Compositions, mixtures, organic electroluminescent elements, and electronic devices
A composition of specific compounds stabilizes component ratios in vapor deposition for organic electroluminescent elements, addressing inconsistencies in film quality and ensuring consistent performance.
Patent Information
- Application Number
- JP2025021903
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2025-02-13
- Publication Date
- 2026-08-25
AI Technical Summary
Existing vapor deposition methods for organic electroluminescent elements face challenges in maintaining consistent mixing ratios of components, particularly during long-term continuous deposition, leading to variations in film quality across substrates.
A composition comprising specific compounds represented by formulas (1) and (2) is used, which suppresses fluctuations in component ratios during film formation, ensuring stable quality in organic electroluminescent elements.
The solution enables consistent quality in organic EL elements through stable component ratios, even during prolonged vapor deposition processes.
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Abstract
Description
[Technical Field]
[0001] The present invention relates to novel compositions, mixtures, organic electroluminescent elements, and electronic devices. [Background technology]
[0002] Vacuum deposition is generally used as a method for forming the organic layer that constitutes an organic electroluminescent element (hereinafter also referred to as an "organic EL element"). Conventionally, a co-deposition method has been used to form a mixed layer consisting of multiple components, in which each component is vaporized from a separate deposition source (crucible) and deposited simultaneously. In co-evaporation, temperature control and other parameters can be performed independently for each evaporation source, making it easier to adjust the mixing ratio in the evaporated film by controlling the vaporization rate of each material. Furthermore, even when continuously depositing on multiple substrates, it is possible to form films with a constant mixing ratio. On the other hand, using multiple evaporation sources complicates the manufacturing process, leading to challenges such as increased manufacturing burden and costs.
[0003] As a technology to solve the above problems, a vapor deposition technique is attracting attention in which a so-called premixed material, which is a mixture of multiple materials (organic compounds) in advance, is vaporized from a single vapor deposition source to form a film. As an example of premix technology, Patent Document 1 discloses a mixture containing two types of compounds. [Prior art documents] [Patent Documents]
[0004] [Patent Document 1] International Publication No. 2021 / 015266 [Overview of the Initiative] [Problems that the invention aims to solve]
[0005] The object of the present invention is to provide a composition that enables vapor deposition in which fluctuations in the component ratio in the mixed film during the film formation process are suppressed in a vapor deposition process using mixed materials.
Means for Solving the Problem
[0006] The premix technique can eliminate the above-mentioned drawbacks in the co-evaporation method. However, compared with the co-evaporation method, it is difficult to form a vapor-deposited film having a desired mixing ratio. Further, when continuous vapor deposition is performed on a plurality of substrates, there is a problem that the mixing ratio varies depending on the substrates and it is difficult to obtain a constant quality. In an actual organic EL element manufacturing site, since the vapor deposition process is continued continuously for several weeks to several months, it is important to be able to manufacture a mixed film at a stable ratio over a long period. That is, the above problems in the premix technique are important problems to be solved. As a result of investigations by the present inventors, it has been found that the above problems can be solved by using a composition of a combination of compounds having a specific structure, and a stable organic EL element of a certain quality can be obtained by continuous vapor deposition, and the present invention has been completed.
[0007] According to the present invention, the following compositions, mixtures, organic electroluminescence elements, electronic devices, etc. are provided. 1. A composition comprising a compound represented by formula (1) and a compound represented by formula (2).
Chemical Formula
[0008] According to the present invention, a composition is provided that enables vapor deposition using a mixed material in which fluctuations in the component ratio in the mixed film during the film formation process are suppressed. Furthermore, according to the present invention, organic EL elements of a consistent quality can be stably provided by continuous deposition. [Brief explanation of the drawing]
[0009] [Figure 1] This figure shows a schematic configuration of an organic EL element according to one aspect of the present invention. [Modes for carrying out the invention]
[0010] [Definition] In this specification, the term "hydrogen atom" includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.
[0011] In this specification, in chemical structural formulas, any bondable positions where symbols such as "R" or "D" representing a deuterium atom are not explicitly indicated shall be assumed to be bonded to hydrogen atoms, i.e., light hydrogen atoms, deuterium atoms, or tritium atoms.
[0012] In this specification, the ring-forming carbon number refers to the number of carbon atoms among the atoms constituting the ring itself in a compound with a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, fused ring compounds, crosslinked compounds, carbocyclic compounds, and heterocyclic compounds). If the ring is substituted by a substituent, the carbon atoms in the substituent are not included in the ring-forming carbon number. The same applies to the "ring-forming carbon number" described below unless otherwise specified. For example, a benzene ring has 6 ring-forming carbon atoms, a naphthalene ring has 10 ring-forming carbon atoms, a pyridine ring has 5 ring-forming carbon atoms, and a furan ring has 4 ring-forming carbon atoms. Also, for example, the ring-forming carbon number of a 9,9-diphenylfluorenyl group is 13, and the ring-forming carbon number of a 9,9'-spirobifluorenyl group is 25. Furthermore, when a benzene ring is substituted with an alkyl group, for example, the number of carbon atoms in that alkyl group is not included in the number of ring-forming carbon atoms of the benzene ring. Therefore, the number of ring-forming carbon atoms in a benzene ring substituted with an alkyl group is 6. Similarly, when a naphthalene ring is substituted with an alkyl group, for example, the number of carbon atoms in that alkyl group is not included in the number of ring-forming carbon atoms of the naphthalene ring. Therefore, the number of ring-forming carbon atoms in a naphthalene ring substituted with an alkyl group is 10.
[0013] In this specification, the number of ring-forming atoms refers to the number of atoms that constitute the ring itself in compounds with a ring-bonded structure (e.g., monocyclic compounds, fused rings, and ring aggregates) (e.g., monocyclic compounds, fused ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of ring-forming atoms) and atoms included in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. The same applies to "number of ring-forming atoms" as described below unless otherwise specified. For example, the number of ring-forming atoms in a pyridine ring is 6, the number of ring-forming atoms in a quinazoline ring is 10, and the number of ring-forming atoms in a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring, or the number of atoms constituting substituents, are not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms in a pyridine ring to which hydrogen atoms or substituents are bonded is 6. Furthermore, for example, hydrogen atoms bonded to the carbon atom of the quinazoline ring, or atoms constituting substituents, are not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring-forming atoms of a quinazoline ring to which hydrogen atoms or substituents are bonded is 10.
[0014] In this specification, the expression "substituted or unsubstituted ZZ group having XX to YY carbon atoms" means that "XX to YY carbon atoms" represents the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of substituents when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.
[0015] In this specification, the expression "ZZ group with substituted or unsubstituted atoms of XX to YY" means that "atom count XX to YY" represents the number of atoms when the ZZ group is unsubstituted, and does not include the number of substituent atoms when it is substituted. Here, "YY" is greater than "XX", where "XX" is an integer of 1 or more, and "YY" is an integer of 2 or more.
[0016] In this specification, an unsubstituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is "unsubstituted ZZ group," and a substituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is "substituted ZZ group." In this specification, "unsubstituted" in the context of a "substituted or unsubstituted ZZ group" means that the hydrogen atoms in the ZZ group are not replaced by substituents. The hydrogen atoms in an "unsubstituted ZZ group" are light hydrogen atoms, deuterium atoms, or tritium atoms. Furthermore, in this specification, "substituted" in the context of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. Similarly, "substituted" in the context of "BB group substituted with AA group" means that one or more hydrogen atoms in the BB group are replaced by an AA group.
[0017] "Substituents as described herein" The substituents described herein will be explained below.
[0018] The number of ring-forming carbon atoms in the "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring-forming atoms in the "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkyl group" as described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkenyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkynyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted cycloalkyl groups" described herein is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted arylene group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring-forming atoms in the "unsubstituted divalent heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkylene group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein.
[0019] • "substituted or unsubstituted aryl groups" Specific examples of "substituted or unsubstituted aryl groups" as described herein (Specific Examples Group G1) include the following unsubstituted aryl groups (Specific Examples Group G1A) and substituted aryl groups (Specific Examples Group G1B), etc. (Here, "unsubstituted aryl group" refers to the case where "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and "substituted aryl group" refers to the case where "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" simply includes both "unsubstituted aryl groups" and "substituted aryl groups." A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced by substituents. Examples of "substituted aryl groups" include the groups in which one or more hydrogen atoms of an "unsubstituted aryl group" in specific example group G1A below are replaced by substituents, and the examples of substituted aryl groups in specific example group G1B below. Note that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl groups" described herein also include groups in which the hydrogen atoms bonded to the carbon atom of the aryl group itself in the "substituted aryl group" in specific example group G1B below are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted aryl group" in specific example group G1B below are further replaced by substituents.
[0020] • Unsubstituted aryl groups (specific examples group G1A): Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-Naphthyl group, 2-Naphthyl group, anthryl group, Benzoantryl group, Phenanthryl group, Benzophenanthryl group, Phenalenyl group, Pyrenyl group, Chrysenyl group, Benzocrisenyl group, Triphenylenyl group, benzotriphenylenyl group, Tetraceryl group, Pentacenyl group, Fluorenyl group, 9,9'-Spirobifluorenyl group, Benzofluorenyl group, Dibenzofluorenyl group, Fluoranthenyl group, Benzofluoranthenyl group, Perilenyl group, and A monovalent aryl group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).
[0021] [ka]
[0022] [ka]
[0023] • Substitutive aryl groups (Specific examples group G1B): o-Tryl group, m-tolyl group, p-tril group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, Meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, Cyanophenyl group, Triphenylsilylphenyl group, Trimethylsilylphenyl group, Phenylnaphthyl group, Naphthylphenyl group, and A group obtained by replacing one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the general formulas (TEMP-1) to (TEMP-15) above with substituents.
[0024] • "Substitutable or unsubstituted heterocyclic groups" The “heterocyclic group” as described herein is a cyclic group containing at least one heteroatom in its ring-forming atoms. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron. The "heterocyclic group" as described herein is either a monocyclic group or a fused-cyclic group. The term "heterocyclic group" as used herein refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples of "substituted or unsubstituted heterocyclic groups" as described herein (Specific Examples Group G2) include the following unsubstituted heterocyclic groups (Specific Examples Group G2A) and substituted heterocyclic groups (Specific Examples Group G2B), etc. (Here, "unsubstituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group," and "substituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group.") In this specification, the term "heterocyclic group" simply includes both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups." A "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of "substituted heterocyclic groups" include the groups in specific example group G2A below in which hydrogen atoms of an "unsubstituted heterocyclic group" are replaced, and the examples of substituted heterocyclic groups in specific example group G2B below. Note that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic groups" described herein also include groups in which hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself are further replaced by substituents, and groups in which hydrogen atoms of substituents are further replaced by substituents.
[0025] The specific examples group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).
[0026] Specific examples group G2B includes, for example, substituted heterocyclic groups containing a nitrogen atom (Specific Examples Group G2B1), substituted heterocyclic groups containing an oxygen atom (Specific Examples Group G2B2), substituted heterocyclic groups containing a sulfur atom (Specific Examples Group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (Specific Examples Group G2B4).
[0027] • Unsubstituted heterocyclic groups containing a nitrogen atom (specific examples group G2A1): Pyrrolyl group, imidazolyl group, Pyrazolyl group, Triazolyl group, Tetrazolyl group, Oxazolyl group, isoxazolyl group, Oxadiazolyl group, Thiazolyl group, isothiazolyl group, Thiadianzolyl group, Pyridyl group, Pyridazinyl group, Pyrimidinyl group, pyrazinyl group, Triazinyl group, Indolyl group, isoindolyl group, indolidinyl group, Quinolidinyl group, quinolyl group, Isoquinolyl group, cinnolyl group, Phthalazinyl group, Quinazolinyl group, Quinoxalinyl group, Benzimidazolyl group, Indazolyl group, Phenanthrolinyl group, Phenantridinyl group, Acridinyl group, Phenazinyl group, Carbazolyl group, Benzocarbazolyl group, Morpholino group, Phenoxadinyl group, Phenothiazinyl group, Azacarbazolyl group and diazacarbazolyl group.
[0028] • Unsubstituted heterocyclic groups containing an oxygen atom (specific examples group G2A2): Frill group, Oxazolyl group, isoxazolyl group, Oxadiazolyl group, xanthenyl group, Benzofuranyl group, Isobenzofuranyl group, Dibenzofuranyl group, Naphthobenzofuranyl group, Benzoxazolyl group, Benzoisoxazolyl group, Phenoxadinyl group, Morpholino group, Dinaphthofuranyl group, Azadibenzofuranyl group, Diazadibenzofuranyl group, Azanaftobenzofuranyl group, and Diazanaphthobenzofuranyl group.
[0029] • Unsubstituted heterocyclic groups containing a sulfur atom (specific examples group G2A3): Thienyl group, Thiazolyl group, isothiazolyl group, Thiadianzolyl group, Benzothiophenyl group (benzothienyl group), Isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), Naphthobenzothiophenyl group (naphthobenzothienyl group), Benzothiazolyl group, Benzoisothiazolyl group, Phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), azadibenzothiophenyl group (azadibenzothienyl group), Diazadibenzothiophenyl group (diazadibenzothienyl group), Azanaphtobenzothiophenyl group (azanaphthobenzothienyl group), and Diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).
[0030] • Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (Specific examples group G2A4):
[0031] [ka]
[0032] [ka]
[0033] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each of these is independently an oxygen atom, a sulfur atom, NH, or CH2. However, X A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH. In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A If at least one of the members is NH or CH2, the monovalent heterocyclic groups derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) include monovalent groups obtained by removing one hydrogen atom from these NH or CH2 members.
[0034] • Heterocyclic groups with substitutions containing a nitrogen atom (Specific examples group G2B1): (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazole-9-yl group, Phenylcarbazole-9-yl group, Methyl benzimidazolyl group, Ethyl benzimidazolyl group, Phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, Phenylquinazolinyl group, and Biphenylylquinazolinyl group.
[0035] • Heterocyclic groups with substitutions containing an oxygen atom (Specific examples group G2B2): Phenyldibenzofuranyl group, Methyldibenzofuranyl group, t-butyldibenzofuranyl group, and A monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].
[0036] • Heterocyclic groups with substitutions containing a sulfur atom (specific examples group G2B3): Phenyldibenzothiophenyl group, Methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and A monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].
[0037] • Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific examples group G2B4):
[0038] The aforementioned "one or more hydrogen atoms of a monovalent heterocyclic group" refers to hydrogen atoms bonded to the ring-forming carbon atoms of the monovalent heterocyclic group, X A and Y A A hydrogen atom bonded to a nitrogen atom when at least one of them is NH, and X A and Y AThis refers to one or more hydrogen atoms selected from the hydrogen atoms of the methylene group when one of the atoms is CH2.
[0039] • "Substituted or unsubstituted alkyl groups" Specific examples of "substituted or unsubstituted alkyl groups" as described herein (Specific Examples Group G3) include the following unsubstituted alkyl groups (Specific Examples Group G3A) and substituted alkyl groups (Specific Examples Group G3B). (Here, "unsubstituted alkyl group" refers to the case where "substituted or unsubstituted alkyl group" is "unsubstituted alkyl group," and "substituted alkyl group" refers to the case where "substituted or unsubstituted alkyl group" is "substituted alkyl group.") Hereafter, "alkyl group" simply refers to both "unsubstituted alkyl groups" and "substituted alkyl groups." A "substituted alkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced by substituents. Specific examples of "substituted alkyl groups" include the groups in which one or more hydrogen atoms in the "unsubstituted alkyl groups" (specific example group G3A) below are replaced by substituents, and examples of substituted alkyl groups (specific example group G3B). In this specification, the alkyl group in "unsubstituted alkyl group" refers to a linear alkyl group. Therefore, "unsubstituted alkyl groups" include both linear "unsubstituted alkyl groups" and branched "unsubstituted alkyl groups". The examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed here are merely examples, and the "substituted alkyl groups" described herein also include groups in which the hydrogen atoms of the alkyl group itself in the "substituted alkyl groups" of specific example group G3B are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted alkyl groups" of specific example group G3B are further replaced by substituents.
[0040] • Unsubstituted alkyl groups (specific examples group G3A): Methyl group, Ethyl group, n-propyl group, Isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group.
[0041] • Substituting alkyl groups (specific examples group G3B): Heptafluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.
[0042] • "Substituted or unsubstituted alkenyl groups" Specific examples of "substituted or unsubstituted alkenyl groups" as described herein (Specific Examples Group G4) include the following unsubstituted alkenyl groups (Specific Examples Group G4A) and substituted alkenyl groups (Specific Examples Group G4B), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply includes both "unsubstituted alkenyl groups" and "substituted alkenyl groups." A "substituted alkenyl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted alkenyl group" are replaced by substituents. Specific examples of "substituted alkenyl groups" include groups in which the "unsubstituted alkenyl group" (Specific Example Group G4A) has substituents, and examples of substituted alkenyl groups (Specific Example Group G4B). Note that the examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl groups" described herein also include groups in which the hydrogen atoms of the alkenyl group itself in the "substituted alkenyl group" of Specific Example Group G4B are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted alkenyl group" of Specific Example Group G4B are further replaced by substituents.
[0043] • Unsubstituted alkenyl groups (specific examples group G4A): vinyl group, allyl group, 1-Butenyl group, 2-butenyl group, and 3-Butenyl group.
[0044] • Substitutive alkenyl groups (specific examples group G4B): 1,3-butanedienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.
[0045] • "Substituted or unsubstituted alkynyl groups" Specific examples of "substituted or unsubstituted alkynyl groups" as described herein (Specific Examples Group G5) include the following unsubstituted alkynyl groups (Specific Examples Group G5A), etc. (Here, "unsubstituted alkynyl group" refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group.") Hereafter, when simply referred to as "alkynyl group," it includes both "unsubstituted alkynyl groups" and "substituted alkynyl groups." A "substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced by substituents. Specific examples of "substituted alkynyl groups" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl group" (specific example group G5A) are replaced by substituents.
[0046] • Unsubstituted alkynyl groups (specific examples group G5A): Ethynyl group
[0047] • "Substituted or unsubstituted cycloalkyl groups" Specific examples of "substituted or unsubstituted cycloalkyl groups" as described herein (Specific Examples Group G6) include the following unsubstituted cycloalkyl groups (Specific Examples Group G6A) and substituted cycloalkyl groups (Specific Examples Group G6B), etc. (Here, "unsubstituted cycloalkyl group" refers to the case where "substituted or unsubstituted cycloalkyl group" is "unsubstituted cycloalkyl group," and "substituted cycloalkyl group" refers to the case where "substituted or unsubstituted cycloalkyl group" is "substituted cycloalkyl group.") In this specification, the term "cycloalkyl group" simply includes both "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups." A "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced by a substituent. Specific examples of "substituted cycloalkyl groups" include the groups in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" (specific example group G6A) are replaced by a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed here are merely examples, and the "substituted cycloalkyl groups" described herein also include groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself are replaced by a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted cycloalkyl group" of specific example group G6B are further replaced by a substituent.
[0048] • Unsubstituted cycloalkyl groups (specific examples group G6A): Cyclopropyl group, Cyclobutyl group, Cyclopentyl group, Cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.
[0049] • Substituting cycloalkyl groups (specific examples group G6B): 4-methylcyclohexyl group.
[0050] · "-Si(R 901 )(R 902 )(R 903 ) represented by the base -Si(R 901 )(R 902 )(R 903 ) Examples of the base represented by (Example Group G7) are: -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) Here are some examples. G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6. In -Si(G1)(G1)(G1), the multiple G1s are either identical or different from one another. In -Si(G1)(G2)(G2), the multiple G2s are either identical or different from one another. In -Si(G1)(G1)(G2), the multiple G1s are either identical or different from one another. In -Si(G2)(G2)(G2), the multiple G2s are either identical or different from one another. In -Si(G3)(G3)(G3), the multiple G3s are either identical or different from one another. In -Si(G6)(G6)(G6), the multiple G6s are either identical or different from one another.
[0051] ·「-O-(R 904 ) represented by the base The following information pertains to the -O-(R904 ) Examples of the base represented by (Example Group G8) are: -O(G1), -O(G2), -O(G3), and -O(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6.
[0052] · "-S-(R 905 ) represented by the base -S-(R 905 ) Examples of the base represented by (example group G9) are: -S(G1), -S(G2), -S(G3), and -S(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6.
[0053] · "-N(R 906 )(R 907 ) represented by the base -N(R) as described in this specification 906 )(R 907 ) Examples of the base represented by (Example Group G10) are: -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6. In -N(G1)(G1), multiple G1s are either identical or different from one another. In -N(G2)(G2), multiple G2s are either identical or different from one another. In -N(G3)(G3), multiple G3s are either identical or different from one another. In -N(G6)(G6), multiple G6s are either identical or different from one another.
[0054] • "Halogen atom" Specific examples of "halogen atoms" as described herein (Specific Examples Group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.
[0055] • "Substituted or unsubstituted fluoroalkyl groups" The terms "substituted or unsubstituted fluoroalkyl groups" as used herein refer to groups in which at least one hydrogen atom bonded to the carbon atoms constituting the alkyl group is replaced by a fluorine atom, and also include groups in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group are replaced by fluorine atoms (perfluoro groups). The number of carbon atoms in an "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. A "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced by substituents. The terms "substituted fluoroalkyl groups" as used herein also include groups in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent are further replaced by substituents. Specific examples of "unsubstituted fluoroalkyl groups" include the example of a group in which one or more hydrogen atoms in the aforementioned "alkyl group" (specific example group G3) are replaced by fluorine atoms.
[0056] • "Substituted or unsubstituted haloalkyl groups" The terms "substituted or unsubstituted haloalkyl groups" as used herein refer to groups in which at least one hydrogen atom bonded to the carbon atoms constituting the alkyl group is replaced by a halogen atom, and also include groups in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group are replaced by halogen atoms. The number of carbon atoms in an "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. A "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of a "haloalkyl group" are replaced by substituents. The terms "substituted haloalkyl groups" as used herein also include groups in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent are further replaced by substituents. Specific examples of "unsubstituted haloalkyl groups" include groups in which one or more hydrogen atoms of the aforementioned "alkyl group" (specific example group G3) are replaced by halogen atoms. Haloalkyl groups are sometimes referred to as alkyl halogens.
[0057] • "Substituted or unsubstituted alkoxy groups" A specific example of a "substituted or unsubstituted alkoxy group" as described herein is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. The number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein.
[0058] • "substituted or unsubstituted alkylthio groups" A specific example of the "substituted or unsubstituted alkylthio group" described herein is the group represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. The number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein.
[0059] • "Substituted or unsubstituted aryloxy groups" A specific example of a "substituted or unsubstituted aryloxy group" as described herein is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.
[0060] • "Substituted or unsubstituted arylthio groups" A specific example of the "substituted or unsubstituted arylthio group" described herein is the group represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.
[0061] • "Substituted or unsubstituted trialkylsilyl groups" A specific example of the "trialkylsilyl group" described herein is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) are either identical or different from one another. Unless otherwise specified herein, the number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[0062] • "Substituted or unsubstituted aralkyl groups" Specific examples of the "substituted or unsubstituted aralkyl group" described herein include the group represented by -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3, and G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. Therefore, an "aralkyl group" is a group in which the hydrogen atom of an "alkyl group" is replaced by an "aryl group" as a substituent, and is one form of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" in which an "unsubstituted aryl group" is substituted, and the number of carbon atoms in the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified herein. Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.
[0063] Unless otherwise specified herein, the substituted or unsubstituted aryl groups are preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, pyrenyl, chrysenyl, triphenylenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl.
[0064] Unless otherwise specified herein, the substituted or unsubstituted heterocyclic groups are preferably pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, benzimidazolyl, phenanthrolinyl, carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, or 9-carbazolyl), benzocarbazolyl, azacarbazolyl, diazacarbazolyl, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, aza These include dibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazole-1-yl group, (9-phenyl)carbazole-2-yl group, (9-phenyl)carbazole-3-yl group, or (9-phenyl)carbazole-4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazole-9-yl group, phenylcarbazole-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group, etc.
[0065] In this specification, unless otherwise specified, the carbazolyl group is specifically one of the following groups:
[0066] [ka]
[0067] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically one of the following groups:
[0068] [ka]
[0069] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a binding site.
[0070] In this specification, unless otherwise specified, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups:
[0071] [ka]
[0072] In the general formulas (TEMP-34) to (TEMP-41) above, * represents a binding site.
[0073] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t-butyl groups.
[0074] • "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described herein is a divalent group derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described above. Specific examples of the "substituted or unsubstituted arylene group" (Specific Examples Group G12) include the divalent group derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described in Specific Examples Group G1.
[0075] • "Substitutable or unsubstituted divalent heterocyclic groups" Unless otherwise specified, the “substituted or unsubstituted divalent heterocyclic groups” described herein refer to divalent groups derived by removing one hydrogen atom from the heterocycle of the “substituted or unsubstituted heterocyclic groups” described above. Specific examples of “substituted or unsubstituted divalent heterocyclic groups” (Specific Examples Group G13) include the divalent groups derived by removing one hydrogen atom from the heterocycle of the “substituted or unsubstituted heterocyclic groups” described in Specific Examples Group G2.
[0076] • "Substituted or unsubstituted alkylene groups" Unless otherwise specified, the "substituted or unsubstituted alkylene groups" described herein are divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl groups" described above. Specific examples of "substituted or unsubstituted alkylene groups" (Specific Examples Group G14) include the divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl groups" described in Specific Examples Group G3.
[0077] Unless otherwise specified herein, the substituted or unsubstituted arylene groups are preferably any of the following general formulas (TEMP-42) to (TEMP-68).
[0078] [ka]
[0079] [ka]
[0080] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each of these is independently either a hydrogen atom or a substituent. In the above general formulas (TEMP-42) to (TEMP-52), * represents a binding site.
[0081] [ka]
[0082] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each of these is independently either a hydrogen atom or a substituent. Equations Q9 and Q 10 These elements may be bonded to each other via single bonds to form a ring. In the above general formulas (TEMP-53) to (TEMP-62), * represents a binding site.
[0083] [ka]
[0084] In the general formulas (TEMP-63) to (TEMP-68) above, Q1 to Q8 are each independently a hydrogen atom or a substituent. In the above general formulas (TEMP-63) to (TEMP-68), * represents a binding site.
[0085] Unless otherwise specified herein, the substituted or unsubstituted divalent heterocyclic groups described herein are preferably any of the following general formulas (TEMP-69) to (TEMP-102).
[0086] [ka]
[0087] [ka]
[0088] [ka]
[0089] In the general formulas (TEMP-69) to (TEMP-82) above, Q1 to Q9 are each independently a hydrogen atom or a substituent.
[0090] [ka]
[0091] [ka]
[0092] [ka]
[0093] [ka]
[0094] In the general formulas (TEMP-83) to (TEMP-102) above, Q1 to Q8 are each independently a hydrogen atom or a substituent.
[0095] The above is a description of the substituents described herein.
[0096] • "When they combine to form a ring" In this specification, the phrase "one or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring, combine to form a substituted or unsubstituted fused ring, or do not combine with each other" means the following: "one or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring," "one or more pairs of adjacent elements combine to form a substituted or unsubstituted fused ring," and "one or more pairs of adjacent elements do not combine with each other." In this specification, the cases in which "one or more pairs of adjacent elements bond to each other to form a substituted or unsubstituted monoring" and "one or more pairs of adjacent elements bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "cases where elements bond to form a ring") will be explained below. An example will be given of an anthracene compound represented by the following general formula (TEMP-103), whose parent skeleton is an anthracene ring.
[0097] [ka]
[0098] For example, R921 ~R 930 In the case where "one or more pairs of adjacent groups are joined together to form a ring," the pairs of adjacent groups that make up one set are R 921 and R 922 The pair, R 922 and R 923 The pair, R 923 and R 924 The pair, R 924 and R 930 The pair, R 930 and R 925 The pair, R 925 and R 926 The pair, R 926 and R 927 The pair, R 927 and R 928 The pair, R 928 and R 929 The pair with, and R 929 and R 921 They are a pair.
[0099] The phrase "one or more pairs" above means that two or more pairs of adjacent pairs may simultaneously form a ring. For example, R 921 and R 922 and are joined to form a ring Q A Forms R 925 and R 926 and are joined to form a ring Q B If the above general formula (TEMP-103) is formed, the anthracene compound represented by the above general formula (TEMP-104) is represented by the following general formula (TEMP-104).
[0100] [ka]
[0101] The case where "two or more adjacent elements form a ring" includes not only cases where two adjacent elements are joined, as in the example above, but also cases where three or more adjacent elements are joined. For example, R 921 and R 922 and are joined to form a ring Q A Forms R 922 and R923 and are joined to form a ring Q C It forms three adjacent (R 921 , R 922 and R 923 This refers to the case where a set consisting of ) is bonded to each other to form a ring and condenses onto the anthracene matrix skeleton, in which case the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C R 922 Share.
[0102] [ka]
[0103] The formed "mono-ring" or "condensed-ring" may be saturated or unsaturated, based solely on the structure of the formed ring. Even when "a pair of adjacent rings" forms a "mono-ring" or "condensed-ring," the "mono-ring" or "condensed-ring" can be saturated or unsaturated. For example, ring Q formed in the general formula (TEMP-104) A and ring Q B These are, respectively, a "single ring" or a "condensed ring". Also, ring Q formed in the general formula (TEMP-105) is A , and ring Q C This is a "condensed ring". The ring Q of the general formula (TEMP-105) A and Q C This refers to the Q environment. A and Q C The ring Q of the general formula (TMEP-104) is formed by the condensation of the two rings. A If it is a benzene ring, then ring Q A It is a single ring. The ring Q of the general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a condensed ring.
[0104] "Unsaturated rings" include aromatic hydrocarbon rings, aromatic heterocycles, as well as aliphatic hydrocarbon rings (e.g., cyclohexene, cyclohexadiene, etc.) having unsaturated bonds in their ring structure, i.e., double and / or triple bonds, and non-aromatic heterocycles (e.g., dihydropyran, imidazoline, pyrazoline, quinolidine, indoline, isoindoline, etc.) having unsaturated bonds. "Saturated rings" include aliphatic hydrocarbon rings without unsaturated bonds, or non-aromatic heterocycles without unsaturated bonds. Specific examples of aromatic hydrocarbon rings include structures in which the groups listed as examples in specific example group G1 are terminated by hydrogen atoms. A concrete example of an aromatic heterocycle is the structure in which the aromatic heterocycle group listed as a concrete example in concrete example group G2 is terminated by a hydrogen atom. Specific examples of aliphatic hydrocarbon rings include structures in which the groups listed as examples in specific example group G6 are terminated by hydrogen atoms. "To form a ring" means to form a ring with only multiple atoms of the parent skeleton, or with multiple atoms of the parent skeleton and one or more additional arbitrary atoms. For example, as shown in the general formula (TEMP-104), 921 and R 922 A ring Q is formed when these two elements are bonded together. A R 921 The carbon atoms of the anthracene skeleton to which R is bonded, 922 It refers to a ring formed by the carbon atoms of the anthracene skeleton to which it is bonded, and one or more arbitrary atoms. A specific example is R 921 and R 922 And the environment Q A When forming R 921 The carbon atoms of the anthracene skeleton to which R is bonded, 922 When the carbon atoms of the anthracene skeleton bonded to the four carbon atoms form a monocyclic unsaturated ring, R 921 and R 922 The ring formed by these two is a benzene ring.
[0105] Here, "any atom" is preferably at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms, unless otherwise specified herein. In any atom (for example, carbon atoms or nitrogen atoms), bonds that do not form a ring may be terminated with hydrogen atoms or the like, or substituted with "any substituents" as described later. If any atom other than carbon atoms is included, the formed ring is a heterocycle. Unless otherwise specified herein, the "one or more arbitrary atoms" constituting a 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, the preferred form is a monoring or a fused ring. Unless otherwise specified herein, the "unsaturated ring" is preferred over the "saturated ring". Unless otherwise specified herein, “monocyclic” is preferably a benzene ring. Unless otherwise specified herein, the “unsaturated ring” is preferably a benzene ring. When "one or more sets of two or more adjacent atoms" "bond to each other to form a substituted or unsubstituted monoring" or "bond to each other to form a substituted or unsubstituted fused ring", unless otherwise specified herein, preferably, one or more sets of two or more adjacent atoms bond to each other to form a substituted or unsubstituted "unsaturated ring" consisting of multiple 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 substituents, the substituents are, for example, "any substituents" as described later. Specific examples of substituents when the above-mentioned "monocyclic ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described herein" above. When the above-mentioned "saturated ring" or "unsaturated ring" has substituents, the substituents are, for example, "any substituents" as described later. Specific examples of substituents when the above-mentioned "mono-ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described herein" above. The above explains the cases in which "one or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring" and "one or more pairs of adjacent elements combine to form a substituted or unsubstituted fused ring" ("the case of combining to form a ring").
[0107] • Substituents in the phrase "substituted or unsubstituted" In one embodiment described herein, the substituent referred to as "substituted or unsubstituted" (which may be referred to herein as "any substituent") is, for example, Unsubstituted alkyl groups with 1 to 50 carbon atoms, Unsubstituted alkenyl groups with 2 to 50 carbon atoms, Unsubstituted alkynyl groups with 2 to 50 carbon atoms, Unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, Unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, and Unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms It is a base selected from the group consisting of, Here, R 901 ~R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If there are two or more of them, then there are two or more R 901 They are either identical or different from each other. R 902 If there are two or more of them, then there are two or more R 902 They are either identical or different from each other. R 903 If there are two or more of them, then there are two or more R 903 They are either identical or different from each other. R 904 If there are two or more of them, then there are two or more R 904 They are either identical or different from each other. R 905 If there are two or more of them, then there are two or more R 905 They are either identical or different from each other. R 906 If there are two or more of them, then there are two or more R 906 They are either identical or different from each other. R 907 If there are two or more of them, then there are two or more R 907 They are either identical or different from one another.
[0108] In one embodiment, the substituent in the case of "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 50 carbon atoms, A ring-forming aryl group with 6 to 50 carbon atoms, and Heterocyclic groups with 5 to 50 ring-forming atoms It is a group selected from the group consisting of the following.
[0109] In one embodiment, the substituent in the case of "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 18 carbon atoms, A ring-forming aryl group with 6 to 18 carbon atoms, and Heterocyclic groups with 5 to 18 ring-forming atoms It is a group selected from the group consisting of the following.
[0110] Specific examples of each of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents as described herein" above.
[0111] Unless otherwise specified herein, adjacent substituents may form a "saturated ring" or an "unsaturated ring," preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, and more preferably a benzene ring. Unless otherwise specified herein, any substituent may have further substituents, such as those described above.
[0112] In this specification, a numerical range expressed using "AA~BB" means a range that includes the numerical value AA, which is listed before "AA~BB", as the lower limit, and the numerical value BB, which is listed after "AA~BB", as the upper limit.
[0113] [Novel composition] A composition according to one aspect of the present invention is characterized by comprising a compound represented by formula (1) (hereinafter also referred to as the "first component") and a compound represented by formula (2) (hereinafter also referred to as the "second component"). Formulas (1) and (2) will be discussed later. It should be noted that, as is obvious from the definition, the compound represented by formula (1) and the compound represented by formula (2) are different compounds.
[0114] When vapor deposition is performed using a composition having the above configuration, the balance of vaporization amounts of the first and second components can be maintained for a long period of time. In particular, when performing continuous vapor deposition on multiple substrates, it becomes possible to deposit films with a stable component ratio from the beginning to the end of the vapor deposition process. This minimizes the occurrence of defective products and raw material loss, thereby increasing yield and improving productivity. It should be noted that the above effect is not intended to mean that films can be deposited at a constant ratio on all substrates subjected to the continuous vapor deposition process. Even when using a composition according to one aspect of the present invention, it is conceivable that the component ratio may fluctuate somewhat, especially in the final stage of the process, but it means that the proportion of time during which films can be deposited at a stable ratio can be greatly improved.
[0115] In one embodiment of the present invention, the mixing ratio of the first component and the second component is not particularly limited, and the mixing ratio of the materials can be appropriately determined according to the properties of each compound and the effects desired from the composition.
[0116] In one embodiment, the content ratio (mass ratio) of the first component to the second component in the composition according to one aspect of the present invention is usually 1:99 to 99:1, preferably 10:90 to 90:10, and more preferably 30:70 to 70:30.
[0117] In one embodiment, a composition according to one aspect of the present invention consists only of a first component and a second component, or substantially only of a first component and a second component. In the latter case, it may contain unavoidable impurities. In one embodiment, the composition according to one aspect of the present invention has a first component and a second component that are 80% or more by mass, 90% or more by mass, 95% or more by mass, 99% or more by mass, 99.5% or more by mass, 99.9% or more by mass, 99.99% or more by mass, or 100% by mass. In one embodiment, the composition according to one aspect of the present invention has a first component and a second component that are 80 mol% or more, 90 mol% or more, 95 mol% or more, 99 mol% or more, 99.5 mol% or more, 99.9 mol% or more, 99.99 mol% or more, or 100 mol%.
[0118] The details of each compound are described below.
[0119] (Component 1) The first component is a compound represented by the following formula (1). [ka] [In equation (1), R 102 , R 111 ~R 114 , and R 121 ~R 128 One of them is substituent α. The substituent α is a substituted or unsubstituted phenyl group. R 101 and R 131 ~R 135 , as well as R that is not substituent α 102 , R 111 ~R 114 , and R 121 ~R 128 Each of these is independently either a hydrogen atom or a substituent β. R 101 , R 102 , R 111 ~R 114 , R 121 ~R 128 , and R 131 ~R 135 Two or more adjacent pairs of these pairs cannot be combined with each other. The four Rs 101 They may be the same or different from each other. The three R's 102 They may be the same or different from each other. The substituent β is, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901)(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Cyano group, Nitro group, -P(=O)(R 931 )(R 932 A base represented by ) -Ge(R 933 )(R 934 )(R 935 A base represented by ) -B(R 936 )(R 937 A base represented by ) -B(OR 938 )(OR 939 A base represented by ) -OS(=O)2(R 940 A base represented by ) Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, and Monovalent heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms It is selected from the group consisting of the following. If there are two or more substituents β, the two or more substituents β may be the same or different from each other. R 801 , R 802 , R 901 ~R 907 , and R 931 ~R 940 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a monovalent heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms. R 801 , R 802 , R 901 ~R 907 , and R 931 ~R 940 If there are two or more of them, then there are two or more R 801 , R 802 , R 901 ~R 907 , and R 931 ~R 940 Each of these may be the same or different.
[0120] In formula (1), a bond shown crossing the carbon-carbon bond of a benzene ring represents a bond to any of the bondable carbon atoms on the benzene ring. In other words, the structure (E1) in equation (1) below encompasses the structures (E1-1) to (E1-4) below. Note that in structures (E1) and (E1-1) to (E1-4), some parts of the structure in equation (1) are omitted. [ka] [ka]
[0121] The three R's in equation (1) 102 And, R 121 ~R 128 The same explanation can be applied to the carbazole-9-yl group to which is bonded, and to the bond that appears to cross the carbon-carbon bond of the benzene ring. That is, three R 102 And, R 121 ~R 128 The carbazole-9-yl group to which it is bonded means that it is bonded to one of the four bondable carbon atoms on the benzene ring. Furthermore, the four R's in equation (2) described later... 201 And, R 211 ~R 218 The same explanation can be applied to the carbazole-9-yl group to which it is bonded, in relation to the bond that appears to cross the carbon-carbon bond of the benzene ring. That is, four R 201 And, R 211 ~R 218 The carbazole-9-yl group to which it is bonded means that it is bonded to one of the five bondable carbon atoms on the benzene ring.
[0122] In one embodiment, R in formula (1) 121 ~R 128 One of them is substituent α. In one embodiment, R in formula (1) 123 and R 126 One of them is substituent α.
[0123] In one embodiment, the substituent β is Substituted or unsubstituted alkyl groups with 1 to 30 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 30 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 30 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 30 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 30 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Cyano group, Nitro group, -P(=O)(R 931 )(R 932 A base represented by ) -Ge(R 933 )(R 934 )(R 935 A base represented by ) -B(R 936 )(R 937 A base represented by ) -B(OR 938 )(OR 939 A base represented by ) -OS(=O)2(R 940 A base represented by ) Substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms, and Monovalent heterocyclic groups with 5 to 30 substituted or unsubstituted ring-forming atoms It is selected from the group consisting of the following.
[0124] In one embodiment, R is not the substituent α in formula (1). 101 , R 102 , R 111 ~R 114 , R 121 ~R 128 , and R 131 ~R 135 This is a hydrogen atom.
[0125] In one embodiment, the compound represented by formula (1) has at least one deuterium atom.
[0126] In one embodiment, R in formula (1) 101 It is a deuterium atom. In one embodiment, R in formula (1) 102 It is a deuterium atom. In one embodiment, R in formula (1) 111 ~R 114 It is a deuterium atom. In one embodiment, R is the hydrogen atom in formula (1). 121 ~R128 It is a deuterium atom. In one embodiment, R in formula (1) 131 ~R 135 It is a deuterium atom.
[0127] In one embodiment, R is the hydrogen atom in formula (1). 101 , R 102 , R 111 ~R 114 , R 121 ~R 128 , and R 131 ~R 135 It is a deuterium atom.
[0128] In one embodiment, the compound represented by formula (1) is the compound represented by the following formula (1-1). [ka] [In equation (1-1), R 101 , R 102 , R 111 ~R 114 , R 121 ~R 128 , and R 131 ~R 135 This is as defined in equation (1) above.
[0129] In one embodiment, R in formula (1-1) 121 ~R 128 At least one of them is substituent α. In one embodiment, R in formula (1-1) 123 and R 126 One of them is substituent α.
[0130] In one embodiment, the substituent in formula (1) when referring to "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 50 carbon atoms, Alkenyl groups with 2 to 50 carbon atoms, Alkynyl groups with 2 to 50 carbon atoms, Cycloalkyl groups with 3 to 50 carbon atoms forming the ring, -Si(R901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, A ring-forming aryl group with 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms. R 901 ~R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a monovalent heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms.
[0131] In one embodiment, the substituent in formula (1) when referring to "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 50 carbon atoms, A ring-forming aryl group with 6 to 50 carbon atoms, and Heterocyclic groups with 5 to 50 ring-forming atoms A group selected from the group consisting of,
[0132] In one embodiment, the substituent in formula (1) when referring to "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 18 carbon atoms, A ring-forming aryl group with 6 to 18 carbon atoms, and Heterocyclic groups with 5 to 18 ring-forming atoms It is a group selected from the group consisting of the following.
[0133] Compounds represented by formula (1) can be synthesized by using known reactions and starting materials that are appropriate for the target product.
[0134] The following are specific examples of compounds represented by formula (1), but these are merely examples, and compounds represented by formula (1) are not limited to the examples below.
[0135] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0136] (Second component) The second component is a compound represented by the following formula (2). [ka] [In equation (2), At least two of Z1 to Z3 are N, and the ones that are not N are C(R) 2a ) R 2a , R 201 , R 211 ~R218 , R 221 ~R 228 , and R 231 ~R 238 Each of these is independently either a hydrogen atom or a substituent β. R 2a , R 201 , R 211 ~R 218 , R 221 ~R 228 , and R 231 ~R 238 Two or more adjacent pairs of these pairs cannot be combined with each other. The four Rs 201 They may be the same or different from each other. The substituent β is as defined in formula (1) above.
[0137] In one embodiment, Z1 to Z3 in equation (2) are N.
[0138] In one embodiment, the compound represented by formula (2) is the compound represented by the following formula (2-1). [ka] [In equation (2-1), R 201 , R 211 ~R 218 , R 221 ~R 228 , and R 231 ~R 238 This is as defined in equation (1) above.
[0139] In one embodiment, R in formula (2) 201 , R 211 ~R 218 , R 221 ~R 228 , and R 231 ~R 238 This is a hydrogen atom.
[0140] In one embodiment, the compound represented by formula (2) has at least one deuterium atom.
[0141] In one embodiment, R is the hydrogen atom in formula (2). 211 ~R 218 , R 221 ~R 228 , and R 231 ~R 238 It is a deuterium atom.
[0142] In one embodiment, R is the hydrogen atom in formula (2). 201 , R 211 ~R 218 , R 221 ~R 228 , and R 231 ~R 238 It is a deuterium atom.
[0143] In one embodiment, R in formula (2) 201 It is a deuterium atom. In one embodiment, R in formula (2) 211 ~R 218 It is a deuterium atom. In one embodiment, R in formula (2) 221 ~R 228 It is a deuterium atom. In one embodiment, R in formula (2) 231 ~R 238 It is a deuterium atom.
[0144] In one embodiment, the substituent in formula (2) when referring to "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 50 carbon atoms, Alkenyl groups with 2 to 50 carbon atoms, Alkynyl groups with 2 to 50 carbon atoms, Cycloalkyl groups with 3 to 50 carbon atoms forming the ring, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, A ring-forming aryl group with 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms. R 901 ~R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a monovalent heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms.
[0145] In one embodiment, the substituent in formula (2) when referring to "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 50 carbon atoms, A ring-forming aryl group with 6 to 50 carbon atoms, and Heterocyclic groups with 5 to 50 ring-forming atoms A group selected from the group consisting of,
[0146] In one embodiment, the substituent in formula (2) when referring to "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 18 carbon atoms, A ring-forming aryl group with 6 to 18 carbon atoms, and Heterocyclic groups with 5 to 18 ring-forming atoms It is a group selected from the group consisting of the following.
[0147] The compound represented by formula (2) can be synthesized by using known reactions and starting materials that are appropriate for the target product.
[0148] The following are specific examples of compounds represented by formula (2), but these are merely examples, and compounds represented by formula (2) are not limited to the examples below.
[0149] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0150] [Organic EL element] An organic EL element according to one aspect of the present invention (including a first organic EL element and a second organic EL element, which will be described later) will be explained.
[0151] A schematic configuration of an organic EL element according to one aspect of the present invention will be described with reference to Figure 1. An organic EL element 1 according to one aspect of the present invention comprises a substrate 2, an anode 3, an organic light-emitting layer 5, a cathode 10, an organic layer 4 between the anode 3 and the light-emitting layer 5, and an organic layer 6 between the light-emitting layer 5 and the cathode 10. Organic layer 4 and organic layer 6 may each be a single layer or consist of multiple layers.
[0152] (First organic EL element) A first organic EL element according to one aspect of the present invention comprises 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 composition according to one aspect of the present invention.
[0153] A first organic EL element according to one aspect of the present invention, as described above, has 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 a composition according to one aspect of the present invention, other than that, conventionally known materials and element configurations can be applied as long as they do not impair the effects of the present invention.
[0154] (Second organic EL element) A second organic EL element according to one aspect of the present invention comprises 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 represented by formula (1) and a compound represented by formula (2).
[0155] The details of the compound represented by formula (1) and the compound represented by formula (2) are as described in the composition of one embodiment of the present invention described above.
[0156] Here, "at least one of the organic layers contains the compound represented by formula (1) and the compound represented by formula (2)" means that if the organic EL element has one organic layer, that one organic layer contains the compound represented by formula (1) and the compound represented by formula (2), and if the organic EL element has two or more organic layers, one or more of the two or more organic layers contain the compound represented by formula (1) and the compound represented by formula (2).
[0157] A second organic EL element according to one aspect of the present invention, as described above, has a cathode, an anode, and one or more organic layers disposed between the cathode and the anode, and conventionally known materials and element configurations can be applied as long as they do not impair the effects of the present invention, except that at least one of the organic layers contains a compound represented by formula (1) and a compound represented by formula (2).
[0158] The total content of the compound represented by formula (1) (first component) and the compound represented by formula (2) (second component) in at least one of the organic layers is preferably 80% by mass or more and 99% by mass or less of the total content of the layer. The content ratio (mass ratio) of the first component to the second component in the layer is usually 1:99 to 99:1, preferably 10:90 to 90:10, and more preferably 30:70 to 70:30.
[0159] In one embodiment, an organic EL element according to one aspect of the present invention includes an anode, a light-emitting layer, and a cathode in that order, and at least one organic layer in the light-emitting layer includes a composition according to one aspect of the present invention, or a compound represented by formula (1) (first component) and a compound represented by formula (2) (second component).
[0160] In one embodiment, an organic EL element according to one aspect of the present invention includes an anode, a light-emitting layer, and a cathode in that order, and at least one organic layer in the light-emitting layer contains a composition according to one aspect of the present invention. In one embodiment, an organic EL element according to one aspect of the present invention includes an anode, a light-emitting layer, and a cathode in that order, wherein at least one organic layer in the light-emitting layer includes a compound represented by formula (1) (first component) and a compound represented by formula (2) (second component).
[0161] In one embodiment, an organic EL element according to one aspect of the present invention has an emissive layer having one or more layers, and at least one of the one or more layers contains the composition or a compound represented by formula (1) and a compound represented by formula (2).
[0162] In one embodiment, an organic EL element according to one aspect of the present invention further comprises at least one of the one or more layers containing the composition or the compound represented by formula (1) and the compound represented by formula (2), which further includes a phosphorescent metal complex or a fluorescent material.
[0163] In one embodiment, an organic EL element according to one aspect of the present invention further comprises at least one of the one or more layers containing the composition or the compound represented by formula (1) and the compound represented by formula (2), including a sensitizing material and a fluorescent material.
[0164] In one embodiment, the sensitizing material is one or more compounds selected from the group consisting of phosphorescent metal complexes and delayed-fluorescence compounds.
[0165] (Phosphorescent metal complex) The phosphorescent metal complex is not particularly limited as long as it is a metal complex capable of emitting phosphorescence. In one embodiment, the phosphorescent metal complex contains heavy metal atoms.
[0166] In one embodiment, the phosphorescent metal complex contains one or more metal atoms selected from the group consisting of platinum (Pt), iridium (Ir), osmium (Os), ruthenium (Ru), rhodium (Rh), palladium (Pd), copper (Cu), silver (Ag), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm).
[0167] In one embodiment, the phosphorescent metal complex is a compound represented by the following formula (P1). M(L1) n1 (L2) n2 ...(P1) [In equation (P1), M is a transition metal selected from the group consisting of first transition metals, second transition metals, and third transition metals. L1 is at least one ligand selected from the group consisting of ligands represented by formula (P11), formula (P12), and formula (P13), which will be described later. n1 is 1, 2, or 3. L2 is at least one ligand selected from the group consisting of monosessate ligands, disessate ligands, and trisessate ligands. n2 is 0, 1, 2, 3, or 4.
[0168] Examples of first transition metals include scandium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, and copper. Examples of second transition metals include yttrium, zirconium, niobium, molybdenum, technetium, ruthenium, rhodium, palladium, and silver. Examples of third transition metals include lanthanum, cerium, praseodymium, neodymium, promethium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, lutetium, hafnium, tantalum, tungsten, rhenium, osmium, iridium, platinum, and gold.
[0169] The ligands represented by formula (P11), formula (P12), and formula (P13) will be explained below. [ka]
[0170] In equations (P11) to (P13), The CY1, CY2, CY3, and CY4 rings are each independently selected from the group consisting of carbon rings with 5 to 30 ring-forming carbon atoms and heterorings with 3 to 30 ring-forming atoms. Y1 to Y4 are independent of each other. single bond, double bond, Substituted or unsubstituted ring-forming arylene groups with 6 to 50 carbon atoms, Divalent heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms, -O-, -S-, -C(=O)-, -S(=O)-, -C(R5)(R6)-, -C(R5)=C(R6)- -C(R5)=, -Si(R5)(R6)-, -B(R)-, -N(R5)-, and Selected from the group consisting of -P(R5)-. a1, a2, and a3 are each independently 1, 2, or 3. a4 is 0, 1, 2, or 3, and if a4 is 0, the CY1 ring and CY4 ring are not connected to each other. T1, T2, T3, and T4 are each independent of each other. chemical bond, -O-, -S-, -B(R7)-, -N(R7)-, -P(R7)-, -C(R7)(R8)-, -Si(R7)(R8)-, -Ge(R7)(R8)-, -C(=O)- and It is selected from the group consisting of -C(=S)-. *1, *2, *3, and *4 are the bonding sites with M. R1 to R8 are each independent of each other. hydrogen atom, halogen atom, Cyano group, Nitro group, Amidino group, Hydrazino group, Hydrazono group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl groups with 3 to 50 ring-forming atoms, Substituted or unsubstituted ring-forming cycloalkenyl groups with 3 to 50 carbon atoms, A heterocycloalkenyl group with 3 to 50 substituted or unsubstituted ring-forming atoms, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, Substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, Substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic groups, -Si(R251 )(R 252 )(R 253 A base represented by ) -O-(R 254 A base represented by ) -S-(R 255 A base represented by ) -N(R 256 )(R 257 A base represented by ) -C(=O)R 258 A base represented by -C(=O)(OR 259 A base represented by ) -S(=O)2(OR 260 A base represented by ) -OP(=O)(OR 261 )(OR 262 A base represented by ) -C(R 263 )(R 264 )(R 265 A base represented by ) -B(R 266 )(R 267 A base represented by ) -P(R 268 )(R 269 A base represented by ) -S(=O)(R 270 A base represented by ) -S(=O)2(R 271 A base represented by ) -P(=O)(R 272 )(R 273 A group represented by ) and -P(=S)(R 274 )(R 275 Selected from the bases represented by ). One or more pairs of adjacent R1-R8 are: They combine with each other to form a substituted or unsubstituted monoring, They bond to each other to form substituted or unsubstituted fused rings, or They do not combine with each other. One or more pairs of adjacent items from R1-R8 and Y1-Y4 are: They combine with each other to form a substituted or unsubstituted monoring, They bond to each other to form substituted or unsubstituted fused rings, or They do not combine with each other. b1, b2, b3, and b4 are independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. R 251 ~R 275 Each of them operates independently. hydrogen atom, halogen atom, -O-(R 276 A base represented by ) -N(R 277 )(R 278 A base represented by ) Cyano group, Nitro group, Amidino group, Hydrazino group, Hydrazono group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl groups with 3 to 50 ring-forming atoms, Substituted or unsubstituted ring-forming cycloalkenyl groups with 3 to 50 carbon atoms, A heterocycloalkenyl group with 3 to 50 substituted or unsubstituted ring-forming atoms, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A ring-forming aryl group having 6 to 50 carbon atoms, substituted with or unsubstituted alkyl groups having 1 to 50 carbon atoms. A ring-forming aryl group having 6 to 50 carbon atoms, substituted with a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms. A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, Substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, Substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic groups, The group is selected from the group consisting of biphenylyl groups and terphenylyl groups. R 276 ~R 278 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms.
[0171] In one embodiment, the CY1 to CY4 rings in the compound represented by formula (P1) are, independently, benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, chrysene, cyclopentadiene, 1,2,3,4-tetrahydronaphthalene, carbene, thiophene, furan, selenofen, indole, benzoboro, benzophosphole, indene, benzosilol, benzogermol, benzothiophene, benzoselenophen, benzofuran, carbazole, dibenzoboro, dibenzophosphole, fluorene, dibenzosilol, dibenzogermol, dibenzothiophene, dibenzoselenophen, dibenzofuran, dibenzothiophene-5-oxide, 9H-fluoren-9-one, dibenzothiophene-5,5-dioxide, azaindole, azabenzobolol, azabenzophosphole, azaindene, azabenzosilol, azabenzogermol, azabenzothiophene, aza Benzoselenophen, azabenzofuran, azacarbazole, azadibenzobolol, azadibenzophosphorus, azafluorene, azadibenzosilol, azadibenzogermol, azadibenzothiophene, azadibenzoselenophene, azadibenzofuran, azadibenzothiophene-5-oxide, aza-9H-fluoren-9-one, azadibenzothiophene-5,5-dioxide, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isopropyl alcohol Selected from the group consisting of noline, quinoxaline, quinazoline, phenanthroline, pyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, benzopyrazole, benzimidazole, benzoxazole, benzothiazole, benzoxadiazole, benzothiadiazole, benzothiadiazole, 5,6,7,8-tetrahydroisoquinoline, and 5,6,7,8-tetrahydroquinoline.
[0172] In one embodiment, At least one of the CY1 ring and CY2 ring in formula (P11), At least one of the CY1-CY3 rings in formula (P12), and At least one of the CY1-CY4 rings in formula (P13) is a carbene.
[0173] In one embodiment, Y1 to Y4 in formulas (P11) to (P13) are each independently, It is at least one selected from the group consisting of single bonds, double bonds, -O-, -S-, -C(R5)(R6)-, and -N(R5)-.
[0174] In one embodiment, At least one of R1 and R2 in equation (P11), At least one of R1 to R3 in equation (P12), and In equation (P13), at least one of R1 to R4 is an electron-donating group.
[0175] Examples of electron-donating groups include iso-propyl groups, tert-butyl groups, and substituents selected from the group consisting of the following formulas (10-1) to (10-61).
[0176] [ka] [ka]
[0177] In equations (10-1) to (10-61), * indicates the bond position with an adjacent atom.
[0178] In this specification, deuterium atoms are denoted as D in chemical formulas, and light hydrogen atoms are denoted as H or omitted. In this specification, methyl groups may be denoted as Me, phenyl groups as Ph, isopropyl groups as i-Pr, and t-butyl groups as t-Bu in chemical formulas.
[0179] In one embodiment, at least one of R1 and R2 in formula (P11) is not a hydrogen atom (i.e., a substituent), and / or Y1 is -N(R5)-, and R5 is a substituted ring-forming aryl group having 6 to 50 carbon atoms.
[0180] In one embodiment, at least one of R1 to R3 in formula (P12) is not hydrogen (i.e., it is a substituent), and / or at least one of Y1 and Y2 is -N(R5)-, where R5 is a substituted ring-forming aryl group having 6 to 50 carbon atoms.
[0181] In one embodiment, at least one of R1 to R4 in formula (P13) is not hydrogen (i.e., it is a substituent), and / or at least one of Y1 to Y4 is -N(R5)-, where R5 is a substituted ring-forming aryl group having 6 to 50 carbon atoms.
[0182] (Specific examples of phosphorescent metal complexes) Specific examples of phosphorescent metal complexes include the following compounds. However, the present invention is not limited to these specific examples of compounds.
[0183] [ka] [ka] [ka]
[0184] (Fluorescent material) The fluorescent material is not particularly limited as long as it is a compound capable of emitting fluorescence. In one embodiment, the fluorescent material is a compound that does not exhibit thermally activated delayed fluorescence. In one embodiment, the fluorescent material is a compound that does not exhibit delayed fluorescence. In one embodiment, the fluorescent material is not a phosphorescent metal complex. In one embodiment, the fluorescent material is not a metal complex.
[0185] Examples of fluorescent materials include bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl-substituted pyrene derivatives, bisarylaminochrysene derivatives, aryl-substituted chrysene derivatives, bisarylaminofluorantene derivatives, aryl-substituted fluorantene derivatives, indenoperylene derivatives, acenaphthofluorantene derivatives, compounds containing boron atoms, pyrometenoboron complex compounds, compounds having a pyrometene skeleton, metal complexes of compounds having a pyrometene skeleton, diketopyrrolopyrrole derivatives, perylene derivatives, and naphthacene derivatives.
[0186] In one embodiment, the fluorescent material is one or more compounds selected from the group consisting of compounds represented by the following formula (41).
[0187] [ka]
[0188] In equation (41), Rings a, b, and c are independent of each other. A substituted or unsubstituted ring-forming aromatic hydrocarbon ring with 6 to 50 carbon atoms, or It is a heterocycle with 5 to 50 ring-forming atoms, either substituted or unsubstituted. L 401 and L 402 These are O, S, Se, and NR, respectively, independently. 40 , C(R 41 )(R 42 ), or Si(R 43 )(R 44 ) L 403 The equation is B, P, or P=O. R 40~R 44 Each of them operates independently. It combines with the a, b, or c ring to form a substituted or unsubstituted monoring, It bonds with the aforementioned ring a, ring b, or ring c to form a substituted or unsubstituted fused ring, or It does not bond with the aforementioned rings a, b, and c. R 41 and R 42 teeth, They combine with each other to form a substituted or unsubstituted monoring, They bond to each other to form substituted or unsubstituted fused rings, or They do not combine with each other. R 43 and R 44 teeth, They combine with each other to form a substituted or unsubstituted monoring, They bond to each other to form substituted or unsubstituted fused rings, or They do not combine with each other. R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 40 ~R 44 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -C(R 45 )=N represents an iminyl group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 45 teeth, Substituted or unsubstituted ring-forming aryl groups with 6 to 60 carbon atoms, A heterocyclic group with 5 to 60 substituted or unsubstituted ring-forming atoms, A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, These are substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms forming a ring. R 40 ~R 45 If there are two or more of them, then there are two or more R 40 ~R 45 Each of these may be the same or different.
[0189] In one embodiment, the compound represented by formula (41) is the compound represented by the following formula (410).
[0190] [ka]
[0191] In equation (410), Rings a, b, and c are independent of each other. A substituted or unsubstituted ring-forming aromatic hydrocarbon ring with 6 to 50 carbon atoms, or It is a heterocycle with 5 to 50 ring-forming atoms, either substituted or unsubstituted. R 401 and R 402 Each of them operates independently. It combines with the a, b, or c ring to form a substituted or unsubstituted monoring, It bonds with the aforementioned ring a, ring b, or ring c to form a substituted or unsubstituted fused ring, or It does not bond with the aforementioned rings a, b, and c. R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 401 and R 402 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -C(R 45 )=N represents an iminyl group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms.
[0192] In one embodiment, the compound represented by formula (41) is a compound selected from the group consisting of compounds represented by the following formulas (41-1) to (41-6).
[0193] [ka] [ka] [ka]
[0194] In equation (41-1), Xa is O, S, Se, C(R 403 )(R 404 ), or NR 405 That is the case. R 401 and R 421 The group, R 421 ~R 423 A set of two or more adjacent elements, R 423 and R 402 The group, R 402 and R 424 The group, R 424 ~R 427 A set of two or more adjacent elements, R 427 and R 412 The set of, and R 412 and R 411 From the group consisting of these pairs, one or more pairs are selected: They combine with each other to form a substituted or unsubstituted monoring, They bond to each other to form substituted or unsubstituted fused rings, or They do not combine with each other. R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 401 and R 402 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -C(R 45 )=N represents an iminyl group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 403 ~R 405 , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring 411 , R 412 , and R 421 ~R 427 Each of these is independently either a hydrogen atom or the substituent RX. The substituent RX is, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901~R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 ~R 907 If there are two or more of them, then there are two or more R 901 ~R 907 Each of these may be the same or different. If multiple substituents RX exist, they may be the same or different.
[0195] In equation (41-2), Xa is O, S, Se, C(R 403 )(R 404 ), or NR 405 That is the case. R 401 and R 421 The group, R 421 ~R 423 A set of two or more adjacent elements, R 423 and R 402 The group, R 402 and R 424 The group, R 424 ~R 427 A set of two or more adjacent elements, R 413 and R 414 The combination with, and R 414 and R 401 From the group consisting of pairs, one or more pairs are selected: They combine with each other to form a substituted or unsubstituted monoring, They bond to each other to form substituted or unsubstituted fused rings, or They do not combine with each other. R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 401 and R 402 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -C(R 45 )=N represents an iminyl group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 403 ~R 405 , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring 413 , R 414 , and R 421 ~R 427 Each of these is independently either a hydrogen atom or the substituent RX. The substituent RX is defined as described in formula (41-1) above. R 403 ~R 405 If there are two or more of them, then there are two or more R 403 ~R 405 Each of these may be the same or different.
[0196] In equation (41-3), Xa and Xb are independently O, S, Se, C(R) 403 )(R 404 ), or NR 405 That is the case. R 401 and R 421 The group, R 421 ~R 423 A set of two or more adjacent elements, R 423 and R 402 The group, R 415 and R 416 The group, R 416 and R 412 The set of, and R 412 and R 411 From the group consisting of these pairs, one or more pairs are selected: They combine with each other to form a substituted or unsubstituted monoring, They bond to each other to form substituted or unsubstituted fused rings, or They do not combine with each other. R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 401 and R 402 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -C(R 45 )=N represents an iminyl group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 403 ~R 405 , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring 411 , R 412 , R 415 , R 416 , and R 421 ~R 423 Each of these is independently either a hydrogen atom or the substituent RX. The substituent RX is defined as described in formula (41-1) above. R 403 ~R 405 If there are two or more of them, then there are two or more R 403 ~R 405 Each of these may be the same or different.
[0197] In equation (41-4), Xa and Xb are independently O, S, Se, C(R) 403 )(R 404 ), or NR 405 That is the case. R 401and R 421 The group, R 421 ~R 423 A set of two or more adjacent elements, R 423 and R 402 The group, R 402 and R 418 The group, R 418 and R 417 The set of, and R 412 and R 411 From the group consisting of these pairs, one or more pairs are selected: They combine with each other to form a substituted or unsubstituted monoring, They bond to each other to form substituted or unsubstituted fused rings, or They do not combine with each other. R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 401 and R 402 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -C(R 45 )=N represents an iminyl group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 403 ~R 405 , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring 411 , R 412 , R 417 , R 418 , and R 421 ~R 423 Each of these is independently either a hydrogen atom or the substituent RX. The substituent RX is defined as described in formula (41-1) above. R 403 ~R 405If there are two or more of them, then there are two or more R 403 ~R 405 Each of these may be the same or different.
[0198] In equation (41-5), Xa and Xb are independently O, S, Se, C(R) 403 )(R 404 ), or NR 405 That is the case. R 401 and R 421 The group, R 421 ~R 423 A set of two or more adjacent elements, R 423 and R 402 The group, R 402 and R 418 The group, R 418 and R 417 The group, R 413 and R 414 The set of, and R 414 and R 401 From the group consisting of these pairs, one or more pairs are selected: They combine with each other to form a substituted or unsubstituted monoring, They bond to each other to form substituted or unsubstituted fused rings, or They do not combine with each other. R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 401 and R 402 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -C(R 45 )=N represents an iminyl group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 403 ~R405 , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring 413 , R 414 , R 417 , R 418 , and R 421 ~R 423 Each of these is independently either a hydrogen atom or the substituent RX. The substituent RX is defined as described in formula (41-1) above. R 403 ~R 405 If there are two or more of them, then there are two or more R 403 ~R 405 Each of these may be the same or different.
[0199] In equation (41-6), R 401 and R 421 The group, R 421 ~R 423 A set of two or more adjacent elements, R 423 and R 402 The group, R 402 and R 424 The group, R 424 ~R 427 A set of two or more adjacent elements, R 427 and R 428 The group, R 428 ~R 431 A set consisting of two or more adjacent items, and R 431 and R 401 From the group consisting of these pairs, one or more pairs are selected: They combine with each other to form a substituted or unsubstituted monoring, They bond to each other to form substituted or unsubstituted fused rings, or They do not combine with each other. R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 401 and R 402 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -C(R 45 )=N represents an iminyl group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 421 ~R 431 Each of these is independently either a hydrogen atom or the substituent RX. The substituent RX is defined as described in formula (41-1) above.
[0200] In one embodiment, in a compound represented by formulas (41-1) to (41-5), R 412 and R 411 The group, R 413 and R 414 The group, R 415 and R 416 The set of, and R 417 and R 418 One or more pairs selected from the group consisting of these pairs can combine with each other to form a substituted or unsubstituted monoring, or combine with each other to form a substituted or unsubstituted fused ring.
[0201] In one embodiment, the compound represented by formula (41) is the compound represented by the following formula (41-7).
[0202] [ka]
[0203] In equation (41-7), Xa is O, S, Se, C(R 403 )(R 404 ), or NR 405 That is the case. R 401 and R 421 The group, R 421~R 423 A set of two or more adjacent elements, R 423 and R 402 The group, R 402 and R 424 The pair, R 424 ~R 427 A set consisting of two or more adjacent items, and R 437 ~R 440 From among the groups consisting of two or more adjacent pairs, one or more pairs are selected: They combine with each other to form a substituted or unsubstituted monoring, They bond to each other to form substituted or unsubstituted fused rings, or They do not combine with each other. R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 401 and R 402 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 403 ~R 405 , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring 421 ~R 427 and R 437 ~R 440 Each of these is independently either a hydrogen atom or the substituent RX. The substituent RX is defined as described in formula (41-1) above.
[0204] (Method for producing the compound represented by formula (41)) The compound represented by formula (41) can be produced by known methods. Furthermore, the compound represented by formula (41) can also be produced by following known methods and using known alternative reactions and starting materials tailored to the target compound.
[0205] (Specific examples of compounds represented by formula (41)) Examples of compounds represented by formula (41) include the following compounds. In the examples below, D represents a deuterium atom, Me represents a methyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.
[0206] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0207] (Maximum peak wavelength) In one embodiment, the maximum peak wavelength of the phosphorescent metal complex and the maximum peak wavelength of the fluorescent material are preferably 480 nm or less and 475 nm or less, respectively.
[0208] In one embodiment, the maximum peak wavelength of the phosphorescent metal complex and the maximum peak wavelength of the fluorescent material are preferably 430 nm or higher and 440 nm or higher, respectively.
[0209] In this specification, the maximum peak wavelength of fluorescence emission may be referred to as the maximum peak wavelength of fluorescence emission, and the maximum peak wavelength of phosphorescence emission may be referred to as the maximum peak wavelength of phosphorescence emission.
[0210] In one embodiment of an organic EL element, the phosphorescent metal complex and the fluorescent material exhibit blue light emission. In this specification, blue light emission refers to light emission in which the maximum peak wavelength of the emission spectrum (fluorescence spectrum or phosphorescent spectrum) is in the range of 430 nm or more and 480 nm or less.
[0211] (Emission spectrum half-width) In one embodiment, the emission spectrum full width at half maximum (FWHM) of the fluorescent material is 40 nm or less, and preferably 30 nm or less.
[0212] In one embodiment, the emission spectrum full width at half maximum (FWHM) of the fluorescent material is 5 nm or more, and preferably 10 nm or more.
[0213] FWHM is an abbreviation for full width at half maximum.
[0214] In this specification, the maximum fluorescence emission peak wavelength is defined as the wavelength at which the compound being measured is 10 -6 moles / liter or more, 10 -5For a toluene solution dissolved at a concentration of mol / liter or less, the fluorescence spectrum measured is defined as the wavelength at which the emission intensity is maximized. The emission spectrum half-width (FWHM) is the full width at half-width at the peak of the fluorescence spectrum. A fluorescence spectrum analyzer can be used to measure the fluorescence spectrum. For example, a fluorescence spectrum analyzer manufactured by JASCO Corporation (model name: FP-8300) can be used. However, the fluorescence spectrum analyzer is not limited to the example given here.
[0215] The maximum phosphorescence peak wavelength can be measured by the following method. The compound to be measured is placed in EPA (diethyl ether:isopentane:ethanol = 5:5:2 (volume ratio)) and 10 -5 mol / L or more 10 -4 Dissolve the EPA solution to a concentration of mol / L or less, and place this EPA solution in a quartz cell to prepare the measurement sample. Measure the phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this sample at a low temperature (77 K). The maximum value at the shortest wavelength among the maximum values of this phosphorescence spectrum is defined as the maximum phosphorescence peak wavelength. A spectrofluorometer F-7000 (manufactured by Hitachi High-Tech Science Corporation) can be used to measure phosphorescence. However, the measurement apparatus is not limited to this; a combination of a cooling device, a low-temperature container, an excitation light source, and a light-receiving device may also be used.
[0216] (Stokes shift) In one embodiment, the Stokes shift of the fluorescent material is 25 nm or less, and preferably 20 nm or less. If the Stokes shift of a fluorescent material is 20 nm or less, the excitation energy can be easily reduced.
[0217] In one embodiment, the Stokes shift of the fluorescent material is 5 nm or more, and preferably 10 nm or more. If the Stokes shift of a fluorescent material is 10 nm or greater, self-absorption is suppressed, making it easier to reduce efficiency losses.
[0218] The Stokes shift can be measured using the following method. The compound to be measured is 2.0 × 10 -5 Prepare the sample for measurement by dissolving the compound in toluene at a concentration of mol / L. Irradiate the sample, placed in a quartz cell, with continuous ultraviolet-visible light at room temperature (300K) and measure the absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength). A spectrophotometer can be used for absorption spectrum measurement; for example, Hitachi High-Tech Science's U-3900 / 3900H spectrophotometer can be used. Also, the compound to be measured should be 4.9 × 10⁻⁶ -6 Prepare a sample for measurement by dissolving the substance in toluene at a concentration of mol / L. Irradiate the sample, placed in a quartz cell, with excitation light at room temperature (300K) and measure the fluorescence spectrum (vertical axis: fluorescence intensity, horizontal axis: wavelength). A spectrophotometer can be used for fluorescence spectrum measurement; for example, the Hitachi High-Tech Science F-7000 spectrofluorometer can be used. From these absorption and fluorescence spectra, calculate the difference between the absorption maximum wavelength and the fluorescence maximum wavelength to determine the Stokes shift (SS). The unit of Stokes shift SS is nm.
[0219] In one embodiment, when at least one of one or more light-emitting layers contains a compound represented by formula (1), a compound represented by formula (2), and a fluorescent material, when the organic EL element is made to emit light, the fluorescent compound mainly emits light in the light-emitting layer.
[0220] The maximum peak wavelength of light emitted from an organic EL element is measured as follows. Current density is 10 mA / cm² 2 The spectral radiance spectrum of an organic EL element is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta) when a voltage is applied to the element in such a manner. In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum with the maximum emission intensity is measured and defined as the maximum peak wavelength (unit: nm).
[0221] (Sensitizing material) The sensitizing material is not particularly limited as long as it is a compound that can transfer the energy it absorbs to other substances. In one embodiment, the sensitizing material is one or more compounds selected from the group consisting of phosphorescent metal complexes and delayed-fluorescence compounds.
[0222] The phosphorescent metal complexes are as described above.
[0223] (Delayed fluorescence compounds) The delayed fluorescence compound is not particularly limited as long as it is a compound capable of emitting delayed fluorescence. In one embodiment, the delayed-fluorescence compound is not a phosphorescent metal complex. In one embodiment, the delayed-fluorescence compound is not a metal complex.
[0224] In one embodiment, the delayed-fluorescence compound is a compound represented by the following formula (H1).
[0225] [ka]
[0226] In equation (H1), A H This is a group having at least one substructure selected from the group consisting of formulas (a-1), (a-2), (a-3), (a-4), (a-5), (a-6), (a-7), and (a-8) described later. D H This is a group represented by formulas (221), (222), or (223) described later. L H teeth, single bond, A substituted or unsubstituted aryl ring with 6 to 50 carbon atoms, or It is a heterocycle with 5 to 50 ring-forming atoms, either substituted or unsubstituted. m is 1, 2, 3, 4, or 5. A H If there are multiple A HThey may be the same or they may be different. n is 1, 2, 3, 4, or 5. D H If there are multiple D H They may be the same or they may be different.
[0227] [ka]
[0228] In equations (a-1) to (a-8), * independently indicates the bonding position with other atoms in the molecule of the delayed-fluorescence compound.
[0229] [ka] [ka] [ka]
[0230] R in equation (221) 21 ~R 28 Of the sets of two or more adjacent items, one or more sets are: They combine with each other to form a substituted or unsubstituted monoring, They bond to each other to form substituted or unsubstituted fused rings, or They do not combine with each other. R in equation (222) 221 ~R 228 Of the sets of two or more adjacent items, one or more sets are: They combine with each other to form a substituted or unsubstituted monoring, They bond to each other to form substituted or unsubstituted fused rings, or They do not combine with each other. R in equation (223) 231 ~R 238 Of the sets of two or more adjacent items, one or more sets are: They combine with each other to form a substituted or unsubstituted monoring, They bond to each other to form substituted or unsubstituted fused rings, or They do not combine with each other. R that does not form a substituted or unsubstituted monoring and does not form a substituted or unsubstituted fused ring. 21 ~R 28 , R 221 ~R 228 , and R 231 ~R 238 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 908 A base represented by -COOR 909 A base represented by halogen atom, Cyano group, Nitro group, -P(=O)(R 931 )(R 932 A base represented by ) -Ge(R 933 )(R 934 )(R 935 A base represented by ) -B(R 936 )(R937 A base represented by ) A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. In equations (222) and (223), Rings A, B, and C are each independently selected from the group consisting of ring structures represented by formulas (224) and (225) described later. Rings A, B, and C condense with adjacent rings at any given position. p, px, and py are each independently 1, 2, 3, or 4. When p is 2, 3, or 4, the multiple rings A may be the same or different. If px is 2, 3, or 4, the multiple rings B may be the same or different. If py is 2, 3, or 4, the multiple rings C may be the same or different. In equations (221) to (223), * represents L H This indicates the bonding position.
[0231] [ka]
[0232] In equation (224), r is 0, 2, or 4. If r is 2 or 4, multiple R 29 The group consisting of is They combine with each other to form a substituted or unsubstituted monoring, They bond to each other to form substituted or unsubstituted fused rings, or They do not combine with each other. In equation (225), X A is a sulfur atom, an oxygen atom, or C(R 291 )(R 292 ) R 291 and R 292 The group consisting of is They combine with each other to form a substituted or unsubstituted monoring, They bond to each other to form substituted or unsubstituted fused rings, or They do not combine with each other. R that does not form a substituted or unsubstituted monoring and does not form a substituted or unsubstituted fused ring. 29 , R 291 , and R 292 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 908 A base represented by -COOR 909 A base represented by halogen atom, Cyano group, Nitro group, -P(=O)(R 931 )(R 932 A base represented by ) -Ge(R 933 )(R 934 )(R 935 A base represented by ) -B(R 936 )(R 937 A base represented by ) A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 29 , R 291 , R 292 , and X A If there are two or more of them, then there are two or more R 29 , R 291 , R 292 , and X A Each of these may be the same or different. R 901 ~R 909 and R 931 ~R 937 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 ~R 909 and R 931 ~R 937 If there are two or more of them, then there are two or more R 901 ~R 909 and R 931 ~R 937 Each of these may be the same or different.
[0233] In one embodiment, the delayed-fluorescence compound is a compound represented by the following formula (H10).
[0234] [ka]
[0235] In equation (H10), C N It is a cyano group. L HThese are substituted or unsubstituted aromatic hydrocarbon rings with 6 to 30 carbon atoms. D 11 and D 12 These are, independently, groups represented by formulas (221), (222), or (223). m is 1, 2, 3, 4, or 5. nx is 0, 1, 2, 3, 4, or 5. ny is 0, 1, 2, 3, 4, or 5. nx + ny is 1, 2, 3, 4, or 5. D 11 and D 12 They may be the same or they may be different. If nx is 2, 3, 4, or 5, multiple D 11 They may be the same or they may be different. If ny is 2, 3, 4, or 5, multiple D 12 They may be the same or they may be different.
[0236] In one embodiment, the delayed-fluorescence compound is a compound represented by the following formula (H100).
[0237] [ka]
[0238] In equation (H100), L H , D 11 , D 12 m, nx, and ny are defined as in equation (H10) above. R is independent of each other. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 908 A base represented by -COOR 909 A base represented by Cyano group, Nitro group, -P(=O)(R 931 )(R 932 A base represented by ) -Ge(R 933 )(R 934 )(R 935 A base represented by ) -B(R 936 )(R 937 A base represented by ) A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. However, at least one R is a substituent, and at least one R as a substituent is L of the compound represented by formula (H100). H The atoms are bonded to each other by a carbon-carbon bond, and k is an integer greater than or equal to 1. Multiple instances of R may be the same or different.
[0239] In one embodiment, the delayed-fluorescence compound is a compound represented by the following formula (H101).
[0240] [ka]
[0241] In equation (H101), D11 and D 12 This is as defined in formula (H10) above. R is defined as in the above formula (H100). m is 1, 2, 3, or 4. nx is 0, 1, 2, 3, or 4. ny is 0, 1, 2, 3, or 4. k is 1, 2, 3, or 4. nx + ny is 1, 2, 3, or 4. m + nx + ny + k = 6.
[0242] In one embodiment, the delayed-fluorescence compound is a compound represented by the following formulas (H110), (H120), or (H130).
[0243] [ka]
[0244] In formulas (H110), (H120), and (H130), D 11 and D 12 This is as defined in formula (H10) above. R is defined as in the above formula (H100). nx is 0, 1, 2, or 3. ny is 0, 1, 2, or 3. k is 1, 2, or 3. nx + ny is 1, 2, or 3. nx + ny + k = 4.
[0245] In one embodiment, the group represented by formula (222) in the delayed-fluorescence compound is selected from the group consisting of the following groups: (22A), (22B), (22C), (22D), (22E), and (22F).
[0246] [ka]
[0247] [ka]
[0248] [ka]
[0249] [ka]
[0250] [ka]
[0251] [ka]
[0252] In equations (22A), (22B), (22C), (22D), (22E), and (22F), R 221 ~R 228 This is as defined in equation (222) above. R 229 and R 230 R in equation (224) is 29 It is synonymous with [the above]. X A This is as defined in equation (225) above. In equations (22A), (22B), (22C), (22D), (22E), and (22F), * indicates the bond position.
[0253] In an organic EL element according to one embodiment, when the delayed fluorescence compound is a compound represented by formula (H101), the * in formulas (22A), (22B), (22C), (22D), (22E), and (22F) is bonded to the benzene ring itself, as explicitly shown in formula (H101).
[0254] In one embodiment of a delayed-fluorescence compound, X A This is either a sulfur atom or an oxygen atom.
[0255] In one embodiment of a delayed-fluorescence compound, X A However, C(R 291 )(R 292 If R is the case, 291 and R 292 Preferably, each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group, and is either a substituted or unsubstituted C1-C50 alkyl group or a substituted or unsubstituted ring-forming C6-C50 aryl group.
[0256] In one embodiment of a delayed-fluorescence compound, R 21 ~R 28 No two or more adjacent pairs of these pairs can be combined with each other. In one embodiment of a delayed-fluorescence compound, R 221 ~R 228 No two or more adjacent pairs of these pairs can be combined with each other. In one embodiment of a delayed-fluorescence compound, R 231 ~R 238 No two or more adjacent pairs of these pairs can be combined with each other.
[0257] In one embodiment of the delayed-fluorescence compound, R is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heterocyclic group.
[0258] In one embodiment of the delayed-fluorescence compound, R is independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted ring-forming C6-C18 aryl group, or a substituted or unsubstituted ring-forming C5-C18 heterocyclic group.
[0259] R in the delayed fluorescence compound of one embodiment 21 ~R 28 R 221 ~R 228 R 231 ~R 238 and R 29 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms.
[0260] R in the delayed fluorescence compound of one embodiment 21 ~R 28 R 221 ~R 228 R 231 ~R 238 and R 29 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring-forming atoms.
[0261] R in the delayed fluorescence compound of one embodiment is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms. R in the delayed fluorescence compound of one embodiment 21 ~R 28 R 221 ~R 228 R 231 ~R 238 and R 29 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms.
[0262] In the delayed fluorescence compound of one embodiment, each R is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring-forming atoms. In the delayed fluorescence compound of one embodiment, R 21 ~R 28 , R 221 ~R 228 , R 231 ~R 238 , and R 29 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring-forming atoms.
[0263] In the compound according to one embodiment, the substituent in the case of "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted alkenyl group having 2 to 25 carbon atoms, an unsubstituted alkynyl group having 2 to 25 carbon atoms, an unsubstituted cycloalkyl group having 3 to 25 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) group represented by -S-(R 905 ) group represented by -N(R 906 )(R 907 ) group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 908 ) group represented by -COOR 909 ) group represented by -P(=O)(R 931 )(R 932 ) group represented by -Ge(R 933 )(R 934 )(R 935A base represented by ) -B(R 936 )(R 937 A base represented by ) -S(=O)2R 938 A base represented by halogen atom, Cyano group, Nitro group, Unsubstituted ring-forming aryl groups with 6 to 25 carbon atoms, or It is an unsubstituted heterocyclic group with 5 to 25 ring-forming atoms. Here, R 901 ~R 909 and R 931 ~R 938 Each of them operates independently. hydrogen atom, Unsubstituted alkyl groups with 1 to 25 carbon atoms, Unsubstituted ring-forming aryl groups with 6 to 25 carbon atoms, or It is an unsubstituted heterocyclic group with 5 to 25 ring-forming atoms.
[0264] In a compound according to one embodiment, the substituent in the case of "substituted or unsubstituted" is a halogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring-forming atoms.
[0265] In a compound according to one embodiment, the substituent referred to as "substituted or unsubstituted" is an unsubstituted C1-C10 alkyl group, an unsubstituted ring-forming C6-C12 aryl group, or an unsubstituted ring-forming C5-C12 heterocyclic group.
[0266] In the compound according to one embodiment, all groups described as "substituted or unsubstituted" are "unsubstituted" groups.
[0267] (Method for producing delayed-fluorescence compounds) The delayed-fluorescence compound in one embodiment can be produced by known methods. Furthermore, the delayed-fluorescence compound can also be produced by following known methods and using known alternative reactions and raw materials tailored to the target compound.
[0268] (Specific examples of delayed-fluorescence compounds) Specific examples of delayed-fluorescence compounds in one embodiment include the following compounds. However, the present invention is not limited to these specific examples.
[0269] [ka] [ka] [ka] [ka] [ka] [ka]
[0270] In one embodiment, when the sensitizing material is a delayed-fluorescence compound, the content of the delayed-fluorescence compound in the light-emitting layer is 5% by mass or more, or 10% by mass or more. In one embodiment, the content of the delayed fluorescence compound in the light-emitting layer is 50% by mass or less, or 30% by mass or less.
[0271] In one embodiment, when the sensitizing material is a phosphorescent metal complex, the content of the phosphorescent metal complex in the light-emitting layer is 5% by mass or more, or 10% by mass or more. In one embodiment, the content of the phosphorescent metal complex in the light-emitting layer is 50% by mass or less, or 30% by mass or less.
[0272] In one embodiment, the content of the fluorescent material in the light-emitting layer is 0.5% by mass or more, or 1% by mass or more. In one embodiment, the content of the fluorescent material in the light-emitting layer is 10% by mass or less, or 5% by mass or less. This embodiment does not exclude the case in which at least one of the one or more light-emitting layers contains materials other than the compound represented by formula (1), the compound represented by formula (2), the sensitizing material, and the fluorescent material. In one embodiment, at least one of the one or more light-emitting layers may contain only one of the compound represented by formula (1), the compound represented by formula (2), the sensitizing material, and the fluorescent material, or it may contain two or more of each.
[0273] According to one embodiment of the organic EL element, the lifespan of the organic EL element can be extended. According to one aspect of the organic EL element according to one embodiment, the lifespan of the organic EL element can be improved by including a sensitizing material (preferably a blue sensitizing material), a compound represented by formula (1), a compound represented by formula (2), and a fluorescent material in the light-emitting layer.
[0274] When the first and second components are used as host materials for the light-emitting layer, the total content of the first and second components in at least one organic layer of the light-emitting layer is preferably 80% by mass or more and 99% by mass or less relative to the entire layer. The content ratio (mass ratio) of the first component to the second component in the layer is usually 1:99 to 99:1, preferably 10:90 to 90:10, and more preferably 30:70 to 70:30. The dopant material content in the layer is preferably 1% by mass or more and 20% by mass or less relative to the entire layer.
[0275] In one embodiment, an organic EL element according to one aspect of the present invention has a hole transport band between the anode and the light-emitting layer.
[0276] The hole transport band is a collective term for one or more layers arranged between the anode and the light-emitting layer. The hole transport band may consist of, for example, layers called an electron blocking layer, a hole transport layer, and a hole injection layer, which will be described later, starting from the light-emitting layer side. It may be a laminated structure including all of these layers, or it may be a layer configuration of 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 it may be formed using two or more types of materials in combination.
[0277] In one aspect of the present invention, it is preferable that the organic EL element has a hole transport layer between the anode and the light-emitting layer.
[0278] In one embodiment, an organic EL element according to one aspect of the present invention has an electron transport band between the cathode and the light-emitting layer.
[0279] The electron transport band is a collective term for one or more layers placed between the cathode and the light-emitting layer. The electron transport band may consist of, for example, layers called a hole blocking layer, an exciton blocking layer, an electron transport layer, and an electron injection layer, starting from the light-emitting layer side, and may be a laminated structure including all of these layers, or a layer configuration 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 electron transport layers with different compositions may be laminated. Each layer may be formed using only one type of material, or it may be formed using two or more types of materials in combination.
[0280] In one aspect of the present invention, it is preferable that the organic EL element has an electron transport layer between the cathode and the light-emitting layer.
[0281] A typical element configuration of the organic EL element of the present invention is an example of a structure in which the following structures are stacked on a substrate. (1) Anode / Emitting layer / Cathode (2) Anode / Hole transport zone / Emitting layer / Cathode (3) Anode / Emitting layer / Electron transport band / Cathode (4) Anode / Hole transport band / Emitting layer / Electron transport band / Cathode (The " / " indicates that each layer is stacked adjacent to another.)
[0282] The following describes materials that can be used in an organic EL element according to one aspect of the present invention, as well as materials other than the above-mentioned compounds that constitute each layer.
[0283] (substrate) The substrate is used as a support for the light-emitting element. Examples of substrates include glass, quartz, and plastic. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples include plastic substrates made of polycarbonate or polyvinyl chloride.
[0284] (anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or more). Specifically, examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), or nitrides of metallic materials (e.g., titanium nitride).
[0285] (Hole injection layer) The hole injection layer is a layer containing a material with high hole injection properties. Suitable materials 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, or polymer compounds (oligomers, dendrimers, polymers, etc.).
[0286] (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, etc., 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 higher hole transport properties than electron transport properties. Furthermore, the layer containing the substance with high hole transport properties may be a single layer, or it may be a layer of two or more layers made of the above substances stacked together.
[0287] (Electron blocking layer, hole blocking layer, exciton blocking layer) An electron blocking layer, a hole blocking layer, an exciton (triplet) blocking layer, etc., may be provided adjacent to the light-emitting layer. An electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer. A hole blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron transport layer. An exciton blocking layer is a layer that prevents excitons generated in the light-emitting layer from diffusing to adjacent layers, thereby confining the excitons within the light-emitting layer.
[0288] (Guest (dopant) material for the luminescent layer) The light-emitting layer is a layer containing a highly luminescent substance, and various materials can be used. For example, as highly luminescent substances, 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. As blue fluorescent materials that can be used in the light-emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluorantene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc., can be used. As green fluorescent materials that can be used in the light-emitting layer, aromatic amine derivatives, etc., can be used. As red fluorescent materials that can be used in the light-emitting layer, tetracene derivatives, diamine derivatives, etc., can be used. Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used as blue phosphorescent materials that can be used in the light-emitting layer. Iridium complexes and the like are used as green phosphorescent materials that can be used in the light-emitting layer. Metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used as red phosphorescent materials that can be used in the light-emitting layer.
[0289] (Host material for the light-emitting layer) The light-emitting layer may be configured by dispersing the highly luminescent substance (guest material) described above in another substance (host material). As the substance for dispersing the highly luminescent substance, various materials can be used in addition to the materials used in the present invention described above (compounds represented by formula (1) and formula (2)), and it is preferable to use a substance that has a lower lowest unoccupied orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) than the highly luminescent substance. The following materials are used as host materials for dispersing highly luminescent substances: 1) metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes; 2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives; 3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives; and 4) aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives. The light-emitting layer may or may not contain the above-mentioned other substances in addition to the compound represented by formula (1) and the compound represented by formula (2).
[0290] (electron transport layer) The electron transport layer is a layer containing a material with high electron transport properties. The electron transport layer can contain: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymer compounds.
[0291] (electron injection layer) The electron injection layer is a layer containing a material with high electron injection potential. The electron injection layer may contain metal complex compounds such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and 8-hydroxyquinolinolatolithium (Liq), as well as lithium oxide (LiO2). x Alkali metals, alkaline earth metals, or compounds thereof can be used.
[0292] (cathode) For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof with a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.
[0293] In an organic EL element according to one aspect of the present invention, the thickness of each layer is not particularly limited, but generally, in order to suppress defects such as pinholes, keep the applied voltage low, and improve luminous efficiency, a range of several nm to 1 μm is usually preferred.
[0294] In an organic EL element according to one aspect of the present invention, the method of forming each layer is not particularly limited. Conventional known formation methods such as vacuum deposition and spin coating can be used. Each layer, such as the light-emitting layer, can be formed by known methods such as vacuum deposition, molecular beam deposition (MBE), or coating methods such as dipping with a solution dissolved in a solvent, spin coating, casting, bar coating, and roll coating.
[0295] [Manufacturing method for organic EL elements] A method for manufacturing an organic EL element in one aspect of the present invention can be expressed as follows. A method for manufacturing an organic electroluminescent element comprising a cathode, an anode, and one or more organic layers disposed between the cathode and the anode, The method involves heating and vaporizing a composition containing a compound represented by formula (1) and a compound represented by formula (2) from a vapor deposition source to form at least one of the organic layers. A method for manufacturing an organic electroluminescent element.
[0296] The composition used in the above-described manufacturing method is as described in the composition in one aspect of the present invention described above.
[0297] According to one aspect of the present invention, the balance between the vaporization amounts of the compound represented by formula (1) and the compound represented by formula (2) can be maintained for a long period of time. In particular, when performing continuous deposition on multiple substrates, it becomes possible to deposit films with a stable component ratio from the beginning to the end of the deposition process. This minimizes the occurrence of defective products and the loss of raw materials, thereby increasing yield and improving productivity. It should be noted that the above effect is not intended to mean that films can be deposited at a constant ratio on all substrates subjected to the continuous deposition process. Even when using the manufacturing method according to one aspect of the present invention, it is conceivable that the component ratio may fluctuate somewhat, especially in the final stage of the process, but it means that the proportion of time during which films can be deposited at a stable ratio can be greatly improved.
[0298] In one aspect of the present invention, a method for manufacturing an organic EL element is used to deposit at least one organic layer of the organic EL element by a vapor deposition method using the above-mentioned composition. The layer to be deposited with the composition is not particularly limited and may be any organic layer. Furthermore, two or more of the above-mentioned organic layers may be deposited by vapor deposition using the composition.
[0299] Furthermore, the method for forming each layer other than the layer formed by vapor deposition of the above composition is not particularly limited, and the method described for forming each layer in an organic EL element according to one aspect of the present invention can be used.
[0300] [Electronic equipment] An electronic device according to one aspect of the present invention is characterized by comprising an organic EL element according to one aspect of the present invention. Specific examples of electronic devices include display components such as organic EL panel modules, display devices such as televisions, mobile phones, or personal computers, and light-emitting devices such as lighting or vehicle lights.
[0301] [Mixture] A mixture according to one aspect of the present invention is characterized by comprising a composition according to one aspect of the present invention. In other words, a mixture according to one aspect of the present invention is characterized by comprising a compound represented by formula (1) and a compound represented by formula (2). The details of the compound represented by formula (1) and the compound represented by formula (2) are as described in the composition of one embodiment of the present invention described above.
[0302] Examples of the form of the mixture according to one aspect of the present invention include, but are not limited to, powder, solid, and pellet forms.
[0303] In one embodiment, the mixture according to one aspect of the present invention is in solid form.
[0304] In one embodiment, the mixture according to one aspect of the present invention is in pellet form.
[0305] <Other ingredients, etc.> A mixture according to one aspect of the present invention may or may not contain components other than the compound represented by formula (1) and the compound represented by formula (2).
[0306] In one embodiment, the mixture consists only of the compound represented by formula (1) and the compound represented by formula (2), or substantially only of the compound represented by formula (1) and the compound represented by formula (2). In the latter case, it may contain unavoidable impurities. In one embodiment, the mixture consists of 80% or more by mass of the compound represented by formula (1), 90% or more by mass of the compound represented by formula (2), 95% or more by mass of the compound represented by formula (2), 99.5% or more by mass of the compound represented by formula (1), 99.99% or more by mass, or 100% by mass of the compound represented by formula (2). In one embodiment, the mixture contains 80 mol% or more, 90 mol% or more, 95 mol% or more, 99 mol% or more, 99.5 mol% or more, 99.9 mol% or more, 99.99 mol% or more, or 100 mol% of the compound represented by formula (1) and the compound represented by formula (2).
[0307] <Mixture and method for producing the same> A mixture according to one aspect of the present invention may contain a compound represented by formula (1) and a compound represented by formula (2) in a single particle, or it may be a mixture of particles consisting of a compound represented by formula (1) and particles consisting of a compound represented by formula (2). One embodiment of the present invention provides a method for producing a mixture, for example, by grinding and mixing the compound represented by formula (1) and the compound represented by formula (2) using a mortar and pestle, or by placing the compound represented by formula (1) and the compound represented by formula (2) in a container, heating and melting them in a chemically inert environment, then cooling them to ambient temperature, and grinding the resulting mixture with a mixer to obtain the mixture. The latter method allows for mixing the compound represented by formula (1) and the compound represented by formula (2) at a molecular level, making it easier to control the ratio of their sublimation areas within a desired range and enabling more uniform deposition. Furthermore, it prevents problems such as uneven mixing that may occur during the transport of the mixture. The mixture may be compressed and molded into pellets.
[0308] In one embodiment, the mixture according to one aspect of the present invention is a mixture obtained by heating, melting, and solidifying the mixture. [Examples]
[0309] The following describes embodiments of the present invention. The present invention is not limited in any way by these embodiments.
[0310] <Compound> The compound represented by formula (1) (the first component) used in Examples 1 to 3 and Comparative Example 2 is shown below. [ka]
[0311] The compound represented by formula (2) (second component) used in Examples 1 to 3 and Comparative Example 1 is shown below. [ka]
[0312] The comparative compounds used in Comparative Examples 1 and 2 are shown below. [ka]
[0313] The structures of the other compounds used in the fabrication of the organic EL element in Example 3 are shown below. [ka]
[0314] Example 1 <Preparation of the mixture> 0.15 g of the first component (compound h-1) and 0.15 g of the second component (compound e-1) were weighed out and mixed while being ground in a mortar to prepare the mixture.
[0315] <Continuous vapor deposition test> Using the obtained mixture, a continuous vapor deposition test was conducted as follows. A crucible containing a total of 0.3g of the mixture is placed in a vacuum deposition machine at 1 × 10 -4 The glass substrate was heated under a vacuum of less than Pa, and the temperature was adjusted to achieve a deposition rate of 1 Å / sec, allowing a 100 nm film to be deposited. The glass substrate was replaced as needed, and the deposition process continued. The first substrate to be deposited was referred to as "Substrate No. 1," and subsequent substrates were referred to as "No. 2," "No. 3," and so on.
[0316] The obtained deposited film was evaluated based on the following criteria. The results are shown in Table 1. • Component ratio in the vapor-deposited film For each vapor-deposited film formed on a substrate, the mixing ratio of the first and second components was measured as follows. The vapor-deposited film formed on a glass substrate was eluted with tetrahydrofuran (THF), and the resulting solution was subjected to HPLC measurement using a high-performance liquid chromatography (HPLC) apparatus (apparatus name: Shimadzu Corporation "LC-2040CPlus") to calculate the area of the first and second components. By comparing the obtained area with the results of the HPLC measurements of the first and second components, the mass ratio of the first and second components contained in the film was calculated. ·Deposition ratio stability The area (%) of the first and second components obtained by HPLC measurement on substrate No. 1 was set to 100.0%, and the relative area values of the first and second components on each substrate from substrate No. 2 onwards were calculated and evaluated as the deposition ratio stability.
[0317] [Table 1]
[0318] Example 2 <Preparation of the mixture> A mixture was prepared in the same manner as in Example 1, except that 0.18 g of the first component (compound h-1) and 0.12 g of the second component (compound e-1) were used.
[0319] <Continuous vapor deposition test> Using the obtained mixture, a continuous deposition test was performed in the same manner as in Example 1, and the component ratios in the deposited film and the deposition ratio stability were evaluated. The results are shown in Table 2.
[0320] [Table 2]
[0321] Comparative Example 1 <Preparation of the mixture> The mixture was prepared in the same manner as in Example 1, except that compound h-2 was used instead of compound h-1 as the first component.
[0322] <Continuous vapor deposition test> Using the obtained mixture, a continuous deposition test was performed in the same manner as in Example 1, and the component ratio in the deposited film and the deposition ratio stability were evaluated. The results are shown in Table 3.
[0323] [Table 3]
[0324] Since the mass ratio of e-1 was 0% in substrate No. 1, the deposition ratio stability could not be calculated.
[0325] Comparative Example 2 <Preparation of the mixture> The mixture was prepared in the same manner as in Example 1, except that compound e-2 was used instead of compound e-1 as the second component.
[0326] <Continuous vapor deposition test> Using the obtained mixture, a continuous deposition test was performed in the same manner as in Example 1, and the component ratio in the deposited film and the deposition ratio stability were evaluated. The results are shown in Table 4.
[0327] [Table 4]
[0328] Example 3 <Preparation of the mixture> Mixture 1 was prepared by weighing 0.15 g of the first component (compound h-1) and 0.15 g of the second component (compound e-1) and mixing them while grinding them in a mortar.
[0329] <Fabrication of Organic EL Devices> A glass substrate (manufactured by Geomatic Co., Ltd.) with a 25mm x 75mm x 1.1mm thick ITO transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 1 minute. The ITO film thickness was set to 130 nm. After cleaning, the glass substrate with the transparent electrode was mounted in the substrate holder of the vacuum deposition apparatus. First, compound HT-1 and compound HI-1 were co-deposited onto the surface on which the transparent electrode was formed, so as to cover the transparent electrode, with compound HI-1 accounting for 3% by mass, thereby forming a hole injection layer with a thickness of 10 nm. Compound HT-1 was deposited onto the hole injection layer to form a first hole transport layer with a thickness of 60 nm. Compound EBL-1 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 5 nm. Mixture 1 (host material: a mixture of 0.15 g of compound h-1 and 0.15 g of compound e-1), prepared in the above <Preparation of Mixture>, compound PD-1 (sensitizing material), and compound BD-1 (fluorescent material) were co-deposited onto the second hole transport layer such that the proportion of compound PD-1 was 11% by mass and the proportion of compound BD-1 was 1.2% by mass, thereby forming a luminescent layer with a thickness of 30 nm. Compound HBL-1 was deposited onto the light-emitting layer to form a hole barrier layer with a thickness of 5 nm. Compound ET-1 and Liq were co-deposited onto a hole barrier layer so that the proportion of Liq was 50% by mass, forming an electron transport layer with a thickness of 30 nm. LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 1 nm. A cathode with a thickness of 50 nm was formed by depositing metallic aluminum onto the electron injection layer.
[0330] The series of steps described above for the fabrication of organic EL elements were repeated four times without adding any materials, resulting in the creation of a total of five organic EL elements. The first element created will be referred to as "No. 1," and subsequent elements will be referred to as "No. 2," "No. 3," and so on.
[0331] The element configuration of the organic EL element in Example 3 is schematically shown below. ITO(130) / HT-1:HI-1(10:3%) / HT-1(60) / EBL-1(5) / Mixture 1:PD-1:BD-1(30:11%:1.2%) / HBL-1(5) / ET-1:Liq(30:50%) / LiF(1) / Al(50) The numbers in parentheses represent the film thickness (in nm). Furthermore, the percentages in parentheses for the hole injection layer and electron transport layer indicate the proportion (mass %) of the latter compound in that layer. In the light-emitting layer, the numbers in parentheses, expressed as percentages, indicate the proportion (by mass) of the second and subsequent compounds in that layer.
[0332] <Evaluation of Organic EL Devices> • External quantum efficiency (EQE) Current density is 10.00 mA / cm² 2 A voltage was applied to the organic EL element in such a manner, and the EL emission spectrum was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). • Element life The fabricated organic EL element has a current density of 10.00 mA / cm². 2 A voltage was applied to achieve the desired result, and the time it took for the brightness to reach 95% of the initial brightness (LT95 (unit: hours)) was measured as the lifetime.
[0333] The efficiency and lifespan of element No. 1 are set to 100%, and the efficiency and lifespan of elements No. 2 to 5 are shown as relative values in Table 5.
[0334] [Table 5]
Claims
1. A composition comprising a compound represented by formula (1) and a compound represented by formula (2). 【Chemistry 112】 [In equation (1), R 102 , R 111 ~R 114 , and R 121 ~R 128 One of them is substituent α. The substituent α is a substituted or unsubstituted phenyl group. R 101 and R 131 ~R 135 , and R other than the substituent α 102 , R 111 ~R 114 , and R 121 ~R 128 is each independently a hydrogen atom or a substituent β. R 101 , R 102 , R 111 ~R 114 , R 121 ~R 128 , and R 131 ~R 135 Two or more adjacent pairs of these pairs cannot be combined with each other. The four Rs 101 They may be the same or different from each other. The three Rs 102 They may be the same or different from each other. The substituent β is, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by - COOR 802 A base represented by halogen atom, Cyano group, Nitro group, -P (=O) (R 931 ) (Caution 932 ) a base represented by -Ge(R) 933 ) (Caution 934 ) (Caution 935 ) a base represented by -B(R) 936 ) (Caution 937 ) a base represented by -B (OR 938 ) ( OR 939 ) a base represented by -O-S (=O) 2 (R 940 ) a base represented by A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and Monovalent heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms It is selected from the group consisting of the following. If there are two or more substituents β, the two or more substituents β may be the same or different from each other. R 801 , R 802 , R 901 ~R 907 , and R 931 ~R 940 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, It is a monovalent heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms. R 801 , R 802 , R 901 ~R 907 , and R 931 ~R 940 If there are two or more of them, then there are two or more R 801 , R 802 , R 901 ~R 907 , and R 931 ~R 940 Each of these may be the same or different. In equation (2), Z 1 ~Z 3 At least two of them are N, and Z is not N. 1 ~Z 3 C(R) 2a ) R 2a , R 201 , R 211 ~R 218 , R 221 ~R 228 , and R 231 ~R 238 Each of these is independently either a hydrogen atom or a substituent β. R 2a , R 201 , R 211 ~R 218 , R 221 ~R 228 , and R 231 ~R 238 Two or more adjacent pairs of these pairs cannot be combined with each other. The four Rs 201 They may be the same or different from each other. The substituent β is as defined in formula (1) above.
2. In equation (1), R 121 ~R 128 The composition according to claim 1, wherein one of them is substituent α.
3. The substituent β is Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, Substituted or unsubstituted haloalkyl groups having 1 to 30 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 30 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 30 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 30 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) group, -N(R) 906 ) (Caution 907 ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, -C(=O)R 801 A base represented by - COOR 802 A base represented by halogen atom, Cyano group, Nitro group, -P (=O) (R 931 ) (Caution 932 ) a base represented by -Ge(R 933 )(R 934 )(R 935 ) group represented by -B(R) 936 ) (Caution 937 ) a base represented by -B (OR 938 ) ( OR 939 ) a base represented by -O-S (=O) 2 (R 940 ) a base represented by Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms, and Monovalent heterocyclic groups with 5 to 30 substituted or unsubstituted ring-forming atoms A composition according to claim 1 or 2, selected from the group consisting of the following.
4. In formula (1), R is not the substituent α. 101 , R 102 , R 111 ~R 114 , R 121 ~R 128 , and R 131 ~R 135 The composition according to any one of claims 1 to 3, wherein the atom is a hydrogen atom.
5. The composition according to any one of claims 1 to 4, wherein the compound represented by formula (1) has at least one deuterium atom.
6. In equation (1), R is a hydrogen atom. 101 , R 102 , R 111 ~R 114 , R 121 ~R 128 , and R 131 ~R 135 The composition according to any one of claims 1 to 5, wherein the atom is a deuterium atom.
7. The composition according to any one of claims 1 to 6, wherein the compound represented by formula (1) is the compound represented by the following formula (1-1). 【Chemistry 113】 [In equation (1-1), R 101 , R 102 , R 111 ~R 114 , R 121 ~R 128 , and R 131 ~R 135 This is as defined in formula (1) above.
8. In the above formula (1-1), R 121 ~R 128 The composition according to claim 7, wherein at least one of the substituents is α.
9. In equation (2), Z 1 ~Z 3 The composition according to any one of claims 1 to 8, wherein N is present.
10. The composition according to any one of claims 1 to 9, wherein the compound represented by formula (2) is the compound represented by the following formula (2-1). 【Chemical 114】 [In equation (2-1), R 201 , R 211 ~R 218 , R 221 ~R 228 , and R 231 ~R 238 This is as defined in formula (1) above.
11. In equation (2), R 201 , R 211 ~R 218 , R 221 ~R 228 , and R 231 ~R 238 The composition according to any one of claims 1 to 10, wherein the atom is a hydrogen atom.
12. The composition according to any one of claims 1 to 11, wherein the compound represented by formula (2) has at least one deuterium atom.
13. In equation (2), R is a hydrogen atom. 211 ~R 218 , R 221 ~R 228 , and R 231 ~R 238 The composition according to any one of claims 1 to 12, wherein the atom is a deuterium atom.
14. In equation (2), R is a hydrogen atom. 201 , R 211 ~R 218 , R 221 ~R 228 , and R 231 ~R 238 The composition according to any one of claims 1 to 13, wherein the atom is a deuterium atom.
15. A mixture comprising the composition according to any one of claims 1 to 14.
16. The mixture according to claim 15, which is in solid form.
17. The mixture according to claim 15 or 16, which is in pellet form.
18. A mixture obtained by heating, melting, and solidifying the mixture according to any one of claims 15 to 17.
19. Cathode and, Anode and, One or more organic layers disposed between the cathode and the anode, It has, At least one of the organic layers comprises the composition described in any one of claims 1 to 14. Organic electroluminescent element.
20. Cathode and, Anode and, One or more organic layers disposed between the cathode and the anode, It has, At least one of the organic layers contains a compound represented by formula (1) and a compound represented by formula (2). Organic electroluminescent element. 【Chemical 115】 [In equation (1), R 102 , R 111 ~R 114 , and R 121 ~R 128 One of them is substituent α. The substituent α is a substituted or unsubstituted phenyl group. R 101 and R 131 ~R 135 , as well as R other than the substituent α 102 , R 111 ~R 114 , and R 121 ~R 128 Each of these is independently either a hydrogen atom or a substituent β. R 101 , R 102 , R 111 ~R 114 , R 121 ~R 128 , and R 131 ~R 135 Two or more adjacent pairs of these pairs cannot be combined with each other. The four Rs 101 They may be the same or different from each other. The three Rs 102 They may be the same or different from each other. The substituent β is, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 ) (Caution 902 ) (Caution 903 ) a base represented by -O-(R 904 ) a base represented by -S-(R 905 ) a base represented by -N(R) 906 ) (Caution 907 ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by - COOR 802 A base represented by halogen atom, Cyano group, Nitro group, -P (=O) (R 931 ) (Caution 932 ) a base represented by -Ge(R) 933 ) (Caution 934 ) (Caution 935 ) a base represented by -B(R) 936 ) (Caution 937 ) a base represented by -B (OR 938 ) ( OR 939 ) a base represented by -O-S (=O) 2 (R 940 ) a base represented by A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and Monovalent heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms It is selected from the group consisting of the following. If there are two or more substituents β, the two or more substituents β may be the same or different from each other. R 801 , R 802 , R 901 ~R 907 and R 931 ~R 940 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, It is a monovalent heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms. R 801 , R 802 , R 901 ~R 907 and R 931 ~R 940 If there are two or more of them, then there are two or more R 801 , R 802 , R 901 ~R 907 and R 931 ~R 940 Each of these may be the same or different. In equation (2), Z 1 ~Z 3 At least two of them are N, and Z is not N. 1 ~Z 3 C(R) 2a ) R 2a , R 201 , R 211 ~R 218 , R 221 ~R 228 , and R 231 ~R 238 Each of these is independently either a hydrogen atom or a substituent β. R 2a , R 201 , R 211 ~R 218 , R 221 ~R 228 , and R 231 ~R 238 Two or more adjacent pairs of these pairs cannot be combined with each other. The four Rs 201 They may be the same or different from each other. The substituent β is as defined in formula (1) above.
21. The device includes an anode, a light-emitting layer, and a cathode in this order, and at least one organic layer in the light-emitting layer is The aforementioned composition, or The compound represented by formula (1) and the compound represented by formula (2) An organic electroluminescent element according to claim 19 or 20, comprising:
22. The light-emitting layer has one or more layers, At least one of the one or two or more layers is The aforementioned composition, or The compound represented by formula (1) and the compound represented by formula (2) The organic electroluminescent element according to claim 21, comprising:
23. The organic electroluminescent element according to claim 22, wherein at least one of the one or more layers containing the composition or the compound represented by formula (1) and the compound represented by formula (2) further comprises a phosphorescent metal complex or a fluorescent material.
24. The organic electroluminescent element according to claim 22, wherein at least one of the one or more layers containing the composition or the compound represented by formula (1) and the compound represented by formula (2) further comprises a sensitizing material and a fluorescent material.
25. The organic electroluminescent element according to claim 24, wherein the sensitizing material is one or more compounds selected from the group consisting of phosphorescent metal complexes and delayed-fluorescence compounds.
26. The organic electroluminescent element according to any one of claims 21 to 25, wherein there is a hole transport band between the anode and the light-emitting layer.
27. An organic electroluminescent element according to any one of claims 21 to 26, wherein there is an electron transport band between the cathode and the light-emitting layer.
28. An electronic device comprising an organic electroluminescent element according to any one of claims 19 to 27.
Citation Information
Patent Citations
Mixture, organic electroluminescent element, and electronic device
WO2021015266A1