208] Pyrazinyl,

[0209] Triazine,

[0210] Indolyl,

[0211] Isoindolyl,

[0212] Indolizine

[0213] Quinolizinyl,

[0214] Quinoline,

[0215] Isoquinolinyl,

[0216] Cinnoline,

[0217] Phthalocyanine

[0218] Quinazoline,

[0219] Quinoxaline,

[0220] Benzimidazolyl,

[0221] Indazolyl,

[0222] Phenanthroline,

[0223] Phenanthridinyl,

[0224] Acridinium,

[0225] Phenazine,

[0226] Carbazolyl,

[0227] Benzocarbazolyl,

[0228] Morpholinyl,

[0229] Phenoxazine,

[0230] Phenothiazine,

[0231] Azacarbazolyl and diazacarbazolyl.

[0232] · Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): furyl,

[0233] Oxazolyl,

[0234] Isoxazolyl,

[0235] Oxadiazolyl,

[0236] Cuckoo ton base,

[0237] Benzofuranyl,

[0238] Isobenzofuranyl,

[0239] Dibenzofuranyl,

[0240] Naphthobenzofuranyl,

[0241] Benzoxazolyl,

[0242] Benzisoxazolyl,

[0243] Phenoxazine,

[0244] Morpholinyl,

[0245] dinaphthofuranyl,

[0246] Azadibenzofuranyl,

[0247] Diazadibenzofuranyl,

[0248] Azanaphthobenzofuranyl and

[0249] naphthyridinylbenzofuranyl.

[0250] Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3):

[0251] Thienyl,

[0252] Thiazolyl,

[0253] Isothiazolyl,

[0254] Thiadiazole,

[0255] benzothienyl,

[0256] Isobenzothienyl (isobenzothieny1),

[0257] dibenzothienyl,

[0258] naphthobenzothienyl,

[0259] Benzothiazolyl,

[0260] Benzisothiazolyl,

[0261] Phenothiazine,

[0262] dinaphthothienyl,

[0263] azadibenzothienyl,

[0264] diazadibenzothienyl,

[0265] azanaphthobenzothienyl, and

[0266] diazanaphthobenzothienyl.

[0267] A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formula (TEMP-16) to (TEMP-33) (Specific example group G2A4):

[0268] [Chemical formula 7]

[0269]

[0270] [Chemical formula 8]

[0271]

[0272] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each independently represents an oxygen atom, a sulfur atom, NH or CH2. A and Y A At least one of them is an oxygen atom, a sulfur atom or NH.

[0273] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A When at least any one of is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the above general formula (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0274] Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):

[0275] (9-phenyl)carbazolyl,

[0276] (9-biphenyl)carbazolyl,

[0277] (9-phenyl)phenylcarbazolyl,

[0278] (9-naphthyl)carbazolyl,

[0279] Diphenylcarbazole-9-yl,

[0280] Phenylcarbazol-9-yl,

[0281] Methylbenzimidazolyl,

[0282] Ethylbenzimidazolyl,

[0283] Phenyl triazine,

[0284] Biphenyl triazine,

[0285] Diphenyltriazine,

[0286] Phenylquinazolinyl and

[0287] Biphenylquinazolinyl.

[0288] Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0289] Phenyldibenzofuranyl,

[0290] Methyldibenzofuranyl,

[0291] tert-Butyldibenzofuranyl and

[0292] The monovalent residue of spiro[9H-xanthen-9,9'-[9H]fluorene].

[0293] Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

[0294] Phenyldibenzothiophene,

[0295] Methyldibenzothiophene,

[0296] tert-Butyldibenzothienyl and

[0297] The monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0298] · Groups in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) are replaced with substituents (Specific example group G2B4):

[0299] The above-mentioned "one or more hydrogen atoms of the monovalent heterocyclic group" refers to hydrogen atoms bonded to carbon atoms constituting the ring of the monovalent heterocyclic group, A and Y A When at least one of the is NH, the hydrogen atom bonded to the nitrogen atom and X A and Y A When one of them is CH2, one or more hydrogen atoms among the hydrogen atoms of the methylene group.

[0300] "Substituted or unsubstituted alkyl"

[0301] As specific examples of "substituted or unsubstituted alkyl" described in this specification (specific example group G3), the following unsubstituted alkyl (specific example group G3A) and substituted alkyl (specific example group G3B) can be cited. (Here, unsubstituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when only "alkyl" is expressed, both "unsubstituted alkyl" and "substituted alkyl" are included.

[0302] "Substituted alkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl" are replaced by a substituent. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl" (specific example group G3A) are replaced by a substituent, and examples of substituted alkyl (specific example group G3B) can be cited. In the present specification, the alkyl group in "unsubstituted alkyl" refers to a chain alkyl group. Therefore, "unsubstituted alkyl" includes "unsubstituted alkyl" as a straight chain and "unsubstituted alkyl" as a branched chain. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples, and the "substituted alkyl" recorded in the present specification also includes groups in which the hydrogen atoms of the alkyl group itself in the "substituted alkyl" of the specific example group G3B are further replaced by a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted alkyl" of the specific example group G3B are further replaced by a substituent.

[0303] Unsubstituted alkyl (specific example group G3A):

[0304] methyl,

[0305] Ethyl,

[0306] n-propyl,

[0307] Isopropyl,

[0308] n-Butyl,

[0309] Isobutyl,

[0310] sec-butyl, and

[0311] Tert-butyl.

[0312] Substituted alkyl (specific example group G3B):

[0313] Heptafluoropropyl (including isomers),

[0314] Pentafluoroethyl,

[0315] 2,2,2-Trifluoroethyl and

[0316] Trifluoromethyl.

[0317] "Substituted or unsubstituted alkenyl"

[0318] As specific examples of "substituted or unsubstituted alkenyl" described in this specification (specific example group G4), the following unsubstituted alkenyl (specific example group G4A) and substituted alkenyl (specific example group G4B) can be cited. (Here, unsubstituted alkenyl refers to the case where "substituted or unsubstituted alkenyl" is "unsubstituted alkenyl", and "substituted alkenyl" refers to the case where "substituted or unsubstituted alkenyl" is "substituted alkenyl".) In this specification, when simply expressed as "alkenyl", both "unsubstituted alkenyl" and "substituted alkenyl" are included.

[0319] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" are replaced by a substituent. Specific examples of "substituted alkenyl" include the following "unsubstituted alkenyl" (specific example group G4A) groups with substituents and examples of substituted alkenyl (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples, and the "substituted alkenyl" recorded in this specification also includes groups in which the hydrogen atoms of the alkenyl itself in the "substituted alkenyl" of the specific example group G4B are further replaced by a substituent and groups in which the hydrogen atoms of the substituent in the "substituted alkenyl" of the specific example group G4B are further replaced by a substituent.

[0320] Unsubstituted alkenyl (specific example group G4A):

[0321] Vinyl,

[0322] Allyl,

[0323] 1-Butenyl,

[0324] 2-Butenyl and

[0325] 3-Butenyl.

[0326] Substituted alkenyl (specific example group G4B):

[0327] 1,3-Butadienyl,

[0328] 1-Methylvinyl,

[0329] 1-methylallyl,

[0330] 1,1-dimethylallyl,

[0331] 2-Methylallyl and

[0332] 1,2-Dimethylallyl.

[0333] "Substituted or unsubstituted alkynyl"

[0334] As specific examples of "substituted or unsubstituted alkynyl" described in this specification (specific example group G5), the following unsubstituted alkynyl (specific example group G5A) etc. can be cited. (Here, unsubstituted alkynyl refers to the case where "substituted or unsubstituted alkynyl" is "unsubstituted alkynyl".) When simply expressed as "alkynyl" below, both "unsubstituted alkynyl" and "substituted alkynyl" are included.

[0335] "Substituted alkynyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl" are replaced by a substituent. Specific examples of "substituted alkynyl" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl" (specific example group G5A) are replaced by a substituent.

[0336] Unsubstituted alkynyl (specific example group G5A):

[0337] Ethylene

[0338] "Substituted or unsubstituted cycloalkyl"

[0339] As specific examples of "substituted or unsubstituted cycloalkyl" described in the present specification (specific example group G6), the following unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B) can be cited. (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl".) In the present specification, when only "cycloalkyl" is expressed, both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.

[0340] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" are replaced by a substituent. Specific examples of "substituted cycloalkyl" include the following "unsubstituted cycloalkyl" (specific example group G6A) in which one or more hydrogen atoms are replaced by a substituent, and examples of substituted cycloalkyl (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples, and the "substituted cycloalkyl" recorded in this specification also includes the group in which one or more hydrogen atoms bonded to the carbon atoms of the cycloalkyl itself in the "substituted cycloalkyl" of the specific example group G6B are replaced by a substituent, and the group in which the hydrogen atom of the substituent in the "substituted cycloalkyl" of the specific example group G6B is further replaced by a substituent.

[0341] Unsubstituted cycloalkyl (specific example group G6A):

[0342] Cyclopropyl,

[0343] Cyclobutyl,

[0344] Cyclopentyl,

[0345] Cyclohexyl,

[0346] 1-adamantyl,

[0347] 2-adamantyl,

[0348] 1-Norbornyl and

[0349] 2-Norborneol.

[0350] Substituted cycloalkyl (specific example group G6B):

[0351] 4-Methylcyclohexyl.

[0352] ·“-Si(R 901 )(R 902 )(R 903 )"

[0353] As described in this specification, -Si(R 901}(R 902 )(R 903 ) as a specific example (specific example group G7), can be cited:

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

[0355] -Si(G1)(G2)(G2),

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

[0357] -Si(G2)(G2)(G2),

[0358] -Si(G3)(G3)(G3), and

[0359] -Si(G6)(G6)(G6)

[0360] Here,

[0361] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0362] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0363] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0364] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0365] A plurality of G1's in -Si(G1)(G1)(G1) are the same as or different from each other.

[0366] The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other.

[0367] A plurality of G1's in -Si(G1)(G1)(G2) are the same as or different from each other.

[0368] Multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other.

[0369] Multiple G3 in -Si(G3)(G3)(G3) are the same as or different from each other.

[0370] Multiple G6's in -Si(G6)(G6)(G6) are the same as or different from each other.

[0371] ·“-O-(R 904 )"

[0372] As described in this specification, -O-(R 904 ) as a specific example (specific example group G8), can be cited:

[0373] -O(G1),

[0374] -O(G2),

[0375] -O(G3) and

[0376] -O(G6).

[0377] Here,

[0378] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0379] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0380] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0381] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0382] ·“-S-(R 905 )"

[0383] As described in this specification, -S-(R 905 ) as a specific example (specific example group G9), can be cited:

[0384] -S(G1),

[0385] -S(G2),

[0386] -S(G3) and

[0387] -S(G6).

[0388] Here,

[0389] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0390] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0391] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0392] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0393] ·“-N(R 906 )(R 907 )"

[0394] As described in this specification, -N(R 906 )(R 907 ) are shown as specific examples (specific example group G10), and include

[0395] -N(G1)(G1),

[0396] -N(G2)(G2),

[0397] -N(G1)(G2),

[0398] -N(G3)(G3) and

[0399] -N(G6)(G6).

[0400] Here,

[0401] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0402] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0403] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0404] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0405] - A plurality of G1's in N(G1)(G1) are the same as or different from each other.

[0406] - The multiple G2s in N(G2)(G2) are the same as or different from each other.

[0407] - The multiple G3 in N(G3)(G3) are the same as or different from each other.

[0408] - A plurality of G6's in N(G6)(G6) are the same as or different from each other.

[0409] "Halogen atoms"

[0410] Specific examples of the "halogen atom" described in the present specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0411] "Substituted or unsubstituted fluoroalkyl"

[0412] The "substituted or unsubstituted fluoroalkyl group" described in the present specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in a "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). The carbon number of the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification. The "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. It should be noted that the "substituted fluoroalkyl group" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in a "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced with fluorine atoms.

[0413] "Substituted or unsubstituted haloalkyl"

[0414] The "substituted or unsubstituted haloalkyl group" described in the present specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in a "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The carbon number of the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification. The "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of a "haloalkyl group" are replaced with a substituent. It should be noted that the "substituted haloalkyl group" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in a "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in a "substituted haloalkyl group" are further replaced with a substituent. Specific examples of "unsubstituted haloalkyl" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (specific example group G3) are replaced with halogen atoms. A haloalkyl group is sometimes referred to as a halogenated alkyl group.

[0415] "Substituted or unsubstituted alkoxy"

[0416] A specific example of the "substituted or unsubstituted alkoxy group" described in the present specification is a group represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification.

[0417] "Substituted or unsubstituted alkylthio"

[0418] A specific example of the "substituted or unsubstituted alkylthio group" described in the present specification is a group represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification.

[0419] "Substituted or unsubstituted aryloxy group"

[0420] A specific example of the "substituted or unsubstituted aryloxy group" described in the present specification is a group represented by -O(G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise described in the present specification.

[0421] "Substituted or unsubstituted arylthio"

[0422] A specific example of the "substituted or unsubstituted arylthio group" described in the present specification is a group represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise described in the present specification.

[0423] "Substituted or unsubstituted trialkylsilyl"

[0424] A specific example of a "trialkylsilyl group" described in the present specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. A plurality of G3's in -Si(G3)(G3)(G3) are the same or different from each other. The number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise described in the present specification.

[0425] "Substituted or unsubstituted aralkyl"

[0426] A specific example of the "substituted or unsubstituted aralkyl group" described in the present specification is a group represented by -(G3)-(G1), wherein G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. Therefore, the "aralkyl group" is a group in which the hydrogen atom of the "alkyl group" is replaced by the "aryl group" as a substituent, and is one embodiment of the "substituted alkyl group". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the carbon number of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise described in the present specification.

[0427] Specific examples of the “substituted or unsubstituted aralkyl group” include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl and 2-β-naphthylisopropyl.

[0428] The substituted or unsubstituted aryl group described in the present specification is preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl and 9,9-diphenylfluorenyl, etc.

[0429] The substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidyl group, a triazine group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group or 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzofuranyl group benzothiophenyl, azadibenzothiophenyl, diazadibenzothiophenyl, (9-phenyl)carbazyl ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl or (9-phenyl)carbazol-4-yl), (9-biphenyl)carbazyl, (9-phenyl)phenylcarbazyl, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazine, biphenyltriazine, diphenyltriazine, phenyldibenzofuranyl and phenyldibenzothiophenyl, etc.

[0430] In the present specification, the carbazolyl group is specifically any of the following groups unless otherwise described in the present specification.

[0431] [Chemical formula 9]

[0432]

[0433] In the present specification, the (9-phenyl)carbazolyl group is specifically any of the following groups unless otherwise specified in the present specification.

[0434] [Chemical formula 10]

[0435]

[0436] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0437] In the present specification, the dibenzofuranyl group and the dibenzothienyl group are specifically any of the following groups unless otherwise specified in the present specification.

[0438] [Chemical formula 11]

[0439]

[0440] In the above general formulas (TEMP-34) to (TEMP-41), * represents a bonding position.

[0441] The substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, or the like, unless otherwise described in the present specification.

[0442] "Substituted or unsubstituted arylene group"

[0443] Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted aryl group" by removing one hydrogen atom on the 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.

[0444] "Substituted or unsubstituted divalent heterocyclic group"

[0445] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom on the heterocyclic ring. Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in specific example group G2 by removing one hydrogen atom on the heterocyclic ring.

[0446] "Substituted or unsubstituted alkylene"

[0447] Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted alkyl group" by removing one hydrogen atom on the alkyl chain. Specific examples of the "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived from the "substituted or unsubstituted alkyl group" described in specific example group G3 by removing one hydrogen atom on the alkyl chain.

[0448] The substituted or unsubstituted arylene group described in the present specification is preferably any one of the following general formulae (TEMP-42) to (TEMP-68) unless otherwise described in the present specification.

[0449] [Chemical formula 12]

[0450]

[0451] [Chemical formula 13]

[0452]

[0453] In the above general formulae (TEMP-42) to (TEMP-52), Q1 to Q10 are each independently a hydrogen atom or a substituent.

[0454] In the above general formulas (TEMP-42) to (TEMP-52), * represents a bonding position.

[0455] [Chemical formula 14]

[0456]

[0457] In the above general formulae (TEMP-53) to (TEMP-62), Q1 to Q10 are each independently a hydrogen atom or a substituent.

[0458] Formulas Q9 and Q10 may be bonded to each other via a single bond to form a ring.

[0459] In the above general formulas (TEMP-53) to (TEMP-62), * represents a bonding position.

[0460] [Chemical formula 15]

[0461]

[0462] In the above general formulae (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0463] In the above general formulas (TEMP-63) to (TEMP-68), * represents a bonding position.

[0464] The substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the following general formulae (TEMP-69) to (TEMP-102) unless otherwise described in the present specification.

[0465] [Chemical formula 16]

[0466]

[0467] [Chemical formula 17]

[0468]

[0469] [Chemical formula 18]

[0470]

[0471] In the above general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0472] [Chemical formula 19]

[0473]

[0474] [Chemical formula 20]

[0475]

[0476] [Chemical formula 21]

[0477]

[0478] [Chemical formula 22]

[0479]

[0480] In the above general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0481] The above is the description of the “substituents described in the present specification”.

[0482] ・"When bonding to form a ring"

[0483] In the present specification, the expression "one or more groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other" means the case where "one or more groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted monocyclic ring", the case where "one or more groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted condensed ring" and the case where "one or more groups consisting of two or more adjacent groups ... are not bonded to each other".

[0484] Hereinafter, the case of "one or more groups of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case of "one or more groups of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted condensed ring" in this specification (hereinafter, these cases are sometimes collectively referred to as "cases of bonding to form a ring.") are described. The case of an anthracene compound represented by the following general formula (TEMP-103) in which the mother skeleton is an anthracene ring is described as an example.

[0485] [Chemical formula 23]

[0486]

[0487] For example, in the921 ~R 930 In the case of "one or more groups of two or more adjacent groups are bonded to each other to form a ring", the group of two adjacent groups as one group means that R 921 With R 922 Group, R 922 With R 923 Group, R 923 With R 924 Group, R 924 With R 930 Group, R 930 With R 925 Group, R 925 With R 926 Group, R 926 With R 927 Group, R 927 With R 928 Group, R 928 With R 929 The group, and R 929 With R 921 group.

[0488] The above-mentioned "one or more groups" means that two or more groups of the above-mentioned two or more adjacent groups can simultaneously form a ring. 921 With R 922 Bonded to each other to form ring Q A And at the same time R 925 With R 926 Bonded to each other to form ring Q B When the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0489] [Chemical formula 24]

[0490]

[0491] The case where "a group of two or more adjacent groups" forms a ring includes not only the case where a group of "two" adjacent groups are bonded as in the above example, but also the case where a group of "three or more" adjacent groups are bonded. For example, R 921 With R 922 Bonded to each other to form ring Q A , and R 922 With R 923 Bonded to each other to form ring Q C , consisting of three adjacent (R 921 , R 922 and R 923) are bonded to each other to form a ring and fused to the anthracene mother skeleton. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and Ring Q C Total R 922 .

[0492] [Chemical formula 25]

[0493]

[0494] In the "monocyclic ring" or "condensed ring" formed, the structure of the ring formed alone may be a saturated ring or an unsaturated ring. Even when "one of the two adjacent groups" forms a "monocyclic ring" or a "condensed ring", the "monocyclic ring" or "condensed ring" may form a saturated ring or an unsaturated ring. For example, in the general formula (TEMP-104), the ring Q formed A and Ring Q B Each is a "single ring" or a "condensed ring". In addition, the ring Q formed in the above general formula (TEMP-105) A And Ring Q C The ring Q of the above general formula (TEMP-105) is A With Ring Q C By RingQ A With Ring Q C The ring Q of the above general formula (TMEP-104) is fused to form a fused ring. A If it is a benzene ring, then ring Q A The ring Q of the above general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a condensed ring.

[0495] The "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.

[0496] Specific examples of the aromatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G1 are terminated with hydrogen atoms.

[0497] Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in Specific Example Group G2 are terminated with hydrogen atoms.

[0498] Specific examples of the aliphatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G6 are terminated with hydrogen atoms.

[0499] "Forming a ring" means that a ring is formed only by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton and one or more other optional elements. For example, R 921 With R 922 The ring Q formed by mutual bonding A It refers to R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 The carbon atom of the anthracene skeleton to which the bonding occurs forms a ring with one or more optional elements. 921 With R 922 Ring Q A In the case of R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 When the carbon atom of the anthracene skeleton to which the carbon atom is bonded forms a monocyclic unsaturated ring with four carbon atoms, R 921 With R 922 The ring formed is a benzene ring.

[0500] Here, "optional element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur as long as it is not otherwise described in this specification. In the optional element (for example, in the case of carbon or nitrogen), the bond that does not form a ring can be terminated by hydrogen atoms or the like, or can be replaced by "optional substituents" described later. When an optional element other than carbon is included, the formed ring is a heterocycle.

[0501] Unless otherwise specified in the present specification, the number of "one or more optional elements" constituting a monocyclic or condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.

[0502] Unless otherwise specified in the present specification, "monocyclic ring" is preferred among "monocyclic ring" and "condensed ring".

[0503] In the present specification, unless otherwise specified, among "saturated ring" and "unsaturated ring", "unsaturated ring" is preferred.

[0504] Unless otherwise specified in the present specification, a "monocyclic ring" is preferably a benzene ring.

[0505] Unless otherwise specified in the present specification, the "unsaturated ring" is preferably a benzene ring.

[0506] In the case of "one or more groups consisting of two or more adjacent groups" "bonded to each other to form a substituted or unsubstituted single ring" or "bonded to each other to form a substituted or unsubstituted condensed ring", unless otherwise stated in the present specification, it is preferably one or more groups consisting of two or more adjacent groups bonded to each other to form a substituted or unsubstituted "unsaturated ring" formed by multiple atoms of the parent skeleton and one or more and fifteen or less elements selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0507] When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the above-mentioned "substituents described in the present specification".

[0508] When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above-mentioned "substituents described in the present specification".

[0509] The above is an explanation of the case where "one or more groups of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted single ring" and the case where "one or more groups of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted condensed ring" ("the case where they are bonded to form a ring").

[0510] ·Substituents when expressed as "substituted or unsubstituted"

[0511] In one embodiment of the present specification, the substituent described as "substituted or unsubstituted" (sometimes referred to as "optional substituent" in the present specification) is selected from, for example, unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0512] unsubstituted alkenyl having 2 to 50 carbon atoms,

[0513] unsubstituted alkynyl having 2 to 50 carbon atoms,

[0514] unsubstituted cycloalkyl having 3 to 50 ring carbon atoms,

[0515] -Si(R 901 )(R 902 )(R 903 ),

[0516] -O-(R 904 ),

[0517] -S-(R 905 ),

[0518] -N(R 906) (R 907 ),

[0519] Halogen atoms, cyano, nitro,

[0520] unsubstituted aryl group having 6 to 50 ring carbon atoms and

[0521] Unsubstituted heterocyclic group having 5 to 50 ring atoms

[0522] The groups in the group etc.

[0523] Here, R 901 ~R 907 Each independently

[0524] Hydrogen atoms,

[0525] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0526] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0527] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0528] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0529] In R 901 When there are two or more R 901 Same or different from each other,

[0530] In R 902 When there are two or more R 902 Same or different from each other,

[0531] In R 903 When there are two or more R 903 Same or different from each other,

[0532] In R 904 When there are two or more R 904 Same or different from each other,

[0533] In R 905 When there are two or more R 905 Same or different from each other,

[0534] In R 906 When there are two or more R 906 Same or different from each other,

[0535] In R907 When there are two or more R 907 Same as or different from each other.

[0536] In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

[0537] an alkyl group having 1 to 50 carbon atoms,

[0538] An aryl group having 6 to 50 ring carbon atoms and

[0539] A heterocyclic group having 5 to 50 ring atoms

[0540] The groups in the group.

[0541] In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

[0542] an alkyl group having 1 to 18 carbon atoms,

[0543] An aryl group having 6 to 18 ring carbon atoms and

[0544] A heterocyclic group having 5 to 18 ring atoms

[0545] The groups in the group.

[0546] Specific examples of each group of the above-mentioned optional substituent are the specific examples of the substituent described in the above-mentioned section "substituent described in the present specification".

[0547] Unless otherwise stated in the present specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably a benzene ring.

[0548] Unless otherwise specified in the present specification, an optional substituent may further have a substituent. The substituent further possessed by the optional substituent is the same as the optional substituent described above.

[0549] In this specification, the numerical range expressed using "AA to BB" means a range including the numerical value AA described before "AA to BB" as the lower limit value and the numerical value BB described after "AA to BB" as the upper limit value.

[0550] Hereinafter, the compound of the present invention will be described.

[0551] A compound according to one embodiment of the present invention is represented by the following formula (1).

[0552] Herein, only the compound of the present invention represented by formula (1) and the formula included in formula (1) described later may be referred to as "inventive compound (1)". In addition, the compound involved in another embodiment of the present invention is represented by formula (2) described later. Only the compound of the present invention represented by formula (2) described later and the formula included in formula (2) described later may be referred to as "inventive compound (2)". In addition, when both "inventive compound (1)" and "inventive compound (2)" are meant, these may be referred to as "inventive compound" only.

[0553] [Chemical formula 26]

[0554]

[0555] Hereinafter, symbols in formula (1) and the formulae described later included in formula (1) will be described. It should be noted that the same symbols have the same meanings.

[0556] In formula (1),

[0557] R 1 and R 2 One of them is methyl and the other is unsubstituted phenyl,

[0558] R 1 With R 2 They are not bonded to each other and thus do not form a ring structure.

[0559] R 3 and R 4 One of them is methyl and the other is unsubstituted phenyl,

[0560] R 3 With R 4 They are not bonded to each other and thus do not form a ring structure.

[0561] R 11 ~R 18 and R 21 ~R 28 A hydrogen atom.

[0562] in,

[0563] Selected from R 11 ~R 18 One of them is a single bond to *a,

[0564] Selected from R 21 ~R 28 One of them is a single bond bonded to *b.

[0565] Preferably selected from R 12 , R 13 , R 14 , R 15 , R16 and R 17 One of them is a single bond bonded to *a, and is more preferably selected from R 12 and R 17 One of them is a single bond bonded to *a.

[0566] Preferably selected from R 22 , R 23 , R 24 , R 25 , R 26 and R 27 One of them is a single bond bonded to *b, and is more preferably selected from R 22 and R 27 One of them is a single bond bonded to *b.

[0567] L 1 and L 2 Each is independently a single bond, or a substituted or unsubstituted phenylene group.

[0568] L 1 and L 2 Preferred is a single bond.

[0569] Ar 1 It is a group represented by any one of formulae (1-1) to (1-6).

[0570] [Chemical formula 27]

[0571]

[0572] In formulas (1-1) to (1-6),

[0573] R 31 ~R 35 , R 41 ~R 46 , R 51 ~R 55 , R 61 ~R 68 , R 71 ~R 82 , R 91 ~R 100 , R 101 ~R 108 , R 111 ~R 116 , R 121 ~R 125 and R 131 ~R 135Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0574] R 31 ~R 35 , R 41 ~R 46 , R 51 ~R 55 , R 61 ~R 68 , R 71 ~R 82 , R 91 ~R 100 , R 101 ~R 108 , R 111 ~R 116 , R 121 ~R 125 and R 131 ~R 135 Each independently is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; more preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; further preferably a hydrogen atom.

[0575] R 31 ~R 35 , R 41 ~R 46 , R 51 ~R 55 , R 61 ~R 68 , R 71 ~R 82 , R 91 ~R 100 , R 101 ~R 108 , R 111 ~R 116 , R 121 ~R 125 and R 131 ~R 135 The details of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms represented by are the same as those described in the above section "Substituents described in the present specification".

[0576] R31 ~R 35 , R 41 ~R 46 , R 51 ~R 55 , R 61 ~R 68 , R 71 ~R 82 , R 91 ~R 100 , R 101 ~R 108 , R 111 ~R 116 , R 121 ~R 125 and R 131 ~R 135 The unsubstituted alkyl group represented by is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, more preferably methyl, ethyl, isopropyl, or tert-butyl, further preferably methyl or tert-butyl.

[0577] R 31 ~R 35 , R 41 ~R 46 , R 51 ~R 55 , R 61 ~R 68 , R 71 ~R 82 , R 91 ~R 100 , R 101 ~R 108 , R 111 ~R 116 , R 121 ~R 125 and R 131 ~R 135 The details of the substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms are the same as those described in the above section "Substituents described in the present specification".

[0578] R 31 ~R 35 , R 41 ~R 46 , R 51 ~R 55 , R 61 ~R 68 , R 71 ~R 82 , R 91 ~R 100 , R 101 ~R 108 , R111 ~R 116 , R 121 ~R 125 and R 131 ~R 135 The unsubstituted cycloalkyl represented by is preferably cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, or 2-norbornyl, more preferably cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl, further preferably cyclopentyl or cyclohexyl.

[0579] R 31 ~R 35 , R 41 ~R 46 , R 51 ~R 55 , R 61 ~R 68 , R 71 ~R 82 , R 91 ~R 100 , R 101 ~R 108 , R 111 ~R 116 , R 121 ~R 125 and R 131 ~R 135 The details of the halogen atom represented by are the same as those described in the above section of "substituents described in the present specification", and a fluorine atom is preferred.

[0580] R 31 ~R 35 , R 41 ~R 46 , R 51 ~R 55 , R 61 ~R 68 , R 71 ~R 82 , R 91 ~R 100 , R 101 ~R 108 , R 111 ~R 116 , R 121 ~R 125 and R 131 ~R 135 The details of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms are the same as those described in the above "substituents described in the present specification".

[0581] R 31 ~R 35 , R 41~R 46 , R 51 ~R 55 , R 61 ~R 68 , R 71 ~R 82 , R 91 ~R 100 , R 101 ~R 108 , R 111 ~R 116 , R 121 ~R 125 and R 131 ~R 135 The unsubstituted aryl group represented by is preferably a phenyl group, a biphenyl group, a naphthyl group, or a phenanthryl group, more preferably a phenyl group, a biphenyl group, or a naphthyl group, and further preferably a phenyl group.

[0582] R 31 ~R 35 , R 41 ~R 46 , R 51 ~R 55 , R 61 ~R 68 , R 71 ~R 82 , R 91 ~R 100 , R 101 ~R 108 , R 111 ~R 116 , R 121 ~R 125 and R 131 ~R 135 The details of the substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms are the same as those described in the above "substituents described in the present specification".

[0583] The unsubstituted heterocyclic group is preferably a dibenzofuranyl group or a dibenzothiophenyl group.

[0584] X 1 is an oxygen atom, a sulfur atom, or CR a R b ,

[0585] R a and R b are each independently a hydrogen atom, a methyl group, or a substituted or unsubstituted phenyl group, R a They may bond with each other to form a substituted or unsubstituted ring.

[0586] In one embodiment of the present invention, X 1Preferably, X is an oxygen atom. 1 Preferably, X is a sulfur atom. 1 Preferably CR a R b , R a and R b Preferred is a methyl group or a substituted or unsubstituted phenyl group.

[0587] The above R a With R b The details of the optionally substituted or unsubstituted ring formed by bonding to each other are the same as those described in the above "substituents described in the present specification", and are selected from a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocycle, and a substituted or unsubstituted non-aromatic heterocycle.

[0588] The aromatic hydrocarbon ring is, for example, a benzene ring, a biphenylene ring, a naphthalene ring, or a fluorene ring, and is preferably a naphthalene ring or a fluorene ring.

[0589] The aliphatic hydrocarbon ring is, for example, a cyclopentene ring, a cyclopentadiene ring, a cyclohexene ring, a cyclohexadiene ring, or a hydrocarbon ring obtained by partially hydrogenating the aromatic hydrocarbon ring.

[0590] The above-mentioned aromatic heterocyclic ring is, for example, a pyrrole ring, a furan ring, a thiophene ring, a pyridine ring, an imidazole ring, a pyrazole ring, an indole ring, an isoindole ring, a benzofuran ring, an isobenzofuran ring, a benzothiophene ring, a benzimidazole ring, an indazole ring, a dibenzofuran ring, a naphthiobenzofuran ring, a dibenzothiophene ring, a naphthiobenzothiophene ring, a carbazole ring, or a benzocarbazole ring, preferably a dibenzofuran ring or a dibenzothiophene ring.

[0591] The non-aromatic heterocycle is, for example, a heterocycle obtained by partially hydrogenating the aromatic heterocycle.

[0592] In one embodiment of the present invention, R a With R b They may not bond to each other to form a substituted or unsubstituted ring.

[0593] Selected from R 31 ~R 35 One of them is a single bond to *c,

[0594] Selected from R41~R4 6 One of them is a single bond bonded to *d, selected from R41 to R4 6 The other one in is a single bond bonded to *e,

[0595] Selected from R 6 5~R 6 One of 8 is a single bond bonded to *f,

[0596] Selected from R 79 ~R 82 One of them is a single bond to *g,

[0597] Selected from R 91 and R 97 ~R 100 One of them is a single bond to *h,

[0598] Selected from R 105 ~R 108 One of them is a single bond bonded to *i,

[0599] Selected from R 111 ~R 116 One of them is a single bond bonded to *j, selected from R 111 ~R 116 The other one of them is a single bond bonded to *k, selected from R 111 ~R 116 The other one in is a single bond bonded to *1.

[0600] R is selected from the group consisting of 31 ~R 35 Two adjacent R selected from R which are not any of the above single bonds 41 ~R 46 Two adjacent ones in R 51 ~R 55 Two adjacent R selected from the group consisting of R which are not the above single bonds 61 ~R 68 Two adjacent R selected from the group consisting of R which are not the above single bonds 71 ~R 82 Two adjacent R selected from the group consisting of R which are not the above single bonds 91 ~R 100 Two adjacent R selected from the group consisting of R which are not the above single bonds 101 ~R 108 Two adjacent R selected from R which are not any of the above single bonds 111 ~R 116 Two adjacent ones in R 121 ~R 125 Two adjacent ones in R 131 ~R 135 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring structure.

[0601] The benzene ring A1 and benzene ring B1, benzene ring A1 and benzene ring C1, benzene ring A1 and benzene ring D1, benzene ring A1 and benzene ring E1, benzene ring A1 and benzene ring F1, benzene ring B1 and benzene ring C1, benzene ring D1 and benzene ring E1, and benzene ring D1 and benzene ring F1 are not crosslinked.

[0602] ** indicates the bonding position with the central nitrogen atom N,

[0603] m is 0 or 1, n is 0 or 1,

[0604] In formula (1-1) and (1-2), when m is 0 and n is 0, *e is bonded to the central nitrogen atom N, when m is 0 and n is 1, *c is bonded to the central nitrogen atom N, and when m is 1 and n is 0, *e is bonded to a member selected from R 31 ~R 35 1 bond in

[0605] In formulas (1-3) to (1-6), when m is 0, *c is bonded to the central nitrogen atom N,

[0606] In R 12 or R 17 is a single bond bonded to *a, R 22 or R 27 When it is a single bond bonding to *b, the formula (1-1) excludes the p-biphenyl group.

[0607] That is, in R 12 or R 17 is a single bond bonded to *a, R 22 or R 27 When is a single bond bonded to *b, m is 1 and n is 0, in formula (1-1), R 31 , R 32 , R 34 and R 35 One of them is a single bond bonded to *c, preferably selected from R 31 and R 35 One of them is a single bond bonded to *c.

[0608] In addition, in R 12 or R 17 is a single bond bonded to *a, R 22 or R 27 When is a single bond bonded to *b, m is 0 and n is 1, in formula (1-1), R 46 is a single bond bonded to *d, selected from R 41 , R 42 , R 44 and R 45 One of them is a single bond bonded to *e, preferably selected from R 41 and R 45 One of them is a single bond bonded to *e.

[0609] In addition, the p-biphenyl group refers to the following formula.

[0610] [Chemical formula 28]

[0611]

[0612] In formulas (1-1) and (1-2), in one embodiment of the present invention, m is preferably 0 and n is 0, in another embodiment, m is preferably 0 and n is 1, in still another embodiment, m is preferably 1 and n is 0, and in still another embodiment, m is preferably 1 and n is 1.

[0613] In formula (1-1), m or n is preferably 0.

[0614] In formulae (1-3) to (1-6), in one embodiment of the present invention, m is preferably 0, and in another embodiment, m is preferably 1.

[0615] The group represented by formula (1-1) is more preferably a substituted or unsubstituted group selected from the following formulae.

[0616] [Chemical formula 29]

[0617]

[0618] (In the formula, optional substituents are omitted.)

[0619] The group represented by formula (1-2) is preferably a substituted or unsubstituted group selected from the following formulae.

[0620] [Chemical formula 30]

[0621]

[0622] (In the formula, optional substituents are omitted.)

[0623] The group represented by formula (1-3) is preferably a substituted or unsubstituted group selected from the following formulae.

[0624] [Chemical formula 31]

[0625]

[0626] (In the formula, optional substituents are omitted.)

[0627] The group represented by formula (1-4) is preferably an unsubstituted group selected from the following formulae.

[0628] [Chemical formula 32]

[0629]

[0630] (In the formula, optional substituents are omitted.)

[0631] The group represented by formula (1-5) is preferably a substituted or unsubstituted group selected from the following formulae.

[0632] [Chemical formula 33]

[0633]

[0634] [Chemical formula 34]

[0635]

[0636] (In the formula, optional substituents are omitted.)

[0637] The group represented by formula (1-6) is preferably a substituted or unsubstituted group selected from the following formulae.

[0638] [Chemical formula 35]

[0639]

[0640] (In the formula, optional substituents are omitted.)

[0641] Ar 1 It is preferably a group represented by any one of formulae (1-1), (1-2), (1-5), and (1-6), and more preferably a group represented by formula (1-1).

[0642] As one embodiment of the present invention,

[0643] (1-1) R is not a single bond to *c 31 ~R 35 can be hydrogen,

[0644] (1-2) R is not a single bond bonded to *d and is not a single bond bonded to *e 41 ~R 46 can be all hydrogen atoms,

[0645] (1-3)R 51 ~R 55 can be all hydrogen atoms,

[0646] (1-4)R 6 1~R 64 , and R which is not a single bond bonded to *f 65 ~R 68 can be all hydrogen atoms,

[0647] (1-5)R 71 ~R 78 , and R which is not a single bond bonded to *g 79 ~R 82 can be all hydrogen atoms,

[0648] (1-6)R 92 ~R 96 , and R which is not a single bond bonded to *h 91 and R97 ~R 100 can be all hydrogen atoms,

[0649] (1-7)R 101 ~R 104 , and R which is not a single bond bonded to *i 105 ~R 108 can be all hydrogen atoms,

[0650] (1-8) R is not a single bond bonded to *j, not a single bond bonded to *k, and not a single bond bonded to *1 111 ~R 116 , R 121 ~R 125 and R 131 ~R 135 They may all be hydrogen atoms.

[0651] A compound according to another embodiment of the present invention is represented by the following formula (2).

[0652] [Chemical formula 36]

[0653]

[0654] Hereinafter, symbols in formula (2) and the formulae described later included in formula (2) will be described. It should be noted that the same symbols have the same meanings.

[0655] In formula (2),

[0656] Selected from R 201 ~R 204 One of them is methyl, selected from R 201 ~R 204 The other three are unsubstituted phenyl groups,

[0657] R 201 With R 202 do not bond to each other and thus do not form a ring structure,

[0658] R 203 With R 204 They are not bonded to each other and thus do not form a ring structure.

[0659] R 211 ~R 218 and R 221 ~R 228 A hydrogen atom.

[0660] in,

[0661] Selected from R 211 ~R 218 One of them is a single bond to *m,

[0662] Selected from R 221 ~R 228 One of them is a single bond bonded to *n.

[0663] Preferably selected from R 212 , R 213 , R 214 , R 215 , R 216 and R 217 One of them is a single bond bonded to *m, and is more preferably selected from R 212 and R 217 One of them is a single bond bonded to *m.

[0664] Preferably selected from R 222 , R 223 , R 224 , R 225 , R 226 and R 227 One of them is a single bond bonded to *n, and is more preferably selected from R 222 and R 227 One of them is a single bond bonded to *n.

[0665] L 11 and L 12 Each is independently a single bond, or a substituted or unsubstituted phenylene group.

[0666] L 11 and L 12 Preferred is a single bond.

[0667] Ar 11 It is a group represented by any one of formulae (2-1) to (2-6).

[0668] [Chemical formula 37]

[0669]

[0670] In formulas (2-1) to (2-6),

[0671] R 231 ~R 235 , R 241 ~R 246 , R 251 ~R 255 , R 261 ~R 268 , R 271 ~R 282 , R 291 ~R 300 , R 301 ~R 308 , R 311 ~R 316 , R 321~R 325 and R 331 ~R 335 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0672] R2 31 ~R2 35 , R2 41 ~R2 46 , R2 51 ~R2 55 , R2 61 ~R2 68 , R2 71 ~R2 82 , R2 91 ~R 300 , R 301 ~R 308 , R 311 ~R 316 , R 321 ~R 325 and R 331 ~R 335 Each independently is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; more preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; further preferably a hydrogen atom.

[0673] R 231 ~R 235 , R 241 ~R 246 , R 251 ~R 255 , R 261 ~R 268 , R 271 ~R 282 , R 291 ~R 300 , R 301 ~R 308 , R 311 ~R 316 , R 321 ~R 325 and R 331 ~R 335 The details of each group are the same as those for R 31~R 35 , R 41 ~R 46 , R 51 ~R 55 , R 61 ~R 68 , R 71 ~R 82 , R 91 ~R 100 , R 101 ~R 108 , R 111 ~R 116 , R 121 ~R 125 and R 131 ~R 135 The details of the corresponding groups described are the same, and the preferred groups and the like are also the same.

[0674] X 2 is an oxygen atom, a sulfur atom, or CR c R d ,

[0675] R c and R d are each independently a hydrogen atom or a methyl group, R c With R d They are not bonded to each other and thus do not form a ring structure.

[0676] In one embodiment of the present invention, X 2 Preferably, X is an oxygen atom. 2 Preferably, X is a sulfur atom. 2 Preferably CR c R d , R c and R d Preferred is a methyl group or a substituted or unsubstituted phenyl group.

[0677] Selected from R 231 ~R 235 One of them is a single bond bonded to *o,

[0678] Selected from R2 4 1~R2 46 One of them is a single bond bonded to *p, selected from R2 4 1~R2 46 The other one in is a single bond bonded to *q,

[0679] Selected from R2 6 5~R2 6 One of 8 is a single bond bonded to *r,

[0680] Selected from R27 9~R28 2 One of them is a single bond to *s,

[0681] Selected from R 291 and R 297 ~R 300 One of them is a single bond to *t,

[0682] Selected from R 305 ~R 308 One of them is a single bond to *u,

[0683] Selected from R 311 ~R 316 One of them is a single bond bonded to *v, selected from R 311 ~R 316 The other one of them is a single bond bonded to *w, selected from R 311 ~R 316 The other one in is a single bond bonded to *x.

[0684] Two adjacent ones selected from R231 to R235 which are not the above single bonds, and R2 selected from any of the above single bonds 4 1~R2 46 2 adjacent ones selected from R251 to R255, 2 adjacent ones selected from R251 to R255, R2 selected from the above single bonds 6 1~R2 6 8, two adjacent R2 selected from the group consisting of R2 other than the above single bonds 7 1~R 282 Two adjacent R selected from the group consisting of R which are not the above single bonds 291 ~R 300 Two adjacent R selected from the group consisting of R which are not the above single bonds 301 ~R 308 Two adjacent R selected from R which are not any of the above single bonds 311 ~R 316 Two adjacent ones in R 321 ~R 325 Two adjacent ones in R 331 ~R 335 The two adjacent ones in the molecule are not bonded to each other and thus do not form a ring structure.

[0685] The benzene ring A2 and the benzene ring B2, the benzene ring A2 and the benzene ring C2, the benzene ring A2 and the benzene ring D2, the benzene ring A2 and the benzene ring E2, the benzene ring A2 and the benzene ring F2, the benzene ring B2 and the benzene ring C2, the benzene ring D2 and the benzene ring E2, and the benzene ring D2 and the benzene ring F2 are not cross-linked.

[0686] *** indicates the bonding position with the central nitrogen atom N,

[0687] p is 0 or 1, q is 0 or 1,

[0688] In formula (2-1) and (2-2), when p is 0 and q is 0, *q is bonded to the central nitrogen atom N, when p is 0 and q is 1, *o is bonded to the central nitrogen atom N, and when p is 1 and q is 0, *q is bonded to a member selected from R 231 ~R 235 1 bond in

[0689] In formulas (2-3) to (2-6), when p is 0, *o is bonded to the central nitrogen atom N,

[0690] In formula (2-5), in X 2 CR c R d When p is 0, select L 11 and L 12 At least one of them is a substituted or unsubstituted phenylene group,

[0691] In formula (2-5), in X 2 When it is an oxygen atom and p is 1, it is selected from R 306 ~R 308 One of them is a single bond to *u,

[0692] In R21 2 or R21 7 is a single bond bonded to *m, R2 22 or R2 27 In the case of a single bond bonding to *n, the formula (2-1) excludes the p-biphenyl group.

[0693] That is, in R 212 or R 217 is a single bond bonded to *m, R 222 or R 227 When is a single bond bonded to *n, m is 1 and n is 0, in formula (2-1), R 231 , R 232 , R 234 and R 235 One of them is a single bond bonded to *o, preferably selected from R 231 and R 235 One of them is a single bond bonded to *o.

[0694] In addition, in R 212 or R 217 is a single bond bonded to *m, R 222 or R 227 When it is a single bond bonded to *n, m is 0 and n is 1, in formula (2-1), R2 46 is a single bond bonded to *p, selected from R 241 , R 242 , R244 and R 245 One of them is a single bond bonded to *q, preferably selected from R 241 and R 245 One of them is a single bond bonded to *q.

[0695] In formulas (2-1) and (2-2), in one embodiment of the present invention, m is preferably 0 and n is 0, in another embodiment, m is preferably 0 and n is 1, in still another embodiment, m is preferably 1 and n is 0, and in still another embodiment, m is preferably 1 and n is 1.

[0696] In formula (2-1), m or n is preferably 0.

[0697] In formulae (1-3) to (1-6), in one embodiment of the present invention, m is preferably 0, and in another embodiment, m is preferably 1.

[0698] Preferred groups represented by formula (2-1) are the same as preferred groups represented by formula (1-1).

[0699] Preferred groups represented by formula (2-2) are the same as preferred groups represented by formula (1-2).

[0700] Preferred groups represented by formula (2-3) are the same as preferred groups represented by formula (1-3).

[0701] Preferred groups represented by formula (2-4) are the same as preferred groups represented by formula (1-4).

[0702] Preferred groups represented by formula (2-5) are the same as preferred groups represented by formula (1-5).

[0703] Preferred groups represented by formula (1-6) are the same as preferred groups represented by formula (1-6).

[0704] Ar 11 The group is preferably a group represented by any one of formulae (2-1), (2-2), (2-5) and (2-6), and more preferably a group represented by formula (2-1).

[0705] As one embodiment of the present invention,

[0706] (2-1) R2 that is not a single bond bonded to *o 3 1~R 2 3 5 can be all hydrogen atoms,

[0707] (2-2) R is not a single bond bonded to *p and is not a single bond bonded to *q 24 1~R2 46 can be all hydrogen atoms,

[0708] (2-3)R 2 51~R25 5 can be all hydrogen atoms,

[0709] (2-4)R2 6 1~R2 64 , and R2 which is not a single bond bonded to *r 65 ~R2 6 8 can all be hydrogen atoms,

[0710] (2-5)R 271 ~R 278 , and R which is not a single bond bonded to *s 279 ~R 282 can be all hydrogen atoms,

[0711] (2-6)R 292 ~R 296 , and R which is not a single bond bonded to *t 291 and R 297 ~R 300 can be all hydrogen atoms,

[0712] (2-7)R 301 ~R 304 , and R which is not a single bond to *u 305 ~R 308 can be all hydrogen atoms,

[0713] (2-8) R is not a single bond bonded to *v, not a single bond bonded to *w, and not a single bond bonded to *x 311 ~R 316 , R 321 ~R 325 and R 331 ~R 335 They may all be hydrogen atoms.

[0714] As mentioned above, the "hydrogen atom" used in the present specification includes a protium atom, a deuterium atom, and a tritium atom. Therefore, the inventive compound may contain a deuterium atom of natural origin.

[0715] In addition, deuterium atoms can be deliberately introduced into the invention compound by using a deuterated compound as part or all of the raw material compound. Therefore, in one embodiment of the present invention, the invention compound contains at least one deuterium atom. That is, the invention compound (1) can be a compound represented by formula (1), at least one of the hydrogen atoms contained in the compound is a deuterium atom, and the invention compound (2) can be a compound represented by formula (2), at least one of the hydrogen atoms contained in the compound is a deuterium atom.

[0716] In the compound represented by formula (1),

[0717] Selected from R 1 and R 2 A hydrogen atom possessed by a methyl group or an unsubstituted phenyl group represented by any one of ;

[0718] R 3 and R 4 A hydrogen atom possessed by a methyl group or an unsubstituted phenyl group represented by any one of ;

[0719] R 11 ~R 18 and R 21 ~R 28 A hydrogen atom represented by any one of ;

[0720] L 1 and L 2 a hydrogen atom possessed by a substituted or unsubstituted phenylene group represented by any one of ;

[0721] R 31 ~R 35 , R 41 ~R 46 , R 51 ~R 55 , R 61 ~R 68 , R 71 ~R 82 , R 91 ~R 100 , R 101 ~R 108 , R 111 ~R 116 , R 121 ~R 125 and R 131 ~R 135 Any one of which represents a hydrogen atom; R 31 ~R 35 , R 41 ~R 46 , R 51 ~R 55 , R 61 ~R 68 , R 71 ~R 82 , R 91 ~R 100 , R 101 ~R 108 , R 111 ~R 116 , R 121 ~R 125 and R 131 ~R 135 A hydrogen atom possessed by a substituted or unsubstituted alkyl group, cycloalkyl group, aryl group or heterocyclic group represented by any one of ;

[0722] R a and R b Any one of which represents a hydrogen atom; R a and R b A hydrogen atom possessed by a methyl group or a substituted or unsubstituted phenyl group represented by any one of

[0723] At least one hydrogen atom in may be a deuterium atom.

[0724] In the compound represented by formula (2),

[0725] Selected from R2 0 1~R2 04 A hydrogen atom possessed by a methyl group or an unsubstituted phenyl group represented by any one of ;

[0726] R 211 ~R 218 and R 221 ~R 228 A hydrogen atom represented by any one of ;

[0727] L 11 and L 12 a hydrogen atom possessed by a substituted or unsubstituted phenylene group represented by any one of ;

[0728] R 231 ~R 235 , R 241 ~R 246 , R 251 ~R 255 , R 261 ~R 268 , R 271 ~R 282 , R 291 ~R 300 , R 301 ~R 308 , R 311 ~R 316 , R 321 ~R 325 and R 331 ~R 335 Any one of which represents a hydrogen atom; R 231 ~R 235 , R 241 ~R 246 , R 251 ~R 255 , R 261 ~R 268 , R 271 ~R 282 , R 291 ~R 300 , R 301 ~R308 , R 311 ~R 316 , R 321 ~R 325 and R 331 ~R 335 A hydrogen atom possessed by a substituted or unsubstituted alkyl group, cycloalkyl group, aryl group or heterocyclic group represented by any one of ;

[0729] R c and R d Any one of which represents a hydrogen atom; R c and R d A hydrogen atom possessed by a methyl group or a substituted or unsubstituted phenyl group represented by any one of

[0730] At least one hydrogen atom in may be a deuterium atom.

[0731] The deuteration rate of the invention compound depends on the deuteration rate of the raw material compound used. Even if a raw material with a specified deuteration rate is used, it is possible to contain protium isotopes at a certain ratio of natural origin. Therefore, for the scheme of the deuteration rate of the invention compound shown below, the ratio calculated by counting only the number of deuterium atoms represented in the chemical formula includes a ratio that takes into account trace amounts of isotopes of natural origin.

[0732] The deuteration rate of the compound of the invention is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, further preferably 10% or more, further preferably 50% or more.

[0733] The compound of the invention may be a mixture of 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, further preferably 5% or more, further preferably 10% or more, further preferably 50% or more, and less than 100%.

[0734] The ratio of the number of deuterium atoms to the total number of hydrogen atoms in the compound of the invention is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, further preferably 10% or more, and is 100% or less.

[0735] Details of substituents (optional substituents) included in the definitions of the above formulae when expressed as “substituted or unsubstituted” are the same as those described in “substituents when expressed as “substituted or unsubstituted””.

[0736] The compounds of the invention can be easily produced by those skilled in the art with reference to the synthesis examples described below and known synthesis methods.

[0737] Specific examples of the compounds of the invention are shown below, but the compounds of the invention are not limited to the following exemplified compounds.

[0738] In the following specific examples, D represents a deuterium atom.

[0739] [Chemical formula 38]

[0740]

[0741] [Chemical formula 39]

[0742]

[0743] [Chemical formula 40]

[0744]

[0745] [Chemical formula 41]

[0746]

[0747] [Chemical formula 42]

[0748]

[0749] [Chemical formula 43]

[0750]

[0751] [Chemical formula 44]

[0752]

[0753] [Chemical formula 45]

[0754]

[0755] [Chemical formula 46]

[0756]

[0757] [Chemical formula 47]

[0758]

[0759] [Chemical formula 48]

[0760]

[0761] [Chemical formula 49]

[0762]

[0763] [Chemical formula 50]

[0764]

[0765] [Chemical formula 51]

[0766]

[0767] [Chemical formula 52]

[0768]

[0769] [Chemical formula 53]

[0770]

[0771] [Chemical formula 54]

[0772]

[0773] [Chemical formula 55]

[0774]

[0775] [Chemical formula 56]

[0776]

[0777] [Chemical formula 57]

[0778]

[0779] [Chemical formula 58]

[0780]

[0781] [Chemical formula 59]

[0782]

[0783] [Chemical formula 60]

[0784]

[0785] [Chemical formula 61]

[0786]

[0787] [Chemical formula 62]

[0788]

[0789] [Chemical formula 63]

[0790]

[0791] [Chemical formula 64]

[0792]

[0793] [Chemical formula 65]

[0794]

[0795] [Chemical formula 66]

[0796]

[0797] [Chemical formula 67]

[0798]

[0799] [Chemical formula 68]

[0800]

[0801] [Chemical formula 69]

[0802]

[0803] [Chemical formula 70]

[0804]

[0805] [Chemical formula 71]

[0806]

[0807] [Chemical formula 72]

[0808]

[0809] [Chemical formula 73]

[0810]

[0811] [Chemical formula 74]

[0812]

[0813] [Chemical formula 75]

[0814]

[0815] [Chemical formula 76]

[0816]

[0817] [Chemical formula 77]

[0818]

[0819] [Chemical formula 78]

[0820]

[0821] [Chemical formula 79]

[0822]

[0823] [Chemical formula 80]

[0824]

[0825] [Chemical formula 81]

[0826]

[0827] [Chemical formula 82]

[0828]

[0829] [Chemical formula 83]

[0830]

[0831] [Chemical formula 84]

[0832]

[0833] [Chemical formula 85]

[0834]

[0835] [Chemical formula 86]

[0836]

[0837] [Chemical formula 87]

[0838]

[0839] [Chemical formula 88]

[0840]

[0841] [Chemical formula 89]

[0842]

[0843] [Chemical formula 90]

[0844]

[0845] [Chemical formula 91]

[0846]

[0847] [Chemical formula 92]

[0848]

[0849] [Chemical formula 93]

[0850]

[0851] [Chemical formula 94]

[0852]

[0853] [Chemical formula 95]

[0854]

[0855] [Chemical formula 96]

[0856]

[0857] [Chemical formula 97]

[0858]

[0859] [Chemical formula 98]

[0860]

[0861] [Chemical formula 99]

[0862]

[0863] [Chemical formula 100]

[0864]

[0865] [Chemical Formula 101]

[0866]

[0867] [Chemical formula 102]

[0868]

[0869] [Chemical formula 103]

[0870]

[0871] [Chemical formula 104]

[0872]

[0873] [Chemical formula 105]

[0874]

[0875] [Chemical formula 106]

[0876]

[0877] [Chemical formula 107]

[0878]

[0879] [Chemical formula 108]

[0880]

[0881] [Chemical formula 109]

[0882]

[0883] [Chemical formula 110]

[0884]

[0885] [Chemical formula 111]

[0886]

[0887] [Chemical formula 112]

[0888]

[0889] [Chemical formula 113]

[0890]

[0891] [Chemical formula 114]

[0892]

[0893] [Chemical formula 115]

[0894]

[0895] [Chemical formula 116]

[0896]

[0897] [Chemical formula 117]

[0898]

[0899] [Chemical formula 118]

[0900]

[0901] [Chemical formula 119]

[0902]

[0903] [Chemical formula 120]

[0904]

[0905] [Chemical formula 121]

[0906]

[0907] [Chemical formula 122]

[0908]

[0909] [Chemical formula 123]

[0910]

[0911] [Chemical formula 124]

[0912]

[0913] [Chemical formula 125]

[0914]

[0915] Materials for organic EL devices

[0916] The material for an organic EL element of the present invention contains the compound of the invention. The content of the compound of the invention in the material for an organic EL element is 1% by mass or more (including 100%), preferably 10% by mass or more (including 100%), more preferably 50% by mass or more (including 100%), further preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). The material for an organic EL element of the present invention is useful in the manufacture of an organic EL element.

[0917] Organic EL elements

[0918] The organic EL device of the present invention comprises an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer comprises a light-emitting layer, and at least one layer of the organic layer comprises the compound of the present invention.

[0919] As examples of organic layers containing the invention compound, a hole transport region (hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer, etc.) disposed between the anode and the light-emitting layer, a light-emitting layer, a spacer layer, an electron transport region (electron injection layer, electron transport layer, hole blocking layer, etc.) disposed between the cathode and the light-emitting layer, etc., can be cited, but are not limited thereto. The invention compound is preferably a material for the hole transport region or the light-emitting layer of a fluorescent or phosphorescent EL element, more preferably a material for the hole transport region, further preferably a material for a hole injection layer, a hole transport layer, an electron blocking layer, or an exciton blocking layer, and particularly preferably a material for a hole injection layer or a hole transport layer.

[0920] The organic EL element of the present invention may be a single-color light-emitting element of a fluorescent or phosphorescent light-emitting type, or a white light-emitting element of a fluorescent / phosphorescent mixed type, or a simple type having a single light-emitting unit, or a series type having a plurality of light-emitting units, wherein a fluorescent light-emitting element is preferred. Here, "light-emitting unit" refers to: a minimum unit comprising an organic layer, at least one of which is a light-emitting layer, and in which injected holes and electrons recombine to emit light.

[0921] For example, as a typical element structure of a simple organic EL element, the following element structure can be cited.

[0922] (1) Anode / light-emitting unit / cathode

[0923] In addition, the above-mentioned light-emitting unit may also be a multilayer type having a plurality of phosphorescent light-emitting layers or fluorescent light-emitting layers. In this case, a spacer layer may be provided between each light-emitting layer for the purpose of preventing the excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer. The following shows a typical layer structure of a simplified light-emitting unit. The layers in parentheses are optional.

[0924] (a) (hole injection layer / ) hole transport layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[0925] (b) (hole injection layer / ) hole transport layer / phosphorescent light emitting layer electron transport layer ( / electron injection layer)

[0926] (c) (hole injection layer / ) hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / electron transport layer ( / electron injection layer)

[0927] (d) (hole injection layer / ) hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer / electron transport layer ( / electron injection layer)

[0928] (e) (hole injection layer / ) hole transport layer / phosphorescent light emitting layer / spacer layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[0929] (f) (hole injection layer / hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer / spacer layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[0930] (g) (hole injection layer / ) hole transport layer / first phosphorescent emitting layer / spacer layer / second phosphorescent emitting layer / spacer layer / fluorescent emitting layer / electron transport layer ( / electron injection layer)

[0931] (h) (hole injection layer / ) hole transport layer / phosphorescent emitting layer / spacer layer / first fluorescent emitting layer / second fluorescent emitting layer / electron transport layer ( / electron injection layer)

[0932] (i) (hole injection layer / ) hole transport layer / electron blocking layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[0933] (j) (hole injection layer / ) hole transport layer / electron blocking layer / phosphorescent light emitting layer / electron transport layer ( / electron injection layer)

[0934] (k) (hole injection layer / ) hole transport layer / exciton blocking layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[0935] (1) (hole injection layer / ) hole transport layer / exciton blocking layer / phosphorescent light emitting layer / electron transport layer ( / electron injection layer)

[0936] (m) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light emitting layer / electron transport layer ( / electron injection layer)

[0937] (n) (hole injection layer / ) first hole transport layer / second hole transport layer / phosphorescent light emitting layer / electron transport layer ( / electron injection layer)

[0938] (o) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer)

[0939] (p) (hole injection layer / ) first hole transport layer / second hole transport layer / phosphorescent light emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer)

[0940] (q) (hole injection layer / ) hole transport layer / fluorescent light emitting layer / hole blocking layer / electron transport layer ( / electron injection layer)

[0941] (r) (hole injection layer / ) hole transport layer / phosphorescent light emitting layer / hole blocking layer / electron transport layer ( / electron injection layer)

[0942] (s) (hole injection layer / ) hole transport layer / fluorescent light emitting layer / exciton blocking layer / electron transport layer ( / electron injection layer)

[0943] (t) (hole injection layer / ) hole transport layer / phosphorescent light emitting layer / exciton blocking layer / electron transport layer ( / electron injection layer)

[0944] (m) (hole injection layer / ) first hole transport layer / second hole transport layer / third hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer)

[0945] (n) (hole injection layer / ) first hole transport layer / second hole transport layer / third hole transport layer / fluorescent light emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer)

[0946] Each of the phosphorescent or fluorescent light-emitting layers can be configured to emit light of different colors. Specifically, in the light-emitting unit (f), a layer structure such as (hole injection layer / ) hole transport layer / first phosphorescent light-emitting layer (red light emission) / second phosphorescent light-emitting layer (green light emission) / spacer layer / fluorescent light-emitting layer (blue light emission) / electron transport layer can be cited.

[0947] It should be noted that an electron blocking layer may be appropriately provided between each light-emitting layer and the hole transport layer or the spacer layer. In addition, a hole blocking layer may be appropriately provided between each light-emitting layer and the electron transport layer. By providing an electron blocking layer or a hole blocking layer, electrons or holes may be confined in the light-emitting layer to increase the recombination probability of charges in the light-emitting layer, thereby improving the luminous efficiency.

[0948] As a typical device structure of a tandem organic EL device, the following device structures can be mentioned.

[0949] (2) Anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode

[0950] Here, the first light emitting unit and the second light emitting unit may be independently selected from the light emitting units described above, for example.

[0951] The intermediate layer is also generally referred to as an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, or an intermediate insulating layer, and can be made of a known material that supplies electrons to the first light-emitting unit and holes to the second light-emitting unit.

[0952] Figure 1Schematic diagram showing an example of the structure of the organic EL element of the present invention. The organic EL element 1 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10 arranged between the anode 3 and the cathode 4. The light-emitting unit 10 has a light-emitting layer 5. There is a hole transport region 6 (hole injection layer, hole transport layer, etc.) between the light-emitting layer 5 and the anode 3, and there is an electron transport region 7 (electron injection layer, electron transport layer, etc.) between the light-emitting layer 5 and the cathode 4. In addition, an electron blocking layer (not shown) can be provided on the anode 3 side of the light-emitting layer 5, and a hole blocking layer (not shown) can be provided on the cathode 4 side of the light-emitting layer 5. In this way, electrons and holes can be confined in the light-emitting layer 5 to further improve the generation efficiency of excitons in the light-emitting layer 5.

[0953] Figure 2 Schematic diagram showing another structure of the organic EL element of the present invention. The organic EL element 11 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 20 disposed between the anode 3 and the cathode 4. The light-emitting unit 20 has a light-emitting layer 5. The hole transport region disposed between the anode 3 and the light-emitting layer 5 is formed by a hole injection layer 6a, a first hole transport layer 6b, and a second hole transport layer 6c. In addition, the electron transport region disposed between the light-emitting layer 5 and the cathode 4 is formed by a first electron transport layer 7a and a second electron transport layer 7b.

[0954] Figure 3 Schematic diagram showing another structure of the organic EL element of the present invention. The organic EL element 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. The hole transport region disposed between the anode 3 and the light-emitting layer 5 is formed by a hole injection layer 6a, a first hole transport layer 6b, a second hole transport layer 6c, and a third hole transport layer 6d. In addition, the electron transport region disposed between the light-emitting layer 5 and the cathode 4 is formed by a first electron transport layer 7a and a second electron transport layer 7b.

[0955] It should be noted that in the present invention, the subject combined with the fluorescent dopant material (fluorescent luminescent material) is called a fluorescent subject, and the subject combined with the phosphorescent dopant material is called a phosphorescent subject. The fluorescent subject and the phosphorescent subject are not distinguished only by the molecular structure. That is, the phosphorescent subject refers to the material that forms the phosphorescent luminescent layer containing the phosphorescent dopant, and does not mean that it cannot be used as a material for forming the fluorescent luminescent layer. The same is true for the fluorescent subject.

[0956] substrate

[0957] The substrate is used as a support of the organic EL element. As the substrate, for example, a plate of glass, quartz, plastic, etc. can be used. In addition, a flexible substrate can also be used. As the flexible substrate, for example, a plastic substrate formed of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, etc. can be cited. In addition, an inorganic vapor-deposited film can also be used.

[0958] anode

[0959] The anode formed on the substrate preferably uses a metal, alloy, conductive compound, and a mixture thereof with a large work function (specifically, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO: Indium Tin Oxide, indium tin oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, graphene, etc. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the above metals (such as titanium nitride), etc. can be mentioned.

[0960] These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering a target in which 1 to 10 wt% of zinc oxide is added to indium oxide, and indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering a target in which 0.5 to 5 wt% of tungsten oxide and 0.1 to 1 wt% of zinc oxide are added to indium oxide. In addition, it can also be produced by vacuum evaporation, coating, inkjet, spin coating, etc.

[0961] The hole injection layer formed adjacent to the anode is formed using a material that easily allows hole injection regardless of the work function of the anode. Therefore, materials commonly used as electrode materials (such as metals, alloys, conductive compounds and mixtures thereof, elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0962] It is also possible to use elements belonging to the first or second group of the periodic table as materials with a small work function, i.e., alkali metals such as lithium (Li), cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing them. It should be noted that when using alkali metals, alkaline earth metals, and alloys containing them to form anodes, vacuum evaporation methods and sputtering methods can be used. In addition, when using silver paste, coating methods, inkjet methods, etc. can be used.

[0963] Hole injection layer

[0964] The hole injection layer is a layer containing a material with high hole injection properties (hole injection material), and is formed between the anode and the light-emitting layer, or, if present, between the hole transport layer and the anode.

[0965] As hole injecting materials other than the invention compound, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. can be used.

[0966] Examples of hole injection layer materials include low molecular weight organic compounds such as 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNT PD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) and other aromatic amine compounds.

[0967] High molecular weight compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, high molecular weight compounds such as poly(N-vinylcarbazole) (abbreviated as PVK), poly(4-vinyltriphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD) can be mentioned. In addition, high molecular weight compounds to which an acid is added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[0968] In addition, an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K) is also preferably used.

[0969] [Chemical formula 126]

[0970]

[0971] (In the above formula, R 21 ~R 26 Each independently represents a cyano group, -CONH2, a carboxyl group, or a -COOR 27 (R 27 represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms). In addition, R 21 and R 22 , R 23 and R 24 and R 25 and R 26 Two adjacent ones of can be bonded to each other to form a group represented by -CO-O-CO-. )

[0972] As R 27 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl and the like can be mentioned.

[0973] Hole transport layer

[0974] 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 a hole injection layer is present, between the hole injection layer and the light-emitting layer. The inventive compound can be used alone or in combination with the following compounds for the hole transport layer.

[0975] The hole transport layer may be a single-layer structure or a multilayer structure comprising more than two layers. For example, the hole transport layer may be a two-layer structure comprising a first hole transport layer (anode side) and a second hole transport layer (cathode side). 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. In addition, the hole transport layer may be a three-layer structure comprising a first hole transport layer, a second hole transport layer and a third hole transport layer in sequence from the anode side. That is, a third hole transport layer may be configured between the second hole transport layer and the light-emitting layer.

[0976] In one embodiment of the present invention, the hole transport layer of the single-layer structure is preferably adjacent to the light-emitting layer. In addition, the hole transport layer closest to the cathode in the multi-layer structure, such as the second hole transport layer of the two-layer structure, is preferably adjacent to the light-emitting layer. In addition, the third hole transport layer of the three-layer structure is preferably adjacent to the light-emitting layer.

[0977] In another embodiment of the present invention, an electron blocking layer or the like described below may be interposed between the hole transport layer and the light emitting layer in the single layer structure or between the hole transport layer closest to the light emitting layer in the multilayer structure.

[0978] In the above-mentioned two-layer hole transport layer, the compound of the invention may be contained in one of the first hole transport layer and the second hole transport layer, or may be contained in both of them.

[0979] In one embodiment of the present invention, the invention compound is preferably contained only in the first hole transport layer. In another embodiment, the invention compound is preferably contained only in the second hole transport layer. In still another embodiment, the invention compound is preferably contained in both the first hole transport layer and the second hole transport layer.

[0980] In the hole transport layer of the three-layer structure, the invention compound may be included in at least one of the first to third hole transport layers. That is, the invention compound may be included in only one layer selected from the first to third hole transport layers (only the first hole transport layer, only the second hole transport layer, or only the third hole transport layer), only two layers selected from the first to third hole transport layers (only the first hole transport layer and the second hole transport layer, only the first hole transport layer and the third hole transport layer, or only the second hole transport layer and the third hole transport layer), or all of the first to third hole transport layers.

[0981] In one embodiment of the present invention, the compound of the invention contained in one or both of the first hole transport layer and the second hole transport layer is preferably a protium body from the viewpoint of production cost.

[0982] In another embodiment of the present invention, the compound of the invention contained in at least one of the first to third hole transport layers is preferably a protium body from the viewpoint of production cost.

[0983] The above-mentioned protium compound refers to a compound of the invention in which all hydrogen atoms in the compound of the invention are protium atoms.

[0984] Therefore, the present invention includes an organic EL device in which one or both of the first hole transport layer and the second hole transport layer contain an invention compound consisting essentially of a protium body. "An invention compound consisting essentially of a protium body" means that the content of the protium body is 90 mol% or more, preferably 95 mol% or more, and more preferably 99 mol% or more (each including 100%) relative to the total amount of the invention compound.

[0985] As hole transport layer materials other than the inventive compound, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used.

[0986] Examples of the aromatic amine compound include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated as BAFLP), 4,4'-bis[N-(9,9-dimethylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), The above compounds have 10 -6 cm 2 / Vs and above hole mobility.

[0987] Examples of the carbazole derivative include 4,4′-di(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: PCzPA).

[0988] Examples of the anthracene derivative include 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth).

[0989] A polymer compound such as poly(N-vinylcarbazole) (abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation: PVTPA) may also be used.

[0990] However, any compound other than the above compounds may be used as long as the compound has a higher hole-transporting property than an electron-transporting property.

[0991] Dopant materials for the light-emitting layer

[0992] The light-emitting layer is a layer containing a material with high luminescence (dopant material), and various materials can be used. For example, fluorescent materials and phosphorescent materials can be used as dopant materials. Fluorescent materials are compounds that emit light using a singlet excited state, and phosphorescent materials are compounds that emit light using a triplet excited state.

[0993] As the blue fluorescent material that can be used for the light-emitting layer, pyrene derivatives, styrylamine derivatives, Derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. Specifically, N, N'-bis [4- (9H-carbazole-9-yl) phenyl] -N, N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4- (9H-carbazole-9-yl) -4'- (10-phenyl-9-anthracenyl) triphenylamine (abbreviation: YGAPA), 4- (10-phenyl-9-anthracenyl) -4'- (9-phenyl-9H-carbazole-3-yl) triphenylamine (abbreviation: PCBAPA), etc. can be mentioned.

[0994] As green fluorescent light-emitting materials that can be used for the light-emitting layer, aromatic amine derivatives can be used. Specifically, N-(9,10-diphenyl-2-anthracenyl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCABPhA), N-(9,10-diphenyl-2-anthracenyl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPAPhA), PA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviated as 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviated as DPhAPhA), etc.

[0995] As the red fluorescent luminescent material that can be used for the light-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.

[0996] In one embodiment of the present invention, the light-emitting layer preferably contains a fluorescent light-emitting material (fluorescent dopant material).

[0997] As a blue phosphorescent material that can be used for the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes can be used. Specifically, bis[2-(4', 6'-difluorophenyl)pyridine-N, C2']iridium(III)tetrakis(1-pyrazolyl)borate (abbreviated as FIr6), bis[2-(4', 6'-difluorophenyl)pyridine-N, C2']iridium(III)picolinate (abbreviated as FIrpic), bis[2-(3', 5'bistrifluoromethylphenyl)pyridine-N, C2']iridium(III)picolinate (abbreviated as Ir(CF3ppy)2(pic)), bis[2-(4', 6'-difluorophenyl)pyridine-N, C2']iridium(III)acetylacetonate (abbreviated as FIracac), etc. can be cited.

[0998] As green phosphorescent materials that can be used for the light-emitting layer, iridium complexes can be used, such as tris(2-phenylpyridine-N,C2')iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridine-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazole)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), bis(benzo[h]quinoline)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)), and the like.

[0999] As the red phosphorescent light-emitting material that can be used for the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes can be used. Specifically, organic metal complexes such as bis[2-(2'-benzo[4,5-α]thienyl)pyridine-N,C3']iridium(III)acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinoline-N,C2')iridium(III)acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrinplatinum(II) (abbreviation: PtOEP) can be cited.

[1000] In addition, rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviated as: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedione)(monophenanthroline)europium(III) (abbreviated as: Eu(DBM)3(Phen)), and tris[1-(2-thiophenoyl)-3,3,3-trifluoroacetonate](monophenanthroline)europium(III) (abbreviated as: Eu(TTA)3(Phen)) can be used as phosphorescent materials because the luminescence comes from rare earth metal ions (electron transitions between different multiplicities).

[1001] In one embodiment of the present invention, the light-emitting layer preferably contains a phosphorescent light-emitting material (phosphorescent dopant material).

[1002] Host material of the light-emitting layer

[1003] The light-emitting layer may be a structure in which the above-mentioned dopant material is dispersed in another material (host material). It is preferable to use a material having a higher lowest unoccupied molecular orbital level (LUMO level) and a lower highest occupied molecular orbital level (HOMO level) than the dopant material.

[1004] As the main material, for example,

[1005] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes,

[1006] (2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives,

[1007] (3) Carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or Derivatives and other condensed aromatic compounds,

[1008] (4) Aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives.

[1009] For example, metal complexes such as tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-hydroxyquinoline)aluminum(III) (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium(II) (abbreviated as BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO), and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ) can be used;

[1010] 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2',2"-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP) and other heterocyclic compounds;

[1011] 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviated as DPPA), 9,10-di(2-naphthyl)anthracene (abbreviated as DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviated as : t-BuDNA), 9,9'-bianthracene (abbreviated as: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviated as: DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviated as: DPNS2), 3,3',3"-(benzene-1,3,5-triyl)tripyrene (abbreviated as: TPB3), 9,10-diphenylanthracene (abbreviated as: DPAnth), 6,12-dimethoxy-5,11-diphenyl Equi-fused aromatic compounds; and

[1012] N,N-diphenyl-9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole-3-amine (abbreviated as: CzA1PA), 4-(10-phenyl-9-anthracenyl)triphenylamine (abbreviated as: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole-3-amine (abbreviated as: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthracenyl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviated as: PCAPBA), N-(9,10-diphenyl-2-anthracenyl)-N,9-diphenyl- Aromatic amine compounds such as 9H-carbazole-3-amine (abbreviation: 2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). Two or more types of the host material may be used.

[1013] In particular, in the case of a blue fluorescent element, it is preferable to use the anthracene compound described below as a host material.

[1014] [Chemical formula 127]

[1015]

[1016] [Chemical formula 128]

[1017]

[1018] [Chemical formula 129]

[1019]

[1020] Electron transport layer

[1021] The electron transport layer is a layer containing a material with a high electron transport property (electron transport material), and is formed between the light emitting layer and the cathode, or, if an electron injection layer exists, between the electron injection layer and the light emitting layer.

[1022] The electron transport layer may be a single-layer structure or a multilayer structure comprising more than two layers. For example, the electron transport layer may be a two-layer structure comprising a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one embodiment of the present invention, the electron transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, or the electron transport layer closest to the anode in the multilayer structure, such as the first electron transport layer of the two-layer structure, is preferably adjacent to the light-emitting layer. In another embodiment of the present invention, a hole blocking layer described later may be sandwiched between the electron transport layer of the single-layer structure and the light-emitting layer, or between the electron transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer.

[1023] The electron transport layer may be, for example,

[1024] (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes,

[1025] (2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives,

[1026] (3)Polymer compounds.

[1027] Examples of the metal complex include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinolato)beryllium (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenol)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviation: ZnBTZ).

[1028] Examples of the heteroaromatic compound include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), and 4,4′-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs).

[1029] Examples of the polymer compound include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).

[1030] The above materials are 10 -6 cm 2 It should be noted that materials other than the above may be used for the electron transport layer as long as the electron transport property is higher than the hole transport property.

[1031] Electron injection layer

[1032] The electron injection layer is a layer containing a material with high electron injection. The electron injection layer can use alkali metals such as lithium (Li), cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), strontium (Sr), rare earth metals such as europium (Eu), ytterbium (Yb), and compounds containing these metals. As such a compound, for example: alkali metal oxides, alkali metal halides, organic complexes containing alkali metals, alkaline earth metal oxides, alkaline earth metal halides, organic complexes containing alkaline earth metals, rare earth metal oxides, rare earth metal halides, and organic complexes containing rare earth metals. In addition, a variety of these compounds can also be used in combination.

[1033] Alternatively, a material having an electron transport property and containing an alkali metal, an alkaline earth metal or a compound thereof may be used, specifically, a material containing magnesium (Mg) in Alq, etc. In this case, electron injection from the cathode can be performed more efficiently.

[1034] Alternatively, the electron injection layer may also use a composite material mixed with an organic compound and an electron donor (donor). Such a composite material has excellent electron injection and electron transport properties because the organic compound accepts electrons from the electron donor. At this time, as an organic compound, it is preferably a material with excellent transmission of the accepted electrons. Specifically, for example, the material (metal complex, heteroaromatic compound, etc.) constituting the electron transport layer described above can be used. As an electron donor, any material that exhibits electron donating properties to an organic compound can be used. Specifically, alkali metals, alkaline earth metals and rare earth metals are preferred, and lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. can be cited. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, and lithium oxide, calcium oxide, barium oxide, etc. can be cited. In addition, a Lewis base such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviated as: TTF) can also be used.

[1035] cathode

[1036] The cathode preferably uses a metal, alloy, conductive compound, and mixtures thereof with a small work function (specifically, less than 3.8 eV). Specific examples of such cathode materials include elements belonging to the first or second group of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys thereof (e.g., MgAg, AlLi), and rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys thereof.

[1037] It should be noted that when an alkali metal, an alkaline earth metal, or an alloy containing them is used to form the cathode, a vacuum deposition method or a sputtering method may be used. In addition, when a silver paste or the like is used, a coating method or an inkjet method may be used.

[1038] It should be noted that, by providing an electron injection layer, a cathode can be formed using various conductive materials such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the size of the work function. These conductive materials can be formed into films using sputtering, inkjet, spin coating, etc.

[1039] Insulation layer

[1040] Organic EL elements are prone to pixel defects due to leakage and short circuits due to the application of an electric field to ultra-thin films. To prevent this, an insulating layer formed of an insulating thin film layer may be inserted between a pair of electrodes.

[1041] Examples of materials that can be used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. It should be noted that mixtures and laminates thereof may also be used.

[1042] Spacer

[1043] For example, when a fluorescent light-emitting layer and a phosphorescent light-emitting layer are stacked, the spacer layer is a layer disposed between the fluorescent light-emitting layer and the phosphorescent light-emitting layer for the purpose of preventing the excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer or adjusting the carrier balance. In addition, the spacer layer may also be disposed between a plurality of phosphorescent light-emitting layers.

[1044] Since the spacer layer is disposed between the light-emitting layers, it is preferably a material having both electron transport and hole transport properties. In addition, in order to prevent the diffusion of triplet energy in the adjacent phosphorescent light-emitting layer, the triplet energy is preferably above 2.6 eV. As the material for the spacer layer, the same material as the material for the hole transport layer mentioned above can be cited.

[1045] Barrier layer

[1046] Blocking layers such as an electron blocking layer, a hole blocking layer, and an exciton blocking layer may also be provided adjacent to the light-emitting layer. An electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer, and a hole blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron transport layer. The exciton blocking layer has the function of preventing excitons generated in the light-emitting layer from diffusing to the surrounding layers and confining the excitons in the light-emitting layer.

[1047] Each layer of the organic EL element can be formed by a conventionally known vapor deposition method, coating method, etc. For example, it can be formed by a vapor deposition method such as a vacuum vapor deposition method, a molecular beam vapor deposition method (MBE method), or a known method based on a coating method such as a dip coating method, a spin coating method, a casting method, a rod coating method, a roll coating method, etc. using a solution of a layer-forming compound.

[1048] The thickness of each layer is not particularly limited. Generally, if the thickness is too thin, defects such as pinholes are easily generated, while if it is too thick, a high driving voltage is required and the efficiency is deteriorated. Therefore, it is usually 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm.

[1049] In the organic EL element having a two-layer or three-layer hole transport layer of the present invention, the total thickness of the first hole transport layer and the second hole transport layer is preferably 30 nm to 150 nm, more preferably 40 nm to 130 nm.

[1050] In one embodiment of the present invention, the thickness of the second hole transport layer of the two-layer structure or three-layer structure is preferably 5 nm or more, more preferably 20 nm or more, further preferably 25 nm or more, particularly preferably 35 nm or more, and preferably 100 nm or less.

[1051] In one embodiment of the present invention, the thickness of the hole transport layer adjacent to the light-emitting layer is preferably 5 nm or more, more preferably 10 nm or more, and is preferably 20 nm or less, more preferably 17 nm or less.

[1052] In another embodiment of the present invention, the thickness of the hole transport layer adjacent to the light-emitting layer is preferably 5 nm or more, more preferably 20 nm or more, further preferably 25 nm or more, particularly preferably 30 nm or more, and preferably 100 nm or less.

[1053] In addition, in the organic EL element having a hole transport layer with a two-layer structure or a three-layer structure according to the present invention, the ratio of the film thickness D2 of the second hole transport layer to the film thickness D1 of the first hole transport layer is preferably 0.3 < D2 / D1 < 4.0, more preferably 0.5 < D2 / D1 < 3.5, and further preferably 0.75 < D2 / D1 < 3.0.

[1054] As a preferred embodiment of the organic EL element of the present invention, for example, there can be cited

[1055] (1) An organic EL element having a hole transport layer composed of two layers

[1056] · A first embodiment in which the second hole transport layer contains the inventive compound and the first hole transport layer does not contain the inventive compound;

[1057] · A second embodiment in which both the first hole transport layer and the second hole transport layer contain the inventive compound;

[1058] · A third embodiment in which the first hole transport layer contains the inventive compound and the second hole transport layer does not contain the inventive compound;

[1059] (2) An organic EL element having a hole transport layer composed of three layers

[1060] · A fourth embodiment in which the first hole transport layer contains the inventive compound and the second and third hole transport layers do not contain the inventive compound;

[1061] · A fifth embodiment in which the second hole transport layer contains the inventive compound and the first and third hole transport layers do not contain the inventive compound;

[1062] · A sixth embodiment in which the third hole transport layer contains the inventive compound and the first and second hole transport layers do not contain the inventive compound;

[1063] · A seventh embodiment in which the first and second hole transport layers contain the inventive compound and the third hole transport layer does not contain the inventive compound;

[1064] · An eighth embodiment in which the first and third hole transport layers contain the inventive compound and the second hole transport layer does not contain the inventive compound;

[1065] · A tenth embodiment in which the second and third hole transport layers contain the inventive compound and the first hole transport layer does not contain the inventive compound;

[1066] · A tenth embodiment in which the first to third hole transport layers all contain the inventive compound; and so on.

[1067] The organic EL element can be used in display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and electronic devices such as lighting and light-emitting devices for vehicle lamps.

[1068] Example

[1069] Hereinafter, the present invention will be described in further detail using examples, but the present invention is not limited to the following examples.

[1070] Invention compound used in the manufacture of the organic EL device of Example 1

[1071] [Chemical formula 130]

[1072]

[1073] Comparative compound used in the manufacture of the organic EL device of Comparative Example 1

[1074] [Chemical formula 131]

[1075]

[1076] Other compounds used in the manufacture of the organic EL devices of Example 1 and Comparative Example 1

[1077] [Chemical formula 132]

[1078]

[1079] Fabrication of organic EL elements (I)

[1080] Example 1

[1081] A 25 mm×75 mm×1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.

[1082] The cleaned glass substrate with a transparent electrode was mounted on a substrate holder of a vacuum evaporation device, and compound 1 and compound HA were co-evaporated on the surface of the side where the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 10 nm. The mass ratio of compound 1 to compound HA (compound 1:HA) was 97:3.

[1083] Next, Compound 1 was deposited on the hole injection layer to form a first hole transport layer having a film thickness of 75 nm.

[1084] Next, compound HT2 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 15 nm.

[1085] Next, a 20 nm thick BH (host material): BD1 (dopant material) film was formed on the second hole transport layer. The BH:BD1 film functions as a light-emitting layer. The BH [chemical compound BH1 and BH2 (both host materials)] contained in the light-emitting layer is 1:1 in mass ratio, and the concentration of BD1 is 2 mass % relative to the entire light-emitting layer.

[1086] Next, compound ET1 was vapor-deposited on the light-emitting layer to form a first electron transport layer having a thickness of 3 nm.

[1087] Next, compound ET2 and Liq were co-evaporated on the first electron transport layer to form a second electron transport layer with a film thickness of 30 nm. The mass ratio of compound ET2 to Liq (ET2:Liq) was 67:33.

[1088] Next, LiF and Yb were co-evaporated on the second electron transport layer to form an electron injecting electrode with a film thickness of 1 nm. The mass ratio of LiF to Yb (LiF:Yb) was 50:50.

[1089] Then, metal Al was vapor-deposited on the electron injecting electrode to form a metal cathode having a film thickness of 50 nm.

[1090] The layer structure of the organic EL device (I) of Example 1 obtained in this manner is shown below.

[1091] ITO (130) / Compound 1: HA = 97: 3 (10) / Compound 1 (75) / HT2 (15) / BH1: BH2: BD = 50: 50: 2 (25) / ET1 (3) / ET2: Liq = 67: 33 (30) / LiF: Yb = 50: 50 (1) / Al (50)

[1092] In the above-mentioned layer constitution, the numbers in parentheses are film thickness (nm), and the ratios are by mass ratio.

[1093] Determination of External Quantum Efficiency (EQE)

[1094] The obtained organic EL device (I) was subjected to a current density of 10 mA / cm at room temperature. 2 The device was driven with a direct current constant current. The brightness was measured using a brightness meter (Spectroradiometer CS-1000 manufactured by Minolta Corporation), and the external quantum efficiency (%) was calculated based on the results. The results are shown in Table 1.

[1095] Comparative Example 1

[1096] An organic EL device (I) was prepared in the same manner as in Example 1 except that the materials of the hole injection layer and the first hole transport layer were changed to the compounds shown in Table 1 below instead of Compound 1, and the external quantum efficiency (EQE) was measured.

[1097] [Table 1]

[1098] Table 1

[1099]

[1100] As is clear from the results in Table 1, the organic EL device including the compound of the invention (Compound 1) has a more excellent external quantum efficiency than the organic EL device including the comparative compound 1.

[1101] Invention compounds used in the production of organic EL devices (II) of Examples 2 and 3

[1102] [Chemical formula 133]

[1103]

[1104] Comparative compounds used in the manufacture of organic EL devices (II) of Comparative Examples 2 and 3

[1105] [Chemical formula 134]

[1106]

[1107] Other compounds used in the production of organic EL devices (II)

[1108] [Chemical formula 135]

[1109]

[1110] Fabrication of organic EL elements (II)

[1111] Example 2

[1112] A 25 mm×75 mm×1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.

[1113] The cleaned glass substrate with a transparent electrode was mounted on a substrate holder of a vacuum evaporation device, and compound 2 and compound HA were co-evaporated on the surface of the side where the transparent electrode was formed in a manner covering the transparent electrode to form a hole injection layer with a thickness of 10 nm. The mass ratio of compound 2 to compound HA (compound 2:HA) was 97:3.

[1114] Next, Compound 2 was deposited on the hole injection layer to form a first hole transport layer having a film thickness of 80 nm.

[1115] Next, compound HT3 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 10 nm.

[1116] Next, compound BH3 (host material) and compound BD2 (dopant material) were co-evaporated on the second hole transport layer to form a 25 nm thick light emitting layer. The mass ratio of compound BH3 to compound BD2 (BH3:BD2) was 96:4.

[1117] Next, compound ET3 was vapor-deposited on the light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[1118] Next, compound ET4 and Liq were co-evaporated on the first electron transport layer to form a second electron transport layer with a film thickness of 20 nm. The mass ratio of compound ET4 to Liq (ET4:Liq) was 50:50.

[1119] Next, LiF was vapor-deposited on the second electron transport layer to form an electron injecting electrode with a film thickness of 1 nm.

[1120] Then, metal Al was vapor-deposited on the electron injecting electrode to form a metal cathode having a film thickness of 50 nm.

[1121] The layer structure of the organic EL device (II) of Example 2 obtained in this manner is shown below.

[1122] ITO (130) / Compound 2: HA = 97: 3 (10) / Compound 2 (80) / HT3 (10) / BH3:

[1123] BD2=96:4(25) / ET3(5) / ET4:Liq=50:50(20) / LiF(1) / A1(50)

[1124] In the above-mentioned layer constitution, the numbers in parentheses are film thickness (nm), and the ratios are by mass ratio.

[1125] Determination of 95% lifespan

[1126] The obtained organic EL device (II) was subjected to a current density of 50 mA / cm 2 The battery was driven by a direct current constant current, and the time (h) until the luminance decreased to 95% of the initial luminance was measured, and this time was defined as the 95% lifespan (LT95).

[1127] Example 3, and Comparative Examples 2 and 3

[1128] An organic EL device (II) was prepared in the same manner as in Example 2 except that the materials for the hole injection layer and the first hole transport layer were changed to the compounds shown in Table 2 below instead of Compound 2, and the 95% lifetime was measured.

[1129] [Table 2]

[1130] Table 2

[1131]

[1132] From the results in Table 2, it can be seen that the organic EL elements containing the inventive compounds (Compounds 2 and 3) have a longer life than the organic EL elements containing the comparative compounds 2 and 3.

[1133] Inventive compounds used in the production of organic EL devices (III) of Examples 4 and 5

[1134] [Chemical formula 136]

[1135]

[1136] Comparative compound used in the preparation of the organic EL device (III) of Comparative Example 4 [Chemical Formula 137]

[1137]

[1138] Other compounds used in the production of organic EL devices (III)

[1139] [Chemical formula 138]

[1140]

[1141] Fabrication of organic EL elements (III)

[1142] Example 4

[1143] A 25 mm×75 mm×1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.

[1144] The cleaned glass substrate with a transparent electrode was mounted on a substrate holder of a vacuum evaporation device, and compound 4 and compound HA were co-evaporated on the surface of the side where the transparent electrode was formed in a manner covering the transparent electrode to form a hole injection layer with a thickness of 10 nm. The mass ratio of compound 4 to compound HA (compound 4:HA) was 97:3.

[1145] Next, Compound 4 was deposited on the hole injection layer to form a first hole transport layer having a film thickness of 75 nm.

[1146] Next, compound HT4 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 15 nm.

[1147] Next, a 20 nm thick BH (host material): BD3 (dopant material) film was formed on the second hole transport layer. The BH:BD3 film functions as a light-emitting layer. The BH [chemical compound BH1 and BH2 (both host materials)] contained in the light-emitting layer has a mass ratio of 3:2, and the concentration of BD3 is 2 mass % relative to the entire light-emitting layer.

[1148] Next, compound ET5 was vapor-deposited on the light-emitting layer to form a first electron transport layer with a film thickness of 3 nm.

[1149] Next, compound ET2 and Liq were co-evaporated on the first electron transport layer to form a second electron transport layer with a film thickness of 30 nm. The mass ratio of compound ET2 to Liq (ET2:Liq) was 50:50.

[1150] Next, LiF and Yb were co-evaporated on the second electron transport layer to form an electron injecting electrode with a film thickness of 1 nm. The mass ratio of LiF to Yb (LiF:Yb) was 50:50.

[1151] Then, metal Al was vapor-deposited on the electron injecting electrode to form a metal cathode having a film thickness of 50 nm.

[1152] The layer structure of the organic EL device (III) of Example 4 obtained in this manner is shown below.

[1153] ITO (130) / Compound 4: HA = 97: 3 (10) / Compound 4 (75) / HT4 (15) / BH1: BH2: BD3 = 60: 40: 2 (20) / ET5 (3) / ET2: Liq = 50: 50 (30) / LiF: Yb = 50: 50 (1) / Al (50)

[1154] In the above-mentioned layer constitution, the numbers in parentheses are film thickness (nm), and the ratios are by mass ratio.

[1155] Determination of External Quantum Efficiency (EQE)

[1156] The external quantum efficiency (%) of the obtained organic EL device (III) was determined in the same manner as in Example 1. The results are shown in Table 3.

[1157] Example 5 and Comparative Example 4

[1158] An organic EL device (III) was prepared in the same manner as in Example 4 except that the materials for the hole injection layer and the first hole transport layer were changed to the compounds shown in Table 3 below instead of Compound 4, and the external quantum efficiency (EQE) was measured.

[1159] [Table 3]

[1160] Table 3

[1161]

[1162] As is clear from the results in Table 3, the organic EL device including the inventive compounds (Compounds 4 and 5) has a more excellent external quantum efficiency than the organic EL device including the comparative compound 4.

[1163] Invention compounds used in the production of organic EL devices (IV) of Examples 6 and 7

[1164] [Chemical formula 139]

[1165]

[1166] Comparative compound used in the preparation of the organic EL device (IV) of Comparative Example 5

[1167] [Chemical formula 1401

[1168]

[1169] Other compounds used in the production of organic EL devices (IV)

[1170] [Chemical formula 141]

[1171]

[1172] Fabrication of organic EL elements (IV)

[1173] Example 6

[1174] A 25 mm×75 mm×1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.

[1175] The cleaned glass substrate with the transparent electrode was mounted on a substrate holder of a vacuum evaporation device, and compound HT5 and compound HA were co-evaporated on the surface of the side where the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT5 to compound HA (compound HT5:HA) was 97:3.

[1176] Next, compound HT5 was vapor-deposited on the hole injection layer to form a first hole transport layer having a film thickness of 40 nm.

[1177] Next, Compound 1 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 40 nm.

[1178] Next, compound HT3 was vapor-deposited on the second hole transport layer to form a third hole transport layer with a film thickness of 5 nm.

[1179] Next, compound BH4 (host material) and compound BD1 (dopant material) were co-evaporated on the third hole transport layer to form a 20 nm thick light emitting layer. The mass ratio of compound BH4 to compound BD1 (BH4:BD1) was 99:1.

[1180] Next, compound ET3 was vapor-deposited on the light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[1181] Next, compound ET6 and Liq were co-evaporated 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 ET6 to Liq (ET6:Liq) was 50:50.

[1182] Next, Yb was vapor-deposited on the second electron transport layer to form an electron injecting electrode with a film thickness of 1 nm.

[1183] Then, metal Al was vapor-deposited on the electron injecting electrode to form a metal cathode having a film thickness of 50 nm.

[1184] The layer structure of the organic EL device (IV) of Example 6 obtained in this manner is shown below.

[1185] ITO(130) / HT5:HA=97:3(10) / HT5(40) / Compound 1(40) / HT3(5) / BH4:

[1186] BD1=99:1(20) / ET3(5) / ET6:Liq=50:50(25) / Yb(1) / A1(50)

[1187] In the above-mentioned layer constitution, the numbers in parentheses are film thickness (nm), and the ratios are by mass ratio.

[1188] Determination of External Quantum Efficiency (EQE)

[1189] The external quantum efficiency (%) of the obtained organic EL device (IV) was determined in the same manner as in Example 1. Table 4 shows the results.

[1190] Example 7 and Comparative Example 5

[1191] An organic EL device (IV) was prepared in the same manner as in Example 6 except that the second hole transport layer material was changed to a compound shown in Table 4 below instead of Compound 1, and the external quantum efficiency (EQE) was measured.

[1192] [Table 4]

[1193] Table 4

[1194]

[1195] As is clear from the results in Table 4, the organic EL device including the inventive compounds (Compounds 1 and 6) has a more excellent external quantum efficiency than the organic EL device including the comparative compound 5.

[1196] Inventive compounds synthesized in the synthesis examples

[1197] [Chemical formula 142]

[1198]

[1199] Intermediate Synthesis Example 1: Synthesis of Intermediate A

[1200] [Chemical formula 143]

[1201]

[1202] Under an argon atmosphere, a mixture of 29.2 g (87.6 mmol) of 2-amino-9,9-diphenylfluorene, 28.8 g (85.9 mmol) of 2-bromo-9-methyl-9-phenyl-9H-fluorene, 1.57 g (1.71 mmol) of tris(dibenzylideneacetone)dipalladium(0), 2.14 g (3.44 mmol) of BINAP, 20.6 g (214 mmol) of sodium tert-butoxide, and 580 mL of xylene was stirred at 120°C for 5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 15.1 g of intermediate A as a white solid. The yield was 30%.

[1203] Intermediate Synthesis Example 2: Synthesis of Intermediate B

[1204] [Chemical formula 144]

[1205]

[1206] Under argon atmosphere, a mixture of 6.77 g (40.0 mmol) of 2-aminobiphenyl, 13.4 g (40.0 mmol) of 2-bromo-9-methyl-9-phenyl-9H-fluorene, 0.730 g (0.797 mmol) of tris(dibenzylideneacetone)dipalladium(0), 1.00 g (1.61 mmol) of BINAP, 4.23 g (44.0 mmol) of sodium tert-butoxide, and 200 mL of toluene was stirred at 90° C. for 7 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 16.6 g of intermediate B as a white solid. The yield was 97%.

[1207] Synthesis Example 1: Synthesis of Compound 1

[1208] [Chemical formula 145]

[1209]

[1210] Under argon atmosphere, a mixture of 7.28 g (15.0 mmol) of N-[1,1'-biphenyl]-2-yl-9,9-diphenyl-9H-fluorene-2-amine, 6.03 g (18.0 mmol) of 2-bromo-9-methyl-9-phenyl-9H-fluorene, 0.275 g (0.30 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.348 g (1.20 mmol) of tri-tert-butylphosphonium tetrafluoroborate, 2.02 g (21.0 mmol) of sodium tert-butoxide, and 150 mL of xylene was stirred at 120°C for 7 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 5.20 g of a white solid. The yield was 47%.

[1211] The obtained substance was subjected to mass spectrometry analysis, which revealed compound 1 with a relative molecular weight of 739.96 and m / e=740.

[1212] Synthesis Example 2: Synthesis of Compound 2

[1213] [Chemical formula 146]

[1214]

[1215] In Synthesis Example 1, intermediate B was used instead of N-[1,1′-biphenyl]-2-yl-9,9-diphenyl-9H-fluoren-2-amine, and toluene was used instead of xylene, and a white solid was obtained by the same operation with a yield of 46%.

[1216] The obtained substance was analyzed by mass spectrometry and was found to be Compound 2 (relative molecular weight 677.89, m / e=678).

[1217] Synthesis Example 3: Synthesis of Compound 3

[1218] [Chemical formula 147]

[1219]

[1220] In Synthesis Example 1, Intermediate A was used instead of N-[1,1′-biphenyl]-2-yl-9,9-diphenyl-9H-fluoren-2-amine, and a white solid was obtained by the same operation. The yield was 44%.

[1221] The obtained substance was analyzed by mass spectrometry and was found to be Compound 3 (m / e=842, relative molecular weight 842.10).

[1222] Synthesis Example 4: Synthesis of Compound 4

[1223] [Chemical formula 148]

[1224]

[1225] In Synthesis Example 1, a white solid was obtained by the same operation except that Intermediate A was used instead of N-[1,1′-biphenyl]-2-yl-9,9-diphenyl-9H-fluoren-2-amine and 2-bromodibenzofuran was used instead of 2-bromo-9-methyl-9-phenyl-9H-fluorene. The yield was 39%.

[1226] The obtained substance was analyzed by mass spectrometry and was found to be Compound 4 (m / e=754, relative molecular weight: 753.95).

[1227] Synthesis Example 5: Synthesis of Compound 5

[1228] [Chemical formula 149]

[1229]

[1230] In Synthesis Example 1, intermediate A was used instead of N-[1,1′-biphenyl]-2-yl-9,9-diphenyl-9H-fluoren-2-amine, and 2-bromodibenzothiophene was used instead of 2-bromo-9-methyl-9-phenyl-9H-fluorene, and a white solid was obtained by the same operation with a yield of 43%.

[1231] The obtained substance was analyzed by mass spectrometry and was found to be Compound 5 (relative molecular weight 770.01, m / e=770).

[1232] Synthesis Example 6: Synthesis of Compound 6

[1233] [Chemical formula 150]

[1234]

[1235] In Synthesis Example 1, intermediate A was used instead of N-[1,1′-biphenyl]-2-yl-9,9-diphenyl-9H-fluoren-2-amine, and 4-bromodibenzofuran was used instead of 2-bromo-9-methyl-9-phenyl-9H-fluorene, and a white solid was obtained by the same operation with a yield of 48%.

[1236] The obtained substance was analyzed by mass spectrometry and was found to be Compound 6 (relative molecular weight 753.95, m / e=754).

[1237] Explanation of symbols

[1238] 1, 11, 12 Organic EL elements

[1239] 2 substrate

[1240] 3 Anode

[1241] 4 Cathode

[1242] 5. Luminous layer

[1243] 6 Hole transport region (hole transport layer)

[1244] 6a Hole injection layer

[1245] 6b 1st hole transport layer

[1246] 6c Second hole transport layer

[1247] 6d Third hole transport layer

[1248] 7 Electron transport region (electron transport layer)

[1249] 7a 1st electron transport layer

[1250] 7b Second electron transport layer

[1251] 10, 20, 30 light units

Claims

1. A compound represented by the following formula (1), In formula (1), R 1 and R 2 One of them is methyl and the other is unsubstituted phenyl, R 1 With R 2 They are not bonded to each other and thus do not form a ring structure. R 3 and R 4 One of them is methyl and the other is unsubstituted phenyl, R 3 With R 4 They are not bonded to each other and thus do not form a ring structure. R 11 ~R 18 and R 21 ~R 28 is a hydrogen atom, in, Selected from R 12 and R 17 One of them is a single bond to *a, Selected from R 22 and R 27 One of them is a single bond to *b, L 1 and L 2 are each independently a single bond, or a substituted or unsubstituted phenylene group, Ar 1 is a group represented by any one of formulae (1-1) to (1-6), In formulas (1-1) to (1-6), R 31 ~R 35 , R 41 ~R 46 , R 51 ~R 55 , R 61 ~R 68 , R 71 ~R 82 , R 91 ~R 100 , R 101 ~R 108 , R 111 ~R 116 , R 121 ~R 125 and R 131 ~R 135 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, X 1 is an oxygen atom, a sulfur atom, or CR a R b , R a and R b are each independently a hydrogen atom, a methyl group, or a substituted or unsubstituted phenyl group, R a With R b are optionally bonded to each other to form a substituted or unsubstituted ring, in, Selected from R 31 ~R 35 One of them is a single bond to *c, Selected from R 41 ~R 46 One of them is a single bond bonded to *d, selected from R 41 ~R 46 The other one in is a single bond bonded to *e, Selected from R 65 ~R 68 One of them is a single bond to *f, Selected from R 79 ~R 82 One of them is a single bond to *g, Selected from R 91 and R 97 ~R 100 One of them is a single bond to *h, Selected from R 105 ~R 108 One of them is a single bond bonded to *i, Selected from R 111 ~R 116 One of them is a single bond bonded to *j, selected from R 111 ~R 116 The other one of them is a single bond bonded to *k, selected from R 111 ~R 116 The other one in is a single bond bonded to *1, is selected from R which is not a single bond 31 ~R 35 Two adjacent R selected from R which are not any of the single bonds 41 ~R 46 Two adjacent ones in R 51 ~R 55 Two adjacent R selected from R which are not the single bonds 61 ~R 68 Two adjacent R selected from R which are not the single bonds 71 ~R 82 Two adjacent R selected from R which are not the single bonds 91 ~R 100 Two adjacent R selected from R which are not the single bonds 101 ~R 108 Two adjacent R selected from R which are not any of the single bonds 111 ~R 116 Two adjacent ones in R 121 ~R 125 Two adjacent ones in R 131 ~R 135 The two adjacent ones in are not bonded to each other and thus do not form a ring structure. The benzene ring A1 and the benzene ring B1, the benzene ring A1 and the benzene ring C1, the benzene ring A1 and the benzene ring D1, the benzene ring A1 and the benzene ring E1, the benzene ring A1 and the benzene ring F1, the benzene ring B1 and the benzene ring C1, the benzene ring D1 and the benzene ring E1, and the benzene ring D1 and the benzene ring F1 are not cross-linked, ** indicates the bonding position with the central nitrogen atom N, The group represented by the formula (1-2) is a substituted or unsubstituted group selected from the following formulas, In formula (1-1), m is 0 and n is 1, or m is 1 and n is 1, In formulas (1-3) to (1-6), m is 0 or 1, n is 0 or 1, In formula (1-1), *c is bonded to the central nitrogen atom N, In formulas (1-3) to (1-6), when m is 0, *c is bonded to the central nitrogen atom N, Formula (1-1) excludes p-biphenyl.

2. The compound according to claim 1, wherein L 1 and L 2 For a single key.

3. The compound according to claim 1 or 2, wherein Ar 1 It is a group represented by any one of formulae (1-1), (1-2), (1-5) and (1-6).

4. The compound according to any one of claims 1 to 3, wherein R 31 ~R 35 , R 41 ~R 46 , R 51 ~R 55 , R 61 ~R 68 , R 71 ~R 82 , R 91 ~R 100 , R 101 ~R 108 , R 111 ~R 116 , R 121 ~R 125 and R 131 ~R 135 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

5. The compound according to any one of claims 1 to 4, wherein R is not a single bond to *c 31 ~R 35 All are hydrogen atoms.

6. The compound according to any one of claims 1 to 5, wherein R is not a single bond bonded to *d and is not a single bond bonded to *e 41 ~R 46 All are hydrogen atoms.

7. The compound according to any one of claims 1 to 6, wherein R 51 ~R 55 All are hydrogen atoms.

8. The compound according to any one of claims 1 to 7, wherein R 61 ~R 64 and R which is not a single bond to *f 65 ~R 68 All are hydrogen atoms.

9. The compound according to any one of claims 1 to 8, wherein R 71 ~R 78 and R which is not a single bond to *g 79 ~R 82 All are hydrogen atoms.

10. The compound according to any one of claims 1 to 9, wherein R 92 ~R 96 , and R which is not a single bond bonded to *h 91 and R 97 ~R 100 All are hydrogen atoms.

11. The compound according to any one of claims 1 to 10, wherein R 101 ~R 104 and R which is not a single bond to *i 105 ~R 108 All are hydrogen atoms.

12. The compound according to any one of claims 1 to 11, wherein R is not a single bond bonded to *j, is not a single bond bonded to *k, and is not a single bond bonded to *1 111 ~R 116 , R 121 ~R 125 and R 131 ~R 135 All are hydrogen atoms.

13. The compound according to any one of claims 1 to 12, wherein The compound represented by the formula (1) contains at least one deuterium atom. 14 . A material for an organic electroluminescent device, comprising the compound according to claim 1 . 15 . An organic electroluminescent device comprising a cathode, an anode, and an organic layer located between the cathode and the anode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer includes the compound according to claim 1 .

16. The organic electroluminescent element according to claim 15, wherein: The organic layer includes a hole transport region between the anode and the light emitting layer, and the hole transport region includes the compound.

17. The organic electroluminescent element according to claim 16, wherein: The hole transport region includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side. The first hole transport layer contains the compound, or the second hole transport layer contains the compound, or both the first hole transport layer and the second hole transport layer contain the compound.

18. The organic electroluminescent element according to claim 17, wherein: The first hole transport layer includes the compound.

19. The organic electroluminescent element according to claim 17 or 18, wherein: The second hole transport layer is adjacent to the light emitting layer.

20. The organic electroluminescent element according to claim 16, wherein The hole transport region includes a first hole transport layer, a second hole transport layer, and a third hole transport layer in order from the anode side. Only one layer selected from the first to third hole transport layers contains the compound, only two layers selected from the first to third hole transport layers contain the compound, or all of the first to third hole transport layers contain the compound.

21. The organic electroluminescent element according to claim 20, wherein: The light-emitting layer is directly in contact with the third hole transport layer.

22. The organic electroluminescent element according to any one of claims 15 to 21, wherein The light-emitting layer includes a fluorescent dopant material.

23. The organic electroluminescent element according to any one of claims 15 to 21, wherein The light-emitting layer includes a phosphorescent dopant material. 24 . An electronic device comprising the organic electroluminescent element according to claim 15 .

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