JP2014218457A - Isoindoline-based compound and manufacturing method therefor - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an isoindoline-based compound having high color density with high brightness, high fastness and useful as a coloring agent, and to provide a manufacturing method therefor.SOLUTION: There is provided an isoindoline-based compound represented by the general formula (1) and there is provided a method for manufacturing an isoindoline-based compound including reacting a specific pyrrolinone compound and a specific imino compound. (1), where A represents a substituted or unsubstituted aromatic ring group or a substituted or unsubstituted heterocyclic group, a ring X represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heterocyclic ring, Rrepresents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted aralkyl group.

Description

The present invention relates to a novel isoindoline compound and a method for producing the same. More specifically, it is used as a blue colorant for plastic colorants, inks, paints, inks for ink jet printers, color toners, etc., and has a clear, high color density and high fastness, and an indoline compound and a method for producing the same About.

Conventionally, various compounds such as anthraquinones, phthalocyanines, and indigo have been developed and used as blue colorants.
For example, Patent Document 1 discloses an anthraquinone dye as a highly durable blue coloring agent for resin coloring. However, this anthraquinone dye has a drawback of low color density.
Patent Document 2 discloses that a phthalocyanine compound is used for coloring a color filter or the like. However, the phthalocyanine compound has a problem that the extinction coefficient is lowered due to aggregation and aggregation of molecules.
The isoindoline-based colorant is a compound having a completely different structure from the compound of the present invention. However, Patent Documents 3 to 5 disclose that complexes and pigments having various structures are used for coloring resins and the like. ing. However, a colorant having excellent overall durability such as color characteristics such as coloring power, sharpness, hue, light resistance, heat resistance, solvent resistance, and migration resistance has not been obtained.

JP 2005-520906 gazette Japanese Patent Laid-Open No. 08-302224 JP 61-133270 A Japanese Patent Laid-Open No. 62-020561 Japanese Patent Application Laid-Open No. 07-196937

An object of the present invention is to provide an isoindoline-based compound having a clear and high color density and useful as a colorant having high fastness and a method for producing the same.

As a result of intensive studies on the above problems, the present inventors have determined that the isoindoline-based compound having a specific structure has coloring properties, vividness, color characteristics such as hue, light resistance, heat resistance, solvent resistance, migration resistance, etc. As a result, the present invention has been completed. That is, the present invention
(I) an isoindoline compound represented by the general formula (1),
[Wherein, A represents a substituted or unsubstituted aromatic ring group, a substituted or unsubstituted heterocyclic group, ring X represents a substituted or unsubstituted aromatic ring, a substituted or unsubstituted heterocyclic ring, and R ₁ represents A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aralkyl group are shown. ]

(Ii) A is a substituted or unsubstituted benzene ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted anthracene ring, substituted or unsubstituted pyridine ring, substituted or unsubstituted quinoline ring, substituted or unsubstituted Pyrrole ring, substituted or unsubstituted indole ring, substituted or unsubstituted thiophene ring, substituted or unsubstituted benzothiophene ring, substituted or unsubstituted furan ring, substituted or unsubstituted benzofuran ring, ring X substituted Or unsubstituted benzene ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted anthracene ring, substituted or unsubstituted pyridine ring, substituted or unsubstituted pyrazine ring, substituted or unsubstituted carbazole ring, substituted or unsubstituted Substituted dibenzofuran ring, substituted or unsubstituted quinoline ring, substituted or unsubstituted quinoxaline ring, substituted Unsubstituted phenothiazine ring, a substituted or unsubstituted acridone ring, isoindoline compounds of substituted or unsubstituted anthraquinone ring, a substituted or unsubstituted thianthrene ring, a substituted or unsubstituted phenoxazine ring (i),

(Iii) A is a substituted or unsubstituted benzene ring, substituted or unsubstituted pyridine ring, substituted or unsubstituted pyrrole ring, substituted or unsubstituted thiophene ring, substituted or unsubstituted benzothiophene ring, substituted or unsubstituted Wherein the ring X is a substituted or unsubstituted benzene ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted anthracene ring, substituted or unsubstituted pyridine ring, substituted or unsubstituted carbazole ring, substituted Or an isoindoline of (i) or (ii) which is an unsubstituted dibenzofuran ring, a substituted or unsubstituted acridone ring, a substituted or unsubstituted anthraquinone ring, a substituted or unsubstituted thianthrene ring, a substituted or unsubstituted phenothiazine ring Compound,

(Iv) A is unsubstituted, or as a substituent, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, substituted or unsubstituted, respectively Benzene ring, naphthalene ring, anthracene ring, pyridine ring, quinoline ring, pyrrole ring, indole ring, having at least one selected from alkylthio groups, substituted or unsubstituted amino groups, and substituted or unsubstituted heterocyclic groups , A thiophene ring, a benzothiophene ring, a furan ring, or a benzofuran ring, wherein ring X is unsubstituted, or each has a halogen atom, hydroxyl group, nitro group, substituted or unsubstituted alkyl group, substituted or unsubstituted Substituted aryl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted aralkyl group, Or an unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, an unsubstituted or unsubstituted arylthio group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted arylcarbonyl group And a benzene ring, naphthalene ring, anthracene ring, pyridine ring, pyrazine ring, carbazole ring, dibenzofuran ring, quinoline ring, quinoxaline ring, phenothiazine ring, acridone ring having at least one selected from a substituted or unsubstituted amino group , An anthraquinone ring, a thianthrene ring, or a phenoxazine ring (i) to (iii) any of the isoindoline compounds,

(V) A is unsubstituted or as a substituent, a halogen atom, a cyano group, an alkyl group having 1 to 8 carbon atoms, a halogenated alkyl group having 1 to 8 carbon atoms, or a dialkyl having 3 to 18 carbon atoms in total. A benzene ring, a pyridine ring, a pyrrole ring, a thiophene ring, a benzothiophene ring, or at least one selected from an aminoalkoxy group, a dialkylamino group having 2 to 16 carbon atoms in total, and an alkoxy group having 1 to 8 carbon atoms, or It is a furan ring, ring X is unsubstituted, or each has a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or a dialkylamino group having 2 to 16 carbon atoms as a substituent. A benzene ring having at least one selected from aryloxy groups having 6 to 18 carbon atoms and arylcarbonyl groups having 7 to 19 carbon atoms, naphtha Down ring, an anthracene ring, a pyridine ring, a carbazole ring, a dibenzofuran ring, acridone ring, an anthraquinone ring, a thianthrene ring or a phenothiazine ring,, R ₁ is a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, carbon atoms 2 (I) to (iv) any isoindoline compound which is a substituted or unsubstituted alkenyl group having 8 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms,

(Vi) reacting a pyrrolinone compound represented by the general formula (2) with an imino compound represented by the general formula (3), (4) or (5); ) Method for producing any isoindoline-based compound,
[In the formula, A represents a substituted or unsubstituted aromatic group, a substituted or unsubstituted heterocyclic group, and R ₁ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted group. An aryl group, a substituted or unsubstituted aralkyl group is shown. ]
[Wherein, ring X represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heterocyclic ring, and R ₂ represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, substituted or unsubstituted A substituted aryl group, a substituted or unsubstituted aralkyl group, R ₃ represents a substituted or unsubstituted alkyl group, R ₄ and R ₅ each independently represents a substituted or unsubstituted alkyl group, R ₄ And R ₅ may combine to form a ring. ]

(Vii) In the general formula (2), A is a substituted or unsubstituted benzene ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted anthracene ring, substituted or unsubstituted pyridine ring, substituted or unsubstituted quinoline Ring, substituted or unsubstituted pyrrole ring, substituted or unsubstituted indole ring, substituted or unsubstituted thiophene ring, substituted or unsubstituted benzothiophene ring, substituted or unsubstituted furan ring, substituted or unsubstituted benzofuran ring In general formulas (3), (4) and (5), ring X is a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted Pyridine ring, substituted or unsubstituted pyrazine ring, substituted or unsubstituted carbazole ring, substituted or unsubstituted dibenzofuran ring, substituted or unsubstituted Is an unsubstituted quinoline ring, substituted or unsubstituted quinoxaline ring, substituted or unsubstituted phenothiazine ring, substituted or unsubstituted acridone ring, substituted or unsubstituted anthraquinone ring, substituted or unsubstituted thianthrene ring, substituted or unsubstituted A substituted phenoxazine ring, wherein R ₄ and R ₅ are substituted or unsubstituted alkyl groups, R ₄ and R ₅ are substituted oxygen atoms, and a substituted or unsubstituted dioxolane ring formed with these common basic carbon atoms , A method for producing (vi), wherein R ₄ and R ₅ are substituted oxygen atoms and substituted or unsubstituted dioxane rings formed together with these common basic carbon atoms,
About.

According to the present invention, a novel isoindoline useful as a blue colorant that is comprehensively excellent in durability such as color characteristics such as coloring power, sharpness, hue, light resistance, heat resistance, solvent resistance, migration resistance, etc. A compound and a method for producing the same are provided.

2 is an IR spectrum diagram of the compound (1) -1 produced in Example 1. FIG. 1 is a visible light absorption spectrum diagram of the compound (1) -1 produced in Example 1. FIG. 4 is an IR spectrum diagram of the compound (1) -27 produced in Example 3. FIG. 2 is a visible light absorption spectrum diagram of the compound (1) -27 produced in Example 3. FIG.

Hereinafter, the present invention will be described in detail.
[Isoindoline compounds]
The first invention of the present invention is an isoindoline compound represented by the general formula (1).
[Wherein, A represents a substituted or unsubstituted aromatic ring group, a substituted or unsubstituted heterocyclic group, ring X represents a substituted or unsubstituted aromatic ring, a substituted or unsubstituted heterocyclic ring, and R ₁ represents A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aralkyl group are shown. ]

In general formula (1), A is preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted quinoline ring. , Substituted or unsubstituted pyrrole ring, substituted or unsubstituted indole ring, substituted or unsubstituted thiophene ring, substituted or unsubstituted benzothiophene ring, substituted or unsubstituted furan ring, substituted or unsubstituted benzofuran ring is there.
A is more preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrrole ring, a substituted or unsubstituted thiophene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted A substituted furan ring.

When A has a substituent, the substituent includes a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group A substituted or unsubstituted amino group or a substituted or unsubstituted heterocyclic group is preferable.
More preferably, the substituent is a halogen atom, a cyano group, an alkyl group having 1 to 8 carbon atoms, a halogenated alkyl group having 1 to 8 carbon atoms, a dialkylaminoalkoxy group having 3 to 18 carbon atoms, or 2 to 2 carbon atoms. 16 dialkylamino groups and C1-C8 alkoxy groups.

A is unsubstituted or substituted as a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio, respectively. Benzene ring, naphthalene ring, anthracene ring, pyridine ring, quinoline ring, pyrrole ring, indole ring, thiophene having at least one selected from a group, a substituted or unsubstituted amino group, and a substituted or unsubstituted heterocyclic group What is a ring, a benzothiophene ring, a furan ring, or a benzofuran ring is preferable.
More preferably, A is unsubstituted or a halogen atom, a cyano group, an alkyl group having 1 to 8 carbon atoms, a halogenated alkyl group having 1 to 8 carbon atoms, or a total carbon number of 3 to 18 as a substituent. A benzene ring, a pyridine ring, a pyrrole ring, a thiophene ring, a benzothiophene ring, having at least one selected from a dialkylaminoalkoxy group, a dialkylamino group having 2 to 16 carbon atoms in total, and an alkoxy group having 1 to 8 carbon atoms, Or a furan ring.

Examples of the substituent for ring A are shown below.
Examples of the substituent for A that is a halogen atom include a chlorine atom, a fluorine atom, a bromine atom, and an iodine atom, with a chlorine atom and a fluorine atom being preferred.

As what a substituent is a substituted or unsubstituted alkyl group, a C1-C12 substituted or unsubstituted alkyl group is preferable, and a C1-C8 substituted or unsubstituted alkyl group is more preferable.
Examples of unsubstituted alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl Group, tert-pentyl group, n-hexyl group, 1-methylpentyl group, 4-methyl-2-pentyl group, 2-ethylbutyl group, n-heptyl group, 1-methylhexyl group, n-octyl group, 1- Examples thereof include linear or branched unsubstituted alkyl groups such as methylheptyl group and 2-ethylhexyl group.
Examples of the substituted alkyl group include, for example, a methoxymethyl group, an ethoxymethyl group, an n-butoxymethyl group, an n-hexyloxymethyl group, a (2-ethylbutyloxy) methyl group, and 2- (4′-pentenyloxy). An alkyl group having an alkyloxy group or an alkenyloxy group, such as an ethyl group, for example, an alkyl group having an aralkyloxy group, such as a benzyloxymethyl group or 2- (benzyloxymethoxy) ethyl group, a phenyloxymethyl group, 4 -Alkyl groups having an aryloxy group such as a chlorophenyloxymethyl group and 4- (2'-phenyloxyethoxy) butyl group, for example, a thioalkyl group such as an n-butylthiomethyl group and a 2-n-octylthioethyl group Alkyl group having, for example, fluoromethyl group, trifluoromethyl , Pa - fluoroethyl group, 4-fluoro-cyclohexyl group, dichloromethyl group, 4-chloro cyclohexyl group include alkyl groups having a halogen atom such as 7-chloro-heptyl group.
As the substituent is a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms is preferable, and a substituted or unsubstituted aryl group having 6 to 14 carbon atoms is more preferable.

  Examples of the substituted or unsubstituted aryl group include a phenyl group, 1-naphthyl group, 2-naphthyl group, 2-anthracenyl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 1-pyrenyl group, Unsubstituted aryl groups such as 2-pyrenyl group, 2-perylenyl group, 3-perylenyl group, 2-fluoranthenyl group, 3-fluoranthenyl group, 7-fluoranthenyl group, 8-fluoranthenyl group, For example, 1-methyl-2-pyrenyl group, 2-methylphenyl group, 4-ethylphenyl group, 4- (4′-tert-butylcyclohexyl) phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group, 4 -Has an alkyl group such as ethyl-1-naphthyl group, 6-n-butyl-2-naphthyl group, 2,4-dimethylphenyl group, etc. Aryl groups such as 4-methoxyphenyl group, 3-ethoxyphenyl group, 2-ethoxyphenyl group, 4-n-propoxyphenyl group, 3-n-propoxyphenyl group, 4-isopropoxyphenyl group, 3-iso Propoxyphenyl group, 2-isopropoxyphenyl group, 2-sec-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2-methyl-5-methoxyphenyl group, 2-phenyloxy Aryl group having alkoxy group such as phenyl group or aryloxy group, 4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group, 2,6-diphenylphenyl group, 4- (2′-naphthyl) Phenyl group, 2-phenyl-1-naphthyl group, 1-phenyl-2-naphthyl group, 7 -Aryl groups having an aryl group such as phenyl-1-pyrenyl group, such as 4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 2- Halogen atoms such as chloro-5-methylphenyl group, 2-chloro-6-methylphenyl group, 2-methyl-3-chlorophenyl group, 2-methoxy-4-fluorophenyl group, 2-fluoro-4-methoxyphenyl group An aryl group having 2-, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 3,5-bistrifluoromethylphenyl group, 4-perfluoroethylphenyl group, 4- Methylthiophenyl group, 4-ethylthiophenyl group, 4-cyanophenyl group, 3-cyanophene Etc. Le group.

As what a substituent is a substituted or unsubstituted alkoxy group, a C1-C18 substituted or unsubstituted alkoxy group is preferable, and a C1-C8 substituted or unsubstituted alkoxy group is more preferable.
Examples of the unsubstituted alkoxy group include, for example, methoxy group, ethoxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, isobutyloxy group, tert-butyloxy group, sec-butyloxy group, n-pentyloxy Group, isopentyloxy group, n-hexyloxy group, 2-methylpentyloxy group, 1,1-dimethylbutyloxy group, 1,2,2-trimethylpropyloxy group, 2-ethylbutyloxy group, 1,3 -Dimethylhexyloxy group, cyclohexyloxy group, methylcyclopentyloxy group, n-heptyloxy group, n-heptyloxy group, n-octyloxy group, 3,5,5-trimethylhexyloxy group, n-decyloxy group, n -Undecyloxy group, n-dodecyloxy group, 1-adamantyloxy group, Examples include linear, branched or cyclic unsubstituted alkoxy groups such as an n-pentadecyloxy group.
Examples of the substituted alkoxy group include, for example, a methoxymethoxy group, an ethoxymethoxy group, an n-propyloxymethoxy group, an n-butyloxymethoxy group, an isobutyloxymethoxy group, a tert-butyloxymethoxy group, and an n-pentyloxymethoxy group. 2-methoxyethoxy group, 2-ethoxyethoxy group, 2-n-propyloxyethoxy group, 2-isopropyloxyethoxy group, 2-n-butyloxyethoxy group, 2-isobutyloxyethoxy group, 2-tert-butyl Oxyethoxy group, 2-sec-butyloxyethoxy group, 2-n-pentyloxyethoxy group, 2-isopentyloxyethoxy group, 2-tert-pentyloxyethoxy group, 2-sec-pentyloxyethoxy group, 2- Cyclopentyloxyethoxy group, 2-n-hexyloxyeth Si group, 2- (4-ethylcyclohexyloxy) ethoxy group, 2-n-nonyloxyethoxy group, 2- (3,5,5-trimethylhexyloxy) ethoxy group, 2-n-decyloxyethoxy group, 2 -N-dodecyloxyethoxy group, 3-methoxypropyloxy group, 3-ethoxypropyloxy group, 3- (n-propyloxy) propyloxy group, 2-isopentyloxypropyloxy group, 2-methoxybutyloxy group, Alkoxy such as 4-ethoxybutyloxy group, 4- (n-propyloxy) butyloxy group, 4-isopropyloxybutyloxy group, 5-methoxypentyloxy group, 5-ethoxymethoxy group, 6-n-propylhexyloxy group An alkoxy group substituted with a group;

Methoxymethoxymethoxy group, ethoxymethoxymethoxy group, propyloxymethoxymethoxy group, butyloxymethoxymethoxy group, methoxyethoxymethoxy group, ethoxyethoxymethoxy group, propyloxyethoxymethoxy group, methoxymethoxyethoxy group, ethoxymethoxyethoxy group, propyloxy Methoxyethoxy group, butyloxymethoxyethoxy group, propyloxyethoxyethoxy group, butyloxyethoxyethoxy group, propyloxybutyloxyethoxy group, methoxymethoxypropyloxy group, ethoxymethoxypropyloxy group, butyloxymethoxypropyloxy group, methoxymethoxy Butyloxy group, ethoxymethoxybutyloxy group, butyloxymethoxybutyloxy group, ethoxyethoxybutyl Alkoxy group, (4 Echirushikuro hexyloxy) ethoxyethoxy group, [4- (3,5,5-trimethyl hexyloxy) butyloxy] alkoxy group substituted with an alkoxyalkoxy group such as ethoxy group;
Alkoxy groups substituted with alkoxycarbonyl groups such as methoxycarbonylmethoxy group, ethoxycarbonylmethoxy group, n-propyloxycarbonylmethoxy group, isopropyloxycarbonylmethoxy group, (4'-ethylcyclohexyloxy) carbonylmethoxy group, methoxycarbonylethoxy An alkoxy group substituted with an alkoxycarbonyl group such as a group, ethoxycarbonylethoxy group, n-propyloxycarbonylethoxy group, ethoxycarbonylpropyloxy group;

Methylaminomethoxy group, 2-methylaminoethoxy group, 2- (2-methylaminoethoxy) ethoxy group, 4-methylaminobutyloxy group, 1-methylaminopropan-2-yloxy group, 3-methylaminopropyloxy group 2-methylamino-2-methylpropyloxy group, 2-ethylaminoethoxy group, 2- (2-ethylaminoethoxy) ethoxy group, 3-ethylaminopropyloxy group, 1-ethylaminopropyloxy group, 2- An alkoxy group substituted with an alkylamino group such as isopropylaminoethoxy group, 2- (n-butylamino) ethoxy group, 3- (n-hexylamino) propyloxy group, 4- (cyclohexylamino) butyloxy group;
Dimethylaminomethoxy group, 2-dimethylaminoethoxy group, 2- (2-dimethylaminoethoxy) ethoxy group, 4-dimethylaminobutyloxy group, 1-dimethylaminopropan-2-yloxy group, 3-dimethylaminopropyloxy group 2-dimethylamino-2-methylpropyloxy group, 2-diethylaminoethoxy group, 2- (2-diethylaminoethoxy) ethoxy group, 3-diethylaminopropyloxy group, 1-diethylaminopropyloxy group, 2-diisopropylaminoethoxy group An alkoxy group substituted with a dialkylamino group such as 2- (di-n-butylamino) ethoxy group, 2-piperidylethoxy group, 3- (di-n-hexylamino) propyloxy group;
Alkoxy substituted with alkylaminoalkoxy groups such as methylaminomethoxymethoxy group, methylaminoethoxyethoxy group, methylaminoethoxypropyloxy group, ethylaminoethoxypropyloxy group, 4- (2′-isobutylaminopropyloxy) butyloxy group Group;

Alkoxy groups substituted with dialkylaminoalkoxy groups such as dimethylaminomethoxymethoxy group, dimethylaminoethoxyethoxy group, dimethylaminoethoxypropyloxy group, diethylaminoethoxypropyloxy group, 4- (2′-diisobutylaminopropyloxy) butyloxy group ;
Methylthiomethoxy group, 2-methylthioethoxy group, 2-ethylthioethoxy group, 2-n-propylthioethoxy group, 2-isopropylthioethoxy group, 2-n-butylthioethoxy group, 2-isobutylthioethoxy group, ( An alkoxy group substituted with an alkylthio group such as a 3,5,5-trimethylhexylthio) hexyloxy group;
2-N-morpholinylethoxy group, 2-N-pyridylethoxy group, 2-N-pyrrolylethoxy group, 2- (2-furyl) ethoxy group, 2- (1-indolyl) ethoxy group, 2- ( 3-thienyl) ethoxy group, 3-N-morpholinylpropyloxy group, 3-N-pyridylpropyloxy group, 3-N-pyrrolylpropyloxy group, 3- (1-indolyl) propyloxy group and the like An alkoxy group substituted with a ring group; and the like.

As what a substituent is a substituted or unsubstituted alkylthio group, a C1-C18 substituted or unsubstituted alkylthio group is preferable, and a C1-C8 substituted or unsubstituted alkylthio group is more preferable.
Examples of the unsubstituted alkylthio group include, for example, methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, isobutylthio group, tert-butylthio group, sec-butylthio group, n-pentylthio group, Isopentylthio group, n-hexylthio group, 2-methylpentylthio group, 1,1-dimethylbutylthio group, 1,2,2-trimethylpropylthio group, 2-ethylbutylthio group, 1,3-dimethylhexyl Thio group, cyclohexylthio group, methylcyclopentylthio group, n-heptylthio group, n-heptylthio group, n-octylthio group, 3,5,5-trimethylhexylthio group, n-decylthio group, n-undecylthio group, n-dodecylthio group, 1-adamantylthio group, n-pentadecylthio group, etc., straight chain, branched or ring And an unsubstituted alkylthio group.
Examples of substituted alkylthio groups include, for example, methoxymethylthio group, ethoxymethylthio group, n-propyloxymethylthio group, n-butyloxymethylthio group, isobutyloxymethylthio group, tert-butyloxymethylthio group, n-pentyloxymethylthio group 2-methoxyethylthio group, 2-ethoxyethylthio group, 2-n-propyloxyethylthio group, 2-isopropyloxyethylthio group, 2-n-butyloxyethylthio group, 2-isobutyloxyethylthio group 2-tert-butyloxyethylthio group, 2-sec-butyloxyethylthio group, 2-n-pentyloxyethylthio group, 2-isopentyloxyethylthio group, 2-sec-pentyloxyethylthio group, 2-n-hexyloxyethylthio group, 2- (4-ethylcyclo Xyloxy) ethylthio group, 2-n-nonyloxyethylthio group, 2- (3,5,5-trimethylhexyloxy) ethylthio group, 2-n-decyloxyethylthio group, 2-n-dodecyloxyethylthio group 3-methoxypropylthio group, 3-ethoxypropylthio group, 3- (n-propylthio) propylthio group, 2-isopentyloxypropylthio group, 2-methoxybutylthio group, 4-ethoxybutylthio group, 4- An alkylthio group substituted with an alkoxy group such as (n-propyloxy) butylthio group, 5-methoxypentylthio group, 5-ethoxypentylthio group, 6-n-propyloxyhexylthio group;
Methoxymethoxymethylthio group, ethoxymethoxymethylthio group, propyloxymethoxymethylthio group, butyloxymethoxymethylthio group, ethoxyethoxymethylthio group, propyloxyethoxymethylthio group, methoxymethoxyethylthio group, ethoxymethoxyethylthio group, propyloxymethoxyethylthio group Group, butyloxymethoxyethylthio group, propyloxyethoxyethylthio group, butyloxyethoxyethylthio group, propyloxybutyloxyethylthio group, methoxymethoxypropylthio group, ethoxymethoxypropylthio group, butyloxymethoxypropylthio group, Butyloxymethoxybutylthio group, ethoxyethoxybutylthio group, cyclohexyloxyethoxyethylthio group, [4- (3,5,5-tri Ethylhexyl oxy) butyloxy] alkylthio group substituted with an alkoxyalkoxy group such as an ethylthio group;
In alkoxycarbonyl groups such as methoxycarbonylmethylthio group, ethoxycarbonylmethylthio group, n-propyloxycarbonylmethylthio group, methoxycarbonylethylthio group, ethoxycarbonylethylthio group, n-propyloxycarbonylethylthio group, ethoxycarbonylpropylthio group, etc. A substituted alkylthio group;
Methylaminomethylthio group, 2-methylaminoethylthio group, 2- (2-methylaminoethoxy) ethylthio group, 4-methylaminobutylthio group, 1-methylaminopropan-2-yloxy group, 3-methylaminopropylthio Group, 2-ethylaminoethylthio group, 2- (2-ethylaminoethoxy) ethylthio group, 3-ethylaminopropylthio group, 1-ethylaminopropylthio group, 2-isopropylaminoethylthio group, 2- (n An alkylthio group substituted with an alkylamino group such as a -butylamino) ethylthio group, a 3- (n-hexylamino) propylthio group, or a 4- (cyclohexylamino) butylthio group;
Dimethylaminomethylthio group, 2-dimethylaminoethylthio group, 4-dimethylaminobutylthio group, 1-dimethylaminopropan-2-ylthio group, 3-dimethylaminopropylthio group, 2-diethylaminoethylthio group, 3-diethylamino Dialkylamino groups such as propylthio group, 2-diisopropylaminoethylthio group, 2- (di-n-butylamino) ethylthio group, 2-piperidylethylthio group, 3- (di-n-hexylamino) propylthio group; A substituted alkylthio group;
Methylthiomethylthio group, 2-methylthioethylthio group, 2-ethylthioethylthio group, 2-n-propylthioethylthio group, 2-isopropylthioethylthio group, 2-n-butylthioethylthio group, 2-isobutyl An alkylthio group substituted with an alkylthio group such as a thioethylthio group or a (3,5,5-trimethylhexylthio) hexylthio group;
2-N-morpholinylethylthio group, 2-N-pyridylethylthio group, 2-N-pyrrolylethylthio group, 2- (2-furyl) ethylthio group, 2- (1-indolyl) ethylthio group, 2- (3-thienyl) ethylthio group, 3-N-morpholinylpropylthio group, 3-N-pyridylpropylthio group, 3-N-pyrrolylpropylthio group, 3- (1-indolyl) propylthio group, etc. An alkylthio group substituted with a heterocyclic group of
As the substituent being a substituted or unsubstituted amino group, an amino group or a substituted amino group having 1 to 24 carbon atoms is preferable, and a dialkylamino group having 2 to 16 carbon atoms is more preferable.

As the substituent of the substituted amino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group is preferable.
Examples include methylamino group, ethylamino group, propylamino group, butylamino group, pentylamino group, hexylamino group, heptylamino group, octylamino group, 2-ethylhexylamino group, cyclohexylamino group, 3, 5 Monoalkylamino groups such as, 5-trimethylhexylamino group, nonylamino group, decylamino group;
Dimethylamino group, diethylamino group, methylethylamino group, di-n-propylamino group, di-n-butylamino group, di-n-pentylamino group, N-methyl-N-ethylamino group, N-ethyl- Dialkylamino groups such as N-isopropylamino group, N-ethyl-N-cyclohexylamino group, N-methyl-Nn-octylamino group;
N-methyl-N-phenylamino group, N-ethyl-N-phenylamino group, N-ethyl-N- (2,4-dimethylphenyl) amino group, Nn-propyl-N- (2-ethoxyphenyl) ) Aryl group such as amino group, N-methyl-N- (3-chlorophenyl) amino group, diphenylamino group, di- (p-tolyl) amino group, N-methyl-N- (2-naphthyl) amino group Having an amino group;
Benzylamino group, phenethylamino group, 3-phenylpropylamino group, 4-ethylbenzylamino group, 4-isopropylbenzylamino group, dibenzylamino group, diphenethylamino group, bis (4-ethylbenzyl) amino group, bis An amino group having an aralkyl group such as (4-isopropylbenzyl) amino group, N-ethyl-N-benzylamino group, N-methyl-N-phenethylamino group, and the like.
Examples of the substituent as a substituted or unsubstituted heterocyclic group include an alkyl group, an alkoxy group, an alkylthio group, an amino group, a morpholino group optionally having a halogen atom, a pyridyl group, a piperidinyl group, Indolyl group, furyl group, furfuryl group, thiophenyl group and the like can be mentioned.

In general formula (1), ring X is preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted pyridine ring, or a substituted or unsubstituted benzene. Ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted anthracene ring, substituted or unsubstituted pyridine ring, substituted or unsubstituted pyrazine ring, substituted or unsubstituted carbazole ring, substituted or unsubstituted dibenzofuran ring, Substituted or unsubstituted quinoline ring, substituted or unsubstituted quinoxaline ring, substituted or unsubstituted phenothiazine ring, substituted or unsubstituted acridone ring, substituted or unsubstituted anthraquinone ring, substituted or unsubstituted thianthrene ring, substituted or An unsubstituted phenoxazine ring.
Ring X is more preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted carbazole ring, substituted or unsubstituted A substituted dibenzofuran ring, a substituted or unsubstituted acridone ring, a substituted or unsubstituted anthraquinone ring, a substituted or unsubstituted thianthrene ring, and a substituted or unsubstituted phenothiazine ring.

When the ring X has a substituent, the substituent includes a halogen atom, a hydroxyl group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, substituted or unsubstituted Aralkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, unsubstituted or unsubstituted arylthio group, substituted or unsubstituted amino group, substituted or unsubstituted Are preferably an alkylcarbonyl group or a substituted or unsubstituted arylcarbonyl group.
More preferably, the substituent is a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 12 carbon atoms in total, an aryloxy group having 6 to 18 carbon atoms, or carbon. It is an arylcarbonyl group of formula 8-19.

Ring X is unsubstituted or substituted as a halogen atom, hydroxyl group, nitro group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted aryl group, substituted or Unsubstituted aralkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, unsubstituted or unsubstituted arylthio group, substituted or unsubstituted alkylcarbonyl group, substituted Or a benzene ring, naphthalene ring, anthracene ring, pyridine ring, pyrazine ring, carbazole ring, dibenzofuran ring, quinoline ring, quinoxaline having at least one selected from an unsubstituted arylcarbonyl group and a substituted or unsubstituted amino group Ring, phenothiazine ring, acridone ring, anthraki A non-ring, a thianthrene ring, or a phenoxazine ring is preferred.
More preferably, the ring X is unsubstituted or each has a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or a dialkylamino group having 2 to 12 carbon atoms as a substituent. , A benzene ring, a naphthalene ring, an anthracene ring, a pyridine ring, a carbazole ring, a dibenzofuran ring, an acridone ring, having at least one selected from aryloxy groups having 6 to 18 carbon atoms and arylcarbonyl groups having 7 to 19 carbon atoms , Anthraquinone ring, thianthrene ring, or phenothiazine ring.
Examples of substituents for ring X are shown below.
Examples in which the substituent is a halogen atom include chlorine, bromine, fluorine, and iodine.
As what a substituent is a substituted or unsubstituted alkyl group, a C1-C12 substituted or unsubstituted alkyl group is preferable, and a C1-C8 substituted or unsubstituted alkyl group is more preferable.

Examples of the unsubstituted alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, Neopentyl group, tert-pentyl group, n-hexyl group, 1-methylpentyl group, 4-methyl-2-pentyl group, 2-ethylbutyl group, n-heptyl group, cyclohexyl group, 1-methylhexyl group, n-octyl And linear, branched or cyclic alkyl groups such as 1-methylheptyl group and 2-ethylhexyl group.
Examples of the alkyl group having a substituent include a methoxymethyl group, an ethoxymethyl group, an n-butoxymethyl group, an n-hexyloxymethyl group, a (2-ethylbutyloxy) methyl group, and 2- (4′-pentenyloxy). ) An alkyl group having an alkyloxy group or an alkenyloxy group such as an ethyl group, for example, an alkyl group having an aralkyloxy group such as a benzyloxymethyl group or 2- (benzyloxymethoxy) ethyl group, a phenyloxymethyl group, Examples thereof include alkyl groups having an aryloxy group such as a 4-chlorophenyloxymethyl group and a 4- (2′-phenyloxyethoxy) butyl group.
As the substituent is a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkenyl group having 2 to 12 carbon atoms is preferable, and a substituted or unsubstituted alkenyl group having 2 to 8 carbon atoms is more preferable.

Examples of the substituted or unsubstituted alkenyl group include a vinyl group, a propenyl group, a 1-butenyl group, an isobutenyl group, a 1-pentenyl group, a 2-pentenyl group, a 2-methyl-1-butenyl group, and a 2-cyclopentenyl group. 1-vinylhexyl group, styryl group, styrylmethyl group, 2-styrylethyl group, and the like.
As what a substituent is a substituted or unsubstituted aryl group, a C6-C24 substituted or unsubstituted aryl group is preferable, and a C6-C18 substituted or unsubstituted aryl group is more preferable.

  Examples of the substituted or unsubstituted aryl group include a phenyl group, 1-naphthyl group, 2-naphthyl group, 2-anthracenyl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 1-pyrenyl group, Unsubstituted aryl groups such as 2-pyrenyl group, 2-perylenyl group, 3-perylenyl group, 2-fluoranthenyl group, 3-fluoranthenyl group, 7-fluoranthenyl group, 8-fluoranthenyl group, For example, 1-methyl-2-pyrenyl group, 2-methylphenyl group, 4-ethylphenyl group, 4- (4′-tert-butylcyclohexyl) phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group, 4 -Has an alkyl group such as ethyl-1-naphthyl group, 6-n-butyl-2-naphthyl group, 2,4-dimethylphenyl group, etc. Aryl groups such as 4-methoxyphenyl group, 3-ethoxyphenyl group, 2-ethoxyphenyl group, 4-n-propoxyphenyl group, 3-n-propoxyphenyl group, 4-isopropoxyphenyl group, 3-iso Propoxyphenyl group, 2-isopropoxyphenyl group, 2-sec-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2-methyl-5-methoxyphenyl group, 2-phenyloxy Aryl group having alkoxy group such as phenyl group or aryloxy group, 4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group, 2,6-diphenylphenyl group, 4- (2′-naphthyl) Phenyl group, 2-phenyl-1-naphthyl group, 1-phenyl-2-naphthyl group, 7 -Aryl groups having an aryl group such as phenyl-1-pyrenyl group, such as 4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 2- Halogen atoms such as chloro-5-methylphenyl group, 2-chloro-6-methylphenyl group, 2-methyl-3-chlorophenyl group, 2-methoxy-4-fluorophenyl group, 2-fluoro-4-methoxyphenyl group An aryl group having 2-, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 3,5-bistrifluoromethylphenyl group, 4-perfluoroethylphenyl group, 4- Methylthiophenyl group, 4-ethylthiophenyl group, 4-cyanophenyl group, 3-cyanophene Etc. Le group.

As the substituent is a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkyl group having 7 to 25 carbon atoms is preferable, and a substituted or unsubstituted aralkyl group having 7 to 19 carbon atoms is more preferable.
Examples of the substituted or unsubstituted aralkyl group include benzyl group, α-methylbenzyl group, phenethyl group, α-methylphenethyl group, α, α-dimethylbenzyl group, α, α-dimethylphenethyl group, 4-methylphenethyl group. Group, an aralkyl group having an unsubstituted or alkyl group such as 4-methylbenzyl group, 4-isopropylbenzyl group, for example, an aryl such as 4-benzylbenzyl group, 4-phenethylbenzyl group, 4-phenylbenzyl group, etc. Or an aralkyl group having an aralkyl group, such as 4-methoxybenzyl group, 4-n-tetradecyloxybenzyl group, 4-n-heptadecyloxybenzyl group, 3,4-dimethoxybenzyl group, 4-methoxymethylbenzyl Group, 4-vinyloxymethylbenzyl group, 4-benzyloxybenzyl group, 4- Aralkyl group having a substituent group, such as E phenethyl oxy benzyl group. For example, an aralkyl group having a hydroxyl group such as a 4-hydroxybenzyl group and a 4-hydroxy-3-methoxybenzyl group, for example, a halogen atom such as a 4-fluorobenzyl group, a 3-chlorobenzyl group, and a 3,4-dichlorobenzyl group And an aralkyl group having a 2-furfuryl group, a diphenylmethyl group, a 1-naphthylmethyl group, a 2-naphthylmethyl group, and the like.

As what a substituent is a substituted or unsubstituted alkoxy group, a C1-C18 substituted or unsubstituted alkoxy group is preferable, and a C1-C8 substituted or unsubstituted alkoxy group is more preferable.
Specific examples of the unsubstituted alkoxy group include, for example, methoxy group, ethoxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, isobutyloxy group, tert-butyloxy group, sec-butyloxy group, n- Pentyloxy group, isopentyloxy group, n-hexyloxy group, 2-methylpentyloxy group, 1,1-dimethylbutyloxy group, 1,2,2-trimethylpropyloxy group, 2-ethylbutyloxy group, 1 , 3-dimethylhexyloxy group, cyclohexyloxy group, methylcyclopentyloxy group, n-heptyloxy group, n-heptyloxy group, n-octyloxy group, 3,5,5-trimethylhexyloxy group, n-decyloxy group , N-undecyloxy group, n-dodecyloxy group, 1-adamantyloxy Examples thereof include linear, branched or cyclic unsubstituted alkoxy groups such as a cis group and an n-pentadecyloxy group.

Examples of the substituted alkoxy group include, for example, a methoxymethoxy group, an ethoxymethoxy group, an n-propyloxymethoxy group, an n-butyloxymethoxy group, an isobutyloxymethoxy group, a tert-butyloxymethoxy group, and an n-pentyloxymethoxy group. 2-methoxyethoxy group, 2-ethoxyethoxy group, 2-n-propyloxyethoxy group, 2-isopropyloxyethoxy group, 2-n-butyloxyethoxy group, 2-isobutyloxyethoxy group, 2-n-pentyl Oxyethoxy group, 2-isopentyloxyethoxy group, 2-cyclopentyloxyethoxy group, 2-n-hexyloxyethoxy group, 2- (4-ethylcyclohexyloxy) ethoxy group, 2-n-nonyloxyethoxy group, 2 -(3,5,5-trimethylhexyloxy) Ethoxy group, 2-n-decyloxyethoxy group, 2-n-dodecyloxyethoxy group, 3-methoxypropyloxy group, 3-ethoxypropyloxy group, 3- (n-propyloxy) propyloxy group, 2-iso Pentyloxypropyloxy group, 2-methoxybutyloxy group, 4-ethoxybutyloxy group, 4- (n-propyloxy) butyloxy group, 4-isopropyloxybutyloxy group, 5-methoxypentyloxy group, 5-ethoxymethoxy An alkoxy group substituted with an alkoxy group such as a group;
Methoxymethoxymethoxy group, ethoxymethoxymethoxy group, propyloxymethoxymethoxy group, butyloxymethoxymethoxy group, methoxyethoxymethoxy group, ethoxyethoxymethoxy group, propyloxyethoxymethoxy group, methoxymethoxyethoxy group, ethoxymethoxyethoxy group, propyloxy Methoxyethoxy group, butyloxymethoxyethoxy group, propyloxyethoxyethoxy group, butyloxyethoxyethoxy group, propyloxybutyloxyethoxy group, methoxymethoxypropyloxy group, ethoxymethoxypropyloxy group, butyloxymethoxypropyloxy group, methoxymethoxy Butyloxy group, ethoxymethoxybutyloxy group, butyloxymethoxybutyloxy group, ethoxyethoxybutyl Alkoxy group, (4 Echirushikuro hexyloxy) ethoxyethoxy group, [4- (3,5,5-trimethyl hexyloxy) butyloxy] alkoxy group substituted with an alkoxyalkoxy group such as ethoxy group;
Alkoxy groups substituted with alkoxycarbonyl groups such as methoxycarbonylmethoxy group, ethoxycarbonylmethoxy group, n-propyloxycarbonylmethoxy group, isopropyloxycarbonylmethoxy group, (4'-ethylcyclohexyloxy) carbonylmethoxy group, methoxycarbonylethoxy An alkoxy group substituted with an alkoxycarbonyl group such as a group, ethoxycarbonylethoxy group, n-propyloxycarbonylethoxy group, ethoxycarbonylpropyloxy group;
Methylaminomethoxy group, 2-methylaminoethoxy group, 2- (2-methylaminoethoxy) ethoxy group, 4-methylaminobutyloxy group, 1-methylaminopropan-2-yloxy group, 3-methylaminopropyloxy group 2-methylamino-2-methylpropyloxy group, 2-ethylaminoethoxy group, 2- (2-ethylaminoethoxy) ethoxy group, 3-ethylaminopropyloxy group, 1-ethylaminopropyloxy group, 2- An alkoxy group substituted with an alkylamino group such as isopropylaminoethoxy group, 2- (n-butylamino) ethoxy group, 3- (n-hexylamino) propyloxy group, 4- (cyclohexylamino) butyloxy group;
Dimethylaminomethoxy group, 2-dimethylaminoethoxy group, 2- (2-dimethylaminoethoxy) ethoxy group, 4-dimethylaminobutyloxy group, 1-dimethylaminopropan-2-yloxy group, 3-dimethylaminopropyloxy group 2-dimethylamino-2-methylpropyloxy group, 2-diethylaminoethoxy group, 2- (2-diethylaminoethoxy) ethoxy group, 3-diethylaminopropyloxy group, 1-diethylaminopropyloxy group, 2-diisopropylaminoethoxy group An alkoxy group substituted with a dialkylamino group such as 2- (di-n-butylamino) ethoxy group, 2-piperidylethoxy group, 3- (di-n-hexylamino) propyloxy group;
Alkoxy substituted with alkylaminoalkoxy groups such as methylaminomethoxymethoxy group, methylaminoethoxyethoxy group, methylaminoethoxypropyloxy group, ethylaminoethoxypropyloxy group, 4- (2′-isobutylaminopropyloxy) butyloxy group Group;
Alkoxy groups substituted with dialkylaminoalkoxy groups such as dimethylaminomethoxymethoxy group, dimethylaminoethoxyethoxy group, dimethylaminoethoxypropyloxy group, diethylaminoethoxypropyloxy group, 4- (2′-diisobutylaminopropyloxy) butyloxy group ;
Methylthiomethoxy group, 2-methylthioethoxy group, 2-ethylthioethoxy group, 2-n-propylthioethoxy group, 2-isopropylthioethoxy group, 2-n-butylthioethoxy group, 2-isobutylthioethoxy group, ( 3,5,5-trimethylhexylthio) alkoxy group substituted with an alkylthio group such as hexyloxy group; and the like.

As the substituent is a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group having 6 to 24 carbon atoms is preferable, and a substituted or unsubstituted aryloxy group having 6 to 18 carbon atoms is more preferable. preferable.
The substituted or unsubstituted aryloxy group includes a heteroaryloxy group, and includes a phenyloxy group, a 2-methylphenyloxy group, a 4-methylphenyloxy group, a 4-ethylphenyloxy group, and a 4-isopropylphenyloxy group. 4-isobutylphenyloxy group, 4-n-pentylphenyloxy group, 4-tert-pentylphenyloxy group, 4-cyclohexylphenyloxy group, 4-n-octylphenyloxy group, 4-n-decylphenyloxy group 4-n-dodecylphenyloxy group, 4-n-hexadecylphenyloxy group, 2,3-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 3,4 , 5-trimethylphenyloxy group, 5-indanyloxy group, 1,2 3,4-tetrahydro-6-naphthyloxy group, 3-methoxyphenyloxy group, 3-ethoxyphenyloxy group, 4-n-propoxyphenyloxy group, 4-n-butoxyphenyloxy group, 4-n-pentyloxy Phenyloxy group, 4-cyclohexyloxyphenyloxy group, 4-n-octyloxyphenyloxy group, 4-n-decyloxyphenyloxy group, 4-n-dodecyloxyphenyloxy group, 4-n-hexadecyloxyphenyl Oxy group, 2,3-dimethoxyphenyloxy group, 2,5-dimethoxyphenyloxy group, 3,5-dimethoxyphenyloxy group, 2-methoxy-4-methylphenyloxy group, 3-methoxy-4-methylphenyloxy Group, 3-methyl-4-methoxyphenyloxy group, 2-fluoro Enyloxy group, 4-fluorophenyloxy group, 3-chlorophenyloxy group, 4-bromophenyloxy group, 3-trifluoromethylphenyloxy group, 3,5-difluorophenyloxy group, 3,4-dichlorophenyloxy group, 2 -Methyl-4-chlorophenyloxy group, 3-chloro-4-methylphenyloxy group, 3-methoxy-4-fluorophenyloxy group, 3-fluoro-4-methoxyphenyloxy group, 4-phenylphenyloxy group, 3 -Phenylphenyloxy group, 4- (4'-methylphenyl) phenyloxy group, 4- (4'-methoxyphenyl) phenyloxy group, 1-naphthyloxy group, 4-methyl-1-naphthyloxy group, 6- n-butyl-2-naphthyloxy group, 7-ethoxy-2-naphthyloxy group, 2-thieni Examples include a ruoxy group, a 2-pyridyloxy group, and a 4-pyridyloxy group.

As what a substituent is a substituted or unsubstituted alkylthio group, a C1-C18 substituted or unsubstituted alkylthio group is preferable, and a C1-C8 substituted or unsubstituted alkylthio group is more preferable.
Examples of the unsubstituted alkylthio group include, for example, methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, isobutylthio group, tert-butylthio group, sec-butylthio group, n-pentylthio group, Isopentylthio group, n-hexylthio group, 2-methylpentylthio group, 1,1-dimethylbutylthio group, 1,2,2-trimethylpropylthio group, 2-ethylbutylthio group, 1,3-dimethylhexyl Thio group, cyclohexylthio group, methylcyclopentylthio group, n-heptylthio group, n-heptylthio group, n-octylthio group, 3,5,5-trimethylhexylthio group, n-decylthio group, n-undecylthio group, n-dodecylthio group, 1-adamantylthio group, n-pentadecylthio group, etc., straight chain, branched or ring And an unsubstituted alkylthio group.
Examples of substituted alkylthio groups include, for example, methoxymethylthio group, ethoxymethylthio group, n-propyloxymethylthio group, n-butyloxymethylthio group, isobutyloxymethylthio group, tert-butyloxymethylthio group, n-pentyloxymethylthio group 2-methoxyethylthio group, 2-ethoxyethylthio group, 2-n-propyloxyethylthio group, 2-isopropyloxyethylthio group, 2-n-butyloxyethylthio group, 2-isobutyloxyethylthio group 2-tert-butyloxyethylthio group, 2-sec-butyloxyethylthio group, 2-n-pentyloxyethylthio group, 2-isopentyloxyethylthio group, 2-sec-pentyloxyethylthio group, 2-n-hexyloxyethylthio group, 2- (4-ethylcyclo Xyloxy) ethylthio group, 2-n-nonyloxyethylthio group, 2- (3,5,5-trimethylhexyloxy) ethylthio group, 2-n-decyloxyethylthio group, 2-n-dodecyloxyethylthio group 3-methoxypropylthio group, 3-ethoxypropylthio group, 3- (n-propylthio) propylthio group, 2-isopentyloxypropylthio group, 2-methoxybutylthio group, 4-ethoxybutylthio group, 4- An alkylthio group substituted with an alkoxy group such as (n-propyloxy) butylthio group, 5-methoxypentylthio group, 5-ethoxypentylthio group, 6-n-propyloxyhexylthio group;
Methoxymethoxymethylthio group, ethoxymethoxymethylthio group, propyloxymethoxymethylthio group, butyloxymethoxymethylthio group, ethoxyethoxymethylthio group, propyloxyethoxymethylthio group, methoxymethoxyethylthio group, ethoxymethoxyethylthio group, propyloxymethoxyethylthio group Group, butyloxymethoxyethylthio group, propyloxyethoxyethylthio group, butyloxyethoxyethylthio group, propyloxybutyloxyethylthio group, methoxymethoxypropylthio group, ethoxymethoxypropylthio group, butyloxymethoxypropylthio group, Butyloxymethoxybutylthio group, ethoxyethoxybutylthio group, cyclohexyloxyethoxyethylthio group, [4- (3,5,5-tri Ethylhexyl oxy) butyloxy] alkylthio group substituted with an alkoxyalkoxy group such as an ethylthio group;
In alkoxycarbonyl groups such as methoxycarbonylmethylthio group, ethoxycarbonylmethylthio group, n-propyloxycarbonylmethylthio group, methoxycarbonylethylthio group, ethoxycarbonylethylthio group, n-propyloxycarbonylethylthio group, ethoxycarbonylpropylthio group, etc. A substituted alkylthio group;
Methylaminomethylthio group, 2-methylaminoethylthio group, 2- (2-methylaminoethoxy) ethylthio group, 4-methylaminobutylthio group, 1-methylaminopropan-2-yloxy group, 3-methylaminopropylthio Group, 2-ethylaminoethylthio group, 2- (2-ethylaminoethoxy) ethylthio group, 3-ethylaminopropylthio group, 1-ethylaminopropylthio group, 2-isopropylaminoethylthio group, 2- (n An alkylthio group substituted with an alkylamino group such as a -butylamino) ethylthio group, a 3- (n-hexylamino) propylthio group, or a 4- (cyclohexylamino) butylthio group;
Dimethylaminomethylthio group, 2-dimethylaminoethylthio group, 4-dimethylaminobutylthio group, 1-dimethylaminopropan-2-ylthio group, 3-dimethylaminopropylthio group, 2-diethylaminoethylthio group, 3-diethylamino Dialkylamino groups such as propylthio group, 2-diisopropylaminoethylthio group, 2- (di-n-butylamino) ethylthio group, 2-piperidylethylthio group, 3- (di-n-hexylamino) propylthio group; A substituted alkylthio group;
Methylthiomethylthio group, 2-methylthioethylthio group, 2-ethylthioethylthio group, 2-n-propylthioethylthio group, 2-isopropylthioethylthio group, 2-n-butylthioethylthio group, 2-isobutyl An alkylthio group substituted with an alkylthio group such as a thioethylthio group or a (3,5,5-trimethylhexylthio) hexylthio group;
2-N-morpholinylethylthio group, 2-N-pyridylethylthio group, 2-N-pyrrolylethylthio group, 2- (2-furyl) ethylthio group, 2- (1-indolyl) ethylthio group, 2- (3-thienyl) ethylthio group, 3-N-morpholinylpropylthio group, 3-N-pyridylpropylthio group, 3-N-pyrrolylpropylthio group, 3- (1-indolyl) propylthio group, etc. An alkylthio group substituted with a heterocyclic group of
As the substituent being a substituted or unsubstituted arylthio group, a substituted or unsubstituted arylthio group having 6 to 24 carbon atoms is preferable, and a substituted or unsubstituted arylthio group having 6 to 18 carbon atoms is more preferable.

  The substituted or unsubstituted arylthio group includes a heteroarylthio group, and includes a phenylthio group, a 2-methylphenylthio group, a 4-methylphenylthio group, a 3-ethylphenylthio group, and a 4-n-propylphenylthio group. 4-n-butylphenylthio group, 4-isobutylphenylthio group, 4-tert-butylphenylthio group, 4-n-pentylphenylthio group, 4-n-hexylphenylthio group, 4-cyclohexylphenylthio group 4-n-octylphenylthio group, 4-n-dodecylphenylthio group, 4-n-octadecylphenylthio group, 2,5-dimethylphenylthio group, 3,4-dimethylphenylthio group, 5-indanylthio group 1,2,3,4-tetrahydro-6-naphthylthio group, 2-methoxyphenylthio group, 3-methoxy Phenylthio group, 4-ethoxyphenylthio group, 4-n-propoxyphenylthio group, 2,4-dimethoxyphenylthio group, 3,5-diethoxyphenylthio group, 2-methoxy-4-methylphenylthio group, 2 -Methyl-4-methoxyphenylthio group, 2-fluorophenylthio group, 4-fluorophenylthio group, 2-chlorophenylthio group, 4-bromophenylthio group, 4-trifluoromethylphenylthio group, 3-trifluoro Methylphenylthio group, 2,4-difluorophenylthio group, 2,4-dichlorophenylthio group, 2-chloro-4-methoxyphenylthio group, 2-naphthylthio group, 4-methyl-1-naphthylthio group, 4-ethoxy -1-naphthylthio group, 2-pyridylthio group, 4-aminophenylthio group, 4- (N, N-dimethyl) Ruamino) phenylthio group, 4- (N, N-diethylamino) -1-naphthylthio group, 4- [N, N-di (4′-methylphenyl) amino] phenylthio group, 4- (N-phenoxadiyl) phenylthio Group and the like.

As the substituent is a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted alkylcarbonyl group having 2 to 13 carbon atoms is preferred, and a substituted or unsubstituted alkylcarbonyl group having 2 to 9 carbon atoms in total. Is more preferable.
Examples of the substituted or unsubstituted alkylcarbonyl group include formyl group, acetyl group, propionyl group, butyryl group, valeryl group, iso-valeryl group, sec-valeryl group, trimethylacetyl group, hexanoyl group, t-butylacetyl group, heptanoyl Group, octanoyl group, 2-ethylhexanoyl group, nonanoyl group, decanoyl group, undecanoyl group, lauroyl group, tridecanoyl group, tetraadecanoyl group, pentadecanoyl group, hexadecanoyl group, heptadecanoyl group, octadecanoyl group, Oleoyl group, cyclopentanecarbonyl group, cyclohexanecarbonyl group, 6-chlorohexanoyl group, 6-bromohexanoyl group, trifluoroacetyl group, pentafluoropropionyl group, perfluorooctanoyl group, 2,2,4, 4, , 5,7,7,7- nonafluoro-3,6-oxa heptanoyl group, methoxyacetyl group, 3,6-oxa heptanoyl group, cinnamoyl group and the like.

As the substituent is a substituted or unsubstituted arylcarbonyl group, a substituted or unsubstituted arylcarbonyl group having 7 to 25 carbon atoms is preferable, and a substituted or unsubstituted arylcarbonyl group having 7 to 19 carbon atoms in total. Is more preferable.
Examples of the substituted or unsubstituted arylcarbonyl group include benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, 4-ethylbenzoyl group, 4-n-propylbenzoyl group, 4-tert- Butylbenzoyl group, 2,4-dimethylbenzoyl group, 2,4,6-trimethylbenzoyl group, 2,4,5-trimethylbenzoyl group, 4-ethylbenzoyl group, 4-isopropylbenzoyl group, 4-n-butylbenzoyl group Group, 4-isobutylbenzoyl group, 4-sec-butylbenzoyl group, 4-tert-butylbenzoyl group, 4-n-pentylbenzoyl group, 4-isopentylbenzoyl group, 4-neopentibenzoyl group, 4-isohexyl Benzoyl group, 4-cyclohexylbenzoyl group, 4-octylbenzoyl group 4-cyanobenzoyl group, 4-nitrobenzoyl group, 4-trifluoromethylbenzoyl group, 3-bromobenzoyl group, 2-fluorobenzoyl group, 4-chlorobenzoyl group, 2,6-dichlorobenzoyl group, 2,4- Examples thereof include a difluorobenzoyl group, a naphthylcarbonyl-1-yl group, and a naphthylcarbonyl-2-yl group.

As the substituent being a substituted or unsubstituted amino group, an amino group or a substituted amino group having 1 to 24 carbon atoms is preferable, and a dialkylamino group having 2 to 16 carbon atoms is more preferable.
As the substituent of the substituted amino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group is preferable.
Examples include methylamino group, ethylamino group, propylamino group, butylamino group, pentylamino group, hexylamino group, heptylamino group, octylamino group, 2-ethylhexylamino group, cyclohexylamino group, 3, 5 Monoalkylamino groups such as, 5-trimethylhexylamino group, nonylamino group, decylamino group;
Dimethylamino group, diethylamino group, methylethylamino group, di-n-propylamino group, di-n-butylamino group, di-n-pentylamino group, N-methyl-N-ethylamino group, N-ethyl- Dialkylamino groups such as N-isopropylamino group, N-ethyl-N-cyclohexylamino group, N-methyl-Nn-octylamino group;
N-methyl-N-phenylamino group, N-ethyl-N-phenylamino group, N-ethyl-N- (2,4-dimethylphenyl) amino group, Nn-propyl-N- (2-ethoxyphenyl) ) Aryl group such as amino group, N-methyl-N- (3-chlorophenyl) amino group, diphenylamino group, di- (p-tolyl) amino group, N-methyl-N- (2-naphthyl) amino group Having an amino group;
Benzylamino group, phenethylamino group, 3-phenylpropylamino group, 4-ethylbenzylamino group, 4-isopropylbenzylamino group, dibenzylamino group, diphenethylamino group, bis (4-ethylbenzyl) amino group, bis An amino group having an aralkyl group such as (4-isopropylbenzyl) amino group, N-ethyl-N-benzylamino group, N-methyl-N-phenethylamino group, and the like.

In the general formula (1), R ₁ is preferably a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 12 carbon atoms, a substituted or unsubstituted 6 to 24 carbon atoms. An aryl group, a substituted or unsubstituted aralkyl group having 7 to 25 carbon atoms in total.
More preferably, R ₁ is a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 8 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms. .
Examples of the unsubstituted alkyl group for R ₁ include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group. Group, neopentyl group, tert-pentyl group, n-hexyl group, 1-methylpentyl group, 4-methyl-2-pentyl group, 2-ethylbutyl group, n-heptyl group, 1-methylhexyl group, n-octyl group Straight-chain or branched unsubstituted alkyl groups such as 1-methylheptyl group and 2-ethylhexyl group.

Examples of R ₁ substituted alkyl groups include, for example, methoxymethyl group, ethoxymethyl group, n-butoxymethyl group, n-hexyloxymethyl group, (2-ethylbutyloxy) methyl group, 2- (4′- An alkyl group having an alkyloxy group or an alkenyloxy group such as a pentenyloxy) ethyl group, for example, an alkyl group having an aralkyloxy group such as a benzyloxymethyl group or a 2- (benzyloxymethoxy) ethyl group, phenyloxymethyl Group, an alkyl group having an aryloxy group such as 4-chlorophenyloxymethyl group, 4- (2′-phenyloxyethoxy) butyl group, for example, n-butylthiomethyl group, 2-n-octylthioethyl group, etc. Alkyl groups having a thioalkyl group such as fluoromethyl group, trifluoromethyl Examples thereof include alkyl groups having a halogen atom such as a til group, a perfluoroethyl group, a 4-fluorocyclohexyl group, a dichloromethyl group, a 4-chlorocyclohexyl group, and a 7-chloroheptyl group.
Examples of those in which R ₁ is a substituted or unsubstituted alkenyl group include, for example, vinyl group, propenyl group, 1-butenyl group, isobutenyl group, 1-pentenyl group, 2-pentenyl group, 2-methyl-1-butenyl. Group, 2-cyclopentenyl group, 1-vinylhexyl group, styryl group, styrylmethyl group, 2-styrylethyl group and the like.

Examples of those in which R ₁ is a substituted or unsubstituted aryl group include, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, 2-anthracenyl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group. Group, 1-pyrenyl group, 2-pyrenyl group, 2-perylenyl group, 3-perylenyl group, 2-fluoranthenyl group, 3-fluoranthenyl group, 7-fluoranthenyl group, 8-fluoranthenyl group, etc. An unsubstituted aryl group such as 1-methyl-2-pyrenyl group, 2-methylphenyl group, 4-ethylphenyl group, 4- (4′-tert-butylcyclohexyl) phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group, 4-ethyl-1-naphthyl group, 6-n-butyl-2-naphthyl group, 2,4-dimethylphenyl group Aryl groups having any alkyl group, for example, 4-methoxyphenyl group, 3-ethoxyphenyl group, 2-ethoxyphenyl group, 4-n-propoxyphenyl group, 3-n-propoxyphenyl group, 4-isopropoxyphenyl group 3-isopropoxyphenyl group, 2-isopropoxyphenyl group, 2-sec-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2-methyl-5-methoxyphenyl group, An aryl group having an alkoxy group or an aryloxy group such as 2-phenyloxyphenyl group, 4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group, 2,6-diphenylphenyl group, 4- (2 '-Naphthyl) phenyl group, 2-phenyl-1-naphthyl group, 1-phenyl An aryl group having an aryl group such as 2-naphthyl group and 7-phenyl-1-pyrenyl group, such as 4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 4-chlorophenyl group, 4- Bromophenyl group, 2-chloro-5-methylphenyl group, 2-chloro-6-methylphenyl group, 2-methyl-3-chlorophenyl group, 2-methoxy-4-fluorophenyl group, 2-fluoro-4-methoxy Aryl group having a halogen atom such as phenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 3,5-bistrifluoromethylphenyl group, 4-perfluoro Ethylphenyl group, 4-methylthiophenyl group, 4-ethylthiophenyl group, 4-cyanopheny Group, 3-cyanophenyl group.

Examples of those in which R ₁ is a substituted or unsubstituted aralkyl group include, for example, benzyl group, α-methylbenzyl group, phenethyl group, α-methylphenethyl group, α, α-dimethylbenzyl group, α, α-dimethyl group. Aralkyl groups which are unsubstituted or have an alkyl group such as phenethyl group, 4-methylphenethyl group, 4-methylbenzyl group, 4-isopropylbenzyl group, for example, 4-benzylbenzyl group, 4-phenethylbenzyl group, 4-phenyl Aralkyl groups having an aryl group or an aralkyl group such as a benzyl group, for example, 4-methoxybenzyl group, 4-n-tetradecyloxybenzyl group, 4-n-heptadecyloxybenzyl group, 3,4-dimethoxybenzyl Group, 4-methoxymethylbenzyl group, 4-vinyloxymethylbenzyl group, 4-benzyloxy Shibenjiru group, an aralkyl group having a substituent group such as 4-phenethyloxycarbonyl benzyl group. For example, an aralkyl group having a hydroxyl group such as a 4-hydroxybenzyl group and a 4-hydroxy-3-methoxybenzyl group, for example, a halogen atom such as a 4-fluorobenzyl group, a 3-chlorobenzyl group, and a 3,4-dichlorobenzyl group And an aralkyl group having a 2-furfuryl group, a diphenylmethyl group, a 1-naphthylmethyl group, a 2-naphthylmethyl group, and the like.

Specific examples of the isoindoline-based compound represented by the general formula (1) of the present invention are shown in Table 1 below, but are not limited thereto.
Table 1

[Method for producing isoindoline-based compound]
According to a second aspect of the present invention, there is provided a method for reacting the pyrrolinone compound represented by the general formula (2) with the imino compound represented by the general formula (3), (4) or (5). It is a manufacturing method of the isoindoline type compound represented by Formula (1).
[Wherein, A represents a substituted or unsubstituted aromatic ring, a substituted or unsubstituted heterocyclic ring, and R ₁ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group. Represents a substituted or unsubstituted aralkyl group. ]
[Wherein, ring X represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heterocyclic ring, and R ₂ represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, substituted or unsubstituted A substituted aryl group, a substituted or unsubstituted aralkyl group, R ₃ represents a substituted or unsubstituted alkyl group, R ₄ and R ₅ each independently represents a substituted or unsubstituted alkyl group, R ₄ And R ₅ may combine to form a ring. ]

In the general formula (2), A and R ₁ have the same meanings as those shown in the general formula (1), and preferred ranges and specific examples are also the same.
In the general formulas (3), (4) and (5), the ring X has the same meaning as that shown in the general formula (1), and preferred ranges and specific examples are also the same.
In the general formulas (3), (4) and (5), R ₂ is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms. A substituted or unsubstituted aryl group having 6 to 24 carbon atoms and a substituted or unsubstituted aralkyl group having 7 to 25 carbon atoms.
More preferably, R ₂ is a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, carbon It is a substituted or unsubstituted aralkyl group of formula 7-19.
More preferably, R ₂ is a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, carbon It is a substituted or unsubstituted aralkyl group of formula 7-13.

Specific examples of R ₂ are shown below.
Examples of the unsubstituted alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, Neopentyl group, tert-pentyl group, n-hexyl group, 1-methylpentyl group, 4-methyl-2-pentyl group, 2-ethylbutyl group, n-heptyl group, 1-methylhexyl group, n-octyl group, 1 -Linear, branched or cyclic such as methylheptyl group, 2-ethylhexyl group, n-decyl group, n-dodecyl group, n-hexadecyl group, n-octadecyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group An alkyl group is mentioned.
Specific examples of the alkyl group having a substituent include, for example, methoxymethyl group, ethoxymethyl group, n-butoxymethyl group, n-hexyloxymethyl group, (2-ethylbutyloxy) methyl group, 2- (4 ′ An alkyl group having an alkyloxy group or an alkenyloxy group, such as a -pentenyloxy) ethyl group, for example, an alkyl group having an aralkyloxy group, such as a benzyloxymethyl group or 2- (benzyloxymethoxy) ethyl group, phenyloxy Alkyl groups having an aryloxy group such as a methyl group, 4-chlorophenyloxymethyl group, 4- (2′-phenyloxyethoxy) butyl group, for example, n-butylthiomethyl group, 2-n-octylthioethyl group An alkyl group having a thioalkyl group such as a fluoromethyl group, Ruoromechiru group, Pa - fluoroethyl group, 4-fluoro-cyclohexyl group, dichloromethyl group, 4-chloro cyclohexyl group include alkyl groups having a halogen atom such as 7-chloro-heptyl group.
Examples of the substituted or unsubstituted alkenyl group include a vinyl group, a propenyl group, a 1-butenyl group, an isobutenyl group, a 1-pentenyl group, a 2-pentenyl group, a 2-methyl-1-butenyl group, and a 2-cyclopentenyl group. 1-vinylhexyl group, styryl group, styrylmethyl group, 2-styrylethyl group, and the like.

  Examples of the substituted or unsubstituted aryl group include a phenyl group, 1-naphthyl group, 2-naphthyl group, 2-anthracenyl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 1-pyrenyl group, Unsubstituted aryl groups such as 2-pyrenyl group, 2-perylenyl group, 3-perylenyl group, 2-fluoranthenyl group, 3-fluoranthenyl group, 7-fluoranthenyl group, 8-fluoranthenyl group, For example, 1-methyl-2-pyrenyl group, 2-methylphenyl group, 4-ethylphenyl group, 4- (4′-tert-butylcyclohexyl) phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group, 4 -Has an alkyl group such as ethyl-1-naphthyl group, 6-n-butyl-2-naphthyl group, 2,4-dimethylphenyl group, etc. Aryl groups such as 4-methoxyphenyl group, 3-ethoxyphenyl group, 2-ethoxyphenyl group, 4-n-propoxyphenyl group, 3-n-propoxyphenyl group, 4-isopropoxyphenyl group, 3-iso Propoxyphenyl group, 2-isopropoxyphenyl group, 2-sec-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2-methyl-5-methoxyphenyl group, 2-phenyloxy Aryl group having alkyloxy group or aryloxy group such as phenyl group, 4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group, 2,6-diphenylphenyl group, 4- (2′-naphthyl) ) Phenyl group, 2-phenyl-1-naphthyl group, 1-phenyl-2-naphthyl group Aryl groups having an aryl group such as 7-phenyl-1-pyrenyl group, such as 4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, Such as 2-chloro-5-methylphenyl group, 2-chloro-6-methylphenyl group, 2-methyl-3-chlorophenyl group, 2-methoxy-4-fluorophenyl group, 2-fluoro-4-methoxyphenyl group, etc. Aryl group having a halogen atom, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 3,5-bistrifluoromethylphenyl group, 4-perfluoroethylphenyl group, 4-methylthiophenyl group, 4-ethylthiophenyl group, 4-cyanophenyl group, 3-cyano Such as Eniru group, and the like.

  Examples of the substituted or unsubstituted aralkyl group include benzyl group, α-methylbenzyl group, phenethyl group, α-methylphenethyl group, α, α-dimethylbenzyl group, α, α-dimethylphenethyl group, 4-methylphenethyl group. Group, an aralkyl group having an unsubstituted or alkyl group such as 4-methylbenzyl group, 4-isopropylbenzyl group, for example, an aryl such as 4-benzylbenzyl group, 4-phenethylbenzyl group, 4-phenylbenzyl group, etc. Or an aralkyl group having an aralkyl group, such as 4-methoxybenzyl group, 4-n-tetradecyloxybenzyl group, 4-n-heptadecyloxybenzyl group, 3,4-dimethoxybenzyl group, 4-methoxymethylbenzyl Group, 4-vinyloxymethylbenzyl group, 4-benzyloxybenzyl group, 4- Aralkyl group having a substituent group, such as E phenethyl oxy benzyl group. For example, an aralkyl group having a hydroxyl group such as a 4-hydroxybenzyl group and a 4-hydroxy-3-methoxybenzyl group, for example, a halogen atom such as a 4-fluorobenzyl group, a 3-chlorobenzyl group, and a 3,4-dichlorobenzyl group And an aralkyl group having a 2-furfuryl group, a diphenylmethyl group, a 1-naphthylmethyl group, a 2-naphthylmethyl group, and the like.

R ₃ in the general formula (4) is preferably a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, more preferably a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, still more preferably. It is a C1-C12 substituted or unsubstituted alkyl group.

Specific examples of R ₃ are shown below.
Examples of the unsubstituted alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, Neopentyl group, tert-pentyl group, n-hexyl group, 1-methylpentyl group, 4-methyl-2-pentyl group, 2-ethylbutyl group, n-heptyl group, 1-methylhexyl group, n-octyl group, n -Linear, branched or cyclic alkyl groups such as -decyl group, n-dodecyl group, n-octadecyl group, 1-methylheptyl group, 2-ethylhexyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group .

Specific examples of the alkyl group having a substituent include, for example, methoxymethyl group, ethoxymethyl group, n-butoxymethyl group, n-hexyloxymethyl group, (2-ethylbutyloxy) methyl group, 2- (4 ′ An alkyl group having an alkyloxy group or an alkenyloxy group, such as a -pentenyloxy) ethyl group, for example, an alkyl group having an aralkyloxy group, such as a benzyloxymethyl group or 2- (benzyloxymethoxy) ethyl group, phenyloxy Alkyl groups having an aryloxy group such as a methyl group, 4-chlorophenyloxymethyl group, 4- (2′-phenyloxyethoxy) butyl group, for example, n-butylthiomethyl group, 2-n-octylthioethyl group An alkyl group having a thioalkyl group such as a fluoromethyl group, Ruoromechiru group, Pa - fluoroethyl group, 4-fluoro-cyclohexyl group, dichloromethyl group, 4-chloro cyclohexyl group include alkyl groups having a halogen atom such as 7-chloro-heptyl group.
When R ₄ and R ₅ in the general formula (5) are substituted or unsubstituted alkyl groups, preferred ranges and specific examples are the same as those shown for R ₃ in the general formula (4).
Further, the ring formed by combining R ₄ and R ₅ is preferably a 5- to 7-membered ring which may have a substituent. Each of R ₄ and R ₅ is substituted by an oxygen atom and a common basic carbon thereof. A substituted or unsubstituted dioxolane ring or dioxane ring formed with an atom is more preferable.

Specific examples are shown below.
The substituent in the case where the formed ring has a substituent is the same as the substituent that R ₄ and R ₅ have when they are substituted alkyl groups. In particular, a dioxolane ring or a dioxane ring, each of which may have one or more alkyl groups having 1 to 8 carbon atoms, is preferable.
When a specific example is represented by a portion where R ₃ and R ₄ are bonded, for example, ethane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5- Diyl group, hexane-1,6-diyl group, 1-methylethane-1,2-diyl group, 1-n-butylethane-1,2-diyl group, 2-ethylpropane-1,3-diyl group, 1- Methyl-propane-1,3-diyl group, 1-n-butyl-propane-1,3-diyl group, 2-n-butyl-butane-1,4-diyl group, 2,4-dimethyl-butane-1 , 4-diyl group, 3-isopentyl-pentane-1,5-diyl group, 2,3,4-trimethylpentane-1,5-diyl group, 2,3,4,5-tetramethylhexane-1,6 -A diyl group is mentioned.
Although the specific example of the pyrrolinone compound represented by General formula (2) is shown in following Table 2, it is not limited to these.

Table 2

The pyrrolinone compound represented by the general formula (2) is known from JP-A-61-115056, JP-A-61-115960, JP-A-7-285920, etc., and is produced by referring to a known method. can do. For example, the compound of specific example (2) -2 can be produced by heating diethyl 2-benzoylsuccinate and ammonium acetate in acetic acid.
Specific examples of the imino compounds represented by the general formulas (3), (4), and (5) are shown in Table 3 below, but are not limited thereto.

Table 3

  The imino compounds represented by the general formulas (3), (4), and (5) are known in JP-A-8-113561, JP-A-8-199081, JP-A-8-222553, and the like. It can be manufactured with reference to the method. For example, the compound of specific example (5) -1 can be obtained by stirring 1,1-dimethoxy-3-iminoisone indoline and 4-methylbenzoic acid in acetone for 30 minutes and filtering the precipitate.

(Method for producing isoindoline-based compound)
The pyrrolinone compound represented by the general formula (2) and the imino compound represented by the general formula (3), (4) or (5) in the presence or absence of a solvent, preferably under heating. By reacting, the isoindoline compound represented by the general formula (1) can be produced.
The use ratio of the pyrrolinone compound represented by the general formula (2) and the imino compound represented by the general formula (3), (4) or (5) is that the imino compound is 1 mol per pyrrolinone compound. 2-10 times mole, Preferably it is 2-5 times mole, More preferably, it is 2-3 times mole.
The reaction temperature is 40 to 250 ° C, preferably 50 to 220 ° C, more preferably 60 to 200 ° C. When the reaction temperature is 40 ° C. or lower, it takes a long time to produce the isoindoline compound represented by the general formula (1), and when it is higher than 250 ° C., by-products may increase.
The reaction time is 10 minutes to 24 hours, preferably 20 minutes to 12 hours, more preferably 30 minutes to 8 hours.
When the pyrrolinone compound or imino compound is a solid, it is preferable to use a solvent for the reaction, but it is not essential.
The solvent is not particularly limited as long as it does not adversely affect the reaction, alcohols, aromatic hydrocarbons such as toluene, xylene, mesitylene, pseudocumene, chlorobenzene and dichlorobenzene, organic acids such as acetic acid and trifluoroacetic acid, Aprotic solvents such as DMF, DMAC and DMI can be used.
The usage-amount of a solvent is 1-500 times volume with respect to the pyrrolinone compound represented by General formula (2) used for reaction, Preferably it is 5-200 times volume, More preferably, it is 10-100 times volume.
After the reaction, when the solvent is used, if the solvent used is other than alcohols, most of the solvent is distilled off, then alcohols such as methanol, ethanol, isopropyl alcohol, etc. are added and cooled to near room temperature. Precipitate. By filtering this, an isoindoline compound represented by the general formula (1) can be obtained.
If necessary, a high-purity product can be obtained by further adding known purification operations such as recrystallization and column chromatography to the product.

EXAMPLES Hereinafter, although a synthesis example and an Example demonstrate this invention further in detail, this invention is not limited to these.
(Synthesis Example 1) Synthesis of pyrrolinone compound (specific example compound (2) -2) 139.1 g of diethyl 2-benzoylsuccinate and 102.1 g of ammonium acetate were added to 300 mL of acetic acid and stirred at 100 to 105 ° C for 24 hours. After cooling, the reaction mixture was drained into 500 mL of water. The precipitate was collected by filtration, the filter paste was dispersed and washed with 500 mL of methanol, and dried to obtain 52 g of Compound No. (2) -2 of the pyrrolinone compound shown in Table 2 as a white powder. Melting point: 180-181 ° C
The obtained compound was confirmed to be the target compound from the following analysis results.
MS: (EI) m / z 231M +)
Elemental analysis values: measured values (C: 67.56%, H: 5.69%, N: 6.04%); theoretical values (C: 67.52%, H: 5.67%, N: 6 .06%)

(Synthesis Example 2) Synthesis of Pyrrolinone Compound (Specific Example Compound (2) -3) Synthesis except that 153.2 g of 2-isopropyl benzoyl succinate was used in place of 139.1 g of diethyl 2-benzoyl succinate in Synthesis Example 1. The same operation as in Example 1 was carried out to obtain 49.1 g of Compound No. (2) -3 of the pyrrolinone compound shown in Table 2 as a white powder. Melting point: 148-150 ° C
The obtained compound was confirmed to be the target compound from the following analysis results.
MS: (EI) m / z 245M +)
Elemental analysis values: measured values (C: 68.59%, H: 6.20%, N: 5.69%); theoretical values (C: 68.56%, H: 6.16%, N: 5 .71%)

(Synthesis Example 3) Pyrrolinone Compound (Synthesis of Specific Example Compound (2) -15) In place of 139.1 g of diethyl 2-benzoylsuccinate in Synthesis Example 1, 156.4 g of diethyl 2- (4-chlorobenzoyl) succinate was used. The procedure was the same as in Synthesis Example 1 except that the compound number (2) -15 of the pyrrolinone compound shown in Table 2 was obtained as white powder to obtain 70.4 g, melting point: 195-196 ° C.
The obtained compound was confirmed to be the target compound from the following analysis results.
MS: (EI) m / z 265M +)
Elemental analysis values: measured values (C: 58.81%, H: 4.58%, N: 5.26%); theoretical values (C: 58.77%, H: 4.55%, N: 5.27) %)

(Synthesis Example 4) Synthesis of imino compound (specific compound example compound (3) -22) To 100 mL of methanol, 21.7 g of 4-n-butoxy-1,3-diiminoisoindoline and 4-methylbenzoic acid 13. 6g was added and it stirred at 60-65 degreeC for 30 minutes. After cooling, it was filtered. The filter paste was washed with methanol and dried to obtain 32.5 g of Compound No. (3) -22 of the imino compound shown in Table 1 as a white powder.
Melting point: 162-163 ° C. (with decomposition)
The obtained compound was confirmed to be the target compound from the following analysis results.
Elemental analysis values: measured values (C: 68.00%, H: 6.59%, N: 11.86%); theoretical values (C: 67.97%, H: 6.56%, N: 11) .89%)

(Synthesis Example 5) Synthesis of imino compound (specific example compound (4) -7) 18.8 g of 1-isopropoxy-3-iminoisoindoline and 15.7 g of 4-chlorobenzoic acid were added to 300 mL of toluene, and 15-20 Stir at 4 ° C. for 4 hours. After cooling, the crystallized product was collected by filtration, washed with toluene and dried to obtain 32.2 g of Compound No. (4) -7 of the imino compound shown in Table 1 as a white powder.
Melting point: 126-127 ° C. (with decomposition)
The obtained compound was confirmed to be the target compound from the following analysis results.
Elemental analysis values: measured values (C: 62.74%, H: 5.01%, N: 8.09%); theoretical values (C: 62.70%, H: 4.97%, N: 8 .12%)

(Synthesis example 6) Synthesis of imino compound (specific example compound (5) -2) 1,1-diethoxy-3-iminoisoindoline instead of 18.8 g of 1-isopropoxy-3-iminoisoindoline in synthesis example 5 22 g, except that 13.6 g of 4-methylbenzoic acid was used instead of 15.7 g of 4-chlorobenzoic acid. The same procedure as in Synthesis Example 5 was repeated, and the compound number of the imino compound shown in Table 1 (5 ) -2 was obtained as white powder to obtain 31.0 g. Melting point: 75-76 ° C. (with decomposition)
The obtained compound was confirmed to be the target compound from the following analysis results.
Elemental analysis values: measured values (C: 67.44%, H: 6.81%, N: 7.83%); theoretical values (C: 67.40%, H: 6.79%, N: 7 .86%)

Synthesis Example 7 Synthesis of Imino Compound (Specific Example Compound (5) -13) Instead of 18.8 g of 1-isopropoxy-3-iminoisoindoline in Synthesis Example 5, 1,1- (1′-methylethylenedi) Oxy) -3-iminoisoindoline 20.4 g, instead of 15.7 g of 4-chlorobenzoic acid, 13.6 g of 2-methylbenzoic acid was used. The compound number (5) -13 of the imino compound shown in 3 was obtained as a white powder to obtain 30.9 g. Melting point: 116 ° C. (with decomposition)
The obtained compound was confirmed to be the target compound from the following analysis results.
Elemental analysis values: measured values (C: 67.07%, H: 5.95%, N: 8.21%); theoretical values (C: 67.05%, H: 5.92%, N: 8 .23%)

[Example 1] Production of compound (1) -1 2.31 g of the pyrrolinone compound number (2) -2 shown in Table 2 above and the compound number (5)-of the imino compound shown in Table 3 above 1.7 g of 13 was used and heated and stirred at an internal temperature of 180 ° C. for 1 hour. After cooling the reaction product, 100 ml of methanol was added and refluxed for 1 hour with stirring. After cooling, the precipitate was filtered, washed with 20 ml of methanol and dried to obtain 2.2 g of Compound No. (1) -1 of the isoindoline compound of the present invention shown in Table 1 as a dark blue powder.
Melting point: 250 ° C. or higher (decomposition. According to TG-DTA analysis).
The obtained compound was confirmed to be the target compound from the following analysis results.
MS: (EI) m / z 573 (M +)
IR: νNH: 3270 cm ⁻¹ νC═O: 1692 cm ⁻¹
An IR spectrum diagram is shown in FIG.
Elemental analysis values: measured values (C: 71.22%, H: 4.69%, N: 7.22%); theoretical values (C: 71.19%, H: 4.74%, N: 7 .33%)
Absorption spectrum in THF: maximum absorption is 602 nm
An absorption spectrum (in THF) is shown in FIG.

Example 2 Production of Compound (1) -1 2.31 g of the pyrrolinone compound number (2) -2 shown in Table 2 above and the compound number (3)-of the imino compound shown in Table 3 above 1.33 g of 1 was used and heated and stirred in 100 ml of toluene at an internal temperature of 110 ° C. for 2 hours.
Toluene was concentrated and removed from the reaction solution with an evaporator, 100 ml of methanol was added to the residue, and the mixture was refluxed for 1 hour with stirring. After cooling, the precipitate was filtered, washed with 20 ml of methanol and dried to obtain 1.9 g of Compound No. (1) -1 of the isoindoline compound of the present invention shown in Table 1 as a dark blue powder.
Melting point: 250 ° C. or higher (decomposition. According to TG-DTA analysis).
The obtained compound was confirmed to be the target compound from the following analysis results.
MS: (EI) m / z 573 (M +)
Elemental analysis values: measured values (C: 71.17%, H: 4.77%, N: 7.44%); theoretical values (C: 71.19%, H: 4.74%, N: 7 .33%)

Example 3 Production of Compound (1) -27 Except for using 1.77 g of Compound No. (3) -22 instead of Compound No. (5) -13 of the imino compound shown in Table 3 in Example 1. Were operated in the same manner as in Example 1 to obtain 1.9 g of Compound No. (1) -27 of the isoindoline compound of the present invention shown in Table 1 as a dark blue powder.
Melting point: 250 ° C. or higher (decomposition. According to TG-DTA analysis).
The obtained compound was confirmed to be the target compound from the following analysis results.
MS: (EI) m / z 645 (M +)
IR: νC═O: 1707 cm ⁻¹
The IR spectrum is shown in FIG.
Elemental analysis values: measured values (C: 71.00%, H: 5.31%, N: 6.66%); theoretical values (C: 70.68%, H: 5.46%, N: 6 .51%)
Absorption spectrum in THF: maximum absorption is 612 nm
An absorption spectrum (in THF) is shown in FIG.

[Examples 4 to 35]
In the pyrrolinone compound and the imino compound in Example 1, the same operations as in Example 1 were performed using the compounds described in Table 4 below instead of Compound No. (2) -2 and Compound No. (5) -13. And an isoindoline compound was obtained.
The analysis results are shown in Table 5.

The isoindoline-based compound of the present invention has a high color density, a clear hue even when dissolved in a solvent, and high fastness.
Therefore, it is very useful as a blue colorant for plastic colorants, inks, paints, inks for inkjet printers, color toners and the like.

Claims (7)

An isoindoline compound represented by the general formula (1).
[Wherein, A represents a substituted or unsubstituted aromatic ring group, a substituted or unsubstituted heterocyclic group, ring X represents a substituted or unsubstituted aromatic ring, a substituted or unsubstituted heterocyclic ring, and R ₁ represents A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aralkyl group are shown. ]   A is a substituted or unsubstituted benzene ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted anthracene ring, substituted or unsubstituted pyridine ring, substituted or unsubstituted quinoline ring, substituted or unsubstituted pyrrole ring, A substituted or unsubstituted indole ring, a substituted or unsubstituted thiophene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted furan ring, a substituted or unsubstituted benzofuran ring, and ring X is substituted or unsubstituted Benzene ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted anthracene ring, substituted or unsubstituted pyridine ring, substituted or unsubstituted pyrazine ring, substituted or unsubstituted carbazole ring, substituted or unsubstituted dibenzofuran Ring, substituted or unsubstituted quinoline ring, substituted or unsubstituted quinoxaline ring, substituted or unsubstituted Conversion of phenothiazine ring, a substituted or unsubstituted acridone ring, a substituted or unsubstituted anthraquinone ring, a substituted or unsubstituted thianthrene ring, a substituted or unsubstituted phenoxazine ring, isoindoline compound of claim 1. A is a substituted or unsubstituted benzene ring, substituted or unsubstituted pyridine ring, substituted or unsubstituted pyrrole ring, substituted or unsubstituted thiophene ring, substituted or unsubstituted benzothiophene ring, substituted or unsubstituted furan ring Wherein ring X is a substituted or unsubstituted benzene ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted anthracene ring, substituted or unsubstituted pyridine ring, substituted or unsubstituted carbazole ring, substituted or unsubstituted The isoindoline compound according to claim 1 or 2, which is a dibenzofuran ring, a substituted or unsubstituted acridone ring, a substituted or unsubstituted anthraquinone ring, a substituted or unsubstituted thianthrene ring, or a substituted or unsubstituted phenothiazine ring. A is unsubstituted or substituted as a halogen atom, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted alkylthio group, respectively. A benzene ring, a naphthalene ring, an anthracene ring, a pyridine ring, a quinoline ring, a pyrrole ring, an indole ring, a thiophene ring, having at least one selected from a substituted or unsubstituted amino group, and a substituted or unsubstituted heterocyclic group , A benzothiophene ring, a furan ring, or a benzofuran ring, wherein ring X is unsubstituted, or a halogen atom, a hydroxyl group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl as a substituent, respectively Group, substituted or unsubstituted aryl group, substituted or unsubstituted aralkyl group, substituted or Is an unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, an unsubstituted or unsubstituted arylthio group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted arylcarbonyl group And a benzene ring, naphthalene ring, anthracene ring, pyridine ring, pyrazine ring, carbazole ring, dibenzofuran ring, quinoline ring, quinoxaline ring, phenothiazine ring, acridone ring having at least one selected from a substituted or unsubstituted amino group The isoindoline compound according to any one of claims 1 to 3, which is an anthraquinone ring, a thianthrene ring, or a phenoxazine ring. A is unsubstituted or as a substituent, a halogen atom, a cyano group, an alkyl group having 1 to 8 carbon atoms, a halogenated alkyl group having 1 to 8 carbon atoms, or a dialkylaminoalkoxy group having 3 to 18 carbon atoms in total. A benzene ring, a pyridine ring, a pyrrole ring, a thiophene ring, a benzothiophene ring, or a furan ring having at least one selected from a dialkylamino group having 2 to 16 carbon atoms in total and an alkoxy group having 1 to 8 carbon atoms Yes, ring X is unsubstituted or each has a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a dialkylamino group having 2 to 16 carbon atoms in total, or a carbon number A benzene ring or a naphthalene ring having at least one selected from an aryloxy group having 6 to 18 carbon atoms and an arylcarbonyl group having 7 to 19 carbon atoms Anthracene ring, a pyridine ring, a carbazole ring, a dibenzofuran ring, acridone ring, an anthraquinone ring, a thianthrene ring or a phenothiazine ring,, R ₁ is a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, 2 to 8 carbon atoms The isoindoline compound according to any one of claims 1 to 4, which is a substituted or unsubstituted alkenyl group or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms. The pyrrolinone compound represented by the general formula (2) is reacted with the imino compound represented by the general formula (3), (4) or (5). A method for producing an isoindoline-based compound.
[In the formula, A represents a substituted or unsubstituted aromatic group, a substituted or unsubstituted heterocyclic group, and R ₁ represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted group. An aryl group, a substituted or unsubstituted aralkyl group is shown. ]
[Wherein, ring X represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heterocyclic ring, and R ₂ represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, substituted or unsubstituted A substituted aryl group, a substituted or unsubstituted aralkyl group, R ₃ represents a substituted or unsubstituted alkyl group, R ₄ and R ₅ each independently represents a substituted or unsubstituted alkyl group, R ₄ And R ₅ may combine to form a ring. ] In the general formula (2), A is a substituted or unsubstituted benzene ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted anthracene ring, substituted or unsubstituted pyridine ring, substituted or unsubstituted quinoline ring, substituted Or an unsubstituted pyrrole ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted thiophene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted furan ring, a substituted or unsubstituted benzofuran ring, In general formulas (3), (4) and (5), ring X is a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted pyridine ring, Substituted or unsubstituted pyrazine ring, substituted or unsubstituted carbazole ring, substituted or unsubstituted dibenzofuran ring, substituted or unsubstituted Substituted quinoline ring, substituted or unsubstituted quinoxaline ring, substituted or unsubstituted phenothiazine ring, substituted or unsubstituted acridone ring, substituted or unsubstituted anthraquinone ring, substituted or unsubstituted thianthrene ring, substituted or unsubstituted A phenoxazine ring, wherein R ₄ and R ₅ are substituted or unsubstituted alkyl groups, R ₄ and R ₅ are substituted oxygen atoms and a substituted or unsubstituted dioxolane ring formed together with these common basic carbon atoms, R The production method according to claim 6, wherein ₄ and R ₅ are substituted or unsubstituted dioxane rings formed together with the oxygen atom to be substituted and the common basic carbon atom.