JP2015143341A - Compound and coloring curable resin composition - Google Patents

Abstract

Disclosed is a dye capable of forming a color filter having excellent heat resistance. A compound represented by formula (I) and a dye comprising the tautomerism thereof. [R1A to R8A are each independently H, halogen atom, hydroxy group or alkyl; R9A to R12A are each independently H / amino or substituted / unsubstituted alkyl or substituted / unsubstituted aryl with halogen atom; A is substituted / unsubstituted heteroaromatic; two of R1 to R4 are alkylphenyl having a sulfonic acid group and the rest are each independently alkyl; R5 to R16 are each independently H, halogen atom, hydroxy or alkyl R17 is phenylamino having alkyl or alkoxy) [Selection] None

Description

  The present invention relates to a compound and a colored curable resin composition.

Patent Document 1 describes a compound represented by the formula (A-III-1) as a colored curable resin composition for forming a color filter included in a liquid crystal display device or the like or a solid-state imaging device. .

US 8,282,862

  Conventionally known colored curable resin compositions containing the above-mentioned compounds have not been sufficiently satisfactory in terms of heat resistance.

［式（Ｉ）中、Ｒ^１Ａ〜Ｒ^８Ａは、それぞれ独立して、水素原子、ハロゲン原子、ヒドロキシ基又は炭素数１〜２０のアルキル基（該アルキル基を構成する炭素原子間に酸素原子が挿入されていてもよい）を表す。
Ｒ^９Ａ〜Ｒ^１２Ａは、それぞれ独立して、水素原子、アミノ基でもしくはハロゲン原子で置換されていてもよい炭素数１〜２０のアルキル基（該アルキル基を構成する炭素原子間に酸素原子が挿入されていてもよい）又は置換基を有していてもよいアリール基を表す。Ｒ^９ＡとＲ^１０Ａとが結合してそれらが結合する窒素原子とともに環を形成してもよく、Ｒ^１１AとＲ^１２Aとが結合してそれらが結合する窒素原子とともに環を形成してもよい。
Ａは、置換基を有していてもよいヘテロ芳香族基を表す。
Ｒ^１〜Ｒ^４のうちの２つは、それぞれ独立して式（ｉ）で表される基であり、残り２つは、それぞれ独立して炭素数１〜２０のアルキル基（該アルキル基を構成する炭素原子間に酸素原子が挿入されていてもよい）を表す。

（式（ｉ）中、ｎは１〜８の整数を表し、＊は窒素原子との結合の手を表す。）
Ｒ^５〜Ｒ^１６は、それぞれ独立して、水素原子、ハロゲン原子、ヒドロキシ基又は炭素数１〜２０のアルキル基（該アルキル基を構成する炭素原子間に酸素原子が挿入されていてもよい）を表す。
Ｒ^１７は、式（ｉｉ）で表される基である。

（式（ｉｉ）中、Ｒ^１８は、炭素数１〜４のアルキル基又は炭素数１〜４のアルコキシ基を表し、＊は炭素原子との結合の手を表す。）]
［２］[１]に記載の式（Ｉ）で表される染料を含む着色剤（Ａ）と、樹脂（Ｂ）と、重合性化合物（Ｃ）と、重合開始剤（Ｄ）とを含む着色硬化性樹脂組成物。
［３］着色剤（Ａ）が、アントラキノン染料およびテトラアザポルフィリン染料からなる群から選ばれる少なくとも１つの染料（Ａ２）をさらに含む［２］に記載の着色硬化性樹脂組成物。
［４］無色の金属錯体（Ｆ）をさらに含む［２］または［３］に記載の着色硬化性樹脂組成物。
［５］［２］〜［４］のいずれかに記載の着色硬化性樹脂組成物から形成される塗膜。
［６］［２］〜［４］のいずれかに記載の着色硬化性樹脂組成物から形成されるカラーフィルタ。
［７］［６］に記載のカラーフィルタを含む表示装置。 The present invention provides the following [1] to [7].
[1] A dye represented by the formula (I).

[In the formula (I), R ^{1A to} R ^8A each independently represents a hydrogen atom, a halogen atom, a hydroxy group or an alkyl group having 1 to 20 carbon atoms (an oxygen atom is present between carbon atoms constituting the alkyl group). May be inserted).
R ^{9A to} R ^12A are each independently a hydrogen atom, an amino group, or an alkyl group having 1 to 20 carbon atoms which may be substituted with a halogen atom (an oxygen atom is present between carbon atoms constituting the alkyl group). Which may be inserted) or an aryl group which may have a substituent. R ^9A and R ^10A may be bonded to form a ring with the nitrogen atom to which they are bonded, or R ^11A and R ^12A may be bonded to form a ring with the nitrogen atom to which they are bonded.
A represents a heteroaromatic group which may have a substituent.
Two of R ^{1 to} R ⁴ are each independently a group represented by the formula (i), and the other two are independently an alkyl group having 1 to 20 carbon atoms (the alkyl group is An oxygen atom may be inserted between the constituent carbon atoms).

(In formula (i), n represents an integer of 1 to 8, and * represents a bond to a nitrogen atom.)
R ^{5 to} R ¹⁶ are each independently a hydrogen atom, a halogen atom, a hydroxy group or an alkyl group having 1 to 20 carbon atoms (an oxygen atom may be inserted between carbon atoms constituting the alkyl group). Represents.
R ¹⁷ is a group represented by formula (ii).

(In formula (ii), R ¹⁸ represents an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and * represents a bond with a carbon atom.)]
[2] A colorant (A) containing the dye represented by the formula (I) according to [1], a resin (B), a polymerizable compound (C), and a polymerization initiator (D) are included. Colored curable resin composition.
[3] The colored curable resin composition according to [2], wherein the colorant (A) further includes at least one dye (A2) selected from the group consisting of an anthraquinone dye and a tetraazaporphyrin dye.
[4] The colored curable resin composition according to [2] or [3], further including a colorless metal complex (F).
[5] A coating film formed from the colored curable resin composition according to any one of [2] to [4].
[6] A color filter formed from the colored curable resin composition according to any one of [2] to [4].
[7] A display device including the color filter according to [6].

  The colored curable resin composition containing the compound of the present invention can form a color filter having excellent heat resistance.

The present invention is a colored curable resin composition comprising a compound represented by the formula (I) and a compound represented by the formula (I).
The compound represented by the formula (I) can be used as a dye.

式（Ｉ）中、Ｒ^１Ａ〜Ｒ^８Ａは、それぞれ独立して、水素原子、ハロゲン原子、ヒドロキシ基又は炭素数１〜２０のアルキル基（該アルキル基を構成する炭素原子間に酸素原子が挿入されていてもよい）を表す。
Ｒ^９Ａ〜Ｒ^１２Ａは、それぞれ独立して、水素原子、アミノ基でもしくはハロゲン原子で置換されていてもよい炭素数１〜２０のアルキル基（該アルキル基を構成する炭素原子間に酸素原子が挿入されていてもよい）又は置換基を有していてもよいアリール基を表す。Ｒ^９ＡとＲ^１０Ａとが結合してそれらが結合する窒素原子とともに環を形成してもよく、Ｒ^１１AとＲ^１２Aとが結合してそれらが結合する窒素原子とともに環を形成してもよい。
Ａは、置換基を有していてもよいヘテロ芳香族基を表す。
Ｒ^１〜Ｒ^４のうちの２つは、それぞれ独立して式（ｉ）で表される基であり、残り２つは、それぞれ独立して炭素数１〜２０のアルキル基（該アルキル基を構成する炭素原子間に酸素原子が挿入されていてもよい）を表す。

（式（ｉ）中、ｎは１〜８の整数を表し、＊は窒素原子との結合の手を表す。）
Ｒ^５〜Ｒ^１６は、それぞれ独立して、水素原子、ハロゲン原子、ヒドロキシ基又は炭素数１〜２０のアルキル基（該アルキル基を構成する炭素原子間に酸素原子が挿入されていてもよい）を表す。
Ｒ^１７は、式（ｉｉ）で表される基である。

（式（ｉｉ）中、Ｒ^１８は、炭素数１〜４のアルキル基又は炭素数１〜４のアルコキシ基を表し、＊は炭素原子との結合の手を表す。） The compound represented by formula (I) (hereinafter sometimes referred to as dye (A1)) also includes tautomers thereof.

In formula (I), R ^{1A to} R ^8A each independently represents a hydrogen atom, a halogen atom, a hydroxy group or an alkyl group having 1 to 20 carbon atoms (an oxygen atom is inserted between carbon atoms constituting the alkyl group). May be used).
R ^{9A to} R ^12A are each independently a hydrogen atom, an amino group, or an alkyl group having 1 to 20 carbon atoms which may be substituted with a halogen atom (an oxygen atom is present between carbon atoms constituting the alkyl group). Which may be inserted) or an aryl group which may have a substituent. R ^9A and R ^10A may be bonded to form a ring with the nitrogen atom to which they are bonded, or R ^11A and R ^12A may be bonded to form a ring with the nitrogen atom to which they are bonded.
A represents a heteroaromatic group which may have a substituent.
Two of R ^{1 to} R ⁴ are each independently a group represented by the formula (i), and the other two are independently an alkyl group having 1 to 20 carbon atoms (the alkyl group is An oxygen atom may be inserted between the constituent carbon atoms).

(In formula (i), n represents an integer of 1 to 8, and * represents a bond to a nitrogen atom.)
R ^{5 to} R ¹⁶ are each independently a hydrogen atom, a halogen atom, a hydroxy group or an alkyl group having 1 to 20 carbon atoms (an oxygen atom may be inserted between carbon atoms constituting the alkyl group). Represents.
R ¹⁷ is a group represented by formula (ii).

(In formula (ii), R ¹⁸ represents an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and * represents a bond with a carbon atom.)

  In the formula (I), examples of the halogen atom include a fluorine atom, a chlorine atom, and an iodine atom.

Examples of the alkyl group having 1 to 20 carbon atoms include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, A linear alkyl group having 1 to 20 carbon atoms such as a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an icosyl group;
Isopropyl group, isobutyl group, sec-butyl group, isopentyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 1-ethylbutyl group, 2-ethylbutyl group, 1- Methylhexyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 5-methylhexyl group, 1-ethylpentyl group, 2-ethylpentyl group, 3-ethylpentyl group, 1-propylbutyl Group, 1- (1-methylethyl) butyl group, 1- (1-methylethyl) -2-methylpropyl group, 1-methylheptyl group, 2-methylheptyl group, 3-methylheptyl group, 4-methylheptyl group Group, 5-methylheptyl group, 6-methylheptyl group, 1-ethylhexyl group, 2-ethylhexyl group, 3-ethylhexyl 4-ethylhexyl group, 1-n-propylpentyl group, 2-propylpentyl group, 1- (1-methylethyl) pentyl group, 1-butylbutyl group, tert-butyl group, 1,1-dimethylpropyl group, 1 , 1-dimethylbutyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 1-ethyl-2-methylpropyl group, 1,1-dimethylpentyl group, 1 , 2-dimethylpentyl group, 1,3-dimethylpentyl group, 1,4-dimethylpentyl group, 2,2-dimethylpentyl group, 2,3-dimethylpentyl group, 2,4-dimethylpentyl group, 3,3 -Dimethylpentyl group, 3,4-dimethylpentyl group, 1-ethyl-1-methylbutyl group, 1-ethyl-2-methylbutyl group, 1-ethyl-3-methylbutyl group 2-ethyl-1-methylbutyl group, 2-ethyl-3-methylbutyl group, 1,1-dimethylhexyl group, 1,2-dimethylhexyl group, 1,3-dimethylhexyl group, 1,4-dimethylhexyl group, 1,5-dimethylhexyl group, 2,2-dimethylhexyl group, 2,3-dimethylhexyl group, 2,4-dimethylhexyl group, 2,5-dimethylhexyl group, 3,3-dimethylhexyl group, 3, 4-dimethylhexyl group, 3,5-dimethylhexyl group, 4,4-dimethylhexyl group, 4,5-dimethylhexyl group, 1-ethyl-2-methylpentyl group, 1-ethyl-3-methylpentyl group, 1-ethyl-4-methylpentyl group, 2-ethyl-1-methylpentyl group, 2-ethyl-2-methylpentyl group, 2-ethyl-3-methylpentyl group, 2-ethyl Til-4-methylpentyl group, 3-ethyl-1-methylpentyl group, 3-ethyl-2-methylpentyl group, 3-ethyl-3-methylpentyl group, 3-ethyl-4-methylpentyl group, 1- Propyl-1-methylbutyl group, 1-propyl-2-methylbutyl group, 1-propyl-3-methylbutyl group, 1- (1-methylethyl) -1-methylbutyl group, 1- (1-methylethyl) -2- A branched alkyl group having 3 to 20 carbon atoms such as methylbutyl group, 1- (1-methylethyl) -3-methylbutyl group, 1,1-diethylbutyl group, 1,2-diethylbutyl group;
Examples of the cycloalkyl group include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a 2-methylpentyl group, a 2-methylhexyl group, a 2,5-dimethylpentyl group, and a 2,6-dimethylhexyl group.

  In the alkyl group having 1 to 20 carbon atoms, examples of the group in which an oxygen atom is inserted between carbon atoms constituting the alkyl group include groups represented by the following formulae. In the following formula, * represents a carbon atom or a bond with a carbon atom. Among these, in the alkyl group having 1 to 10 carbon atoms, a group in which an oxygen atom is inserted between carbon atoms constituting the alkyl group is preferable, and in the alkyl group having 1 to 6 carbon atoms, the alkyl group is constituted. A group in which an oxygen atom is inserted between carbon atoms is more preferable.

The halogen atom represented by R ^{1A to} R ^8A is preferably a fluorine atom or a chlorine atom.

As the alkyl group having 1 to 20 carbon atoms represented by R ^{1A to} R ^8A , a group represented by the following formula is preferable. * Represents a bond with a carbon atom.

R ^{1A to} R ^8A are each independently preferably a hydrogen atom and an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group, an ethyl group, a propyl group, and a butyl group, and a hydrogen atom and a methyl group. Is more preferable.

As an amino group, an amino group; an amino group substituted with one alkyl group having 1 to 4 carbon atoms such as an N-methylamino group or an N-ethylamino group; a dimethylamino group, a diethylamino group, an ethylmethylamino group, or the like And an amino group substituted with two alkyl groups having 1 to 4 carbon atoms.
As a C1-C20 alkyl group substituted by the amino group or the halogen atom represented by R ^<9A > -R < ^12A >, group represented by a following formula is mentioned, for example. In the following formula, * represents a bond with a nitrogen atom.

In the aryl group which may have a substituent represented by R ^{9A to} R ^12A , the substituent includes a halogen atom such as a fluorine atom, a chlorine atom and iodine; a carbon such as a chloromethyl group and a trifluoromethyl group Examples thereof include a haloalkyl group having 1 to 6 carbon atoms; an alkoxy group having 1 to 6 carbon atoms such as a methoxy group and an ethoxy group; a hydroxy group; a sulfamoyl group; an alkylsulfonyl group having 1 to 6 carbon atoms such as a methylsulfonyl group.

In the aryl group which may have a substituent represented by R ^{9A to} R ^12A , examples of the aryl group include aryl groups having 6 to 10 carbon atoms such as a phenyl group, a tolyl group, a xylyl group, and a naphthyl group. Preferably a phenyl group.

Examples of the aryl group that may have a substituent represented by R ^{9A to} R ^12A include groups represented by the following formulas. In the following formula, * represents a bond with a nitrogen atom.

^{Examples of} the ring formed by combining R ^9A and R ^10A and R ^11A and R ^12A together with the nitrogen atom to which they are bonded include a pyrrolidine ring, a morpholine ring, a piperidine ring, and a piperazine ring.

R ^{9A to} R ^12A are preferably a hydrogen atom, a methyl group, an ethyl group, or a phenyl group.

A represents a heteroaromatic group which may have a substituent.
Heteroaromatic groups include pyrrole, imidazole, thiazole, oxazole, furan, thiophene, triazole, pyrazole, isoxazole, isothiazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, indole, benzofuran, benzothiophene, benzimidazole, benz Examples include thiazole, quinoline, isoquinoline, quinazoline, quinoxaline, and the like. A heteroaromatic group having a nitrogen atom is preferable as a constituent element of the ring.
Examples of the substituent that the heteroaromatic group may have include a halogen atom such as a fluorine atom, a chlorine atom and iodine; a haloalkyl group having 1 to 6 carbon atoms such as a chloromethyl group and a trifluoromethyl group; a methyl group, C1-C4 alkyl groups, such as an ethyl group, a butyl group, and a propyl group; C1-C6 alkoxy groups, such as a methoxy group and an ethoxy group; Hydroxy group; Amino group;
As an amino group, an amino group; an amino group substituted with one alkyl group having 1 to 4 carbon atoms such as an N-methylamino group or an N-ethylamino group; a dimethylamino group, a diethylamino group, an ethylmethylamino group, or the like And an amino group substituted with two alkyl groups having 1 to 4 carbon atoms.
Examples of the substituent that the heteroaromatic group may have include an alkyl group having 1 to 4 carbon atoms and an amino group.

[Ｒ^１ａ〜Ｒ^２５ａは、水素原子、アミノ基でもしくはハロゲン原子で置換されていてもよい炭素数１〜２０のアルキル基（該アルキル基を構成する炭素原子間に酸素原子が挿入されていてもよい）又は置換されていてもよいアリール基を表し、＊は炭素原子との結合の手を表す。]
Ｒ^１ａ〜Ｒ^２５ａで表されるアミノ基でもしくはハロゲン原子で置換されていてもよい炭素数１〜２０のアルキル基としては、Ｒ^９A〜Ｒ^１２Aで表されるアミノ基でまたはハロゲン原子で置換された炭素数１〜２０のアルキル基と同じものが挙げられる。
Ｒ^１ａ〜Ｒ^２５ａで表される置換されていてもよいアリール基としては、Ｒ^９A〜Ｒ^１２Aで表される置換されていてもよいアリール基と同じものが挙げられる。 Examples of A include a group represented by the formula (A-1) to a group represented by the formula (A-10), and among them, a group represented by the formula (A-1) is preferable.

[R ^{1a to} R ^25a is a C 1-20 alkyl group optionally substituted with a hydrogen atom, an amino group or a halogen atom (an oxygen atom is inserted between carbon atoms constituting the alkyl group). Or an aryl group which may be substituted, and * represents a bond to a carbon atom. ]
The alkyl group having 1 to 20 carbon atoms which may be substituted with an amino group represented by R ^{1a to} R ^25a or a halogen atom is substituted with an amino group represented by R ^{9A to} R ^12A or a halogen atom. The same thing as the C1-C20 alkyl group made | formed is mentioned.
Examples of the ^optionally substituted aryl group represented by R ^{1a to} R ^25a include the same as the optionally substituted aryl group represented by R ^{9A to} R ^12A .

Specific examples of the group represented by the formula (A-1) include the following groups.

[＊は窒素原子との結合の手を表す。] Two of R ^{1 to} R ⁴ are groups represented by the formula (i). R ¹ and R ³ are preferably groups represented by formula (i).
Examples of the group represented by the formula (i) include a group represented by the formula (i-1) to a group represented by the formula (i-6). From the viewpoint of obtaining raw materials, the group represented by the formula (i-1) ) To a group represented by formula (i-3) are preferable, and a group represented by formula (i-1) is more preferable.

[* Represents a bond with a nitrogen atom. ]

As the alkyl group having 1 to 20 carbon atoms represented by R ^{1 to} R ⁴ (an oxygen atom may be inserted between carbon atoms constituting the alkyl group), a methyl group or an ethyl group is preferable.

As an alkyl group having 1 to 20 carbon atoms represented by R ^{5 to} R ¹⁶ (an oxygen atom may be inserted between carbon atoms constituting the alkyl group), a methyl group or an ethyl group is preferable.

The group represented by R ^{5 to} R ¹⁶ is preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom.

In formula (ii) represented by R ¹⁷ , examples of the alkyl group having 1 to 4 carbon atoms represented by R ¹⁸ include a methyl group, an ethyl group, a propyl group, and a butyl group, and a methyl group or an ethyl group is preferable. .
Examples of the alkoxy group having 1 to 4 carbon atoms include a methoxy group and an ethoxy group, and an ethoxy group is preferable.

[＊は炭素原子との結合の手を表す。] Examples of the group represented by the formula (ii) include a group represented by the formula (ii-1) to a group represented by the formula (ii-6). From the viewpoint of solubility, the group represented by the formula (ii-4) ) To a group represented by the formula (ii-6) are preferable, and a group represented by the formula (ii-5) is particularly preferable.

[* Represents a bond to a carbon atom. ]

Specific examples of the compound represented by the formula (I) include compounds represented by the following formula.

  Next, the manufacturing method of the compound represented by Formula (I) is demonstrated.

Examples of the method for producing the compound represented by the formula (I) include a compound represented by the formula (1-a) synthesized according to the description of WO2012-53211

The method of mixing the salt of the anion and metal cation which are represented by Formula (1-b) in a solvent is mentioned. Examples of the metal cation forming the salt include alkali metal cations such as lithium cation, sodium cation and potassium cation.

Solvents include N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, acetonitrile, ethyl acetate, toluene, methanol, ethanol, isopropanol, acetone, tetrahydrofuran, dioxane, water and chloroform. Is mentioned.
Among these, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, methanol, ethanol, isopropanol and water are preferable, and water is more preferable.
When the solvent is water, an acid such as acetic acid or hydrochloric acid may be added.
The mixing of the compound represented by the formula (1-a) and the salt of the anion and metal cation represented by the formula (1-b) may be performed by dissolving both in the above solvent, You may carry out without making it melt | dissolve.

  The mixing temperature of the compound represented by the formula (1-a) and the salt of the anion and metal cation represented by the formula (1-b) is preferably 0 ° C. to 150 ° C., more preferably 10 ° C. to 120 ° C. ° C, more preferably 20 ° C to 100 ° C. The mixing time is preferably 1 hour to 72 hours, more preferably 2 hours to 48 hours, and even more preferably 3 hours to 24 hours.

When a solvent compatible with water is used, a reaction solution of a compound represented by the formula (1-a) and a salt of an anion and a metal cation represented by the formula (1-b) is used as necessary. The compound represented by the formula (I) can be taken out as a solid by further stirring for 1 to 3 hours and then filtering.
When a solvent that is incompatible with water is used, water is added to the reaction solution of the compound represented by formula (1-a) and the salt of an anion and metal cation represented by formula (1-b). The dye represented by the formula (I) can be taken out as a solid by precipitating crystals and then filtering.

  The colored curable resin composition of the present invention includes a colorant (A) containing a compound represented by the formula (I), a resin (B), a polymerizable compound (C), and a polymerization initiator (D). including. As needed, you may contain a solvent (E) and a colorless metal complex (F).

<Colorant (A)>
The colorant (A) contains the dye (A1), and further contains at least one dye (A2) selected from the group consisting of an anthraquinone dye and a tetraazaporphyrin dye (hereinafter sometimes referred to as a dye (A2)). May be included.

As the anthraquinone dye, a known substance may be used. As an anthraquinone dye, for example,
C. I. Solvent Yellow 117 (hereinafter, CI Solvent Yellow is omitted, and only the number is described), 163, 167, 189,
C. I. Solvent orange 77, 86,
C. I. Solvent Red 111, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 222, 227, 230, 245, 247,
C. I. Solvent violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60,
C. I. Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139,
C. I. Solvent Green 3, 28, 29, 32, 33,
C. I. Acid Red 80,
C. I. Acid Green 25, 27, 28, 41,
C. I. Acid Violet 34,
C. I. Acid Blue 25, 27, 40, 45, 78, 80, 112
C. I. Disperse Yellow 51,
C. I. Disperse violet 26, 27,
C. I. Disperse Blue 1, 14, 56, 60,
C. I. Direct Blue 40,
C. I. Modern Red 3, 11,
C. I. Modern Blue 8
Etc. The anthraquinone dye is preferably soluble in an organic solvent, and more preferably a blue, violet or red anthraquinone dye.

  More preferable anthraquinone dyes include compounds represented by formula (3-1) to compounds represented by formula (3-11).

  As an anthraquinone dye, the compound represented by Formula (3-4) and the compound represented by Formula (3-11) are more preferable. When these anthraquinone dyes are used, a high-contrast coating film or pattern can be formed, and there is little generation of foreign matter, and a coating film or pattern with excellent light resistance can be formed.

The tetraazaporphyrin dye is a compound having a tetraazaporphyrin skeleton in the molecule. Further, when the tetraazaporphyrin dye is an acid dye or a basic dye, it may form a salt with any cation or anion.
Specific examples of the tetraazaporphyrin dye include a compound represented by the formula (2-1) to a compound represented by the formula (2-38).

As the tetraazaporphyrin dye, a compound represented by the formula (2-29) is preferable.
A composition containing this tetraazaporphyrin dye can form a high-contrast coating film or pattern, and generates less foreign matter.

  The content of the dye (A1) is preferably 0.5 to 100% by mass, more preferably 0.5 to 80% by mass, and still more preferably 40 to 100% by mass with respect to the total amount of the colorant (A). 80% by mass.

  The content of the dye (A2) is preferably 0 to 99.5% by mass and more preferably 0.5 to 20% by mass with respect to the total amount of the colorant (A).

  In addition to the dyes (A1) and (A2), the colorant (A) further contains other dyes, pigments (P), or a mixture thereof for toning, that is, to adjust spectral characteristics. You may go out.

  Examples of the dye include oil-soluble dyes, acid dyes, basic dyes, direct dyes, mordant dyes, amine salts of acid dyes, sulfonamide derivatives of acid dyes, and the like, for example, Color Index (The Society of Dyers and Compounds classified as dyes by Colourists) and known dyes described in dyeing notes (color dyeing company). According to chemical structure, azo dye, cyanine dye, triphenylmethane dye, xanthene dye, phthalocyanine dye, naphthoquinone dye, quinoneimine dye, methine dye, azomethine dye, squarylium dye, acridine dye, styryl dye, coumarin dye, quinoline And dyes and nitro dyes. Of these, organic solvent-soluble dyes are preferably used.

Specifically, C.I. I. Solvent Yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 162;
C. I. Solvent Red 45, 49, 125, 130, 218;
C. I. Solvent Orange 2, 7, 11, 15, 26, 56;
C. I. Solvent Blue 4, 5, 37, 67, 70, 90;
C. I. Solvent Green 1, 4, 5, 7, 34, 35, etc. I. Solvent dyes,
C. I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;
C. I. Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44, 50, 51, 52, 57, 66, 73, 87, 88, 91, 92, 94, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 158, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227,228,249,252,257,258,260,261,266,268,270,274,277,280,281,289,308,312,315,316,339,341,345,346,349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426;
C. I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;
C. I. Acid Violet 6B, 7, 9, 17, 19, 30, 102;
C. I. Acid Blue 1, 7, 9, 15, 18, 22, 29, 42, 59, 60, 62, 70, 72, 74, 82, 83, 86, 87, 90, 92, 93, 100, 102, 103, 104, 113, 117, 120, 126, 130, 131, 142, 147, 151, 154, 158, 161, 166, 167, 168, 170, 171, 184, 187, 192, 199, 210, 229, 234, 236, 242, 243, 256, 259, 267, 285, 296, 315, 335;
C. I. Acid Green 1, 3, 5, 9, 16, 50, 58, 63, 65, 80, 104, 105, 106, 109, etc. I. Acid dyes,

C. I. Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141;
C. I. Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250;
C. I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C. I. Direct violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;
C. I. Direct Blue 1, 2, 6, 8, 15, 22, 25, 41, 57, 71, 76, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 2 5,246,247,248,249,250,251,252,256,257,259,260,268,274,275,293;
C. I. Direct green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82, etc. I. Direct dyes,
C. I. C. such as Disperse Yellow 54, 76 I. Disperse dyes,
C. I. Basic Red 1, 10;
C. I. Basic Blue 1, 3, 5, 7, 9, 19, 24, 25, 26, 28, 29, 40, 41, 54, 58, 59, 64, 65, 66, 67, 68;
C. I. C. such as Basic Green 1; I. Basic dyes,
C. I. Reactive Yellow 2, 76, 116;
C. I. Reactive Orange 16;
C. I. Reactive Red 36; I. Reactive dyes,
C. I. Modern yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
C. I. Modern Red 1, 2, 4, 9, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 30, 32, 33, 36, 37, 38, 39, 41, 43 45, 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90, 94, 95;
C. I. Modern orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;
C. I. Modern violet 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53, 58;
C. I. Modern Blue 1, 2, 3, 7, 9, 12, 13, 15, 16, 19, 20, 21, 22, 26, 30, 31, 39, 40, 41, 43, 44, 49, 53, 61 74, 77, 83, 84;
C. I. Modern Green 1, 3, 4, 5, 10, 15, 26, 29, 33, 34, 35, 41, 43, 53, etc. I. Modern dyes,
C. I. C. of Bat Green 1 etc. I. Vat dye,
Etc.
Of these, blue dyes, violet dyes and red dyes are preferred.
These dyes may be used alone or in combination of two or more.

The pigment (P) is not particularly limited, and a known pigment can be used. Examples thereof include pigments classified as pigments according to a color index (published by The Society of Dyers and Colorists).
Examples of the pigment include 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, 194, 214;
C. I. Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;
C. I. Red pigments such as CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265;
C. I. Blue pigments such as CI Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60;
C. I. Violet color pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38;
C. I. Green pigments such as CI Pigment Green 7, 36, 58;
C. I. Brown pigments such as CI Pigment Brown 23 and 25;
C. I. And black pigments such as CI Pigment Black 1 and 7.

  The pigment (P) is preferably a phthalocyanine pigment or a dioxazine pigment, more preferably C.I. I. At least one selected from the group consisting of CI Pigment Blue 15: 6 and CI Pigment Violet 23. By including the pigment, it is easy to optimize the transmission spectrum, and the heat resistance, light resistance and chemical resistance of the color filter are improved.

  The content of the colorant (A) is preferably 5% by mass or more and 70% by mass or less, more preferably 5% by mass or more and 60% by mass or less, and further preferably 5% by mass with respect to the total amount of the solid content. % To 50% by mass. When the content of the colorant (A) is within the above range, a desired spectrum and color density can be obtained.

  In this specification, the “total amount of solids” refers to the total amount of components obtained by removing the solvent (E) from the colored curable resin composition. The total amount of solids and the content of each component relative thereto can be measured by known analytical means such as liquid chromatography or gas chromatography, for example.

<Resin (B)>
Although it does not specifically limit as resin (B), It is preferable that it is alkali-soluble resin (B). The alkali-soluble resin (B) (hereinafter sometimes referred to as “resin (B)”) is derived from at least one monomer (a) selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride. A copolymer containing structural units.
Examples of such a resin (B) include the following resins [K1] to [K6].
Resin [K1] at least one monomer (a) selected from the group consisting of unsaturated carboxylic acid and unsaturated carboxylic acid anhydride (hereinafter sometimes referred to as “(a)”), and having 2 to 4 carbon atoms A copolymer of a monomer (b) having a cyclic ether structure and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b)”);
Resin [K2] (a) and (b), monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter referred to as “(c)”) In some cases)
Resin [K3] Copolymer of (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) with a copolymer of (b) and (c) 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 and 1,4-cyclohexene dicarboxylic acid;
Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene, 5-carboxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-carboxy-6-methylbicyclo Bicyclounsaturated compounds containing a carboxy group such as [2.2.1] hept-2-ene, 5-carboxy-6-ethylbicyclo [2.2.1] hept-2-ene;
Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6- Unsaturated dicarboxylic acid anhydrides such as tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride;
Unsaturated mono [(meth) acryloyloxyalkyl] esters of polyvalent carboxylic acids such as succinic acid mono [2- (meth) acryloyloxyethyl] and phthalic acid mono [2- (meth) acryloyloxyethyl] Kind;
Examples thereof include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α- (hydroxymethyl) acrylic acid.
Of these, acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerization reactivity and the solubility of the resulting resin in an alkaline aqueous solution.

(B) is, for example, a polymerizable compound having a C2-C4 cyclic ether structure (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond. Say.
(B) is preferably a monomer having a C2-C4 cyclic ether and a (meth) acryloyloxy group.

  Examples of (b) include a monomer having an oxiranyl group and an ethylenically unsaturated bond, a monomer having an oxetanyl group and an ethylenically unsaturated bond, and a tetrahydrofuryl group and an ethylenically unsaturated bond. And monomers.

  (B) is preferably a monomer having an oxiranyl group and an ethylenically unsaturated bond in that the reliability of the obtained color filter such as heat resistance and chemical resistance can be further increased. .

Examples of (c) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, and 2-ethylhexyl (meth). Acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decan-8-yl (meth) acrylate (in this technical field, it is called “dicyclopentanyl (meth) acrylate” as a common name. In the case of “tricyclodecyl (meth) acrylate”) There is a bird) Black (in the art, it is said that "dicyclopentenyl (meth) acrylate" as trivial name.) [5.2.1.0 ^2,6] decene-8-yl (meth) acrylate, dicyclopenta Nyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, benzyl (meth) acrylate, etc. (Meth) acrylic acid esters of
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, diethyl itaconate;
Bicyclo [2.2.1] hept-2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-ethylbicyclo [2.2.1] hept-2-ene, 5- Hydroxybicyclo [2.2.1] hept-2-ene, 5-hydroxymethylbicyclo [2.2.1] hept-2-ene, 5- (2′-hydroxyethyl) bicyclo [2.2.1] Hept-2-ene, 5-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 (cyclohexyloxycarbonyl) bicyclo [2.2.1] hept-2-ene, etc. Bicyclounsaturated compounds;
N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3 -Dicarbonylimide derivatives such as maleimide propionate, N- (9-acridinyl) maleimide;
Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyl toluene, 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.
Among these, styrene, vinyltoluene, benzyl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decan-8-yl (meth) acrylate, N from the viewpoint of copolymerization reactivity and heat resistance. -Phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1] hept-2-ene are preferred.
In the present 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.

Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer, 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 / (Meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] decyl (meth) acrylate / (meth) acrylic acid / N-cyclohexylmaleimide copolymer, 3 , 4-epoxytricyclo [5.2.1.0 ^2.6] decyl (meth) acrylate / (meth) acrylic acid / vinyl toluene copolymer, 3- menu Resin such as ru-3- (meth) acryloyloxymethyloxetane / (meth) acrylic acid / styrene copolymer [K2]; benzyl (meth) acrylate / (meth) acrylic acid copolymer, styrene / (meth) Acrylic acid copolymer, resin such as benzyl (meth) acrylate / tricyclodecyl (meth) acrylate / (meth) acrylic acid copolymer [K3]; benzyl (meth) acrylate / (meth) acrylic acid copolymer Resin with glycidyl (meth) acrylate added to tricyclodecyl (meth) acrylate / styrene / (meth) acrylic acid copolymer, resin with glycidyl (meth) acrylate added, tricyclodecyl (meth) acrylate / Benzyl (meth) acrylate / (meth) acrylic acid copolymer with glycidyl (meth) acrylate Resin [K4] such as a resin to which a relate is added; a resin obtained by reacting a copolymer of tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate with (meth) acrylic acid, tricyclodecyl (meth) acrylate / Resin such as a resin obtained by reacting a copolymer of styrene / glycidyl (meth) acrylate with (meth) acrylic acid [K5]; a copolymer of tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate (meth) Examples thereof include a resin [K6] such as a resin obtained by reacting acrylic acid with a resin further reacted with tetrahydrophthalic anhydride.

  For example, the resin [K1] can be obtained by, for example, a method described in the document “Experimental Method for Polymer Synthesis” (Takayuki Otsu, published by Kagaku Dojin Co., Ltd., First Edition, First Edition, issued March 1, 1972) and It can manufacture with reference to the cited reference described in the said literature.

The resin (B) is preferably a kind selected from the group consisting of a resin [K1], a resin [K2] and a resin [K3], and more preferably from a group consisting of a resin [K2] and a resin [K3]. It is the kind chosen. When these resins are used, the colored curable resin composition is excellent in developability.
Resin [K2] is more preferable from the viewpoint of adhesion between the coloring pattern and the substrate.

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

  The acid value of the resin (B) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, and still more preferably 70 to 135 mg-KOH / g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide necessary to neutralize 1 g of the resin (B), and can be determined by titration with an aqueous potassium hydroxide solution, for example.

  Content of resin (B) becomes like this. Preferably it is 7-65 mass% with respect to the total amount of solid content, More preferably, it is 13-60 mass%, More preferably, it is 17-55 mass%. When the content of the resin (B) is in the above range, a colored pattern can be formed, and the resolution and remaining film ratio of the colored 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 a compound having a polymerizable ethylenically unsaturated bond. Is a (meth) acrylic acid ester compound.

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

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

  Especially, it is preferable that a polymeric compound (C) is a polymeric compound which has 3 or more of ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa ( (Meth) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritol nona (meth) acrylate, tris (2- (meth) acryloyloxyethyl) ) Isocyanurate, ethylene glycol modified pentaerythritol tetra (meth) acrylate, ethylene glycol modified dipentaerythritol Hexa (meth) acrylate, propylene glycol modified pentaerythritol tetra (meth) acrylate, propylene glycol modified dipentaerythritol hexa (meth) acrylate, caprolactone modified pentaerythritol tetra (meth) acrylate, caprolactone modified dipentaerythritol hexa (meth) acrylate, etc. Among them, dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate are preferable.

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

The content of the polymerizable compound (C) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and further preferably 17 to 55% by mass with respect to the total amount of the solid content. is there.
Further, the content ratio of the resin (B) and the polymerizable compound (C) [resin (B): polymerizable compound (C)] is based on mass, preferably 20:80 to 80:20, more preferably. Is 35: 65-80: 20.
When the content of the polymerizable compound (C) is within the above range, the remaining film ratio at the time of forming the colored pattern and the chemical resistance of the color filter tend to be improved.

<Polymerization initiator (D)>
The polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating an active radical, an acid or the like by the action of light or heat and initiating polymerization, and a known polymerization initiator can be used.
Examples of the polymerization initiator (D) include O-acyloxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds.

  Examples of the O-acyloxime compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane. -1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1- [9-ethyl-6- (2-Methylbenzoyl) -9H-carbazol-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- {2-methyl-4- (3,3-dimethyl-2, 4-Dioxacyclopentanylmethyloxy) benzoyl} -9H-carbazol-3-yl] ethane-1-imine, N-acetoxy-1- 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] -3-cyclopentylpropane-1-imine, N-benzoyloxy-1- [9-ethyl-6- (2-methylbenzoyl) ) -9H-carbazol-3-yl] -3-cyclopentylpropan-1-one-2-imine and the like. Commercial products such as Irgacure (registered trademark) OXE01, OXE02 (above, manufactured by BASF), N-1919 (manufactured by ADEKA) may be used. Among these, O-acyloxime compounds include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1 At least one selected from the group consisting of -on-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan-1-one-2-imine is preferred, and N-benzoyloxy -1- (4-Phenylsulfanylphenyl) octane-1-one-2-imine is more preferred. When these O-acyloxime compounds are used, a color filter with high brightness tends to be obtained.

  Examples of the alkylphenone compound include 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] butan-1-one, Irgacure (registered trademark) 369,907 379 (above, manufactured by BASF), 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propane- 1-one, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) pro Down-1-one oligomer, alpha, alpha-diethoxyacetophenone, and benzyl dimethyl ketal.

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

  Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4- Methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxy Styryl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4 -Bis (trichloromethyl) -6- [2- (furan-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino- 2-methylpheny ) Ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine.

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

  Furthermore, as the polymerization initiator (D), benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl- Benzophenone compounds such as 4′-methyldiphenyl sulfide, 3,3 ′, 4,4′-tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone; 9,10-phenanthrenequinone, Examples include quinone compounds such as 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds.

  The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds and biimidazole compounds, 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, more preferably 1 to 30 parts per 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). Part by mass.

<Solvent (E)>
A solvent (E) is not specifically limited, The solvent normally used in the said field | area can be used. For example, an ester solvent (a solvent containing —COO— in the molecule and not containing —O—), an ether solvent (a 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 (containing OH in the molecule, -O-,- A solvent not containing CO- and -COO-), an aromatic hydrocarbon solvent, an amide solvent, dimethyl sulfoxide and the like.

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

  Ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether , Propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethyl Glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, methyl anisole, and the like.

  Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 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 ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, dipropylene glycol methyl ether acetate and the like.

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

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

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

The content of the solvent (E) is preferably 70 to 95% by mass and more preferably 75 to 92% by mass with respect to 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 when the color filter is formed, the color density does not become insufficient and the display characteristics tend to be good.

［式（１０）中、Ｒ^8１〜Ｒ^8４は、それぞれ独立に、水素原子、炭素数１〜４のアルキル基又はヒドロキシ基を表す。］ <Colorless metal complex (F)>
The colored curable resin composition of the present invention may contain a colorless metal complex (F).
Examples of the colorless metal complex (F) include a zinc complex represented by the formula (10).

[In Formula (10), R < ⁸¹ > -R < ⁸⁴ > represents a hydrogen atom, a C1-C4 alkyl group, or a hydroxyl group each independently. ]

Examples of the alkyl group having 1 to 4 carbon atoms in R ^{81 to} R ⁸⁴ in the formula (10) include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert group. -A butyl group is mentioned. Specific examples of the zinc complex represented by the formula (10) include those shown in Table 1. Among these, the zinc complex represented by the formula (10) -18 is preferable from the viewpoint of heat resistance.

  The content of the colorless metal complex is preferably 0.1% by mass or more and 30% by mass or less, and more preferably 0.5% by mass or more and 15% by mass or less with respect to the colorant (A).

<Other ingredients>
The colored curable resin composition of the present invention comprises, if necessary, a polymerization initiation aid, a leveling agent (H), an antioxidant, a filler, other polymer compounds, an adhesion promoter, a light stabilizer, a chain transfer. An additive known in the art, such as an agent, may be included.
Examples of the leveling agent (H) include silicone surfactants, fluorine surfactants, and silicone surfactants having a fluorine atom. These may have a polymerizable group in the side chain.
The antioxidant is not particularly limited as long as it is an antioxidant generally used industrially, and a phenol-based antioxidant, a phosphorus-based antioxidant, a sulfur-based antioxidant, and the like can be used.

<Method for producing colored curable resin composition>
The colored curable resin composition of the present invention can be prepared by mixing the dye (A1), the resin (B), the polymerizable compound (C) and the polymerization initiator (D) as the colorant (A). If necessary, the dye (A2), the colorless metal complex (F), the solvent (E), the leveling agent (H), the antioxidant (J) and other components may be mixed.
The pigment in the case of containing the pigment (P) 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 diameter of the pigment is about 0.2 μm or less. . Under the present circumstances, you may mix | blend a part or all of the said pigment dispersant and resin (B) as needed. The desired colored curable resin composition can be prepared by mixing the remaining components in the pigment dispersion thus obtained so as to have a predetermined concentration.
It is preferable to prepare a solution by dissolving the dye of the colorant (A) in part or all of the solvent (E) in advance. The solution is preferably filtered with a filter having a pore size of about 0.01 to 1 μm.
The colored curable resin composition after mixing is preferably filtered with a filter having a pore size of about 0.01 to 10 μm.

<Color filter manufacturing method>
Examples of the method for producing a colored pattern from the colored curable resin composition of the present invention include a photolithographic method, an inkjet method, and a printing method. Of these, the photolithographic method is preferable. The photolithographic method is a method in which the colored curable resin composition is applied to a substrate, dried to form a colored composition layer, and the colored composition layer is exposed through a photomask and developed. In the photolithography method, a colored coating film that is a cured product of the colored composition layer can be formed by not using a photomask and / or not developing during exposure. The colored pattern and the colored coating film thus formed are the color filter of the present invention.
The film thickness of the color filter to be produced is not particularly limited, and can be adjusted as appropriate according to the purpose and application. ~ 6 μm.

  As the substrate, quartz glass, borosilicate glass, alumina silicate glass, glass plate such as soda lime glass coated with silica on the surface, resin plate such as polycarbonate, polymethyl methacrylate, polyethylene terephthalate, silicon, on the substrate In addition, aluminum, silver, or a silver / copper / palladium alloy thin film is used. On these substrates, another color filter layer, a resin layer, a transistor, a circuit, and the like may be formed.

Formation of each color pixel by the photolithographic method can be performed by a known or commonly used apparatus and conditions. For example, it can be produced as follows.
First, a colored curable resin composition is applied on a substrate, dried by heating (pre-baking) and / or drying under reduced pressure to remove volatile components such as a solvent, and a smooth colored composition layer is obtained.
Examples of the coating method include spin coating, slit coating, and slit and spin coating.
30-120 degreeC is preferable and the temperature in the case of performing heat drying has more preferable 50-110 degreeC. In addition, the heating time is preferably 10 seconds to 60 minutes, and more preferably 30 seconds to 30 minutes.
When performing vacuum drying, it is preferable to carry out in the temperature range of 20-25 degreeC under the pressure of 50-150 Pa.
The film thickness of the coloring composition layer is not particularly limited, and may be appropriately selected according to the film thickness of the target color filter.

Next, the coloring composition layer is exposed through a photomask for forming a target coloring pattern. The pattern on the photomask is not particularly limited, and a pattern according to the intended use is used.
The light source used for exposure is preferably a light source that generates light having a wavelength of 250 to 450 nm. For example, light less than 350 nm can be cut using a filter that cuts this wavelength range, or light near 436 nm, 408 nm, and 365 nm can be selectively extracted using a bandpass filter that extracts these wavelength ranges. Or you may. Specifically, examples of the light source include a mercury lamp, a light emitting diode, a metal halide lamp, and a halogen lamp.
Use an exposure device such as a mask aligner or a stepper because the entire exposure surface can be illuminated with parallel rays uniformly, or the photomask can be accurately aligned with the substrate on which the colored composition layer is formed. Is preferred.

A colored pattern is formed on the substrate by developing the exposed colored composition layer in contact with a developer. By the development, the unexposed portion of the colored composition layer is dissolved in the developer and removed.
As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, tetramethylammonium hydroxide is preferable. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. Further, the developer may contain a surfactant.
The developing method may be any of paddle method, dipping method, 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.

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

  By using the colored curable resin composition of the present invention, a color filter having particularly high brightness can be produced. The color filter is useful as a color filter used in display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state image sensors.

EXAMPLES Hereinafter, although an Example demonstrates this invention in detail, this invention is not limited by these Examples. In the examples, “%” and “part” representing the content or amount used are based on mass unless otherwise specified.
In the following, the structure of the compound was confirmed by mass spectrometry (LC; Agilent 1200 type, MASS; Agilent LC / MSD type).

Synthesis example 1
The following reaction was performed in a nitrogen atmosphere. A flask equipped with a condenser and a stirrer was charged with 32.2 parts of potassium thiocyanate and 160.0 parts of acetone, and then stirred at room temperature for 30 minutes. Subsequently, 50.0 parts of 2-fluorobenzoic acid chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise over 10 minutes. After completion of the dropwise addition, the mixture was further stirred at room temperature for 2 hours. Next, the reaction mixture was ice-cooled, and 40.5 parts of N-ethyl-o-toluidine (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise. After completion of dropping, the mixture was further stirred at room temperature for 30 minutes. Next, after cooling the reaction mixture with ice, 34.2 parts of a 30% aqueous sodium hydroxide solution was added dropwise. After completion of dropping, the mixture was further stirred at room temperature for 30 minutes. Then, 31.3 parts of chloroacetic acid was added dropwise at room temperature. After completion of the dropwise addition, the mixture was stirred for 7 hours under heating and reflux. Next, after allowing the reaction mixture to cool to room temperature, the reaction solution was poured into 120.0 parts of tap water, 200 parts of toluene was added, and the mixture was stirred for 30 minutes. Next, the stirring was stopped and the mixture was allowed to stand for 30 minutes. After the aqueous layer was discarded by a liquid separation operation, the organic layer was washed with 200 parts of 1N hydrochloric acid, then with 200 parts of tap water, and finally with 200 parts of saturated saline. An appropriate amount of bowsho was added to the organic layer and stirred for 30 minutes, followed by filtration to obtain a dried organic layer. The obtained organic layer was evaporated using an evaporator to obtain a pale yellow liquid. The resulting pale yellow liquid was purified by column chromatography. The purified pale yellow liquid was dried at 60 ° C. under reduced pressure to obtain 49.9 parts of a compound represented by the formula (BI-1). Yield 51%

Synthesis example 2
The following reaction was performed in a nitrogen atmosphere. 9. 9.9 parts of a compound represented by the formula (BI-1), 4,4′-bis (diethylamino) benzophenone (manufactured by Tokyo Chemical Industry Co., Ltd.) After adding 0 parts and 20.0 parts of toluene, 14.8 parts of phosphorus oxychloride was added and stirred at 95-100 ° C. for 3 hours. The reaction mixture was then cooled to room temperature and diluted with 170.0 parts isopropanol. Next, the diluted reaction solution was poured into 300.0 parts of saturated brine, and then 100 parts of toluene was added and stirred for 30 minutes. Next, the stirring was stopped and the mixture was allowed to stand for 30 minutes. After the aqueous layer was discarded by a liquid separation operation, the organic layer was washed with 300 parts of saturated brine. An appropriate amount of bowsho was added to the organic layer and stirred for 30 minutes, followed by filtration to obtain a dried organic layer. The obtained organic layer was evaporated using an evaporator to obtain a blue-violet solid. The resulting blue-violet solid was purified by column chromatography. The purified blue-violet solid was dried at 60 ° C. under reduced pressure to obtain 17.2 parts of a compound represented by the formula (A-II-1). Yield 85%

Identification of compound represented by formula (A-II-1) (mass spectrometry) ionization mode = ESI +: m / z = 619.3 [M-Cl] ⁺
Exact Mass: 654.3

液（ｄ−２）中に、液（ｄ−１）を２０−３０℃で、１時間かけて加え、その後２４時間撹拌した。生じた沈殿物をろ過し、水１０００部で洗浄した後、２４時間、６０度で減圧乾燥させ、式（Ｉ−１）で表される化合物を１．３部得た。 Synthesis example 3
A liquid (d-1) was prepared by dissolving 0.65 part of the compound represented by the formula (A-II-1) in 100 parts of water. On the other hand, a liquid (d-2) was prepared by dissolving 1.0 part of the compound represented by the following formula (A-II-3) in 50 parts of water.

The liquid (d-1) was added to the liquid (d-2) at 20-30 ° C over 1 hour, and then stirred for 24 hours. The resulting precipitate was filtered and washed with 1000 parts of water, and then dried under reduced pressure at 60 degrees for 24 hours to obtain 1.3 parts of a compound represented by the formula (I-1).

(Preparation of colored curable resin composition)
Example 1
Colorant (A): 20 parts of a compound represented by formula (I-1);
Colorant (A): 6 parts of a dye represented by formula (3-11);
Alkali-soluble resin (B): 53 parts of resin (B-2) (solid content conversion);
Polymerizable compound (C): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 16 parts;
Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF; O-acyloxime compound) 4.1 parts;
Solvent (E): 120 parts of propylene glycol monomethyl ether acetate;
Solvent (E): 380 parts of 4-hydroxy-4-methyl-2-pentanone;
Leveling agent (H): polyether-modified silicone oil (Tore Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.12 parts;
Antioxidant (J): 6-tert-butyl-4- [3-[(2,4,8,10-tetra-tert-butyldibenzo [d, f] [1,3,2] dioxaphosphine Pin-6-yl) oxy] propyl] -2-methylphenol (Sumilyzer (registered trademark) GP; manufactured by Sumitomo Chemical Co., Ltd.) 0.2 part and zinc complex (F): (10) -18 6.1 part Were mixed to obtain a colored curable resin composition.
Example 2
Colorant (A): 18 parts of a compound represented by formula (I-1);
Alkali-soluble resin (B): 50 parts of resin (B-2) (in terms of solid content);
Polymerizable compound (C): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 16 parts;
Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF; O-acyloxime compound) 4.1 parts;
Solvent (E): 150 parts of propylene glycol monomethyl ether acetate;
Solvent (E): 400 parts of 4-hydroxy-4-methyl-2-pentanone;
Leveling agent (H): polyether-modified silicone oil (Tore Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.12 parts;
Antioxidant (J): 6-tert-butyl-4- [3-[(2,4,8,10-tetra-tert-butyldibenzo [d, f] [1,3,2] dioxaphosphine Pin-6-yl) oxy] propyl] -2-methylphenol (Sumilyzer (registered trademark) GP; manufactured by Sumitomo Chemical Co., Ltd.) 0.3 part was mixed to obtain a colored curable resin composition.
Example 3
Colorant (A): 20 parts of a compound represented by formula (I-1);
Colorant (A): 6 parts of a dye represented by formula (3-11);
Alkali-soluble resin (B): 53 parts of resin (B-2) (solid content conversion);
Polymerizable compound (C): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 16 parts;
Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF; O-acyloxime compound) 4.1 parts;
Solvent (E): 220 parts of propylene glycol monomethyl ether acetate;
Solvent (E): 480 parts of 4-hydroxy-4-methyl-2-pentanone;
Leveling agent (H): polyether-modified silicone oil (Tore Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.1 part;
Antioxidant (J): 6-tert-butyl-4- [3-[(2,4,8,10-tetra-tert-butyldibenzo [d, f] [1,3,2] dioxaphosphine Pin-6-yl) oxy] propyl] -2-methylphenol (Sumilyzer (registered trademark) GP; manufactured by Sumitomo Chemical Co., Ltd.) 0.4 part was mixed to obtain a colored curable resin composition.

Comparative Example 1
Colorant (A): 26 parts of a compound represented by formula (A-III-1);
Alkali-soluble resin (B): 53 parts of resin (B-1) (in terms of solid content);
Polymerizable compound (C): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 16 parts;
Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF; O-acyloxime compound) 4 parts;
Solvent (E): 120 parts of propylene glycol monomethyl ether acetate;
Solvent (E): 480 parts of 4-hydroxy-4-methyl-2-pentanone;
In addition, 0.15 part of leveling agent (H): polyether-modified silicone oil (Tore Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) was mixed to obtain a colored curable resin composition.

[Production of color filters]
The colored curable resin composition was applied on a 2-inch square glass substrate (# 1737; manufactured by Corning) by spin coating, and then pre-baked at 100 ° C. for 3 minutes to form a colored composition layer. After cooling, using an exposure machine (TME-150RSK; manufactured by Topcon Corporation), exposure was performed at an exposure amount of 150 mJ / cm ² (based on 365 nm) in an air atmosphere. A photomask was not used. The colored composition layer after exposure was post-baked in an oven at 180 ° C. for 20 minutes to produce a color filter (film thickness: 2.8 μm).

[Heat resistance evaluation]
The coating film of the colored curable resin composition was heated at 230 ° C. for 20 minutes, and the color difference (ΔEab *) before and after the heating of the coating film was measured using a colorimeter (OSP-SP-200; manufactured by OLYMPUS). The coating films obtained in Examples 1, 2, and 3 were subjected to the above heat resistance evaluation. As a result, the color difference (ΔEab *) was 4.2, 5.6, and 5.4, respectively. Moreover, as a result of carrying out heat resistance evaluation similarly about the comparative example 1, color difference ((DELTA) Eab *) was 8.1 and it turned out that this-application compound is excellent in heat resistance.

  When the colored curable resin composition containing the compound of the present invention is used, a color filter having excellent heat resistance can be provided. The color filter is useful as a color filter used in display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state image sensors.

Claims (7)

A compound represented by formula (I).

[In the formula (I), R ^{1A to} R ^8A each independently represents a hydrogen atom, a halogen atom, a hydroxy group or an alkyl group having 1 to 20 carbon atoms (an oxygen atom is present between carbon atoms constituting the alkyl group). May be inserted).
R ^{9A to} R ^12A are each independently a hydrogen atom, an amino group, or an alkyl group having 1 to 20 carbon atoms which may be substituted with a halogen atom (an oxygen atom is present between carbon atoms constituting the alkyl group). Which may be inserted) or an aryl group which may have a substituent. R ^9A and R ^10A may be bonded to form a ring with the nitrogen atom to which they are bonded, or R ^11A and R ^12A may be bonded to form a ring with the nitrogen atom to which they are bonded.
A represents a heteroaromatic group which may have a substituent.
Two of R ^{1 to} R ⁴ are each independently a group represented by the formula (i), and the other two are independently an alkyl group having 1 to 20 carbon atoms (the alkyl group is An oxygen atom may be inserted between the constituent carbon atoms).

(In formula (i), n represents an integer of 1 to 8, and * represents a bond to a nitrogen atom.)
R ^{5 to} R ¹⁶ are each independently a hydrogen atom, a halogen atom, a hydroxy group or an alkyl group having 1 to 20 carbon atoms (an oxygen atom may be inserted between carbon atoms constituting the alkyl group). Represents.
R ¹⁷ is a group represented by formula (ii).

(In formula (ii), R ¹⁸ represents an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and * represents a bond with a carbon atom.)]   A color curable composition comprising a colorant (A) comprising the compound represented by formula (I) according to claim 1, a resin (B), a polymerizable compound (C), and a polymerization initiator (D). Resin composition.   The colored curable resin composition according to claim 2, wherein the colorant (A) further comprises at least one dye (A2) selected from the group consisting of an anthraquinone dye and a tetraazaporphyrin dye.   The colored curable resin composition according to claim 2 or 3, further comprising a colorless metal complex (F).   The coating film formed from the colored curable resin composition in any one of Claims 2-4.   A color filter formed from the colored curable resin composition according to claim 2.   A display device comprising the color filter according to claim 6.