TWI887429B - Compound, coloring composition, color filter and display device - Google Patents

Abstract

The object of the present invention is to provide a compound and a coloring composition capable of forming a color filter having excellent heat resistance. The compound of the present invention is characterized by being represented by formula (I), and the coloring composition of the present invention is characterized by comprising the compound represented by formula (I) and a red color material. [In formula (I), R ³ represents a halogen atom or an electron-donating group]

Description

Compound, coloring composition, color filter and display device

The present invention relates to a compound useful as a coloring agent, a coloring composition containing the compound, a color filter formed from the coloring composition, and a display device including the color filter.

Color filters used in display devices such as liquid crystal display devices, electroluminescence display devices, and plasma displays, or solid-state imaging devices such as charge coupled devices (CCDs) or complementary metal-oxide-semiconductor transistors (CMOS) sensors are made of a coloring composition. Among them, there are cases where red color filters are made of a coloring composition containing a yellow coloring material in addition to a red coloring material. As the yellow coloring material, C.I. Pigment Yellow 185 is known (Patent Document 1). [Prior Art Document] [Patent Document]

[Patent Document 1] Japanese Patent Publication No. 2012-203146

[Problem to be solved by the invention] However, there is a case where the color filter formed by the coloring composition containing the yellow color material cannot fully satisfy the heat resistance. Therefore, the problem of the present invention is to provide a compound and a coloring composition that can form a color filter with excellent heat resistance. [Means for solving the problem]

The gist of the present invention is as follows. [1] A compound represented by formula (I): [In formula (I), R ¹ , R ² , R ⁴ and R ⁵ each 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 - may also be substituted by -O-, -S-, -S(O) ₂ - or -CO-; the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may also be substituted by a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; R ³ represents a halogen atom or an electron donating group; R ¹ and R ² 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 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-; 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 - 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 by 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 compound as described in [1], wherein Q ¹ and Q ² in formula (I) are independently a group represented by formula (QQ1) or formula (QQ2), [In formula (QQ1) to formula (QQ2), R ^Q1 to R ^Q10 each 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 - may be substituted by -O-, -S-, -S(O) ₂ - or -CO-, the hydrogen atom constituting the monovalent hydrocarbon 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 ^Q1 to R ^Q4 may each bond with one or more selected from R ^Q1 to R ^Q4 to form a ring, R ^Q5 to R ^Q10 may each bond with one or more selected from R ^Q5 to R ^Q10 to form a ring; M and MM have the same meanings as described above; ※ indicates a bond]. [3] A coloring composition comprising the compound as described in [1] or [2], and a red colorant. [4] The coloring composition as described in [3], further comprising a resin. [5] The coloring composition as described in [3] or [4], further comprising a polymerizable compound and a polymerization initiator. [6] A color filter formed by the coloring composition as described in any one of [3] to [5]. [7] A display device comprising the color filter as described in [6]. [Effects of the Invention]

According to the compound and the coloring composition of the present invention, a color filter having improved heat resistance can be provided.

[Compound] The compound of the present invention is a compound represented by formula (I) (hereinafter, sometimes referred to as compound (I)). Hereinafter, the present invention is described in detail using formula (I), and it is assumed that compound (I) also includes its tautomers.

[In formula (I), R ¹ , R ² , R ⁴ and R ⁵ each 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 - may also be substituted by -O-, -S-, -S(O) ₂ - or -CO-; the hydrogen atom constituting the monovalent hydrocarbon group and the monovalent heterocyclic group may also be substituted by a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M or MM; R ³ represents a halogen atom or an electron donating group; R ¹ and R ² 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 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-; 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 - 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]

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

The monovalent carbon group represented by R ¹ , R ² , R ⁴ , R ⁵ and Z ¹ to Z ⁴ has 1 to 40 carbon atoms, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, further preferably 1 to 18 carbon atoms, and particularly preferably 1 to 12 carbon atoms.

The monovalent hydrocarbon group having 1 to 40 carbon atoms represented by R ¹ , R ² , R ⁴ , 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 or cyclic (alicyclic hydrocarbon group).

Examples of the saturated or unsaturated chain alkyl group represented by R ¹ , R ² , R ⁴ , R ⁵ and Z ¹ to Z ⁴ include: linear chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl; branched chain alkyl groups such as isopropyl, isobutyl, sec-butyl, t-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 and 2-ethylhexyl; Alkenyl groups include ethenyl (vinyl), propenyl (e.g., 1-propenyl, 2-propenyl (allyl)), 1-methylethenyl, butenyl (e.g., 1-butenyl, 2-butenyl, 3-butenyl), 3-methyl-1-butenyl, 1,3-butadienyl, 1-(2-propenyl)ethenyl, 1-(1-methylethenyl)ethenyl, 1,2-dimethyl-1-propenyl, pentenyl (e.g., 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl), and hexenyl (e.g., 1-hexenyl, 5-hexenyl); alkynyl groups include ethynyl, propynyl (e.g., 1-propynyl, 2-propynyl), octynyl (e.g., 1-octynyl, 7-octynyl), butynyl, pentynyl, and hexynyl.

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 group represented by R ¹ , R ² , R ⁴ , R ⁵ and Z ¹ to Z ⁴ include cycloalkyl groups such as cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-1-en-1-yl, cyclohex-2-en-1-yl and cyclohex-3-en-1-yl), cycloheptenyl and cyclooctenyl; and saturated or unsaturated polycyclic alkyl groups such as norbornyl, norbornenyl, adamantyl and bicyclo[2.2.2]octyl.

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.

Examples of the aromatic hydrocarbon group represented by R ¹ , R ² , R ⁴ , R ⁵ and Z ¹ to Z ⁴ include phenyl, o-tolyl, m-tolyl, p-tolyl, 2,4-dimethylphenyl, 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 2,4-diisopropylphenyl, 2,6-diisopropylphenyl, 4-vinylphenyl, o-t-butylphenyl, m-t-butylphenyl, p-t-butylphenyl, 3,5-di(t-butyl)phenyl, 1-naphthyl, 2-naphthyl, 6-methyl-2-naphthyl, fluorenyl, phenanthrenyl, anthracenyl, perylenyl and pyrenyl.

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

The alkyl group represented by R ¹ , R ² , R ⁴ , R ⁵ and Z ¹ to Z ⁴ may be a group formed by combining the above-mentioned alkyl groups. Examples of the group formed by combining the above-mentioned alkyl groups include a group formed by combining at least one selected from an aromatic alkyl group, a chain alkyl group and an alicyclic alkyl group with an aromatic alkyl group; a group formed by combining a chain alkyl group and an alicyclic alkyl group, and the like.

Examples of the group formed by combining an aromatic hydrocarbon group with at least one selected from an aromatic hydrocarbon group, a chain hydrocarbon group, and an alicyclic hydrocarbon group include aralkyl groups such as benzyl, (4-methylphenyl)methyl, and phenethyl; arylalkenyl groups such as 1-phenylethenyl, 2-phenylethenyl (phenyl vinyl), 2,2-diphenylvinyl, and 2-phenyl-2-(1-naphthyl)vinyl; arylalkynyl groups such as phenylethynyl; aryl groups (preferably phenyl groups) such as (phenylethynyl)phenyl to which an arylalkynyl group is bonded; phenyl groups such as biphenyl and terphenyl to which one or more phenyl groups are bonded; cyclohexylmethylphenyl, benzylphenyl, and (dimethyl(phenyl)methyl)phenyl; The carbon number of these is preferably 7-30, more preferably 7-20, further preferably 7-18, and particularly preferably 7-15.

In addition, as a group formed by combining a chain alkyl group and an alicyclic alkyl group, 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 groups may be mentioned. The carbon number of these groups 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 , R ² , R ⁴ , R ⁵ and Z ¹ to Z ⁴ refers to a group containing a heteroatom as a constituent element of the ring. The monovalent heterocyclic group refers to a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from the heterocyclic ring. The monovalent heterocyclic group having 1 to 40 carbon atoms may be monocyclic or polycyclic. Examples of the heteroatom include a nitrogen atom, an oxygen atom and a sulfur atom.

The heterocyclic group has preferably 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, further preferably 3 to 18 carbon atoms, and particularly preferably 3 to 12 carbon atoms.

Examples of heterocyclic rings containing nitrogen atoms include: aziridine, azetidine, pyrrolidine, piperidine, and piperazine; pyrrole, pyrazole, imidazole, 1,2,3-triazole, and 1,2,4-triazole; pyridine, pyrazine, pyrimidine, pyrazine, and 1,3,5-triazine. six-membered unsaturated heterocyclic rings such as indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 3-methylquinoxaline, quinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, benzopiperidine, etc.; condensed bicyclic heterocyclic rings such as carbazole, acridine and phenazine, 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; bicyclic saturated heterocyclic rings such as 1,4-dioxaspiro[4.5]decane, 1,4-dioxaspiro[4.5]nonane, and 1,4-dioxaspiro[4.4]nonane; α-acetone, β-propiolactone, γ-butyrolactone, γ-valerolactone, and δ-valerolactone; Lactone-type heterocyclic rings such as lactone; five-membered unsaturated heterocyclic rings such as furan, 2,3-dimethylfuran, 2,5-dimethylfuran; six-membered unsaturated heterocyclic rings such as 2H-pyran, 4H-pyran; condensed bicyclic heterocyclic rings such as benzofuran, benzopyran, benzodioxole, 1,3-benzodioxole, benzodioxane, chromane and isochromane; condensed tricyclic heterocyclic rings such as oxanthracene and dibenzofuran, etc.

Examples of the heterocyclic ring containing a sulfur atom include five-membered saturated heterocyclic rings such as dithiolane; six-membered saturated heterocyclic rings such as thiazane, 1,3-dithiane, and 2-methyl-1,3-dithiane; five-membered unsaturated heterocyclic rings such as thiophene, thiopyran, and benzothiopyran; condensed bicyclic heterocyclic rings such as benzothiopyran and benzothiophene; and condensed tricyclic heterocyclic rings such as thianthrene and dibenzothiophene.

Examples of the heterocyclic ring containing a nitrogen atom and an oxygen atom 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 and isoxazole; condensed bicyclic heterocyclic rings such as benzoxazole, benzoisoxazole, benzoxazine, benzodioxane, and benzimidazolinone; condensed tricyclic heterocyclic rings such as phenoxazine, and the like.

Examples of the heterocyclic ring containing a nitrogen atom and a sulfur atom include monocyclic heterocyclic rings such as thiazole, condensed bicyclic heterocyclic rings such as benzothiazole, and condensed tricyclic heterocyclic rings such as phenothiazine.

-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-, -S(O) ₂ - or -CO-. Examples of such groups include:

-SiH ₃ ; Silyl groups having 1 to 3 alkyl groups such as -Si(CH ₃ ) ₃ , -Si(CH ₂ CH ₃ ) ₃ , -Si(CH ₃ ) ₂ (CH ₂ CH ₃ ) ; -Si(OH) ₃ , -Si(OCH ₃ ) ₃ , -Si(OCH ₂ CH ₃ ) ₃ , -Si(O(CH ₂ ) ₂ CH ₃ ) ₃ , -SiH ₂ (OH) , -Si(CH ₃ ) ₂ (OCH ₃ ) ; Amine groups; Amines having one or two alkyl groups such as N-methylamine, N,N-dimethylamine, N-ethylamine, N,N-diethylamine, N-propylamine, N,N-dipropylamine, N-isopropylamine, N,N-diisopropylamine, N-butylamine, N,N-dibutylamine, N-isobutylamine, N,N-diisobutylamine, N-sec-butylamine, N,N-di-sec-butylamine, N-t-butylamine, N,N-di-t-butylamine, N-phenylamine, N,N-diphenylamine, N,N-ethylmethylamine, N,N-propylmethylamine, N,N-isopropylmethylamine, N,N-butylmethylamine, N,N-t-butylmethylamine and N,N-phenylmethylamine; Oxy groups (alkoxy and aryloxy groups) bonded to a alkyl group, such as methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, t-butoxy, pentyloxy, hexyloxy, (2-ethyl)hexyloxy, phenyloxy, m-tolyloxy, and 3,4-xylyloxy; cyclopropyl; formyl; alkanoyl groups, such as acetyl, propionyl, butyryl, t-butyryl, pentyl, hexyl, (2-ethyl)hexyl, and benzoyl; Oxycarbonyl groups bonded to a alkyl group such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyl)hexyloxycarbonyl, phenyloxycarbonyl, and o-tolyloxycarbonyl; Benzyl groups bonded to a alkyl group such as methylthio, ethylthio, propylthio, butylthio, tert-butylthio, pentylthio, hexylthio, (2-ethylhexyl)thio, phenylthio, and o-tolylthio; Sulfonylamine; N-methylamine sulfonyl, N,N-dimethylamine sulfonyl, N-ethylamine sulfonyl, N,N-diethylamine sulfonyl, N-propylamine sulfonyl, N,N-dipropylamine sulfonyl, N-isopropylamine sulfonyl, N,N-diisopropylamine sulfonyl, N-butylamine sulfonyl, N,N-dibutylamine sulfonyl, N-isobutylamine sulfonyl, N,N-diisobutylamine sulfonyl, N-sec-butylamine sulfonyl, N,N-di-sec-butylamine sulfonyl, Amine sulfonyl groups having one or two alkyl groups such as butylamine sulfonyl, N-tert-butylamine sulfonyl, N,N-di-tert-butylamine sulfonyl, N-phenylamine sulfonyl, N,N-diphenylamine sulfonyl, N,N-ethylmethylamine sulfonyl, N,N-propylmethylamine sulfonyl, N,N-isopropylmethylamine sulfonyl, N,N-butylmethylamine sulfonyl, N,N-tert-butylmethylamine sulfonyl and N,N-phenylmethylamine sulfonyl; N-formylamino; N-acetylamino, N-propionylamino, N-butyrylamino, N-2,2-dimethylpropionylamino, N-pentanylamino, N-hexanylamino, N-(2-ethyl)hexanylamino, N-benzylamino and the like N-alkylamino; hydroxyl; alkyloxy groups such as formyloxy, acetyloxy, propionyloxy, butyryloxy, 2,2-dimethylpropionyloxy, pentanyloxy, hexanyloxy, (2-ethyl)hexanyloxy, benzyloxy and the like; Sulfonyl groups substituted with a alkyl group such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2-ethyl)hexylsulfonyl, phenylsulfonyl and p-tolylsulfonyl; Carbamoyl; N-methylaminoformyl, N,N-dimethylaminoformyl, N-ethylaminoformyl, N,N-diethylaminoformyl, N-propylaminoformyl, N,N-dipropylaminoformyl, N-isopropylaminoformyl, N,N-diisopropylaminoformyl, N-butylaminoformyl, N,N-dibutylaminoformyl, N-isobutylaminoformyl, N,N-diisobutylaminoformyl, N-sec-butylaminoformyl, N,N-di-sec-butylaminoformyl, aminoformyl group having one or two alkyl groups such as methylaminoformyl, N-tert-butylaminoformyl, N,N-di-tert-butylaminoformyl, N-phenylaminoformyl, N,N-diphenylaminoformyl, N,N-ethylmethylaminoformyl, N,N-propylmethylaminoformyl, N,N-isopropylmethylaminoformyl, N,N-butylmethylaminoformyl, N,N-tert-butylmethylaminoformyl and N,N-phenylmethylaminoformyl.

In addition, 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.

The electron donating group represented by R ³ is a group having the property of donating electrons to the bonding atom side more easily than a hydrogen atom. As the electron donating group, a group whose substituent constant (σ _p ) of the Hammett equation takes a negative value can be cited. For the σ _p value of the electron donating group, for example, the values described in Table 1 of C. Hansch et al., "A Survey of Hammett Substituent Constants and Resonance and Field Parameters" (Chem. Rev.) (Vol.91, p.165-195 (1991)) can be used.

The σ _p value of the electron donating group represented by R ³ is, for example, less than 0, preferably -0.10 or less, more preferably -0.20 or less, and may be -0.95 or more, preferably -0.80 or more, more preferably -0.60 or more.

Specifically, the electron-donating group represented by R ³ includes: linear or branched alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl; cycloalkyl groups such as cyclopropyl, cyclobutyl, and cyclopentyl; alkenyl groups such as vinyl, allyl, and 1-propenyl; cycloalkenyl groups such as 1-cyclopentenyl and 1-cyclohexenyl; aryl groups such as phenyl; aralkyl groups such as benzyl and phenethyl; alkoxy groups such as methoxy, ethoxy, propoxy, and butoxy; aryloxy groups such as phenyloxy; hydroxyl groups; amino groups; amino groups having one or two alkyl groups such as methylamino, ethylamino, n-propylamino, dimethylamino, and diethylamino; amino groups having one or two aryl groups such as phenylamino; hydroxylamino, and the like.

The carbon number of the alkyl group which the linear or branched alkyl group, alkoxy group, and amine group may have is preferably 1 to 20, more preferably 1 to 12, further preferably 1 to 8, particularly preferably 1 to 4.

The carbon number of the cycloalkyl group is preferably 3 or more and 20 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 8 or less.

The carbon number of the alkenyl group is preferably 2 or more and 20 or less, more preferably 2 or more and 12 or less, and even more preferably 2 or more and 8 or less.

The carbon number of the cycloalkenyl group is preferably 4 or more and 20 or less, more preferably 4 or more and 12 or less, and even more preferably 4 or more and 8 or less.

The carbon number of the aryl group which the aryl group, aryloxy group and amine group may have is preferably 6 or more and 20 or less, more preferably 6 or more and 12 or less, and even more preferably 6 or more and 10 or less.

The carbon number of the aralkyl group is preferably 7 or more and 20 or less, more preferably 7 or more and 12 or less.

The electron donating group represented by R ³ is preferably a linear or branched alkyl group, an alkoxy group, a hydroxyl group, an amino group, or an amino group having one or two alkyl groups, more preferably an alkoxy group, a hydroxyl group, or an amino group, and particularly preferably an alkoxy group having 1 to 4 carbon atoms.

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

As the metal atom which may have a ligand represented by M and MM, there can be mentioned metal atoms belonging to Group 2 to Group 15 of the periodic table. As the metal atom, 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 the metal atom which may have a ligand, the compound (I) from which the metal atom which may have a ligand is removed is also included. The compound (I) also contains such an oligomer or polymer. The charge of the compound (I) is 0.

Z ¹ to Z ⁴ may be the same or different, and are preferably the same. Z ¹ to Z ⁴ are preferably independently a hydrogen atom or a monovalent alkyl group having 1 to 40 carbon atoms; more preferably independently a hydrogen atom, a linear alkyl group or a branched alkyl group (hereinafter referred to as "alkyl" in some cases); further preferably independently a hydrogen atom or an alkyl group having 1 to 12 carbon atoms; particularly preferably a hydrogen atom.

Examples of N(Z ¹ )(Z ² )(Z ³ )(Z ⁴ ) represented by M and MM include: NH ₄ ; groups in which three of Z ¹ to Z ⁴ are hydrogen atoms and one is an alkyl group, such as NH ₃ (CH ₂ CH ₃ ) and NH ₃ ((CH ₂ ) ₇ CH ₃ ) ; groups in which two of Z 1 to Z 4 are hydrogen atoms and two are alkyl groups, such as NH ₂ (CH ₃ ) ₂ and NH ₂ (CH ₂ CH ₃ ) ₂ ; groups in which one of Z ¹ to Z ⁴ is a hydrogen atom and three are alkyl groups, such as NH(CH ₃ ) ₃ and NH(CH ₂ CH ₃ ) ₃ ; groups in which Z ¹ to Z ⁴ are hydrogen atoms and three are alkyl groups, such as N(CH ₃ ) ₄ and N(CH ₂ CH ₃ ) ₄ ^{. 4} are all alkyl groups, among which NH ₄ is preferred.

M is preferably a hydrogen atom or an alkali metal atom, more preferably a hydrogen atom, a sodium atom or a potassium atom.

As MM, preferred are: alkaline metal atoms, Mg which may have ligands, Ca which may have ligands, Sr which may have ligands, Ba which may have ligands, Ni which may have ligands, Zn which may have ligands, Cu which may have ligands, Fe which may have ligands, Co which may have ligands, Sn which may have ligands, Mn which may have ligands, Al which may have ligands, or Cr which may have ligands.

R ¹ , R ² , R ⁴ , and R ⁵ are preferably independently a hydrogen atom, a halogen atom, or a monovalent hydrocarbon group having 1 to 40 carbon atoms, more preferably independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 12 carbon atoms, and particularly preferably a hydrogen atom.

R ³ is preferably a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group, an amino group, or an amino group having one or two alkyl groups, more preferably a halogen atom, an alkoxy group, a hydroxyl group, or an amino group, and particularly preferably a chlorine atom, a fluorine atom, or an alkoxy group having 1 to 4 carbon atoms.

^Q1 and ^Q2 each independently represent a divalent hydrocarbon group or a divalent heterocyclic group. The divalent hydrocarbon group includes a group formed by removing one hydrogen atom constituting the monovalent hydrocarbon group, and the divalent heterocyclic group includes a group formed by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the monovalent 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 - 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, -SO ₃ M, -CO ₂ M or MM.

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

It is preferred that ^Q1 and ^Q2 are each independently any one of the groups represented by Formula (QQ1) to Formula (QQ19).

[In formulae (QQ1) to (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 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 - may be substituted by -O-, -S-, -S(O) ₂ - or -CO-; the hydrogen atom constituting the monovalent hydrocarbon 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 ^Q1 to R ^Q94 may each bond 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 bonding bond]

As the halogen atom, the same groups as those described above can be cited, and the preferred embodiments thereof are also the same.

Examples of the monovalent alkyl group having 1 to 40 carbon atoms and the monovalent heterocyclic group having 1 to 40 carbon atoms represented by R ^Q1 to R ^Q94 include the same ones as those described above for the monovalent alkyl group having 1 to 40 carbon atoms and the monovalent heterocyclic group having 1 to 40 carbon atoms, and the preferred embodiments thereof are also the same.

M and MM have the same meanings as described above, and their preferred embodiments are also the same.

R ^Q1 to R ^Q94 are preferably independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, CO ₂ M, or a monovalent hydrocarbon group having 1 to 40 carbon atoms, more preferably independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 12 carbon atoms, more preferably independently a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, an ethyl group, or a propyl group, and most preferably a hydrogen atom.

As ^Q1 and ^Q2 , it is more preferred that they are each independently any one of the groups represented by formula (QQ1) to formula (QQ12), further preferably that they are each independently any one of the groups represented by formula (QQ1) to formula (QQ5), further preferably that they are each independently a group represented by formula (QQ1) or formula (QQ2), and most preferably that ^Q1 and ^Q2 are a group represented by formula (QQ2).

Examples of the compound (I) include compounds represented by formula (Ia1) to formula (Ia200) shown in Tables 1 and 2 below.

[Table 1]

[Table 2]

In Tables 1 and 2, Qa1 to Qa5 represent groups represented by the following formulae (* indicates a bond).

As compound (I), compounds represented by formula (Ia1) to formula (Ia48) and formula (Ia73) to formula (Ia80) are preferred, compounds represented by formula (Ia1) to formula (Ia16), formula (Ia41) to formula (Ia48) and formula (Ia73) to formula (Ia80) are more preferred, and compounds represented by formula (Ia1) to formula (Ia16) are further preferred.

Compound (I) can be produced, for example, by reacting a compound represented by formula (pt1), a compound represented by formula (pt2), and a compound represented by formula (pt3). Hereinafter, this production method may be referred to as production method 1.

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

The amount of the compound represented by formula (pt2) used in the reaction of production method 1 is usually 0.1 mol to 30 mol, preferably 1 mol to 20 mol, more preferably 1 mol to 16 mol, further preferably 1 mol to 10 mol, based on 1 mol of the compound represented by formula (pt1).

The amount of the compound represented by formula (pt3) used in the reaction of production method 1 is usually 0.1 mol to 30 mol, preferably 1 mol to 20 mol, more preferably 1 mol to 16 mol, further preferably 1 mol to 10 mol, based on 1 mol of the compound represented by formula (pt1).

The reaction temperature 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 is usually 0.5 hours to 500 hours.

The reaction of Production Method 1 is usually carried out in the presence of a solvent.

As the solvent, there can be listed: 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 hexane; toluene, trimethylbenzene (e.g. Aromatic hydrocarbon solvents such as 1,3,5-trimethylbenzene), decahydronaphthalene, tetrahydronaphthalene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichlorobenzene, trichlorobenzene (for example, 1,3,5-trichlorobenzene), 1-chloronaphthalene, 2-chloronaphthalene; nitrated hydrocarbon solvents such as nitrobenzene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, among which methyl benzoate is preferred.

The amount of the solvent used is usually 1 to 1000 parts by mass based on 1 part by mass of the compound represented by formula (pt1) in the reaction of 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 an acid coexists.

As the acid, there may be mentioned: 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, etc.; 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 may be mentioned: hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acids, more preferably, there may be mentioned carboxylic acids, and further preferably, there may be mentioned benzoic acid.

The amount of the acid used in the reaction of Preparation Method 1 is generally 1 mol to 90 mol, preferably 1 mol to 70 mol, more preferably 1 mol to 50 mol, further preferably 1 mol to 30 mol, based on 1 mol of the compound represented by Formula (pt1).

The method for removing compound (I) from the reaction mixture is not particularly limited, and the compound (I) can be removed by various known methods. For example, after the reaction is completed, a solvent such as methanol, which is difficult to dissolve compound (I) in the reaction mixture but is easy to dissolve compounds other than compound (I), is mixed with the reaction mixture and filtered to remove compound (I). 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, or a mixed solvent thereof, an alkaline aqueous solution such as sodium hydroxide solution, and/or an acidic aqueous solution such as hydrochloric acid, and then washed with water, a low-boiling alcohol such as methanol, or a mixed solvent thereof to remove compound (I). Furthermore, the reaction mixture may be purified by column chromatography and/or recrystallization. Alternatively, after the reaction is completed, the solvent of the reaction mixture may be removed, and the obtained residue may be purified by column chromatography and/or recrystallization. After the reaction is completed, the reaction mixture may be purified by column chromatography and/or recrystallization.

In addition, 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 compound (I') in the presence of a base to produce a compound represented by formula (IM1) (hereinafter, sometimes referred to as compound (IM1)), and further, reacting compound (IM1) with a compound represented by formula (pt3).

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 of the compound represented by formula (pt1) and the compound represented by formula (pt2), the amount of the compound represented by formula (pt2) used is generally 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).

In the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3), the amount of the compound represented by formula (pt3) used 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 and reaction time in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2), and the reaction temperature and reaction time in the reaction between the compound represented by formula (IM1) and the compound represented by formula (pt3) are the same as the reaction temperature and reaction time in production method 1, and the preferred embodiments thereof are also the same.

The reaction of the compound represented by formula (pt1) with the compound represented by formula (pt2), and the reaction of the compound represented by formula (IM1) with the compound represented by formula (pt3) are usually carried out in the presence of a solvent. Examples of the solvent include the solvents exemplified in Production Method 1, and the preferred embodiments are the same.

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 based on 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 the formula (IM1) and the compound represented by the formula (pt3) is usually 1 part by mass to 1000 parts by mass based on 1 part by mass of the compound represented by the formula (IM1).

In the reaction of the compound represented by formula (pt1) with the compound represented by formula (pt2), and the reaction of the compound represented by formula (IM1) with the compound represented by formula (pt3), it is preferred that an acid coexists. Examples of the acid include the acids exemplified in Production Method 1, and the preferred embodiments are the same.

The amount of the acid used in the reaction between the compound represented by formula (pt1) and the compound represented by formula (pt2) is generally 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, based on 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 generally 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, based on 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), and 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) are not particularly limited, and various known methods can be used for extraction, for example, the method exemplified in Production Method 1.

Examples of the base used in the hydrolysis reaction of the compound represented by formula (I') in the presence of a base include organic acids 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, and the like. Alkali, metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, 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 an inorganic base, and particularly preferably potassium hydroxide.

The amount of the base used in the hydrolysis reaction of the compound represented by formula (I') in the presence of a base is usually 0.1 mol to 100 mol, preferably 1 mol to 70 mol, and more preferably 2 mol to 40 mol, based on 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 a base 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, based on 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 a base is usually 0 to 100°C, preferably 5 to 100°C, more preferably 20 to 100°C, further preferably 40 to 100°C, particularly preferably 60 to 100°C.

The reaction time for the hydrolysis reaction of the compound represented by formula (I') in the presence of a base is preferably continued until the disappearance of the compound represented by formula (I') is confirmed, and is usually 0.5 to 120 hours, preferably 1 to 72 hours, and more preferably 1 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 a base is not particularly limited, and various known methods can be used, for example, the methods exemplified in Production Method 1.

The coloring composition containing compound (I) can produce a color filter with a richer color.

[Coloring composition] The coloring composition of the present invention comprises compound (I) and a red colorant. Compound (I) and the red colorant can be used as a colorant (hereinafter, sometimes referred to as colorant (A)). The coloring composition of the present invention may include at least one selected from a resin (hereinafter referred to as resin (B)), a polymerizable compound (hereinafter referred to as polymerizable compound (C)), a polymerization initiator (hereinafter referred to as polymerization initiator (D)), a solvent (hereinafter referred to as solvent (E)), and a leveling agent (hereinafter referred to as leveling agent (F)). It is more preferred to include at least one selected from resin (B), polymerizable compound (C), polymerization initiator (D), and solvent (E), and it is further preferred to include at least one selected from resin (B), polymerizable compound (C), and polymerization initiator (D). In addition, when the polymerizable compound (C) is included, it is preferred to also include a polymerization initiator (D). Furthermore, in this specification, the compounds exemplified as components may be used alone or in combination unless otherwise specified.

[Colorant (A)] The colorant (A) includes a compound (I) and a red colorant. Since the colorant (A) includes the compound (I) and the red colorant, a color filter having good heat resistance can be obtained. In addition, compared with the existing yellow colorant, the compound (I) has a greater absorption at a longer wavelength (e.g., around 500 nm). Therefore, when the compound (I) is combined with the red colorant to form a red color filter, the color filter can be made into a thin film with a dark color, which is preferable in this respect.

[[Compound (I)]] Compound (I) is a compound represented by the above formula (I), and its preferred embodiment is also the same.

The content of the compound (I) is preferably 1% by mass or more, more preferably 3% by mass or more, and further preferably 5% by mass or more, and is preferably 50% by mass or less, more preferably 30% by mass or less, further preferably 20% by mass or less, and particularly preferably 15% by mass or less, relative to the total amount of the coloring agent (A). When the content of the compound (I) is within the above range, the heat resistance of the color filter produced becomes good.

[[Red color material]] As a red color material, it can be a red dye or a red pigment, preferably a red pigment.

As the red dye, a known red dye can be used, for example, the known red dyes listed in the Color Index (published by The Society of Dyers and Colourists) and the Dyeing Notes (Shikisensha). Specifically, the following can be cited: 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. Acid Red 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, 9 2. 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426; C.I. 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. Basic Red 1, 9, 10; C.I. Reactive Red 36; C.I. Mordant Red 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, etc.

In addition, as a red dye, Lumogen (registered trademark) F Red 305 (manufactured by BASF), which is a product of BASF, can also be used.

As the red pigment, a known red pigment can be used, for example, red pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Specifically, C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 178, 179, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273, 291, etc. are exemplified. Among them, at least one red pigment selected from C.I. Pigment Red 177, 254, and 291 is preferred, and at least one red pigment selected from C.I. Pigment Red 177 and 291 is particularly preferred.

The content of the red colorant is preferably 50 mass % or more, more preferably 70 mass % or more, further preferably 80 mass % or more, and is preferably 99 mass % or less, more preferably 95 mass % or less, based on the total amount of the coloring agent (A).

The total amount of the compound (I) and the red colorant is preferably 70 mass % or more, more preferably 80 mass % or more, further preferably 90 mass % or more, particularly preferably 95 mass % or more, and may be 100 mass % based on the total amount of the coloring agent (A).

Regarding compound (I), by containing a dispersant in a solvent and performing a dispersion treatment, a dispersion liquid in which compound (I) is more uniformly dispersed in the solution can be obtained.

The content of the compound (I) in the dispersion is preferably 1 mass % or more, more preferably 3 mass % or more, and is preferably 30 mass % or less, more preferably 20 mass % or less, and further preferably 15 mass % or less.

As the solvent, the solvents listed as the solvent (E) described later can be used.

Examples of the dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. Examples of the dispersant include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Lubrizol), EFKA (manufactured by CIBA), Ajisper (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (manufactured by BYK-chemie), and BYK (manufactured by BYK-chemie).

When a dispersant is used, the amount used is preferably 0.1 parts by mass or more and 5 parts by mass or less, and more preferably 0.5 parts by mass or more and 2.5 parts by mass or less, relative to 1 part by mass of compound (I). When the amount of the dispersant used is within the above range, a dispersion liquid in a uniform dispersed state tends to be obtained.

[[Colorant (A1)]] The colorant (A) may contain a colorant other than the compound (I) and the red colorant (sometimes referred to as the colorant (A1)).

If the coloring agent (A1) is a coloring agent other than compound (I) and a red color material, it may be a dye or a pigment. As the dye, a known dye may be used, for example, the known dyes recorded 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.

Specifically, the dyes with the following C.I. numbers can be listed. Examples include: 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 Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99; C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; C.I. Solvent Blue 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 Green) 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35 and other C.I. solvent dyes, 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, 9 9, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 15 7, 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 Orange: 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173; C.I. Acid Violet: 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; C.I. Acid Blue: 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, 12 6, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324: 1, 335, 340; C.I. Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109, etc. C.I. Acid Dyes, C.I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141; C.I. Direct Orange Orange) 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; C.I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; C.I. Direct Blue (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 ,101,106,107,108,109,113,114,115,117,119,120,137,149,150,153,155,156,158,159,160,161,162,163,164,165,166,1 67, 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 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82 and other C.I. Direct Dyes, C.I. Disperse Yellow 51, 54, 76; C.I. Disperse Violet 26, 27; C.I. Disperse Blue 1, 14, 56, 60 and other C.I. Disperse Dyes, C.I. Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; C.I. Basic Violet 2; C.I. Basic Green 1 and other C.I. Alkaline dyes, C.I. Reactive Yellow 2, 76, 116; C.I. Reactive Orange 16 and other C.I. Reactive dyes, C.I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; C.I. Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; C.I. Mordant Violet 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, 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 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.

Further, Lumogen (registered trademark) as a product of BASF can be listed, and Lumogen (registered trademark) F Yellow 083 (manufactured by BASF), Lumogen (registered trademark) F Yellow 170 (manufactured by BASF), and Lumogen (registered trademark) F Orange 240 (manufactured by BASF) can be listed.

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

As the pigment, known pigments can be used, for example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Specifically, we can list: C.I. Yellow Pigment 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 Blue Blue) 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60 and other blue pigments; C.I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other purple pigments; C.I. Pigment Green 7, 36, 58, 59, 62, 63 and other green pigments; C.I. Pigment Brown 23, 25 and other brown pigments; C.I. Pigment Black 1, 7, 31, 32 and other black pigments, etc.

The pigment may be subjected to rosin treatment, surface treatment using pigment derivatives with acidic or alkaline groups, grafting treatment on the pigment surface using polymer compounds, micronization treatment using sulfuric acid micronization method, or cleaning treatment using organic solvents or water to remove impurities, or removal treatment of ionic impurities using ion exchange method, etc., as needed. The pigment preferably has a uniform particle size. In addition, by containing a dispersant and performing a dispersion treatment, a dispersion in which the pigment is more uniformly dispersed in the solution can be obtained.

As the dispersant, the above-mentioned dispersant can be used.

When a dispersant is used, its usage amount is preferably 0.1 to 5 parts by mass, more preferably 0.2 to 2.5 parts by mass, relative to 1 part by mass of the pigment. If the usage amount of the dispersant is within the above range, there is a tendency to obtain a uniformly dispersed dispersion.

The content of the coloring agent (A) is preferably 5 mass % or more and 60 mass % or less, more preferably 8 mass % or more and 55 mass % or less, and still more preferably 10 mass % or more and 50 mass % or less, relative to the total amount of the solid components of the coloring composition. When the content of the coloring agent (A) is within the above range, the color concentration when the color filter is manufactured is sufficient, and the necessary amount of the resin (B) or the polymerizable compound (C) can be contained in the composition, so that a pattern with sufficient mechanical strength can be formed.

Furthermore, the so-called "total amount of solid components" in this specification refers to the amount after deducting the content of the solvent from the total amount of the coloring composition. The total amount of solid components and the content of each component relative thereto can be measured by known analytical methods such as liquid chromatography or gas chromatography.

[Resin (B)] The resin (B) is preferably an alkali-soluble resin, and more preferably a polymer having a structural unit derived from a 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, in addition to the structural unit derived from the monomer (a), a structural unit 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/or 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" have the same meaning.

Examples of monomers (a) include: unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-vinylbenzoic acid, m-vinylbenzoic acid, and p-vinylbenzoic acid; unsaturated dicarboxylic acids such as 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, and 1,4-cyclohexene dicarboxylic acid; Bicyclic unsaturated compounds containing carboxyl groups such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Unsaturated dicarboxylic anhydrides such as 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, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; Unsaturated mono[(meth)acryloxyalkyl]esters of polycarboxylic acids having a valence 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 from the viewpoint of copolymerization reactivity or solubility of the obtained resin in an alkaline aqueous solution.

The monomer (b) refers to a polymerizable compound having a cyclic ether structure with 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 the monomer (b) include a monomer having an oxycyclopropyl group and an ethylenic unsaturated bond (hereinafter referred to as "monomer (b1)"), a monomer having an oxycyclobutyl group and an ethylenic unsaturated bond (hereinafter referred to as "monomer (b2)"), and a monomer having a tetrahydrofuranyl group and an ethylenic unsaturated bond (hereinafter referred to as "monomer (b3)").

Examples of the monomer (b1) include a monomer having a structure in which a linear or branched chain aliphatic unsaturated hydrocarbon is epoxidized (hereinafter referred to as "monomer (b1-1)") and a monomer having a structure in which alicyclic unsaturated hydrocarbon is epoxidized (hereinafter referred to as "monomer (b1-2)").

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

Examples of the monomer (b1-2) include 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.)), a compound represented by formula (BI) and a compound represented by formula (BII).

[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]

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

Examples of the alkyl group in which a hydrogen atom is substituted with a hydroxyl group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group.

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 the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group.

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).

Examples of the compound represented by formula (BI) include compounds represented by any one of formulas (BI-1) to (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).

Examples of the compound represented by formula (BII) include compounds represented by any one of formulas (BII-1) to (BII-15), among which preferred are compounds represented by formulas (BII-1), (BII-3), (BII-5), (BII-7), (BII-9) and (BII-11) to (BII-15), and more preferred are compounds represented by formulas (BII-1), (BII-7), (BII-9) and (BII-15).

The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination of two or more. The compound represented by formula (BI) and the compound represented by formula (BII) may 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 to 95:5, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20 on a molar basis.

As the monomer (b2), a monomer having an oxycyclobutyl group and a (meth)acryloxy group is more preferred. As the monomer (b2), for example, 3-methyl-3-methacryloxymethyloxycyclobutane, 3-methyl-3-acryloxymethyloxycyclobutane, 3-ethyl-3-methacryloxymethyloxycyclobutane, 3-ethyl-3-acryloxymethyloxycyclobutane, 3-methyl-3-methacryloxyethyloxycyclobutane, 3-methyl-3-acryloxyethyloxycyclobutane, 3-ethyl-3-methacryloxyethyloxycyclobutane, 3-ethyl-3-acryloxyethyloxycyclobutane, etc. can be listed.

The monomer (b3) is more preferably a monomer having a tetrahydrofuranyl group and a (meth)acryloyloxy group. Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.

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, dicyclopentanyloxyethyl (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; (meth)acrylates containing a halogen atom such as 2,2,3,3,4,4,5,5-octafluoropentyl (meth)acrylate; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate and diethyl itaconate; 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-methoxy 5,6-di(2'-hydroxyethyl)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-di(2'-hydroxyethyl) ... [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 Bicyclic unsaturated compounds such as 5-(tert-butoxycarbonyl)bicyclo[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; Dicarbonyl imide derivatives such as 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)maleimide; 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 selected from (meth)acrylate 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl/(meth)acrylic acid copolymer, (meth)acrylate 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 weight average molecular weight of the resin (B) in terms of polystyrene is preferably 3,000 or more and 100,000 or less, more preferably 5,000 or more and 50,000 or less, and still more preferably 5,000 or more and 30,000 or less. When the molecular weight is within the above range, the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed portion in the developer is good, and the resolution of the colored pattern is improved.

The dispersion degree [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1.1 or more and 6 or less, and more preferably 1.2 or more and 4 or less.

The acid value is preferably 50 mg-KOH/g or more and 170 mg-KOH/g or less, more preferably 60 mg-KOH/g or more and 160 mg-KOH/g or less, and still more preferably 70 mg-KOH/g or more and 150 mg-KOH/g or less in terms of solid content. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be obtained, for example, by titration using an aqueous potassium hydroxide solution.

The content of the resin (B) is preferably 7% by mass or more and 65% by mass or less, more preferably 13% by mass or more and 60% by mass or less, and still more preferably 17% by mass or more and 55% by mass or less, relative to the total amount of the solid components. When the content of the resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern tend to be improved.

[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 an ethylenic unsaturated bond, etc., preferably a (meth)acrylate compound.

Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinyl pyrrolidone, and the monomer (a), monomer (b), and monomer (c).

Examples of polymerizable compounds having two ethylenically 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)acryloyloxy)propene. The present invention relates to 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, and preferably dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

The content of the polymerizable compound (C) is preferably 5% by mass or more and 65% by mass or less, more preferably 7% by mass or more and 60% by mass or less, further preferably 8% by mass or more and 55% by mass or less, and particularly preferably 10% by mass or more and 40% by mass or less, relative to the total amount of the solid components of the coloring composition. When the content of the polymerizable compound (C) is within the above range, the residual film rate during the formation of the coloring pattern and the chemical resistance of the color filter tend to be improved.

[Polymerization initiator (D)] The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active free radicals, acids, etc. by the action of light or heat to initiate polymerization, and a known polymerization initiator can be used. Examples of the polymerization initiator (D) include oxime compounds (e.g., O-acyl oxime compounds, etc.), phenylalkyl ketone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds, etc.

Examples of the O-acyl oxime compound include 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 PBG-327 (produced by Changzhou Qiangli Electronic New Materials Co., Ltd.), Irgacure OXE01, OXE02 (produced by BASF) and N-1919 (produced by ADEKA Co., Ltd.) can also be used. Among them, as the O-acyl oxime compound, it is preferred to be selected from N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, 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, preferably at least one selected from the group consisting of N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine and 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 carboalkoxy groups (for example, see Japanese Patent Publication No. 7-10913, etc.).

Examples of the triazine compounds include 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.

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzyldiphenylphosphine oxide, etc. 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 titanocene compounds, etc. These are preferably used in combination with a polymerization initiator aid. As polymerization initiation aids, there are: amine compounds such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.); alkoxyanthracene compounds such as 9,10-dimethoxyanthracene and 2-ethyl-9,10-dimethoxyanthracene; thioanthrone compounds such as 2-isopropylthioanthrone, 4-isopropylthioanthrone, and 2,4-diethylthioanthrone; carboxylic acid compounds such as phenylthioacetic acid, dimethylphenylthioacetic acid, and methoxyphenylthioacetic acid.

The polymerization initiator (D) is preferably a polymerization initiator comprising at least one selected from the group consisting of an alkyl phenoxide compound, a triazine compound, an acyl phosphine oxide compound, an oxime compound and a biimidazole compound, 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 0.1 parts by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 25 parts by mass or less, and further preferably 3 parts by mass or more and 25 parts by mass or less, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, there is a tendency to increase the sensitivity and shorten the exposure time, thereby improving the productivity of the color filter.

[Solvent (E)] The solvent (E) is not particularly limited, and a solvent commonly used in the field can be used. Examples of the solvent (E) include ester solvents (solvents containing -CO-O- and not containing -O- in the molecule), ether solvents (solvents containing -O- and not containing -CO-O- in the molecule), ether ester solvents (solvents containing -CO-O- and -O- in the molecule), ketone solvents (solvents containing -CO- and not containing -CO-O- in the molecule), alcohol solvents (solvents containing OH and not containing -O-, -CO-, and -CO-O- in the molecule), aromatic hydrocarbon solvents, amide solvents, and dimethyl sulfoxide.

Examples of the ester solvent include 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.

Examples of the ether solvent include 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.

Examples of the ether ester solvent include 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, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate.

Examples of 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.

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

Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene and mesitylene.

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

Among the above solvents, an organic solvent having a boiling point of 120° C. or higher and 180° C. or lower at 1 atm is preferred in terms of coating properties and drying properties. Preferred examples of the solvent 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 examples 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) is preferably 70% by mass or more and 95% by mass or less, and more preferably 75% by mass or more and 92% by mass or less, relative to the total amount of the coloring composition of the present invention. In other words, the total content of the solid components of the coloring composition is preferably 5% by mass or more and 30% by mass or less, and more preferably 8% by mass or more and 25% by mass or less. If the content of the solvent (E) is within the above range, there is a tendency that the flatness during coating is improved, and the color concentration is not insufficient when forming a color filter, and the display characteristics tend to be improved.

[Leveling agent (F)] As leveling agent (F), silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms can be listed. These may also have a polymerizable group in the side chain.

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) (manufactured by Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan 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 (registered trademark) 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, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronics Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemical Laboratories Co., Ltd.), etc.

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

When the leveling agent (F) is contained, its content is preferably 0.001 mass % or more and 0.2 mass % or less, more preferably 0.002 mass % or more and 0.1 mass % or less, and further preferably 0.01 mass % or more and 0.05 mass % or less, relative to the total amount of the coloring composition. The content does not include the content of the dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[Other ingredients] The coloring composition of the present invention may also contain polymerization initiation aids, fillers, other polymer compounds, adhesion promoters, light stabilizers, chain transfer agents and other additives known in the art as needed.

[Method for producing coloring composition] The coloring composition of the present invention can be prepared, for example, by mixing a coloring agent (A) comprising a compound (I) and a red colorant, and optionally a resin (B), a polymerizable compound (C), a polymerization initiator (D), a solvent (E), a leveling agent (F), and other components. The mixing can be performed by a known or conventional device or condition.

The coloring agent (A) can be used in the following state: it is pre-mixed with a part or all of the solvent (E) and dispersed to an average particle size of about 0.2 μm or less using a bead mill or the like. At this time, a part or all of the dispersant and the resin (B) can also be formulated as needed. It is preferred to prepare the target coloring composition by mixing the remaining components in the dispersion obtained in this way in a manner to form a prescribed concentration. When using a bead mill, the diameter of the beads is preferably not less than 0.05 mm and not more than 0.5 mm, and the material of the beads can be glass, ceramics, metal, etc.

[Color filter] As methods for producing the coloring pattern of the color filter using the coloring composition of the present invention, photolithography, inkjet method, printing method, etc. can be listed. Among them, photolithography is preferred. Photolithography is a method of applying the coloring composition on a substrate, drying it to form a composition layer, and exposing and developing the composition layer through a photomask. In photolithography, by not using a photomask during exposure and/or not performing development, a coloring coating film can be formed as a cured product of the composition layer.

The film thickness of the color filter (cured film) is, for example, 0.1 μm or more and 30 μm or less, preferably 0.1 μm or more and 20 μm or less, and further preferably 0.5 μm or more and 6 μm or less.

As the substrate, glass plates such as quartz glass, borosilicate glass, alumina silicate glass, sodium calcium glass with silicon dioxide coating on the surface, or resin plates such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicon, or aluminum, silver, silver/copper/palladium alloy thin films, etc. can be used. Other color filter layers, resin layers, transistors, circuits, etc. can also be formed on these substrates. In addition, a substrate obtained by subjecting a silicon substrate to HMDS (Hexamethyldisilazane) treatment can also be used.

The formation of pixels of various colors by photolithography can be performed by known or customary devices or conditions. For example, it can be produced as follows. First, the coloring composition is applied to the substrate, and the volatile components such as the solvent are removed by heat drying (pre-baking) and/or reduced pressure drying to obtain a smooth composition layer. As coating methods, there can be listed: spin coating, slit coating, slit and spin coating, etc. The temperature during heat drying is preferably above 30°C and below 120°C, and more preferably above 50°C and below 110°C. In addition, as the heating time, it is preferably above 10 seconds and below 60 minutes, and more preferably above 30 seconds and below 30 minutes. When the reduced pressure drying is performed, it is preferably performed at a pressure of 50 Pa to 150 Pa and a temperature range of 20°C to 25°C. The film thickness of the component layer is not particularly limited and can be appropriately selected according to the film thickness of the target color filter.

Next, the composition layer is exposed through a mask for forming a target coloring pattern. The pattern on the mask is not particularly limited, and a pattern corresponding to the target application is used. As the light source used in the exposure, a light source that generates light with a wavelength of 250 nm to 450 nm is preferred. For example, light less than 350 nm can be cut off using a filter that cuts off this wavelength region, or light near 436 nm, 408 nm, and 365 nm can be selectively extracted using a band pass filter that extracts these wavelength regions. Specifically, mercury lamps, light-emitting diodes, metal halide lamps, halogen lamps, etc. can be listed. In order to evenly irradiate the entire exposure surface with parallel light or to accurately align the positions of the mask and the substrate, it is preferable to use a miniaturized projection exposure device or a proximity exposure device such as a mask aligner and a stepper.

The exposed component layer is brought into contact with a developer to form a colored pattern on the substrate. By developing, the unexposed part of the component layer is dissolved in the developer and removed. As the developer, for example, an aqueous solution of alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide is preferred. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 mass% or more and 10 mass% or less, and more preferably 0.03 mass% or more and 5 mass% or less. Furthermore, the developer may also contain a surfactant. The developing method may be any one of a coating method, an immersion method, and a spray method. Furthermore, during development, the substrate may be tilted at any angle. It is better to wash with water after developing.

Furthermore, it is preferred to post-bake the obtained colored pattern. The post-bake temperature is preferably 80° C. or higher and 250° C. or lower, more preferably 100° C. or higher and 245° C. or lower. The post-bake time is preferably 1 minute or higher and 120 minutes or lower, more preferably 2 minutes or higher and 30 minutes or lower.

The coloring pattern and coloring film thus obtained are useful as a color filter, and the color filter is useful as a color filter used in a display device (e.g., a liquid crystal display device, an organic electroluminescence (EL) device, etc.), electronic paper, a solid-state imaging element, etc. [Example]

The present invention is described in more detail below by way of examples, but the present invention is not limited to these examples. In the examples, % and parts indicating the content or usage amount are based on mass unless otherwise specified.

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

[Example 1] 1 mol of 4-amino-6-fluoro-2-methylquinoline (manufactured by Sigma-Aldrich Japan Co., Ltd.), 8 mol of 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 21 mol of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 73 times the weight of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) of 1 mol of 4-amino-6-fluoro-2-methylquinoline were mixed. The mixture was stirred for 120 hours while being kept at 170°C. The mixture was cooled to room temperature, and methanol of 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 (I-1).

<Identification of the compound represented by formula (I-1)> (Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 537 (Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 535 Exact mass: 536

[Example 2] 1 mol of 4-amino-6-methoxy-2-methylquinoline (manufactured by Sigma-Aldrich Japan Co., Ltd.), 8 mol of 2,3-naphthalene dicarboxylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), 21 mol of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 73 times the weight of methyl benzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) of 1 mol of 4-amino-6-methoxy-2-methylquinoline were mixed. The mixture was stirred for 120 hours while being kept at 170°C. The mixture was cooled to room temperature, and methanol of 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 (I-2).

<Identification of the compound represented by formula (I-2)> (Mass analysis) Ionization mode = ESI+: m/z = [M+H] ⁺ 549 (Mass analysis) Ionization mode = ESI-: m/z = [MH] ^- 547 Exact mass: 548

(Pigment synthesis example) According to the contents of Japanese Patent Laid-Open No. 2002-179979, the following compound (I-3) was synthesized.

(Resin Synthesis Example 1) A suitable amount of nitrogen was passed through a flask equipped with 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 copolymer (resin B-1) solution having a solid content of 35.1% and a viscosity of 125 mPa·s measured by a B-type viscometer (23°C). The weight average molecular weight Mw of the generated copolymer was 9.2×10 ³ , the degree of dispersion was 2.08, and the acid value calculated as solid content was 77 mg-KOH/g. Resin B-1 has the following structural units.

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. Apparatus: HLC-8120GPC (manufactured by Tosoh Co., Ltd.) Column: TSK-GELG2000HXL Column temperature: 40°C Solvent: THF (tetrahydrofuran) Flow rate: 1.0 mL/min Solid content concentration of test liquid: 0.001 mass% to 0.01 mass% Injection volume: 50 μL Detector: refractive index (RI) Calibration standard substance: TSK standard polystyrene (TSK STANDARD POLYSTYRENE) F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Co., Ltd.) The ratio (Mw/Mn) of the weight average molecular weight and number average molecular weight converted to polystyrene obtained above was set as the dispersion degree.

(Preparation Example 1 of Coloring Dispersion Liquid) 〔Preparation of Coloring Dispersion Liquid (P-1)〕 The compound represented by formula (I-2), the compound represented by formula (I-3), the dispersant, the resin B-1, and the solvent E-1 were added to form the composition of Table 3, and zirconia beads were added and vibrated. The zirconia beads were removed by filtration to prepare a coloring dispersion liquid (P-1).

(Preparation Example 2 of Coloring Dispersion Liquid) 〔Preparation of Coloring Dispersion Liquid (P-2)〕 C.I. Pigment Yellow 185, the compound represented by formula (I-3), dispersant, resin B-1, and solvent E-1 were added to form the composition shown in Table 3, and zirconia beads were added and vibrated. The zirconia beads were removed by filtration to prepare a coloring dispersion liquid (P-2).

[Table 3] Unit (piece) Coloring Dispersion P-1 P-2 Composition Compound (I-2) 4 - PY185 - 4 Compound (I-3) 1 1 Dispersant (solid component) 7.5 7.5 Resin (B-1) (solid content) 4 4 Solvent (E-1) 83.5 83.5 Zirconia beads 300 300

In Table 3, each component represents the following compound. Compound (I-2): Compound represented by formula (I-2) PY185: C.I. Pigment Yellow 185 Compound (I-3): Compound represented by formula (I-3) Dispersant (solid component): BYK-LP N 6919 (manufactured by BYK) Resin (B-1) (solid component): Resin B-1 Solvent (E-1): Propylene glycol monomethyl ether acetate Zirconia beads: diameter 0.1 mm

(Preparation Example 3 of Coloring Dispersion Liquid) 〔Preparation of Coloring Dispersion Liquid (P-3)〕 The components are mixed in the following proportions to obtain a coloring dispersion liquid (P-3). C.I. Pigment Red 291                                                 12.0% Dispersant (solid content)                                 3.5% Resin (solid content)                                5.0% Propylene glycol monomethyl ether acetate                             79.5%

(Preparation Example 4 of Coloring Dispersion Liquid) 〔Preparation of Coloring Dispersion Liquid (P-4)〕 The components are mixed in the following proportions to obtain a coloring dispersion liquid (P-4). C.I. Pigment Red 177                                         13.0% Dispersant (solid content)                         4.6% Resin (solid content)                            4.6% Propylene glycol monomethyl ether acetate                             77.8%

[Example 3, Comparative Example 1] (Preparation of coloring composition) The components are mixed in a manner to obtain a coloring composition as shown in Table 4.

[Table 4] Unit (piece) Embodiment 3 Comparative example 1 Coloring Dispersion P-1 147.7 - P-2 - 148.3 P-3 353.3 291.7 P-4 185.3 244.2 Resin B-1 18.0 18.4 Polymeric compounds C-1 50.0 50.0 Polymerization initiator D-1 5.0 5.0 Solvent E-1 417.0 426.0 E-2 230.5 229.0 Leveling agent F-1 0.2 0.2

In Table 4, each component represents the following compound. Resin (B-1): Resin B-1 (solid component) Polymerizable compound (C-1): Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) Polymerization initiator (D-1): N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine (PBG-327; oxime compound; manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.) Solvent (E-1): Propylene glycol monomethyl ether acetate Solvent (E-2): Diacetone alcohol Leveling agent (F-1): Polyether modified silicone oil (solid component) (Toray Dow Corning (Toray Dow Corning) (Toray Silicone) (Toray Dow Corning ... Silicone) SH8400")

(Production of color filter (color coating)) A coloring composition was applied by spin coating on a 5 cm square glass substrate (Eagle 2000; manufactured by Corning) and then pre-baked at 100°C for 3 minutes to form a coloring composition layer. After cooling, the coloring composition layer formed on the substrate was irradiated with light at an exposure dose of 100 mJ/ ^cm2 (365 nm reference) in an atmospheric environment using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.). After light irradiation, the coloring composition layer was post-baked in an oven at 230°C for 30 minutes to obtain a coloring film.

(Color change evaluation) The obtained thin film on the glass substrate was measured for spectroscopy using a colorimeter (OSP-SP-200; manufactured by Olympus Co., Ltd.), and the xy chromaticity coordinates (x, y) and Y in the XYZ color system of the International Commission on Illumination (CIE) were measured using the isochromatic function of the C light source. The measurement results of the xy chromaticity coordinates are shown in Table 5. Thereafter, additional baking was performed at 230°C for 120 minutes in an oven. After the additional baking, the xy chromaticity coordinates and Y were measured again, and the color difference ΔEab* before and after heating was calculated based on the measured values using the method described in Japanese Industrial Standards (JIS) Z 8730:2009 (7. Color difference calculation method). The results are shown in Table 5. The smaller the color difference ΔEab*, the smaller the color change.

[Table 5] Embodiment 3 Comparative example 1 x 0.661 0.661 y 0.324 0.324 Color difference ΔEab* 0.7 0.8 [Industrial Availability]

According to the compound and the coloring composition of the present invention, a color filter having improved heat resistance can be provided. Therefore, the color filter formed by the compound and the coloring composition of the present invention is useful as a color filter used in a display device (for example, a liquid crystal display device, an organic EL device, an electronic paper, etc.) and a solid-state imaging element.

without

Claims (7)

A compound represented by formula (I):

[In formula (I), R ¹ , R ² , R ⁴ and R ⁵ each 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 ³ represents an alkoxy group having 1 to 4 carbon atoms; R ¹ and R ² 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 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; 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 with -Si(-)(-)-, -CH(-)- constituting the divalent alkyl group and the divalent heterocyclic group may be substituted with -N(-)-, -CH= constituting the divalent alkyl group and the divalent heterocyclic group may be substituted with -N=, and -CH ₂ - constituting the divalent alkyl group and the divalent heterocyclic group may be substituted with -O-, -S-, or -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]. The compound according to claim 1, wherein ^Q1 and ^Q2 in formula (I) are independently a group represented by formula (QQ1) or formula (QQ2),

[In formula (QQ1) to formula (QQ2), R ^Q1 to R ^Q10 each 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 ^Q1 to R ^Q4 may be bonded to one or more selected from R ^Q1 to R ^Q4 to form a ring, and R ^Q5 to R ^Q10 may be bonded to one or more selected from R ^Q5 to R ^Q10 to form a ring; M and MM have the same meanings as described above; ※ indicates a bond]. A coloring composition comprising the compound as described in claim 1 or claim 2, and a red colorant. The coloring composition as described in claim 3 further comprises a resin. The coloring composition as described in claim 3 or claim 4 further comprises a polymerizable compound and a polymerization initiator. A color filter formed by a coloring composition as described in any one of claim 3 to claim 5. A display device comprising a color filter as described in claim 6.