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 (D). JPEG2026098007000266.jpg5274 (Each symbol in each formula is as defined in the specification.) An organic electroluminescent element comprising the compound, and an electronic device comprising such an organic electroluminescent element.

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

[0004] [Patent Document 1] International Publication No. 2012 / 177006 [Patent Document 2] Korean Published Patent No. 10-2016-0035971 [Patent Document 3] International Publication No. 2016 / 208862 [Patent Document 4] International Publication No. 2020 / 175948 [Patent Document 5] Korean Published Patent No. 10-2020-0131929 [Patent Document 6] International Publication No. 2022 / 71424 [Patent Document 7] U.S. Patent Application Publication No. 2018 / 0226585 [Patent Document 8] International Publication No. 2022 / 230967 [Patent Document 9] International Publication No. 2022 / 71350 [Patent Document 10] International Publication No. 2022 / 250028 [Patent Document 11] International Publication No. 2023 / 013575 [Overview of the project] [Problems that the invention aims to solve]

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

[0006] The present invention has been made to solve the aforementioned problems, and aims to provide a compound that further improves the performance of an organic EL element, an organic EL element with improved element performance, and an electronic device containing such an organic EL element. [Means for solving the problem]

[0007] The present inventors have diligently researched the performance of organic EL elements containing the compounds described in the above-mentioned patent document and other compounds, and have found that monoamines represented by the following formulas (A), (B), (C), or (D) provide organic EL elements with improved element performance.

[0008] In one embodiment, the present invention provides a compound represented by the following formula (A). [ka] (In formula (A), N * It is the central nitrogen atom. L a1 This is a single bond or a group represented by the following formulas (i) to (iii): L a1 When it is a single bond, Ara1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted naphthobenzothiophenyl group, or a substituted or unsubstituted 1-phenanthryl group, L a1 when is a group represented by the following formulas (i) to (iii), Ar a1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted naphthobenzothiophenyl group.

Chemical formula

[0009] In another aspect, the present invention provides a compound represented by the following formula (B).

Chemical formula

Chemical formula

[0010] In yet another embodiment, the present invention provides a compound represented by the following formula (C). [ka] (In formula (C), N * It is the central nitrogen atom. L c1 This is a single bond, a group represented by the following formulas (vi) or (vii). [ka] (In equations (vi) and (vii), R c31 ~R c35 One of the options selected is a single bond that connects to *c2, R c41 ~R c48 One of the selected options is a single bond that connects to *c5, Rc41 ~R c48 The other one chosen from among them is a single bond that joins *c6. R that is not a single bond c31 ~R c35 , and R that is not a single bond c41 ~R c48 These are, independently, a hydrogen atom, an unsubstituted C1-C50 alkyl group, an unsubstituted C2-C50 alkenyl group, an unsubstituted C2-C50 alkynyl group, an unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), halogen atoms, cyano groups, nitro groups, unsubstituted aryl groups with 6 to 50 ring-forming carbon atoms, or unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms, R 901 ~R 905 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 substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group. 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 903 If 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 one another. *c1 and *c4 are the central nitrogen atoms N * This represents the binding position to, *c3 and *c7 represent the bond positions to ring G. R that is not a single bond c31 ~R c35 , and R that is not a single bond c41 ~R c48 Two adjacent elements selected from this set do not join to each other and do not form a ring. Ar c1 This is a group represented by the following formula (c1) or (c2). [ka] (In formula (c1), *c8 is the central nitrogen atom N * This indicates the connection position to the destination. L c2 This refers to a substituted or unsubstituted arylene group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group with 5 to 30 ring-forming atoms. R c101 ~R c108 One of the options selected is a single bond that connects to *c9. R that is not a single bond c101 ~R c108 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heterocyclic group. R that is not a single bond c101 ~R c108 Two adjacent elements selected from this list do not join to each other and do not form a ring. However, L c2 R is a substituted or unsubstituted phenylene group, c101 , R c104 , R c105 and R c108 When one of the selected bonds is a single bond that connects to *c9, L c2 The substituted or unsubstituted phenylene group represented by is a substituted or unsubstituted o-phenylene group, or a substituted or unsubstituted m-phenylene group. [ka] (In formula (c2), *c10 is the central nitrogen atom N * This indicates the connection position to the destination. L c3 This refers to a substituted or unsubstituted arylene group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group with 5 to 30 ring-forming atoms. X c1 This is either an oxygen atom or a sulfur atom. R c111 ~R c118 One of the options selected is a single bond that connects to *c11. R that is not a single bond c111 ~R c118 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heterocyclic group. R that is not a single bond c111 ~R c118 Two adjacent elements selected from the set may join together to form a substituted or unsubstituted ring structure, or they may not join together and therefore not form a ring structure. R c1 ~R c4 This is a hydrogen atom. R c11 ~R c17 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, The aforementioned R c11 ~R c17 Two adjacent elements selected from this list do not join to each other and do not form a ring. Rings E and F may or may not be bridged. R c21 This is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group. R c22 ~R c29Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heterocyclic group.

[0011] In yet another embodiment, the present invention provides a compound represented by the following formula (D). [ka] (In formula (D), N * It is the central nitrogen atom. L d1 This is a group represented by the following formula (viii). [ka] (In formula (viii), R d31 and R d35 One of the options selected is a single bond that connects to *d3. R that is not a single bond d31 and R d35 These are, independently, a hydrogen atom, an unsubstituted C1-C50 alkyl group, an unsubstituted C2-C50 alkenyl group, an unsubstituted C2-C50 alkynyl group, an unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), halogen atoms, cyano groups, nitro groups, unsubstituted aryl groups with 6 to 50 ring-forming carbon atoms, or unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms, R 901 ~R 905 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 substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group. R901 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 903 If 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 one another. *d2 is the central nitrogen atom N * Represents the binding position to *d1 is R d21 ~R d28 It combines with one selected from the options. R that is not a single bond d31 ~R d35 Two adjacent elements selected from this set do not join to each other and do not form a ring. Ar d1 This is a group represented by one of the following formulas (d1) to (d3). [ka] (In formula (d1), *d7 is the central nitrogen atom N * This indicates the connection position to the destination. R d101 ~R d105 One of the selected options is a single bond that connects to *d8, R d106 ~R d110 One of the options selected is a single bond that joins to *d9. R that is not a single bond d101 ~R d105 , and R that is not a single bond d106 ~R d110Each of these is independently a hydrogen atom, an unsubstituted C1-C10 alkyl group, an unsubstituted ring-forming C6-C12 aryl group, or an unsubstituted ring-forming C5-C12 heterocyclic group. R that is not a single bond d101 ~R d105 Two adjacent elements selected from this set do not join with each other and do not form a ring. R that is not a single bond d106 ~R d110 Two adjacent elements selected from this list do not join to each other and do not form a ring. R d111 ~R d115 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heterocyclic group. R d111 ~R d115 Two adjacent elements selected from this list do not join to each other and do not form a ring. m is either 0 or 1, and n is either 0 or 1. When m=0 and n=0, *d9 represents *d7, When m=0 and n=1, *d8 represents *d7, When m=1 and n=0, *d9 represents *d8. [ka] (In formula (d2), *d10 is the central nitrogen atom N * This indicates the connection position to the destination. L d2 This refers to a substituted or unsubstituted arylene group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group with 5 to 30 ring-forming atoms. R d121 ~R d128 One of the options selected is a single bond that connects to *d11. R that is not a single bond d121 ~R d128Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heterocyclic group. R that is not a single bond d121 ~R d128 Two adjacent elements selected from this set do not join to each other and do not form a ring. [ka] (In equation (d3), *d12 is the central nitrogen atom N * This indicates the connection position to the destination. L d3 This refers to a substituted or unsubstituted arylene group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group with 5 to 30 ring-forming atoms. X d1 This is either an oxygen atom or a sulfur atom. R d131 ~R d138 One of the options selected is a single bond that connects to *a14. R that is not a single bond d131 ~R d138 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heterocyclic group. R that is not a single bond d131 ~R d138 Two adjacent elements selected from the set may join together to form a substituted or unsubstituted ring structure, or they may not join together and therefore not form a ring structure. R d1 ~R d4 This is a hydrogen atom. R d11 ~R d17 Each of these is independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. The aforementioned R d11 ~R d17Two adjacent elements selected from this list do not join to each other and do not form a ring. Ring H and ring I may or may not be bridged. *R is not a single bond attached to d1. d21 ~R d28 Each of these is independently a hydrogen atom or a substituted or unsubstituted ring-forming carbon-6 aryl group. *R is not a single bond attached to d1. d21 ~R d28 At least one of these selected is the aforementioned substituted or unsubstituted ring-forming aryl group with 6 carbon atoms.

[0012] In yet another embodiment, the present invention provides a material for an organic EL element comprising a compound represented by formula (A), (B), (C), or (D).

[0013] In yet another embodiment, the present invention provides an organic electroluminescent element comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer comprises a compound represented by formula (A), (B), (C), or (D).

[0014] In yet another embodiment, the present invention provides an electronic device comprising the organic electroluminescent element. [Effects of the Invention]

[0015] Organic EL elements containing the compound represented by formula (A), (B), (C), or (D) exhibit improved element performance. [Brief explanation of the drawing]

[0016] [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]

[0017] [Definition] In this specification, the term "hydrogen atom" includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0018] 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.

[0019] 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.

[0020] 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.

[0021] 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.

[0022] 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.

[0023] 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.

[0024] "Substituents as described herein" The substituents described herein will be explained below.

[0025] 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.

[0026] • "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.

[0027] • 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, 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).

[0028] [ka]

[0029] [ka]

[0030] • 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.

[0031] • "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 is either a monocyclic group or a fused-cyclic 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.

[0032] 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).

[0033] 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).

[0034] • 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.

[0035] • 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.

[0036] • 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).

[0037] • 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):

[0038] [ka]

[0039] [ka]

[0040] 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.

[0041] • 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.

[0042] • 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].

[0043] • 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].

[0044] • 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):

[0045] 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.

[0046] • "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.

[0047] • 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.

[0048] • Substituting alkyl groups (specific examples group G3B): Heptafluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.

[0049] • "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.

[0050] • Unsubstituted alkenyl groups (specific examples group G4A): vinyl group, allyl group, 1-Butenyl group, 2-butenyl group, and 3-Butenyl group.

[0051] • 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.

[0052] • "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.

[0053] • Unsubstituted alkynyl groups (specific examples group G5A): Ethynyl group

[0054] • "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.

[0055] • 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.

[0056] • Substituting cycloalkyl groups (specific examples group G6B): 4-methylcyclohexyl group.

[0057] · "-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.

[0058] ·「-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.

[0059] · "-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.

[0060] · "-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) 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. 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), multiple G6s are either identical or different from one another.

[0061] • "Halogen atom" Specific examples of "halogen atoms" as described herein (Specific Examples Group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0062] • "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.

[0063] • "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.

[0064] • "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.

[0065] • "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.

[0066] • "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.

[0067] • "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.

[0068] • "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.

[0069] • "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 atoms of an "alkyl group" are 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.

[0070] 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.

[0071] 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.

[0072] In this specification, unless otherwise specified, the carbazolyl group is specifically one of the following groups:

[0073] [ka]

[0074] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically one of the following groups:

[0075] [ka]

[0076] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bond position.

[0077] In this specification, unless otherwise specified, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups:

[0078] [ka]

[0079] In the general formulas (TEMP-34) to (TEMP-41) above, * represents a bond position.

[0080] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t-butyl groups.

[0081] • "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.

[0082] • "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.

[0083] • "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.

[0084] Unless otherwise specified herein, the substituted or unsubstituted arylene groups are preferably any of the following general formulas (TEMP-42) to (TEMP-68).

[0085] [ka]

[0086] [ka]

[0087] 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.

[0088] [ka]

[0089] 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.

[0090] [ka]

[0091] 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.

[0092] 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).

[0093] [ka]

[0094] [ka]

[0095] [ka]

[0096] In the general formulas (TEMP-69) to (TEMP-82) above, Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0097] [ka]

[0098] [ka]

[0099] [ka]

[0100] [ka]

[0101] In the general formulas (TEMP-83) to (TEMP-102) above, Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0102] The above is a description of the substituents described herein.

[0103] • "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.

[0104] [ka]

[0105] 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.

[0106] 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).

[0107] [ka]

[0108] 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.

[0109] [ka]

[0110] 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 (TEMP-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 (TEMP-104) A If it is a naphthalene ring, then ring Q A It is a condensed ring.

[0111] 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.

[0112] 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.

[0113] 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").

[0114] • 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, an unsubstituted alkyl group having 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, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted 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.

[0115] 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.

[0116] 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.

[0117] Specific examples of each of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents as described herein" above.

[0118] 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.

[0119] 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.

[0120] The compounds of the present invention will be described below. The compounds of the present invention are represented by formula (A), (B), (C), or (D). Hereinafter, formula (A), (B), (C), or (D), and the symbols in each of the formulas (A), (B), (C), or (D) described later will be explained. Unless otherwise specified, the same symbols have the same meaning. The compounds of the present invention represented by formula (A), (B), (C), or (D), and the formulas described later that are included in formula (A), (B), (C), or (D), are sometimes referred to as "inventive compounds."

[0121] The first compound of the present invention (inventive compound (A)) is represented by the following formula (A).

[0122] [ka]

[0123] In formula (A), N * It is the central nitrogen atom. L a1 This is a single bond or a group represented by the following formulas (i) to (iii): L a1When it is a single bond, Ar a1 This is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted naphthobenzothiophenyl group, or a substituted or unsubstituted 1-phenanthryl group. L a1 When the group is represented by the following formulas (i) to (iii), Ar a1 This is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted naphthobenzothiophenyl group.

[0124] [ka]

[0125] In formulas (i) to (iii), R a21 ~R a25 One of the selected options is a single bond that connects to *a2, R a31 ~R a38 One of the selected options is a single bond that connects to *a5, R a31 ~R a38 The other one chosen from is a single bond that joins *a6, R a41 ~R a45 One of the selected options is a single bond that connects to *a9, R a51 ~R a55 The other one selected is a single bond that connects to *a10.

[0126] In one embodiment of the present invention, preferably R a21 , R a22 , R a24 , or R a25 This is a single bond that connects to a2, more preferably Ra22 or R a24 This is a single bond that connects to *a2.

[0127] R that is not a single bond a21 ~R a25 , R which is not a single bond a31 ~R a38 , R which is not a single bond a41 ~R a45 , and R that is not a single bond a51 ~R a55 Each of these independently comprises a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, preferably 1 to 20, more preferably 1 to 6 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, preferably 2 to 20, more preferably 2 to 6 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, preferably 2 to 20, more preferably 2 to 6 carbon atoms, an unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, preferably 3 to 20, more preferably 3 to 6 carbon atoms, and -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), halogen atoms, cyano groups, nitro groups, unsubstituted aryl groups having 6 to 50, preferably 6 to 30, more preferably 6 to 18 ring-forming carbon atoms, or unsubstituted heterocyclic groups having 5 to 50, preferably 5 to 30, more preferably 5 to 18 ring-forming atoms, R 901 ~R 905 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, preferably 1 to 20, more preferably 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, preferably 3 to 20, more preferably 3 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, preferably 6 to 30, more preferably 6 to 18 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, preferably 5 to 30, more preferably 5 to 18 carbon 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 R902 They are either identical or different from each other. R 903 If 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 one another. *a1, *a4, and *8 are the central nitrogen atoms N * This represents the binding position to, *a3, *a7, and *11 are Ar a1 This indicates the connection position to the destination. R that is not a single bond a21 ~R a25 , R which is not a single bond a31 ~R a38 , R which is not a single bond a41 ~R a45 , and R that is not a single bond a51 ~R a55 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0128] R that is not a single bond a21 ~R a25 , R which is not a single bond a31 ~R a38 , R which is not a single bond a41 ~R a45 , and R that is not a single bond a51 ~R a55 Details of the unsubstituted C1-C50 alkyl group represented by are as described above in the section "Substituents as described herein". The unsubstituted alkyl group is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, or a t-butyl group, and more preferably a methyl group, an isopropyl group, or a t-butyl group.

[0129] R that is not a single bond a21 ~R a25, R which is not a single bond a31 ~R a38 , R which is not a single bond a41 ~R a45 , and R that is not a single bond a51 ~R a55 Details of the unsubstituted C2-C50 alkenyl group represented by are as described above in the section "Substituents as described herein".

[0130] R that is not a single bond a21 ~R a25 , R which is not a single bond a31 ~R a38 , R which is not a single bond a41 ~R a45 , and R that is not a single bond a51 ~R a55 Details of the 2 to 50 unsubstituted alkynyl groups represented by are as described above in the section "Substituents as described herein".

[0131] R that is not a single bond a21 ~R a25 , R which is not a single bond a31 ~R a38 , R which is not a single bond a41 ~R a45 , and R that is not a single bond a51 ~R a55 Details of the unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms represented by are as described above in the section "Substituents as described herein". The unsubstituted cycloalkyl group is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, or an adamantyl group.

[0132] R that is not a single bond a21 ~R a25 , R which is not a single bond a31 ~R a38 , R which is not a single bond a41 ~R a45 , and R that is not a single bond a51 ~R a55The details of the halogen atom represented are as described above in the section "Substituents as described herein," and it is preferably a fluorine atom.

[0133] R that is not a single bond a21 ~R a25 , R which is not a single bond a31 ~R a38 , R which is not a single bond a41 ~R a45 , and R that is not a single bond a51 ~R a55 Details of the unsubstituted ring-forming aryl group having 6 to 50 carbon atoms represented by are as described above in the section "Substituents as described herein". The unsubstituted aryl group is preferably a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, or a fluorenyl group.

[0134] R that is not a single bond a21 ~R a25 , R which is not a single bond a31 ~R a38 , R which is not a single bond a41 ~R a45 , and R that is not a single bond a51 ~R a55 Details of the unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms represented by are as described above in the section "Substituents as described herein". The unsubstituted heterocyclic group is preferably a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.

[0135] The aforementioned R 901 ~R 905 Details of the unsubstituted C1-C50 alkyl group represented by and preferred examples thereof are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0136] The aforementioned R 901 ~R 905Details and preferred examples of unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0137] The aforementioned R 901 ~R 905 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 50 carbon atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0138] The aforementioned R 901 ~R 905 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0139] R that is not a single bond a21 ~R a25 , R which is not a single bond a31 ~R a38 , R which is not a single bond a41 ~R a45 , and R that is not a single bond a51 ~R a55 Each of these is independently preferably a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.

[0140] R that is not a single bond a21 ~R a25 All of them may be hydrogen atoms, and R which is not a single bond a31 ~R a38 However, they may all be hydrogen atoms, and the R that is not a single bond may also be a41 ~R a45However, they may all be hydrogen atoms, and the R that is not a single bond may also be a51 ~R a55 However, they could all be hydrogen atoms.

[0141] In one embodiment of the present invention, L a1 It is preferable that the bond is a single bond. In another embodiment of the present invention, L a1 It is preferable that the group is represented by formula (i) above.

[0142] In one embodiment of the present invention, Ar a1 Preferably, is a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted carbazolyl group, more preferably a substituted or unsubstituted 1-naphthyl group, or a group represented by the following formula (a4).

[0143] [ka]

[0144] In formula (a4), *a15 is L a1 This indicates the connection position to the destination. R a151 ~R a158 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms. R a151 ~R a158 Two adjacent elements selected from the set do not bond to each other and therefore do not form a ring structure.

[0145] In one embodiment of the present invention, L a1 It is a single bond, and Ar a1 It is preferable that the group is a substituted or unsubstituted naphthyl group. In another embodiment of the present invention, L a1 is a group represented by the above formula (i), and Ar a1It is preferably a substituted or unsubstituted carbazolyl group, L a1 is a group represented by the above formula (i), and Ar a1 It is more preferable that the group is represented by formula (a4) above.

[0146] The aforementioned R a151 ~R a158 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are described below as R, which is not a single bond. a101 ~R a105 , and R that is not a single bond a106 ~R a110 As described above, this applies to unsubstituted alkyl groups with 1 to 10 carbon atoms.

[0147] The aforementioned R a151 ~R a158 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 12 carbon atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 As described above, this applies to unsubstituted ring-forming aryl groups with 6 to 12 carbon atoms.

[0148] The aforementioned R a151 ~R a158The unsubstituted heterocyclic groups with 5 to 13 ring-forming atoms represented by include, for example, pyrrolyl, furyl, thienyl, pyridyl, imidazopyridyl, pyridadinyl, pyrimidinyl, pyrazinyl, triazinyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, and indolyl groups. Isoindolyl group, indolidinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, benzooxazolyl group, benzothiazolyl group, indazolyl group, benzoisoxazolyl group, benzoisothiazolyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group (be The group is an isobenzothienyl group (hereinafter the same), an isobenzothiophenyl group (isobenzothienyl group, hereinafter the same), a dibenzothiophenyl group (dibenzothienyl group, hereinafter the same), or a carbazolyl group, preferably a pyrrolyl group, furyl group, thienyl group, pyridyl group, pyrimidinyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, benzimidazolyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group, isobenzothiophenyl group, dibenzothiophenyl group, or a carbazolyl group, more preferably a benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group, isobenzothiophenyl group, dibenzothiophenyl group, or a carbazolyl group (9-carbazolyl group, or 1-, 2-, 3- or 4-carbazolyl group). The substituted heterocyclic groups with 5 to 13 ring-forming atoms are, for example, 9-phenylcarbazolyl group, 9-biphenylylcarbazolyl group, 9-phenylphenylcarbazolyl group, 9-naphthylcarbazolyl group, phenyldibenzofuranyl group, or phenyldibenzothiophenyl group (phenyldibenzothienyl group, the same applies hereinafter). The aforementioned substituted or unsubstituted heterocyclic groups having 5 to 13 ring-forming atoms include isomers if present.

[0149] In another embodiment of the present invention, Ara1 This is preferably a substituted or unsubstituted 1-phenanthryl group, and more preferably a group represented by the following formula (a5).

[0150] [ka]

[0151] In formula (a5), *a20 is L a1 This indicates the connection position to the destination. R a161 ~R a169 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms. R a161 ~R a169 Two adjacent elements selected from the set do not bond to each other and therefore do not form a ring structure.

[0152] The aforementioned R a161 ~R a169 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are described below as R, which is not a single bond. a101 ~R a105 , and R that is not a single bond a106 ~R a110 As described above, this applies to unsubstituted alkyl groups with 1 to 10 carbon atoms.

[0153] The aforementioned R a161 ~R a169 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 12 carbon atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 As described above, this applies to unsubstituted ring-forming aryl groups with 6 to 12 carbon atoms.

[0154] The aforementioned R a161 ~Ra169 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 13 ring-forming atoms represented by R a151 ~R a158 As described above, this applies to unsubstituted heterocyclic groups with 5 to 13 ring-forming atoms.

[0155] In one embodiment of the present invention, R a161 ~R a169 It is preferable that it be a hydrogen atom.

[0156] Ar a2 This is a group represented by one of the following formulas (a1) to (a3).

[0157] [ka]

[0158] In formula (a1), *a12 is the central nitrogen atom N * This indicates the connection position to the destination. R a101 ~R a105 One of the selected bonds is a single bond that connects to *a13, R a106 ~R a110 One of the options selected is a single bond that connects to *a14. R that is not a single bond a101 ~R a105 , and R that is not a single bond a106 ~R a110 Each of these is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 12 ring-forming carbon atoms. R that is not a single bond a101 ~R a105 Two adjacent elements selected from this set do not join with each other and do not form a ring. R that is not a single bond a106 ~R a110 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0159] R that is not a single bond a101 ~R a105 , and R that is not a single bond a106 ~R a110 The unsubstituted C1-C10 alkyl group represented by is, for example, a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, or decyl group, preferably a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, or hexyl group, more preferably a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, or t-butyl group, even more preferably a methyl group or a t-butyl group, and even more preferably a t-butyl group.

[0160] R that is not a single bond a101 ~R a105 , and R that is not a single bond a106 ~R a110 The unsubstituted ring-forming aryl group having 6 to 12 carbon atoms represented by is, for example, a phenyl group, a biphenyl group, or a naphthyl group, preferably a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group, more preferably a phenyl group or a 1- or 2-naphthyl group, and even more preferably a phenyl group.

[0161] R that is not a single bond a101 ~R a105 , and R that is not a single bond a106 ~R a110The unsubstituted heterocyclic groups with 5 to 12 ring-forming atoms represented by include, for example, pyrrolyl, furyl, thienyl, pyridyl, imidazopyridyl, pyridadinyl, pyrimidinyl, pyrazinyl, triazinyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, and indolyl groups. Isoindolyl group, indolidinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, benzooxazolyl group, benzothiazolyl group, indazolyl group, benzoisoxazolyl group, benzoisothiazolyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group (be The group is an isobenzothienyl group (hereinafter the same), an isobenzothiophenyl group (isobenzothienyl group, hereinafter the same), a dibenzothiophenyl group (dibenzothienyl group, hereinafter the same), or a carbazolyl group, preferably a pyrrolyl group, furyl group, thienyl group, pyridyl group, pyrimidinyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, benzimidazolyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group, isobenzothiophenyl group, dibenzothiophenyl group, or a carbazolyl group, more preferably a benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group, isobenzothiophenyl group, dibenzothiophenyl group, or a carbazolyl group (9-carbazolyl group, or 1-, 2-, 3- or 4-carbazolyl group). The substituted heterocyclic groups with 5 to 12 ring-forming atoms are, for example, 9-phenylcarbazolyl group, 9-biphenylylcarbazolyl group, 9-phenylphenylcarbazolyl group, 9-naphthylcarbazolyl group, phenyldibenzofuranyl group, or phenyldibenzothiophenyl group (phenyldibenzothienyl group, the same applies hereinafter). The aforementioned substituted or unsubstituted heterocyclic groups having 5 to 12 ring-forming atoms include isomers if present.

[0162] R a111 ~Ra115 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms. R a111 ~R a115 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0163] The aforementioned R a111 ~R a115 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0164] The aforementioned R a111 ~R a115 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 12 carbon atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0165] The aforementioned R a111 ~R a115 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 13 ring-forming atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The above applies to heterocyclic groups with 5 to 12 ring-forming atoms represented by .

[0166] R that is not a single bond a101 ~R a105 All of them may be hydrogen atoms, and R which is not a single bond a106 ~R a110 R may all be hydrogen atoms, a111 ~R a115It is also possible that all of them are hydrogen atoms.

[0167] m is either 0 or 1, and n is either 0 or 1. When m=0 and n=0, *a14 represents *a12, When m=0 and n=1, *a13 represents *a12, When m=1 and n=0, *a14 represents *a13.

[0168] In one embodiment of the present invention, m is 0 and n is 0. In this case, *a14 represents *a12, and equation (a1) is expressed by the following equation.

[0169] [ka]

[0170] In another embodiment of the present invention, m is 0 and n is 1. In this case, *a13 represents *a12, and formula (a1) is expressed by the following formula.

[0171] [ka]

[0172] In another embodiment of the present invention, m is 1 and n is 0. In this case, *a14 represents *a13, and formula (a1) is expressed by the following formula.

[0173] [ka]

[0174] In another embodiment of the present invention, m is 1 and n is 1. In this case, formula (a1) is expressed as follows:

[0175] [ka]

[0176] The base represented by formula (a1) is preferably represented by the following formula. In the following formula, R is omitted for simplification. R is not the single bond mentioned above. a101 ~R a105 , and R that is not a single bond a106 ~R a110 , or the R a111 ~R a115 It is identical to [the other one].

[0177] [ka]

[0178] The base represented by formula (a1) is more preferably represented by the following formula.

[0179] [ka]

[0180] [ka]

[0181] In formula (a2), *a15 is the central nitrogen atom N * This indicates the connection position to the destination. R a131 ~R a138 One of the options selected is a single bond that connects to *a16. R a121 ~R a124 , and R that is not a single bond a131 ~R a138 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms. R a121 ~R a124 , and R that is not a single bond a131 ~R a138Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0182] The aforementioned R a121 ~R a124 , and R that is not a single bond a131 ~R a138 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0183] The aforementioned R a121 ~R a124 , and R that is not a single bond a131 ~R a138 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 12 carbon atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0184] The aforementioned R a121 ~R a124 , and R that is not a single bond a131 ~R a138 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 13 ring-forming atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The above applies to heterocyclic groups with 5 to 12 ring-forming atoms represented by .

[0185] In one embodiment of the present invention, R a132 , R a133 , R a136 , and R a137 Preferably, one of the selected bonds is a single bond that connects to *a16.

[0186] The aforementioned R a121 ~R a124All of them may be hydrogen atoms, and R which is not a single bond a131 ~R a138 These may all be hydrogen atoms.

[0187] The aforementioned R a121 ~R a124 At least one of those selected may be a deuterium atom.

[0188] [ka]

[0189] In formula (a3), *a17 is the central nitrogen atom N * This indicates the connection position to the destination. L a2 This is a substituted or unsubstituted arylene group having 6 to 30, preferably 6 to 18, more preferably 6 to 12, ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30, preferably 5 to 18, more preferably 5 to 12, ring-forming atoms.

[0190] Said L a2 The unsubstituted ring-forming arylene group having 6 to 30 carbon atoms represented by is, for example, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, anthreene group, a benzoantrylene group, a phenanthrylene group, a benzophenanthrylene group, a phenalenylene group, a picenylene group, a pentaphenylene group, a pyrenylene group, a chrysenylene group, a benzochrysenylene group, a triphenylenylene group, a fluorantheylene group, a fluorenylene group, or a 9,9'-spirobifluorenylene group, preferably a phenylene group, a biphenylene group, a terphenylene group, or a naphthylene group, more preferably a phenylene group or a biphenylene group, and even more preferably a phenylene group.

[0191] Said L a2 The unsubstituted, divalent heterocyclic group with 5 to 30 ring-forming atoms represented by this symbol is a divalent group obtained by removing one hydrogen atom from an unsubstituted, heterocyclic group with 5 to 30 ring-forming atoms. Unsubstituted heterocyclic groups with 5 to 30 ring-forming atoms include, for example, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridyl, pyridadinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, indolidine, quinolidinyl, quinolyl, isoquinolyl, cinnolyl, phthalazinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, indazolyl, phenanthrolinyl, phenanthridine, acridinyl, phenazinyl, carbazolyl, benzocarbazolyl, furyl, xanthenyl The group is a benzofuranyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzoisoxazolyl group, phenoxazinyl group, thienyl group, benzothiophenyl group, isobenzothiophenyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, benzothiazolyl group, benzoisothiazolyl group, or phenothiazinyl group, preferably a carbazolyl group (9-carbazolyl group, or 1-, 2-, 3- or 4-carbazolyl group), benzofuranyl group, isobenzofuranyl group, naphthobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group, isobenzothiophenyl group, dibenzothiophenyl group, or naphthobenzothiophenyl group.

[0192] L a2 Preferably, it is a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, more preferably a substituted or unsubstituted ring-forming arylene group having 6 to 12 carbon atoms, even more preferably a substituted or unsubstituted phenylene group, and even more preferably an unsubstituted phenylene group.

[0193] X a1 This is an oxygen atom or a sulfur atom, preferably an oxygen atom. R a141 ~R a148 One of the options selected is a single bond that connects to *a18.

[0194] R that is not a single bond a141 ~R a148 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms. R that is not a single bond a141 ~R a148 Two adjacent elements selected from the set may join to form a substituted or unsubstituted ring structure, or they may not join to each other and therefore not form a ring structure.

[0195] R that is not a single bond a141 ~R a148 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0196] R that is not a single bond a141 ~R a148 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 12 carbon atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0197] R that is not a single bond a141 ~R a148 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 13 ring-forming atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The above applies to heterocyclic groups with 5 to 12 ring-forming atoms represented by .

[0198] R that is not a single bond a141 ~R a148It is also possible that all of them are hydrogen atoms.

[0199] Ar a2 Preferably, it has at least one deuterium atom. Also, Ar a2 Preferably, the group is represented by formula (a2) above.

[0200] R a1 ~R a4 This is a hydrogen atom. R a11 ~R a17 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, preferably 1 to 20, more preferably 1 to 6 carbon atoms, The aforementioned R a11 ~R a17 Two adjacent elements selected from this list do not join to each other and do not form a ring. Ring A and Ring B may or may not be bridged. When ring A and ring B are bridged, The ring structure formed by the bridging of ring A and ring B has at least one deuterium atom, If ring A and ring B are not bridged, R a1 ~R a4 At least one of the atoms selected is a deuterium atom.

[0201] Furthermore, the phrase "the ring structure formed by the bridging of ring A and ring B has at least one deuterium atom" means that deuterium is directly bonded to the ring constituent atoms that make up the ring structure formed by the bridging of ring A and ring B.

[0202] The aforementioned R a11 ~R a17 Details of the unsubstituted C1-C50 alkyl group represented by and preferred examples thereof are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0203] The aforementioned Ra11 ~R a17 These may all be hydrogen atoms.

[0204] The ring structure formed by the bridge of ring A and ring B is, for example, a dibenzofuran structure, a dibenzothiophene structure, a carbazole structure, or a fluorantene structure, and is preferably a dibenzofuran structure.

[0205] In one embodiment of the present invention, R a1 ~R a4 All of them are deuterium atoms, and Ar a2 is a group represented by the above formula (a2), and R a121 ~R a124 Preferably, all of them are deuterium atoms.

[0206] The compound represented by formula (A) may contain only deuterium atoms.

[0207] The second compound of the present invention (inventive compound (B)) is represented by the following formula (B).

[0208] [ka]

[0209] In formula (B), N * It is the central nitrogen atom. L b1 This is a single bond, a group represented by formula (iv) or (v) below.

[0210] [ka]

[0211] In equations (iv) and (v), R b41 ~R b45 One of the options is a single bond that connects to *b2, R b51 ~R b58One of the selected options is a single bond that connects to *b5, R b51 ~R b58 The other one chosen from among them is a single bond that joins *b6.

[0212] In one embodiment of the present invention, preferably R b43 This is a single bond that connects to *b2. R that is not a single bond b41 ~R b45 , and R that is not a single bond b51 ~R b58 Each of these independently comprises a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, preferably 1 to 20, more preferably 1 to 6 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, preferably 2 to 20, more preferably 2 to 6 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, preferably 2 to 20, more preferably 2 to 6 carbon atoms, an unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, preferably 3 to 20, more preferably 3 to 6 carbon atoms, and -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), halogen atoms, cyano groups, nitro groups, unsubstituted aryl groups having 6 to 50, preferably 6 to 30, more preferably 6 to 18 ring-forming carbon atoms, or unsubstituted heterocyclic groups having 5 to 50, preferably 5 to 30, more preferably 5 to 18 ring-forming atoms, R 901 ~R 905 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, preferably 1 to 20, more preferably 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, preferably 3 to 20, more preferably 3 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, preferably 6 to 30, more preferably 6 to 18 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, preferably 5 to 30, more preferably 5 to 18 carbon 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 902If 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 903 If 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 one another. *b1 and *b4 are the central nitrogen atoms N * This represents the binding position to, *b3 and *b7 are Ar b1 This indicates the connection position to the destination. R that is not a single bond b41 ~R b45 , and R that is not a single bond b51 ~R b58 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0213] R that is not a single bond b41 ~R b45 , and R that is not a single bond b51 ~R b58 Details of the unsubstituted C1-C50 alkyl group represented by and preferred examples thereof are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0214] R that is not a single bond b41 ~R b45 , and R that is not a single bond b51 ~R b58 Details of the unsubstituted C2-C50 alkenyl group represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0215] R that is not a single bond b41 ~R b45 , and R that is not a single bond b51 ~R b58 Details of the unsubstituted alkynyl groups 2 to 50 represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0216] R that is not a single bond b41 ~R b45 , and R that is not a single bond b51 ~R b58 Details and preferred examples of unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0217] R that is not a single bond b41 ~R b45 , and R that is not a single bond b51 ~R b58 Details of the halogen atom represented and preferred examples thereof are R, which is not a single bond. a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0218] R that is not a single bond b41 ~R b45 , and R that is not a single bond b51 ~R b58 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 50 carbon atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0219] R that is not a single bond b41 ~R b45 , and R that is not a single bond b51 ~R b58 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0220] The aforementioned R 901 ~R 905 Details of the unsubstituted C1-C50 alkyl group represented by and preferred examples thereof are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0221] The aforementioned R 901 ~R 905 Details and preferred examples of unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0222] The aforementioned R 901 ~R 905 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 50 carbon atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0223] The aforementioned R 901 ~R 905 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38It is as described above.

[0224] R other than the single bond b41 ~R b45 and R other than the single bond b51 ~R b58 are each independently preferably a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.

[0225] R other than the single bond b41 ~R b45 may all be hydrogen atoms, and R other than the single bond b51 ~R b58 may all be hydrogen atoms.

[0226] In one embodiment of the present invention, L b1 is preferably a single bond. In another embodiment of the present invention, L b1 is preferably a group represented by the above formula (iv).

[0227] Ar b1 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, preferably 6 to 18, more preferably 6 to 12, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms, preferably 5 to 18, more preferably 5 to 13.

[0228] The above Ar b1The unsubstituted aryl group having 6 to 30 ring-forming carbon atoms represented by is, for example, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a benzoanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a fluorenyl group, a fluoranthenyl group, a perylenyl group, or a triphenylenyl group, preferably a phenyl group, a biphenylyl group, a terphenylyl group, or a naphthyl group, more preferably a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, or a 1- or 2-naphthyl group, still more preferably a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, or a 1- or 2-naphthyl group.

[0229] Said Ar b1 The details and preferred examples of the unsubstituted heterocyclic group having 5 to 30 ring-forming atoms represented by are as described above for said L a2 as described above.

[0230] In one aspect of the present invention, Ar b1 is preferably a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, still more preferably a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, and even more preferably an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms.

[0231] In another aspect of the present invention, Ar b1 is preferably a group represented by any of the following formulas (b1) to (b6), and more preferably a group represented by the following formula (b2).

[0232]

Chemical formula

[0233] In formula (b1), *b8 is L b1 This is the binding position to [the target]. R b101 ~R b105 One of the selected options is a single bond that connects to *b9, R b106 ~R b110 One of the options selected is a single bond that connects to *b10. R that is not a single bond b101 ~R b105 , and R b106 ~R b110 Each of these is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, or an unsubstituted ring-forming aryl group having 6 to 12 carbon atoms. R that is not a single bond b101 ~R b105 Two adjacent elements selected from this list do not join to each other and do not form a ring. R that is not a single bond b106 ~R b110 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0234] R that is not a single bond b101 ~R b105 , and R b106 ~R b110 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0235] R that is not a single bond b101 ~R b105 , and R b106 ~R b110 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 12 carbon atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~Ra110 The details are as stated above.

[0236] R b111 ~R b115 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms. R b111 ~R b115 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0237] The aforementioned R b111 ~R b115 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0238] The aforementioned R b111 ~R b115 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 12 carbon atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0239] The aforementioned R b111 ~R b115 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 13 ring-forming atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The above applies to heterocyclic groups with 5 to 12 ring-forming atoms represented by .

[0240] R that is not a single bond b101 ~R b105All of them may be hydrogen atoms, and R which is not a single bond b106 ~R b110 R may all be hydrogen atoms, b111 ~R b115 It is also possible that all of them are hydrogen atoms.

[0241] m is 0, 1, or 2, and n is 0 or 1. When m=0 and n=0, *b10 represents *b8. When m=0 and n=1, *b9 represents *b8. When m=1 and n=0, *b10 represents *b9.

[0242] In one embodiment of the present invention, m is 0 and n is 0. In this case, *b10 represents *b8, and formula (b1) is expressed by the following formula.

[0243] [ka]

[0244] In another embodiment of the present invention, m is 0 and n is 1. In this case, *b9 represents *b8, and formula (b1) is expressed by the following formula.

[0245] [ka]

[0246] In another embodiment of the present invention, m is 1 and n is 0. In this case, *b10 represents *b9, and formula (b1) is expressed by the following formula.

[0247] [ka]

[0248] In another embodiment of the present invention, m is 1 and n is 1. In this case, formula (b1) is expressed as follows:

[0249] [ka]

[0250] In another aspect of the present invention, m is 2 and n is 0. In this case, *b10 represents *b9, and the formula (b1) is represented by the following formula.

[0251]

Chemical formula

[0252] In another aspect of the present invention, m is 2 and n is 1. In this case, the formula (b1) is represented by the following formula.

[0253]

Chemical formula

[0254] The group represented by the formula (b1) is preferably represented by the following formula. In the following formula, R is omitted for simplicity. R is the above R<00009�5>~R<00009�6>and R<00009�7>~R<00009�8>or R<00009�9>~R b115 is the same as.

[0255]

Chemical formula

[0256] The group represented by the formula (b1) is more preferably represented by the following formula.

[0257]

Chemical formula

[0258]

Chemical formula

[0259] [[ID=7۴]] In the formula (b2), *b11 is L b1 This is the binding position to [the target]. R b121 ~R b128 One of the options selected is a single bond that connects to *b12. R that is not a single bond b121 ~R b128 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms. R that is not a single bond b121 ~R b128 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0260] R that is not a single bond b121 ~R b128 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0261] R that is not a single bond b121 ~R b128 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 12 carbon atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0262] In one embodiment of the present invention, preferably R b122 , R b123 , R b126 , and R b127 One of the options selected is a single bond that connects to *b12.

[0263] *R is not a single bond attached to b12. b121 ~R b128 These may all be hydrogen atoms.

[0264] [ka]

[0265] In equation (b3), *b13 is L b1 This is the binding position to [the target]. R b131 ~R b140 One of the options selected is a single bond that connects to *b14. R that is not a single bond b131 ~R b140 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms. R that is not a single bond b131 ~R b140 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0266] R that is not a single bond b131 ~R b140 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0267] R that is not a single bond b131 ~R b140 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 12 carbon atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0268] In one embodiment of the present invention, preferably R b137 , R b138 and R b139 One of the options selected is a single bond that connects to *b14.

[0269] *R is not a single bond attached to b14. b131 ~R b140 These may all be hydrogen atoms.

[0270] [ka]

[0271] In formula (b4), *b15 is L b1 This is the binding position to [the target]. X b1 It consists of an oxygen atom, a sulfur atom, and CR. A R B , or NR C That is the case. R A and R B Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18, more preferably 1 to 10, and even more preferably 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, preferably 3 to 18, more preferably 3 to 10, and even more preferably 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, preferably 6 to 18, and even more preferably 6 to 12 carbon atoms, which may be bonded to each other to form a substituted or unsubstituted ring structure, or they may not be bonded to each other and therefore not form a ring.

[0272] The aforementioned R A and R BThe unsubstituted C1-C30 alkyl group represented by is, for example, a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, or dodecyl group, preferably a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, or pentyl group, more preferably a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, or t-butyl group, even more preferably a methyl group, ethyl group, isopropyl group, or t-butyl group, and even more preferably a methyl group.

[0273] The aforementioned R A and R B Details and preferred examples of unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0274] The aforementioned R A and R B Details of the unsubstituted ring-forming aryl group having 6 to 30 carbon atoms represented by and preferred examples thereof are as follows: b1 The details are as stated above.

[0275] The aforementioned R A and R B Unsubstituted monocycles formed by this process include, for example, benzene rings, cyclopentane rings, and cyclohexane rings. The aforementioned R A and R B The unsubstituted condensed rings formed by this process include, for example, naphthalene rings and anthracene rings. Also, R A and R B However, when they bond to each other to form an unsubstituted monoring or an unsubstituted fused ring, R A and R BThese may form a ring together with the fluorene skeleton to which they are bonded, forming a spiro ring. The spiro ring is a hydrocarbon ring or a heterocycle, and can be selected from monorings, fused rings, bridged bicyclo rings, or bridged tricyclo rings. Examples of substituted or unsubstituted spiro rings are shown below, but are not limited to these. * indicates the bond position of the fluorene skeleton to the benzene ring.

[0276] [ka]

[0277] R C This is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18, more preferably 1 to 10, even more preferably 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, preferably 6 to 18, more preferably 6 to 12 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms, preferably 5 to 18, more preferably 5 to 13 carbon atoms.

[0278] The aforementioned R C Details of the unsubstituted C1-C30 alkyl group represented by and preferred examples thereof are as follows: A and R B The details are as stated above.

[0279] The aforementioned R C Details of the unsubstituted ring-forming aryl group having 6 to 30 carbon atoms represented by and preferred examples thereof are as follows: b1 The details are as stated above.

[0280] The aforementioned R C Details of the unsubstituted ring-forming heterocyclic group having 5 to 30 carbon atoms represented by and preferred examples thereof are as follows: a2 The details are as stated above.

[0281] l is either 0 or 1. When l is 0, R A , R B , R C , and R b141 ~R b148One of the selected bonds is either a single bond that connects to *b16, or R A Or R B A substituted or unsubstituted ring-forming aryl group with 6 to 30 carbon atoms that can be represented by R A Or R B A substituted or unsubstituted ring structure that can be formed by the bonding of these elements with each other, or R C A substituted or unsubstituted aryl group with 6 to 30 carbon atoms that can be represented is bonded to *b16 via a single bond. When l is 1, R b141 and R b142 , R b142 and R b143 , or R b143 and R b144 One of the R atoms is a single bond that connects to *a, and the other is a single bond that connects to *b, and is not a single bond that connects to both *a and *b. b141 ~R b144 , R b145 ~R b148 , R A , R B , R C , and R b200 ~R b203 One of the selected bonds is either a single bond that connects to *b16, or R A Or R B A substituted or unsubstituted ring-forming aryl group with 6 to 30 carbon atoms that can be represented by, or R A Or R B A substituted or unsubstituted ring structure that can be formed by the bonding of these elements with each other, or R C A substituted or unsubstituted aryl group with 6 to 30 carbon atoms that can be represented is bonded to *b16 via a single bond. R that is not a single bond b141 ~R b148 , and R that is not a single bond b200 ~R b203 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heterocyclic group. R that is not a single bond b141 ~R b148 , and R that is not a single bond b200~R b203 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0282] R that is not a single bond b141 ~R b148 , and R that is not a single bond b200 ~R b203 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0283] R that is not a single bond b141 ~R b148 , and R that is not a single bond b200 ~R b203 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 12 carbon atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0284] R that is not a single bond b141 ~R b148 , and R that is not a single bond b200 ~R b203 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 13 ring-forming atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The above applies to heterocyclic groups with 5 to 12 ring-forming atoms represented by .

[0285] R that is not a single bond b141 ~R b148 These may all be hydrogen atoms, and the R that is not a single bond may be b200 ~R b203 These may all be hydrogen atoms.

[0286] [ka]

[0287] In formula (b5), *b17 is L b1 This is the binding position to [the target]. R b151 ~R b155 One of the selected options is a single bond that connects to *b18, R b151 ~R b155 The other one chosen from among them is a single bond that connects to *b19. R that is not a single bond b151 ~R b155 Each of these is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, or an unsubstituted phenyl group. R that is not a single bond b151 ~R b155 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0288] R that is not a single bond b151 ~R b155 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0289] R b161 ~R b165 and R b171 ~R b175 Each of these is independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms. R b161 ~R b165 At least one adjacent pair selected from may bond to each other to form one or more unsubstituted benzene rings, or they may not bond to each other to form a ring. R b171 ~R b175At least one adjacent pair selected from may bond to each other to form one or more unsubstituted benzene rings, or they may not bond to each other and therefore not form rings.

[0290] The aforementioned R b161 ~R b165 and R b171 ~R b175 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0291] R that is not a single bond b151 ~R b155 All of them may be hydrogen atoms, and R which is not a single bond b161 ~R b165 All of them may be hydrogen atoms, and R which is not a single bond b171 ~R b175 It is also possible that all of them are hydrogen atoms.

[0292] [ka]

[0293] In formula (b6), *b20 is L b1 This is the binding position to [the target]. R b181 ~R b192 One of the options selected is a single bond that connects to *b21. R that is not a single bond b181 ~R b192 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms. R that is not a single bond b181 ~R b192 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0294] R that is not a single bond b181 ~R b192 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0295] R that is not a single bond b181 ~R b192 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 12 carbon atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0296] R that is not a single bond b181 ~R b192 It is also possible that all of them are hydrogen atoms.

[0297] R b1 ~R b4 This is a hydrogen atom. R b11 ~R b17 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, preferably 1 to 20, more preferably 1 to 6 carbon atoms, The aforementioned R b11 ~R b17 Two adjacent elements selected from this list do not join to each other and do not form a ring. Rings C and D may or may not be bridged.

[0298] The aforementioned R b11 ~R b17 Details of the unsubstituted C1-C50 alkyl group represented by and preferred examples thereof are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0299] The aforementioned R b11 ~R b17 However, they could all be hydrogen atoms.

[0300] The ring structure formed by the bridge of ring C and ring D is, for example, a dibenzofuran structure, a dibenzothiophene structure, a carbazole structure, or a fluorantene structure, and is preferably a dibenzofuran structure.

[0301] R b21 ~R b24 and R b31 ~R b38 Each of these independently comprises a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, preferably 1 to 20, more preferably 1 to 6 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, preferably 2 to 20, more preferably 2 to 6 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, preferably 2 to 20, more preferably 2 to 6 carbon atoms, an unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, preferably 3 to 20, more preferably 3 to 6 carbon atoms, and -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), halogen atoms, cyano groups, nitro groups, unsubstituted aryl groups having 6 to 50, preferably 6 to 30, more preferably 6 to 18 ring-forming carbon atoms, or unsubstituted heterocyclic groups having 5 to 50, preferably 5 to 30, more preferably 5 to 18 ring-forming atoms, R 901 ~R 905 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, preferably 1 to 20, more preferably 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, preferably 3 to 20, more preferably 3 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, preferably 6 to 30, more preferably 6 to 18 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, preferably 5 to 30, more preferably 5 to 18 carbon atoms. R 901 If there are two or more of them, then there are two or more R 901They 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 903 If 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 one another.

[0302] The aforementioned R b21 ~R b24 and R b31 ~R b38 Details of the unsubstituted C1-C50 alkyl group represented by and preferred examples thereof are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0303] The aforementioned R b21 ~R b24 and R b31 ~R b38 Details of the unsubstituted C2-C50 alkenyl group represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0304] The aforementioned R b21 ~R b24 and R b31 ~R b38 Details of the unsubstituted alkynyl groups 2 to 50 represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0305] The aforementioned R b21 ~R b24 and R b31 ~R b38 Details and preferred examples of unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0306] The aforementioned R b21 ~R b24 and R b31 ~R b38 Details of the halogen atom represented and preferred examples thereof are R, which is not a single bond. a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0307] The aforementioned R b21 ~R b24 and R b31 ~R b38 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 50 carbon atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0308] The aforementioned R b21 ~R b24 and R b31 ~R b38 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0309] The aforementioned R 901 ~R 905Details of the unsubstituted C1-C50 alkyl group represented by and preferred examples thereof are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0310] The aforementioned R 901 ~R 905 Details and preferred examples of unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0311] The aforementioned R 901 ~R 905 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 50 carbon atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0312] The aforementioned R 901 ~R 905 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0313] The aforementioned R b21 ~R b24 and R b31 ~R b38 Each of these is independently preferably a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.

[0314] R that is not a single bond b21 ~R b24However, they may all be hydrogen atoms, R b31 ~R b38 However, they could all be hydrogen atoms.

[0315] The compound represented by formula (B) may contain at least one deuterium atom. If the compound represented by formula (B) contains a deuterium atom, R b1 ~R b4 At least one of the atoms selected is a deuterium atom, L b1 R may have at least one deuterium atom, b1 ~R b4 All of them are deuterium atoms, L b1 is a base represented by formula (iv), and R b41 ~R b45 It is also possible that all of them are deuterium atoms.

[0316] The third compound of the present invention (inventive compound (C)) is represented by the following formula (C).

[0317] [ka]

[0318] In formula (C), N * It is the central nitrogen atom. L c1 This is a single bond, a group represented by the following formulas (vi) or (vii).

[0319] [ka]

[0320] In equations (vi) and (vii), R c31 ~R c35 One of the options selected is a single bond that connects to *c2, R c41 ~R c48 One of the selected options is a single bond that connects to *c5, R c41 ~R c48The other one chosen from among them is a single bond that joins *c6.

[0321] In one embodiment of the present invention, preferably R c33 This is a single bond that connects to *c2.

[0322] R that is not a single bond c31 ~R c35 , and R that is not a single bond c41 ~R c48 Each of these independently comprises a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, preferably 1 to 20, more preferably 1 to 6 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, preferably 2 to 20, more preferably 2 to 6 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, preferably 2 to 20, more preferably 2 to 6 carbon atoms, an unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, preferably 3 to 20, more preferably 3 to 6 carbon atoms, and -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), halogen atoms, cyano groups, nitro groups, unsubstituted aryl groups having 6 to 50, preferably 6 to 30, more preferably 6 to 18 ring-forming carbon atoms, or unsubstituted heterocyclic groups having 5 to 50, preferably 5 to 30, more preferably 5 to 18 ring-forming atoms, R 901 ~R 905 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, preferably 1 to 20, more preferably 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, preferably 3 to 20, more preferably 3 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, preferably 6 to 30, more preferably 6 to 18 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, preferably 5 to 30, more preferably 5 to 18 carbon 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 902They are either identical or different from each other. R 903 If 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 one another. *c1 and *c4 are the central nitrogen atoms N * This represents the binding position to, *c3 and *c7 represent the bond positions to ring G. R that is not a single bond c31 ~R c35 , and R that is not a single bond c41 ~R c48 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0323] R that is not a single bond c31 ~R c35 , and R that is not a single bond c41 ~R c48 Details of the unsubstituted C1-C50 alkyl group represented by and preferred examples thereof are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0324] R that is not a single bond c31 ~R c35 , and R that is not a single bond c41 ~R c48 Details of the unsubstituted C2-C50 alkenyl group represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0325] R that is not a single bond c31~R c35 , and R that is not a single bond c41 ~R c48 Details of the unsubstituted alkynyl groups 2 to 50 represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0326] R that is not a single bond c31 ~R c35 , and R that is not a single bond c41 ~R c48 Details and preferred examples of unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0327] R that is not a single bond c31 ~R c35 , and R that is not a single bond c41 ~R c48 Details of the halogen atom represented and preferred examples thereof are R, which is not a single bond. a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0328] R that is not a single bond c31 ~R c35 , and R that is not a single bond c41 ~R c48 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 50 carbon atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0329] R that is not a single bond c31 ~R c35 , and R that is not a single bondc41 ~R c48 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0330] The aforementioned R 901 ~R 905 Details of the unsubstituted C1-C50 alkyl group represented by and preferred examples thereof are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0331] The aforementioned R 901 ~R 905 Details and preferred examples of unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0332] The aforementioned R 901 ~R 905 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 50 carbon atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0333] The aforementioned R 901 ~R 905 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0334] R that is not a single bond c31 ~R c35 , and R that is not a single bond c41 ~R c48 Each of these is independently preferably a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.

[0335] R that is not a single bond c31 ~R c35 However, they may all be hydrogen atoms, and the R that is not a single bond may also be c41 ~R c48 However, they could all be hydrogen atoms.

[0336] In one embodiment of the present invention, L c1 It is preferable that the bond is a single bond. In another embodiment of the present invention, L c1 It is preferable that the group is represented by the above formula (vi).

[0337] Ar c1 This is a group represented by the following formula (c1) or (c2).

[0338] [ka]

[0339] In formula (c1), *c8 is the central nitrogen atom N * This indicates the connection position to the destination. L c2 This is a substituted or unsubstituted arylene group having 6 to 30, preferably 6 to 18, more preferably 6 to 12, ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30, preferably 5 to 18, more preferably 5 to 12, ring-forming atoms.

[0340] Said L c2 Details of the unsubstituted ring-forming carbon 6-30 arylene group represented by and preferred examples thereof are as follows: a2 The details are as stated above.

[0341] Said L c2 Details and preferred examples of the unsubstituted, divalent heterocyclic group with 5 to 30 ring-forming atoms represented by L a2 The details are as stated above.

[0342] L c2 Preferably, it is a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, more preferably a substituted or unsubstituted ring-forming arylene group having 6 to 12 carbon atoms, even more preferably a substituted or unsubstituted phenylene group, even more preferably a substituted or unsubstituted p-phenylene group, and even more preferably an unsubstituted p-phenylene group.

[0343] R c101 ~R c108 One of the options selected is a single bond that connects to *c9. R that is not a single bond c101 ~R c108 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms. R that is not a single bond c101 ~R c108 Two adjacent elements selected from this list do not join to each other and do not form a ring. However, L c2 R is a substituted or unsubstituted phenylene group, c101 , R c104 , R c105 and R c108 When one of the selected bonds is a single bond that connects to *c9, L c2 The substituted or unsubstituted phenylene group represented by is a substituted or unsubstituted o-phenylene group, or a substituted or unsubstituted m-phenylene group.

[0344] In one embodiment of the present invention, R c102 , R c103 , R c106 , and R c107Preferably, one of the selected bonds is a single bond that connects to *c9.

[0345] R that is not a single bond c101 ~R c108 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0346] R that is not a single bond c101 ~R c108 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 12 carbon atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0347] R that is not a single bond c101 ~R c108 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 13 ring-forming atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The above applies to heterocyclic groups with 5 to 12 ring-forming atoms represented by .

[0348] R that is not a single bond c101 ~R c108 It is also possible that all of them are hydrogen atoms.

[0349] [ka]

[0350] In formula (c2), *c10 is the central nitrogen atom N * This indicates the connection position to the destination. L c3This is a substituted or unsubstituted arylene group having 6 to 30, preferably 6 to 18, more preferably 6 to 12, ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30, preferably 5 to 18, more preferably 5 to 12, ring-forming atoms.

[0351] Said L c3 Details of the unsubstituted ring-forming carbon 6-30 arylene group represented by and preferred examples thereof are as follows: a2 The details are as stated above.

[0352] Said L c3 Details and preferred examples of the unsubstituted, divalent heterocyclic group with 5 to 30 ring-forming atoms represented by L a2 The details are as stated above.

[0353] L c3 Preferably, it is a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, more preferably a substituted or unsubstituted ring-forming arylene group having 6 to 12 carbon atoms, even more preferably a substituted or unsubstituted phenylene group, even more preferably a substituted or unsubstituted p-phenylene group, and even more preferably an unsubstituted p-phenylene group.

[0354] Ar c1 Preferably, the group is represented by the formula (c1) described above.

[0355] X c1 This is an oxygen atom or a sulfur atom, preferably an oxygen atom.

[0356] R c111 ~R c118 One of the options selected is a single bond that connects to *c11. R that is not a single bond c111 ~R c118 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms. R that is not a single bond c111 ~R c118 Two adjacent elements selected from the set may join to form a substituted or unsubstituted ring structure, or they may not join to each other and therefore not form a ring structure.

[0357] R that is not a single bond c111 ~R c118 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0358] R that is not a single bond c111 ~R c118 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 12 carbon atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0359] R that is not a single bond c111 ~R c118 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 13 ring-forming atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The above applies to heterocyclic groups with 5 to 12 ring-forming atoms represented by .

[0360] R that is not a single bond c111 ~R c118 It is also possible that all of them are hydrogen atoms.

[0361] R c1 ~R c4 This is a hydrogen atom. R c11 ~R c17Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, preferably 1 to 20, more preferably 1 to 6 carbon atoms, The aforementioned R c11 ~R c17 Two adjacent elements selected from this list do not join to each other and do not form a ring. Rings E and F may or may not be bridged.

[0362] The aforementioned R c11 ~R c17 Details of the unsubstituted C1-C50 alkyl group represented by and preferred examples thereof are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0363] The aforementioned R c11 ~R c17 However, they could all be hydrogen atoms.

[0364] The ring structure formed by the bridge of ring E and ring F is, for example, a dibenzofuran structure, a dibenzothiophene structure, a carbazole structure, or a fluorantene structure, and is preferably a dibenzofuran structure.

[0365] R c21 This is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0366] R c21 This is preferably a substituted or unsubstituted phenyl group, more preferably an unsubstituted phenyl group.

[0367] R c22 ~R c29Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms.

[0368] The aforementioned R c22 ~R c29 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0369] The aforementioned R c22 ~R c29 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 12 carbon atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0370] The aforementioned R c22 ~R c29 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 13 ring-forming atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The above applies to heterocyclic groups with 5 to 12 ring-forming atoms represented by .

[0371] The aforementioned R c22 ~R c29 It is also possible that all of them are hydrogen atoms.

[0372] The compound represented by formula (C) may contain at least one deuterium atom. If the compound represented by formula (C) contains a deuterium atom, R c1 ~R c4 At least one of the atoms selected is a deuterium atom, and Arc1 is a group represented by the above formula (c1), and L c2 R may have at least one deuterium atom, c1 ~R c4 All of them are deuterium atoms, and Ar c1 is a group represented by the above formula (c1), and L c2 This is an unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, and the L c2 The unsubstituted ring-forming arylene group with 6 to 30 carbon atoms represented by may have all its hydrogen atoms be deuterium atoms.

[0373] The fourth compound of the present invention (inventive compound (D)) is represented by the following formula (D).

[0374] [ka]

[0375] In formula (D), N * It is the central nitrogen atom. L d1 This is a group represented by the following formula (viii).

[0376] [ka]

[0377] In formula (viii), R d31 and R d35 One of the options selected is a single bond that connects to *d3.

[0378] R that is not a single bond d31 ~R d35Each of these independently comprises a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, preferably 1 to 20, more preferably 1 to 6 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, preferably 2 to 20, more preferably 2 to 6 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, preferably 2 to 20, more preferably 2 to 6 carbon atoms, an unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, preferably 3 to 20, more preferably 3 to 6 carbon atoms, and -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), halogen atoms, cyano groups, nitro groups, unsubstituted aryl groups having 6 to 50, preferably 6 to 30, more preferably 6 to 18 ring-forming carbon atoms, or unsubstituted heterocyclic groups having 5 to 50, preferably 5 to 30, more preferably 5 to 18 ring-forming atoms, R 901 ~R 905 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, preferably 1 to 20, more preferably 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, preferably 3 to 20, more preferably 3 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, preferably 6 to 30, more preferably 6 to 18 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, preferably 5 to 30, more preferably 5 to 18 carbon 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 903 If 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 905They are either identical or different from one another. *d2 is the central nitrogen atom N * This represents the binding position to, *d1 is R d21 ~R d28 It combines with one selected from the options. R that is not a single bond d31 ~R d35 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0379] R that is not a single bond d31 ~R d35 Details of the unsubstituted C1-C50 alkyl group represented by and preferred examples thereof are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0380] R that is not a single bond d31 ~R d35 Details of the unsubstituted C2-C50 alkenyl group represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0381] R that is not a single bond d31 ~R d35 Details of the unsubstituted alkynyl groups 2 to 50 represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0382] R that is not a single bond d31 ~R d35 Details and preferred examples of unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38The details are as stated above.

[0383] R that is not a single bond d31 ~R d35 Details of the halogen atom represented and preferred examples thereof are R, which is not a single bond. a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0384] R that is not a single bond d31 ~R d35 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 50 carbon atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0385] R that is not a single bond d31 ~R d35 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0386] The aforementioned R 901 ~R 905 Details of the unsubstituted C1-C50 alkyl group represented by and preferred examples thereof are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0387] The aforementioned R 901 ~R 905 Details and preferred examples of unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~Ra38 The details are as stated above.

[0388] The aforementioned R 901 ~R 905 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 50 carbon atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0389] The aforementioned R 901 ~R 905 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms represented by are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0390] R that is not a single bond d31 ~R d35 Each of these is independently preferably a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.

[0391] R that is not a single bond d31 ~R d35 However, they could all be hydrogen atoms.

[0392] Ar d1 The group is represented by any of the following formulas (d1) to (d3), and preferably by the following formula (d2).

[0393] [ka]

[0394] In formula (d1), *d7 is the central nitrogen atom N * This indicates the connection position to the destination. R d101~R d105 One of the selected options is a single bond that connects to *d8, R d106 ~R d110 One of the options selected is a single bond that joins to *d9. R that is not a single bond d101 ~R d105 , and R d106 ~R d110 Each of these is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, or an unsubstituted ring-forming aryl group having 6 to 12 carbon atoms. R that is not a single bond d101 ~R d105 Two adjacent elements selected from this list do not join to each other and do not form a ring. R that is not a single bond d106 ~R d110 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0395] R that is not a single bond d101 ~R d105 , and R d106 ~R d110 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0396] R that is not a single bond d101 ~R d105 , and R d106 ~R d110 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 12 carbon atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0397] R d111 ~R d115Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms. R d111 ~R d115 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0398] The aforementioned R d111 ~R d115 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0399] The aforementioned R d111 ~R d115 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 12 carbon atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0400] The aforementioned R d111 ~R d115 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 13 ring-forming atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The above applies to heterocyclic groups with 5 to 12 ring-forming atoms represented by .

[0401] R that is not a single bond d101 ~R d105 All of them may be hydrogen atoms, and R which is not a single bond d106 ~R d110 R may all be hydrogen atoms, d111 ~R d115 It is also possible that all of them are hydrogen atoms.

[0402] m is either 0 or 1, and n is either 0 or 1. When m=0 and n=0, *d9 represents *d7, When m=0 and n=1, *d8 represents *d7, When m=1 and n=0, *d9 represents *d8.

[0403] In one embodiment of the present invention, m is 0 and n is 0. In this case, *d9 represents *d7, and equation (d1) is expressed by the following equation.

[0404] [ka]

[0405] In another embodiment of the present invention, m is 0 and n is 1. In this case, *d8 represents *d7, and equation (d1) is expressed by the following equation.

[0406] [ka]

[0407] In another embodiment of the present invention, m is 1 and n is 0. In this case, *d9 represents *d8, and equation (d1) is expressed by the following equation.

[0408] [ka]

[0409] In another embodiment of the present invention, m is 1 and n is 1. In this case, formula (d1) is expressed as follows:

[0410] [ka]

[0411] In another embodiment of the present invention, m is 2 and n is 0. In this case, *d9 represents *d8, and equation (d1) is expressed by the following equation.

[0412] [ka]

[0413] In another embodiment of the present invention, m is 2 and n is 1. In this case, formula (d1) is expressed as follows:

[0414] [ka]

[0415] The base represented by formula (d1) is preferably represented by the following formula. In the following formula, R is omitted for simplification. R is the aforementioned R d101 ~R d105 and R d106 ~R d110 , or R d111 ~R d115 It is identical to [the other one].

[0416] [ka]

[0417] The group represented by formula (d1) is more preferably represented by the following formula.

[0418] [ka]

[0419] [ka]

[0420] In formula (d2), *d10 is the central nitrogen atom N * This indicates the connection position to the destination. L d2This is a substituted or unsubstituted arylene group having 6 to 30, preferably 6 to 18, more preferably 6 to 12, ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30, preferably 5 to 18, more preferably 5 to 12, ring-forming atoms.

[0421] Said L d2 Details of the unsubstituted ring-forming carbon 6-30 arylene group represented by and preferred examples thereof are as follows: a2 The details are as stated above.

[0422] Said L d2 Details and preferred examples of the unsubstituted, divalent heterocyclic group with 5 to 30 ring-forming atoms represented by L a2 The details are as stated above.

[0423] L d2 Preferably, it is a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, more preferably a substituted or unsubstituted ring-forming arylene group having 6 to 12 carbon atoms, even more preferably a substituted or unsubstituted phenylene group, even more preferably a substituted or unsubstituted p-phenylene group, and even more preferably an unsubstituted p-phenylene group.

[0424] R that is not a single bond d121 ~R d128 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms. R that is not a single bond d121 ~R d128 Two adjacent elements selected from this list do not join to each other and do not form a ring.

[0425] R that is not a single bond d121 ~R d128 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110The details are as stated above.

[0426] R that is not a single bond d121 ~R d128 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 12 carbon atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0427] In one embodiment of the present invention, preferably R d122 , R d123 , R d126 , and R d127 One of the options selected is a single bond that connects to *b12.

[0428] *R that is not a single bond attached to d11 d121 ~R d128 These may all be hydrogen atoms.

[0429] [ka]

[0430] In equation (d3), *d12 is the central nitrogen atom N * This indicates the connection position to the destination. L d3 This is a substituted or unsubstituted arylene group having 6 to 30, preferably 6 to 18, more preferably 6 to 12, ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30, preferably 5 to 18, more preferably 5 to 12, ring-forming atoms.

[0431] Said L d3 Details of the unsubstituted ring-forming carbon 6-30 arylene group represented by and preferred examples thereof are as follows: a2 The details are as stated above.

[0432] Said L d3Details and preferred examples of the unsubstituted, divalent heterocyclic group with 5 to 30 ring-forming atoms represented by L a2 The details are as stated above.

[0433] L d3 Preferably, it is a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, more preferably a substituted or unsubstituted ring-forming arylene group having 6 to 12 carbon atoms, even more preferably a substituted or unsubstituted phenylene group, even more preferably a substituted or unsubstituted p-phenylene group, and even more preferably an unsubstituted p-phenylene group.

[0434] X d1 This is an oxygen atom or a sulfur atom, preferably an oxygen atom.

[0435] R d131 ~R d138 One of the options selected is a single bond that connects to *c11. R that is not a single bond d131 ~R d138 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms. R that is not a single bond d131 ~R d138 Two adjacent elements selected from the set may join to form a substituted or unsubstituted ring structure, or they may not join to each other and therefore not form a ring structure.

[0436] R that is not a single bond d131 ~R d138 Details of the unsubstituted C1-C10 alkyl group represented by and preferred examples thereof are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0437] R that is not a single bondd131 ~R d138 Details and preferred examples of the unsubstituted ring-forming aryl group with 6 to 12 carbon atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The details are as stated above.

[0438] R that is not a single bond d131 ~R d138 Details and preferred examples of unsubstituted heterocyclic groups with 5 to 13 ring-forming atoms represented by are as follows: a101 ~R a105 , and R that is not a single bond a106 ~R a110 The above applies to heterocyclic groups with 5 to 12 ring-forming atoms represented by .

[0439] R that is not a single bond d131 ~R d138 It is also possible that all of them are hydrogen atoms.

[0440] R d1 ~R d4 This is a hydrogen atom. R d11 ~R d17 Each of these is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, preferably 1 to 20, more preferably 1 to 6 carbon atoms, The aforementioned R d11 ~R d17 Two adjacent elements selected from this list do not join to each other and do not form a ring. Ring H and ring I may or may not be bridged.

[0441] The aforementioned R d11 ~R d17 Details of the unsubstituted C1-C50 alkyl group represented by and preferred examples thereof are as follows: a21 ~R a25 , and R that is not a single bond a31 ~R a38 The details are as stated above.

[0442] The aforementioned R d11 ~R d17 However, they could all be hydrogen atoms.

[0443] The ring structure formed by the bridge of ring H and ring I is, for example, a dibenzofuran structure, a dibenzothiophene structure, a carbazole structure, or a fluorantene structure, and is preferably a dibenzofuran structure.

[0444] *R is not a single bond attached to d1. d21 ~R d28 Each of these is independently a hydrogen atom or a substituted or unsubstituted ring-forming carbon-6 aryl group. *R is not a single bond attached to d1. d21 ~R d28 At least one of these selected is the substituted or unsubstituted ring-forming aryl group having 6 carbon atoms.

[0445] The aforementioned R d21 ~R d28 An example of an unsubstituted ring-forming aryl group with 6 carbon atoms represented by this is the phenyl group.

[0446] In one embodiment of the present invention, R d21 , R d24 , R d25 , and R d28 Preferably, at least one selected from is the aforementioned substituted or unsubstituted ring-forming aryl group having 6 carbon atoms, R d21 , R d24 , R d25 , and R d28 It is more preferable that one of those selected is the aforementioned substituted or unsubstituted ring-forming aryl group having 6 carbon atoms.

[0447] The compound represented by formula (D) may contain at least one deuterium atom. If the compound represented by formula (D) contains a deuterium atom, R d1 ~R d4 At least one of those selected may be a deuterium atom, and Ar d1is a group represented by the above formula (d2), and L d2 R may have at least one deuterium atom, d1 ~R d4 All of them are deuterium atoms, and Ar d1 is a group represented by the above formula (d2), and L d2 This is an unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, and the L d2 The unsubstituted ring-forming arylene group with 6 to 30 carbon atoms represented by may have all its hydrogen atoms be deuterium atoms.

[0448] 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, deuterium atoms may be intentionally introduced into the inventive compound by using a deuterized compound as part or all of the raw material compound. The inventive compound may be a compound represented by formula (A) in which at least one of the hydrogen atoms contained in the compound is a deuterium atom; the inventive compound may be a compound represented by formula (B) in which at least one of the hydrogen atoms contained in the compound is a deuterium atom; the inventive compound may be a compound represented by formula (C) in which at least one of the hydrogen atoms contained in the compound is a deuterium atom; or the inventive compound may be a compound represented by formula (D) in which at least one of the hydrogen atoms contained in the compound is a deuterium atom.

[0449] At least one of the hydrogen atoms selected from the hydrogen atoms listed below may be a deuterium atom. Note that "substituted or unsubstituted," carbon number, and atomic number are omitted below. L in equation (A) a1 A hydrogen atom possessed by a group represented by any of the formulas (i) to (iii) shown by; Ar in equation (A) a1 The hydrogen atoms of the phenyl group, naphthyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, naphthobenzofuranyl group, or naphthobenzothiophenyl group represented by; Ar in equation (A)a2 A hydrogen atom possessed by a group represented by any of the formulas (a1) to (a3) ​​shown by; R in equation (A) a1 ~R a4 A hydrogen atom represented by any of the following; R in equation (A) a11 ~R a17 A hydrogen atom represented by any of the following; R in equation (A) a11 ~R a17 When any of them is an alkyl group, the hydrogen atoms that the alkyl group has; The hydrogen atoms in the ring structure formed by the bridging of ring A and ring B in formula (A); L in equation (B) b1 The hydrogen atom of the group represented by formula (iv) or (v) represented by; Ar in equation (B) b1 The aryl group represented by or the hydrogen atom of the heterocyclic group; R in equation (B) b1 ~R b4 A hydrogen atom represented by any of the following; R in equation (B) b11 ~R b17 A hydrogen atom represented by any of the following; R in equation (B) b11 ~R b17 When any of them is an alkyl group, the hydrogen atoms that the alkyl group has; The hydrogen atoms in the ring structure formed by the bridging of ring C and ring D in formula (B); R in equation (B) b21 ~R b24 and R b31 ~R b38 A hydrogen atom represented by any of the following; R in equation (B) b21 ~R b24 and R b31 ~R b38 Any of these is an alkyl group, alkenyl group, alkynyl group, cycloalkyl group, -Si(R 901 )(R 902 )(R 903 A group represented by -O-(R 904 A group represented by -S-(R 905 ), aryl group, or heterocyclic group, the hydrogen atoms they possess; L of equation (C) c1 The hydrogen atom of the group represented by formula (vi) or (vii); Ar in equation (C) c1 The hydrogen atom of the group represented by formula (c1) or (c2); R in equation (C) c1 ~R c4 A hydrogen atom represented by any of the following; R in equation (C) c11 ~R c17 A hydrogen atom represented by any of the following; R in equation (C) c11 ~R c17 When any of them is an alkyl group, the hydrogen atoms that the alkyl group has; The hydrogen atoms in the ring structure formed by the bridging of rings E and F in formula (C); R in equation (C) c21 The hydrogen atoms of the phenyl group, naphthyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, naphthobenzofuranyl group, or naphthobenzothiophenyl group represented by; R in equation (C) c22 ~R c29 A hydrogen atom represented by any of the following; R in equation (C) c22 ~R c29 When any of these is an alkyl group, an aryl group, or a heterocyclic group, the hydrogen atoms they possess; L in equation (D) d1 The hydrogen atoms possessed by the group represented by formula (viii); Ar in equation (D) d1 The hydrogen atoms present in the group represented by formulas (d1) to (d3); R in equation (D) d1 ~R d4 A hydrogen atom represented by any of the following; R in equation (D) d11 ~R d17 A hydrogen atom represented by any of the following; R in equation (D) d11 ~R d17 When any of them is an alkyl group, the hydrogen atoms that the alkyl group has; The hydrogen atoms in the ring structure formed by the bridging of ring H and ring I in formula (D); R in equation (D) d21 ~R d28 A hydrogen atom represented by any of the following; R in equation (D) d21 ~R d28 When either of these is an aryl group, the hydrogen atom of the aryl group;

[0450] The deuterated ratio of the inventive compound depends on the deuterated ratio of the raw materials used. Even when raw materials with a predetermined deuterated ratio are used, a certain proportion of naturally occurring light hydrogen isotopes may be present. Therefore, the deuterated ratio of the inventive compound includes a ratio that takes into account trace amounts of naturally occurring isotopes, in addition to the ratio that can be determined simply by 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.

[0451] 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.

[0452] When the "substituted or unsubstituted XX group" included in the definition of each of the above formulas is a substituted XX group, the details of the substituent are as described in "Substituents in the case of 'substituted or unsubstituted'", and are preferably an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring-forming carbon atoms, or a heterocyclic group (heteroaryl group) having 5 to 13 ring-forming atoms, and more preferably an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 12 ring-forming carbon atoms. The details of each group (alkyl group, aryl group, heterocyclic group) are as described above.

[0453] Those skilled in the art can easily produce the inventive compound by referring to the following synthesis examples and known synthesis methods.

[0454] 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.

[0455] Exemplary compounds of formula (A) [ka]

[0456] [ka]

[0457] [ka]

[0458] [ka]

[0459] [ka]

[0460] [ka]

[0461]

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[0462]

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[0463]

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[0464]

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[0465]

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[0466]

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[0467]

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[0468]

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[0469]

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[0470]

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[0471]

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[0472]

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[0473]

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[0474]

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[0475]

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[0477]

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[0478]

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[0479]

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[0480]

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[0481]

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[0482]

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[0483]

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[0486]

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[0487]

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[0488]

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[0489]

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[0490]

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[0491]

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[0492]

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[0493]

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[0494]

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[0495]

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[0496]

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[0497]

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[0498]

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[0499]

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[0500]

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[0501]

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[0502]

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[0503]

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[0505]

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[0506]

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[0507]

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[0508]

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[0509]

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[0510]

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[0511]

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[0512]

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[0513]

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[0514]

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[0515]

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[0516]

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[0517]

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[0518]

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[0519]

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[0520]

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[0521]

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[0522]

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[0526]

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[0527]

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[0528]

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[0530]

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[0567] [ka]

[0568] [ka]

[0569] Exemplary compounds of formula (B) [ka]

[0570] [ka]

[0571] [ka]

[0572] [ka]

[0573] [ka]

[0574] [ka]

[0575] [ka]

[0576] [ka]

[0577] [ka]

[0578] Exemplary compounds of formula (C) [ka]

[0579] [ka]

[0580] [ka]

[0581] [ka]

[0582] [ka]

[0583] [ka]

[0584] [ka]

[0585] [ka]

[0586] [ka]

[0587] [ka]

[0588] [ka]

[0589] [ka]

[0590] [ka]

[0591] [ka]

[0592] [ka]

[0593] [ka]

[0594] [ka]

[0595] [ka]

[0596] Exemplary compounds of formula (D) [ka]

[0597] [ka]

[0598] [ka]

[0599] [ka]

[0600] [ka]

[0601] [ka]

[0602] [ka]

[0603] [ka]

[0604] [ka]

[0605] [ka]

[0606] [ka]

[0607] [ka]

[0608] 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.

[0609] 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.

[0610] 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.

[0611] 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 / First fluorescence emission layer / Second fluorescence emission layer / Electron transport layer ( / Electron injection layer) (c) (Hole injection layer / ) Hole transport layer / Phosphorescent layer / Space layer / Fluorescent layer / Electron transport layer ( / Electron injection layer) (d) (Hole injection layer / ) Hole transport layer / First phosphorescent layer / Second phosphorescent layer / Space layer / Fluorescent layer / Electron transport layer ( / Electron injection layer) (e) (Hole injection layer / ) Hole transport layer / Phosphorescent layer / Space layer / First fluorescence layer / Second fluorescence layer / Electron transport layer ( / Electron injection layer) (f) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Fluorescence layer / Electron transport layer ( / Electron injection layer) (g) (Hole injection layer / ) Hole transport layer / Exciton blocking layer / Fluorescence layer / Electron transport layer ( / Electron injection layer) (h)(Hole injection layer / )First hole transport layer / Second hole transport layer / Fluorescence-emitting layer / Electron transport layer( / Electron injection layer) (i) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Fluorescence layer / First electron transport layer / Second electron transport layer ( / Electron injection layer) (j)(Hole injection layer / )Hole transport layer / Fluorescence layer / Hole blocking layer / Electron transport layer( / Electron injection layer) (k)(hole injection layer / )hole transport layer / fluorescence layer / exciton blocking layer / electron transport layer( / electron injection layer) (l)(Hole injection layer / )First hole transport layer / Second hole transport layer / First fluorescence emission layer / Second fluorescence emission layer / First electron transport layer / Second 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)

[0612] 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 (sometimes referred to as 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. Furthermore, hole transport layers adjacent to the light-emitting layer in a multilayer structure containing two or more hole transport layers, such as the second hole transport layer in the two-layer structure or the third hole transport layer in the three-layer structure, may also function as electron blocking layers. In other words, if the hole transport layer is a multilayer structure containing two or more hole transport layers, the hole transport layers adjacent to the light-emitting layer in the multilayer structure can also be used as electron blocking layers.

[0613] 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.

[0614] 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 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10 disposed between the anode 3 and the cathode 4. The light-emitting unit 10 has a light-emitting layer 5. 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. In addition, an electron blocking layer (not shown) may be provided on the anode 3 side of the light-emitting layer 5, and a hole blocking layer (not shown) may be provided on the cathode 4 side of the light-emitting layer 5. This confines electrons and holes in the light-emitting layer 5, further increasing the exciton generation efficiency in the light-emitting layer 5.

[0615] Figure 2 is a schematic diagram showing another configuration of the organic EL element of the present invention. The organic EL element 11 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 20 disposed between the anode 3 and the cathode 4. The light-emitting unit 20 has a light-emitting layer 5. The hole transport 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.

[0616] 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.

[0617] 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.

[0618] 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.

[0619] 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).

[0620] 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.

[0621] Hole transport band As described above, the organic layer may include a hole transport band between the anode and the light-emitting layer. The hole transport band is composed of a hole injection layer, a hole transport layer, an electron blocking layer, etc. It is preferable that the hole transport band contains the inventive compound. It is preferable that at least one of these layers constituting the hole transport layer contains the inventive compound, and it is more preferable that the hole transport layer contains the inventive compound.

[0622] 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.

[0623] 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.

[0624] 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.

[0625] 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.

[0626] 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.

[0627] Furthermore, it is also preferable to use an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K).

[0628] [ka]

[0629] (In the above formula, R 221 ~R 226 These are, independently, a cyano group, -CONH2, a carboxyl group, or -COOR. 227 (R 227 (represents an alkyl group with 1 to 20 carbon atoms or a cycloalkyl group with 3 to 20 carbon atoms). Also, R 221 and R 222 , R 223 and R 224 , and R 225 and R 226 Two adjacent elements selected from the group may bond to each other to form a group represented by -CO-O-CO-. R 227 Examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, cyclopentyl group, and cyclohexyl group.

[0630] 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.

[0631] 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, the hole transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, and the hole transport layer closest to the cathode in the multilayer structure, for example, the second hole transport layer in the two-layer structure or the third hole transport layer in the three-layer structure, is preferably adjacent to the light-emitting layer. In another embodiment of the present invention, an electron blocking layer, etc., described later, may be interposed between the hole transport layer of the single-layer structure and the light-emitting layer, or between the hole transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer. When the hole transport layer has a two-layer structure, at least one of the first hole transport layer and the second hole transport layer contains the inventive compound. That is, the inventive compound is contained in only the first hole transport layer, only the second hole transport layer, or in both the first and second hole transport layers. In one embodiment of the present invention, it is preferable that the inventive compound is contained in the second hole transport layer. That is, it is preferable that the inventive compound is contained only in the second hole transport layer, or that the inventive compound is contained in both the first hole transport layer and the second hole transport layer. If the hole transport layer has a three-layer structure, at least one of the first to third hole transport layers contains the inventive compound. That is, the inventive compound is 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, it is preferable that the inventive compound is contained in the third hole transport layer. That is, it is preferable that the inventive compound is contained only in the third hole transport layer, or that the inventive compound is contained in the third hole transport layer and one or both of the first hole transport layer and the second hole transport layer. In one embodiment of the present invention, the inventive compound contained in each hole transport layer is preferably a light hydrogen compound from the viewpoint of manufacturing cost. The light hydrogen compound is an inventive compound in which all hydrogen atoms in the inventive compound are light hydrogen atoms. Accordingly, the present invention includes an organic EL element containing an inventive compound in which one or both of the first hole transport layer and the second hole transport layer (in the case of a two-layer structure), or at least one of the first to third hole transport layers, consists 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 (each including 100%).

[0632] 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.

[0633] 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 other than those mentioned above may be used if it has higher hole transport properties than electron transport properties.

[0634] In the organic EL element having a two-layer hole transport layer of the present invention, it is preferable that the first hole transport layer contains one or more compounds represented by the following formula (11) or formula (12). In the organic EL element having a three-layer hole transport layer of the present invention, it is preferable that one or both of the first hole transport layer and the second hole transport layer contain one or more compounds represented by the following formulas (11) or (12). In the organic EL element having an n-layer structure (where n is an integer of 4 or more) of hole transport layers according to the present invention, it is preferable that at least one of the first to (n-1) hole transport layers contains one or more compounds represented by the following formula (11) or formula (12).

[0635] [ka] [In formulas (11) and (12) above, L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 Each of these is independently an arylene group with 6 to 50 ring-forming carbon atoms, either single-bonded, substituted, or unsubstituted, or a divalent heterocyclic group with 5 to 50 ring-forming atoms, k is 1, 2, 3, or 4. If k is 1, L E2 This is a substituted or unsubstituted arylene group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 ring-forming atoms. If k is 2, 3, or 4, then 2, 3, or 4 L E2 They are either identical or different from each other. If k is 2, 3, or 4, multiple L E2 They either bond to each other to form a substituted or unsubstituted monoring, or bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other. L that does not form the aforementioned monoring and does not form the aforementioned condensed ring E2This is a substituted or unsubstituted arylene group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 ring-forming atoms. A 1 B 1 , C 1 , A 2 B 2 , C 2 , and D 2 These are, independently, substituted or unsubstituted aryl groups with 6 to 50 ring-forming carbon atoms, substituted or unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms, or -Si(R' 901 )(R' 902 )(R' 903 ) and R' 901 , R' 902 and R' 903 These are, independently, substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms. R' 901 If multiple R's exist, 901 They are either identical or different from each other. R' 902 If multiple R's exist, 902 They are either identical or different from each other. R' 903 If multiple R's exist, 903 They are either identical or different from one another.

[0636] In formulas (11) and (12), A1, B1, C1, A2, B2, C2, and D2 are preferably each independently selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibensofuranil group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group. Furthermore, more preferably, in formula (11), at least one of A1, B1, and C1, and in formula (12), at least one of A2, B2, C2, and D2 is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibensofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group or a substituted or unsubstituted carbazolyl group.

[0637] The fluorenyl groups that A1, B1, C1, A2, B2, C2, and D2 can take may have substituents at the 9-position, for example, a 9,9-dimethylfluorenyl group or a 9,9-diphenylfluorenyl group. Furthermore, the substituents at the 9-position may form a ring, for example, a fluorene skeleton or a xanthene skeleton.

[0638] L A1 , L B1 , L C1 , L A2 , L B2 , L C2 and L D2 Preferably, each is independently a single-bonded, substituted, or unsubstituted ring-forming arylene group having 6 to 12 carbon atoms.

[0639] Specific examples of compounds represented by formulas (11) and (12) include the following compounds.

[0640] [ka]

[0641] 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. In one embodiment of the organic EL element according to the present invention, the light-emitting layer may be a single layer. Furthermore, in another embodiment of the organic EL element according to the present invention, the light-emitting layer may include a first light-emitting layer and a second light-emitting layer.

[0642] 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).

[0643] 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).

[0644] 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).

[0645] In one embodiment of the present invention, it is preferable that the light-emitting layer includes a fluorescent light-emitting material (fluorescent dopant material).

[0646] 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).

[0647] 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)).

[0648] 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).

[0649] 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.

[0650] 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.

[0651] 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.

[0652] 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.

[0653] In particular, for blue fluorescent elements, it is preferable to use the following anthracene compounds as the host material.

[0654] [ka]

[0655] [ka]

[0656] [ka]

[0657] In one embodiment of the organic EL element according to the present invention, when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, at least one of the components constituting the first light-emitting layer is different from the components constituting the second light-emitting layer. For example, this includes embodiments in which the dopant material contained in the first light-emitting layer is different from the dopant material contained in the second light-emitting layer, or embodiments in which the host material contained in the first light-emitting layer is different from the host material contained in the second light-emitting layer.

[0658] In the organic EL element of the present invention, the light-emitting layer may contain a light-emitting compound (hereinafter sometimes simply referred to as "fluorescent compound") that exhibits fluorescence emission with a main peak wavelength of 500 nm or less.

[0659] The method for measuring the main peak wavelength of a compound is as follows: Prepare a 5 μmol / L toluene solution of the compound to be measured, place it in a quartz cell, and measure the emission spectrum of the sample at room temperature (300 K) (vertical axis: emission intensity, horizontal axis: wavelength). The emission spectrum can be measured using a spectrofluorometer (instrument name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is defined as the principal peak wavelength. In this specification, the principal peak wavelength may be referred to as the fluorescence emission principal peak wavelength (FL-peak).

[0660] The fluorescent compound may be the dopant material or the host material.

[0661] If the light-emitting layer is a single layer, either only one of the dopant material or the host material may be the fluorescent compound, or both may be the fluorescent compound. Furthermore, if the light-emitting layer includes a first light-emitting layer (anode side) and a second light-emitting layer (cathode side), only one of the first or second light-emitting layer may contain the fluorescent compound, or both light-emitting layers may contain the fluorescent compound. If the first light-emitting layer contains the fluorescent compound, only one of the dopant material and host material contained in the first light-emitting layer may contain the fluorescent compound, or both may contain the fluorescent compound. Furthermore, if the second light-emitting layer contains the fluorescent compound, only one of the dopant material and host material contained in the second light-emitting layer may contain the fluorescent compound, or both may contain the fluorescent compound.

[0662] Electron transport band The electron transport band consists of an electron injection layer, an electron transport layer, a hole blocking layer, etc. Any layer of the electron transport band, particularly the electron transport layer, preferably contains one or more selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, organic complexes containing alkali metals, organic complexes containing alkaline earth metals, and organic complexes containing rare earth metals.

[0663] 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.

[0664] 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.

[0665] 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).

[0666] 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).

[0667] 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).

[0668] 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.

[0669] 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.

[0670] 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.

[0671] 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.

[0672] 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.

[0673] 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.

[0674] 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.

[0675] 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.

[0676] In the organic EL element having a two-layer or three-layer hole transport layer of the present invention, the sum of the thickness of the first hole transport layer and the thickness of the second hole transport layer is preferably 30 nm or more and 150 nm or less, and more preferably 40 nm or more and 130 nm or less. Furthermore, in one embodiment of the present invention, the thickness of the second hole transport layer in the two-layer or three-layer structure is preferably 5 nm or more, more preferably 20 nm or more, even more preferably 25 nm or more, particularly preferably 35 nm or more, and also preferably 100 nm or less. Furthermore, in one embodiment of the present invention, the thickness of the hole transport layer adjacent to the light-emitting layer is preferably 5 nm or more, more preferably 20 nm or more, even more preferably 25 nm or more, particularly preferably 30 nm or more, and also preferably 100 nm or less. In the organic EL device having a hole transport layer with a two-layer structure or a three-layer structure 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, and even more preferably 0.75 < D2 / D1 < 3.0.

[0677] Preferred embodiments of the organic EL device of the present invention include, for example, (1) An organic EL device having a hole transport layer with a two-layer structure · 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 hole transport layer with a three-layer structure · 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; · A tenth embodiment in which all of the first to third hole transport layers contain the inventive compound; and the like.

[0678] Electronic device An organic EL element according to one embodiment of the present invention can be used in electronic devices such as display devices and light-emitting devices. Examples of display devices include display components such as organic EL panel modules, televisions, mobile phones, tablets, or personal computers. Examples of light-emitting devices include lighting fixtures or vehicle lights.

[0679] 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]

[0680] The present invention will be described in more detail below using examples, but the present invention is not limited to the following examples.

[0681] The inventive compound used in the production of the organic EL element (I) in Examples 1 to 7 [ka]

[0682] Comparative compounds used in the production of organic EL elements (I) of Comparative Examples 1 and 2 [ka]

[0683] Other compounds used in the production of organic EL elements (I) in Examples 1-8 and Comparative Examples 1 and 2 [ka]

[0684] 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. After cleaning, a glass substrate with an ITO transparent electrode was mounted in the substrate holder of a vacuum deposition apparatus. First, compound HT-1 and compound HA were co-deposited onto the surface where 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 HT-1 to compound HA (HT-1:HA) was 97:3. Next, compound HT-1 was deposited onto the hole injection layer to form a first hole transport layer with a thickness of 85 nm. Next, compound Inv-1 was deposited onto this first hole transport layer to form a second hole transport layer with a thickness of 5 nm. Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited onto this second hole transport layer to form a light-emitting layer with a thickness of 20 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 99:1. Next, compound ET-1 was deposited onto this light-emitting layer to form a first electron transport layer with a thickness of 5 nm. Next, compound ET-2 and Liq were co-deposited onto this first electron transport layer to form a second electron transport layer with a thickness of 31 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50. Next, Liq 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 80 nm. The layer structure of the organic EL element (I) obtained in this way is shown below. ITO(130) / HT-1:HA=97:3(10) / HT-1(85) / Compound Inv-1(5) / BH-1:BD-1=99:1(20) / ET-1(5) / ET-2:Liq=50:50(31) / Liq(1) / Al(80) In the above layer configuration, the numbers in parentheses represent the film thickness (nm), and the ratios represent the mass ratios.

[0685] Examples 2-8, and Comparative Examples 1 and 2 An organic EL element (I) was fabricated in the same manner as in Example 1, except that the compound listed in Table 1 was used instead of compound Inv-1 as the second hole transport layer material.

[0686] Measurement of element lifetime (LT95) The resulting organic EL element (I) was subjected to a current density of 50 mA / cm². 2 The device was driven by DC current, and the time it took for the brightness to decrease to 95% of the initial brightness was measured. This was defined as the 95% lifetime (LT95). The results are shown in Table 1.

[0687] [Table 1]

[0688] As is clear from the results in Table 1, the organic EL element (I) containing the inventive compounds (compounds Inv-1 to Inv-3, compounds Inv-13 to Inv-17) has a longer lifespan than the organic EL element (I) containing comparative compound Ref-1 or comparative compound Ref-2.

[0689] Inventive compound used in the production of organic EL elements (II) in Examples 9-16 [ka]

[0690] Comparative compounds used in the production of organic EL elements (II) of Comparative Examples 3 and 4 [ka]

[0691] Other compounds used in the production of organic EL elements (II) in Examples 9-16 and Comparative Examples 3-5 [ka]

[0692] Fabrication of organic EL elements (II) Example 9 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. After cleaning, a glass substrate with an ITO transparent electrode was mounted in the substrate holder of a vacuum deposition apparatus. First, compound HT-2 and compound HA were co-deposited onto the surface where 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 HT-2 to compound HA (HT-2:HA) was 97:3. Next, compound HT-2 was deposited onto the hole injection layer to form a first hole transport layer with a thickness of 85 nm. Next, compound Inv-4 was deposited onto this first hole transport layer to form a second hole transport layer with a thickness of 10 nm. Next, compound BH-1 (host material) and compound BD-2 (dopant material) were co-deposited onto this second hole transport layer to form a light-emitting layer with a thickness of 20 nm. The mass ratio of compound BH-1 to compound BD-2 (BH-1:BD-2) was 99:1. Next, compound ET-1 was deposited onto this light-emitting layer to form a first electron transport layer with a thickness of 5 nm. Next, compound ET-2 and Liq were co-deposited onto this first electron transport layer to form a second electron transport layer with a thickness of 31 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50. Next, Liq 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 structure of the organic EL element (II) obtained in this way is shown below. ITO(130) / HT-2:HA=97:3(10) / HT-2(85) / Compound Inv-4(10) / BH-1:BD-2=99:1(20) / ET-1(5) / ET-2:Liq=50:50(31) / Liq(1) / Al(50) In the above layer configuration, the numbers in parentheses represent the film thickness (nm), and the ratios represent the mass ratios.

[0693] Examples 10-16 and Comparative Examples 3-5 Organic EL element (II) was fabricated in the same manner as in Example 9, except that the compound listed in Table 2 was used instead of compound Inv-4 as the second hole transport layer material.

[0694] Measurement of element lifetime (LT95) The obtained organic EL element (II) was subjected to a current density of 30 mA / cm². 2 The device was driven by DC current, and the time it took for the brightness to decrease to 95% of the initial brightness was measured. This was defined as the 95% lifetime (LT95). The results are shown in Table 2.

[0695] [Table 2]

[0696] As is clear from the results in Table 2, the organic EL element (II) containing the inventive compounds (compounds Inv-4, Inv-6 to Inv-12) has a longer lifespan than the organic EL element (II) containing comparative compound Ref-3, comparative compound Ref-4, or comparative compound Ref-5.

[0697] The inventive compound synthesized in the synthesis example. [ka]

[0698] [ka]

[0699] Intermediate synthesis example 1: Synthesis of intermediate A [ka]

[0700] Under an argon atmosphere, a mixture of 15.7 g (60.0 mmol) of 4,4,5,5-tetramethyl-2-(2-naphthalenyl-1,3,4,5,6,7,8-d7)-1,3,2-dioxaborolane (starting material 1), 10.1 g (30.0 mmol) of 4-bromo-N-(4-bromophenyl-2,3,5,6-d4)-benzene-2,3,5,6-d4-amine (starting material 2), 0.673 g (0.9 mmol) of bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 45 mL of 2M aqueous sodium carbonate solution, and 200 mL of DME (1,2-dimethoxyethane) was refluxed to boiling point for 7 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain intermediate A, a white solid of 11.7 g. The yield was 88%.

[0701] Intermediate synthesis example 2: Synthesis of intermediate B [ka]

[0702] Under an argon atmosphere, a mixture of 10.5 g (36.6 mmol) of 1-bromo-3-iodobenzene-2,3,4,6-d4 (starting material 1), 11.0 g (33.3 mmol) of 4,4,5,5-tetramethyl-2-(5-phenyl-1-naphthalenyl)-1,3,2-dioxaborolane (starting material 2), 0.770 g (0.67 mmol) of tetrakis(triphenylphosphine)palladium(0), 50 mL of 2M aqueous sodium carbonate solution, and 222 mL of DME (1,2-dimethoxyethane) was refluxed to boiling point for 7 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain intermediate B, a white solid of 7.33 g. The yield was 61%.

[0703] Intermediate synthesis example 3: Synthesis of intermediate C In intermediate synthesis example 2, the same procedure was followed except that the starting materials 1 and 2 were the compounds and amounts listed in Table 3, to obtain intermediate C. The yield of intermediate C is shown in Table 3.

[0704] Intermediate synthesis example 4: Synthesis of intermediate D In intermediate synthesis example 2, the same procedure was followed except that the starting materials 1 and 2 were the compounds and amounts listed in Table 3, to obtain intermediate D. The yield of intermediate D is shown in Table 3.

[0705] [Table 3]

[0706] Synthesis Example 1: Synthesis of Compound Inv-1 [ka]

[0707] Under an argon atmosphere, a mixture of 3.22 g (10.0 mmol) of 9-(3-bromophenyl)-9H-carbazole (intermediate 1), 4.44 g (10.0 mmol) of intermediate A (intermediate 2), 0.183 g (0.2 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.232 g (0.8 mmol) of tri-tert-butylphosphonium tetrafluoroborate, 1.35 g (14.0 mmol) of sodium-t-butoxide, and 67 mL of xylene was stirred at 110°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 and recrystallization to obtain 5.14 g of a white solid. The yield was 73%. The obtained compound, identified by mass spectrometry, was compound Inv-1, with a molecular weight of 684.97 and a m / e ratio of 685.

[0708] Synthesis Examples 2-17: Synthesis of Inventive Compounds Inv-2-Inv-17 In Synthesis Example 1, the same procedure was followed except that intermediates 1 and 2 were the compounds and quantities listed in Tables 4-6, to obtain the inventive compounds Inv-2 to Inv-17. The yields of each of the inventive compounds Inv-2 to Inv-17 are shown in Tables 4-6.

[0709] [Table 4]

[0710] [Table 5]

[0711] [Table 6] [Explanation of Symbols]

[0712] 1, 11, 12 Organic EL elements 2 circuit boards 3 Anode 4 cathode 5. Emitting layer 5a First light-emitting layer 5b Second light-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 (D). 【Chemistry 1】 (In formula (D), N * It is the central nitrogen atom. L ｄ１ This is a base represented by the following formula (viiii). 【Chemistry 2】 (In formula (viii), R ｄ３１ and R ｄ３５ One of the options selected is a single bond that connects to *d3. R that is not a single bond ｄ３１ ~R ｄ３５ Each of these is independently a hydrogen atom, an unsubstituted C1-C6 alkyl group, an unsubstituted ring-forming C3-C6 cycloalkyl group, an unsubstituted ring-forming C6-C18 aryl group, or an unsubstituted ring-forming C5-C18 heterocyclic group. *d2 is the central nitrogen atom N * Represents the binding position to * d1 is coupled to one selected from R ｄ２１ ~R ｄ２８ and is coupled to one selected therefrom. R that is not a single bond ｄ３１ ~R ｄ３５ Two adjacent elements selected from this set do not join to each other and do not form a ring. Ar ｄ１ This is a group represented by one of the following formulas (d1) to (d3). 【Transformation 3】 (In formula (d1), *d7 is the central nitrogen atom N * This indicates the connection position to the destination. R ｄ１０１ ~R ｄ１０５ One of the selected is a single bond that connects to *d8, R ｄ１０６ ~R ｄ１１０ One of the options selected is a single bond that connects to *d9. R that is not a single bond ｄ１０１ ~R ｄ１０５ , and R that is not a single bond ｄ１０６ ~R ｄ１１０ Each of these is independently a hydrogen atom, an unsubstituted C1-C10 alkyl group, an unsubstituted ring-forming C6-C12 aryl group, or an unsubstituted ring-forming C5-C12 heterocyclic group. R that is not a single bond ｄ１０１ ~R ｄ１０５ Two adjacent elements selected from this set do not join with each other and do not form a ring. R that is not a single bond ｄ１０６ ~R ｄ１１０ Two adjacent elements selected from this set do not join with each other and do not form a ring. R ｄ１１１ ~R ｄ１１５ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heterocyclic group. R ｄ１１１ ~R ｄ１１５ Two adjacent elements selected from this set do not join with each other and do not form a ring. m is either 0 or 1, and n is either 0 or 1. When m=0 and n=0, *d9 represents *d7, When m=0 and n=1, *d8 represents *d7, When m=1 and n=0, *d9 represents *d8. 【Chemistry 4】 (In formula (d2), *d10 is the central nitrogen atom N * This indicates the connection position to the destination. L ｄ２ This is a substituted or unsubstituted arylene group having 6 to 18 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 18 ring-forming atoms. R ｄ１２１ ~R ｄ１２８ One of the options selected is a single bond that connects to *d11. R that is not a single bond ｄ１２１ ~R ｄ１２８ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heterocyclic group. R that is not a single bond ｄ１２１ ~R ｄ１２８ Two adjacent elements selected from this set do not join to each other and do not form a ring. 【Transformation 5】 (In equation (d3), *d12 is the central nitrogen atom N * This indicates the connection position to the destination. L ｄ３ This is a substituted or unsubstituted arylene group having 6 to 18 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 18 ring-forming atoms. X ｄ１ This is either an oxygen atom or a sulfur atom. R ｄ１３１ ~R ｄ１３８ One of the options selected is a single bond that connects to *a14. R that is not a single bond ｄ１３１ ~R ｄ１３８ Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted ring-forming C6-C12 aryl group, or a substituted or unsubstituted ring-forming C5-C13 heterocyclic group. R that is not a single bond ｄ１３１ ~R ｄ１３８ Two adjacent elements selected from the set may join together to form a substituted or unsubstituted ring structure, or they may not join together and therefore not form a ring structure. R ｄ１ ~R ｄ４ This is a hydrogen atom. R ｄ１１ ~R ｄ１７ Each of these is independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. The aforementioned R ｄ１１ ~R ｄ１７ Two adjacent elements selected from this set do not join with each other and do not form a ring. Ring H and ring I may or may not be bridged. *R is not a single bond attached to d1. ｄ２１ ~R ｄ２８ Each of these is independently a hydrogen atom, or a substituted or unsubstituted ring-forming carbon-6 aryl group. *R is not a single bond attached to d1. ｄ２１ ~R ｄ２８ At least one of these selected is the substituted or unsubstituted ring-forming aryl group having 6 carbon atoms.

2. Ar ｄ１ The compound according to claim 1, wherein is a group represented by formula (d2).

3. L ｄ２ The compound according to claim 1 or 2, wherein is a substituted or unsubstituted phenylene group.

4. L ｄ２ The compound according to claim 1 or 2, wherein is a substituted or unsubstituted p-phenylene group.

5. Ar ｄ１ The compound according to claim 1 or 2, wherein is a group represented by formula (d1).

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

7. R ｄ１ ~R ｄ４ The compound according to claim 1 or 2, wherein at least one selected from is a deuterium atom.

8. Ar ｄ１ However, the group is represented by the above formula (d2), L ｄ２ The compound according to claim 1 or 2, wherein the compound has at least one deuterium atom.

9. R ｄ１ ~R ｄ４ All of them are deuterium atoms, Ar ｄ１ The group is represented by the above formula (d2), L ｄ２ This is an unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, and the L ｄ２ The compound according to claim 1 or 2, wherein all hydrogen atoms in the unsubstituted ring-forming arylene group having 6 to 30 carbon atoms represented by are deuterium atoms.

10. Ar ｄ１ The compound according to claim 1 or 2, wherein at least one hydrogen atom selected from the hydrogen atoms of the group represented by formulas (d1) to (d3) is a deuterium atom.

11. R ｄ１１１ ~R ｄ１１５ , R ｄ１２１ ~R ｄ１２４ , R which is not a single bond ｄ１３１ ~R ｄ１３８ , R which is not a single bond ｄ１１ ~R ｄ１７ , and R which is not a single bond bonded to *d1 ｄ２１ ~R ｄ２８ The compound according to claim 1 or 2, wherein the substituent in the phrase "substituted or unsubstituted" is a group selected from the group consisting of alkyl groups having 1 to 6 carbon atoms, aryl groups having 6 to 18 ring-forming carbon atoms, and heterocyclic groups having 5 to 18 ring-forming atoms.

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

13. 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.

14. The organic electroluminescent element according to claim 13, 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.

15. The organic electroluminescent element according to claim 14, 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 one or both of the first hole transport layer and the second hole transport layer contain the compound.

16. The organic electroluminescent element according to claim 13, wherein the light-emitting layer includes a fluorescent dopant material.

17. The organic electroluminescent element according to claim 13, wherein the light-emitting layer includes a phosphorescent dopant material.

18. An electronic device comprising the organic electroluminescent element described in claim 13.

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