JP2013235257A - Coloring agent dispersion liquid - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a coloring agent dispersion liquid suitable for obtaining a colored curable composition enabling production of a color filter with high brightness.SOLUTION: In a coloring agent dispersion liquid, a coloring agent is dispersed in a solvent with a dispersant. The coloring agent contains a xanthene dye and substantially does not contain pigment. The content of the xanthene dye is 40 mass% or more and 100 mass% or less with respect to the total mass of the coloring agent. The dispersant has an amine group and an amine value of the dispersant is 0-55 mgKOH/g.

Description

  The present invention relates to a colorant dispersion and the like.

  Colored curable compositions are used in the production of color filters used in display devices such as liquid crystal display devices, electroluminescence display devices, and plasma displays. As such a colored curable composition, a colored curable composition produced by dispersing a pigment in a solvent and further mixing a xanthene dye is used (Patent Document 1 (Example 1). )).

JP 2010-32999 A

  The brightness of the color filter obtained from the colored curable composition is not always satisfactory.

The present invention includes the following inventions.
[1] A colorant dispersion in which a colorant is dispersed in a solvent by a dispersant,
The colorant comprises a xanthene dye and is substantially free of pigment;
The xanthene dye content is 40% by mass or more and 100% by mass or less based on the total amount of the colorant,
A colorant dispersion in which the dispersant has an amine group and the dispersant has an amine value of 0 to 55 mgKOH / g.
[2] The colorant dispersion according to [1], wherein the amine value of the dispersant is 2 to 40 mg KOH / g.
[3] The solvent contains propylene glycol monomethyl ether acetate, and the content of propylene glycol monomethyl ether acetate is 40% by mass or more and 99% by mass or less based on the total amount of the solvent [1] or [2] The colorant dispersion described.
[4] The colorant dispersion according to any one of [1] to [3], further including a resin.
[5] A colored curable composition comprising the colorant dispersion according to any one of [1] to [4], a polymerizable compound, and a polymerization initiator.
[6] Further comprising a pigment composition prepared separately from the colorant dispersion,
The colored curable composition according to [5], wherein the pigment composition comprises a pigment, a solvent, and at least one selected from the group consisting of a pigment dispersant and a resin.
[7] A color filter formed from the colored curable composition according to [5] or [6].
[8] A display device including the color filter according to [7].

  A color filter with high brightness can be obtained from the colored curable composition prepared from the colorant dispersion of the present invention.

1. Colorant dispersion The colorant dispersion of the present invention comprises a colorant (A) dispersed in a solvent (B) by a dispersant (D), and the colorant (A) contains a xanthene dye (A1). The pigment is substantially free of pigment, and the colorant (A) has a xanthene dye (A1) content of 40% by mass or more and 100% by mass or less based on the total amount of the colorant. Further, the dispersant (D) has an amine group and an amine value of 0 to 55 mgKOH / g. The colorant (A) contains a dispersant (D) having a predetermined amine value and a xanthene dye (A1), is substantially free of a pigment, and the content of the xanthene dye is based on the total amount of the colorant, When a colored curable composition is prepared using a colorant dispersion liquid of 40% by mass or more and 100% by mass or less, a colored curable composition capable of producing a high brightness color filter is obtained. Furthermore, the contrast is also increased.
Hereinafter, each component will be described in detail. In addition, in this specification, unless otherwise indicated, the compound illustrated as each component can be used individually or in combination of multiple types.

1-1. Colorant (A)
The colorant (A) contains a xanthene dye (A1) and substantially does not contain a pigment. Content of a xanthene dye (A1) is 40 mass% or more with respect to the total amount of a coloring agent (A), Preferably it is 60 mass% or more. The colorant may further contain a dye other than the xanthene dye (A1) (sometimes referred to as “other dye (A3)”).
When the colorant (A) has the above-described configuration, the color filter obtained from the colored curable composition produced from the colorant dispersion of the present invention has high brightness.

1-1-1. Xanthene dye (A1)
The xanthene dye (A1) is a dye containing a compound having a xanthene skeleton in the molecule. Examples of the xanthene dye (A1) include C.I. I. Acid Red 51 (hereinafter, the description of CI Acid Red is omitted and only the number is described. Others are also the same), 52, 87, 92, 94, 289, 388, C.I. I. Acid Violet 9, 30, 102, C.I. I. Basic Red 1 (Rhodamine 6G), 2, 3, 4, 8, C.I. I. Basic Red 10 (Rhodamine B), 11, C.I. I. Basic violet 10, 11, 25, C.I. I. Solvent Red 218, C.I. I. Modern Tread 27, C.I. I. Reactive red 36 (rose bengal B), sulforhodamine G, xanthene dyes described in JP 2010-32999 A, xanthene dyes described in Japanese Patent No. 4492760, and the like.

  Among these, as the xanthene dye (A1), a dye containing a compound represented by the formula (1a) (hereinafter sometimes referred to as “compound (1a)”) is preferable. Compound (1a) may be a tautomer thereof. When using a compound (1a), content of the compound (1a) in a xanthene dye (A1) becomes like this. Preferably it is 50 mass% or more, More preferably, it is 70 mass% or more, More preferably, it is 90 mass% or more. In particular, it is preferable to use only the compound (1a) as the xanthene dye (A1).

[In Formula (1a), R ^{1 to} R ⁴ each independently have a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a substituent. Represents a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and —CH ₂ — contained in the saturated hydrocarbon group is replaced by —O—, —CO— or —NR ¹¹ —. May be. R ¹ and R ² may combine to form a ring with an adjacent nitrogen atom, or R ³ and R ⁴ may combine to form a ring with an adjacent nitrogen atom.
R ^{5 _{is, -OH, -SO 3 -, -SO}} 3 H, -SO 3 - Z +, -CO 2 H, -CO 2 - Z +, -CO 2 R 8, -SO 3 R 8 or -SO ₂ represents NR ⁹ R ¹⁰
R ⁶ and R ⁷ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
m represents an integer of 0 to 5. When m is 2 or more, the plurality of R ⁵ may be the same or different.
a represents an integer of 0 or 1.
X represents a halogen atom.
Z ⁺ represents ⁺ N (R ¹¹ ) ₄ , Na ⁺ or K ⁺ , and four R ¹¹ may be the same or different.
R ⁸ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom.
R ⁹ and R ¹⁰ each independently represent a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and are included in the saturated aliphatic hydrocarbon group. —CH ₂ — may be replaced by —O—, —CO—, —NH— or —NR ⁸ —, and R ⁹ and R ¹⁰ are bonded to form a 3- to 10-membered ring together with the adjacent nitrogen atom. The heterocyclic ring may be formed.
R ¹¹ represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R ^{1 to} R ⁴ include a methyl group, an ethyl group, a propyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group. , Dodecyl group, hexadecyl group, icosyl group and other linear alkyl groups; isopropyl group, isobutyl group, isopentyl group, neopentyl group, 2-ethylhexyl group and other branched chain alkyl groups; cyclopropyl group, cyclopentyl group, cyclohexyl group , An alicyclic saturated hydrocarbon group having 2 to 20 carbon atoms such as a cycloheptyl group, a cyclooctyl group, and a tricyclodecyl group.
The hydrogen atom contained in the saturated hydrocarbon group in R ^{1 to} R ⁴ may be substituted with, for example, an aromatic hydrocarbon group having 6 to 10 carbon atoms or a halogen atom.
Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms in R ^{1 to} R ⁴ include a phenyl group, a toluyl group, a xylyl group, a mesityl group, a propylphenyl group, and a butylphenyl group.

Examples of the substituent that the saturated hydrocarbon group or the aromatic hydrocarbon group may have include a halogen atom, —R ⁸ , —OH, —OR ⁸ , —SO ₃ ⁻ , —SO ₃ H, —SO _{^{3 - Z +, -CO 2 H}} , -CO 2 R 8, -SR 8, -SO 2 R 8, -SO 3 R 8 and -SO ₂ NR ⁹ R ¹⁰ can be mentioned. Among them, as the _{^{substituent, -SO 3 -, -SO 3 H}} , -SO 3 - Z + and preferably _{^{-SO 2 NR 9 R 10, -SO}} 3 - Z + and -SO ₂ NR ⁹ R ¹⁰ Is more preferable. As —SO ₃ ⁻ Z ⁺ , —SO ₃ ^{− +} N (R ¹¹ ) ₄ is preferable. When R ^{1 to} R ⁴ are these groups, the color curable composition prepared from the colorant dispersion of the present invention containing the compound (1a) is less likely to generate foreign matter and has excellent heat resistance. A filter can be formed.

Examples of the ring formed by combining R ¹ and R ² together with the adjacent nitrogen atom, and the ring formed by combining R ³ and R ⁴ together with the adjacent nitrogen atom include the following.

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R ^{8 to} R ¹¹ include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a nonyl group. Linear alkyl groups such as decyl group, dodecyl group, hexadecyl group, icosyl group; branched alkyl groups such as isopropyl group, isobutyl group, isopentyl group, neopentyl group, 2-ethylhexyl group; cyclopropyl group, cyclopentyl group , An alicyclic saturated hydrocarbon group having 3 to 20 carbon atoms such as a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and a tricyclodecyl group.
The monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R ⁹ and R ¹⁰ may have a substituent. Examples of the substituent include a hydroxy group and a halogen atom.

Examples of —OR ⁸ include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, and an icosyloxy group.

Examples of —CO ₂ R ⁸ include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a hexyloxycarbonyl group, and an icosyloxycarbonyl group.

Examples of —SR ⁸ include a methylsulfanyl group, an ethylsulfanyl group, a butylsulfanyl group, a hexylsulfanyl group, a decylsulfanyl group, and an icosylsulfanyl group.
Examples of —SO ₂ R ⁸ include a methylsulfonyl group, an ethylsulfonyl group, a butylsulfonyl group, a hexylsulfonyl group, a decylsulfonyl group, and an icosylsulfonyl group.
Examples of —SO ₃ R ⁸ include a methoxysulfonyl group, an ethoxysulfonyl group, a propoxysulfonyl group, a tert-butoxysulfonyl group, a hexyloxysulfonyl group, and an icosyloxysulfonyl group.

—SO ₂ NR ⁹ R ¹⁰ includes, for example, a sulfamoyl group;
N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N- sec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N- (1-ethylpropyl) sulfamoyl group, N- (1,1-dimethylpropyl) sulfamoyl group, N- (1,2-dimethylpropyl) sulfamoyl group, N- (2,2-dimethylpropyl) sulfamoyl group, N- (1-methylbutyl) sulfamoyl group, N- (2-methylbutyl) sulfamoyl group, N- (3 -Methylbutyl) sulfamoyl group, N-cyclopentylsulfamoyl group, N-hexylsulfamoyl N- (1,3-dimethylbutyl) sulfamoyl group, N- (3,3-dimethylbutyl) sulfamoyl group, N-heptylsulfamoyl group, N- (1-methylhexyl) sulfamoyl group, N- (1 , 4-Dimethylpentyl) sulfamoyl group, N-octylsulfamoyl group, N- (2-ethylhexyl) sulfamoyl group, N- (1,5-dimethyl) hexylsulfamoyl group, N- (1,1,2, , 2-tetramethylbutyl) sulfamoyl group and the like N-1 substituted sulfamoyl group;
N, N-dimethylsulfamoyl group, N, N-ethylmethylsulfamoyl group, N, N-diethylsulfamoyl group, N, N-propylmethylsulfamoyl group, N, N-isopropylmethylsulfa Moyl group, N, N-tert-butylmethylsulfamoyl group, N, N-butylethylsulfamoyl group, N, N-bis (1-methylpropyl) sulfamoyl group, N, N-heptylmethylsulfamoyl And N, N-2-substituted sulfamoyl groups such as a group.

R ^{5 _{is, -CO 2 H, -CO 2 -}} Z +, -CO 2 R 8, -SO 3 -, -SO 3 - Z +, -SO 3 H or SO ₂ NHR ⁹ are preferred, SO ₃ ^{-, _{-SO 3 - Z +, -SO 3}} H or SO ₂ NHR ⁹ is more preferable.
m is preferably 1 to 4, and more preferably 1 or 2.

The alkyl group having 1 to 6 carbon atoms in R ⁶ and R ^7, among the alkyl groups listed above, are those having 1 to 6 carbon atoms.

Examples of the aralkyl group having 7 to 10 carbon atoms in R ¹¹ include a benzyl group, a phenylethyl group, and a phenylbutyl group.

Z ⁺ is ⁺ N (R ¹¹ ) ₄ , Na ⁺ or K ⁺ , preferably ⁺ N (R ¹¹ ) ₄ .
⁺ N (R ¹¹⁾ ₄ of the four R ¹¹ in, it is preferred that at least two of a monovalent saturated hydrocarbon group having 5 to 20 carbon atoms. It is preferable that the total number of carbon atoms of the four R ¹¹ is 20 to 80, and more preferably from 20 to 60. When ⁺ N (R ¹¹ ) ₄ is present in compound (1a), a colored curable composition prepared from the colorant dispersion of the present invention containing compound (1a) when R ¹¹ is any of these groups Therefore, a color filter with few foreign matters can be formed.

  The compound (1a) is preferably a compound represented by the formula (2a) (hereinafter sometimes referred to as “compound (2a)”). Compound (2a) may be a tautomer thereof.

[In the formula (2a), R ^{21 to} R ²⁴ each independently represents a hydrogen atom, —R ²⁶ or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. Represent. R ²¹ and R ²² may combine to form a ring with an adjacent nitrogen atom, or R ²³ and R ²⁴ may combine to form a ring with an adjacent nitrogen atom.
R ²⁵ is, -SO ₃ ^- represents a Z1 ⁺ or _{^{-SO 2 NHR 26 -, -SO 3}} H, -SO 3.
m1 represents the integer of 0-5. When m1 is 2 or more, the plurality of R ²⁵ may be the same or different.
a1 represents an integer of 0 or 1.
X1 represents a halogen atom.
R ²⁶ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
Z1 ⁺ represents ⁺ N (R ²⁷ ) ₄ , Na ⁺ or K ⁺ , and the four R ²⁷ may be the same or different.
R ²⁷ represents a monovalent saturated hydrocarbon group or a benzyl group having 1 to 20 carbon atoms. ]

Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms in R ^{21 to} R ²⁴ include the same groups as those mentioned as the aromatic hydrocarbon group for R ^{1 to} R ⁴ . Hydrogen atoms contained in the aromatic hydrocarbon _{^{group, -SO 3 -, -SO 3 H}} , -SO 3 - Z1 +, may be substituted by -SO ₃ R ²⁶ or -SO ₂ NHR ^26.
As a combination of R ^{21 to} R ²⁴ , R ²¹ and R ²³ are hydrogen atoms, R ²² and R ²⁴ are monovalent aromatic hydrocarbon groups having 6 to 10 carbon atoms, and the aromatic hydrocarbons hydrogen atoms contained in the _{^{groups, -SO 3 -, -SO 3 H}} , -SO 3 - Z1 +, those substituted by -SO ₃ R ²⁶ or -SO ₂ NHR ²⁶ preferred. A more preferred combination is that R ²¹ and R ²³ are hydrogen atoms, R ²² and R ²⁴ are monovalent aromatic hydrocarbon groups having 6 to 10 carbon atoms, and hydrogen contained in the aromatic hydrocarbon group atom, -SO ₃ ^- are those which are substituted with Z1 ⁺ or -SO ₂ NHR ^26. When R ^{21 to} R ²⁴ are these groups, a color filter having excellent heat resistance can be formed from the colored curable composition prepared from the colorant dispersion of the present invention containing the compound (2a).

The ring formed by combining R ²¹ and R ²² together with the adjacent nitrogen atom, and the ring formed by combining R ²³ and R ²⁴ together with the adjacent nitrogen atom include R ¹ and R ² bonded together. And the same ring as that formed with the nitrogen atom. Among these, an aliphatic heterocyclic ring is preferable. Examples of the aliphatic heterocycle include the following.

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R ²⁶ and R ²⁷ include the same groups as those exemplified as the saturated hydrocarbon group in R ^{8 to} R ¹¹ .
When R ²¹ to R ²⁴ is -R ^26, -R ²⁶ each independently is preferably a methyl group or an ethyl group. As the R ²⁶ in -SO ₃ R ²⁶ and -SO ₂ NHR ^26, preferably branched alkyl group having 3 to 20 carbon atoms, more preferably a branched alkyl group having 6 to 12 carbon atoms, A 2-ethylhexyl group is more preferred. When R ²⁶ is these groups, a color filter with less generation of foreign matters can be formed from the colored curable composition of the present invention containing the compound (2a).

Z1 ⁺ is ⁺ N (R ²⁷ ) ₄ , Na ⁺ or K ⁺ , preferably ⁺ N (R ²⁷ ) ₄ .
⁺ N (R ²⁷⁾ ₄ of the four R ²⁷ in, it is preferred that at least two of a monovalent saturated hydrocarbon group having 5 to 20 carbon atoms. It is preferable that the total number of carbon atoms of the four R ²⁷ is 20 to 80, and more preferably from 20 to 60. When ⁺ N (R ²⁷ ) ₄ is present in compound (2a), a colored curable composition prepared from the colorant dispersion of the present invention containing compound (2a) when R ²⁷ is any of these groups Therefore, it is possible to form a color filter with less generation of foreign matter.

  m1 is preferably 1 to 4, and more preferably 1 or 2.

Moreover, as a compound (1a), all of R < ²¹ > -R < ²⁴ > represented by the said Formula (2a) is respectively independently C1-C20, especially a C1-C10 monovalent saturated hydrocarbon group. Or a compound represented by the formula (3a) (hereinafter sometimes referred to as “compound (3a)”) is also preferable. Compound (3a) may be a tautomer thereof.

[In Formula (3a), R ³¹ and R ³² each independently represent a monovalent saturated hydrocarbon group having 1 to 10 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group has 6 carbon atoms. To 10 aromatic hydrocarbon groups or halogen atoms, and the hydrogen atom contained in the aromatic hydrocarbon group may be substituted with an alkoxy group having 1 to 3 carbon atoms, —CH ₂ — contained in the hydrocarbon group may be replaced by —O—, —CO— or —NR ¹¹ —.
R ³³ and R ³⁴ each independently represents an alkyl group, an alkylsulfanyl group, or an alkylsulfonyl group having 1 to 4 carbon atoms having 1 to 4 carbon atoms having 1 to 4 carbon atoms.
R ³¹ and R ³³ may combine to form a ring with the adjacent nitrogen atom and carbon atom on the benzene ring, and R ³² and R ³⁴ combine to form a ring with the adjacent nitrogen atom and carbon atom on the benzene ring. A ring may be formed.
p and q represent the integer of 0-5 each independently. When p is 2 or more, the plurality of R ³³ may be the same or different, and when q is 2 or more, the plurality of R ³⁴ may be the same or different.
R ¹¹ represents the same meaning as described above. ]

Examples of the monovalent saturated hydrocarbon group having 1 to 10 carbon atoms in R ³¹ and R ³² include those having 1 to 10 carbon atoms among those in R ⁸ .
Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms which may be present as a substituent include the same groups as those in R ¹ .
As a C1-C3 alkoxy group, a methoxy group, an ethoxy group, and a propoxy group are mentioned, for example.
R ³¹ and R ³² are preferably each independently a monovalent saturated hydrocarbon group having 1 to 3 carbon atoms.

Examples of the alkyl group having 1 to 4 carbon atoms in R ³³ and R ³⁴ 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.
Examples of the alkylsulfanyl group having 1 to 4 carbon atoms in R ³³ and R ³⁴ include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, a butylsulfanyl group, and an isopropylsulfanyl group.
The alkylsulfonyl group of 1 to 4 carbon atoms in R ³³ and R ^34, methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group and a butylsulfonyl group and isopropylsulfonyl group.
R ³³ and R ³⁴ are each independently preferably an alkyl group having 1 to 4 carbon atoms, and more preferably both are methyl groups.

  p and q are each independently preferably an integer of 0 to 2, and more preferably 0 or 1.

Examples of compound (1a) include compounds represented by formula (1-1) to formula (1-63). In the formula, R ⁴⁰ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, preferably a branched alkyl group having 6 to 12 carbon atoms, more preferably a 2-ethylhexyl group.

Among the compounds, the compounds represented by the formula (1-1) to the formula (1-23) or the formula (1-37) to the formula (1-63) correspond to the compound (2a), and the formula (1- The compound represented by any one of 24) to formula (1-36) corresponds to the compound (3a).
Among these, C.I. I. Acid red 289 sulfonamidation product, C.I. I. Quaternary ammonium salt of Acid Red 289, C.I. I. Acid violet 102 sulfonamidate or C.I. I. The quaternary ammonium salt of Acid Violet 102 is preferred. Examples of such a compound include compounds represented by formula (1-1) to formula (1-8), formula (1-11), or formula (1-12).
A compound represented by any one of the formulas (1-24) to (1-33) is also preferable in that it is excellent in dispersibility in an organic solvent.

  As the xanthene dye (A1), a commercially available xanthene dye (for example, “Chugai Amino Fast Pin RH / C” manufactured by Chugai Kasei Co., Ltd., “Rhodamin 6G” manufactured by Taoka Chemical Industry Co., Ltd.) is used. be able to. Moreover, it can also synthesize | combine with reference to Unexamined-Japanese-Patent No. 2010-32999 using the commercially available xanthene dye as a starting material.

1-1-2. Other dyes (A3)
Other dyes (A3) are not particularly limited as long as they are dyes other than xanthene dyes (A1), and are oil-soluble dyes, acid dyes, basic dyes, direct dyes, mordant dyes, amine salts of acid dyes and acid dyes Dyes such as sulfonamide derivatives, for example, dyes with color index (published by The Society of Dyens and Colorists), ie C.I. I. Examples include compounds classified as having a hue other than pigments, and known dyes described in dyeing notes (color dyeing company). Also, according to chemical structure, azo dye, anthraquinone dye, cyanine dye, phthalocyanine dye, naphthoquinone dye, quinoneimine dye, methine dye, azomethine dye, squarylium dye, acridine dye, styryl dye, coumarin dye, quinoline dye, nitro dye, etc. Is mentioned.

1-2. Solvent (B)
A solvent (B) 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-,- Solvents not containing CO- and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide and the like can be used.

  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, propylene glycol diacetate, 1,3-butylene glycol diacetate and the like.

  Examples of ether solvents include ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether; diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, and the like. Diethylene glycol monoalkyl ethers; propylene glycol monoalkyl ethers such as propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether; tetrahydrofuran, tetrahydropyran, 1,4-dioxane Which cyclic ethers; diethylene glycol dialkyl ethers such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether; dipropylene glycol dialkyl ethers such as dipropylene glycol dimethyl ether; anisole, phenetole, methyl And phenol ethers such as anisole; 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol and the like.

  Examples of ether ester solvents include ethylene glycol monoalkyl ether acetates such as ethylene glycol monomethyl ether acetate and ethylene glycol monoethyl ether acetate; propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate and the like. Propylene glycol monoalkyl ether acetates; diethylene glycol monoalkyl ether acetates such as diethylene glycol monoethyl ether acetate and diethylene glycol monobutyl ether acetate; dipropylene glycol monoalkyl ether acetates such as dipropylene glycol monomethyl ether acetate Methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, 2; -Methyl methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, 2-ethoxy-2 -Ethyl methyl propionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl 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, and glycerin.

  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.

  Of the above solvents, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether or 4-hydroxy-4-methyl-2-pentanone is preferred.

In particular, a solvent containing an ether ester solvent is preferable. In this case, the content of the ether ester solvent is preferably 40% by mass to 100% by mass with respect to the total amount of the solvent (B), and 40% by mass to 99% by mass in terms of dispersion stability. It is more preferable that The lower limit of the content of the ether ester solvent is preferably 60% by mass, more preferably 70% by mass.
The ether ester solvent is preferably at least one selected from the group consisting of ethylene glycol monoalkyl ether acetates, propylene glycol monoalkyl ether acetates and diethylene glycol monoalkyl ether acetates, more preferably propylene glycol monomethyl ether acetate. It is.
When the solvent (B) is a mixed solvent, the solvent combined with the ether ester solvent is preferably at least one selected from the group consisting of an ether solvent and a ketone solvent, and more preferably propylene glycol monomethyl ether and 4-hydroxy It is at least one selected from the group consisting of -4-methyl-2-pentanone.
It is preferable that the solvent (B) is such a solvent because a high brightness color filter can be produced from the colored curable composition prepared from the colorant dispersion of the present invention.
The solvent (B) is preferably a solvent having a solubility (23 ° C.) of the colorant (A) of 5% by mass or less, and the solubility (23 ° C.) of the colorant (A) is 0.3 to 3% by mass. It is more preferable that the solvent is A solvent (B) in which the solubility of the xanthene dye (A1) is in the above range is particularly preferable.

  The colorant dispersion of the present invention preferably contains a dispersant (D) and further contains a resin (C).

1-3. Dispersant (D)
The dispersant (D) is not particularly limited as long as it has an amine group and has an amine value of 0 to 55 mgKOH / g (preferably 2 to 40 mgKOH / g) as long as it is used for dispersing a colorant. For example, a polymer dispersing agent is mentioned.
Examples of the polymer dispersant include acrylic dispersants and urethane dispersants.
Examples of the acrylic dispersant include an acrylic block copolymer, and the acrylic block copolymer includes a colorant adsorption block containing a basic group as a colorant adsorption group (also referred to as a dye adsorption group). Furthermore, it is preferable to use a block copolymer having a colorant adsorbing block containing an acid group as a colorant adsorbing group and a block not containing a colorant adsorbing group.
As the colorant-adsorbing group, the colorant-adsorbing block further containing an acid group in addition to the colorant-adsorbing block containing a basic group is constituted by using a monomer having an acidic group together with a monomer having a basic group. Can be mentioned.

The monomer having a basic group is a monomer having a primary amino group, a secondary amino group, a tertiary amino group, or a quaternary ammonium group,
Specifically, N, N-dimethylaminoethyl (meth) acrylate, N, N-diethylaminoethyl (meth) acrylate, N, N-dimethylacrylamide, diethylacrylamide, dimethylaminopropylmethacrylamide, acryloylmorpholine, vinylimidazole, A reaction product of 2-vinylpyridine, a monomer having an amino group and a caprolactone skeleton, a monomer having a glycidyl group such as glycidyl (meth) acrylate, and a compound having one secondary amino group in the molecule; (Meth) acryloylalkyl isocyanate compound and 4- (2-aminomethyl) -pyridine, 4- (2-aminoethyl) -pyridine, 4- (2-hydroxyethyl) pyridine, 1- (2-aminoethyl) -piperazine, 2-Amino-6-methoxybenzothiazole 1- (2-hydroxyethyl-imidazole), N, N- diallyl melamine, N, such as the reaction product of N- dimethyl-1,3-propane diamine.

  As the monomer having an acidic group, a monomer having a carboxy group, a sulfonic acid group, or a phosphoric acid group, specifically, as a monomer having a carboxy group, acrylic acid, methacrylic acid, As monomers having a sulfonic acid group, such as unsaturated monocarboxylic acid compounds such as crotonic acid, unsaturated dicarboxylic acid compounds such as maleic acid, fumaric acid and itaconic acid, and half esters thereof, 2-acrylamido-2-methyl- As monomers having a phosphate group, such as 1-propanesulfonic acid, 2-methacrylamide-2-methyl-1-propanesulfonic acid, styrenesulfonic acid, acid phosphonyl (meth) acrylate, acid phosphonylethyl (meta ) Acrylate and the like.

Constituent components of the block not containing the colorant adsorbing group include aromatic vinyl compounds such as styrene, α-methylstyrene, vinyltoluene, and benzyl chloride, methyl (meth) acrylate, ethyl (meth) acrylate, and butyl (meth). Examples thereof include unsaturated carboxylic acid alkyl esters such as acrylate, unsaturated carboxylic acid arylalkyl esters such as benzyl (meth) acrylate, polycaprolactone-containing monomers, polyalkylene glycol monoester monomers, and the like.
The acrylic block copolymer can be obtained by living anionic polymerization or the like, and a conventionally known polymerization method can be used.

  The acrylic block copolymer has an amine value of 0 to 55 mgKOH / g, preferably 0 to 50 mgKOH / g, and more preferably 2 to 40 mgKOH / g. The amine value means an amine value per 1 g of the solid content of the acrylic block copolymer, and a 0.1 mol / L hydrochloric acid aqueous solution is used, and potentiometric titration (for example, COMMITITE (AUTO TITRATOR COM-900, BURET B -900, TITSTATIONK-900), manufactured by Hiranuma Sangyo Co., Ltd., and then converted to an equivalent of potassium hydroxide.

  Commercially available products of the acrylic block copolymer include “Disperbyk (registered trademark) -112 (amine value 36 mgKOH / g)” and “Disperbyk (registered trademark) -2000 (amine value 4 mgKOH / g) manufactured by Big Chemie Japan. ) "," Disperbyk-2001 (amine number 29 mgKOH / g) "," Disperbyk (registered trademark) -2020 (amine number 38 mgKOH / g) "," Disperbyk (registered trademark) -2050 (amine number 30 mgKOH / g) ", “Disperbyk (registered trademark) -2070 (amine value 20 mgKOH / g)” and the like can be mentioned.

As the urethane-based dispersant, the isocyanate group of the polyisocyanate compound has a compound having a number average molecular weight of 300 to 10,000 having one or more hydroxy groups in the molecule and a functional group capable of reacting with the isocyanate group in the molecule. Those obtained by reacting a basic group-containing compound can be used. As a method for obtaining such a urethane-based dispersant, a method described in JP-A-60-166318 can be used.
Examples of the polyisocyanate compound constituting the urethane-based dispersant include isocyanate compounds having two or more isocyanate groups. For example, 2,4-tolylene diisocyanate and 2,4-tolylene diisocyanate are used in two amounts. 2,6-tolylene diisocyanate, p-xylene diisocyanate, m-xylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 1,5-naphthylene diisocyanate, 3,3'-dimethylbiphenyl-4,4'-diisocyanate Aromatic diisocyanate compounds such as hexamethylene diisocyanate, isophorone diisocyanate, 4,4'-methylenebis (cyclohexyl isocyanate), methylcyclohexane-2,4 (or 2,6) diisocyanate, 1, -Aliphatic and alicyclic polyisocyanates such as (isocyanatomethylene) cyclohexane; polyisocyanates having isocyanuric groups based on the diisocyanates (polyisocyanates having isocyanuric groups formed by trimerization of the diisocyanates), polyols And polyisocyanates obtained by reacting diisocyanates with polyisocyanates, polyisocyanates obtained by biuret reaction of diisocyanate compounds, and the like. Among the polyisocyanate compounds, for example, polyisocyanates having an isocyanuric group based on diisocyanates such as tolylene diisocyanate and isophorone diisocyanate are preferable.

Examples of the compound having one or more hydroxy groups in the molecule constituting the urethane dispersant include polyether compounds and polyester compounds.
Examples of the polyether compound include polyalkylene glycols such as polyethylene glycol, polypropylene glycol, polybutylene glycol, and polytetramethylene glycol; ethylene glycol, propanediol, propylene glycol, tetramethylene glycol, pentamethylene glycol, hexanediol, Neopentyl glycol, glycerin, trimethylolpropane, pentaerythritol, diglycerin, ditrimethylolpropane, alkylene glycols such as dipentaerythritol, low molecular monools such as methanol and ethanol, ethylene oxide modified products, propylene oxide modified products, Examples include butylene oxide-modified products and tetrahydrofuran-modified products.

  Examples of the polyester compound include ethylene glycol, propanediol, propylene glycol, tetramethylene glycol, pentamethylene glycol, hexanediol, neopentyl glycol, glycerin, trimethylolpropane, pentaerythritol, diglycerin, ditrimethylolpropane, dipenta. Ε-caprolactone-modified, γ-butyrolactone-modified, δ-valerolactone-modified, methylvalerolactone-modified; alkylene glycols such as erythritol, low-molecular monools such as methanol and ethanol; adipic acid, dimer acid, etc. An aliphatic polyester polyol which is an esterified product of an aliphatic dicarboxylic acid and a polyol such as neopentyl glycol or methylpentanediol; terephthalic acid Polyester polyols such as aromatic polyester polyols, which are esterified products of an aromatic dicarboxylic acid and a polyol such as neopentyl glycol; polycarbonate polyols, acrylic polyols, polytetramethylene hexaglyceryl ether (tetraglycerin-modified tetrahydrofuran), etc. An esterified product of a polyvalent hydroxy group compound and a dicarboxylic acid such as fumaric acid, phthalic acid, isophthalic acid, itaconic acid, adipic acid, sebacic acid or maleic acid; a polyhydroxy group-containing compound such as glycerin and a fatty acid ester And polyhydric hydroxy group-containing compounds such as monoglycerides obtained by transesterification. Among the compounds having one or more hydroxy groups in the molecule, an ε-caprolactone adduct of alcohols is preferable.

  The number average molecular weight of the compound having one or more hydroxy groups in the molecule is 300 to 10,000, preferably 300 to 6,000. The number average molecular weight and the weight average molecular weight can be measured by a column chromatography method.

The basic group-containing compound having a functional group capable of reacting with an isocyanate group in the molecule constituting the urethane-based dispersant is not particularly limited, but a polyol having an N, N-disubstituted amino group or a heterocyclic nitrogen atom, It is preferably at least one compound selected from the group consisting of polythiols and amines. As these compounds, compounds that are known and commonly used in the technical field of dispersants can be used. These compounds have an active hydrogen atom of Zelevitinoff and at least one nitrogen atom-containing basic group.
Examples of such compounds include N, N-dimethyl-1,3-propanediamine, N, N-diethyl-1,4-butanediamine, 2-dimethylaminoethanol, 1- (2-aminoethyl)- Piperazine, 2- (1-pyrrolidyl) -ethylamine, 4-amino-2-methoxypyrimidine, 4- (2-aminoethyl) -pyridine, 1- (2-hydroxyethyl) -piperazine, 4- (2-hydroxyethyl) ) -Morpholine, 2-mercaptopyrimidine, 2-mercaptobenzimidazole, 2-amino-6-methoxybenzothiazole, N, N-diallyl-melamine, 3-amino-1,2,4-triazole, 1- (2 -Hydroxyethyl) -imidazole, 3-mercapto-1,2,4-triazole, and the like. Of these, amines having a heterocyclic nitrogen atom are preferred.

  The reaction in the synthesis of the urethane dispersant is not particularly limited, and can be performed by a conventionally known method. The amine value of the urethane-based dispersant is also 0 to 55 mgKOH / g, preferably 5 to 40 mgKOH / g.

  Moreover, as a commercial item of the said urethane type dispersing agent, Disperbyk-161 (Amine number 11 mgKOH / g, the Big Chemie company make), Disperbyk-162 (Amine number 13 mgKOH / g Big Chemie company make), Disperbyk-167 (Amine number 13 mgKOH / g, manufactured by Big Chemie), Disperbyk-182 (amine value 13 mgKOH / g, manufactured by Big Chemie), and the like.

  As the dispersant, the acrylic dispersant is preferable.

1-4. Resin (C)
The resin (C) is not particularly limited, but is preferably an alkali-soluble resin. Examples of the resin (C) include the following resins [K1] to [K6].
Resin [K1] At least one (a) selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride (hereinafter sometimes referred to as “(a)”), 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)”);
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] Resin obtained by reacting (b) with a copolymer of (a) and (c);
Resin [K5] Resin obtained by reacting (a) with a copolymer of (b) and (c);
Resin [K6] A resin obtained by reacting (a) 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) refers to a polymerizable compound having, for example, 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. . (B) is preferably a monomer having a C2-C4 cyclic ether structure and a (meth) acryloyloxy group.
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.

  Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b1)”), and a single monomer having an oxetanyl group and an ethylenically unsaturated bond. Monomer (b2) (hereinafter sometimes referred to as “(b2)”), monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (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)”) And a monomer (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as “(b1-2)”).

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

  Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celoxide (registered trademark) 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth). Acrylate (for example, Cyclomer (registered trademark) A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth) acrylate (for example, Cyclomer M100; manufactured by Daicel Corporation), represented by the formula (I) And a compound represented by the formula (II).

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

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

Examples of the alkanediyl group include methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane- Examples include 1,6-diyl group.
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—, more preferably a single bond, * —CH _2. CH ₂ —O— (* represents a bond with O).

  Examples of the compound represented by the formula (I) include compounds represented by the formula (I-1) to the formula (I-15). Preferably 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 these is mentioned. More preferably, the compound represented by Formula (I-1), Formula (I-7), Formula (I-9) or Formula (I-15) is mentioned.

  Examples of the compound represented by the formula (II) include compounds represented by the formula (II-1) to the formula (II-15). Preferably 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 these is mentioned. More preferably, the compound represented by Formula (II-1), Formula (II-7), Formula (II-9), or Formula (II-15) is mentioned.

  The compound represented by formula (I) and the compound represented by formula (II) may be used alone or in combination with the compound represented by formula (I) and the compound represented by formula (II). May be. 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 5 on a molar basis. 90:10, more preferably 20:80 to 80:20.

  (B2) is more preferably a monomer having an oxetanyl group and a (meth) acryloyloxy group. (B2) includes 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 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.

  (B3) is more preferably a monomer having a tetrahydrofuryl group and a (meth) acryloyloxy group. Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Biscoat V # 150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.

  (B) is preferably (b1) in that the color filter obtained can have higher reliability such as heat resistance and chemical resistance. Furthermore, (b1-2) is more preferable in that the storage stability of the colored curable composition is excellent.

Examples of (c) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, and 2-ethylhexyl (meth). Acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decan-8-yl (meth) acrylate (in 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 monomers such as styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene; nitrile monomers such as acrylonitrile and methacrylonitrile; halogenation such as vinyl chloride and vinylidene chloride Vinyls; Amide monomers such as acrylamide and methacrylamide; Vinyl acetates; Diene monomers such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene.
Among these, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1] hept-2-ene and the like are preferable from the viewpoint of copolymerization reactivity and heat resistance. preferable.

In the resin [K1], the ratio of the structural unit derived from each is the total structural unit constituting the resin [K1]
Structural unit derived from (a); 2 to 60 mol%
Structural unit derived from (b); 40-98 mol%
It is preferable that
Structural unit derived from (a); 10-50 mol%
Structural unit derived from (b); 50-90 mol%
It is more preferable that
When the ratio of the structural units of the resin [K1] is in the above range, the storage stability of the colored curable composition, the developability when forming a colored pattern, and the solvent resistance of the resulting color filter tend to be excellent. There is.

  The resin [K1] is, 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 the document Can be produced with reference to the cited references described in 1.

  Specifically, a predetermined amount of (a) and (b), a polymerization initiator, a solvent, and the like are placed in a reaction vessel, for example, by substituting oxygen with nitrogen to create a deoxygenated atmosphere, with stirring, The method of heating and heat retention is mentioned. In addition, the polymerization initiator, the solvent, and the like used here are not particularly limited, and those usually used in the field can be used. For example, as polymerization initiators, azo compounds (2,2′-azobisisobutyronitrile, 2,2′-azobis (2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.) Any solvent may be used as long as it dissolves each monomer. Examples of the solvent (E) for the colored curable composition of the present invention include the solvents described later.

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

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

  Resin [K2] can be produced, for example, in the same manner as the method described as the production method of resin [K1].

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

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

Next, the C2-C4 cyclic ether which (b) has is reacted with a part of the carboxylic acid and / or carboxylic anhydride derived from (a) in the copolymer.
Subsequent to the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced from nitrogen to air, and (b) a reaction catalyst of carboxylic acid or carboxylic anhydride and cyclic ether (for example, tris ( Dimethylaminomethyl) phenol, etc.) and a polymerization inhibitor (eg, hydroquinone, etc.) are placed in a flask and reacted, for example, at 60-130 ° C. for 1-10 hours to produce resin [K4]. it can.
The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). By making this range, the storage stability of the colored curable composition, the developability when forming the pattern, and the solvent resistance, heat resistance, mechanical strength and sensitivity of the resulting pattern tend to be good. There is. Since the reactivity of the cyclic ether is high and unreacted (b) hardly remains, (b1) is preferable as (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, reaction temperature, and time can be appropriately adjusted in consideration of the production equipment and the amount of heat generated by polymerization. In addition, like the polymerization conditions, the charging method and the reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, and the like.

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

Further, under the same conditions as in the method for producing the resin [K4], the cyclic ether derived from (b) of the copolymer of (b) and (c) is added to the carboxylic acid or carboxylic acid anhydride of (a). Resin [K5] can be obtained by reacting the product.
As for the usage-amount of (a) made to react with the said copolymer, 5-80 mol is preferable with respect to 100 mol of (b). Since the reactivity of the cyclic ether is high and unreacted (b) hardly remains, (b1) is preferable as (b) used for the resin [K5], and (b1-1) is more preferable.

The resin [K6] is a resin obtained by further reacting the carboxylic acid anhydride with the resin [K5].
Carboxylic anhydride is reacted with a hydroxy group generated by reaction of cyclic ether with carboxylic acid or carboxylic anhydride.
Carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1 2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride (highmic acid anhydride) and the like. It is done. As for the usage-amount of carboxylic acid anhydride, 0.5-1 mol is preferable with respect to 1 mol of usage-amount of (a).

As the resin (C), specifically, 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] Resin such as decyl 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 acrylate / (meth) acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo [5.2.1.0 ^{2, 6]} decyl acrylate / (meth) acrylic acid / styrene monomer copolymer, 3-methyl-3- (meth) acryloyl Resin such as xymethyloxetane / (meth) acrylic acid / styrene copolymer [K2]; Resin such as benzyl (meth) acrylate / (meth) acrylic acid copolymer, styrene / (meth) acrylic acid copolymer [ K3]; a resin obtained by adding glycidyl (meth) acrylate to a benzyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (tricyclodecyl (meth) acrylate / styrene / (meth) acrylic acid copolymer) Resin [K4] such as resin added with meth) acrylate, resin obtained by adding glycidyl (meth) acrylate to tricyclodecyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer; A copolymer of cyclodecyl (meth) acrylate / glycidyl (meth) acrylate (meta Resin [K5] such as a resin obtained by reacting acrylic acid, a resin obtained by reacting a copolymer of tricyclodecyl (meth) acrylate / styrene / glycidyl (meth) acrylate with (meth) acrylic acid; tricyclodecyl (meta And resin [K6] such as a resin obtained by further reacting a copolymer of acrylate / glycidyl (meth) acrylate with (meth) acrylic acid and further reacting with tetrahydrophthalic anhydride.
Especially, as resin (C), resin [K1] and resin [K2] are preferable.

The polystyrene equivalent weight average molecular weight of the resin (C) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and further preferably 5,000 to 30,000. .
The molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (C) is preferably 1.1 to 6, and more preferably 1.2 to 4.

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

1-5. Method for Producing Colorant Dispersion Disperse colorant (A) in solvent (B) with dispersant (D), and further disperse resin (C) in solvent (B) as necessary. Thus, a colorant dispersion can be produced.
The dispersion treatment refers to mixing until particles such as the colorant (A) and the resin (C) are in a dispersed state. By this dispersion treatment, the particles are pulverized into small particles. The dispersed state means a state in which particles are floated in the solvent (B) in the mixed solution.

  The content of the colorant (A) in the colorant dispersion of the present invention is preferably 2% by mass or more, more preferably 5% by mass or more, and 30% by mass or less with respect to the total amount of the colorant dispersion. Is preferable, and 20 mass% or less is more preferable.

Further, the content of the solvent (B) is preferably 60% by mass or more, more preferably 75% by mass or more, preferably 93% by mass or less, and preferably 90% by mass or less, with respect to the total amount of the colorant dispersion. More preferably, it is 85 mass% or less most preferably.
When the colorant dispersion contains the resin (C), the content of the resin (C) is preferably 1% by mass or more, more preferably 2% by mass or more, with respect to the total amount of the colorant dispersion, It is preferably at most 7 mass%, more preferably at most 7 mass%. When the content of the resin (C) is within the above range, the dispersion state tends to be stable.
The content of the dispersant (D) in the colorant dispersion is preferably 1% by mass or more, more preferably 2% by mass or less, and preferably 20% by mass or less, based on the total amount of the colorant dispersion. More preferably, it is 10 mass% or less. When the content of the dispersant (D) is within the above range, the dispersion state tends to be stable.

When the colorant (A) is dispersed in the solvent (B) and when the mixture is dispersed, the temperature is preferably 120 ° C. or lower, more preferably 70 ° C. or lower. Although the minimum of the temperature at the time of carrying out acid separation is not specifically limited, Usually, it is 20 degreeC.
The dispersion time is preferably 0.5 hours or longer, more preferably 2 hours or longer, 48 hours or shorter, more preferably 20 hours or shorter.
Examples of the apparatus used for dispersion include a roll mill, a high speed stirring apparatus, a bead mill, a ball mill, a sand mill, a paint conditioner, an ultrasonic disperser, and a high pressure disperser.
The obtained colorant dispersion is preferably filtered with a filter having a pore size of about 1.0 to 5.0 μm.

2. Colored curable composition The colored curable composition of the present invention contains a polymerizable compound (E) and a polymerization initiator (F) in addition to the colorant dispersion described above.

2-1. Polymerizable compound (E)
The polymerizable compound (E) is a compound that can be polymerized by an active radical and an acid generated from the polymerization initiator (F) described later, and examples thereof include a compound having a polymerizable ethylenically unsaturated bond. Preferably, a (meth) acrylic acid ester compound is used.

Among them, the polymerizable compound (E) is preferably a polymerizable compound having 3 or more (preferably 4 to 10, more preferably 5 to 8) ethylenically unsaturated bonds, and more preferably 3 or more (preferably 4). To 10 and more preferably 5 to 8), an ester of (meth) acrylic acid with an alcohol having an OH group (for example, pentaerythritol, a condensate thereof, or a modified product thereof) is preferable. Examples of such polymerizable compounds include pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tripentaerythritol octa (meth) acrylate, and 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 Over DOO, propylene glycol-modified dipentaerythritol hexa (meth) acrylate, caprolactone-modified pentaerythritol tetra (meth) acrylate, caprolactone-modified dipentaerythritol hexa (meth) acrylate. Of these, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and the like are preferable.
The weight average molecular weight of the polymerizable compound (E) is preferably 150 or more and 2,900 or less, more preferably 250 or more and 1,500 or less.

  The content of the polymerizable compound (E) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and still more preferably 17 to 65% by mass with respect to the solid content of the colored curable composition. 55% by mass. When the content of the polymerizable compound (E) is within the above range, the curing is sufficiently performed, the remaining film ratio in development is improved, and the undercut is difficult to enter into the colored pattern, so that the adhesion is improved. It is preferable because it tends to be good.

2-2. Polymerization initiator (F)
The polymerization initiator (F) is not particularly limited as long as it is a compound that generates an active radical, an acid or the like by the action of light or heat and can initiate polymerization, and a known polymerization initiator may be used. it can.
As the polymerization initiator (F), a compound that generates an active radical by the action of light is preferable, and an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an oxime compound, and a biimidazole compound are more preferable.

  The alkylphenone compound is a compound having a partial structure represented by the formula (d2) or a partial structure represented by the formula (d3). In these partial structures, the benzene ring may have a substituent.

Examples of the compound having a partial structure represented by the formula (d2) include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one, 2-dimethylamino-1- (4 -Morpholinophenyl) -2-benzylbutan-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butan-1-one Etc. Commercial products such as Irgacure (registered trademark) 369, 907 and 379 (manufactured by BASF) may be used.
Examples of the compound having a partial structure represented by the formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1- [4- (2 -Hydroxyethoxy) phenyl] propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomer of 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propan-1-one, α, α-diethoxy Examples include acetophenone and benzyl dimethyl ketal.
In terms of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by the formula (d2), such as 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one. And 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutan-1-one is more preferred.

  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-methoxystyryl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (Trichloromethyl) -6- [2- (furan-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2- Methylphenyl) ete Le] -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. Commercial products such as Irgacure (registered trademark) 819 (manufactured by BASF) may be used.

  The oxime compound is a compound having a partial structure represented by the formula (d1). Hereinafter, * represents a bond.

  Examples of the oxime compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one- 2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1- [9-ethyl-6- (2-methylbenzoyl) ) -9H-carbazol-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- {2-methyl-4- (3,3-dimethyl-2,4-dioxacyclo) Pentanylmethyloxy) 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-carbazole-3 -Yl] -3-cyclopentylpropane-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 them, N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan-1-one-2-imine is preferred. When these oxime compounds are used, when the colored curable composition of the present invention is prepared as a blue colored curable composition, the brightness of the obtained color filter tends to be high.

  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 (trialkoxy) Nyl) biimidazole (for example, see JP-B-48-38403, JP-A-62-174204, etc.), and the phenyl group at the 4,4′5,5′-position is substituted with a carboalkoxy group. Examples thereof include imidazole compounds (for example, see JP-A-7-10913). Preferably, 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole, 2,2′-bis (2,3-dichlorophenyl) -4,4 ′, 5 Examples include 5'-tetraphenylbiimidazole and 2,2'-bis (2,4-dichlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole.

  Further, as the polymerization initiator (F), 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. These are preferably used in combination with a polymerization initiation assistant (F1) (particularly amines) described later.

  Examples of the acid generator that generates an acid by light include 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4 -Onium salts such as acetoxyphenyl methyl benzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, Examples thereof include nitrobenzyl tosylate and benzoin tosylate.

  The content of the polymerization initiator (F) is the resin (C) in the colored curable composition of the present invention (when the resin (C ′) described later is included, the resin (C ′) is also included) and Preferably it is 0.1-30 mass parts with respect to 100 mass parts of total amounts of a polymeric compound (E), More preferably, it is 1-20 mass parts. When the content of the photopolymerization initiator is within the above range, the sensitivity is increased, the exposure time is shortened, and the productivity is improved.

  The colored curable composition of the present invention may further include at least one selected from the group consisting of a polymerization initiation assistant (F1) and a leveling agent (G).

2-3. Polymerization initiation aid (F1)
The colored curable composition of the present invention may further contain a polymerization initiation assistant (F1). The polymerization initiation assistant (F1) is a compound or a sensitizer used for accelerating the polymerization of the polymerizable compound initiated by the polymerization initiator, and is usually combined with the polymerization initiator (F). Used.
Examples of the polymerization initiation assistant (F1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.
Examples of amine compounds 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, and 4,4′-bis (diethylamino) benzophenone is preferred. Commercial products such as EAB-F (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, 9,10-di. Examples include butoxyanthracene and 2-ethyl-9,10-dibutoxyanthracene.

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

  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, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid and the like can be mentioned.

  When the polymerization initiation assistant (F1) is used, the amount used thereof is the resin (C) in the colored curable composition of the present invention (including the resin (C ′) when the resin (C ′) described later is included). And 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass with respect to 100 parts by mass of the total amount of the polymerizable compound (E). When the amount of the polymerization initiation assistant (F1) is within this range, it is possible to form a pattern with higher sensitivity and to improve the productivity of the pattern.

2-4. Leveling agent (G)
Examples of the leveling agent (G) include silicone surfactants, fluorine surfactants, and silicone surfactants having a fluorine atom. These may have a polymerizable group in the side chain.
Examples of the silicone surfactant include a surfactant having a siloxane bond. Specifically, Torre Silicone (trade name) DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH30PA, 8400 (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 (made by Momentive Performance Materials Japan GK) Is mentioned.

  Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain. Specifically, Florard (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), MegaFac (registered trademark) F142D, F171, F172, F173, F177, F183, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), Ftop (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals), Surflon (registered trademark) S381, S382, SC101, SC105 (Asahi Glass Co., Ltd.), E5844 (Daikin Fine Chemical Laboratory Co., Ltd.) and the like.

  Examples of the silicone-based surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain. Specifically, Megafac (registered trademark) R08, BL20, F475, F477, F443 (manufactured by DIC Corporation) and the like can be mentioned.

  The content of the leveling agent (G) is preferably 0.001% by mass to 0.2% by mass, and preferably 0.002% by mass to 0%, based on the total amount of the colored curable composition of the present invention. .1% by mass or less, more preferably 0.005% by mass or more and 0.05% by mass or less. This content does not include the content of the pigment dispersant (D ′) described later. When the content of the leveling agent (G) is within the above range, the flatness of the color filter can be improved.

2-5. Resin (C ')
When the colorant dispersion of the present invention does not contain a resin, it is preferable to add a resin (“resin (C ′)”) when preparing a colored curable composition. Moreover, when a colorant dispersion liquid contains resin (C), you may add resin (C ') further when preparing a colored curable composition. As resin (C ') used when preparing a colored curable composition, the same thing as resin (C) is mentioned. The resin (C ′) may be the same as the resin (C), but may be of a different type.

  The total content of the resin (C) and the resin (C ′) is preferably 7 to 65% by mass, more preferably 10 to 60% by mass, and still more preferably 13% with respect to the total amount of solids. It is -60 mass%, Most preferably, it is 13-55 mass%. If the resin content is in the above range, the resolution of the colored pattern and the remaining film ratio of the colored pattern tend to be improved.

  The colored curable composition of the present invention preferably further contains at least one selected from the group consisting of a solvent (B ′) and a colorant (A ′).

2-6. Solvent (B ')
Examples of the solvent used for preparing the colored curable composition (hereinafter referred to as “solvent (B ′)”) include the same solvents as those for the solvent (B).

  Preferably, it is an organic solvent having a boiling point at 1 atm of 120 ° C. or more and 180 ° C. or less, more preferably propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, 3-ethoxypropion, from the viewpoint of coating property and drying property. Ethyl acetate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol ethyl methyl ether, 3-methoxybutyl acetate, 3-methoxy-1-butanol, 4-hydroxy-4-methyl-2-pentanone, N, N-dimethylformamide and the like, more preferably propylene glycol monomethyl ether acetate, ethyl lactate, 4-hydroxy-4-methyl-2-pe Thanong, diethylene glycol ethyl methyl ether, 3-methoxybutyl acetate, 3-methoxy-1-butanol, ethyl 3-ethoxypropionate, and the like.

  The total content of the solvent (B) and the solvent (B ′) in the colored curable composition is preferably 40 to 95% by mass, more preferably 45 to 92%, based on the total amount of the colored curable composition. % By mass. In other words, the solid content of the colored curable composition is preferably 5 to 60% by mass, more preferably 8 to 55% by mass. When the content of the solvent is in the above range, the flatness at the time of application is good, and the color characteristics are not insufficient when the color filter is formed, so that the display characteristics tend to be good.

2-7. Colorant (A ')
Examples of the colorant (A ′) used when preparing the colored curable composition include the same colorant (A) and pigment (A2).

  The total content of the colorant (A) and the colorant (A ′) is preferably 5 to 60% by mass, more preferably 8 to 55% by mass, based on the solid content of the colored curable composition. Yes, more preferably 10 to 50% by mass. When the content of the colorant is in the above range, the color density when it is used as a color filter is sufficient, and a resin or a polymerizable compound can be contained in the composition in a required amount, so that the mechanical strength is high. A sufficient color filter can be formed. Here, solid content of a colored curable composition means the total amount of the component remove | excluding the solvent from the colored curable composition of this invention. The solid content and the content of each component relative thereto can be measured by a known analysis means such as liquid chromatography or gas chromatography.

2-8. Pigment Composition When the colored curable composition of the present invention contains a pigment (A2), it is preferable to prepare a pigment composition separately from the colorant dispersion and use it for the preparation of the colored curable composition of the present invention. . The pigment composition preferably contains the pigment (A2) and the solvent (B ″). The pigment (A2) is preferably mixed with a solvent (B ″) 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. The solvent (B ″) is a part or all of the solvent (B ′).
The pigment composition preferably further contains at least one selected from the group consisting of a resin (C ″) and a pigment dispersant (D ′). The resin (C ″) is a part or all of the resin (C ′). By dispersing at least one selected from the group consisting of a resin (C ″) and a pigment dispersant (D ′) and dispersing the pigment (A2), the pigment (A2) is uniformly dispersed in the solution. It becomes a state.

2-8-1. Pigment (A2)
The pigment (A2) is not particularly limited, and known pigments can be used. Examples thereof include organic pigments and inorganic pigments, and compounds classified as pigments by the Color Index (published by The Society of Dyers and Colorists) Etc.

Examples of the organic pigment include C.I. 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. And green pigments such as CI Pigment Green 7, 36, and 58.

  Among them, C.I. I. Pigment red violet 23, C.I. I. Pigment Blue 15: 3 and 15: 6 are preferable. I. Pigment Blue 15: 6 is more preferable.

  Examples of inorganic pigments include metal compounds such as metal oxides and metal complex salts. Specifically, iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony and other metal compounds. Oxides or mixed metal oxides may be mentioned.

  The pigment (A2) is optionally treated with rosin, surface treatment using a pigment derivative or dispersant into which an acidic group or basic group has been introduced, graft treatment on the pigment surface with a polymer compound, Atomization treatment by a sulfuric acid atomization method or the like, a cleaning treatment with an organic solvent or water for removing impurities, a removal treatment by an ion exchange method of ionic impurities, or the like may be performed. The pigment (A2) preferably has a uniform particle size.

  Further, when the pigment (A2) is used, the content of the pigment (A2) is preferably 1 to 99% by mass, more preferably based on the total amount of the colorant (A) and the colorant (A ′). Is 50 to 99 mass%, more preferably 70 to 99 mass%.

2-8-2. Pigment dispersant (D ')
As the pigment dispersant (D ′), in addition to the same as the dispersant (D) described above, a synergist type dispersant can be used.

  Examples of the synergist type dispersant (pigment derivative type dispersant) include phthalocyanine derivatives. As a commercial item of a synergist type dispersant, “Solsperse (registered trademark) 5000 (copper phthalocyanine derivative)” manufactured by Lou Breeze Co., Ltd. and the like can be mentioned.

  When the synergist type dispersant is included, the content thereof is preferably 0.1 parts by mass or more, more preferably 0.5 parts by mass or more, and still more preferably 1 part by mass or more with respect to 100 parts by mass of the pigment. 20 mass parts or less are preferable, More preferably, it is 10 mass parts or less, More preferably, it is 8 mass parts or less.

  When the polymer dispersant and synergist type dispersant are used in combination as the pigment dispersant (D ′), the mass ratio (polymer dispersant / synergist type dispersant) is preferably 70/30 to 99/1. More preferably, it is 80 / 20-97 / 3, More preferably, it is 85 / 15-95 / 5.

  The amount of the pigment dispersant (D ′) used is preferably 100 parts by mass or less, more preferably 5 parts by mass or more and 50 parts by mass or less per 100 parts by mass of the pigment (A2).

The total content of the dispersant (D) and the pigment dispersant (D ′) is preferably 0.1% by mass or more, more preferably 0.5% by mass with respect to the total amount of the colored curable composition. % Or more, more preferably 1% by mass or more, preferably 20% by mass or less, more preferably 10% by mass or less, and still more preferably 5% by mass or less.
When the amount of the pigment dispersant (D ′) used is in the above range, the dispersion state of the pigment is good.

The content of the pigment (A2) in the pigment composition is preferably 5% by mass or more, more preferably 10% by mass or more, preferably 30% by mass or less, and 20% by mass with respect to the total amount of the pigment composition. The following is more preferable.
The content of the solvent (B ″) in the pigment composition is preferably 60% by mass or more, more preferably 75% by mass or more, and preferably 90% by mass or less, based on the total amount of the pigment composition. Preferably it is 85 mass% or less.
When the resin (C ″) is included, the content of the resin (C ″) in the pigment composition is preferably 1% by mass or more, more preferably 2% by mass or more with respect to the total amount of the pigment composition. Yes, 15 mass% or less is preferable, More preferably, it is 7 mass% or less.
When the pigment dispersant (D ′) is contained, the content of the pigment dispersant (D ′) in the pigment composition is preferably 1% by mass or more, more preferably 2% by mass with respect to the total amount of the pigment composition. It is above, 20 mass% or less is preferable, More preferably, it is 10 mass% or less.

2-9. Other Components The colored curable composition of the present invention is known in the art as necessary, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, etc. Various additives (hereinafter referred to as “other components”) may be included.

2-10. Manufacturing method of colored curable composition The colored curable composition of this invention is used as needed, for example, the coloring agent dispersion liquid of this invention, a polymeric compound (E), and a polymerization initiator (F). It can be prepared by mixing the polymerization initiation assistant (F1), the leveling agent (G), the pigment composition and other components.
When the colorant dispersion does not contain the resin (C), it is preferable to add the resin (C ′) when preparing the colored curable composition. When the colorant dispersion includes the resin (C), the resin (C ′) may be further added when preparing the colored curable composition.
When preparing a colored curable composition, you may add a coloring agent (A ') and / or a solvent (B') further.
The colored curable composition prepared by mixing as described above is preferably filtered with a filter having a pore size of about 0.01 to 10 μm.

3. Method for Producing Color Filter Examples of a method for producing a color pattern of a color filter from the colored curable composition of the present invention include a photolithographic method, an ink jet method, and a printing method. Of these, the photolithographic method is preferable. The photolithographic method is a method in which the colored curable composition is applied to a substrate, dried to form a composition layer, the composition layer is exposed through a photomask, and developed. In the photolithography method, a colored coating film that is a cured product of the composition layer can be formed by not using a photomask and / or not developing during exposure.
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, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.5. ~ 6 μm.

  As the substrate, quartz glass, borosilicate glass, alumina silicate glass, glass plate such as 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 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 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 composition layer is not particularly limited, and may be appropriately selected according to the film thickness of the target color filter.

Next, the 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. Specific examples include mercury lamps, light emitting diodes, metal halide lamps, halogen lamps, and the like.
It is preferable to use an exposure apparatus such as a mask aligner or a stepper because the entire exposure surface can be irradiated with parallel light rays uniformly and the photomask and substrate can be accurately aligned.

By developing the exposed composition layer in contact with a developer, a colored pattern is formed on the substrate. By the development, the unexposed portion of the composition layer is dissolved and removed in the developer. 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.

  The colored pattern and the colored coating film thus obtained are useful as a color filter because of their high brightness, and the color filter can be used for display devices (for example, liquid crystal display devices, organic EL devices, etc.), electronic paper, solid-state imaging devices. It is useful as a color filter used for the above.

Hereinafter, the present invention will be described in more detail with reference to examples. However, the present invention is not limited to the following examples, and may be appropriately modified and implemented within a range that can meet the purpose described above and below. All of which are within the scope of the present invention. Unless otherwise specified, “%” and “parts” in the examples are% by mass and parts by mass.
In the following synthesis examples, the compounds were identified by mass spectrometry (LC; Agilent 1200 type, MASS; Agilent LC / MSD type).

[Synthesis Example 1]
20 parts of the compound represented by the formula (1x) and 200 parts of N-ethyl-o-toluidine (manufactured by Wako Pure Chemical Industries, Ltd.) were mixed under shading conditions, and the resulting solution was stirred at 110 ° C. for 6 hours. did. The obtained reaction solution was cooled to room temperature, then added to a mixed solution of 800 parts of water and 50 parts of 35% hydrochloric acid, and stirred at room temperature for 1 hour, whereby crystals were precipitated. The precipitated crystals were obtained as a suction filtration residue and dried to obtain 24 parts of a compound represented by the formula (1-24). The yield was 80%.

Identification of compound represented by formula (1-24) (mass spectrometry) ionization mode = ESI +: m / z = [M + H] ⁺ 603.4
Exact Mass: 602.2

[Synthesis Example 2]
A compound represented by the formula (1-32) was obtained in the same manner as in Synthesis Example 1 except that N-propyl-2,6-dimethylaniline was used instead of N-ethyl-o-toluidine.

Identification of compound represented by formula (1-32) (mass spectrometry) ionization mode = ESI +: m / z = [M + H] ⁺ 659.9
Exact Mass: 658.9

[Synthesis Example 3]
In a flask equipped with a condenser and a stirrer, 15 parts of a mixture of the compound represented by formula (A0-1) and the compound represented by formula (A0-2) (manufactured by Chugai Kasei), 150 parts of chloroform and N , N-dimethylformamide (8.9 parts) was added, and 10.9 parts of thionyl chloride was added dropwise while maintaining the temperature at 20 ° C. or lower with stirring. After completion of the dropwise addition, the temperature was raised to 50 ° C., the reaction was continued for 5 hours at the same temperature, and then cooled to 20 ° C. While maintaining the reaction solution after cooling at 20 ° C. or lower with stirring, a mixed solution of 12.5 parts of 2-ethylhexylamine and 22.1 parts of triethylamine was added dropwise. Then, it was made to react by stirring at the same temperature for 5 hours. Next, after the solvent of the obtained reaction mixture was distilled off with a rotary evaporator, a small amount of methanol was added and stirred vigorously. This mixture was added to a mixture of 375 parts of ion-exchanged water with stirring to precipitate crystals. 10. Precipitated crystals are filtered off, washed well with ion-exchanged water, dried under reduced pressure at 60 ° C., and dye A1 (mixture of compounds represented by formula (A1-1) to formula (A1-8)). Three parts were obtained.

[Synthesis Example 4]
50.0 parts of the compound represented by the formula (1x) and 350 parts of isopropyl alcohol (manufactured by Wako Pure Chemical Industries, Ltd.) are mixed at room temperature, and 18.1 parts of diethylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) are mixed into the mixture. Was added dropwise at a temperature not exceeding 20 ° C. and stirred at 20 ° C. for 3 hours. The reaction solution was added to 2100 parts of 10% hydrochloric acid. The obtained precipitate was obtained as a residue of suction filtration, washed with 373 parts of ion exchange water and then dried to obtain 23.6 parts of a compound represented by the formula (1y). The yield was 43%.

Identification of compound represented by formula (1y) (mass spectrometry) ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 442.1
Exact Mass: 441.1

[Synthesis Example 5]
5.0 parts of the compound represented by the formula (1y) and 35 parts of N-methylpyrrolidone (manufactured by Wako Pure Chemical Industries, Ltd.) are mixed at room temperature, and dipropylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) is mixed into the mixture. 3.4 parts were added dropwise at a temperature not exceeding 20 ° C., the temperature was raised to 80 ° C. and the mixture was stirred for 3 hours. After cooling the reaction solution to room temperature, 3.4 parts of concentrated hydrochloric acid was added, and the resulting mixture was added to 315 parts of saturated brine. The obtained precipitate was obtained as a residue of suction filtration, washed with 630 parts of ion-exchanged water and dried to obtain 3.9 parts of a compound represented by the formula (1-51). The yield was 69%.

Identification of compound represented by formula (1-51) (mass spectrometry) ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 507.7
Exact Mass: 506.7

[Synthesis Example 6]
10.0 parts of the compound represented by the formula (1x) and 40 parts of isopropyl alcohol (manufactured by Wako Pure Chemical Industries, Ltd.) are mixed at room temperature, and 7.2 parts of diethylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) are mixed into the mixture. Was added dropwise, and the mixture was heated to 65 ° C. and stirred for 3 hours. The reaction solution was cooled to room temperature and then charged into 280 parts of 0.5% brine. The obtained precipitate was obtained as a residue of suction filtration, washed with 200 parts of ion-exchanged water and dried to obtain 8.0 parts of a compound represented by the formula (1-55). The yield was 68%.

Identification of compound represented by formula (1-55) (mass spectrometry) ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 479.3
Exact Mass: 478.2

[Synthesis Example 7]
An appropriate amount of nitrogen was passed through a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the nitrogen atmosphere, and 300 parts of diethylene glycol ethyl methyl ether was added and heated to 85 ° C. with stirring. Then 54 parts of methacrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decan-8-yl acrylate and 3,4-epoxytricyclo [5.2.1.0 ^{2, 6} ] 306 parts of a mixture of decane-9-yl acrylate (content ratio is 50:50 in molar ratio) and 24 parts of 2,2-azobis (2,4-dimethylvaleronitrile) are dissolved in 316 parts of diethylene glycol ethyl methyl ether. The solution was dropped into the flask over 5 hours. After completion of dropping, the mixture was kept at 85 ° C. for 4 hours and then cooled to room temperature to obtain a copolymer solution. This copolymer is referred to as “resin C1”. The solid content of the resin C1 solution was 37.0% by weight, and the viscosity measured with a B-type viscometer (23 ° C.) was 88 mPa · s. The weight average molecular weight of Resin C1 was 7.5 × 10 ³ , the acid value in terms of solid content was 91 mg-KOH / g, and the molecular weight distribution was 1.93. Resin C1 has the following structural units.

[Synthesis Example 8]
A suitable amount of nitrogen was passed through a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the nitrogen atmosphere, and 371 parts of propylene glycol monomethyl ether acetate was added and heated to 85 ° C. with stirring. Then 54 parts acrylic acid, 3,4-epoxy tricyclo [5.2.1.0 ^2,6 ] decan-8-yl acrylate and 3,4-epoxy tricyclo [5.2.1.0 ^{2, 6} ] A mixed solution prepared by dissolving 225 parts of a mixture of decan-9-yl acrylate (content ratio is 50:50 by mole) and 81 parts of vinyltoluene (isomer mixture) in 80 parts of propylene glycol monomethyl ether acetate. Was dropped into the flask over 4 hours.
On the other hand, a solution prepared by dissolving 30 parts of a polymerization initiator 2,2-azobis (2,4-dimethylvaleronitrile) in 160 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After completion of the dropwise addition of the initiator solution, the mixture was kept at 85 ° C. for 4 hours and then cooled to room temperature to obtain a copolymer solution. This copolymer is referred to as "resin C2." The solid content of the resin C2 solution was 37.5%, and the viscosity measured with a B-type viscometer (23 ° C.) was 246 mPa · s. Resin C2 had a weight average molecular weight of 1.06 × 10 ⁴ , an acid value in terms of solid content of 115 mg-KOH / g, and a molecular weight distribution of 2.01. Resin C2 has the following structural units.

[Synthesis Example 9]
After introducing 182 g of propylene glycol monomethyl ether acetate into a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel and a nitrogen introduction tube, and changing the atmosphere in the flask from air to nitrogen, the temperature was raised to 100 ° C., 70.5 g (0.40 mol) of benzyl methacrylate, 43.0 g (0.5 mol) of methacrylic acid, 22.0 g (0.10 mol) of monomethacrylate having a tricyclodecane skeleton (FA-513M manufactured by Hitachi Chemical Co., Ltd.) ) And 136 g of propylene glycol monomethyl ether acetate, a solution obtained by adding 3.6 g of 2,2′-azobisisobutyronitrile was added dropwise, and stirring was continued at 100 ° C.
Next, the atmosphere in the flask was changed from nitrogen to air, and 35.5 g of glycidyl methacrylate [0.25 mol, (50 mol% with respect to the carboxyl group of methacrylic acid used in this reaction)], trisdimethylaminomethylphenol, 0.5%. 9 g and 0.145 g of hydroquinone were charged into the flask, and the reaction was continued at 110 ° C. to obtain a resin C3 solution having a solid content acid value of 79 mgKOH / g. The weight average molecular weight in terms of polystyrene measured by GPC was 30,000.

[Synthesis Example 10]
Nitrogen was flowed at 0.02 L / min into a flask equipped with a stirrer, thermometer, reflux condenser and dropping funnel to form a nitrogen atmosphere, 305 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 70 ° C. with stirring. did. Next, 60 parts of acrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl acrylate (a compound represented by the formula (I-1) and a formula (II-1) The compound is mixed in a molar ratio of 50:50.) A solution is prepared by dissolving in 440 parts and 140 parts of propylene glycol monomethyl ether acetate, and the solution is added using a dropping funnel over 4 hours. It was dripped in the flask kept at 70 degreeC.

  On the other hand, a solution prepared by dissolving 30 parts of a polymerization initiator 2,2′-azobis (2,4-dimethylvaleronitrile) in 225 parts of propylene glycol monomethyl ether acetate was placed in a flask using another dropping funnel over 4 hours. It was dripped. After completion of the dropwise addition of the polymerization initiator solution, the mixture was kept at 70 ° C. for 4 hours, and then cooled to room temperature. The weight average molecular weight Mw was 9073, the molecular weight distribution was 2.16, the solid content was 34.8%, A resin C4 solution having a solution acid value of 28 mg KOH / g (acid value in terms of solid content is 81 mg KOH / g) was obtained.

The weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin obtained in the synthesis example were measured using the GPC method under the following conditions.
Apparatus; K2479 (manufactured by Shimadzu Corporation)
Column; SHIMADZU Shim-pack GPC-80M
Column temperature: 40 ° C
Solvent; THF (tetrahydrofuran)
Flow rate: 1.0 mL / min
Detector; RI
Standard material for calibration: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)
The polystyrene-converted weight average molecular weight and number average molecular weight ratio (Mw / Mn) obtained above was defined as molecular weight distribution.

[Example 1]
(Preparation of colorant dispersion 1)
Xanthene dye (a1); compound represented by formula (1-32) 9.60 parts solvent (B); propylene glycol monomethyl ether acetate 58.21 parts solvent (B); propylene glycol monomethyl ether 5.76 parts resin ( C); Resin C2 (converted to solid content) 3.17 parts Dispersant (D); Acrylic dispersant (Disperbyk (registered trademark) 2000; manufactured by BYK Chemie; amine value 4 mg KOH / g) 3.70 parts; 360 parts of zirconia beads having a diameter of 2 mm were put into a mayonnaise bottle having a capacity of 140 ml, and kneaded at 60 ° C. for 10 hours with a paint conditioner for dispersion treatment. Thereafter, the zirconia beads were removed to obtain a dispersion. The dispersion was filtered through a membrane filter having a pore size of 1.0 μm to obtain a colorant dispersion 1.
In addition, about the compound represented by Formula (1-32), the solubility to the propylene glycol monomethyl ether acetate / propylene glycol monomethyl ether solvent (content ratio is 9/1 on a mass basis) at 23 ° C. was 3%. .

(Preparation of colored curable composition)
The following components were mixed to obtain a colored curable composition.
Colorant dispersion 1 28 parts Polymerizable compound (E): Dipentaerythritol hexaacrylate ((KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts Polymerization initiator (F); N-benzoyloxy- 1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF; O-acyloxime compound) 5 parts Polymerization initiator (F); 2-methyl- 2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one (Irgacure (registered trademark) 907; manufactured by BASF; alkylphenone compound) 2 parts Polymerization initiator (F1); 2,4-diethylthioxanthone (KAYACURE (registered trademark) DETX; manufactured by Nippon Kayaku Co., Ltd .; thioxanthone compound) 10 parts Agent (G): Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.2 part Resin (C ′): Resin C1 solution 99 parts Solvent (B ′): Propylene glycol monomethyl ether acetate 456 parts Solvent (B '): 186 parts of propylene glycol monomethyl ether Pigment composition 1 258 parts

However, the pigment composition 1 was prepared as follows.
(Preparation of pigment composition 1)
Pigment (A2); C.I. I. Pigment Blue 15: 6 9.22 parts Solvent (B ″); Propylene glycol monomethyl ether acetate 58.21 parts Solvent (B ″); Propylene glycol monomethyl ether 5.76 parts Resin (C ″); Resin C2 ( 3.17 parts Pigment dispersant (D ′); Copper phthalocyanine derivative (Solsperse 5000; manufactured by Lubrizol) 0.38 parts Pigment dispersant (D ′); Acrylic dispersant (Disperbyk (registered trademark)) 2000; manufactured by Big Chemie) 3.26 parts were mixed, and the pigment was sufficiently dispersed using a bead mill to obtain pigment composition 1.

[Comparative Example 1]
Pigment: C.I. I. Pigment Blue 15: 6 20 parts Acrylic pigment dispersant 5 parts Propylene glycol monomethyl ether acetate 137 parts are mixed, and the pigment is sufficiently dispersed using a bead mill.
Colorant: Dye A1 (Formula (A1-1) to Formula (A1-8)) 3.5 parts Resin: Resin C3 solution 157 parts Polymerizable compound: Dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd.)
50 parts Polymerization initiator: OXE-01 (manufactured by Ciba Specialty Chemicals) 15 parts Solvent: 289 parts of 4-hydroxy-4-methyl-2-pentanone were mixed to obtain a colored curable composition.

[Comparative Example 2]
Pigment: C.I. I. Pigment Blue 15: 6 12 parts Dye: Dye A1 (Formula (A1-1) to Formula (A1-8)) 1.8 parts Dispersant 1: Acrylic dispersant (Disperbyk (registered trademark) -116; manufactured by Big Chemie) Amine value 65 mgKOH / g) 18.1 parts
Dispersant 2: Copper phthalocyanine derivative (Solsperse 5000, manufactured by Avicia) 0.4 part Solvent 1: 47.9 parts of propylene glycol monomethyl ether acetate were sequentially added to a beaker, and all components were mixed. Then, the dispersion process was performed for 5 hours with the paint shaker using the zirconia bead of 0.65 mm diameter. The obtained uniform dispersion was filtered to remove the beads, whereby a pigment composition 2 was obtained.

(Preparation of colored curable composition)
The following components were mixed to obtain a colored curable composition.
Pigment composition 2 223 parts Resin: Resin C3 solution 133 parts Polymerizable compound: (E): Dipentaerythritol hexaacrylate ((KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts Polymerization initiator (F ); N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF; O-acyloxime compound) 15 parts Leveling agent (G ): Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.1 part Solvent (B ′): 425 parts of propylene glycol monomethyl ether acetate

[Comparative Example 3]
(Preparation of colorant dispersion 2)
Xanthene dye (a1); compound represented by formula (1-32) 9.60 parts solvent (B); propylene glycol monomethyl ether acetate 58.21 parts solvent (B); propylene glycol monomethyl ether 5.76 parts resin ( C); Resin C2 (in terms of solid content) 3.17 parts Dispersant (D); Acrylic dispersant (Disperbyk (registered trademark) -116; amine value 65 mgKOH / g, manufactured by Big Chemie) 3.26 parts, 0 360 parts of zirconia beads having a diameter of 2 mm were put into a mayonnaise bottle having a capacity of 140 ml, and kneaded at 60 ° C. for 10 hours with a paint conditioner for dispersion treatment. Thereafter, the zirconia beads were removed to obtain a dispersion. The dispersion was filtered through a membrane filter having a pore size of 1.0 μm to obtain a colorant dispersion 2.
In addition, about the compound represented by Formula (1-32), the solubility to the propylene glycol monomethyl ether acetate / propylene glycol monomethyl ether solvent (content ratio is 9/1 on a mass basis) at 23 ° C. was 3%. .

(Preparation of colored curable composition)
The following components were mixed to obtain a colored curable composition.
Colorant dispersion 2 28 parts Polymerizable compound (E): Dipentaerythritol hexaacrylate ((KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts Polymerization initiator (F); N-benzoyloxy- 1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF; O-acyloxime compound) 5 parts Polymerization initiator (F); 2-methyl- 2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one (Irgacure (registered trademark) 907; manufactured by BASF; alkylphenone compound) 2 parts Polymerization initiator (F1); 2,4-diethylthioxanthone (KAYACURE (registered trademark) DETX; manufactured by Nippon Kayaku Co., Ltd .; thioxanthone compound) 10 parts Agent (G): Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.2 part Resin (C ′): Resin C1 solution 99 parts Solvent (B ′): Propylene glycol monomethyl ether acetate 456 parts Solvent (B '): 186 parts of propylene glycol monomethyl ether Pigment composition 1 258 parts

<Preparation of colored pattern>
A colored curable composition was applied by spin coating on a 2-inch square glass substrate (Eagle XG; manufactured by Corning), and then pre-baked at 100 ° C. for 3 minutes to obtain a colored composition layer. After cooling, the distance between the colored composition layer and the quartz glass photomask substrate as 100 [mu] m, an exposure machine; using (TME-150RSK Topcon Co.), an air atmosphere of 40 mJ / cm ² It exposed with the exposure amount (365 nm reference | standard). A photomask having a 100 μm line and space pattern was used. The colored composition layer after exposure is immersed and developed in an aqueous developer containing 0.12% of a nonionic surfactant and 2% of sodium carbonate at 25 ° C. for 70 seconds, washed with water, and then in an oven at 230 ° C. for 20 minutes. Post-baking was performed to obtain a colored pattern.

<Film thickness measurement>
The film thickness of the obtained colored pattern was measured using a film thickness measuring device (DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd.). The results are shown in Table 1.

<Chromaticity evaluation>
About the obtained coloring pattern, spectrum was measured using the colorimeter (OSP-SP-200; Olympus Co., Ltd.), and the xy chromaticity coordinate in the XYZ color system of CIE using the characteristic function of C light source (X, y) and tristimulus value Y were measured. The larger the value of Y, the higher the brightness. The results are shown in Table 1.

<Contrast evaluation>
A colored coating film on a glass substrate was prepared by performing the same operation as that for forming a colored pattern except that the exposure was performed without using a photomask and development was not performed. About the obtained colored coating film, contrast was measured with a blank value of 30000 using a contrast meter (CT-1; manufactured by Aisaka Electric Co., Ltd., color difference meter BM-5A; manufactured by Topcon Co., Ltd., light source: F-10). did. A sample coated with a polarizing film (POLAX-38S; manufactured by Luceo Co., Ltd.) was used as a measurement sample. The results are shown in Table 1. If the contrast of the colored coating film is high, the same is true for the colored pattern obtained using the same colored curable composition.

[Example 2]
A colored composition is obtained by performing the same operation as in Example 1 except that the compound represented by formula (1-32) is replaced with the compound represented by formula (1-24) (xanthene dye (a2)). A colored curable composition is obtained in the same manner as in Example 1 except that this colored composition is used. The same operation as in Example 1 is performed, and a color filter with high brightness is obtained from the colored curable composition in the same manner as in Example 1.

Example 3
(Preparation of colorant dispersion 3)
Xanthene dye (a3); compound represented by formula (1-55) 4.80 parts solvent (B); propylene glycol monomethyl ether acetate 69.54 parts solvent (B); 4-hydroxy-4-methyl-2- Pentanone 2.64 parts Resin (C); Resin C2 (solid content conversion) 1.44 parts Dispersant (D); Acrylic dispersant Disperbyk (registered trademark) 2000 (manufactured by Big Chemie; amine value 4 mgKOH / g) 58 parts and 360 parts of 0.2 mm diameter zirconia beads were put into a mayonnaise bottle having a capacity of 140 ml, and kneaded at 60 ° C. for 10 hours with a paint conditioner for dispersion treatment. Thereafter, the zirconia beads were removed to obtain a dispersion. The dispersion was filtered through a membrane filter having a pore size of 1.0 μm to obtain a colorant dispersion 3.
In addition, about the compound represented by Formula (1-55), the propylene glycol monomethyl ether acetate / 4-hydroxy-4-methyl-2-pentanone solvent (content ratio is 9/1 on a mass basis) at 23 ° C. The solubility was 1%.

Example 4
(Preparation of colorant dispersion 4)
Xanthene dye (a3); Compound represented by formula (1-55) 4.00 parts Xanthene dye (a4); Compound represented by formula (1-51) 4.00 parts Solvent (B); Propylene glycol monomethyl Ether acetate 68.56 parts Solvent (B); 4-hydroxy-4-methyl-2-pentanone 2.40 parts Resin (C); Resin C2 (solid content conversion) 2.40 parts Dispersant (D); Acrylic Dispersant Disperbyk (registered trademark) 2000 (manufactured by Big Chemie; amine value 4 mg KOH / g) 1.58 parts and 360 parts of 0.2 mm diameter zirconia beads were charged into a 140 ml mayonnaise bottle, and a paint conditioner was used. The dispersion treatment was performed by kneading at 60 ° C. for 10 hours. Thereafter, the zirconia beads were removed to obtain a dispersion. The dispersion was filtered through a membrane filter having a pore size of 1.0 μm to obtain a colorant dispersion 4.

Example 5
(Preparation of colorant dispersion 5)
Xanthene dye (a4); compound represented by formula (1-51) 8.00 parts solvent (B); propylene glycol monomethyl ether acetate 62.55 parts solvent (B); propylene glycol monomethyl ether 4.41 parts resin ( C); Resin C2 (in terms of solid content) 2.40 parts Dispersant (D); Acrylic dispersant Disperbyk (registered trademark) 2000 (manufactured by Big Chemie; amine value 4 mg KOH / g) 2.64 parts, 0.2 mm 360 parts of zirconia beads having a diameter were put into a mayonnaise bottle having a capacity of 140 ml, and kneaded at 60 ° C. for 10 hours with a paint conditioner for dispersion treatment. Thereafter, the zirconia beads were removed to obtain a dispersion. The dispersion was filtered through a membrane filter having a pore size of 1.0 μm to obtain a colorant dispersion 5.
In addition, about the compound represented by Formula (1-51), the solubility to the propylene glycol monomethyl ether acetate / propylene glycol monomethyl ether solvent (content ratio is 9/1 on a mass basis) at 23 ° C. is 1.5%. there were.

[Reference Example 1]
(Production of Pigment Composition 3)
Pigment composition 3 was prepared as follows.
Pigment (A2); C.I. I. Pigment Red 254 8.86 parts Solvent (B ″); Propylene glycol monomethyl ether acetate 58.24 parts Solvent (B ″); Propylene glycol monomethyl ether 5.76 parts Resin (C ″); Resin C2 (solid content Conversion) 3.30 parts Pigment dispersant (D ′); 3.84 parts of acrylic dispersant were mixed, and pigment composition 3 was obtained by sufficiently dispersing the pigment using a bead mill.

Example 6
(Preparation of colored curable composition)
The following components were mixed to obtain a colored curable composition.
Colorant dispersion 3 97 parts Polymerizable compound (E): Dipentaerythritol hexaacrylate ((KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts Polymerization initiator (F); N-benzoyloxy- 1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF; O-acyloxime compound) 13 parts Leveling agent (G): polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.1 part Resin (C ′): Resin C4 solution 50 parts Solvent (B ′): Propylene glycol monomethyl ether acetate 622 parts Solvent (B ′): 4-hydroxy -4-methyl-2-pentanone 22 parts Pigment composition 3 479 parts

Example 7
(Preparation of colored curable composition)
The following components were mixed to obtain a colored curable composition.
Colorant dispersion 4 57 parts Polymerizable compound (E): Dipentaerythritol hexaacrylate ((KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts Polymerization initiator (F); N-benzoyloxy- 1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF; O-acyloxime compound) 13 parts Leveling agent (G): polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.1 part Resin (C ′): Resin C4 solution 50 parts Solvent (B ′): Propylene glycol monomethyl ether acetate 438 parts Solvent (B ′): Propylene glycol monomethyl Ether 246 parts Pigment composition 3 483 parts

Example 8
(Preparation of colored curable composition)
The following components were mixed to obtain a colored curable composition.
Colorant dispersion 5 75 parts Polymerizable compound (E): Dipentaerythritol hexaacrylate ((KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts Polymerization initiator (F); N-benzoyloxy- 1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF; O-acyloxime compound) 13 parts Leveling agent (G): polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.1 part Resin (C ′): Resin C4 solution 50 parts Solvent (B ′): Propylene glycol monomethyl ether acetate 456 parts Solvent (B ′): Propylene glycol monomethyl Ether 226 parts Pigment composition 3 482 parts

  For the colored curable compositions obtained in Examples 6 to 8, in the same manner as the colored curable compositions of Example 1 and Comparative Examples 1 to 3, colored pattern production, film thickness measurement, chromaticity evaluation, A contrast evaluation was performed. The results are shown in Table 2.

  As Comparative Example 4, the dye A1 (formula (A1-1) to formula (A1-8)) and the pigment composition 3 were mixed, but the chromaticity was not comparable and the toning was impossible.

  A colored curable composition capable of forming a high brightness color filter is obtained from the colorant dispersion of the present invention.

Claims (8)

A colorant dispersion in which a colorant is dispersed in a solvent by a dispersant,
The colorant comprises a xanthene dye and is substantially free of pigment;
The xanthene dye content is 40% by mass or more and 100% by mass or less based on the total amount of the colorant,
A colorant dispersion in which the dispersant has an amine group and the dispersant has an amine value of 0 to 55 mgKOH / g.   The colorant dispersion according to claim 1, wherein the amine value of the dispersant is 2 to 40 mgKOH / g.   The colorant dispersion according to claim 1 or 2, wherein the solvent contains propylene glycol monomethyl ether acetate, and the content of propylene glycol monomethyl ether acetate is 40% by mass or more and 99% by mass or less based on the total amount of the solvent. liquid.   Furthermore, the coloring agent dispersion liquid in any one of Claims 1-3 containing resin.   The colored curable composition containing the coloring agent dispersion liquid in any one of Claims 1-4, a polymeric compound, and a polymerization initiator. A pigment composition prepared separately from the colorant dispersion;
The colored curable composition according to claim 5, wherein the pigment composition is a pigment composition comprising a pigment, a solvent, and at least one selected from the group consisting of a pigment dispersant and a resin.   A color filter formed from the colored curable composition according to claim 5. A display device comprising the color filter according to claim 7.