Compound, organic electroluminescent element, and electronic device
By integrating a compound with specific structures into the organic layers of organic electroluminescence elements, the performance of these elements is enhanced, resulting in lower driving voltage and longer lifespan.
Patent Information
- Application Number
- PCT/JP2024/043813
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2023-12-12
- Filing Date
- 2024-12-11
- Publication Date
- 2025-06-19
AI Technical Summary
Conventional organic electroluminescence (EL) elements have not achieved sufficient device performance, and further improvements are needed to enhance their performance.
Incorporating a specific compound with a structure represented by formula (S1) and formula (S2) into at least one layer of the organic layers of the organic EL element.
The use of this compound leads to a higher-performance organic EL element with improved efficiency, reduced driving voltage, and extended lifespan.
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Figure JP2024043813_19062025_PF_FP_ABST
Abstract
Description
Compound, organic electroluminescent element, and electronic device
[0001] The present invention relates to a novel compound, an organic electroluminescence element, and an electronic device.
[0002] When a voltage is applied to an organic electroluminescence element (hereinafter also referred to as an organic EL element), holes are injected from the anode and electrons are injected from the cathode into the light-emitting layer, where they recombine to form excitons.
[0003] Conventional organic EL elements have not yet achieved sufficient element performance. Although improvements to organic EL elements have been made gradually to enhance element performance, further improvements in performance are still required. Patent Document 1 discloses a compound having a specific structure for use in an organic EL element.
[0004] US Patent Application Publication No. 2016 / 0126463 Chinese Patent Application Publication No. 112838168 International Publication No. 2008 / 145239
[0005] An object of the present invention is to provide an organic EL device with higher performance.
[0006] As a result of extensive research to achieve the above object, the present inventors have discovered that a high-performance organic EL element can be obtained by using a compound having a specific structure in at least one of the organic layers of the organic EL element, and have completed the present invention.
[0007] According to the present invention, the following compounds and the like are provided: 1. A compound comprising a structure represented by the following formula (S1) and a structure represented by the following formula (S2). [In formula (S1), X 1 is a single bond, O, or S.] 2. An organic electroluminescence element comprising: a cathode; an anode; and one or more organic layers disposed between the cathode and the anode, wherein at least one of the organic layers contains the compound described in 1. 3. An electronic device comprising the organic electroluminescence element described in 2.
[0008] According to the present invention, an organic EL device with higher performance can be provided.
[0009] 1 is a diagram showing a schematic configuration of an organic EL element according to one embodiment of the present invention.
[0010] [Definitions] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.
[0011] In this specification, in a chemical structural formula, a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded to a possible bonding position that is not explicitly marked with a symbol such as "R" or "D" representing a deuterium atom.
[0012] As used herein, the term "number of ring carbon atoms" refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. For example, a 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and a 9,9'-spirobifluorenyl group has 25 ring carbon atoms. When a benzene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of a benzene ring substituted with an alkyl group is 6. Furthermore, when the naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.
[0013] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, and a ring assembly). Atoms that do not constitute the ring (e.g., hydrogen atoms terminating the bonds of atoms constituting the ring) and atoms contained in the substituent when the ring is substituted with a substituent are not included in the number of ring atoms. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms or atoms constituting a substituent bonded to the pyridine ring is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. Furthermore, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring, so the number of ring atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.
[0014] In this specification, the "number of carbon atoms XX to YY" in the expression "substituted or unsubstituted ZZ group having carbon atoms XX to YY" represents the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.
[0015] In this specification, the "number of atoms XX to YY" in the expression "substituted or unsubstituted ZZ group having number of atoms XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of substituents when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.
[0016] In this specification, an unsubstituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group". In this specification, "unsubstituted" in the case of a "substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protist atom, a deuterium atom, or a tritium atom. Furthermore, in this specification, "substituted" in the case of a "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. Similarly, "substituted" in the case of a "BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced with an AA group.
[0017] "Substituents Described in This Specification" The substituents described in this specification are explained below.
[0018] The number of ring carbon atoms of an "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 atoms of an "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 of an "unsubstituted alkyl group" 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 of an "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 of an "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 carbon atoms of an "unsubstituted cycloalkyl group" described herein is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified herein. Unless otherwise specified herein, the number of ring carbon atoms of an "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 atoms of an "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 of an "unsubstituted alkylene group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[0019] "Substituted or Unsubstituted Aryl Group" Specific examples (Specific Example Group G1) of the "substituted or unsubstituted aryl group" described herein include the following unsubstituted aryl group (Specific Example Group G1A) and substituted aryl group (Specific Example Group G1B). (Here, an unsubstituted aryl group refers to a case where a "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and a substituted aryl group refers to a case where a "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" simply refers to both an "unsubstituted aryl group" and a "substituted aryl group." A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with substituents. Examples of the "substituted aryl group" include a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with substituents in the "unsubstituted aryl group" of the following Specific Example Group G1A, and examples of the substituted aryl group of the following Specific Example Group G1B. It should be noted that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl groups" described in this specification also include groups in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl groups" of the following specific example group G1B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted aryl groups" of the following specific example group G1B is further replaced with a substituent.
[0020] Unsubstituted aryl groups (specific example group G1A): 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, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a benzanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a triphenylenyl group, a benzotriphenylenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, A 9,9'-spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a fluoranthenyl group, a benzofluoranthenyl group, a perylenyl group, and a monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).
[0021]
[0022]
[0023] Substituted aryl groups (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl 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 in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by the above general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.
[0024] "Substituted or Unsubstituted Heterocyclic Group" The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom among the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom. The "heterocyclic group" described herein is a monocyclic group or a fused ring group. The "heterocyclic group" described herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described herein include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, an unsubstituted heterocyclic group refers to when a "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and a substituted heterocyclic group refers to when a "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when simply referring to a "heterocyclic group", it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group". A "substituted heterocyclic group" means a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with substituents. Specific examples of the "substituted heterocyclic group" include groups in which hydrogen atoms of an "unsubstituted heterocyclic group" in the following specific example group G2A are replaced, and examples of substituted heterocyclic groups in the following specific example group G2B. The examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic groups" described in this specification also include groups in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic groups" of specific example group G2B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted heterocyclic groups" of specific example group G2B is further replaced with a substituent.
[0025] Specific example 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 ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).
[0026] Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced with substituents (specific example group G2B4).
[0027] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolidinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, an indazolyl group, a phenanthrolinyl group, a phenanthridinyl group, an acridinyl group, a phenazinyl group, a carbazolyl group, Benzocarbazolyl group, morpholino group, phenoxazinyl group, phenothiazinyl group, azacarbazolyl group, and diazacarbazolyl group.
[0028] Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): a furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a xanthenyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a benzoxazolyl group, a benzisoxazolyl group, a phenoxazinyl group, a morpholino group, a dinaphthofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, an azanaphthobenzofuranyl group, and a diazanaphthobenzofuranyl group.
[0029] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a benzothiophenyl group (benzothienyl group), an isobenzothiophenyl group (isobenzothienyl group), a dibenzothiophenyl group (dibenzothienyl group), a naphthobenzothiophenyl group (naphthobenzothienyl group), a benzothiazolyl group, a benzisothiazolyl group, a phenothiazinyl group, a dinaphthothiophenyl group (dinaphthothienyl group), an azadibenzothiophenyl group (azadibenzothienyl group), a diazadibenzothiophenyl group (diazadibenzothienyl group), an azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and a diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).
[0030] Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4):
[0031]
[0032]
[0033] In the general formulae (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH 2 However, X A and Y A At least one of X is an oxygen atom, a sulfur atom, or NH. A and Y A At least one of the groups is NH or CH 2 In this case, the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) may contain any of these NH, CH 2 and monovalent groups obtained by removing one hydrogen atom from the group consisting of:
[0034] Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): a (9-phenyl)carbazolyl group, a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a (9-naphthyl)carbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a methylbenzimidazolyl group, an ethylbenzimidazolyl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenylquinazolinyl group, and a biphenylylquinazolinyl group.
[0035] Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): a phenyldibenzofuranyl group, a methyldibenzofuranyl group, a t-butyldibenzofuranyl group, and a monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].
[0036] Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3): a phenyldibenzothiophenyl group, a methyldibenzothiophenyl group, a t-butyldibenzothiophenyl group, and a monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].
[0037] Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4):
[0038] The "one or more hydrogen atoms of the monovalent heterocyclic group" refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, X A and Y A a hydrogen atom bonded to a nitrogen atom when at least one of A and Y A One of them is CH 2 and n is 0 or more. The methylene group in the formula (I) is one or more hydrogen atoms selected from the hydrogen atoms of the methylene group in the formula (I).
[0039] "Substituted or Unsubstituted Alkyl Group" Specific examples (Specific Example Group G3) of the "substituted or unsubstituted alkyl group" described herein include the following unsubstituted alkyl group (Specific Example Group G3A) and substituted alkyl group (Specific Example Group G3B). (Here, the term "unsubstituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and the term "substituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereinafter, the term "alkyl group" includes both an "unsubstituted alkyl group" and a "substituted alkyl group." A "substituted alkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced with substituents. Specific examples of the "substituted alkyl group" include the following "unsubstituted alkyl group" (Specific Example Group G3A) in which one or more hydrogen atoms are replaced with substituents, and the examples of the substituted alkyl group (Specific Example Group G3B). In this specification, the alkyl group in an "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the term "unsubstituted alkyl group" includes a straight-chain "unsubstituted alkyl group" and a branched "unsubstituted alkyl group." The examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes groups in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" of specific example group G3B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted alkyl group" of specific example group G3B is further replaced with a substituent.
[0040] Unsubstituted alkyl groups (specific example group G3A): a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, and a t-butyl group.
[0041] Substituted alkyl groups (specific example group G3B): a heptafluoropropyl group (including isomers), a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, and a trifluoromethyl group.
[0042] "Substituted or Unsubstituted Alkenyl Group" Specific examples (Specific Example Group G4) of the "substituted or unsubstituted alkenyl group" described herein include the following unsubstituted alkenyl group (Specific Example Group G4A) and substituted alkenyl group (Specific Example Group G4B). (Here, an unsubstituted alkenyl group refers to a case where a "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and a "substituted alkenyl group" refers to a case where a "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply refers to both an "unsubstituted alkenyl group" and a "substituted alkenyl group." A "substituted alkenyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced with substituents. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl groups" (specific example group G4A) having a substituent, and examples of substituted alkenyl groups (specific example group G4B). The examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl group" described in this specification also includes groups in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl groups" of specific example group G4B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted alkenyl groups" of specific example group G4B is further replaced with a substituent.
[0043] Unsubstituted alkenyl groups (specific example group G4A): a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, and a 3-butenyl group.
[0044] Substituted alkenyl groups (specific example group G4B): a 1,3-butadienyl group, a 1-methylvinyl group, a 1-methylallyl group, a 1,1-dimethylallyl group, a 2-methylallyl group, and a 1,2-dimethylallyl group.
[0045] - "Substituted or Unsubstituted Alkynyl Group" Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl group (specific example group G5A). (Here, an unsubstituted alkynyl group refers to a case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, the term "alkynyl group" includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group." A "substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" have been replaced with a substituent. Specific examples of the "substituted alkynyl group" include a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" (specific example group G5A) have been replaced with a substituent.
[0046] Unsubstituted alkynyl groups (specific example group G5A): ethynyl group
[0047] "Substituted or Unsubstituted Cycloalkyl Group" Specific examples (Specific Example Group G6) of the "substituted or unsubstituted cycloalkyl group" described herein include the following unsubstituted cycloalkyl group (Specific Example Group G6A) and substituted cycloalkyl group (Specific Example Group G6B). (Here, the term "unsubstituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group," and the term "substituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group.") In this specification, the term "cycloalkyl group" simply refers to both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group." A "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced with substituents. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (Specific Example Group G6A) in which one or more hydrogen atoms are replaced with substituents, and the examples of the substituted cycloalkyl group (Specific Example Group G6B). The examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed here are merely examples, and the "substituted cycloalkyl groups" described in this specification also include groups in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl groups" of specific example group G6B are replaced with substituents, and groups in which a hydrogen atom of a substituent in the "substituted cycloalkyl groups" of specific example group G6B is further replaced with a substituent.
[0048] Unsubstituted cycloalkyl groups (specific example group G6A): a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a 2-norbornyl group.
[0049] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.
[0050] -Si(R 901 ) (R 902 ) (R 903 A group represented by —Si(R 901 ) (R 902) (R 903 Specific examples (specific example group G7) of the group represented by the formula (G1) include -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, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. The multiple G1s in -Si(G1)(G1)(G1) may be the same or different. - Multiple G2 in Si(G1)(G2)(G2) are the same as or different from each other. - Multiple G1 in Si(G1)(G1)(G2) are the same as or different from each other. - Multiple G2 in Si(G2)(G2)(G2) are the same as or different from each other. - Multiple G3 in Si(G3)(G3)(G3) are the same as or different from each other. - Multiple G6 in Si(G6)(G6)(G6) are the same as or different from each other.
[0051] ・「-O-(R 904 A group represented by —O—(R 904 ) (Specific example group G8) includes -O(G1), -O(G2), -O(G3), and -O(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
[0052] ・"-S-(R 905 A group represented by —S—(R 905) (Specific example group G9) includes -S(G1), -S(G2), -S(G3), and -S(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
[0053] ・「-N(R 906 ) (R 907 A group represented by —N(R 906 ) (R 907 Specific examples (specific example group G10) of groups represented by the formula (G1) include -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. Multiple G1s in -N(G1)(G1) may be the same as or different from one another. Multiple G2s in -N(G2)(G2) may be the same as or different from one another. Multiple G3s in -N(G3)(G3) may be the same as or different from one another. The multiple G6s in -N(G6)(G6) are the same as or different from each other.
[0054] "Halogen Atom" Specific examples (specific example group G11) of the "halogen atom" described in this specification include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
[0055] "Substituted or unsubstituted fluoroalkyl group" As used herein, a "substituted or unsubstituted fluoroalkyl group" refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). Unless otherwise specified herein, the number of carbon atoms in an "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. A "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. Note that the "substituted fluoroalkyl group" described herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in a "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include the examples of the above-mentioned "alkyl group" (specific example group G3) in which one or more hydrogen atoms have been replaced with fluorine atoms.
[0056] "Substituted or unsubstituted haloalkyl group" As used herein, a "substituted or unsubstituted haloalkyl group" refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with 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 with a substituent. Note that the "substituted haloalkyl group" described herein also includes a "substituted haloalkyl group" in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain are further replaced with a substituent, and a "substituted haloalkyl group" in which one or more hydrogen atoms of the substituent are further replaced with a substituent. Specific examples of the "unsubstituted haloalkyl group" include the examples of the above-mentioned "alkyl group" (specific example group G3) in which one or more hydrogen atoms are replaced with halogen atoms. A haloalkyl group may also be referred to as a halogenated alkyl group.
[0057] - "Substituted or unsubstituted alkoxy group" A specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.
[0058] - "Substituted or unsubstituted alkylthio group" A specific example of the "substituted or unsubstituted alkylthio group" described in this specification is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.
[0059] - "Substituted or unsubstituted aryloxy group" A specific example of the "substituted or unsubstituted aryloxy group" described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. Unless otherwise specified in this specification, the number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.
[0060] - "Substituted or unsubstituted arylthio group" A specific example of the "substituted or unsubstituted arylthio group" described in this specification is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. Unless otherwise specified in this specification, the number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.
[0061] - "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Multiple G3s in -Si(G3)(G3)(G3) are the same as or different from one another. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[0062] "Substituted or unsubstituted aralkyl group" A specific example of the "substituted or unsubstituted aralkyl group" described in this specification is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. Therefore, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one embodiment of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group," 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 in this specification. Specific examples of the "substituted or unsubstituted aralkyl group" include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group, an α-naphthylmethyl group, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group, a 1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, a β-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethyl group, a 1-β-naphthylisopropyl group, and a 2-β-naphthylisopropyl group.
[0063] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described in this specification is 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, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, or the like.
[0064] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic group described in this specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an aza Examples of such groups include a dibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group (a (9-phenyl)carbazol-1-yl group, a (9-phenyl)carbazol-2-yl group, a (9-phenyl)carbazol-3-yl group, or a (9-phenyl)carbazol-4-yl group), a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group.
[0065] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.
[0066]
[0067] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically any of the following groups:
[0068]
[0069] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a binding site.
[0070] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.
[0071]
[0072] In the general formulae (TEMP-34) to (TEMP-41), * represents a binding site.
[0073] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like.
[0074] "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group". Specific examples (specific example group G12) of the "substituted or unsubstituted arylene group" include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1.
[0075] "Substituted or unsubstituted divalent heterocyclic group" Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom on the heterocycle from the above-mentioned "substituted or unsubstituted heterocyclic group". Specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group" include divalent groups derived by removing one hydrogen atom on the heterocycle from the "substituted or unsubstituted heterocyclic group" described in specific example group G2.
[0076] "Substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group". Specific examples (specific example group G14) of the "substituted or unsubstituted alkylene group" include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3.
[0077] Unless otherwise specified in the present specification, the substituted or unsubstituted arylene group described in the present specification is preferably any one of the groups represented by the following general formulae (TEMP-42) to (TEMP-68).
[0078]
[0079]
[0080] In the general formulae (TEMP-42) to (TEMP-52), Q 1 ~Q 10 are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-42) to (TEMP-52), * represents a binding site.
[0081]
[0082] In the general formulae (TEMP-53) to (TEMP-62), Q 1 ~Q 10 are each independently a hydrogen atom or a substituent. 9 and Q 10 may be bonded to each other via a single bond to form a ring. In the general formulae (TEMP-53) to (TEMP-62), * represents a bonding site.
[0083]
[0084] In the general formulae (TEMP-63) to (TEMP-68), Q 1 ~Q 8 are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-63) to (TEMP-68), * represents a binding site.
[0085] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any one of the groups represented by the following general formulae (TEMP-69) to (TEMP-102).
[0086]
[0087]
[0088]
[0089] In the general formulae (TEMP-69) to (TEMP-82), Q 1 ~Q 9 are each independently a hydrogen atom or a substituent.
[0090]
[0091]
[0092]
[0093]
[0094] In the general formulae (TEMP-83) to (TEMP-102), Q 1 ~Q 8 are each independently a hydrogen atom or a substituent.
[0095] The above is the explanation of "substituents described in this specification."
[0096] "When bonded to form a ring" In this specification, when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle, bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other," it means when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle," when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring," and when "one or more pairs of adjacent groups do not bond to each other." In this specification, the cases when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle" and "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "when bonded to form a ring") will be explained below. An anthracene compound represented by the following general formula (TEMP-103), in which the main skeleton is an anthracene ring, will be described as an example.
[0097]
[0098] For example, R 921~R 930 In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," the pair of adjacent two groups is R 921 and R 922 With the pair, R 922 and R 923 With the pair, R 923 and R 924 With the pair, R 924 and R 930 With the pair, R 930 and R 925 With the pair, R 925 and R 926 With the pair, R 926 and R 927 With the pair, R 927 and R 928 With the pair, R 928 and R 929 and R 929 and R 921 It is paired with.
[0099] The above-mentioned "one or more pairs" means that two or more pairs of adjacent two or more groups may simultaneously form a ring. For example, R 921 and R 922 and are bonded to each other to form ring Q A and simultaneously form R 925 and R 926 and are bonded to each other to form ring Q B When the anthracene compound represented by the general formula (TEMP-103) is formed, the anthracene compound represented by the general formula (TEMP-104) is represented by the following general formula (TEMP-104).
[0100]
[0101] The case where a "set of two or more adjacent groups" forms a ring includes not only the case where a set of "two" adjacent groups is bonded as in the above example, but also the case where a set of "three or more" adjacent groups is bonded. For example, R 921 and R 922 and are bonded to each other to form ring Q A and R 922 and R 923 and are bonded to each other to form ring Q C and three adjacent (R 921 , R 922 and R923 In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105): A and Ring Q C is R 922 Share.
[0102]
[0103] The "monocyclic ring" or "fused ring" formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when "one pair of adjacent two" forms a "monocyclic ring" or a "fused ring", the "monocyclic ring" or the "fused ring" may form a saturated ring or an unsaturated ring. For example, in the case of the ring Q formed in the general formula (TEMP-104), A and Ring Q B are "monocyclic rings" or "fused rings". A , and ring Q C is a "fused ring". A and Tamaki Q C That is, Ring Q A and Tamaki Q C The ring Q in the general formula (TMEP-104) is fused to form a fused ring. A is a benzene ring, then ring Q A The ring Q in the general formula (TMEP-104) is a monocyclic ring. A is a naphthalene ring, then ring Q A is a fused ring.
[0104] "Unsaturated rings" include aromatic hydrocarbon rings and aromatic heterocycles, as well as aliphatic hydrocarbon rings having an unsaturated bond, i.e., a double bond and / or a triple bond, in the ring structure (e.g., cyclohexene, cyclohexadiene, etc.), and non-aromatic heterocycles having an unsaturated bond (e.g., dihydropyran, imidazoline, pyrazoline, quinolizine, indoline, isoindoline, etc.). "Saturated rings" include aliphatic hydrocarbon rings having no unsaturated bonds, or non-aromatic heterocycles having no unsaturated bonds. Specific examples of aromatic hydrocarbon rings include structures in which the groups listed as specific examples in Specific Example Group G1 are terminated with a hydrogen atom. Specific examples of aromatic heterocycles include structures in which the aromatic heterocyclic groups listed as specific examples in Specific Example Group G2 are terminated with a hydrogen atom. Specific examples of aliphatic hydrocarbon rings include structures in which the groups listed as specific examples in Specific Example Group G6 are terminated with a hydrogen atom. "Forming a ring" means forming a ring with only multiple atoms of the parent skeleton, or with multiple atoms of the parent skeleton and one or more optional atoms. For example, R 921 and R 922 and a ring Q formed by bonding together A is R 921 and the carbon atom of the anthracene skeleton to which R 922 It means a ring formed by the carbon atom of the anthracene skeleton to which R is bonded and one or more arbitrary atoms. 921 and R 922 Todekan Q A In the case where R 921 and the carbon atom of the anthracene skeleton to which R 922 When a monocyclic unsaturated ring is formed by the carbon atom of the anthracene skeleton to which R is bonded and four carbon atoms, R 921 and R 922 The ring formed by
[0105] Here, unless otherwise specified herein, the "any atom" is preferably at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. In any atom (for example, in the case of a carbon atom or a nitrogen atom), a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "any substituent" described below. When any atom other than a carbon atom is included, the formed ring is a heterocycle. Unless otherwise specified herein, the "one or more any atoms" constituting the monocycle or fused ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5. Unless otherwise specified herein, of the "monocycle" and the "fused ring," the "monocycle" is preferred. Unless otherwise specified herein, of the "saturated ring" and the "unsaturated ring," the "unsaturated ring" is preferred. Unless otherwise specified herein, the "monocycle" is preferably a benzene ring. Unless otherwise specified herein, the "unsaturated ring" is preferably a benzene ring. When "one or more pairs of adjacent two or more rings" "combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring," unless otherwise specified in this specification, preferably, one or more pairs of adjacent two or more rings combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and at least one atom selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.
[0106] When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents Described Herein." When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents Described Herein." The above is an explanation of the case where "one or more pairs of adjacent two or more rings are bonded to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent two or more rings are bonded to form a substituted or unsubstituted fused ring" ("when bonded to form a ring").
[0107] Substituents in the case of "substituted or unsubstituted" In one embodiment of the present specification, the substituents in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituents" in the present specification) include, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 ) (R 902 ) (R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 ) (R 907 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and an unsubstituted heterocyclic group having 5 to 50 ring atoms, 901 ~R 907 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. 901 When there are two or more R901 are the same or different from each other, R 902 When there are two or more R 902 are the same or different from each other, R 903 When there are two or more R 903 are the same or different from each other, R 904 When there are two or more R 904 are the same or different from each other, R 905 When there are two or more R 905 are the same or different from each other, R 906 When there are two or more R 906 are the same or different from each other, R 907 When there are two or more R 907 are the same or different from each other.
[0108] In one embodiment, the substituent in the "substituted or unsubstituted" is a group selected from the group consisting of an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and a heterocyclic group having 5 to 50 ring atoms.
[0109] In one embodiment, the substituent in the "substituted or unsubstituted" is a group selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heterocyclic group having 5 to 18 ring atoms.
[0110] Specific examples of each group of the above optional substituents are the specific examples of the substituents described above in the section "Substituents described in this specification."
[0111] Unless otherwise specified in this specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring. Unless otherwise specified in this specification, any optional substituent may further have a substituent. The substituents further possessed by the optional substituent are the same as those of the optional substituents described above.
[0112] In this specification, a numerical range expressed using "AA to BB" means a range that includes the number AA written before "AA to BB" as the lower limit and the number BB written after "AA to BB" as the upper limit.
[0113] [Novel Compound] A compound according to one aspect of the present invention includes a structure represented by the following formula (S1) and a structure represented by the following formula (S2). [In formula (S1), X 1 is a single bond, O, or S.
[0114] When the compound according to one embodiment of the present invention is used in an organic layer of an organic EL device, the device performance can be improved. Specifically, an organic EL device having a low driving voltage and a long life can be realized.
[0115] A compound according to one embodiment of the present invention includes a specific nitrogen-containing heterocyclic structure represented by formula (S1) and a benzanthracene structure, and it is believed that the above-described effects can be achieved by employing such a structure. Although the reason for the above-described effects is not entirely clear, combining the specific nitrogen-containing heterocyclic structure represented by formula (S1) with the benzanthracene structure makes it possible to resolve the problem of high driving voltage that has traditionally been a concern with compounds having a benzanthracene structure. Furthermore, the high electron-donating ability of the nitrogen atom is thought to improve hole injection into the light-emitting layer, thereby contributing to a further reduction in driving voltage. Similarly, although not entirely clear, it is believed that the nitrogen-containing heterocyclic structure has increased molecular rigidity compared to, for example, a conventional phenylcarbazole structure, thereby suppressing molecular motion and contributing to a longer lifetime.
[0116] The structure represented by formula (S1) and the structure represented by formula (S2) may each independently have a substituent or may be unsubstituted. The substituent will be described later. A substituted or unsubstituted monocyclic or fused ring may be fused to the structure represented by formula (S1).
[0117] The phrase "a compound comprising a structure represented by formula (S1) and a structure represented by formula (S2)" means that the compound comprises both a structure represented by formula (S1) and a structure represented by formula (S2) as parts of the molecule. For example, the compound may comprise a structure represented by formula (S1) and a structure represented by formula (S2) as moieties within a single molecule. Similarly, the compound may comprise a moiety comprising a structure represented by formula (S1) and a moiety comprising a structure represented by formula (S2) within a single molecule.
[0118] In the compound according to one embodiment of the present invention, atoms constituting the structure represented by Formula (S1) (excluding atoms of substituents) and atoms constituting the structure represented by Formula (S2) (excluding atoms of substituents) are not shared. Furthermore, the structure represented by Formula (S1) and the structure represented by Formula (S2) are not fused via one or more single rings or fused rings to form a fused ring containing both the structure represented by Formula (S1) and the structure represented by Formula (S2).
[0119] For example, compounds of the following formulae (E1) and (E2), in which a structure represented by formula (S1) and a structure represented by formula (S2) are fused together by sharing two or more carbon atoms, are not included in the compounds according to one embodiment of the present invention. Furthermore, compounds of the following formulae (E3), in which a structure represented by formula (S1) and a structure represented by formula (S2) share a benzene ring, are not included in the compounds according to one embodiment of the present invention. Furthermore, compounds of the following formulae (E4) and (E5), in which a structure represented by formula (S1) and a structure represented by formula (S2) are fused together via a benzene ring, are not included in the compounds according to one embodiment of the present invention.
[0120] A compound including a structure represented by formula (S1) and a structure represented by formula (S2) is composed of a structure represented by formula (S1), a structure represented by formula (S2), and a single bond or one or more linking groups. For example, a compound such as the following formula (E6), in which the structure represented by formula (S1) and the structure represented by formula (S2) are linked by a phenylene group, is included in the compounds according to one embodiment of the present invention. Furthermore, for example, a compound such as the following formula (E7), in which a structure in which a benzene ring is fused to the structure represented by formula (S1) and the structure represented by formula (S2) are linked by a single bond, is included in the compounds according to one embodiment of the present invention.
[0121] In one embodiment, the compound according to one aspect of the present invention contains at least 36 carbon atoms and one nitrogen atom (X 1 is a single bond), contains at least 36 carbon atoms, 1 nitrogen atom, and 1 oxygen atom (X 1is O), or contains at least 36 carbon atoms, 1 nitrogen atom, and 1 sulfur atom (where X 1 is S), when it has a linking group connecting the structure represented by formula (S1) and the structure represented by formula (S2), it further contains atoms that constitute the linking group.
[0122] In one embodiment, the compound according to one aspect of the present invention is represented by the following formula (1): [In formula (1), X 1 is as defined in the formula (S1). 1 ~R 11 At least one pair of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or to form a substituted or unsubstituted fused ring, or do not form the monocyclic ring or the fused ring. 1 ~R 11 One of them is (L 1 ) n1 represents a single bond with R 1 ~R 11 One of the atoms constituting a substituted or unsubstituted monocyclic or condensed ring formed by bonding together one or more pairs of adjacent two or more of the 1 ) n1 is bonded to by a single bond. 21 ~R 32 At least one pair of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or to form a substituted or unsubstituted fused ring, or do not form the monocyclic ring or the fused ring. 21 ~R 32 One of them is (L 1 ) n1 represents a single bond with R 21 ~R 32 and one of the atoms constituting the substituted or unsubstituted monocyclic or fused ring formed by bonding together one or more pairs of adjacent two or more of the above-mentioned groups is (L 1 ) n1and R which does not represent the single bond and does not form the single ring or the fused ring. 1 ~R 11 and R 21 ~R 32 are each independently a hydrogen atom or a substituent R. 1 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms. n1 is an integer of 0 to 3. When n1 is 0, (L 1 ) n1 When n1 is 2 or more, two or more L 1 are connected in series with each other. When n1 is 2 or more, two or more L 1 may be the same or different. The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 ) (R 902 ) (R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 ) (R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. 901 ~R 907 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. 901 ~R 907 When there are two or more R 901 ~R 907may be the same or different. When two or more substituents R are present, the two or more substituents R may be the same or different.
[0123] In formula (1), when n1 is 0, (L 1 ) n1 is a single bond, and the structure (X 1 In formula (1), when n1 is 2 or more, two or more L 1 are connected in series with each other. It is obvious from the definition, for example, when n1 is 2, two L 1 is X 1 and a ring having a benzanthracene skeleton are connected in series between the fused ring containing "(X 1 a fused ring containing 1 -L 1 -(a ring having a benzoanthracene skeleton) structure. 1 The fused ring containing two L 1 The ring having the benzanthracene skeleton is bonded to one of the two L 1 When n1 is 3, three L 1 is X 1 and a ring having a benzanthracene skeleton are connected in series between the fused ring containing "(X 1 a fused ring containing 1 -L 1 -L 1 -(benzoanthracene ring) structure.
[0124] In one embodiment, R 7 ~R 10 One of them is (L 1 ) n1 In one embodiment, R 7 (L 1 ) n1 In one embodiment, R 8 (L 1 ) n1In one embodiment, R 9 (L 1 ) n1 In one embodiment, R 10 (L 1 ) n1 represents a single bond with
[0125] In one embodiment, R 21 , R 24 , R 27 , R 29 , R 30 , and R 32 One of them is (L 1 ) n1 In one embodiment, R 21 , R 24 , R 27 , and R 32 One of them is (L 1 ) n1 In one embodiment, R 27 (L 1 ) n1 In one embodiment, R 32 (L 1 ) n1 represents a single bond with
[0126] In one embodiment, R 7 ~R 10 One of them is (L 1 ) n1 represents a single bond with R 21 , R 24 , R 27 , R 29 , R 30 , and R 32 One of them is (L 1 ) n1 represents a single bond with
[0127] In one embodiment, R 1 ~R 11 At least one pair of adjacent two or more of the above does not form the single ring or the fused ring.
[0128] In one embodiment, the R 1 ~R 11is a hydrogen atom.
[0129] In one embodiment, R 21 ~R 32 At least one pair of adjacent two or more of the above does not form the single ring or the fused ring.
[0130] In one embodiment, the R 21 ~R 31 is a hydrogen atom, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group. 21 ~R 31 is a hydrogen atom.
[0131] In one embodiment, X 1 is a single bond or O. In one embodiment, X 1 is a single bond.
[0132] In one embodiment, L 1 represents a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.
[0133] In one embodiment, L 1 represents a single bond, an unsubstituted phenylene group, or an unsubstituted naphthylene group.
[0134] In one embodiment, n1 is 0. In one embodiment, n1 is 1.
[0135] In one embodiment, the compound represented by formula (1) is a compound represented by any one of formulas (11) to (18) below. [In formulas (11) to (18), X 1 , n1, and L 1 is as defined in the above formula (1). 101 ~R 111 At least one pair of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or to form a substituted or unsubstituted fused ring, or to form neither a monocyclic ring nor a fused ring. 121 ~R 132At least one pair of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or to form a substituted or unsubstituted fused ring, or do not form the monocyclic ring or the fused ring. 101 ~R 111 and R 121 ~R 132 are each independently a hydrogen atom or a substituent R. The substituent R is as defined in formula (1).
[0136] In one embodiment, the compound represented by formula (1) is a compound represented by formula (111): [In formula (111), R 101 ~R 109 , R 111 , and R 132 is as defined in the above formulas (11) to (18).
[0137] In one embodiment, the compound represented by formula (1) is a compound represented by formula (112): [In formula (112), R 101 ~R 108 , R 110 ~R 111 , R 132 , n1, and L 1 is as defined in the above formulas (11) to (18).
[0138] In one embodiment, the compound represented by formula (1) is a compound represented by formula (113): [In formula (113), R 101 ~R 107 , R 109 ~R 111 , R 132 , n1, and L 1 is as defined in the above formulas (11) to (18).
[0139] In one embodiment, the compound represented by formula (1) is a compound represented by formula (114): [In formula (114), R 101 ~R 106 , R 108 ~R111 , R 132 , n1, and L 1 is as defined in the above formulas (11) to (18).
[0140] In one embodiment, the compound represented by formula (1) is a compound represented by formula (115): [In formula (115), R 101 ~R 109 , R 111 , R 127 , n1, and L 1 is as defined in the above formulas (11) to (18).
[0141] In one embodiment, R 127 is a hydrogen atom, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.
[0142] In one embodiment, R 132 is a hydrogen atom.
[0143] In one embodiment, when the structure represented by formula (S1) and the structure represented by formula (S2) have a substituent, the substituent, and the substituent in the case of "substituted or unsubstituted" in formula (1), are an alkyl group having 1 to 50 carbon atoms, an alkenyl group having 2 to 50 carbon atoms, an alkynyl group having 2 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 ) (R 902 ) (R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 ) (R 907 ), a halogen atom, a cyano group, a nitro group, an aryl group having 6 to 50 ring carbon atoms, or a heterocyclic group having 5 to 50 ring atoms. 901 ~R 907 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
[0144] In one embodiment, when the structure represented by formula (S1) and the structure represented by formula (S2) have a substituent, the substituent, and the substituent in the case of "substituted or unsubstituted" in formula (1), are groups selected from the group consisting of: an alkyl group having 1 to 50 carbon atoms; an aryl group having 6 to 50 ring carbon atoms; and a heterocyclic group having 5 to 50 ring atoms.
[0145] In one embodiment, when the structure represented by formula (S1) and the structure represented by formula (S2) have a substituent, the substituent, and the substituent in the case of being "substituted or unsubstituted" in formula (1), are groups selected from the group consisting of: an alkyl group having 1 to 18 carbon atoms; an aryl group having 6 to 18 ring carbon atoms; and a heterocyclic group having 5 to 18 ring atoms.
[0146] In one embodiment, the compound according to one aspect of the present invention does not have a deuterium atom in the molecule as a hydrogen atom.
[0147] As used herein, the phrase "having no deuterium atoms as hydrogen atoms" means that, among all hydrogen atoms in the molecule, the ratio of deuterium atoms to the total of protons and deuterium atoms is equal to or less than the natural abundance. In other words, a compound according to one embodiment of the present invention that does not have deuterium atoms as hydrogen atoms in the molecule may contain deuterium atoms at a ratio equal to or less than the natural abundance. Whether the ratio of deuterium atoms to the total of protons and deuterium atoms is equal to or less than the natural abundance can be confirmed using a nuclear magnetic resonance spectrometer.
[0148] In one embodiment, the compound according to one aspect of the present invention has at least one deuterium atom in the molecule as a hydrogen atom.
[0149] In one embodiment, at least one of the hydrogen atoms in the structure represented by formula (S1) and the hydrogen atoms in the structure represented by formula (S2) is a deuterium atom.
[0150] In one embodiment, at least one of the hydrogen atoms in the structure represented by formula (S1) is a deuterium atom. In one embodiment, at least one of the hydrogen atoms in the structure represented by formula (S2) is a deuterium atom.
[0151] In one embodiment, at least one of the hydrogen atoms in the structure represented by formula (S1) is a deuterium atom, and at least one of the hydrogen atoms in the structure represented by formula (S2) is a deuterium atom.
[0152] In one embodiment, R in formula (1) is a hydrogen atom. 1 ~R 11 and R 21 ~R 32 , R is a substituent R 1 ~R 11 and R 21 ~R 32 a hydrogen atom possessed by R 1 ~R 11 and R 21 ~R 32 when one or more pairs of adjacent two or more of the groups bond to each other to form a single ring or a condensed ring, a hydrogen atom possessed by the single ring or the condensed ring; 1 At least one of the hydrogen atoms contained in is a deuterium atom.
[0153] In one embodiment, R in formula (1) is a hydrogen atom. 1 ~R 11 , R is a substituent R 1 ~R 11 a hydrogen atom possessed by R 1 ~R 11 When one or more pairs of adjacent two or more of the above are bonded to each other to form a single ring or a condensed ring, at least one of the hydrogen atoms in the single ring or the condensed ring is a deuterium atom.
[0154] In one embodiment, R in formula (1) is a hydrogen atom. 21 ~R 32 , R is a substituent R 21 ~R 32 a hydrogen atom possessed by R 21 ~R 32 When one or more pairs of adjacent two or more of the above are bonded to each other to form a single ring or a condensed ring, at least one of the hydrogen atoms in the single ring or the condensed ring is a deuterium atom.
[0155] In one embodiment, R in formula (1) is a hydrogen atom. 1 ~R 11 , R is a substituent R 1 ~R 11 a hydrogen atom possessed by R 1 ~R 11 when one or more pairs of adjacent two or more of R are bonded to each other to form a single ring or a condensed ring, at least one of the hydrogen atoms in the single ring or the condensed ring is a deuterium atom, and R is a hydrogen atom 21 ~R 32 , R is a substituent R 21 ~R 32 a hydrogen atom possessed by R 21 ~R 32 When one or more pairs of adjacent two or more of the above are bonded to each other to form a single ring or a condensed ring, at least one of the hydrogen atoms in the single ring or the condensed ring is a deuterium atom.
[0156] As used herein, "having deuterium atoms as hydrogen atoms" or "hydrogen atoms are deuterium atoms" means that, in the hydrogen atoms, the ratio of deuterium atoms to the total of protium atoms and deuterium atoms is higher than the natural abundance. The fact that the ratio of deuterium atoms to the total of protium atoms and deuterium atoms is higher than the natural abundance can be confirmed by a nuclear magnetic resonance spectrometer.
[0157] The compound according to one embodiment of the present invention can be synthesized by following the examples and using known alternative reactions and raw materials suited to the target compound.
[0158] Specific examples of the compound according to one embodiment of the present invention are described below, but these are merely illustrative, and the compound according to one embodiment of the present invention is not limited to the following specific examples.
[0159]
[0160] [Material for Organic Electroluminescence Device] The compound according to one embodiment of the present invention is useful as a material for an organic EL device, for example, as a material used in the electron transport region of an organic EL device.
[0161] [Organic EL Element] An organic EL element according to one embodiment of the present invention includes a cathode, an anode, and one or more organic layers disposed between the cathode and the anode, and at least one of the organic layers contains the compound according to one embodiment of the present invention (a compound including a structure represented by formula (S1) and a structure represented by formula (S2)).
[0162] The organic EL element according to one aspect of the present invention has the above-described configuration, and thus can improve its performance.
[0163] The organic EL device according to one aspect of the present invention has one or more organic layers disposed between a cathode and the anode. At least one of the organic layers contains the compound according to one aspect of the present invention. However, conventionally known materials and device configurations can be used in the organic EL device as long as the effects of the present invention are not impaired.
[0164] In one embodiment, the organic EL device of the present invention includes an anode, an emitting layer, and a cathode in this order, and at least one organic layer in the emitting layer includes a compound according to one aspect of the present invention (a compound including a structure represented by formula (S1) and a structure represented by formula (S2)).
[0165] In one embodiment, the organic EL device according to one aspect of the present invention has a hole transporting region between the anode and the light-emitting layer.
[0166] In one embodiment, the organic EL device according to one aspect of the present invention has an electron transporting region between the cathode and the light-emitting layer.
[0167] The schematic configuration of an organic EL element according to one aspect of the present invention will be described with reference to Fig. 1. In one embodiment, an organic EL element 1 according to one aspect of the present invention includes a substrate 2, an anode 3, an emitting layer 5, a cathode 10, a hole transporting region 4 between the anode 3 and the emitting layer 5, and an electron transporting region 6 between the emitting layer 5 and the cathode 10.
[0168] A typical example of the device configuration of the organic EL device of the present invention is a structure in which the following structures are laminated on a substrate: (1) anode / light-emitting layer / cathode (2) anode / hole-transporting region / light-emitting layer / cathode (3) anode / light-emitting layer / electron-transporting region / cathode (4) anode / hole-transporting region / light-emitting layer / electron-transporting region / cathode (" / " indicates that each layer is laminated adjacent to each other).
[0169] The hole transport region is a general term for one or more layers disposed between the anode and the light-emitting layer. The hole transport region is composed of, for example, layers called an electron blocking layer, a hole transport layer, and a hole injection layer, which will be described later from the light-emitting layer side. The hole transport region may have a laminated structure including all of these layers, or may have a layered structure including only some of these layers. Furthermore, two or more types of layers may be used for each of the above layers. For example, two types of hole transport layers with different compositions may be laminated. Each layer may be formed using only one type of material, or may be formed using two or more types of materials in combination.
[0170] The electron transport region is a general term for one or more layers disposed between the cathode and the light-emitting layer. The electron transport region is composed of, for example, layers called a hole-blocking layer, an exciton-blocking layer, an electron-transporting layer, and an electron-injection layer, which will be described later, from the light-emitting layer side. The electron transport region may have a laminated structure including all of these layers, or may have a layered structure including only some of these layers. Furthermore, two or more types of layers may be used for each of the above layers. For example, two types of electron-transporting layers with different compositions may be laminated. Each layer may be formed using only one type of material, or two or more types of materials in combination.
[0171] Hereinafter, members that can be used in the organic EL element according to one embodiment of the present invention, and materials that constitute each layer will be described.
[0172] (Light-emitting layer) In one embodiment, the light-emitting layer includes a compound according to one aspect of the present invention.
[0173] In one embodiment, the light-emitting layer further contains a compound represented by any one of the following formulas (D11) to (D41): The compound according to one aspect of the present invention and the compound represented by any one of formulas (D11) to (D41) are different from each other.
[0174] Formulas (D11) to (D41) will be described later.
[0175] (Compound Represented by Formula (D11)) The compound represented by formula (D11) will be described. In formula (D11), three Z's each independently represent CR a or a nitrogen atom. Ring A1 and ring A2 are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms. R a If there are multiple R a At least one pair of adjacent two or more of the groups of nD11 and nD12 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or do not form the monocyclic ring or the fused ring. nD11 and nD12 are each independently 0, 1, 2, 3, or 4. R b If there are multiple R b At least one pair of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or to form a substituted or unsubstituted fused ring, or to form neither a monocyclic ring nor a fused ring. c If there are multiple R c At least one pair of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or do not form the monocyclic ring or the fused ring. a , R b , and R c each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 ) (R 902 ) (R 903 ), -O-(R 904 ), -S-(R905 ), -N(R 906 ) (R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. 901 ~R 907 is as defined in the above formula (1).
[0176] The "aromatic hydrocarbon ring" of ring A1 and ring A2 has the same structure as the compound in which a hydrogen atom has been introduced into the above-mentioned "aryl group having 6 to 50 ring carbon atoms." The "aromatic hydrocarbon ring" of ring A1 and ring A2 contains, as ring-forming atoms, the two carbon atoms on the central fused bicyclic structure of formula (D11). Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms" include compounds in which a hydrogen atom has been introduced into the "substituted or unsubstituted aryl group" described in specific example group G1.
[0177] The "heterocycles" of ring A1 and ring A2 have the same structure as the compounds obtained by introducing a hydrogen atom into the above-mentioned "heterocyclic group having 5 to 50 ring atoms". The "heterocycles" of ring A1 and ring A2 contain, as ring-forming atoms, the two carbon atoms on the central fused bicyclic structure of formula (D11). Specific examples of the "substituted or unsubstituted heterocycle having 5 to 50 ring atoms" include compounds obtained by introducing a hydrogen atom into the "substituted or unsubstituted heterocyclic group" described in specific example group G2.
[0178] Rb is bonded to any of the carbon atoms forming the aromatic hydrocarbon ring as ring A1, or any of the atoms forming the heterocycle as ring A1.
[0179] Rc is bonded to any of the carbon atoms forming the aromatic hydrocarbon ring as ring A2, or any of the atoms forming the heterocycle as ring A2.
[0180] In one embodiment, at least one of Ra, Rb, and Rc is a group represented by the following formula (D11a): In one embodiment, at least two of Ra, Rb, and Rc are groups represented by the following formula (D11a):
[0181] [In formula (D11a), L D101 represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms. D101 represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the following formula (D11b): (In formula (D11b), L D102 and L D103 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms. D102 and Ar D103 The groups consisting of are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other. D102 and Ar D103 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0182] Specific examples of the compound represented by formula (D11) are listed below, but these are merely illustrative, and the compound represented by formula (D11) is not limited to the following specific examples.
[0183]
[0184] (Compound Represented by Formula (D21)) The compound represented by formula (D21) will be explained. In formula (D21), R D201 and R D202 , R D202 and R D203 , and R D203 and R D204 At least one pair of R is bonded to each other to form a divalent group represented by the following formula (D22): D205 and R D206 , R D206 and R D207, and R D207 and R D208 At least one pair of these bonds are bonded to each other to form a divalent group represented by the following formula (D23): R that does not form a divalent group represented by formula (D22) D201 ~R D204 , and R D211 ~R D214 At least one of R is a monovalent group represented by the following formula (D24): D205 ~R D208 , and R D221 ~R D224 At least one of X is a monovalent group represented by the following formula (D24): D2 is an oxygen atom, a sulfur atom, or NR D209 R which does not form a divalent group represented by the formula (D22) or (D23) and is not a monovalent group represented by the formula (D24) D201 ~R D208 , R which is not a monovalent group represented by formula (D24) D211 ~R D214 and R D221 ~R D224 , and R D209 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 ) (R 902 ) (R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 ) (R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. In formula (D24), Ar D201 and Ar D202are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. D201 ~L D203 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or a divalent linking group formed by bonding 2 to 4 groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms. * indicates the bonding position with the ring structure represented by formula (D21) or the group represented by formula (D22) or (D23). R 901 ~R 907 is as defined in the above formula (1).
[0185] In formula (D21), the positions at which the divalent group represented by formula (D22) and the divalent group represented by formula (D23) are formed are not particularly limited, and R D201 ~R D208 The group can be formed at any possible position.
[0186] Specific examples of the compound represented by formula (D21) include the compounds described in WO 2014 / 104144 and the compounds shown below, but these are merely illustrative, and the compound represented by formula (21) is not limited to the specific examples below.
[0187]
[0188] (Compound Represented by Formula (D31)) The compound represented by formula (D31) will be explained. In formula (D31), R D301 ~R D307 and R D311 ~R D317 At least one pair of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or to form a substituted or unsubstituted fused ring, or do not form the monocyclic ring or the fused ring. D301 ~R D307 and RD311 ~R D317 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 ) (R 902 ) (R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 ) (R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. D321 and R D322 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 ) (R 902 ) (R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 ) (R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. 901 ~R 907 is as defined in the above formula (1).
[0189] "R D301 ~R D307 and R D311 ~R D317 "A set of two or more adjacent pairs of R D301 and R D302 A set consisting of R D302 and R D303 A set consisting of R D303 and R D304 A set consisting of RD305 and R D306 A set consisting of R D306 and R D307 A set consisting of R D301 and R D302 and R D303 It is a combination of a set consisting of:
[0190] In one embodiment, R D301 ~R D307 and R D311 ~R D317 At least one of the groups is —N(R 906 ) (R 907 In one embodiment, R D301 ~R D307 and R D311 ~R D317 The two are -N(R 906 ) (R 907 )
[0191] In one embodiment, R D301 ~R D307 and R D311 ~R D317 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0192] Specific examples of the compound represented by formula (D31) are shown below, but these are merely illustrative, and the compound represented by formula (D31) is not limited to the following specific examples.
[0193]
[0194] (Compound Represented by Formula (D41)) The compound represented by formula (D41) will be explained. In formula (D41), ring a, ring b, and ring c each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms. D401 and R D402each independently bond to the ring a, ring b, or ring c to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring. D401 and R D402 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
[0195] Ring a, ring b, and ring c are rings (substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring carbon atoms, or substituted or unsubstituted heterocyclic rings having 5 to 50 ring atoms) fused to the central fused bicyclic structure of formula (D41) composed of atom B and two N atoms.
[0196] The "aromatic hydrocarbon rings" of ring a, ring b, and ring c have the same structure as the compounds in which a hydrogen atom has been introduced into the above-mentioned "aryl group." The "aromatic hydrocarbon ring" of ring a includes three carbon atoms on the central fused bicyclic structure of formula (D41) as ring-forming atoms. The "aromatic hydrocarbon rings" of ring b and ring c include two carbon atoms on the central fused bicyclic structure of formula (D41) as ring-forming atoms. Specific examples of "substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring carbon atoms" include compounds in which a hydrogen atom has been introduced into the "aryl group" described in specific example group G1. The "heterocyclic rings" of ring a, ring b, and ring c have the same structure as the compounds in which a hydrogen atom has been introduced into the above-mentioned "heterocyclic group." The "heterocyclic ring" of ring a includes three carbon atoms on the central fused bicyclic structure of formula (D41) as ring-forming atoms. The "heterocycle" of ring b and ring c contains the two carbon atoms on the central fused bicyclic structure of formula (D41) as ring-forming atoms. Specific examples of the "substituted or unsubstituted heterocycle having 5 to 50 ring atoms" include compounds in which a hydrogen atom has been introduced into the "heterocyclic group" described in specific example group G2.
[0197] R D401 and R D402may each independently bond to ring a, ring b, or ring c to form a substituted or unsubstituted heterocyclic ring. In this case, the heterocyclic ring contains the nitrogen atom on the central fused bicyclic structure of formula (D41). In this case, the heterocyclic ring may contain a heteroatom other than the nitrogen atom. R D401 and R D402 is bonded to ring a, ring b, or ring c specifically means that an atom constituting ring a, ring b, or ring c is bonded to R D401 and R D402 It means that the atoms constituting R are bonded together. D401 is bonded to ring a, and R D401 A two-ring (or three- or more-ring) nitrogen-containing heterocyclic ring may be formed by condensing a ring containing R with ring a. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing two- or more-ring condensed heterocyclic groups in specific example group G2. D401 When is bonded to ring b, R D402 When R is bonded to ring a, D402 The same applies when is bonded to ring c.
[0198] In one embodiment, ring a, ring b, and ring c in formula (D41) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having ring carbon atoms of 6 to 50. In one embodiment, ring a, ring b, and ring c in formula (D41) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.
[0199] In one embodiment, R in formula (D41) D401 and R D402 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0200] In one embodiment, the compound represented by formula (D41) is a compound represented by formula (D42): (In formula (D42), R D401A is R D411 and R D421R is bonded to one or more selected from the group consisting of: to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. D402A is R D413 and R D414 and R which does not form a substituted or unsubstituted heterocycle. D401A and R D402A are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. D411 ~R D421 At least one pair of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring. D411 ~R D421 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 ) (R 902 ) (R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 ) (R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. 901 ~R 907 is as defined in the above formula (1).
[0201] R in formula (D42) D401A and R D402A is R in formula (D41). D401 and R D402 For example, R D401A and R D411 may be bonded to form a two-ring (or three- or more-ring) fused nitrogen-containing heterocycle in which a ring containing the ring is fused with a benzene ring corresponding to ring a. Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing two- or more-ring fused heterocyclic groups in specific example group G2. D401A and R D412 When R D402A and R D413 is bonded, and R D402A and R D414 The same applies when the two are combined.
[0202] R D411 ~R D421 One or more pairs of adjacent two or more of R may be bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring. D411 and R D412 may be bonded to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like is fused to the six-membered ring to which they are bonded, and the fused ring formed is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring.
[0203] In one embodiment, R D411 ~R D421 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
[0204] In one embodiment, R D411 ~R D421 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
[0205] In one embodiment, R D411 ~R D421 are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[0206] In one embodiment, R D411 ~R D421 are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and R D411 ~R D421 At least one of the groups is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[0207] In one embodiment, the compound represented by formula (D42) is a compound represented by formula (D43): (In formula (D43), R D431 is R D446 R may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring. D433 is R D447 R may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring. D434 is R D451 R may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring. D441 is R D442 R may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring. D431 ~R D451 At least one pair of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring. D431 ~R D451are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 ) (R 902 ) (R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 ) (R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. 901 ~R 907 is as defined in the above formula (1).
[0208] R D431 is R D446 may be bonded to form a substituted or unsubstituted heterocycle. For example, R D431 and R D446 is bonded to form R D446 may be bonded to a benzene ring, a ring containing N, and a benzene ring corresponding to ring a, which are fused to form a nitrogen-containing heterocyclic ring having three or more fused rings. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing heterocyclic group having three or more fused rings in the specific example group G2. D433 and R D447 When R D434 and R D451 is bonded, and R D441 and R D442 The same applies when the two are combined.
[0209] In one embodiment, R D431 ~R D451 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
[0210] In one embodiment, R D431~R D451 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
[0211] In one embodiment, R D431 ~R D451 are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[0212] In one embodiment, R D431 ~R D451 are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and R D431 ~R D451 At least one of the groups is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[0213] In one embodiment, the compound represented by formula (D43) is a compound represented by formula (D43A): (In formula (D43A), R D461 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. D462 ~R D465 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0214] In one embodiment, R D461 ~R D465 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0215] In one embodiment, R D461 ~R D465 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[0216] In one embodiment, the compound represented by formula (D43) is a compound represented by formula (D43B): (In formula (D43B), R D471 and R D472 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 906 ) (R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. D473 ~R D475 each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 906 ) (R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. 906 and R 907 is as defined in the above formula (1).
[0217] In one embodiment, the compound represented by formula (D43) is a compound represented by formula (D43B'): (In formula (D43B′), R D472 ~R D475 is as defined in the formula (D43B) above.
[0218] In one embodiment, R D471 ~R D475At least one of the above is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 906 ) (R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0219] In one embodiment, R D472 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, -N(R 906 ) (R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R D471 and R D473 ~R D475 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, —N(R 906 ) (R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0220] In one embodiment, the compound represented by formula (D43) is a compound represented by formula (D43C): (In formula (D43C), R D481 and R D482 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. D483 ~R D486 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0221] In one embodiment, the compound represented by formula (D43) is a compound represented by formula (D43C'): (In formula (D43C′), R D483 ~R D486 is as defined in the formula (D43C) above.
[0222] In one embodiment, R D481 ~R D486 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0223] In one embodiment, R D481 ~R D486 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0224] In one embodiment, the compound represented by formula (D41) is a compound represented by formula (D44): (In formula (D44), X D401 is O or S. D401B is R D487 and R D497 R is bonded to one or more selected from the group consisting of: to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. D402B is R D489 and R D490 and R which does not form a substituted or unsubstituted heterocycle. D401B and R D402B are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. D487 ~R D497At least one pair of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring. D487 ~R D497 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 ) (R 902 ) (R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 ) (R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. 901 ~R 907 is as defined in the above formula (1).
[0225] In one embodiment, R D401B and R D402B are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0226] In one embodiment, R D487 ~R D497 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0227] The compound represented by formula (D41) can be prepared by first connecting the ring a, ring b, and ring c to a linking group (N—R D401 and groups containing N-R D402An intermediate is produced by linking the rings a, b, and c with a linking group (a group containing B) (first reaction), and the final product is produced by linking the rings a, b, and c with a linking group (a group containing B) (second reaction). In the first reaction, an amination reaction such as the Bachburt-Hartwig reaction can be applied. In the second reaction, a tandem hetero-Friedel-Crafts reaction or the like can be applied.
[0228] Specific examples of the compound represented by formula (D41) are shown below, but these are merely illustrative, and the compound represented by formula (D41) is not limited to the following specific examples.
[0229]
[0230] In addition to the compounds represented by the above-mentioned formula (D11), formula (D21), formula (D31), or formula (D41), the light-emitting layer can also use, for example, the compounds shown below.
[0231]
[0232] In one embodiment, the light-emitting layer contains a compound represented by formula (D31) or (D41) above.
[0233] In one embodiment, the light-emitting layer includes, from the anode side, a first layer and a second layer, and the first layer includes a compound according to one aspect of the present invention (a compound including a structure represented by formula (S1) and a structure represented by formula (S2)). In one embodiment, the light-emitting layer includes, from the anode side, a first layer, a second layer, and one or more further layers, and the first layer includes a compound according to one aspect of the present invention (a compound including a structure represented by formula (S1) and a structure represented by formula (S2)).
[0234] In one embodiment, the first layer contains a compound according to one aspect of the present invention and a compound represented by any one of Formulas (D11) to (D41). In one embodiment, the first layer contains a compound according to one aspect of the present invention as a host material (which may also be referred to as a matrix material). In one embodiment, the first layer further contains a dopant material. In one embodiment, the first layer contains a compound represented by any one of Formulas (D11) to (D41) as a dopant material (which may also be referred to as a guest material, an emitter, or a light-emitting material).
[0235] In one embodiment, the first layer contains more than 1.1 wt %, 1.2 wt % or more, or 1.5 wt % or more of the dopant material based on the total weight of the first layer, hi one embodiment, the first layer contains 10 wt % or less, 7 wt % or less, or 5 wt % or less of the dopant material based on the total weight of the first layer.
[0236] In one embodiment, the first layer contains at least 60%, at least 70%, at least 80%, at least 90%, or at least 95% by weight of the host material based on the total weight of the first layer, hi one embodiment, the first layer contains up to 99% by weight of the host material based on the total weight of the first layer.
[0237] The first layer may contain materials other than the host material and the dopant material.
[0238] The first layer may contain only one type of host material or two or more types of dopant materials.
[0239] The light-emitting layer is a layer containing a highly light-emitting substance, and various materials can be used. For example, as the highly light-emitting substance, in addition to the compounds represented by any of Formulas (D11) to (D41) described above, fluorescent compounds that emit fluorescence and phosphorescent compounds that emit phosphorescence can be used. Fluorescent compounds are compounds that can emit light from a singlet excited state, and phosphorescent compounds are compounds that can emit light from a triplet excited state. Examples of blue fluorescent materials that can be used in the light-emitting layer include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, and triarylamine derivatives. Examples of green fluorescent materials that can be used in the light-emitting layer include aromatic amine derivatives. Examples of red fluorescent materials that can be used in the light-emitting layer include tetracene derivatives and diamine derivatives. Examples of blue phosphorescent materials that can be used in the light-emitting layer include metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Examples of green phosphorescent materials that can be used in the light-emitting layer include iridium complexes. As the red phosphorescent material that can be used in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used.
[0240] The light-emitting layer may have a structure in which the highly luminescent substance (guest material) described above is dispersed in another substance (host material). As a substance for dispersing the highly luminescent substance, various substances can be used, in addition to the materials used in the present invention (compounds according to one embodiment of the present invention) described above. It is preferable to use a substance having a lower lowest unoccupied molecular orbital (LUMO) level and a lower highest occupied molecular orbital (HOMO) level than the highly luminescent substance. Examples of substances for dispersing the highly luminescent substance (host material) include: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives; 3) fused aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and chrysene derivatives; and 4) aromatic amine compounds such as triarylamine derivatives and fused polycyclic aromatic amine derivatives. Furthermore, a delayed fluorescent (thermally activated delayed fluorescent) compound can also be used as the host material. It is also preferable that the light-emitting layer contains the material used in the present invention described above and a delayed fluorescent host compound. The light-emitting layer may or may not contain the other substances described above in addition to the material used in the present invention described above.
[0241] (Second Layer) The second layer contains at least one compound different from that of the first layer described above. In one embodiment, the second layer contains a host material (second host material). The host material can be any of the substances listed as the host material (first host material) of the first layer described above. In one embodiment, the second host material is a compound different from the first host material contained in the first layer. A delayed fluorescent (thermally activated delayed fluorescent) compound can also be used as the host material. The light-emitting layer can also contain the compound according to one aspect of the present invention described above and a delayed fluorescent host compound.
[0242] In one embodiment, the second layer further includes a dopant material (second dopant material). The dopant material may be any of the substances listed above as the dopant material (first dopant material) for the first layer. In one embodiment, the second dopant material is a compound represented by any of Formulas (D11) to (D41) above. In one embodiment, the second dopant material is a different compound from the first dopant material. In one embodiment, the second dopant material is the same compound as the first dopant material.
[0243] In one embodiment, the second layer contains more than 1.1 wt. %, 1.2 wt. % or more, or 1.5 wt. % or more of the dopant material based on the total weight of the second layer, hi one embodiment, the second layer contains 10 wt. % or less, 7 wt. % or less, or 5 wt. % or less of the dopant material based on the total weight of the second layer.
[0244] In one embodiment, the second layer contains at least 60%, at least 70%, at least 80%, at least 90%, or at least 95% by weight of the host material based on the total weight of the second layer, hi one embodiment, the second layer contains up to 99% by weight of the host material based on the total weight of the second layer.
[0245] The second layer may contain materials other than the host material and the dopant material.
[0246] The second layer may contain only one type of host material or two or more types of dopant materials.
[0247] The second layer may be a fluorescent or phosphorescent emissive layer, hi one embodiment, the second layer is a fluorescent emissive layer.
[0248] (Substrate) The substrate is used as a support for the light-emitting element. For example, glass, quartz, plastic, etc. can be used as the substrate. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples thereof include plastic substrates made of polycarbonate or polyvinyl chloride.
[0249] (Anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), or nitrides of metal materials (e.g., titanium nitride).
[0250] (Hole Injection Layer) The hole injection layer is a layer containing a substance with high hole injection properties. Examples of the substance with high hole injection properties 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, aromatic amine compounds, and polymer compounds (oligomers, dendrimers, polymers, etc.).
[0251] (Hole Transport Layer) The hole transport layer is a layer containing a substance with high hole transport properties. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, and the like can be used for the hole transport layer. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used. However, other substances may be used as long as they have a higher hole transport property than electron transport property. The layer containing the substance with high hole transport properties may be a single layer or may be a stack of two or more layers made of the above substances.
[0252] (Electron Blocking Layer, Hole Blocking Layer, Exciton Blocking Layer) An electron blocking layer, hole blocking layer, exciton (triplet) blocking layer, or the like may be provided adjacent to the light-emitting layer. The electron blocking layer is a layer that has the function of blocking electrons from leaking from the light-emitting layer to the hole transport layer. The hole blocking layer is a layer that has the function of blocking holes from leaking from the light-emitting layer to the electron transport layer. The exciton blocking layer is a layer that has the function of blocking excitons generated in the light-emitting layer from diffusing to adjacent layers and confining the excitons within the light-emitting layer.
[0253] (Electron Transport Layer) The electron transport layer is a layer containing a substance with high electron transport properties. For the electron transport layer, 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex, 2) a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative, or a phenanthroline derivative, or 3) a polymer compound can be used.
[0254] (Electron Injection Layer) The electron injection layer is a layer containing a substance with high electron injection properties. Examples of the electron injection layer include lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), metal complex compounds such as 8-hydroxyquinolinolato-lithium (Liq), lithium oxide (LiO x ), alkaline metals such as Cr, alkaline earth metals, or compounds thereof can be used.
[0255] (Cathode) For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such a cathode material include elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.
[0256] In the organic EL element according to one embodiment of the present invention, the thickness of each layer is not particularly limited, but in order to generally suppress defects such as pinholes, keep the applied voltage low, and improve the luminous efficiency, it is usually preferable that the thickness be in the range of several nm to 1 μm.
[0257] In the organic EL element according to one embodiment of the present invention, the method for forming each layer is not particularly limited. Conventionally known methods such as vacuum deposition and spin coating can be used. Each layer, such as the light-emitting layer, can be formed by a known method such as vacuum deposition, molecular beam deposition (MBE), or a coating method such as dipping a solution in a solvent, spin coating, casting, bar coating, or roll coating.
[0258] [Electronic Device] An electronic device according to an aspect of the present invention is characterized by comprising the organic EL element according to an aspect of the present invention. Specific examples of the electronic device include display components such as organic EL panel modules, display devices for televisions, mobile phones, and personal computers, and light-emitting devices such as lighting and vehicle lamps.
[0259] <Compounds> Compounds according to one embodiment of the present invention used in the production of the organic EL devices of Examples 1 to 16 are shown below. The following compounds are compounds containing a structure represented by formula (S1) and a structure represented by formula (S2).
[0260] The comparative compounds used in the production of the organic EL devices of Comparative Examples 1 and 2 are shown below.
[0261] The structures of other compounds used in the production of the organic EL devices of Examples 1 to 16 and Comparative Examples 1 and 2 are shown below.
[0262] Example 1 <Preparation of Organic EL Device> An organic EL device was prepared as follows. A 25 mm × 75 mm × 1.1 mm thick glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was 130 nm. The cleaned glass substrate with the transparent electrode was attached to a substrate holder in a vacuum deposition apparatus, and compound HIL-1 was first vapor-deposited on the surface on which the transparent electrode was formed, covering the transparent electrode, to form a first hole transport layer with a thickness of 5 nm. Compound HTL-1 was vapor-deposited on the first hole transport layer to form a second hole transport layer with a thickness of 80 nm. Compound EBL-1 was vapor-deposited on the second hole transport layer to form a third hole transport layer with a thickness of 10 nm. On the third hole-transporting layer, compound BH1-1 (host material) and compound BD-1 (dopant material) were co-deposited such that the proportion of compound BD-1 was 2% by mass, thereby forming a first light-emitting layer with a thickness of 5 nm. On the first light-emitting layer, compound BH-2 (host material) and compound BD-1 (dopant material) were co-deposited such that the proportion of compound BD-1 was 2% by mass, thereby forming a second light-emitting layer with a thickness of 20 nm. On the second light-emitting layer, compound aET-1 was deposited by vapor deposition to form a first electron-transporting layer with a thickness of 10 nm. On the first electron-transporting layer, compound bET-1 was deposited by vapor deposition to form a second electron-transporting layer with a thickness of 15 nm. On the second electron-transporting layer, LiF was deposited by vapor deposition to form an electron-injecting layer with a thickness of 1 nm. On the electron-injecting layer, metal Al was deposited by vapor deposition to form a cathode with a thickness of 80 nm.
[0263] The device configuration of the organic EL device of Example 1 is shown in outline as follows: ITO(130) / HIL-1(5) / HTL-1(80) / EBL-1(10) / BH1-1:BD-1(5:2%) / BH-2:BD-1(20:2%) / aET-1(10) / bET-1(15) / LiF(1) / Al(80) The numbers in parentheses indicate the film thickness (unit: nm). The percentage numbers in parentheses indicate the proportion (mass %) of the latter compound in the corresponding layer.
[0264] <Evaluation of Organic EL Device> The fabricated organic EL device was evaluated as follows. The results are shown in Table 1. In Table 1, the driving voltage is shown as a relative value when Comparative Example 1 is set to ±0 V, and the device life is shown as a relative value when Comparative Example 1 is set to 100. Driving voltage The initial characteristics of the organic EL device were evaluated at room temperature by applying a DC (direct current) constant current of 10 mA / cm 2 Measured at room temperature and a current density of 50 mA / cm 2 A voltage was applied to the organic EL element so that the voltage was 95% of the initial voltage, and the time (LT95 (unit: h)) until the luminance reached 95% of the initial luminance was measured.
[0265] Examples 2 to 8 Organic EL devices were fabricated and evaluated in the same manner as in Example 1, except that in forming the first light-emitting layer, the compound BH1-1 was replaced with a compound shown in Table 1. The results are shown in Table 1.
[0266] Comparative Example 1 An organic EL device was produced and evaluated in the same manner as in Example 1, except that in forming the first light-emitting layer, compound Ref-1 was used instead of compound BH1-1. The results are shown in Table 1.
[0267]
[0268] Example 9 <Preparation of Organic EL Device> An organic EL device was prepared as follows. A 25 mm × 75 mm × 1.1 mm thick glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was 130 nm. The cleaned glass substrate with the transparent electrode was attached to a substrate holder in a vacuum deposition apparatus. First, compounds HTL-2 and HIL-2 were co-deposited on the surface on which the transparent electrode was formed, so as to cover the transparent electrode, with the proportion of compound HIL-2 being 10% by mass, to form a first hole transport layer with a thickness of 10 nm. Compound HTL-2 was vapor-deposited on the first hole transport layer to form a second hole transport layer with a thickness of 85 nm. Compound EBL-2 was vapor-deposited on the second hole transport layer to form a third hole transport layer with a thickness of 5 nm. On the third hole-transport layer, compound BH1-1 (host material) and compound BD-2 (dopant material) were co-deposited such that the proportion of compound BD-2 was 2% by mass, thereby forming a first light-emitting layer with a thickness of 10 nm. On the first light-emitting layer, compound BH-3 (host material) and compound BD-2 (dopant material) were co-deposited such that the proportion of compound BD-2 was 2% by mass, thereby forming a second light-emitting layer with a thickness of 10 nm. On the second light-emitting layer, compound aET-2 was co-deposited such that the proportion of Liq was 50% by mass, thereby forming a first electron-transport layer with a thickness of 5 nm. On the first electron-transport layer, compound bET-2 and Liq were co-deposited such that the proportion of Liq was 50% by mass, thereby forming a second electron-transport layer with a thickness of 25 nm. On the second electron-transport layer, Liq was co-deposited such that the proportion of Liq was 50% by mass, thereby forming a second electron-transport layer with a thickness of 1 nm. On the second electron-transport layer, Liq was co-deposited such that the proportion of Liq was 50% by mass, thereby forming a cathode with a thickness of 80 nm.
[0269] The device configuration of the organic EL device of Example 9 is shown in outline as follows: ITO(130) / HTL-2:HIL-2(10:10%) / HTL-2(85) / EBL-2(5) / BH1-1:BD-2(10:2%) / BH-3:BD-2(10:2%) / aET-2(5) / bET-2:Liq(25:50%) / Liq(1) / Al(80). The numbers in parentheses indicate film thickness (unit: nm). The percentage numbers in parentheses indicate the proportion (mass %) of the latter compound in the corresponding layer.
[0270] <Evaluation of Organic EL Element> The prepared organic EL element was evaluated in the same manner as in Example 1. The results are shown in Table 2. In Table 2, the driving voltage is shown as a relative value when Comparative Example 2 is set to ±0 V, and the element lifetime is shown as a relative value when Comparative Example 2 is set to 100.
[0271] Examples 10 to 16 Organic EL devices were fabricated and evaluated in the same manner as in Example 9, except that in forming the first light-emitting layer, the compound shown in Table 2 was used instead of compound BH1-1. The results are shown in Table 2.
[0272] Comparative Example 2 An organic EL device was produced and evaluated in the same manner as in Example 9, except that in forming the first light-emitting layer, compound Ref-1 was used instead of compound BH1-1. The results are shown in Table 2.
[0273]
[0274] <Synthesis of Compounds> (Synthesis Example 1) Synthesis of Compound BH1-1 Compound BH1-1 was synthesized according to the following synthetic route.
[0275] Under an argon atmosphere, 2.85 g (10.0 mmol) of Intermediate 1-A, 3.07 g (10.0 mmol) of Intermediate 1-B, 0.183 g (0.2 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.328 g (0.8 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 12.5 mL (25.0 mmol) of 2 M aqueous sodium carbonate, and 67 mL of 1,4-dioxane were charged into a flask and heated under stirring for 8 hours. After cooling to room temperature (25°C), the solvent was distilled off, and the resulting solid was purified by silica gel column chromatography to obtain 3.28 g (70% yield) of a white solid. This white solid was identified as Compound BH1-1 by LC-MS analysis.
[0276] (Synthesis Example 2) Synthesis of Compound BH1-2 Compound BH1-2 was synthesized according to the following synthesis route.
[0277] (Synthesis of Intermediate 2-C) Under an argon atmosphere, 15.4 g (92.0 mmol) of Intermediate 2-A, 20.6 g (98.0 mmol) of Intermediate 2-B, 60.1 g (184 mmol) of cesium carbonate, and 153 mL of dimethylformamide were placed in a flask and refluxed with heating and stirring for 8 hours. After cooling to room temperature (25°C), the solvent was distilled off, and the resulting solid was purified by silica gel column chromatography to obtain 30.9 g of a white solid (yield 94%).
[0278] (Synthesis of Intermediate 2-D) Under an argon atmosphere, 3.73 g (10.5 mmol) of Intermediate 2-C, 0.36 g (0.31 mmol) of tetrakis(triphenylphosphine)palladium(0), 2.89 g (20.9 mmol) of potassium carbonate, and 104 mL of dimethylacetamide were placed in a flask and heated with stirring at 150°C for 24 hours. After stirring, the mixture was cooled to room temperature (25°C), and then 100 mL of water was added, and the precipitated solid was filtered. The obtained solid was purified by silica gel column chromatography to obtain 1.98 g of a white solid (yield 66%).
[0279] (Synthesis of Compound BH1-2) 0.52 g (yield 39%) of a white solid was obtained in the same manner as in the synthesis of Compound BH1-1, except that Intermediates 2-D and 2-E were used instead of Intermediates 1-A and 1-B. LC-MS analysis identified the white solid as Compound BH1-2.
[0280] (Synthesis Example 3) Synthesis of Compound BH1-3 Compound BH1-3 was synthesized according to the following synthesis route.
[0281] (Synthesis of Intermediate 3-C) Intermediate 3-C was synthesized in the same manner as in the synthesis of Intermediate 2-C, except that Intermediates 3-A and 3-B were used instead of Intermediates 2-A and 2-B in the synthesis of Intermediate 2-C, and 50.0 g of a white solid was obtained (yield: 62%).
[0282] (Synthesis of Intermediate 3-D) Intermediate 3-D was synthesized in the same manner as in the synthesis of Intermediate 2-D, except that Intermediate 3-C was used instead of Intermediate 2-C, and 27.4 g of a white solid was obtained (yield: 70%).
[0283] (Synthesis of Intermediate 3-E) Under an argon atmosphere, 27.4 g (94.0 mmol) of Intermediate 3-D, 47.7 g (188 mmol) of bis(pinacolato)diboron, 0.42 g (1.9 mmol) of palladium(II) acetate, 3.6 g (7.5 mmol) of XPhos, 27.7 g (282 mmol) of potassium acetate, and 470 mL of 1,2-dimethoxyethane were placed in a flask and refluxed with heating and stirring for 8 hours. After cooling to room temperature (25°C), the solvent was distilled off, and the resulting solid was purified by silica gel column chromatography to obtain 17.6 g of a white solid (49% yield). After stirring for an additional 6 hours while returning to room temperature (25°C), ice water was added to the reaction solution. After thorough stirring, the aqueous phase was removed, the remaining organic phase was concentrated, and the residue was purified by silica gel column chromatography to obtain 12.5 g of a white solid (72% yield).
[0284] (Synthesis of Intermediate 3-G) A white solid (2.53 g, 39% yield) was obtained in the same manner as in the synthesis of Compound BH1-1, except that Intermediates 3-E and 3-F were used instead of Intermediates 1-A and 1-B.
[0285] (Synthesis of Compound BH1-3) A white solid (1.13 g, 58% yield) was obtained in the same manner as in the synthesis of Compound BH1-1, except that Intermediates 2-E and 3-G were used instead of Intermediates 1-A and 1-B. LC-MS analysis identified the white solid as Compound BH1-3.
[0286] (Synthesis Example 4) Synthesis of Compound BH1-4 Compound BH1-4 was synthesized according to the following synthesis route.
[0287] Under an argon atmosphere, 2.40 g (8.4 mmol) of Intermediate 1-A, 3.07 g (8.0 mmol) of Intermediate 4-A, 0.147 g (0.16 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.252 g (0.64 mmol) of DavePhos, 12.5 mL (25.0 mmol) of a 2 M aqueous cesium carbonate solution, and 53 mL of 1,4-dioxane were charged into a flask and heated under stirring for 7 hours. After cooling to room temperature (25°C), the solvent was distilled off, and the resulting solid was purified by silica gel column chromatography to obtain 3.32 g (76% yield) of a white solid. This white solid was identified as Compound BH1-4 by LC-MS analysis.
[0288] (Synthesis Example 5) Synthesis of Compound BH1-5
[0289] A white solid (2.57 g, 53% yield) was obtained in the same manner as in the synthesis of compound BH1-1, except that intermediates 2-D and 5-A were used instead of intermediates 1-A and 1-B. LC-MS analysis identified the white solid as compound BH1-5.
[0290] (Synthesis Example 6) Synthesis of Compound BH1-6 Compound BH1-6 was synthesized according to the following synthesis route.
[0291] (Synthesis of Intermediate 6-B) Under an argon atmosphere, 5.0 g (17.82 mmol) of Intermediate 6-A, 2.79 g (17.82 mmol) of 2-chlorophenylboronic acid, 0.82 g (0.71 mmol) of tetrakis(triphenylphosphine)palladium(0), 26.7 mL (53.5 mmol) of a 2 M aqueous solution of sodium carbonate, and 156 mL of 1,2-dimethoxyethane were placed in a flask and refluxed with heating for 7 hours while stirring. After cooling to room temperature (25°C), the solvent was distilled off, and the resulting solid was purified by silica gel column chromatography to obtain 4.16 g (73% yield) of a pale yellow solid.
[0292] (Synthesis of Intermediate 6-C) Under an argon atmosphere, 4.16 g (13.33 mmol) of Intermediate 6-B, 3.05 g (15.99 mmol) of copper(I) iodide, 2.88 g (15.99 mmol) of 1,10-phenanthroline, 14.73 g (107 mmol) of potassium carbonate, and 133 mL of dimethylacetamide were placed in a flask and refluxed with heating at 110° C. for 5 hours while stirring. Thereafter, the mixture was cooled to room temperature (25° C.), and the solvent was distilled off. The resulting solid was purified by silica gel column chromatography to obtain 2.57 g (70% yield) of a white solid.
[0293] (Synthesis of Compound BH1-6) A white solid (1.98 g, 45% yield) was obtained in the same manner as in the synthesis of Compound BH1-1, except that Intermediates 2-E and 6-C were used instead of Intermediates 1-A and 1-B. LC-MS analysis identified the white solid as Compound BH1-6.
[0294] (Synthesis Example 7) Synthesis of Compound BH1-7 Compound BH1-7 was synthesized according to the following synthesis route.
[0295] (Synthesis of Intermediate 7-A) 4.10 g of a white solid was obtained (yield 64%) in the same manner as in the synthesis of Compound BH1-1, except that Intermediate 2-D and 2-chlorophenylboronic acid were used instead of Intermediates 1-A and 1-B.
[0296] (Synthesis of Compound BH1-7) A white solid (2.75 g, 43% yield) was obtained in the same manner as in the synthesis of Compound BH1-1, except that Intermediates 7-A and 2-E were used instead of Intermediates 1-A and 1-B. LC-MS analysis identified the white solid as Compound BH1-7.
[0297] (Synthesis Example 8) Synthesis of Compound BH1-8
[0298] A white solid (3.53 g, yield 73%) was obtained in the same manner as in the synthesis of compound BH1-1, except that intermediates 3-D and 2-E were used instead of intermediates 1-A and 1-B. LC-MS analysis identified the white solid as compound BH1-8.
[0299] Although several embodiments and / or examples of the present invention have been described in detail above, those skilled in the art will readily be able to make numerous modifications to these exemplary embodiments and / or examples without substantially departing from the novel teachings and advantages of the present invention. Accordingly, these numerous modifications are within the scope of the present invention. The contents of all documents cited in this specification and of the applications from which this application claims priority under the Paris Convention are incorporated by reference in their entirety.
Claims
1. A compound comprising a structure represented by the following formula (S1) and a structure represented by the following formula (S2): [In formula (S1), X 1 is a single bond, O, or S.
2. The compound according to claim 1, which is a compound represented by the following formula (1): [In formula (1), X 1 is as defined in formula (S1). 1 ~R 11 Among R which do not form a monocycle or a condensed ring, one or more pairs of adjacent R which do not form a monocycle or a condensed ring are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other to form a monocycle or a condensed ring. 1 ~R 11 One of them is (L 1 ) n1 or R 1 ~R 11 One of the atoms constituting a substituted or unsubstituted monocyclic or condensed ring formed by bonding together one or more pairs of adjacent two or more of the above is (L 1 ) n1 is bonded to by a single bond. 21 ~R 32 Among R which do not form a monocycle or a condensed ring, one or more pairs of adjacent R which do not form a monocycle or a condensed ring are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other to form a monocycle or a condensed ring. 21 ~R 32 One of them is (L 1 ) n1 or R 21 ~R 32 One of the atoms constituting the substituted or unsubstituted monocyclic or condensed ring formed by bonding together one or more pairs of adjacent two or more of the 1 ) n1 is bonded to by a single bond. R does not represent a single bond and does not form a single ring or a condensed ring. 1 ~R 11 and R 21 ~R 32 are each independently a hydrogen atom or a substituent R. 1 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms. n1 is an integer of 0 to 3. When n1 is 0, (L 1 ) n1 is a single bond. When n1 is 2 or more, L is 2 or more. 1 are connected in series to each other. When n1 is 2 or more, L is 2 or more. 1 may be the same or different. The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 ) (R 902 ) (R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 ) (R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. 901 ~R 907 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. 901 ~R 907 When there are two or more R 901 ~R 907 may be the same or different. When two or more substituents R are present, the two or more substituents R may be the same or different.
3. R 7 ~R 10 One of them is (L 1 ) n1 The compound according to claim 2, wherein 4. R 21 , R 24 , R 27 , R 29 , R 30 , and R 32 One of them is (L 1 ) n1 4. The compound according to claim 2 or 3, wherein 5. R 21 ~R 32 The compound according to any one of claims 2 to 4, wherein one or more pairs of adjacent two or more of 6. R not representing a single bond 21 ~R 31 The compound according to any one of claims 2 to 5, wherein is a hydrogen atom.
7. X 1 The compound according to any one of claims 1 to 6, wherein is a single bond.
8. L 1 The compound according to any one of claims 2 to 7, wherein is a single bond, or a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.
9. The compound according to any one of claims 2 to 8, wherein n1 is 0.
10. R 1 ~R 11 The compound according to any one of claims 2 to 9, wherein one or more pairs of adjacent two or more of 11. R not representing a single bond 1 ~R 11 The compound according to any one of claims 2 to 10, wherein is a hydrogen atom.
12. The compound according to any one of claims 2 to 11, wherein the compound represented by formula (1) is a compound represented by any one of the following formulas (11) to (18): [In the formulas (11) to (18), X 1 , n1, and L 1 is as defined in formula (1). 101 ~R 111 Among these, one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or to each other to form a substituted or unsubstituted fused ring, or to not form the monocyclic ring or the fused ring. 121 ~R 132 Among R which do not form a monocycle or a condensed ring, one or more pairs of adjacent R which do not form a monocycle or a condensed ring are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other to form a monocycle or a condensed ring. 101 ~R 111 and R 121 ~R 132 are each independently a hydrogen atom or a substituent R. The substituent R is as defined in formula (1).
13. The compound according to any one of claims 2 to 12, wherein the compound represented by formula (1) is a compound represented by the following formula (111): [In formula (111), R 101 ~R 109 , R 111 , R 132 , n1, and L 1 is as defined in the above formulas (11) to (18).
14. The compound according to any one of claims 2 to 12, wherein the compound represented by formula (1) is a compound represented by the following formula (112): [In formula (112), R 101 ~R 108 , R 110 ~R 111 , R 132 , n1, and L 1 is as defined in the above formulas (11) to (18).
15. The compound according to any one of claims 2 to 12, wherein the compound represented by formula (1) is a compound represented by the following formula (113): [In formula (113), R 101 ~R 107 , R 109 ~R 111 , R 132 , n1, and L 1 is as defined in the above formulas (11) to (18).
16. The compound according to any one of claims 2 to 12, wherein the compound represented by formula (1) is a compound represented by the following formula (114): [In formula (114), R 101 ~R 106 , R 108 ~R 111 , R 132 , n1, and L 1 is as defined in the above formulas (11) to (18).
17. R 132 The compound according to any one of claims 12 to 16, wherein is a hydrogen atom.
18. The compound according to any one of claims 2 to 12, wherein the compound represented by formula (1) is a compound represented by the following formula (115): [In formula (115), R 101 ~R 109 , R 111 , R 127 , n1, and L 1 is as defined in the above formulas (11) to (18).
19. The compound according to any one of claims 1 to 18, which is a material for an organic electroluminescence device.
20. An organic electroluminescence device comprising: a cathode; an anode; and one or more organic layers disposed between the cathode and the anode, wherein at least one of the organic layers contains a compound according to any one of claims 1 to 19.
21. The organic electroluminescence device according to claim 20, comprising an anode, an emitting layer, and a cathode in this order, and at least one of the organic layers in the emitting layer contains the compound.
22. The organic electroluminescence device according to claim 21, wherein the light-emitting layer comprises, from the anode side, a first layer and a second layer, and the first layer comprises the compound.
23. The organic electroluminescence device according to claim 21 or 22, wherein the light-emitting layer further contains a compound represented by any one of the following formulas (D11) to (D41): [In formula (D11), each of three Z's independently represents CR a or a nitrogen atom. Ring A1 and ring A2 are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms. a When there are multiple R a At least one pair of adjacent pairs of nD11 and nD12 are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or do not form the monocyclic ring or the fused ring. nD11 and nD12 are each independently 0, 1, 2, 3, or 4. R b When there are multiple R b At least one pair of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or to each other to form a substituted or unsubstituted fused ring, or to neither form the monocyclic ring nor the fused ring. c When there are multiple R c Among adjacent pairs of R, one or more pairs of R that are bonded to each other to form a substituted or unsubstituted monocycle, R that are bonded to each other to form a substituted or unsubstituted condensed ring, or R that are not bonded to each other to form a monocycle or a condensed ring. a , R b , and R c each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 ) (R 902 ) (R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 ) (R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. 901 ~R 907 is as defined in the above formula (1). In formula (D21), R D201 and R D202 , R D202 and R D203 , and R D203 and R D204 At least one pair of R is bonded to each other to form a divalent group represented by the following formula (D22). D205 and R D206 , R D206 and R D207 , and R D207 and R D208 At least one pair of these are bonded to each other to form a divalent group represented by the following formula (D23). R which does not form a divalent group represented by formula (D22) D201 ~R D204 , and R D211 ~R D214 At least one of R which does not form a divalent group represented by formula (D23) is a monovalent group represented by formula (D24). D205 ~R D208 , and R D221 ~R D224 At least one of X is a monovalent group represented by the following formula (D24). D2 is an oxygen atom, a sulfur atom, or NR D209 R does not form a divalent group represented by the formula (D22) or (D23) and is not a monovalent group represented by the formula (D24). D201 ~R D208 R which is not a monovalent group represented by formula (D24) D211 ~R D214 and R D221 ~R D224 , and R D209 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 ) (R 902 ) (R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 ) (R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. (In formula (D24), Ar D201 and Ar D202 each independently represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. D201 ~L D203 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or a divalent linking group formed by bonding 2 to 4 groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms. * indicates the bonding position with the ring structure represented by formula (D21) or the group represented by formula (D22) or formula (D23). R 901 ~R 907 is as defined in the above formula (1). In formula (D31), R D301 ~R D307 and R D311 ~R D317 Among R which do not form a monocycle or a condensed ring, one or more pairs of adjacent R which do not form a monocycle or a condensed ring are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other to form a monocycle or a condensed ring. D301 ~R D307 and R D311 ~R D317 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 ) (R 902 ) (R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 ) (R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. D321 and R D322 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 ) (R 902 ) (R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 ) (R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. 901 ~R 907 is as defined in formula (1). In formula (D41), ring a, ring b and ring c each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms. D401 and R D402 each independently forms a substituted or unsubstituted heterocycle together with the ring a, ring b, or ring c, or does not form a substituted or unsubstituted heterocycle. D401 and R D402 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.] 24. The organic electroluminescence device according to any one of claims 21 to 23, further comprising a hole transporting region between said anode and said light emitting layer.
25. The organic electroluminescence device according to any one of claims 21 to 24, further comprising an electron transporting region between the cathode and the light-emitting layer.
26. An electronic device comprising the organic electroluminescence element according to any one of claims 20 to 25.
Citation Information
Patent Citations
Novel materials for organic electroluminescent devices
JP2010528070A
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