Deuterated compound production method

Abstract

A deuterated compound production method for producing a deuterated compound, the method comprising a first step for obtaining a first solution by dissolving or dispersing a compound having an aromatic ring in a solvent, and a second step for deuterating at least a portion of the compound having an aromatic ring in the first solution by dissolving or dispersing, in the first solution, an acid and a deuterium source simultaneously or separately, wherein the deuterium source is a compound that is solid at 25°C and 1 atm, that has one or more deuterium atoms, and that is different from the deuterated compound.

Description

Method for producing deuterated compounds

[0001] This invention relates to a method for producing deuterated compounds.

[0002] Deuterated compounds (compounds containing deuterium atoms) are used in various fields. As a method for producing deuterated compounds, for example, Patent Document 1 describes a method that includes the steps of: providing a liquid composition containing an aromatic compound having aromatic hydrogen dissolved or dispersed in a first deuterated solvent; and treating the liquid composition with a first acid having a pKa of 1 or less in water at 20 to 75°C to produce a first deuterated material. Patent Document 2 also describes a method that includes the steps of: a first step of dissolving an organic compound in a solvent that is not substituted with deuterium or is partially substituted with deuterium; and a second step of reacting the solution from the first step with a deuterium source.

[0003] International Publication No. 2011 / 053334, U.S. Patent Application Publication No. 2022 / 396533, Specification

[0004] The object of the present invention is to provide a method for producing a deuterated compound that can improve the deuteration rate.

[0005] According to one aspect of the present invention, a method for producing a deuterated compound is provided, comprising: a first step of dissolving or dispersing a compound having an aromatic ring in a solvent to obtain a first solution; and a second step of dissolving or dispersing an acid and a deuterium source in the first solution simultaneously or separately to deuterate at least a portion of the compound having an aromatic ring in the first solution, wherein the deuterium source is a compound that is solid at 25°C and 1 atm, has one or more deuterium atoms, and is a compound different from the deuterated compound.

[0006] According to one aspect of the present invention, a method for producing a deuterated compound that can improve the deuteration rate can be provided.

[0007] This graph shows the proportion of deuterated compounds in the mixture obtained in Example 1.

[0008] [Definition] In this specification, the term "hydrogen atom" includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0009] 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.

[0010] 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 "ring-forming carbon number" as 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, a 9,9-diphenylfluorenyl group has 13 ring-forming carbon atoms, and a 9,9'-spirobifluorenyl group has 25 ring-forming carbon atoms. Furthermore, if a benzene ring is substituted with an alkyl group as a substituent, the number of carbon atoms in the alkyl group is not included in the ring-forming carbon number of the benzene ring. Therefore, the ring-forming carbon number of a benzene ring substituted with an alkyl group is 6. Furthermore, if an alkyl group is substituted as a substituent on the naphthalene ring, 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.

[0011] 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 assemblies) (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 a substituent, 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.

[0012] In this specification, the expression "substituted or unsubstituted ZZ group having XX to YY carbon atoms" means that "XX to YY carbon atoms" refers to 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.

[0013] In this specification, the expression "ZZ group with substituted or unsubstituted atoms number XX to YY" means that "number of atoms XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, and does not include the number of substituent atoms 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.

[0014] In this specification, an unsubstituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group," and a substituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is a "substituted ZZ group." In this specification, "unsubstituted" in the case of "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. Also, in this specification, "substituted" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by substituents. Similarly, "substituted" in the case of "BB group substituted with AA group" means that one or more hydrogen atoms in the BB group are replaced by AA group.

[0015] "Substituents described herein" Hereinafter, substituents described herein will be explained.

[0016] The number of ring-forming carbon atoms in the "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, 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, more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkyl group" described herein is 1 to 50, preferably 1 to 20, 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, 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, more preferably 2 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted cycloalkyl group" described herein is 3 to 50, preferably 3 to 20, 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.

[0017] ・"Substitutable or unsubstituted aryl groups" Specific examples of "substituted or unsubstituted aryl groups" as described herein (Specific Example Group G1) include the following unsubstituted aryl groups (Specific Example Group G1A) and substituted aryl groups (Specific Example Group G1B). (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, when simply referred to as "aryl group," it includes both "unsubstituted aryl groups" and "substituted aryl groups." A "substituted aryl group" means 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 group in which one or more hydrogen atoms of an "unsubstituted aryl group" in Specific Example Group G1A below are replaced by substituents, and the example of a substituted aryl group in Specific Example Group G1B below. The examples of "unsubstituted aryl groups" and "substituted aryl groups" listed herein are merely examples. 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 groups" of specific examples group G1B below are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted aryl groups" of specific examples group G1B below are further replaced by substituents.

[0018] - 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, crisenyl group, benzocrisenyl group, triphenylenyl group, benzotriphenylenyl group, tetracerenyl group, pentaceryl group, fluorenyl group, 9,9'-spirobifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, fluoranthenyl group, benzofluoranthenyl group, perilenyl group, and monovalent aryl groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0019]

[0020]

[0021] Substitutive aryl groups (specific examples group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, cyanophenyl group, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, A naphthylphenyl group, and a monovalent group derived from the ring structure represented by the general formulas (TEMP-1) to (TEMP-15) in which one or more hydrogen atoms are replaced by substituents.

[0022] - "Substituted or unsubstituted heterocyclic groups" The "heterocyclic groups" described herein are cyclic groups containing at least one heteroatom in the ring-forming atoms. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron. The "heterocyclic groups" described herein are monocyclic groups or fused ring groups. The "heterocyclic groups" described herein are aromatic heterocyclic groups or non-aromatic heterocyclic groups. Specific examples of "substituted or unsubstituted heterocyclic groups" described herein (Specific Examples Group G2) include the following unsubstituted heterocyclic groups (Specific Examples Group G2A) and substituted heterocyclic groups (Specific Examples Group G2B). (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" alone includes both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups." A "substituted heterocyclic group" means 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 the following example group G2A in which hydrogen atoms of an "unsubstituted heterocyclic group" are replaced, and the examples of substituted heterocyclic groups in the following example group G2B. Furthermore, 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 the hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself in the "substituted heterocyclic groups" of specific examples group G2B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted heterocyclic groups" of specific examples group G2B are further replaced by substituents.

[0023] The specific examples group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (Specific Examples Group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (Specific Examples Group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (Specific Examples 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 Examples Group G2A4).

[0024] Specific examples group G2B includes, for example, the following 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).

[0025] ・Unsubstituted heterocyclic groups containing nitrogen atoms (specific examples group G2A1): Pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyridyl group, pyridadinyl 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, phenanthridineyl group, acridinyl group, phenadinyl group, carbazolyl group, Benzocarbazolyl group, morpholino group, phenoxazinyl group, phenothiazinyl group, azacarbazolyl group, and diazacarbazolyl group.

[0026] - Unsubstituted heterocyclic groups containing an oxygen atom (specific examples group G2A2): furyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzoisoxazolyl group, phenoxazinyl group, morpholino group, dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, azanaftobenzofuranyl group, and diazanaftobenzofuranyl group.

[0027] - Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl 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), azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0028] - Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0029] ​​​​​​​​​​​​​​​​​​​​​​​​​​- Substitutive heterocyclic groups 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, methylbenzimidazolyl group, ethylbenzimidazolyl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenylquinazolinyl group, and biphenylylquinazolinyl group.

[0033] - Heterocyclic groups with oxygen atoms substituted (specific examples group G2B2): Phenyldibenzofuranyl group, methyldibenzofuranyl group, t-butyldibenzofuranyl group, and monovalent residues of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0034] - Substitutive heterocyclic groups containing a sulfur atom (specific examples group G2B3): Phenyldibenzothiophenyl group, methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and monovalent residues of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0035] - 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):

[0036] 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 one of XA and YA is CH ２ This refers to one or more hydrogen atoms selected from the hydrogen atoms of the methylene group in that case.

[0037] ・"Substitutable 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 an "unsubstituted alkyl group," and "substituted alkyl group" refers to the case where "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereafter, when simply referred to as "alkyl group," it includes both "unsubstituted alkyl groups" and "substituted alkyl groups." "Substitutable alkyl group" means 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 group in which one or more hydrogen atoms in the following "unsubstituted alkyl group" (Specific Examples Group G3A) are replaced by substituents, and examples of substituted alkyl groups (Specific Examples Group G3B). In this specification, the alkyl group in "unsubstituted alkyl group" means a chain-like alkyl group. Therefore, "unsubstituted alkyl groups" include both linear and branched "unsubstituted alkyl groups." The examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed here are merely examples; the "substituted alkyl groups" described herein also include groups in which the hydrogen atoms of the alkyl group itself are further replaced by substituents, as well as groups in which the hydrogen atoms of the substituents are further replaced by substituents.

[0038] 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.

[0039] Substitutive alkyl groups (specific examples group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group, and trifluoromethyl group.

[0040] - "Substitutable 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). (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" means a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced by substituents. Specific examples of "substituted alkenyl groups" include groups in which the "unsubstituted alkenyl groups" (specific example group G4A) have 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 groups" of specific example group G4B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted alkenyl groups" of specific example group G4B are further replaced by substituents.

[0041] - Unsubstituted alkenyl groups (specific examples group G4A): vinyl group, allyl group, 1-butenyl group, 2-butenyl group, and 3-butenyl group.

[0042] Substitutable 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.

[0043] ・"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, an unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl groups" is an "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" means 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 the following groups in which one or more hydrogen atoms in an "unsubstituted alkynyl group" (Specific Examples Group G5A) are replaced by substituents, etc.

[0044] • Unsubstituted alkynyl groups (specific examples group G5A): Ethynyl group.

[0045] ・"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). (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, "cycloalkyl group" simply includes both "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups." "Substituted cycloalkyl group" means a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced by substituents. Specific examples of "substituted cycloalkyl groups" include the following groups in which one or more hydrogen atoms in the "unsubstituted cycloalkyl group" (Specific Examples Group G6A) are replaced by substituents, and examples of substituted cycloalkyl groups (Specific Examples Group G6B). The examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed herein are merely examples. 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 substituents, as well as groups in which the hydrogen atoms of the substituents in the "substituted cycloalkyl groups" of specific examples group G6B are further replaced by substituents.

[0046] 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.

[0047] Substitutive cycloalkyl groups (specific examples group G6B): 4-methylcyclohexyl group.

[0048] - Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ The group represented by ) as described herein -Si(R ９０１ ) (Caution ９０２) (Caution ９０３ Specific examples of the group represented by (Specific Examples Group G7) include -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6). Here, G1 is a "substituted or unsubstituted aryl group" as described in Specific Examples Group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in Specific Examples Group G2. G3 is a "substituted or unsubstituted alkyl group" as described in Specific Examples Group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Examples Group G6. In -Si(G1)(G1)(G1), the multiple G1s are either identical or different from one another. - In Si(G1)(G2)(G2), multiple G2s are either identical or different from each other. - In Si(G1)(G1)(G2), multiple G1s are either identical or different from each other. - In Si(G2)(G2)(G2), multiple G2s are either identical or different from each other. - In Si(G3)(G3)(G3), multiple G3s are either identical or different from each other. - In Si(G6)(G6)(G6), multiple G6s are either identical or different from each other.

[0049] ・"-O-(R ９０４ The group represented by ) as described herein -O-(R ９０４ Specific examples of the group represented by (Specific Examples Group G8) include -O(G1), -O(G2), -O(G3), and -O(G6). Here, G1 is a "substituted or unsubstituted aryl group" as described in Specific Examples Group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in Specific Examples Group G2. G3 is a "substituted or unsubstituted alkyl group" as described in Specific Examples Group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Examples Group G6.

[0050] ・"-S-(R ９０５ The group represented by ) as described herein -S-(R ９０５Specific examples of the group represented by (Specific Examples Group G9) include -S (G1), -S (G2), -S (G3), and -S (G6). Here, G1 is a "substituted or unsubstituted aryl group" as described in Specific Examples Group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in Specific Examples Group G2. G3 is a "substituted or unsubstituted alkyl group" as described in Specific Examples Group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Examples Group G6.

[0051] -N(R) ９０６ ) (Caution ９０７ The group represented by ) as described herein -N(R ９０６ ) (Caution ９０７ Specific examples of the group represented by (Specific Examples Group G10) include -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6). Here, G1 is a "substituted or unsubstituted aryl group" as described in Specific Examples Group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in Specific Examples Group G2. G3 is a "substituted or unsubstituted alkyl group" as described in Specific Examples Group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Examples Group G6. In -N(G1)(G1), the multiple G1s are either identical or different from each other. In -N(G2)(G2), the multiple G2s are either identical or different from each other. In -N(G3)(G3), the multiple G3s are either identical or different from each other. -N(G6)(G6) The multiple G6s are either identical or different from one another.

[0052] ・"Halogen atom" Specific examples of "halogen atom" as described herein (Specific Examples Group G11) include fluorine atom, chlorine atom, bromine atom, and iodine atom.

[0053] - "Substituted or unsubstituted fluoroalkyl groups" The "substituted or unsubstituted fluoroalkyl groups" described 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. "Substituted fluoroalkyl groups" refer to groups in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced by substituents. The "substituted fluoroalkyl groups" described 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 groups in which one or more hydrogen atoms in the aforementioned "alkyl group" (specific example group G3) are replaced by fluorine atoms.

[0054] - "Substituted or unsubstituted haloalkyl groups" The "substituted or unsubstituted haloalkyl groups" described 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. "Substituted haloalkyl groups" refer to groups in which one or more hydrogen atoms of a "haloalkyl group" are replaced by substituents. The "substituted haloalkyl groups" described 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 in the aforementioned "alkyl group" (specific example group G3) are replaced by halogen atoms. Haloalkyl groups are sometimes referred to as alkyl halides.

[0055] - "Substituted or unsubstituted alkoxy groups" Specific examples of "substituted or unsubstituted alkoxy groups" as described herein include the group represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group" 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.

[0056] - "substituted or unsubstituted alkylthio group" 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.

[0057] - "substituted or unsubstituted aryloxy group" A specific example of the "substituted or unsubstituted aryloxy group" described herein is a group represented by -O(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 aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.

[0058] - "substituted or unsubstituted arylthio group" 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.

[0059] - "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described herein is a group represented by -Si(G3)(G3)(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) are either the same or different from each other. The number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein.

[0060] - "Substituted or unsubstituted aralkyl group" A specific example of the "substituted or unsubstituted aralkyl group" described herein is a 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.

[0061] 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.

[0062] 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.

[0063] In this specification, unless otherwise specified, the carbazolyl group is specifically one of the following groups:

[0064]

[0065] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically one of the following groups:

[0066]

[0067] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents the bond position.

[0068] In this specification, unless otherwise specified, the dibenzofuranyl group and the dibenzothiophenyl group specifically refer to any of the following groups:

[0069]

[0070] In the general formulas (TEMP-34) to (TEMP-41) above, * represents the bond position.

[0071] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t-butyl groups.

[0072] - "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 "substituted or unsubstituted arylene groups" (Specific Examples Group G12) include divalent groups derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described in Specific Examples Group G1.

[0073] - "Substitutable or unsubstituted divalent heterocyclic groups" Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic groups" described herein are 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 divalent groups derived by removing one hydrogen atom from the heterocycle of the "substituted or unsubstituted heterocyclic groups" described in Specific Examples Group G2.

[0074] - "Substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described herein is a divalent group derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl group" described above. Specific examples of the "substituted or unsubstituted alkylene group" (Specific Examples Group G14) include the divalent group derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl group" described in Specific Examples Group G3.

[0075] Unless otherwise specified herein, the substituted or unsubstituted arylene groups are preferably any of the following general formulas (TEMP-42) to (TEMP-68).

[0076]

[0077]

[0078] In the above general formulas (TEMP-42) to (TEMP-52), Q １ ~Q １０ Each of these is independently a hydrogen atom or a substituent. In the general formulas (TEMP-42) to (TEMP-52) above, * represents a bond position.

[0079]

[0080] In the above general formulas (TEMP-53) to (TEMP-62), Q １ ~Q １０ Each of these is independently either a hydrogen atom or a substituent. Formula Q ９ and Q １０ These elements may be bonded to each other via single bonds to form a ring. In the general formulas (TEMP-53) to (TEMP-62), * indicates a bond position.

[0081]

[0082] In the above general formulas (TEMP-63) to (TEMP-68), Q １ ~Q ８ Each of these is independently a hydrogen atom or a substituent. In the general formulas (TEMP-63) to (TEMP-68), * represents a bond position.

[0083] 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).

[0084]

[0085]

[0086]

[0087] In the above general formulas (TEMP-69) to (TEMP-82), Q １ ~Q ９ Each of these is independently either a hydrogen atom or a substituent.

[0088]

[0089]

[0090]

[0091]

[0092] In the above general formulas (TEMP-83) to (TEMP-102), Q １ ~Q ８ Each of these is independently either a hydrogen atom or a substituent.

[0093] The above is a description of the substituents described herein.

[0094] ・"When they combine to form a ring" In this specification, "one or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring, or do not combine with each other" means the case in which "one or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring," the case in which "one or more pairs of adjacent elements combine to form a substituted or unsubstituted fused ring," and the case in which "one or more pairs of adjacent elements do not combine with each other." The cases in this specification where "one or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring" and the case where "one or more pairs of adjacent elements combine to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "when they combine to form a ring") will be explained below. We will explain using the example of an anthracene compound represented by the following general formula (TEMP-103), whose parent skeleton is an anthracene ring.

[0095]

[0096] For example, R ９２１~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 group, R ９２２ and R ９２３ The group, R ９２３ and R ９２４ The group, R ９２４ and R ９３０ The group, R ９３０ and R ９２５ The group, R ９２５ and R ９２６ The group, R ９２６ and R ９２７ The group, R ９２７ and R ９２８ The group, R ９２８ and R ９２９ The pair with, and R ９２９ and R ９２１ They are a pair.

[0097] The phrase "one or more sets" above means that two or more sets of the above-mentioned sets of two or more adjacent elements may simultaneously form a ring. For example, R ９２１ and R ９２２ and are joined to each other to form a ring Q Ａ Forms R ９２５ and R ９２６ and are joined to each other 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).

[0098]

[0099] 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 each other to form a ring Q Ａ Forms R ９２２ and R ９２３ and are joined to each other to form a ring Q Ｃ It forms three adjacent (R ９２１ , R ９２２ and R９２３ A combination consisting of ) combines with each other to form a ring and condenses with the anthracene backbone. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q Ａ and ring Q Ｃ share R ９２２ .

[0100]

[0101] The "monocyclic ring" or "condensed ring" formed is, as the structure of only the formed ring, either a saturated ring or an unsaturated ring. Even when "one set of two adjacent sets" forms a "monocyclic ring" or "condensed ring", the "monocyclic ring" or "condensed ring" can form a saturated ring or an unsaturated ring. For example, in the general formula (TEMP-104), ring Q Ａ and ring Q Ｂ are each a "monocyclic ring" or "condensed ring". Also, in the general formula (TEMP-105), ring Q Ａ , and ring Q Ｃ are "condensed rings". Ring Q Ａ and ring Q Ｃ in the general formula (TEMP-105) are a condensed ring formed by the condensation of ring Q Ａ and ring Q Ｃ . If ring Q Ａ in the general formula (TMEP-104) is a benzene ring, ring Q Ａ is a monocyclic ring. If ring Q Ａ in the general formula (TMEP-104) is a naphthalene ring, ring Q Ａ is a condensed ring.

[0102] "Unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. "Saturated ring" means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of the aromatic hydrocarbon ring include structures in which the groups listed as specific examples in Specific Example Group G1 are terminated by hydrogen atoms. Specific examples of the aromatic heterocyclic ring include structures in which the aromatic heterocyclic groups listed as specific examples in Specific Example Group G2 are terminated by hydrogen atoms. Specific examples of the aliphatic hydrocarbon ring include structures in which the groups listed as specific examples in Specific Example Group G6 are terminated by hydrogen atoms. "Forming a ring" means forming a ring with only a plurality of atoms of the parent skeleton or a plurality of atoms of the parent skeleton and one or more arbitrary elements. For example, in the general formula (TEMP-104), R ９２１ and R ９２２ are bonded to each other to form a ring Q Ａ means a ring formed by a carbon atom of the anthracene skeleton to which R ９２１ is bonded, a carbon atom of the anthracene skeleton to which R ９２２ is bonded, and one or more arbitrary elements. Specific examples include, when R ９２１ and R ９２２ form a ring Q Ａ , a single-ring unsaturated ring is formed by a carbon atom of the anthracene skeleton to which R ９２１ is bonded, a carbon atom of the anthracene skeleton to which R ９２２ is bonded, and four carbon atoms. When R ９２１ and R ９２２ form a ring, the ring formed is a benzene ring.

[0103] Here, "any element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur, unless otherwise specified herein. In any element (for example, carbon or nitrogen), bonds that do not form a ring may be terminated with a hydrogen atom or the like, or substituted with "any substituent" as described later. If any element other than carbon is included, the formed ring is a heterocycle. Unless otherwise specified herein, "one or more any elements" 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, of "monocycle" and "fused ring," "monocycle" is preferred. Unless otherwise specified herein, of "saturated ring" and "unsaturated ring," "unsaturated ring" is preferred. Unless otherwise specified herein, "monocycle" is preferably a benzene ring. Unless otherwise specified herein, "unsaturated ring" is preferably a benzene ring. When "one or more sets of two or more adjacent elements" "bond to each other to form a substituted or unsubstituted monoring" or "bond to each other to form a substituted or unsubstituted fused ring", unless otherwise specified herein, preferably, one or more sets of two or more adjacent elements bond to each other to form a substituted or unsubstituted "unsaturated ring" consisting of multiple atoms of the parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur elements, ranging from one to fifteen.

[0104] The substituents in the case where the above-mentioned "mono-ring" or "fused ring" has substituents are, for example, "any substituents" as described later. Specific examples of substituents in the case where the above-mentioned "mono-ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described in this specification" above. The substituents in the case where the above-mentioned "saturated ring" or "unsaturated ring" has substituents are, for example, "any substituents" as described later. Specific examples of substituents in the case where the above-mentioned "mono-ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described in this specification" above. The above explains the cases where "one or more sets of two or more adjacent elements are bonded to each other to form a substituted or unsubstituted mono-ring" and where "one or more sets of two or more adjacent elements are bonded to each other to form a substituted or unsubstituted fused ring" ("when they are bonded to form a ring").

[0105] - Substituents in the case of "substituted or unsubstituted" In one embodiment of this specification, the substituents in the case of "substituted or unsubstituted" (which may be referred to as "any substituents" in this specification) are, for example, unsubstituted C1-C50 alkyl groups, unsubstituted C2-C50 alkenyl groups, unsubstituted C2-C50 alkynyl groups, unsubstituted ring-forming C3-C50 cycloalkyl groups, -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ ), -O-(R ９０４ ), -S-(R ９０５ ), -N(R ９０６ ) (Caution ９０７ ), a group selected from the group consisting of halogen atoms, cyano groups, nitro groups, unsubstituted aryl groups with 6 to 50 ring-forming atoms, and unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms, where R ９０１ ~R ９０７ 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. ９０１ If there are two or more of them, then there are two or more R９０１ 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.

[0106] In one embodiment, the substituent in the case of "substituted or unsubstituted" is a group selected from the group consisting of alkyl groups having 1 to 50 carbon atoms, aryl groups having 6 to 50 ring-forming carbon atoms, and heterocyclic groups having 5 to 50 ring-forming atoms.

[0107] In one embodiment, the substituent in the case of "substituted or unsubstituted" is a group selected from the group consisting of alkyl groups having 1 to 18 carbon atoms, aryl groups having 6 to 18 ring-forming carbon atoms, and heterocyclic groups having 5 to 18 ring-forming atoms.

[0108] Specific examples of each of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents as described herein" above.

[0109] Unless otherwise specified herein, any 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, the same as those described above for any substituent.

[0110] In this specification, a numerical range expressed using "AA to BB" means a range that includes the numerical value AA, which is written before "AA to BB", as the lower limit, and the numerical value BB, which is written after "AA to BB", as the upper limit.

[0111] [First Embodiment] The method for producing a deuterated compound according to this embodiment is a method for producing a deuterated compound, comprising: a first step of dissolving or dispersing a compound having an aromatic ring in a solvent to obtain a first solution; and a second step of dissolving or dispersing an acid and a deuterium source in the first solution simultaneously or separately to deuterate at least a portion of the compound having an aromatic ring in the first solution. In the method for producing a deuterated compound according to this embodiment, the deuterium source is a compound that is solid at 25°C and 1 atm, has one or more deuterium atoms, and is a compound different from the deuterated compound.

[0112] Conventionally, reactions that introduce deuterium into compounds have been known to use liquid compounds as deuterium sources. For example, a reaction combining deuterated benzene (hereinafter sometimes referred to as "heavy benzene") with a strong acid is known. However, depending on the compound to which deuterium is to be introduced, the application of these deuterium sources may be difficult. Furthermore, there is a high demand for conditions that can suppress the effects of heavy benzene and strong acids (such as compound degradation). In addition, from a safety perspective, it is desirable to avoid carcinogenic benzene. According to the method for producing deuterated compounds of this embodiment, by using a compound that is solid at 25°C and 1 atm as a deuterium source, it is possible to produce deuterated compounds with an improved deuterated rate, and ease of handling and safety during production are also improved.

[0113] As described later, the deuterated compounds (products) produced by the deuterated compound production method according to this embodiment are often not a single compound, but a mixture of compounds with different numbers of deuterium atoms. The "deuterated rate" of the deuterated compounds (products) produced by the deuterated compound production method according to this embodiment refers to the ratio of deuterium atoms to the total hydrogen atoms in the product obtained by the deuterated compound production method according to this embodiment. If the product is a single compound, it refers to the deuterated rate of that single compound; if the product is a mixture, it refers to the average value of the deuterated rates of the compounds contained in the mixture. According to the deuterated compound production method according to this embodiment, it can be expected that a larger amount of compounds with a larger number of deuterium atoms can be obtained for each deuterated compound in the mixture that is the product.

[0114] In the following, we will first describe the raw materials and other components used in the production of the deuterated compound according to this embodiment.

[0115] (Compounds having aromatic rings) In the method for producing a deuterated compound according to this embodiment, a compound having an aromatic ring (starting compound) is used as the compound to be deuterated. In this specification, an aromatic ring means a ring in which the number of π electrons is 4n + 2 (where n is a positive integer including 0). The aromatic ring is at least one of an aromatic hydrocarbon ring and an aromatic heterocycle.

[0116] As for the aromatic hydrocarbon ring, an aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms is preferred, an aromatic hydrocarbon ring having 6 to 30 ring-forming carbon atoms is more preferred, a condensed aromatic hydrocarbon ring having 10 to 30 ring-forming carbon atoms is even more preferred, a condensed aromatic hydrocarbon ring having 10 to 21 ring-forming carbon atoms is even more preferred, and a condensed aromatic hydrocarbon ring having 12 to 18 ring-forming carbon atoms is still even more preferred. Furthermore, as for the aromatic heterocycle, an aromatic heterocycle having 5 to 50 ring-forming atoms is preferred, an aromatic heterocycle having 5 to 30 ring-forming atoms is more preferred, a condensed aromatic heterocycle having 9 to 30 ring-forming atoms is even more preferred, a condensed aromatic heterocycle having 9 to 18 ring-forming atoms is even more preferred, and a condensed aromatic heterocycle having 9 to 17 ring-forming atoms is still even more preferred.

[0117] In the method for producing a deuterated compound according to this embodiment, if the compound having an aromatic ring (raw material compound) has an aromatic heterocycle, examples of heteroatoms contained in the aromatic heterocycle include nitrogen atoms, oxygen atoms, sulfur atoms, silicon atoms, phosphorus atoms, and boron atoms. In the method for producing a deuterated compound according to this embodiment, if the compound having an aromatic ring (raw material compound) has an aromatic heterocycle, it is preferable that the aromatic heterocycle contains an oxygen atom as a heteroatom.

[0118] In the method for producing a deuterated compound according to this embodiment, the compound having an aromatic ring (raw material compound) is preferably a compound having one or more aromatic hydrocarbon rings and one or more aromatic heterocycles. In one embodiment of the method for producing a deuterated compound according to this embodiment, the compound having an aromatic ring (raw material compound) has a structure in which the aromatic hydrocarbon ring and the aromatic heterocycle are bonded via a single bond.

[0119] In the method for producing a deuterated compound according to this embodiment, it is preferable that at least one of the aromatic hydrocarbon rings is selected from the group consisting of rings represented by the following formulas (101) to (181). The structure of the aromatic hydrocarbon ring is not limited to the following formulas.

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128] (In formulas (101) to (181) above, * represents, independently, the bonding position of the bond to another structure in the compound having the aromatic ring.)

[0129] In the method for producing a deuterated compound according to this embodiment, it is preferable that at least one of the aromatic heterocycles is selected from the group consisting of rings represented by the following formulas (201) to (224).

[0130]

[0131]

[0132] (In formulas (201) to (224) above, * represents, independently, the bonding position of the bond to another structure in the compound having the aromatic ring.)

[0133] In the method for producing a deuterated compound according to this embodiment, the rings represented by formulas (101) to (181) and the rings represented by formulas (201) to (224) may further have one or more substituents, or may not have substituents.

[0134] In one embodiment, when the rings represented by formulas (101) to (181) and (201) to (224) have substituents, the substituents are selected from the group consisting of alkyl groups having 1 to 50 carbon atoms, aryl groups having 6 to 50 ring-forming carbon atoms, and heterocyclic groups having 5 to 50 ring-forming atoms.

[0135] In one embodiment, when the rings represented by formulas (101) to (181) and (201) to (224) have substituents, the substituents are selected from the group consisting of alkyl groups having 1 to 30 carbon atoms, aryl groups having 6 to 30 ring-forming carbon atoms, and heterocyclic groups having 5 to 30 ring-forming atoms.

[0136] In one embodiment, when the rings represented by formulas (101) to (181) and (201) to (224) have substituents, the substituents are selected from the group consisting of alkyl groups having 1 to 18 carbon atoms, aryl groups having 6 to 18 ring-forming carbon atoms, and heterocyclic groups having 5 to 18 ring-forming atoms.

[0137] In the method for producing a deuterated compound according to this embodiment, the number of rings in the compound having an aromatic ring (raw material compound) is preferably two or more, and more preferably three or more. Furthermore, in the method for producing a deuterated compound according to this embodiment, the number of rings in the compound having an aromatic ring (raw material compound) is preferably six or less, and more preferably five or less.

[0138] In the method for producing a deuterated compound according to this embodiment, the compound having an aromatic ring (raw material compound) preferably contains at least one of an anthracene ring and a xanthene ring. In this case, the anthracene ring contained in the compound having an aromatic ring (raw material compound) may be a benzanthracene ring or another anthracene derivative. The xanthene ring contained in the compound having an aromatic ring (raw material compound) may be a xanthene derivative such as a benzoxanthene ring.

[0139] Compounds having an aromatic ring (raw material compound) preferably contain a benzanthracene ring, and more preferably contain a benz[a]anthracene ring. Compounds having an aromatic ring (raw material compound) preferably contain a benzoxanthene ring, and more preferably contain a benzo[kl]xanthene ring. Compounds having an aromatic ring (raw material compound) preferably contain both a benzanthracene ring and a benzoxanthene ring. Compounds having an aromatic ring (raw material compound) preferably contain both a benzanthracene ring and a benzo[kl]xanthene ring. Compounds having an aromatic ring (raw material compound) may also preferably contain both a benz[a]anthracene ring and a benzoxanthene ring. Compounds having an aromatic ring (raw material compound) preferably contain both a benz[a]anthracene ring and a benzo[kl]xanthene ring.

[0140] In the method for producing a deuterated compound according to this embodiment, it is also preferable that the compound having an aromatic ring (raw material compound) has at least one ring selected from the group consisting of rings represented by formulas (138) to (152) and at least one ring selected from the group consisting of rings represented by formulas (201) to (224). In this case, it is also preferable that the compound having an aromatic ring (raw material compound) is a compound in which * in at least one ring selected from the group consisting of rings represented by formulas (138) to (152) and * in at least one ring selected from the group consisting of rings represented by formulas (201) to (224) are linked by a single bond. For example, a compound in which * in the ring represented by formula (138) and * in the ring represented by formula (201) are linked by a single bond is represented by the following formula (A1).

[0141]

[0142] In the method for producing a deuterated compound according to this embodiment, the compound having an aromatic ring (raw material compound) may be a compound having only an aromatic hydrocarbon ring (a compound having only an aromatic hydrocarbon ring as a ring contained in the molecule). An example of a compound having an aromatic ring (raw material compound) is a compound having only an aromatic hydrocarbon ring is a compound in which a hydrogen atom is bonded to the bonding position* in formulas (101) to (181).

[0143] Furthermore, in the method for producing a deuterated compound according to this embodiment, the compound having an aromatic ring (starting compound) may be a compound having only an aromatic heterocycle (a compound having only an aromatic heterocycle as a ring contained in the molecule). An example of a compound having an aromatic ring (starting compound) being a compound having only an aromatic heterocycle is a compound in which a hydrogen atom is bonded to the bond position* in formulas (201) to (224).

[0144] In the method for producing a deuterated compound according to this embodiment, it is preferable that the compound having an aromatic ring (raw material compound) does not contain deuterium atoms. In this specification, a compound that does not contain deuterium atoms and in which all hydrogen atoms are light hydrogen atoms may be referred to as a "light hydrogen compound".

[0145] In the method for producing a deuterated compound according to this embodiment, it is preferable that the compound having an aromatic ring (starting compound) does not contain substituted or unsubstituted amino groups.

[0146] In the method for producing a deuterated compound according to this embodiment, it is preferable that the compound having an aromatic ring (raw material compound) is not a compound selected from the group consisting of naphthalene, anthracene, and pyrene. In the method for producing a deuterated compound according to this embodiment, it is preferable that the compound having an aromatic ring (raw material compound) is not anthracene with 14 ring-forming carbon atoms.

[0147] (Specific examples of compounds having aromatic rings) Specific examples of compounds having aromatic rings (raw material compounds) used in the method for producing deuterated compounds according to this embodiment include, for example, the following compounds. However, the present invention is not limited to these specific aromatic compounds.

[0148]

[0149] (Deuterium Source) The deuterium source used in the method for producing the deuterated compound according to this embodiment is a compound that is solid at 25°C and 1 atm and has one or more deuterium atoms. The deuterium source is a different compound from the deuterated compound produced by the method for producing the deuterated compound according to this embodiment.

[0150] In the method for producing a deuterated compound according to this embodiment, the deuterium source is preferably a compound that is solid at 30°C and 1 atm, and more preferably a compound that is solid at 50°C and 1 atm.

[0151] In the method for producing a deuterated compound according to this embodiment, it is preferable that the deuterium source is not in a frozen state. In this case, it is preferable that the deuterium source, which is dissolved or dispersed in the first solution in the second step described later, is not in a frozen state.

[0152] In the method for producing a deuterated compound according to this embodiment, the deuterium source is preferably a compound with a melting point of 100°C or lower, and more preferably a compound with a melting point of 80°C or lower.

[0153] In the method for producing a deuterated compound according to this embodiment, the deuterium source is preferably an organic compound.

[0154] In the method for producing a deuterated compound according to this embodiment, the deuterium source preferably includes one or more structures selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. The aromatic hydrocarbon ring included in the deuterium source is preferably an aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, more preferably an aromatic hydrocarbon ring having 6 to 30 ring-forming carbon atoms, and even more preferably an aromatic hydrocarbon ring having 6 to 18 ring-forming carbon atoms. The aromatic heterocycle included in the deuterium source is preferably a condensed aromatic heterocycle having 5 to 50 ring-forming carbon atoms, more preferably a condensed aromatic heterocycle having 5 to 30 ring-forming carbon atoms, and even more preferably a condensed aromatic heterocycle having 5 to 18 ring-forming carbon atoms.

[0155] In the method for producing a deuterated compound according to this embodiment, the deuterium source preferably includes a condensed ring structure.

[0156] It is preferable that one or more hydrogen atoms bonded to the fused ring structure in the deuterium source are deuterium atoms. It is also preferable that all of the hydrogen atoms bonded to the fused ring structure in the deuterium source are deuterium atoms.

[0157] In the method for producing a deuterated compound according to this embodiment, the deuterium source is preferably an aromatic compound. The aromatic compound used as the deuterium source is a compound that has a different structure or deuteration rate from the compound having an aromatic ring (raw material compound) to which the deuterium atom is to be introduced.

[0158] The deuterium source preferably contains one or more rings selected from the group consisting of condensed aromatic hydrocarbon rings and condensed aromatic heterocycles as a condensed ring structure.

[0159] The condensed aromatic hydrocarbon ring contained in the deuterium source is preferably a condensed aromatic hydrocarbon ring having 10 to 50 ring-forming carbon atoms, more preferably a condensed aromatic hydrocarbon ring having 10 to 30 ring-forming carbon atoms, and even more preferably a condensed aromatic hydrocarbon ring having 10 to 18 ring-forming carbon atoms.

[0160] The condensed aromatic heterocycle contained in the deuterium source is preferably a condensed aromatic heterocycle having 9 to 50 ring-forming carbon atoms, more preferably a condensed aromatic heterocycle having 9 to 30 ring-forming carbon atoms, and even more preferably a condensed aromatic heterocycle having 9 to 18 ring-forming carbon atoms.

[0161] The deuterium source preferably includes one or more rings selected from the group consisting of condensed aromatic hydrocarbon rings in which all hydrogen atoms are deuterium atoms and condensed aromatic heterocycles in which all hydrogen atoms are deuterium atoms.

[0162] In the method for producing a deuterated compound according to this embodiment, the deuterium source is preferably a fused ring structure having two or more rings. In the method for producing a deuterated compound according to this embodiment, the deuterium source is preferably a fused ring structure having five or fewer rings, and more preferably a fused ring structure having four or fewer rings.

[0163] In the method for producing a deuterated compound according to this embodiment, it is preferable that the total number of ring-forming carbons and ring-forming atoms of the rings contained in the deuterium source is less than the total number of ring-forming carbons and ring-forming atoms of the rings contained in the compound having the aromatic ring (raw material compound) described above.

[0164] In the method for producing a deuterated compound according to this embodiment, it is preferable that the total number of rings contained in the deuterium source is less than the total number of rings contained in the compound having the aromatic ring (raw material compound) described above.

[0165] Examples of ring structures and fused ring structures contained in deuterium sources include naphthalene rings, anthracene rings, phenanthrene rings, and paradichlorobenzene rings.

[0166] In the method for producing a deuterated compound according to this embodiment, the deuterium source preferably includes one or more rings selected from the group consisting of a naphthalene ring in which one or more hydrogen atoms are deuterium atoms, an anthracene ring in which one or more hydrogen atoms are deuterium atoms, a phenanthrene ring in which one or more hydrogen atoms are deuterium atoms, and a paradichlorobenzene ring in which one or more hydrogen atoms are deuterium atoms. It is more preferable that the source includes one or more rings selected from the group consisting of a naphthalene ring in which all hydrogen atoms are deuterium atoms, an anthracene ring in which all hydrogen atoms are deuterium atoms, a phenanthrene ring in which all hydrogen atoms are deuterium atoms, and a paradichlorobenzene ring in which all hydrogen atoms are deuterium atoms.

[0167] In the method for producing a deuterated compound according to this embodiment, the deuterium source preferably includes a naphthalene ring in which all hydrogen atoms are deuterium atoms.

[0168] In the method for producing a deuterated compound according to this embodiment, the deuterium source is preferably a total deuterium compound. In this specification, "total deuterium compound" means a compound in which all hydrogen atoms in the compound used as the deuterium source are deuterium atoms.

[0169] In the method for producing a deuterated compound according to this embodiment, it is also preferable that the deuterium source be naphthalene (naphthalene-d8), in which all hydrogen atoms are deuterium atoms.

[0170] In the method for producing a deuterated compound according to this embodiment, it is also preferable that the deuterium source is not a total deuterium compound.

[0171] (Specific examples of deuterium sources) Specific examples of deuterium sources used in the method for producing deuterated compounds according to this embodiment include, for example, the following compounds. However, the present invention is not limited to these specific examples of deuterium sources.

[0172]

[0173] (Acid) In the method for producing the deuterated compound according to this embodiment, the acid dissociation constant pKa of the acid in water at 25°C is preferably 0 or less, and more preferably less than 0.

[0174] In the method for producing a deuterated compound according to this embodiment, the acid dissociation constant pKa of the acid in water at 25°C is preferably -5 or less, and more preferably -10 or less. In the method for producing a deuterated compound according to this embodiment, the acid dissociation constant pKa of the acid in water at 25°C is preferably -25 or more, and more preferably -20 or more.

[0175] In the method for producing a deuterated compound according to this embodiment, the acid preferably contains a sulfur atom as a constituent atom. Examples of acids containing a sulfur atom as a constituent atom include sulfuric acid and sulfonic acid. In the method for producing a deuterated compound according to this embodiment, the acid preferably contains a halogen atom as a constituent atom, and more preferably contains a fluorine atom as a constituent atom. In the production method according to this embodiment, the acid preferably has a haloalkyl group, more preferably has a fluoroalkyl group, and even more preferably contains a perfluoroalkyl group in which all hydrogen atoms of the alkyl group are replaced with fluorine atoms. In the method for producing a deuterated compound according to this embodiment, the acid preferably contains an oxygen atom as a constituent atom. In the method for producing a deuterated compound according to this embodiment, the acid preferably contains an oxygen atom and a sulfur atom as constituent atoms. In the method for producing a deuterated compound according to this embodiment, the acid preferably contains a sulfonic acid group. In the method for producing a deuterated compound according to this embodiment, the acid preferably contains at least one atom selected from the group consisting of sulfur, oxygen, and fluorine atoms as a constituent atom. In the production method according to this embodiment, the acid more preferably contains sulfur, oxygen, and fluorine atoms as constituent atoms. In the manufacturing method according to this embodiment, the acid may contain hydrogen atoms or carbon atoms.

[0176] (Solvent) The solvent in the method for producing the deuterated compound according to this embodiment is not particularly limited, as long as it can dissolve or disperse at least the compound having an aromatic ring (starting compound), the acid, and the deuterium source. Examples of solvents include protic solvents and aprotic solvents. In the production method according to this embodiment, the solvent is preferably an aprotic solvent. In the production method according to this embodiment, not only a single solvent but also a combination of multiple solvents can be used. In the method for producing the deuterated compound according to this embodiment, the solvent is preferably free of deuterium atoms.

[0177] In the method for producing a deuterated compound according to this embodiment, the solvent may preferably contain halogen atoms as constituent atoms. Examples of solvents containing halogen atoms as constituent atoms include ortho-dichlorobenzene, meta-dichlorobenzene, and para-dichlorobenzene. In one aspect of the production method according to this embodiment, the solvent is at least one selected from the group consisting of ortho-dichlorobenzene, meta-dichlorobenzene, and para-dichlorobenzene.

[0178] In one embodiment of the manufacturing method according to this embodiment, an aliphatic hydrocarbon solvent may or may not be used. Examples of aliphatic hydrocarbon solvents include linear, branched, or cyclic aliphatic hydrocarbon solvents. In one embodiment, the aliphatic hydrocarbon solvent may be saturated or unsaturated.

[0179] In the method for producing a deuterated compound according to this embodiment, the solvent may also preferably contain nitrogen atoms as constituent atoms.

[0180] Furthermore, in the method for producing the deuterated compound according to this embodiment, it is also preferable that the solvent contains oxygen atoms as constituent atoms.

[0181] The solvent used in the method for producing the deuterated compound according to this embodiment may be a solvent containing nitrogen and oxygen atoms as constituent atoms, such as nitric acid.

[0182] (Other substances that can be used in the method for producing deuterated compounds) In the method for producing deuterated compounds of this embodiment, a catalyst may be used in the second step. Examples of catalysts in this case include aluminum catalysts, platinum catalysts, and palladium catalysts.

[0183] In the method for producing the deuterated compound of this embodiment, it is preferable not to use a platinum catalyst.

[0184] In the method for producing the deuterated compound of this embodiment, it is also preferable not to use a catalyst selected from the group consisting of platinum catalysts, rhodium catalysts, and ruthenium catalysts.

[0185] In the method for producing the deuterated compound of this embodiment, it is also preferable not to use a metal catalyst selected from the group consisting of platinum, palladium, rhodium, ruthenium, nickel, cobalt, their oxides, their complexes, and combinations thereof.

[0186] In the method for producing the deuterated compound of this embodiment, it is also preferable not to use a metal catalyst.

[0187] In the method for producing the deuterated compound of this embodiment, it is preferable not to use metal halides.

[0188] Next, each step of the method for producing the deuterated compound according to this embodiment will be described.

[0189] [First Step] The first step is to dissolve or disperse a compound having an aromatic ring (raw material compound) in a solvent to obtain a first solution. In this specification, "solution" includes not only a state in which the raw materials are dissolved in a solvent, but also a state in which the raw materials are dispersed in a solvent.

[0190] In the method for producing a deuterated compound according to this embodiment, the temperature and time in the first step can be set appropriately according to the materials used, and can be set, for example, in accordance with the examples described later.

[0191] [Second Step] The second step is to dissolve or disperse an acid and a deuterium source in the first solution described above, either simultaneously or separately, to deuterate at least a portion of the aromatic ring-containing compound (starting compound) in the first solution.

[0192] In the second step, when the acid and the deuterium source are dissolved or dispersed separately in the first solution, for example, as in the example described later, the deuterium source may be dissolved or dispersed in the first solution to obtain a deuterium source-containing solution, and then the acid may be dissolved or dispersed in the deuterium source-containing solution. Alternatively, for example, the acid may be dissolved or dispersed in the first solution to obtain an acid-containing solution, and then the deuterium source may be dissolved or dispersed in the acid-containing solution.

[0193] In the method for producing a deuterated compound according to this embodiment, the temperature in the second step is preferably set considering the rate of deuteration and the degree of damage to the compound having an aromatic ring (raw material compound). For example, the temperature in the second step is preferably set in the range of room temperature (25°C) or higher and 100°C or lower.

[0194] In the method for producing a deuterated compound according to this embodiment, the temperature in the first and second steps is preferably room temperature (25°C) or higher, and more preferably 28°C or higher. Furthermore, in the method for producing a deuterated compound according to this embodiment, the temperature in the first and second steps is preferably 35°C or lower, and more preferably 30°C or lower. According to the method for producing a deuterated compound according to this embodiment, it is considered that deuterium is easily released from the deuterium source. Therefore, the activity can be improved without heating as in the conventional method, and the deuterated compound can be produced at around room temperature.

[0195] In the method for producing a deuterated compound according to this embodiment, the method for dissolving or dispersing the compound having an aromatic ring (raw material compound) in a solvent in the first step, and the method for dissolving or dispersing the acid and deuterium source in the first solution in the second step are not particularly limited. For example, in the second step, as in the examples described later, the deuterium source may be dissolved or dispersed in the first solution to obtain a deuterium source-containing solution, and then the acid may be added dropwise to the deuterium source-containing solution.

[0196] In one embodiment of the method for producing a deuterated compound according to this embodiment, heavy water is not used in the first and second steps.

[0197] In one embodiment, in one embodiment of the method for producing a deuterated compound according to this embodiment, heavy water or light water is used after the second step for the purpose of stopping the reaction.

[0198] In one embodiment, the method for producing the deuterated compound according to this embodiment does not use a liquid deuterated compound at 25°C and 1 atm.

[0199] The deuterated compounds produced by the method for producing deuterated compounds according to this embodiment are often not a single compound, but a mixture of compounds containing different numbers of deuterium atoms. The deuterated compound produced by the method for producing deuterated compounds according to this embodiment preferably has a deuterated ratio of 20% or more, more preferably 25% or more, and even more preferably 30% or more, as an indicator of the mixing ratio of compounds containing different numbers of deuterium atoms. If the deuterated compound produced by the method for producing deuterated compounds according to this embodiment is a mixture, the deuterated ratio of the mixture can be determined by following the method described in the examples below. Furthermore, because the deuterated compound produced by the method for producing deuterated compounds according to this embodiment is a mixture of compounds containing different numbers of deuterium atoms, there is variation in the deuterated ratio. Therefore, the average number of deuterium atoms in one molecule of the deuterated compound produced by the method for producing deuterated compounds according to this embodiment N Ｄ The number of average light hydrogen atoms in one molecule of the deuterated compound produced by the method for producing the deuterated compound according to this embodiment is N. Ｈ The total number of hydrogen atoms in one molecule of the deuterated compound produced by the method for producing the deuterated compound according to this embodiment is N. Ａ (=N Ｄ +N Ｈ Based on ) and , it can also be calculated using the following formula (formula W1). In the following formula (formula W1), R Ｄ This represents the deuteration rate of the compound. Ｄ = (N Ｄ / N Ａ ) × 100 … (Number W1)

[0200] Furthermore, if the deuterated compound produced by the method for producing a deuterated compound according to this embodiment is a mixture of compounds with different numbers of deuterium atoms, it is preferable that the proportion of deuterated compounds in which one-quarter or more, preferably one-third or more, of the hydrogen atoms in the molecule are deuterium atoms is 50% or more of the total mixture, based on the number of atoms.

[0201] The deuterated compound produced by the method for producing the deuterated compound of this embodiment can be used as a material for various applications, and can be used as a material for organic EL elements, for example. An organic EL element comprises one or more light-emitting units between the anode and cathode electrodes. This light-emitting unit may have one or more layers containing at least one selected from the group consisting of organic compounds and inorganic substances. The inorganic substance is at least one of an inorganic compound and an element. Preferably, the light-emitting unit contains one or more layers selected from the group consisting of a layer composed of an organic compound, a layer composed of an inorganic substance, and a layer composed of both organic compounds and inorganic substances.

[0202] In an organic EL device, the light-emitting unit includes one or more light-emitting layers. In addition to the one or more light-emitting layers, other layers that may be included in the light-emitting unit include, for example, layers that can be used in an organic EL device. The layers that can be used in an organic EL device are not particularly limited, but include, for example, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a barrier layer.

[0203] The light-emitting unit of an organic EL element preferably has one of the following layer configurations: • Electron barrier layer / Light-emitting layer / Hole barrier layer • Hole injection layer / Electron barrier layer / Light-emitting layer / Hole barrier layer • Hole transport layer / Electron barrier layer / Light-emitting layer / Hole barrier layer • Hole injection layer / Hole transport layer / Electron barrier layer / Light-emitting layer / Hole barrier layer / Electron injection layer • Electron barrier layer / Light-emitting layer / Hole barrier layer / Electron transport layer / Electron barrier layer / Light-emitting layer / Hole barrier layer / Electron transport layer / Hole injection layer • Hole injection layer / Electron barrier layer / Light-emitting layer / Hole barrier layer / Electron transport layer • Hole injection layer / Sub-barrier layer / Emitting layer / Hole barrier layer / Electron transport layer / Electron injection layer / Hole transport layer / Electron barrier layer / Emitting layer / Hole barrier layer / Electron injection layer / Hole transport layer / Electron barrier layer / Emitting layer / Hole barrier layer / Electron transport layer / Hole transport layer / Hole transport layer / Hole transport layer / Electron barrier layer / Emitting layer / Hole barrier layer / Electron injection layer / Hole transport layer / Hole transport layer / Electron barrier layer / Emitting layer / Hole barrier layer / Electron transport layer / Hole injection layer / Hole transport layer / Electron barrier layer / Emitting layer / Hole barrier layer / Electron transport layer / Electron injection layer

[0204] The deuterated compound produced by the method for producing the deuterated compound of this embodiment is preferably contained in one or more layers in the light-emitting unit of the organic EL element. The deuterated compound may be contained in multiple layers.

[0205] Deuterated compounds may be contained alone in a single layer, or together with at least one other compound. The other compounds contained in a single layer together with the deuterated compound may, independently, be undeuterated compounds (sometimes referred to as non-deuterated compounds) or deuterated compounds.

[0206] [Modifications of Embodiments] The present invention is not limited to the embodiments described above, and any modifications, improvements, etc., that can achieve the objectives of the present invention are included in the present invention.

[0207] The following describes examples of the present invention. The present invention is not limited in any way by these examples.

[0208] [Example 1] Example 1 relates to a method for producing compound BH-1 as a deuterated compound. The production scheme for compound BH-1 is shown below. Note that R in compound BH-1 １ ~R ２０ Each of these is independently either a light hydrogen atom or a deuterium atom (D).

[0209]

[0210] (Preparation of Deuterium Compound) In a 100 mL flask, 1.0 g of a light hydrogen compound (compound BH-A), which is a compound having an aromatic ring (starting compound), was dissolved in 40 mL of ortho-dichlorobenzene as a solvent to obtain the first solution. Next, 6.1 g of naphthalene-d8 (20 equivalents per 1 equivalent of light hydrogen compound) was dissolved in the first solution as a deuterium source. To this solution (solution containing the deuterium source), 0.40 mL of trifluoromethanesulfonic acid was added dropwise at room temperature (25°C), and the mixture was stirred at 25°C for 24 hours. After stirring, 5 mL of heavy water was added, and the organic layer was extracted with dichloromethane. The organic layer was concentrated, and the resulting residue was purified by silica gel column chromatography to obtain 803 mg of a white solid (yield: 80%). This white solid was identified as compound BH-1 as a deuterated compound based on the results of mass spectral analysis described later.

[0211] (Calculation of Deuterated Rate) The deuterated rate of compound BH-1 was calculated using the following method. The mass spectrum of compound BH-1 was measured using a liquid chromatograph-mass spectrometer (LCMS-8050, Shimadzu Corporation). From the shape of the measured mass spectrum, the mixing ratio of compounds with different numbers of deuterium atoms was determined by multiple regression analysis. Furthermore, the proportion of deuterated hydrogen atoms out of the total hydrogen atoms calculated from this was used as the "deuterated rate". As a result, the deuterated rate of compound BH-1 as a mixture was 39.7%.

[0212] The manufacturing method of Example 1 yielded a mixture of deuterated compounds with different numbers of deuterium atoms in their molecules. Figure 1 is a graph showing the proportion of deuterated compounds in the mixture obtained in Example 1. In the graph of Figure 1, the vertical axis is the normalized MS intensity, and the horizontal axis is the mass-to-charge ratio. In the graph of Figure 1, "Original," "Fitting," "D-conversion rate," "Deviation," "Dnumber," and "ratio%" have the following meanings: "Original": MS spectrum of the measured sample "Fitting": Simulation result by multiple regression analysis "D-conversion rate": Deuteration rate "Deviation": Error between actual and simulation "Dnumber": Number of deuterium atoms contained in one molecule "ratio%": Proportion of the compound contained in the mixture

[0213] [Comparative Example 1] Comparative Example 1 relates to a method for producing compound Ref-1. The production scheme for compound Ref-1 is shown below. Note that R in compound Ref-1 １０１ ~R １２０ Each of these is independently either a light hydrogen atom (H) or a deuterium atom (D).

[0214]

[0215] Comparative Example 1 was prepared in the same manner as in Example 1, except that deuterated benzene (10 v / w) (46 equivalents) was used instead of naphthalene-d8 (6.1 g) (20 equivalents) as the deuterium source. When the deuterated rate was calculated in the same manner as in Example 1, the deuterated rate of the compound Ref-1 mixture obtained by the production method of Comparative Example 1 was 16%. In the production method of the deuterated compound of Comparative Example 1, the amount of deuterium source used was defined as 1 (v / w) when 1 mL of deuterated benzene was used per 1 g of compound BH-A (light hydrogen compound).

[0216] The manufacturing method in Example 1 used a compound that is solid at 25°C and 1 atm as the deuterium source. Compared to the manufacturing method in Comparative Example 1, which used heavy benzene that is liquid at 25°C and 1 atm as the deuterium source, this method produced a deuterated compound (compound BH-1) with a higher deuterated ratio as a mixture. Furthermore, since the manufacturing method in Example 1 does not use heavy benzene, it was possible to produce the deuterated compound under safer manufacturing conditions compared to the manufacturing method in Comparative Example 1.

Claims

1. A method for producing a deuterated compound, comprising: a first step of dissolving or dispersing a compound having an aromatic ring in a solvent to obtain a first solution; and a second step of dissolving or dispersing an acid and a deuterium source in the first solution simultaneously or separately to deuterate at least a portion of the compound having an aromatic ring in the first solution, wherein the deuterium source is a compound that is solid at 25°C and 1 atm, has one or more deuterium atoms, and is a compound different from the deuterated compound.

2. The method for producing a deuterated compound according to claim 1, wherein in the second step, the deuterium source is dissolved or dispersed in the first solution to obtain a solution containing a deuterium source, and then the acid is dissolved or dispersed in the solution containing a deuterium source.

3. The method for producing a deuterated compound according to claim 1, wherein in the second step, the acid is dissolved or dispersed in the first solution to obtain an acid-containing solution, and then the deuterium source is dissolved or dispersed in the acid-containing solution.

4. The method for producing a deuterated compound according to any one of claims 1 to 3, wherein the deuterium source is a compound that is solid at 30°C and 1 atm.

5. The method for producing a deuterated compound according to any one of claims 1 to 3, wherein the deuterium source is a compound that is solid at 50°C and 1 atm.

6. The method for producing a deuterated compound according to any one of claims 1 to 5, wherein the compound having the aromatic ring does not contain a deuterium atom.

7. A method for producing a deuterated compound according to any one of claims 1 to 6, wherein the deuterium source includes a condensed ring structure.

8. The method for producing a deuterated compound according to any one of claims 1 to 7, wherein the deuterium source comprises a naphthalene ring in which all hydrogen atoms are deuterium atoms.

9. A method for producing a deuterated compound according to any one of claims 1 to 8, wherein the deuterium source is not a total deuterium compound.

10. The method for producing a deuterated compound according to any one of claims 1 to 9, wherein the compound having the aromatic ring comprises at least one of an anthracene ring and a xanthene ring.

11. The method for producing a deuterated compound according to claim 10, wherein the anthracene ring is a benzanthracene ring.

12. A method for producing a deuterated compound according to any one of claims 1 to 11, wherein the acid dissociation constant pKa of the acid in water at 25°C is 0 or less.

13. The method for producing a deuterated compound according to any one of claims 1 to 12, wherein the deuterium source is a compound having a melting point of 100°C or less.

14. The method for producing a deuterated compound according to any one of claims 1 to 12, wherein the deuterium source is a compound having a melting point of 80°C or lower.

15. A method for producing a deuterated compound according to any one of claims 1 to 14, wherein the acid contains a sulfur atom as a constituent atom.

16. A method for producing a deuterated compound according to any one of claims 1 to 15, wherein the solvent contains halogen atoms as constituent atoms.

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