JP7046997B2 - A compound and a colored curable resin composition containing the compound. - Google Patents

Description

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

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

Japanese Unexamined Patent Publication No. 2006-154740 (Example 8)

The problem is that the colorant sublimates in the step of forming the color filter from the color-curable resin composition containing the compound represented by the formula (d0).

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 independent groups containing a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, an aryl group, an acryloyl group, and a methacryloyl group, respectively. Or represents a group containing a silicon atom.
R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ independently have a hydrogen atom, a halogen atom, a cyano group, a carboxyl group, a nitro group, and 1 to 20 carbon atoms. 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.
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 contains a group containing an acryloyl group, a group containing a methacryloyl group, or a group containing a methacryloyl group. It is a group containing a silicon atom. ]
[2] The compound according to [1], wherein 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 -,-. It may be substituted with OCO-, -COO-, -OCONH-, -CONH- or -NHCO-, and the hydrogen atom contained in the alkanediyl group may have a hydroxyl group and may have 1 to 4 carbon atoms. It may be substituted with an alkyl group of.
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 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 the 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-, It may be substituted with -COO-, -OCONH-, -CONH- or -NHCO-, and the hydrogen atom contained in the alkanediyl group may have a hydroxyl group as an alkyl group having 1 to 4 carbon atoms. It 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 a halogenated copper phthalocyanine pigment and a halogenated zinc phthalocyanine pigment.
[7] The colorant according to [5] or [6], 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.
[8] The green pigment is C.I. I. Pigment Green 36 and C.I. I. The colorant according to any one of [5] to [7], which is at least one selected from the group consisting of Pigment Green 58.
[9] A color curable resin composition containing the colorant, resin, polymerizable compound and polymerization initiator according to any one of [4] to [8].
[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 a color filter is formed from a color curable resin composition containing the compound of the present invention, sublimation of the colorant can be suppressed.

<Compound represented by the formula (Z) (hereinafter, may be referred to as compound (Z))>.

[In the formula (Z), R ¹ and R ² are independent groups containing a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, an aryl group, an acryloyl group, and a methacryloyl group, respectively. Or represents a group containing a silicon atom.
R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ independently have a hydrogen atom, a halogen atom, a cyano group, a carboxyl group, a nitro group, and 1 to 20 carbon atoms. 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.
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 contains a group containing an acryloyl group, a group containing a methacryloyl group, or a group containing a methacryloyl group. It is a group containing a silicon atom. ]

The monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ¹ and R ² includes 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. , A branched chain alkyl group having 3 to 20 carbon atoms such as an isobutyl group, a sec-butyl group, a tert-butyl group, an isopentyl group, a neopentyl group and a 2-ethylhexyl group; and an alkyl group having 1 to 20 carbon atoms;
Examples thereof include an alicyclic saturated hydrocarbon group having 3 to 20 carbon atoms such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group and a tricyclodecyl group.
The aryl groups represented by R ¹ and R ² include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2,3-dimethylphenyl group, a 2,4-dimethylphenyl group, and 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, 4-ethylphenyl group, etc. Examples thereof include a phenyl group in which the group may be substituted, preferably a tolyl group or a dimethylphenyl group.

As R ¹ and R ² , an alkyl group having 1 to 20 carbon atoms is preferable, and a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 5 to 10 carbon atoms is more preferable. Ethyl groups or 2-ethylhexyl groups are more preferred, and ethyl groups are even more preferred.

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

Alkyl groups 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 methyl group, ethyl group, 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. Can be mentioned.

The alkoxy groups 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, and a butoxy group. Examples thereof 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 contains a group containing an acryloyl group, a group containing a methacryloyl group, or a group containing a methacryloyl group. It is a group containing a silicon atom.

A group containing an acryloyl group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ or a group containing a methacryloyl group is a group composition. As a unit, it means a group having at least one acryloyl group or a methacryloyl group.
The carbon number of the group containing an acryloyl group is usually 3 to 16, preferably 3 to 12, and more preferably 3 to 8.
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 metaacryloyl 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-, It may be substituted with -COO-, -OCONH-, -CONH- or -NHCO-, and the hydrogen atom contained in the alkanediyl group may have a hydroxyl group as an alkyl group having 1 to 4 carbon atoms. It 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 arcandyl group having 1 to 10 carbon atoms represented by R ^15A 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 and a 2-methyltri. Examples thereof include a methylene group, an isopentylene group, an isohexylene group, an isooctylene group and a 2-ethylhexylene group, and an alcandiyl group having 1 to 6 carbon atoms is preferable, and an alcandiyl group having 1 to 4 carbon atoms is more preferable.
As the alkanediyl group having 1 to 10 carbon atoms represented by R ^15A , a group in which —CH ₂ − contained in the alkanediyl group is substituted with —O— is preferable. The number of —O— in R ^15A is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. At least one of the -O- may be bound to R ^16A . Of -CH _2- , * -CH _2- , which is a bond of nitrogen atom or carbon atom, is -O-, -CO-, -NR ^11- , -OCO-, -COO-, -OCONH-,-. It is preferably not substituted with 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. , Methyl group, ethyl group, propyl group or butyl group is preferable, and ethyl group is more preferable.

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

Examples of the group containing an acryloyl group or a metaacryloyl group include a group represented by (ii-1) to a group represented by (ii-42), and a group represented by (ii-1) is preferable. A group represented by (ii-8) and a group represented by (ii-13) to a group represented by (ii-22), more preferably a group represented by (ii-1) to (ii-1). It is 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.

A 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 component of the group. Means the group.
The number of carbon atoms of the group containing a silicon atom is usually 1 to 30, preferably 1 to 20, and more preferably 1 to 10.
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 -,-. It may be substituted with OCO-, -COO-, -OCONH-, -CONH- or -NHCO-, and the hydrogen atom contained in the alkanediyl group may have a hydroxyl group and may have 1 to 4 carbon atoms. It may be substituted with an alkyl group of.
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 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 alkanediyl groups 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.
The alkyl groups having 1 to 4 carbon atoms which may be substituted with the hydrogen atom of the arcandyl group of R ^11A 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.

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 .

Alkyl groups having 1 to 4 carbon atoms represented by R ^12A , R ^13A and R ^14A include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group and tert-butyl. Groups, cyclopropyl groups and cyclobutyl groups can be mentioned.
The alkoxy groups 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. Can be mentioned.
It is preferable 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 further preferable.

Examples of the group containing a silicon atom include the groups described below. Examples of the group in which R ^11A is single-bonded or in which -CH _2- is contained in R ^11A is not substituted include the groups represented by the following (* indicates a bond).

Examples of the group in which -CH _2- is substituted with -O- contained in R ^11A include the groups represented by the following (* indicates a bond).

Examples of the group in which -CH _2- is substituted with -CO- contained in R ^11A include the groups represented by the following (* indicates a bond).

The groups in which -CH _2- is substituted with -NR ^10- contained in R ^11A are preferably -NH-, -NCH _3- , and -NC ₂ H _5- , and the preferred groups are the groups represented by the following. (* Indicates a bond).

Examples of the group in which -CH _2- is substituted with -OCO- contained in R ^11A include the groups represented by the following (* indicates a bond).

Examples of the group in which -CH _2- is substituted with -COO- contained in R ^11A include the groups represented by the following (* indicates a bond).

Examples of the group in which -CH _2- is substituted with -OCONH- contained in R ^11A include the groups represented by the following (* indicates a bond).

Examples of the group in which -CH _2- is substituted with -CONH- contained in R ^11A include the groups represented by the following (* indicates a bond).

Examples of the group in which -CH _2- is substituted with -NHCO- contained in R ^11A include the groups represented by the following (* indicates a bond).

As a group in which the hydrogen atom contained in the alkanediyl group contained in R ^11A may be substituted with an alkyl group having 1 to 4 carbon atoms which may have a hydroxyl group, a group represented by the following is used. (* Indicates a bond).

As a group containing a silicon atom, -CH _2- contained in the alkanediyl group represented by R ^11A is represented by the formula (Z1) in which -OCO-, -COO- or -OCONH- is substituted. The group is more preferable, and the group represented by the formula (Z1) in which -CH _2- 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 represented by the following.

R ³ , R ⁴ , R ⁵ and R ⁶ are preferably hydrogen atoms or alkyl groups having 1 to 20 carbon atoms, respectively, and are preferably hydrogen atoms or alkyl groups having 1 to 8 carbon atoms. It is more preferably a hydrogen atom or a methyl group, and particularly preferably a hydrogen atom.
R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are preferably hydrogen atoms, alkyl groups or carboxyl groups having 1 to 20 carbon atoms, respectively, and hydrogen atoms, alkyl groups or carboxyl groups having 1 to 8 carbon atoms, respectively. It is more preferably a group, and even more preferably a hydrogen atom or a carboxyl group.
At least one of R ⁷ , R ⁸ , R ⁹ and R ¹⁰ is preferably a group containing an acryloyl group, a group containing a methacryloyl group or a group containing a silicon atom, preferably 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 R 10 are used. It is preferable that at least one of R ⁹ , more preferably either R ⁸ or R ⁹ , is 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 a compound represented by the formula (Z-1) to a compound represented by the formula (Z-56).

Compound (Z) can be described, for example, in Days 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 represented by the compound represented by the formula (2-A), the compound represented by the formula (2-B), and ethyl cyanoacetate. Can be produced by subjecting to 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 hour to 24 hours, more preferably 8 hours to 16 hours. Examples of the solvent include methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, N-methylpyrrolidone and the like, with 1-pentanol being preferred.

[In the formula (2-A) and the formula (2-B), R ¹ to R ⁴ and R ⁶ to R ¹⁰ have the same meanings as described above, respectively. ]

The amount of the compound represented by the formula (2-A) to be used is preferably 1 mol to 10 mol, more preferably 1 to 5 mol, based on 1 mol of the compound represented by the formula (2-B). It is more preferably 1 mol.
The amount of ethyl cyanoacetate to be used is preferably 1 mol to 10 mol, more preferably 1 to 5 mol, still more 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, more preferably 0.3 to 0.4 mol, based on 1 mol of the compound represented by the formula (2-B).
After obtaining the compound represented by the formula (Z) in which R ⁵ = hydrogen atom, any substituent may be introduced into R ⁵ by using a known method.

Examples of the method for obtaining the compound represented by the formula (Z) which is the target compound from the reaction mixture include a method in which the temperature of the reaction mixture is appropriately adjusted to precipitate crystals and the crystals are collected 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. , N-Methylpyrrolidone or a mixture thereof and the like, 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 the present specification, the compound represented by the formula (z5a) and the compound represented by the formula (z5b) may be collectively referred to as a 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 above. ]

The divalent linking group represented by R ¹¹³ includes 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. Examples thereof include an arcandyl group having 1 to 10 carbon atoms such as a group, an isohexylene group, an isooctylene group and a 2-ethylhexylene group. -CH _2- contained in the alkanediyl group is substituted with -O-, -CO-, -NR ^10- , -OCO-, -COO-, -OCONH-, -CONH- or -NHCO-. May be good. R ¹⁰ has the same meaning as above.
Examples of the hydrophilic group represented by R ¹¹⁴ and R ¹¹⁵ include a hydroxy group and a carboxy group. However, R ¹¹⁴ and R ¹¹⁵ do not represent the same group, and it is preferable 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 component of the group, and is preferably a group represented by the formula (Z1).

[In the formula, R ^11A , R ^12A , R ^13A and R ^14A have the same meanings as described above.
* Represents a bond with R ¹¹⁵ . ]
The group represented by * -R ¹¹³ -R ¹¹⁶ (* represents a bond with a carbon atom) corresponds to R ⁸ and R ⁹ in compound (Z).

The reaction between the compound represented by the formula (z5) and the compound represented by the 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 hour to 12 hours, more preferably 1 hour to 4 hours.

The amount of the compound represented by the formula (z6) to be used is usually 1 mol or more and 8 mol or less, preferably 1 mol or more and 4 mol or less, with respect to 1 mol of the compound represented by the formula (z5).
During the reaction, it is more preferable to add an acidic catalyst in order to allow the reaction to proceed 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, more preferably 0.8 to 2 mol, based on 1 mol of the compound represented by the formula (z6).

Examples of the method for obtaining the compound of the present invention as the target compound from the reaction mixture include a method in which the reaction mixture is mixed with an acid (for example, acetic acid or the like) and water, and the precipitated crystals are collected by filtration. For the acid, it is preferable to prepare an aqueous solution of the acid in advance and then add 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 adding the reaction mixture to the aqueous acid solution, it is preferable to stir at the same temperature for about 0.5 to 2 hours. It is preferable that the collected crystals are washed with water or the like and then dried. Further, if necessary, it may be further purified by a known method such as recrystallization.

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

The divalent linking group represented by R ¹¹¹ includes 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. Examples thereof include an arcandyl group having 1 to 10 carbon atoms such as a group, an isohexylene group, an isooctylene group and a 2-ethylhexylene group. -CH _2- contained in the alkanediyl group is substituted with -O-, -CO-, -NR ^11- , -OCO-, -COO-, -OCONH-, -CONH- or -NHCO-. May be good. R ¹¹ has the same meaning as 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 a methacryloyl group as a constituent unit of the group.
The group represented by * -R ¹¹¹ -R ¹¹⁰ (* represents a bond with a carbon atom) corresponds to R ⁸ and R ⁹ in compound (Z).

The reaction between the compound represented by the formula (z8) and the compound represented by the 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 hour to 12 hours, more preferably 1 hour to 4 hours.

The amount of the compound represented by the formula (z9) to be used is usually 1 mol or more and 8 mol or less, preferably 1 mol or more and 4 mol or less, with respect to 1 mol of the compound represented by the formula (z8).
During the reaction, it is more preferable to add an acidic catalyst in order to allow the reaction to proceed 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, more preferably 0.8 to 2 mol, based on 1 mol of the compound represented by the formula (z9).

Examples of the method for obtaining the compound of the present invention, which is the 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 color-curable resin composition of the present invention contains a colorant (A) containing the 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. Further, 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 the solvent (E) and the 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 may be used alone or in combination of a plurality of 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, and brominated zinc phthalocyanine pigments. Examples thereof include halogenated zinc phthalocyanine pigments such as C.I. I. Pigment Green 7, 10, 15, 25, 36, 47, 58 and other green pigments.
The green pigment (P) is preferably at least one selected from the group consisting of a halogenated copper phthalocyanine pigment and a halogenated zinc phthalocyanine pigment.
More preferably, it is at least one selected from the group consisting of chlorinated copper phthalocyanine pigments, brominated copper phthalocyanine pigments and brominated zinc phthalocyanine pigments.
C. I. More preferably, it is at least one selected from the group consisting of pigment greens 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 even more preferred.

The colorant (A) may contain 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, and more preferably 0.1% by mass or more and 80% by mass or less with respect to the total amount of the colorant (A). It is 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, the content thereof is preferably 10% by mass or more and 99.99% by mass or less, and more preferably 20% by mass or more and 99.9% by mass with respect to the total amount of the colorant (A). It is mass% or less, more preferably 35% by mass or more and 99% by mass or less, and even more preferably 40% by mass or more and 98% by mass or less.
When the green pigment (P) is contained, the content ratio of the compound (Z) to 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, 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, still more preferably 50% by mass or more, based on the total amount of the colorant (A). , More preferably 70% by mass or more, particularly preferably 80% by mass or more, and the upper limit may be 100% by mass or less and 95% by mass or less.

The content of the colorant (A) is usually 1% by mass or more and 99% by mass or less, preferably 2% by mass or more and 90% by mass or less, based on the total solid content of the coloring 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, and particularly preferably 5% by mass or less. It is 50% by mass or less. When the content of the colorant (A) is within the above range, desired spectroscopy and color density can be obtained.

As used herein, the term "total amount of solids" refers to the total amount of components of the colored curable resin composition of the present invention excluding the solvent (E). The total amount of solid content and the content of each component relative to the total amount of solid content can be measured by a known analytical means such as, for example, 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 an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride can be used. More preferred. Examples of such a resin include the following resins [K1] to [K6].
Resin [K1] At least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (a) (hereinafter sometimes referred to as "(a)"), and a cyclic ether structure having 2 to 4 carbon atoms. A 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)"). Copolymer with);
Copolymer of resin [K3] (a) and (c);
Resin [K4] A resin obtained by reacting (b) with a copolymer of (a) and (c);
Resin [K5] A 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-cyclohexendicarboxylic 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 [2.2.1] Bicyclounsaturated compounds containing a carboxy group such as hept-2-ene and 5-carboxy-6-ethylbicyclo [2.2.1] hept-2-ene;
Maleic anhydride, citraconic acid anhydride, itaconic acid anhydride, 3-vinylphthalic acid anhydride, 4-vinylphthalic acid anhydride, 3,4,5,6-tetrahydrophthalic acid anhydride, 1,2,3,6- Unsaturated dicarboxylic acid anhydrides such as tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride;
Unsaturated mono [(meth) acryloyloxyalkyl] esters of divalent or higher valent carboxylic acids such as monosuccinic acid mono [2- (meth) acryloyloxyethyl] and mono [2- (meth) acryloyloxyethyl] phthalates. 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 copolymerizability and solubility of the obtained resin in an alkaline aqueous 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 oxylan ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond. say. In (b), a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group is preferable.
In addition, in this specification, "(meth) acrylic acid" represents at least one selected from the group consisting of acrylic acid and methacrylic acid. Notations such as "(meth) acryloyl" and "(meth) acrylate" have the same meaning.

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

As (b1), for example, a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter referred to as “(b1-1)”). There is), a monomer (b1-2) having an epoxidized structure of an alicyclic unsaturated hydrocarbon (hereinafter, may be 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 (Glysidyloxymethyl) styrene and the like can be mentioned.

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

[In the formulas (I) and (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. You may.
X ^a and X ^b represent a single bond, * -R ^{c-, * -R c-O-, * -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 a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group and the like.
Alkyl groups in which the hydrogen atom is substituted with hydroxy include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group and 1-hydroxy. Examples thereof include -1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, 4-hydroxybutyl group and the like.
Examples of R ^a and R ^b include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group and a 2-hydroxyethyl group, and more preferably a hydrogen atom and a methyl group.

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

Examples of the compound represented by the formula (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) is preferable, and the compound represented by the formula (I-1), the formula (I-7), the formula (I-9) or 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, formula (II-1), formula (II-3), formula (II-5), formula (II-7), formula (II-9) or formula (II-11) to formula (II-15). The compound represented by the formula (II-1), the formula (II-7), the formula (II-9) or the compound represented by the 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 the compound represented by the formula (I) and the compound represented by the formula (II) may be used in combination. You may. When these are used in combination, the content ratio of the compound represented by the formula (I) and the compound represented by the formula (II) is preferably 5:95 to 95: 5, more preferably 10:90 to the molar basis. It is 90:10, 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-methacrylloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, and 3-ethyl-3-acryloyloxymethyloxetane. , 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, Viscort V # 150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate and the like.

As (b), (b1) is preferable in that the reliability of the obtained color filter such as heat resistance and chemical resistance can be further improved. Further, (b1-2) is more preferable in that the color-curable resin composition has excellent storage stability.

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 ] Decane-8-yl (meth) acrylate (In the art, it is commonly referred to as "dicyclopentanyl (meth) acrylate", and in the case of "tricyclodecyl (meth) acrylate". ), Tricyclo [5.2.1.0 ^2,6 ] decene-8-yl (meth) acrylate (in the art, it is commonly referred to as "dicyclopentenyl (meth) acrylate". ), Dicyclopentanyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, benzyl (Meta) 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 diethyl itaconic acid;
Bicyclo [2.2.1] hept-2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-ethylbicyclo [2.2.1] hept-2-ene, 5- Hydroxybicyclo [2.2.1] hept-2-ene, 5-hydroxymethylbicyclo [2.2.1] hept-2-ene, 5- (2'-hydroxyethyl) bicyclo [2.2.1] Hept-2-ene, 5-methoxybicyclo [2.2.1] hept-2-ene, 5-ethoxybicyclo [2.2.1] hept-2-ene, 5,6-dihydroxybicyclo [2.2] .1] Hept-2-ene, 5,6-di (hydroxymethyl) bicyclo [2.2.1] Hept-2-ene, 5,6-di (2'-hydroxyethyl) bicyclo [2.2. 1] Hept-2-ene, 5,6-dimethoxybicyclo [2.2.1] hept-2-ene, 5,6-diethoxybicyclo [2.2.1] hept-2-ene, 5-hydroxy -5-Methylbicyclo [2.2.1] hept-2-ene, 5-hydroxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-hydroxymethyl-5-methylbicyclo [2] .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) Oxycarbonyl) Bicyclo unsaturated compounds such as bicyclo [2.2.1] hept-2-ene;
N-Phenylmaleimide, N-Cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidebenzoate, N-succinimidyl-4-maleimidebutyrate, N-succinimidyl-6-maleimide caproate, N-succinimidyl-3 -Dicarbonylimide derivatives such as maleimide propionate, 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 ] decane-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 the ratio of all the structural units constituting the resin [K1].
Structural unit derived from (a); 2-60 mol%
Structural unit derived from (b); 40-98 mol%
Is preferable
Structural unit derived from (a); 10-50 mol%
Structural unit derived from (b); 50-90 mol%
Is more preferable.
When the ratio of the structural units of the resin [K1] is within the above range, the color-curable resin composition is excellent in storage stability, developability when forming a color pattern, and solvent resistance of the obtained color filter. Tend.

The resin [K1] is, for example, the method described in the document "Experimental Method for Polymer Synthesis" (written by Takayuki Otsu, Kagaku-Dojin Co., Ltd., 1st edition, 1st printing, published on March 1, 1972) and the relevant document. It can be manufactured with reference to the cited documents 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 for example, oxygen is replaced with nitrogen to create a deoxidized atmosphere, and the mixture is stirred. Examples thereof include a method of heating and keeping warm. The polymerization initiator, solvent and the like used here are not particularly limited, and those usually used in the art can be used. For example, as the polymerization initiator, an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), etc.) or an organic peroxide (benzoyl peroxide, etc.) As the solvent, any solvent may be used as long as it dissolves each monomer, and examples of the solvent (E) of the colored curable resin composition of the present invention include a solvent described later.

As the obtained copolymer, the solution after the reaction may be used as it is, a concentrated or diluted solution may be used, or the copolymer is taken out as a solid (powder) by a method such as reprecipitation. You may use the one. In particular, by using the solvent contained in the color-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 color-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 the ratio of 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); 1-65 mol%
Is preferable
Structural unit derived from (a); 5-40 mol%
Structural unit derived from (b); 5-80 mol%
Structural unit derived from (c); 5-60 mol%
Is more preferable.
When the ratio of the structural units of the resin [K2] is within the above range, the storage stability of the color-curable resin composition, the developability when forming a color 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 the ratio of all the structural units constituting the resin [K3].
Structural unit derived from (a); 2-60 mol%
Structural unit derived from (c); 40-98 mol%
Is preferable
Structural unit derived from (a); 10-50 mol%
Structural unit derived from (c); 50-90 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 a carboxylic acid anhydride having (a) a cyclic ether having 2 to 4 carbon atoms of (b) obtained by obtaining a polymer of (a) and (c). 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 for producing the resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as that mentioned in the resin [K3].

Next, the cyclic ether having 2 to 4 carbon atoms of (b) is reacted with a part of the carboxylic acid and / or the carboxylic acid anhydride derived from (a) in the copolymer.
Following the production of the copolymer of (a) and (c), the atmosphere in the flask was replaced with air from nitrogen, and (b) a reaction catalyst of carboxylic acid or carboxylic acid anhydride and cyclic ether (for example, Tris (for example, Tris). Resin [K4] can be produced by putting (dimethylaminomethyl) phenol etc.) and a polymerization inhibitor (for example, hydroquinone etc.) in a flask and reacting at 60 to 130 ° C. for 1 to 10 hours, for example. can.
The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, based on 100 mol of (a). Within this range, the storage stability of the colored curable resin composition, the developability when forming a pattern, and the balance between the solvent resistance, heat resistance, mechanical strength and sensitivity of the obtained pattern are improved. Tend. Since the reactivity of the cyclic ether is high and the unreacted (b) is unlikely to remain, (b1) is preferable as the (b) used for the resin [K4], and (b1-1) is more preferable.
The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass with respect to 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 with respect to 100 parts by mass of the total amount of (a), (b) and (c).
The reaction conditions such as the charging method, the reaction temperature and the time can be appropriately adjusted in consideration of the production equipment, the calorific value due to 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, the calorific value due to the polymerization, and the like.

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

Further, under the same conditions as the method for producing the resin [K4], the carboxylic acid or carboxylic acid anhydride of (a) is added to the cyclic ether derived from (b) of the copolymer of (b) and (c). The resin [K5] can be obtained by reacting an object.
The amount of (a) used to react with the copolymer is preferably 5 to 80 mol with respect to 100 mol of (b). Since the reactivity of the cyclic ether is high and the unreacted (b) is unlikely to remain, (b1) is preferable as the (b) used for the resin [K5], and (b1-1) is more preferable.

The resin [K6] is a resin obtained by further reacting the resin [K5] with a carboxylic acid anhydride. The carboxylic acid anhydride is reacted with the hydroxy group generated by the reaction of the cyclic ether with the carboxylic acid or the carboxylic acid anhydride.
Examples of the carboxylic acid anhydride include maleic anhydride, citraconic acid anhydride, itaconic acid 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 with respect to 1 mol of the amount used in (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 such as decyl (meth) acrylate / (meth) acrylic acid copolymer [K1]; glycidyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / styrene / (Meta) 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) acrylic loyloxymethyloxetane / Resin such as (meth) acrylic acid / styrene copolymer [K2]; benzyl (meth) acrylate / (meth) acrylic acid copolymer, styrene / (meth) acrylic acid copolymer, benzyl (meth) acrylate / Resin such as tricyclodecyl (meth) acrylate / (meth) acrylic acid copolymer [K3]; resin in which glycidyl (meth) acrylate is added to benzyl (meth) acrylate / (meth) acrylic acid copolymer. Tricyclodecyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid, a resin obtained by adding glycidyl (meth) acrylate to a tricyclodecyl (meth) acrylate / styrene / (meth) acrylic acid copolymer. Resin such as a resin to which glycidyl (meth) acrylate is added to a polymer [K4]; a resin obtained by reacting a (meth) acrylic acid with a copolymer of tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate. Resin [K5] such as a resin obtained by reacting a copolymer of cyclodecyl (meth) acrylate / styrene / glycidyl (meth) acrylate with (meth) acrylic acid; tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate. Examples thereof include a resin [K6] such as a resin obtained by reacting a copolymer with (meth) acrylic acid and further reacting with a tetrahydrophthalic acid 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 the kind of choice. With these resins, the colored curable resin composition is excellent in developability. The resin [K2] is more preferable from the viewpoint of the adhesion between the coloring pattern and the substrate.

The polystyrene-equivalent weight average molecular weight of the resin (B) is usually 3,000 to 100,000, preferably 5,000 to 50,000, more preferably 5,000 to 35,000, and further. 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 hardness of the coating film is improved, the residual film ratio is high, the solubility of the unexposed portion in the developing solution is good, and the resolution of the coloring 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, and 70 mg-KOH / g. ~ 135 mg-KOH / g is particularly preferable. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be obtained by titration using, for example, 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% by mass with respect to the total amount of solid content. It is by mass, particularly preferably 17% by mass to 55% by mass. When the content of the resin (B) is within the above range, the coloring pattern is easily formed, and the resolution and the residual film ratio of the coloring pattern 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 compounds having a polymerizable ethylenically unsaturated bond, which is preferable. 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., as well as 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, and triethylene glycol di. Examples thereof include (meth) acrylate, bis (acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di (meth) acrylate.

Above all, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylol propantri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa (dipentaerythritol hexa (). Meta) 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.
Of these, 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, and more preferably 250 or more and 1,500 or less.

The content of the polymerizable compound (C) is preferably 1 to 70% by mass, preferably 2 to 65% by mass, and 5 to 65% by mass, based on the total amount of solids. It is preferably 7 to 65% by mass, more preferably 10 to 60% by mass, more preferably 13 to 60% by mass, still more preferably 17 to 55% by mass. be.
The content ratio of the resin (B) to the polymerizable compound (C) [resin (B): polymerizable compound (C)] is based on mass, preferably 20:80 to 80:20, more preferably. Is from 35:65 to 80:20.
When the content of the polymerizable compound (C) is within the above range, the residual film ratio at the time of forming the coloring pattern and the chemical resistance of the color filter tend to be improved.

<Polymer Initiator (D)>
The polymerization initiator (D) is not particularly limited as long as it is a compound that can initiate polymerization by generating active radicals, acids and the like by the action of light or heat, 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-acyloxime compound, and a biimidazole compound.

The O-acyloxym compounds are N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one. -2-Imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-on-2-imine, N-acetoxy-1- [9-ethyl-6- (2-methyl) Benzoyl) -9H-carbazole-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- {2-methyl-4- (3,3-dimethyl-2,4-dioxa) Cyclopentanylmethyloxy) benzoyl} -9H-carbazole-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole-3-yl] ] -3-Cyclopentylpropane-1-imine, N-benzoyloxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole-3-yl] -3-cyclopentylpropane-1-one- 2-Imine and the like can be mentioned. Commercially available products such as Irgacure OXE01, OXE02 (above, manufactured by BASF), N-1919 (manufactured by ADEKA) may be used. Among them, the O-acyloxym compounds are N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-on-2-imine and 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-cyclopentylpropane-1-on-2-imine is preferable, and N-benzoyloxy is preferable. -1- (4-Phenylsulfanylphenyl) octane-1-on-2-imine is more preferred.

Alkylphenone compounds are 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutane-1-one. , 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butane-1-one, 2-hydroxy-2-methyl-1-phenylpropane -1-one, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propan-1-one, 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-( Examples thereof include oligomers of 4-isopropenylphenyl) propan-1-one, α, α-diethoxyacetophenone, benzyldimethylketal, Irgacure 369, 907, 379 (all manufactured by BASF).

The biimidazole compounds are 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,3-dichlorophenyl) -4,4'. , 5,5'-Tetraphenylbiimidazole (see, for example, JP-A-6-75372, JP-A-6-75373, etc.), 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-Tetraphenyl biimidazole, 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, Japanese Patent Publication No. 48-38403, Japanese Patent Application Laid-Open No. 62-174204, etc.), an imidazole compound in which the phenyl group at the 4,4'5,5'-position is substituted with a carboalkoxy group (for example, For example, Japanese Patent Application Laid-Open No. 7-10913) and the like can be mentioned. Of these, compounds represented by the following formulas 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- (fran-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 and benzoin isobutyl ether; benzophenone, o-methyl benzoyl benzoate, 4-phenylbenzophenone, 4-benzoyl- Benzoyl compounds such as 4'-methyldiphenylsulfide, 3,3', 4,4'-tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone; 9,10-phenanthlenquinone, Kinon compounds such as 2-ethylanthraquinone and camphorquinone; examples thereof include 10-butyl-2-chloroacrydone, benzyl, methyl phenylglycoxylate, and titanosen compounds. These are preferably used in combination with the polymerization initiation aid (D1) (particularly amines) described later.

The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound and a biimidazole compound, and more preferably. Is a polymerization initiator containing an O-acyloxime 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, 0. It is 1 to 30 parts by mass, more preferably 1 to 30 parts by mass.

<Polymerization initiation aid (D1)>
The polymerization initiator (D1) is a compound or a sensitizer used to promote the polymerization of the polymerizable compound initiated by the polymerization initiator. When the polymerization initiator (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.

Examples of the amine compound include 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 known as Michler's ketone), 4,4'-bis (diethylamino) benzophenone, 4,4'-bis ( Ethylmethylamino) benzophenone and the like can be mentioned, with 4,4'-bis (diethylamino) benzophenone being preferred. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used.

Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, and 9,10-dibutoxy. Anthracene, 2-ethyl-9,10-dibutoxyanthracene and the like can be mentioned.

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

Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, and 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 with respect to 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 coloring 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 the art can be used. For example, an ester solvent (solvent containing -COO- in the molecule and not containing -O-), an ether solvent (solvent containing -O- in the molecule and not containing -COO-), an ether ester solvent (intramolecular). Solvent containing -COO- and -O-), Ketone solvent (solvent containing -CO- in the molecule and not containing -COO-), alcohol solvent (solvent containing OH in the molecule, -O-,- CO- and -COO-free solvents), aromatic hydrocarbon solvents, amide solvents, dimethylsulfoxide and the like.

Ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutate, 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.

Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, and 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, phenyletol, methyl anisol and the like.

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

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

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-. Preference is given to methoxy-1-butanol, 4-hydroxy-4-methyl-2-pentanone, N, N-dimethylformamide, N-methylpyrrolidone and the like, such as propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethylene glycol monobutyl ether and 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, 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 in the above range, the flatness at the time of coating is good, and the color density is not insufficient when the color filter is formed, so that the display characteristics tend to be good.

<Leveling agent (F)>
Examples of the leveling agent (F) include a silicone-based surfactant, a fluorine-based surfactant, and a silicone-based surfactant having a fluorine atom. These may have a polymerizable group in the side chain.
Examples of the silicone-based surfactant include a surfactant having a siloxane bond in the molecule. Specifically, Torre 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, TSF4460 (manufactured by Momentive Performance Materials Japan GK), etc. Can be mentioned.

Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, Florard (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafuck (registered trademark) F142D, F171, F172, F173, F177, F183, F554, and F554. R30, RS-718-K (manufactured by DIC Co., Ltd.), Ftop (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronics 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 Laboratory Co., Ltd.).

Examples of the silicone-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specific examples thereof include Megafuck (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, and more preferably 0.001% by mass or more and 0. It is 5% by mass or less, more preferably 0.001% by mass or more and 0.2% by mass or less, preferably 0.002% by mass or more and 0.1% by mass or less, and more preferably 0.005% by mass or more and 0. .07% by mass or less. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

<Other ingredients>
The colored curable resin composition of the present invention is an additive known in the art such as a filler, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents and the like, if necessary. May include.

<Manufacturing method of colored curable resin composition>
The color-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 a leveling agent (F), a polymerization initiator (D1) and other components.
When the pigment (P) is contained, the pigment is preferably mixed with a part or all of the solvent (E) in advance and dispersed using a bead mill or the like until the average particle size of the pigment becomes about 0.2 μm or less. .. At this time, if necessary, a pigment dispersant and a part or all of the resin (B) may be blended. As the pigment dispersant, a commercially available surfactant can be used, and the surface activity of silicone-based, fluorine-based, ester-based, cationic-based, anionic-based, nonionic-based, amphoteric, polyester-based, polyamine-based, acrylic-based, etc. Agents and the like can be mentioned. Examples of the surfactant include polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid-modified polyesters, tertiary amine-modified polyurethanes, polyethylene imines and the like. , KP (manufactured by Shin-Etsu Chemical Industry Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solpers (manufactured by Geneca Co., Ltd.), EFKA (manufactured by BASF Japan Co., Ltd.), Azispar (registered trademark) (Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (manufactured by Big Chemie) and the like can be mentioned, and these can be used alone or in combination of two or more. The desired colored curable resin composition can be prepared by mixing the remaining components with the pigment dispersion liquid thus obtained so as to have a predetermined concentration.
It is preferable that the compound (Z) is previously dissolved in a part or all of the solvent (E) 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.
It is preferable to filter the colored curable resin composition after mixing with a filter having a pore size of about 0.01 to 10 μm.

<Manufacturing method of color filter>
Examples of the method for producing a colored pattern from the colored curable resin composition of the present invention include a photolithography method, an inkjet method, a printing method and the like. Of these, the photolithography method is preferable. The photolithography method is a method in which the colored curable resin composition is applied to a substrate and dried to form a colored composition layer, and the colored composition layer is exposed and developed through a photomask. In the photolithography method, a colored coating film which is a cured product of the colored composition layer can be formed by not using a photomask at the time of exposure and / or not developing. The colored pattern and the colored coating film thus formed are the color filters of the present invention.
The film thickness of the color filter to be produced is not particularly limited and can be appropriately adjusted according to the purpose, application and the like. For example, 0.1 to 30 μm, preferably 0.1 to 20 μm, still more preferably 0.5. It is ~ 6 μm.

The substrate includes a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, soda lime glass whose surface is silica-coated, a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate, silicon, or on the substrate. Aluminum, silver, silver / copper / palladium alloy thin films, etc. are formed on the glass. Another color filter layer, resin layer, transistor, circuit 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 conventional device or condition. For example, it can be produced as follows.
First, the colored curable resin composition is applied onto a substrate and dried by heating and drying (pre-baking) and / or under reduced pressure to remove volatile components such as a solvent to obtain a smooth colored composition layer.
Examples of the coating method include a spin coating method, a slit coating method, a slit and spin coating method, and the like.
The temperature for heat drying is preferably 30 to 120 ° C, more preferably 50 to 110 ° C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.
When drying under reduced pressure, it is preferable to carry out drying under a pressure of 50 to 150 Pa in a temperature range of 20 to 25 ° C.
The film thickness of the coloring composition layer is not particularly limited, and may be appropriately selected depending on the film thickness of the target color filter.

The coloring composition layer is then exposed via a photomask to form the desired coloring pattern. The pattern on the photomask is not particularly limited, and a pattern according to the intended use is used.
As the light source used for exposure, a light source that generates light having a wavelength of 250 to 450 nm is preferable. For example, light less than 350 nm is cut by using a filter that cuts this wavelength range, and light near 436 nm, 408 nm, and 365 nm is selectively extracted by using a bandpass filter that extracts these wavelength ranges. You may do it. Specific examples thereof include mercury lamps, light emitting diodes, metal halide lamps, halogen lamps and the like.
An exposure device such as a mask aligner and a stepper should be used because it is possible to uniformly irradiate the entire exposed surface with parallel rays and to accurately align the photomask with the substrate on which the coloring composition layer is formed. Is preferable.

By bringing the exposed coloring composition layer into contact with a developing solution for development, a coloring pattern is formed on the substrate. By development, the unexposed portion of the coloring composition layer is dissolved in a developing solution and removed.
As the developing solution, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, or tetramethylammonium hydroxide is preferable. 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. Further, the developer may contain a surfactant.
The developing method may be any of a paddle method, a dipping method, a spray method and the like. Further, the substrate may be tilted at an arbitrary angle during development.
After development, it is preferable to wash with water.

Further, it is preferable to post-bake the obtained coloring pattern. The post-bake 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.

This application claims the benefit of priority under Japanese Patent Application No. 2014-186017 filed on September 12, 2014. The entire contents of the specification of Japanese Patent Application No. 2014-186017 filed on September 12, 2014 are incorporated herein by reference.

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

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 (manufactured by Tokyo Chemical Industry Co., Ltd.) ), 2.73 parts, 1-pentanol (manufactured by Tokyo Chemical Industry Co., Ltd.) 157 parts and ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) 7.43 parts, and stirred at 120 ° C. for 3 hours. And the 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 the mixture was stirred at 120 ° C. for 14 hours to obtain a mixture (2).
The obtained mixture (1) and the mixture (2) are mixed, and further, ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) 3.76 parts and 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. The above reaction solution was cooled to room temperature, and the precipitated crystals were obtained as a residue of suction filtration. 140 parts of tetrahydrofuran was added to this residue, and the mixture was stirred at 70 ° C. for 1 hour, and then an insoluble material was obtained as a residue by suction filtration. 120 parts of tetrahydrofuran was added to this residue, and the mixture was stirred at 70 ° C. for 1 hour, and then an insoluble material was obtained as a residue by suction filtration. 340 parts of N, N-dimethylformamide was added to this residue, heated to 90 ° C. to dissolve, and then allowed to stand at 0 ° C. to 5 ° C. The precipitated crystals were obtained as a residue of suction filtration. The residue was dried under reduced pressure at 60 ° C. to obtain 5.69 parts of the 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. Drying under reduced pressure at 60 ° C. for 24 hours gave 4.2 parts of the compound represented by the formula (Z-1).

Identification of the compound represented by the formula (Z-1) (mass spectrometry) Ionization mode = ESI +: m / z = 479.2 [M + 1] ⁺
Exact Mass: 478.2

Example 2
In Example 1, the compound represented by the following formula (d-1) is used in place of 3-amino-4-hydroxybenzoic acid, and the compound is synthesized in the same manner as in Example 1 and is represented by the formula (Ad1-2). 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 acid anhydride was further added, and the temperature 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. Drying under reduced pressure at 60 ° C. for 24 hours gave 3.8 parts of the compound represented by the formula (Z-41).

Identification of the compound represented by the 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 flowed 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. with stirring. Then, in the flask, 19 parts of methacrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decane-8-ylacrylate and 3,4-epoxytricyclo [5.2. 1.0 ^2,6 ] A solution of 171 parts of a mixture of decane-9-ylacrylate (content ratio is 50:50 in molar ratio) in 40 parts of propylene glycol monomethyl ether acetate was dissolved in 40 parts of propylene glycol monomethyl ether acetate over about 5 hours using a dropping pump. And dropped. On the other hand, a solution prepared by dissolving 26 parts of the polymerization initiator 2,2'-azobis (2,4-dimethylvaleronitrile) in 120 parts of propylene glycol monomethyl ether acetate was placed in a flask over about 5 hours using another dropping pump. Dropped. After the dropping of the polymerization initiator was completed, the mixture was kept at the same temperature for about 3 hours and then cooled to room temperature to obtain a solution of the copolymer (resin B1) having a solid content of 43.5%. The weight average molecular weight of the obtained resin B1 was 8000, the molecular weight distribution was 1.98, and the acid value in terms of solid content was 53 mgKOH / g.

[Preparation of Color Curable Resin Composition]
Example 3
Colorant (A): C.I. I. Pigment Green 58 (Pigment) 27 copies;
Acrylic pigment dispersant 12 parts;
Resin (B): Resin B1 (solid content equivalent) 9.5 parts; and solvent (E): propylene glycol monomethyl ether acetate
180 copies;
Was mixed, and a pigment dispersion liquid (3) in which the pigment was sufficiently dispersed was obtained using a bead mill.

Colorant (A): 2.0 parts of the compound represented by the formula (Z-1);
Resin (B): Resin B1 (solid content equivalent) 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) octane-1-on-2-imine (Irgacure® OXE-01; BASF; O-acyloxime compound) 9.8 copies;
Solvent (E): Propylene glycol monomethyl ether acetate
670 copies;
Leveling agent (F): 0.15 parts of polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.); and 228.5 parts of pigment dispersion (3);
Was mixed to obtain a colored curable resin composition (J1).

Example 4
C.I. of colorant (A). I. Pigment Green 58 (pigment) to C.I. I. A color-curable resin composition (J2) was obtained in the same manner as in Example 3 except that the pigment green 36 (pigment) was used.

Example 5
The color curable resin composition (J3) is the same as in Example 3 except that the compound represented by the formula (Z-1) of the colorant (A) is replaced with the compound represented by the formula (Z-41). ) Was obtained.

Example 6
C.I. of colorant (A). I. Pigment Green 58 (pigment) to C.I. I. A color-curable resin composition (J4) was obtained in the same manner as in Example 5 except that the pigment green 36 (pigment) was used.

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

Colorant (A): 1.0 part of the compound represented by the formula (d0);
Resin (B): Resin B1 (solid content equivalent) 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) octane-1-on-2-imine (Irgacure® OXE-01; BASF; O-acyloxime compound) 9.8 copies;
Solvent (E): Propylene glycol monomethyl ether acetate
670 copies;
Leveling agent (F): 0.15 parts of polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.); and 228.5 parts of pigment dispersion (5);
Was 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 (manufactured by Taoka Chemical Industry Co., Ltd., average molecular weight 10700, acid value 70 mgKOH / 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) Octane-1-on-2-imine (Irgacure® OXE01; BASF Japan, Inc.) 0.58 parts;
Leveling agent: Polyether-modified silicone (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.01 parts;
Solvent: Propylene glycol monomethyl ether 46.6 parts;
Solvent: Propylene glycol monomethyl ether acetate 6.8 parts;
Was mixed to obtain a resin composition for sublimation test (SJS).

[Formation of resin coating film (SJSM) for sublimation test]
The sublimation test resin composition (SJS) obtained above was applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning Inc.) by a spin coating method, and the volatile components were volatilized at 100 ° C. for 3 minutes. .. After cooling, light was irradiated with an exposure amount of 150 mJ / cm ² (based on 365 nm) under an atmospheric atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). A resin coating film (SJSM) for sublimation test (thickness 2.2 μm) was formed by heating at 220 ° C. for 2 hours in an oven.

Example 7
[Preparation of coloring pattern and evaluation of sublimation]
The colored curable resin composition (J1) obtained in Example 3 is applied onto a 2-inch square glass substrate (Eagle XG; manufactured by Corning Inc.) 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 quartz glass photomask was set to 200 μm, and an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) was used in an air atmosphere at 80 mJ / cm ² The exposure amount (based on 365 nm) was used. As the photomask, a photomask having a line-and-space pattern of 100 μm was used. The colored composition layer after exposure was immersed in an aqueous solution containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 25 ° C. for 70 seconds to develop and washed with water. The film thickness was measured. The results are shown in Table 1.
The colored coating film and the sublimation test resin coating film (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 sublimation test resin coating film (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 sublimation property. The results are shown in Table 1. In Table 1, ◯ indicates that the colorant does not have sublimation property, and × indicates that the colorant has sublimation property.

Examples 8 to 10 and Comparative Example 2
Except for replacing the colored curable resin composition (J1) obtained in Example 3 with the colored curable resin composition (J2) to the colored curable resin composition (J5), the same as in Example 7. In the same manner, a coloring pattern was obtained and the sublimation property was evaluated. The results are shown in Table 1.

When a color filter is formed from a color curable resin composition containing the compound of the present invention, sublimation of the colorant can be suppressed. A color filter using a 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 the formula (Z).

[In the formula (Z), R ¹ and R ² are independent groups containing a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, an aryl group, an acryloyl group, or a methacryloyl group . Represents .
R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ independently have a hydrogen atom, a halogen atom, a cyano group, a carboxyl group, a nitro group, and 1 to 20 carbon atoms. Represents an alkyl group, an alkoxy group having 1 to 20 carbon atoms, a group containing an acryloyl group, or a group containing a methacryloyl group.
However, 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 group containing a methacryloyl group .
The group containing an acryloyl group or the group containing a methacryloyl group is a group represented by the 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. May be good.
R ^16A represents an acryloyl group or a methacryloyl group.
* Represents a bond with a nitrogen atom or a carbon atom. ]] A colorant containing 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 a halogenated copper phthalocyanine pigment and a halogenated zinc phthalocyanine pigment. 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. The colorant according to any one of claims 3 to 5, which is at least one selected from the group consisting of Pigment Green 58. A color curable resin composition containing the colorant, resin, polymerizable compound and polymerization initiator according to any one of claims 2 to 6. A color filter formed from the colored curable resin composition according to claim 7. A liquid crystal display device including the color filter according to claim 8.