JP2020090676A - Compound, and colored curable resin composition including compound - Google Patents

Abstract

To provide a compound with which it is possible to suppress sublimation of a colorant when a color filter is formed from a colored curable resin composition.SOLUTION: The compound is represented by formula (Z) in the figure. (In formula (Z), Rand Reach independently represent H, a C1-20 monovalent saturated hydrocarbon group, an aryl group, a group including an acryloyl group, a group including a methacryloyl group, or a group including a silicon atom; and Rto Reach independently represent H, a halogen atom, a cyano group, a carboxyl group, a nitro group, a C1-20 alkyl group, a C1-20 alkoxy group, a group including an acryloyl group, or the like.)SELECTED DRAWING: None

Description

The present invention relates to a compound, a colorant containing the compound, a colored curable resin composition, and the like.

Dyes are used for color display using reflected light or transmitted light in the fields of, for example, fiber materials, liquid crystal display devices, and inkjets. As such a dye, coumarin 6 represented by the following formula is known.

JP, 2006-154740, A (Example 8).

In the step of forming a color filter from the colored curable resin composition containing the compound represented by the formula (d0), there is a problem that the colorant sublimes.

The present invention includes the following inventions.
[1] A compound represented by the formula (Z).

[In the formula (Z), R ¹ and R ² are each independently a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, an aryl group, a group containing an acryloyl group, or a group containing a methacryloyl group. Alternatively, it represents a group containing a silicon atom.
R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are each independently a hydrogen atom, a halogen atom, a cyano group, a carboxyl group, a nitro group, or a carbon number of 1 to 20. Represents an alkyl group, an alkoxy group having 1 to 20 carbon atoms, a group containing an acryloyl group, a group containing a methacryloyl group or a group containing a silicon atom.
Provided that at least ^one of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ contains an acryloyl group, a group containing a methacryloyl group, or A group containing a silicon atom. ]
[2] The compound according to [1], wherein the group containing a silicon atom is a group represented by formula (Z1).

[In the formula, R ^11A represents a single bond or an alkanediyl group having 1 to 10 carbon atoms, and —CH ₂ — contained in the alkanediyl group is —O—, —CO—, —NR ¹⁰ —, —. OCO-, -COO-, -OCONH-, -CONH- or -NHCO- may be substituted, and the hydrogen atom contained in the alkanediyl group has 1 to 4 carbon atoms which may have a hydroxyl group. It may be substituted with an alkyl group.
R ¹⁰ represents a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
R ^12A , R ^13A and R ^14A each independently represent a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
* Represents a bond with a nitrogen atom or a carbon atom. ]
[3] The compound according to [1] or [2], wherein the group containing an acryloyl group or the group containing a methacryloyl group is a group represented by formula (Z2).

[In the formula, R ^15A represents an alkanediyl group having 1 to 10 carbon atoms, and —CH ₂ — contained in the alkanediyl group is —O—, —CO—, —NR ¹¹ —, —OCO—, -COO-, -OCONH-, -CONH- or -NHCO- may be substituted, and the hydrogen atom contained in the alkanediyl group is an alkyl group having 1 to 4 carbon atoms and optionally having a hydroxyl group. May be replaced with.
R ¹¹ represents a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
R ^16A represents an acryloyl group or a methacryloyl group.
* Represents a bond with a nitrogen atom or a carbon atom. ]
[4] A colorant containing the compound according to any one of [1] to [3].
[5] The colorant according to [4], which further contains a green pigment.
[6] The colorant according to [5], wherein the green pigment is at least one selected from the group consisting of halogenated copper phthalocyanine pigments and halogenated zinc phthalocyanine pigments.
[7] The colorant according to [5] or [6], wherein the green pigment is at least one selected from the group consisting of chlorinated copper phthalocyanine pigments, brominated copper phthalocyanine pigments and brominated zinc phthalocyanine pigments.
[8] The green pigment is C.I. I. Pigment Green 36 and C.I. I. Pigment Green 58, the coloring agent according to any one of [5] to [7], which is at least one selected from the group consisting of Pigment Green 58.
[9] A colored curable resin composition containing the colorant according to any one of [4] to [8], a resin, a polymerizable compound and a polymerization initiator.
[10] A color filter formed from the colored curable resin composition according to [9].
[11] A liquid crystal display device including the color filter according to [10].

When forming a color filter from a colored curable resin composition containing the compound of the present invention, sublimation of the colorant can be suppressed.

<Compound represented by Formula (Z) (hereinafter, sometimes referred to as Compound (Z))>

[In the formula (Z), R ¹ and R ² are each independently a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, an aryl group, a group containing an acryloyl group, or a group containing a methacryloyl group. Alternatively, it represents a group containing a silicon atom.
R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are each independently a hydrogen atom, a halogen atom, a cyano group, a carboxyl group, a nitro group, or a carbon number of 1 to 20. Represents an alkyl group, an alkoxy group having 1 to 20 carbon atoms, a group containing an acryloyl group, a group containing a methacryloyl group or a group containing a silicon atom.
Provided that at least ^one of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ contains an acryloyl group, a group containing a methacryloyl group, or A group containing a silicon atom. ]

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ¹ and R ² include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, and an n-hexyl group. , N-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-dodecyl group, n-hexadecyl group, icosyl group, and other linear alkyl groups having 1 to 20 carbon atoms; isopropyl group , An isobutyl group, a sec-butyl group, a tert-butyl group, an isopentyl group, a neopentyl group, a 2-ethylhexyl group and the like, a branched chain alkyl group having 3 to 20 carbon atoms;
Examples thereof include alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and tricyclodecyl group.
Examples of the aryl group represented by R ¹ and R ² include phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2, Alkyl such as 5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2-ethylphenyl group, 3-ethylphenyl group and 4-ethylphenyl group Examples thereof include a phenyl group which may be substituted with a group and the like, and a tolyl group or a dimethylphenyl group is preferable.

R ¹ and R ² are each independently preferably an alkyl group having 1 to 20 carbon atoms, more preferably a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 5 to 10 carbon atoms, An ethyl group or a 2-ethylhexyl group is more preferable, and an ethyl group is even more preferable.

*-NR ¹ R ² (* represents a bond with a carbon atom) is preferably a group represented by the following formula.

Examples of the alkyl group having 1 to 20 carbon atoms represented by R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ include a methyl group, an ethyl group, an n-propyl group and isopropyl. Group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, 2-ethylhexyl group, octyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and methylcyclohexyl group Is mentioned.

Examples of the alkoxy group having 1 to 20 carbon atoms represented by R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, Examples include a pentyloxy group, a hexyloxy group, a heptyloxy group and an octyloxy group.

Examples of the halogen atom represented by R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ include a fluorine atom, a chlorine atom and a bromine atom.

However, at least ^one of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ is a group containing an acryloyl group, a group containing a methacryloyl group, or A group containing a silicon atom.

The group containing an acryloyl group or the group containing a methacryloyl group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ is a group structure. The unit means a group having at least one acryloyl group or methacryloyl group.
The group containing an acryloyl group usually has 3 to 16 carbon atoms, preferably 3 to 12 carbon atoms, and more preferably 3 to 8 carbon atoms.
The carbon number of the group containing a methacryloyl group is usually 4 to 17, preferably 4 to 13, and more preferably 4 to 9.
The group containing an acryloyl group is preferably a group containing an acryloyloxy group.
The group containing a methacryloyl group is preferably a group containing a methacryloyloxy group.
As the group containing an acryloyl group or the group containing a methacryloyl group, a group represented by the formula (Z2) is preferable.

[In the formula, R ^15A represents an alkanediyl group having 1 to 10 carbon atoms, and —CH ₂ — contained in the alkanediyl group is —O—, —CO—, —NR ¹¹ —, —OCO—, -COO-, -OCONH-, -CONH- or -NHCO- may be substituted, and the hydrogen atom contained in the alkanediyl group is an alkyl group having 1 to 4 carbon atoms and optionally having a hydroxyl group. May be replaced with.
R ¹¹ represents a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
R ^16A represents an acryloyl group or a methacryloyl group.
* Represents a bond with a nitrogen atom or a carbon atom. ]

Examples of the alkanediyl group having 1 to 10 carbon atoms represented by R ^15A include methylene group, ethylene group, trimethylene group, tetramethylene group, pentamethylene group, hexamethylene group, isopropylene group, isobutylene group and 2-methyltrimethyl group. Examples thereof include a methylene group, an isopentylene group, an isohexylene group, an isooctylene group and a 2-ethylhexylene group, an alkanediyl group having 1 to 6 carbon atoms is preferable, and an alkanediyl group having 1 to 4 carbon atoms is more preferable.
The C 1-10 alkanediyl group represented by R ^15A is preferably a group in which —CH ₂ — contained in the alkanediyl group is substituted with —O—. The number of —O— in R ^15A is preferably 1 to 3, more preferably 1 or 2, and further preferably 1. At least one of the -O- may be bonded to R ^16A . Note -CH ₂ - a nitrogen atom or a bond carbon atoms * -CH ₂ of the - is, -O -, - CO -, - NR 11 -, - OCO -, - COO -, - OCONH -, - It is preferably not substituted by CONH- and -NHCO-.
Examples of the alkyl group having 1 to 4 carbon atoms which may have a hydroxyl group include a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a sec-butyl group and a tert-butyl group. A methyl group, an ethyl group, a propyl group or a butyl group is preferable, and an ethyl group is more preferable.

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ¹¹ include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group and decyl group. Groups, dodecyl groups, hexadecyl groups, icosyl groups, isopropyl groups, isobutyl groups, sec-butyl groups, tert-butyl groups, isopentyl groups, neopentyl groups, 2-ethylhexyl groups, and other alkyl groups having 1 to 20 carbon atoms;
Examples thereof include alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and tricyclodecyl group.
R ¹¹ is preferably an alkyl group having 1 to 4 carbon atoms or a hydrogen atom, and more preferably a methyl group or a hydrogen atom.

Examples of the group containing an acryloyl group or a methacryloyl group include the group represented by (ii-1) to the group represented by (ii-42), and preferably the group represented by (ii-1) The group represented by (ii-8) and the group represented by (ii-13) to the group represented by (ii-22), and more preferably the group represented by (ii-1) to ( A group represented by ii-8), more preferably a group represented by (ii-1) or a group represented by (ii-5). In the formula, * represents a bond.

The group containing a silicon atom represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ includes a silicon atom as a constituent of the group. Means a group.
The silicon atom-containing group usually has 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 10 carbon atoms.
As the group containing a silicon atom, a group represented by the formula (Z1) is preferable.

[In the formula, R ^11A represents a single bond or an alkanediyl group having 1 to 10 carbon atoms, and —CH ₂ — contained in the alkanediyl group is —O—, —CO—, —NR ¹⁰ —, —. OCO-, -COO-, -OCONH-, -CONH- or -NHCO- may be substituted, and the hydrogen atom contained in the alkanediyl group has 1 to 4 carbon atoms which may have a hydroxyl group. It may be substituted with an alkyl group.
R ¹⁰ represents a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
R ^12A , R ^13A and R ^14A each independently represent a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
* Represents a bond with a nitrogen atom or a carbon atom. ]

Examples of the alkanediyl group having 1 to 10 carbon atoms represented by R ^11A include the same ones as the alkanediyl group having 1 to 10 carbon atoms represented by R ^15A . R ^11A is preferably an alkanediyl group having 1 to 6 carbon atoms, and more preferably an alkanediyl group having 1 to 4 carbon atoms.
Examples of the alkyl group having 1 to 4 carbon atoms which may substitute the hydrogen atom of the alkanediyl group of R ^11A include methoxy group, ethoxy group, propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group and tert. And a butoxy group.

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ¹⁰ include the same as the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ¹¹ .

Examples of the alkyl group having 1 to 4 carbon atoms represented by R ^12A , R ^13A and R ^14A include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group and a tert-butyl group. Groups, cyclopropyl groups and cyclobutyl groups.
Examples of the alkoxy group having 1 to 4 carbon atoms represented by R ^12A , R ^13A and R ^14A include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group and a tert-butoxy group. Is mentioned.
It is preferred that R ^12A , R ^13A and R ^14A are all the same group.
R ^12A , R ^13A and R ^14A are each independently preferably an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and an alkyl group having 1 to 2 carbon atoms or 1 carbon atom The alkoxy group of ˜2 is more preferable, and the methyl group is still more preferable.

Examples of the group containing a silicon atom include the groups described below. ^{Examples of the group in} which R ^11A is a single bond or is not substituted with —CH ₂ — contained in R ^11A include groups represented by the following (* represents a bond).

^Examples of the group in which —CH ₂ — included in R ^11A is substituted with —O— include groups represented by the following (* represents a bond).

Examples of the group in which —CH ₂ — contained in R ^11A is replaced by —CO— include groups represented by the following (* represents a bond).

The group in which —CH ₂ — contained in R ^11A is replaced by —NR ¹⁰ — is preferably —NH—, —NCH ₃ —, or —NC ₂ H ₅ —, and a preferable group is a group represented by the following. (* represents a bond).

Examples of the group in which —CH ₂ — contained in R ^11A is substituted with —OCO— include groups represented by the following (* represents a bond).

Examples of the group in which —CH ₂ — contained in R ^11A is replaced with —COO— include groups represented by the following (* represents a bond).

Examples of the group in which —CH ₂ — contained in R ^11A is substituted with —OCONH— include the groups shown below (* represents a bond).

Examples of the group in which —CH ₂ — contained in R ^11A is replaced with —CONH— include the groups shown below (* represents a bond).

Examples of the group in which —CH ₂ — contained in R ^11A is replaced with —NHCO— include the groups shown below (* represents a bond).

The hydrogen atom contained in the alkanediyl group contained in R ^11A may be substituted by an alkyl group having 1 to 4 carbon atoms which may have a hydroxyl group, (* represents a bond).

The group containing a silicon atom is represented by formula (Z1) in which —CH ₂ — contained in the alkanediyl group represented by R ^11A is substituted with —OCO—, —COO— or —OCONH—. A group is more preferable, and a group represented by formula (Z1) in which —CH ₂ — contained in the alkanediyl group represented by R ^11A is substituted with —COO— is further preferable. The group containing a silicon atom is preferably a group shown below.

R ³ , R ⁴ , R ⁵ and R ⁶ are each independently preferably a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and are preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. A hydrogen atom or a methyl group is more preferable, and a hydrogen atom is particularly preferable.
R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are preferably each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or a carboxyl group, and a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a carboxyl group. A group is more preferable, and a hydrogen atom or a carboxyl group is further preferable.
R ^7, at least one of R ^8, R ⁹ and R ^10, a group containing an acryloyl group is preferably a group containing a group or a silicon atom containing methacryloyl group, R ^7, R ^8, R ⁹ and R It is preferable that any one of ¹⁰ is a group containing an acryloyl group, a group containing a methacryloyl group or a group containing a silicon atom.
Further, at least one of R ⁸ and R ⁹ is preferably a group containing an acryloyl group, a group containing a methacryloyl group or a group containing a silicon atom, and R ⁷ and R ¹⁰ are hydrogen atoms, and R ⁸ and At least one of R ⁹ and, more preferably, either R ⁸ or R ⁹ is preferably a group containing an acryloyl group, a group containing a methacryloyl group or a group containing a silicon atom.

Specific examples of the compound (Z) include compounds represented by the formula (Z-1) to compounds represented by the formula (Z-56).

The compound (Z) can be prepared according to, for example, Dyes and Pigments (2008), 77,556-558. It can be manufactured according to the method described in.
Specifically, the compound represented by the formula (Z) in which R ⁵ =hydrogen atom is a compound represented by the formula (2-A), a compound represented by the formula (2-B) and ethyl cyanoacetate. Can be produced by a cyclization reaction in the presence of benzoic acid and a solvent.
The reaction temperature is preferably 0°C to 200°C, more preferably 100°C to 150°C. The reaction time is preferably 1 to 24 hours, more preferably 8 to 16 hours. Examples of the solvent include methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, and N-methylpyrrolidone, and 1-pentanol is preferable.

[In the formula (2-A) and the formula (2-B), R ^{1 to} R ⁴ and R ^{6 to} R ¹⁰ each have the same meaning as described above. ]

The amount of the compound represented by the formula (2-A) used is preferably 1 mol to 10 mol, and more preferably 1 to 5 mol, relative to 1 mol of the compound represented by the formula (2-B). And more preferably 1 mol.
The amount of ethyl cyanoacetate used is preferably 1 mol to 10 mol, more preferably 1 to 5 mol, and further preferably 1 mol, relative to 1 mol of the compound represented by the formula (2-B). Is.
The amount of benzoic acid used is preferably 0.1 mol to 3 mol, and more preferably 0.3 to 0.4 mol, per 1 mol of the compound represented by formula (2-B).
After obtaining the compound represented by the formula (Z) in which R ⁵ =hydrogen atom, an arbitrary substituent may be introduced into R ⁵ by a known method.

Examples of the method of obtaining the compound represented by the formula (Z), which is the target compound, from the reaction mixture include a method of appropriately adjusting the temperature of the reaction mixture to precipitate crystals, and collecting the crystals by filtration. The crystals collected by filtration are water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, acetic acid, ethyl acetate, hexane, toluene, N,N-dimethylformamide. It is preferable to wash with a solvent such as N, N-methylpyrrolidone or a mixed solution thereof, and then dry. If necessary, it may be further purified by a known method such as column chromatography or recrystallization.

Further, for example, the compound (Z) in which R ⁹ is a group containing a silicon atom can be obtained by reacting the compound represented by the formula (z5a) with the compound represented by the formula (z6). The compound represented by the formula (z5a) can be produced by diazo coupling the compound represented by the formula (2-A) and the compound represented by the formula (z4a).
Similarly, the compound (Z) in which R ⁸ is a group containing a silicon atom can be obtained by reacting the compound represented by the formula (z5b) with the compound represented by the formula (z6). The compound represented by the formula (z5b) can be produced by diazo coupling the compound represented by the formula (2-A) and the compound represented by the formula (z4b).
In this specification, the compound represented by the formula (z5a) and the compound represented by the formula (z5b) may be collectively referred to as the compound represented by the formula (z5).

[In the formula, R ¹¹³ represents a divalent linking group.
R ¹¹⁴ and R ¹¹⁵ each independently represent a hydrophilic group.
R ¹¹⁶ represents a group containing a silicon atom.
R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ have the same meanings as described above. ]

^Examples of the divalent linking group represented by R ¹¹³ include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, an isopropylene group, an isobutylene group, a 2-methyltrimethylene group, and an isopentylene group. Group, an isohexylene group, an isooctylene group, an alkanediyl group having 1 to 10 carbon atoms such as a 2-ethylhexylene group. It is, -O - - -CH ₂ contained in the alkanediyl ^{group, - CO -, - NR 10} -, - OCO -, - COO -, - OCONH -, - CONH- or -NHCO- with substituted Good. R ¹⁰ has the same meaning as described above.
Examples of the hydrophilic group represented by R ¹¹⁴ and R ¹¹⁵ include a hydroxy group and a carboxy group. However, it is preferable that R ¹¹⁴ and R ¹¹⁵ do not represent the same group, and that R ¹¹⁴ is a carboxyl group and R ¹¹⁵ is a hydroxyl group.
The group containing a silicon atom represented by R ¹¹⁶ represents a group containing a silicon atom as a constituent element of the group, and is preferably a group represented by the formula (Z1).

^{IN FORMULA} , R ^{< 11A} >, R ^{< 12A} >, R ^<13A > AND R ^<14A > ^{REPRESENT A SAID MEANING} .
* Represents a bond with R ¹¹⁵ . ]
* -R ¹¹³ -R ¹¹⁶ (* represents a bond to the carbon atom) is a group represented by the equivalent to R ⁸ and R ⁹ in the compound (Z).

The reaction between the compound represented by formula (z5) and the compound represented by formula (z6) is preferably carried out in the presence of a halogenated solvent such as chloroform. The reaction temperature is preferably -10°C to 100°C, more preferably 0°C to 50°C. The reaction time is preferably 1 to 12 hours, more preferably 1 to 4 hours.

The amount of the compound represented by the formula (z6) used is usually 1 mol or more and 8 mol or less, preferably 1 mol or more and 4 mol or less, relative to 1 mol of the compound represented by the formula (z5).
During the reaction, it is more preferable to add an acidic catalyst so that the reaction proceeds smoothly.
Examples of the acidic catalyst include mineral acids such as sulfuric acid and hydrochloric acid.
The amount of these catalysts used is arbitrary, but is preferably 0.01 to 4 mol, and more preferably 0.8 to 2 mol, relative to 1 mol of the compound represented by the formula (z6).

Examples of the method for obtaining the compound of the present invention, which is a target compound, from the reaction mixture include a method in which the reaction mixture is mixed with an acid (eg, acetic acid) and water and the precipitated crystals are collected by filtration. The acid is preferably prepared by preparing an aqueous solution of the acid in advance and then adding the reaction mixture to the aqueous solution. The temperature at which the reaction mixture is added is usually 10°C or higher and 50°C or lower, preferably 20°C or higher and 50°C or lower, and more preferably 20°C or higher and 30°C or lower. After the reaction mixture is added to the acid aqueous solution, it is preferable to stir at the same temperature for about 0.5 to 2 hours. The crystals collected by filtration are preferably washed with water or the like and then dried. If necessary, it may be further purified by a known method such as recrystallization.

Further, for example, the compound (Z) in which R ⁹ is a group containing an acryloyl group or a group containing a methacryloyl group is obtained by reacting a compound represented by the formula (z8a) with a compound represented by the formula (z9). Can be obtained by The compound represented by formula (z8a) can be produced by reacting the compound represented by formula (2-A) with the compound represented by formula (z7a).
The compound (Z) in which R ⁹ is a group containing an acryloyl group or a group containing a methacryloyl group can be obtained by reacting a compound represented by the formula (z8b) with a compound represented by the formula (z9). it can. The compound represented by formula (z8b) can be produced by reacting the compound represented by formula (2-A) with the compound represented by formula (z7b).
In this specification, the compound represented by the formula (z8a) and the compound represented by the formula (z8b) may be collectively referred to as the compound represented by the formula (z8).

[In the formula, R ¹¹¹ represents a divalent linking group.
R ¹¹⁰ represents a group containing an acryloyl group or a group containing a methacryloyl group.
R ¹¹² represents a halogen atom.
R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ have the same meanings as described above. ]

^Examples of the divalent linking group represented by R ¹¹¹ include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, an isopropylene group, an isobutylene group, a 2-methyltrimethylene group and an isopentylene group. Group, an isohexylene group, an isooctylene group, an alkanediyl group having 1 to 10 carbon atoms such as a 2-ethylhexylene group. It is, -O - - -CH ₂ contained in the alkanediyl ^{group, - CO -, - NR 11} -, - OCO -, - COO -, - OCONH -, - CONH- or -NHCO- with substituted Good. R ¹¹ has the same meaning as described above.
Examples of the halogen atom represented by R ¹¹² include a chlorine atom and a bromine atom.
Examples of the group containing an acryloyl group or the group containing a methacryloyl group represented by R ¹¹⁰ include a group having at least one acryloyl group or methacryloyl group as a constitutional unit of the group.
* -R ¹¹¹ -R ¹¹⁰ (* represents. A bond to the carbon atom) is a group represented by the equivalent to R ⁸ and R ⁹ in the compound (Z).

The reaction between the compound represented by formula (z8) and the compound represented by formula (z9) is preferably carried out in the presence of a halogenated solvent such as chloroform. The reaction temperature is preferably -10°C to 100°C, more preferably 0°C to 50°C. The reaction time is preferably 1 to 12 hours, more preferably 1 to 4 hours.

The amount of the compound represented by the formula (z9) used is usually 1 mol or more and 8 mol or less, preferably 1 mol or more and 4 mol or less, relative to 1 mol of the compound represented by the formula (z8).
During the reaction, it is more preferable to add an acidic catalyst so that the reaction proceeds smoothly. Examples of the acidic catalyst include mineral acids such as sulfuric acid and hydrochloric acid.
The amount of these catalysts used is arbitrary, but is preferably 0.01 to 4 mol, and more preferably 0.8 to 2 mol, relative to 1 mol of the compound represented by the formula (z9).

Examples of the method for obtaining the compound of the present invention, which is a target compound, from the reaction mixture include the same method as the method for obtaining the compound (Z) in which R ⁸ or R ⁹ is a group containing a silicon atom.

The compound (Z) of the present invention can be used as a dye.

The colored curable resin composition of the present invention contains a colorant (A) containing a compound (Z), a resin (B), a polymerizable compound (C) and a polymerization initiator (D).
As the colorant (A), two or more kinds of the compound (Z) may be used. As the colorant (A), a dye other than the compound (Z) or a green pigment (P) may be used.
The colored curable resin composition of the present invention preferably further contains at least one selected from the group consisting of a solvent (E) and a leveling agent (F).
The colored curable resin composition of the present invention may further contain a polymerization initiation aid (D1).
In the present specification, the compounds exemplified as each component can be used alone or in combination of two or more kinds unless otherwise specified.

As the dye other than the compound (Z), a yellow dye or a red dye is preferable, and a yellow dye is particularly preferable. Examples of the yellow dye include dyes having a pyridone skeleton.

Examples of the green pigment (P) include halogenated copper phthalocyanine pigments such as fluorinated copper phthalocyanine pigments, chlorinated copper phthalocyanine pigments and brominated copper phthalocyanine pigments; fluorinated zinc phthalocyanine pigments, chlorinated zinc phthalocyanine pigments, brominated zinc phthalocyanine pigments. And halogenated zinc phthalocyanine pigments such as C.I. I. Pigment Green 7, 10, 15, 25, 36, 47, 58 and the like green pigments.
The green pigment (P) is preferably at least one selected from the group consisting of halogenated copper phthalocyanine pigments and halogenated zinc phthalocyanine pigments,
More preferably at least one selected from the group consisting of chlorinated copper phthalocyanine pigment, brominated copper phthalocyanine pigment and brominated zinc phthalocyanine pigment,
C. I. More preferably, it is at least one selected from the group consisting of Pigment Green 36 and 58.
Since the color difference after the sublimation test is small, the green pigment (P) is preferably a halogenated copper phthalocyanine pigment, and more preferably at least one selected from the group consisting of a chlorinated copper phthalocyanine pigment and a brominated copper phthalocyanine pigment. , C.I. I. Pigment Green 36 is more preferable.

The colorant (A) may include other pigments, for example,
Specifically, C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, Yellow pigments such as 147, 148, 150, 153, 154, 166, 173, 180, 194, 214;
C. I. Pigment Blue 15, 15:3, 15:4, 15:6, 60 and other blue pigments; and the like.

The content of the compound (Z) is preferably 0.01% by mass or more and 90% by mass or less, more preferably 0.1% by mass or more and 80% by mass or less, based on the total amount of the colorant (A). , More preferably 1% by mass or more and 65% by mass or less, and even more preferably 2% by mass or more and 60% by mass or less.
When the green pigment (P) is contained, its content is preferably 10% by mass or more and 99.99% by mass or less, more preferably 20% by mass or more and 99.9% by mass based on the total amount of the colorant (A). It is not more than 35% by mass, more preferably not less than 35% by mass and not more than 99% by mass, still more preferably not less than 40% by mass and not more than 98% by mass.
When the green pigment (P) is included, the content ratio of the compound (Z) and the green pigment (P) [compound (Z):green pigment (P)] is preferably 1:99 to 50:50, more preferably It is 2:98 to 30:70, and more preferably 3:97 to 20:80.

The total content of the compound (Z) and the green pigment (P) is preferably 10% by mass or more, more preferably 30% by mass or more, further preferably 50% by mass or more, based on the total amount of the colorant (A). Is more preferably 70% by mass or more, particularly preferably 80% by mass or more, and the upper limit is 100% by mass or less, and may be 95% by mass or less.

The content of the colorant (A) is usually 1% by mass or more and 99% by mass or less, and preferably 2% by mass or more and 90% by mass or less, based on the total solid content of the colored curable resin composition. , More preferably 3% by mass or more and 80% by mass or less, further preferably 5% by mass or more and 70% by mass or less, still more preferably 5% by mass or more and 60% by mass or less, particularly preferably 5% by mass. It is 50 mass% or less. When the content of the colorant (A) is within the above range, desired spectrum and color density can be obtained.

In the present specification, the “total amount of solids” refers to the total amount of components excluding the solvent (E) from the colored curable resin composition of the present invention. The total amount of solid content and the content of each component relative thereto can be measured by a known analysis means such as liquid chromatography or gas chromatography.

<Resin (B)>
The resin (B) is not particularly limited, but is preferably an alkali-soluble resin, and an addition polymer having a structural unit derived from at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides can be used. More preferable. Examples of such a resin include the following resins [K1] to [K6].
Resin [K1] At least one kind (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter sometimes referred to as “(a)”), and a cyclic ether structure having 2 to 4 carbon atoms Copolymer with a monomer (b) having an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)");
Resins [K2] (a) and (b) and a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter referred to as "(c)"). In some cases) with a copolymer;
Copolymer of resin [K3] (a) and (c);
Resin [K4] Resin obtained by reacting (b) with a copolymer of (a) and (c);
Resin [K5] Resin obtained by reacting (a) with a copolymer of (b) and (c);
Resin [K6] A resin obtained by reacting a copolymer of (b) and (c) with (a) and further reacting with a carboxylic acid anhydride.

Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid;
Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid, 1,4-cyclohexene dicarboxylic acid;
Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo Bicyclo unsaturated compounds containing a carboxy group such as [2.2.1] hept-2-ene and 5-carboxy-6-ethylbicyclo [2.2.1] hept-2-ene;
Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6- Unsaturated dicarboxylic acid anhydrides such as tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride;
Unsaturated mono[(meth)acryloyloxyalkyl]esters of divalent or higher valent polycarboxylic acids such as mono[2-(meth)acryloyloxyethyl]succinate and mono[2-(meth)acryloyloxyethyl]phthalate. Kind;
Examples thereof include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid.
Of these, acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerization reactivity and the solubility of the resulting resin in an aqueous alkaline solution.

(B) is, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. Say. (B) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.
In addition, in this specification, "(meth)acrylic acid" represents at least one selected from the group consisting of acrylic acid and methacrylic acid. The expressions such as “(meth)acryloyl” and “(meth)acrylate” have the same meaning.

Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b1)”), a monomer having an oxetanyl group and an ethylenically unsaturated bond. A monomer (b2) (hereinafter sometimes referred to as “(b2)”), a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b3)”), etc. Can be mentioned.

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

Examples of (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, and p. -Vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, 2,4,6-tris (Glycidyloxymethyl) styrene etc. are mentioned.

Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane, and 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer M100; manufactured by Daicel Corporation), formula Examples thereof include compounds represented by (I) and compounds represented by formula (II).

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

Examples of the alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group and tert-butyl group.
Examples of the alkyl group having a hydrogen atom substituted with hydroxy include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, and a 1-hydroxy group. Examples thereof include a 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.
R ^a and R ^b are preferably a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group or a 2-hydroxyethyl group, and more preferably a hydrogen atom or a methyl group.

Examples of the alkanediyl group include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane- 1,6-diyl group and the like can be mentioned.
Examples of X ^a and X ^b include ^a single bond, a methylene group, an ethylene group, *—CH ₂ —O— and *—CH ₂ CH ₂ —O—, and a more preferred single bond, *—CH ₂ CH ₂ —O— can be mentioned (* represents a bond with O).

Examples of the compound represented by the formula (I) include compounds represented by any of the formulas (I-1) to (I-15). Among them, formula (I-1), formula (I-3), formula (I-5), formula (I-7), formula (I-9) or formula (I-11) to formula (I-15). The compound represented by the formula (I-1), the formula (I-7), the formula (I-9) or the compound represented by the formula (I-15) is more preferable.

Examples of the compound represented by the formula (II) include compounds represented by any of the formulas (II-1) to (II-15). Among them, the formula (II-1), the formula (II-3), the formula (II-5), the formula (II-7), the formula (II-9) or the formula (II-11) to the formula (II-15). The compound represented by formula (II-1), formula (II-7), formula (II-9) or formula (II-15) is more preferable.

The compound represented by the formula (I) and the compound represented by the formula (II) may be used alone or in combination with the compound represented by the formula (I) and the compound represented by the formula (II). You may. When these are used in combination, the content ratio of the compound represented by formula (I) and the compound represented by formula (II) is on a molar basis, preferably 5:95 to 95:5, more preferably 10:90 to. 90:10, and more preferably 20:80 to 80:20.

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

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

It is preferable that (b1) is (b1) because the heat resistance and chemical resistance of the obtained color filter can be further improved. Furthermore, (b1-2) is more preferable in that the storage stability of the colored curable resin composition is excellent.

Examples of (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, and 2-ethylhexyl (meth). Acrylate, dodecyl(meth)acrylate, lauryl(meth)acrylate, stearyl(meth)acrylate, cyclopentyl(meth)acrylate, cyclohexyl(meth)acrylate, 2-methylcyclohexyl(meth)acrylate, tricyclo[5.2.1.0]. ^2,6 ]Decan-8-yl(meth)acrylate (in the art, it is referred to as “dicyclopentanyl(meth)acrylate” by a trivial name. In addition, in the case of “tricyclodecyl(meth)acrylate”, ,), tricyclo[5.2.1.0 ^2,6 ]decen-8-yl(meth)acrylate (known in the art as “dicyclopentenyl (meth)acrylate” as a trivial name). ), dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, benzyl (Meth)acrylic acid esters such as (meth)acrylate;
Hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;
Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and itaconic acid diethyl;
Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5- Hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]. Hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2] .1] hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2. 1] hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy -5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2 2.1] hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(cyclohexyl) Bicyclo unsaturated compounds such as oxycarbonyl)bicyclo[2.2.1]hept-2-ene;
N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3 -Dicarbonylimide derivatives such as maleimide propionate and N-(9-acridinyl)maleimide;
Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene. , Isoprene, 2,3-dimethyl-1,3-butadiene and the like.
Of these, styrene, vinyltoluene, benzyl(meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decan-8-yl(meth)acrylate, N from the viewpoint of copolymerization reactivity and heat resistance. -Phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene and the like are preferable.

In the resin [K1], the ratio of the structural units derived from each is such that in all the structural units constituting the resin [K1],
Structural unit derived from (a); 2 to 60 mol%
Structural unit derived from (b); 40 to 98 mol%
Is preferred,
Structural unit derived from (a); 10 to 50 mol%
Structural unit derived from (b); 50 to 90 mol%
Is more preferable.
When the ratio of the structural unit of the resin [K1] is within the above range, the storage stability of the colored curable resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained color filter are excellent. Tend.

The resin [K1] can be obtained, for example, by the method described in the document “Experimental Method for Polymer Synthesis” (Takayuki Otsu, Kagaku Dojin, 1st edition, 1st edition, published on March 1, 1972) and the document. It can be manufactured by referring to the cited document described in.

Specifically, a predetermined amount of (a) and (b), a polymerization initiator, a solvent and the like are placed in a reaction vessel, and oxygen is replaced by, for example, nitrogen to create a deoxygenated atmosphere, while stirring, The method of heating and keeping warm is mentioned. The polymerization initiator, solvent and the like used here are not particularly limited, and those generally used in the relevant field can be used. For example, as a polymerization initiator, an azo compound (2,2′-azobisisobutyronitrile, 2,2′-azobis(2,4-dimethylvaleronitrile) or the like) or an organic peroxide (benzoyl peroxide or the like) The solvent may be any solvent that can dissolve each monomer, and examples thereof include the solvent described below as the solvent (E) of the colored curable resin composition of the present invention.

The obtained copolymer may be used as the solution after the reaction as it is, or may be used as a concentrated or diluted solution, or taken out as a solid (powder) by a method such as reprecipitation. You may use the thing. In particular, by using the solvent contained in the colored curable resin composition of the present invention as a solvent during this polymerization, the solution after the reaction can be used as it is for the preparation of the colored curable resin composition of the present invention. Therefore, the manufacturing process of the colored curable resin composition of the present invention can be simplified.

In the resin [K2], the ratio of the structural units derived from each is such that in all the structural units constituting the resin [K2],
Structural unit derived from (a); 2-45 mol%
Structural unit derived from (b): 2-95 mol%
Structural unit derived from (c): 1 to 65 mol%
Is preferred,
Structural unit derived from (a); 5 to 40 mol%
Structural unit derived from (b); 5 to 80 mol%
Structural unit derived from (c); 5 to 60 mol%
Is more preferable.
When the ratio of the structural unit of the resin [K2] is within the above range, the storage stability of the colored curable resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained color filter, It tends to have excellent heat resistance and mechanical strength.

The resin [K2] can be produced, for example, in the same manner as the method described as the method for producing the resin [K1].

In the resin [K3], the ratio of the structural units derived from each is such that in all the structural units constituting the resin [K3],
Structural unit derived from (a); 2 to 60 mol%
Structural unit derived from (c); 40 to 98 mol%
Is preferred,
Structural unit derived from (a); 10 to 50 mol%
Structural unit derived from (c); 50 to 90 mol%
Is more preferable.
The resin [K3] can be produced, for example, in the same manner as the method described as the method for producing the resin [K1].

The resin [K4] is a carboxylic acid and/or carboxylic anhydride obtained by obtaining a copolymer of (a) and (c) and having a cyclic ether having 2 to 4 carbon atoms in (b). It can be manufactured by adding to.
First, the copolymer of (a) and (c) is produced in the same manner as the method described as the method of producing the resin [K1]. In this case, it is preferable that the ratio of the structural units derived from each is the same as that of the resin [K3].

Next, a part of the carboxylic acid and/or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms contained in (b).
Subsequent to the production of the copolymer of (a) and (c), the atmosphere in the flask was replaced with nitrogen from air, and (b) the reaction catalyst of the carboxylic acid or carboxylic acid anhydride and the cyclic ether (for example, tris( Resin [K4] can be produced by placing (dimethylaminomethyl)phenol etc.) and a polymerization inhibitor (eg hydroquinone etc.) in a flask and reacting at 60 to 130° C. for 1 to 10 hours. it can.
The amount of (b) used is preferably 5 to 80 mol, and more preferably 10 to 75 mol, based on 100 mol of (a). By setting it in this range, the storage stability of the colored curable resin composition, the developability in forming a pattern, and the solvent resistance, heat resistance, mechanical strength and sensitivity of the obtained pattern are well balanced. Tend. Since the cyclic ether has high reactivity and unreacted (b) hardly remains, (b1) is preferable as the (b) used in the resin [K4], and further (b1-1) is more preferable.
The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass based on 100 parts by mass of the total amount of (a), (b) and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass based on 100 parts by mass of the total amount of (a), (b) and (c).
Reaction conditions such as a charging method, a reaction temperature and a time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization and the like. As with the polymerization conditions, the charging method and the reaction temperature can be appropriately adjusted in consideration of the production equipment and the amount of heat generated by the polymerization.

As the resin [K5], in the first step, a copolymer of (b) and (c) is obtained in the same manner as in the method for producing the resin [K1] described above. Similarly to the above, the obtained copolymer may be used as it is after the reaction, or may be used as a concentrated or diluted solution, or as a solid (powder) by a method such as reprecipitation. You may use what was taken out as.
The ratios of the structural units derived from (b) and (c) are, respectively, with respect to the total number of moles of all the structural units constituting the copolymer.
Structural unit derived from (b); 5-95 mol%
Structural unit derived from (c); 5-95 mol%
Is preferred,
Structural unit derived from (b); 10 to 90 mol%
Structural unit derived from (c): 10 to 90 mol%
Is more preferable.

Furthermore, under the same conditions as in the method for producing the resin [K4], the carboxylic acid or carboxylic acid anhydride contained in (a) is added to the cyclic ether derived from (b) in the copolymer of (b) and (c). The resin [K5] can be obtained by reacting the substances.
The amount of (a) used to react with the above copolymer is preferably 5 to 80 mol per 100 mol of (b). Since the cyclic ether has high reactivity and the unreacted (b) hardly remains, (b1) is preferable as the (b) used in the resin [K5], and further (b1-1) is preferable.

The resin [K6] is a resin obtained by further reacting the resin [K5] with a carboxylic acid anhydride. The hydroxy group generated by the reaction between the cyclic ether and the carboxylic acid or the carboxylic acid anhydride is reacted with the carboxylic acid anhydride.
Examples of the carboxylic acid anhydride include maleic anhydride, citraconic 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 and the like. The amount of the carboxylic acid anhydride used is preferably 0.5 to 1 mol per 1 mol of the amount used of (a).

Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ] Resin [K1] such as decyl (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/vinyltoluene copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane /Resin [K2] such as (meth)acrylic acid/styrene copolymer; benzyl(meth)acrylate/(meth)acrylic acid copolymer, styrene/(meth)acrylic acid copolymer, benzyl(meth)acrylate/ Resin [K3] such as tricyclodecyl (meth)acrylate/(meth)acrylic acid copolymer; resin obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate/(meth)acrylic acid copolymer, Resin prepared by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate/styrene/(meth)acrylic acid copolymer, tricyclodecyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer Resin [K4] such as a resin obtained by adding glycidyl (meth)acrylate to a polymer; a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate with (meth)acrylic acid, tri A resin [K5] such as a resin obtained by reacting a copolymer of cyclodecyl (meth)acrylate/styrene/glycidyl (meth)acrylate with (meth)acrylic acid; of tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate Examples of the resin include a resin [K6] such as a resin obtained by reacting a copolymer with (meth)acrylic acid and tetrahydrophthalic anhydride.

The resin (B) is preferably one selected from the group consisting of resin [K1], resin [K2] and resin [K3], and more preferably from the group consisting of resin [K2] and resin [K3]. It is a kind of choice. With these resins, the colored curable resin composition has excellent developability. The resin [K2] is more preferable from the viewpoint of adhesion between the colored pattern and the substrate.

The weight average molecular weight of the resin (B) in terms of polystyrene is usually 3,000 to 100,000, preferably 5,000 to 50,000, more preferably 5,000 to 35,000, and It is preferably 5,000 to 30,000, and particularly preferably 6,000 to 30,000. When the molecular weight is in the above range, the coating film hardness is improved, the residual film ratio is high, the solubility of the unexposed area in the developing solution is good, and the resolution of the colored pattern tends to be improved.
The molecular weight distribution [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, and more preferably 1.2 to 4.

The acid value of the resin (B) is usually 20 mg-KOH/g to 170 mg-KOH/g, preferably 30 mg-KOH/g to 170 mg-KOH/g, and more preferably 40 mg-KOH/g to 170 mg. -KOH/g, more preferably 50 mg-KOH/g to 170 mg-KOH/g. Among them, 50 mg-KOH/g to 150 mg-KOH/g is preferable, 60 mg-KOH/g to 150 mg-KOH/g is more preferable, 60 mg-KOH/g to 135 mg-KOH/g is further preferable, 70 mg-KOH/g. ~135 mg-KOH/g is particularly preferred. Here, the acid value is a value measured as an amount (mg) of potassium hydroxide necessary to neutralize 1 g of the resin (B), and can be determined by, for example, titration using an aqueous potassium hydroxide solution.

The content of the resin (B) is preferably 7% by mass to 65% by mass, more preferably 10% by mass to 60% by mass, and further preferably 13% by mass to 60% with respect to the total amount of the solid content. %, and particularly preferably 17% to 55% by mass. When the content of the resin (B) is within the above range, the colored pattern can be easily formed, and the resolution of the colored pattern and the residual film rate tend to be improved.

<Polymerizable compound (C)>
The polymerizable compound (C) is a compound that can be polymerized by an active radical and/or an acid generated from the polymerization initiator (D), and examples thereof include a compound having a polymerizable ethylenic unsaturated bond, and the like. Is a (meth)acrylic acid ester compound.

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

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

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

The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, more preferably 250 or more and 1,500 or less.

The content of the polymerizable compound (C) is preferably 1 to 70% by mass, more preferably 2 to 65% by mass, and still more preferably 5 to 65% by mass with respect to the total amount of the solid content. Is preferable, 7 to 65 mass% is preferable, and among them, 10 to 60 mass% is more preferable, 13 to 60 mass% is more preferable, and 17 to 55 mass% is more preferable. is there.
The content ratio [resin (B):polymerizable compound (C)] of the resin (B) and the polymerizable compound (C) is on a mass basis, preferably 20:80 to 80:20, and more preferably Is 35:65 to 80:20.
When the content of the polymerizable compound (C) is within the above range, the residual film rate at the time of forming a colored 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 capable of generating an active radical, an acid or the like by the action of light or heat and initiating polymerization, and a known polymerization initiator can be used.
Examples of the polymerization initiator (D) include an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyl oxime compound and a biimidazole compound.

O-acyl oxime compounds include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one. 2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methyl Benzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxa Cyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl ]-3-Cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one- 2-imine and the like can be mentioned. Commercially available products such as Irgacure OXE01, OXE02 (all manufactured by BASF) and N-1919 (manufactured by ADEKA) may be used. Among them, the O-acyl oxime compound is N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1. At least one selected from the group consisting of -on-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, and N-benzoyloxy More preferred is -1-(4-phenylsulfanylphenyl)octan-1-one-2-imine.

The alkylphenone compounds include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one and 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one. , 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, 2-hydroxy-2-methyl-1-phenylpropane -1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-( An oligomer of 4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, benzyl dimethyl ketal, Irgacure 369, 907, 379 (all manufactured by BASF) and the like can be mentioned.

The biimidazole compound includes 2,2′-bis(2-chlorophenyl)-4,4′,5,5′-tetraphenylbiimidazole and 2,2′-bis(2,3-dichlorophenyl)-4,4′. , 5,5'-Tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4', 5,5′-Tetraphenylbiimidazole, 2,2′-bis(2-chlorophenyl)-4,4′,5,5′-tetra(alkoxyphenyl)biimidazole, 2,2′-bis(2-chlorophenyl) )-4,4',5,5'-Tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)bi Imidazole (see, for example, JP-B-48-38403, JP-A-62-174204, etc.), an imidazole compound in which the phenyl group at the 4,4'5,5'-position is substituted with a carbalkoxy group ( For example, refer to JP-A-7-10913). Among them, compounds represented by the following formula and mixtures thereof are preferable.

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

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.

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

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

The content of the polymerization initiator (D) is preferably 0.1 to 40 parts by mass with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C), and among them, preferably 0. The amount is 1 to 30 parts by mass, and more preferably 1 to 30 parts by mass.

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

As the amine compound, triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4- 2-Ethylhexyl dimethylaminobenzoate, N,N-dimethylparatoluidine, 4,4′-bis(dimethylamino)benzophenone (commonly called Michler's ketone), 4,4′-bis(diethylamino)benzophenone, 4,4′-bis( Examples thereof include ethylmethylamino)benzophenone, and among them, 4,4′-bis(diethylamino)benzophenone is preferable. You may use commercial items, such as EAB-F (made by Hodogaya Chemical Co., Ltd.).

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

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

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

When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass, and more preferably 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). It is preferably 1 to 20 parts by mass. When the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with higher sensitivity, and the productivity of the color filter tends to be improved.

<Solvent (E)>
The solvent (E) is not particularly limited, and a solvent usually used in this field can be used. For example, ester solvent (solvent containing -COO- in the molecule and not containing -O-), ether solvent (solvent containing -O- in the molecule, not containing -COO-), ether ester solvent (intramolecular) A solvent containing -COO- and -O-), a ketone solvent (a solvent containing -CO- in the molecule and not containing -COO-), an alcohol solvent (containing OH in the molecule, -O-,- CO- and -COO--free solvents), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide and the like.

As the ester solvent, methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate. , Methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, γ-butyrolactone and the like.

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

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

As the ketone solvent, 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, isophorone Etc.

Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin and the like.
Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, mesitylene and the like.
Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and the like.

These solvents may be used alone or in combination of two or more.
Among them, propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 3-methoxybutyl acetate, 3- Methoxy-1-butanol, 4-hydroxy-4-methyl-2-pentanone, N,N-dimethylformamide, N-methylpyrrolidone and the like are preferred, and propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethylene glycol monobutyl ether, di Propylene glycol methyl ether acetate, ethyl lactate, 3-methoxybutyl acetate, 3-methoxy-1-butanol, ethyl 3-ethoxypropionate, 4-hydroxy-4-methyl-2-pentanone, N,N-dimethylformamide, N -Methylpyrrolidone and the like are more preferable.

The content of the solvent (E) is preferably 70 to 95% by mass, and more preferably 75 to 92% by mass, based on the total amount of the colored curable resin composition. In other words, the solid content of the colored curable resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass.
When the content of the solvent (E) is within the above range, the flatness at the time of coating becomes good, and the color density does not become insufficient when a color filter is formed, so that the display characteristics tend to be good.

<Leveling agent (F)>
Examples of the leveling agent (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having a fluorine atom. These may have a polymerizable group in the side chain.
Examples of silicone-based surfactants include surfactants having a siloxane bond in the molecule. Specifically, Toray silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324. , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan LLC) and the like. Can be mentioned.

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

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

The content of the leveling agent (F) is preferably 0.0005% by mass or more and 0.6% by mass or less, more preferably 0.001% by mass or more and 0.1% by mass or less with respect to the total amount of the colored curable resin composition. 5 mass% or less, more preferably 0.001 mass% or more and 0.2 mass% or less, preferably 0.002 mass% or more and 0.1 mass% or less, and more preferably 0.005 mass% or more 0 It is 0.07 mass% or less. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

<Other ingredients>
The colored curable resin composition of the present invention contains, if necessary, fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, and other additives known in the art. May be included.

<Method for producing colored curable resin composition>
The colored curable resin composition of the present invention includes, for example, a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and a solvent (E) used as necessary, It can be prepared by mixing the leveling agent (F), the polymerization initiation aid (D1) and other components.
When the pigment (P) is contained, it is preferable that the pigment is mixed with a part or all of the solvent (E) in advance and dispersed using a bead mill or the like until the average particle diameter of the pigment becomes about 0.2 μm or less. .. At this time, part or all of the pigment dispersant and the resin (B) may be blended if necessary. As the pigment dispersant, commercially available surfactants can be used, and surfactants such as silicone type, fluorine type, ester type, cationic type, anionic type, nonionic type, amphoteric type, polyester type, polyamine type, acrylic type, etc. Agents and the like. Examples of the surfactant include polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid-modified polyesters, tertiary amine-modified polyurethanes, polyethyleneimines, and the like. , KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solpers (manufactured by Zeneca Co., Ltd.), EFKA (manufactured by BASF Japan Co., Ltd.), Azisper (registered trademark) (Manufactured by Ajinomoto Fine-Techno Co., Inc.), Disperbyk (manufactured by Big Chemie) and the like can be mentioned, and these can be used alone or in combination of two or more kinds. The target colored curable resin composition can be prepared by mixing the remaining components in the pigment dispersion liquid thus obtained so as to have a predetermined concentration.
The compound (Z) is preferably dissolved in a part or all of the solvent (E) in advance to prepare a solution. It is preferable to filter the solution with a filter having a pore size of about 0.01 to 1 μm.
The colored curable resin composition after mixing is preferably filtered with a filter having a pore size of about 0.01 to 10 μm.

<Method of manufacturing color filter>
Examples of the method for producing a colored pattern from the colored curable resin composition of the present invention include a photolithographic method, an inkjet method, a printing method and the like. Among them, the photolithographic method is preferable. The photolithographic method is a method in which the colored curable resin composition is applied to a substrate, dried to form a colored composition layer, and the colored composition layer is exposed through a photomask and developed. In the photolithographic method, a colored coating film that is a cured product of the coloring composition layer can be formed by not using a photomask during exposure and/or not developing. The colored pattern or colored coating film thus formed is the color filter of the present invention.
The film thickness of the color filter to be produced is not particularly limited and may be appropriately adjusted depending on the purpose and application. For example, it is 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.5. ~6 μm.

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

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

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

A colored pattern is formed on the substrate by bringing the colored composition layer after exposure into contact with a developing solution for development. By the development, the unexposed portion of the colored composition layer is dissolved and removed in the developer.
The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.02 to 5% by mass, and even more preferably 0.03 to 5% by mass. Furthermore, the developing solution may contain a surfactant.
The developing method may be a paddle method, a dipping method, a spray method or the like. Further, the substrate may be tilted at an arbitrary angle during development.
After development, it is preferable to wash with water.

Furthermore, it is preferable to perform post-baking on the obtained colored pattern. The post-baking temperature is preferably 150 to 250°C, more preferably 160 to 235°C. The post-baking time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.

The present application claims the benefit of priority based on Japanese Patent Application No. 2014-186017 filed on September 12, 2014. The entire content of the specification of Japanese Patent Application No. 2014-186017 filed on Sep. 12, 2014 is incorporated herein by reference.

Next, the present invention will be described more specifically with reference to Examples and the like.
In Examples and Comparative Examples,% and parts indicating the content or the amount used are based on mass unless otherwise specified.
The structure of the compound was confirmed by mass spectrometry (LC; model 1200 manufactured by Agilent, MASS; model LC/MSD6130 manufactured by Agilent).

Example 1
3-Amino-4-hydroxybenzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) 10 parts, 4-(diethylamino)salicylaldehyde (manufactured by Tokyo Chemical Industry Co., Ltd.) 12.8 parts, benzoic acid (Tokyo Chemical Industry Co., Ltd.) )), 2.73 parts, 1-pentanol (Tokyo Kasei Kogyo Co., Ltd.) 157 parts and ethyl cyanoacetate (Tokyo Kasei Kogyo Co., Ltd.) 7.43 parts are mixed and stirred at 120° C. for 3 hours. Then, a mixture (1) was obtained.
Ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) 7.46 parts, benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) 2.79 parts, 1-pentanol (manufactured by Tokyo Chemical Industry Co., Ltd.) 49.8 parts And 12.7 parts of 4-(diethylamino)salicylaldehyde (manufactured by Tokyo Chemical Industry Co., Ltd.) were added and stirred at 120° C. for 14 hours to obtain a mixture (2).
The obtained mixture (1) and the mixture (2) were mixed, and further, ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) 3.76 parts, benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) 1.41 parts , 1-pentanol (manufactured by Tokyo Chemical Industry Co., Ltd.) 52.5 parts and 4-(diethylamino)salicylaldehyde (manufactured by Tokyo Chemical Industry Co., Ltd.) 6.35 parts were added, and the mixture was stirred at 120° C. for 8 hours. After cooling the above reaction solution to room temperature, precipitated crystals were obtained as a residue of suction filtration. To this residue was added 140 parts of tetrahydrofuran, and the mixture was stirred at 70° C. for 1 hour, and then an insoluble matter was obtained as a residue by suction filtration. Tetrahydrofuran (120 parts) was added to this residue, and the mixture was stirred at 70° C. for 1 hour, and then an insoluble matter was obtained as a residue by suction filtration. To this residue was added 340 parts of N,N-dimethylformamide, and the mixture was heated to 90°C to dissolve it, and then allowed to stand at 0°C to 5°C. The precipitated crystals were obtained as the residue of suction filtration. The residue was dried under reduced pressure at 60° C. to obtain 5.69 parts of a compound represented by the formula (Ad1-1).

Then, 3.8 parts of the compound represented by the formula (Ad1-1) and 1.4 parts of 2-(trimethylsilyl)ethanol were added to 100 parts of dehydrated chloroform. To the obtained mixture, 2.3 parts of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and 1.5 parts of 4-dimethylaminopyridine were further added, and the mixture was stirred at 30°C for 6 hours. Water was added to the obtained reaction mixture, the organic layer was extracted, and chloroform was distilled off to obtain a yellow solid. It dried at 60 degreeC under reduced pressure for 24 hours, and obtained 4.2 parts of compounds represented by Formula (Z-1).

Identification of Compound Represented by Formula (Z-1) (Mass Spectrometry) Ionization Mode=ESI+: m/z=479.2 [M+1] ⁺
Exact Mass: 478.2

Example 2
In Example 1, except that a compound represented by the following formula (d-1) was used instead of 3-amino-4-hydroxybenzoic acid, synthesis was performed in the same manner as in Example 1, and the compound represented by the formula (Ad1-2) was used. The compound represented was obtained.

Next, 3.6 parts of the compound represented by the formula (Ad1-2) and 2.0 parts of triethylamine were added to 300 parts of chloroform, 3.1 parts of methacrylic anhydride was further added, and the mixture was kept at 50° C. for 3 hours. did. 300 parts of water was added to the obtained mixture, the organic layer was extracted, and chloroform was distilled off to obtain a yellow solid. It dried at 60 degreeC under reduced pressure for 24 hours, and obtained 3.8 parts of compounds represented by a formula (Z-41).

Identification of Compound Represented by Formula (Z-41) (Mass Spectrometry) Ionization Mode=ESI+: m/z=419.4 [M+1] ⁺
Exact Mass: 418.4

Synthesis example 1
An appropriate amount of nitrogen was made to flow into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to create a nitrogen atmosphere, 100 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 85°C while stirring. Then, 19 parts of methacrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2. A solution of 171 parts of a mixture of 1.0 ^2,6 ]decan-9-yl acrylate (content ratio is 50:50 in molar ratio) in 40 parts of propylene glycol monomethyl ether acetate is used for about 5 hours using a dropping pump. Was dropped. On the other hand, a solution prepared by dissolving 26 parts of a polymerization initiator 2,2′-azobis(2,4-dimethylvaleronitrile) in 120 parts of propylene glycol monomethyl ether acetate was put into the flask for about 5 hours using another dropping pump. Dropped. After the dropping of the polymerization initiator was completed, the temperature was maintained at the same temperature for about 3 hours and then cooled to room temperature to obtain a solution of a copolymer (resin B1) having a solid content of 43.5%. The resin B1 thus obtained had a weight average molecular weight of 8000, a molecular weight distribution of 1.98, and an acid value in terms of solid content of 53 mgKOH/g.

[Preparation of colored curable resin composition]
Example 3
Colorant (A): C.I. I. Pigment Green 58 (Pigment) 27 parts;
12 parts of acrylic pigment dispersant;
Resin (B): Resin B1 (solid content conversion) 9.5 parts; and Solvent (E): Propylene glycol monomethyl ether acetate.
180 copies;
Were mixed, and a pigment dispersion liquid (3) in which the pigment was sufficiently dispersed using a bead mill was obtained.

Colorant (A): 2.0 parts of the compound represented by formula (Z-1);
Resin (B): Resin B1 (solid content conversion) 40 parts;
Polymerizable compound (C): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 49 parts;
Polymerization initiator (D): N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF; O-acyl oxime compound) 9.8 copies;
Solvent (E): Propylene glycol monomethyl ether acetate
670 copies;
Leveling agent (F): polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.15 part; and pigment dispersion liquid (3) 228.5 parts;
Were mixed to obtain a colored curable resin composition (J1).

Example 4
C. of the colorant (A). I. Pigment Green 58 (pigment) with C.I. I. Pigment Green 36 (pigment) was replaced with the same procedure as in Example 3 to obtain a colored curable resin composition (J2).

Example 5
Colored curable resin composition (J3) in the same manner as in Example 3 except that the compound represented by formula (Z-1) of the colorant (A) was replaced with the compound represented by formula (Z-41). ) Got.

Example 6
C. of the colorant (A). I. Pigment Green 58 (pigment) with C.I. I. A colored curable resin composition (J4) was obtained in the same manner as in Example 5 except for using Pigment Green 36 (pigment).

Comparative Example 1
Colorant (A): C.I. I. Pigment Green 58 (Pigment) 27 parts;
12 parts of acrylic pigment dispersant;
Resin (B): Resin B1 (solid content conversion) 9.5 parts; and Solvent (E): Propylene glycol monomethyl ether acetate.
180 copies;
Were mixed, and a pigment dispersion liquid (5) in which the pigment was sufficiently dispersed using a bead mill was obtained.

Coloring agent (A): 1.0 part of the compound represented by formula (d0);
Resin (B): Resin B1 (solid content conversion) 40 parts;
Polymerizable compound (C): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 49 parts;
Polymerization initiator (D): N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF; O-acyl oxime compound) 9.8 copies;
Solvent (E): Propylene glycol monomethyl ether acetate
670 copies;
Leveling agent (F): polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.15 part; and pigment dispersion liquid (5) 228.5 parts;
Were mixed to obtain a colored curable resin composition (J5).

[Film thickness measurement]
The film thickness was measured using DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd.

[Preparation of resin composition for sublimation test (SJS)]
Resin: Methacrylic acid/benzyl methacrylate (molar ratio: 30/70) copolymer (Taoka Chemical Industry Co., Ltd., average molecular weight 10700, acid value 70 mg KOH/g) 33.8% propylene glycol monomethyl ether acetate solution 40.2 Department;
Polymerizable compound: dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 5.8 parts;
Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE01; manufactured by BASF Japan Ltd.) 0.58 parts;
Leveling agent: polyether modified silicone (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.01 part;
Solvent: propylene glycol monomethyl ether 46.6 parts;
Solvent: propylene glycol monomethyl ether acetate 6.8 parts;
Were mixed to obtain a resin composition for sublimation test (SJS).

[Formation of resin coating film (SJSM) for sublimation test]
The resin composition for sublimation test (SJS) obtained above was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning Incorporated) by a spin coating method to volatilize volatile components at 100° C. for 3 minutes. .. After cooling, light exposure was performed using an exposure device (TME-150RSK; manufactured by Topcon Corp.) in the atmosphere at an exposure dose of 150 mJ/cm ² (365 nm standard). It was heated at 220° C. for 2 hours in an oven to form a resin coating film for sublimation test (SJSM) (film thickness 2.2 μm).

Example 7
[Preparation of colored pattern and evaluation of sublimability]
The colored curable resin composition (J1) obtained in Example 3 was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning Incorporated) by a spin coating method, and then prebaked at 100° C. for 3 minutes for coloring. A composition layer was formed. After cooling, the distance between the substrate on which the colored composition layer was formed and the photomask made of quartz glass was set to 200 μm, and an exposure machine (TME-150RSK; made by Topcon Corp.) was used to obtain 80 mJ/cm ^{2 in the} atmosphere. Exposure amount (365 nm standard). As the photomask, a photomask having a line and space pattern of 100 μm was used. The exposed colored composition layer was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25° C. for 70 seconds for development, and washed with water. The film thickness was measured. The results are shown in Table 1.
The colored coating film and the resin coating film for sublimation test (SJSM) obtained above were opposed to each other with an interval of 70 μm and post-baked at 230° C. for 10 minutes to obtain a colored pattern. .. The color difference (ΔEab*) before and after heating of the resin coating film for sublimation test (SJSM) was measured using a colorimeter (OSP-SP-200; manufactured by OLYMPUS). The color difference (ΔEab*) was 4.0. When the color difference (ΔEab*) is 5.0 or more, it indicates that the colorant has sublimability. The results are shown in Table 1. In Table 1, ◯ means that the colorant has no sublimation property, and x means that the colorant has sublimation property.

Examples 8 to 10 and Comparative Example 2
Example 7 except that the colored curable resin composition (J1) obtained in Example 3 was replaced with the colored curable resin composition (J2) to the colored curable resin composition (J5), respectively. Similarly, a colored pattern was obtained and sublimation was evaluated. The results are shown in Table 1.

When forming a color filter from a colored curable resin composition containing the compound of the present invention, sublimation of the colorant can be suppressed. The color filter using the colored curable resin composition containing the compound of the present invention is suitably used for a display device such as a liquid crystal display device.

Claims (9)

A compound represented by formula (Z).

[In the formula (Z), R ¹ and R ² are each independently a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, an aryl group, a group containing an acryloyl group, or a group containing a methacryloyl group. Alternatively, it represents a group containing a silicon atom.
R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are each independently a hydrogen atom, a halogen atom, a cyano group, a carboxyl group, a nitro group, or a carbon number of 1 to 20. Represents an alkyl group, an alkoxy group having 1 to 20 carbon atoms, a group containing an acryloyl group, a group containing a methacryloyl group or a group containing a silicon atom.
Provided that at least one of R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ is a group containing an acryloyl group or a methacryloyl group,
The group containing a silicon atom is a group represented by the formula (Z1),

[In the formula, R ^11A represents a single bond or an alkanediyl group having 1 to 10 carbon atoms, and —CH ₂ — contained in the alkanediyl group is —O—, —CO—, —NR ¹⁰ —, —. OCO-, -COO-, -OCONH-, -CONH- or -NHCO- may be substituted, and the hydrogen atom contained in the alkanediyl group has 1 to 4 carbon atoms which may have a hydroxyl group. It may be substituted with an alkyl group.
R ¹⁰ represents a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
R ^12A , R ^13A and R ^14A each independently represent a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
* Represents a bond with a nitrogen atom or a carbon atom. ]
The group containing an acryloyl group or the group containing a methacryloyl group is a group represented by formula (Z2).

[In the formula, R ^15A represents an alkanediyl group having 1 to 10 carbon atoms, and —CH ₂ — contained in the alkanediyl group is —O—, —CO—, —OCO—, —COO—, — It may be substituted with OCONH-, -CONH- or -NHCO-, and the hydrogen atom contained in the alkanediyl group is substituted with an alkyl group having 1 to 4 carbon atoms which may have a hydroxyl group. Good.
R ^16A represents an acryloyl group or a methacryloyl group.
* Represents a bond with a nitrogen atom or a carbon atom. ]] A colorant comprising the compound according to claim 1. The colorant according to claim 2, further comprising a green pigment. The colorant according to claim 3, wherein the green pigment is at least one selected from the group consisting of halogenated copper phthalocyanine pigments and halogenated zinc phthalocyanine pigments. The colorant according to claim 3 or 4, wherein the green pigment is at least one selected from the group consisting of a chlorinated copper phthalocyanine pigment, a brominated copper phthalocyanine pigment, and a brominated zinc phthalocyanine pigment. The green pigment is C.I. I. Pigment Green 36 and C.I. I. Pigment Green 58, at least one selected from the group consisting of Pigment Green 58. The colorant according to claim 3. A colored curable resin composition containing the colorant according to any one of claims 2 to 6, a resin, a polymerizable compound, and a polymerization initiator. A color filter formed from the colored curable resin composition according to claim 7. A liquid crystal display device comprising the color filter according to claim 8.