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

Abstract

The present invention provides compounds that further improve the performance of organic EL elements, organic electroluminescent elements with improved element performance, and electronic devices containing such organic electroluminescent elements. [Solution] A compound represented by the following formula (2), an organic electroluminescent element containing the compound, and an electronic device containing the organic electroluminescent element. JPEG2026097877000158.jpg62147

Description

[Technical Field]

[0001] The present invention relates to compounds, materials for organic electroluminescent elements, organic electroluminescent elements, and electronic devices including said organic electroluminescent elements. [Background technology]

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

[0003] Patent documents 1 to 4 disclose compounds to be used as materials for organic electroluminescent devices. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] U.S. Patent No. 10840455 [Patent Document 2] U.S. Patent Application Publication No. 2019 / 0148650 [Patent Document 3] International Publication No. 2019 / 139419 [Patent Document 4] International Publication No. 2014 / 034795 [Overview of the project] [Problems that the invention aims to solve]

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

[0006] The present invention has been made to solve the above problems, and an object thereof is to provide a compound that can further improve the performance of an organic EL element, an organic EL element having improved element performance, and an electronic device including such an organic EL element.

Means for Solving the Problems

[0007] As a result of intensive studies on the performance of organic EL elements containing the compounds described in Patent Documents 1 to 4, the present inventors have found that the performance of organic EL elements containing the compound represented by the following formula (1) and the compound represented by the following formula (2) is further improved.

[0008] [[ID=I5]]In one aspect, the present invention provides a compound represented by the following formula (1).

Chemical Formula

[0009] In formula (1), ]>R , 4 , , 4 , 18 , 28 , 18 , 11 , 3 , , 3 , , 11 , 21 and R 2 One of them is a methyl group and the other is an unsubstituted phenyl group, R 1 and R 2 do not bond to each other and thus do not form a ring structure. R 3 and R 4 One of them is a methyl group and the other is an unsubstituted phenyl group, R 3 and R 4 do not bond to each other and thus do not form a ring structure. R 11 ~R 18 and R 21 ~R 28 are hydrogen atoms. However, R 11 ~R 18One of the selected options is a single bond that connects to *a, R 21 ~R 28 One of the options selected is a single bond that connects to *b. L 1 and L 2 Each of these is independently a single bond, or a substituted or unsubstituted phenylene group. Ar 1 This is a base represented by any of the formulas (1-1) to (1-6). [ka]

[0010] 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 of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group. X 1 is an oxygen atom, a sulfur atom, or CR a R b And, R a and R b Each of these is independently a hydrogen atom, a methyl group, or a substituted or unsubstituted phenyl group, and R a and R bThese elements may combine with each other to form a substituted or unsubstituted ring. however, R 31 ~R 35 One of the selected options is a single bond that connects to *c, R 41 ~R 46 One of the selected options is a single bond that connects to *d, R 41 ~R 46 The other one chosen from is a single bond that joins *e, R 65 ~R 68 One of the selected options is a single bond that connects to *f, R 79 ~R 82 One of the selected options is a single bond that connects to *g, R 91 , and R 97 ~R 100 One of the selected options is a single bond that connects to *h, R 105 ~R 108 One of the options is a single join that connects to *i, R 111 ~R 116 One of the selected options is a single bond that connects to *j, R 111 ~R 116 Another one chosen from is a single bond that joins *k, R 111 ~R 116 Another one chosen from among them is a single bond that joins *l, R that is not a single bond 31 ~R 35 Two adjacent R bonds selected from the above, which are not any of the single bonds mentioned above. 41 ~R 46 Two adjacent elements are selected from R 51 ~R 55 Two adjacent R bonds selected from the single bond, which are not single bonds. 61 ~R 68 Two adjacent R bonds selected from the single bond, which are not single bonds. 71 ~R 82 Two adjacent R bonds selected from the single bond, which are not single bonds. 91 ~R 100Two adjacent ones selected from, the R that is not the single bond 101 ~R 108 Two adjacent ones selected from, the R that is not any single bond 111 ~R 116 Two adjacent ones selected from, R 121 ~R 125 Two adjacent ones selected from, R 131 ~R 135 Two adjacent ones selected from do not bond to each other, and thus do not form a ring structure 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 ** represents the bonding position to the central nitrogen atom N m is 0 or 1, n is 0 or 1 In formulas (1-1) and (1-2), when m is 0 and n is 0, *e bonds to the central nitrogen atom N, when m is 0 and n is 1, *c bonds to the central nitrogen atom N, when m is 1 and n is 0, *e bonds to one selected from 31 ~R 35 and is bonded to one selected from In formulas (1-3) to (1-6), when m is 0, *c bonds to the central nitrogen atom N R 12 or R 17 is a single bond that bonds to *a, and when R 22 or R 27 is a single bond that bonds to *b, formula (1-1) excludes the p-biphenyl group

[0011] In another aspect, the present invention provides a compound represented by the following formula (2).

Chemical formula

[0012] In formula (2), R 201 ~R 204 One selected from is a methyl group, R201 ~R 204 The other three selected from ~R are unsubstituted phenyl groups, R 201 and R 202 do not bond to each other, and thus do not form a ring structure, R 203 and R 204 do not bond to each other, and thus do not form a ring structure. R 211 ~R 218 and R 221 ~R 228 are hydrogen atoms. However, R 211 ~R 218 One selected from ~R is a single bond bonding to *m, R 221 ~R 228 One selected from ~R is a single bond bonding to *n. L 11 and L 12 are each independently a single bond or a substituted or unsubstituted phenylene group. Ar 11 is a group represented by any one of formulas (2-1) to (2-6).

Chemical formula

[0013] In formulas (2-1) to (2-6), 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 335Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group. X 2 is an oxygen atom, a sulfur atom, or CR c R d And, R c and R d Each is independently a hydrogen atom or a methyl group, and R c and R d They do not bond to each other and therefore do not form a ring structure. however, R 231 ~R 235 One of the selected options is a single bond that connects to *o, R 241 ~R 246 One of the selected options is a single bond that connects to *p, R 241 ~R 246 The other one chosen from is a single bond that joins *q, R 265 ~R 268 One of the options is a single bond that joins *r, R 279 ~R 282 One of the options is a single bond that joins *s, R 291 , and R 297 ~R 300 One of the selected options is a single bond that connects to *t. R 305 ~R 308 One of the options is a single bond that connects to *u, R 311 ~R 316 One of the selected options is a single bond that connects to *v, R 311 ~R 316 Another one selected from is a single bond that joins *w, R 311 ~R 316 Another one chosen from is a single join that connects to *x, R that is not a single bond 231 ~R 235 Two adjacent R bonds selected from the above, which are not any of the single bonds mentioned above. 241 ~R 246 Two adjacent elements are selected from R 251 ~R 255 Two adjacent R bonds selected from the single bond, which are not single bonds. 261 ~R 268 Two adjacent R bonds selected from the single bond, which are not single bonds. 271 ~R 282 Two adjacent R bonds selected from the single bond, which are not single bonds. 291 ~R 300 Two adjacent R bonds selected from the single bond, which are not single bonds. 301 ~R 308 Two adjacent R bonds selected from the above, which are not any of the single bonds mentioned above. 311 ~R 316 Two adjacent elements are selected from R 321 ~R 325 Two adjacent elements are selected from R 331 ~R 335 Two adjacent elements selected from these elements do not bond to each other and therefore do not form a ring structure. The benzene rings A2 and B2, A2 and C2, A2 and D2, A2 and E2, A2 and F2, B2 and C2, D2 and E2, and D2 and F2 are not crosslinked. *** indicates the bond position to the central nitrogen atom N. p is 0 or 1, q is 0 or 1, In equations (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 R 231 ~R 235 Combine with one selected from, In equations (2-3) to (2-6), when p is 0, *o is bonded to the central nitrogen atom N. In equation (2-5), X 2 CR c R dAnd when p is 0, L 11 and L 12 At least one of those selected is a substituted or unsubstituted phenylene group, In equation (2-5), X 2 When is an oxygen atom and p is 1, R 306 ~R 308 One of the options is a single bond that connects to *u, R 212 or R 217 It is a single bond that connects to *m, and R 222 or R 227 If it is a single bond attached to *n, then formula (2-1) is obtained by removing the p-biphenyl group.

[0014] In yet another embodiment, the present invention provides a material for an organic electroluminescent device having at least one compound selected from the compound represented by formula (1) and the compound represented by formula (2).

[0015] In yet another embodiment, the present invention provides an organic electroluminescent element having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer contains at least one selected from the compound represented by formula (1) and the compound represented by formula (2).

[0016] In yet another embodiment, the present invention provides an electronic device comprising the organic electroluminescent element. [Effects of the Invention]

[0017] Organic EL elements containing the compound represented by formula (1) exhibit improved element performance. Furthermore, organic EL elements containing the compound represented by formula (2) also exhibit improved element performance. [Brief explanation of the drawing]

[0018] [Figure 1] This is a schematic diagram showing an example of the layer configuration of an organic EL element according to one aspect of the present invention. [Figure 2] This is a schematic diagram showing another example of the layer configuration of an organic EL element according to one aspect of the present invention. [Figure 3] This is a schematic diagram showing yet another example of the layer configuration of an organic EL element according to one aspect of the present invention. [Modes for carrying out the invention]

[0019] [Definition] In this specification, the term "hydrogen atom" includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0020] In this specification, in chemical structural formulas, any bondable positions where symbols such as "R" or "D" representing a deuterium atom are not explicitly indicated shall be assumed to be bonded to hydrogen atoms, i.e., light hydrogen atoms, deuterium atoms, or tritium atoms.

[0021] In this specification, the ring-forming carbon number refers to the number of carbon atoms among the atoms constituting the ring itself in a compound with a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, fused ring compounds, crosslinked compounds, carbocyclic compounds, and heterocyclic compounds). If the ring is substituted by a substituent, the carbon atoms in the substituent are not included in the ring-forming carbon number. The same applies to the "ring-forming carbon number" described below unless otherwise specified. For example, a benzene ring has 6 ring-forming carbon atoms, a naphthalene ring has 10 ring-forming carbon atoms, a pyridine ring has 5 ring-forming carbon atoms, and a furan ring has 4 ring-forming carbon atoms. Also, for example, the ring-forming carbon number of a 9,9-diphenylfluorenyl group is 13, and the ring-forming carbon number of a 9,9'-spirobifluorenyl group is 25. Furthermore, when a benzene ring is substituted with an alkyl group, for example, the number of carbon atoms in that alkyl group is not included in the number of ring-forming carbon atoms of the benzene ring. Therefore, the number of ring-forming carbon atoms in a benzene ring substituted with an alkyl group is 6. Similarly, when a naphthalene ring is substituted with an alkyl group, for example, the number of carbon atoms in that alkyl group is not included in the number of ring-forming carbon atoms of the naphthalene ring. Therefore, the number of ring-forming carbon atoms in a naphthalene ring substituted with an alkyl group is 10.

[0022] In this specification, the number of ring-forming atoms refers to the number of atoms that constitute the ring itself in compounds with a ring-bonded structure (e.g., monocyclic compounds, fused rings, and ring aggregates) (e.g., monocyclic compounds, fused ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of ring-forming atoms) and atoms included in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. The same applies to "number of ring-forming atoms" as described below unless otherwise specified. For example, the number of ring-forming atoms in a pyridine ring is 6, the number of ring-forming atoms in a quinazoline ring is 10, and the number of ring-forming atoms in a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring, or the number of atoms constituting substituents, are not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms in a pyridine ring to which hydrogen atoms or substituents are bonded is 6. Furthermore, for example, hydrogen atoms bonded to the carbon atom of the quinazoline ring, or atoms constituting substituents, are not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring-forming atoms of a quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

[0023] In this specification, the expression "substituted or unsubstituted ZZ group having XX to YY carbon atoms" means that "XX to YY carbon atoms" represents the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of substituents when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0024] In this specification, the expression "ZZ group with substituted or unsubstituted atoms of XX to YY" means that "atom count XX to YY" represents the number of atoms when the ZZ group is unsubstituted, and does not include the number of substituent atoms when it is substituted. Here, "YY" is greater than "XX", where "XX" is an integer of 1 or more, and "YY" is an integer of 2 or more.

[0025] In this specification, an unsubstituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is "unsubstituted ZZ group," and a substituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is "substituted ZZ group." In this specification, "unsubstituted" in the context of a "substituted or unsubstituted ZZ group" means that the hydrogen atoms in the ZZ group are not replaced by substituents. The hydrogen atoms in an "unsubstituted ZZ group" are light hydrogen atoms, deuterium atoms, or tritium atoms. Furthermore, in this specification, "substituted" in the context of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. Similarly, "substituted" in the context of "BB group substituted with AA group" means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0026] "Substituents as described herein" The substituents described herein are described below. Unless otherwise specified, each substituent described herein is defined as follows:

[0027] The number of ring-forming carbon atoms in the "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring-forming atoms in the "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkyl group" as described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkenyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkynyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted cycloalkyl groups" described herein is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted arylene group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring-forming atoms in the "unsubstituted divalent heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkylene group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein.

[0028] • "substituted or unsubstituted aryl groups" Specific examples of "substituted or unsubstituted aryl groups" as described herein (Specific Examples Group G1) include the following unsubstituted aryl groups (Specific Examples Group G1A) and substituted aryl groups (Specific Examples Group G1B), etc. (Here, "unsubstituted aryl group" refers to the case where "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and "substituted aryl group" refers to the case where "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" simply includes both "unsubstituted aryl groups" and "substituted aryl groups." A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced by substituents. Examples of "substituted aryl groups" include the groups in which one or more hydrogen atoms of an "unsubstituted aryl group" in specific example group G1A below are replaced by substituents, and the examples of substituted aryl groups in specific example group G1B below. Note that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl groups" described herein also include groups in which the hydrogen atoms bonded to the carbon atom of the aryl group itself in the "substituted aryl group" in specific example group G1B below are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted aryl group" in specific example group G1B below are further replaced by substituents.

[0029] • Unsubstituted aryl groups (specific examples group G1A): Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, m-terphenyl-3'-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-Naphthyl group, 2-Naphthyl group, anthryl group, Benzoantryl group, Phenanthryl group, Benzophenanthryl group, phenalenyl group, Pyrenyl group, Chrysenyl group, Benzocrisenyl group, Triphenylenyl group, benzotriphenylenyl group, Tetraceryl group, Pentacenyl group, Fluorenyl group, 9,9'-Spirobifluorenyl group, Benzofluorenyl group, Dibenzofluorenyl group, Fluoranthenyl group, Benzofluoranthenyl group, Perilenyl group, and A monovalent aryl group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0030] [ka]

[0031] [ka]

[0032] • Substitutive aryl groups (Specific examples group G1B): o-Tryl group, m-tolyl group, p-tril group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, Meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, Cyanophenyl group, Triphenylsilylphenyl group, Trimethylsilylphenyl group, Phenylnaphthyl group, Naphthylphenyl group, and A group obtained by replacing one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the general formulas (TEMP-1) to (TEMP-15) above with substituents.

[0033] • "Substitutable or unsubstituted heterocyclic groups" The "heterocyclic group" as described herein is a cyclic group containing at least one heteroatom in its ring-forming atoms. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron. The "heterocyclic group" as described herein may be a monocyclic group or a fused ring group. The term "heterocyclic group" as used herein refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples of "substituted or unsubstituted heterocyclic groups" as described herein (Specific Examples Group G2) include the following unsubstituted heterocyclic groups (Specific Examples Group G2A) and substituted heterocyclic groups (Specific Examples Group G2B), etc. (Here, "unsubstituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group," and "substituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group.") In this specification, the term "heterocyclic group" simply includes both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups." A "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of "substituted heterocyclic groups" include the groups in specific example group G2A below in which hydrogen atoms of an "unsubstituted heterocyclic group" are replaced, and the examples of substituted heterocyclic groups in specific example group G2B below. Note that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic groups" described herein also include groups in which hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself are further replaced by substituents, and groups in which hydrogen atoms of substituents are further replaced by substituents.

[0034] The specific examples group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (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).

[0035] Specific examples group G2B includes, for example, substituted heterocyclic groups containing a nitrogen atom (Specific Examples Group G2B1), substituted heterocyclic groups containing an oxygen atom (Specific Examples Group G2B2), substituted heterocyclic groups containing a sulfur atom (Specific Examples Group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (Specific Examples Group G2B4).

[0036] • Unsubstituted heterocyclic groups containing a nitrogen atom (specific examples group G2A1): Pyrrolyl group, imidazolyl group, Pyrazolyl group, Triazolyl group, Tetrazolyl group, Oxazolyl group, isoxazolyl group, Oxadiazolyl group, Thiazolyl group, isothiazolyl group, Thiadianzolyl group, Pyridyl group, Pyridazinyl group, Pyrimidinyl group, pyrazinyl group, Triazinyl group, Indolyl group, isoindolyl group, indolidinyl group, quinolidinyl group, quinolyl group, Isoquinolyl group, cinnolyl group, Phthalazinyl group, Quinazolinyl group, Quinoxalinyl group, Benzimidazolyl group, Indazolyl group, Phenanthrolinyl group, Phenantridinyl group, Acridinyl group, Phenazinyl group, Carbazolyl group, Benzocarbazolyl group, Morpholino group, Phenoxadinyl group, Phenothiazinyl group, Azacarbazolyl group and diazacarbazolyl group.

[0037] • Unsubstituted heterocyclic groups containing an oxygen atom (specific examples group G2A2): Frill group, Oxazolyl group, isoxazolyl group, Oxadiazolyl group, xanthenyl group, Benzofuranyl group, Isobenzofuranyl group, Dibenzofuranyl group, Naphthobenzofuranyl group, Benzoxazolyl group, Benzoisoxazolyl group, Phenoxadinyl group, Morpholino group, Dinaphthofuranyl group, Azadibenzofuranyl group, Diazadibenzofuranyl group, Azanaftobenzofuranyl group, and Diazanaphthobenzofuranyl group.

[0038] • Unsubstituted heterocyclic groups containing a sulfur atom (specific examples group G2A3): Thienyl group, Thiazolyl group, isothiazolyl group, Thiadianzolyl group, Benzothiophenyl group (benzothienyl group), Isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), Naphthobenzothiophenyl group (naphthobenzothienyl group), Benzothiazolyl group, benzoisothiazolyl group, Phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), azadibenzothiophenyl group (azadibenzothienyl group), Diazadibenzothiophenyl group (diazadibenzothienyl group), Azanaphtobenzothiophenyl group (azanaphthobenzothienyl group), and Diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0039] • 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 examples group G2A4):

[0040] [ka]

[0041] [ka]

[0042] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each of these is independently an oxygen atom, a sulfur atom, NH, or CH2. However, X A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH. In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A If at least one of the members is NH or CH2, the monovalent heterocyclic groups derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) include monovalent groups obtained by removing one hydrogen atom from these NH or CH2 members.

[0043] • Heterocyclic groups with substitutions containing a nitrogen atom (Specific examples group G2B1): (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazole-9-yl group, Phenylcarbazole-9-yl group, Methyl benzimidazolyl group, Ethyl benzimidazolyl group, Phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, Phenylquinazolinyl group and biphenylylquinazolinyl group.

[0044] • Heterocyclic groups with substitutions containing an oxygen atom (Specific examples group G2B2): Phenyldibenzofuranyl group, Methyldibenzofuranyl group, t-butyldibenzofuranyl group, and A monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0045] • Heterocyclic groups with substitutions containing a sulfur atom (specific examples group G2B3): Phenyldibenzothiophenyl group, Methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and A monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0046] • Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific examples group G2B4):

[0047] The aforementioned "one or more hydrogen atoms of a monovalent heterocyclic group" means one or more hydrogen atoms selected from the hydrogen atoms bonded to the ring-forming carbon atoms of the monovalent heterocyclic group, the hydrogen atoms bonded to the nitrogen atom when at least one of XA and YA is NH, and the hydrogen atoms of the methylene group when one of XA and YA is CH2.

[0048] • "Substituted or unsubstituted alkyl groups" Specific examples of "substituted or unsubstituted alkyl groups" as described herein (Specific Examples Group G3) include the following unsubstituted alkyl groups (Specific Examples Group G3A) and substituted alkyl groups (Specific Examples Group G3B). (Here, "unsubstituted alkyl group" refers to the case where "substituted or unsubstituted alkyl group" is "unsubstituted alkyl group," and "substituted alkyl group" refers to the case where "substituted or unsubstituted alkyl group" is "substituted alkyl group.") Hereafter, "alkyl group" simply refers to both "unsubstituted alkyl groups" and "substituted alkyl groups." A "substituted alkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced by substituents. Specific examples of "substituted alkyl groups" include the groups in which one or more hydrogen atoms in the "unsubstituted alkyl groups" (specific example group G3A) below are replaced by substituents, and examples of substituted alkyl groups (specific example group G3B). In this specification, the alkyl group in "unsubstituted alkyl group" refers to a linear alkyl group. Therefore, "unsubstituted alkyl groups" include both linear "unsubstituted alkyl groups" and branched "unsubstituted alkyl groups". The examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed here are merely examples, and the "substituted alkyl groups" described herein also include groups in which the hydrogen atoms of the alkyl group itself in the "substituted alkyl groups" of specific example group G3B are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted alkyl groups" of specific example group G3B are further replaced by substituents.

[0049] • Unsubstituted alkyl groups (specific examples group G3A): Methyl group, Ethyl group, n-propyl group, Isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group.

[0050] • Substituting alkyl groups (specific examples group G3B): Heptafluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.

[0051] • "Substituted or unsubstituted alkenyl groups" Specific examples of "substituted or unsubstituted alkenyl groups" as described herein (Specific Examples Group G4) include the following unsubstituted alkenyl groups (Specific Examples Group G4A) and substituted alkenyl groups (Specific Examples Group G4B), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply includes both "unsubstituted alkenyl groups" and "substituted alkenyl groups." A "substituted alkenyl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted alkenyl group" are replaced by substituents. Specific examples of "substituted alkenyl groups" include groups in which the "unsubstituted alkenyl group" (Specific Example Group G4A) has substituents, and examples of substituted alkenyl groups (Specific Example Group G4B). Note that the examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl groups" described herein also include groups in which the hydrogen atoms of the alkenyl group itself in the "substituted alkenyl group" of Specific Example Group G4B are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted alkenyl group" of Specific Example Group G4B are further replaced by substituents.

[0052] • Unsubstituted alkenyl groups (specific examples group G4A): vinyl group, allyl group, 1-Butenyl group, 2-butenyl group, and 3-Butenyl group.

[0053] • Substitutive alkenyl groups (specific examples group G4B): 1,3-butanedienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.

[0054] • "Substituted or unsubstituted alkynyl groups" Specific examples of "substituted or unsubstituted alkynyl groups" as described herein (Specific Examples Group G5) include the following unsubstituted alkynyl groups (Specific Examples Group G5A), etc. (Here, "unsubstituted alkynyl group" refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group.") Hereafter, when simply referred to as "alkynyl group," it includes both "unsubstituted alkynyl groups" and "substituted alkynyl groups." A "substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced by substituents. Specific examples of "substituted alkynyl groups" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl group" (specific example group G5A) are replaced by substituents.

[0055] • Unsubstituted alkynyl groups (specific examples group G5A): Ethynyl group

[0056] • "Substituted or unsubstituted cycloalkyl groups" Specific examples of "substituted or unsubstituted cycloalkyl groups" as described herein (Specific Examples Group G6) include the following unsubstituted cycloalkyl groups (Specific Examples Group G6A) and substituted cycloalkyl groups (Specific Examples Group G6B), etc. (Here, "unsubstituted cycloalkyl group" refers to the case where "substituted or unsubstituted cycloalkyl group" is "unsubstituted cycloalkyl group," and "substituted cycloalkyl group" refers to the case where "substituted or unsubstituted cycloalkyl group" is "substituted cycloalkyl group.") In this specification, the term "cycloalkyl group" simply includes both "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups." A "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced by a substituent. Specific examples of "substituted cycloalkyl groups" include the groups in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" (specific example group G6A) are replaced by a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed here are merely examples, and the "substituted cycloalkyl groups" described herein also include groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself are replaced by a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted cycloalkyl group" of specific example group G6B are further replaced by a substituent.

[0057] • Unsubstituted cycloalkyl groups (specific examples group G6A): Cyclopropyl group, Cyclobutyl group, Cyclopentyl group, Cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.

[0058] • Substituting cycloalkyl groups (specific examples group G6B): 4-methylcyclohexyl group.

[0059] · "-Si(R 901 )(R 902 )(R 903 ) a base represented by -Si(R 901 )(R 902 )(R 903 ) Examples of the base represented by (Example Group G7) are: -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) Here are some examples. G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6. In -Si(G1)(G1)(G1), the multiple G1s are either identical or different from one another. In -Si(G1)(G2)(G2), the multiple G2s are either identical or different from one another. In -Si(G1)(G1)(G2), the multiple G1s are either identical or different from one another. In -Si(G2)(G2)(G2), the multiple G2s are either identical or different from one another. In -Si(G3)(G3)(G3), the multiple G3s are either identical or different from one another. In -Si(G6)(G6)(G6), the multiple G6s are either identical or different from one another.

[0060] ·「-O-(R 904 ) a base represented by The following information pertains to the -O-(R 904 ) Examples of the base represented by (Example Group G8) are: -O(G1), -O(G2), -O(G3), and -O(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6.

[0061] · "-S-(R 905 ) a base represented by -S-(R 905 ) Examples of the base represented by (example group G9) are: -S(G1), -S(G2), -S(G3), and -S(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6.

[0062] · "-N(R 906 )(R 907 ) a base represented by -N(R) as described in this specification 906 )(R 907 ) Examples of the base represented by (Example Group G10) are: -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) Here are some examples. G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6. In -N(G1)(G1), multiple G1s are either identical or different from one another. In -N(G2)(G2), multiple G2s are either identical or different from one another. In -N(G3)(G3), multiple G3s are either identical or different from one another. In -N(G6)(G6), the multiple G6s are either identical or different from one another.

[0063] • "Halogen atom" Specific examples of "halogen atoms" as described herein (Specific Examples Group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0064] • "Substituted or unsubstituted fluoroalkyl groups" The terms "substituted or unsubstituted fluoroalkyl groups" as used herein refer to groups in which at least one hydrogen atom bonded to the carbon atoms constituting the alkyl group is replaced by a fluorine atom, and also include groups in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group are replaced by fluorine atoms (perfluoro groups). The number of carbon atoms in an "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. A "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced by substituents. The terms "substituted fluoroalkyl groups" as used herein also include groups in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent are further replaced by substituents. Specific examples of "unsubstituted fluoroalkyl groups" include the example of a group in which one or more hydrogen atoms in the aforementioned "alkyl group" (specific example group G3) are replaced by fluorine atoms.

[0065] • "Substituted or unsubstituted haloalkyl groups" The terms "substituted or unsubstituted haloalkyl groups" as used herein refer to groups in which at least one hydrogen atom bonded to the carbon atoms constituting the alkyl group is replaced by a halogen atom, and also include groups in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group are replaced by halogen atoms. The number of carbon atoms in an "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. A "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of a "haloalkyl group" are replaced by substituents. The terms "substituted haloalkyl groups" as used herein also include groups in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent are further replaced by substituents. Specific examples of "unsubstituted haloalkyl groups" include groups in which one or more hydrogen atoms of the aforementioned "alkyl group" (specific example group G3) are replaced by halogen atoms. Haloalkyl groups are sometimes referred to as alkyl halogens.

[0066] • "Substituted or unsubstituted alkoxy groups" A specific example of a "substituted or unsubstituted alkoxy group" as described herein is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. The number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein.

[0067] • "substituted or unsubstituted alkylthio groups" A specific example of the "substituted or unsubstituted alkylthio group" described herein is the group represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. The number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein.

[0068] • "Substituted or unsubstituted aryloxy groups" A specific example of a "substituted or unsubstituted aryloxy group" as described herein is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.

[0069] • "Substituted or unsubstituted arylthio groups" A specific example of the "substituted or unsubstituted arylthio group" described herein is the group represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.

[0070] • "Substituted or unsubstituted trialkylsilyl groups" A specific example of the "trialkylsilyl group" described herein is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) are either identical or different from one another. Unless otherwise specified herein, 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.

[0071] • "Substituted or unsubstituted aralkyl groups" Specific examples of the "substituted or unsubstituted aralkyl group" described herein include the group represented by -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3, and G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. Therefore, an "aralkyl group" is a group in which the hydrogen atom of an "alkyl group" is replaced by an "aryl group" as a substituent, and is one form of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" in which an "unsubstituted aryl group" is substituted, and the number of carbon atoms in the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified herein. Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.

[0072] Unless otherwise specified herein, the substituted or unsubstituted aryl groups are 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, anthryl, phenanthryl, pyrenyl, chrysenyl, triphenylenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl.

[0073] Unless otherwise specified herein, the substituted or unsubstituted heterocyclic groups are preferably pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, benzimidazolyl, phenanthrolinyl, carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, or 9-carbazolyl), benzocarbazolyl, azacarbazolyl, diazacarbazolyl, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, aza These include dibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazole-1-yl group, (9-phenyl)carbazole-2-yl group, (9-phenyl)carbazole-3-yl group, or (9-phenyl)carbazole-4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazole-9-yl group, phenylcarbazole-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group, etc.

[0074] In this specification, unless otherwise specified, the carbazolyl group is specifically one of the following groups:

[0075] [ka]

[0076] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically one of the following groups:

[0077] [ka]

[0078] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bond position.

[0079] In this specification, unless otherwise specified, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups:

[0080] [ka]

[0081] In the general formulas (TEMP-34) to (TEMP-41) above, * represents a bond position.

[0082] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t-butyl groups.

[0083] • "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described herein is a divalent group derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described above. Specific examples of the "substituted or unsubstituted arylene group" (Specific Examples Group G12) include the divalent group derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described in Specific Examples Group G1.

[0084] • "Substitutable or unsubstituted divalent heterocyclic groups" Unless otherwise specified, the “substituted or unsubstituted divalent heterocyclic groups” described herein refer to divalent groups derived by removing one hydrogen atom from the heterocycle of the “substituted or unsubstituted heterocyclic groups” described above. Specific examples of “substituted or unsubstituted divalent heterocyclic groups” (Specific Examples Group G13) include the divalent groups derived by removing one hydrogen atom from the heterocycle of the “substituted or unsubstituted heterocyclic groups” described in Specific Examples Group G2.

[0085] • "Substituted or unsubstituted alkylene groups" Unless otherwise specified, the "substituted or unsubstituted alkylene groups" described herein are divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl groups" described above. Specific examples of "substituted or unsubstituted alkylene groups" (Specific Examples Group G14) include the divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl groups" described in Specific Examples Group G3.

[0086] Unless otherwise specified herein, the substituted or unsubstituted arylene groups are preferably any of the following general formulas (TEMP-42) to (TEMP-68).

[0087] [ka]

[0088] [ka]

[0089] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each of these is independently either a hydrogen atom or a substituent. In the general formulas (TEMP-42) to (TEMP-52) above, * represents a bond position.

[0090] [ka]

[0091] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each of these is independently either a hydrogen atom or a substituent. Equations Q9 and Q 10 These elements may be bonded to each other via single bonds to form a ring. In the general formulas (TEMP-53) to (TEMP-62) above, * represents a bond position.

[0092] [ka]

[0093] In the general formulas (TEMP-63) to (TEMP-68) above, Q1 to Q8 are each independently a hydrogen atom or a substituent. In the general formulas (TEMP-63) to (TEMP-68) above, * represents a bond position.

[0094] Unless otherwise specified herein, the substituted or unsubstituted divalent heterocyclic groups described herein are preferably any of the following general formulas (TEMP-69) to (TEMP-102).

[0095] [ka]

[0096] [ka]

[0097] [ka]

[0098] In the general formulas (TEMP-69) to (TEMP-82) above, Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0099] [ka]

[0100] [ka]

[0101] [ka]

[0102] [ka]

[0103] In the general formulas (TEMP-83) to (TEMP-102) above, Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0104] The above is a description of the substituents described herein.

[0105] • "When they combine to form a ring" In this specification, the phrase "one or more pairs of adjacent elements join together to form a substituted or unsubstituted monoring, join together to form a substituted or unsubstituted fused ring, or do not join together" means the case where "one or more pairs of adjacent elements join together to form a substituted or unsubstituted monoring," the case where "one or more pairs of adjacent elements join together to form a substituted or unsubstituted fused ring," and the case where "one or more pairs of adjacent elements do not join together." In this specification, the cases in which "one or more pairs of adjacent elements bond to each other to form a substituted or unsubstituted monoring" and "one or more pairs of adjacent elements bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "cases where elements bond to form a ring") will be explained below. An example will be given of an anthracene compound represented by the following general formula (TEMP-103), whose parent skeleton is an anthracene ring.

[0106] [ka]

[0107] For example, R921 ~R 930 In the case where "one or more pairs of adjacent groups are joined together to form a ring," the pairs of adjacent groups that make up one set are R 921 and R 922 The pair, R 922 and R 923 The pair, R 923 and R 924 The pair, R 924 and R 930 The pair, R 930 and R 925 The pair, R 925 and R 926 The pair, R 926 and R 927 The pair, R 927 and R 928 The pair, R 928 and R 929 The pair with, and R 929 and R 921 They are a pair.

[0108] The phrase "one or more pairs" above means that two or more pairs of adjacent pairs may simultaneously form a ring. For example, R 921 and R 922 and are joined to form a ring Q A Forms R 925 and R 926 and are joined to form a ring Q B If the above general formula (TEMP-103) is formed, the anthracene compound represented by the above general formula (TEMP-104) is represented by the following general formula (TEMP-104).

[0109] [ka]

[0110] The case where "two or more adjacent elements form a ring" includes not only cases where two adjacent elements are joined, as in the example above, but also cases where three or more adjacent elements are joined. For example, R 921 and R 922 and are joined to form a ring Q A Forms R 922 and R923 and are joined to form a ring Q C It forms three adjacent (R 921 , R 922 and R 923 This refers to the case where a set consisting of ) is bonded to each other to form a ring and condenses onto the anthracene matrix skeleton, in which case the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C R 922 Share.

[0111] [ka]

[0112] The formed "mono-ring" or "condensed-ring" may be saturated or unsaturated, based solely on the structure of the formed ring. Even when "a pair of adjacent rings" forms a "mono-ring" or "condensed-ring," the "mono-ring" or "condensed-ring" can be saturated or unsaturated. For example, ring Q formed in the general formula (TEMP-104) A and ring Q B These are, respectively, a "single ring" or a "condensed ring". Also, ring Q formed in the general formula (TEMP-105) is A , and ring Q C This is a "condensed ring". The ring Q of the general formula (TEMP-105) A and Q C This refers to the Q environment. A and Q C The ring Q of the general formula (TMEP-104) is formed by the condensation of the two rings. A If it is a benzene ring, then ring Q A It is a single ring. The ring Q of the general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a condensed ring.

[0113] An "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocycle. A "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocycle. Specific examples of aromatic hydrocarbon rings include structures in which the groups listed as examples in specific example group G1 are terminated by hydrogen atoms. A concrete example of an aromatic heterocycle is the structure in which the aromatic heterocycle group listed as a concrete example in concrete example group G2 is terminated by a hydrogen atom. Specific examples of aliphatic hydrocarbon rings include structures in which the groups listed as examples in example group G6 are terminated by hydrogen atoms. "To form a ring" means to form a ring with only multiple atoms of the parent skeleton, or with multiple atoms of the parent skeleton and one or more additional arbitrary elements. For example, as shown in the general formula (TEMP-104), 921 and R 922 A ring Q is formed when these two elements are bonded together. A R 921 The carbon atoms of the anthracene skeleton to which R is bonded, 922 It refers to a ring formed by the carbon atoms of the anthracene skeleton to which the R atoms are bonded, and one or more arbitrary elements. A specific example is R 921 and R 922 And the environment Q A When forming R 921 The carbon atoms of the anthracene skeleton to which R is bonded, 922 When the carbon atoms of the anthracene skeleton bonded to the four carbon atoms form a monocyclic unsaturated ring, R 921 and R 922 The ring formed by these two is a benzene ring.

[0114] Here, "any element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur, unless otherwise specified herein. In any element (for example, carbon or nitrogen), bonds that do not form a ring may be terminated with a hydrogen atom or the like, or substituted with "any substituent" as described later. If any element other than carbon is included, the formed ring is a heterocycle. The "one or more arbitrary elements" constituting the monoring or fused ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5, unless otherwise specified herein. Unless otherwise specified herein, the preferred form is a monoring or a fused ring. Unless otherwise specified herein, the "unsaturated ring" is preferred over the "saturated ring". Unless otherwise specified herein, “monocyclic” is preferably a benzene ring. Unless otherwise specified herein, the “unsaturated ring” is preferably a benzene ring. When "one or more sets of two or more adjacent elements" "bond to each other to form a substituted or unsubstituted monoring" or "bond to each other to form a substituted or unsubstituted fused ring", unless otherwise specified herein, preferably, one or more sets of two or more adjacent elements bond to each other to form a substituted or unsubstituted "unsaturated ring" consisting of multiple atoms of the parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur elements, ranging from one to fifteen.

[0115] When the above-mentioned "monocyclic ring" or "fused ring" has substituents, the substituents are, for example, "any substituents" as described later. Specific examples of substituents when the above-mentioned "monocyclic ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described herein" above. When the above-mentioned "saturated ring" or "unsaturated ring" has substituents, the substituents are, for example, "any substituents" as described later. Specific examples of substituents when the above-mentioned "mono-ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described herein" above. The above explains the cases in which "one or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring" and "one or more pairs of adjacent elements combine to form a substituted or unsubstituted fused ring" ("the case of combining to form a ring").

[0116] • Substituents in the phrase "substituted or unsubstituted" In one embodiment described herein, the substituent referred to as "substituted or unsubstituted" (which may be referred to herein as "any substituent") is, for example, Unsubstituted alkyl groups with 1 to 50 carbon atoms, Unsubstituted alkenyl groups with 2 to 50 carbon atoms, Unsubstituted alkynyl groups with 2 to 50 carbon atoms, Unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, Unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, and Unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms It is a base selected from the group consisting of, Here, R 901 ~R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, It is a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms. R 901 If there are two or more of them, then there are two or more R 901 They are either identical or different from each other. R 902 If there are two or more of them, then there are two or more R 902 They are either identical or different from each other. R 903If there are two or more of them, then there are two or more R 903 They are either identical or different from each other. R 904 If there are two or more of them, then there are two or more R 904 They are either identical or different from each other. R 905 If there are two or more of them, then there are two or more R 905 They are either identical or different from each other. R 906 If there are two or more of them, then there are two or more R 906 They are either identical or different from each other. R 907 If there are two or more of them, then there are two or more R 907 They are either identical or different from one another.

[0117] In one embodiment, the substituent in the case of "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 50 carbon atoms, A ring-forming aryl group with 6 to 50 carbon atoms, and Heterocyclic groups with 5 to 50 ring-forming atoms It is a group selected from the group consisting of the following.

[0118] In one embodiment, the substituent in the case of "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 18 carbon atoms, Ring-forming aryl groups with 6 to 18 carbon atoms, and Heterocyclic groups with 5 to 18 ring-forming atoms It is a group selected from the group consisting of the following.

[0119] Specific examples of each of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents as described herein" above.

[0120] Unless otherwise specified herein, adjacent substituents may form a "saturated ring" or an "unsaturated ring," preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, and more preferably a benzene ring. Unless otherwise specified herein, any substituent may have further substituents, such as those described above.

[0121] In this specification, a numerical range expressed using "AA~BB" means a range that includes the numerical value AA, which is listed before "AA~BB", as the lower limit, and the numerical value BB, which is listed after "AA~BB", as the upper limit.

[0122] The compounds of the present invention will be described below. A compound according to one aspect of the present invention is represented by the following formula (1). However, the compound of the present invention represented by formula (1) and the formula included in formula (1) described later may be simply referred to as "inventive compound (1)". Furthermore, compounds relating to other aspects of the present invention are represented by formula (2) described later. The compound of the present invention represented by formula (2) described later and the formula included in formula (2) described later may be simply referred to as "inventive compound (2)". Moreover, when referring to both "inventive compound (1)" and "inventive compound (2)", they may be simply referred to as "inventive compound". [ka]

[0123] The following explains the symbols in equation (1) and the equation (1) described later. Note that the same symbols have the same meaning.

[0124] In formula (1), R 1 and R 2 One of them is a methyl group, and the other is an unsubstituted phenyl group. R 1and R 2 They do not bond to each other and therefore do not form a ring structure. R 3 and R 4 One of them is a methyl group, and the other is an unsubstituted phenyl group. R 3 and R 4 They do not bond to each other and therefore do not form a ring structure. R 11 ~R 18 , and R 21 ~R 28 This is a hydrogen atom. however, R 11 ~R 18 One of the selected options is a single bond that connects to *a, R 21 ~R 28 One of the options selected is a single bond that connects to *b.

[0125] R 12 , R 13 , R 14 , R 15 , R 16 , and R 17 Preferably, one of the selected bonds is a single bond that connects to *a, R 12 , and R 17 It is more preferable that the one selected from among them is a single bond that connects to *a.

[0126] R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 Preferably, one of the selected bonds is a single bond that connects to *b, R 22 , and R 27 It is more preferable that the one selected from among them is a single bond that connects to *b.

[0127] L 1 and L 2 Each of these is independently a single bond, or a substituted or unsubstituted phenylene group. L 1 and L2 It is preferable that the bond is a single bond.

[0128] Ar 1 This is a base represented by any of the formulas (1-1) to (1-6). [ka]

[0129] 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 of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group.

[0130] 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 of these is independently preferably a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group; more preferably a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group, and even more preferably a hydrogen atom.

[0131] 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 Details of the substituted or unsubstituted C1-C50 alkyl groups represented by are as described above in the section "Substituents as described herein". 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 135The unsubstituted alkyl group represented by is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group, more preferably a methyl group, an ethyl group, an isopropyl group, or a t-butyl group, and even more preferably a methyl group or a t-butyl group.

[0132] 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 Details of the substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms represented by are as described above in the section "Substituents as described herein". 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 135The unsubstituted cycloalkyl group represented by is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, or a 2-norbornyl group; more preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group; and even more preferably a cyclopentyl group or a cyclohexyl group.

[0133] 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 as described above in the section "Substituents as described herein," and it is preferably a fluorine atom.

[0134] 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 Details of the substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms represented by are as described in "Substituents as described herein". 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 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 even more preferably a phenyl group.

[0135] 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 Details of the substituted or unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms represented by are as described in "Substituents as described herein". The unsubstituted heterocyclic group is preferably a dibenzofuranyl group or a dibenzothiophenyl group.

[0136] X 1 is an oxygen atom, a sulfur atom, or CR a R b And, R a and R bEach of these is independently a hydrogen atom, a methyl group, or a substituted or unsubstituted phenyl group, and R a and R b These elements may combine with each other to form a substituted or unsubstituted ring.

[0137] In one embodiment of the present invention, X 1 is preferably an oxygen atom. In other embodiments, X 1 is preferably a sulfur atom. In yet another embodiment, X 1 Preferably CR a R b And R a and R b Preferably, this is a methyl group, or a substituted or unsubstituted phenyl group.

[0138] The aforementioned R a and R b Details of any substituted or unsubstituted rings formed by the bonding of these elements are as described above in "Substituents as described herein," and are selected from substituted or unsubstituted aromatic hydrocarbon rings, substituted or unsubstituted aliphatic hydrocarbon rings, substituted or unsubstituted aromatic heterocycles, and substituted or unsubstituted non-aromatic heterocycles.

[0139] The aromatic hydrocarbon ring is, for example, a benzene ring, a biphenylene ring, a naphthalene ring, or a fluorene ring, preferably a naphthalene ring or a fluorene ring. 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.

[0140] The aromatic heterocycle 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 naphthobenzofuran ring, a dibenzothiophene ring, a naphthobenzothiophene ring, a carbazole ring, or a benzocarbazole ring, preferably a dibenzofuran ring or a dibenzothiophene ring. The aforementioned non-aromatic heterocycle is, for example, a heterocycle obtained by partially hydrogenating the above aromatic heterocycle.

[0141] In one embodiment of the present invention, R a and R b These elements do not necessarily have to bond to each other to form a substituted or unsubstituted ring.

[0142] R 31 ~R 35 One of the selected options is a single bond that connects to *c, R 41 ~R 46 One of the selected options is a single bond that connects to *d, R 41 ~R 46 The other one chosen from is a single bond that joins *e, R 65 ~R 68 One of the selected options is a single bond that connects to *f, R 79 ~R 82 One of the selected options is a single bond that connects to *g, R 91 , and R 97 ~R 100 One of the selected options is a single bond that connects to *h, R 105 ~R 108 One of the options is a single join that connects to *i, R 111 ~R 116 One of the selected options is a single bond that connects to *j, R 111 ~R 116 Another one chosen from is a single bond that joins *k, R 111~R 116 Another option chosen from this is a single join that connects to *l.

[0143] R that is not a single bond 31 ~R 35 Two adjacent R bonds selected from the above, which are not any of the single bonds mentioned above. 41 ~R 46 Two adjacent elements are selected from R 51 ~R 55 Two adjacent R bonds selected from the single bond, which are not single bonds. 61 ~R 68 Two adjacent R bonds selected from the single bond, which are not single bonds. 71 ~R 82 Two adjacent R bonds selected from the single bond, which are not single bonds. 91 ~R 100 Two adjacent R bonds selected from the single bond, which are not single bonds. 101 ~R 108 Two adjacent R bonds selected from the above, which are not any of the single bonds mentioned above. 111 ~R 116 Two adjacent elements are selected from R 121 ~R 125 Two adjacent elements are selected from R 131 ~R 135 Two adjacent elements selected from the set do not bond to each other and therefore do not form a ring structure.

[0144] 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.

[0145] ** indicates the bond position to the central nitrogen atom N, m is 0 or 1, n is 0 or 1, In equations (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 R 31 ~R 35 Combine with one selected from, In equations (1-3) to (1-6), when m is 0, *c is bonded to the central nitrogen atom N. R 12 or R 17 It is a single bond that connects to *a, and R 22 or R 27 If it is a single bond attached to *b, then formula (1-1) excludes the p-biphenyl group. That is, R 12 or R 17 It is a single bond that connects to *a, and R 22 or R 27 When is a single bond attached to *b, and m is 1 and n is 0, in equation (1-1), R 31 , R 32 , R 34 , and R 35 One of the selected bonds is a single bond that connects to *c, preferably R 31 and R 35 One of the options selected is a single bond that connects to *c. Also, R 12 or R 17 It is a single bond that connects to *a, and R 22 or R 27 When is a single bond attached to *b, and m is 0 and n is 1, in equation (1-1), R 46 is a single bond that joins *d, and R 41 , R 42 ,, R 44 , and R 45 One of the selected bonds is a single bond that joins *e, preferably R 41 and R 45 One of the options chosen is a single bond that connects to *e. The p-biphenyl group is represented by the following formula.

[0146] [ka]

[0147] Formulas (1-1) and (1-2) are, in one embodiment of the present invention, preferably m is 0 and n is 0; in another embodiment, preferably m is 0 and n is 1; in yet another embodiment, preferably m is 1 and n is 0; and in yet another embodiment, preferably m is 1 and n is 1. In equation (1-1), it is preferable that m or n is 0. In formulas (1-3) to (1-6), m is preferably 0 in one embodiment of the present invention, and m is preferably 1 in another embodiment.

[0148] The group represented by formula (1-1) is more preferably a substituted or unsubstituted group selected from the following formulas. [ka] (Any substituents have been omitted from the formula.)

[0149] The group represented by formula (1-2) is preferably a substituted or unsubstituted group selected from the following formulas. [ka] (Any substituents have been omitted from the formula.)

[0150] The group represented by formula (1-3) is preferably a substituted or unsubstituted group selected from the following formulas. [ka] (Any substituents have been omitted from the formula.)

[0151] The group represented by formula (1-4) is preferably an unsubstituted group selected from the following formulas. [ka] (Any substituents have been omitted from the formula.)

[0152] The group represented by formula (1-5) is preferably a substituted or unsubstituted group selected from the following formulas. [ka]

[0153] [ka] (Any substituents have been omitted from the formula.)

[0154] The group represented by formula (1-6) is preferably a substituted or unsubstituted group selected from the following formulas. [ka] (Any substituents have been omitted from the formula.)

[0155] Ar 1 It is preferable that the group is represented by any of the formulas (1-1), (1-2), (1-5), and (1-6), and more preferably by the formula (1-1).

[0156] In one aspect of the present invention, (1-1)*c is not a single bond R 31 ~R 35 However, it could all be hydrogen. (1-2) R is not a single bond attached to *d and is not a single bond attached to *e. 41 ~R 46 However, they could all be hydrogen atoms. (1-3)R 51 ~R 55 However, they could all be hydrogen atoms. (1-4)R 61 ~R 64 , and R which is not a single bond attached to *f 65 ~R 68 However, they could all be hydrogen atoms. (1-5)R 71 ~R 78, and R which is not a single bond attached to *g 79 ~R 82 However, they could all be hydrogen atoms. (1-6)R 92 ~R 96 , as well as R which is not a single bond attached to *h 91 and R 97 ~R 100 However, they could all be hydrogen atoms. (1-7)R 101 ~R 104 , and R which is not a single bond attached to *i 105 ~R 108 However, they could all be hydrogen atoms. (1-8) R is not a single bond attached to *j, nor is it a single bond attached to *k, nor is it a single bond attached to *l. 111 ~R 116 , R 121 ~R 125 , and R 131 ~R 135 However, they could all be hydrogen atoms.

[0157] Compounds according to other embodiments of the present invention are represented by the following formula (2). [ka]

[0158] The following explains the symbols in equation (2) and the equation (2) described later. Note that the same symbols have the same meaning.

[0159] In formula (2), R 201 ~R 204 One of the selected groups is a methyl group, R 201 ~R 204 The other three selected from are unsubstituted phenyl groups. R 201 and R 202 They do not bond to each other and therefore do not form a ring structure. R 203 and R 204 They do not bond to each other and therefore do not form a ring structure. R211 ~R 218 , and R 221 ~R 228 This is a hydrogen atom. however, R 211 ~R 218 One of the options selected is a single bond that joins *m, R 221 ~R 228 One of the options selected is a single bond that connects to *n.

[0160] R 212 , R 213 , R 214 , R 215 , R 216 , and R 217 Preferably, one of the selected bonds is a single bond that connects to *m, R 212 , and R 217 It is more preferable that the one selected from these is a single bond that connects to *m.

[0161] R 222 , R 223 , R 224 , R 225 , R 226 , and R 227 Preferably, one of the selected bonds is a single bond that connects to *n, R 222 , and R 227 It is more preferable that the one selected from these is a single bond that connects to *n.

[0162] L 11 and L 12 Each of these is independently a single bond, or a substituted or unsubstituted phenylene group. L 11 and L 12 It is preferable that the bond is a single bond.

[0163] Ar 11 This is a base represented by any of the formulas (2-1) to (2-6). [ka]

[0164] In formulas (2-1) to (2-6), 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 of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group.

[0165] 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 335Each of these is independently preferably a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group; more preferably a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group, and even more preferably a hydrogen atom.

[0166] 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 Details of each group represented by 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 base described in relation to this are the same, and all preferred bases are also the same.

[0167] X 2is an oxygen atom, a sulfur atom, or CR c R d And, R c and R d Each is independently a hydrogen atom or a methyl group, and R c and R d They do not bond to each other and therefore do not form a ring structure.

[0168] In one embodiment of the present invention, X 2 is preferably an oxygen atom. In other embodiments, X 2 is preferably a sulfur atom. In yet another embodiment, X 2 Preferably CR c R d And R c and R d Preferably, this is a methyl group, or a substituted or unsubstituted phenyl group.

[0169] R 231 ~R 235 One of the selected options is a single bond that connects to *o, R 241 ~R 246 One of the selected options is a single bond that connects to *p, R 241 ~R 246 The other one chosen from is a single bond that joins *q, R 265 ~R 268 One of the options is a single bond that joins *r, R 279 ~R 282 One of the options is a single bond that joins *s, R 291 , and R 297 ~R 300 One of the selected options is a single bond that connects to *t. R 305 ~R 308 One of the options is a single bond that connects to *u, R 311 ~R 316 One of the selected options is a single bond that connects to *v, R 311 ~R 316Another one selected from is a single bond that joins *w, R 311 ~R 316 Another one chosen from this is a single join that connects to *x.

[0170] R that is not a single bond 231 ~R 235 Two adjacent R bonds selected from the above, which are not any of the single bonds mentioned above. 241 ~R 246 Two adjacent elements are selected from R 251 ~R 255 Two adjacent R bonds selected from the single bond, which are not single bonds. 261 ~R 268 Two adjacent R bonds selected from the single bond, which are not single bonds. 271 ~R 282 Two adjacent R bonds selected from the single bond, which are not single bonds. 291 ~R 300 Two adjacent R bonds selected from the single bond, which are not single bonds. 301 ~R 308 Two adjacent R bonds selected from the above, which are not any of the single bonds mentioned above. 311 ~R 316 Two adjacent elements are selected from R 321 ~R 325 Two adjacent elements are selected from R 331 ~R 335 Two adjacent elements selected from the set do not bond to each other and therefore do not form a ring structure.

[0171] The following rings do not crosslink: benzene ring A2 and benzene ring B2, benzene ring A2 and benzene ring C2, benzene ring A2 and benzene ring D2, benzene ring A2 and benzene ring E2, benzene ring A2 and benzene ring F2, benzene ring B2 and benzene ring C2, benzene ring D2 and benzene ring E2, and benzene ring D2 and benzene ring F2.

[0172] *** indicates the bond position to the central nitrogen atom N. p is 0 or 1, q is 0 or 1, In equations (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 R231 ~R 235 Combine with one selected from, In equations (2-3) to (2-6), when p is 0, *o is bonded to the central nitrogen atom N. In equation (2-5), X 2 CR c R d And when p is 0, L 11 and L 12 At least one of those selected is a substituted or unsubstituted phenylene group, In equation (2-5), X 2 When is an oxygen atom and p is 1, R 306 ~R 308 One of the options is a single bond that connects to *u, R 212 or R 217 It is a single bond that connects to *m, and R 222 or R 227 If it is a single bond attached to *n, then formula (2-1) is obtained by removing the p-biphenyl group. That is, R 212 or R 217 It is a single bond that connects to *m, and R 222 or R 227 When is a single bond connecting to *n, and m is 1 and n is 0, in equation (2-1), R 231 , R 232 , R 234 , and R 235 One of the selected bonds is a single bond that connects to *o, preferably R 231 and R 235 One of the options selected is a single bond that connects to *o. Also, R 212 or R 217 It is a single bond that connects to *m, and R 222 or R 227 When is a single bond that connects to *n, and m is 0 and n is 1, in equation (2-1), R 246 is a single bond that connects to *p, and R 241 , R 242 ,, R 244 , and R 245 One of the selected bonds is a single bond that connects to *q, preferably R 241and R 245 One of the options selected is a single bond that connects to *q.

[0173] Formulas (2-1) and (2-2) are, in one embodiment of the present invention, preferably m is 0 and n is 0; in another embodiment, preferably m is 0 and n is 1; in yet another embodiment, preferably m is 1 and n is 0; and in yet another embodiment, preferably m is 1 and n is 1. In equation (2-1), it is preferable that m or n is 0. In formulas (1-3) to (1-6), m is preferably 0 in one embodiment of the present invention, and m is preferably 1 in another embodiment.

[0174] The preferred group represented by formula (2-1) is the same as the preferred group represented by formula (1-1).

[0175] The preferred group represented by formula (2-2) is the same as the preferred group represented by formula (1-2).

[0176] The preferred group represented by formula (2-3) is the same as the preferred group represented by formula (1-3).

[0177] The preferred group represented by formula (2-4) is the same as the preferred group represented by formula (1-4).

[0178] The preferred groups represented by formula (2-5) are the same as the preferred groups represented by formula (1-5).

[0179] The preferred group represented by formula (1-6) is the same as the preferred group represented by formula (1-6).

[0180] Ar 11 It is preferable that the group is represented by any of the formulas (2-1), (2-2), (2-5), and (2-6), and more preferably by the formula (2-1).

[0181] In one aspect of the present invention, (2-1) R is not a single bond attached to o.231 ~R 235 However, they could all be hydrogen atoms. (2-2) R is not a single bond attached to *p and is not a single bond attached to *q. 241 ~R 246 However, they could all be hydrogen atoms. (2-3)R 251 ~R 255 However, they could all be hydrogen atoms. (2-4)R 261 ~R 264 , and R that is not a single bond to *r 265 ~R 268 However, they could all be hydrogen atoms. (2-5)R 271 ~R 278 , and R which is not a single bond attached to *s 279 ~R 282 However, they could all be hydrogen atoms. (2-6)R 292 ~R 296 , as well as R which is not a single bond attached to *t 291 and R 297 ~R 300 However, they could all be hydrogen atoms. (2-7)R 301 ~R 304 , and R which is not a single bond attached to *u 305 ~R 308 However, they could all be hydrogen atoms. (2-8) R is not a single bond attached to *v, nor is it a single bond attached to *w, nor is it a single bond attached to *x. 311 ~R 316 , R 321 ~R 325 , and R 331 ~R 335 However, they could all be hydrogen atoms.

[0182] As stated above, the term "hydrogen atom" as used herein includes light hydrogen atoms, deuterium atoms, and tritium atoms. Therefore, the inventive compound may contain naturally occurring deuterium atoms. Furthermore, by using a compound in which some or all of the starting compounds are deuterated, deuterium atoms may be intentionally introduced into the inventive compound. Therefore, in one aspect of the present invention, the inventive compound contains at least one deuterium atom. That is, the inventive compound (1) may be a compound represented by formula (1), wherein at least one of the hydrogen atoms contained in the compound is a deuterium atom, and the inventive compound (2) may be a compound represented by formula (2), wherein at least one of the hydrogen atoms contained in the compound is a deuterium atom.

[0183] In the compound represented by formula (1), R 1 and R 2 each represent a hydrogen atom of a methyl group or an unsubstituted phenyl group; R 3 and R 4 each represent a hydrogen atom of a methyl group or an unsubstituted phenyl group; R 11 ~R 18 and R 21 ~R 28 each represent a hydrogen atom; L 1 and L 2 each represent a hydrogen atom of a substituted or unsubstituted phenylene group; R 31 ~R 35 R 41 ~R 46 R 51 ~R 55 R 61 ~R 68 R 71 ~R 82 R <000E1AD>~R 100 R 101 ~R 108 R 111 ~R 116 R 121 ~R 125 and R 131 ~R 135 each represent a hydrogen atom; R 31 ~R 35 R 41 ~R 46 R51 ~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 of the substituents or unsubstituted alkyl, cycloalkyl, aryl, or heteroaryl groups represented by ~R, R may be a hydrogen atom; R a and R b Any of the hydrogen atoms represented by R may be a hydrogen atom; R a and R b Any of the hydrogen atoms represented by R may be a hydrogen atom, a methyl group, or a substituted or unsubstituted phenyl group; At least one hydrogen atom selected from may be a deuterium atom.

[0184] In the compound represented by formula (2), R 201 ~R 204 Any of the hydrogen atoms represented by R may be a hydrogen atom, a methyl group, or an unsubstituted phenyl group; R 211 ~R 218 、and R 221 ~R<> 228 <>Any of the hydrogen atoms represented by R may be a hydrogen atom; L 11 and L 12 Any of the hydrogen atoms represented by L may be a substituted or unsubstituted phenylene group; 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[[ID=<<100>>]] 311 [[ID=<<101>>]]~R[[ID=<<102>>]] 316, R 321 ~R 325 , and R 331 ~R 335 A hydrogen atom represented by either of the following; 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 A hydrogen atom in a substituted or unsubstituted alkyl group, cycloalkyl group, aryl group, or heterocyclic group represented by any of the above; R c and R d A hydrogen atom represented by either of the following; R c and R d The hydrogen atoms of the methyl group, substituted and unsubstituted phenyl group represented by any of the above; At least one of the hydrogen atoms selected may be a deuterium atom.

[0185] The deuterated ratio of the inventive compound depends on the deuterated ratio of the raw material compound used. Even when using raw materials with a predetermined deuterated ratio, a certain proportion of naturally occurring light hydrogen isotopes may be present. Therefore, the deuterated ratios of the inventive compound shown below include a ratio that takes into account trace amounts of naturally occurring isotopes, in addition to the ratio obtained by simply counting the number of deuterium atoms represented by the chemical formula. The deuteration rate of the inventive compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, and even more preferably 50% or more.

[0186] The inventive compound may be a mixture containing a deuterated compound and a non-deuterated compound, or a mixture of two or more compounds having different deuterated rates. The deuterated rate of such a mixture is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, even more preferably 50% or more, and less than 100%. Furthermore, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the inventive compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, and even more preferably 10% or more, and 100% or less.

[0187] Details of the substituents (any substituents) in the case of "substituted or unsubstituted" included in the definitions of each of the above formulas are as described in "Substituents in the case of 'substituted or unsubstituted'".

[0188] Those skilled in the art can easily produce the inventive compound by referring to the synthesis examples and known synthesis methods described later.

[0189] The following are specific examples of the inventive compounds, but the invention is not limited to these example compounds. In the specific examples below, D represents a deuterium atom.

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[0278] Materials for organic EL devices The organic EL element material of the present invention contains the inventive compound. The content of the inventive compound in the organic EL element material 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%), even more preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). The organic EL element material of the present invention is useful for the manufacture of organic EL elements.

[0279] Organic EL element The organic EL element of the present invention includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer includes a light-emitting layer, and at least one layer of the organic layer contains the inventive compound. Examples of organic layers containing the inventive compound include, but are not limited to, hole transport bands (hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer, etc.) provided between the anode and the light-emitting layer, light-emitting layer, space layer, electron transport bands (electron injection layer, electron transport layer, hole blocking layer, etc.) provided between the cathode and the light-emitting layer. The inventive compound is preferably used as a material for the hole transport band or light-emitting layer of a fluorescent or phosphorescent EL element, more preferably as a material for the hole transport band, even more preferably as a material for the hole injection layer, hole transport layer, electron blocking layer, or exciton blocking layer, and particularly preferably as a material for the hole injection layer or hole transport layer.

[0280] The organic EL element of the present invention may be a monochromatic light-emitting element of the fluorescent or phosphorescent type, or a white light-emitting element of the fluorescent / phosphorescent hybrid type, and may be a simple type having a single light-emitting unit, or a tandem type having multiple light-emitting units, but a fluorescent light-emitting element is preferred. Here, "light-emitting unit" refers to the smallest unit that includes an organic layer, of which at least one layer is a light-emitting layer, and emits light when injected holes and electrons recombine.

[0281] For example, the following are typical device configurations for simple organic EL elements. (1) Anode / Light-emitting unit / Cathode Furthermore, the above-mentioned light-emitting unit may be a multilayer type having multiple phosphorescent and fluorescent light-emitting layers. In this case, a space layer may be provided between each light-emitting layer to prevent excitons generated in the phosphorescent layer from diffusing into the fluorescent light-emitting layer. A typical layer configuration of a simple light-emitting unit is shown below. The layers in parentheses are arbitrary. (a) (Hole injection layer / ) Hole transport layer / Fluorescence layer / Electron transport layer ( / Electron injection layer) (b) (Hole injection layer / ) Hole transport layer / Phosphorescent layer Electron transport layer ( / Electron injection layer) (c) (Hole injection layer / ) Hole transport layer / First fluorescence emission layer / Second fluorescence emission layer / Electron transport layer ( / Electron injection layer) (d) (Hole injection layer / ) Hole transport layer / First phosphorescent layer / Second phosphorescent layer / Electron transport layer ( / Electron injection layer) (e) (Hole injection layer / ) Hole transport layer / Phosphorescent layer / Space layer / Fluorescent layer / Electron transport layer ( / Electron injection layer) (f) (Hole injection layer / ) Hole transport layer / First phosphorescent layer / Second phosphorescent layer / Space layer / Fluorescent layer / Electron transport layer ( / Electron injection layer) (g) (Hole injection layer / ) Hole transport layer / First phosphorescent layer / Space layer / Second phosphorescent layer / Space layer / Fluorescent layer / Electron transport layer ( / Electron injection layer) (h)(Hole injection layer / )Hole transport layer / Phosphorescent layer / Space layer / First fluorescence layer / Second fluorescence layer / Electron transport layer( / Electron injection layer) (i) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Fluorescence layer / Electron transport layer ( / Electron injection layer) (j)(Hole injection layer / )Hole transport layer / Electron blocking layer / Phosphorescent layer / Electron transport layer( / Electron injection layer) (k)(hole injection layer / )hole transport layer / exciton blocking layer / fluorescence layer / electron transport layer( / electron injection layer) (l)(Hole injection layer / )Hole transport layer / Exciton blocking layer / Phosphorescent layer / Electron transport layer( / Electron injection layer) (m)(hole injection layer / )first hole transport layer / second hole transport layer / fluorescence layer / electron transport layer( / electron injection layer) (n)(hole injection layer / )first hole transport layer / second hole transport layer / phosphorescent layer / electron transport layer( / electron injection layer) (o)(Hole injection layer / )First hole transport layer / Second hole transport layer / Fluorescence-emitting layer / First electron transport layer / Second electron transport layer( / Electron injection layer) (p)(hole injection layer / )first hole transport layer / second hole transport layer / phosphorescent layer / first electron transport layer / second electron transport layer( / electron injection layer) (q)(hole injection layer / )hole transport layer / fluorescence layer / hole blocking layer / electron transport layer( / electron injection layer) (r)(hole injection layer / )hole transport layer / phosphorescent layer / hole blocking layer / electron transport layer( / electron injection layer) (s)(hole injection layer / )hole transport layer / fluorescence layer / exciton blocking layer / electron transport layer( / electron injection layer) (t)(hole injection layer / )hole transport layer / phosphorescent layer / exciton blocking layer / electron transport layer( / electron injection layer) (m)(Hole injection layer / )First hole transport layer / Second hole transport layer / Third hole transport layer / First fluorescence emission layer / Second fluorescence emission layer / First electron transport layer / Second electron transport layer( / Electron injection layer) (n)(Hole injection layer / )First hole transport layer / Second hole transport layer / Third hole transport layer / Fluorescence-emitting layer / First electron transport layer / Second electron transport layer( / Electron injection layer)

[0282] Each of the phosphorescent or fluorescent layers described above may exhibit a different emission color from one another. Specifically, the light-emitting unit (f) may have a layer configuration such as (hole injection layer / ) hole transport layer / first phosphorescent layer (red emission) / second phosphorescent layer (green emission) / space layer / fluorescent layer (blue emission) / electron transport layer. Furthermore, an electron blocking layer may be provided between each light-emitting layer and the hole transport layer or space layer as appropriate. A hole blocking layer may also be provided between each light-emitting layer and the electron transport layer as appropriate. By providing electron blocking layers or hole blocking layers, electrons or holes can be confined within the light-emitting layer, increasing the probability of charge recombination in the light-emitting layer and improving the luminescence efficiency.

[0283] Typical device configurations for tandem organic EL elements include the following: (2) Anode / First light-emitting unit / Intermediate layer / Second light-emitting unit / Cathode Here, the first light-emitting unit and the second light-emitting unit can, for example, be independently selected from the light-emitting units described above. The above-mentioned intermediate layer is generally also called an intermediate electrode, intermediate conductive layer, charge generation layer, electron extraction layer, connecting layer, or intermediate insulating layer, and a known material configuration can be used to supply electrons to the first light-emitting unit and holes to the second light-emitting unit.

[0284] Figure 1 is a schematic diagram showing an example of the configuration of an organic EL element of the present invention. The organic EL element 1 comprises a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10 disposed between the anode 3 and the cathode 4. The light-emitting unit 10 has a light-emitting layer 5. There is a hole transport band 6 (hole injection layer, hole transport layer, etc.) between the light-emitting layer 5 and the anode 3, and an electron transport band 7 (electron injection layer, electron transport layer, etc.) between the light-emitting layer 5 and the cathode 4. Furthermore, an electron blocking layer (not shown) may be provided on the anode 3 side of the light-emitting layer 5, and a hole blocking layer (not shown) may be provided on the cathode 4 side of the light-emitting layer 5. This allows electrons and holes to be confined in the light-emitting layer 5, further increasing the exciton generation efficiency in the light-emitting layer 5.

[0285] Figure 2 is a schematic diagram showing another configuration of the organic EL element of the present invention. The organic EL element 11 includes 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 band disposed between the anode 3 and the light-emitting layer 5 is formed from a hole injection layer 6a, a first hole transport layer 6b, and a second hole transport layer 6c. The electron transport band disposed between the light-emitting layer 5 and the cathode 4 is formed from a first electron transport layer 7a and a second electron transport layer 7b.

[0286] Figure 3 is a schematic diagram showing another configuration 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 band disposed between the anode 3 and the light-emitting layer 5 is formed from a hole injection layer 6a, a first hole transport layer 6b, a second hole transport layer 6c, and a third hole transport layer 6d. The electron transport band disposed between the light-emitting layer 5 and the cathode 4 is formed from a first electron transport layer 7a and a second electron transport layer 7b.

[0287] In this invention, a host combined with a fluorescent dopant material (fluorescent material) is referred to as a fluorescent host, and a host combined with a phosphorescent dopant material is referred to as a phosphorescent host. Fluorescent hosts and phosphorescent hosts are not distinguished solely by their molecular structure. That is, a phosphorescent host refers to a material that forms a phosphorescent layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material for forming a fluorescent layer. The same applies to fluorescent hosts.

[0288] substrate The substrate is used as a support for the organic EL element. Examples of substrates include glass, quartz, and plastic plates. Flexible substrates may also be used. Examples of flexible substrates include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Inorganic vapor-deposited films can also be used.

[0289] anode For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or more). Specifically, examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium oxide containing tungsten oxide and zinc oxide, graphene, etc. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the above metals (e.g., titanium nitride).

[0290] These materials are typically deposited by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1-10 wt% zinc oxide relative to indium oxide, while indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5-5 wt% tungsten oxide and 0.1-1 wt% zinc oxide relative to indium oxide. Other methods such as vacuum deposition, coating, inkjet printing, and spin coating may also be used.

[0291] The hole injection layer formed in contact with the anode is formed using a material that facilitates hole injection regardless of the anode's work function; therefore, materials commonly used as electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, elements belonging to Group 1 or Group 2 of the periodic table) can be used. Materials with low work functions, such as elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these, can also be used. When forming an anode using alkali metals, alkaline earth metals, or alloys containing these, vacuum deposition or sputtering methods can be used. Furthermore, when using silver paste or similar materials, coating methods or inkjet methods can be employed.

[0292] Hole injection layer The hole injection layer is a layer containing a material with high hole injection potential (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.

[0293] Other hole-injectable materials besides the inventive compound include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, and the like.

[0294] These are low-molecular-weight organic compounds: 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), and 1,3,5-tris[N-(4-di Aromatic amine compounds such as phenylaminophenyl)-N-phenylamino]benzene (abbreviated as DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviated as PCzPCN1) can also be used as hole implantation layer materials.

[0295] Polymeric compounds (oligomers, dendrimers, polymers, etc.) can also be used. Examples of polymeric compounds include 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). In addition, polymeric compounds to which acids such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can be added can also be used.

[0296] Furthermore, it is also preferable to use an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K). [ka]

[0297] (In the above formula, R 21 ~R 26 These are, independently, a cyano group, -CONH2, a carboxyl group, or -COOR. 27 (R 27 (represents an alkyl group with 1 to 20 carbon atoms or a cycloalkyl group with 3 to 20 carbon atoms). Also, R 21 and R 22 , R 23 and R 24 , and R 25 and R 26 Two adjacent elements selected from the group may bond to each other to form a group represented by -CO-O-CO-. R 27 Examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, cyclopentyl group, and cyclohexyl group.

[0298] Hole transport layer The hole transport layer is a layer containing a material with high hole transport properties (hole transport material), and is formed between the anode and the light-emitting layer, or, if present, between the hole injection layer and the light-emitting layer. The inventive compound may be used alone or in combination with the following compounds in the hole transport layer.

[0299] The hole transport layer may be a single-layer structure or a multilayer structure containing two or more layers. For example, the hole transport layer may be a two-layer structure containing a first hole transport layer (anode side) and a second hole transport layer (cathode side). In other words, the hole transport band may include the first hole transport layer on the anode side and the second hole transport layer on the cathode side. Alternatively, the hole transport layer may be a three-layer structure containing a first hole transport layer, a second hole transport layer, and a third hole transport layer in order from the anode side. In other words, the third hole transport layer may be placed between the second hole transport layer and the light-emitting layer. In one embodiment of the present invention, it is preferable that the single-layer hole transport layer is adjacent to the light-emitting layer, and it is also preferable that the hole transport layer closest to the cathode in the multilayer structure, for example, the second hole transport layer in the two-layer structure, is adjacent to the light-emitting layer. Furthermore, for example, it is preferable that the third hole transport layer in the three-layer structure is adjacent to the light-emitting layer. In another embodiment of the present invention, an electron blocking layer, or the like, described later, 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 and the light-emitting layer. In the aforementioned two-layer hole transport layer, the inventive compound may be contained in either the first hole transport layer or the second hole transport layer, or in both. In one embodiment of the present invention, it is preferable that the inventive compound is contained only in the first hole transport layer; in another embodiment, it is preferable that the inventive compound is contained only in the second hole transport layer; and in yet another embodiment, it is preferable that the inventive compound is contained in both the first and second hole transport layers. In the aforementioned three-layer hole transport layer, at least one of the first to third hole transport layers may contain the inventive compound. That is, the inventive compound may be contained 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 and second hole transport layers, only the first and third hole transport layers, or only the second and third hole transport layers), or in all of the first to third hole transport layers. In one embodiment of the present invention, the inventive compound contained in one or both of the first hole transport layer and the second hole transport layer is preferably a light hydrogen compound from the viewpoint of manufacturing cost. In another embodiment of the present invention, the inventive compound contained in at least one of the first to third hole transport layers is preferably a light hydrogen compound from the viewpoint of manufacturing cost. The aforementioned light hydrogen compound refers to the inventive compound in which all hydrogen atoms are light hydrogen atoms. Accordingly, the present invention includes an organic EL element comprising an inventive compound in which one or both of the first hole transport layer and the second hole transport layer consist substantially only of light hydrogen. "Inventive compound consisting substantially only of light hydrogen" means that the content ratio of light hydrogen to the total amount of the inventive compound is 90 mol% or more, preferably 95 mol% or more, and more preferably 99 mol% or more (including 100% in each case).

[0300] Other hole transport layer materials besides the inventive compound can be used, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, and the like. Examples of aromatic amine compounds 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-phenylfluoren-9-yl)triphenylamine (abbreviated as BAFLP), and 4,4'-bis[N-(9,9-dimethylfluoren-2-yl Examples include )-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The above compounds are 10 -6 cm 2 It has a hole mobility of / Vs or greater.

[0301] Examples of carbazole derivatives include 4,4'-di(9-carbazolyl)biphenyl (abbreviated as CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviated as CzPA), and 9-phenyl-3-[4-(10-phenyl-9-antryl)phenyl]-9H-carbazole (abbreviated as PCzPA). Examples of anthracene derivatives include 2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviated as t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviated as DNA), and 9,10-diphenylanthracene (abbreviated as DPAnth). High molecular weight compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used. However, any compound with higher hole transport properties than electron transport properties may be used, other than those mentioned above.

[0302] Dopant material for the light-emitting layer The light-emitting layer is a layer containing a highly luminescent material (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 from a singlet excited state, and phosphorescent materials are compounds that emit light from a triplet excited state.

[0303] Examples of blue fluorescent materials that can be used in the light-emitting layer include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluorantene derivatives, fluorene derivatives, diamine derivatives, and triarylamine derivatives. Specifically, these include N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviated as YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviated as YGAPA), and 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCBAPA).

[0304] Aromatic amine derivatives can be used as green fluorescent luminescent materials that can be used in the light-emitting layer. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[ Examples include 9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), and N,N,9-triphenylanthracene-9-amine (abbreviation: DPhAPhA).

[0305] As red fluorescent materials that can be used in the light-emitting layer, tetracene derivatives and diamine derivatives can be used. Specifically, examples include N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviated as p-mPhTD) and 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluorantene-3,10-diamine (abbreviated as p-mPhAFD).

[0306] In one embodiment of the present invention, it is preferable that the light-emitting layer includes a fluorescent light-emitting material (fluorescent dopant material).

[0307] Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used as blue phosphorescent materials that can be used in the light-emitting layer. Specifically, examples include bis[2-(4',6'-difluorophenyl)pyridinate-N,C2']iridium(III)tetrakis(1-pyrazolyl)borate (abbreviated as FIr6), bis[2-(4',6'-difluorophenyl)pyridinate-N,C2']iridium(III) picolinate (abbreviated as FIrpic), bis[2-(3',5'bistrifluoromethylphenyl)pyridinate-N,C2']iridium(III) picolinate (abbreviated as Ir(CF3ppy)2(pic)), and bis[2-(4',6'-difluorophenyl)pyridinate-N,C2']iridium(III) acetylacetonate (abbreviated as FIracac).

[0308] Iridium complexes and the like are used as green phosphorescent materials that can be used in the light-emitting layer. Examples include tris(2-phenylpyridinato-N,C2')iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazolato)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), and bis(benzo[h]quinolinate)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)).

[0309] Metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used as red phosphorescent materials that can be used in the light-emitting layer. Specifically, examples include organometallic complexes such as bis[2-(2'-benzo[4,5-α]thienyl)pyridinate-N,C3']iridium(III) acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinolinate-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP).

[0310] Furthermore, rare earth metal complexes such as tris(acetylacetonate)(monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: Eu(DBM)3(Phen)), and tris[1-(2-tenoyl)-3,3,3-trifluoroacetonate](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3(Phen)) can be used as phosphorescent materials because the emission is due to electron transitions between different multiplicities from rare earth metal ions.

[0311] In one embodiment of the present invention, it is preferable that the light-emitting layer includes a phosphorescent material (phosphor dopant material).

[0312] Host material for the light-emitting layer The light-emitting layer may be configured by dispersing the dopant material described above in another material (host material). It is preferable to use a material that has a lower least unoccupied orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) than the dopant material.

[0313] For example, host materials include (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes, (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives, (3) Condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives, (4) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives are used.

[0314] For example, metal complexes such as tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ); Heterocyclic compounds such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), vasophenanthroline (abbreviation: BPhen), and vasocuproin (abbreviation: BCP); 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviated as CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)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-Bu DNA), 9,9'-biantryl (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)tripylene (abbreviated as TPB3), 9,10-diphenylanthracene (abbreviated as DPAnth), 6,12-dimethoxy-5,11-diphenylchrysene, and other condensed aromatic compounds; and N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H Aromatic amine compounds such as -carbazole-3-amine (abbreviated as 2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as DFLDPBi), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB) can be used. Multiple types of host materials may be used.

[0315] In particular, for blue fluorescent elements, it is preferable to use the following anthracene compounds as the host material.

[0316] [ka]

[0317] [ka]

[0318] [ka]

[0319] electron transport layer The electron transport layer is a layer containing a material with high electron transport properties (electron transport material), and is formed between the light-emitting layer and the cathode, or, if present, between the electron injection layer and the light-emitting layer. The electron transport layer may be a single layer or a multilayer structure containing two or more layers. For example, the electron transport layer may be a two-layer structure containing a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one embodiment of the present invention, it is preferable that the electron transport layer of the single layer structure is adjacent to the light-emitting layer, and it is also preferable that the electron transport layer closest to the anode in the multilayer structure, for example, the first electron transport layer of the two-layer structure, is adjacent to the light-emitting layer. In another embodiment of the present invention, a hole blocking layer, etc., described later may be interposed between the electron transport layer of the single layer structure and the light-emitting layer, or between the electron transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer.

[0320] For example, the electron transport layer includes: (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, (2) Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, (3) Polymer compounds can be used.

[0321] Examples of metal complexes include tris(8-quinolinolato)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviated as BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviated as BAlq), bis(8-quinolinolato)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviated as ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviated as ZnBTZ).

[0322] Examples of heteroaromatic compounds include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), vasophenanthroline (abbreviated as BPhen), vasocuproin (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviated as BzOs).

[0323] Examples of polymer compounds include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy).

[0324] The above materials are 10 -6 cm 2 The material has an electron mobility of / Vs or higher. However, any material with higher electron transport properties than hole transport properties may be used for the electron transport layer.

[0325] electron injection layer The electron injection layer is a layer containing a material with high electron injection potential. The electron injection layer can contain alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), rare earth metals such as europium (Eu) and ytterbium (Yb), and compounds containing these metals. Examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, rare earth metal halides, and rare earth metal-containing organic complexes. Furthermore, multiple compounds can be used in combination. In addition, materials containing alkali metals, alkaline earth metals, or compounds thereof in an electron-transporting material, specifically those containing magnesium (Mg) in Alq, may also be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, a composite material formed by mixing an organic compound with an electron donor may be used in the electron injection layer. Such a composite material exhibits excellent electron injection and electron transport properties because the organic compound accepts electrons from the electron donor. In this case, the organic compound is preferably a material with excellent electron transport properties, and specifically, for example, the materials that constitute the electron transport layer described above (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor can be any material that exhibits electron-donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides and alkaline earth metal oxides are also preferred, such as lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (abbreviated as TTF) can also be used.

[0326] cathode For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof with a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these. Furthermore, when forming a cathode using alkali metals, alkaline earth metals, or alloys containing these, vacuum deposition or sputtering methods can be used. Additionally, when using silver paste or similar materials, coating or inkjet methods can be employed. Furthermore, by providing an electron injection layer, cathodes can be formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium tin oxide containing silicon oxide, regardless of the magnitude of the work function. These conductive materials can be deposited using methods such as sputtering, inkjet printing, or spin coating.

[0327] insulating layer Organic EL elements are prone to pixel defects due to leakage and short circuits because an electric field is applied to an ultrathin film. To prevent this, an insulating layer consisting of an insulating thin film layer may be inserted between a pair of electrodes. Examples of materials used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. Mixtures or laminates of these materials may also be used.

[0328] Space layer The space layer described above is, for example, a layer provided between a fluorescent emission layer and a phosphorescent emission layer when stacking them, to prevent excitons generated in the phosphorescent emission layer from diffusing into the fluorescent emission layer, or to adjust the carrier balance. Furthermore, a space layer can also be provided between multiple phosphorescent emission layers. Since the space layer is provided between the light-emitting layers, it is preferable that the material possesses both electron-transporting and hole-transporting properties. Furthermore, in order to prevent the diffusion of triplet energy within the adjacent phosphorescent light-emitting layer, it is preferable that the triplet energy be 2.6 eV or higher. Examples of materials used for the space layer include those used for the hole-transporting layer described above.

[0329] blocking layer Blocking layers such as electron blocking layers, hole blocking layers, and exciton blocking layers may 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. An exciton blocking layer has the function of preventing excitons generated in the light-emitting layer from diffusing into surrounding layers and confining the excitons within the light-emitting layer.

[0330] Each layer of the organic EL element can be formed by conventionally known deposition methods, coating methods, etc. For example, they can be formed by known deposition methods such as vacuum deposition and molecular beam deposition (MBE), or by coating methods such as dipping, spin coating, casting, bar coating, and roll coating using a solution of the compound that forms the layer.

[0331] While there are no particular restrictions on the film thickness of each layer, generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and conversely, if it is too thick, a high driving voltage is required, resulting in poor efficiency. Therefore, the thickness is usually 5 nm to 10 μm, with 10 nm to 0.2 μm being more preferable.

[0332] In the organic EL device 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 or more and 150 nm or less, more preferably 40 nm or more and 130 nm or less. Also, in one aspect of the present invention, the thickness of the second hole transport layer of the two-layer or three-layer structure is preferably 5 nm or more, more preferably 20 nm or more, still more preferably 25 nm or more, particularly preferably 35 nm or more, and is preferably 100 nm or less. Also, in one aspect 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. Also, in another aspect 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, still more preferably 25 nm or more, particularly preferably 30 nm or more, and is preferably 100 nm or less. Also, in the organic EL device having a two-layer or three-layer hole transport layer of 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, still more preferably 0.75 < D2 / D1 < 3.0.

[0333] Preferred embodiments of the organic EL device of the present invention include, for example, (1) An organic EL device having a two-layer hole transport layer · 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; · A second embodiment in which both the first hole transport layer and the second hole transport layer contain the inventive compound; · 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; (2) An organic EL device having a three-layer hole transport layer · 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; • 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; • 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; • 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; • 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; • 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; Examples include a tenth embodiment in which all of the first to third hole transport layers contain the inventive compound; and so on.

[0334] The aforementioned 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 vehicle light fixtures. [Examples]

[0335] The present invention will be described in more detail below using examples, but the present invention is not limited to the following examples.

[0336] The inventive compound used in the manufacture of the organic EL element in Example 1 [ka]

[0337] Comparative compound used in the manufacture of the organic EL element of Comparative Example 1 [ka]

[0338] Other compounds used in the production of the organic EL elements in Example 1 and Comparative Example 1 [ka]

[0339] Fabrication of organic EL elements (I) Example 1 A glass substrate with a 25mm x 75mm x 1.1mm 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 set to 130 nm. The glass substrate with the transparent electrode, after cleaning, was mounted in the substrate holder of the vacuum deposition apparatus. First, compound 1 and compound HA were co-deposited onto the surface on which the transparent electrode was formed, covering the transparent electrode, to form 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. Next, compound 1 was deposited onto the hole injection layer to form a first hole transport layer with a thickness of 75 nm. Next, compound HT2 was deposited onto this first hole transport layer to form a second hole transport layer with a thickness of 15 nm. Next, a 20 nm thick BH (host material):BD1 (dopant material) film was deposited on this second hole transport layer. This BH:BD1 film functions as an emissive layer. The BH [compounds BH1 and BH2 (both host materials)] contained in the emissive layer are in a mass ratio of 1:1, and the concentration of BD1 is 2% by mass relative to the entire emissive layer. Next, compound ET1 was deposited onto this light-emitting layer to form a first electron transport layer with a thickness of 3 nm. Next, compound ET2 and Liq were co-deposited onto this first electron transport layer to form a second electron transport layer with a thickness of 30 nm. The mass ratio of compound ET2 to Liq (ET2:Liq) was 67:33. Next, LiF and Yb were co-deposited onto this second electron transport layer to form an electron injection electrode with a thickness of 1 nm. The mass ratio of LiF to Yb (LiF:Yb) was 50:50. Then, metallic aluminum was deposited onto this electron-injection electrode to form a metallic cathode with a thickness of 50 nm. The layer configuration of the organic EL element (I) of Example 1 obtained in this way is shown below. 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) In the above layer configuration, the numbers in parentheses represent the film thickness (nm), and the ratios represent the mass ratios.

[0340] Measurement of external quantum efficiency (EQE) The obtained organic EL element (I) was subjected to a current density of 10 mA / cm² at room temperature. 2 The system was driven by a constant DC current. Brightness was measured using a luminance meter (Minolta CS-1000 spectroradiometer), and the external quantum efficiency (%) was determined from the results. The results are shown in Table 1.

[0341] Comparative Example 1 An organic EL device (I) was fabricated in the same manner as in Example 1, except that the hole injection layer and the first hole transport layer material were replaced with the compounds shown in Table 1 below instead of compound 1, and the external quantum efficiency (EQE) was measured. The results are shown in Table 1.

[0342] [Table 1]

[0343] As is clear from the results in Table 1, the organic EL element containing the inventive compound (compound 1) exhibits superior external quantum efficiency compared to the organic EL element containing comparative compound 1.

[0344] The inventive compound used in the production of the organic EL elements (II) of Examples 2 and 3 [ka]

[0345] Comparative compounds used in the production of organic EL elements (II) of Comparative Examples 2 and 3 [ka]

[0346] Other compounds used in the manufacture of organic EL elements (II) [ka]

[0347] Fabrication of organic EL elements (II) Example 2 A glass substrate with a 25mm x 75mm x 1.1mm 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 set to 130 nm. The glass substrate with the transparent electrode, after cleaning, was mounted in the substrate holder of the vacuum deposition apparatus. First, compound 2 and compound HA were co-deposited onto the surface on which the transparent electrode was formed, 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. Next, compound 2 was deposited onto the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, compound HT3 was deposited onto this first hole transport layer to form a second hole transport layer with a thickness of 10 nm. Next, compound BH3 (host material) and compound BD2 (dopant material) were co-deposited onto this second hole transport layer to form a light-emitting layer with a thickness of 25 nm. The mass ratio of compound BH3 to compound BD2 (BH3:BD2) was 96:4. Next, compound ET3 was deposited onto this light-emitting layer to form a first electron transport layer with a thickness of 5 nm. Next, compound ET4 and Liq were co-deposited onto this first electron transport layer to form a second electron transport layer with a thickness of 20 nm. The mass ratio of compound ET4 to Liq (ET4:Liq) was 50:50. Next, LiF was deposited onto this second electron transport layer to form an electron injection electrode with a thickness of 1 nm. Then, metallic aluminum was deposited onto this electron-injection electrode to form a metallic cathode with a thickness of 50 nm. The layer configuration of the organic EL element (II) of Example 2 obtained in this way is shown below. ITO (130) / Compound 2:HA=97:3 (10) / Compound 2 (80) / HT3 (10) / BH3:BD2=96:4 (25) / ET3 (5) / ET4:Liq=50:50 (20) / LiF(1) / Al (50) In the above layer configuration, the numbers in parentheses represent the film thickness (nm), and the ratios represent the mass ratios.

[0348] 95% lifespan measurement The resulting organic EL element (II) was subjected to a current density of 50 mA / cm². 2 The device was driven with a constant DC current, and the time (h) until the brightness decreased to 95% of the initial brightness was measured. This was defined as the 95% lifetime (LT95). The results are shown in Table 2.

[0349] Example 3, and Comparative Examples 2 and 3 Organic EL element (II) was fabricated in the same manner as in Example 2, except that the hole injection layer and the first hole transport layer material were replaced with the compounds shown in Table 2 below instead of compound 2, and the 95% lifetime was measured. The results are shown in Table 2.

[0350] [Table 2]

[0351] As is clear from the results in Table 2, organic EL elements containing the bright compounds (compounds 2 and 3) have a longer lifespan than organic EL elements containing comparative compounds 2 and 3.

[0352] The inventive compound used in the production of the organic EL element (III) in Examples 4 and 5 [ka]

[0353] Comparative compound used in the manufacture of the organic EL element (III) of Comparative Example 4 [ka]

[0354] Other compounds used in the manufacture of organic EL elements (III) [ka]

[0355] Fabrication of organic EL elements (III) Example 4 A glass substrate with a 25mm x 75mm x 1.1mm 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 set to 130 nm. The glass substrate with the transparent electrode, after cleaning, was mounted in the substrate holder of the vacuum deposition apparatus. First, compound 4 and compound HA were co-deposited onto the surface on which the transparent electrode was formed, 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. Next, compound 4 was deposited onto the hole injection layer to form a first hole transport layer with a thickness of 75 nm. Next, compound HT4 was deposited onto this first hole transport layer to form a second hole transport layer with a thickness of 15 nm. Next, a 20 nm thick BH (host material):BD3 (dopant material) film was deposited on this second hole transport layer. This BH:BD3 film functions as an emissive layer. The BH [compounds BH1 and BH2 (both host materials)] contained in the emissive layer are in a mass ratio of 3:2, and the concentration of BD3 is 2% by mass relative to the entire emissive layer. Next, compound ET5 was deposited on this light-emitting layer to form a first electron transport layer with a thickness of 3 nm. Next, compound ET2 and Liq were co-deposited onto this first electron transport layer to form a second electron transport layer with a thickness of 30 nm. The mass ratio of compound ET2 to Liq (ET2:Liq) was 50:50. Next, LiF and Yb were co-deposited onto this second electron transport layer to form an electron injection electrode with a thickness of 1 nm. The mass ratio of LiF to Yb (LiF:Yb) was 50:50. Then, metallic aluminum was deposited onto this electron-injection electrode to form a metallic cathode with a thickness of 50 nm. The layer configuration of the organic EL element (III) of Example 4 obtained in this way is shown below. 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) In the above layer configuration, the numbers in parentheses represent the film thickness (nm), and the ratios represent the mass ratios.

[0356] Measurement of external quantum efficiency (EQE) The external quantum efficiency (%) of the obtained organic EL element (III) was determined in the same manner as in Example 1. The results are shown in Table 3.

[0357] Example 5 and Comparative Example 4 An organic EL device (III) was fabricated in the same manner as in Example 4, except that the hole injection layer and the first hole transport layer material were replaced with the compounds shown in Table 3 below instead of compound 4, and the external quantum efficiency (EQE) was measured. The results are shown in Table 3.

[0358] [Table 3]

[0359] As is clear from the results in Table 3, the organic EL elements containing the inventive compounds (compounds 4 and 5) exhibit superior external quantum efficiency compared to the organic EL elements containing comparative compound 4.

[0360] The inventive compound used in the production of the organic EL elements (IV) of Examples 6 and 7 [ka]

[0361] Comparative compound used in the manufacture of the organic EL element (IV) of Comparative Example 5 [ka]

[0362] Other compounds used in the manufacture of organic light-emitting diodes (IV) [ka]

[0363] Fabrication of organic light-emitting diodes (IV) Example 6 A glass substrate with a 25mm x 75mm x 1.1mm 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 set to 130 nm. The glass substrate with the transparent electrode, after cleaning, was mounted in the substrate holder of the vacuum deposition apparatus. First, compound HT5 and compound HA were co-deposited onto the surface on which the transparent electrode was formed, covering the transparent electrode, to form 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. Next, compound HT5 was deposited onto the hole injection layer to form a first hole transport layer with a thickness of 40 nm. Next, compound 1 was deposited onto this first hole transport layer to form a second hole transport layer with a thickness of 40 nm. Next, compound HT3 was deposited onto this second hole transport layer to form a third hole transport layer with a thickness of 5 nm. Next, compound BH4 (host material) and compound BD1 (dopant material) were co-deposited onto this third hole transport layer to form a light-emitting layer with a thickness of 20 nm. The mass ratio of compound BH4 to compound BD1 (BH4:BD1) was 99:1. Next, compound ET3 was deposited onto this light-emitting layer to form a first electron transport layer with a thickness of 5 nm. Next, compound ET6 and Liq were co-deposited onto this first electron transport layer to form a second electron transport layer with a thickness of 25 nm. The mass ratio of compound ET6 to Liq (ET6:Liq) was 50:50. Next, Yb was deposited onto this second electron transport layer to form an electron injection electrode with a thickness of 1 nm. Then, metallic aluminum was deposited onto this electron-injection electrode to form a metallic cathode with a thickness of 50 nm. The layer configuration of the organic EL element (IV) of Example 6 obtained in this manner is shown below. ITO (130) / HT5:HA=97:3 (10) / HT5 (40) / Compound 1 (40) / HT3 (5) / BH4:BD1=99:1 (20) / ET3 (5) / ET6:Liq=50:50 (25) / Yb (1) / Al (50) In the above layer configuration, the numbers in parentheses represent the film thickness (nm), and the ratios represent the mass ratios.

[0364] Measurement of external quantum efficiency (EQE) The external quantum efficiency (%) of the obtained organic EL element (IV) was determined in the same manner as in Example 1. The results are shown in Table 4.

[0365] Example 7 and Comparative Example 5 An organic EL device (IV) was fabricated in the same manner as in Example 6, except that the second hole transport layer material was changed from compound 1 to one of the compounds shown in Table 4 below, and the external quantum efficiency (EQE) was measured. The results are shown in Table 4.

[0366] [Table 4]

[0367] As is clear from the results in Table 4, the organic EL elements containing the inventive compounds (compounds 1 and 6) exhibit superior external quantum efficiency compared to the organic EL elements containing comparative compound 5.

[0368] The inventive compound synthesized in the synthesis example. [ka]

[0369] Intermediate synthesis example 1: Synthesis of intermediate A [ka]

[0370] 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-t-butoxide, and 580 mL of xylene was stirred at 120°C for 5 hours. After the reaction mixture was cooled to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain intermediate A, a white solid of 15.1 g. The yield was 30%.

[0371] Intermediate synthesis example 2: Synthesis of intermediate B [ka]

[0372] Under an 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 t-butoxide, and 200 mL of toluene was stirred at 90°C for 7 hours. After the reaction mixture was cooled to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain intermediate B, a white solid of 16.6 g. The yield was 97%.

[0373] Synthesis Example 1: Synthesis of Compound 1 [ka]

[0374] Under an argon atmosphere, a mixture of 7.28 g (15.0 mmol) of N-[1,1'-biphenyl]-2-yl-9,9-diphenyl-9H-fluoren-2-amine, 6.03 g (18.0 mmol) of 2-bromo-9-methyl-9-phenyl-9H-fluoren, 0.275 g (0.30 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.348 g (1.20 mmol) of tri-t-butylphosphonium tetrafluoroborate, 2.02 g (21.0 mmol) of sodium-t-butoxide, and 150 mL of xylene was stirred at 120°C for 7 hours. After cooling the reaction mixture to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain 5.20 g of a white solid. The yield was 47%. The obtained compound was identified as compound 1 based on mass spectral analysis, with a molecular weight of 739.96 and a m / e ratio of 740.

[0375] Synthesis Example 2: Synthesis of Compound 2 [ka]

[0376] In Synthesis Example 1, a white solid was obtained by the same procedure using intermediate B instead of N-[1,1'-biphenyl]-2-yl-9,9-diphenyl-9H-fluoren-2-amine and toluene instead of xylene. The yield was 46%. The obtained compound, as determined by mass spectrometry analysis (molecular weight 677.89, m / e = 678), was compound 2.

[0377] Synthesis Example 3: Synthesis of Compound 3 [ka]

[0378] In Synthesis Example 1, a white solid was obtained by the same procedure using intermediate A instead of N-[1,1'-biphenyl]-2-yl-9,9-diphenyl-9H-fluoren-2-amine. The yield was 44%. The obtained compound, as determined by mass spectral analysis (molecular weight 842.10, m / e = 842), was compound 3.

[0379] Synthesis Example 4: Synthesis of Compound 4 [ka]

[0380] In Synthesis Example 1, a white solid was obtained by the same procedure using intermediate A instead of N-[1,1'-biphenyl]-2-yl-9,9-diphenyl-9H-fluoren-2-amine and 2-bromodibenzofuran instead of 2-bromo-9-methyl-9-phenyl-9H-fluorene. The yield was 39%. The obtained compound, as determined by mass spectrometry analysis (molecular weight 753.95, m / e = 754), was compound 4.

[0381] Synthesis Example 5: Synthesis of Compound 5 [ka]

[0382] In Synthesis Example 1, a white solid was obtained by the same procedure using intermediate A instead of N-[1,1'-biphenyl]-2-yl-9,9-diphenyl-9H-fluoren-2-amine and 2-bromodibenzothiophene instead of 2-bromo-9-methyl-9-phenyl-9H-fluorene. The yield was 43%. The obtained compound, as determined by mass spectral analysis (molecular weight 770.01, m / e = 770), was compound 5.

[0383] Synthesis Example 6: Synthesis of Compound 6 [ka]

[0384] In Synthesis Example 1, a white solid was obtained by the same procedure using intermediate A instead of N-[1,1'-biphenyl]-2-yl-9,9-diphenyl-9H-fluoren-2-amine and 4-bromodibenzofuran instead of 2-bromo-9-methyl-9-phenyl-9H-fluorene. The yield was 48%. The obtained compound, as determined by mass spectrometry (molecular weight 753.95, m / e = 754), was compound 6. [Explanation of Symbols]

[0385] 1, 11, 12 Organic EL elements 2 circuit boards 3 Anode 4 cathode 5. Emitting layer 6. Hole transport zone (hole transport layer) 6a Hole injection layer 6b First Hole Transport Layer 6c Second Hole Transport Layer 6d Third Hole Transport Layer 7. Electron transport band (electron transport layer) 7a First electron transport layer 7b Second electron transport layer 10, 20, 30 Light-emitting units

Claims

1. A compound represented by the following formula (2). 【Chemistry 1】 (In formula (2), R ２０１ ~R ２０４ One of the selected groups is a methyl group, R ２０１ ~R ２０４ The other three selected from are unsubstituted phenyl groups. R ２０１ and R ２０２ They do not bond to each other and therefore do not form a ring structure. R ２０３ and R ２０４ They do not bond to each other and therefore do not form a ring structure. R ２１１ to R ２１８ and R ２２１ to R ２２８ is a hydrogen atom. however, R ２１２ , and R ２１７ One of the selected options is a single bond that connects to *m, R ２２２ , and R ２２７ One of the options selected is a single bond that connects to *n. L １１ and L １２ Each of these is independently a single bond, or a substituted or unsubstituted phenylene group. Ar １１ This is a base represented by any of the formulas (2-1) to (2-5). 【Chemistry 2】 (In formulas (2-1) to (2-5), R ２３１ ~R ２３５ , R ２４１ ~R ２４６ , R ２５１ ~R ２５５ , R ２６１ ~R ２６８ , R ２７１ ~R ２８２ , R ２９１ ~R ３００ , and R ３０１ ~R ３０８ Each of these is independently a hydrogen atom, an unsubstituted C1-C6 alkyl group, an unsubstituted ring-forming C3-C6 cycloalkyl group, or an unsubstituted ring-forming heterocyclic group with 5-18 atoms. X ２ is an oxygen atom or CR ｃ R ｄ And, R ｃ and R ｄ Each is independently a hydrogen atom or a methyl group, and R ｃ and R ｄ They do not bond to each other and therefore do not form a ring structure. however, R ２３１ ~R ２３５ One of the selected options is a single bond that connects to *o, R ２４１ ~R ２４６ One of the selected bonds is a single bond that connects to *p, R ２４１ ~R ２４６ The other one chosen from among them is a single bond that joins *q, R ２６５ ~R ２６８ One of the selected options is a single bond that connects to *r, R ２７９ ~R ２８２ One of the selected options is a single bond that connects to *s, R ２９１ , and R ２９７ ~R ３００ One of the selected options is a single bond that connects to *t. R ３０５ ~R ３０８ One of the selected options is a single bond that connects to *u, R that is not a single bond ２３１ ~R ２３５ Two adjacent R bonds selected from the above, which are not any of the single bonds mentioned above. ２４１ ~R ２４６ Two adjacent elements are selected from R ２５１ ~R ２５５ Two adjacent R bonds selected from the single bond, which are not single bonds. ２６１ ~R ２６８ Two adjacent R bonds selected from the single bond, which are not single bonds. ２７１ ~R ２８２ Two adjacent R bonds selected from the single bond, which are not single bonds. ２９１ ~R ３００ Two adjacent R bonds selected from the single bond, which are not single bonds. ３０１ ~R ３０８ Two adjacent elements selected from these elements do not bond to each other and therefore do not form a ring structure. The benzene rings A2 and B2, A2 and C2, A2 and E2, A2 and F2, and B2 and C2 are not crosslinked. *** represents the bond position to the central nitrogen atom N, p is 0 or 1, q is 0 or 1, In equations (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 R ２３１ ~R ２３５ It combines with one selected from, In equations (2-3) to (2-5), when p is 0, *o is bonded to the central nitrogen atom N. In equation (2-5), X ２ CR ｃ R ｄ And when p is 0, L １１ and L １２ At least one of those selected is a substituted or unsubstituted phenylene group, In equation (2-5), X ２ When is an oxygen atom and p is 1, R ３０６ ~R ３０８ One of the selected options is a single bond that connects to *u, R ２１２ or R ２１７ It is a single bond that connects to *m, R ２２２ or R ２２７ If it is a single bond attached to *n, then formula (2-1) excludes the p-biphenyl group.

2. L １１ and L １２ The compound according to claim 1, wherein each of them is independently a single bond or an unsubstituted phenylene group.

3. L １１ and L １２ The compound according to claim 1 or 2, wherein the bond is a single bond.

4. Ar １１ The compound according to claim 1 or 2, wherein is a group represented by any one of formulas (2-1), (2-2), and (2-5).

5. Ar １１ The compound according to claim 1 or 2, wherein is a group represented by either formula (2-1) or (2-5).

6. Ar １１ The compound according to claim 1 or 2, wherein Ar is a group represented by formula (2-1).

7. The compound according to claim 1 or 2, wherein in formula (2-1), p or q is 0.

8. The compound according to claim 1 or 2, wherein the group represented by formula (2-1) is a substituted or unsubstituted group represented by the following formula. 【Transformation 3】

9. *R is not a single bond that connects to o. ２３１ ~R ２３５ The compound according to claim 1 or 2, wherein all atoms are hydrogen atoms.

10. *R is not a single bond attached to p, nor is it a single bond attached to q. ２４１ ~R ２４６ The compound according to claim 1 or 2, wherein all atoms are hydrogen atoms.

11. R ２５１ ~R ２５５ The compound according to claim 1 or 2, wherein all atoms are hydrogen atoms.

12. R ２６１ to R ２６４ and R which is not a single bond bonded to *r ２６５ to R ２６８ The compound according to claim 1 or 2, wherein all are hydrogen atoms.

13. R ２７１ ~R ２７８ , and R which is not a single bond attached to *s ２７９ ~R ２８２ The compound according to claim 1 or 2, wherein all atoms are hydrogen atoms.

14. R ２９２ ~R ２９６ , as well as R which is not a single bond attached to *t ２９１ and R ２９７ ~R ３００ The compound according to claim 1 or 2, wherein all atoms are hydrogen atoms.

15. R ３０１ ~R ３０４ , and R which is not a single bond attached to *u ３０５ ~R ３０８ The compound according to claim 1 or 2, wherein all atoms are hydrogen atoms.

16. *R is not a single bond attached to v, nor is it a single bond attached to w, nor is it a single bond attached to x. ３１１ ~R ３１６ , R ３２１ ~R ３２５ , and R ３３１ ~R ３３５ The compound according to claim 1 or 2, wherein all atoms are hydrogen atoms.

17. The compound according to claim 1 or 2, wherein the compound represented by formula (2) contains at least one deuterium atom.

18. A material for an organic electroluminescent element having the compound described in claim 1 or 2.

19. An organic electroluminescent element having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer contains the compound described in claim 1 or 2.

20. The organic electroluminescent element according to claim 19, wherein the organic layer includes a hole transport band between the anode and the light-emitting layer, and the hole transport band includes the compound.

21. The organic electroluminescent element according to claim 20, wherein the hole transport band includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side, and the first hole transport layer, the second hole transport layer, or both contain the compound.

22. The organic electroluminescent element according to claim 21, wherein the first hole transport layer contains the compound.

23. The organic electroluminescent element according to claim 21, wherein the second hole transport layer is adjacent to the light-emitting layer.

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

25. The organic electroluminescent element according to claim 24, wherein the light-emitting layer and the third hole transport layer are in direct contact.

26. The organic electroluminescent element according to claim 19, wherein the light-emitting layer includes a fluorescent dopant material.

27. The organic electroluminescent element according to claim 19, wherein the light-emitting layer includes a phosphorescent dopant material.

28. An electronic device comprising the organic electroluminescent element described in claim 19.

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