WO2020170957A1

WO2020170957A1 - Colored composition, compound, color filter, and display device

Info

Publication number: WO2020170957A1
Application number: PCT/JP2020/005746
Authority: WO
Inventors: 勝成織田
Original assignee: 住友化学株式会社
Priority date: 2019-02-18
Filing date: 2020-02-14
Publication date: 2020-08-27
Also published as: KR20210127754A; TW202035387A; JP2020132878A; JP7535381B2; CN113454167A; CN113454167B

Abstract

The purpose of the present invention is to provide a colored composition including a compound having a maximum absorption wavelength on the longest wavelength side of the absorption spectrum and/or a compound having a wavelength of a shoulder peak on the longest wavelength side of the absorption spectrum to the longer wavelength side of the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of conventionally known C.I. Pigment Yellow 138.　The present invention relates to a colored composition including a compound represented by formula (I) and a solvent.

Description

Coloring composition, compound, color filter and display device

The present invention relates to a coloring composition, compound, color filter and display device.

The coloring composition is used for manufacturing a color filter used for a display device such as a liquid crystal display device and an electroluminescence display device. Examples of the coloring agent contained in the coloring composition include C.I. I. Pigment Yellow 138 is known (Patent Document 1).

(C.I. Pigment Yellow 138)

JP, 2013-82906, A

In recent years, display devices have been under development to expand the color reproduction range that can be displayed, and as a part thereof, color filters with deeper colors are required. In order to meet the demand, C.I. I. Pigment Yellow 138, a compound having a maximum absorption wavelength on the longest wavelength side of the absorption spectrum, and/or a shoulder peak on the longest wavelength side of the absorption spectrum. There is a need for colored compositions that include compounds having wavelengths of
With the wavelength of the shoulder peak on the longest wavelength side of the above absorption spectrum,
The compound is
C. I. Pigment Yellow 138 does not have the maximum absorption wavelength on the longest wavelength side of the absorption spectrum on the longer wavelength side than the maximum absorption wavelength on the longest wavelength side,
And,
When the absorption spectrum has two or more inflection points on the longer wavelength side than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum,
It means the wavelength of the average value of the wavelengths of the inflection points on the longest wavelength side of the absorption spectrum and the wavelengths of the inflection points on the second longest wavelength side of the absorption spectrum.

The present invention provides the following [1] to [6].
[1] A coloring composition containing a compound represented by the following formula (I) and a solvent.

[In the formula (I),
R ¹ to R ⁵ are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms or a carbon atom. Represents a monovalent heterocyclic group of the numbers 1 to 40,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
—CH ₂ — constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with —O—, —S—, —S(O) ₂ — or —CO—,
The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M or MM.
R ¹ and R ² , R ² and R ³ , and R ³ and R ⁴ may be bonded to each other to form a ring.
M represents a hydrogen atom, an alkali metal atom, a metal atom which may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ).
MM represents an alkali metal atom, a metal atom which may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ).
Z ¹ to Z ⁴ each independently represent a hydrogen atom, a monovalent hydrocarbon group having 1 to 40 carbon atoms or a monovalent heterocyclic group having 1 to 40 carbon atoms,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
—CH ₂ — constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with —O—, —S—, —S(O) ₂ — or —CO—,
The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M or MM.
Q ¹ and Q ² each independently represent a divalent hydrocarbon group or a divalent heterocyclic group,
-C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N=,
—CH ₂ — constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with —O—, —S—, —S(O) ₂ — or —CO—,
The hydrogen atom constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M or MM.
When there are a plurality of Z ¹ to Z ⁴ , M and MM, they may be the same or different from each other. ]
[2] The coloring composition according to [1], which contains a resin.
[3] The coloring composition according to any one of [1] to [2], which contains a polymerizable compound and a polymerization initiator.
[4] A color filter formed of the coloring composition according to any one of [1] to [3].
[5] A display device including the color filter according to [4].
[6] A compound represented by the formula (I).

[In the formula (I),
R ¹ to R ⁵ are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms or a carbon atom. Represents a monovalent heterocyclic group of the numbers 1 to 40,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
—CH ₂ — constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with —O—, —S—, —S(O) ₂ — or —CO—,
The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M or MM.
R ¹ and R ² , R ² and R ³ , and R ³ and R ⁴ may be bonded to each other to form a ring.
M represents a hydrogen atom, an alkali metal atom, a metal atom which may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ).
MM represents an alkali metal atom, a metal atom which may have a ligand, or N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ).
Z ¹ to Z ⁴ each independently represent a hydrogen atom, a monovalent hydrocarbon group having 1 to 40 carbon atoms or a monovalent heterocyclic group having 1 to 40 carbon atoms,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
—CH ₂ — constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with —O—, —S—, —S(O) ₂ — or —CO—,
The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M or MM.
Q ¹ and Q ² each independently represent a divalent hydrocarbon group or a divalent heterocyclic group,
-C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N=,
—CH ₂ — constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with —O—, —S—, —S(O) ₂ — or —CO—,
The hydrogen atom constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M or MM.
When there are a plurality of Z ¹ to Z ⁴ , M and MM, they may be the same or different from each other. ]

According to the present invention, C.I. I. Pigment Yellow 138 is provided, which provides a coloring composition and a compound that can be used for forming a darker color filter.

[Coloring composition]
The coloring composition of the present invention contains a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) and a solvent (hereinafter sometimes referred to as solvent (E)).

Compound (I) also includes its tautomers and salts thereof.
The compound (I) can be used as a colorant.
The coloring composition of the present invention may contain one or more compounds (I).
The coloring composition of the present invention may contain a resin (hereinafter, sometimes referred to as resin (B)).
The colored composition of the present invention may be referred to as a polymerizable compound (hereinafter, referred to as a polymerizable compound (C)).
) May be included.
The colored composition of the present invention may contain a polymerization initiator (hereinafter sometimes referred to as a polymerization initiator (D)).
The colored composition of the present invention may contain a polymerization initiation auxiliary agent (hereinafter sometimes referred to as a polymerization initiation auxiliary agent (D1)).
The coloring composition of the present invention may be referred to as a colorant other than the compound (I) (hereinafter, referred to as a colorant (A1). In the following, the compound (I) and the colorant (A1) are referred to as a “colorant (A)”. May be collectively referred to as ".").
The colorant (A1) may contain one kind or two or more kinds of colorants.
The colorant (A1) preferably contains at least one selected from yellow colorants, orange colorants, red colorants and green colorants.
The coloring composition of the present invention may contain a leveling agent (hereinafter sometimes referred to as a leveling agent (F)).
The coloring composition of the present invention may contain an antioxidant (hereinafter sometimes referred to as an antioxidant (G)).

[Compound (I)]
Hereinafter, the present invention will be described in more detail with reference to the partial structure of the compound (I). In each partial structure, only a substituent bonded to the ring structure is bonded at any site of the ring structure. Even if it is not included, the following examples include embodiments in which the substituent is bonded to all the sites of the ring structure. One or two or more substituents may be bonded to a ring structure, and when two or more substituents are bonded to a ring structure, the substituents may be the same or different. Good.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom, a chlorine atom and a bromine atom are preferable.

The hydrocarbon group represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ has 1 to 40 carbon atoms, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and further preferably 1 carbon atom. It is -18, particularly preferably 1-12.
The monovalent hydrocarbon group having 1 to 40 carbon atoms represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. The hydrogen group may be saturated or unsaturated, and may be linear or cyclic (alicyclic hydrocarbon group).

The saturated or unsaturated chain hydrocarbon group represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ is a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group. , Nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, icosyl group, henicosyl group, docosyl group, tricosyl group, tetracosyl group, pentacosyl group Group, hexacosyl group, heptacosyl group, octacosyl group, nonacosyl group, triacontyl group, hentriacontyl group, dotriacontyl group, tritriacontyl group, tetratriacontyl group, pentatriacontyl group, hexatriacontyl group, heptatria group A straight chain alkyl group such as a contyl group, an octatriacontyl group, a nonatriacontyl group and a tetracontyl group;
Isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, 2-ethylbutyl group, 3,3-dimethylbutyl group, 1,1,3,3-tetramethylbutyl group, 1-methylbutyl group, 1-ethyl Propyl group, 3-methylbutyl group, neopentyl group, 1,1-dimethylpropyl group, 2-methylpentyl group, 3-ethylpentyl group, 1,3-dimethylbutyl group, 2-propylpentyl group, 1-ethyl-1 , 2-dimethylpropyl group, 1-methylpentyl group, 4-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, 2-ethylhexyl group, 1-methylhexyl group, 1-ethylpentyl group, 1- Propylbutyl group, 3-ethylheptyl group, 2,2-dimethylheptyl group, 1-methylheptyl group, 1-ethylhexyl group, 1-propylpentyl group, 1-methyloctyl group, 1-ethylheptyl group, 1-propyl A branched chain alkyl group such as hexyl group, 1-butylpentyl group, 1-methylnonyl group, 1-ethyloctyl group, 1-propylheptyl group and 1-butylhexyl group;
Ethenyl group (vinyl group), propenyl group (eg 1-propenyl group, 2-propenyl group (allyl group)), 1-methylethenyl group, butenyl group (eg 1-butenyl group, 2-butenyl group, 3-butenyl) Group), 3-methyl-1-butenyl group, 1,3-butadienyl group, 1-(2-propenyl)ethenyl group, 1-(1-methylethenyl)ethenyl group, 1,2-dimethyl-1-propenyl group, A pentenyl group (eg, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group), 1-(1,1-dimethylethyl)ethenyl group, 1,3-dimethyl-1-butenyl group, Hexenyl group (eg, 1-hexenyl group, 5-hexenyl group), heptenyl group (eg, 1-heptenyl group, 6-heptenyl group), octenyl group (eg, 1-octenyl group, 7-octenyl group), nonenyl group (Eg, 1-nonenyl group, 8-nonenyl group), decenyl group (eg, 1-decenyl group, 9-decenyl group), undecenyl group, dodecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, heptadecenyl group An alkenyl group such as an octadecenyl group, a nonadecenyl group, an icosenyl group, a 1,1-dimethyl-2-propenyl group, a 1-ethyl-2-propenyl group and a 1-methyl-1-butenyl group;
Ethynyl group, propynyl group (eg 1-propynyl group, 2-propynyl group), octynyl group (eg 1-octynyl group, 7-octynyl group), butynyl group, pentynyl group, hexynyl group, heptynyl group, nonynyl group, Alkynyl groups such as decynyl group, undecynyl group, dodecynyl group, tridecynyl group, tetradecynyl group, pentadecynyl group, hexadecynyl group, heptadecynyl group, octadecynyl group, nonadecynyl group and icosinyl group;
Etc. The saturated or unsaturated chain hydrocarbon group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, further preferably 1 to 18 carbon atoms, and particularly preferably 1 to 12 carbon atoms. Of these, a linear or branched alkyl group having 1 to 12 carbon atoms is particularly preferable.

Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ include cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl Group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2, 2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, cyclooctyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group, 3 Cycloalkyl groups such as 3,3,5,5-tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octylcyclohexyl group and 4-cyclohexylcyclohexyl group; cyclohexenyl group (eg cyclohex-1-en-1-yl) Group, cyclohex-2-en-1-yl group, cyclohex-3-en-1-yl group), cycloheptenyl group, cyclooctenyl group and the like cycloalkenyl group; norbornyl group, norbornenyl group, adamantyl group and bicyclo[2.2 .2] saturated or unsaturated polycyclic hydrocarbon groups such as octyl group; and the like. The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, further preferably 3 to 18 carbon atoms, and particularly preferably 3 to 12 carbon atoms. Of these, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and an adamantyl group are particularly preferable.

Examples of the aromatic hydrocarbon group represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ include phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, 3-ethyl group. Phenyl group, 4-ethylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3 ,5-dimethylphenyl group, 4-vinylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert -Butylphenyl group, 3,5-di(tert-butyl)phenyl group, 3,5-di(tert-butyl)-4-methylphenyl group, 4-butylphenyl group, 4-pentylphenyl group, 2,6 -Bis(1-methylethyl)phenyl group, 2,4,6-tris(1-methylethyl)phenyl group, 4-cyclohexylphenyl group, 2,4,6-trimethylphenyl group, 4-octylphenyl group, 4 -(1,1,3,3-Tetramethylbutyl)phenyl group, 1-naphthyl group, 2-naphthyl group, 6-methyl-2-naphthyl group, 5,6,7,8-tetrahydro-1-naphthyl group , 5,6,7,8-tetrahydro-2-naphthyl group, fluorenyl group, phenanthryl group, anthryl group, 2-dodecylphenyl group, 3-dodecylphenyl group, 4-dodecylphenyl group, perylenyl group, chrysenyl group and pyrenyl group Aromatic hydrocarbon groups such as groups; and the like. The aromatic hydrocarbon group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, further preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms.

The hydrocarbon groups represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ are the above-mentioned hydrocarbon groups (for example, aromatic hydrocarbon groups and at least chain hydrocarbon groups and alicyclic hydrocarbon groups). 1) in combination,
Benzyl group, (2-methylphenyl)methyl group, (3-methylphenyl)methyl group, (4-methylphenyl)methyl group, (2-ethylphenyl)methyl group, (3-ethylphenyl)methyl group, (4 -Ethylphenyl)methyl group, (2-(tert-butyl)phenyl)methyl group, (3-(tert-butyl)phenyl)methyl group, (4-(tert-butyl)phenyl)methyl group, (3,5 -Dimethylphenyl)methyl group, 1-phenylethyl group, 1,1-diphenylethyl group, phenethyl group, 1-methyl-1-phenylethyl group, (1-naphthyl)methyl group, (2-naphthyl)methyl group, etc. An aralkyl group of
Arylalkenyl groups such as 1-phenylethenyl group, 2-phenylethenyl group (phenylvinyl group), 2,2-diphenylethenyl group, 2-phenyl-2-(1-naphthyl)ethenyl group; phenylethynyl group And the like; phenyl groups to which one or more phenyl groups such as biphenylyl group and terphenylyl group are bonded; cyclohexylmethylphenyl group, benzylphenyl group, (dimethyl(phenyl)methyl)phenyl group and the like.
The carbon number of these is preferably 4 to 30, more preferably 4 to 20, further preferably 4 to 18, and particularly preferably 4 to 12. The lower limit of these ranges is preferably 7.
The groups represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ are, for example, cyclopropyl groups which are a combination of the above-mentioned hydrocarbon groups (eg, chain hydrocarbon group and alicyclic hydrocarbon group). One of methyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, (2-methylcyclohexyl)methyl group, cyclohexylethyl group, adamantylmethyl group, etc. It may be an alkyl group to which the above alicyclic hydrocarbon group is bonded.
The carbon number of these is preferably 4 to 30, more preferably 4 to 20, further preferably 4 to 18, and particularly preferably 4 to 12.

The monovalent heterocyclic group having 1 to 40 carbon atoms represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ represents a group containing a hetero atom as a constituent element of the ring. The monovalent heterocyclic group having 1 to 40 carbon atoms may be monocyclic or polycyclic. Examples of the hetero atom include a nitrogen atom, an oxygen atom and a sulfur atom.
The heterocyclic group preferably has 3 to 30 carbon atoms, more preferably has 3 to 20 carbon atoms, further preferably has 3 to 18 carbon atoms, and particularly preferably has 3 to 12 carbon atoms.

As the heterocycle containing a nitrogen atom,
Monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine;
Pyrrole such as pyrrole, 1-methylpyrrole and 2,5-dimethylpyrrole, pyrazole, 1-methylpyrazole, 2-methylpyrazole, 3-methylpyrazole, 4-methylpyrazole, 5-methylpyrazole and other pyrazole, imidazole, 1 5-membered unsaturated heterocycles such as 1,2,3-triazole and 1,2,4-triazole;
6-membered unsaturated heterocycles such as pyrimidines such as pyridine, pyridazine, pyridimine, 6-methylpyrimidine, pyrazine and 1,3,5-triazine;
Indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, quinoxaline such as 5,6,7,8-tetrahydro(3-methyl)quinoxaline, 3-methylquinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine , Fused purine, pteridine, benzopyrazole, benzopiperidine, and other condensed bicyclic heterocycles;
And fused tricyclic heterocycles such as carbazole, acridine and phenazine; and the like.

As a heterocycle containing an oxygen atom,
Monocyclic saturated heterocycles such as oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane and 1,4-dioxane, 1-cyclopentyldioxolane, 2-cyclopentyldioxolane;
Bicyclic saturated heterocycles such as 1,4-dioxaspiro[4.5]decane, 1,4-dioxaspiro[4.5]nonane and 1,4-dioxaspiro[4.4]nonane;
Lactone-based heterocycles such as α-acetolactone, β-propiolactone, γ-butyrolactone, γ-valerolactone and δ-valerolactone;
5-membered unsaturated heterocycles such as furan, 2,3-dimethylfuran, and 2,5-dimethylfuran;
6-membered unsaturated heterocycle such as 2H-pyran, 4H-pyran;
Condensed bicyclic heterocycles such as benzofuran such as 1-benzofuran, benzopyran, benzopyran such as 4-methylbenzopyran, benzodioxole, 1,3-benzodioxole, benzodioxane, chroman and isochroman;
Fused tricyclic heterocycles such as xanthene and dibenzofuran; and the like.

As the heterocycle containing a sulfur atom,
5-membered saturated heterocycle such as dithiolane;
6-membered saturated heterocycles such as thiane, 1,3-dithiane, 2-methyl-1,3-dithiane;
Thiophenes such as thiophene, 3-methylthiophene, 2-carboxythiophene, etc., 5-membered unsaturated heterocycles such as thiopyran such as 2H-thiopyran, 4H-thiopyran, benzothiopyran such as benzotetrahydrothiopyran, and 6-membered unsaturated ring Heterocycle;
A condensed bicyclic heterocycle such as benzothiopyran such as benzothiopyran or benzotetrahydrothiopyran, or benzothiophene;
Condensed tricyclic heterocycles such as thianthrene and dibenzothiophene; and the like.

As the heterocycle containing a nitrogen atom and an oxygen atom,
A monocyclic saturated heterocycle such as morpholine, 2-pyrrolidone, 1-methyl-2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone, 1-methyl-2-piperidone and 2-methyl-2-piperidone;
Monocyclic unsaturated heterocycles such as oxazole, oxazole such as 4-methyloxazole, 2-methylisoxazole, 3-methylisoxazole, 4-methylisoxazole, isoxazole such as 5-methylisoxazole;
Fused bicyclic heterocycles such as benzoxazole, benzisoxazole, benzoxazine, benzodioxane, benzimidazoline;
Fused tricyclic heterocycles such as phenoxazine; and the like.

As the heterocycle containing a nitrogen atom and a sulfur atom,
Monocyclic heterocycles such as thiazoles such as thiazole, 2-methylthiazole, 3-methylthiazole, 4-methylthiazole, 5-methylthiazole and 2,4-dimethylthiazole;
Fused bicyclic heterocycles such as benzothiazole;
Condensed tricyclic heterocycles such as phenothiazine; and the like.

Note that the bonding position of the above-mentioned heterocyclic group is a part where any hydrogen atom contained in each heterocycle is eliminated.

The above-mentioned heterocyclic group may be a group in which the above-mentioned heterocycle and the above-mentioned hydrocarbon group are combined, and examples thereof include a tetrahydrofurylmethyl group.

Further, the above heterocyclic group may be represented by the following formula. * Represents a bond.

-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
—CH ₂ — constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with —O—, —S—, —S(O) ₂ — or —CO—,
The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M or MM. Examples of such a group include the following groups.

For example, trichloromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, 2,2-dibromoethyl group, 2,2,3,3-tetrafluoropropyl group, 2-ethoxyethyl group, 2 -Butoxyethyl group, 2-nitropropyl group, diethylaminoethyl group, (4-methoxyphenyl)methyl group, (2-methoxyphenyl)methyl group, (3-methoxyphenyl)methyl group, (4-nitrophenyl)methyl group , (2,4-dichlorophenyl)methyl group, (4-fluorophenyl)methyl group, (3,5-difluorophenyl)methyl group, 2,2,2-trifluoro-1-trifluoromethyl-1-phenylethyl Group, (phenoxy)(phenyl)methyl group, (benzyloxy)(phenyl)methyl group, pyrrolylmethyl group, pyrrolylethyl group, (4-aminophenyl)methyl group, (4-cyanophenyl)methyl group, 2-hydroxy-1 -Methyl-1-phenylethyl group, 2-chloro-1-methyl-1-phenylethyl group;
-CH ₂ CH ₂ OCH ₂ CH ₃ , -CH ₂ CH ₂ O(CH ₂ ) ₃ CH ₃ , -(CH ₂ CH ₂ O) ₂ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₃ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₄ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₅ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₆ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₇ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₈ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₉ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₁₀ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₁₁ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₁₂ CH ₂ CH ₃ , -(CH ₂ CH ₂ O) ₁₃ CH ₃ , -CH ₂ CH ₂ OH, -(CH ₂ CH ₂ O) ₂ H, -(CH ₂ CH ₂ O) ₃ H, -(CH ₂ CH ₂ O) ₄ H, -(CH ₂ CH ₂ O) ₅ H, -(CH ₂ CH ₂ O) ₆ H, -(CH ₂ CH ₂ O) ₇ H, -(CH ₂ CH ₂ O) ₈ H, -(CH ₂ CH ₂ O) ₉ H, -(CH ₂ CH ₂ O) ₁₀ H, -(CH ₂ CH ₂ O) ₁₁ H, -(CH ₂ CH ₂ O) ₁₂ H, -(CH ₂ CH ₂ O) ₁₃ H, -CH ₂ CH ₂ OCH ₃ , -(CH ₂ CH ₂ O) ₂ CH ₃ ,- (CH ₂ CH ₂ O) ₃ CH ₃ , -(CH ₂ CH ₂ O) ₄ CH ₃ , -(CH ₂ CH ₂ O) ₅ CH ₃ , -(CH ₂ CH ₂ O) ₆ CH ₃ , -(CH ₂ CH ₂ O) ₇ CH ₃ , -(CH ₂ CH ₂ O) ₈ CH ₃ , -(CH ₂ CH ₂ O) ₉ CH ₃ , -(CH ₂ CH ₂ O) ₁₀ CH ₃ , -(CH ₂ CH -CH of the above monovalent hydrocarbon group or monovalent heterocyclic group such as ₂ O) ₁₁ CH ₃ , -(CH ₂ CH ₂ O) ₁₂ CH ₃ and -(CH ₂ CH ₂ O) ₁₃ CH ₃ A group in which ₂ -is replaced by -O-;
Examples of the alkyl group having a substituent such as (hereinafter, these may be referred to as a group A group).

For example, 4-bromophenyl group, 4-nitrophenyl group, 4-methoxyphenyl group, 2,4-dichlorophenyl group, pentafluorophenyl group, 2-aminophenyl group, 2-methyl-4-chlorophenyl group, 4-hydroxy An aryl group having a substituent such as a -1-naphthyl group, a 4,5,8-trichloro-2-naphthyl group, an anthraquinonyl group, and a 2-aminoanthraquinonyl group (hereinafter, these may be referred to as a group B group. ) Is mentioned.

For example, formyl group; acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, 2-ethylhexanoyl group, heptanoyl group, octanoyl group, nonanoyl group, decanoyl group, undecanoyl group, Dodecanoyl group, henicosanoyl group, benzoyl group,

And a carbonyl group to which the above group A to B group or the above monovalent hydrocarbon group or monovalent heterocyclic group is bonded,

A carbonyl group to which a hydrocarbon group having 1 to 30 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is preferably bonded,
A carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is preferably bonded,
A carbonyl group having a hydrocarbon group having 1 to 18 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is preferably bonded,
A carbonyl group to which a hydrocarbon group having 1 to 12 carbon atoms, a group of the above groups A to B, or the above monovalent hydrocarbon group or a preferable monovalent heterocyclic group is bonded is particularly preferable.
* Represents a bond.

For example, methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, tert-butoxycarbonyl group, butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethylhexyl)oxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group. Group, nonyloxycarbonyl group, decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, phenyloxycarbonyl group, icosyloxycarbonyl group,

And an oxycarbonyl group to which the above group A to B group or the above monovalent hydrocarbon group or monovalent heterocyclic group is bonded,

An oxycarbonyl group to which a hydrocarbon group having 1 to 30 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is preferably bonded,
An oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is bonded is more preferable,
An oxycarbonyl group to which a hydrocarbon group having 1 to 18 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is preferably bonded,
An oxycarbonyl group to which a hydrocarbon group having 1 to 12 carbon atoms, a group of the above groups A to B, or the above monovalent hydrocarbon group or a preferable monovalent heterocyclic group is bonded is particularly preferable.
* Represents a bond.

For example, formyloxy group; acetoxy group, propanoyloxy group, butanoyloxy group, (2,2-dimethylpropanoyl)oxy group, pentanoyloxy group, hexanoyloxy group, (2-ethylhexanoyl)oxy group, Heptanoyloxy group, octanoyloxy group, nonanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, ethenylcarbonyloxy group, (2-propenyl ) A carbonyloxy group, a (1-methylethenyl)carbonyloxy group, and a group of the above groups A to B or a carbonyloxy group to which the above monovalent hydrocarbon group or monovalent heterocyclic group is bonded, and the like,

A carbonyloxy group to which a hydrocarbon group having 1 to 30 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is preferably bonded,
A carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is bonded is more preferable,
A carbonyloxy group to which a hydrocarbon group having 1 to 18 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is preferably bonded,
A carbonyloxy group to which a hydrocarbon group having 1 to 12 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is preferably bonded is particularly preferable.

For example, hydroxy group; methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, neopentyloxy group, 1-ethyl-1,2- Dimethylpropoxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethylhexyl)oxy group, stearyloxy group, icosyloxy group, 1-phenylethoxy Group, 1-methyl-1-phenylethoxy group, phenyloxy group, benzyloxy group, 2,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 2,6 -Dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 3,5-dimethylphenyloxy group, 2,3-dicyanophenyloxy group, 2,4-dicyanophenyloxy group, 2,5-dicyanophenyloxy group , 2,6-dicyanophenyloxy group, 3,4-dicyanophenyloxy group, 3,5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxyphenyloxy group, 3-methoxyphenyloxy group, 4 -Ethoxyphenyloxy group, 2-ethoxyphenyloxy group, 3-ethoxyphenyloxy group;
Trichloromethoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, 2,2,3,3-tetrafluoropropoxy group, 3,3,3-trifluoro-2-trifluoromethyl-2- Methylpropoxy group, 2-butoxyethoxy group, 2-nitropropoxy group, -OCH ₂ CH ₂ OH, -O(CH ₂ CH ₂ O) ₄ H, -OCH ₂ CF ₂ CF ₂ H, -OCH ₂ CH ₂ O (CH ₂ ) ₃ CH ₃ , -OCH ₂ CH ₂ OCH ₂ CH ₃ , -O(CH ₂ CH ₂ O) ₂ CH ₂ CH ₃ , -O(CH ₂ CH ₂ O) ₄ CH ₂ CH ₃ , -OCH ₂ CH ₂ O(CH ₂ ) ₃ CH ₃ ,

And an oxy group or the like to which the above group A to B group or the above monovalent hydrocarbon group or monovalent heterocyclic group is bonded,

An oxy group to which a hydrocarbon group having 1 to 30 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is bonded, or a hydroxy group is preferable,
An oxy group or a hydroxy group to which a preferable one of a hydrocarbon group having 1 to 20 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is bonded,
An oxy group or a hydroxy group, to which a hydrocarbon group having 1 to 18 carbon atoms, a group of the above groups A to B, or the above-mentioned monovalent hydrocarbon group or a monovalent heterocyclic group is bonded, or a hydroxy group is further preferable,
An oxy group or a hydroxy group bonded to a hydrocarbon group having 1 to 12 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a preferable monovalent heterocyclic group described above is particularly preferable.
* Represents a bond.

For example, mercapto group; methylthio group, ethylthio group, propylthio group, butylthio group, tert-butylthio group, pentylthio group, hexylthio group, (2-ethylhexyl)thio group, heptylthio group, octylthio group, nonylthio group, decylthio group, undecylthio group, Dodecylthio group, icosylthio group, phenylthio group, o-tolylthio group,

And a mercapto group in which a hydrogen atom is substituted with the above group A to B or the above monovalent hydrocarbon group or monovalent heterocyclic group, and the like,

A mercapto group or a mercapto group in which a hydrogen atom is substituted with a hydrocarbon group having 1 to 30 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is preferable. Preferably
A mercapto group or a mercapto group in which a hydrogen atom is substituted with a hydrocarbon group having 1 to 20 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is preferable. More preferably,
A mercapto group or a mercapto group in which a hydrogen atom is substituted with a hydrocarbon group having 1 to 18 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is preferable. More preferably,
A mercapto group or a mercapto group in which a hydrogen atom is substituted with a hydrocarbon group having 1 to 12 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is preferable. Especially preferred.
* Represents a bond.

For example, methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, (2-ethylhexyl)sulfonyl group, heptylsulfonyl group, octylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, Decylsulfonyl group, dodecylsulfonyl group, icosylsulfonyl group, phenylsulfonyl group, p-tolylsulfonyl group,

And a sulfonyl group to which the above group A to B group or the above monovalent hydrocarbon group or monovalent heterocyclic group is bonded,

A sulfonyl group to which a hydrocarbon group having 1 to 30 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is preferably bonded,
A sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms, a group of the above groups A to B, or the above monovalent hydrocarbon group or a monovalent heterocyclic group is bonded is more preferable,
A sulfonyl group having a hydrocarbon group having 1 to 18 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is preferably bonded,
A sulfonyl group to which a hydrocarbon group having 1 to 12 carbon atoms, a group of the above groups A to B, or the above monovalent hydrocarbon group or a preferable monovalent heterocyclic group is bonded is particularly preferable.
* Represents a bond.

For example,
Sulfamoyl group;
N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N- (Sec-Butyl)sulfamoyl group, N-(tert-butyl)sulfamoyl group, N-pentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N-hexylsulfamoyl group, N-(2- Ethylhexyl)sulfamoyl group, N-heptylsulfamoyl group, N-octylsulfamoyl group, N-nonylsulfamoyl group, N-decylsulfamoyl group, N-undecylsulfamoyl group, N-dodecylsulfa group Moyl group, N-icosylsulfamoyl group, N-phenylsulfamoyl group, -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ , -SO ₂ NHCH ₂ CH ₂ CH ₂ Si(OCH ₂ CH ₃ ) ₃ and a sulfamoyl group substituted by one of the groups A to B or the monovalent hydrocarbon group or monovalent heterocyclic group described above;

N,N-dimethylsulfamoyl group, N-ethyl-N-methylsulfamoyl group, N,N-diethylsulfamoyl group, N-propyl-N-methylsulfamoyl group, N,N-dipropyls Rufamoyl group, N-isopropyl-N-methylsulfamoyl group, N,N-diisopropylsulfamoyl group, N,N-diisobutylsulfamoyl group, N,N-di(sec-butyl)sulfamoyl group, N -(Tert-butyl)-N-methylsulfamoyl group, N,N-di(tert-butyl)sulfamoyl group, N-butyl-N-methylsulfamoyl group, N,N-dibutylsulfamoyl group, N-butyl-N-octylsulfamoyl group, N,N-dipentylsulfamoyl group, N,N-bis(1-ethylpropyl)sulfamoyl group, N-butyl-N-hexylsulfamoyl group, N- Hexyl-N-methylsulfamoyl group, N,N-dihexylsulfamoyl group, N-(2-ethylhexyl)-N-methylsulfamoyl group, N,N-bis(2-ethylhexyl)sulfamoyl group, N , N-diheptylsulfamoyl group, N-octyl-N-methylsulfamoyl group, N,N-dioctylsulfamoyl group, N,N-dinonylsulfamoyl group, N-decyl-N-methylsulfyl group Famoyl group, N-undecyl-N-methylsulfamoyl group, N-dodecyl-N-methylsulfamoyl group, N-icosyl-N-methylsulfamoyl group, N-phenyl-N-methylsulfamoyl group A group, an N,N-diphenylsulfamoyl group, and
Examples thereof include the groups of the groups A to B, the monovalent hydrocarbon group, and the sulfamoyl group substituted with two selected from the monovalent heterocyclic group.

One or two selected from a hydrocarbon group having 1 to 30 carbon atoms, a group of the above groups A to B, a preferable one of the above monovalent hydrocarbon groups and a preferable one of the above monovalent heterocyclic groups. A substituted sulfamoyl group, —SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ or a sulfamoyl group is preferable,
One or two selected from a hydrocarbon group having 1 to 20 carbon atoms, a group of the above groups A to B, a preferable one of the above monovalent hydrocarbon groups and a preferable one of the above monovalent heterocyclic groups. A substituted sulfamoyl group, —SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ or a sulfamoyl group is more preferable,
One or two selected from a hydrocarbon group having 1 to 18 carbon atoms, a group of the above groups A to B, a preferable one of the above monovalent hydrocarbon groups and a preferable one of the above monovalent heterocyclic groups. A substituted sulfamoyl group, —SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ or a sulfamoyl group is more preferable,
One or two selected from a hydrocarbon group having 1 to 12 carbon atoms, a group of the above groups A to B, a preferable one of the above monovalent hydrocarbon groups and a preferable one of the above monovalent heterocyclic groups. Substituted sulfamoyl groups, -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ or sulfamoyl groups are especially preferred.

For example,
Carbamoyl group;
N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-isopropylcarbamoyl group, N-butylcarbamoyl group, N-isobutylcarbamoyl group, N-(sec-butyl)carbamoyl group, N-(tert -Butyl)carbamoyl group, N-pentylcarbamoyl group, N-(1-ethylpropyl)carbamoyl group, N-hexylcarbamoyl group, N-(2-ethylhexyl)carbamoyl group, N-heptylcarbamoyl group, N-octylcarbamoyl group , N-nonylcarbamoyl group, N-decylcarbamoyl group, N-undecylcarbamoyl group, N-dodecylcarbamoyl group, N-icosylcarbamoyl group, N-phenylcarbamoyl group, -CONH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ , —CONHCH ₂ CH ₂ CH ₂ Si(OCH ₂ CH ₃ ) ₃ , and one of the groups A to B or the monovalent hydrocarbon group or monovalent heterocyclic group A substituted carbamoyl group or the like;

N,N-dimethylcarbamoyl group, N-ethyl-N-methylcarbamoyl group, N,N-diethylcarbamoyl group, N-propyl-N-methylcarbamoyl group, N,N-dipropylcarbamoyl group, N-isopropyl-N -Methylcarbamoyl group, N,N-diisopropylcarbamoyl group, N,N-diisobutylcarbamoyl group, N,N-di(sec-butyl)carbamoyl group, N-(tert-butyl)-N-methylcarbamoyl group, N, N-di(tert-butyl)carbamoyl group, N-butyl-N-methylcarbamoyl group, N,N-dibutylcarbamoyl group, N-butyl-N-octylcarbamoyl group, N,N-dipentylcarbamoyl group, N,N -Bis(1-ethylpropyl)carbamoyl group, N-butyl-N-hexylcarbamoyl group, N-hexyl-N-methylcarbamoyl group, N,N-dihexylcarbamoyl group, N-(2-ethylhexyl)-N-methyl Carbamoyl group, N,N-bis(2-ethylhexyl)carbamoyl group, N,N-diheptylcarbamoyl group, N-octyl-N-methylcarbamoyl group, N,N-dioctylcarbamoyl group, N,N-dinonylcarbamoyl group Group, N-decyl-N-methylcarbamoyl group, N-undecyl-N-methylcarbamoyl group, N-dodecyl-N-methylcarbamoyl group, N-icosyl-N-methylcarbamoyl group, N-phenyl-N-methylcarbamoyl group A group, an N,N-diphenylcarbamoyl group, and
And a carbamoyl group substituted with two selected from the above groups A to B, the above monovalent hydrocarbon group and the above monovalent heterocyclic group,

One or two selected from a hydrocarbon group having 1 to 30 carbon atoms, a group of the above groups A to B, a preferable one of the above monovalent hydrocarbon groups and a preferable one of the above monovalent heterocyclic groups. A substituted carbamoyl group or a carbamoyl group is preferable,
One or two selected from a hydrocarbon group having 1 to 20 carbon atoms, a group of the above groups A to B, a preferable one of the above monovalent hydrocarbon groups and a preferable one of the above monovalent heterocyclic groups. A substituted carbamoyl group or a carbamoyl group is more preferable,
One or two selected from a hydrocarbon group having 1 to 18 carbon atoms, a group of the above groups A to B, a preferable one of the above monovalent hydrocarbon groups and a preferable one of the above monovalent heterocyclic groups. A substituted carbamoyl group or a carbamoyl group is more preferable,
One or two selected from a hydrocarbon group having 1 to 12 carbon atoms, a group of the above groups A to B, a preferable one of the above monovalent hydrocarbon groups and a preferable one of the above monovalent heterocyclic groups. Substituted carbamoyl groups or carbamoyl groups are particularly preferred.

For example,
Amino group;
N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-(sec-butyl)amino group, N-(tert -Butyl)amino group, N-pentylamino group, N-(1-ethylpropyl)amino group, N-hexylamino group, N-(2-ethylhexyl)amino group, N-heptylamino group, N-octylamino group , N-nonylamino group, N-decylamino group, N-undecylamino group, N-dodecylamino group, N-icosylamino group, N-phenylamino group, and the above groups A to B or the above monovalent groups An amino group substituted with one hydrocarbon group or a monovalent heterocyclic group;

N,N-dimethylamino group, N-ethyl-N-methylamino group, N,N-diethylamino group, N-propyl-N-methylamino group, N,N-dipropylamino group, N-isopropyl-N- Methylamino group, N,N-diisopropylamino group, N,N-diisobutylamino group, N,N-di(sec-butyl)amino group, N-(tert-butyl)-N-methylamino group, N,N -Di(tert-butyl)amino group, N-butyl-N-methylamino group, N,N-dibutylamino group, N-butyl-N-octylamino group, N,N-dipentylamino group, N,N- Bis(1-ethylpropyl)amino group, N-butyl-N-hexylamino group, N-hexyl-N-methylamino group, N,N-dihexylamino group, N-(2-ethylhexyl)-N-methylamino Group, N,N-bis(2-ethylhexyl)amino group, N,N-diheptylamino group, N-octyl-N-methylamino group, N,N-dioctylamino group, N,N-dinonylamino group, N -Decyl-N-methylamino group, N-undecyl-N-methylamino group, N-dodecyl-N-methylamino group, N-icosyl-N-methylamino group, N-phenyl-N-methylamino group, N , N-diphenylamino group, and
Examples include the groups of the above groups A to B, the above monovalent hydrocarbon group, and an amino group substituted with two selected from the above monovalent heterocyclic group,

One or two selected from a hydrocarbon group having 1 to 30 carbon atoms, a group of the above groups A to B, a preferable one of the above monovalent hydrocarbon groups and a preferable one of the above monovalent heterocyclic groups. A substituted amino group, or an amino group is preferable,
One or two selected from a hydrocarbon group having 1 to 20 carbon atoms, a group of the above groups A to B, a preferable one of the above monovalent hydrocarbon groups and a preferable one of the above monovalent heterocyclic groups. A substituted amino group or an amino group is more preferable,
One or two selected from a hydrocarbon group having 1 to 18 carbon atoms, a group of the above groups A to B, a preferable one of the above monovalent hydrocarbon groups and a preferable one of the above monovalent heterocyclic groups. A substituted amino group or an amino group is more preferable,
One or two selected from a hydrocarbon group having 1 to 12 carbon atoms, a group of the above groups A to B, a preferable one of the above monovalent hydrocarbon group and a preferable one of the above monovalent heterocyclic group. Substituted amino groups or amino groups are especially preferred.

For example, formylamino group; acetylamino group, propanoylamino group, butanoylamino group, (2,2-dimethylpropanoyl)amino group, pentanoylamino group, hexanoylamino group, (2-ethylhexanoyl)amino group. Group, heptanoylamino group, octanoylamino group, nonanoylamino group, decanoylamino group, undecanoylamino group, dodecanoylamino group, henicosanoylamino group, benzoylamino group,

And a carbonylamino group to which the above group A to B group or the above monovalent hydrocarbon group or monovalent heterocyclic group is bonded,

A carbonylamino group to which a hydrocarbon group having 1 to 30 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is preferably bonded,
A carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms, a group of the above groups A to B, or a monovalent hydrocarbon group or a monovalent heterocyclic group described above is bonded is more preferable,
A carbonylamino group to which a hydrocarbon group having 1 to 18 carbon atoms, a group of the above groups A to B, or the above-mentioned monovalent hydrocarbon group or a monovalent heterocyclic group is bonded is more preferable,
A carbonylamino group to which a hydrocarbon group having 1 to 12 carbon atoms, a group of the above groups A to B, or the above monovalent hydrocarbon group or a preferable monovalent heterocyclic group is bonded is particularly preferable.
* Represents a bond.

For example,
-SiH ₃ ;
-Si(CH ₃ ) ₃ ,
_{_{_{-Si (CH 2 CH 3) 3}}} ,
--Si((CH ₂ ) ₂ CH ₃ ) ₃ ,
_{_{-Si (CH (CH 3) 2}} ) 3,
--Si((CH ₂ ) ₃ CH ₃ ) ₃ ,
--Si((CH ₂ ) ₄ CH ₃ ) ₃ ,
--Si((CH ₂ ) ₅ CH ₃ ) ₃ ,
_{_{-Si ((CH 2) 6 CH}} 3) 3,
--Si((CH ₂ ) ₇ CH ₃ ) ₃ ,
--Si((CH ₂ ) ₈ CH ₃ ) ₃ ,
_{_{-Si ((CH 2) 9 CH}} 3) 3,
_{_{-Si ((CH 2) 10 CH}} 3) 3,
--Si((CH ₂ ) ₁₁ CH ₃ ) ₃ ,
_{_{-Si ((CH 2) 12 CH}} 3) 3,
_{_{_{-Si (C 6 H 5) 3}}} ,
-Si(C ₁₀ H ₇ ) ₃ ,
--Si(CH ₃ ) ₂ (CH ₂ CH ₃ ),
_{_{-Si (CH 3) 2 ((}} CH 2) 2 CH 3),
--Si(CH ₃ ) ₂ (CH(CH ₃ ) ₂ ),
_{_{-Si (CH 3) 2 ((}} CH 2) 3 CH 3),
--Si(CH ₃ ) ₂ ((CH ₂ ) ₅ CH ₃ ),
_{_{-Si (CH 3) 2 ((}} CH 2) 7 CH 3),
_{_{-Si (CH 3) 2 ((}} CH 2) 9 CH 3),
_{_{-Si (CH 3) 2 ((}} CH 2) 11 CH 3),
_{_{-Si (CH 3) 2 ((}} CH 2) 13 CH 3),
--Si(CH ₃ ) ₂ ((CH ₂ ) ₁₅ CH ₃ ),
_{_{-Si (CH 3) 2 ((}} CH 2) 17 CH 3),
--Si(CH ₃ ) ₂ ((CH ₂ ) ₁₉ CH ₃ ),
_{_{-Si (CH 3) 2 ((}} CH 2) 29 CH 3),
-Si(CH ₃ ) ₂ (C ₆ H ₅ ),
--Si(CH ₃ )(C ₆ H ₅ ) ₂ ,
-Si(CH ₃ ) ₂ (C ₁₀ H ₇ ),
And —SiH _3, etc. substituted with one, two or three selected from the above groups A to B, the above monovalent hydrocarbon group and the above monovalent heterocyclic group;

-Si(OH) ₃ ;
-Si(OCH ₃ ) ₃ ,
-Si(OCH ₂ CH ₃ ) ₃ ,
_{_{-Si (O (CH 2) 2}} CH 3) 3,
_{_{-Si (OCH (CH 3) 2}} ) 3,
_{_{-Si (O (CH 2) 3}} CH 3) 3,
_{_{-Si (O (CH 2) 4}} CH 3) 3,
_{_{-Si (O (CH 2) 5}} CH 3) 3,
_{_{-Si (O (CH 2) 6}} CH 3) 3,
_{_{-Si (O (CH 2) 7}} CH 3) 3,
_{_{-Si (O (CH 2) 8}} CH 3) 3,
_{_{-Si (O (CH 2) 9}} CH 3) 3,
_{_{-Si (O (CH 2) 10}} CH 3) 3,
_{_{-Si (O (CH 2) 11}} CH 3) 3,
-Si(OC ₆ H ₅ ) ₃ ,
-Si(OC ₁₀ H ₇ ) ₃ ,
--Si(OCH ₃ ) ₂ (OCH ₂ CH ₃ ),
--Si(OCH ₃ ) ₂ (O(CH ₂ ) ₂ CH ₃ ),
--Si(OCH ₃ ) ₂ (OCH(CH ₃ ) ₂ ),
--Si(OCH ₃ ) ₂ (O(CH ₂ ) ₃ CH ₃ ),
--Si(OCH ₃ ) ₂ (O(CH ₂ ) ₅ CH ₃ ),
--Si(OCH ₃ ) ₂ (O(CH ₂ ) ₇ CH ₃ ),
--Si(OCH ₃ ) ₂ (O(CH ₂ ) ₉ CH ₃ ),
_{_{-Si (OCH 3) 2 (O}} (CH 2) 11 CH 3),
--Si(OCH ₃ ) ₂ (O(CH ₂ ) ₁₃ CH ₃ ),
--Si(OCH ₃ ) ₂ (O(CH ₂ ) ₁₅ CH ₃ ),
--Si(OCH ₃ ) ₂ (O(CH ₂ ) ₁₇ CH ₃ ),
_{_{-Si (OCH 3) 2 (O}} (CH 2) 19 CH 3),
--Si(OCH ₃ ) ₂ (O(CH ₂ ) ₂₉ CH ₃ ),
-Si(OCH ₃ ) ₂ (OC ₆ H ₅ ),
--Si(OCH ₃ )(OC ₆ H ₅ ) ₂ ,
--Si(OCH ₃ ) ₂ (OC ₁₀ H ₇ ),
And —Si(OH) ₃ substituted with one, two or three selected from the above groups A to B, the above monovalent hydrocarbon group and the above monovalent heterocyclic group;

-SiH(OH) ₂ ;
--Si(CH ₃ )(OCH ₃ ) ₂ ,
_{_{-Si ((CH 2) 11 CH}} 3) (O (CH 2) 11 CH 3) 2,
_{_{-Si (C 6 H 5) (}} OC 6 H 5) 2,
--Si(CH ₃ )(OH) ₂ ,
_{_{-Si ((CH 2) 36 CH}} 3) (OH) 2,
_{_{-Si (C 6 H 5) (}} OH) 2,
And —SiH(OH) ₂ substituted with one, two or three selected from the above groups A to B, the above monovalent hydrocarbon group and the above monovalent heterocyclic group;

-SiH ₂ (OH);
--Si(CH ₃ ) ₂ (OCH ₃ ),
_{_{-Si ((CH 2) 11 CH}} 3) 2 (O (CH 2) 11 CH 3),
-Si(C ₆ H ₅ ) ₂ (OC ₆ H ₅ ),
--Si(CH ₃ ) ₂ (OH),
_{_{-Si ((CH 2) 17 CH}} 3) 2 (OH),
-Si(C ₆ H ₅ ) ₂ (OH),
And —SiH ₂ (OH) substituted with one, two or three selected from the above groups A to B, the above monovalent hydrocarbon group and the above monovalent heterocyclic group;
,

One or two selected from a hydrocarbon group having 1 to 30 carbon atoms, a group of the above groups A to B, a preferable one of the above monovalent hydrocarbon groups and a preferable one of the above monovalent heterocyclic groups. Or preferably —SiH ₃ , —Si(OH) ₃ , —SiH(OH) ₂ and —SiH ₂ (OH), or —Si(OH) ₃ substituted with _three ,
One or two selected from a hydrocarbon group having 1 to 20 carbon atoms, a group of the above groups A to B, a preferable one of the above monovalent hydrocarbon groups and a preferable one of the above monovalent heterocyclic groups. Or more preferably —SiH ₃ , —Si(OH) ₃ , —SiH(OH) ₂ and —SiH ₂ (OH), or —Si(OH) ₃ substituted with _three ,
One or two selected from a hydrocarbon group having 1 to 18 carbon atoms, a group of the above groups A to B, a preferable one of the above monovalent hydrocarbon groups and a preferable one of the above monovalent heterocyclic groups. Or more preferably —SiH ₃ , —Si(OH) ₃ , —SiH(OH) ₂ and —SiH ₂ (OH) or —Si(OH) ₃ substituted with _three ,
One or two selected from a hydrocarbon group having 1 to 12 carbon atoms, a group of the above groups A to B, a preferable one of the above monovalent hydrocarbon groups and a preferable one of the above monovalent heterocyclic groups. Or, 3-substituted 3-SiH ₃ , -Si(OH) ₃ , -SiH(OH) ₂ and -SiH ₂ (OH), or -Si(OH) ₃ is particularly preferable.

Examples thereof include a phthalimidomethyl group (C ₆ H ₄ (CO) ₂ N—CH ₂ —) which may have a substituent, and examples of the substituent include the above halogen atom and the above groups A to B. At least one selected from the group consisting of a group, the above monovalent hydrocarbon group, the above monovalent heterocyclic group and the like.

Other groups include --SCOCH ₃ ,

Etc.
* Represents a bond.

The monovalent hydrocarbon group or the monovalent heterocyclic group _{^{^{said, -SO 3 - N + (C}}} 12 H 25) (CH 3) 3, -CO 2 - N + (C 12 H 25) (CH ₃ ) ₃ , —SO ₃ ⁻ , —CO ₂ ^{— and the} like may be substituted.

R ¹ and R ² , R ² and R ³ , and R ³ and R ⁴ may be bonded to each other to form a ring.

Examples of the alkali metal atom represented by M and MM include alkali metal atoms such as lithium atom, sodium atom and potassium atom.

Examples of the metal atom of the metal atom which may have a ligand represented by M and MM include metal atoms belonging to Groups 2 to 15 of the periodic table of the elements. The metal atom of the metal atom which may have a ligand is more preferably Mg, Ca, Sr, Ba, Cd, Ni, Zn, Cu, Hg, Fe, Co, Sn, Pb, Mn, Al, Cr, Rh, Ir, Pd, Ti, Zr, Hf, Si, Ge, and more preferably Mg, Ca, Sr, Ba, Ni, Zn, Cu, Fe, Co, Sn, Mn, Al, Cr is preferable, and Mg, Ca, Sr, Ba, Ni, Zn, Cu, Fe, Co, Mn, Al, and Cr are particularly preferable.

The ligand of the metal atom which may have a ligand is not particularly limited, and may be, for example, a halogen atom, NO, NO ₃ , SO ₄ , CH ₃ CO ₂ , OH, or the like,
A ligand coordinated to the metal atom, a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom contained in the same ligand may be coordinated to the same metal atom,
A plurality of different ligands may be coordinated to the same metal atom on the metal atom,
It may form an oligomer or a polymer.
When the compound (I) contains a metal atom which may have a ligand, the ligand also contains a compound (I) from which the metal atom which may have a ligand is removed. R.
Such oligomers or polymers are also contained in the compound (I) of the present invention.
However, the charge of the compound (I) is 0.

Examples of the compound (I) include metal salts represented by the following formulas (EN1) to (EN5).
However, in the formulas (EN1) to (EN5), the structure shown in () is repeatedly bonded like an oligomer and a polymer.
For example, the metal salt represented by the formula (EN1) is one in which the same ligand is coordinated to the same metal atom.
For example, the metal salts represented by the formulas (EN2) to (EN3) are those in which a plurality of different ligands are coordinated to the same metal atom to form an oligomer.
For example, the metal salts represented by the formulas (EN4) to (EN5) are those in which a plurality of different ligands are coordinated to the same metal atom to form an oligomer or a polymer.

As N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ) represented by M and MM,
NH ₄ ;
A group in which one alkyl group is substituted on NH ₄ such as NH ₃ ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), and NH ₃ ((CH ₂ ) ₁₇ CH ₃ );
_{_{N (CH 3) 3 ((}} CH 2) 15 CH 3), N (CH 3) 3 ((CH 2) 11 CH 3), N (CH 3) 2 ((CH 2) 11 CH 3) 2, N (CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) _{2 and} other groups in which 4 alkyl groups are substituted on NH ₄ .
And NH _4, substituted with one, two, three or four selected from the groups A to B, the monovalent hydrocarbon group and the monovalent heterocyclic group.
Etc.

M is
Hydrogen atom;
Alkali metal atom;
Mg which may have a ligand, Ca which may have a ligand, Sr which may have a ligand, Ba which may have a ligand, coordination Child which may have a child, Zn which may have a ligand, Cu which may have a ligand, Fe which may have a ligand, and a ligand. Co which may have, Sn which may have a ligand, Mn which may have a ligand, Al which may have a ligand, which has a ligand Optionally Cr;
NH ₄ ;
A group in which one alkyl group is substituted on NH ₄ such as NH ₃ ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), and NH ₃ ((CH ₂ ) ₁₇ CH ₃ );
_{_{N (CH 3) 3 ((}} CH 2) 15 CH 3), N (CH 3) 3 ((CH 2) 11 CH 3), N (CH 3) 2 ((CH 2) 11 CH 3) 2, N A group in which 4 alkyl groups are substituted on NH ₄ such as (CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) ₂ is preferable,

Hydrogen atom;
Sodium atom, potassium atom;
Mg which may have a ligand, Ca which may have a ligand, Sr which may have a ligand, Ba which may have a ligand, coordination Child which may have a child, Zn which may have a ligand, Cu which may have a ligand, Fe which may have a ligand, and a ligand. Co which may have, Mn which may have a ligand, Al which may have a ligand, and Cr which may have a ligand;
NH ₄ ;
A group in which one alkyl group is substituted on NH ₄ such as NH ₃ ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), and NH ₃ ((CH ₂ ) ₁₇ CH ₃ );
_{_{N (CH 3) 3 ((}} CH 2) 15 CH 3), N (CH 3) 3 ((CH 2) 11 CH 3), N (CH 3) 2 ((CH 2) 11 CH 3) 2, N A group in which four alkyl groups are substituted on NH ₄ such as (CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) ₂ is more preferable.

MM is
Alkali metal atom;
Mg which may have a ligand, Ca which may have a ligand, Sr which may have a ligand, Ba which may have a ligand, coordination Child which may have a child, Zn which may have a ligand, Cu which may have a ligand, Fe which may have a ligand, and a ligand. Co which may have, Sn which may have a ligand, Mn which may have a ligand, Al which may have a ligand, which has a ligand Optionally Cr;
NH ₄ ;
A group in which one alkyl group is substituted on NH ₄ such as NH ₃ ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), and NH ₃ ((CH ₂ ) ₁₇ CH ₃ );
_{_{N (CH 3) 3 ((}} CH 2) 15 CH 3), N (CH 3) 3 ((CH 2) 11 CH 3), N (CH 3) 2 ((CH 2) 11 CH 3) 2, N A group in which 4 alkyl groups are substituted on NH ₄ such as (CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) ₂ is preferable,

Sodium atom, potassium atom;
Mg which may have a ligand, Ca which may have a ligand, Sr which may have a ligand, Ba which may have a ligand, coordination Child which may have a child, Zn which may have a ligand, Cu which may have a ligand, Fe which may have a ligand, and a ligand. Co which may have, Mn which may have a ligand, Al which may have a ligand, and Cr which may have a ligand;
NH ₄ ;
A group in which one alkyl group is substituted on NH ₄ such as NH ₃ ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), and NH ₃ ((CH ₂ ) ₁₇ CH ₃ );
_{_{N (CH 3) 3 ((}} CH 2) 15 CH 3), N (CH 3) 3 ((CH 2) 11 CH 3), N (CH 3) 2 ((CH 2) 11 CH 3) 2, N A group in which four alkyl groups are substituted on NH ₄ such as (CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) ₂ is more preferable.

Q ¹ and Q ² each independently represent a divalent hydrocarbon group or a divalent heterocyclic group,
-C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N=,
—CH ₂ — constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with —O—, —S—, —S(O) ₂ — or —CO—,
The hydrogen atom constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M or MM.
The group replacing the hydrogen atom constituting the divalent hydrocarbon group and the divalent heterocyclic group is preferably a halogen atom, a cyano group, a nitro group, —SO ₃ H, or —CO ₂ H.

Q ¹ and Q ² may be the same or different and are preferably the same.
Q ¹ and Q ² are preferably groups represented by formulas (QQ1) to (QQ19).

[In the formulas (QQ1) to (QQ19),
R ^Q1 to R ^Q94 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms or a carbon atom. Represents a monovalent heterocyclic group of the numbers 1 to 40,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
—CH ₂ — constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with —O—, —S—, —S(O) ₂ — or —CO—,
The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M or MM.
R ^Q1 to R ^Q94 may be bonded to one or more ^members selected from R ^Q1 to R ^Q94 to form a ring.
M and MM have the same meanings as described above.
* Represents a bond. ]

A monovalent hydrocarbon group having 1 to 40 carbon atoms represented by R ^Q1 to R ^Q94 or a monovalent heterocyclic group having 1 to 40 carbon atoms,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
—CH ₂ — constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with —O—, —S—, —S(O) ₂ — or —CO—,
The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group is a group which may be replaced with a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M or MM. Is
A monovalent hydrocarbon group having 1 to 40 carbon atoms or a monovalent heterocyclic group having 1 to 40 carbon atoms represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ ,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
—CH ₂ — constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with —O—, —S—, —S(O) ₂ — or —CO—,
The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group is a group which may be replaced with a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M or MM. The same can be mentioned.

Preferred examples of R ^Q1 to R ^Q94 are the same as those of R ¹ to R ⁵ and Z ¹ to Z ⁴ .

Q ¹ and Q ² are
The groups represented by formulas (QQ1) to (QQ12) are preferable,
More preferably, it is a group represented by formula (QQ1) to formula (QQ5),
The groups represented by formulas (QQ1) to (QQ4) are more preferable,
A group represented by formula (QQ1) and formula (QQ2) is particularly preferable,
A group represented by formula (QQ2) is more preferred.

Examples of formulas (QQ1) to (QQ19) include the following formulas (Qa1) to (Qa50);
Formula (Qb1) to Formula (Qb27);
Formula (Qc1) to Formula (Qc56);
Formula (Qd1) to Formula (Qd41);
Formula (Qe1) to Formula (Qe16);
Formula (Qf1) to Formula (Qf15);
Formula (Qg1) to Formula (Qg40);
Formula (Qh1) to Formula (Qh40);
Formula (Qj1) to Formula (Qj29);
Formula (Qk1) to Formula (Qk22);
Formula (Qm1) to Formula (Qm20);
Formula (Qn1) to Formula (Qn16);
Formula (Qо1) to Formula (Qо15);
Formula (Qp1) to Formula (Qp83);
Formula (Qq1) to Formula (Qq72);
Formula (Qr1) to Formula (Qr17);
Formula (Qs1) to Formula (Qs26);
Formula (Qt1) to Formula (Qt26);
Formula (Qu1) to Formula (Qu17);
Formula (Qv1) to Formula (Qv26);
Formula (Qx1) to Formula (Qx2); and Formula (Qy1) to Formula (Qy10)
And the like. However, * represents a bond.

Examples of the compound (I) include compounds represented by the formula (Ia) shown in Tables 1 to 14 below or alkali metal salts thereof.
The symbols in the “Q ¹ ”column and the “Q ² ” column in Tables 1 to 14 correspond to the groups represented by the above formulas.
* Represents a bond.

Examples of the compound (I) include compounds represented by the formula (Ib) shown in Tables 15 to 31 below or an alkali metal salt thereof.

In formula (Ib), any one of R ^Ib1 to R ^Ib5 is a substituent that is not a hydrogen atom (hereinafter sometimes referred to as an RR group), and the other four are hydrogen atoms.
The symbols described in the “Q ¹ ”column and the “Q ² ” column in Tables 15 to 31 respectively correspond to the groups represented by the above formulas.
The symbols described in the "RR" column in Tables 15 to 31 represent RR groups, which are represented by the following formulas (a1) to (a69);
Formula (b1) to Formula (b4);
Formula (c1) to Formula (c4);
Formula (d1) to Formula (d5);
Formula (e1) to Formula (e20);
Formula (f1) to Formula (f5);
Formula (g1) to Formula (g9);
Formula (h1) to Formula (h9);
Formula (j1) to Formula (j9);
Formula (k1) to Formula (k4);
Formula (m1) to Formula (m9);
Formula (n1) to Formula (n3);
Expression (о1) to Expression (о5);
Formula (p1) to Formula (p23);
Formula (q1) to Formula (q26);
Formula (r1) to Formula (r26);
Formula (s1) to Formula (s26);
It corresponds to the group represented by
Numerical values described in the “No” column in Tables 15 to 31 represent the positions substituted by the RR groups,
“1” represents that the RR group is substituted for R ^Ib1 ;
“2” represents that the RR group is substituted for R ^Ib2 ,
“3” represents that the RR group is substituted with R ^Ib3 ,
“4” represents that the RR group is substituted for R ^Ib4 ,
"5" represents that the RR group is substituted for ^RIb5 .
* Represents a bond.

Examples of the compound (I) include compounds represented by the formula (If) shown in the following Tables f1 to f44 or alkali metal salts thereof.
The symbols in the “Q ¹ ”column and the “Q ² ” column in Tables f1 to f44 correspond to the groups represented by the above formulas.
* Represents a bond.

Examples of the compound (I) include compounds represented by the formula (It) shown in Tables t1 to t5 below, compounds represented by the formula (Iu) shown in Tables u1 to u11 below, and alkali metals thereof. Examples include salt.
In Tables t1 to t5 and Tables u1 to u11, the symbols in the “aq” column, the “Q ¹ ”column, the “Q ² ”column, and the “Q ^u+1 ” column are the above formulas, respectively. And a group represented by the following formulas (aq1) to (aq36).
In the column “Q ^u+1 ”in Table u1 to Table u11, the group represented by Q ¹ and the group represented by Q ² in the compound represented by the formula (Iu) are described in the column “Q ^u+1 ”. Represents the group corresponding to the symbol.
In the groups represented by the following formulas (aq1) to (aq36), # represents a bond with Q ¹ and & represents a bond with Q ² .

Examples of the compound (I) include compounds represented by the formula (Ia1) to the formula (Ia2216) and the formula (Ib1) to the formula (Ib1312),
A compound represented by the formula (If1) to the formula (If13090),
The compounds represented by the formulas (It1) to (It900) and the compounds represented by the formulas (Iu1) to (Iu3238) are added to -SO ₃ H, -CO ₂ H, -SO ₃ NH ₄ , -CO ₂ NH ₄ , —SO ₂ NH ₂ , —CONH ₂ , phthalimidomethyl group (C ₆ H ₄ (CO) ₂ N—CH ₂ —), —SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ , A compound in which one or more selected from —N(CH ₃ )((CH ₂ ) ₁₁ CH ₃ ), a fluorine atom, a chlorine atom and a bromine atom is substituted is also included.

For example, a compound represented by the formula (Ia1) in Table 1 in which —SO ₃ H is substituted has the following structure. However, in the formula, —(SO ₃ H) means that —SO ₃ H replaces all or one or more hydrogen atoms of the compound represented by the formula (Ia1).

Examples of such a compound include compounds represented by formula (Ic1) to formula (Ic12) in which all of the hydrogen atoms of the aromatic ring are substituted with one or more selected from a fluorine atom, a chlorine atom and a bromine atom. Can also be mentioned.

Examples of the compound (I) include compounds represented by the formula (Ia1) to the formula (Ia2216) and the formula (Ib1) to the formula (Ib1312),
A compound represented by the formula (If1) to the formula (If13090):
The compounds represented by the formulas (It1) to (It900) and the compounds represented by the formulas (Iu1) to (Iu3238) are added to -SO ₃ H, -CO ₂ H, -SO ₃ NH ₄ , -CO ₂ NH ₄ , —SO ₂ NH ₂ , —CONH ₂ , phthalimidomethyl group (C ₆ H ₄ (CO) ₂ N—CH ₂ —), —SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ , A compound in which 1 to 6 of at least one selected from --N(CH ₃ )((CH ₂ ) ₁₁ CH ₃ ), a fluorine atom, a chlorine atom and a bromine atom is substituted is also included.

For example, a compound represented by the formula (Ia1) in Table 1 in which 1 to 6 —SO ₃ H is substituted has the following structure. However, in the formula, -(SO ₃ H) _{1 to 6} means that any one of 1 to 6 hydrogen atoms of the compound represented by the formula (Ia1) is replaced by -SO ₃ H. It shall be.

Examples of the compound (I) include compounds represented by the formula (Ia1) to the formula (Ia2216) and the formula (Ib1) to the formula (Ib1312),
A compound represented by the formula (If1) to the formula (If13090),
The compounds represented by the formulas (It1) to (It900) and the compounds represented by the formulas (Iu1) to (Iu3238) are substituted with one or more selected from -SO ₃ ^- and -CO ₂ ^- . With anions,
Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Ni ²⁺ , Zn ²⁺ , Fe ²⁺ , Co ²⁺ , Sn ²⁺ , Mn ²⁺ , Al ³⁺ , Fe ³⁺ , Cr ³⁺ , Mention may be made of metal salts consisting of one or more cations selected from Sn ⁴⁺ , Mn ⁴⁺ , Cu ²⁺ , Li ⁺ , Na ⁺ and K ⁺ .

Examples of the compound (I) include anions represented by the formula (Id) and anions represented by the formula (Ih) shown in Tables 32 to 33 and h1 to h6 below.
Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Ni ²⁺ , Zn ²⁺ , Fe ²⁺ , Co ²⁺ , Sn ²⁺ , Mn ²⁺ , Al ³⁺ , Fe ³⁺ , Cr ³ ^Mention may be made of metal salts comprising one or more cations selected from ⁺ , Sn ⁴⁺ , Mn ⁴⁺ , Cu ²⁺ , Li ⁺ , Na ⁺ and K ⁺ .

The symbols described in the “Q ¹ ”column and the “Q ² ” column in Tables 32 to 33 and Tables h1 to h6 are the groups represented by the above formulas and the following formulas (Qw1) to ( It corresponds to the group represented by Qw11).

Examples of such metal salts include metal salts represented by the formula (Ie) shown in Tables 34 to 38 below and metal salts represented by the formula (Ik) shown in Tables k1 to k14.
As a symbol described in the “Met” column in Tables 34 to 38 and Tables k1 to k14, Mg2+ represents Mg ²⁺ ,
Ca2 + represents Ca ^2+,
Sr2 + represents Sr ^2+,
Ba2 + represents the Ba ^2+,
Ni2 + represents the Ni ^2+,
Zn2+ represents Zn2 ⁺ ,
Fe2 + represents the Fe ^2+,
Co2 + represents the Co ^2+,
Sn2 ⁺ represents Sn2 ⁺ ,
Mn2 + represents the Mn ^2+,
Al3 + represents Al ^3+,
Fe3 + represents the Fe ^3+,
Cr3 + represents the Cr ^3+,
Sn4 + represents a Sn ^4+,
Mn4 + represents the Mn ^4+,
Cu2 + represents the Cu ^2+,
Li+ represents Li ⁺ ,
Na+ represents Na ⁺ ,
K+ represents K ⁺ .

The symbols described in the “Q ¹ ”column and the “Q ² ” column in Tables 34 to 38 and Tables k1 to k14 correspond to the groups represented by the above formulas, respectively.
M in formula (Ie) and formula (Ik) is an integer of 1 or more, preferably an integer of 1 to 20, and more preferably an integer of 1 to 10.
N in formula (Ie) and formula (Ik) is an integer of 1 or more, preferably an integer of 1 to 20, and more preferably an integer of 1 to 10.
However, when the compound (I) of the present invention is the above-mentioned oligomer or polymer, m and n are the ratio of the number of ligands and the number of metal atoms such that the charge of the compound (I) becomes zero. The compound (I) is the above-mentioned oligomer or polymer by representing the smallest integer.

As compound (I),
A compound represented by formula (Ia1) to formula (Ia2216);
Compounds represented by formula (If1) to formula (If13090);
Compounds represented by formula (It1) to formula (It900); and compounds represented by formula (Iu1) to formula (Iu3238);
A compound represented by formula (Ib8);
A compound represented by formula (Ib14):
A compound represented by formula (Ia1) to formula (Ia2216),
A compound represented by the formula (If1) to the formula (If13090),
A compound represented by formula (It1) to formula (It900),
A compound represented by formula (Iu1) to formula (Iu3238),
A compound represented by the formula (Ib8) and a compound represented by the formula (Ib14),
--SO ₃ H, --CO ₂ H, --SO ₃ NH ₄ , --CO ₂ NH ₄ , --SO ₂ NH ₂ , --CONH ₂ , phthalimidomethyl group (C ₆ H ₄ (CO) ₂ N--CH ₂ --) , --SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ , --N(CH ₃ )((CH ₂ ) ₁₁ CH ₃ ), one or more selected from a fluorine atom, a chlorine atom and a bromine atom. A substituted compound; and a compound represented by formula (Ia1) to formula (Ia2216),
A compound represented by the formula (If1) to the formula (If13090),
A compound represented by formula (It1) to formula (It900),
A compound represented by formula (Iu1) to formula (Iu3238),
A compound represented by the formula (Ib8) and a compound represented by the formula (Ib14),
And one or more selected from the substituted anions, ^- -SO ₃ ^- and -CO ₂
Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Ni ²⁺ , Zn ²⁺ , Fe ²⁺ , Co ²⁺ , Sn ²⁺ , Mn ²⁺ , Al ³⁺ , Fe ³⁺ , Cr ³⁺ , Sn ⁴⁺ , Mn ⁴⁺ , Cu ²⁺ , Li ⁺ , Na ^+, and a metal salt consisting of one or more cations selected from K ⁺ are preferable,

A compound represented by formula (Ia1) to formula (Ia2216);
Compounds represented by formula (If1) to formula (If13090);
A compound represented by formula (It1) to formula (It900);
Compounds represented by formula (Iu1) to formula (Iu3238);
A compound represented by formula (Ia1) to formula (Ia2216),
A compound represented by the formula (If1) to the formula (If13090),
A compound represented by formula (It1) to formula (It900),
A compound represented by formula (Iu1) to formula (Iu3238),
A compound represented by the formula (Ib8) and a compound represented by the formula (Ib14),
-SO ₃ H, -CO ₂ H, -SO ₃ NH ₄ , -CO ₂ NH ₄ , a compound in which at least one selected from a fluorine atom, a chlorine atom and a bromine atom is substituted; and formula (Id1) to formula ( An anion represented by Id304) and an anion represented by formulas (Ih1) to (Ih1666),
Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Ni ²⁺ , Zn ²⁺ , Fe ²⁺ , Co ²⁺ , Sn ²⁺ , Mn ²⁺ , Al ³⁺ , Fe ³⁺ , Cr ³⁺ , Sn ⁴⁺ , Mn ⁴⁺ , Cu ²⁺ , Li ⁺ , Na ^+, and a metal salt consisting of one or more cations selected from K ⁺ are more preferable,

A compound represented by formula (Ia1) to formula (Ia2216);
Compounds represented by formula (If1) to formula (If13090);
A compound represented by formula (It1) to formula (It900);
Compounds represented by formula (Iu1) to formula (Iu3238);
A compound represented by formula (Ia1) to formula (Ia2216),
A compound represented by the formula (If1) to the formula (If13090),
A compound represented by formula (It1) to formula (It900),
A compound represented by formula (Iu1) to formula (Iu3238),
A compound represented by the formula (Ib8) and a compound represented by the formula (Ib14),
A compound in which one or more selected from --SO ₃ H, --CO ₂ H, --SO ₃ NH ₄ , --CO ₂ NH ₄ , chlorine atom and bromine atom;
Compounds represented by formula (Ie1) to formula (Ie76); and compounds represented by formula (Ik1) to formula (Ik114) compounds represented by formula (Ik1615) to formula (Ik1633);
Compounds represented by formula (Ik1822) to formula (Ik1983);
A compound represented by formula (Ie117);
A compound represented by formula (Ie123):
A compound represented by the formula (Ik172):
A compound represented by the formula (Ik171):
A compound represented by the formula (Ik1777):
A compound represented by the formula (Ik181):
A compound represented by the formula (Ik397):
A compound represented by formula (Ie273); and a compound represented by formula (Ie116);
Is more preferable,

A compound represented by formula (Ia1) to formula (Ia2216);
Compounds represented by formula (If1) to formula (If13090);
A compound represented by formula (It1) to formula (It900);
Compounds represented by formula (Iu1) to formula (Iu3238);
Compounds represented by formula (Ib8); and compounds represented by formula (Ib14) are particularly preferable,

Compounds represented by formulas (Ia1) to (Ia1241), compounds represented by formulas (It1) to (It900) are more preferable,

A compound represented by formula (Ia1), a compound represented by formula (Ia2), a compound represented by formula (Ia3), a compound represented by formula (Ia10), a compound represented by formula (Ia22), A compound represented by formula (Ia23), a compound represented by formula (Ia33), a compound represented by formula (Ia35), a compound represented by formula (Ia315), a compound represented by formula (Ia696), A compound represented by the formula (Ia703), a compound represented by the formula (Ia973), a compound represented by the formula (It232), a compound represented by the formula (It242), and a compound represented by the formula (It750). Is particularly preferred,

A compound represented by formula (Ia1), a compound represented by formula (Ia2), a compound represented by formula (Ia3), a compound represented by formula (Ia22), a compound represented by formula (Ia23), A compound represented by the formula (Ia35), a compound represented by the formula (Ia696), a compound represented by the formula (Ia703), a compound represented by the formula (Ia973), a compound represented by the formula (It232), A compound represented by the formula (It242) and a compound represented by the formula (It750) are extremely preferable,

A compound represented by formula (Ia1), a compound represented by formula (Ia2), a compound represented by formula (Ia3), a compound represented by formula (Ia696), a compound represented by formula (Ia703), The compound represented by the formula (Ia973), the compound represented by the formula (It232), the compound represented by the formula (It242), and the compound represented by the formula (It750) are most preferable.

The compound represented by formula (I) can be produced by reacting the compound represented by formula (pt1) with the compound represented by formula (pt2) and the compound represented by formula (pt3). ..

In formulas (pt1) to (pt3), R ¹ to R ⁵ , Q ¹ and Q ² have the same meanings as described above.

The amount of the compound represented by the formula (pt2) used in the reaction between the compound represented by the formula (pt1), the compound represented by the formula (pt2) and the compound represented by the formula (pt3) is It is usually 0.1 to 30 mol, preferably 1 to 20 mol, more preferably 1 to 16 mol, and further preferably 1 to 10 per 1 mol of the compound represented by (pt1). It is a mole.

The amount of the compound represented by the formula (pt3) used in the reaction between the compound represented by the formula (pt1), the compound represented by the formula (pt2) and the compound represented by the formula (pt3) is It is usually 0.1 to 30 mol, preferably 1 to 20 mol, more preferably 1 to 16 mol, and further preferably 1 to 10 per 1 mol of the compound represented by (pt1). It is a mole.

The reaction temperature is usually −100 to 300° C., preferably 0 to 280° C., more preferably 50 to 250° C., further preferably 100 to 230° C., and particularly preferably 150 to 200° C. ..

-The reaction time is usually 0.5 hours to 500 hours.

The reaction of the compound represented by the formula (pt1) with the compound represented by the formula (pt2) and the compound represented by the formula (pt3) is usually carried out in the presence of a solvent.

As the solvent, water; a nitrile solvent such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1 -Alcohol solvents such as octanol and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran and diphenyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic carbonization such as hexane Hydrogen solvent; aromatic hydrocarbon solvent such as toluene, trimethylbenzene (eg, 1,3,5-trimethylbenzene), decalin, tetralin; methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1, 3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene and other halogenated hydrocarbon solvents; nitrobenzene and other nitrated hydrocarbon solvents; N,N-dimethylformamide, N,N-dimethylacetamide, N- Amide solvents such as methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide,

Preferably, diphenyl ether, methyl benzoate, trimethylbenzene (eg, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and dimethyl sulfoxide,

More preferably, diphenyl ether, methyl benzoate, trimethylbenzene (eg 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (eg 1,3,5-trichlorobenzene). , 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone,

More preferred is methyl benzoate.

The amount of the solvent used is the compound represented by the formula (pt1) in the reaction of the compound represented by the formula (pt1) with the compound represented by the formula (pt2) and the compound represented by the formula (pt3). It is usually 1 to 1000 parts by mass with respect to 1 part by mass.

In the reaction of the compound represented by the formula (pt1) with the compound represented by the formula (pt2) and the compound represented by the formula (pt3), at least one selected from an acid and a metal salt may coexist. preferable.

Examples of the acid include inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid; acetic acid. , Carboxylic acids such as trifluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid and tartaric acid; and the like, preferably hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfone. Examples thereof include acids, p-toluenesulfonic acid and carboxylic acids, more preferably carboxylic acids, and further preferably benzoic acid.

The amount of the acid used in the reaction of the compound represented by the formula (pt1) with the compound represented by the formula (pt2) and the compound represented by the formula (pt3) is the same as the compound 1 represented by the formula (pt1). The amount is usually 1 to 90 mol, preferably 1 to 70 mol, more preferably 1 to 50 mol, and further preferably 1 to 30 mol, relative to mol.

Examples of metal salts include zinc chloride and aluminum chloride.

The amount of the metal salt used in the reaction of the compound represented by the formula (pt1) with the compound represented by the formula (pt2) and the compound represented by the formula (pt3) is the compound represented by the formula (pt1). It is usually 0.01 to 30 mol, preferably 0.01 to 20 mol, more preferably 0.01 to 10 mol, and further preferably 0.01 to 3 mol, relative to 1 mol. ..

The method of taking out the compound (I) from the reaction mixture is not particularly limited, and it can be taken out by various known methods.
For example, after the completion of the reaction, the compound (I) in the reaction mixture may be difficult to dissolve, but a compound other than the compound (I) is likely to dissolve, and a solvent such as methanol and the reaction mixture are thoroughly mixed The compound (I) can be taken out by filtration. Furthermore, an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, or N-methylpyrrolidone, a sulfoxide solvent such as dimethylsulfoxide, or a mixed solvent thereof, an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and/ Alternatively, the compound (I) may be taken out by washing the obtained residue with an acidic aqueous solution such as hydrochloric acid and then washing with water, a low boiling point alcohol such as methanol or a mixed solvent thereof. Further, it may be purified by column chromatography and/or recrystallization.
Alternatively, after completion of the reaction, the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and/or recrystallization or the like,
After completion of the reaction, the reaction mixture may be purified by column chromatography and/or recrystallization or the like.
After completion of the reaction, the compound (I) in the reaction mixture may be difficult to dissolve, but compounds other than the compound (I) are likely to dissolve, and a solvent such as methanol and the reaction mixture are well mixed and then filtered. By doing so, the compound (I) can be taken out. Further, it may be purified by column chromatography and/or recrystallization.

The compound represented by the formula (I) is a compound represented by the formula (I′) by reacting a compound represented by the formula (pt1) with a compound represented by the formula (pt2) (hereinafter, compound (I') is sometimes produced, and then,
The compound represented by formula (I′) is hydrolyzed in the presence of a base to produce a compound represented by formula (IM1) (hereinafter, sometimes referred to as compound (IM1)), and further,
It can be produced by reacting the compound represented by the formula (IM1) with the compound represented by the formula (pt3).

In the formula (pt1), the formula (pt2), the formula (pt3), the formula (I′) and the formula (IM1), R ¹ to R ⁵ , Q ¹ and Q ² have the same meanings as described above.

In the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2), the amount of the compound represented by the formula (pt2) used is 1 mol of the compound represented by the formula (pt1). On the other hand, it is usually 0.1 to 60 mol, preferably 1 to 40 mol, more preferably 1 to 32 mol, and further preferably 2 to 20 mol.

The amount of the compound represented by the formula (pt3) used in the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) is 1 mol of the compound represented by the formula (IM1). On the other hand, it is usually 0.1 to 30 mol, preferably 1 to 20 mol, more preferably 1 to 16 mol, and further preferably 1 to 10 mol.

Reaction temperature in the reaction of the compound represented by the formula (pt1) and the compound represented by the formula (pt2), or the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) The reaction temperature in is usually −100 to 300° C., preferably 0 to 280° C., more preferably 50 to 250° C., further preferably 100 to 230° C., particularly preferably 150 to 200° C. is there.

Reaction time in the reaction of the compound represented by the formula (pt1) and the compound represented by the formula (pt2), or the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) The reaction time in is usually 0.5 hours to 500 hours.

The reaction of the compound represented by the formula (pt1) with the compound represented by the formula (pt2) or the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) is usually , In the presence of a solvent.

As a solvent in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) or the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) Is water; a nitrile solvent such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol , Alcohol solvents such as phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane An aromatic hydrocarbon solvent such as toluene, trimethylbenzene (eg, 1,3,5-trimethylbenzene), decalin, tetralin; methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5) 5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene and other halogenated hydrocarbon solvents; nitrobenzene and other nitrated hydrocarbon solvents; N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone An amide solvent such as; a sulfoxide solvent such as dimethyl sulfoxide;

More preferably, diphenyl ether, methyl benzoate, trimethylbenzene (eg, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene). , 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone,

More preferred is methyl benzoate.

The amount of the solvent used in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) is usually 1 to 1000 parts by mass with respect to 1 part by mass of the compound represented by the formula (pt1). It is a department.

The amount of the solvent used in the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) is usually 1 to 1000 with respect to 1 part by mass of the compound represented by the formula (IM1). It is a mass part.

In the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) or the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3), an acid is used. It is preferable that one or more selected from the group and metal salts coexist.

As an acid in a reaction of a compound represented by the formula (pt1) with a compound represented by the formula (pt2) or a reaction between a compound represented by the formula (IM1) and a compound represented by the formula (pt3) Are inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid; acetic acid, tricarboxylic acid. Carboxylic acids such as fluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid and tartaric acid; and the like, preferably hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, Examples thereof include p-toluenesulfonic acid and carboxylic acid, more preferably carboxylic acid, and further preferably benzoic acid.

The amount of the acid used in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) is usually 1 to 90 mol relative to 1 mol of the compound represented by the formula (pt1). It is preferably 1 to 70 mol, more preferably 1 to 50 mol, and further preferably 1 to 30 mol.

The amount of the acid used in the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) is usually 1 to 90 mol with respect to 1 mol of the compound represented by the formula (IM1). And preferably 1 to 70 mol, more preferably 1 to 50 mol, and further preferably 1 to 30 mol.

Metal salt in the reaction of the compound represented by the formula (pt1) with the compound represented by the formula (pt2) or the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) Examples thereof include zinc chloride and aluminum chloride.

The amount of the metal salt used in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt2) is usually 0.01 to 100 mol with respect to 1 mol of the compound represented by the formula (pt1). The amount is 30 mol, preferably 0.01 to 20 mol, more preferably 0.01 to 10 mol, and further preferably 0.01 to 3 mol.

The amount of the metal salt used in the reaction between the compound represented by the formula (IM1) and the compound represented by the formula (pt3) is usually 0.01 with respect to 1 mol of the compound represented by the formula (IM1). To 30 mol, preferably 0.01 to 20 mol, more preferably 0.01 to 10 mol, still more preferably 0.01 to 3 mol.

The method for extracting the compound represented by formula (I′) from the reaction mixture in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2) is not particularly limited, and various known methods can be used. Can be retrieved in any way.
For example, after the reaction is completed, the compound (I′) in the reaction mixture may be difficult to dissolve, but a compound other than the compound (I′) is easily dissolved, and a solvent such as methanol and the reaction mixture are well mixed. After that, the compound (I′) can be taken out by filtering. Furthermore, an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, or N-methylpyrrolidone, a sulfoxide solvent such as dimethylsulfoxide, or a mixed solvent thereof, an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and/ Alternatively, the compound (I′) may be taken out by washing the obtained residue with an acidic aqueous solution such as hydrochloric acid and then washing with water, a low boiling point alcohol such as methanol or a mixed solvent thereof. Further, it may be purified by column chromatography and/or recrystallization.
Alternatively, after completion of the reaction, the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and/or recrystallization or the like,
After completion of the reaction, the reaction mixture may be purified by column chromatography and/or recrystallization or the like.
After completion of the reaction, the compound (I′) in the reaction mixture may be difficult to dissolve, but compounds other than the compound (I′) are likely to dissolve, and after thoroughly mixing a solvent such as methanol and the reaction mixture with each other. The compound (I′) can be taken out by filtration. Further, it may be purified by column chromatography and/or recrystallization.

The method for extracting the compound represented by formula (I) from the reaction mixture in the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3) is not particularly limited, and various known methods can be used. Can be retrieved in any way.
For example, after the completion of the reaction, the compound (I) in the reaction mixture may be difficult to dissolve, but a compound other than the compound (I) is likely to dissolve, and a solvent such as methanol and the reaction mixture are thoroughly mixed The compound (I) can be taken out by filtration. Furthermore, an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, or N-methylpyrrolidone, a sulfoxide solvent such as dimethylsulfoxide, or a mixed solvent thereof, an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and/ Alternatively, the compound (I) may be taken out by washing the obtained residue with an acidic aqueous solution such as hydrochloric acid and then washing with water, a low boiling point alcohol such as methanol or a mixed solvent thereof. Further, it may be purified by column chromatography and/or recrystallization.
Alternatively, after completion of the reaction, the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and/or recrystallization or the like,
After completion of the reaction, the reaction mixture may be purified by column chromatography and/or recrystallization or the like.
After completion of the reaction, the compound (I) in the reaction mixture may be difficult to dissolve, but compounds other than the compound (I) are likely to dissolve, and a solvent such as methanol and the reaction mixture are well mixed and then filtered. By doing so, the compound (I) can be taken out. Further, it may be purified by column chromatography and/or recrystallization.

Examples of the base in the hydrolysis reaction of the compound represented by the formula (I′) in the presence of a base include triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, piperidine, 1,8-diazabicyclo[5.4 .0] undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, and other organic bases, sodium Metal alkoxides such as methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, organic metal compounds such as methyl lithium, butyl lithium, tert-butyl lithium and phenyl lithium, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate. , Potassium carbonate, lithium hydroxide, sodium hydroxide, and inorganic bases such as potassium hydroxide,
Inorganic bases are preferred,
Lithium hydroxide, sodium hydroxide, and potassium hydroxide are more preferable,
More preferred are sodium hydroxide and potassium hydroxide,
Potassium hydroxide is especially preferred.

The amount of the base used in the hydrolysis reaction of the compound represented by the formula (I′) in the presence of a base is usually 0.1 to 100 mol, based on 1 mol of the compound represented by the formula (I′). , Preferably 1 to 70 mol, more preferably 2 to 40 mol.

The amount of water used in the hydrolysis reaction of the compound represented by the formula (I′) in the presence of a base is usually 1 to 1000 parts by mass relative to 1 part by mass of the compound represented by the formula (I′). It is preferably 1 to 200 parts by mass, more preferably 1 to 100 parts by mass, still more preferably 1 to 50 parts by mass.

The reaction temperature in the hydrolysis reaction of the compound represented by the formula (I′) in the presence of a base is usually 0 to 100° C., preferably 5 to 100° C., more preferably 20 to 100° C. And more preferably 40 to 100° C., particularly preferably 60 to 100° C.

The reaction time in the hydrolysis reaction of the compound represented by the formula (I′) in the presence of a base is usually 0.5 to 120 hours, preferably 1 to 72 hours, and more preferably 1 to 72 hours. 24 hours.

The method of extracting the compound represented by formula (IM1) from the reaction mixture in the hydrolysis reaction of the compound represented by formula (I′) in the presence of a base is not particularly limited, and various known methods can be used. it can.
For example, after completion of the reaction, the compound (IM1) can be taken out by adding an acidic aqueous solution such as hydrochloric acid to the reaction mixture for neutralization and then filtering. Furthermore, amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, sulfoxide solvents such as dimethylsulfoxide, ketone solvents such as acetone, alcohol solvents such as methanol, nitrile solvents such as acetonitrile, The compound (IM1) may be taken out by washing the obtained residue with water or a mixed solvent thereof, an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and/or an acidic aqueous solution such as a hydrochloric acid. Further, it may be purified by column chromatography and/or recrystallization.
Alternatively, after completion of the reaction, the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and/or recrystallization or the like,
After completion of the reaction, the reaction mixture may be purified by column chromatography and/or recrystallization or the like.

The compound represented by the formula (I) is obtained by reacting the compound represented by the formula (pt1) with the compound represented by the formula (pt3). IM2), which is sometimes referred to as IM2).
It can be produced by reacting the compound represented by the formula (IM2) with the compound represented by the formula (pt2).

In formula (pt1), formula (pt2), formula (pt3) and formula (IM2), R ¹ to R ⁵ , Q ¹ and Q ² have the same meanings as described above.

The amount of the compound represented by the formula (pt3) used in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is 1 mol of the compound represented by the formula (pt1). On the other hand, it is usually 0.1 to 10 mol, preferably 0.1 to 5 mol, more preferably 0.5 to 2 mol, and further preferably 0.8 to 1.5 mol. Is.

The reaction temperature in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is usually −100 to 300° C., preferably 0 to 280° C., more preferably 50. To 250° C., more preferably 100 to 230° C., and particularly preferably 120 to 200° C.

The reaction time in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is usually 0.5 hours to 500 hours.

The reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is usually carried out in the presence of a solvent.

As the solvent in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3), water; a nitrile solvent such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1- Alcohol solvents such as butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether; acetone, methyl Ketone solvents such as isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; aromas such as toluene, trimethylbenzene (eg 1,3,5-trimethylbenzene), decalin, tetralin, etc. Group hydrocarbon solvent; halogenated hydrocarbon solvent such as methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene; nitrobenzene Nitrated hydrocarbon solvents such as; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide;

Preferably, phenol, diphenyl ether, methyl benzoate, trimethylbenzene (eg, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene) ), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and dimethylsulfoxide,

More preferably, phenol, diphenyl ether, methyl benzoate, trimethylbenzene (eg, 1,3,5-trimethylbenzene), decalin, tetralin, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-triene). Chlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone,

More preferably, phenol and methyl benzoate are mentioned,

Particularly preferred is phenol.

The amount of the solvent used in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is usually 1 to 1000 with respect to 1 part by mass of the compound represented by the formula (pt1). It is a mass part, preferably 1 to 200 mass parts, more preferably 1 to 100 mass parts, and further preferably 1 to 50 mass parts.

The method for extracting the compound (IM2) from the reaction mixture in the reaction of the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is not particularly limited, and various known methods can be used. it can.
For example, after the reaction is completed, the compound (IM2) in the reaction mixture may be difficult to dissolve, but a compound other than the compound (IM2) is likely to be dissolved, and a solvent such as methanol and the reaction mixture are well mixed. The compound (IM2) can be extracted by filtration.
Further, amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, sulfoxide solvents such as dimethylsulfoxide, ketone solvents such as acetone, alcohol solvents such as methanol, nitrile solvents such as acetonitrile, The compound (IM2) can be taken out by washing the obtained residue with water or a mixed solvent thereof, an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and/or an acidic aqueous solution such as a hydrochloric acid.
Further, it may be purified by column chromatography and/or recrystallization.
Alternatively, after completion of the reaction, the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and/or recrystallization or the like,
After completion of the reaction, the reaction mixture may be purified by column chromatography and/or recrystallization or the like.
After completion of the reaction, the compound (IM2) in the reaction mixture is difficult to dissolve, but compounds other than the compound (IM2) are easily dissolved. Add the reaction mixture to a solvent such as methanol, mix well, and then filter. The compound (IM2) can be extracted by Further, it may be purified by column chromatography and/or recrystallization.

The amount of the compound represented by the formula (pt2) used in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is 1 mol of the compound represented by the formula (IM2). On the other hand, it is usually 0.1 to 30 mol, preferably 1 to 20 mol, more preferably 1 to 16 mol, and further preferably 1 to 10 mol.

The reaction temperature in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is usually −100 to 300° C., preferably 0 to 280° C., more preferably 50. To 250° C., more preferably 100 to 230° C., and particularly preferably 150 to 200° C.

The reaction time in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is usually 0.5 hours to 500 hours.

The reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is usually carried out in the presence of a solvent.

As a solvent in the reaction of the compound represented by the formula (IM2) with the compound represented by the formula (pt2), water; a nitrile solvent such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1- Alcohol solvents such as butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether; acetone, methyl Ketone solvents such as isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; aromas such as toluene, trimethylbenzene (eg 1,3,5-trimethylbenzene), decalin, tetralin, etc. Group hydrocarbon solvent; halogenated hydrocarbon solvent such as methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene; nitrobenzene Nitrated hydrocarbon solvents such as; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide;

More preferred is methyl benzoate.

The amount of the solvent used in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is usually 1 to 1000 with respect to 1 part by mass of the compound represented by the formula (IM2). It is a mass part.

In the reaction of the compound represented by the formula (IM2) and the compound represented by the formula (pt2), it is preferable that at least one selected from an acid and a metal salt coexist.

Examples of the acid in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) include hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, phosphoric acid and the like. Inorganic acids; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid; carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid and tartaric acid And the like, preferably hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid, more preferably carboxylic acid, and further preferably Examples include benzoic acid.

The amount of the acid used in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is usually 1 to 90 mol with respect to 1 mol of the compound represented by the formula (IM2). And preferably 1 to 70 mol, more preferably 1 to 50 mol, and further preferably 1 to 30 mol.

Examples of the metal salt in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) include zinc chloride and aluminum chloride.

The amount of the metal salt used in the reaction between the compound represented by the formula (IM2) and the compound represented by the formula (pt2) is usually 0.01 with respect to 1 mol of the compound represented by the formula (IM2). To 30 mol, preferably 0.01 to 20 mol, more preferably 0.01 to 10 mol, still more preferably 0.01 to 3 mol.

The method for extracting the compound represented by formula (I) from the reaction mixture in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) is not particularly limited, and various known methods can be used. Can be retrieved in any way.
For example, after the completion of the reaction, the compound (I) in the reaction mixture may be difficult to dissolve, but a compound other than the compound (I) is likely to dissolve, and a solvent such as methanol and the reaction mixture are thoroughly mixed The compound (I) can be taken out by filtration. Furthermore, an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, or N-methylpyrrolidone, a sulfoxide solvent such as dimethylsulfoxide, or a mixed solvent thereof, an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and/ Alternatively, the compound (I) may be taken out by washing the obtained residue with an acidic aqueous solution such as hydrochloric acid and then washing with water, a low boiling point alcohol such as methanol or a mixed solvent thereof. Further, it may be purified by column chromatography and/or recrystallization.
Alternatively, after completion of the reaction, the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and/or recrystallization or the like,
After completion of the reaction, the reaction mixture may be purified by column chromatography and/or recrystallization or the like.
After completion of the reaction, the compound (I) in the reaction mixture may be difficult to dissolve, but compounds other than the compound (I) are likely to dissolve, and a solvent such as methanol and the reaction mixture are well mixed and then filtered. By doing so, the compound (I) can be taken out. Further, it may be purified by column chromatography and/or recrystallization.

The compound represented by the formula (I) is obtained by reacting the compound represented by the formula (pt1) with the compound represented by the formula (pt3). IM2) may be produced), and then the compound represented by formula (IM2) is reacted with the compound represented by formula (pt2).

As a solvent in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3), water; a nitrile solvent such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1- Alcohol solvents such as butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether; acetone, methyl Ketone solvents such as isobutyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; aroma such as toluene, trimethylbenzene (eg 1,3,5-trimethylbenzene), decalin, tetralin, etc. Group hydrocarbon solvent; halogenated hydrocarbon solvent such as methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene; nitrobenzene And the like; nitrated hydrocarbon solvents such as; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide;

More preferably, phenol and methyl benzoate are mentioned,

Particularly preferred is phenol.

The method for extracting the compound (IM2) from the reaction mixture in the reaction of the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is not particularly limited, and various known methods can be used. it can.
For example, after the reaction is completed, the compound (IM2) in the reaction mixture may be difficult to dissolve, but a compound other than the compound (IM2) is likely to be dissolved, and a solvent such as methanol and the reaction mixture are well mixed. The compound (IM2) can be extracted by filtration.
Further, amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, sulfoxide solvents such as dimethylsulfoxide, ketone solvents such as acetone, alcohol solvents such as methanol, nitrile solvents such as acetonitrile, The compound (IM2) can be taken out by washing the obtained residue with water or a mixed solvent thereof, an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and/or an acidic aqueous solution such as a hydrochloric acid.
Further, it may be purified by column chromatography and/or recrystallization.
Alternatively, after completion of the reaction, the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and/or recrystallization or the like,
After completion of the reaction, the reaction mixture may be purified by column chromatography and/or recrystallization or the like.
After completion of the reaction, the compound (IM2) in the reaction mixture may be difficult to dissolve, but compounds other than the compound (IM2) are likely to dissolve, and a solvent such as methanol and the reaction mixture are well mixed and then filtered. By doing so, the compound (IM2) can be taken out. Further, it may be purified by column chromatography and/or recrystallization.

More preferred is methyl benzoate.

The method for extracting the compound represented by formula (I) from the reaction mixture in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) is not particularly limited, and various known methods can be used. Can be retrieved in any way.
For example, after the completion of the reaction, the compound (I) in the reaction mixture may be difficult to dissolve, but a compound other than the compound (I) is likely to dissolve, and a solvent such as methanol and the reaction mixture are thoroughly mixed The compound (I) can be taken out by filtration. Furthermore, an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, or N-methylpyrrolidone, a sulfoxide solvent such as dimethylsulfoxide, or a mixed solvent thereof, an alkaline aqueous solution such as an aqueous sodium hydroxide solution, and/ Alternatively, the compound (I) may be taken out by washing the obtained residue with an acidic aqueous solution such as hydrochloric acid and then washing with water, a low boiling point alcohol such as methanol or a mixed solvent thereof. Further, it may be purified by column chromatography and/or recrystallization.
Alternatively, after completion of the reaction, the solvent of the reaction mixture may be distilled off, and the obtained residue may be purified by column chromatography and/or recrystallization or the like. It may be purified by recrystallization or the like.
After completion of the reaction, the compound (I) in the reaction mixture may be difficult to dissolve, but compounds other than the compound (I) are likely to dissolve, and a solvent such as methanol and the reaction mixture are well mixed and then filtered. By doing so, the compound (I) can be taken out. Further, it may be purified by column chromatography and/or recrystallization.

A sulfo group or —SO ₃ M can be introduced into compound (I) by reacting compound (I) with a sulfating agent such as fuming sulfuric acid or chlorosulfonic acid.
A compound obtained by introducing a sulfo group or —SO ₃ M into compound (I) (hereinafter, also referred to as “sulfonated compound (I)”) is also a compound of the present invention.

The amount of SO ₃ used in fuming sulfuric acid is usually 1 to 200 moles, preferably 2 to 150 moles, more preferably 3 to 100 moles, and further preferably 1 mole of Compound (I). Is 5 to 80 mol.

SO ₃ in fuming sulfuric acid is usually 1 to 90 parts by mass, preferably 5 to 70 parts by mass, more preferably 10 to 60 parts by mass, and further preferably 15 to 10 parts by mass based on 100 parts by mass of fuming sulfuric acid. 50 parts by mass.

The amount of chlorosulfonic acid used is usually 1 to 500 mol, preferably 1 to 300 mol, more preferably 1 to 200 mol, and further preferably 1 to 150 mol, relative to 1 mol of compound (I). It is a mole.

When introducing a sulfo group or —SO ₃ M into compound (I) using chlorosulfonic acid, the reaction may be carried out in the presence of a solvent.
Examples of the solvent include halogenated hydrocarbon solvents such as methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene), 1-chloronaphthalene and 2-chloronaphthalene. To be

The amount of the solvent used is usually 1 to 1000 parts by mass with respect to 1 part by mass of the compound (I).

The reaction temperature for sulfonation is usually −20 to 200° C., preferably −10 to 150° C., more preferably 0 to 100° C. The reaction time is usually 0.5 to 300 hours.

The method for taking out the sulfonated compound (I) from the reaction mixture is not particularly limited, and it can be taken out by various known methods.
For example, after completion of the reaction, the sulfonated compound (I) can be taken out by dropping the reaction mixture on ice and filtering the obtained mixture. Further, it may be purified by column chromatography and/or recrystallization.
Alternatively, after completion of the reaction, the reaction mixture is added dropwise to ice, and the resulting mixture is difficult to dissolve the sulfonated compound (I), but the compounds other than the sulfonated compound (I) are easily dissolved, such as an alcohol such as methanol. The sulfonated compound (I) can be taken out by mixing with a solvent, a nitrile solvent such as acetonitrile and a hydrophilic organic solvent such as a mixed solvent thereof, and filtering. Further, it may be purified by column chromatography and/or recrystallization.
Alternatively, after completion of the reaction, the reaction mixture is added dropwise to ice, the resulting mixture is neutralized with an aqueous solution of ammonia, a water-soluble amine or a mixture thereof, and the mixture is then mixed with an alcohol solvent such as methanol, acetonitrile or the like. The sulfonated compound (I) can be taken out by mixing with a hydrophilic organic solvent such as the nitrile solvent and the mixed solvent thereof, filtering and distilling off the solvent of the obtained filtrate. Further, it may be purified by column chromatography and/or recrystallization.

By reacting compound (I) having —SO ₃ H and/or —CO ₂ H (hereinafter sometimes referred to as “acid-containing group compound (I)”) with a salt having MM, —SO A compound (I) having ₃ (MM) and/or --CO ₂ (MM) (hereinafter sometimes referred to as “MM-containing compound (I)”) can be produced.

The amount of the MM-containing salt used is usually 0.01 to 100 mol, preferably 0.02 to 50 mol, and more preferably 0.1 to 100 mol, based on 1 mol of the acid-containing compound (I). It is 30 mol.

The reaction temperature is usually 0 to 100° C., preferably 0 to 80° C., more preferably 0 to 60° C., and further preferably 0 to 40° C.

-The reaction time is usually 0.5 hours to 500 hours.

The reaction between the acid-containing group compound (I) and the salt having MM is usually carried out in the presence of a solvent.
As the solvent, water; a nitrile solvent such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, Alcohol solvent such as 1-octanol and phenol; Amine solvent; Ether solvent such as diethyl ether, tetrahydrofuran and diphenyl ether; Ketone solvent such as acetone and methyl isobutyl ketone; Ester solvent such as ethyl acetate and methyl benzoate; Aliphatic such as hexane Hydrocarbon solvent; aromatic hydrocarbon solvent such as toluene, trimethylbenzene (eg, 1,3,5-trimethylbenzene), decalin, tetralin; methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1 , 3,5-Trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene and the like halogenated hydrocarbon solvents; nitrobenzene and other nitrated hydrocarbon solvents; N,N-dimethylformamide, N,N-dimethylacetamide, N An amide solvent such as methylpyrrolidone; a sulfoxide solvent such as dimethyl sulfoxide,
Water; nitrile solvent such as acetonitrile; alcohol solvent such as methanol, ethanol, 1-propanol, 2-propanol; ether solvent such as tetrahydrofuran; ketone solvent such as acetone; N,N-dimethylformamide, N,N-dimethylacetamide, Amide solvents such as N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; and mixed solvents thereof are preferable, and water is more preferable.

The amount of the solvent used is usually 1 to 1000 parts by mass, preferably 10 to 500 parts by mass, and more preferably 20 to 300 parts by mass with respect to 1 part by mass of the acid-containing group compound (I). ..

The reaction between the acid-containing compound (I) and the salt having MM may be carried out in the presence of a base.

Examples of the base include triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, piperidine, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3]. .0]non-5-ene, 1,5-diazabicyclo[4.3.0]non-5-ene and other organic bases, sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide and the like Metal alkoxides, organic metal compounds such as methyl lithium, butyl lithium, tert-butyl lithium and phenyl lithium, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide and the like Inorganic bases and the like,
Inorganic bases are preferred,
Lithium hydroxide, sodium hydroxide, and potassium hydroxide are more preferable,
More preferred are sodium hydroxide and potassium hydroxide,
Sodium hydroxide is especially preferred.

The amount of the base used is usually 1 to 100 mol, preferably 1 to 50 mol, more preferably 1 to 20 mol, and further preferably 1 mol of the acid-containing group compound (I). It is 1 to 10 mol.

The method for taking out the MM-containing compound (I) from the reaction mixture is not particularly limited, and it can be taken out by various known methods.
For example, the compound (I) having —SO ₃ (MM) and/or —CO ₂ (MM) can be taken out by filtering the reaction mixture after completion of the reaction. Further, amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, sulfoxide solvents such as dimethylsulfoxide, ketone solvents such as acetone, alcohol solvents such as methanol, nitrile solvents such as acetonitrile, The obtained residue may be washed with water or a mixed solvent thereof, and then purified by washing with water, a low boiling point alcohol such as methanol, or a mixed solvent thereof.

[Coloring composition]
The coloring composition of the present invention contains the compound (I) and the solvent (E). According to the coloring composition of the present invention, C.I. I. As compared with the coloring composition containing Pigment Yellow 138, a darker color filter can be formed. The color filter formed from the colored composition of the present invention is suitably used for a display device such as a liquid crystal display device. The colored composition of the present invention is preferably a yellow composition, an orange composition, a red composition and a green composition.

The solid content of the coloring composition is less than 100% by mass, preferably 0.01% by mass or more and less than 100% by mass, more preferably 0.1% by mass, based on the total amount of the coloring composition. % Or more and 99.9 mass% or less, more preferably 0.1 mass% or more and 99 mass% or less, particularly preferably 1 mass% or more and 90 mass% or less, and further preferably 1 mass% or more and 80 mass% or less. % Or less, particularly preferably 1% by mass or more and 70% by mass or less, very preferably 1% by mass or more and 60% by mass or less, and most preferably 1% by mass or more and 50% by mass or less.
In the present specification, the “total amount of solid content” refers to the total amount of components excluding the solvent (E) from the colored composition of the present invention. The total amount of solid content and the content of each component relative thereto can be measured by a known analysis means such as liquid chromatography or gas chromatography.

The content of the compound (I) in the coloring composition is 100% by mass or less, preferably 0.0001% by mass or more and 99.9999% by mass or less, and more preferably 0.0001% by mass in the total solid content. Mass% or more and 99 mass% or less, more preferably 0.0001 mass% or more and 90 mass% or less, particularly preferably 0.0001 mass% or more and 80 mass% or less, and more preferably 0.0001 mass%. Or more and 70 mass% or less, particularly preferably 0.0001 mass% or more and 60 mass% or less, very preferably 0.0001 mass% or more and 55 mass% or less, and most preferably 0.1 mass% or more and 55 mass% or less. It is not more than mass %.

[Solvent (E)]
The solvent (E) is not particularly limited, and a solvent usually used in this field can be used.
The solvent (E) is, for example, an ester solvent (a solvent containing —CO—O— in the molecule but not —O—), an ether solvent (containing —O— in the molecule, and —CO—O— Non-solvent), ether ester solvent (solvent containing -CO-O- and -O- in the molecule), ketone solvent (solvent containing -CO- and not -CO-O-), alcohol Examples thereof include solvents (solvents containing OH in the molecule and not containing —O—, —CO— and —CO—O—), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like.

Ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate. , Methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate and γ-butyrolactone.

As the ether solvent, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether , Propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl Examples thereof include ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole and methylanisole.

Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, and 3-ethoxy. Ethyl propionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, Ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl Examples thereof include ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate and dipropylene glycol methyl ether acetate.

Ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone and isophorone. Etc.

Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol and glycerin.

As the aromatic hydrocarbon solvent, benzene, toluene, xylene, mesitylene, etc. may be mentioned.

Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone.

These solvents may be used in combination of two or more.

Among the above solvents, organic solvents having a boiling point of 120° C. or more and 180° C. or less at 1 atm are preferable from the viewpoints of coating properties and drying properties. The solvent is preferably propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2. -Pentanone and N,N-dimethylformamide, more preferably propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate, and 4-hydroxy-4-methyl-2-pentanone. Etc.

The content of the solvent (E) is less than 100% by mass, preferably 99.99% by mass or less, and more preferably 0.1% by mass or more and 99.9% by mass, based on the total amount of the coloring composition. Or less, more preferably 1% by mass or more and 99.9% by mass or less, particularly preferably 10% by mass or more and 99% by mass or less, more preferably 20% by mass or more and 99% by mass or less, particularly preferably 30% by mass. Or more and 99 mass% or less, very preferably 40 mass% or more and 99 mass% or less, and most preferably 50 mass% or more and 99 mass% or less.

[Resin (B)]
The resin (B) is preferably an alkali-soluble resin, and at least one monomer selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter referred to as “monomer (a)”). It is more preferable that the polymer has a structural unit derived from.
The resin (B) is a structural unit derived from a monomer having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as “monomer (b)”), And a copolymer having another structural unit.
The other structural unit is a monomer copolymerizable with the monomer (a) (provided that it is different from the monomer (a) and the monomer (b). In some cases)), a structural unit having an ethylenically unsaturated bond, and the like.

In the present specification, “(meth)acrylic acid” represents at least one selected from the group consisting of acrylic acid and methacrylic acid. The expressions such as “(meth)acryloyl” and “(meth)acrylate” have the same meaning.

Examples of the monomer (a) include acrylic acid, methacrylic acid, crotonic acid, and unsaturated monocarboxylic acids such as o-, m-, p-vinylbenzoic acid;
Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexene dicarboxylic acid;
Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo A bicyclo unsaturated compound containing a carboxy group such as [2.2.1] hept-2-ene, 5-carboxy-6-ethylbicyclo [2.2.1] hept-2-ene;
Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6- Unsaturated dicarboxylic acid anhydrides such as tetrahydrophthalic acid anhydride, dimethyltetrahydrophthalic acid anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride;
Unsaturated mono[(meth)acryloyloxyalkyl]esters of divalent or higher polyvalent carboxylic acids such as mono[2-(meth)acryloyloxyethyl]succinate and mono[2-(meth)acryloyloxyethyl]phthalate ;
unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid;
Etc.

Among these, acrylic acid, methacrylic acid, o-, m-, p-vinylbenzoic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerization reactivity and solubility of the obtained resin in an alkaline aqueous solution.

The monomer (b) is a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of oxirane ring, oxetane ring and tetrahydrofuran ring) and an ethylenically unsaturated bond. Say.
The monomer (b) is preferably a monomer having a cyclic ether structure having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

Examples of the monomer (b) include a monomer having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “monomer (b1)”), an oxetanyl group and an ethylenic unsaturated bond. A monomer having a saturated bond (hereinafter, sometimes referred to as "monomer (b2)") and a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter, "monomer (b3)". )” in some cases.) and the like.

Examples of the monomer (b1) include a monomer having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter referred to as “monomer (b1-1)”). And a monomer having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter, may be referred to as “monomer (b1-2)”).

As the monomer (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferable.
Examples of the monomer (b1-1) include, for example:
Glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α- Methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2,4-bis(glycidyl) Oxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris (Glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, 2,4,6-tris(glycidyloxymethyl)styrene, etc. Can be mentioned.

Examples of the monomer (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celoxide (registered trademark) 2000; manufactured by Daicel Corporation), 3,4-epoxy. Cyclohexylmethyl (meth)acrylate (for example, Cyclomer (registered trademark) A400; manufactured by Daicel), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer (registered trademark) M100; Daicel, Ltd.) Production), compounds represented by formula (BI), compounds represented by formula (BII), and the like.

[In the formulas (BI) and (BII), R ^a and R ^b each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is a hydroxy group. May be substituted with.
X ^a and X ^b are each independently a single ^{bond, * - R c -, *} - R c -O -, * - represents the R ^c -S- or * -R ^c -NH-.
R ^c represents an alkanediyl group having 1 to 6 carbon atoms.
* Represents a bond with O. ]

Examples of the alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group and tert-butyl group.

Examples of the alkyl group having a hydrogen atom substituted with hydroxy include, for example, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1 Examples thereof include -hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group and 4-hydroxybutyl group.

R ^a and R ^b are preferably a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group or a 2-hydroxyethyl group, and more preferably a hydrogen atom or a methyl group.

Examples of the alkanediyl group include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, Hexane-1,6-diyl group and the like can be mentioned.

X ^a and X ^b are preferably a single bond, a methylene group, an ethylene group, *—CH ₂ —O— and *—CH ₂ CH ₂ —O—, more preferably a single bond, *—CH ₂ CH ₂ —O— can be mentioned (* represents a bond with O).

Examples of the compound represented by the formula (BI) include compounds represented by any of the formulas (BI-1) to (BI-15). Among them, formula (BI-1), formula (BI-3), formula (BI-5), formula (BI-7), formula (BI-9) and formula (BI-11) to formula (BI-15) Compounds represented by formula (BI-1), formula (BI-7), formula (BI-9) and formula (BI-15) are more preferable.

Examples of the compound represented by the formula (BII) include compounds represented by any of the formulas (BII-1) to (BII-15), and among them, the compound represented by the formula (BII-1) and the formula (BII-1) is preferable. The compounds represented by (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) and formula (BII-11) to formula (BII-15) can be mentioned. Preferred are compounds represented by formula (BII-1), formula (BII-7), formula (BII-9) and formula (BII-15).

The compound represented by the formula (BI) and the compound represented by the formula (BII) may be used alone or in combination of two or more kinds. You may use together the compound represented by Formula (BI) and the compound represented by Formula (BII). When the compound represented by the formula (BI) and the compound represented by the formula (BII) are used in combination, the content ratio thereof [the compound represented by the formula (BI): the compound represented by the formula (BII)] is On a molar basis, it is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and further preferably 20:80 to 80:20.

As the monomer (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable.
Examples of the monomer (b2) include 3-methyl-3-methacryloyloxymethyl oxetane, 3-methyl-3-acryloyloxymethyl oxetane, 3-ethyl-3-methacryloyloxymethyl oxetane, 3-ethyl-3 -Acryloyloxymethyl oxetane, 3-methyl-3-methacryloyloxyethyl oxetane, 3-methyl-3-acryloyloxyethyl oxetane, 3-ethyl-3-methacryloyloxyethyl oxetane, 3-ethyl-3-acryloyloxyethyl oxetane, etc. Is mentioned.

As the monomer (b3), a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferable.
Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (for example, Biscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate and the like.

The monomer (b) is preferably the monomer (b1) from the viewpoint that the obtained color filter can have higher reliability such as heat resistance and chemical resistance. Further, the monomer (b1-2) is more preferable in that the storage stability of the coloring composition is excellent.

Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, and 2-ethylhexyl. (Meth)acrylate, dodecyl(meth)acrylate, lauryl(meth)acrylate, stearyl(meth)acrylate, cyclopentyl(meth)acrylate, cyclohexyl(meth)acrylate, 2-methylcyclohexyl(meth)acrylate, tricyclo[5.2. 1.0 ^2,6 ]Decan-8-yl(meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decan-9-yl(meth)acrylate, tricyclo[5.2.1.0 ^{2 ,6} ]decen-8-yl(meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decen-9-yl(meth)acrylate, dicyclopentanyloxyethyl(meth)acrylate, isobornyl(meth) ) (Meth)acrylic acid esters such as acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate and benzyl (meth)acrylate;
Hydroxy group-containing (meth)acrylic acid ester such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;
2,2,3,3,4,4,5,5-octafluoropentyl (meth)acrylate and other halogen atom-containing (meth)acrylic acid esters;
Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate and diethyl itaconic acid;
Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5- Hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1] Hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2] .1]Hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2. 1] hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy -5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2 1.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexyl) Oxycarbonyl)bicyclo[2.2.1]hept-2-ene and other bicyclo unsaturated compounds;
N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3 -Dicarbonylimide derivatives such as maleimide propionate and N-(9-acridinyl)maleimide;
Vinyl group-containing aromatic compounds such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, 9-vinylcarbazole and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; Halogenated hydrocarbons such as vinyl and vinylidene chloride; vinyl group-containing amides such as (meth)acrylamide; esters such as vinyl acetate; dienes such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene ; And the like.

Of these, styrene, vinyltoluene, tricyclo[5.2.1.0 ^2,6 ]decan-8-yl(meth)acrylate, tricyclo[5.2.1] from the viewpoint of copolymerization reactivity and heat resistance. .0 ^2,6 ]Decan-9-yl(meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decen-8-yl(meth)acrylate, tricyclo[5.2.1.0 ^{2, 6} ]decen-9-yl(meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, phenyl(meth)acrylate, 2,2 , 3,3,4,4,5,5-octafluoropentyl (meth)acrylate, 9-vinylcarbazole, benzyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate and 2-ethylhexyl (meth)acrylate preferable.

Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ] Decyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/benzyl (meth)acrylate/(meth) Acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/9-vinylcarbazole/(meth)acrylic acid copolymer, 3,4-epoxy Tricyclo[5.2.1.0 ^2,6 ]decyl(meth)acrylate/phenyl(meth)acrylate/o-vinylbenzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0] ^2,6 ]decyl(meth)acrylate/phenyl(meth)acrylate/m-vinylbenzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl(meth)acrylate/ Phenyl(meth)acrylate/p-vinylbenzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl(meth)acrylate/phenyl(meth)acrylate/(meth)acrylic Acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/2,2,3,3,4,4,5,5-octafluoropentyl( (Meth)acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate/styrene/(meth)acrylic acid copolymer , 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl(meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5. 2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2. 1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/vinyltoluene copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/ (Meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymerization Body, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl(meth)acrylate/tricyclo[5.2.1.0 ^2,6 ]decenyl(meth)acrylate/(meth)acrylic Acid/N-cyclohexylmaleimide copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane/(meth)acrylic acid/styrene copolymer, benzyl (meth)acrylate/(meth)acrylic acid copolymer , Styrene/(meth)acrylic acid copolymer, and resins described in JP-A-9-106071, JP-A-2004-29518 and JP-A-2004-361455.
Among them, the resin (B) is preferably a copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b).
The resin (B) may be a combination of two or more kinds. In this case, the resin (B) is at least
It is preferable to contain at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b),
More preferably, at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1) is included,
It is more preferable to include at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1-2),
3,4-Epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^{2 ,6} ]decyl(meth)acrylate/benzyl(meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl(meth)acrylate/( (Meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth) Acrylic acid/vinyltoluene copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer It is particularly preferable to include one or more selected from

The polystyrene-equivalent weight average molecular weight (Mw) of the resin (B) is preferably 1,000 to 100,000, more preferably 1,000 to 50,000, and further preferably 1,000 to 30, 000, particularly preferably 3,000 to 30,000, particularly preferably 5,000 to 30,000.

The dispersity [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1 to 6, more preferably 1 to 5, and further preferably 1 to 4.

The acid value (converted to solid content) of the resin (B) is preferably 10 to 500 mg-KOH/g, more preferably 20 to 450 mg-KOH/g, further preferably 20 to 400 mg-KOH/g, and even more preferably Is 20 to 370 mg-KOH/g, more preferably 30 to 370 mg-KOH/g, even more preferably 30 to 350 mg-KOH/g, particularly preferably 30 to 340 mg-KOH/g, most preferably It is 30 to 335 mg-KOH/g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide necessary to neutralize 1 g of the resin (B), and can be determined by, for example, titration with an aqueous potassium hydroxide solution.

In the coloring composition, the content of the resin (B) is less than 100% by mass, preferably 0.00001% by mass or more and 99.99999% by mass or less, and more preferably 1% by mass based on the total amount of solids. % By mass to 99% by mass, more preferably 1% by mass to 97% by mass, particularly preferably 1% by mass to 95% by mass, and further preferably 3% by mass to 95% by mass. Yes, particularly preferably 5 mass% or more and 95 mass% or less, and very preferably 10 mass% or more and 95 mass% or less.

[Preparation of Compound (I)-Containing Liquid]
In the coloring composition of the present invention, a compound (I)-containing solution containing the compound (I) and the solvent (E) is prepared in advance, and then the coloring composition is prepared using the compound (I)-containing solution. Good. When the compound (I) does not dissolve in the solvent (E), the compound (I)-containing liquid may be prepared by dispersing the compound (I) in the solvent (E) and mixing them. The compound (I)-containing liquid may contain a part or all of the solvent (E) contained in the coloring composition.
The compound (I)-containing liquid is included in the coloring composition of the present invention.

The solid content of the compound (I)-containing liquid is less than 100% by mass, preferably 0.01% by mass or more and 99.99% by mass or less, based on the total amount of the compound (I)-containing liquid. It is more preferably 0.1% by mass or more and 99.9% by mass or less, further preferably 0.1% by mass or more and 99% by mass or less, particularly preferably 1% by mass or more and 90% by mass or less, and further preferably 1% by mass. Or more and 80% by mass or less, particularly preferably 1% by mass or more and 70% by mass or less, very preferably 1% by mass or more and 60% by mass or less, and most preferably 1% by mass or more and 50% by mass or less.

The content rate of the compound (I) in the compound (I)-containing liquid is 100% by mass or less, preferably 0.0001% by mass or more and 99.9999% by mass in the total amount of solids in the compound (I)-containing liquid. Or less, more preferably 0.0001% by mass or more and 99% by mass or less, further preferably 1% by mass or more and 99% by mass or less, particularly preferably 3% by mass or more and 99% by mass or less, and further preferably Is 5% by mass or more and 99% by mass or less.

The compound (I) is, if necessary, rosin-treated, surface-treated with a derivative having an acidic group or a basic group introduced therein, grafted with a polymer compound or the like on the surface of the compound (I), and atomized with sulfuric acid. Method, salt milling method or the like, atomization treatment, cleaning treatment with an organic solvent or water for removing impurities, removal treatment of ionic impurities by ion exchange method or the like may be performed.
In addition, the compound (I) may be subjected to crystal structure conversion, particle shaping and/or substantially uniform particle size treatment, if necessary;
The compound (I) was mixed with water and/or an organic solvent, stirred and/or stirred while heating to obtain a suspension, and the suspension was filtered to change the crystal structure. Treatment to obtain compound (I);
A treatment for changing the crystal structure of compound (I) by recrystallization;
After the compound (I) is mixed with water, sulfuric acid or an organic solvent and stirred and/or heated to obtain a solution or suspension, the solution or suspension is mixed with the compound (I). ) Is mixed with a poor solvent to obtain a suspension, and the suspension is filtered to obtain a compound (I) having a changed crystal structure;
The compound (I), the derivative, water and/or an organic solvent are mixed and stirred with stirring and/or heating to obtain a suspension, which is then filtered to obtain a crystal structure. A process of obtaining a mixture containing the compound (I) in which the compound (I) is changed and/or a process of mixing the compound (I) with a derivative;
Recrystallization of a mixture of compound (I) and a derivative to obtain a mixture containing compound (I) having a changed crystal structure and/or treatment of mixing compound (I) with a derivative;
Compound (I), a derivative, water, sulfuric acid or an organic solvent are mixed and stirred with stirring and/or heating to obtain a solution or suspension, and then the solution or suspension, Treatment with compound (I) mixed with a poor solvent to obtain a suspension, and then filtration of the suspension to obtain a mixture containing compound (I) having a changed crystal structure and/or compound (I) A process of mixing a derivative with a derivative;
Etc. may be applied.
When a plurality of kinds of compound (I) or a derivative is used, these treatments may be carried out individually, or a plurality of kinds may be mixed and treated.
The particle size of compound (I) is preferably substantially uniform.

The organic solvent used for the crystal structure conversion,
Nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol, etc. Alcohol solvent; amine solvent; ether solvent such as diethyl ether, tetrahydrofuran, diphenyl ether; ketone solvent such as acetone and methyl isobutyl ketone; ester solvent such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvent such as hexane; toluene, trimethyl Aromatic hydrocarbon solvents such as benzene (eg, 1,3,5-trimethylbenzene), decalin, tetralin; methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene) ), 1-chloronaphthalene, 2-chloronaphthalene and other halogenated hydrocarbon solvents; nitrobenzene and other nitrated hydrocarbon solvents; N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and other amide solvents A sulfoxide solvent such as dimethyl sulfoxide; and the like.

As the poor solvent,
Nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol, etc. Alcohol solvent; amine solvent; ether solvent such as diethyl ether, tetrahydrofuran, diphenyl ether; ketone solvent such as acetone and methyl isobutyl ketone; ester solvent such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvent such as hexane; toluene, trimethyl Aromatic hydrocarbon solvents such as benzene (eg, 1,3,5-trimethylbenzene), decalin, tetralin; methylene chloride, chloroform, 1,2-dichlorobenzene, trichlorobenzene (eg, 1,3,5-trichlorobenzene) ), 1-chloronaphthalene, 2-chloronaphthalene and other halogenated hydrocarbon solvents; nitrobenzene and other nitrated hydrocarbon solvents; and the like.

Examples of the derivative include a compound represented by the formula (z) and a compound represented by the formula (z1).

When the compound (I)-containing liquid contains a derivative, the content rate of the derivative is 0.01 parts by mass or more and 100 parts by mass or less, and 0.01 parts by mass or more based on 100 parts by mass of the compound (I). It is preferably 70 parts by mass or less, more preferably 0.1 parts by mass or more and 50 parts by mass or less, still more preferably 0.1 parts by mass or more and 30 parts by mass or less, and particularly preferably 0.1 parts by mass or more and 20 parts by mass or less.

The compound (I) can be uniformly dispersed in the compound (I)-containing liquid by subjecting the compound (I) to a dispersant and performing a dispersion treatment. When a plurality of types of compound (I) are used, each may be subjected to a dispersion treatment alone, or a plurality of types may be mixed and dispersed.

Examples of the dispersant include surfactants, and any of cationic, anionic, nonionic and amphoteric surfactants may be used. Specific examples thereof include polyester-based, polyamine-based and acrylic-based surfactants. You may use these dispersants individually or in combination of 2 or more types. As the dispersant, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Sols Perth (registered trademark) (manufactured by Zeneca Corporation), and EFKA (registered trademark) are trade names. (Manufactured by BASF), Azisper (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Inc.), DISPERBYK (registered trademark) (manufactured by Big Chemie), BYK (registered trademark) (manufactured by Big Chemie), and the like. ..

When the compound (I)-containing liquid contains a dispersant, the amount of the dispersant (solid content) used is, for example, 0.01 part by mass or more and 10000 parts by mass or less with respect to 100 parts by mass of the compound (I). , Preferably 0.01 parts by mass or more and 5000 parts by mass or less, more preferably 0.01 parts by mass or more and 1000 parts by mass or less, further preferably 0.1 parts by mass or more and 500 parts by mass or less, and particularly preferably Is 0.1 part by mass or more and 300 parts by mass or less, more preferably 1 part by mass or more and 300 parts by mass or less, and particularly preferably 5 parts by mass or more and 260 parts by mass or less.
When the amount of the dispersant used is within the above range, a more uniform dispersion of the compound (I)-containing liquid tends to be obtained.

The coloring composition of the present invention contains a resin (B), and a compound (I)-containing solution containing a compound (I) and a solvent (E) is prepared in advance, and then the compound (I)-containing solution is used. When the colored composition of the invention is prepared, the compound (I)-containing liquid may previously contain a part or all, preferably a part, of the resin (B) contained in the colored composition. By preliminarily containing the resin (B), the dispersion stability of the compound (I)-containing liquid can be further improved.

When the compound (I)-containing liquid contains the resin (B), the content of the resin (B) is, for example, 0.01 part by mass or more and 10000 parts by mass or less, relative to 100 parts by mass of the compound (I), It is preferably 0.01 parts by mass or more and 5000 parts by mass or less, more preferably 0.01 parts by mass or more and 1000 parts by mass or less, further preferably 0.1 parts by mass or more and 500 parts by mass or less, and particularly preferably It is 0.1 part by mass or more and 300 parts by mass or less.

[Polymerizable compound (C)]
The polymerizable compound (C) is a compound that can be polymerized with an active radical and/or an acid generated from the polymerization initiator (D), and is, for example, a compound having a polymerizable ethylenic unsaturated bond, and preferably It is a (meth)acrylic acid ester compound.

Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate and N-vinylpyrrolidone. Etc., and the above-mentioned monomers (a), (b) and (c).

Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate and triethylene glycol di. Examples thereof include (meth)acrylate, bis(acryloyloxyethyl)ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such a polymerizable compound include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa( (Meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl) ) Isocyanurate, ethylene glycol modified pentaerythritol tetra(meth)acrylate, ethylene glycol modified dipentaerythritol hexa(meth)acrylate, propylene glycol modified pentaerythritol tetra(meth)acrylate, propylene glycol modified dipentaerythritol hexa(meth)acrylate, Examples thereof include caprolactone-modified pentaerythritol tetra(meth)acrylate and caprolactone-modified dipentaerythritol hexa(meth)acrylate, and preferably dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

The weight average molecular weight of the polymerizable compound (C) is preferably 50 or more and 4000 or less, more preferably 50 or more and 3500 or less, still more preferably 50 or more and 3000 or less, and particularly preferably 150 or more and 2900 or less. And particularly preferably 250 or more and 1,500 or less.

The content of the polymerizable compound (C) is less than 100% by mass, preferably 0.00001% by mass or more and 99.99999% by mass or less, and more preferably, with respect to the total amount of solids in the coloring composition. Is 1 mass% or more and 99 mass% or less, more preferably 1 mass% or more and 97 mass% or less, particularly preferably 1 mass% or more and 95 mass% or less, and further preferably 1 mass% or more and 90 mass% or less. Or less, particularly preferably 2% by mass or more and 80% by mass or less, and very preferably 3% by mass or more and 70% by mass or less.

[Polymerization initiator (D)]
The polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating active radicals, acids and the like by the action of light or heat and initiating polymerization, and known polymerization initiators can be used.
Examples of the polymerization initiator (D) include oxime compounds such as O-acyloxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds and acylphosphine oxide compounds.

Examples of the O-acyl oxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane- 1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)- 3-Cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl -6-(2-Methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl) -2,4-Dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)- 9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3- Examples thereof include cyclopentylpropan-1-one-2-imine. As the O-acyl oxime compound, commercially available products such as Irgacure OXE01, OXE02 (all manufactured by BASF) and N-1919 (manufactured by ADEKA) may be used. Among them, O-acyl oxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane- At least one selected from the group consisting of 1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine is preferable, and N-benzoyl Oxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine is more preferred.

Examples of the alkylphenone compound include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one and 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1- Examples thereof include on and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one. As the alkylphenone compound, commercially available products such as Irgacure 369, 907, 379 (all manufactured by BASF) may be used.
Examples of the alkylphenone compound include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, Mention may also be made of 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone and benzyldimethyl ketal.

Examples of the biimidazole compound include 2,2′-bis(2-chlorophenyl)-4,4′,5,5′-tetraphenylbiimidazole and 2,2′-bis(2,3-dichlorophenyl)-4. , 4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4, 4',5,5'-Tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2 '-Bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B-48-38403 and JP-A-62-174204). And a biimidazole compound in which the phenyl group at the 4,4′,5,5′-position is substituted with a carboalkoxy group (see, for example, JP-A-7-10913).

Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine and 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl). -1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)- 1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis( Trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methyl) Phenyl)ethenyl]-1,3,5-triazine and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine. ..

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. A commercially available product such as Irgacure (registered trademark) 819 (manufactured by BASF) may be used.

Further, as the polymerization initiator (D), benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl- Benzophenone compounds such as 4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone and 2,4,6-trimethylbenzophenone; 9,10-phenanthrenequinone, Quinone compounds such as 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds.
These are preferably used in combination with the below-mentioned polymerization initiation auxiliary agent (hereinafter sometimes referred to as polymerization initiation auxiliary agent (D1)), particularly amines.

The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, oxime compounds and biimidazole compounds, and more preferably oxime compounds. A polymerization initiator containing the same, more preferably a polymerization initiator containing an O-acyl oxime compound.

The content of the polymerization initiator (D) is preferably 0.001% by mass or more and 60% by mass or less, more preferably 0.01% by mass based on the total amount of the resin (B) and the polymerizable compound (C). It is from 50% by mass to 50% by mass.

[Polymerization initiation aid (D1)]
The colored composition of the present invention may contain a polymerization initiation aid (D1). The polymerization initiation aid (D1) is a compound or a sensitizer used for promoting the polymerization of the polymerizable compound (C) whose polymerization is initiated by the polymerization initiator (D). When the polymerization initiator auxiliary agent (D1) is contained, it is usually used in combination with the polymerization initiator (D).
Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds and carboxylic acid compounds.

As the amine compound, triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4- 2-Ethylhexyl dimethylaminobenzoate, N,N-dimethylparatoluidine, 4,4′-bis(dimethylamino)benzophenone (commonly called Michler's ketone), 4,4′-bis(diethylamino)benzophenone and 4,4′-bis( Examples thereof include ethylmethylamino)benzophenone, and preferably 4,4′-bis(diethylamino)benzophenone. Further, as the amine compound, a commercially available product such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used.

Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene and 9,10-dibutoxy. Examples thereof include anthracene and 2-ethyl-9,10-dibutoxyanthracene.

Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone and 1-chloro-4-propoxythioxanthone.

As the carboxylic acid compound, phenylsulfanyl acetic acid, methylphenylsulfanyl acetic acid, ethylphenylsulfanyl acetic acid, methylethylphenylsulfanyl acetic acid, dimethylphenylsulfanyl acetic acid, methoxyphenylsulfanyl acetic acid, dimethoxyphenylsulfanyl acetic acid, chlorophenylsulfanyl acetic acid, dichlorophenylsulfanyl acetic acid, N -Phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine and naphthoxyacetic acid.

When these polymerization initiation aids (D1) are used, their content is preferably 0.00001% by mass or more and 60% by mass or less based on the total amount of the resin (B) and the polymerizable compound (C). , And more preferably 0.0001 mass% or more and 50 mass% or less.

[Colorant (A1)]
The coloring composition of the present invention may contain a colorant other than the compound (I) (hereinafter, sometimes referred to as colorant (A1)). The colorant (A1) may contain one kind or two or more kinds of colorants. The colorant (A1) preferably contains at least one selected from a yellow colorant, an orange colorant, a red colorant and a green colorant, and contains at least one selected from a yellow colorant and a green colorant. Is more preferable.

The colorant (A1) may be a dye or a pigment. As the dye, known dyes can be used, and examples thereof include known dyes described in Color Index (The Society of Dyers and Colourists Publishing) and Dyeing Note (Shikiso Co., Ltd.). Also, according to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes. Examples thereof include dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinophthalone dyes and isoindoline dyes. You may use these dyes individually or in combination of 2 or more types.

Specific examples include dyes having the following color index (CI) numbers.
C. I. Solvent Yellow 4, 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, 189;
C. I. Solvent Red 24, 45, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;
C. I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99;
C. I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;
C. I. Solvent Blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;
C. I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35 and the like C.I. I. Solvent dye,
C. I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;
C. I. Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426;
C. I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;
C. I. Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;
C. I. Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340;
C. I. Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, C. 104, 105, 106, 109, etc. I. Acid dyes,
C. I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;
C. I. Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250;
C. I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C. I. Direct violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;
C. I. Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 87, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293;
C. I. C. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82 and the like. I. Direct dyes,
C. I. Disperse Yellow 51, 54, 76;
C. I. Disperse Violet 26, 27;
C. I. C. such as Disperse Blue 1, 14, 56, 60. I. Disperse dye,
C. I. Basic Red 1, 10;
C. I. Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89;
C. I. Basic Violet 2;
C. I. Basic Red 9;
C. I. C. such as Basic Green 1; I. Basic dye,
C. I. Reactive Yellow 2, 76, 116;
C. I. Reactive Orange 16;
C. I. C. such as Reactive Red 36; I. Reactive dye,
C. I. Modant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
C. I. Mordan tread 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38 , 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95;
C. I. Modern Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;
C. I. Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28 , 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58;
C. I. Modant blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43 , 44, 48, 49, 53, 61, 74, 77, 83, 84;
C. I. C. such as Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53. I. Modant dye,
C. I. C. such as Bat Green 1 I. Vat dye etc.

In addition, BASF's product Lumogen (registered trademark) is mentioned, and Lumogen (registered trademark) F Yellow 083 (manufactured by BASF), Lumogen (registered trademark) F Yellow 170 (manufactured by BASF), Lumogen (registered trademark) F Orange 240. (Manufactured by BASF) and Lumogen (registered trademark) F Red 305 (manufactured by BASF).

Further, the compound represented by the formula (z) and the compound represented by the formula (z1) are also included.

As the pigment, known pigments can be used, and examples thereof include pigments classified as pigments by Color Index (published by The Society of Dyers and Colorists). These may be used alone or in combination of two or more.
Specifically, C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, Yellow pigments such as 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231;
C. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and the like orange pigments;
C. I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 178, 179, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, Red pigments such as 265, 266, 268, 269, 273;
C. I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60 and other blue pigments;
C. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other violet color pigments;
C. I. Pigment Green 7, 36, 58, 59, 62, 63 and other green pigments;
C. I. Pigment Brown 23, 25 and other brown pigments;
C. I. Pigment Black 1, 7, 31, 32 and the like black pigments.

As the colorant (A1), a yellow dye and a yellow pigment (hereinafter, these may be collectively referred to as “yellow colorant” in some cases), an orange dye and an orange pigment (hereinafter, these are collectively referred to as “orange colorant”) Red dye and red pigment (hereinafter, these may be collectively referred to as “red colorant”), green dye and green pigment (hereinafter, these may be collectively referred to as “green colorant”) Are present), yellow colorants and green colorants are more preferable, yellow pigments and green pigments are further preferable, and green pigments are particularly preferable.

The yellow dye includes dyes whose hue is classified as yellow among the above dyes, and the yellow pigments include pigments whose hue is classified as yellow among the above pigments.
As the yellow colorant, yellow dyes and yellow pigments are preferable, yellow pigments are more preferable, quinophthalone pigments, metal-containing pigments and isoindoline pigments are further preferable, and C.I. I. Pigment Yellow 129, 138, 139, 150, 185, 231 are particularly preferable, and C.I. I. Pigment Yellow 138, 139, 150, 185, 231 is more preferable.

The orange dye includes dyes whose hue is classified as orange among the above dyes, and the orange pigments include pigments whose hue is classified as orange among the above pigments.
The orange colorant is preferably an orange dye or an orange pigment, more preferably an orange pigment, and C.I. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 are more preferable.

The red dye includes dyes whose hue is classified as red among the above dyes, and the red pigments include pigments whose hue is classified as red among the above pigments.
As the red colorant, red dyes and red pigments are preferable, and azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, perylene dyes, azo pigments, diketopyrrolopyrrole pigments, anthraquinone pigments, triphenylmethane dyes, xanthene pigments. And perylene pigments are more preferred, and C.I. I. Acid Red 52, C.I. I. Pigment Red 144, 177, 179, 242, 254 and 269 are more preferable.

Further, as a yellow colorant, an orange colorant or a red colorant, a xanthene compound described in JP2013-235257A may be used.

Examples of the green dye include dyes whose hue is classified as green among the above dyes, and examples of green pigments include pigments whose hue is classified as green among the above pigments.
As the green colorant, a green dye and a green pigment are preferable, a green pigment is more preferable, a phthalocyanine pigment is further preferable, a halogenated copper phthalocyanine pigment, a halogenated zinc phthalocyanine pigment and a halogenated aluminum zinc phthalocyanine pigment are particularly preferable, and C.I. I. Pigment Green 7, 36, 58, 59, 62 and 63 are more preferable.

[Preparation of Liquid Containing Colorant (A1)]
When the coloring composition of the present invention contains the colorant (A1), a colorant (A1)-containing liquid containing the colorant (A1) and the solvent (E) is prepared in advance, and then the colorant (A1)-containing liquid May be used to prepare the coloring composition. When the colorant (A1) does not dissolve in the solvent (E), the colorant (A1)-containing liquid can be prepared by dispersing the colorant (A1) in the solvent (E) and mixing them. The colorant (A1)-containing liquid may contain a part or all of the solvent (E) contained in the coloring composition.

The content of the solid content in the colorant (A1)-containing liquid is less than 100% by mass, preferably 0.01% by mass or more and 99.99% by mass or less, based on the total amount of the colorant (A1)-containing liquid. And more preferably 0.1% by mass or more and 99.9% by mass or less, further preferably 0.1% by mass or more and 99% by mass or less, and particularly preferably 1% by mass or more and 90% by mass or less. , More preferably 1% by mass or more and 80% by mass or less, particularly preferably 1% by mass or more and 70% by mass or less, very preferably 1% by mass or more and 60% by mass or less, and most preferably 1% by mass or more. It is 50 mass% or less.

The content of the colorant (A1) in the colorant (A1)-containing liquid is 100% by mass or less, preferably 0.0001% by mass or more and 99% by mass, in the total amount of solids in the colorant (A1)-containing liquid. 0.0099% by mass or less, more preferably 0.0001% by mass or more and 99% by mass or less, further preferably 1% by mass or more and 99% by mass or less, and particularly preferably 3% by mass or more and 99% by mass or less. Yes, and more preferably 5 mass% or more and 99 mass% or less.

The colorant (A1) is, if necessary, rosin treatment, surface treatment using a derivative having an acidic group or a basic group introduced therein, graft treatment with a polymer compound or the like on the surface of the colorant (A1), sulfuric acid. Atomization treatment by atomization method, salt milling method, etc., cleaning treatment with organic solvent or water for removing impurities, removal treatment of ionic impurities by ion exchange method, crystal structure conversion similar to compound (I) Alternatively, the particles may be shaped and/or substantially uniformized in particle size. The particle size of the colorant (A1) is preferably substantially uniform.

The colorant (A1) can be made to be in a state of being uniformly dispersed in the colorant (A1)-containing liquid by performing a dispersion treatment by adding a dispersant. Each of the colorants (A1) may be subjected to a dispersion treatment alone or a mixture of a plurality of types may be subjected to a dispersion treatment.

When the colorant (A1)-containing liquid contains a dispersant, the amount of the dispersant (solid content) used is, for example, 0.01 part by mass or more and 10000 parts by mass or less with respect to 100 parts by mass of the colorant (A1). Is preferably 0.01 parts by mass or more and 5000 parts by mass or less, more preferably 0.01 parts by mass or more and 1000 parts by mass or less, and further preferably 0.1 parts by mass or more and 500 parts by mass or less, It is particularly preferably 0.1 part by mass or more and 300 parts by mass or less, more preferably 1 part by mass or more and 300 parts by mass or less, and particularly preferably 5 parts by mass or more and 260 parts by mass or less.
When the amount of the dispersant used is within the above range, a more uniformly dispersed liquid containing the colorant (A1) tends to be obtained.

The coloring composition of the present invention contains a resin (B), and a colorant (A1)-containing liquid containing a colorant (A1) and a solvent (E) is prepared in advance, and then the colorant (A1)-containing liquid is used. Then, when preparing the coloring composition of the present invention, the colorant (A1)-containing liquid may contain a part or all, preferably a part of the resin (B) contained in the coloring composition in advance. Good. By preliminarily containing the resin (B), the dispersion stability of the colorant (A1)-containing liquid can be further improved.

When the colorant (A1)-containing liquid contains the resin (B), the content of the resin (B) is, for example, 0.01 part by mass or more and 10000 parts by mass or less with respect to 100 parts by mass of the colorant (A1). Yes, preferably 0.01 parts by mass or more and 5000 parts by mass or less, more preferably 0.01 parts by mass or more and 1000 parts by mass or less, further preferably 0.1 parts by mass or more and 500 parts by mass or less, and especially It is preferably 0.1 part by mass or more and 300 parts by mass or less.

When the coloring composition of the present invention contains the coloring agent (A1), the content of the coloring agent (A) in which the compound (I) and the coloring agent (A1) are combined in the coloring composition is based on the total solid content. On the other hand, it is 100 mass% or less, preferably 0.0001 mass% or more and 99.9999 mass% or less, more preferably 0.0001 mass% or more and 99 mass% or less, and further preferably 0.0001 mass%. % Or more and 90% by mass or less, particularly preferably 0.0001% by mass or more and 80% by mass or less, more preferably 0.0001% by mass or more and 70% by mass or less, and particularly preferably 0.0001% by mass or more. It is 60 mass% or less, very preferably 0.0001 mass% or more and 55 mass% or less, and most preferably 0.1 mass% or more and 55 mass% or less.

When the coloring composition of the present invention contains the colorant (A1), the content of the compound (I) is usually 0.0001 mass% or more in the total amount of the colorant (A), and preferably 0. 0003 mass% or more, more preferably 0.0005 mass% or more, further preferably 0.001 mass% or more, the upper limit is less than 100 mass%, preferably 99.9999 mass% or less. , More preferably 99% by mass or less, further preferably 98% by mass or less, and particularly preferably 97% by mass or less.

[Leveling agent (F)]
Examples of the leveling agent (F) include a silicone-based surfactant, a fluorine-based surfactant, and a fluorine-containing silicone-based surfactant. These may have a polymerizable group in the side chain.

Examples of silicone-based surfactants include surfactants having a siloxane bond in the molecule. Specifically, Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324. , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan LLC). ..

Examples of the fluorinated surfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, Florard (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, and F543. R30, RS-718-K (manufactured by DIC Corporation), F-Top (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, Examples thereof include S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Laboratories, Inc.).

Examples of the silicone-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specific examples thereof include Megafac (registered trademark) R08, BL20, F475, F477 and F443 (manufactured by DIC Corporation).

When the leveling agent (F) is contained, its content is usually 0.00001% by mass or more and 5% by mass or less, preferably 0.00001% by mass or more and 3% by mass or less, based on the total amount of the coloring composition. And more preferably 0.0001% by mass or more and 2% by mass or less, and further preferably 0.0001% by mass or more and 1% by mass or less.
When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[Antioxidant (G)]
From the viewpoint of improving the heat resistance and light resistance of the colorant, it is preferable to use the antioxidant alone or in combination of two or more kinds. The antioxidant is not particularly limited as long as it is an industrially commonly used antioxidant, and a phenol-based antioxidant, a phosphorus-based antioxidant, a sulfur-based antioxidant and the like can be used.

Examples of the phenolic antioxidant include Irganox 1010 (Irganox 1010: pentaerythritol tetrakis [3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], manufactured by BASF), Irganox 1076 (Irganox 1076: octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, manufactured by BASF), Irganox 1330 (Irganox 1330: 3,3',3'',5,5') , 5″-hexa-tert-butyl-a,a′,a″-(mesitylene-2,4,6-toluyl)tri-p-cresol, manufactured by BASF), Irganox 3114 (Irganox 3114:1, 3,5-Tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF), Irga Knox 3790 (Irganox 3790: 1,3,5-tris((4-tert-butyl-3-hydroxy-2,6-xylyl)methyl)-1,3,5-triazine-2,4,6(1H, 3H,5H)-trione, manufactured by BASF), Irganox 1035 (Irganox 1035: thiodiethylenebis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], manufactured by BASF), Irganox 1135 (Irganox 1135: benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy, C7-C9 side chain alkyl ester, manufactured by BASF), Irganox 1520L (Irganox 1520L: 4,6-bis( Octylthiomethyl)-o-cresol, manufactured by BASF), Irganox 3125 (manufactured by Irganox 3125, manufactured by BASF), Irganox 565 (Irganox 565:2,4-bis(n-octylthio)-6-(4-hydroxy3′) ,5'-di-tert-butylanilino)-1,3,5-triazine, manufactured by BASF), ADEKA STAB AO-80 (ADEKA STAB AO-80:3,9-bis(2-(3-(3-tert-butyl) -4-hydroxy-5-methylphenyl)propionyloxy)-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro(5,5)undecane, manufactured by ADEKA), Sumilizer BHT ( Sumilizer B HT, manufactured by Sumitomo Chemical Co., Ltd., Sumilizer GA-80 (Sumilizer GA-80, manufactured by Sumitomo Chemical Co., Ltd.), Sumilizer GS (Sumilizer GS, manufactured by Sumitomo Chemical Co., Ltd.), Cyanox 1790 (Cyanox 1790, Co., Ltd.) ) Cytec) and vitamin E (manufactured by Eisai Co., Ltd.).

Examples of the phosphorus-based antioxidant include Irgafos 168 (Irgafos 168: tris(2,4-di-tert-butylphenyl)phosphite, manufactured by BASF), Irgafos 12 (Irgafos 12: Tris [2-[[2 , 4,8,10-Tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphine-6-yl]oxy]ethyl]amine, manufactured by BASF), Irgafos 38 (Irgafos 38: Bis(2,4-bis(1,1-dimethylethyl)-6-methylphenyl)ethyl ester phosphorous acid, manufactured by BASF), ADEKA STAB 329K (manufactured by ADEKA), ADEKA STAB PEP36 (manufactured by ADEKA) , ADEKA STAB PEP-8 (manufactured by ADEKA Corporation), Sandstab P-EPQ (manufactured by Clariant), Weston 618 (Weston 618, manufactured by GE), Weston 619G (Western 619G, manufactured by GE), Ultranox 626 (Ultranox 626) , GE) and Sumilizer GP: 6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-tert-butyldibenz[ d, f] [1.3.2] dioxaphosphepin) (manufactured by Sumitomo Chemical Co., Ltd.) and the like.

Examples of the sulfur-based antioxidants include dialkylthiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl or distearyl, and β-alkylmercaptopropiones such as tetrakis[methylene(3-dodecylthio)propionate]methane. Examples thereof include acid ester compounds.

[Other ingredients]
The coloring composition of the present invention may optionally contain additives known in the art, such as a filler, another polymer compound, an adhesion promoter, a light stabilizer and a chain transfer agent.
Examples of the adhesion promoter include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, and 3-glycid. Xypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercapto Propyltrimethoxysilane, 3-sulfanylpropyltrimethoxysilane, 3-isocyanatepropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-amino Propylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, 3-aminopropyltrimethoxysilane, 3 -Aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, N-phenyl-3-aminopropyltriethoxysilane and the like can be mentioned.

[Method for producing colored composition]
The coloring composition of the present invention includes, for example, the compound (I), the solvent (E), and, if necessary, the resin (B), the polymerizable compound (C), the polymerization initiator (D), the polymerization initiation auxiliary agent. It can be prepared by mixing (D1), colorant (A1), leveling agent (F), antioxidant (G) and/or other components. The mixing can be performed by a known or common apparatus and conditions.
The compound (I) is mixed with a part or all of the solvent (E) in advance and dispersed using a bead mill or the like until the average particle size of the compound (I) becomes about 0.2 μm or less. It is preferably used in the state of the containing liquid. At this time, part or all of the dispersant and the resin (B) may be blended, if necessary.
The colorant (A1) is previously mixed with a part or all of the solvent (E) and dispersed using a bead mill or the like until the average particle diameter of the colorant (A1) becomes about 0.2 μm or less. It is preferably used in the state of the (A1) containing liquid. At this time, part or all of the dispersant and the resin (B) may be blended, if necessary.
The compound (I) is preferably used in the state of a solution (the solution is included in the compound (I)-containing solution) previously dissolved in a part or all of the solvent (E). Further, the compound (I)-containing liquid is preferably filtered with a filter having a pore size of 0.01 μm or more and 1 μm or less.
The colorant (A1) is preferably used in the state of a solution (the solution is included in the colorant (A1)-containing liquid) previously dissolved in a part or all of the solvent (E). Furthermore, it is preferable to filter the colorant (A1)-containing liquid with a filter having a pore size of 0.01 μm or more and 1 μm or less.
The colored composition after mixing is preferably filtered with a filter having a pore size of 0.01 μm or more and 10 μm or less.

[Color filter]
A color filter can be formed from the colored composition of the present invention.
A colored coating film can be formed by applying the coloring composition to a substrate, removing volatile components such as a solvent, and drying. The colored coating film thus formed is included in the color filter of the present invention.
Examples of the method for forming the colored pattern include a photolithographic method, an inkjet method, a printing method and the like. Among them, the photolithographic method is preferable. The photolithographic method is a method in which the coloring composition is applied to a substrate and dried to form a coloring composition layer, and the coloring composition layer is exposed through a photomask and developed. In the photolithographic method, a colored coating film that is a cured product of the coloring composition layer can be formed by not using a photomask during exposure and/or not developing. The colored pattern and the colored coating film thus formed are the color filter of the present invention.
The film thickness of the color filter to be produced is not particularly limited and can be appropriately adjusted depending on the purpose, application, etc., and is, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably Is 0.5 to 6 μm.

As the substrate, quartz glass, borosilicate glass, alumina silicate glass, a glass plate such as soda lime glass whose surface is coated with silica, a resin plate such as polycarbonate, polymethylmethacrylate, polyethylene terephthalate, silicon, or the above substrate. Aluminum, silver, silver/copper/palladium alloy thin film, etc. are used. Other color filter layers, resin layers, transistors, circuits, and the like may be formed on these substrates.

The formation of each color pixel by the photolithography method can be performed by a known or commonly used apparatus and conditions. For example, it can be manufactured as follows.
First, the coloring composition is applied onto a substrate, and dried by heating (pre-baking) and/or vacuum drying to remove volatile components such as a solvent and drying to obtain a smooth coloring composition layer.
Examples of the coating method include a spin coating method, a slit coating method, and a slit and spin coating method.
The temperature for heat drying is preferably 30 to 120°C, more preferably 50 to 110°C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When drying under reduced pressure, it is preferable to perform the drying under a pressure of 50 to 150 Pa and a temperature range of 20 to 25°C. The thickness of the coloring composition layer is not particularly limited and may be appropriately selected depending on the intended thickness of the color filter.

Next, the coloring composition layer is exposed through a photomask for forming a desired coloring pattern.
The pattern on the photomask is not particularly limited, and a pattern according to the intended use is used. The light source used for exposure is preferably a light source that emits light having a wavelength of 250 to 450 nm. For example, light of less than 350 nm is cut using a filter that cuts this wavelength range, or light of about 436 nm, 408 nm, and 365 nm is selectively extracted using a bandpass filter that extracts these wavelength ranges. You may. Specific examples of the light source include a mercury lamp, a light emitting diode, a metal halide lamp and a halogen lamp.
An exposure device such as a mask aligner or stepper is used because it is possible to uniformly irradiate the entire exposed surface with parallel light rays and to perform accurate alignment between the photomask and the substrate on which the colored composition layer is formed. It is preferable.

A colored pattern is formed on the substrate by bringing the colored composition layer after exposure into contact with a developing solution for development. By the development, the unexposed portion of the colored composition layer is dissolved in the developing solution and removed.
As the developing solution, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate and tetramethylammonium hydroxide is preferable.
The concentration of the alkaline compound is preferably 0.01 to 10% by mass, more preferably 0.02 to 5% by mass. The developer may contain a surfactant.
The developing method may be a paddle method, a dipping method, a spray method or the like. Further, the substrate may be tilted at an arbitrary angle during development.
The substrate after development is preferably washed with water.
Furthermore, it is preferable to post-bake the obtained colored pattern.
The post-baking temperature is preferably 150 to 250°C, more preferably 160 to 235°C. The post-baking time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes. The color filter, which is the colored pattern or the colored coating film thus obtained, may be subjected to a surface coating treatment in order to impart various characteristics.

The color filter is useful as a color filter used for a display device (for example, a liquid crystal display device, an organic EL device, an electronic paper, etc.) and a solid-state image pickup device, and particularly as a color filter used for a liquid crystal display device.

The present application claims the benefit of priority based on Japanese Patent Application No. 2019-026911 filed on February 18, 2019. The entire contents of the specification of Japanese Patent Application No. 2019-026911 filed on February 18, 2019 are incorporated herein by reference.

Hereinafter, the present invention will be described more specifically with reference to Examples, but the present invention is not limited to the following Examples, and may be appropriately modified within a range compatible with the gist of the above and the following. Of course, it is possible to carry out, and all of them are included in the technical scope of the present invention. In the following, "part" means "part by mass" and "%" means "% by mass" unless otherwise specified.

In the following synthesis examples, the structure of the compound was confirmed by mass spectrometry (LC: 1200 type manufactured by Agilent, MASS; LC/MSD6130 type manufactured by Agilent).

The polystyrene equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by the GPC method under the following conditions.
Device: HLC-8120GPC (manufactured by Tosoh Corporation)
Column: TSK-GELG2000HXL
Column temperature: 40°C
Solvent: Tetrahydrofuran Flow rate: 1.0 mL/min Solid concentration of analytical sample: 0.001 to 0.01% by mass
Injection volume: 50 μL
Detector: RI
Calibration standard material: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)
The ratio (Mw/Mn) of the polystyrene-reduced weight average molecular weight (Mw) and number average molecular weight (Mn) obtained above was taken as the dispersity.

Example 1
3.02 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 8,33 parts of 2,3-naphthalenedicarboxylic acid anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), benzoic acid (Tokyo Kasei) 11.7 parts of Kogyo Co., Ltd. and 66.7 parts of methyl benzoate (Tokyo Kasei Kogyo Co., Ltd.) were mixed.
The mixture was stirred for 9 hours while maintaining the temperature at 170°C.
To this mixture, 13.6 parts of 2,3-naphthalenedicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 22.9 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and methyl benzoate (Tokyo Chemical Industry Co., Ltd.) 66.4 parts manufactured by Co., Ltd. were added.
The mixture was stirred for 49 hours, keeping at 170°C.
To this mixture, 8.32 parts of 2,3-naphthalenedicarboxylic acid anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 11.7 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and methyl benzoate (Tokyo Chemical Industry Co., Ltd.) (Manufactured by K.K.) 43.5 parts was added.
The mixture was stirred for 28 hours while maintaining the temperature at 170°C.
The mixture was cooled to room temperature, and 1300 parts of methanol was added to the mixture.
The mixture was stirred at room temperature and then filtered, and the obtained residue was washed 7 times with 400 parts of methanol.
The obtained residue was dried under reduced pressure at 60°C.
To this residue was added 875 parts of N,N-dimethylformamide.
The mixture was stirred at room temperature and then filtered, and the obtained residue was washed 3 times with the same volume of N,N-dimethylformamide as the obtained residue.
The residue was washed 3 times with 200 parts of methanol.
The obtained residue was dried under reduced pressure at 60° C. to obtain 7.25 parts of a compound represented by the formula (Ia2).

<Identification of compound represented by formula (Ia2)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 519
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 517
Exact Mass: 518

Example 2
2.05 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), tetrachlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) 8.16 parts, benzoic acid (Tokyo Chemical Industry Co., Ltd.) )) and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) 58.6 parts.
The mixture was stirred for 5 hours, keeping at 170°C.
To this mixture, 3.72 parts of tetrachlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 8.00 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and methyl benzoate (Tokyo Chemical Industry Co., Ltd.) 18.0 parts).
The mixture was stirred for 6 hours while maintaining the temperature at 170°C.
To this mixture, 1.89 parts of tetrachlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 4.09 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and methyl benzoate (Tokyo Chemical Industry Co., Ltd.) 54.5 parts).
The mixture was stirred for 6 hours while maintaining the temperature at 170°C.
11.4 parts of tetrachlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 12.6 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and methyl benzoate (Tokyo Chemical Industry Co., Ltd.) were added to this mixture. 18.4 parts).
The mixture was stirred for 16 hours, keeping at 170°C.
The mixture was cooled to room temperature and 1200 parts of methanol was added to the mixture.
The mixture was stirred at room temperature and then filtered, and the obtained residue was washed 8 times with 400 parts of methanol.
The obtained residue was dried under reduced pressure at 60° C. to obtain 8.88 parts of a compound represented by the formula (Ia23).

<Identification of compound represented by formula (Ia23)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 691
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 689
Exact Mass: 690

Example 3
4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) 1.01 part, 4-phenylethynyl phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) 3.49 parts, benzoic acid (Tokyo Chemical Industry Co., Ltd.) (Manufactured by KK) and 3.87 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed.
The mixture was stirred for 20 hours while maintaining the temperature at 170°C.
To this mixture, 0.476 parts of 4-phenylethynylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.32 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and methyl benzoate (Tokyo Chemical Industry ( Co., Ltd.) 3.3 parts was added.
The mixture was stirred at 170° C. for 10 hours.
To this mixture, 0.801 part of 4-phenylethynylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 2.90 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and methyl benzoate (Tokyo Chemical Industry ( (Manufactured by K.K.) 9.13 parts was added.
The mixture was stirred for 29 hours, keeping at 170°C.
This mixture was cooled to room temperature, 400 parts of methanol was added to this mixture, and the mixture was stirred for 1 hour.
The mixture was filtered and the resulting residue was washed 6 times with 140 parts of methanol.
The obtained residue was dried under reduced pressure at 60° C. to obtain 3.12 parts of the compound represented by the formula (Ia22).

<Identification of compound represented by formula (Ia22)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 619
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 617
Exact Mass: 618

Example 4
4-Amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) 4.04 parts, trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) 10.8 parts, benzoic acid (Tokyo Chemical Industry Co., Ltd.) 15.6 parts) and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) 92.3 parts were mixed.
The mixture was stirred at 167°C for 5 hours.
To this mixture, 40.2 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) was added.
The mixture was stirred for 9 hours while maintaining the temperature at 167°C.
To this mixture was added 28.0 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).
The mixture was stirred for 11 hours while maintaining the temperature at 170°C.
The mixture was cooled to room temperature and 2000 parts of methanol was added to the mixture.
The mixture was stirred at room temperature.
173 parts of methanol was added to the obtained mixture.
The mixture was filtered and the residue obtained was washed once with 124 parts of methanol, once with 160 parts and once with 400 parts.
The obtained residue is dried under reduced pressure at 60° C. to give a compound represented by the formula (Ia10), a compound represented by the formula (Ia2143), a compound represented by the formula (Ia850) and a compound represented by the formula (Ia315). This gave 9.91 parts of a mixture of compounds.

<Identification of Compound Represented by Formula (Ia10)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 507
(Mass spectrometry) Ionization mode=ESI-: m/z=[M−H] ⁻ 505
Exact Mass: 506

<Identification of compound represented by formula (Ia2143)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 521
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 519
Exact Mass: 520

<Identification of compound represented by formula (Ia850)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 521
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 519
Exact Mass: 520

<Identification of compound represented by formula (Ia315)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 535
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 533
Exact Mass: 534

Example 5
5.23 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 14.2 parts of 3-nitrophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), benzoic acid (Tokyo Chemical Industry Co., Ltd.) 20.2 parts) and 119 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).
The mixture was stirred for 12 hours while maintaining the temperature at 168°C.
To this mixture, 7.12 parts of 3-nitrophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 10.3 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and methyl benzoate (Tokyo Chemical Industry Co., Ltd.) 16.0 parts).
The mixture was stirred for 26 hours, keeping at 170°C.
The mixture was cooled to room temperature and 2400 parts of methanol was added to the mixture.
The resulting mixture was stirred at room temperature and then filtered.
The obtained residue was washed 5 times with 400 parts of methanol.
The obtained residue was dried under reduced pressure at 60° C. to obtain 13.0 parts of the compound represented by the formula (Ia35).

<Identification of compound represented by formula (Ia35)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 509
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 507
Exact Mass: 508

Example 6
4-Amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) 3.67 parts, phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) 7.59 parts, benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) ) 14.4 parts and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) 84.3 parts were mixed.
The mixture was stirred at 170° C. for 10 hours.
To this mixture, 7.92 parts of phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 15.5 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) 45 parts were added.
The mixture was stirred for 9 hours while maintaining the temperature at 170°C.
To this mixture was added 9 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).
The mixture was stirred for 18 hours, keeping at 170°C.
To this mixture, 7.77 parts of phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 14.6 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) 11.1 parts were added.
The mixture was stirred for 27 hours while maintaining the temperature at 170°C.
To this mixture, 3.88 parts of phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 7.33 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) 12.3 parts was added.
The mixture was stirred for 8 hours while maintaining the temperature at 170°C.
The mixture was cooled to room temperature and 2800 parts of methanol was added to the mixture.
The resulting mixture was stirred at room temperature and then filtered.
The obtained residue was washed twice with 400 parts of methanol and once with 800 parts of methanol.
The obtained residue was dried under reduced pressure at 60°C to obtain 7.67 parts of a compound represented by the formula (Ia1).

<Identification of compound represented by formula (Ia1)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 419
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 417
Exact Mass: 418

Example 7
A mixture of the compound represented by the formula (Ia10), the compound represented by the formula (Ia2143), the compound represented by the formula (Ia850) and the compound represented by the formula (Ia315) obtained in Example 4, 1.05 Parts and 106 parts of water were mixed.
22.1 parts of 1% sodium hydroxide aqueous solution was added to this mixture at room temperature.
To the obtained mixture, at room temperature, 3.23 parts of iron nitrate (III) nonahydrate (manufactured by Wako Pure Chemical Industries, Ltd.) and 8.19 parts of a mixture of 29.1 parts of water were added.
The resulting mixture was filtered and the residue obtained was washed twice with the same volume of water as the residue obtained.
The obtained residue was dried under reduced pressure at 60° C. to obtain 1.17 parts of a mixture containing the compound represented by the formula (Ie12).

Example 8
5.03 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 13.6 parts of 4-nitrophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), benzoic acid (Tokyo Chemical Industry Co., Ltd. 19.5 parts) and 116 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).
The mixture was stirred for 4 hours, keeping at 170°C.
To this mixture, 7.12 parts of 4-nitrophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 10.5 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and methyl benzoate (Tokyo Chemical Industry Co., Ltd.) 30.1 parts).
The mixture was stirred for 18 hours, keeping at 170°C.
To this mixture, 13.6 parts of 4-nitrophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 19.3 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and methyl benzoate (Tokyo Chemical Industry Co., Ltd.) 29.1 parts).
The mixture was stirred for 27 hours while maintaining the temperature at 170°C.
The mixture was cooled to room temperature and 2800 parts of methanol was added to the mixture.
The resulting mixture was stirred at room temperature and then filtered.
The obtained residue was washed 4 times with 400 parts of methanol.
The obtained residue was dried under reduced pressure at 60° C. to obtain 14.8 parts of the compound represented by the formula (Ia33).

<Identification of compound represented by formula (Ia33)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 509
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 507
Exact Mass: 508

Example A-1
4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) 1 mol,
3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) 8 mol,
21 moles of benzoic acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 4-mol of 2-amino-2-methylquinoline (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 73 times the weight of methyl benzoate (Tokyo Kasei Kogyo Co., Ltd.) ))
Were mixed.
The mixture was stirred for 120 hours while maintaining the temperature at 170°C.
The mixture was cooled to room temperature and 13 times the weight of the mixture by weight of methanol was added to the mixture.
The resulting mixture was stirred at room temperature and then filtered.
The obtained residue was washed with methanol.
The obtained residue was purified by column chromatography to obtain the compound represented by the formula (Ia5).

<Identification of compound represented by formula (Ia5)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 447
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 445
Exact Mass: 446

Example A-2
The same procedure as in Example A-1 was performed except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 1,2-naphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.). A compound represented by the formula (Ia3) was obtained.

<Identification of compound represented by formula (Ia3)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 519
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 517
Exact Mass: 518

Example A-3
The procedure was carried out in the same manner as in Example A-1 except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 3-chlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.). A compound represented by (Ia17) was obtained.

<Identification of compound represented by formula (Ia17)>
(Mass Spectrometry) ionization mode = ESI +: m / z = [M + H] + 487
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 485
Exact Mass: 486

Example A-4
Using the same procedure as in Example A-1 except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-chlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), A compound represented by (Ia7) was obtained.

<Identification of compound represented by formula (Ia7)>
(Mass Spectrometry) ionization mode = ESI +: m / z = [M + H] + 487
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 485
Exact Mass: 486

Example A-5
Example 3 was repeated except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 3-acetamidophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.). A compound represented by the formula (Ia36) was obtained.

<Identification of compound represented by formula (Ia36)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 533
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 531
Exact Mass: 532

Example A-6
The procedure was performed in the same manner as in Example A-1 except that 3-methylphthalic anhydride (manufactured by Tokyo Kasei Kogyo Co., Ltd.) was replaced with 3-hydroxyphthalic anhydride (manufactured by Sigma-Aldrich Japan GK). A compound represented by (Ia51) was obtained.

<Identification of compound represented by formula (Ia51)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 451
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 449
Exact Mass: 450

Example A-7
Example 3 was repeated except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 3-fluorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.). A compound represented by the formula (Ia19) was obtained.

<Identification of compound represented by formula (Ia19)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 455
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 453
Exact Mass: 454

Example A-8
The procedure described in Example A-1 was repeated except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with the compound represented by the formula (sm1), and the compound represented by the formula (Ia248) was used. A compound was obtained.

<Identification of Compound Represented by Formula (Ia248)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 507
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 505
Exact Mass: 506

Example A-9
The procedure was performed in the same manner as in Example A-1 except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.). A compound represented by (Ia4) was obtained.

<Identification of compound represented by formula (Ia4)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 447
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 445
Exact Mass: 446

Example A-10
4-Amino-2-methylquinoline (manufactured by Tokyo Kasei Kogyo Co., Ltd.) was replaced with 4-amino-6-fluoro-2-methylquinoline (manufactured by Sigma-Aldrich Japan GK), and 3-methylphthalic anhydride (Tokyo Kasei) The procedure of Example A-1 was repeated except that 2,3-naphthalenedicarboxylic acid anhydride (manufactured by Kogyo Co., Ltd.) was replaced by 2,3-naphthalenedicarboxylic acid anhydride, which was represented by the formula (It242). A compound was obtained.

<Identification of compound represented by formula (It242)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 537
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 535
Exact Mass: 536

Example A-11
4-Amino-2-methylquinoline (manufactured by Tokyo Kasei Kogyo Co., Ltd.) was replaced with 4-amino-6-methoxy-2-methylquinoline (manufactured by Sigma-Aldrich Japan GK), and 3-methylphthalic anhydride (Tokyo Kasei) The procedure of Example A-1 was repeated except that 2,3-naphthalenedicarboxylic acid anhydride (manufactured by Kogyo Co., Ltd.) was replaced by 2,3-naphthalenedicarboxylic acid anhydride (Formula ItIt). A compound was obtained.

<Identification of compound represented by formula (It232)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 549
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 547
Exact Mass: 548

Example A-12
Example A-1 except that 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-amino-6-bromo-2-methylquinoline (manufactured by Sigma-Aldrich Japan GK). The same procedure was performed to obtain a compound represented by the formula (It750).

<Identification of compound represented by formula (It750)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 525
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 523
Exact Mass: 524

Synthesis Example B-1
A mixture of 1 mol of the compound represented by the formula (Ia2) and 20 mol of potassium hydroxide and 10 times by weight of water as much as 1 mol of the compound represented by the formula (Ia2) was mixed.
The mixture was stirred at 90° C. until the compound represented by the formula (Ia2) disappeared.
This mixture was mixed with 36% hydrochloric acid for neutralization.
The mixture was filtered.
The obtained residue was washed with water.
The residue was purified by column chromatography to obtain the compound represented by the formula (IM1-1).

<Identification of Compound Represented by Formula (IM1-1)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 339
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 337
Exact Mass: 338

Synthesis Example B-2
A compound represented by the formula (IM1-2) was obtained in the same manner as in Synthesis Example B-1, except that the compound represented by the formula (Ia2) was replaced with the compound represented by the formula (Ia23). It was

<Identification of Compound Represented by Formula (IM1-2)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 425
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 423
Exact Mass: 424

Synthesis Example B-3
A compound represented by the formula (IM1-3) was obtained in the same manner as in Synthesis Example B-1, except that the compound represented by the formula (Ia2) was replaced with the compound represented by the formula (Ia5). It was

<Identification of compound represented by formula (IM1-3)>
(Mass Spectrometry) ionization mode = ESI +: m / z = [M + H] + 303
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 301
Exact Mass: 302

Synthesis Example B-4
A compound represented by the formula (IM1-4) was obtained in the same manner as in Synthesis Example B-1 except that the compound represented by the formula (Ia2) was replaced with the compound represented by the formula (Ia4). It was

<Identification of Compound Represented by Formula (IM1-4)>
(Mass Spectrometry) ionization mode = ESI +: m / z = [M + H] + 303
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 301
Exact Mass: 302

Synthesis Example B-5
A compound represented by the formula (IM1-5) was obtained in the same manner as in Synthesis Example B-1 except that the compound represented by the formula (Ia2) was replaced with the compound represented by the formula (Ia36). It was

<Identification of Compound Represented by Formula (IM1-5)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 346
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 344
Exact Mass: 345

Synthesis Example B-6
A compound represented by the formula (IM1-6) was obtained in the same manner as in Synthesis Example B-1, except that the compound represented by the formula (Ia2) was replaced with the compound represented by the formula (Ia1). It was

<Identification of Compound Represented by Formula (IM1-6)>
(Mass Spectrometry) ionization mode = ESI +: m / z = [M + H] + 289
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 287
Exact Mass: 288

Example C-1
1 mol of a compound represented by the formula (IM1-1),
8 mol of trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.),
21 mol of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 73 times the weight of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) 73 times the weight of 1 mol of the compound represented by the formula (IM1-1).
Were mixed.
The mixture was stirred for 120 hours while maintaining the temperature at 170°C.
The mixture was cooled to room temperature and 13 times the weight of the mixture by weight of methanol was added to the mixture.
The resulting mixture was stirred at room temperature and then filtered.
The obtained residue was washed with methanol.
The obtained residue was purified by column chromatography to obtain the compound represented by the formula (Ia699).

<Identification of compound represented by formula (Ia699)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 513
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 511
Exact Mass: 512

Example C-2
The compound represented by the formula (IM1-1) is replaced with the compound represented by the formula (IM1-2), and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) is replaced with 2,3-naphthalenedicarboxylic anhydride. A compound represented by the formula (Ia970) was obtained in the same manner as in Example C-1 except that (Tokyo Kasei Kogyo Co., Ltd.) was used.

<Identification of Compound Represented by Formula (Ia970)>
(Mass Spectrometry) ionization mode = ESI +: m / z = [M + H] + 605
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 603
Exact Mass: 604

Example C-3
Trimeric acid anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with tetrachlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), and the procedure was carried out in the same manner as in Example C-1, except that the formula ( A compound represented by Ia703) was obtained.

<Identification of compound represented by formula (Ia703)>
(Mass Spectrometry) ionization mode = ESI +: m / z = [M + H] + 605
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 603
Exact Mass: 604

Example C-4
Trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), and the procedure was carried out in the same manner as in Example C-1. A compound represented by If3796) was obtained.

<Identification of compound represented by formula (If3796)>
(Mass Spectrometry) ionization mode = ESI +: m / z = [M + H] + 483
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 481
Exact Mass: 482

Example C-5
Formula (Ia696) was prepared in the same manner as in Example C-1 except that phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.). A compound represented by

<Identification of compound represented by formula (Ia696)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 469
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 467
Exact Mass: 468

Example C-6
The compound represented by the formula (IM1-1) was replaced with the compound represented by the formula (IM1-2), and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with phthalic anhydride (Tokyo Chemical Industry ( The same procedure as in Example C-1 except that the compound represented by the formula (Ia969) was obtained.

<Identification of compound represented by formula (Ia969)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 555
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 553
Exact Mass: 554

Example C-7
The compound represented by the formula (IM1-1) was replaced with the compound represented by the formula (IM1-2), and trimellitic anhydride (manufactured by Tokyo Kasei Kogyo Co., Ltd.) was replaced with 3-methylphthalic anhydride (Tokyo Kasei). A compound represented by the formula (If2528) was obtained in the same manner as in Example C-1, except that the compound was changed to Kogyo Co., Ltd.).

<Identification of compound represented by formula (If2528)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 569
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 567
Exact Mass: 568

Example C-8
A compound represented by the formula (Ia973) obtained in the same manner as in Example C-1 except that the compound represented by the formula (IM1-1) was replaced with the compound represented by the formula (IM1-2). Got

<Identification of compound represented by formula (Ia973)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 599
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 597
Exact Mass: 598

Example C-9
A compound represented by the formula (If1261) in the same manner as in Example C-1 except that the compound represented by the formula (IM1-1) was replaced with the compound represented by the formula (IM1-3). Got

<Identification of compound represented by formula (If1261)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 477
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 475
Exact Mass: 476

Example C-10
The compound represented by the formula (IM1-1) was replaced with the compound represented by the formula (IM1-3), and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with tetrachlorophthalic anhydride (Tokyo Chemical Co., Ltd.). A compound represented by the formula (If5688) was obtained in the same manner as in Example C-1, except that the compound was changed to Kogyo Co., Ltd.).

<Identification of compound represented by formula (If5688)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 569
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 567
Exact Mass: 568

Example C-11
The compound represented by the formula (IM1-1) is replaced with the compound represented by the formula (IM1-3), and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) is replaced with 2,3-naphthalenedicarboxylic anhydride. A compound represented by the formula (If636) was obtained in the same manner as in Example C-1 except that (Tokyo Kasei Kogyo Co., Ltd.) was used.

<Identification of compound represented by formula (If636)>
(Mass Spectrometry) ionization mode = ESI +: m / z = [M + H] + 483
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 481
Exact Mass: 482

Example C-12
The compound represented by the formula (IM1-1) was replaced with the compound represented by the formula (IM1-3), and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 1,2-naphthalic anhydride ( A compound represented by the formula (If5670) was obtained in the same manner as in Example C-1 except that the compound was changed to Tokyo Chemical Industry Co., Ltd.).

<Identification of Compound Represented by Formula (If5670)>
(Mass Spectrometry) ionization mode = ESI +: m / z = [M + H] + 483
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 481
Exact Mass: 482

Example C-13
The compound represented by the formula (IM1-1) was replaced with the compound represented by the formula (IM1-3), and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 1,8-naphthalic anhydride ( A compound represented by the formula (If5720) was obtained in the same manner as in Example C-1 except that the compound was changed to Tokyo Chemical Industry Co., Ltd.).

<Identification of Compound Represented by Formula (If5720)>
(Mass Spectrometry) ionization mode = ESI +: m / z = [M + H] + 483
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 481
Exact Mass: 482

Example C-14
Example 1 was repeated except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 1,8-naphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.). A compound represented by the formula (Ia712) was obtained.

<Identification of Compound Represented by Formula (Ia712)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 519
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 517
Exact Mass: 518

Example C-15
The compound represented by the formula (IM1-1) is replaced with the compound represented by the formula (IM1-4), and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) is replaced with 2,3-naphthalenedicarboxylic anhydride. A compound represented by the formula (If635) was obtained in the same manner as in Example C-1, except that (Tokyo Kasei Kogyo Co., Ltd.) was used.

<Identification of compound represented by formula (If635)>
(Mass Spectrometry) ionization mode = ESI +: m / z = [M + H] + 483
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 481
Exact Mass: 482

Example C-16
A compound represented by the formula (If1260) was prepared in the same manner as in Example C-1 except that the compound represented by the formula (IM1-1) was replaced with the compound represented by the formula (IM1-4). Got

<Identification of Compound Represented by Formula (If1260)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 477
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 475
Exact Mass: 476

Example C-17
The compound represented by the formula (IM1-1) was replaced with the compound represented by the formula (IM1-4), and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with pyromellitic anhydride (Tokyo Chemical Industry Co., Ltd.). A compound represented by the formula (If13040) was obtained in the same manner as in Example C-1 except that the compound was changed to that manufactured by Co., Ltd.).

<Identification of compound represented by formula (If13040)>
(Mass Spectrometry) ionization mode = ESI +: m / z = [M + H] + 521
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 519
Exact Mass: 520

Example C-18
The compound represented by the formula (IM1-1) was replaced with the compound represented by the formula (IM1-4), and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-tert-butylphthalic anhydride ( A compound represented by the formula (If8454) was obtained in the same manner as in Example C-1 except that the compound was changed to Tokyo Chemical Industry Co., Ltd.).

<Identification of compound represented by formula (If8454)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 489
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 487
Exact Mass: 488

Example C-19
The procedure was performed in the same manner as in Example C-1 except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), and the formula ( A compound represented by If3795) was obtained.

<Identification of compound represented by formula (If3795)>
(Mass Spectrometry) ionization mode = ESI +: m / z = [M + H] + 483
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 481
Exact Mass: 482

Example C-20
The compound represented by the formula (IM1-1) was replaced with the compound represented by the formula (IM1-3), and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-methylphthalic anhydride (Tokyo Chemical Co., Ltd.). A compound represented by the formula (If5671) was obtained in the same manner as in Example C-1 except that the compound was changed to Kogyo Co., Ltd.).

<Identification of compound represented by formula (If5671)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 447
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 445
Exact Mass: 446

Example C-21
The compound represented by the formula (IM1-1) was replaced with the compound represented by the formula (IM1-4), and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 3-methylphthalic anhydride (Tokyo Chemical Co., Ltd.). A compound represented by the formula (If2511) was obtained in the same manner as in Example C-1, except that the compound was changed to Kogyo Co., Ltd.).

<Identification of compound represented by formula (If2511)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 447
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 445
Exact Mass: 446

Example C-22
Example 1 was repeated except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-tert-butylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.). A compound represented by the formula (If3799) was obtained.

<Identification of compound represented by formula (If3799)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 525
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 523
Exact Mass: 524

Example C-23
Trimeritride anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 3-acetamidophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), and the procedure was carried out in the same manner as in Example C-1. A compound represented by (If3814) was obtained.

<Identification of Compound Represented by Formula (If3814)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 526
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 524
Exact Mass: 525

Example C-24
The compound represented by the formula (IM1-1) is replaced with the compound represented by the formula (IM1-5), and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) is replaced with 2,3-naphthalenedicarboxylic anhydride. A compound represented by the formula (If654) was obtained in the same manner as in Example C-1 except that (Tokyo Kasei Kogyo Co., Ltd.) was used.

<Identification of compound represented by formula (If654)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 526
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 524
Exact Mass: 525

Example C-25
The compound represented by the formula (IM1-1) was replaced with the compound represented by the formula (IM1-5), and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with phthalic anhydride (Tokyo Chemical Industry ( A compound represented by the formula (If29) was obtained in the same manner as in Example C-1 except that the compound was changed to a compound (If29).

<Identification of compound represented by formula (If29)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 476
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 474
Exact Mass: 475

Example C-26
A compound represented by the formula (If1279), which was carried out in the same manner as in Example C-1, except that the compound represented by the formula (IM1-1) was replaced with the compound represented by the formula (IM1-5). Got

<Identification of Compound Represented by Formula (If1279)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 520
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 518
Exact Mass: 519

Example C-27
The compound represented by the formula (IM1-1) is replaced by the compound represented by the formula (IM1-5), and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) is represented by the compound represented by the formula (sm1). A compound represented by the formula (If1904) was obtained in the same manner as in Example C-1, except that the compound was replaced by.

<Identification of Compound Represented by Formula (If1904)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 520
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 518
Exact Mass: 519

Example C-28
Represented by formula (Ia728), carried out in the same manner as in Example C-1, except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by the compound represented by formula (sm1). The compound was obtained.

<Identification of compound represented by formula (Ia728)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 513
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 511
Exact Mass: 512

Example C-29
The compound represented by the formula (IM1-1) is replaced with the compound represented by the formula (IM1-6), and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) is replaced with 2,3-naphthalenedicarboxylic anhydride. A compound represented by the formula (Ia657) was obtained in the same manner as in Example C-1 except that (Tokyo Kasei Kogyo Co., Ltd.) was used.

<Identification of compound represented by formula (Ia657)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 469
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 467
Exact Mass: 468

Example C-30
The compound represented by the formula (IM1-1) was replaced with the compound represented by the formula (IM1-6), and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 3-methylphthalic anhydride (Tokyo Chemical Co., Ltd.). A compound represented by the formula (If3171) was obtained in the same manner as in Example C-1, except that the compound was changed to Kogyo Co., Ltd.).

<Identification of compound represented by formula (If3171)>
(Mass Spectrometry) ionization mode = ESI +: m / z = [M + H] + 433
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 431
Exact Mass: 432

Example C-31
The compound represented by the formula (IM1-1) was replaced with the compound represented by the formula (IM1-6), and trimellitic anhydride (manufactured by Tokyo Kasei Kogyo Co., Ltd.) was replaced with 3-chlorophthalic anhydride (Tokyo Kasei). A compound represented by the formula (Ia686) was obtained in the same manner as in Example C-1 except that the compound was changed to Kogyo Co., Ltd.).

<Identification of compound represented by formula (Ia686)>
(Mass spectrometry) Ionization mode=ESI+: m/z=[M+H] ⁺ 453
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 451
Exact Mass: 452

Example E-1
1.61 parts of the compound represented by the formula (Ia5) and 32.7 parts of fuming sulfuric acid (25%) (manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.) were mixed while maintaining the temperature at 10°C to 20°C.
The mixture was stirred for 3 hours, keeping at 5°C to 20°C.
This mixture was added dropwise to 62.2 parts of ice.
The resulting mixture was filtered.
Aqueous 10% ammonia was added to the obtained filtrate to neutralize the obtained filtrate.
The solvent of this mixture was evaporated until the volume of this mixture was halved.
To the resulting mixture was added twice the volume of this mixture as methanol.
This mixture was filtered, and the solvent of the obtained filtrate was evaporated.
The obtained residue is dried under reduced pressure at 60° C.,
A compound represented by the formula (Ia5-SA1) (a compound represented by the formula (Ia5) in which any one hydrogen atom is replaced by —SO ₃ NH ₄ ), and a compound represented by the formula (Ia5-SA2) 0.58 parts of a mixture containing a compound represented by the formula (a compound represented by the formula (Ia5) in which any two hydrogen atoms of the compound are replaced by —SO ₃ NH ₄ ) was obtained.

<Identification of Compound Represented by Formula (Ia5-SA1)>
(Mass Spectrometry) ionization mode _{= ESI-: m / z = [} M-NH 4 + H-H] - 525
Exact Mass: 543

<Identification of Compound Represented by Formula (Ia5-SA2)>
(Mass Spectrometry) ionization mode _{_{= ESI-: m / z = [}} M-NH 4 -NH 4 + H + H-H] - 605
Exact Mass: 640

Example E-2
0.30 parts of the compound represented by formula (Ia1), 3.00 parts of chloroform and 0.55 parts of chlorosulfonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed.
The mixture was stirred for 3 hours, keeping at 60°C.
This mixture was added dropwise to 3.64 parts of ice.
The resulting mixture was filtered and the resulting residue was washed with water.
The residue was washed with methanol.
The residue was dried under reduced pressure at 60° C. to substitute --SO ₃ H for any one hydrogen atom of the compound represented by the formula (Ia1-SA1) (the compound represented by the formula (Ia1)). And a compound represented by the formula (Ia1-SA2) (a compound represented by the formula (Ia1) in which any one hydrogen atom is replaced by —SO ₂ Cl) 18 parts were obtained.

<Identification of Compound Represented by Formula (Ia1-SA1)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 497
Exact Mass: 498

<Identification of compound represented by formula (Ia1-SA2)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 515
Exact Mass: 516

Example E-3
1.00 parts of the compound represented by the formula (Ia2) and 20.6 parts of fuming sulfuric acid (30%) (manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.) were mixed at room temperature.
The mixture was stirred at room temperature for 3 hours.
This mixture was added dropwise to 208 parts of ice.
The resulting mixture was mixed with 110 parts of acetonitrile.
The mixture was filtered and the residue obtained was washed with acetonitrile.
This residue was dried under reduced pressure at 60° C. to replace —SO ₃ H with any one of two hydrogen atoms of the compound represented by the formula (Ia2-SA) (the compound represented by the formula (Ia2)). To obtain 0.40 part of a mixture containing the compound).

<Identification of Compound Represented by Formula (Ia2-SA)>
(Mass Spectrometry) ionization mode = ESI-: m / z = [ M-H] - 677
Exact Mass: 678

Synthesis example 1
An appropriate amount of nitrogen was flown into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80° C. with stirring. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^{2, 6} ] A mixed solution of 289 parts of a mixture of decan-9-yl acrylate (content ratio is 1:1 by molar ratio) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution of 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropping, the mixture was kept at 80° C. for 4 hours and then cooled to room temperature to obtain a solution of a copolymer (resin B1) having a solid content of 35.0%. The obtained resin B1 had a weight average molecular weight of 8,800, a dispersity of 2.1, and an acid value in terms of solid content of 80 mg-KOH/g.

Synthesis example 2
An appropriate amount of nitrogen was flown into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, 340 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80° C. with stirring. Then, 57 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^{2, 6} ] A mixed solution of 54 parts of a mixture of decan-9-yl acrylate (content ratio is 1:1 in molar ratio), 239 parts of benzyl methacrylate and 73 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution of 40 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 197 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropping, the mixture was kept at 80° C. for 3 hours and then cooled to room temperature to obtain a solution of a copolymer (resin B2) having a solid content of 36.8%. The weight average molecular weight of the obtained copolymer was 9,400, the dispersity was 1.89, and the acid value in terms of solid content was 114 mg-KOH/g.

Example 9
The respective components were mixed in the following proportions and the colorant was dispersed using a bead mill to obtain a coloring composition M1.
Coloring agent (A): 4.50 parts of a compound represented by the formula (Ia2);
Colorant (A): 0.500 part of the compound represented by formula (z);
Dispersant solution: DISPERBYK-161 (manufactured by Big Chemie Japan Co., Ltd.)
16.7 parts;
Resin (B): Resin B1 solution 11.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 46.9 parts;
Solvent (E): ethyl lactate 20.0 parts;

Then, the respective components were mixed in the following proportions to obtain a coloring composition 1.
Coloring composition M1 57.6 parts;
Resin (B): Resin B2 solution 27.0 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 15.4 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00630 parts;

The coloring composition 1 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film.
The film thickness of the obtained prebaked colored coating film was measured using DektakXT (manufactured by BRUKER).
The spectrum of this prebaked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table 39 shows the film thickness of this prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this prebaked colored coating film.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

Example 10
A colored composition was obtained in the same manner as in Example 9 except that the compound represented by the formula (Ia2) was replaced with the compound represented by the formula (Ia23). A film was obtained.
Table 39 shows the film thickness of this prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this prebaked colored coating film.

Example 11
The compound represented by the formula (Ia2) is the compound represented by the formula (Ia10) obtained in Example 4, the compound represented by the formula (Ia2143), the compound represented by the formula (Ia850) and the formula (Ia315). A colored composition was obtained in the same manner as in Example 9 except that the mixture of the compounds represented by (4) was used to obtain a pre-baked colored coating film and a post-baked colored coating film.
Table 39 shows the film thickness of this prebaked colored coating film and the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum of this prebaked colored coating film.

Example 12
A colored composition was obtained in the same manner as in Example 9 except that the compound represented by the formula (Ia2) was replaced with the compound represented by the formula (Ia35). A film was obtained.
Table 39 shows the film thickness of this prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this prebaked colored coating film.

Example 13
The respective components were mixed in the following proportions and the colorant was dispersed using a bead mill to obtain a coloring composition M2.
Coloring agent (A): 4.50 parts of a compound represented by formula (Ia1);
Colorant (A): 0.500 part of the compound represented by formula (z);
Dispersant solution: BYK-LPN6919 (manufactured by Big Chemie Japan Co., Ltd.)
8.33 parts;
Resin (B): Resin B1 solution 11.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 55.2 parts;
Solvent (E): ethyl lactate 20.0 parts;

Then, the respective components were mixed in the following proportions to obtain a coloring composition 2.
Coloring composition M2 57.6 parts;
Resin (B): Resin B2 solution 27.0 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 15.4 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00630 parts;

The coloring composition 2 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film.
The film thickness of the obtained prebaked colored coating film was measured using DektakXT (manufactured by BRUKER).
The spectrum of this prebaked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table 39 shows the film thickness of this prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this prebaked colored coating film.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

Example 14
The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M3.
Colorant (A): a compound represented by formula (Ia10) obtained in Example 4, a compound represented by formula (Ia2143), a compound represented by formula (Ia850) and a formula (Ia315). 5.00 parts of a mixture of compounds;
Dispersant solution: DISPERBYK-161 (manufactured by Big Chemie Japan Co., Ltd.)
16.7 parts;
Resin (B): Resin B1 solution 11.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 46.9 parts;
Solvent (E): ethyl lactate 20.0 parts;

Then, the respective components were mixed in the following proportions to obtain a coloring composition 3.
Coloring composition M3 57.6 parts;
Resin (B): Resin B2 solution 27.0 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 15.4 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00630 parts;

The coloring composition 3 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film.
The film thickness of the obtained prebaked colored coating film was measured using DektakXT (manufactured by BRUKER).
The spectrum of this prebaked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table 39 shows the film thickness of this prebaked colored coating film and the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum of this prebaked colored coating film.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

Example 15
A mixture of the compound represented by the formula (Ia10), the compound represented by the formula (Ia2143), the compound represented by the formula (Ia850) and the compound represented by the formula (Ia315) obtained in Example 4 was replaced with the compound represented by the formula: A colored composition was obtained in the same manner as in Example 14 except that the compound represented by (Ia33) was used to obtain a pre-baked colored coating film and a post-baked colored coating film.
Table 39 shows the film thickness of this prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this prebaked colored coating film.

Example 16
The respective components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M4.
Colorant (A): 4.50 parts of a compound represented by the formula (Ia22);
Colorant (A): 0.500 part of the compound represented by formula (z);
Dispersant solution: DISPERBYK-161 (manufactured by Big Chemie Japan Co., Ltd.)
16.7 parts;
Resin (B): Resin B1 solution 11.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 46.9 parts;
Solvent (E): ethyl lactate 20.0 parts;

Then, the respective components were mixed in the following proportions to obtain a coloring composition 4.
Coloring composition M4 48.0 parts;
Resin (B): Resin B2 solution 22.5 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 29.5 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00525 parts;

The coloring composition 4 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film.
The film thickness of the obtained prebaked colored coating film was measured using DektakXT (manufactured by BRUKER).
The spectrum of this prebaked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table 39 shows the film thickness of this prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this prebaked colored coating film.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

Comparative Example 1
The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M5.
Colorant (A): C.I. I. Pigment Yellow 138 12.0 parts;
Dispersant solids 4.21 parts;
Resin solids 5.05 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 74.8 parts;
Solvent (E): Propylene glycol monomethyl ether 3.94 parts;

Then, the respective components were mixed in the following proportions to obtain a coloring composition 5.
24.0 parts of coloring composition M5;
Resin (B): Resin B2 solution 35.0 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 41.0 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00630 parts;

The coloring composition 5 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film.
The film thickness of the obtained prebaked colored coating film was measured using DektakXT (manufactured by BRUKER).
The spectrum of this prebaked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table 39 shows the film thickness of this prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this prebaked colored coating film.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

Comparative example 2
The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M6.
Colorant (A): C.I. I. Pigment Yellow 138 4.50 parts;
Colorant (A): 0.500 part of the compound represented by formula (z);
Dispersant solution: DISPERBYK-161 (manufactured by Big Chemie Japan Co., Ltd.)
16.7 parts;
Resin (B): Resin B1 solution 11.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 46.9 parts;
Solvent (E): ethyl lactate 20.0 parts;

Then, the respective components were mixed in the following proportions to obtain a coloring composition 6.
Coloring composition M6 57.6 parts;
Resin (B): Resin B2 solution 27.0 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 15.4 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00630 parts;

The coloring composition 6 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film.
The film thickness of the obtained prebaked colored coating film was measured using DektakXT (manufactured by BRUKER).
The spectrum of this prebaked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table 39 shows the film thickness of this prebaked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this prebaked colored coating film.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

In Table 39,
The “AAA” column shows the maximum absorption wavelength on the longest wavelength side of the absorption spectrum,
The “BBB” column shows the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Example 17
The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M7.
Colorant (A): 5.00 parts of a mixture containing the compound represented by the formula (Ie12) obtained in Example 7;
Dispersant solution: DISPERBYK-161 (manufactured by Big Chemie Japan Co., Ltd.)
16.7 parts;
Resin (B): Resin B1 solution 11.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 46.9 parts;
Solvent (E): ethyl lactate 20.0 parts;

Then, the respective components were mixed in the following proportions to obtain a coloring composition 7.
Coloring composition M7 57.6 parts;
Resin (B): Resin B2 solution 27.0 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 15.4 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00630 parts;

The coloring composition 7 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.
The film thickness of the obtained post-baked colored coating film was measured using DektakXT (manufactured by BRUKER).
The spectrum of this post-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table 40 shows the film thickness of this post-baked colored coating film and the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum of this post-baked colored coating film.

Comparative Example 3
The respective components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M8.
Colorant (A): C.I. I. Pigment Yellow 138 12.0 parts;
Dispersant solids 4.21 parts;
Resin solids 5.05 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 74.8 parts;
Solvent (E): Propylene glycol monomethyl ether 3.94 parts;

Then, the respective components were mixed in the following proportions to obtain a coloring composition 8.
24.0 parts of coloring composition M8;
Resin (B): Resin B2 solution 35.0 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 41.0 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00630 parts;

The coloring composition 8 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.
The film thickness of the obtained post-baked colored coating film was measured using DektakXT (manufactured by BRUKER).
The spectrum of this post-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table 40 shows the film thickness of this post-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this post-baked colored coating film.

In Table 40,
The "CCC" column indicates the maximum absorption wavelength on the longest wavelength side of the absorption spectrum,
The “DDD” column shows the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Comparative Example 4
The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition MH4.
Colorant (A): C.I. I. Pigment Yellow 138 4.50 parts Colorant (A): compound represented by formula (z) 0.500 parts Dispersant solution: DISPERBYK-161 (manufactured by BYK Japan KK)
16.7 parts Resin (B): Resin B1 solution 11.4 parts Solvent (E): Propylene glycol monomethyl ether acetate 46.9 parts Solvent (E): Ethyl lactate 20.0 parts

Then, the respective components were mixed in the following proportions to obtain a coloring composition H4.
Coloring composition MH4 57.6 parts Resin (B): Resin B2 solution 27.0 parts
Solvent (E): Propylene glycol monomethyl ether acetate 15.4 parts Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00630 parts

The coloring composition H4 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film. The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film. The film thickness of the obtained post-baked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of this post-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table AD1 shows the film thickness of this post-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this post-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

In Tables AD1 to AD21,
The "EEE" column shows the maximum absorption wavelength on the longest wavelength side of the absorption spectrum,
The “FFF” column shows the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Example 6-1
The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M6-1.
Colorant (A): compound represented by formula (Ia51) 4.50 parts Colorant (A): compound represented by formula (z) 0.500 parts Dispersant solution: DISPERBYK-161 (Big Chemie Japan Co., Ltd. Made by company)
16.7 parts Resin (B): Resin B1 solution 11.4 parts Solvent (E): Propylene glycol monomethyl ether acetate 66.9 parts

Then, the respective components were mixed in the following proportions to obtain a colored composition 6-1.
Coloring composition M6-1 57.6 parts Resin (B): Resin B1 solution 28.4 parts
Solvent (E): Propylene glycol monomethyl ether acetate 14.0 parts Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00630 parts

The coloring composition 6-1 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film.
The film thickness of the obtained prebaked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of this prebaked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table AD2 shows the film thickness of this pre-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

Example 6-2 to Example 6-4
A colored composition was obtained in the same manner as in Example 6-1, except that the compound represented by the formula (Ia51) was replaced with the compound described in the column “Colorant AAA” in Table AD3, and prebaked coloring was performed. A coating film and a post-baked colored coating film were obtained.
Table AD3 shows the film thickness of this pre-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Example 7-1
The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M7-1.
Colorant (A): 4.50 parts of a compound represented by the formula (Ia973);
Colorant (A): 0.500 part of the compound represented by formula (z);
Dispersant solution: BYK-LPN6919 (manufactured by Big Chemie Japan Co., Ltd.)
8.33 parts;
Resin (B): Resin B1 solution 11.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 75.2 parts;

Then, the respective components were mixed in the following proportions to obtain a colored composition 7-1.
57.6 parts of Coloring composition M7-1;
Resin (B): Resin B1 solution 28.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 14.0 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00630 parts;

The coloring composition 7-1 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film.
The film thickness of the obtained prebaked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of this prebaked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table AD4 shows the film thickness of this pre-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

Example 7-2 to Example 7-6
A colored composition was obtained in the same manner as in Example 7-1, except that the compound represented by the formula (Ia973) was replaced with the compound described in the column “Colorant AAA” in Table AD5. A coating film and a post-baked colored coating film were obtained.
Table AD5 shows the film thickness of this pre-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Example 7-7
The respective components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M7-7.
Coloring agent (A): 4.50 parts of a compound represented by the formula (If2528);
Colorant (A): 0.500 part of the compound represented by formula (z);
Dispersant solution: BYK-LPN6919 (manufactured by Big Chemie Japan Co., Ltd.)
8.33 parts;
Resin (B): Resin B1 solution 11.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 75.2 parts;

Then, the respective components were mixed in the following proportions to obtain Colored Composition 7-7.
Coloring composition M7-7 57.6 parts;
Resin (B): Resin B1 solution 28.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 14.0 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00630 parts;

The coloring composition 7-7 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film. The film thickness of the obtained post-baked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of this post-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table AD6 shows the film thickness of this post-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this post-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Example 90-1
The respective components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M90-1.
Coloring agent (A): 4.00 parts of the compound represented by formula (Ia5);
Colorant (A): 1.00 part of the compound represented by formula (z);
Dispersant solution: BYK-LPN6919 (manufactured by Big Chemie Japan Co., Ltd.)
12.5 copies;
Resin (B): Resin B1 solution 11.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 71.1 parts;

Then, the respective components were mixed in the following proportions to obtain a coloring composition 90-1.
Coloring composition M90-1 57.6 parts;
Resin (B): Resin B1 solution 24.3 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 18.1 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00630 parts;

The coloring composition 90-1 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film. The film thickness of the obtained prebaked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of this prebaked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table AD7 shows the film thickness of this pre-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

Example 90-2 to Example 90-22
A coloring composition was obtained in the same manner as in Example 90-1 except that the compound represented by the formula (Ia5) was replaced with the compound described in the column “Colorant AAA” in Table AD8, and prebaked coloring was performed. A coating film and a post-baked colored coating film were obtained.
Table AD8 shows the film thickness of this pre-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Example 90-23
The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M90-23.
Colorant (A): 4.00 parts of a compound represented by the formula (If1904);
Colorant (A): 1.00 part of the compound represented by formula (z);
Dispersant solution: BYK-LPN6919 (manufactured by Big Chemie Japan Co., Ltd.)
12.5 copies;
Resin (B): Resin B1 solution 11.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 71.1 parts;

Then, the respective components were mixed in the following proportions to obtain a coloring composition 90-23.
Coloring composition M90-23 57.6 parts;
Resin (B): Resin B1 solution 24.3 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 18.1 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00630 parts;

The coloring composition 90-23 was applied on a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film. The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film. The film thickness of the obtained post-baked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of this post-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table AD9 shows the film thickness of this post-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this post-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Example 91-1
The respective components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M91-1.
Coloring agent (A): 4.00 parts of a compound represented by the formula (If3796);
Colorant (A): 1.00 part of the compound represented by formula (z);
Dispersant solution: BYK-LPN6919 (manufactured by Big Chemie Japan Co., Ltd.)
12.5 copies;
Resin (B): Resin B1 solution 11.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 71.1 parts;

Then, the respective components were mixed in the following proportions to obtain a coloring composition 91-1.
Coloring composition M91-1 51.2 parts;
Resin (B): Resin B1 solution 21.6 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 27.2 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00560 copies;

The coloring composition 91-1 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film. The film thickness of the obtained prebaked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of this prebaked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table AD10 shows the film thickness of this pre-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

Examples 91-2 to 91-4
A coloring composition was obtained in the same manner as in Example 91-1 except that the compound represented by the formula (If3796) was replaced with the compound described in the column of “Colorant AAA” in Table AD11, and prebaked coloring was performed. A coating film and a post-baked colored coating film were obtained.
Table AD11 shows the film thickness of this pre-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Example 17-1
The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M17-1.
Colorant (A): 3.89 parts of a mixture containing the compound represented by the formula (Ia1-SA1) obtained in Example E-2 and the compound represented by the formula (Ia1-SA2);
Colorant (A): 1.25 parts of the compound represented by formula (z);
Dispersant solution: BYK-LPN6919 (manufactured by Big Chemie Japan Co., Ltd.)
12.5 copies;
Resin (B): Resin B1 solution 11.5 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 70.9 parts;

Then, the respective components were mixed in the following proportions to obtain a colored composition 17-1.
Coloring composition M17-1 57.6 parts;
Resin (B): Resin B1 solution 24.3 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 18.1 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00629 copies;

The coloring composition 17-1 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film.
The film thickness of the obtained prebaked colored coating film was measured using DektakXT (manufactured by BRUKER).
The spectrum of this prebaked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table AD12 shows the film thickness of this pre-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

Example 12-1
The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M12-1.
Colorant (A): 3.80 parts of a compound represented by the formula (If1261);
Colorant (A): 1.20 parts of the compound represented by formula (z);
Dispersant solution: BYK-LPN6919 (manufactured by Big Chemie Japan Co., Ltd.)
12.5 copies;
Resin (B): Resin B1 solution 11.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 71.1 parts;

Then, the respective components were mixed in the following proportions to obtain a colored composition 12-1.
Coloring composition M12-1 57.6 parts;
Resin (B): Resin B1 solution 24.3 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 18.1 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00630 parts;

The coloring composition 12-1 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film. The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film. The film thickness of the obtained post-baked colored coating film was measured using DektakXT (manufactured by BRUKER).
The spectrum of this post-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table AD13 shows the film thickness of this post-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this post-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Example 13-1
The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M13-1.
Colorant (A): 5.01 parts of a compound represented by the formula (Ia728);
Dispersant solution: BYK-LPN6919 (manufactured by Big Chemie Japan Co., Ltd.)
12.5 copies;
Resin (B): Resin B1 solution 11.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 71.1 parts;

Then, the respective components were mixed in the following proportions to obtain a colored composition 13-1.
Coloring composition M13-1 57.4 parts;
Resin (B): Resin B1 solution 24.3 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 18.2 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00636 copies;

The coloring composition 13-1 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film. The film thickness of the obtained prebaked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of this prebaked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table AD14 shows the film thickness of this pre-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

Example 14-1
The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M14-1.
Coloring agent (A): 4.66 parts of a compound represented by the formula (Ia703);
Colorant (A): Compound represented by formula (z) 0.497 parts;
Dispersant solution: BYK-LPN6919 (manufactured by Big Chemie Japan Co., Ltd.)
12.5 copies;
Resin (B): Resin B1 solution 11.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 70.9 parts;

Then, the respective components were mixed in the following proportions to obtain a colored composition 14-1.
Coloring composition M14-1 55.5 parts;
Resin (B): Resin B1 solution 24.9 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 19.6 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00635 parts;

The coloring composition 14-1 was applied on a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film. The film thickness of the obtained prebaked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of this prebaked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table AD15 shows the film thickness of this pre-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

Example 16-1
The respective components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M16-1.
Colorant (A): 4.13 parts of a compound represented by the formula (It242);
Colorant (A): compound represented by formula (z) 0.916 parts;
Dispersant solution: BYK-LPN6919 (manufactured by Big Chemie Japan Co., Ltd.)
12.4 parts;
Resin (B): Resin B1 solution 11.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 71.1 parts;

Then, the respective components were mixed in the following proportions to obtain a colored composition 16-1.
Coloring composition M16-1 57.8 parts;
Resin (B): Resin B1 solution 24.1 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 18.1 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00628 parts;

The coloring composition 16-1 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film. The film thickness of the obtained prebaked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of this prebaked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table AD16 shows the film thickness of this pre-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

Example 51-1
The respective components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M51-1.
Coloring agent (A): 2.25 parts of the compound represented by formula (Ia2);
Coloring agent (A): 2.25 parts of the compound represented by formula (Ia5);
Colorant (A): 0.500 part of the compound represented by formula (z);
Dispersant solution: DISPERBYK-161 (manufactured by Big Chemie Japan Co., Ltd.)
16.7 parts;
Resin (B): Resin B1 solution 11.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 46.9 parts;
Solvent (E): ethyl lactate 20.0 parts;

Then, the respective components were mixed in the following proportions to obtain a colored composition 51-1.
Coloring composition M51-1 57.6 parts;
Resin (B): Resin B1 solution 28.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 14.0 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00630 parts;

The coloring composition 51-1 was applied on a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film. The film thickness of the obtained prebaked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of this prebaked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table AD17 shows the film thickness of this pre-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

Example 571-1
The respective components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M571-1.
Coloring agent (A): 2.25 parts of the compound represented by formula (Ia1);
Coloring agent (A): 2.25 parts of the compound represented by formula (Ia5);
Colorant (A): 0.500 part of the compound represented by formula (z);
Dispersant solution: BYK-LPN6919 (manufactured by Big Chemie Japan Co., Ltd.)
8.33 parts;
Resin (B): Resin B1 solution 10.0 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 76.7 parts;

Then, the respective components were mixed in the following proportions to obtain a coloring composition 571-1.
Coloring composition M571-1 57.6 parts;
Resin (B): Resin B1 solution 29.2 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 13.2 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00630 parts;

The coloring composition 571-1 was applied on a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by a spin coating method, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film. The film thickness of the obtained prebaked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of this prebaked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table AD18 shows the film thickness of this pre-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

Example 591-1
The respective components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M591-1.
Coloring agent (A): 2.25 parts of the compound represented by formula (Ia1);
Coloring agent (A): 2.25 parts of the compound represented by formula (Ia248);
Colorant (A): 0.500 part of the compound represented by formula (z);
Dispersant solution: BYK-LPN6919 (manufactured by Big Chemie Japan Co., Ltd.)
12.5 copies;
Resin (B): Resin B1 solution 11.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 71.1 parts;

Then, the respective components were mixed in the following proportions to obtain a coloring composition 591-1.
Coloring composition M591-1 57.6 parts;
Resin (B): Resin B1 solution 24.3 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 18.1 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00630 parts;

The coloring composition 591-1 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film. The film thickness of the obtained prebaked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of this prebaked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table AD19 shows the film thickness of this pre-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

Example 591-2
Example 591-, except that the following colorant (A) is used in the following amounts in place of the compound represented by formula (Ia1) and the compound represented by formula (Ia248) in Example 591-1. A colored composition was obtained in the same manner as in 1 to obtain a pre-baked colored coating film and a post-baked colored coating film.
Colorant (A): a compound represented by the formula (Ia10) obtained in Example 4, a compound represented by the formula (Ia2143), a compound represented by the formula (Ia850) and a formula (Ia315). 2.38 parts of a mixture of compounds;
Colorant (A): 2.12 parts of the compound represented by the formula (Ia51);
Table AD19 shows the film thickness of this pre-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Example 591-3
Example 591-, except that the following colorant (A) is used in the following amounts in place of the compound represented by formula (Ia1) and the compound represented by formula (Ia248) in Example 591-1. A colored composition was obtained in the same manner as in 1 to obtain a pre-baked colored coating film and a post-baked colored coating film.
Colorant (A): 2.38 parts of a compound represented by the formula (Ia248);
Colorant (A): 2.12 parts of the compound represented by the formula (Ia51);
Table AD19 shows the film thickness of this pre-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Example 591-4
Example 591-, except that the following colorant (A) is used in the following amounts in place of the compound represented by formula (Ia1) and the compound represented by formula (Ia248) in Example 591-1. A colored composition was obtained in the same manner as in 1 to obtain a pre-baked colored coating film and a post-baked colored coating film.
Coloring agent (A): 2.64 parts of the compound represented by formula (Ia23);
Colorant (A): 1.86 parts of a compound represented by the formula (Ia17);
Table AD19 shows the film thickness of this pre-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Example 591-5
Example 591-, except that the following colorant (A) was used in the following amounts in place of the compound represented by formula (Ia1) and the compound represented by formula (Ia248) in Example 591-1. A colored composition was obtained in the same manner as in 1 to obtain a pre-baked colored coating film and a post-baked colored coating film.
Colorant (A): 2.17 parts of a compound represented by the formula (Ia19);
Colorant (A): 2.33 parts of the compound represented by formula (Ia17);
Table AD19 shows the film thickness of this pre-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Example 592-1
The components were mixed in the following proportions, and the colorant was dispersed using a bead mill to obtain a coloring composition M592-1.
Colorant (A): 4.00 parts of the compound represented by the formula (Ia1);
Colorant (A): 1.00 part of the compound represented by formula (Ia248);
Dispersant solution: BYK-LPN6919 (manufactured by Big Chemie Japan Co., Ltd.)
12.5 copies;
Resin (B): Resin B1 solution 11.4 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 71.1 parts;

Then, the respective components were mixed in the following proportions to obtain a coloring composition 592-1.
Coloring composition M592-1 57.6 parts;
Resin (B): Resin B1 solution 24.3 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 18.1 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00630 parts;

The coloring composition 592-1 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film. The film thickness of the obtained prebaked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of this prebaked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table AD20 shows the film thickness of this pre-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

Example 592-2
Example 592-Except that the following colorant (A) is used in the following amounts in place of the compound represented by formula (Ia1) and the compound represented by formula (Ia248) in Example 592-1. A colored composition was obtained in the same manner as in 1 to obtain a pre-baked colored coating film and a post-baked colored coating film.
Coloring agent (A): 4.00 parts of the compound represented by formula (Ia5);
Colorant (A): 1.00 part of the compound represented by formula (Ia248);
Table AD20 shows the film thickness of this pre-baked colored coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Example 592-3
Example 592-Using the following amounts of colorants (A) in place of the compound represented by formula (Ia1) and the compound represented by formula (Ia248) in Example 592-1. A colored composition was obtained in the same manner as in 1 to obtain a pre-baked colored coating film and a post-baked colored coating film.
Colorant (A): 4.00 parts of a compound represented by the formula (Ia699);
Colorant (A): 1.00 part of the compound represented by formula (Ia248);
Table AD20 shows the film thickness of this pre-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Example 592-4
Example 592-Using the following amounts of colorants (A) in place of the compound represented by formula (Ia1) and the compound represented by formula (Ia248) in Example 592-1. A colored composition was obtained in the same manner as in 1 to obtain a pre-baked colored coating film and a post-baked colored coating film.
Coloring agent (A): 4.00 parts of the compound represented by formula (Ia5);
Colorant (A): 1.00 parts of a mixture containing the compound of the formula (Ia5-SA1) and the compound of the formula (Ia5-SA2) obtained in Example E-1;
Table AD20 shows the film thickness of this pre-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Example S-1
The respective components were mixed in the following proportions to obtain a coloring composition S-1.
Colorant (A): 2.92 parts of a mixture containing the compound represented by the formula (Ia5-SA1) obtained in Example E-1 and the compound represented by the formula (Ia5-SA2), and N-methylpyrrolidone 97 1 part mixture 51.4 parts;
Resin (B): Resin B1 solution 38.5 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 10.1 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00531 copies;

The coloring composition S-1 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.
The film thickness of the obtained post-baked colored coating film was measured using DektakXT (manufactured by BRUKER).
The spectrum of this post-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table AD21 shows the film thickness of this post-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this post-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Example S-2 The respective components were mixed in the following proportions to obtain a coloring composition S-2.
Colorant (A): Mixture of 1.00 parts of the compound represented by the formula (If5670) and 99.0 parts of N-methylpyrrolidone 59.2 parts;
Resin (B): Resin B1 solution 40.5 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 0.278 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00514 copies;

The coloring composition S-2 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film. The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film. The film thickness of the obtained post-baked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of this post-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table AD21 shows the film thickness of this post-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this post-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Example S-3
The respective components were mixed in the following proportions to obtain a coloring composition S-3.
Colorant (A): 2.24 parts of a mixture containing the compound represented by the formula (Ia2-SA) obtained in Example E-3;
Resin (B): Resin B1 solution 33.6 parts;
Solvent (E): Propylene glycol monomethyl ether acetate 0.581 parts;
Solvent (E): N-methylpyrrolidone 63.6 parts;
Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.)
0.00490 parts;

The coloring composition S-3 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes to form a prebaked colored coating film.
The film thickness of the obtained prebaked colored coating film was measured using DektakXT (manufactured by BRUKER).
The spectrum of this prebaked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda Vision Co., Ltd.).
Table AD21 shows the film thickness of this pre-baked colored coating film, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of this pre-baked colored coating film, or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.
The pre-baked colored coating film was post-baked at 230° C. for 30 minutes to obtain a post-baked colored coating film.

From the above results, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the colored coating film formed from the coloring composition containing the compound of the present invention or the shoulder peak wavelength on the longest wavelength side of the absorption spectrum is C.I. I. It was found that the wavelength was longer than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the colored coating film formed from the coloring composition containing Pigment Yellow 138.

The coloring composition and compound of the present invention are C.I. I. Pigment Yellow 138 can be used to form a color filter having a darker color than that of the coloring composition containing Pigment Yellow 138, and thus is suitably used for a color filter or a display device such as a liquid crystal display device.

Claims

A coloring composition comprising a compound represented by the following formula (I) and a solvent.

[In the formula (I),
R 1 to R 5 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, —SO 3 M, —CO 2 M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms or a carbon atom. Represents a monovalent heterocyclic group of the numbers 1 to 40,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
—CH 2 — constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with —O—, —S—, —S(O) 2 — or —CO—,
The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, —SO 3 M, —CO 2 M or MM.
R 1 and R 2 , R 2 and R 3 , and R 3 and R 4 may be bonded to each other to form a ring.
M represents a hydrogen atom, an alkali metal atom, a metal atom which may have a ligand, or N(Z 1 )(Z 2 )(Z 3 )(Z 4 ).
MM represents an alkali metal atom, a metal atom which may have a ligand, or N(Z 1 )(Z 2 )(Z 3 )(Z 4 ).
Z 1 to Z 4 each independently represent a hydrogen atom, a monovalent hydrocarbon group having 1 to 40 carbon atoms or a monovalent heterocyclic group having 1 to 40 carbon atoms,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
—CH 2 — constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with —O—, —S—, —S(O) 2 — or —CO—,
The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, —SO 3 M, —CO 2 M or MM.
Q 1 and Q 2 each independently represent a divalent hydrocarbon group or a divalent heterocyclic group,
-C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N=,
—CH 2 — constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with —O—, —S—, —S(O) 2 — or —CO—,
The hydrogen atom constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, —SO 3 M, —CO 2 M or MM.
When there are a plurality of Z 1 to Z 4 , M and MM, they may be the same or different from each other. ]
The colored composition according to claim 1, which contains a resin.
The coloring composition according to any one of claims 1 to 2, which contains a polymerizable compound and a polymerization initiator.
A color filter formed of the coloring composition according to any one of claims 1 to 3.
A display device including the color filter according to claim 4.
A compound represented by formula (I).

[In the formula (I),
R 1 to R 5 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, —SO 3 M, —CO 2 M, MM, a monovalent hydrocarbon group having 1 to 40 carbon atoms or a carbon atom. Represents a monovalent heterocyclic group of the numbers 1 to 40,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
—CH 2 — constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with —O—, —S—, —S(O) 2 — or —CO—,
The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, —SO 3 M, —CO 2 M or MM.
R 1 and R 2 , R 2 and R 3 , and R 3 and R 4 may be bonded to each other to form a ring.
M represents a hydrogen atom, an alkali metal atom, a metal atom which may have a ligand, or N(Z 1 )(Z 2 )(Z 3 )(Z 4 ).
MM represents an alkali metal atom, a metal atom which may have a ligand, or N(Z 1 )(Z 2 )(Z 3 )(Z 4 ).
Z 1 to Z 4 each independently represent a hydrogen atom, a monovalent hydrocarbon group having 1 to 40 carbon atoms or a monovalent heterocyclic group having 1 to 40 carbon atoms,
-C(-)(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with -N=,
—CH 2 — constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with —O—, —S—, —S(O) 2 — or —CO—,
The hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, —SO 3 M, —CO 2 M or MM.
Q 1 and Q 2 each independently represent a divalent hydrocarbon group or a divalent heterocyclic group,
-C(-)(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -Si(-)(-)-,
-CH(-)- constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N(-)-,
-CH= constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with -N=,
—CH 2 — constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with —O—, —S—, —S(O) 2 — or —CO—,
The hydrogen atom constituting the divalent hydrocarbon group and the divalent heterocyclic group may be replaced with a halogen atom, a cyano group, a nitro group, —SO 3 M, —CO 2 M or MM.
When there are a plurality of Z 1 to Z 4 , M and MM, they may be the same or different from each other. ]