TWI851660B - Coloring composition, compound, color filter and display device - Google Patents

Abstract

The object of the present invention is to provide a coloring composition comprising: a compound having a maximum absorption wavelength on the longest wavelength side of the absorption spectrum at a longer wavelength than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the previously known CI Pigment Yellow 138, and/or a compound having a wavelength of a shoulder peak on the longest wavelength side of the absorption spectrum. The present invention relates to a coloring composition comprising 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, a compound, a color filter and a display device.

The coloring composition can be used to manufacture color filters used in display devices such as liquid crystal display devices and electroluminescent display devices. As a coloring agent contained in the coloring composition, C.I. Pigment Yellow 138 is known (Patent Document 1).

(C.I. Pigment Yellow 138)

[Prior art literature]

[Patent Literature]

[Patent document 1] Japanese Patent Publication No. 2013-82906

In recent years, the development of display devices for expanding the color reproduction area that can be displayed has been advancing, and as one of the links, color filters are also required to have richer colors. In order to meet this requirement, the following coloring composition is required, which includes: a compound having a maximum absorption wavelength on the longest wavelength side of the absorption spectrum at a longer wavelength than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the previously known C.I. Pigment Yellow 138, and/or a compound having a wavelength of a shoulder peak on the longest wavelength side of the absorption spectrum.

The wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum refers to: for a compound, when there is no maximum absorption wavelength on the longest wavelength side of the absorption spectrum on a wavelength side longer than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of C.I. Pigment Yellow 138, and when there are two or more inflection points of the absorption spectrum on a wavelength side longer than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum, the wavelength is the average value of the wavelength of the inflection point on the longest wavelength side of the absorption spectrum and the wavelength of the inflection point on the second longest wavelength side of the absorption spectrum.

The present invention provides the following [1]~[6].

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

[Chemistry 2]

[In formula (I), R ¹ to R ⁵ independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N=; -CH ₂ - constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) ₂ -or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by 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 independently represent a hydrogen atom, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N=; -CH ₂ - constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) ₂ - or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by 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 alkyl group or a divalent heterocyclic group, -C(-)(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N=, and -CH ₂ - constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -O-, -S-, -S(O) ₂ - or -CO-, the hydrogen atom constituting the divalent alkyl group and the divalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; when there are plural Z ¹ to Z ⁴ , M and MM, they may be the same or different from each other]

[2] The coloring composition as described in [1], which contains a resin.

[3] A coloring composition as described in any one of [1] to [2], comprising a polymerizable compound and a polymerization initiator.

[4] A color filter formed from a coloring composition as described in any one of [1] to [3].

[5] A display device comprising the color filter described in [4].

[6] A compound represented by formula (I).

[In formula (I), R ¹ to R ⁵ independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N=; -CH ₂ - constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) ₂ -or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by 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 independently represent a hydrogen atom, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N=; -CH ₂ - constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) ₂ - or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by 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 alkyl group or a divalent heterocyclic group, -C(-)(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N=, -CH ₂ - may also be substituted with -O-, -S-, -S(O) ₂ - or -CO-, and the hydrogen atoms constituting the divalent alkyl group and the divalent heterocyclic group may also be substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; when there are multiple Z ¹ to Z ⁴ , M and MM, they may be the same or different from each other]

According to the present invention, a coloring composition and a compound are provided that can be used in the formation of a color filter having a darker color than a coloring composition containing C.I. Pigment Yellow 138.

[Coloring composition]

The coloring composition of the present invention comprises: a compound represented by formula (I) (hereinafter, sometimes referred to as compound (I)) and a solvent (hereinafter, sometimes referred to as solvent (E)).

[Chemistry 4]

[In formula (I), R ¹ to R ⁵ independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N=; -CH ₂ - constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) ₂ -or -CO-, the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may be substituted 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 independently represent a hydrogen atom, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -N=; -CH ₂ - constituting the monovalent alkyl group or the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) ₂ - or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by 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 alkyl group or a divalent heterocyclic group, -C(-)(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N=, and -CH ₂ - constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -O-, -S-, -S(O) ₂ - or -CO-, the hydrogen atom constituting the divalent alkyl group and the divalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; when there are plural Z ¹ to Z ⁴ , M and MM, they may be the same or different from each other]

Compound (I) also includes its tautomers or their salts.

Compound (I) can be used as a coloring agent.

The coloring composition of the present invention may contain one or more compounds (I).

The coloring composition of the present invention may also contain a resin (hereinafter referred to as resin (B)).

The coloring composition of the present invention may also contain a polymerizable compound (hereinafter referred to as a polymerizable compound (C)).

The coloring composition of the present invention may also contain a polymerization initiator (hereinafter referred to as a polymerization initiator (D)).

The coloring composition of the present invention may also contain a polymerization initiator (hereinafter referred to as a polymerization initiator (D1)).

The coloring composition of the present invention may also contain a coloring agent other than compound (I) (hereinafter, sometimes referred to as coloring agent (A1); and, hereinafter, sometimes compound (I) and coloring agent (A1) are collectively referred to as "coloring agent (A)").

The coloring agent (A1) may contain one or more coloring agents.

The colorant (A1) preferably includes one or more selected from yellow colorants, orange colorants, red colorants, and green colorants.

The coloring composition of the present invention may also contain a leveling agent (hereinafter, sometimes referred to as a leveling agent (F)).

The coloring composition of the present invention may also contain an antioxidant (hereinafter referred to as antioxidant (G)).

[Compound (I)]

The following lists partial structures of compound (I) to more specifically illustrate the present invention. In each partial structure, even if the substituent bonded to the ring structure is illustrated as being bonded to any one part of the ring structure, the following examples also include the state where the substituent is bonded to all parts of the ring structure. One or more substituents may be bonded to the ring structure. When two or more substituents are bonded to the ring structure, the substituents may be the same or different.

As the halogen atom, there can be listed: fluorine atom, chlorine atom, bromine atom and iodine atom, etc., preferably fluorine atom, chlorine atom and bromine atom.

The carbon number of the alkyl group represented by R ¹ to R ⁵ and Z ¹ to Z ⁴ is 1 to 40, preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 18, and particularly preferably 1 to 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 aliphatic hydrocarbon group may be saturated or unsaturated and may be chain-like or cyclic (alicyclic hydrocarbon group).

Examples of the saturated or unsaturated chain alkyl groups represented by ^R1 to ^R5 and ^Z1 to ^Z4 include linear chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, trineicosyl, dotriacontyl, trictriacontyl, tetratriacontyl, pentatriacontyl, hexatriacontyl, heptatriacontyl, octatriacontyl, nonacosyl, triacontyl, trineicosyl, dotriacontyl, trictriacontyl, tetratriacontyl, pentatriacontyl, hexatriacontyl, heptatriacontyl, octatriacontyl, nonacosyl and tetracontyl; linear chain alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, 2-ethylbutyl, 3,3- Dimethylbutyl, 1,1,3,3-tetramethylbutyl, 1-methylbutyl, 1-ethylpropyl, 3-methylbutyl, neopentyl, 1,1-dimethylpropyl, 2-methylpentyl, 3-ethylpentyl, 1,3-dimethylbutyl, 2-propylpentyl, 1-ethyl-1,2-dimethylpropyl, 1-methylpentyl, 4-methylpentyl, 4-methylhexyl, 5-methylhexyl, 2-ethylhexyl, 1-methylhexyl, 1-ethylpentyl, 1-propylbutyl, 3-ethylheptyl, 2,2-dimethylheptyl, 1-methylheptyl, branched chain alkyl groups such as 1-ethylhexyl, 1-propylpentyl, 1-methyloctyl, 1-ethylheptyl, 1-propylhexyl, 1-butylpentyl, 1-methylnonyl, 1-ethyloctyl, 1-propylheptyl and 1-butylhexyl; ethenyl (vinyl), propenyl (e.g., 1-propenyl, 2-propenyl (allyl)), 1-methylvinyl, butenyl (e.g., 1-butenyl, 2-butenyl, 3-butenyl), 3-methyl-1-butenyl, 1,3-butadienyl, 1 -(2-propenyl)vinyl, 1-(1-methylvinyl)vinyl, 1,2-dimethyl-1-propenyl, pentenyl (e.g., 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl), 1-(1,1-dimethylethyl)vinyl, 1,3-dimethyl-1-butenyl, hexenyl (e.g., 1-hexenyl, 5-hexenyl), heptenyl (e.g., 1-heptenyl, 6-heptenyl), octenyl (e.g., 1-octenyl, 7-octenyl), nonenyl (e.g., 1-nonenyl, 8-nonenyl), Alkenyl groups such as 1-decenyl, 2-decenyl, 1-hexenyl, 2-hexenyl, 3-decenyl, 4-decenyl, 5-decenyl, 6-decenyl, 7-decenyl, 8-decenyl, 10-decenyl, 15-decenyl, 16-decenyl, 17-decenyl, 18-decenyl, 10 ... The carbon number of the saturated or unsaturated chain alkyl group is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 18, and particularly preferably 1 to 12. Among them, a linear or branched chain alkyl group having 1 to 12 carbon atoms is particularly preferred.

Examples of the saturated or unsaturated alicyclic alkyl groups represented by ^R1 to ^R5 and ^Z1 to ^Z4 include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethylcyclohexyl, 1,4-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 3,4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl, 3, cycloalkyl groups such as 3-dimethylcyclohexyl, 4,4-dimethylcyclohexyl, cyclooctyl, 2,4,6-trimethylcyclohexyl, 2,2,6,6-tetramethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (for example, cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, cyclohex-3-en-1-yl), cycloheptenyl and cyclooctenyl; saturated or unsaturated polycyclic alkyl groups such as norbornyl, norbornenyl, adamantyl and bicyclo[2.2.2]octyl, and the like. The carbon number of the saturated or unsaturated alicyclic alkyl group is preferably 3 to 30, more preferably 3 to 20, further preferably 3 to 18, and particularly preferably 3 to 12. Among them, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and adamantyl are particularly preferred.

基及芘基等芳香族烴基等。芳香族烴基的碳數較佳為6~30，更佳為6~20，進而佳為6~18，尤佳為6~12。 Examples of the aromatic hydrocarbon group represented by ^R1 to ^R5 and ^Z1 to ^Z4 include phenyl, o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, o-t-butylphenyl, m-t-butylphenyl, p-t-butylphenyl, 3,5-di(t-butyl)phenyl, 3,5-di(t-butyl)-4-methylphenyl, 4-butylphenyl, 4-pentylphenyl, 2, 6-bis(1-methylethyl)phenyl, 2,4,6-tris(1-methylethyl)phenyl, 4-cyclohexylphenyl, 2,4,6-trimethylphenyl, 4-octylphenyl, 4-(1,1,3,3-tetramethylbutyl)phenyl, 1-naphthyl, 2-naphthyl, 6-methyl-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8-tetrahydro-2-naphthyl, fluorenyl, phenanthrenyl, anthracenyl, 2-dodecylphenyl, 3-dodecylphenyl, 4-dodecylphenyl, peryl,

The number of carbon atoms in the aromatic alkyl group is preferably 6 to 30, more preferably 6 to 20, further preferably 6 to 18, and particularly preferably 6 to 12.

The alkyl group represented by ^R1 to ^R5 and ^Z1 to ^Z4 may be a group formed by combining the alkyl groups listed above (for example, an aromatic alkyl group, and at least one of a chain alkyl group and an alicyclic alkyl group), and examples thereof include benzyl, (2-methylphenyl)methyl, (3-methylphenyl)methyl, (4-methylphenyl)methyl, (2-ethylphenyl)methyl, (3-ethylphenyl)methyl, (4-ethylphenyl)methyl, (2-(tert-butyl)phenyl)methyl, (3-(tert-butyl)phenyl)methyl, (4-(tert-butyl)phenyl)methyl, (3,5-dimethylphenyl)methyl, 1-phenylethyl, 1,1-diphenylethyl, phenethyl, 1-methyl-1-phenylethyl, (1-naphthyl)methyl, and (2-naphthyl)methyl; aralkyl groups such as 1-phenylethenyl, 2-phenylethenyl (phenylethenyl), ... arylalkenyl groups such as phenylethynyl and the like; phenyl groups having one or more phenyl groups bonded thereto such as biphenyl and terphenyl; cyclohexylmethylphenyl, benzylphenyl, and (dimethyl(phenyl)methyl)phenyl, 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 ^R1 to ^R5 and ^Z1 to ^Z4 may be groups formed by combining the above-mentioned alkyl groups (e.g., chain alkyl groups and alicyclic alkyl groups), for example, alkyl groups bonded to one or more alicyclic alkyl groups such as cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl, (2-methylcyclohexyl)methyl, cyclohexylethyl and adamantylmethyl.

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 refers to a group containing a hetero atom as a ring constituent. The monovalent heterocyclic group having 1 to 40 carbon atoms may be a monocyclic group or a polycyclic group. Examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom.

The carbon number of the heterocyclic group is preferably 3 to 30, more preferably 3 to 20, further preferably 3 to 18, and particularly preferably 3 to 12.

Examples of heterocyclic rings containing nitrogen atoms include aziridine, azetidine, pyrrolidine, piperidine, and piperazine; pyrroles such as pyrrole, 1-methylpyrrole, and 2,5-dimethylpyrrole; pyrazoles such as pyrazole, 1-methylpyrrole, 2-methylpyrrole, 3-methylpyrazole, 4-methylpyrazole, and 5-methylpyrazole; imidazole, 1,2,3-triazole, and 1,2,4-triazole; and unsaturated heterocyclic rings such as pyridine, pyrazine, Pyrimidine, 6-methylpyrimidine and other pyrimidines, pyrazine and 1,3,5-triazine and other six-membered unsaturated heterocyclic rings; indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydro(3-methyl)quinoxaline, 3-methylquinoxaline and other quinoxalines, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, benzopiperidine and other condensed tricyclic heterocyclic rings such as carbazole, acridine and phenanthrazine, etc.

Examples of the heterocyclic ring containing an oxygen atom include: monocyclic saturated heterocyclic rings such as cyclopropane, cyclobutane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane and 1,4-dioxane, 1-cyclopentyldioxacyclopentane, 2-cyclopentyldioxacyclopentane; bicyclic saturated heterocyclic rings such as 1,4-dioxaspiro[4.5]decane, 1,4-dioxaspiro[4.5]nonane, 1,4-dioxaspiro[4.4]nonane; α-acetone, β-propiolactone, γ-butyrolactone, γ-valerolactone and δ-valerolactone; esters and other lactone heterocyclic rings; furan, 2,3-dimethylfuran, 2,5-dimethylfuran and other furan and other five-membered unsaturated heterocyclic rings; 2H-pyran, 4H-pyran and other six-membered unsaturated heterocyclic rings; 1-benzofuran and other benzofurans, benzopyran, 4-methylbenzopyran and other benzopyrans, benzodioxole, 1,3-benzodioxole, benzodioxane, chromane and isochromane and other condensed bicyclic heterocyclic rings; oxanthracene, dibenzofuran and other condensed tricyclic heterocyclic rings, etc.

Examples of heterocyclic rings containing sulfur atoms include: five-membered saturated heterocyclic rings such as dithiolane; six-membered saturated heterocyclic rings such as thioane, 1,3-dithiane, and 2-methyl-1,3-dithiane; five-membered unsaturated heterocyclic rings such as thiophene, 3-methylthiophene, and 2-carboxythiophene; 2H-thiopyran, 4H-thiopyran; condensed bicyclic heterocyclic rings such as benzothiopyran, benzotetrahydrothiopyran, and benzothiophene; and condensed tricyclic heterocyclic rings such as thianthrene and dibenzothiophene.

Examples of heterocyclic rings containing nitrogen atoms and oxygen atoms include: monocyclic saturated heterocyclic rings 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 heterocyclic rings such as oxazole, 4-methyloxazole, and isoxazoles such as 2-methylisoxazole, 3-methylisoxazole, 4-methylisoxazole, and 5-methylisoxazole; condensed bicyclic heterocyclic rings such as benzoxazole, benzoisoxazole, benzoxazine, benzodioxane, and benzimidazolinone; condensed tricyclic heterocyclic rings such as phenoxazine, and the like.

Examples of heterocyclic rings containing nitrogen atoms and sulfur atoms include monocyclic heterocyclic rings such as thiazole, 2-methylthiazole, 3-methylthiazole, 4-methylthiazole, 5-methylthiazole, 2,4-dimethylthiazole, etc.; condensed bicyclic heterocyclic rings such as benzothiazole, etc.; condensed tricyclic heterocyclic rings such as phenothiazine, etc.

Furthermore, the bonding position of the heterocyclic group is the part from which any hydrogen atom contained in each heterocyclic ring is detached.

The heterocyclic group may also be a group formed by combining the above-mentioned heterocyclic group and the above-mentioned alkyl group, for example, tetrahydrofuranylmethyl group may be listed.

Furthermore, the heterocyclic group may also be represented by the following formula. ※ represents a bond.

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

For example, there can be mentioned: trichloromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 2,2-dibromoethyl, 2,2,3,3-tetrafluoropropyl, 2-ethoxyethyl, 2-butoxyethyl, 2-nitropropyl, diethylaminoethyl, (4-methoxyphenyl)methyl, (2-methoxyphenyl)methyl, (3-methoxyphenyl)methyl, (4-nitrophenyl)methyl, (2,4-dichlorophenyl)methyl, (4-fluorophenyl)methyl, (3,5-difluorophenyl)methyl, 2,2,2-trifluoro-1-trifluoromethyl-1-phenylethyl, (phenoxy)(phenyl)methyl, (benzyloxy)(phenyl)methyl, pyrrolylmethyl, pyrrolylethyl, (4-aminophenyl)methyl, (4-cyanophenyl)methyl, 2-hydroxy-1-methyl-1-phenylethyl, 2-chloro-1-methyl-1-phenylethyl; -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 ₂ O) ₁₁ CH ₃ , -(CH ₂ CH ₂ O) ₁₂ CH ₃ , -(CH ₂ CH ₂ O) ₁₃ CH ₃ , and an alkyl group having a substituent such as a group in which -CH ₂ - of the above-mentioned monovalent hydrocarbon group or monovalent heterocyclic group is replaced by -O- (hereinafter, these may be referred to as groups of group A).

For example, there can be listed: 4-bromophenyl, 4-nitrophenyl, 4-methoxyphenyl, 2,4-dichlorophenyl, pentafluorophenyl, 2-aminophenyl, 2-methyl-4-chlorophenyl, 4-hydroxy-1-naphthyl, 4,5,8-trichloro-2-naphthyl, anthraquinone, 2-aminoanthraquinone and other aryl groups having substituents (hereinafter, these may be referred to as groups of group B).

For example, there can be mentioned: formyl, acetyl, propionyl, butyryl, 2,2-dimethylpropionyl, pentyl, hexyl, 2-ethylhexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, heneicosyl, benzoyl,

and a carbonyl group bonded to the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group, preferably a carbonyl group bonded to a hydrocarbon group with 1 to 30 carbon atoms, a group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group, and more preferably a carbonyl group bonded to a hydrocarbon group with 1 to 20 carbon atoms, a group A to group B or the monovalent hydrocarbon group Preferably, the carbonyl group is a carbonyl group of a preferred 1-valent alkyl group or a monovalent heterocyclic group, and more preferably, the carbonyl group is bonded to a alkyl group having 1 to 18 carbon atoms, a group of the above group A to group B, or a preferred 1-valent alkyl group or a monovalent heterocyclic group, and more preferably, the carbonyl group is bonded to a alkyl group having 1 to 12 carbon atoms, a group of the above group A to group B, or a preferred 1-valent alkyl group or a monovalent heterocyclic group.

※Indicates key binding.

For example, there can be mentioned methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethylhexyl)oxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, phenyloxycarbonyl, eicosyloxycarbonyl,

and an oxycarbonyl group bonded to the group A to group B or the monovalent alkyl group or the monovalent heterocyclic group, preferably an oxycarbonyl group bonded to a alkyl group with 1 to 30 carbon atoms, a group A to group B or the monovalent alkyl group or the monovalent heterocyclic group, and more preferably an oxycarbonyl group bonded to a alkyl group with 1 to 20 carbon atoms, a group A to group B or the monovalent An oxycarbonyl group of a preferred alkyl group or a monovalent heterocyclic group, further preferably an oxycarbonyl group bonded to a alkyl group having 1 to 18 carbon atoms, a group of the above group A to group B, or a preferred alkyl group or a monovalent heterocyclic group, and particularly preferably an oxycarbonyl group bonded to a alkyl group having 1 to 12 carbon atoms, a group of the above group A to group B, or a preferred alkyl group or a monovalent heterocyclic group.

※Indicates key binding.

For example, the following can be cited: formyloxy, acetyloxy, propionyloxy, butyryloxy, (2,2-dimethylpropionyl)oxy, pentyloxy, hexyloxy, (2-ethylhexyl)oxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, heneicosyloxy, benzyloxy, vinylcarbonyloxy, (2-propenyl)carbonyloxy, (1-methylvinyl)carbonyloxy, and carbonyloxy groups bonded to the groups A to B or the monovalent alkyl or monovalent heterocyclic groups, preferably bonded to A carbonyloxy group having a carbon number of 1 to 30, a group of the above group A to group B, or a preferred monovalent carbon group or monovalent heterocyclic group, more preferably a carbonyloxy group having a carbon number of 1 to 20, a group of the above group A to group B, or a preferred monovalent carbon group or monovalent heterocyclic group, further preferably a carbonyloxy group having a carbon number of 1 to 18, a group of the above group A to group B, or a preferred monovalent carbon group or monovalent heterocyclic group, and particularly preferably a carbonyloxy group having a carbon number of 1 to 12, a group of the above group A to group B, or a preferred monovalent carbon group or monovalent heterocyclic group.

For example, there can be mentioned: hydroxyl; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, t-butoxy, pentyloxy, neopentyloxy, 1-ethyl-1,2-dimethylpropoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, (2-ethylhexyl)oxy, stearyloxy, eicosyloxy, 1-phenylethoxy, 1-methyl-1-phenylethoxy, phenyloxy, benzyloxy, 2,3-dimethylphenyloxy, 2,4-dimethylphenyloxy, 2,5-dimethylphenyloxy, 2,6-dimethylphenyloxy, 3,4-dimethylphenyloxy , 3,5-dimethylphenyloxy, 2,3-dicyanophenyloxy, 2,4-dicyanophenyloxy, 2,5-dicyanophenyloxy, 2,6-dicyanophenyloxy, 3,4-dicyanophenyloxy, 3,5-dicyanophenyloxy, 4-methoxyphenyloxy, 2-methoxyphenyloxy, 3-methoxyphenyloxy, 4-ethoxyphenyloxy, 2-ethoxyphenyloxy, 3-ethoxyphenyloxy; trichloromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 2,2,3,3-tetrafluoropropoxy, 3,3,3-trifluoro-2-trifluoromethyl-2-methylpropoxy, 2-butoxyethoxy, 2-nitropropoxy, -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 , [Chemical 8]

[Chemistry 9]

and an oxy group bonded to the group A to group B or the monovalent alkyl group or the monovalent heterocyclic group, preferably an oxy group or a hydroxy group bonded to a alkyl group having 1 to 30 carbon atoms, a group A to group B or the monovalent alkyl group or the monovalent heterocyclic group, and more preferably a alkyl group having 1 to 20 carbon atoms, a group A to group B or the monovalent alkyl group or the monovalent heterocyclic group. Preferably, it is an oxy or hydroxyl group of a preferred monovalent heterocyclic group, and preferably, it is an oxy or hydroxyl group bonded to a alkyl group having 1 to 18 carbon atoms, a group of the above group A to group B, or a preferred monovalent alkyl group or monovalent heterocyclic group, and more preferably, it is an oxy or hydroxyl group bonded to a alkyl group having 1 to 12 carbon atoms, a group of the above group A to group B, or a preferred monovalent alkyl group or monovalent heterocyclic group.

※Indicates key binding.

For example, there can be mentioned: thio; methylthio, ethylthio, propylthio, butylthio, t-butylthio, pentylthio, hexylthio, (2-ethylhexyl)thio, heptylthio, octylthio, nonylthio, decylthio, undecylthio, dodecylthio, eicosylthio, phenylthio, o-tolylthio,

and a alkyl radical formed by replacing a hydrogen atom with a group of the group A to group B or a monovalent hydrocarbon group or a monovalent heterocyclic group, etc., preferably a alkyl radical formed by replacing a hydrogen atom with a alkyl radical having 1 to 30 carbon atoms, a group of the group A to group B or a monovalent hydrocarbon group or a monovalent heterocyclic group, or a alkyl radical, and more preferably a alkyl radical formed by replacing a hydrogen atom with a alkyl radical having 1 to 20 carbon atoms, a group of the group A to group B or a monovalent hydrocarbon group or a monovalent heterocyclic group. A alkyl group or alkyl group formed by a preferred monovalent heterocyclic group, further preferably a alkyl group or alkyl group formed by replacing a hydrogen atom with a carbon number of 1 to 18 alkyl group, a group of the above group A to group B, or a preferred monovalent alkyl group or monovalent heterocyclic group, and particularly preferably a alkyl group or alkyl group formed by replacing a hydrogen atom with a carbon number of 1 to 12 alkyl group, a group of the above group A to group B, or a preferred monovalent alkyl group or monovalent heterocyclic group.

※Indicates key binding.

For example, there can be mentioned methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2-ethylhexyl)sulfonyl, heptylsulfonyl, octylsulfonyl, nonylsulfonyl, decylsulfonyl, undecylsulfonyl, dodecylsulfonyl, eicosylsulfonyl, phenylsulfonyl, p-tolylsulfonyl,

and a sulfonyl group bonded to the group A~group B or the monovalent hydrocarbon group or the monovalent heterocyclic group, etc., preferably a sulfonyl group bonded to a hydrocarbon group with 1 to 30 carbon atoms, a group A~group B or the monovalent hydrocarbon group or the monovalent heterocyclic group, more preferably a sulfonyl group bonded to a hydrocarbon group with 1 to 20 carbon atoms, a group A~group B or the monovalent hydrocarbon group A sulfonyl group of a preferred alkyl group or a monovalent heterocyclic group, further preferably a sulfonyl group bonded to a alkyl group having 1 to 18 carbon atoms, a group of the above group A to group B, or a sulfonyl group of a preferred monovalent alkyl group or a monovalent heterocyclic group, and particularly preferably a sulfonyl group bonded to a alkyl group having 1 to 12 carbon atoms, a group of the above group A to group B, or a sulfonyl group of a preferred monovalent alkyl group or a monovalent heterocyclic group.

※Indicates key binding.

For example, there can be mentioned: sulfonylamine; N-methylsulfonylamine, N-ethylsulfonylamine, N-propylsulfonylamine, N-isopropylsulfonylamine, N-butylsulfonylamine, N-isobutylsulfonylamine, N-(sec-butyl)sulfonylamine, N-(tert-butyl)sulfonylamine, N-pentylsulfonylamine, N-(1-ethylpropylsulfonylamine, N-isopropyl ...(1-butylpropylsulfonylamine, N-isobutylpropylsulfonylamine, N-(1-butylpropylsulfonylamine, N-isobutylpropylsulfonylamine, N-(2-butylpropylsulfonylamine, N-isobutylpropylsulfonylamine, N-(2-butylpropylsulfonylamine, N-isobutylpropylsulfonylamine, N-(2-butylpropylsulfonylamine, N-isobutylpropylsulfonylamine, N-(2-butylpropylsulfonylamine, N-isobutylpropylsulfonylamine, N-(2-butylpropylsulfonylamine, N-isobutylpropylsulfonylamine, N-(2-butylpropylsulfonylamine, N-isobutylpropylsulfonylamine, N-(2-butylpropylsulfonylamine, amine sulfonyl, N-hexylamine sulfonyl, N-(2-ethylhexyl)amine sulfonyl, N-heptylamine sulfonyl, N-octylamine sulfonyl, N-nonylamine sulfonyl, N-decylamine sulfonyl, N-undecylamine sulfonyl, N-dodecylamine sulfonyl, N-eicosylamine sulfonyl, N-phenylamine sulfonyl, -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 an aminosulfonyl group substituted with a group of the above-mentioned group A to group B or one of the above-mentioned monovalent hydrocarbon groups or monovalent heterocyclic groups; N,N-dimethylaminosulfonyl group, N-ethyl-N-methylaminosulfonyl group, N,N- Diethylamine sulfonyl, N-propyl-N-methylamine sulfonyl, N,N-dipropylamine sulfonyl, N-isopropyl-N-methylamine sulfonyl, N,N-diisopropylamine sulfonyl, N,N-diisobutylamine sulfonyl, N,N-di(sec-butyl)amine sulfonyl, N-(tert-butyl)-N-methylamine sulfonyl, N,N-di(tert-butyl)amine sulfonyl, N-butyl-N- Methylamine sulfonyl, N,N-dibutylamine sulfonyl, N-butyl-N-octylamine sulfonyl, N,N-diamylamine sulfonyl, N,N-bis(1-ethylpropyl)amine sulfonyl, N-butyl-N-hexylamine sulfonyl, N-hexyl-N-methylamine sulfonyl, N,N-dihexylamine sulfonyl, N-(2-ethylhexyl)-N-methylamine sulfonyl, N,N-bis(2-ethylhexyl)-N-methylamine sulfonyl N,N-dihexyl)amine sulfonyl, N,N-diheptylamine sulfonyl, N-octyl-N-methylamine sulfonyl, N,N-dioctylamine sulfonyl, N,N-dinonylamine sulfonyl, N-decyl-N-methylamine sulfonyl, N-undecyl-N-methylamine sulfonyl, N-dodecyl-N-methylamine sulfonyl, N-eicosyl-N-methylamine sulfonyl, N-phenyl-N-methylamine sulfonyl The sulfonyl group is preferably an acyl group, an N,N-diphenylamine sulfonyl group, and an amine sulfonyl group formed by replacing two of the groups selected from the above group A to group B, the monovalent alkyl group and the monovalent heterocyclic group, preferably an amine sulfonyl group formed by replacing one or two of the groups selected from the above group A to group B, the monovalent alkyl group and the monovalent heterocyclic group, -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ or an amine sulfonyl group, more preferably an amine sulfonyl group substituted with one or two selected from a alkyl group having 1 to 20 carbon atoms, a group of the aforementioned group A to group B, a preferred monovalent alkyl group, and a preferred monovalent heterocyclic group, -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ or an amine sulfonyl group, further preferably an amine sulfonyl group substituted with one or two selected from a alkyl group having 1 to 18 carbon atoms, a group of the aforementioned group A to group B, a preferred monovalent alkyl group, and a preferred monovalent heterocyclic group, -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) 2 ₂ or sulfonamide, particularly preferably sulfonamide substituted with one or two selected from a alkyl group having 1 to 12 carbon atoms, a group of Group A to Group B, a preferred monovalent alkyl group and a preferred monovalent heterocyclic group, -SO ₂ NH(CH ₂ ) ₂ N(CH ₂ CH ₃ ) ₂ or sulfonamide.

For example, the following may be mentioned: aminoformyl; N-methylaminoformyl, N-ethylaminoformyl, N-propylaminoformyl, N-isopropylaminoformyl, N-butylaminoformyl, N-isobutylaminoformyl, N-(sec-butyl)aminoformyl, N-(tert-butyl)aminoformyl, N-pentylaminoformyl, N-(1-ethylpropyl)aminoformyl, methylaminoformyl, N-hexylaminoformyl, N-(2-ethylhexyl)aminoformyl, N-heptylaminoformyl, N-octylaminoformyl, N-nonylaminoformyl, N-decylaminoformyl, N-undecylaminoformyl, N-dodecylaminoformyl, N-eicosylaminoformyl, N-phenylaminoformyl, -CONH(CH ₂ ) ₂ N(CH ₂ CH 3 ) ₂ , -CONHCH 2 CH ₂ CH _{2 Si} (OCH _{2 CH 3 ) 3} , and aminoformyl groups substituted with the groups A to B or with one of the monovalent alkyl groups or monovalent heterocyclic groups; N,N-dimethylaminoformyl, N-ethyl-N-methylaminoformyl, N,N-diethylaminoformyl, N-propyl-N-methylaminoformyl, N,N-dipropylaminoformyl, N-isopropyl-N-methylaminoformyl, N,N-diisopropylaminoformyl, N,N-diisobutylaminoformyl, N,N-di(sec-butyl)aminoformyl, N-(tert-butyl)-N-methylaminoformyl, N,N-di(tert-butyl)aminoformyl; N-butyl-N-methylaminoformyl, N,N-dibutylaminoformyl, N-butyl-N-octylaminoformyl, N,N-dipentylaminoformyl, N,N-bis(1-ethylpropyl)aminoformyl, N-butyl-N-hexylaminoformyl, N-hexyl-N-methylaminoformyl, N,N-dihexylaminoformyl, N-(2-ethylhexyl)-N-methylaminoformyl, N,N-bis(2-ethylhexyl)aminoformyl, N,N-diheptylaminoformyl, N-octyl-N-methylaminoformyl, N,N-dioctylaminoformyl, N,N-dinonyl The present invention is preferably an aminoformyl group selected from the group A to the group B, an aminoformyl group in which two of the monovalent alkyl groups and the monovalent heterocyclic groups are substituted, and preferably one or two of the alkyl groups having 1 to 30 carbon atoms, the group selected from the group A to the group B, the preferred monovalent alkyl groups and the preferred monovalent heterocyclic groups are substituted. The aminoformyl group or aminoformyl group is preferably substituted with one or two selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a group of the group A to the group B, a preferred monovalent alkyl group, and a preferred monovalent heterocyclic group. The aminoformyl group or aminoformyl group is further preferably substituted with one or two selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, a group of the group A to the group B, a preferred monovalent alkyl group, and a preferred monovalent heterocyclic group. The aminoformyl group or aminoformyl group is particularly preferably substituted with one or two selected from the group consisting of an alkyl group having 1 to 12 carbon atoms, a group of the group A to the group B, A carbamoyl group in which one or both of the preferred monovalent alkyl group and the preferred monovalent heterocyclic group are substituted, or a carbamoyl group.

For example, the amino groups include: amino; N-methylamino, N-ethylamino, N-propylamino, N-isopropylamino, N-butylamino, N-isobutylamino, N-(sec-butyl)amino, N-(tert-butyl)amino, N-pentylamino, N-(1-ethylpropyl)amino, N-hexylamino, N-(2-ethylhexyl)amino, N-heptylamino, N-octylamino, N-nonylamino, N-decylamino, N-undecylamino, N-dodecylamino, N-eicosylamino, N-phenylamino, and amino groups substituted with the groups A to B or with one of the monovalent alkyl groups or monovalent heterocyclic groups; N,N-dimethylamino, N-ethylamino, N-pentylamino, N-(1-ethylpropyl)amino, N-hexylamino, N-(2-ethylhexyl)amino, N-heptylamino, N-octylamino, N-nonylamino, N-decylamino, N-undecylamino, N-dodecylamino, N-eicosylamino, N-phenylamino, and amino groups substituted with the groups A to B or with the monovalent alkyl groups or monovalent heterocyclic groups; N,N-diethylamine, N-propyl-N-methylamine, N,N-dipropylamine, N-isopropyl-N-methylamine, N,N-diisopropylamine, N,N-diisobutylamine, N,N-di(sec-butyl)amine, N-(tert-butyl)-N-methylamine, N,N-di(tert-butyl)amine, N-butyl-N-methylamine, N,N-dibutylamine, N-butyl-N-octylamine, N,N-dipentylamine, N,N-bis(1-ethylpropyl)amine, N-butyl-N-hexylamine, N-hexyl-N-methylamine, N,N-dihexylamine, N-(2-ethylhexyl)-N-methylamine , N,N-bis(2-ethylhexyl)amine, N,N-diheptylamine, N-octyl-N-methylamine, N,N-dioctylamine, N,N-dinonylamine, N-decyl-N-methylamine, N-undecyl-N-methylamine, N-dodecyl-N-methylamine, N-eicosyl-N-methylamine, N-phenyl-N-methylamine, N,N-diphenylamine, and amino groups substituted with two of the groups A to B, the monovalent alkyl groups, and the monovalent heterocyclic groups, etc., preferably alkyl groups having 1 to 30 carbon atoms, groups A to B, the preferred monovalent alkyl groups, and the preferred monovalent heterocyclic groups An amine group or an amine group substituted with one or two of them, more preferably an amine group or an amine group substituted with one or two of them selected from a alkyl group having 1 to 20 carbon atoms, a group of the group A to the group B, a preferred monovalent alkyl group and a preferred monovalent heterocyclic group, further preferably an alkyl group having 1 to 18 carbon atoms, a group of the group A to the group B The amine group or amine group is substituted by one or two of the preferred monovalent hydrocarbon group and the preferred monovalent heterocyclic group, and is particularly preferably an amine group or amine group substituted by one or two of the preferred monovalent hydrocarbon group and the preferred monovalent heterocyclic group.

For example, the following can be cited: formylamino, acetylamino, propionylamino, butyrylamino, (2,2-dimethylpropionyl)amino, pentylamino, hexylamino, (2-ethylhexyl)amino, heptylamino, octylamino, nonylamino, decylamino, undecylamino, dodecylamino, heneicosylamino, benzylamino, [Chemical 12]

and a carbonylamino group bonded to the group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group, preferably a carbonylamino group bonded to a hydrocarbon group having 1 to 30 carbon atoms, a group A to group B or the monovalent hydrocarbon group or the monovalent heterocyclic group, and more preferably a carbonylamino group bonded to a hydrocarbon group having 1 to 20 carbon atoms, a group A to group B or the monovalent hydrocarbon group Preferably, it is a carbonylamino group that is bonded to a alkyl group having 1 to 18 carbon atoms, a group of the above group A to group B, or a carbonylamino group that is a preferred monovalent alkyl group or a monovalent heterocyclic group, and more preferably, it is a carbonylamino group that is bonded to a alkyl group having 1 to 12 carbon atoms, a group of the above group A to group B, or a carbonylamino group that is a preferred monovalent alkyl group or a monovalent heterocyclic group.

※Indicates key binding.

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 CH3) 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 a group selected from Group A to Group B, -SiH ₃ , etc.; -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 by one, two or three of the groups selected from the groups A to B, the monovalent hydrocarbon groups and the monovalent heterocyclic groups; etc.; -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 by one, two or three of the groups selected from Group A to Group B, the monovalent hydrocarbon group and the monovalent heterocyclic group, etc. ; -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 substituted with one, two or three of the groups selected from Group A and Group B, the monovalent hydrocarbon group and the monovalent heterocyclic group (OH), etc., preferably a alkyl group having 1 to 30 carbon atoms, a group of Group A to Group B, a preferred monovalent alkyl group, and a preferred monovalent heterocyclic group -SiH ₃ , -Si(OH) ₃ , -SiH(OH) ₂ and -SiH ₂ (OH), or -Si(OH) ₃ substituted with one, two or three of them; more preferably is one or two selected from a alkyl group having 1 to 20 carbon atoms, a group of Group A to Group B, a preferred monovalent alkyl group, and a preferred monovalent heterocyclic group; or three substituted -SiH ₃ , -Si(OH) ₃ , -SiH(OH) ₂ and -SiH ₂ (OH), or -Si(OH) ₃ , and preferably one selected from a alkyl group having 1 to 18 carbon atoms, a group of Group A to Group B, a preferred monovalent alkyl group, and a preferred monovalent heterocyclic group , -SiH ₃ , -Si(OH) ₃ , -SiH(OH) ₂ and -SiH ₂ (OH), or -Si(OH) ₃ substituted with two or three of them, preferably selected from carbon One, two or three of the alkyl groups of 1 to 12, the groups of Group A to Group B, the preferred monovalent alkyl groups and the preferred monovalent heterocyclic groups are selected. -SiH ₃ , -Si(OH) ₃ , -SiH(OH) ₂ , -SiH ₂ (OH), or -Si(OH) ₃ substituted.

For example, the o-xylylimidomethyl group (C ₆ H ₄ (CO) ₂ N—CH ₂ —) which may have a substituent can be exemplified, and as the substituent, at least one selected from the group consisting of the halogen atom, the group of Group A to Group B, the monovalent hydrocarbon group, and the monovalent heterocyclic group can be exemplified.

As other bases, we can cite: -SCOCH ₃ ,

wait.

※Indicates key binding.

The monovalent alkyl group or the monovalent heterocyclic group may be substituted by -SO ₃ ^- N ⁺ (C ₁₂ H ₂₅ )(CH ₃ ) ₃ , -CO ₂ ^- N ⁺ (C ₁₂ H ₂₅ )(CH ₃ ) ₃ , -SO ₃ ^- , -CO ₂ ^- or the like.

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

As the metal atom which may have a ligand represented by M and MM, metal atoms belonging to Group 2 to Group 15 of the periodic table of elements can be listed. As the metal atom which may have a ligand, Mg, Ca, Sr, Ba, Cd, Ni, Zn, Cu, Hg, Fe, Co, Sn, Pb, Mn, Al, Cr, Rh, Ir, Pd, Ti, Zr, Hf, Si, Ge are more preferred, Mg, Ca, Sr, Ba, Ni, Zn, Cu, Fe, Co, Sn, Mn, Al, Cr are further preferred, and Mg, Ca, Sr, Ba, Ni, Zn, Cu, Fe, Co, Mn, Al, Cr are particularly preferred.

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, etc. The ligand coordinated to the metal atom and the carbon atom, nitrogen atom, oxygen atom or sulfur atom contained in the same ligand may be coordinated to the same metal atom. In the metal atom, a plurality of different ligands may be coordinated to the same metal atom, and may form an oligomer or a polymer.

In the ligand, when the compound (I) contains a metal atom that can have a ligand, the compound (I) may be obtained by removing the metal atom that can have a ligand.

The compound (I) of the present invention also contains such oligomers or polymers.

Among them, the charge of compound (I) is 0.

Examples of such compounds (I) include metal salts represented by the following formulas (EN1) to (EN5).

Among them, in formula (EN1) to formula (EN5), the structure represented by ( ) indicates repeated bonding like oligomers and polymers.

For example, the metal salt represented by formula (EN1) indicates that the same ligand is coordinated to the same metal atom.

For example, the metal salts represented by formula (EN2) to (EN3) represent multiple different ligands coordinated to the same metal atom to form oligomers.

For example, the metal salts represented by formula (EN4) to (EN5) represent multiple different ligands coordinated to the same metal atom to form oligomers or polymers.

[Chemistry 17]

Examples of N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ) represented by M and MM include NH ₄ ; a group formed by replacing NH 4 with an alkyl group, such as NH ₃ ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), and NH ₃ ((CH ₂ ) ₁₇ CH ₃ ); a group formed by replacing NH ₄ with four alkyl groups, such as 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 , and N(CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) _{2 4} substituted; and NH ₄ substituted by one, two, three or four of the groups selected from Group A to Group B, the monovalent hydrocarbon group and the monovalent heterocyclic group.

M is preferably: a hydrogen atom; an 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, Ni which may have a ligand, Zn which may have a ligand, Cu which may have a ligand, Fe which may have a ligand, Co which may have a ligand, Sn which may have a ligand, Mn which may have a ligand, Al which may have a ligand _, Cr which may have a ligand; _NH4 ; a group in which _NH4 is substituted with an alkyl group such as _NH3 (( _CH2 ) _7CH3 ), _NH3 (( _CH2 ) _11CH3 ) _{, NH3} (( _{CH2 ) 17CH3 )} ; N( _CH3 ) _{3 (} ( _CH2 ) _15CH3 ), N( _CH3 ) ₃ (( _CH2 ) _11CH3 ), N(CH ₃ ) ₂ ((CH ₂ ) ₁₁ CH ₃ ) ₂ , N(CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) ₂ , etc., which are substituted with NH ₄ by four alkyl groups, and more preferably: a hydrogen atom; a sodium atom, a 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, Ni which may have a ligand, Zn which may have a ligand, Cu which may have a ligand, Fe which may have a ligand, Co which may have a ligand, Mn which may have a ligand, Al which may have a ligand, Cr which may have a ligand; NH ₄ ; NH ₃ ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), NH ₃ ((CH ₂ ) ₁₇ CH ₃ ) or a group formed by replacing NH ₄ with one alkyl group such as 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 , or N(CH ₃ ) ₂ ((CH ₂ ) _{17 CH 3} ) ₂ .

MM is preferably: an 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, Ni which may have a ligand, Zn which may have a ligand, Cu which may have a ligand, Fe which may have a ligand, Co which may have a ligand, Sn which may have a ligand, Mn which may _have a ligand, Al which may have a ligand, Cr which may have a ligand; _NH4 ; a group formed by replacing _NH4 with an alkyl group such as _NH3 (( _CH2 ) _7CH3 ), _NH3 (( _CH2 ) _{11CH3 )} , _NH3 (( _{CH2 ) 17CH3} ); N( _CH3 ) _{3 (} (CH2) _15CH3 ), N( _CH3 ) ₃ ( _{( CH2 ) 11CH3} ), N(CH ₃ ) ₂ ((CH ₂ ) ₁₁ CH ₃ ) ₂ , N(CH ₃ ) ₂ ((CH ₂ ) ₁₇ CH ₃ ) ₂ , etc., which are preferably: a _sodium atom, a 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, Ni which may have a ligand, Zn which may have a ligand, Cu which may have a ligand, Fe which may have a ligand, Co which may have a ligand, Mn which may have a ligand, Al which may have a ligand, Cr which may have a ligand; NH ₄ ; NH ₃ ((CH ₂ ) ₇ CH ₃ ), NH ₃ ((CH ₂ ) ₁₁ CH ₃ ), NH ₃ ((CH ₂ ) ₁₇ CH ₃ ) or a group formed by replacing NH ₄ with one alkyl group such as 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 , or N(CH ₃ ) ₂ ((CH ₂ ) _{17 CH 3} ) ₂ .

^Q1 and ^Q2 each independently represent a divalent alkyl group or a divalent heterocyclic group, -C(-)(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -N=, _-CH2- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by -O-, -S-, -S(O) _2- or -CO-, and the hydrogen atom constituting the divalent alkyl group and the divalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, _-SO3M , _-CO2 M or MM.

The group substituting the hydrogen atom constituting the divalent alkyl group and the divalent heterocyclic group is preferably a halogen atom, a cyano group, a nitro group, -SO ₃ H, or -CO ₂ H.

^Q1 and ^Q2 may be the same or different, but are preferably the same.

^Q1 and ^Q2 are preferably groups represented by formula (QQ1) to formula (QQ19).

[Chemistry 19]

[Chemistry 20]

[In formula (QQ1) to formula (QQ19), R ^Q1 to R ^Q94 independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, MM, a monovalent alkyl group having 1 to 40 carbon atoms, or a monovalent heterocyclic group having 1 to 40 carbon atoms; -C(-)(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-; -CH(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N(-)-; -CH= constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N=; -CH ₂ - constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) ₂ - or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted 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 selected from R ^Q1 to R ^Q94 to form a ring; M and MM have the same meanings as described above; ※ indicates a bond] For R ^Q1 to R The monovalent alkyl group having 1 to 40 carbon atoms or the monovalent heterocyclic group having 1 to 40 carbon atoms represented by ^Q94 , wherein -C(-)(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N=, -CH ₂ - constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -O-, -S-, -S(O) ₂ - or -CO-, and the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by a halogen atom, a cyano group, a nitro group, or -SO ₃ The group of M, -CO ₂ M or MM may be a monovalent alkyl 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 , wherein -C(-)(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -Si(-)(-)-, -CH(-)- constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N(-)-, -CH= constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -N=, and -CH ₂ - constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted by -O-, -S-, or -S(O) ₂ - or -CO-, the hydrogen atom constituting the monovalent alkyl group and the monovalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or the same group as MM.

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

Regarding ^Q1 and ^Q2 , groups represented by formula (QQ1) to (QQ12) are preferred, groups represented by formula (QQ1) to (QQ5) are more preferred, groups represented by formula (QQ1) to (QQ4) are further preferred, groups represented by formula (QQ1) and (QQ2) are particularly preferred, and groups represented by formula (QQ2) are further preferred.

As the formula (QQ1) to the formula (QQ19), for example, the following formulas (Qa1) to (Qa50); formula (Qb1) to (Qb27); formula (Qc1) to (Qc56); formula (Qd1) to (Qd41); formula (Qe1) to (Qe16); formula (Qf1) to (Qf15); formula (Qg1) to (Qg40); formula (Qh1) to (Qh40); formula (Qj1) to (Qj29); formula (Qk1) to (Qk22); formula (Qm1) ~Formula (Qm20); Formula (Qn1)~Formula (Qn16); Formula (Qo1)~Formula (Qo15); Formula (Qp1)~Formula (Qp83); Formula (Qq1)~Formula (Qq72); Formula (Qr1)~Formula (Qr17); Formula (Qs1)~Formula (Qs26); Formula (Qt1)~Formula (Qt26); Formula (Qu1)~Formula (Qu17); Formula (Qv1)~Formula (Qv26); Formula (Qx1)~Formula (Qx2); and the bases represented by Formula (Qy1)~Formula (Qy10). Among them, ※ indicates a bond.

[Chemistry 21]

[Chemistry 22]

[Chemistry 23]

[Chemistry 24]

[Chemistry 25]

[Chemistry 27]

[Chemistry 29]

[Chemistry 31]

[Chemistry 33]

[Chemistry 39]

[Chemistry 41]

[Chemistry 42]

[Chemistry 46]

[Chemistry 48]

[Chemistry 50]

[Chemistry 51]

[Chemistry 52]

[Chemistry 53]

[Chemistry 54]

[Chemistry 55]

[Chemistry 56]

[Chemistry 57]

[Chemistry 58]

[Chemistry 60]

As compound (I), for example, compounds represented by formula (Ia) shown in Tables 1 to 14 below or their alkali metal salts can be listed.

In addition, the symbols recorded in the "Q ¹ " column and the "Q ² " column in Tables 1 to 14 respectively correspond to the groups represented by the above formulas.

※Indicates key binding.

[Table 2]

[Table 3]

[Table 4]

[Table 5]

[Table 6]

[Table 7]

[Table 8]

[Table 9]

[Table 10]

[Table 11]

[Table 12]

[Table 13]

[Table 14]

As compound (I), for example, compounds represented by formula (Ib) shown in Tables 15 to 31 below or alkali metal salts thereof can be listed.

[Chemistry 62]

In formula (Ib), any one of R ^Ib1 to R ^Ib5 is a substituent other than a hydrogen atom (hereinafter referred to as an RR group in some cases), and the other four are hydrogen atoms.

The symbols recorded 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 recorded in the "RR" column in Tables 15 to 31 represent RR groups, and correspond to the following formulas (a1) to (a69); formulas (b1) to (b4); formulas (c1) to (c4); formulas (d1) to (d5); formulas (e1) to (e20); formulas (f1) to (f5); formulas (g1) to (g9); formulas (h1) to (h9); formulas (j1) to (j9); formulas (k1) to (k4); formulas (m1) to (m9); For the groups represented by formula (n1) to (n3); formula (o1) to (o5); formula (p1) to (p23); formula (q1) to (q26); formula (r1) to (r26); and formula (s1) to (s26), the values recorded in the "No" column in Tables 15 to 31 respectively indicate the positions where the RR group replaces R ^Ib1 , "1" indicates that the RR group replaces R ^Ib2 , "3" indicates that the RR group replaces R ^Ib3 , "4" indicates that the RR group replaces R ^Ib4 , and "5" indicates that the RR group replaces R ^Ib5 .

※Indicates key binding.

[Table 15]

[Table 16]

[Table 17]

[Table 18]

[Table 19]

[Table 20]

[Table 21]

[Table 22]

[Table 23]

[Table 24]

[Table 25]

[Table 26]

[Table 27]

[Table 28]

[Table 29]

[Table 30]

[Table 31]

[Chemistry 63]

[Chemistry 64]

[Chemistry 65]

[Chemistry 66]

[Chemistry 67]

[Chemistry 70]

[Chemistry 71]

As compound (I), for example, compounds represented by formula (If) shown in the following Table f1 to Table f44 or their alkali metal salts can be listed.

Furthermore, the symbols recorded in the "Q ¹ " column and the "Q ² " column in Tables f1 to f44 respectively correspond to the groups represented by the above formulas.

※Indicates key binding.

[Table f1]

[Table f2]

[Table f3]

[Table f4]

[Table f5]

[Table f6]

[Table f7]

[Table f8]

[Table f9]

[Table f10]

[Table f11]

[Table f12]

[Table f13]

[Table f14]

[Table f15]

[Table f16]

[Table f17]

[Table f18]

[Table f19]

[Table f20]

[Table f21]

[Table f22]

[Table f23]

[Table f24]

[Table f25]

[Table f26]

[Table f27]

[Table f28]

[Table f29]

[Table f30]

[Table f31]

[Table f32]

[Table f33]

[Table f34]

[Table f35]

[Table f36]

[Table f37]

[Table f38]

[Table f39]

[Table f40]

[Table f41]

[Table f42]

[Table f43]

[Table f44]

As compound (I), for example, compounds represented by formula (It) shown in Table t1 to Table t5 below, compounds represented by formula (Iu) shown in Table u1 to Table u11 below, and alkali metal salts thereof can be listed.

Furthermore, the symbols recorded in the "aq" column, "Q ¹ " column, "Q ² " column and "Q ^u+1 " column in Tables t1 to t5 and Tables u1 to u11 correspond to the groups represented by the above formulas and the groups represented by the following formulas (aq1) to (aq36), respectively.

The "Q ^u+1 " column in Tables u1 to u11 indicates that the group represented by Q ¹ and the group represented by Q ² in the compound represented by formula (Iu) are groups corresponding to the symbols described in the "Q ^u+1 " column.

In the groups represented by the following formulae (aq1) to (aq36), # represents a bond with ^Q1 , and & represents a bond with ^Q2 .

[Chemistry 75]

[Chemistry 76]

[Chemistry 77]

[Table t1]

[Table t2]

[Table t3]

[Table t4]

[Table t5]

[Table u1]

[Table u2]

[Table u3]

[Table u4]

[Table u5]

[Table u6]

[Table u7]

[Table u8]

[Table u9]

[Table u10]

[Table u11]

Examples of compound (I) include compounds represented by formula (Ia1) to (Ia2216) and (Ib1) to (Ib1312), compounds represented by formula (If1) to (If13090), compounds represented by formula (It1) to (It900), and compounds represented by formula (Iu1) to (Iu3238) in which a group selected from -SO ₃ H, -CO _{2 H} , -SO 3 NH ₄ , -CO ₂ NH ₄ , -SO ₂ NH ₂ , -CONH ₂ , phthalimidomethyl (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 ), a compound containing one or more of a fluorine atom, a chlorine atom and a bromine atom.

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

As such compounds, for example, compounds in which all hydrogen atoms of the aromatic rings represented by formula (Ic1) to formula (Ic12) are substituted with one or more atoms selected from fluorine atoms, chlorine atoms and bromine atoms can also be cited.

[Chemistry 79]

[Chemistry 80]

Examples of compound (I) include compounds represented by formula (Ia1) to (Ia2216) and (Ib1) to (Ib1312), compounds represented by formula (If1) to (If13090), compounds represented by formula (It1) to (It900), and compounds represented by formula (Iu1) to (Iu3238) substituted with 1 to 6 groups selected from -SO ₃ H, -CO ₂ H, -SO 3 NH ₄ , -CO ₂ NH ₄ , -SO ₂ NH ₂ , -CONH ₂ , phthalimidomethyl (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 ), a compound containing one or more of a fluorine atom, a chlorine atom and a bromine atom.

For example, the compound represented by formula (Ia1) in Table 1 in which 1 to 6 -SO ₃ H atoms are substituted has the following structure. In the formula, -(SO ₃ H) _1-6 means that -SO ₃ H replaces 1 to 6 hydrogen atoms of the compound represented by formula (Ia1).

Examples of compound (I) include compounds represented by formula (Ia1) to (Ia2216) and (Ib1) to (Ib1312), compounds represented by formula (If1) to (If13090), compounds represented by formula (It1) to (It900), and compounds represented by formula (Iu1) to (Iu3238) in which one or more anions selected from -SO ₃ ^- and -CO ₂ ^- and one or more anions selected from 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 Metal salts containing one or more cations among ^{Na +} , Na ⁺ and K ⁺ .

Examples of compound (I) include metal salts comprising an anion represented by formula (Id) and an anion represented by formula (Ih) shown in Tables 32 to 33 and Tables h1 to h6 below, and a cation selected from the group consisting of 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 K ⁺ .

The symbols described in the "Q ¹ " column and the "Q ² " column in Tables 32 to 33 and Tables h1 to h6 correspond to the groups represented by the above formulas and the groups represented by the following formulas (Qw1) to (Qw11), respectively.

[Chemistry 83]

[Chemistry 86]

[Table h1]

[Table h2]

[Table h3]

[Table h4]

[Table h5]

[Table h6]

As the metal salt, for example, the metal salt represented by the formula (Ie) shown in Tables 34 to 38 below and the metal salt represented by the formula (Ik) shown in Tables k1 to k14 can be cited.

As the symbols recorded 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 Ba ²⁺ , Ni2+ represents Ni ²⁺ , Zn2+ represents Zn ²⁺ , Fe2+ represents Fe ²⁺ , Co2+ represents Co ²⁺ , Sn2+ represents Sn ²⁺ , Mn2+ represents Mn ²⁺ , Al3+ represents Al ³⁺ , Fe3+ represents Fe ³⁺ , Cr3+ represents Cr ³⁺ , Sn4+ represents Sn ⁴⁺ , Mn4+ represents Mn ⁴⁺ , Cu2+ represents Cu ²⁺ , Li+ represents Li ⁺ , Na+ represents Na ⁺ , and K+ represents K ⁺ .

The symbols recorded in the "Q ¹ " column and the "Q ² " column in Tables 34 to 38 and Tables k1 to k14 respectively correspond to the groups represented by the above formulas.

In formula (Ie) and formula (Ik), m is an integer greater than 1, preferably an integer between 1 and 20, and more preferably an integer between 1 and 10.

In formula (Ie) and formula (Ik), n is an integer greater than 1, preferably an integer between 1 and 20, and more preferably an integer between 1 and 10.

Wherein, when the compound (I) of the present invention is the oligomer or polymer, m and n represent the minimum integer of the ratio of the number of ligands and the number of metal atoms such that the charge of the compound (I) is zero, thereby indicating that the compound (I) is the oligomer or polymer.

[Table 35]

[Table 36]

[Table 37]

[Table 38]

[Table k1]

[Table k2]

Preferred as compound (I) are compounds represented by formula (Ia1) to (Ia2216); compounds represented by formula (If1) to (If13090); compounds represented by formula (It1) to (It900); compounds represented by formula (Iu1) to (Iu3238); compounds represented by formula (Ib8); compounds represented by formula (Ib14); wherein the compounds represented by formula (Ia1) to (Ia2216), compounds represented by formula (If1) to (If13090), compounds represented by formula (It1) to (It900), compounds represented by formula (Iu1) to (Iu3238), compounds represented by formula (Ib8), and compounds represented by formula (Ib14) are substituted with a group selected from -SO ₃ H, -CO ₂ H, -SO ₃ NH ₄ , _{-CO2NH4 ,} -SO2NH2, _{-CONH2 ,} phthalimidomethyl ( _C6H4 (CO) _2N - _CH2- ) _{, -SO2NH} (CH2) _2N (CH2CH3) ₂ , _-N ( _CH3 )(( _CH2 ) _11CH3 ), _a fluorine atom, a chlorine atom and a _bromine atom; and a compound represented by formula (Ia1) to formula ( _Ia2216 ), a compound represented by formula (If1) to formula (If13090), a compound represented by formula ( _It1 ) to formula (It900), a compound represented by formula (Iu1) to formula (Iu3238), a compound represented by formula (Ib8), and a compound represented by formula (Ib14) substituted with a substituted atom selected from _-SO3- ^and _-CO2 ^- , and one or more anions selected from 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 K ⁺ is more preferably a metal salt of one or more cations in the formula (Ia1) to (Ia2216); a compound represented by (If1) to (If13090); a compound represented by (It1) to (It900); a compound represented by (Iu1) to (Iu3238); a compound represented by (Ia1) to (Ia2216), a compound represented by (If1) to (If13090), a compound represented by (It1) to (It900), a compound represented by (Iu1) to (Iu3238), a compound represented by (Ib8), and a compound represented by (Ib14) substituted with -SO ₃ H, -CO ₂ H, -SO ₃ NH ₄ , -CO ₂ NH ₄ , a compound containing one or more of a fluorine atom, a chlorine atom and a bromine atom; and a metal salt containing an anion represented by formula (Id1) to formula (Id304) and an anion represented by formula (Ih1) to formula (Ih1666), and one or more cations selected from Mg2 ⁺ , Ca2 ⁺ , Sr2 ⁺ , ^{Ba2 +} , ^Ni2 +, Zn2 ⁺ , ^{Fe2 +} , Co2 ⁺ , Sn2+, Mn2+, ^Al3 +, Fe3 ⁺ , Cr3 ⁺ , Sn4 ⁺ , Mn4 ⁺ , Cu2 ⁺ , Li ⁺ , Na ⁺ and K ⁺ , Further preferred are compounds represented by formula (Ia1) to (Ia2216); compounds represented by formula (If1) to (If13090); compounds represented by formula (It1) to (It900); compounds represented by formula (Iu1) to (Iu3238); compounds represented by formula (Ia1) to (Ia2216), compounds represented by formula (If1) to (If13090), compounds represented by formula (It1) to (It900), compounds represented by formula (Iu1) to (Iu3238), compounds represented by formula (Ib8), and compounds represented by formula (Ib14) wherein -SO ₃ H, -CO ₂ H, -SO ₃ NH ₄ , -CO ₂ NH ₄ , a compound containing one or more of chlorine atoms and bromine atoms; a compound represented by formula (Ie1) to formula (Ie76); and a compound represented by formula (Ik1) to formula (Ik114); a compound represented by formula (Ik1615) to formula (Ik1633); a compound represented by formula (Ik1822) to formula (Ik1983); a compound represented by formula (Ie117); a compound represented by formula (Ie123); a compound represented by formula (Ik172); a compound represented by formula (Ik171); a compound represented by formula (Ik1777); a compound represented by formula (Ik181); The compound represented by formula (Ik397); the compound represented by formula (Ie273); and the compound represented by formula (Ie116), preferably: the compound represented by formula (Ia1) to formula (Ia2216); the compound represented by formula (If1) to formula (If13090); the compound represented by formula (It1) to formula (It900); the compound represented by formula (Iu1) to formula (Iu3238); the compound represented by formula (Ib8); and the compound represented by formula (Ib14), and more preferably: the compound represented by formula (Ia1) to formula (Ia124 1), a compound represented by formula (It1) to formula (It900), particularly preferably: 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 formula (Ia703), The compound represented by formula (Ia973), the compound represented by formula (It232), the compound represented by formula (It242), and the compound represented by formula (It750), and the most preferred are: the compound represented by formula (Ia1), the compound represented by formula (Ia2), the compound represented by formula (Ia3), the compound represented by formula (Ia22), the compound represented by formula (Ia23), the compound represented by formula (Ia35), the compound represented by formula (Ia696), the compound represented by formula (Ia703), the compound represented by formula (Ia973) The compound represented by formula (It232), the compound represented by formula (It242), and the compound represented by formula (It750) are preferably: the compound represented by formula (Ia1), the compound represented by formula (Ia2), the compound represented by formula (Ia3), the compound represented by formula (Ia696), the compound represented by formula (Ia703), the compound represented by formula (Ia973), the compound represented by formula (It232), the compound represented by formula (It242), and the compound represented by formula (It750).

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

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

In the reaction of the compound represented by formula (pt1), the compound represented by formula (pt2) and the compound represented by formula (pt3), the amount of the compound represented by formula (pt2) used is usually 0.1 mol to 30 mol, preferably 1 mol to 20 mol, more preferably 1 mol to 16 mol, and even more preferably 1 mol to 10 mol, relative to 1 mol of the compound represented by formula (pt1).

In the reaction of the compound represented by formula (pt1), the compound represented by formula (pt2) and the compound represented by formula (pt3), the amount of the compound represented by formula (pt3) used is usually 0.1 mol to 30 mol, preferably 1 mol to 20 mol, more preferably 1 mol to 16 mol, and even more preferably 1 mol to 10 mol, relative to 1 mol of the compound represented by formula (pt1).

The reaction temperature is usually -100℃~300℃, preferably 0℃~280℃, more preferably 50℃~250℃, further preferably 100℃~230℃, and particularly preferably 150℃~200℃.

The reaction time is usually 0.5 hours to 500 hours.

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

As the solvent, there can be mentioned: water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol, etc.; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether, etc.; ketone solvents such as acetone, methyl isobutyl ketone, etc.; ester solvents such as ethyl acetate, methyl benzoate, etc.; aliphatic hydrocarbon solvents such as oxane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; N,N-dimethylformamide, N,N-dimethylacetyl amine solvents such as amine, N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-di Methylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone, and more preferably methyl benzoate.

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

In the reaction of the compound represented by formula (pt1), the compound represented by formula (pt2) and the compound represented by formula (pt3), it is preferred that at least one selected from an acid and a metal salt coexists.

As the acid, there can be listed: inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid, phosphoric acid, etc.; 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, etc., preferably, there can be listed: hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid, more preferably, there can be listed carboxylic acids, and more preferably, there can be listed benzoic acid.

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

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 formula (pt1), the compound represented by formula (pt2) and the compound represented by formula (pt3) is usually 0.01 mol to 30 mol, preferably 0.01 mol to 20 mol, more preferably 0.01 mol to 10 mol, and even more preferably 0.01 mol to 3 mol, relative to 1 mol of the compound represented by formula (pt1).

The method for removing compound (I) from the reaction mixture is not particularly limited, and it can be removed by various known methods.

For example, after the reaction is completed, if compound (I) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I) is fully mixed with the reaction mixture, and then filtered to remove compound (I). Furthermore, the obtained residue can be washed with amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, sulfoxide solvents such as dimethyl sulfoxide, or mixed solvents thereof, alkaline aqueous solutions such as sodium hydroxide aqueous solutions, and/or acidic aqueous solutions such as hydrochloric acid, and then washed with water, low-boiling alcohols such as methanol, or mixed solvents thereof to remove compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

Alternatively, after the reaction is completed, the solvent of the reaction mixture can be distilled off, and the obtained residue can be purified by column chromatography and/or recrystallization. After the reaction is completed, the reaction mixture can be purified by column chromatography and/or recrystallization.

After the reaction is completed, if compound (I) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I) is fully mixed with the reaction mixture and then filtered to remove compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

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

[Chemistry 90]

In formula (pt1), formula (pt2), formula (pt3), formula (I′) and 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 formula (pt1) and the compound represented by formula (pt2), the amount of the compound represented by formula (pt2) used is usually 0.1 mol to 60 mol, preferably 1 mol to 40 mol, more preferably 1 mol to 32 mol, and even more preferably 2 mol to 20 mol, relative to 1 mol of the compound represented by formula (pt1).

The amount of the compound represented by formula (pt3) used in the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3) is generally 0.1 mol to 30 mol, preferably 1 mol to 20 mol, more preferably 1 mol to 16 mol, and even more preferably 1 mol to 10 mol, relative to 1 mol of the compound represented by formula (IM1).

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

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

The reaction of the compound represented by formula (pt1) with the compound represented by formula (pt2), or the reaction of the compound represented by formula (IM1) with the compound represented by formula (pt3) is usually carried out in the presence of a solvent.

Examples of the solvent in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2), or the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3) include: water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; amine solvents; diisocyanate; Ether solvents such as ethyl ether, tetrahydrofuran, and 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; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, and tetrahydronaphthalene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene; nitric acid solvents such as tantalum; nitrocarbon solvents such as nitrobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, etc., preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone, and more preferably methyl benzoate.

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

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

In the reaction of the compound represented by formula (pt1) with the compound represented by formula (pt2), or the reaction of the compound represented by formula (IM1) with the compound represented by formula (pt3), it is preferred that at least one selected from an acid and a metal salt coexists.

The acid in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2), or the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3) includes: 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; carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid, and tartaric acid, etc., preferably includes: hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acids, more preferably includes any carboxylic acids, and further preferably includes benzoic acid.

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

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

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

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

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

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 the compound can be extracted by various known methods.

For example, after the reaction is completed, if compound (I') in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I') is fully mixed with the reaction mixture, and then filtered to remove compound (I'). Furthermore, the obtained residue can be washed with amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, sulfoxide solvents such as dimethyl sulfoxide, or mixed solvents thereof, alkaline aqueous solutions such as sodium hydroxide aqueous solutions, and/or acidic aqueous solutions such as hydrochloric acid, and then washed with water, low-boiling alcohols such as methanol, or mixed solvents thereof to remove compound (I'). Furthermore, column chromatography and/or recrystallization can also be used for purification.

Alternatively, after the reaction is completed, the solvent of the reaction mixture can be distilled off, and the obtained residue can be purified by column chromatography and/or recrystallization. After the reaction is completed, the reaction mixture can be purified by column chromatography and/or recrystallization.

After the reaction is completed, if compound (I') in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I') is fully mixed with the reaction mixture, and then filtered to remove compound (I'). Furthermore, column chromatography and/or recrystallization can also be used for purification.

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 the compound can be extracted by various known methods.

For example, after the reaction is completed, if compound (I) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I) is fully mixed with the reaction mixture and filtered to remove compound (I). Furthermore, the obtained residue can be washed with amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, sulfoxide solvents such as dimethyl sulfoxide, or mixed solvents thereof, alkaline aqueous solutions such as sodium hydroxide aqueous solutions, and/or acidic aqueous solutions such as hydrochloric acid, and then washed with water, low-boiling alcohols such as methanol, or mixed solvents thereof to remove compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

Alternatively, after the reaction is completed, the solvent of the reaction mixture can be distilled off, and the obtained residue can be purified by column chromatography and/or recrystallization. After the reaction is completed, the reaction mixture can be purified by column chromatography and/or recrystallization.

After the reaction is completed, if compound (I) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I) is fully mixed with the reaction mixture and then filtered to remove compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

Examples of the base used in the hydrolysis reaction of the compound represented by the formula (I') in the presence of a base include organic bases such as 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, sodium methoxide, sodium ethoxide, sodium tert-butoxide, sodium thiophene, sodium t-butoxide, sodium t-butylate ... Metal alkoxides such as potassium tributylate, organic metal compounds such as methyl lithium, butyl lithium, tert-butyl lithium and phenyl lithium, Inorganic bases such as sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide and potassium hydroxide, etc., preferably inorganic bases, more preferably lithium hydroxide, sodium hydroxide and potassium hydroxide, further preferably sodium hydroxide and potassium hydroxide, and particularly preferably potassium hydroxide.

The amount of alkali used in the hydrolysis reaction of the compound represented by formula (I') in the presence of alkali is generally 0.1 mol to 100 mol, preferably 1 mol to 70 mol, and more preferably 2 mol to 40 mol, relative to 1 mol of the compound represented by formula (I').

The amount of water used in the hydrolysis reaction of the compound represented by formula (I') in the presence of an alkali is usually 1 to 1000 parts by mass, preferably 1 to 200 parts by mass, more preferably 1 to 100 parts by mass, and even more preferably 1 to 50 parts by mass, relative to 1 part by mass of the compound represented by formula (I').

The reaction temperature in the hydrolysis reaction of the compound represented by formula (I') in the presence of an alkali is usually 0°C to 100°C, preferably 5°C to 100°C, more preferably 20°C to 100°C, further preferably 40°C to 100°C, and particularly preferably 60°C to 100°C.

The reaction time in the hydrolysis reaction of the compound represented by formula (I') in the presence of an alkali is generally 0.5 hours to 120 hours, preferably 1 hour to 72 hours, and more preferably 1 hour to 24 hours.

The method for 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 an alkali is not particularly limited, and the compound can be extracted by various known methods.

For example, after the reaction is completed, an acidic aqueous solution such as hydrochloric acid is added to the reaction mixture to neutralize it, and then filtered to remove the compound (IM1). Furthermore, the obtained residue can be washed with an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide, a ketone solvent such as acetone, an alcohol solvent such as methanol, a nitrile solvent such as acetonitrile, 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 hydrochloric acid to remove the compound (IM1). Furthermore, column chromatography and/or recrystallization can also be used for purification.

Alternatively, after the reaction is completed, the solvent of the reaction mixture can be distilled off, and the obtained residue can be purified by column chromatography and/or recrystallization. After the reaction is completed, the reaction mixture can be purified by column chromatography and/or recrystallization.

The compound represented by formula (I) can be produced by reacting a compound represented by formula (pt1) with a compound represented by formula (pt3) to produce a compound represented by formula (IM2) (hereinafter, sometimes referred to as compound (IM2)), and then reacting the compound represented by formula (IM2) with a compound represented by formula (pt2).

[Chemistry 91]

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.

In the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt3), the amount of the compound represented by formula (pt3) used is usually 0.1 mol to 10 mol, preferably 0.1 mol to 5 mol, more preferably 0.5 mol to 2 mol, and even more preferably 0.8 mol to 1.5 mol, relative to 1 mol of the compound represented by formula (pt1).

The reaction temperature of the compound represented by formula (pt1) and the compound represented by formula (pt3) is usually -100℃~300℃, preferably 0℃~280℃, more preferably 50℃~250℃, further preferably 100℃~230℃, and particularly preferably 120℃~200℃.

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

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

Examples of the solvent in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt3) include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, and diphenyl ether; acetone, methyl isobutyl ketone, etc. Ketone solvents; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, and tetrahydronaphthalene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; N,N-dimethylformamide, N,N -dimethylacetamide, N-methylpyrrolidone and other amide solvents; dimethyl sulfoxide and other sulfoxide solvents, preferably: phenol, diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, Amine, N-methylpyrrolidone, dimethyl sulfoxide, preferably phenol, diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone, preferably phenol, methyl benzoate, and particularly preferably phenol.

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

The method for extracting the compound (IM2) from the reaction mixture in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is not particularly limited, and the compound (IM2) can be extracted by various known methods.

For example, after the reaction is completed, if the compound (IM2) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than the compound (IM2) is fully mixed with the reaction mixture and then filtered to remove the compound (IM2).

Furthermore, the obtained residue is washed with an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide, a ketone solvent such as acetone, an alcohol solvent such as methanol, a nitrile solvent such as acetonitrile, 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 hydrochloric acid, to remove the compound (IM2).

Furthermore, it can also be purified by column chromatography and/or recrystallization.

Alternatively, after the reaction is completed, the solvent of the reaction mixture can be distilled off, and the obtained residue can be purified by column chromatography and/or recrystallization. After the reaction is completed, the reaction mixture can be purified by column chromatography and/or recrystallization.

After the reaction is completed, the compound (IM2) in the reaction mixture is difficult to dissolve. The reaction mixture is added to a solvent such as methanol that easily dissolves compounds other than the compound (IM2), mixed thoroughly, and filtered to remove the compound (IM2). Furthermore, column chromatography and/or recrystallization can also be used for purification.

In the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2), the amount of the compound represented by formula (pt2) used is usually 0.1 mol to 30 mol, preferably 1 mol to 20 mol, more preferably 1 mol to 16 mol, and even more preferably 1 mol to 10 mol, relative to 1 mol of the compound represented by formula (IM2).

The reaction temperature of the compound represented by formula (IM2) and the compound represented by formula (pt2) is usually -100℃~300℃, preferably 0℃~280℃, more preferably 50℃~250℃, further preferably 100℃~230℃, and particularly preferably 150℃~200℃.

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

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

Examples of the solvent in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, and diphenyl ether; acetone, methyl isocyanate, and the like. Ketone solvents such as butyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, and tetrahydronaphthalene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; N,N- Amine solvents such as dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethyl sulfoxide ... Amine, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone, and more preferably methyl benzoate.

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

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

As the acid in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2), there can be listed: 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; carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid and tartaric acid, etc., preferably, there can be listed: hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid, more preferably, there can be listed carboxylic acids, and further preferably, there can be listed benzoic acid.

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

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

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

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 the compound can be extracted by various known methods.

For example, after the reaction is completed, if compound (I) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I) is fully mixed with the reaction mixture and filtered to remove compound (I). Furthermore, the obtained residue can be washed with amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, sulfoxide solvents such as dimethyl sulfoxide, or mixed solvents thereof, alkaline aqueous solutions such as sodium hydroxide aqueous solutions, and/or acidic aqueous solutions such as hydrochloric acid, and then washed with water, low-boiling alcohols such as methanol, or mixed solvents thereof to remove compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

Alternatively, after the reaction is completed, the solvent of the reaction mixture can be distilled off, and the obtained residue can be purified by column chromatography and/or recrystallization. After the reaction is completed, the reaction mixture can be purified by column chromatography and/or recrystallization.

After the reaction is completed, if compound (I) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I) is fully mixed with the reaction mixture and then filtered to remove compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

The compound represented by formula (I) can be produced by reacting a compound represented by formula (pt1) with a compound represented by formula (pt3) to produce a compound represented by formula (IM2) (hereinafter, sometimes referred to as compound (IM2)), and then reacting the compound represented by formula (IM2) with a compound represented by formula (pt2).

[Chemistry 92]

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 formula (pt3) used in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt3) is usually 0.1 mol to 10 mol, preferably 0.1 mol to 5 mol, more preferably 0.5 mol to 2 mol, and even more preferably 0.8 mol to 1.5 mol, relative to 1 mol of the compound represented by formula (pt1).

The reaction temperature of the compound represented by formula (pt1) and the compound represented by formula (pt3) is usually -100℃~300℃, preferably 0℃~280℃, more preferably 50℃~250℃, further preferably 100℃~230℃, and particularly preferably 120℃~200℃.

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

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

As the solvent in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt3), water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol, etc.; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether, etc.; acetone, methyl isobutyl ketone, etc. Ketone solvents; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, and tetrahydronaphthalene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; N,N-dimethylformamide, N,N -dimethylacetamide, N-methylpyrrolidone and other amide solvents; dimethyl sulfoxide and other sulfoxide solvents, preferably: phenol, diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethylacetamide, Amine, N-methylpyrrolidone, dimethyl sulfoxide, preferably phenol, diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone, preferably phenol, methyl benzoate, and particularly preferably phenol.

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

The method for extracting the compound (IM2) from the reaction mixture in the reaction between the compound represented by the formula (pt1) and the compound represented by the formula (pt3) is not particularly limited, and the compound (IM2) can be extracted by various known methods.

For example, after the reaction is completed, if the compound (IM2) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than the compound (IM2) is fully mixed with the reaction mixture and then filtered to remove the compound (IM2).

Furthermore, the obtained residue is washed with an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide, a ketone solvent such as acetone, an alcohol solvent such as methanol, a nitrile solvent such as acetonitrile, 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 hydrochloric acid, to remove the compound (IM2).

Furthermore, it can also be purified by column chromatography and/or recrystallization.

Alternatively, after the reaction is completed, the solvent of the reaction mixture can be distilled off, and the obtained residue can be purified by column chromatography and/or recrystallization. After the reaction is completed, the reaction mixture can be purified by column chromatography and/or recrystallization.

After the reaction is completed, if the compound (IM2) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than the compound (IM2) is mixed with the reaction mixture thoroughly and then filtered to remove the compound (IM2). Furthermore, column chromatography and/or recrystallization can be used for purification.

In the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2), the amount of the compound represented by formula (pt2) used is usually 0.1 mol to 30 mol, preferably 1 mol to 20 mol, more preferably 1 mol to 16 mol, and even more preferably 1 mol to 10 mol, relative to 1 mol of the compound represented by formula (IM2).

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

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

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

Examples of the solvent in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2) include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, and diphenyl ether; acetone, methyl isocyanate, and the like. Ketone solvents such as butyl ketone; ester solvents such as ethyl acetate and methyl benzoate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; N,N-dichlorobenzene; Amine solvents such as methylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, etc., preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N,N-dimethylformamide, N,N-dimethyl sulfoxide, etc. Amine, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, preferably diphenyl ether, methyl benzoate, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, nitrobenzene, N-methylpyrrolidone, and more preferably methyl benzoate.

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

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

As the acid in the reaction between the compound represented by formula (IM2) and the compound represented by formula (pt2), there can be listed: 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; carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, benzoic acid and tartaric acid, etc., preferably, there can be listed: hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid, more preferably, there can be listed carboxylic acids, and further preferably, there can be listed benzoic acid.

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

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

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

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 the compound can be extracted by various known methods.

For example, after the reaction is completed, if compound (I) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I) is fully mixed with the reaction mixture, and then filtered to remove compound (I). Furthermore, the obtained residue can be washed with amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, sulfoxide solvents such as dimethyl sulfoxide, or mixed solvents thereof, alkaline aqueous solutions such as sodium hydroxide aqueous solutions, and/or acidic aqueous solutions such as hydrochloric acid, and then washed with water, low-boiling alcohols such as methanol, or mixed solvents thereof to remove compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

Alternatively, after the reaction is completed, the solvent of the reaction mixture can be distilled off, and the obtained residue can be purified by column chromatography and/or recrystallization. After the reaction is completed, the reaction mixture can be purified by column chromatography and/or recrystallization.

After the reaction is completed, if compound (I) in the reaction mixture is difficult to dissolve, a solvent such as methanol that easily dissolves compounds other than compound (I) is fully mixed with the reaction mixture and then filtered to remove compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

By reacting Compound (I) with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid, a sulfonic group or -SO ₃ M can be introduced into Compound (I).

A compound obtained by introducing a sulfo group or -SO ₃ M into the compound (I) (hereinafter, sometimes referred to as "sulfonated compound (I)") is also a compound of the present invention.

The amount of SO ₃ used in the fuming sulfuric acid is generally 1 mol to 200 mol, preferably 2 mol to 150 mol, more preferably 3 mol to 100 mol, and even more preferably 5 mol to 80 mol, relative to 1 mol of compound (I).

The amount of SO ₃ in fuming sulfuric acid is generally 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 50 parts by mass, based on 100 parts by mass of fuming sulfuric acid.

The amount of chlorosulfonic acid used is generally 1 mol to 500 mol, preferably 1 mol to 300 mol, more preferably 1 mol to 200 mol, and even more preferably 1 mol to 150 mol, relative to 1 mol of compound (I).

When chlorosulfonic acid is used to introduce a sulfo group or -SO ₃ M into compound (I), the reaction may be carried out in the presence of a solvent.

Examples of the solvent include halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, and 2-chloronaphthalene.

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

The reaction temperature of sulfonation is usually -20℃~200℃, preferably -10℃~150℃, and more preferably 0℃~100℃. The reaction time is usually 0.5 hours~300 hours.

The method for removing the sulfonated compound (I) from the reaction mixture is not particularly limited, and it can be removed by various known methods.

For example, after the reaction is completed, the reaction mixture is added dropwise to ice, and the obtained mixture is filtered to remove the sulfonated compound (I). Furthermore, it can also be purified by column chromatography and/or recrystallization.

Alternatively, after the reaction is completed, the reaction mixture is added dropwise to ice, and the obtained mixture is mixed with a hydrophilic organic solvent such as methanol, an alcohol solvent such as acetonitrile, and a mixed solvent thereof, which is difficult to dissolve the sulfonated compound (I) but easy to dissolve compounds other than the sulfonated compound (I), and filtered to remove the sulfonated compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

Alternatively, after the reaction is completed, the reaction mixture is added dropwise to ice, and the obtained mixture is neutralized with an aqueous solution such as ammonia, a water-soluble amine, or a mixture thereof, and then the mixture is mixed with a hydrophilic organic solvent such as an alcohol solvent such as methanol, a nitrile solvent such as acetonitrile, or a mixed solvent thereof, and filtered to remove the solvent from the obtained filtrate, thereby extracting the sulfonated compound (I). Furthermore, column chromatography and/or recrystallization can also be used for purification.

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

The amount of the salt having MM used is generally 0.01 mol to 100 mol, preferably 0.02 mol to 50 mol, and more preferably 0.1 mol to 30 mol, relative to 1 mol of the compound (I) containing an acid group.

The reaction temperature is usually 0℃~100℃, preferably 0℃~80℃, more preferably 0℃~60℃, and even more preferably 0℃~40℃.

The reaction time is usually 0.5 hours to 500 hours.

The reaction of the compound (I) containing an acid group and the salt having MM is usually carried out in the presence of a solvent.

Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-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 hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, and tetrahydronaphthalene; dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trimethylbenzene), and tetrahydronaphthalene; For example, halogenated hydrocarbon solvents such as 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene; nitrified hydrocarbon solvents such as nitrobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone; dimethyl sulfoxide and other sulfoxide solvents, preferably: water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; and mixed solvents thereof, preferably water.

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

The reaction of the compound (I) containing an acid group and the salt having MM can be carried out in the presence of a base.

Examples of the base include organic bases such as 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, metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, methyl Lithium, butyl lithium, tert-butyl lithium, phenyl lithium and other organic metal compounds, sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, and potassium hydroxide and other inorganic bases, etc., preferably inorganic bases, more preferably lithium hydroxide, sodium hydroxide, and potassium hydroxide, further preferably sodium hydroxide and potassium hydroxide, and particularly preferably sodium hydroxide.

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

The method for removing the MM-containing compound (I) from the reaction mixture is not particularly limited, and it can be removed by various known methods.

For example, after the reaction is completed, the reaction mixture is filtered to remove the compound (I) having -SO ₃ (MM) and/or -CO ₂ (MM). Furthermore, the obtained residue can be washed with an amide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, a sulfoxide solvent such as dimethyl sulfoxide, a ketone solvent such as acetone, an alcohol solvent such as methanol, a nitrile solvent such as acetonitrile, water, or a mixed solvent thereof, and then washed and purified with water, a low-boiling alcohol such as methanol, or a mixed solvent thereof.

[Coloring composition]

The coloring composition of the present invention comprises compound (I) and solvent (E). According to the coloring composition of the present invention, a color filter with a darker color can be formed compared to a coloring composition comprising C.I. Pigment Yellow 138. The color filter formed by the coloring composition of the present invention can be suitably used in display devices such as liquid crystal display devices. The coloring composition of the present invention is preferably a yellow composition, an orange composition, a red composition and a green composition.

The content of the solid component in the coloring composition is less than 100 mass%, preferably 0.01 mass% or more and less than 100 mass%, more preferably 0.1 mass% or more and 99.9 mass% or less, further preferably 0.1 mass% or more and 99 mass% or less, particularly preferably 1 mass% or more and 90 mass% or less, further preferably 1 mass% or more and 80 mass% or less, particularly preferably 1 mass% or more and 70 mass% or less, extremely preferably 1 mass% or more and 60 mass% or less, and most preferably 1 mass% or more and 50 mass% or less.

In this specification, the so-called "total amount of solid components" refers to the total amount of components after removing the solvent (E) from the coloring composition of the present invention. The total amount of solid components and the content of each component relative to it can be measured using known analytical methods such as liquid chromatography or gas chromatography.

The content of compound (I) in the coloring composition in the total amount of solid components is 100% by mass or less, preferably 0.0001% by mass or more and 99.9999% by mass or less, more preferably 0.0001% by mass or more and 99% by mass or less, further preferably 0.0001% by mass or more and 90% by mass or less, particularly preferably 0.0001% by mass or more and 80% by mass or less, further preferably 0.0001% by mass or more and 70% by mass or less, particularly preferably 0.0001% by mass or more and 60% by mass or less, extremely preferably 0.0001% by mass or more and 55% by mass or less, and most preferably 0.1% by mass or more and 55% by mass or less.

[Solvent (E)]

The solvent (E) is not particularly limited, and any solvent commonly used in this field can be used.

Examples of solvents (E) include: ester solvents (solvents containing -CO-O- and no -O- in the molecule), ether solvents (solvents containing -O- and no -CO-O- in the molecule), ether ester solvents (solvents containing -CO-O- and -O- in the molecule), ketone solvents (solvents containing -CO- and no -CO-O- in the molecule), alcohol solvents (solvents containing OH and no -O-, -CO- and -CO-O- in the molecule), aromatic hydrocarbon solvents, amide solvents, and dimethyl sulfoxide, etc.

As ester solvents, there can be listed: methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetylacetate, ethyl acetylacetate, cyclohexanol acetate and γ-butyrolactone, etc.

As ether solvents, there can be listed: 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 ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethyl ether and methyl anisole, etc.

As the ether ester solvent, there can be mentioned: methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, 2-methoxy-2-methylpropionic acid methyl ester, 2-ethoxy-2-methylpropionic acid ethyl ester, 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 ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate and dipropylene glycol methyl ether acetate, etc.

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.

As alcohol solvents, there are: methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol and glycerol, etc.

As aromatic hydrocarbon solvents, we can cite: benzene, toluene, xylene and mesitylene, etc.

As amide solvents, there are: N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone, etc.

Two or more of these solvents may be used in combination.

Among the above solvents, organic solvents having a boiling point of 120°C or higher and 180°C or lower at 1 atm are preferred in terms of coating properties and drying properties. Preferred solvents include 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 preferred solvents include propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate, and 4-hydroxy-4-methyl-2-pentanone.

The content of the solvent (E) relative to the total amount of the coloring composition is less than 100 mass%, preferably 99.99 mass% or less, more preferably 0.1 mass% or more and 99.9 mass% or less, further preferably 1 mass% or more and 99.9 mass% or less, particularly preferably 10 mass% or more and 99 mass% or less, further preferably 20 mass% or more and 99 mass% or less, particularly preferably 30 mass% or more and 99 mass% or less, extremely 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 more preferably a polymer having a structural unit derived from the following monomer (hereinafter referred to as "monomer (a)"), wherein the monomer is at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides.

The resin (B) is preferably a copolymer having structural units derived from a monomer containing a cyclic ether structure having 2 to 4 carbon atoms and an ethylenic unsaturated bond (hereinafter referred to as "monomer (b)"), and other structural units.

As other structural units, there can be listed structural units derived from monomers copolymerizable with monomer (a) (wherein, different from monomer (a) and monomer (b); hereinafter, there is a case where it is referred to as "monomer (c)"), structural units having ethylenic unsaturated bonds, etc.

In this specification, "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. "(meth)acryl" and "(meth)acrylate" also have the same meaning.

Examples of the monomer (a) include acrylic acid, methacrylic acid, crotonic acid, and unsaturated monocarboxylic acids such as o-vinylbenzoic acid, m-vinylbenzoic acid, and p-vinylbenzoic acid; maleic acid, fumaric acid, citric acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid; Phthalic acid and unsaturated dicarboxylic acids such as 1,4-cyclohexenedicarboxylic 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-methyl Bicyclic unsaturated compounds containing a carboxyl group, such as bicyclo[2.2.1]hept-2-ene and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; maleic anhydride, conic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5, Unsaturated dicarboxylic anhydrides such as 6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; unsaturated mono[(meth)acryloxyalkyl] esters of polycarboxylic acids having a valency of more than two such as mono[2-(meth)acryloxyethyl] succinate and mono[2-(meth)acryloxyethyl] phthalate; unsaturated acrylic esters containing a hydroxyl group and a carboxyl group in the same molecule such as α-(hydroxymethyl)acrylic acid, etc.

Among these, acrylic acid, methacrylic acid, o-vinylbenzoic acid, m-vinylbenzoic acid, p-vinylbenzoic acid, and maleic anhydride are preferred in terms of copolymerization reactivity or solubility of the obtained resin in alkaline aqueous solution.

The monomer (b) refers to 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 an oxycyclopropane ring, an oxycyclobutane ring, and a tetrahydrofuran ring) and an ethylenic unsaturated bond.

The monomer (b) is preferably a monomer having a cyclic ether structure with 2 to 4 carbon atoms and a (meth)acryloyloxy group.

Examples of monomer (b) include monomers having an oxocyclopropyl group and an ethylenic unsaturated bond (hereinafter referred to as "monomer (b1)"), monomers having an oxocyclobutyl group and an ethylenic unsaturated bond (hereinafter referred to as "monomer (b2)"), and monomers having a tetrahydrofuranyl group and an ethylenic unsaturated bond (hereinafter referred to as "monomer (b3)").

As monomer (b1), for example, there can be listed: monomers having a structure formed by epoxidation of aliphatic unsaturated hydrocarbons in a straight chain or branched chain (hereinafter, sometimes referred to as "monomer (b1-1)") and monomers having a structure formed by epoxidation of alicyclic unsaturated hydrocarbons (hereinafter, sometimes referred to as "monomer (b1-2)").

As the monomer (b1-1), a monomer having a glyceryl group and an ethylenic unsaturated bond is preferred.

Examples of the monomer (b1-1) include glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (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(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tri(glycidyloxymethyl)styrene, 2,3,5-tri(glycidyloxymethyl)styrene, 2,3,6-tri(glycidyloxymethyl)styrene, 3,4,5- tri(glycidyloxymethyl)styrene and 2,4,6-tri(glycidyloxymethyl)styrene, etc.

As monomers (b1-2), for example, vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide (registered trademark) 2000; manufactured by Daicel (Co., Ltd.)), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer (registered trademark) A400; manufactured by Daicel (Co., Ltd.)), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer (registered trademark) M100; manufactured by Daicel (Co., Ltd.)), compounds represented by formula (BI) and compounds represented by formula (BII), etc. can be cited.

[In formula (BI) and formula (BII), ^Ra and ^Rb independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, wherein the hydrogen atom contained in the alkyl group may be substituted by a hydroxyl group; ^Xa and ^Xb independently represent a single bond, * ^-Rc- , * ^-Rc -O-, * ^-Rc -S- or * ^-Rc -NH-; ^Rc represents an alkanediyl group having 1 to 6 carbon atoms; * represents a bond with O]

As the alkyl group having 1 to 4 carbon atoms, for example, there can be listed: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, etc.

Examples of alkyl groups formed by replacing a hydrogen atom with a hydroxyl group include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl, etc.

As ^Ra and ^Rb , preferably, there can be mentioned a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferably, there can be mentioned a hydrogen atom and a methyl group.

Examples of alkanediyl groups include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, etc.

Preferred _{examples of Xa and Xb include a single bond, methylene, ethylidene, *-CH2-O- and *-CH2CH2-O-. More preferred examples include a single bond and *-CH2CH2} ^{- O-} _{( * represents a} bond with O).

As the compound represented by formula (BI), there can be listed compounds represented by any one of formula (BI-1) to formula (BI-15). Among them, preferred are compounds represented by formula (BI-1), formula (BI-3), formula (BI-5), formula (BI-7), formula (BI-9) and formula (BI-11) to formula (BI-15), and more preferred are compounds represented by formula (BI-1), formula (BI-7), formula (BI-9) and formula (BI-15).

[Chemistry 94]

[Chemistry 95]

As the compound represented by formula (BII), there can be listed compounds represented by any one of formula (BII-1) to formula (BII-15), among which preferred are compounds represented by formula (BII-1), formula (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) and formula (BII-11) to formula (BII-15), and more preferred are compounds represented by formula (BII-1), formula (BII-7), formula (BII-9) and formula (BII-15).

The compound represented by formula (BI) and the compound represented by formula (BII) Can be used alone or in combination of two or more. The compound represented by formula (BI) and the compound represented by formula (BII) can also be used in combination. When the compound represented by formula (BI) and the compound represented by formula (BII) are used in combination, the content ratio [compound represented by formula (BI): compound represented by formula (BII)] is preferably 5:95~95:5 on a molar basis, more preferably 10:90~90:10, and even more preferably 20:80~80:20.

As the monomer (b2), a monomer having an oxacyclobutyl group and a (meth)acryloyloxy group is more preferred.

As monomer (b2), for example, 3-methyl-3-methacryloyloxymethyloxycyclobutane, 3-methyl-3-acryloyloxymethyloxycyclobutane, 3-ethyl-3-methacryloyloxymethyloxycyclobutane, 3-ethyl-3-acryloyloxymethyloxycyclobutane, 3-methyl-3-methacryloyloxyethyloxycyclobutane, 3-methyl-3-acryloyloxyethyloxycyclobutane, 3-ethyl-3-methacryloyloxyethyloxycyclobutane, 3-ethyl-3-acryloyloxyethyloxycyclobutane, etc. can be cited.

As the monomer (b3), a monomer having a tetrahydrofuranyl group and a (meth)acryloyloxy group is more preferred.

Examples of monomers (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, etc.

As the monomer (b), the monomer (b1) is preferred in terms of further improving the reliability of the obtained color filter in terms of heat resistance, chemical resistance, etc. Furthermore, the monomer (b1-2) is more preferred in terms of excellent storage stability of the coloring composition.

Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, t-butyl (meth)acrylate, 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 ]decane-8-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decane-9-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decen-8-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ] (meth)acrylates such as decen-9-yl (meth)acrylate, dicyclopentyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate; (meth)acrylates containing a hydroxyl group such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; 2,2,3,3,4,4,5,5 (meth)acrylate -octafluoropentyl esters and other halogen-containing (meth)acrylates; diethyl maleate, diethyl fumarate and diethyl itaconate and other dicarboxylic acid diesters; 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[2.2.1]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(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene and other bicyclic unsaturated compounds; N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidohexanoate, N-succinimidyl-3-maleimidopropionate and N-(9-acridinyl)maleimido dicarbonyl imide derivatives such as amine; aromatic compounds containing vinyl groups such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, 9-vinylcarbazole and p-methoxystyrene; nitriles containing vinyl groups such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; amides containing vinyl groups such as (meth)acrylamide; esters such as vinyl acetate; dienes such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene, etc.

Among them, preferred are styrene, vinyltoluene, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl (meth)acrylate ^{, tricyclo[5.2.1.0 2,6 ]decane-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 ester, 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, etc.

Specific examples of the resin (B) include 3,4-epoxyhexylmethyl (meth)acrylate/(meth)acrylic acid copolymers, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid copolymers, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymers, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/9-vinylcarbazole/(meth)acrylic acid copolymers, 3,4-epoxytricyclo[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 ester/(meth)acrylic acid/vinyl toluene copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/tricyclo[5.2.1.0 ^2,6 ] decenyl ester/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3-methyl-3-(meth)acryloyloxymethyloxycyclobutane/(meth)acrylic acid/styrene copolymer, benzyl (meth)acrylate/(meth)acrylic acid copolymer, styrene/(meth)acrylic acid copolymer and resins described in Japanese Patent Laid-Open No. 9-106071, Japanese Patent Laid-Open No. 2004-29518 and Japanese Patent Laid-Open No. 2004-361455, etc.

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 types. In this case, the resin (B) is preferably at least a copolymer containing at least one structural unit derived from the monomer (a) and a structural unit derived from the monomer (b), more preferably a copolymer containing at least one structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1), further preferably a copolymer containing at least one structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1-2), and particularly preferably a copolymer containing a structural unit selected from the group consisting of 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, and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer.

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, further preferably 1,000 to 30,000, particularly preferably 3000 to 30000, and particularly preferably 5,000 to 30,000.

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

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

In the coloring composition, the content of the resin (B) is less than 100 mass%, preferably 0.00001 mass% or more and 99.99999 mass% or less, more preferably 1 mass% or more and 99 mass% or less, further preferably 1 mass% or more and 97 mass% or less, particularly preferably 1 mass% or more and 95 mass% or less, further preferably 3 mass% or more and 95 mass% or less, particularly preferably 5 mass% or more and 95 mass% or less, and extremely preferably 10 mass% or more and 95 mass% or less.

[Preparation of liquid containing compound (I)]

The coloring composition of the present invention can be prepared by using a liquid containing compound (I) after pre-preparing a liquid containing compound (I) and a solvent (E). In the case where compound (I) is not dissolved in solvent (E), the liquid containing compound (I) can also be prepared by dispersing compound (I) in solvent (E) and mixing. The liquid containing compound (I) may contain a part or all of the solvent (E) contained in the coloring composition.

Furthermore, the liquid containing compound (I) is contained in the coloring composition of the present invention.

The content of the solid component of the liquid containing compound (I) is less than 100 mass% relative to the total amount of the liquid containing compound (I), preferably 0.01 mass% or more and 99.99 mass% or less, more preferably 0.1 mass% or more and 99.9 mass% or less, further preferably 0.1 mass% or more and 99 mass% or less, particularly preferably 1 mass% or more and 90 mass% or less, further preferably 1 mass% or more and 80 mass% or less, particularly preferably 1 mass% or more and 70 mass% or less, extremely preferably 1 mass% or more and 60 mass% or less, and most preferably 1 mass% or more and 50 mass% or less.

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

If necessary, compound (I) may be subjected to rosin treatment, surface treatment using derivatives that introduce acidic or alkaline groups, grafting treatment on the surface of compound (I) using polymer compounds, micronization treatment using sulfuric acid micronization method, salt milling method, etc., cleaning treatment using organic solvents or water to remove impurities, and removal treatment of ionic impurities using ion exchange method, etc.

In addition, compound (I) may be subjected to the following treatments as necessary: crystal structure conversion, particle shaping and/or particle size uniformization; mixing compound (I) with water and/or an organic solvent, stirring and/or stirring while heating to obtain a suspension, and filtering the suspension to obtain a compound (I) with a changed crystal structure; and changing the crystal structure of compound (I) by recrystallization. treatment; mixing compound (I) with water, sulfuric acid or an organic solvent, stirring and/or stirring while heating to obtain a solution or suspension, mixing the solution or suspension with a poor solvent for compound (I) to obtain a suspension, filtering the suspension to obtain a compound (I) with a changed crystal structure; mixing compound (I) with a derivative, and water and/or an organic solvent, stirring and / or stirring while heating to obtain a suspension, filtering the suspension to obtain a mixture containing compound (I) with a changed crystal structure and/or mixing compound (I) with a derivative; by recrystallizing the mixture of compound (I) and a derivative to obtain a mixture containing compound (I) with a changed crystal structure and/or mixing compound (I) with a derivative ; Compound (I), a derivative, and water, sulfuric acid or an organic solvent are mixed, stirred and/or stirred while heating to obtain a solution or suspension, the solution or suspension is mixed with a poor solvent for compound (I), and after obtaining a suspension, the suspension is filtered to obtain a mixture containing compound (I) with a changed crystal structure and/or a treatment of mixing compound (I) with a derivative, etc.

When multiple compounds (I) or derivatives are used, these treatments may be performed individually or in combination.

The particle size of compound (I) is preferably roughly uniform.

As the organic solvent used in the above-mentioned crystal structure transformation, there can be listed: nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol, etc.; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether, etc.; ketone solvents such as acetone, methyl isobutyl ketone, etc.; ester solvents such as ethyl acetate, methyl benzoate, etc.; aliphatic hydrocarbon solvents such as hexane, etc. solvents; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, etc.; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, etc.; nitrated hydrocarbon solvents such as nitrobenzene, etc.; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc.; sulfoxide solvents such as dimethyl sulfoxide, etc., etc.

As the bad solvents, there can be listed: nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, phenol, etc.; amine solvents; ether solvents such as diethyl ether, tetrahydrofuran, diphenyl ether, etc.; ketone solvents such as acetone, methyl isobutyl ketone, etc.; ester solvents such as ethyl acetate, methyl benzoate, etc.; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene, trimethylbenzene (e.g., 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene, etc.; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (e.g., 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene, etc.; nitrated hydrocarbon solvents such as nitrobenzene, etc.

As derivatives, there can be listed compounds represented by formula (z) and compounds represented by formula (z1).

[Chemistry 99]

When the liquid containing compound (I) contains a derivative, the content of the derivative is 0.01 mass parts or more and 100 mass parts or less, preferably 0.01 mass parts or more and 70 mass parts or less, more preferably 0.1 mass parts or more and 50 mass parts or less, further preferably 0.1 mass parts or more and 30 mass parts or less, and particularly preferably 0.1 mass parts or more and 20 mass parts or less, relative to 100 mass parts of compound (I).

By containing a dispersant and performing a dispersion treatment, compound (I) can be made into a state where compound (I) is uniformly dispersed in a liquid containing compound (I). When using multiple types of compound (I), each can be dispersed individually or multiple types can be mixed and dispersed.

As the dispersant, there can be cited surfactants, which can be any of cationic, anionic, nonionic and amphoteric surfactants. Specifically, there can be cited polyester-based, polyamine-based and acrylic-based surfactants. These dispersants can be used alone or in combination of two or more. As dispersants, if they are expressed by trade names, they include: KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine Technology Co., Ltd.), and others. Fine-Techno (manufactured by) DISPERBYK (registered trademark) (manufactured by BYK-Chemie (manufactured by)), and BYK (registered trademark) (manufactured by BYK-Chemie (manufactured by) etc.

When the liquid containing compound (I) contains a dispersant, the amount of the dispersant (solid component) used is, for example, 0.01 mass parts or more and 10000 mass parts or less, preferably 0.01 mass parts or more and 5000 mass parts or less, more preferably 0.01 mass parts or more and 1000 mass parts or less, further preferably 0.1 mass parts or more and 500 mass parts or less, particularly preferably 0.1 mass parts or more and 300 mass parts or less, further preferably 1 mass parts or more and 300 mass parts or less, and particularly preferably 5 mass parts or more and 260 mass parts or less, relative to 100 mass parts of compound (I).

If the amount of the dispersant used is within the above range, a liquid containing compound (I) in a more uniformly dispersed state tends to be obtained.

When the coloring composition of the present invention includes a resin (B), and a liquid containing compound (I) containing compound (I) and a solvent (E) is prepared in advance and then used to prepare the coloring composition of the present invention, the liquid containing compound (I) may pre-include a part or all of the resin (B) contained in the coloring composition, preferably a part. By pre-including the resin (B), the dispersion stability of the liquid containing compound (I) can be further improved.

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

[Polymerizable compound (C)]

The polymerizable compound (C) is a compound that can be polymerized by active free radicals and/or acids generated from the polymerization initiator (D), such as a polymerizable compound having ethylenic unsaturated bonds, etc., preferably a (meth)acrylate compound.

As polymerizable compounds having one ethylenically unsaturated bond, for example, there can be listed: nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinyl pyrrolidone, etc., as well as the monomer (a), monomer (b) and monomer (c).

Examples of polymerizable compounds having two ethylenic unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(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 ethylenic unsaturated bonds. Examples of such polymerizable compounds include trihydroxymethylpropane 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, tri(2-(meth)acryl)propene oxyethyl) 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, caprolactone modified pentaerythritol tetra(meth)acrylate and caprolactone modified dipentaerythritol hexa(meth)acrylate, etc., 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, further preferably 50 or more and 3000 or less, particularly preferably 150 or more and 2,900 or less, and particularly preferably 250 or more and 1,500 or less.

In the coloring composition, the content of the polymerizable compound (C) is less than 100 mass%, preferably 0.00001 mass% or more and 99.99999 mass% or less, more preferably 1 mass% or more and 99 mass% or less, further preferably 1 mass% or more and 97 mass% or less, particularly preferably 1 mass% or more and 95 mass% or less, further preferably 1 mass% or more and 90 mass% or less, particularly preferably 2 mass% or more and 80 mass% or less, and extremely preferably 3 mass% or more and 70 mass% or less.

[Polymerization initiator (D)]

The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat to initiate polymerization, and a known polymerization initiator can be used.

As polymerization initiators (D), there can be listed: oxime compounds, such as O-acyl oxime compounds, phenyl alkyl ketone compounds, biimidazole compounds, triazine compounds and acyl phosphine oxide compounds, etc.

As the O-acyl oxime compound, for example, there can be mentioned N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, N-acetyloxy-1-[9-ethyl-6-(2 -methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imine, etc. In addition, as the O-acyl oxime compound, commercially available products such as Irgacure OXE01 and OXE02 (both manufactured by BASF) and N-1919 (manufactured by ADEKA Co., Ltd.) can also be used. Among them, as the O-acyl oxime compound, it is preferred to be at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine and N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, and more preferably N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine.

As the alkyl phenone compound, there can be listed: 2-methyl-2-morpholinyl-1-(4-methylthiophenyl)propane-1-one, 2-dimethylamino-1-(4-morpholinylphenyl)-2-benzylbutane-1-one and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butane-1-one. As the alkyl phenone compound, commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) can also be used.

As alkyl phenone compounds, there can also be listed: 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-〔4-(2-hydroxyethoxy)phenyl〕propane-1-one, 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1-one, α,α-diethoxyacetophenone and benzyl dimethyl ketal, etc.

Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, Japanese Patent Laid-Open No. 6-75372, Japanese Patent Laid-Open No. 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)- 4,4',5,5'-tetrakis(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl)biimidazole (for example, see Japanese Patent Publication No. 48-38403, Japanese Patent Publication No. 62-174204, etc.), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with alkoxycarbonyl (carboalkoxy) (for example, see Japanese Patent Publication No. 7-10913, etc.).

As triazine compounds, there are 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 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-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2 -(5-methylfuran-2-yl)vinyl〕-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-〔2-(furan-2-yl)vinyl〕-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-〔2-(4-diethylamino-2-methylphenyl)vinyl〕-1,3,5-triazine and 2,4-bis(trichloromethyl)-6-〔2-(3,4-dimethoxyphenyl)vinyl〕-1,3,5-triazine, etc.

As the acylphosphine oxide compound, 2,4,6-trimethylbenzyldiphenylphosphine oxide and the like can be cited. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) can also be used.

Furthermore, as the polymerization initiator (D), there can be listed: benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzoyl, methyl phenylglyoxylate, and titaniumocene compounds, etc.

These are preferably used in combination with the polymerization initiator described later (hereinafter, sometimes referred to as polymerization initiator (D1)), especially amines.

The polymerization initiator (D) is preferably a polymerization initiator comprising at least one selected from the group consisting of phenylalkyl ketone compounds, triazine compounds, acyl phosphine oxide compounds, oxime compounds and biimidazole compounds, more preferably a polymerization initiator comprising an oxime compound, and further preferably a polymerization initiator comprising an O-acyl oxime compound.

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

[Polymerization initiation aid (D1)]

The coloring composition of the present invention may also contain a polymerization initiator (D1). The polymerization initiator (D1) is a compound or sensitizer used to promote the polymerization of the polymerizable compound (C) that starts polymerization by the polymerization initiator (D). When the polymerization initiator (D1) is included, it is usually used in combination with the polymerization initiator (D).

Examples of polymerization initiation aids (D1) include amine compounds, alkoxyanthracene compounds, thioanthrone compounds, and carboxylic acid compounds.

As the amine compound, there can be listed: triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isopentyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone and 4,4'-bis(ethylmethylamino)benzophenone, etc., preferably 4,4'-bis(diethylamino)benzophenone. In addition, as the amine compound, commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can also be used.

As alkoxyanthracene compounds, there are: 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene and 2-ethyl-9,10-dibutoxyanthracene, etc.

As thioxanthrone compounds, there can be listed: 2-isopropylthioxanthrone, 4- isopropylthioxanthrone, 2,4-diethylthioxanthrone, 2,4-dichlorothioxanthrone and 1-chloro-4-propoxythioxanthrone, etc.

As carboxylic acid compounds, there can be listed: phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine and naphthoxyacetic acid, etc.

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

[Coloring agent (A1)]

The coloring composition of the present invention may also contain a coloring agent other than compound (I) (hereinafter, referred to as coloring agent (A1)). The coloring agent (A1) may contain one or more coloring agents. The coloring agent (A1) preferably contains one or more selected from yellow coloring agents, orange coloring agents, red coloring agents, and green coloring agents, and more preferably contains one or more selected from yellow coloring agents and green coloring agents.

The coloring agent (A1) may be a dye or a pigment. As the dye, a known dye may be used, for example, the known dyes described in the Color Index (published by The Society of Dyers and Colourists) and the Dyeing Notes (Shikisensha) may be listed. In addition, according to the chemical structure, the following may be listed: azo dyes, cyanine dyes, triphenylmethane dyes, oxyanthracene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azoformine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinophthalone dyes, isoindoline dyes, etc. These dyes may be used alone or in combination of two or more.

Specifically, the dyes with the following color index (C.I.) numbers can be listed.

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 ( orange)2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99; C.I. solvent violet (solvent violet)11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; C.I. solvent blue (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 (solvent C.I. solvent dyes such as green)1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc., C.I. acid yellow (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 (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, 19 5, 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 (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 (acid violet) 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; C.I. acid blue (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 (acid C.I. acid dyes such as green)1,3,5,6,7,8,9,11,13,14,15,16,22,25,27,28,41,50,50:1,58,63,65,80,104,105,106,109, etc., C.I. direct yellow (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 (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 (direct orange)26,34,39,41,46,50,52,56,57,61,64,65,68,70,96,97,106,107; C.I. direct purple (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 (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.Direct Green (direct C.I. direct dyes such as blue, ... 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 (basic violet) 2; C.I. basic red 9; C.I. basic green (basic green) 1 and other C.I. alkaline dyes, C.I. reactive yellow (reactive yellow) 2, 76, 116; C.I. reactive orange (reactive orange) 16; C.I. reactive red (reactive red) 36 and other C.I. reactive dyes, C.I. mordant yellow (mordant yellow) yellow)5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; C.I. mordant red (mordant red)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. mordant orange (mordant 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. 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. mordant blue 1, 1: 1, 2, 3, 4, 5 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. mordant green (mordant green) 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53 and other C.I. mordant dyes, C.I. vat green (vat green) 1 and other C.I. vat dyes, etc.

Furthermore, Lumogen (registered trademark) as a product of BASF can be listed, including: 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).

In addition, compounds represented by formula (z) and compounds represented by formula (z1) can be listed.

As the pigment, known pigments can be used, for example, pigments classified as pigments in the Dye Index (published by The Society of Dyers and Colourists). These can be used alone or in combination of two or more.

Specific examples include: C.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, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231 and other yellow pigments; C.I. pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments; C.I. pigment red Red pigments such as 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 178, 179, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273, etc.; C.I. pigment blue (pigment blue) 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60, etc.; C.I. pigment violet (pigment violet) 1, 19, 23, 29, 32, 36, 38, etc.; C.I. pigment green (pigment Green pigments such as C.I. pigment brown (pigment brown) 23, 25, etc.; C.I. pigment black (pigment black) 1, 7, 31, 32, etc.

As the coloring agent (A1), yellow dyes and yellow pigments (hereinafter, these may be collectively referred to as "yellow coloring agents"), orange dyes and orange pigments (hereinafter, these may be collectively referred to as "orange coloring agents"), red dyes and red pigments (hereinafter, these may be collectively referred to as "red coloring agents"), green dyes and green pigments (hereinafter, these may be collectively referred to as "green coloring agents") are preferred, yellow coloring agents and green coloring agents are more preferred, yellow pigments and green pigments are further preferred, and green pigments are particularly preferred.

As yellow dyes, dyes whose hue is classified as yellow can be cited, and as yellow pigments, pigments whose hue is classified as yellow can be cited.

As yellow coloring agents, yellow dyes and yellow pigments are preferred, yellow pigments are more preferred, quinophthalone pigments, metal-containing pigments, isoindoline pigments are further preferred, C.I. Pigment Yellow 129, 138, 139, 150, 185, 231 are particularly preferred, and C.I. Pigment Yellow 138, 139, 150, 185, 231 are further preferred.

As orange dyes, dyes whose hue is classified as orange can be cited, and as orange pigments, pigments whose hue is classified as orange can be cited.

As orange coloring agents, orange dyes and orange pigments are preferred, orange pigments are more preferred, and C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 are further preferred.

As red dyes, dyes whose hue is classified as red can be cited, and as red pigments, pigments whose hue is classified as red can be cited.

As the red coloring agent, red dyes and red pigments are preferred, and azo dyes, anthraquinone dyes, triphenylmethane dyes, oxyanthracene dyes, perylene dyes, azo pigments, diketopyrrolopyrrole pigments, anthraquinone pigments, triphenylmethane dyes, oxyanthracene pigments and perylene pigments are more preferred, and C.I. Acid Red 52, C.I. Pigment Red 144, 177, 179, 242, 254 and 269 are further preferred.

In addition, as a yellow colorant, an orange colorant, or a red colorant, an oxyanthracene compound described in Japanese Patent Publication No. 2013-235257 may also be used.

As green dyes, dyes whose hue is classified as green can be cited, and as green pigments, pigments whose hue is classified as green can be cited.

As green colorants, green dyes and green pigments are preferred, green pigments are more preferred, phthalocyanine pigments are further preferred, copper phthalocyanine halides, zinc phthalocyanine halides and aluminum zinc phthalocyanine halides are particularly preferred, and C.I. Pigment Green 7, 36, 58, 59, 62 and 63 are further preferred.

[Preparation of liquid containing coloring agent (A1)]

When the coloring composition of the present invention contains a coloring agent (A1), a liquid containing a coloring agent (A1) and a solvent (E) may be prepared in advance, and then the coloring composition may be prepared using the liquid containing a coloring agent (A1). When the coloring agent (A1) is not dissolved in the solvent (E), the liquid containing a coloring agent (A1) may be prepared by dispersing the coloring agent (A1) in the solvent (E) and mixing the two. The liquid containing a coloring agent (A1) may contain a part or all of the solvent (E) contained in the coloring composition.

The content of the solid component in the liquid containing the colorant (A1) is less than 100 mass%, preferably 0.01 mass% or more and 99.99 mass% or less, more preferably 0.1 mass% or more and 99.9 mass% or less, further preferably 0.1 mass% or more and 99 mass% or less, particularly preferably 1 mass% or more and 90 mass% or less, further preferably 1 mass% or more and 80 mass% or less, particularly preferably 1 mass% or more and 70 mass% or less, extremely preferably 1 mass% or more and 60 mass% or less, and most preferably 1 mass% or more and 50 mass% or less.

The content of the colorant (A1) in the liquid containing the colorant (A1) is 100% by mass or less in the total amount of solid components in the liquid containing the colorant (A1), preferably 0.0001% by mass or more and 99.9999% 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, particularly preferably 3% by mass or more and 99% by mass or less, further particularly preferably 5% by mass or more and 99% by mass or less.

The coloring agent (A1) may be subjected to rosin treatment, surface treatment using derivatives with acidic or alkaline groups, grafting treatment on the surface of the coloring agent (A1) using polymer compounds, micronization treatment using sulfuric acid micronization method, salt milling method, etc., cleaning treatment using organic solvents or water to remove impurities, removal treatment of ionic impurities using ion exchange method, etc., crystal structure transformation similar to compound (I), particle shaping and/or particle size roughly uniform treatment, etc. The particle size of the coloring agent (A1) is preferably roughly uniform.

The colorant (A1) can be made uniformly dispersed in a liquid containing the colorant (A1) by containing a dispersant and performing a dispersion treatment. The colorant (A1) can be dispersed individually or by mixing multiple types.

As dispersants, surfactants can be listed, and they can be any of cationic, anionic, nonionic, and amphoteric surfactants. Specifically, polyester-based, polyamine-based, and acrylic-based surfactants can be listed. These dispersants can be used alone or in combination of two or more. Dispersants that are indicated by trade names include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), DISPERBYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), and BYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.).

When the liquid containing the coloring agent (A1) contains a dispersant, the amount of the dispersant (solid component) used is, for example, 0.01 mass parts or more and 10000 mass parts or less, preferably 0.01 mass parts or more and 5000 mass parts or less, more preferably 0.01 mass parts or more and 1000 mass parts or less, further preferably 0.1 mass parts or more and 500 mass parts or less, particularly preferably 0.1 mass parts or more and 300 mass parts or less, further preferably 1 mass parts or more and 300 mass parts or less, and particularly preferably 5 mass parts or more and 260 mass parts or less, relative to 100 mass parts of the coloring agent (A1).

If the amount of the dispersant used is within the above range, a liquid containing the colorant (A1) tends to be obtained in a more uniformly dispersed state.

The coloring composition of the present invention contains a resin (B), and a liquid containing a coloring agent (A1) containing a coloring agent (A1) and a solvent (E) is prepared in advance and then used. When the liquid containing a coloring agent (A1) is used to prepare the coloring composition of the present invention, the liquid containing a coloring agent (A1) may contain a part or all of the resin (B) contained in the coloring composition in advance, preferably a part in advance. By pre-including the resin (B), the dispersion stability of the liquid containing the coloring agent (A1) can be further improved.

When the liquid containing the coloring agent (A1) contains the resin (B), the content of the resin (B) is, for example, 0.01 parts by mass or more and 10,000 parts by mass or less, preferably 0.01 parts by mass or more and 5,000 parts by mass or less, more preferably 0.01 parts by mass or more and 1,000 parts by mass or less, further preferably 0.1 parts by mass or more and 500 parts by mass or less, and particularly preferably 0.1 parts by mass or more and 300 parts by mass or less, relative to 100 parts by mass of the coloring agent (A1).

When the coloring composition of the present invention contains the coloring agent (A1), the content of the coloring agent (A) in the coloring composition, which is a combination of the compound (I) and the coloring agent (A1), is 100% by mass or less, preferably 0.0001% by mass or more and 99.9999% by mass or less, more preferably 0.0001% by mass or more and 99% by mass or less, relative to the total amount of the solid components. The preferred range is 0.0001 mass% or more and 90 mass% or less, the particularly preferred range is 0.0001 mass% or more and 80 mass% or less, the further preferred range is 0.0001 mass% or more and 70 mass% or less, the particularly preferred range is 0.0001 mass% or more and 60 mass% or less, the extremely preferred range is 0.0001 mass% or more and 55 mass% or less, and the most preferred range is 0.1 mass% or more and 55 mass% or less.

When the coloring composition of the present invention contains a coloring agent (A1), the content of compound (I) in the total amount of the coloring agent (A) is usually 0.0001 mass % or more, preferably 0.0003 mass % or more, more preferably 0.0005 mass % or more, and further preferably 0.001 mass % or more, and the upper limit is less than 100 mass %, preferably 99.9999 mass % or less, more preferably 99 mass % or less, further preferably 98 mass % or less, and particularly preferably 97 mass % or less.

[Leveling agent (F)]

As leveling agents (F), silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms can be listed. These may also have polymerizable groups in the side chains.

Examples of silicone-based surfactants include surfactants having siloxane bonds in the molecule. Specifically, they include: Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (trade name: Toray Dow Corning) Corning (manufactured by), 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 Co., Ltd.), etc.

As fluorine-based surfactants, surfactants having fluorine-carbon chains in the molecule can be cited. Specifically, they include: Fluorad (registered trademark) FC430, Fluorad (Fluorad) FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafac (registered trademark) F142D, Megafac F171, Megafac F172, Megafac F173, Megafac F177, Megafac F183, Megafac F554, Megafac R30, Megafac RS-718-K (manufactured by DIC Corporation), Eftop (registered trademark) EF301, Eftop EF303, Eftop EF351, Eftop EF352 (manufactured by Mitsubishi Materials Corporation), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by Asahi Glass Corporation) and E5844 (manufactured by Daikin Fine Chemical Laboratories, Ltd.), etc.

As silicone-based surfactants having fluorine atoms, surfactants having siloxane bonds and fluorocarbon chains in the molecule can be cited. Specifically, Megafac (registered trademark) R08, Megafac BL20, Megafac F475, Megafac F477 and Megafac F443 (manufactured by DIC Corporation) can be cited.

When a leveling agent (F) is contained, its content is generally 0.00001 mass % or more and 5 mass % or less, preferably 0.00001 mass % or more and 3 mass % or less, more preferably 0.0001 mass % or more and 2 mass % or less, and even more preferably 0.0001 mass % or more and 1 mass % or less, relative to the total amount of the coloring composition.

If 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 perspective of improving the heat resistance and light resistance of the coloring agent, it is preferred to use an antioxidant alone or in combination of two or more. As an antioxidant, there is no particular limitation as long as it is an antioxidant commonly used in industry, and phenolic antioxidants, phosphorus antioxidants, sulfur antioxidants, etc. can be used.

As the phenolic antioxidant, for example, there can be cited: 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), Irganox 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: Phenylpropionic 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 (Irganox 3125, manufactured by BASF), Irganox 565 (Irganox 565: 2,4-bis(n-octylthio)-6-(4-hydroxy-3',5'-di-tert-butylanilino)-1,3,5-triazine, manufactured by BASF), Adekastab AO-80 (Adekastab AO-80: 3,9-bis(2-(3-(3-tert-butyl-4-hydroxyl -5-methylphenyl)propionyloxy)-1,1-dimethylethyl)-2,4,8,10-tetraoxahyspiro(5,5)undecane, manufactured by ADEKA Co., Ltd.), Sumilizer BHT (manufactured by Sumitomo Chemical Co., Ltd.), Sumilizer GA-80 (manufactured by Sumitomo Chemical Co., Ltd.), Sumilizer GS (manufactured by Sumitomo Chemical Co., Ltd.), Cyanox 1790 (manufactured by Cytec Co., Ltd.) and Vitamin E (manufactured by Eisai Co., Ltd.), etc.

As the phosphorus-based antioxidant, for example, there can be cited: 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-butyl dibenzo [d, f] [1,3,2] dioxaphosphin-6-yl] oxy] ethyl] amine, manufactured by BASF), Irgafos 38 (Irgafos 38: Bis(2,4-bis(1,1-dimethylethyl)-6-methylphenyl)ethyl phosphite, manufactured by BASF), Adekastab 329K (manufactured by ADEKA), Adekastab PEP36 (manufactured by ADEKA), Adekastab PEP-8 (manufactured by ADEKA), Sandstab P-EPQ (manufactured by Clariant), Weston 618 (manufactured by GE), Weston 619G (manufactured by GE), Ultranox 626 (manufactured by 626, manufactured by GE) and Sumilizer GP (Sumilizer GP: 6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-tert-butyldibenzo[d,f][1.3.2]dioxophosphin) (manufactured by Sumitomo Chemical Co., Ltd.), etc.

As the sulfur-based antioxidant, for example, there can be listed: dialkyl thiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl thiodipropionate or distearyl thiodipropionate, and β-alkyl propionate compounds of polyols such as tetrakis[methylene(3-dodecylthio)propionate]methane, etc.

[Other ingredients]

The coloring composition of the present invention may also contain fillers, other polymer compounds, adhesion promoters, light stabilizers, chain transfer agents and other additives known in the technical field as needed.

Examples of the adhesion promoter include vinyl trimethoxysilane, vinyl triethoxysilane, vinyl tri(2-methoxyethoxy)silane, 3-glycidyloxypropyl trimethoxysilane, 3-glycidyloxypropyl methyl dimethoxysilane, 3-glycidyloxypropyl methyl diethoxysilane, 2-(3,4-epoxycyclohexyl)ethyl trimethoxysilane, 3-chloropropyl methyl dimethoxysilane, 3-chloropropyl trimethoxysilane, 3-methacryloyloxypropyl trimethoxysilane, 3-butyl propyl trimethoxysilane, 3-thiophene propyl trimethoxysilane, 3-isocyanate propyl triethoxysilane, N-2-(aminoethyl)-3-aminopropyl methyl dimethoxysilane, N-2-(aminoethyl)-3-aminopropyl methyl diethoxysilane, N-2-(aminoethyl)-3-aminopropyl trimethoxysilane, N-2-(aminoethyl)-3-aminopropyl methyl diethoxysilane, 3-aminopropyl trimethoxysilane, 3-aminopropyl triethoxysilane, N-phenyl-3-aminopropyl trimethoxysilane and N-phenyl-3-aminopropyl triethoxysilane, etc.

[Method for producing coloring composition]

The coloring composition of the present invention can be prepared by mixing, for example, compound (I), solvent (E), and, if necessary, resin (B), polymerizable compound (C), polymerization initiator (D), polymerization initiator aid (D1), coloring agent (A1), leveling agent (F), antioxidant (G) and/or other components. The mixing can be performed by known or conventional devices or conditions.

Compound (I) is preferably used in the form of a liquid containing compound (I), wherein the liquid containing compound (I) is prepared by mixing compound (I) with a part or all of solvent (E) in advance and dispersing compound (I) using a bead mill or the like until the average particle size of compound (I) is about 0.2 μm or less. At this time, part or all of the dispersant and resin (B) may be prepared as needed.

The colorant (A1) is preferably used in the form of a liquid containing the colorant (A1), wherein the liquid containing the colorant (A1) is prepared by pre-mixing the colorant (A1) with a part or all of the solvent (E), and dispersing the colorant (A1) using a bead mill or the like until the average particle size of the colorant (A1) is about 0.2 μm or less. At this time, a part or all of the dispersant and the resin (B) may be prepared as needed.

The compound (I) is preferably used in the form of a solution pre-dissolved in a part or all of the solvent (E) (the solution is contained in the liquid containing the compound (I)). Furthermore, it is preferred to filter the liquid containing the compound (I) using a filter having a pore size of about 0.01 μm or more and about 1 μm or less.

The coloring agent (A1) is preferably used in the form of a solution pre-dissolved in a part or all of the solvent (E) (the solution is contained in the liquid containing the coloring agent (A1)). Furthermore, it is preferred to filter the liquid containing the coloring agent (A1) using a filter with a pore size of about 0.01 μm or more and about 1 μm or less.

It is preferred to filter the mixed coloring composition using a filter with a pore size of about 0.01 μm or more and about 10 μm or less.

[Color filter]

A color filter can be formed from the coloring composition of the present invention.

The coloring composition is applied on a substrate, volatile components such as solvents are removed and dried to form a coloring film. The coloring film thus formed is included in the color filter of the present invention.

As methods for forming a coloring pattern, photolithography, inkjet, printing, etc. can be cited. Among them, photolithography is preferred. Photolithography is a method of coating the coloring composition on a substrate, drying it to form a coloring composition layer, and exposing and developing the coloring composition layer through a photomask. In photolithography, by not using a photomask during exposure and/or not developing, a coloring film can be formed as a cured product of the coloring composition layer. The coloring pattern or coloring film formed in this way is the color filter of the present invention.

The film thickness of the produced color filter is not particularly limited and can be appropriately adjusted according to the purpose or use, for example, 0.1μm~30μm, preferably 0.1μm~20μm, and more preferably 0.5μm~6μm.

As the substrate, quartz glass, borosilicate glass, alumina silicate glass, sodium calcium glass with silicon dioxide coated on the surface, or resin plates such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicon, and aluminum, silver, silver/copper/palladium alloy thin films formed on the substrate can be used. Other color filter layers, resin layers, transistors, circuits, etc. can also be formed on these substrates.

The formation of pixels of various colors by photolithography can be performed by known or conventional devices or conditions. For example, it can be produced in the following manner.

First, the coloring composition is applied to the substrate, and then volatile components such as solvents are removed and dried by heat drying (pre-baking) and/or reduced pressure drying to obtain a smooth coloring composition layer.

As coating methods, there are rotary coating, slit coating, and slit and rotary coating.

The temperature for heating and drying is preferably 30℃~120℃, more preferably 50℃~110℃. In addition, the heating time is preferably 10 seconds~60 minutes, more preferably 30 seconds~30 minutes. When performing reduced pressure drying, it is preferably carried out at a pressure of 50Pa~150Pa and a temperature range of 20℃~25℃. The film thickness of the coloring composition layer is not particularly limited, as long as it is appropriately selected according to the film thickness of the target color filter.

Secondly, the coloring composition layer is interposed with a photomask for forming a target coloring pattern.

The pattern on the mask is not particularly limited, and a pattern corresponding to the target application can be used. As the light source used in the exposure, it is preferably a light source that generates light with a wavelength of 250nm~450nm. For example, for light less than 350nm, a filter that cuts off the wavelength region can be used to cut off, or for light near 436nm, near 408nm, and near 365nm, a bandpass filter that takes out these wavelength regions can be used to selectively take out. As specific examples of light sources, mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps can be listed.

In order to evenly irradiate the entire exposure surface with parallel light or to accurately align the position of the mask and the substrate on which the colored component layer is formed, it is preferable to use an exposure device such as a mask aligner and a stepper.

The exposed coloring composition layer is brought into contact with a developer to form a coloring pattern on the substrate. By developing, the unexposed portion of the coloring composition layer is dissolved in the developer and removed.

As a developer, preferably, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide is used.

The concentration of the alkaline compound is preferably 0.01 mass% to 10 mass%, and more preferably 0.02 mass% to 5 mass%. The developer may contain a surfactant.

The developing method can be any of the liquid coating method, immersion method and spray method. Furthermore, during the development, the substrate can be tilted at any angle.

The substrate is preferably washed with water after development.

Furthermore, it is preferred to post-bake the obtained colored pattern.

The post-baking temperature is preferably 150℃~250℃, more preferably 160℃~235℃. The post-baking time is preferably 1 minute~120 minutes, more preferably 10 minutes~60 minutes. The colored pattern or colored coating film obtained in this way, i.e., the color filter, can also be used in surface coating treatment in order to impart various properties.

The color filter is useful as a color filter used in display devices (e.g., liquid crystal display devices, organic electroluminescence (EL) devices, electronic paper, etc.) and solid-state imaging elements, and is particularly useful as a color filter used in liquid crystal display devices.

This 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.

[Implementation example]

The following examples are given to more specifically illustrate the present invention, but the present invention is not limited to the following examples at all, and can of course be implemented with appropriate changes within the scope of the above and the following subject matter, all of which are included in the technical scope of the present invention. Furthermore, below, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass".

In the following synthesis examples, the structures of the compounds were confirmed by mass analysis (LC; Model 1200 manufactured by Agilent, MASS; Model LC/MSD6130 manufactured by Agilent).

The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were determined by gel permeation chromatography (GPC) under the following conditions.

Device: HLC-8120GPC (manufactured by Tosoh Co., Ltd.)

Column: TSK-GELG2000HXL

Column temperature: 40℃

Solvent: Tetrahydrofuran

Flow rate: 1.0mL/min

Solid content concentration of the analyzed sample: 0.001 mass%~0.01 mass%

Injection volume: 50μL

Detector: RI

Standard materials for calibration: TSK standard polystyrene F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Co., Ltd.)

The ratio (Mw/Mn) of the obtained polystyrene-converted weight average molecular weight (Mw) and number average molecular weight (Mn) is defined as the dispersion degree.

Implementation Example 1

Mix 3.02 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 8.33 parts of 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 11.7 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 66.7 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).

The mixture was stirred for 9 hours while being maintained at 170°C.

13.6 parts of 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 22.9 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 66.4 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

The mixture was stirred for 49 hours while being maintained at 170°C.

8.32 parts of 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 11.7 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 43.5 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

The mixture was stirred for 28 hours while being maintained at 170°C.

The mixture was cooled to room temperature and 1300 parts of methanol were added to the mixture.

The mixture was stirred at room temperature, 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.

Add 875 parts of N,N-dimethylformamide to the residue.

After the mixture was stirred at room temperature, it was filtered and the residue was washed three times with the same volume of N,N-dimethylformamide as the residue.

The residue was washed three times with 200 parts of methanol.

The obtained residue was dried under reduced pressure at 60°C to obtain 7.25 parts of the compound represented by formula (Ia2).

<Identification of the compound represented by formula (Ia2)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 519

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 517

Exact Mass: 518

Example 2

Mix 2.05 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 8.16 parts of tetrachlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 8.05 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 58.6 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).

The mixture was stirred for 5 hours while being maintained at 170°C.

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 18.0 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

The mixture was stirred for 6 hours while being maintained at 170°C.

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 54.5 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

The mixture was stirred for 6 hours while being maintained 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 18.4 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

The mixture was stirred for 16 hours while being maintained at 170°C.

The mixture was cooled to room temperature and 1200 parts of methanol were added to the mixture.

The mixture was stirred at room temperature, 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 the compound represented by formula (Ia23).

<Identification of the compound represented by formula (Ia23)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 691

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 689

Exact Mass: 690

Implementation Example 3

Mix 1.01 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.49 parts of 4-phenylethynylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.95 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 28.7 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).

The mixture was stirred for 20 hours while being maintained at 170°C.

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 3.3 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

The mixture was stirred for 10 hours while being maintained at 170°C.

0.801 parts 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 9.13 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

The mixture was stirred for 29 hours while being maintained at 170°C.

The mixture was cooled to room temperature, 400 parts of methanol was added to the mixture and stirred for 1 hour.

The mixture was filtered and the obtained 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 formula (Ia22).

<Identification of the compound represented by formula (Ia22)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 619

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 617

Exact Mass: 618

Example 4

Mix 4.04 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 10.8 parts of trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 15.6 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 92.3 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).

The mixture was stirred for 5 hours while being maintained at 167°C.

40.2 parts of methyl benzoate (produced by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

The mixture was stirred for 9 hours while being maintained at 167°C.

28.0 parts of methyl benzoate (produced by Tokyo Chemical Industry Co., Ltd.) was added to the mixture.

The mixture was stirred for 11 hours while being maintained at 170°C.

The mixture was cooled to room temperature and 2000 parts of methanol were added to the mixture.

The mixture was stirred at room temperature.

173 parts of methanol were added to the obtained mixture.

The mixture was filtered, and the obtained residue was washed once with 124 parts of methanol, once with 160 parts of methanol, and once with 400 parts of methanol.

The obtained residue was dried under reduced pressure at 60°C to obtain 9.91 parts of a mixture of a compound represented by formula (Ia10), a compound represented by formula (Ia2143), a compound represented by formula (Ia850), and a compound represented by formula (Ia315).

<Identification of the compound represented by formula (Ia10)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 507

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 505

Exact Mass: 506

[Chemistry 106]

<Identification of the compound represented by formula (Ia2143)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 521

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 519

Exact Mass: 520

<Identification of the compound represented by formula (Ia850)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 521

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 519

Exact Mass: 520

<Identification of the compound represented by formula (Ia315)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 535

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 533

Exact Mass: 534

Example 5

Mix 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.), 20.2 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 119 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).

The mixture was stirred for 12 hours while being maintained at 168°C.

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 16.0 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

The mixture was stirred for 26 hours while being maintained at 170°C.

The mixture was cooled to room temperature and 2400 parts of methanol were added to the mixture.

The obtained mixture was stirred at room temperature and then filtered.

The obtained residue was washed five 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 formula (Ia35).

<Identification of the compound represented by formula (Ia35)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 509

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 507

Exact Mass: 508

Example 6

Mix 3.67 parts of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 7.59 parts of phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 14.4 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 84.3 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).

The mixture was stirred for 10 hours while being maintained at 170°C.

Add 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 45 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) to the mixture.

The mixture was stirred for 9 hours while being maintained at 170°C.

Add 9 parts of methyl benzoate (produced by Tokyo Chemical Industry Co., Ltd.) to the mixture.

The mixture was stirred for 18 hours while being maintained at 170°C.

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 11.1 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

The mixture was stirred for 27 hours while being maintained at 170°C.

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 12.3 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

The mixture was stirred for 8 hours while being maintained at 170°C.

The mixture was cooled to room temperature and 2800 parts of methanol were added to the mixture.

The obtained 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 the compound represented by formula (Ia1).

<Identification of the compound represented by formula (Ia1)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 419

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 417

Exact Mass: 418

Example 7

1.05 parts of a mixture of the compound represented by formula (Ia10) obtained in Example 4, the compound represented by formula (Ia2143), the compound represented by formula (Ia850) and the compound represented by formula (Ia315) were mixed with 106 parts of water.

At room temperature, add 22.1 parts of 1% sodium hydroxide aqueous solution to the mixture.

At room temperature, 8.19 parts of a mixture of 3.23 parts of iron nitrate (III) nonahydrate (produced by Wako Pure Chemical Industries, Ltd.) and 29.1 parts of water were added to the obtained mixture.

The obtained mixture was filtered and the obtained residue was washed twice with water having the same volume as the obtained residue.

The obtained residue was dried under reduced pressure at 60°C to obtain 1.17 parts of a mixture containing a compound represented by formula (Ie12).

Example 8

Mix 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.), 19.5 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 116 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.).

The mixture was stirred for 4 hours while being maintained at 170°C.

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 30.1 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

The mixture was stirred for 18 hours while being maintained at 170°C.

13.6 parts of 4-nitrophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 19.9 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 29.1 parts of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the mixture.

The mixture was stirred for 27 hours while being maintained at 170°C.

The mixture was cooled to room temperature and 2800 parts of methanol were added to the mixture.

The obtained 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 formula (Ia33).

<Identification of the compound represented by formula (Ia33)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 509

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 507

Exact Mass: 508

Example A-1

Mix 1 mol of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.), 8 mol of 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 21 mol of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) in an amount 73 times the weight of 1 mol of 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.).

The mixture was stirred for 120 hours while being maintained at 170°C.

The mixture was cooled to room temperature, and methanol in an amount 13 times the weight of the mixture was added to the mixture.

The obtained mixture was stirred at room temperature and then filtered.

The obtained residue is washed with methanol.

The obtained residue is purified by column chromatography to obtain the compound represented by formula (Ia5).

<Identification of the compound represented by formula (Ia5)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 447

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 445

Exact Mass: 446

Example A-2

The same method as Example A-1 was followed 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.) to obtain a compound represented by formula (Ia3).

<Identification of the compound represented by formula (Ia3)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 519

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 517

Exact Mass: 518

Example A-3

The same method as Example A-1 was followed except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was used to replace 3-chlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (Ia17).

[Chemistry 115]

<Identification of the compound represented by formula (Ia17)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 487

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 485

Exact Mass: 486

Example A-4

The same method as Example A-1 was followed 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.) to obtain a compound represented by formula (Ia7).

<Identification of the compound represented by formula (Ia7)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 487

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 485

Exact Mass: 486

Example A-5

The same method as Example A-1 was followed except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was used to replace 3-acetamidophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (Ia36).

<Identification of the compound represented by formula (Ia36)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 533

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 531

Exact Mass: 532

Example A-6

The same method as Example A-1 was followed except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was used to replace 3-hydroxyphthalic anhydride (manufactured by Sigma-Aldrich Japan Co., Ltd.) to obtain a compound represented by formula (Ia51).

<Identification of the compound represented by formula (Ia51)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 451

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 449

Exact Mass: 450

Example A-7

The same method as Example A-1 was followed 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.) to obtain a compound represented by formula (Ia19).

[Chemistry 119]

<Identification of the compound represented by formula (Ia19)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 455

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 453

Exact Mass: 454

Example A-8

The same method as Example A-1 was followed except that 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with the compound represented by formula (sm1) to obtain the compound represented by formula (Ia248).

[Chemistry 121]

<Identification of the compound represented by formula (Ia248)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 507

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 505

Exact Mass: 506

Example A-9

The same method as Example A-1 was followed 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.) to obtain a compound represented by formula (Ia4).

<Identification of the compound represented by formula (Ia4)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 447

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 445

Exact Mass: 446

Example A-10

The same method as in Example A-1 was followed except that 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 4-amino-6-fluoro-2-methylquinoline (manufactured by Sigma-Aldrich Japan Co., Ltd.), and 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.). The compound represented by formula (It242) was obtained.

<Identification of the compound represented by formula (It242)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 537

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 535

Exact Mass: 536

Example A-11

The same method as in Example A-1 was followed except that 4-amino-2-methylquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 4-amino-6-methoxy-2-methylquinoline (manufactured by Sigma-Aldrich Japan Co., Ltd.), and 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.). The compound represented by formula (It232) was obtained.

<Identification of the compound represented by formula (It232)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 549

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 547

Exact Mass: 548

Example A-12

The same method as Example A-1 was followed 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 Co., Ltd.) to obtain a compound represented by formula (It750).

<Identification of the compound represented by formula (It750)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 525

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 523

Exact Mass: 524

Synthesis Example B-1

Mix 1 mol of the compound represented by formula (Ia2), 20 mol of potassium hydroxide, and a mixture of water 10 times the weight of 1 mol of the compound represented by formula (Ia2).

The mixture was stirred while being maintained at 90°C until the compound represented by formula (Ia2) disappeared.

Neutralize the mixture by mixing it with 36% hydrochloric acid.

The mixture was filtered.

The obtained residue is washed with water.

The residue was purified by column chromatography to obtain the compound represented by formula (IM1-1).

<Identification of the compound represented by formula (IM1-1)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 339

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 337

Exact Mass: 338

Synthesis Example B-2

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

[Chemistry 127]

<Identification of the compound represented by formula (IM1-2)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 425

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 423

Exact Mass: 424

Synthesis Example B-3

The compound represented by formula (IM1-3) was obtained by performing the same method as in Synthesis Example B-1 except that the compound represented by formula (Ia2) was replaced by the compound represented by formula (Ia5).

<Identification of the compound represented by formula (IM1-3)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 303

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 301

Exact Mass: 302

Synthesis Example B-4

The compound represented by formula (IM1-4) was obtained by performing the same method as in Synthesis Example B-1 except that the compound represented by formula (Ia2) was replaced by the compound represented by formula (Ia4).

<Identification of the compound represented by formula (IM1-4)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 303

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 301

Exact Mass: 302

Synthesis Example B-5

The compound represented by formula (IM1-5) was obtained by performing the same method as in Synthesis Example B-1 except that the compound represented by formula (Ia2) was replaced by the compound represented by formula (Ia36).

[Chemistry 130]

<Identification of the compound represented by formula (IM1-5)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 346

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 344

Exact Mass: 345

Synthesis Example B-6

The compound represented by formula (IM1-6) was obtained by performing the same method as in Synthesis Example B-1 except that the compound represented by formula (Ia2) was replaced by the compound represented by formula (Ia1).

<Identification of the compound represented by formula (IM1-6)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 289

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 287

Exact Mass: 288

Example C-1

Mix 1 mol of the compound represented by 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 methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) in an amount 73 times the weight of 1 mol of the compound represented by formula (IM1-1).

The mixture was stirred for 120 hours while being maintained at 170°C.

The mixture was cooled to room temperature, and methanol in an amount 13 times the weight of the mixture was added to the mixture.

The obtained mixture was stirred at room temperature and then filtered.

The obtained residue is washed with methanol.

The obtained residue is purified by column chromatography to obtain the compound represented by formula (Ia699).

<Identification of the compound represented by formula (Ia699)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 513

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 511

Exact Mass: 512

Example C-2

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

<Identification of the compound represented by formula (Ia970)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 605

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 603

Exact Mass: 604

Example C-3

The same method as Example C-1 was followed except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with tetrachlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (Ia703).

<Identification of the compound represented by formula (Ia703)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 605

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 603

Exact Mass: 604

Example C-4

The same method as Example C-1 was followed except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (If3796).

[Chemistry 135]

<Identification of the compound represented by formula (If3796)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 483

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 481

Exact Mass: 482

Example C-5

The same method as Example C-1 was followed except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (Ia696).

<Identification of the compound represented by formula (Ia696)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 469

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 467

Exact Mass: 468

Example C-6

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

<Identification of the compound represented by formula (Ia969)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 555

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 553

Exact Mass: 554

Example C-7

The compound represented by formula (If2528) was obtained by carrying out the same method as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-2) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 3-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

<Identification of the compound represented by formula (If2528)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 569

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 567

Exact Mass: 568

Example C-8

The compound represented by formula (Ia973) was obtained by carrying out the same method as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-2).

[Chemistry 139]

<Identification of the compound represented by formula (Ia973)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 599

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 597

Exact Mass: 598

Example C-9

The compound represented by formula (If1261) is obtained by performing the same method as Example C-1 except that the compound represented by formula (IM1-1) is replaced by the compound represented by formula (IM1-3).

[Chemistry 140]

<Identification of the compound represented by formula (If1 261)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 477

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 475

Exact Mass: 476

Example C-10

The same method as Example C-1 was followed except that the compound represented by Formula (IM1-1) was replaced by the compound represented by Formula (IM1-3) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by tetrachlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), to obtain the compound represented by Formula (If5688).

<Identification of the compound represented by formula (If5688)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 569

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 567

Exact Mass: 568

Example C-11

The compound represented by formula (If636) was obtained in the same manner as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-3) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

<Identification of the compound represented by formula (If636)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 483

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 481

Exact Mass: 482

Example C-12

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

<Identification of the compound represented by formula (If5670)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 483

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 481

Exact Mass: 482

Example C-13

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

<Identification of the compound represented by formula (If5720)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 483

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 481

Exact Mass: 482

Example C-14

The same method as Example C-1 was followed except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 1,8-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (Ia712).

<Identification of the compound represented by formula (Ia712)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 519

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 517

Exact Mass: 518

Example C-15

The compound represented by formula (If635) was obtained in the same manner as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-4) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

<Identification of the compound represented by formula (If635)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 483

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 481

Exact Mass: 482

Example C-16

The compound represented by formula (If1260) is obtained by performing the same method as Example C-1 except that the compound represented by formula (IM1-1) is replaced by the compound represented by formula (IM1-4).

<Identification of the compound represented by formula (If1260)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 477

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 475

Exact Mass: 476

Example C-17

The compound represented by formula (If13040) was obtained by carrying out the same method as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-4) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by pyromellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

[Chemistry 148]

<Identification of the compound represented by formula (If1 3040)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 521

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 519

Exact Mass: 520

Example C-18

The compound represented by formula (If8454) was obtained by carrying out the same method as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-4) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 4-tert-butylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

<Identification of the compound represented by formula (If8454)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 489

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 487

Exact Mass: 488

Example C-19

The same method as Example C-1 was followed except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (If3795).

<Identification of the compound represented by formula (If3795)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 483

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 481

Exact Mass: 482

Example C-20

The same method as Example C-1 was followed except that the compound represented by Formula (IM1-1) was replaced by the compound represented by Formula (IM1-3) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 4-methylphthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain the compound represented by Formula (If5671).

<Identification of the compound represented by formula (If5671)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 447

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 445

Exact Mass: 446

Example C-21

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

[Chemistry 152]

<Identification of the compound represented by formula (If2511)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 447

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 445

Exact Mass: 446

Example C-22

The same method as Example C-1 was followed 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.) to obtain a compound represented by formula (If3799).

<Identification of the compound represented by formula (If3799)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 525

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 523

Exact Mass: 524

Example C-23

The same method as Example C-1 was followed except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 3-acetamidophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain a compound represented by formula (If3814).

<Identification of the compound represented by formula (If3814)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 526

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 524

Exact Mass: 525

Example C-24

The compound represented by formula (If654) was obtained by carrying out the same method as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-5) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

<Identification of the compound represented by formula (If654)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 526

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 524

Exact Mass: 525

Example C-25

The same method as Example C-1 was followed except that the compound represented by Formula (IM1-1) was replaced by the compound represented by Formula (IM1-5) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by phthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), to obtain the compound represented by Formula (If29).

[Chemistry 156]

<Identification of the compound represented by formula (If29)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 476

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 474

Exact Mass: 475

Example C-26

The compound represented by formula (If1279) is obtained by performing the same method as Example C-1 except that the compound represented by formula (IM1-1) is replaced by the compound represented by formula (IM1-5).

<Identification of the compound represented by formula (If1 279)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 520

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 518

Exact Mass: 519

Example C-27

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

<Identification of the compound represented by formula (If1904)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 520

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 518

Exact Mass: 519

Example C-28

The same method as Example C-1 was followed except that trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with the compound represented by formula (sm1) to obtain the compound represented by formula (Ia728).

<Identification of the compound represented by formula (Ia728)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 513

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 511

Exact Mass: 512

Example C-29

The compound represented by formula (Ia657) was obtained in the same manner as Example C-1 except that the compound represented by formula (IM1-1) was replaced by the compound represented by formula (IM1-6) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.).

[Chemistry 160]

<Identification of the compound represented by formula (Ia657)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 469

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 467

Exact Mass: 468

Example C-30

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

<Identification of the compound represented by formula (If3171)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 433

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 431

Exact Mass: 432

Example C-31

The same method as Example C-1 was followed except that the compound represented by Formula (IM1-1) was replaced by the compound represented by Formula (IM1-6) and trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced by 3-chlorophthalic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) to obtain the compound represented by Formula (Ia686).

<Identification of the compound represented by formula (Ia686)>

(Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 453

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 451

Exact Mass: 452

Example E-1

1.61 parts of the compound represented by formula (Ia5) and 32.7 parts of fuming sulfuric acid (25%) (manufactured by Fuji Films and Wako Pure Chemical Industries, Ltd.) were mixed while maintaining the temperature at 10°C to 20°C.

The mixture was stirred for 3 hours while being kept at 5℃~20℃.

The mixture was added dropwise to 62.2 parts of ice.

The obtained mixture was filtered.

Add 10% ammonia water to the obtained liquid to neutralize the obtained filter liquid.

Distill the solvent from the mixture until the volume of the mixture is reduced to half.

To the obtained mixture, methanol in a volume twice the volume of the mixture was added.

The mixture is filtered, and the solvent is distilled off from the obtained filtrate.

The obtained residue was dried under reduced pressure at 60°C to obtain 0.58 parts of a mixture of a compound represented by formula (Ia5-SA1) (a compound in which one hydrogen atom of the compound represented by formula (Ia5) is replaced by -SO ₃ NH ₄ ) and a compound represented by formula (Ia5-SA2) (a compound in which two hydrogen atoms of the compound represented by formula (Ia5) are replaced by -SO ₃ NH ₄ ).

<Identification of compounds represented by formula (Ia5-SA1)>

(Mass analysis) Ionization mode = ESI-: m/z = [M-NH ₄ +HH] ^- 525

Exact Mass: 543

<Identification of compounds represented by formula (Ia5-SA2)>

(Mass analysis) Ionization mode = ESI-: m/z = [M-NH ₄ -NH ₄ +H+HH] ^- 605

Exact Mass: 640

Example E-2

Mix 0.30 parts of the compound represented by formula (Ia1), 3.00 parts of chloroform, and 0.55 parts of chlorosulfonic acid (produced by Tokyo Chemical Industry Co., Ltd.).

The mixture was stirred for 3 hours while being maintained at 60°C.

The mixture was added dropwise to 3.64 parts of ice.

The obtained mixture is filtered and the obtained residue is washed with water.

The residue is washed with methanol.

The residue was dried under reduced pressure at 60°C to obtain 0.18 parts of a mixture containing a compound represented by formula (Ia1-SA1) (a compound in which one hydrogen atom of the compound represented by formula (Ia1) is substituted with _-SO3H ) and a compound represented by formula (Ia1-SA2) (a compound in which one hydrogen atom of the compound represented by formula (Ia1) is substituted with _-SO2Cl ).

<Identification of compounds represented by formula (Ia1-SA1)>

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 497

Exact Mass: 498

<Identification of compounds represented by formula (Ia1-SA2)>

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 515

Exact Mass: 516

Example E-3

1.00 parts of the compound represented by formula (Ia2) and 20.6 parts of fuming sulfuric acid (30%) (manufactured by Fuji Films and Wako Pure Chemical Industries, Ltd.) were mixed at room temperature.

The mixture was stirred at room temperature for 3 hours.

The mixture was added dropwise to 208 parts of ice.

The obtained mixture was mixed with 110 parts of acetonitrile.

The mixture was filtered and the resulting residue was washed with acetonitrile.

The residue was dried under reduced pressure at 60°C to obtain 0.40 parts of a mixture containing a compound represented by formula (Ia2-SA) (a compound in which any two hydrogen atoms of the compound represented by formula (Ia2) are replaced by -SO ₃ H).

<Identification of compounds represented by formula (Ia2-SA)>

(Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 677

Exact Mass: 678

Synthesis Example 1

A suitable amount of nitrogen was passed through a flask including a reflux cooler, a dropping funnel and a stirrer to replace the atmosphere with a nitrogen atmosphere, and 280 parts of propylene glycol monomethyl ether acetate was added and heated to 80°C while stirring. Subsequently, a mixed solution of 38 parts of acrylic acid, 289 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-9-yl acrylate (containing ratio of 1:1 in molar ratio) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution prepared by dissolving 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was completed, 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 weight average molecular weight of the obtained resin B1 was 8800, the degree of dispersion was 2.1, and the acid value converted to solid content was 80 mg-KOH/g.

Synthesis Example 2

A suitable amount of nitrogen was passed through a flask including a reflux cooler, a dropping funnel and a stirrer to replace the atmosphere with a nitrogen atmosphere, and 340 parts of propylene glycol monomethyl ether acetate was added and heated to 80°C while stirring. Subsequently, a mixed solution of 57 parts of acrylic acid, 54 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-9-yl acrylate (containing ratio of 1:1 in terms of 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 prepared by dissolving 40 parts of 2,2-azobis(2,4-dimethylvaleronitrile) in 197 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was completed, 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 9400, the degree of dispersion was 1.89, and the acid value calculated as solid content was 114 mg-KOH/g.

Example 9

Mix the components in the following proportions and disperse the colorant using a bead mill to obtain a coloring composition M1.

Colorant (A): 4.50 parts of the compound represented by formula (Ia2); Colorant (A): 0.500 parts of the compound represented by formula (z); Dispersant solution: 16.7 parts of DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 46.9 parts of propylene glycol monomethyl ether acetate; Solvent (E): 20.0 parts of ethyl lactate; Then, the 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 (Toray Dow Corning Co., Ltd.) 0.00630 parts; [Chemical 168]

The coloring composition 1 was applied on a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

The film thickness of the obtained pre-baked pigmented coating film was measured using DektakXT (manufactured by BRUKER).

The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked color coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

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

The compound represented by formula (Ia2) is replaced by the compound represented by formula (Ia23). The same procedure as in Example 9 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

The film thickness of the pre-baked color coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

Example 11

The same process as in Example 9 was performed except that the compound represented by formula (Ia2) was replaced by the compound represented by formula (Ia10) obtained in Example 4, the compound represented by formula (Ia2143), the compound represented by formula (Ia850) and the mixture of the compound represented by formula (Ia315), to obtain a coloring composition, a pre-baked coloring film and a post-baked coloring film.

The film thickness of the pre-baked color coating film and the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

Example 12

The compound represented by formula (Ia2) is replaced by the compound represented by formula (Ia35). The same method as in Example 9 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

The film thickness of the pre-baked color coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

Example 13

Mix the components in the following proportions, and use a bead mill to disperse the colorant to obtain a coloring composition M2.

Colorant (A): 4.50 parts of the compound represented by formula (Ia1); Colorant (A): 0.500 parts of the compound represented by formula (z); Dispersant solution: 8.33 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 55.2 parts of propylene glycol monomethyl ether acetate; Solvent (E): 20.0 parts of ethyl lactate; Then, the 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 (Toray Dow Corning Co., Ltd.) 0.00630 parts; Coloring composition 2 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

The film thickness of the obtained pre-baked pigmented coating film was measured using DektakXT (manufactured by BRUKER).

The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked color coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

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

Mix the components in the following proportions, and use a bead mill to disperse the colorant to obtain a coloring composition M3.

Coloring agent (A): 5.00 parts of a mixture of the compound represented by formula (Ia10), the compound represented by formula (Ia2143), the compound represented by formula (Ia850) and the compound represented by formula (Ia315) obtained in Example 4; Dispersant solution: 16.7 parts of DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 46.9 parts of propylene glycol monomethyl ether acetate; Solvent (E): 20.0 parts of ethyl lactate; Then, the 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 (Toray Dow Corning) (co., Ltd.) 0.00630 parts; Coloring composition 3 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

The film thickness of the obtained pre-baked pigmented coating film was measured using DektakXT (manufactured by BRUKER).

The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked color coating film and the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

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

The same process as in Example 14 was performed except that the compound represented by formula (Ia10), the compound represented by formula (Ia2143), the compound represented by formula (Ia850) and the mixture of the compound represented by formula (Ia315) obtained in Example 4 were replaced by the compound represented by formula (Ia33) to obtain a coloring composition, a pre-baked coloring film and a post-baked coloring film.

The film thickness of the pre-baked color coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

Example 16

Mix the components in the following proportions and disperse the colorant using a bead mill to obtain coloring composition M4.

Colorant (A): 4.50 parts of the compound represented by formula (Ia22); Colorant (A): 0.500 parts of the compound represented by formula (z); Dispersant solution: 16.7 parts of DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 46.9 parts of propylene glycol monomethyl ether acetate; Solvent (E): 20.0 parts of ethyl lactate; Then, the 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 (Toray Dow Corning Co., Ltd.) 0.00525 parts; Coloring composition 4 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

The film thickness of the obtained pre-baked pigmented coating film was measured using DektakXT (manufactured by BRUKER).

The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked color coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

Comparison Example 1

Mix the components in the following proportions and disperse the colorant using a bead mill to obtain coloring composition M5.

Colorant (A): C.I. Pigment Yellow 138 12.0 parts; Dispersant solid content 4.21 parts; Resin solid content 5.05 parts; Solvent (E): Propylene glycol monomethyl ether acetate 74.8 parts; Solvent (E): Propylene glycol monomethyl ether 3.94 parts; Then, the components were mixed in the following proportions to obtain a coloring composition 5.

Coloring composition M5 24.0 parts; Resin (B): Resin B2 solution 35.0 parts; Solvent (E): Propylene glycol monomethyl ether acetate 41.0 parts; Leveling agent (F): Toray Silicone SH8400 (Toray Dow Corning Co., Ltd.) 0.00630 parts; Coloring composition 5 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

The film thickness of the obtained pre-baked pigmented coating film was measured using DektakXT (manufactured by BRUKER).

The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked color coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

Comparison Example 2

Mix the components in the following proportions and disperse the colorant using a bead mill to obtain coloring composition M6.

Colorant (A): C.I. Pigment Yellow 138 4.50 parts; Colorant (A): Compound represented by formula (z) 0.500 parts; Dispersant solution: DISPERBYK-161 (manufactured by BYK-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 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 (Toray Dow Corning) (co., Ltd.) 0.00630 parts; Coloring composition 6 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

The film thickness of the obtained pre-baked pigmented coating film was measured using DektakXT (manufactured by BRUKER).

The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked color coating film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film are shown in Table 39.

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 indicates the maximum absorption wavelength on the longest wavelength side of the absorption spectrum, and the "BBB" column indicates the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Example 17

Mix the components in the following proportions and disperse the colorant using a bead mill to obtain coloring composition M7.

Colorant (A): 5.00 parts of the mixture containing the compound represented by formula (Ie12) obtained in Example 7; Dispersant solution: 16.7 parts of DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 46.9 parts of propylene glycol monomethyl ether acetate; Solvent (E): 20.0 parts of ethyl lactate; Then, the 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 (Toray Dow Corning) (co., Ltd.) 0.00630 parts; Coloring composition 7 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring 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-baking colored coating film was measured using DektakXT (manufactured by BRUKER).

The spectrum of the post-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the post-baked paint film and the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum of the post-baked paint film are shown in Table 40.

Comparison Example 3

Mix the ingredients in the following proportions and disperse the colorant using a bead mill to obtain coloring composition M8.

Colorant (A): 12.0 parts of C.I. Pigment Yellow 138; 4.21 parts of solid content of dispersant; 5.05 parts of solid content of resin; Solvent (E): 74.8 parts of propylene glycol monomethyl ether acetate; Solvent (E): 3.94 parts of propylene glycol monomethyl ether; Then, the components were mixed in the following proportions to obtain a coloring composition 8.

Coloring composition M8 24.0 parts; Resin (B): Resin B2 solution 35.0 parts; Solvent (E): Propylene glycol monomethyl ether acetate 41.0 parts; Leveling agent (F): Toray Silicone SH8400 (Toray Dow Corning Co., Ltd.) 0.00630 parts; Coloring composition 8 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring 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-baking colored coating film was measured using DektakXT (manufactured by BRUKER).

The spectrum of the post-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the post-baked paint film and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked paint film are shown in Table 40.

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

Comparison Example 4

Mix the ingredients in the following proportions and disperse the colorant using a bead mill to obtain a coloring composition MH4.

Colorant (A): C.I. Pigment Yellow 138 4.50 parts

Coloring agent (A): 0.500 parts of the compound represented by formula (z)

Dispersant solution: DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.) 16.7 parts

Resin (B): 11.4 parts of Resin B1 solution

Solvent (E): 46.9 parts of propylene glycol monomethyl ether acetate

Solvent (E): 20.0 parts of ethyl lactate

Then, the components were mixed in the following proportions to obtain a coloring composition H4.

Coloring composition MH4 57.6 parts

Resin (B): 27.0 parts of Resin B2 solution

Solvent (E): 15.4 parts of propylene glycol monomethyl ether acetate

Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00630 parts

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

The film thickness of the post-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD1.

In Tables AD1 to AD21, the "EEE" column indicates the maximum absorption wavelength on the longest wavelength side of the absorption spectrum, and the "FFF" column indicates the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum.

Implementation Example 6-1

Mix the components in the following proportions, and use a bead mill to disperse the colorant to obtain a coloring composition M6-1.

Coloring agent (A): 4.50 parts of the compound represented by formula (Ia51)

Coloring agent (A): 0.500 parts of the compound represented by formula (z)

Dispersant solution: DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.) 16.7 parts

Resin (B): 11.4 parts of Resin B1 solution

Solvent (E): 66.9 parts of propylene glycol monomethyl ether acetate

Then, the components are mixed in the following proportions to obtain a coloring composition 6-1.

Coloring composition M6-1 57.6 parts

Resin (B): 28.4 parts of Resin B1 solution

Solvent (E): 14.0 parts of propylene glycol monomethyl ether acetate

Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00630 parts

The coloring composition 6-1 was applied on a 2-inch square glass substrate (Eagle XG; manufactured by Corning) by spin coating, and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD2.

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~Example 6-4

The compound represented by formula (Ia51) is replaced with the compound listed in the "Colorant AAA" column in Table AD3. The same method as in Example 6-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD3.

Implementation Example 7-1

Mix the components in the following proportions, and use a bead mill to disperse the colorant to obtain the coloring composition M7-1.

Colorant (A): 4.50 parts of the compound represented by formula (Ia973); Colorant (A): 0.500 parts of the compound represented by formula (z); Dispersant solution: 8.33 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 75.2 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring composition 7-1.

Coloring composition M7-1 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 (Toray Dow Corning) (co., Ltd.) 0.00630 parts; Coloring composition 7-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

The film thickness of the obtained pre-baked colored coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD4.

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~Example 7-6

The compound represented by formula (Ia973) is replaced with the compound listed in the "Colorant AAA" column in Table AD5. The same method as Example 7-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD5.

[Table AD5]

Implementation Example 7-7

Mix the ingredients in the following proportions, disperse the colorant using a bead mill, and obtain the coloring composition M7-7.

Colorant (A): 4.50 parts of the compound represented by formula (If2528); Colorant (A): 0.500 parts of the compound represented by formula (z); Dispersant solution: 8.33 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 75.2 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring 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 (Toray Dow Corning Co., Ltd.) 0.00630 parts; Coloring composition 7-7 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

The pre-baked color coating film was post-baked at 230°C for 30 minutes to obtain a post-baked color coating film. The film thickness of the post-baked color coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of the post-baked color coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the post-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD6.

Implementation Example 90-1

Mix the ingredients in the following proportions, and use a bead mill to disperse the colorant to obtain the coloring composition M90-1.

Colorant (A): 4.00 parts of the compound represented by formula (Ia5); Colorant (A): 1.00 parts of the compound represented by formula (z); Dispersant solution: 12.5 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 71.1 parts of propylene glycol monomethyl ether acetate; Then, the 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; Coloring composition 90-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The film thickness of the obtained pre-baked coloring film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD7.

The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

[Table AD7]

Example 90-2~Example 90-22

The compound represented by formula (Ia5) is replaced with the compound listed in the "Colorant AAA" column in Table AD8. The same method as Example 90-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD8.

Example 90-23

Mix the ingredients in the following proportions, and use a bead mill to disperse the colorant to obtain the coloring composition M90-23.

Colorant (A): 4.00 parts of the compound represented by formula (If1904); Colorant (A): 1.00 parts of the compound represented by formula (z); Dispersant solution: 12.5 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 71.1 parts of propylene glycol monomethyl ether acetate; Then, the 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; Coloring composition 90-23 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning) and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The pre-baked coloring film was post-baked at 230°C for 30 minutes to obtain a post-baked coloring film. The film thickness of the obtained post-baking color coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of the post-baking color coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the post-baked painted film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked painted film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD9.

Implementation Example 91-1

Mix the ingredients in the following proportions, and use a bead mill to disperse the colorant to obtain the coloring composition M91-1.

Colorant (A): 4.00 parts of the compound represented by formula (If3796); Colorant (A): 1.00 parts of the compound represented by formula (z); Dispersant solution: 12.5 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 71.1 parts of propylene glycol monomethyl ether acetate; Then, the 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 parts; Coloring composition 91-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The film thickness of the obtained pre-baked coloring film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD10.

The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

[Table AD10]

Example 91-2~Example 91-4

The compound represented by formula (If3796) is replaced with the compound listed in the "Colorant AAA" column in Table AD11. The same method as Example 91-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD11.

Implementation Example 17-1

Mix the components in the following proportions and disperse the colorant using a bead mill to obtain the coloring composition M17-1.

Colorant (A): 3.89 parts of a mixture of a compound represented by formula (Ia1-SA1) and a compound represented by formula (Ia1-SA2) obtained in Example E-2; Colorant (A): 1.25 parts of a compound represented by formula (z); Dispersant solution: 12.5 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.5 parts of resin B1 solution; Solvent (E): 70.9 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring 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 (Toray Dow Corning) (co., Ltd.) 0.00629 parts; Coloring composition 17-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

The film thickness of the obtained pre-baked pigmented coating film was measured using DektakXT (manufactured by BRUKER).

The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD12.

The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

Implementation Example 12-1

Mix the components in the following proportions, and use a bead mill to disperse the colorant to obtain a coloring composition M12-1.

Colorant (A): 3.80 parts of the compound represented by formula (If1261); Colorant (A): 1.20 parts of the compound represented by formula (z); Dispersant solution: 12.5 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 71.1 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring 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; Coloring composition 12-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning) and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The pre-baked coloring film was post-baked at 230°C for 30 minutes to obtain a post-baked coloring film. The film thickness of the obtained post-baking colored coating film was measured using DektakXT (manufactured by BRUKER).

The spectrum of the post-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the post-baked painted film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked painted film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD13.

Implementation Example 13-1

Mix the components in the following proportions, and use a bead mill to disperse the colorant to obtain the coloring composition M13-1.

Colorant (A): 5.01 parts of the compound represented by formula (Ia728); Dispersant solution: 12.5 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 71.1 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring 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 parts; Coloring composition 13-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The film thickness of the obtained pre-baked coloring film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD14.

The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

Implementation Example 14-1

Mix the components in the following proportions and disperse the colorant using a bead mill to obtain the coloring composition M14-1.

Colorant (A): 4.66 parts of the compound represented by formula (Ia703); Colorant (A): 0.497 parts of the compound represented by formula (z); Dispersant solution: 12.5 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 70.9 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring 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; Coloring composition 14-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The film thickness of the obtained pre-baked coloring film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD15.

The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

Implementation Example 16-1

Mix the components in the following proportions and disperse the colorant using a bead mill to obtain the coloring composition M16-1.

Colorant (A): 4.13 parts of the compound represented by formula (It242); Colorant (A): 0.916 parts of the compound represented by formula (z); Dispersant solution: 12.4 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 71.1 parts of propylene glycol monomethyl ether acetate; Then, the components were mixed in the following proportions to obtain a coloring 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; Coloring composition 16-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The film thickness of the obtained pre-baked coloring film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD16.

The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

Implementation Example 51-1

Mix the ingredients in the following proportions, and use a bead mill to disperse the colorant to obtain the coloring composition M51-1.

Colorant (A): 2.25 parts of the compound represented by formula (Ia2); Colorant (A): 2.25 parts of the compound represented by formula (Ia5); Colorant (A): 0.500 parts of the compound represented by formula (z); Dispersant solution: 16.7 parts of DISPERBYK-161 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 46.9 parts of propylene glycol monomethyl ether acetate; Solvent (E): 20.0 parts of ethyl lactate; Then, the components were mixed in the following proportions to obtain a coloring 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; Coloring composition 51-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The film thickness of the obtained pre-baked coloring film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD17.

The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

Implementation Example 571-1

Mix the ingredients in the following proportions and disperse the colorant using a bead mill to obtain the coloring composition M571-1.

Colorant (A): 2.25 parts of the compound represented by formula (Ia1); Colorant (A): 2.25 parts of the compound represented by formula (Ia5); Colorant (A): 0.500 parts of the compound represented by formula (z); Dispersant solution: 8.33 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 10.0 parts of resin B1 solution; Solvent (E): 76.7 parts of propylene glycol monomethyl ether acetate; Then, the 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; Coloring composition 571-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The film thickness of the obtained pre-baked coloring film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD18.

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

Mix the ingredients in the following proportions and disperse the colorant using a bead mill to obtain the coloring composition M591-1.

Colorant (A): 2.25 parts of the compound represented by formula (Ia1); Colorant (A): 2.25 parts of the compound represented by formula (Ia248); Colorant (A): 0.500 parts of the compound represented by formula (z); Dispersant solution: 12.5 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 71.1 parts of propylene glycol monomethyl ether acetate; Then, the 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; Coloring composition 591-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The film thickness of the obtained pre-baked coloring film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD19.

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

In Example 591-1, the following coloring agent (A) in the following amount is used instead of the compound represented by formula (Ia1) and the compound represented by formula (Ia248). The same method as in Example 591-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

Colorant (A): 2.38 parts of a mixture of the compound represented by formula (Ia10), the compound represented by formula (Ia2143), the compound represented by formula (Ia850) and the compound represented by formula (Ia315) obtained in Example 4; Colorant (A): 2.12 parts of the compound represented by formula (Ia51); The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD19.

Example 591-3

In Example 591-1, the following coloring agent (A) is used in the following amount instead of the compound represented by formula (Ia1) and the compound represented by formula (Ia248). The same method as in Example 591-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

Colorant (A): 2.38 parts of the compound represented by formula (Ia248); Colorant (A): 2.12 parts of the compound represented by formula (Ia51); The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD19.

Example 591-4

In Example 591-1, the following coloring agent (A) in the following amount is used instead of the compound represented by formula (Ia1) and the compound represented by formula (Ia248). The same method as in Example 591-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

Colorant (A): 2.64 parts of the compound represented by formula (Ia23); Colorant (A): 1.86 parts of the compound represented by formula (Ia17); The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD19.

Example 591-5

In Example 591-1, the following coloring agent (A) in the following amount is used instead of the compound represented by formula (Ia1) and the compound represented by formula (Ia248). The same method as in Example 591-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

Colorant (A): 2.17 parts of the compound represented by formula (Ia19); Colorant (A): 2.33 parts of the compound represented by formula (Ia17); The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD19.

Example 592-1

Mix the ingredients in the following proportions, and use a bead mill to disperse the colorant to obtain the coloring composition M592-1.

Colorant (A): 4.00 parts of the compound represented by formula (Ia1); Colorant (A): 1.00 parts of the compound represented by formula (Ia248); Dispersant solution: 12.5 parts of BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd.); Resin (B): 11.4 parts of resin B1 solution; Solvent (E): 71.1 parts of propylene glycol monomethyl ether acetate; Then, the 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; Coloring composition 592-1 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The film thickness of the obtained pre-baked coloring film was measured using DektakXT (manufactured by BRUKER). The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD20.

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

In Example 592-1, the following coloring agent (A) in the following amount is used instead of the compound represented by formula (Ia1) and the compound represented by formula (Ia248). The same method as in Example 592-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

Colorant (A): 4.00 parts of the compound represented by formula (Ia5); Colorant (A): 1.00 parts of the compound represented by formula (Ia248); The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD20.

Example 592-3

In Example 592-1, the following coloring agent (A) in the following amount is used instead of the compound represented by formula (Ia1) and the compound represented by formula (Ia248). The same method as in Example 592-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

Colorant (A): 4.00 parts of the compound represented by formula (Ia699); Colorant (A): 1.00 parts of the compound represented by formula (Ia248); The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD20.

Example 592-4

In Example 592-1, the following coloring agent (A) in the following amount is used instead of the compound represented by formula (Ia1) and the compound represented by formula (Ia248). The same method as in Example 592-1 is followed to obtain a coloring composition, a pre-baked coloring film, and a post-baked coloring film.

Colorant (A): 4.00 parts of the compound represented by formula (Ia5); Colorant (A): 1.00 parts of a mixture of the compound represented by formula (Ia5-SA1) and the compound represented by formula (Ia5-SA2) obtained in Example E-1; The film thickness of the pre-baked color coating film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked color coating film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD20.

Example S-1

The ingredients were mixed in the following proportions to obtain the coloring composition S-1.

Coloring agent (A): 2.92 parts of a mixture of the compound represented by formula (Ia5-SA1) and the compound represented by formula (Ia5-SA2) obtained in Example E-1, and 51.4 parts of a mixture of 97.1 parts of N-methylpyrrolidone; Resin (B): 38.5 parts of resin B1 solution; Solvent (E): 10.1 parts of propylene glycol monomethyl ether acetate; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00531 parts; on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), the coloring composition S-1 was applied by spin coating, and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring 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-baking colored coating film was measured using DektakXT (manufactured by BRUKER).

The spectrum of the post-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the post-baked painted film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked painted film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD21.

Example S-2

The ingredients were mixed in the following proportions to obtain the coloring composition S-2.

Colorant (A): 59.2 parts of a mixture of 1.00 parts of a compound represented by the formula (If5670) and 99.0 parts of N-methylpyrrolidone; Resin (B): 40.5 parts of a resin B1 solution; Solvent (E): 0.278 parts of propylene glycol monomethyl ether acetate; Leveling agent (F): 0.00514 parts of Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.); The coloring composition S-2 was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning) and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film. The pre-baked color coating film was post-baked at 230°C for 30 minutes to obtain a post-baked color coating film. The film thickness of the post-baked color coating film was measured using DektakXT (manufactured by BRUKER). The spectrum of the post-baked color coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the post-baked painted film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the post-baked painted film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD21.

Example S-3

The ingredients are mixed in the following proportions to obtain the coloring composition S-3.

Coloring agent (A): 2.24 parts of the mixture containing the compound represented by formula (Ia2-SA) obtained in Example E-3; Resin (B): 33.6 parts of Resin B1 solution; Solvent (E): 0.581 parts of propylene glycol monomethyl ether acetate; Solvent (E): 63.6 parts of N-methylpyrrolidone; Leveling agent (F): Toray Silicone SH8400 (manufactured by Toray Dow Corning Co., Ltd.) 0.00490 parts; on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), the coloring composition S-3 was applied by spin coating, and then pre-baked at 100°C for 3 minutes to form a pre-baked coloring film.

The film thickness of the obtained pre-baked pigmented coating film was measured using DektakXT (manufactured by BRUKER).

The spectrum of the pre-baked colored coating film was measured using a colorimeter: LVmicroZ (manufactured by Lambda-Vision Co., Ltd.).

The film thickness of the pre-baked paint film, and the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the pre-baked paint film or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum are shown in Table AD21.

The pre-baked colored coating film was post-baked at 230°C for 30 minutes to obtain a post-baked colored coating film.

According to the results, the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the colored coating formed by the coloring composition containing the compound of the present invention or the wavelength of the shoulder peak on the longest wavelength side of the absorption spectrum is longer than the maximum absorption wavelength on the longest wavelength side of the absorption spectrum of the colored coating formed by the coloring composition containing C.I. Pigment Yellow 138.

[Industrial availability]

The coloring composition and compound of the present invention can be used in the formation of a color filter with a darker color than a coloring composition containing C.I. Pigment Yellow 138, and therefore can be suitably used in a color filter or a display device such as a liquid crystal display device.

Claims (6)

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

[In formula (I), ^R1 to ^R5 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, _-SO3M , _-CO2M , MM, a monovalent chain or cyclic hydrocarbon group having 1 to 40 carbon atoms, a group in which a hydrogen atom constituting the monovalent chain or cyclic hydrocarbon group is substituted with a halogen atom, a cyano group, a nitro group, _-SO3M , _-CO2M or MM, or a monovalent heterocyclic group having 1 to 40 carbon atoms, wherein a hydrogen atom constituting the monovalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, _-SO3M , _-CO2M or MM; ^R1 and ^R2 , ^R2 and ^R3 , and ^R3 and R4 are independently selected from the group consisting of: 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 chain or cyclic hydrocarbon group having 1 to 40 carbon atoms, a hydrogen atom constituting the monovalent chain or cyclic hydrocarbon group substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM, or a monovalent heterocyclic group having 1 to 40 carbon atoms, wherein the hydrogen atom constituting the monovalent heterocyclic group may be substituted 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 group represented by formula (QQ1) to formula (QQ3) or formula (QQ5);

In the formula, R ^Q1 ~R ^Q16 and R ^Q25 ~R ^Q30 independently represent a hydrogen atom, a halogen atom, a nitro group, -CO ₂ M, a monovalent chain or cyclic hydrocarbon group having 1 to 12 carbon atoms, a methoxycarbonyl group, an ethoxycarbonyl group, an acetylamino group, a propionylamino group or a hydroxyl group, and ※ represents a bond; when there are plural Z ¹ ~Z ⁴ , M and MM, they may be the same or different from each other]. The coloring composition as described in claim 1 comprises a resin. The coloring composition as described in claim 1 or claim 2 comprises a polymerizable compound and a polymerization initiator. A color filter, which is formed by the coloring composition as described in claim 1 or claim 2. A display device comprising a color filter as described in claim 4. A compound represented by formula (I):

[In formula (I), ^R1 to ^R5 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, _-SO3M , _-CO2M , MM, a monovalent chain or cyclic hydrocarbon group having 1 to 40 carbon atoms, a group in which a hydrogen atom constituting the monovalent chain or cyclic hydrocarbon group is substituted with a halogen atom, a cyano group, a nitro group, _-SO3M , _-CO2M or MM, or a monovalent heterocyclic group having 1 to 40 carbon atoms, wherein a hydrogen atom constituting the monovalent heterocyclic group may be substituted with a halogen atom, a cyano group, a nitro group, _-SO3M , _-CO2M or MM; ^R1 and ^R2 , ^R2 and ^R3 , and ^R3 and R4 are independently selected from the group consisting of: 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 chain or cyclic hydrocarbon group having 1 to 40 carbon atoms, a hydrogen atom constituting the monovalent chain or cyclic hydrocarbon group substituted with a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM, or a monovalent heterocyclic group having 1 to 40 carbon atoms, wherein the hydrogen atom constituting the monovalent heterocyclic group may be substituted 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 group represented by formula (QQ1) to formula (QQ3) or formula (QQ5);

In the formula, R ^Q1 ~R ^Q16 and R ^Q25 ~R ^Q30 independently represent a hydrogen atom, a halogen atom, a nitro group, -CO ₂ M, a monovalent chain or cyclic hydrocarbon group having 1 to 12 carbon atoms, a methoxycarbonyl group, an ethoxycarbonyl group, an acetylamino group, a propionylamino group or a hydroxyl group, and ※ represents a bond; when there are plural Z ¹ ~Z ⁴ , M and MM, they may be the same or different from each other].