TW201821416A - Compound and colored curable resin composition - Google Patents

Abstract

To provide a colored curable resin composition capable of forming a color filter excellent in brightness, and to provide a compound contained in the composition. A compound is represented by formula (I) satisfying at least one of (i) to (vi): (i) Ris a saturated hydrocarbon group having -COOM and at least one of Rto Ris an aromatic hydrocarbon group, and -COOM is one piece; (ii) Rand Rare aromatic hydrocarbon groups having -COOM; (iii) Ris an aromatic hydrocarbon group having -COOM and Ris a saturated hydrocarbon group having -COOM; (iv) Ris a saturated hydrocarbon group having -COOM and Ris a saturated hydrocarbon group having -COOM, (v) Ris a saturated hydrocarbon group and Ris an aromatic hydrocarbon group having -COOM, and (vi) Rand Rare hydrogen atoms or saturated hydrocarbon groups, and at least one of Rand Rhas -COOM.

Description

Compound, colored curable resin composition, color filter and display device

FIELD OF THE INVENTION The present invention relates to compounds and colored curable resin compositions.

BACKGROUND OF THE INVENTION A color filter used in a display device such as a liquid crystal display device, an electroluminescence display device, and a plasma display uses a colored curable resin composition at the time of manufacture. As such a coloring curable resin composition, a coloring curable resin composition containing a compound represented by the following formula or the like is known:

[Chemical 1] . Patent Literature

Patent Document 1: Japanese Patent Application Laid-Open No. 2010-32999

SUMMARY OF THE INVENTION Problems to be Solved by the Invention In some cases, the brightness of a color filter formed of a coloring curable resin composition containing a conventionally-known compound described above may not sufficiently meet requirements. Means to solve the problem

The present invention includes the following inventions. [1] a compound represented by formula (I). [Chemical 2] [In the formula (I), R ¹ to R ⁴ each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. -CH ₂ -contained in the hydrocarbon group may be replaced by -O-, -CO-, or -NR ^11- . R ¹ and R ² may form a ring containing a nitrogen atom together, and R ³ and R ⁴ may form a ring containing a nitrogen atom together. R ⁶ and R ⁷ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R ¹¹ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms. However, the compound represented by the formula (I) is required to satisfy at least one of the necessary conditions (i) to (vi): (i) R ¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms with -COOM, and R ² to R At least one of ⁴ is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, and one -COOM contained in one molecule is one. (Ii) R ¹ and R ³ are aromatic hydrocarbon groups having 6 to 10 carbon atoms having -COOM. (Iii) R ¹ is an aromatic hydrocarbon group having 6 to 10 carbon atoms having -COOM, and R ³ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM. (Iv) R ¹ is a saturated hydrocarbon group having 3 to 20 carbon atoms having -COOM, and R ³ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM. (V) R ¹ is a saturated hydrocarbon group having 1 to 20 carbons which may have a substituent, and R ² is an aromatic hydrocarbon group having 6 to 10 carbons having -COOM. (Vi) R ¹ and R ² are a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and at least one of R ³ and R ⁴ is an aromatic hydrocarbon group having 6 to 10 carbon atoms having -COOM . In (i) to (vi), M represents a hydrogen atom, Na ⁺ , K ⁺ , or ⁺ N (R ¹² ) _{4. The} four R ¹² may be the same or different. R ¹² represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms. [2] A colored curable resin composition comprising the compound described in [1], a resin (B), a polymerizable compound (C), and a polymerization initiator (D). [3] A color filter formed from the colored curable resin composition according to [2]. [4] A display device including the color filter according to [3]. Effect of the invention

By using the colored curable resin composition containing the compound of the present invention, a color filter excellent in brightness can be formed.

BEST MODE FOR CARRYING OUT THE INVENTION The compound of the present invention is represented by formula (I). The compounds of the present invention include tautomers, stereoisomers, and their salts. The components and functional groups exemplified below can be used individually or in combination.

[Chemical 3]

[In the formula (I), R ¹ to R ⁴ independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. -CH ₂ -contained in the saturated hydrocarbon group may be replaced by -O-, -CO-, or -NR ^11- . R ¹ and R ² may form a ring containing a nitrogen atom together, and R ³ and R ⁴ may form a ring containing a nitrogen atom together. R ⁶ and R ⁷ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R ¹¹ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms. However, the compound represented by formula (I) satisfies at least one of the necessary conditions (i) to (vi): (i) R ¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms with -COOM, and R ² to R ⁴ At least one of them is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, and one -COOM contained in one molecule is one. (Ii) R ¹ and R ³ are aromatic hydrocarbon groups having 6 to 10 carbon atoms having -COOM. (Iii) R ¹ is an aromatic hydrocarbon group having 6 to 10 carbon atoms having -COOM, and R ³ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM. (Iv) R ¹ is a saturated hydrocarbon group having 3 to 20 carbon atoms having -COOM, and R ³ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM. (V) R ¹ is a saturated hydrocarbon group having 1 to 20 carbons which may have a substituent, and R ² is an aromatic hydrocarbon group having 6 to 10 carbons having -COOM. (Vi) R ¹ and R ² are a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and at least one of R ³ and R ⁴ is an aromatic hydrocarbon group having 6 to 10 carbon atoms having -COOM . In (i) to (vi), M represents a hydrogen atom, Na ⁺ , K ⁺ , or ⁺ N (R ¹² ) _{4. The} four R ¹² may be the same or different. R ¹² represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms. ]

Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms in R ¹ to R ⁴ include phenyl, tolyl, xylyl, mesityl, propylphenyl, and butylphenyl.

Examples of the substituent which the aromatic hydrocarbon group may have include a halogen atom, -R ⁸ , -OH, -OR ⁸ , -SO ₃ H, -SO ₃ ^- Z ⁺ , -COOM, -CO ₂ R ⁸ ,- SR ⁸ , -SO ₂ R ⁸ , -SO ₃ R ^8, or -SO ₂ NR ⁹ R ¹⁰ , and these substituents preferably substitute a hydrogen atom contained in the aromatic hydrocarbon group. Among these, as a substituent group, preferably ^{_{-SO 3 H, -SO 3 - Z}} + and -SO ₂ NR ⁹ R ^10, more preferably -SO ₃ ^- Z ^+, -COOM, and -SO ₂ NR ⁹ R ^10. As this situation -SO ₃ ^- Z ^+, preferably _{^{-SO 3 - + N (R 11}} ) 4. In the aromatic hydrocarbon group, when -COOM is contained as a substituent, -COOM is preferably bonded to a meta position or a para position with respect to the bonding end. When R ¹ to R ⁴ are these groups, the colored curable resin composition of the present invention containing the compound (I) can form a color filter with little generation of foreign matter and excellent heat resistance.

R ⁸ represents a saturated hydrocarbon group having 1 to 20 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom. R ⁹ and R ¹⁰ independently represent a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH ₂ -contained in the saturated aliphatic hydrocarbon group may be -O-, -CO-,- NH- or -NR ⁸ -substitution, R ⁹ and R ¹⁰ may be combined with each other to form a 3 to 10 membered heterocyclic ring containing a nitrogen atom.

Examples of the saturated hydrocarbon group having 1 to 20 carbon atoms in R ¹ to R ⁴ and R ⁸ to R ¹² include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, and the like. Nonyl, decyl, dodecyl, cetyl, eicosyl and other linear alkyl groups; isopropyl, isobutyl, isopentyl, neopentyl, 2-ethylhexyl and other branches Chain alkyl; cycloaliphatic, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, tricyclodecyl and other alicyclic saturated hydrocarbon groups with 3 to 20 carbon atoms. The carbon number of the saturated hydrocarbon group is more preferably 1 to 10. The hydrogen atom contained in the saturated hydrocarbon group in R ¹ to R ⁴ may be substituted by, for example, -COOM as a substituent, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or a halogen atom. In the saturated hydrocarbon group represented by R ¹ to R ⁴ , a hydrogen atom bonded to a terminal carbon atom (primary carbon atom) is preferably substituted with a substituent. Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms in which a hydrogen atom of a saturated hydrocarbon group in R ¹ to R ⁴ can be substituted include those exemplified as the aromatic hydrocarbon group having 6 to 10 carbon atoms in R ¹ to R ⁴ . The same group. The hydrogen atom contained in the saturated hydrocarbon group in R ⁹ and R ¹⁰ may be substituted, for example, by a hydroxyl group or a halogen atom as a substituent.

Examples of the ring formed by R ¹ and R ² and the ring formed by R ³ and R ⁴ include, for example, the following rings. * Indicates a bonding end.

[Chemical 4]

Examples of -OR ⁸ include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, and dioxy Alkoxy and the like.

Examples of -CO ₂ R ⁸ include alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, hexyloxycarbonyl, and eicosyloxycarbonyl.

Examples of -SR ⁸ include alkylsulfanes such as methylsulfanyl, ethylsulfanyl, butylsulfanyl, hexylsulfanyl, decylsulfanyl, and eicosylsulfanyl. Base etc. Examples of -SO ₂ R ⁸ include alkyl groups such as methylsulfonyl, ethylsulfonyl, butylsulfonyl, hexylsulfonyl, decylsulfonyl, and eicosylsulfonyl. Sulfonyl and others. Examples of -SO ₃ R ⁸ include methoxysulfonyl, ethoxysulfonyl, propoxysulfonyl, tert-butoxysulfonyl, hexylsulfonyl, and eicosane. Alkoxysulfonyl and the like.

Examples of -SO ₂ NR ⁹ R ¹⁰ include sulfamoyl groups; N-methylsulfamomethyl groups, N-ethylsulfamomethyl groups, N-propylsulfamomethyl groups, and N-isopropyl groups. Sulfamoyl, N-butylsulfamoyl, N-isobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-pentyl Sulfamoyl, N- (1-ethylpropyl) sulfamoyl, N- (1,1-dimethylpropyl) sulfamoyl, N- (1,2-dimethylpropyl ) Sulfamoyl, N- (2,2-dimethylpropyl) sulfamoyl, N- (1-methylbutyl) sulfamoyl, N- (2-methylbutyl) ammonia Sulfonyl, N- (3-methylbutyl) sulfamoyl, N-cyclopentylsulfamomethyl, N-hexylsulfamomethyl, N- (1,3-dimethylbutyl) Sulfamoyl, N- (3,3-dimethylbutyl) sulfamolfydryl, N-heptylsulfamolyl, N- (1-methylhexyl) sulfamolyl, N- (1 , 4-Dimethylpentyl) sulfamoyl, N-octylsulfamoyl, N- (2-ethylhexyl) sulfamoyl, N- (1,5-dimethylhexyl) amino Sulfonyl, N- (1,1,2,2-tetramethylbutyl) sulfamoyl and other N-1 substituted sulfamomethyl groups; N, N-dimethylsulfamomethyl, N, N -Ethyl Methylsulfamoyl, N, N-diethylsulfamomethyl, N, N-propylmethylsulfamomethyl, N, N-isopropylmethylsulfamomethyl, N, N- Tert-butylmethylsulfamoyl, N, N-butylethylsulfamoyl, N, N-bis (1-methylpropyl) sulfamomethyl, N, N-heptylmethylsulfamoyl Amidino and other N, N-2 substituted sulfamoryl and the like.

Examples of the alkyl group having 1 to 6 carbon atoms in R ⁶ and R ⁷ include alkyl groups having 1 to 6 carbon atoms in the alkyl groups listed above. Among them, R ⁶ and R ^{7 are} preferably a hydrogen atom.

Examples of the aralkyl group having 7 to 10 carbon atoms in R ¹¹ to R ¹² include benzyl, phenylethyl, and phenylbutyl.

Z ⁺ is ⁺ N (R ¹¹ ) ₄ , Na ⁺ or K ⁺ , and is preferably ⁺ N (R ¹¹ ) ₄ . As the ⁺ N (R ¹¹ ) ₄ , at least two of the four R ¹¹ are preferably a saturated hydrocarbon group having 5 to 20 carbon atoms. The total carbon number of the four R ¹¹ is preferably 20 to 80, and more preferably 20 to 60.

However, the compound represented by formula (I) satisfies at least one of the necessary conditions (i) to (vi), and preferably satisfies at least one of the necessary conditions (i), (ii), (iv), and (v). : (I) R ¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms with -COOM, at least one of R ² to R ⁴ is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, and 1 molecule The contained -COOM is one. (Ii) R ¹ and R ³ are aromatic hydrocarbon groups having 6 to 10 carbon atoms having -COOM. (Iii) R ¹ is an aromatic hydrocarbon group having 6 to 10 carbon atoms having -COOM, and R ³ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM. (Iv) R ¹ is a saturated hydrocarbon group having 3 to 20 carbon atoms having -COOM, and R ³ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM. (V) R ¹ is a saturated hydrocarbon group having 1 to 20 carbons which may have a substituent, and R ² is an aromatic hydrocarbon group having 6 to 10 carbons having -COOM. (Vi) R ¹ and R ² are a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and at least one of R ³ and R ⁴ is an aromatic hydrocarbon group having 6 to 10 carbon atoms having -COOM . In (i) to (vi), M represents a hydrogen atom, Na ⁺ , K ⁺ , or ⁺ N (R ¹² ) _{4. The} four R ¹² may be the same or different. R ¹² represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.

M is particularly preferably a hydrogen atom. R ¹² is preferably a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or a benzyl group.

In the necessary condition (i), it is preferable that R ¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms (preferably a saturated hydrocarbon group having 1 to 10 carbon atoms) having COOM, and at least two of R ² to R ⁴ are optionally substituted. An aromatic hydrocarbon group having 6 to 10 carbon atoms. In addition, it is more preferable that R ¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms with COOM (preferably a saturated hydrocarbon group having 1 to 10 carbon atoms), and R ² and R ³ are aromatic hydrocarbon groups having 6 to 10 carbon atoms which may have a substituent. .

In the required condition (ii), R ² and R ⁴ are preferably a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and more preferably a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

In the requirement (iv), R ² and R ⁴ are preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. In addition, R ² is preferably a saturated hydrocarbon group having 3 to 20 carbon atoms having COOM, and more preferably R ¹ and R ² are saturated hydrocarbon groups having 3 to 10 carbon atoms having COOM.

In the requirement (v), it is more preferable that R ³ is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R ⁴ is an aromatic hydrocarbon group having 6 to 10 carbon atoms which has COOM.

As the compound (I), a compound represented by the formula (Ia) (hereinafter sometimes referred to as “compound (Ia)”) is preferred. Compound (Ia) may be its tautomer.

[Chemical 5]

[In the formula (Ia), R ²¹ to R ²⁴ each independently represent a hydrogen atom, —R ²⁶ or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. R ²¹ and R ²² may form a ring containing a nitrogen atom together, and R ²³ and R ²⁴ may form a ring containing a nitrogen atom together. R ²⁶ represents a saturated hydrocarbon group having 1 to 20 carbon atoms that may have COOM. M represents a hydrogen atom, Na ⁺ , K ⁺ , or ⁺ N (R ¹² ) _{4. The} four R ¹² may be the same or different. R ¹² represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms. However, the compound represented by formula (Ia) satisfies at least one of the necessary conditions (ia) to (via): (ia) at least one of R ²¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms with COOM, R At least one of ²² to R ²⁴ is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, and one -COOM contained in one molecule is one. (Iia) R ²¹ and R ²³ are aromatic hydrocarbon groups having 6 to 10 carbon atoms having COOM. (Iiia) R ²¹ is an aromatic hydrocarbon group having 6 to 10 carbon atoms having COOM, and R ²³ is a saturated hydrocarbon group having 1 to 20 carbon atoms having COOM. (Iva) R ²¹ is a saturated hydrocarbon group having 3 to 20 carbon atoms in COOM, and R ²³ is a saturated hydrocarbon group having 1 to 20 carbon atoms in COOM. (Va) R ²¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R ²² is an aromatic hydrocarbon group having 6 to 10 carbon atoms having COOM. (Via) R ²¹ and R ²² are a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R ²³ is an aromatic hydrocarbon group having 6 to 10 carbon atoms having COOM. ]

Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms in R ²¹ to R ²⁴ include the same groups as those exemplified as the aromatic hydrocarbon group in R ¹ to R ⁴ . A hydrogen atom contained in the aromatic hydrocarbon group may be _{^{-COOM, -SO 3 -, -SO 3}} H, -SO 3 - Z1 +, or a substituted -SO ₃ R ²⁵ -SO ₂ NHR ^25. When a hydrogen atom contained in the aromatic hydrocarbon group is replaced with -COOM, -COOM is preferably bonded to the meta or para position with respect to the bonding end. Z1 ⁺ is ⁺ N ( ^R27 ) ₄ , Na ^+, or K ⁺ , and is preferably ⁺ N ( ^R27 ) ₄ . R ²⁵ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms. R ²⁷ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a benzyl group. As the combination of R ²¹ - R ^24, preferably R ²¹ and R ²³ is a hydrogen atom, R ²² and R ²⁴ is an aromatic hydrocarbon group having a carbon number of 6 to 10, the hydrogen atoms contained in the aromatic hydrocarbon group is -SO ₃ ^{- _{, -SO 3 H, -SO 3 -}} Z1 +, -SO 3 R 26 or -SO ₂ NHR ²⁶ group. A more preferred combination is that R ²¹ and R ²³ are hydrogen atoms, R ²² and R ²⁴ are aromatic hydrocarbon groups having 6 to 10 carbon atoms, and the hydrogen atoms contained in the aromatic hydrocarbon groups are replaced by -SO ₃ ^- Z1 ⁺ or- SO ₂ NHR ²⁶ replaced.

Examples of the nitrogen atom-containing ring formed by R ²¹ and R ²² and the nitrogen atom-containing ring formed by R ²³ and R ²⁴ together include the same ring as the ring formed by R ¹ and R ² . Among them, aliphatic heterocycles are preferred. Examples of the aliphatic heterocyclic ring include the following aliphatic heterocyclic rings. * Indicates a bonding end.

[Chemical 6]

Examples of the saturated hydrocarbon group having 1 to 20 carbon atoms in R ²⁵ to R ²⁷ include the same groups as those listed as the saturated hydrocarbon group in R ⁸ to R ¹¹ . When R ²¹ to R ²⁴ are -R ²⁶ , -R ²⁶ is preferably each independently methyl or ethyl. When R ²¹ to R ²⁴ are -R ²⁶ and R ²⁶ has -COOM, it is preferable that a hydrogen atom bonded to a terminal carbon atom (primary carbon atom) of -R ²⁶ is replaced with -COOM. Further, -SO ₂ NHR ^26, and ²⁶ of R -SO ₃ R ^26, preferably branched chain alkyl group having a carbon number of 3 to 20 carbon atoms, more preferably branched chain alkyl group having 6 to 12, more preferably 2 Ethylhexyl.

As the ⁺ N (R ²⁷ ) ₄ , at least two of the four R ²⁷ are preferably a saturated hydrocarbon group having 5 to 20 carbon atoms. The total carbon number of the four R ²⁷ is preferably 20 to 80, and more preferably 20 to 60. When ⁺ N (R ²⁷ ) ₄ is present in the compound (Ia), R ²⁷ may be the same or different.

However, the compound represented by formula (Ia) satisfies at least one of the necessary conditions (ia) to (via), and preferably at least one of the necessary conditions (ia), (iia), (iva), and (va) : (Ia) R ²¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM, at least one of R ²² to R ²⁴ is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, and 1 molecule The contained -COOM is one. (Iia) R ²¹ and R ²³ are aromatic hydrocarbon groups having 6 to 10 carbon atoms having -COOM. (Iiia) R ²¹ is an aromatic hydrocarbon group having 6 to 10 carbon atoms having -COOM, and R ²³ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM. (Iva) R ²¹ is a saturated hydrocarbon group having 3 to 20 carbon atoms having -COOM, and R ²³ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM. (Va) R ²¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R ²² is an aromatic hydrocarbon group having 6 to 10 carbon atoms which has -COOM. (Via) R ²¹ and R ²² are hydrogen atoms or saturated hydrocarbon groups having 1 to 20 carbon atoms which may have a substituent, and at least one of R ²³ and R ²⁴ is an aromatic hydrocarbon group having 6 to 10 carbon atoms in -COOM .

M is particularly preferably a hydrogen atom. R ¹² is preferably a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or a benzyl group.

In the necessary condition (ia), it is preferred that R ²¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms (preferably a saturated hydrocarbon group having 1 to 10 carbon atoms) having -COOM, and at least two of R ²² to R ²⁴ may have a substitution. An aromatic hydrocarbon group having 6 to 10 carbon atoms. Preferably, R ²¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms (preferably a saturated hydrocarbon group having 1 to 10 carbon atoms) having -COOM, and R ²² and R ²³ are aromatic hydrocarbon groups having 6 to 10 carbon atoms which may have a substituent.

In the required condition (iia), R ²² and R ²⁴ are preferably a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and more preferably a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

In the necessary condition (iva), R ²² and R ²⁴ are preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. In addition, R ²² is preferably a saturated hydrocarbon group having 3 to 20 carbon atoms having -COOM, and more preferably R ²¹ and R ²² are saturated hydrocarbon groups having 3 to 10 carbon atoms having -COOM.

In the requirement (va), it is more preferable that R ²³ is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R ²⁴ is an aromatic hydrocarbon group having 6 to 10 carbon atoms which is -COOM.

Moreover, as a compound (I), the compound represented by Formula (Ib) (henceforth a "compound (Ib)" may be mentioned). The compound (Ib) may be its tautomer.

[Chemical 7]

[In the formula (Ib), R ³¹ and R ³² independently represent a saturated hydrocarbon group having 1 to 10 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon groups of R ³¹ and R ³² may be -COOM and 6 to 10 carbon atoms. The aromatic hydrocarbon group or halogen atom is substituted, the hydrogen atom contained in the aromatic hydrocarbon group may be substituted with -COOM or an alkoxy group having 1 to 3 carbon atoms, and -CH contained in the saturated hydrocarbon group of R ³¹ and R ³² described above ₂ -can be replaced by -O-, -CO- or -NR ^11- . R ³³ and R ³⁴ independently represent -COOM, an alkyl group having 1 to 4 carbon atoms, an alkylsulfanyl group having 1 to 4 carbon atoms, or an alkylsulfonyl group having 1 to 4 carbon atoms. R ³¹ and R ³³ may form a ring containing a nitrogen atom together, and R ³² and R ³⁴ may form a ring containing a nitrogen atom together. p and q each independently represent an integer of 0 to 5. When p is 2 or more, a plurality of R ³³ may be the same or different, and when q is 2 or more, a plurality of R ³⁴ may be the same or different. R ¹¹ has the same meaning as described above. M represents a hydrogen atom, Na ⁺ , K ⁺ , or ⁺ N (R ¹² ) _{4. The} four R ¹² may be the same or different. R ¹² represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms. However, the compound represented by the formula (Ib) satisfies at least one of the necessary conditions (ib) to (ivb): (ib) R ³¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms with -COOM, contained in one molecule -COOM is 1. (Iib) At least one of R ³³ and R ³⁴ is -COOM. (Iiib) R ³¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM, and R ³⁴ is -COOM. (Ivb) R ³¹ is a saturated hydrocarbon group having 3 to 20 carbon atoms in -COOM, and R ³² is a saturated hydrocarbon group having 1 to 20 carbon atoms in -COOM. ]

Examples of the saturated hydrocarbon group having 1 to 10 carbon atoms in R ³¹ and R ³² include a group having 1 to 10 carbon atoms in the saturated hydrocarbon group in R ⁸ . Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent include the same groups as the aromatic hydrocarbon group in R ¹ . When a saturated hydrocarbon group represented by R ³¹ and R ³² is substituted with -COOM, a hydrogen atom bonded to a terminal carbon atom (primary carbon atom) is preferably substituted with -COOM. Examples of the alkoxy group having 1 to 3 carbon atoms include a methoxy group, an ethoxy group, and a propoxy group. R ³¹ and R ³² are each independently a 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 methyl, ethyl, propyl, butyl, isopropyl, isobutyl, sec-butyl, and tert-butyl. Examples of the alkylsulfanyl group having 1 to 4 carbon atoms in R ³³ and R ³⁴ include methylsulfanyl group, ethylsulfanyl group, propylsulfanyl group, butylsulfanyl group, and isopropyl group. Sulfanyl and the like. Examples of the alkylsulfonyl group having 1 to 4 carbon atoms in R ³³ and R ³⁴ include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl and isopropyl Sulfonyl and others. R ³³ and R ^{34 are} preferably -COOM or an alkyl group having 1 to 4 carbon atoms, and more preferably -COOM or methyl. When R ³³ and R ³⁴ are -COOM, -COOM is preferably bonded to the meta or para position with respect to the carbon atom bonded to N.

p and q are preferably integers of 0 to 2, and 1 or 2 is preferred.

However, the compound represented by the formula (Ib) preferably satisfies at least one of the requirements (ib) to (ivb), and preferably satisfies at least one of the requirements (ib), (iib), and (ivb). (Ib) R ³¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM, and -COOM contained in one molecule is one. (Iib) At least one of R ³³ and R ³⁴ is -COOM. (Iiib) R ³¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM, and R ³⁴ is -COOM. (Ivb) R ³¹ is a saturated hydrocarbon group having 3 to 20 carbon atoms in -COOM, and R ³³ is a saturated hydrocarbon group having 1 to 20 carbon atoms in -COOM.

M is particularly preferably a hydrogen atom. R ¹² is preferably a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or a benzyl group.

In the requirement (iib), it is preferable that both R ³³ and R ³⁴ are -COOM.

In the necessary condition (ivb), R ³³ is preferably a saturated hydrocarbon group having 3 to 20 carbon atoms in -COOM, and R ³³ and R ^{34 are} more preferably a saturated hydrocarbon group having 3 to 10 carbon atoms in -COOM.

Examples of the compound (I) include compounds represented by the formulae (Aa-1) to (Aa-52).

[Chemical 8]

[Chemical 9]

[Chemical 10]

[Chemical 11]

[Chemical 12]

[Chemical 13]

[Chemical 14]

The colored curable resin composition of the present invention includes a compound (I) as a colorant (A), a resin (B), a polymerizable compound (C), and a polymerization initiator (D).

In the colored curable resin composition of the present invention, the content of the compound (I) is preferably 0.1 to 20% by mass, and more preferably 0.5 to 10% by mass, with respect to the total amount of the solid content of the colored curable resin composition. It is more preferably 0.5 to 5% by mass.

<Colorant (A)> The colorant (A) may contain a dye (A1) and a pigment (A2) in addition to the compound (I).

The dye (A1) is not particularly limited, and known dyes can be used, and examples thereof include solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of the dye include a compound classified as a substance having a color tone other than a pigment in the Outstanding Index (published by The Society of Dyers and Colourists), and a well-known dye described in Dyeing Notes (Dyeing Society). In addition, the chemical structure includes azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, methine dyes, and azo dyes. Methyl base dyes, squaric acid dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, etc. Among these, organic solvent-soluble dyes are preferred. The compound (I) is included in the dye (A1).

Specific examples include CI Solvent Yellow 4 (hereinafter, the description of CI Solvent Yellow is omitted and only the serial number is described), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189; CI Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 218, 222, 227 , 230, 245, 247; CI Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86; CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48 , 51, 59, 60; CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59: 1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32 , 33, 34, 35 and other CI solvent dyes, CI acid yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51 , 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150 , 151, 155, 158, 160, 172, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268 , 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426 ; CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173; CI Acid Violet 6B , 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; CI Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90: 1, 91, 92, 93, 93: 1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324: 1, 335, 340; CI Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50 : 1, 58, 63, 65, 80, 104, 105, 106, 109 and other CI acid dyes, CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141; CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98 , 99, 105, 106, 107, 172, 173 , 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Direct Purple 47, 52, 54, 59, 60, 65, 66, 79 , 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 and other CI direct dyes, CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI disperse dyes such as CI disperse blue 1, 14, 56, 60, CI basic red 1, 10; CI basic blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; CI Basic Violet 2; CI base Red 9; CI basic dyes such as CI Basic Green 1, CI reactive yellow 2, 76, 116; CI reactive orange 16; CI reactive red 36 and other CI reactive dyes; CI mordant yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI mordant red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23 , 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74 , 76, 78, 85, 86, 88, 90, 94, 95; CI Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47 48; CI Mordant Violet 1, 1: 1,2,3,4,5,6,7,8,10,11,14,15,16,17,18,19,21,22,23,24,27 , 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI mordant blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; CI mordant green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53 and other CI mordant dyes, CI Reduction of CI reducing dyes such as Green 1. These dyes can be appropriately selected according to the spectroscopic spectrum of the desired color filter.

The content of the compound (I) in the dye (A1) is preferably 1 to 99% by mass, more preferably 30 to 90% by mass, and still more preferably 40 to 80% by mass with respect to the total amount of the dye (A1).

The dye (A1) preferably contains an anthraquinone dye (Ad).

As the anthraquinone dye (Ad), a known substance can be used. Examples of the anthraquinone dye (Ad) include CI solvent yellow 117, 163, 167, 189, CI solvent orange 77, 86, CI solvent red 111, 143, 145, 146, 150, 151, 155, 168, and 169. , 172, 175, 181, 207, 222, 227, 230, 245, 247, CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60, CI Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111 , 112, 122, 128, 132, 136, 139, CI Solvent Green 3, 28, 29, 32, 33, CI Acid Red 80, CI Acid Green 25, 27, 28, 41, CI Acid Violet 34, CI Acid Blue 25, 27, 40, 45, 78, 80, 112 CI Disperse Yellow 51, CI Disperse Purple 26, 27, CI Disperse Blue 1, 14, 56, 60, CI Direct Blue 40, CI Mordant Red 3, 11, CI Mordant Blue 8 and so on. The anthraquinone dye (Ad) is preferably dissolved in an organic solvent, and more preferably a cyan, purple or red anthraquinone dye.

Among these, as the anthraquinone dye (Ad), a compound represented by the formula (1d) (hereinafter sometimes referred to as "compound (1d)") is preferable.

[Chemical 15]

[In formula (1d), R ⁹¹ and R ⁹² each independently represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, an alicyclic hydrocarbon group having 3 to 10 carbon atoms which may have a substituent, Or by formula (1d ')

[Chemical 16]

(In formula (1d '), R ⁹³ represents an alkyl group having 1 to 6 carbon atoms, a halogen atom, -SO ₃ H, -CO ₂ H, -CO ₂ R ⁹⁴ , -NHCOR ⁹⁴ , -SO ₃ R ⁹⁴ , or- SO ₂ NR ⁹⁴ R ^95. R ⁹⁴ represents an aliphatic hydrocarbon group having 1 to 10 carbon atoms or an alicyclic hydrocarbon group having 3 to 10 carbon atoms. The hydrogen atom contained in the aliphatic hydrocarbon group or the alicyclic hydrocarbon group may be halogenated. Atom, hydroxyl or amino substitution. R ⁹⁵ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 10 carbon atoms. R represents an integer of 0 to 5. When r is 2 or more, a plurality of R ⁹³ may be the same or different. X ⁹¹ represents a single bond or an alkylene group having 1 to 6 carbon atoms.) A group represented by ⁹¹ . ]

When the compound (1d) has -SO ₃ H and / or -CO ₂ H, they may form a salt (for example, Na salt, K salt).

Examples of the aliphatic hydrocarbon group having 1 to 10 carbon atoms in R ⁹¹ and R ⁹² , R ⁹⁴ and R ⁹⁵ include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl. Base, nonyl, decyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, 2-ethylhexyl and the like. Examples of the substituent which these aliphatic hydrocarbon groups may have include a hydroxyl group, a halogen atom, or an amino group, and a hydroxyl group or a halogen atom is preferred.

Examples of the alicyclic hydrocarbon group having 3 to 10 carbon atoms represented by R ⁹¹ , R ⁹² and R ⁹⁴ include cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and tricyclodecyl. . As a substituent which these alicyclic hydrocarbon groups may have, a hydroxyl group, a halogen atom, or an amino group etc. are mentioned, A hydroxyl group or a halogen atom is preferable.

Examples of the alkyl group having 1 to 6 carbon atoms represented by R ⁹³ include methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, sec-butyl, and tert-butyl. Base, isopentyl, neopentyl, etc.

Examples of -CO ₂ R ⁹⁴ include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a hexyloxycarbonyl group, and an eicosyloxycarbonyl group.

Examples of -NHCOR ⁹⁴ include N-ethylamino, N-propylamino, N-butylamino, N-isobutylamido, N-neopentylamino, and the like.

Examples of -SO ₃ R ⁹⁴ include methoxysulfonyl, ethoxysulfonyl, propoxysulfonyl, tert-butoxysulfonyl, hexylsulfonyl, and eicosyloxy. Sulfosulfenyl and the like.

Examples of -SO ₂ NR ⁹⁴ R ⁹⁵ include N-methylsulfamominyl, N-ethylsulfamominyl, N-propylsulfamominyl, N-isopropylsulfamominyl, and N -Butylsulfamoyl, N-isobutylsulfamomethyl, N-sec-butylsulfamomethyl, N-tert-butylsulfamomethyl, N-pentylsulfamomethyl, N- ( 1-ethylpropyl) sulfamoyl, N- (1,1-dimethylpropyl) sulfamoyl, N- (1,2-dimethylpropyl) sulfamoyl, N- (2,2-Dimethylpropyl) sulfamoyl, N- (1-methylbutyl) sulfamomethyl, N- (2-methylbutyl) sulfamomethyl, N- (3 -Methylbutyl) sulfamoyl, N-cyclopentylsulfamomethyl, N-cyclohexylsulfamomethyl, N-hexylsulfamomethyl, N- (1,3-dimethylbutyl ) Sulfamoyl, N- (3,3-dimethylbutyl) sulfamoyl, N-heptylsulfamoyl, N- (1-methylhexyl) sulfamoyl, N- ( 1,4-dimethylpentyl) sulfamoyl, N-octylsulfamoyl, N- (2-ethylhexyl) sulfamoyl, N- (1,5-dimethyl) hexyl N- (1,1,2,2-tetramethylbutyl) sulfamoyl, N- (5-aminopentyl) sulfamoyl and other N-1 substituted sulfamoyl groups N, N-dimethylsulfamominyl, N, N-ethylmethylsulfamominyl, N, N-diethylsulfamominyl, N, N-propylmethylsulfamominyl, N, N-Isopropylmethylsulfamoyl, N, N-tert-butylmethylsulfamoyl, N, N-butylethylsulfamoyl, N, N-bis (1-methyl Propyl) sulfamoyl, N, N-heptylmethylsulfamoyl, etc. N, N-2 substituted sulfamoyl and the like.

Examples of the alkylene group having 1 to 6 carbon atoms in X ⁹¹ include methylene, ethylene, propane-1,3-diyl, propane-1,2-diyl, and butane-1,4. -Diyl, pentane-1,5-diyl, hexane-1,6-diyl, ethane-1,1-diyl, butane-1,3-diyl, 2-methylpropane- 1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, 2-methylbutane-1,4-diyl, and the like.

R ⁹³ is preferably an alkyl group having 1 to 5 carbon atoms which may have a hydroxyl group, -SO ₃ R ⁹⁴ , -SO ₂ NR ⁹⁴ R ⁹⁵ , more preferably -SO ₂ NR ⁹⁴ R ⁹⁵ , and still more preferably -SO ₂ NHR ⁹⁴ ( In each formula, R ⁹⁴ and R ⁹⁵ have the same definitions as above).

Examples of the compound (1d) include compounds represented by the formulae (3-1) to (3-11).

[Chem. 17]

As the anthraquinone dye (Ad), a compound represented by the formula (1d), wherein R ⁹¹ and R ⁹² are a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a phenyl group which may have a halogen atom, and The compound represented by any one of the groups represented by) is more preferably a compound represented by the formula (3-4) or the formula (3-11).

When an anthraquinone dye (Ad) is contained, its content rate is preferably 1 to 99% by mass, more preferably 10 to 70% by mass, and still more preferably 20 to 60% by mass with respect to the total amount of the dye (A1).

The pigment (A2) is not particularly limited, and known pigments can be used, and examples thereof include pigments classified as pigments in the Outstanding Index (published by The Society of Dyers and Colourists). Examples of the pigment include CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 16, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214 and other yellow pigments; CI pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments; 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 and other red pigments; CI Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60 and other cyan pigments; CI Pigment Violet 1, 19, 23, 29, 32 , 36, 38 and other purple pigments; CI Pigment Green 7, 36, 58 and other green pigments; CI Pigment Brown 23 and 25 and other brown pigments; CI Pigment Black 1, 7 and other black pigments.

As the pigment, cyan pigments such as CI Pigment Blue 15, 15: 3, 15: 4, 15: 6, and 60 are preferred; purple pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, and 38 are more preferred, and CI pigments are more preferred. Blue 15: 3, 15: 6 and CI Pigment Violet 23, more preferably CI Pigment Blue 15: 6. By including the pigment described above, the transmission spectrum can be easily optimized, and the light resistance and chemical resistance of the color filter become good.

For pigments, resin treatment, surface treatment using pigment derivatives introduced with acidic or basic groups, etc., graft treatment of pigment surfaces with polymer compounds, etc. can be used if necessary, and sulfuric acid micronization method can be used. Such as a micronization process, such as an organic solvent, water, or the like for removing impurities, or an ionic impurity removal process, such as an ion exchange method. The pigment preferably has a uniform particle size. By performing a dispersion treatment by containing a pigment dispersant, a pigment dispersion liquid in a state where the pigment is uniformly dispersed in the solution can be obtained.

Examples of the pigment dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. These pigment dispersants may be used alone or in combination of two or more kinds. Examples of the pigment dispersant include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Froeren (manufactured by Kyoeisha Chemical Co., Ltd.), ソ ル ス パ ー ス (manufactured by Daika Co., Ltd.), EFKA (manufactured by CIBA) ), Ajax (manufactured by Ajinomoto Fusion Co., Ltd.), Disperbyk (manufactured by BYK Chemical Co., Ltd.), and the like. When using a pigment dispersant, it is preferable that it is 1 mass% or more and 100 mass% or less with respect to the total amount of a pigment (A2), and it is more preferable that it is 5 mass% or more and 50 mass% or less. When the use amount of the pigment dispersant is within the above range, there is a tendency that a pigment dispersion liquid in a uniform dispersed state is obtained.

In the colorant (A), the content ratio of the dye (A1) to the pigment (A2) (dye (A1) / pigment (A2)) is on a mass basis, usually 1/99 to 99/1, and preferably 3/97 ~ 40/60, more preferably 5/95 ~ 30/70.

The content of the colorant (A) is preferably 5 to 60% by mass, more preferably 8 to 55% by mass, and still more preferably 10 to 50% by mass with respect to the total amount of the solid content. When the content of the colorant (A) is within the above range, the color density when the color filter is made is sufficient, and the composition can contain a necessary amount of resin or polymerizable compound, so that a pattern with sufficient mechanical strength can be formed. Here, the “total amount of solid content” in the present specification refers to an amount obtained by removing the content of the solvent from the total amount of the colored curable resin composition. The total amount of the solid component and the content of each component relative to the solid component can be measured by a known analysis means such as liquid chromatography or gas chromatography.

<Resin (B)> The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of the resin (B) include the following resins [K1] to [K6]. Resin [K1]: It has a structural unit derived from at least one (a) (hereinafter sometimes referred to as “(a)”) selected from unsaturated carboxylic acid and unsaturated carboxylic anhydride, and derived from a ring having 2 to 4 carbon atoms. Copolymer of a monomeric ether structure and the structural unit of an ethylenically unsaturated monomer (b) (hereinafter sometimes referred to as "(b)"); Resin [K2]: having a structural unit derived from (a) and derived from (a) b) Copolymerization of a structural unit and a structural unit derived from a monomer (c) copolymerizable with (a) (however, it is different from (a) and (b).) (hereinafter sometimes referred to as "(c)") Resin [K3]: a copolymer having a structural unit derived from (a) and a structural unit derived from (c); resin [K4]: a structural unit having addition of (b) and a structural unit derived from (a) Copolymer with a structural unit derived from (c); Resin [K5]: a copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b) and a structural unit derived from (c); resin [K6] ]: Having a structural unit obtained by adding (a) to a structural unit derived from (b), and further adding a carboxylic anhydride, and (c) derived from A copolymer of structural units.

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, and citraconic acid Acid, mesaconic acid, itaconic acid, 3-vinyl phthalic acid, 4-vinyl phthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6 -Unsaturated dicarboxylic acids such as tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexene dicarboxylic acid; methyl-5-norbornene-2,3-dicarboxylic acid 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] heptane 2-ene, 5-carboxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-carboxy-6-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-6 -Ethylbicyclo [2.2.1] hept-2-ene and other bicyclic unsaturated compounds containing carboxyl groups; maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl Phthalic 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, etc. And dicarboxylic anhydrides; mono [2- (meth) acryloxyethyl] succinate, mono [2- (meth) acryloxyethyl] phthalate, and more Unsaturated mono [(meth) acryloxyalkyl] esters of polycarboxylic acids; unsaturated acrylates such as α- (hydroxymethyl) acrylic acid, which contain a hydroxyl group and a carboxyl group in the same molecule. Among these, acrylic acid, methacrylic acid, maleic anhydride and the like are preferred from the viewpoint of copolymerization reactivity and the solubility of the obtained resin in an alkaline aqueous solution.

(B) For example, a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an ethylene oxide ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond Polymerizable compound. (B) A monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloxy group is preferred. In addition, in this specification, "(meth) acrylic acid" means at least 1 sort (s) chosen from acrylic acid and methacrylic acid. The expressions "(meth) acrylfluorenyl" and "(meth) acrylate" have the same meaning.

Examples of (b) include a monomer (b1) having an ethylene oxide group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), 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)"), and the like.

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

Examples of (b1-1) include glycidyl (meth) acrylate, β-methylglycidyl (meth) acrylate, β-ethylglycidyl (meth) acrylate, and 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-tris (glycidyloxymethyl) styrene, etc.

Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (for example, セ ロ キ サ イ ド 2000; manufactured by Daicel), and (methyl ) 3,4-epoxycyclohexyl methyl acrylate (e.g., Acromel A400; manufactured by Daicel); 3,4-epoxycyclohexyl methyl (meth) acrylate (e.g., M100; Co., Ltd.), a compound represented by formula (BI), a compound represented by formula (BII), and the like.

[Chemical 18]

[In formulae (BI) and (BII), 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 may be substituted with a hydroxyl group. X ^a and X ^b represents a single ^{bond, * - R c -, *} - R c -O -, * - R c -S- or * -R ^c -NH-. R ^c represents an alkylene group having 1 to 6 carbon atoms. * Indicates a bonding end with O. ]

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

Examples of the alkylene group include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, and pentane-1,5. -Diyl, hexane-1,6-diyl and the like. As X ^a and X ^b , a single bond, methylene, ethylene, * -CH ₂ -O- and * -CH ₂ CH ₂ -O- are preferable, and a single bond, *-is more preferable. CH ₂ CH ₂ -O- (* indicates a bonding end with O).

Examples of the compound represented by the formula (BI) include compounds represented by any one of the formulae (BI-1) to (BI-15). Among them, it is preferable to use formula (BI-1), formula (BI-3), formula (BI-5), formula (BI-7), formula (BI-9), or formula (BI-11) to formula (BI- The compound represented by 15) is more preferably a compound represented by formula (BI-1), formula (BI-7), formula (BI-9) or formula (BI-15).

[Chemical 19]

[Chemical 20]

Examples of the compound represented by the formula (BII) include compounds represented by any one of the formulae (BII-1) to (BII-15). Among them, it is preferable to use formula (BII-1), formula (BII-3), formula (BII-5), formula (BII-7), formula (BII-9), or formula (BII-11) to formula (BII- The compound represented by 15) is more preferably a compound represented by formula (BII-1), formula (BII-7), formula (BII-9) or formula (BII-15).

[Chemical 21]

[Chemical 22]

The compound represented by the formula (BI) and the compound represented by the formula (BII) may be used individually, or two or more kinds may be used in combination. When a compound represented by formula (BI) and a compound represented by formula (BII) are used in combination, their content ratio [compound represented by formula (BI): compound represented by formula (BII)] is expressed on a molar basis, It is preferably 5:95 to 95: 5, and more preferably 20:80 to 80:20.

As (b2), a monomer having an oxetanyl group and a (meth) acryloxy group is more preferable. Examples of (b2) include 3-methyl-3-methacryloxymethyloxetane, 3-methyl-3-propenyloxymethyloxetane, 3- Ethyl-3-methacryloxymethyloxetane, 3-ethyl-3-propenemethyloxetane, 3-methyl-3-methacryloxy Ethylethyloxetane, 3-methyl-3-propenyloxyethyloxetane, 3-ethyl-3-methacryloxyethyloxetane, 3 -Ethyl-3-propenyloxyethyloxetane and the like.

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

As (b), it is preferable that (b1) is the point which can further improve the reliability, such as heat resistance and chemical resistance, of the obtained color filter. Furthermore, (b1-2) is more preferable at the point which is excellent in the storage stability of a coloring curable resin composition.

Examples of (c) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, and t-butyl (meth) acrylate. Ester, 2-ethylhexyl (meth) acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate , Cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decane-8-yl ester (in this technical field As a common name, it is called "dicyclopentyl (meth) acrylate." In addition, it is sometimes called "tricyclodecyl (meth) acrylate."), Tricyclo (meth) acrylate [5.2.1.0 ^2,6 ] decene-8-yl ester (in this technical field, as a common name, it is called "dicyclopentenyl (meth) acrylate".), Dicyclopentyloxyethyl (meth) acrylate, ( Isobornyl (meth) acrylate, adamantane (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, (Meth) acrylates such as phenyl (meth) acrylate, naphthyl (meth) acrylate, benzyl (meth) acrylate; 2-hydroxyethyl (meth) acrylate, 2-hydroxy (meth) acrylate (Meth) acrylic esters containing hydroxy groups such as propyl esters; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconic acid; bicyclic [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-bis (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] Geng- 2-ene, 5-cyclohexyloxycarbonyl bicyclo [2.2.1] hept-2-ene, 5-phenoxycarbonylbicyclo [2.2.1] hept-2-ene, 5,6-bis (tert-butane Oxycarbonyl) bicyclic [2.2.1] hept-2-ene, 5,6-bis (cyclohexyloxycarbonyl) bicyclo [2.2.1] hept-2-ene, and other bicyclic unsaturated compounds; N-phenyl Maleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimide-3-maleimide benzoate, N-succinimide Amino-4-maleimide iminobutyrate, N-succinimide imino-6-maleimide hexanoate, N-succinimide imino-3-maleimide propionate, N -(9-acridyl) maleimide and other dicarbonylimine derivatives; styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyl toluene, P-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene and the like. Among these, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, and N-benzylmaleimide are preferred from the viewpoint of copolymerization reactivity and heat resistance. Amine, bicyclo [2.2.1] hept-2-ene, etc.

The ratio of the structural unit derived from each monomer in the resin [K1] is preferably the structural unit derived from (a) among all the structural units constituting the resin [K1]: 2 to 60 mol% of the structural unit derived from (b) : 40 to 98 mol%, more preferably a structural unit derived from (a): 10 to 50 mol% structural unit derived from (b): 50 to 90 mol%. When the ratio of the structural unit of the resin [K1] is within the above-mentioned range, there is a tendency that the storage stability of the colored curable resin composition, the developability when a colored pattern is formed, and the solvent resistance of the obtained color filter tend to be excellent.

The resin [K1] can be referred to, for example, the method described in the document "Experimental Methods for Polymer Synthesis" (Otsu Takayuki Publishing Co., Ltd., 1st Edition, First Press, March 1, 1972) and the document Documented citations.

Specifically, a predetermined amount of (a) and (b), a polymerization initiator, a solvent, and the like are charged into a reaction vessel, and for example, a method of heating and holding heat with stirring while replacing oxygen with nitrogen to form a deoxidizing atmosphere. In addition, the polymerization initiator, solvent, etc. used here are not specifically limited, What can be used normally in this field can be used. Examples of the polymerization initiator include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), etc.), and organic peroxides. As the solvent, it is sufficient to dissolve each monomer as a solvent. Examples of the solvent (E) of the colored curable resin composition of the present invention include solvents described below.

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

The ratio of the structural unit derived from each monomer in the resin [K2] is preferably the structural unit derived from (a) among all the structural units constituting the resin [K2]: 2 to 45 mol% of the structural unit derived from (b) : 2 to 95 mol% Structural unit derived from (c): 1 to 65 mol%, more preferably structural unit derived from (a): 5 to 40 mol% Structural unit derived from (b): 5 to 80 mol% (C) Structural unit: 5 to 60 mol%. If the ratio of the structural unit of the resin [K2] is within the above range, there are storage stability of the colored curable resin composition, developability when a colored pattern is formed, and solvent resistance, heat resistance, and mechanical properties of the obtained color filter. The strength tends to be excellent.

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

The ratio of the structural unit derived from each monomer in the resin [K3] is preferably the structural unit derived from (a) among all the structural units constituting the resin [K3]: 2 to 60 mol% of the structural unit derived from (c) : 40 to 98 mol%, more preferably a structural unit derived from (a): 10 to 50 mol% structural unit derived from (c): 50 to 90 mol%. The resin [K3] can be produced, for example, in the same manner as the method described as the method for producing the resin [K1].

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

Next, the cyclic ether having 2 to 4 carbon atoms in (b) is reacted with a part of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer. Next, the copolymer of (a) and (c) is manufactured, the atmosphere in the flask is replaced with nitrogen, and the reaction catalyst of (b), a carboxylic acid or a carboxylic acid anhydride and a cyclic ether (for example, tris (dimethylcarbamate) Group) phenol, etc.) and polymerization inhibitors (such as hydroquinone, etc.) are put into the flask, and for example, it can be reacted at 60 to 130 ° C for 1 to 10 hours, so that resin [K4] can be produced. The use amount of (b) is preferably 5 to 80 moles, and more preferably 10 to 75 moles, with respect to 100 moles of (a). By setting it as this range, there exists a tendency for the balance of the storage stability of a colored curable resin composition, the developability at the time of pattern formation, and the solvent resistance, heat resistance, mechanical strength, and sensitivity of the obtained pattern to become favorable. Since cyclic ether has high reactivity and unreacted (b) does not easily remain, (b) for resin [K4] is preferably (b1), and more preferably (b1-1). The use amount of the reaction catalyst is preferably 0.001 to 5 parts by mass based on 100 parts by mass of the total amount of (a), (b), and (c). The use amount of the polymerization inhibitor is preferably 0.001 to 5 parts by mass based on 100 parts by mass of the total amount of (a), (b), and (c). The reaction conditions such as the feeding method, the reaction temperature, and the time can be appropriately adjusted in consideration of production equipment, the amount of heat generated by polymerization, and the like. In addition, similarly to the polymerization conditions, it is possible to appropriately adjust the feeding method and the reaction temperature in consideration of production equipment, heat generation from polymerization, and the like.

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

Furthermore, under the same conditions as in the method for producing the resin [K4], the carboxylic acid or carboxylic anhydride contained in (a) is reacted with the cyclic ether derived from (b) which is contained in the copolymer of (b) and (c). , So that the resin [K5] can be obtained. The usage-amount of (a) which reacts with the said copolymer with respect to 100 mol of (b) is preferably 5 to 80 mol. Since cyclic ether has high reactivity and unreacted (b) does not easily remain, (b) for resin [K5] is preferably (b1), and more preferably (b1-1).

The resin [K6] is a resin obtained by further reacting a carboxylic anhydride with a resin [K5]. The carboxylic acid anhydride is reacted with a hydroxyl group produced by the reaction of a cyclic ether with a carboxylic acid or a carboxylic acid anhydride. Examples of the carboxylic acid anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride Dicarboxylic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride, etc. . The use amount of carboxylic anhydride is preferably 0.5 to 1 mol with respect to 1 mol of the use amount of (a).

Specific examples of the resin (B) include 3,4-epoxycyclohexyl methyl (meth) acrylate / (meth) acrylic acid copolymer and 3,4-epoxy tricycloacrylic acid [5.2.1.0 ^2.6 ] Decyl ester / (meth) acrylic acid copolymer [K1]; (meth) acrylic acid / (meth) acrylic 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] decyl ester / vinyl toluene copolymer , Glycidyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / styrene / (meth) acrylic acid copolymer, acrylic acid 3,4 -Epoxytricyclo [5.2.1.0 ^2.6 ] decyl ester / (meth) acrylic acid / N-cyclohexylmaleimide imide copolymer, 3-methyl-3- (meth) propenyloxymethyloxy Resins such as heterocyclobutane / (meth) acrylic acid / styrene copolymer [K2]; resins such as benzyl (meth) acrylate / (meth) acrylic acid copolymer, styrene / (meth) acrylic acid copolymer [ K3]; a resin obtained by adding glycidyl (meth) acrylate and benzyl (meth) acrylate / (meth) acrylic acid copolymer to make glycidyl (meth) acrylate Ester and tricyclodecyl (meth) acrylate / styrene / (meth) acrylic acid copolymer, a resin obtained by adding glycidyl (meth) acrylate and tricyclodecyl (meth) acrylate / ( Resin and other resins made by addition of benzyl (meth) acrylate / (meth) acrylic copolymer [K4]; Tricyclodecyl (meth) acrylate and (meth) acrylic acid / glycidyl (meth) acrylate Resins formed by reacting copolymers of esters, resins made by reacting (meth) acrylic acid with tricyclodecyl (meth) acrylate / styrene / glycidyl (meth) acrylate copolymer [K5 ]; A resin obtained by reacting (meth) acrylic acid with a tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate copolymer and a resin obtained by further reacting with tetrahydrophthalic anhydride Resin [K6] and so on. Among these, as the resin (B), resin [K1] and resin [K2] are preferable, and resin [K2] is particularly preferable.

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

In terms of solid content, the acid value of the resin (B) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, and even more preferably 70 to 135 mg-KOH / g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be obtained by, for example, titration using an aqueous potassium hydroxide solution.

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

<Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by living radicals and / or acids generated by the polymerization initiator (D), and examples thereof include polymerizable ethylenically unsaturated bonds. The compound and the like are preferably a (meth) acrylate compound.

Among these, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, and dipentaerythritol penta (meth) acrylic acid. Ester, dipentaerythritol hexa (meth) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritol nine (meth) acrylate Ester, tris (2- (meth) acryloxyethyl) isocyanurate, ethylene glycol modified pentaerythritol tetra (meth) acrylate, ethylene glycol modified dipentaerythritol hexa (meth) acrylic acid Ester, propylene glycol-modified pentaerythritol tetra (meth) acrylate, propylene glycol-modified pentaerythritol hexa (meth) acrylate, caprolactone-modified pentaerythritol tetra (meth) acrylate, caprolactone-modified dipentaerythritol hexa ( (Meth) acrylates. Among them, dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate are preferred.

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

The content rate of the polymerizable compound (C) with respect to the total amount of the solid content is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and still more preferably 17 to 55% by mass. When the content rate of the polymerizable compound (C) is within the above-mentioned range, the residual film rate at the time of forming a colored pattern and the chemical resistance of the color filter tend to be improved.

<Polymerization Initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating active radicals, acids, and the like by the action of light and heat to initiate polymerization, and a known polymerization initiator can be used. . Examples of the polymerization initiator that generates living radicals include alkylphenylketone compounds, triazine compounds, fluorenylphosphine oxide compounds, O-fluorenyloxime compounds, and biimidazole compounds.

The O-fluorenyl oxime compound is a compound having a partial structure represented by formula (d1). Hereinafter, * indicates a bonding end.

[Chemical 23]

Examples of the O-fluorenyl oxime compound include N-benzyloxy-1- (4-phenylsulfanylphenyl) butane-1-one-2-imine and N-benzyl Phenoxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine, N-benzyloxy-1- (4-phenylsulfanylphenyl) -3-Cyclopentylpropane-1-one-2-imine, N-ethoxyl-1- [9-ethyl-6- (2-methylbenzylidene) -9H-carbazole- 3-yl] ethane-1-imine, N-ethoxy-1--1- [9-ethyl-6-fluorene 2-methyl-4- (3,3-dimethyl-2,4- Dioxolylmethoxy) benzylfluorenyl-9H-carbazol-3-yl] ethane-1-imine, N-ethoxyl-1- [9-ethyl-6- (2-methylbenzyl) -9H-carbazol-3-yl] -3-cyclopentylpropane-1-imine, N-benzyloxy-1- [9-ethyl-6 -(2-methylbenzyl) -9H-carbazol-3-yl] -3-cyclopentylpropane-1-one-2-imine and the like. Commercially available products such as IRGACURE OXE01, OXE02 (the above are manufactured by BASF), and N-1919 (made by ADEKA Corporation) can be used. Among them, the O-fluorenyl oxime compound is preferably selected from N-benzyloxy-1- (4-phenylsulfanylphenyl) butane-1-one-2-imine, N-benzyloxy -1- (4-phenylsulfanylphenyl) octane-1-one-2-imine and N-benzyloxy-1- (4-phenylsulfanylphenyl) -3 -At least one of cyclopentylpropane-1-one-2-imine, more preferably N-benzyloxy-1- (4-phenylsulfanylphenyl) octan-1-one- 2-imine. In the case of these O-fluorenyl oxime compounds, color filters with high brightness tend to be obtained.

The alkyl phenyl ketone 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.

[Chemical 24]

Examples of the compound having a partial structure represented by the formula (d2) include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propane-1-one, and 2- Dimethylamino-1- (4-morpholinophenyl) -2-benzylbutane-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl ] -1- [4- (4-morpholinyl) phenyl] butane-1-one and the like. Commercially available products such as IRGACURE 369, 907, and 379 (above manufactured by BASF) can be used. Examples of the compound having a partial structure represented by the formula (d3) include 2-hydroxy-2-methyl-1-phenylpropane-1-one and 2-hydroxy-2-methyl-1- [4 -(2-hydroxyethoxy) phenyl] propane-1-one, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propane-1 -Oligomers of ketones, α, α-diethoxyacetophenone, benzophenone dimethyl ketal and the like. In terms of sensitivity, as the alkylphenyl ketone compound, a compound having a partial structure represented by formula (d2) is preferred.

Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (tri Chloromethyl) -6- (4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperyl-1,3,5-tri Azine, 2,4-bis (trichloromethyl) -6- (4-methoxystyryl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) vinyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (furan-2-yl ) Vinyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) vinyl]- 1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) vinyl] -1,3,5-triazine Wait.

Examples of the fluorenylphosphine oxide compound include 2,4,6-trimethylbenzylfluorenyldiphenylphosphine oxide and the like. Commercially available products such as IRGACURE (registered trademark) 819 (manufactured by BASF) can be used.

Examples of the biimidazole compound include 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole and 2,2'-bis (2,3 -Dichlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole (for example, refer to Japanese Patent Laid-Open No. 6-75372, Japanese Patent Laid-Open No. 6-75373, etc.), 2,2' -Bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'- Tetrakis (alkoxyphenyl) biimidazole, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetrakis (dialkoxyphenyl) biimidazole, 2,2 '-Bis (2-chlorophenyl) -4,4', 5,5'-tetrakis (trialkoxyphenyl) biimidazole (for example, refer to Japanese Patent Publication No. 48-38403, Japanese Patent Publication No. 62 -174204, etc.), imidazole compounds in which the 4,4 ', 5,5'-phenyl group is substituted with an alkoxycarbonyl group (for example, refer to Japanese Patent Application Laid-Open No. 7-10913).

Further, examples of the polymerization initiator (D) include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether. Compounds; benzophenone, methyl o-benzylidenebenzoate, 4-phenylbenzophenone, 4-benzylidene-4'-methyldiphenylsulfide, 3,3 ', 4,4'-tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone and other benzophenone compounds; 9,10-phenanthrenequinone, 2-ethyl Quinone compounds such as anthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzoin, methyl phenylglyoxylate, titanocene compounds, etc. These are preferably used in combination with a polymerization initiation aid (D1) (particularly, amines) described later.

Examples of the acid generator include 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, and 4-ethoxyloxyphenyldimethylformate. Hydrazone p-toluenesulfonate, 4-ethoxyfluorenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, Onium salts such as phenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, nitrobenzyltosylate, benzoin tosylate, and the like.

As the polymerization initiator (D), a polymerization initiator containing at least one selected from the group consisting of an alkyl phenyl ketone compound, a triazine compound, a fluorenyl phosphine oxide compound, an O-fluorenyl oxime compound, and a biimidazole compound is preferable, and a polymerization initiator is more preferable. Polymerization initiator containing O-fluorenyl oxime compound.

The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above-mentioned range, it tends to increase the sensitivity and shorten the exposure time, and thus the productivity of the color filter is improved.

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

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, and 4-dimethylamino Isoamyl benzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N, N-dimethyl-p-toluidine, 4,4'-bis ( Dimethylamino) benzophenone (commonly known as ketone ketone), 4,4'-bis (diethylamino) benzophenone, 4,4'-bis (ethylmethylamino) benzophenone Among them, 4,4'-bis (diethylamino) benzophenone is preferred. Commercial products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can be used.

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

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, and dimethylphenyl. Thioalkylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, benzene Oxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthyloxyacetic acid, and the like.

When using these polymerization initiation aids (D1), the content is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). Serving. When the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be further formed with high sensitivity, and the productivity of the color filter tends to increase.

<Solvent (E)> The solvent (E) is not particularly limited, and solvents commonly used in this field can be used. For example, ester solvents (solvents containing -COO- and -O-free in the molecule), ether solvents (solvents containing -O- and -COO-free in the molecule), and ether ester solvents (in the molecule Solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO-, -COO-free in the molecule), alcohol solvents (containing OH in the molecule, -O-,- CO- and -COO- solvents), aromatic hydrocarbon solvents, amidine solvents, dimethyl sulfene and the like. These solvents may be used alone or in combination of two or more.

Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, and isoamyl acetate. , Butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetate, ethyl acetate, cyclamate Hexanol acetate and γ-butyrolactone.

Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, and diethylene glycol. Monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3- Methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether , Diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenyl ether and methyl anisole.

Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, and 3-methoxypropionic acid. Methyl ester, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, 2-methoxypropionic acid Ethyl ester, 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, 2- Ethyl ethoxy-2-methylpropanoate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol Monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and Diethylene glycol monobutyl ether acetate and the like.

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

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

Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and 1,3,5-trimethylbenzene.

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

Among the solvents described above, organic solvents having a boiling point at 1 atm of 120 ° C. or higher and 180 ° C. or lower are preferred in terms of coatability and drying properties. As the solvent, propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, and diethylene glycol are preferred. Glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone and N, N-dimethylformamide, more preferably propylene glycol monomethyl ether acetate, 4-hydroxy-4-methyl 2-pentanone, propylene glycol monomethyl ether, ethyl lactate, and ethyl 3-ethoxypropionate.

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

<Leveling agent (F)> Examples of the leveling agent (F) include a silicone-based surfactant, a fluorine-based surfactant, and a silicone-based surfactant having a fluorine atom. These may have a polymerizable group in a side chain. Examples of the silicone-based surfactant include a surfactant having a siloxane bond in the molecule. Specifically, TORAY SILICONE DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade names: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (Manufactured by Shin-Etsu Chemical Industry Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Japan, Japan, Japan, Japan, etc.).

Examples of the fluorine-based surfactant include a surfactant having a fluorocarbon chain in the molecule. Specific examples include Fluoro (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), and メ ガ フ ァ ッ ク (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (Manufactured by DIC), エ ー ト ッ エ (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Corporation), 化 ー ロ ン (registered trademark) S381, S382, SC101, SC105 (Asahi Glass) (Manufactured) and E5844 (manufactured by キ イ ァ ン フ ァ イ ケ ミ カ ル 研究所) and others.

Examples of the above-mentioned organosilicon surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specific examples include メ ガ フ メ ガ ッ ク (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

When the leveling agent (F) is contained, the content ratio is preferably 0.001% by mass or more and 0.2% by mass or less, and more preferably 0.002% by mass or more and 0.1% by mass or less with respect to the total amount of the colored curable resin composition. It is more preferably 0.01% by mass or more and 0.05% by mass or less. In addition, the content rate of the said pigment dispersant is not included in this content rate. When the content rate of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

<Other components> The colored curable resin composition of the present invention may contain fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents and the like, as necessary, as known in the technical field. additive.

<The manufacturing method of a coloring curable resin composition> The coloring curable resin composition of this invention can be made by coloring (A), resin (B), a polymerizable compound (C), a polymerization initiator (D), and It is prepared by mixing the solvent (E), leveling agent (F) and other components to be used as needed. When using a pigment (A2), it is preferable to mix with some or all of a solvent (E) beforehand, and to disperse | distribute using a bead mill etc. until the average particle diameter of a pigment becomes about 0.2 micrometer or less. In this case, a part or all of the pigment dispersant and the resin (B) may be blended as necessary. By mixing the remaining components in the pigment dispersion liquid thus obtained to a predetermined concentration, a desired colored curable resin composition can be prepared. It is preferable that the dye (A1) is separately dissolved in a part or all of the solvent (E) to prepare a solution. This solution is preferably filtered with a filter having a pore size of about 0.01 to 1 μm. It is preferable to filter the colored curable resin composition after mixing with a filter having a pore size of about 0.01 to 10 μm.

<The manufacturing method of a color filter> As a method of manufacturing a coloring pattern from the coloring curable resin composition of this invention, a photolithography method, an inkjet method, a printing method, etc. are mentioned. Among them, photolithography is preferred. The photolithography method is a method in which the colored curable resin composition is applied to a substrate, dried to form a colored composition layer, and the colored composition layer is exposed and developed through a photomask. In the photolithography method, a colored coating film that is a cured product of the coloring composition layer can be formed by using no photomask and / or no development during exposure. The colored pattern and colored coating film thus formed can be used as the color filter of the present invention. The thickness of the produced color filter is not particularly limited, and can be appropriately adjusted according to the purpose, application, and the like, and is, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.5 to 6 μm.

As the substrate, glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, soda lime glass coated with silicon dioxide, etc., polycarbonate, polymethyl methacrylate, polyparaphenylene can be used. Resin plates such as ethylene dicarboxylate, silicon, and products of aluminum, silver, silver / copper / palladium alloy films, and the like are formed on the substrate. Additional color filter layers, resin layers, transistors, circuits, etc. can be formed on these substrates.

The formation of the pixels of each color by the photolithography method can be performed under a known or conventional apparatus and conditions. For example, it can be produced as follows. First, a colored curable resin composition is coated on a substrate, and then dried by heating (pre-baking) and / or drying under reduced pressure to remove volatile components such as solvents and drying, thereby obtaining a smooth colored composition layer. Examples of the coating method include a spin coating method, a slit coating method, a slit and a spin coating method, and the like. The temperature during heating and drying is preferably 30 to 120 ° C, and more preferably 50 to 110 ° C. The heating time is preferably 10 seconds to 60 minutes, and more preferably 30 seconds to 30 minutes. In the case of drying under reduced pressure, it is preferably performed under a pressure of 50 to 150 Pa and a temperature range of 20 to 25 ° C. The film thickness of the coloring composition layer is not particularly limited, and can be appropriately selected according to the film thickness of the target color filter.

Next, the coloring composition layer is exposed through a photomask for forming a target coloring pattern. The pattern on the photomask is not particularly limited, and a pattern suitable for the intended use can be used. As a light source for exposure, a light source which generates light with a wavelength of 250 to 450 nm is preferable. For example, the wavelength range may be cut using a filter that cuts light of less than 350 nm, or these wavelength ranges may be selectively removed using a band-pass filter that extracts light near 436 nm, 408 nm, and 365 nm. Specifically, a mercury lamp, a light emitting diode, a metal halide lamp, a halogen lamp, etc. are mentioned. Since the entire exposure surface can be uniformly irradiated with parallel light rays, and accurate alignment of the photomask and the substrate on which the colored composition layer is formed, it is preferable to use an exposure device such as a mask aligner and a stepper.

The coloring composition layer after exposure is developed by contacting with the developing solution, thereby forming a coloring pattern on the substrate. By the development, the unexposed part of the coloring composition layer is dissolved in the developing solution and removed. As the developing solution, for example, an aqueous solution of a basic compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide is preferable. The concentration of these basic compounds in an aqueous solution is preferably 0.01 to 10% by mass, and more preferably 0.03 to 5% by mass. Furthermore, the developing solution may contain a surfactant. The development method may be any of a spin-on immersion method, a dipping method, and a spray method. Furthermore, the substrate can be tilted at an arbitrary angle during development. After development, washing with water is preferred.

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

By using the colored curable resin composition of the present invention, a color filter having particularly excellent brightness can be manufactured. This color filter can be used as a color filter used in display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging elements. Examples

The present invention will be described more specifically with reference to the following examples. Of course, the present invention is not limited to the following examples. Of course, the present invention can be appropriately modified and implemented within a range suitable for the gist described above and below. All of them are included in the present invention. Within technology. In addition, unless otherwise stated below, "part" means "mass part", and "%" means "mass%".

In the following examples, the structure of the compound was confirmed by mass analysis (LC; Model 1200 manufactured by Agilent, MASS; Model LC / MSD manufactured by Agilent).

[Example 1]

[Chemical 25]

In a flask having a cooling tube and a stirring device, 3 parts of a compound represented by formula (X) (manufactured by Chuka Chemicals), 21 parts of N-methylpyrrolidone, and 1.3 parts of potassium hydroxide were added, and the mixture was stirred at room temperature for 1 hour 2.3 parts of ethyl acrylate was added and stirred at the same temperature for 2 hours. The obtained reaction solution was added to 105 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes. As a result, crystals were precipitated. The precipitated crystals were separated by filtration, sufficiently washed with ion-exchanged water, and dried under reduced pressure at 60 ° C to obtain 3.5 parts of a compound represented by the formula (Aa-1-IM).

[Chem. 26]

Identification (mass analysis) of compound represented by formula (Aa-1-IM) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 675.3 Exact mass: 674.3

A flask having a cooling tube and a stirring device was charged with 1 part of a compound represented by the formula (Aa-1-IM), 7 parts of methanol, and 3.0 parts of an 8% aqueous sodium hydroxide solution, and the mixture was stirred at room temperature for 9 and a half hours. The obtained reaction solution was added to 35 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes. As a result, crystals were precipitated. The precipitated crystals were separated by filtration, washed with ion-exchanged water, and dried under reduced pressure at 60 ° C to obtain 0.9 parts of a compound represented by the formula (Aa-1).

[Chemical 27]

Identification (mass analysis) of compound represented by formula (Aa-1) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 647.5 Accurate mass: 646.2

[Example 2] A flask having a cooling tube and a stirring device was charged with 1 part of a compound represented by formula (X) (manufactured by Chuka Chemicals), 7 parts of N-methylpyrrolidone, 1.0 part of potassium carbonate, and 4-bromobutyric acid. 2.0 parts of ethyl acetate was stirred at 100 ° C for 7 and a half hours. After allowing to cool, 20 parts of 2N hydrochloric acid was added to the obtained reaction solution, and extracted twice with 45 parts of chloroform. The chloroform was laminated together, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and dried under reduced pressure at 60 ° C to obtain 4.1 parts of a compound represented by the formula (Aa-33-IM) in crude form.

[Chemical 28]

Identification (mass analysis) of compound represented by formula (Aa-33-IM) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 803.5 Exact mass: 802.3

A flask having a cooling tube and a stirring device was charged with 4.1 parts of a compound represented by the formula (Aa-33-IM), 9.8 parts of methanol, and 3.5 parts of an 8% aqueous sodium hydroxide solution, and the mixture was stirred at room temperature for 6 hours. The obtained reaction solution was added to 30 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes. As a result, crystals were precipitated. The precipitated crystal was separated by filtration, sufficiently washed with ion-exchanged water, and dried under reduced pressure at 60 ° C to obtain 1.0 part of a compound represented by the formula (Aa-33).

[Chem. 29]

Identification (mass analysis) of compound represented by formula (Aa-33) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 747.5 Exact mass: 746.3

[Example 3] A flask having a cooling tube and a stirring device was charged with 3 parts of a compound represented by formula (X) (manufactured by Sinochem Corporation), 21 parts of N-methylpyrrolidone, and 1.7 parts of potassium tert-butoxy. After stirring at room temperature for 30 minutes, 1.6 parts of 1-bromopropane was added, and the mixture was stirred at the same temperature for 1 hour. The obtained reaction solution was added to 21 parts of 2N hydrochloric acid and stirred at room temperature for 1 hour. As a result, crystals were precipitated. The precipitated crystal was separated by filtration, sufficiently washed with ion-exchanged water, and dried under reduced pressure at 60 ° C to obtain 3.0 parts of a compound represented by the formula (Aa-8-IM1).

[Hua 30]

Identification (mass analysis) of compound represented by formula (Aa-8-IM1) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 617.5 Accurate mass: 616.2

A flask having a cooling tube and a stirring device was charged with 1 part of a compound represented by formula (Aa-8-IM1), 7 parts of N-methylpyrrolidone, 0.45 parts of potassium carbonate, and 0.95 parts of ethyl 4-bromobutyrate. It was stirred at 100 ° C for 5 and a half hours. The obtained reaction solution was added to 35 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes. As a result, crystals were precipitated. The precipitated crystals were separated by filtration, sufficiently washed with ion-exchanged water, and dried under reduced pressure at 60 ° C to obtain 1.2 parts of a compound represented by the formula (Aa-8-IM2).

[Chemical 31]

Identification (mass analysis) of compound represented by formula (Aa-8-IM2) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 731.5 Exact mass: 730.3

A flask having a cooling tube and a stirring device was charged with 1 part of a compound represented by the formula (Aa-8-IM2), 7 parts of methanol, and 2.7 parts of an 8% aqueous sodium hydroxide solution, and stirred at room temperature for 3 and a half hours. The obtained reaction solution was added to 21 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes. As a result, crystals were precipitated. The precipitated crystals were separated by filtration, sufficiently washed with ion-exchanged water, and dried under reduced pressure at 60 ° C to obtain 0.9 parts of a compound represented by the formula (Aa-8).

[Chemical 32]

Identification (mass analysis) of compound represented by formula (Aa-8) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 703.5 Exact mass: 702.3

[Example 4] A flask having a cooling tube and a stirring device was charged with 0.5 part of a compound represented by the formula (Aa-1-IM), 3.5 parts of N-methylpyrrolidone, 0.26 parts of potassium carbonate, and 2.3 parts of 1-bromopropane. It was stirred at room temperature for 80 hours. The obtained reaction solution was added to 70 parts of 2N hydrochloric acid, and the mixture was stirred at room temperature for 30 minutes. As a result, crystals were precipitated. The precipitated crystals were separated by filtration, sufficiently washed with ion-exchanged water, and dried under reduced pressure at 60 ° C to obtain 0.5 parts of a compound represented by the formula (Aa-4-IM2).

[Chemical 33]

Identification (mass analysis) of compound represented by formula (Aa-4-IM2) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 717.5 Exact mass: 716.3

In a flask having a cooling tube and a stirring device, 0.5 part of a compound represented by the formula (Aa-4-IM2), 3.4 parts of methanol, and 1.3 parts of an 8% sodium hydroxide aqueous solution were added, and the mixture was stirred at room temperature for 2 hours. The obtained reaction solution was added to 70 parts of 2N hydrochloric acid, and the mixture was stirred at room temperature for 30 minutes. As a result, crystals were precipitated. The precipitated crystals were separated by filtration, sufficiently washed with ion-exchanged water, and dried under reduced pressure at 60 ° C to obtain 0.4 parts of a compound represented by the formula (Aa-4).

[Chemical 33]

Identification (mass analysis) of compound represented by formula (Aa-4) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 689.5 Exact mass: 688.3

[Example 5] A flask having a cooling tube and a stirring device was charged with 1.5 parts of a compound represented by formula (X) (manufactured by Chuka Chemicals), 10.5 parts of N-methylpyrrolidone, 1.1 parts of potassium carbonate, and 4-bromobutyric acid. 0.5 part of ethyl acetate was stirred at 90 ° C for 4 and a half hours. The obtained reaction solution was added to 52.5 parts of ion-exchanged water, and after stirring at room temperature for 30 minutes, crystals were precipitated. The precipitated crystals were separated by filtration, sufficiently washed with ion-exchanged water, and dried under reduced pressure at 60 ° C. The obtained crude body was purified by silica gel column chromatography (mobile phase: chloroform / methanol-10 / 1) to obtain 0.2 parts of a compound represented by the formula (Aa-5-IM).

[Chem. 35]

Identification (mass analysis) of compound represented by formula (Aa-5-IM) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 689.5 Exact mass: 688.3

A flask having a cooling tube and a stirring device was charged with 0.2 part of the compound represented by the formula (Aa-5-IM), 1.6 parts of methanol, and 1.0 part of 8% aqueous sodium hydroxide solution, and stirred at room temperature for two and a half hours. The obtained reaction solution was added to 16 parts of 2N hydrochloric acid, and the mixture was stirred at room temperature for 30 minutes. As a result, crystals were precipitated. The precipitated crystals were separated by filtration, sufficiently washed with ion-exchanged water, and dried under reduced pressure at 60 ° C to obtain 0.2 parts of a compound represented by the formula (Aa-5).

[Chemical 36]

Identification (mass analysis) of compound represented by formula (Aa-5) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 661.5 Exact mass: 660.3

[Example 6]

[Chem. 37]

In a flask having a cooling tube and a stirring device, 5 parts of 3,6-dichlorosulfofluorescein (manufactured by Chuka Kasei) represented by formula (XX), 35 parts of N-methylpyrrolidone, and 3-amino-4 were added. -12.2 parts of methyl benzoate, stirred at 130 ° C for 7 hours. After leaving to cool, the obtained reaction solution was added to an aqueous solution of 7.5 parts of concentrated hydrochloric acid and 70 parts of ion-exchanged water, and the mixture was stirred at room temperature for 30 minutes, and as a result, crystals were precipitated. The precipitated crystals were separated by filtration, sufficiently washed with ion-exchanged water, and dried under reduced pressure at 60 ° C to obtain 6.6 parts of a compound represented by the formula (Aa-41-IM).

[Chemical 38]

Identification (mass analysis) of compound represented by formula (Aa-41-IM) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 663.5 Exact mass: 662.2

In a flask having a cooling tube and a stirring device, 6 parts of a compound represented by the formula (Aa-41-IM), 42 parts of N-methylpyrrolidone, 5.0 parts of potassium carbonate, and 6.6 parts of 1-bromopropane were added at 90 ° C. Stir for 6 hours. After leaving to cool, the obtained reaction solution was added to 210 parts of ion-exchanged water and stirred at room temperature for 30 minutes. As a result, crystals were precipitated. The precipitated crystals were separated by filtration, sufficiently washed with ion-exchanged water, and dried under reduced pressure at 60 ° C to obtain 5.9 parts of a compound represented by the formula (Aa-44-IM).

[Chemical 39]

Identification (mass analysis) of compound represented by formula (Aa-44-IM) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 747.8 Exact mass: 746.3

A flask having a cooling tube and a stirring device was charged with 3 parts of a compound represented by the formula (Aa-44-IM), 21 parts of methanol, and 8.0 parts of an 8% aqueous sodium hydroxide solution, and stirred at room temperature for 8 hours. The obtained reaction solution was added to 105 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes. As a result, crystals were precipitated. The precipitated crystal was separated by filtration, sufficiently washed with ion-exchanged water, and dried under reduced pressure at 60 ° C to obtain 2.5 parts of a compound represented by the formula (Aa-44).

[Chemical 40]

Identification (mass analysis) of compound represented by formula (Aa-44) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 719.5 Accurate mass: 718.2

[Example 7]

[Chemical 41]

In a flask having a cooling tube and a stirring device, 5 parts of 3,6-dichlorosulfofluorescein (manufactured by Chuka Kasei) represented by formula (XX), 35 parts of N-methylpyrrolidone, and 4-amino-3 were added. -12.2 parts of methyl benzoate, stirred at 130 ° C for 16 hours. After leaving to cool, the obtained reaction solution was added to an aqueous solution of 7.5 parts of concentrated hydrochloric acid and 70 parts of ion-exchanged water, and the mixture was stirred at room temperature for 30 minutes, and as a result, crystals were precipitated. The precipitated crystal was separated by filtration, sufficiently washed with ion-exchanged water, and dried under reduced pressure at 60 ° C to obtain 6.5 parts of a compound represented by the formula (Aa-45-IM).

[Chemical 42]

Identification (mass analysis) of compound represented by formula (Aa-45-IM) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 663.8 Accurate mass: 662.2

In a flask having a cooling tube and a stirring device, 6 parts of a compound represented by the formula (Aa-45-IM), 42 parts of N-methylpyrrolidone, 5.0 parts of potassium carbonate, and 6.6 parts of 1-bromopropane were added at 90 ° C. Stir for 8 hours. After leaving to cool, the obtained reaction solution was added to 210 parts of ion-exchanged water and stirred at room temperature for 30 minutes. As a result, crystals were precipitated. The precipitated crystal was separated by filtration, sufficiently washed with ion-exchanged water, and dried under reduced pressure at 60 ° C to obtain 6.0 parts of a compound represented by the formula (Aa-48-IM).

[Chemical 43]

Identification (mass analysis) of compound represented by formula (Aa-48-IM) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 747.8 Exact mass: 746.3

A flask having a cooling tube and a stirring device was charged with 3 parts of a compound represented by the formula (Aa-48-IM), 21 parts of methanol, and 8.0 parts of an 8% aqueous sodium hydroxide solution, and stirred at room temperature for 8 and a half hours. The obtained reaction solution was added to 105 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes. As a result, crystals were precipitated. The precipitated crystal was separated by filtration, sufficiently washed with ion-exchanged water, and dried under reduced pressure at 60 ° C to obtain 2.0 parts of a compound represented by the formula (Aa-48).

[Chemical 44]

Identification (mass analysis) of compound represented by formula (Aa-48) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 719.5 Accurate mass: 718.2

[Synthesis Example 1] In a flask equipped with a reflux cooler, a dropping funnel, and a stirrer, an appropriate amount of nitrogen was flowed in, replaced with a nitrogen atmosphere, and 371 parts of 1-methoxy-2-propylacetate was placed therein while stirring. While heating to 85 ° C. Next, a mixture of 54 parts of acrylic acid and 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decane-8 or 9-yl ester (trade name) was dropped into the flask over 4 hours. A mixed solution of "E-DCPA", manufactured by Daicel Corporation), 225 parts, 81 parts of vinyl toluene (isomer mixture), and 80 parts of 1-methoxy-2-propyl acetate. On the other hand, 30 parts of the polymerization initiator 2,2-azobis (2,4-dimethylvaleronitrile) was dissolved in 1-methoxy-2-propyl acetate 160 dropwise over 5 hours. Portions of the solution. After the addition of the initiator solution was completed, the solution was kept at the same temperature for 4 hours, and then cooled to room temperature. The viscosity measured by the B-type viscosity (23 ° C) was 246 mPas. The solid content of the resin (B-1) solution was 37.5% by weight, and the acid value in terms of solid content was 115 mg-KOH / g. The weight average molecular weight Mw of the produced copolymer was 10,600, and the molecular weight distribution (Mw / Mn) was 2.01. The resin (B-1) has the following structural units.

[Chemical 45]

The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured using the GPC method under the following conditions. Device: HLC-8120GPC (manufactured by Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40 ° C Solvent: THF Flow rate: 1.0mL / min Solid content concentration of test solution: 0.001 ~ 0.01% by mass Injection volume: 50μL Detector : Reference material for RI calibration: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corp.) The ratio of the number average molecular weight (Mw / Mn) was taken as the molecular weight distribution.

[Example 8] (Preparation of colored curable resin composition) (A) Colorant: CI Pigment Blue 15: 6 (Pigment) 27 parts of acrylic pigment dispersant 9.5 parts of propylene glycol monomethyl ether acetate 222 parts Mix and disperse the pigment sufficiently using a bead mill. Next, (A) colorant: a compound represented by formula (Aa-1) 1.2 parts (A) colorant: CI solvent blue 45 1.5 parts (B) resin: Resin B1 (solid content conversion) 60 parts (C) polymerizable compound: dipentaerythritol hexaacrylate (Kapalak (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 40 parts (D) polymerization initiator: N-benzyl Phenoxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 9 parts (F) leveling agent: Polyether modified silicone oil (TORAY SILICONE SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.15 parts (E) Solvent: 4-hydroxy-4-methyl-2-pentanone 156 parts (E) Solvent: propylene glycol monomethyl 401 parts of ether acetate were mixed to obtain a colored curable resin composition.

[Comparative Example 1] (A) Colorant: CI Pigment Blue 15: 6 (Pigment) 29 parts of acrylic pigment dispersant 10.1 parts of propylene glycol monomethyl ether acetate 236 parts were mixed, and the pigment was sufficiently made using a bead mill (A) Colorant: Dye (Aa-x) 1.4 parts (A) Colorant: CI Solvent Blue 45 1.6 parts (B) Resin: Resin B1 (solid content conversion) 60 parts (C) Polymerization Compound: Dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd.) 40 parts (D) Polymerization initiator: N-benzyloxy-1- (4-phenylsulfanylphenyl) octane-1 -Keto-2-imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 9 parts (F) Leveling agent: polyether modified silicone oil (TORAY SILICONE SH8400: Toray-Dow Corning Co., Ltd.) 0.15 parts (E) Solvent: 156 parts of 4-hydroxy-4-methyl-2-pentanone (E) Solvent: 397 parts of propylene glycol monomethyl ether acetate were mixed to obtain a colored curable resin composition. The dye (Aa-x) is a mixture of compounds represented by the following formulae (A2-2-1) to (A2-2-8). [Chemical 46]

Examples 9 to 14 and Comparative Example 1 A colored curable resin composition was obtained by performing the same operation as in Example 8 except that the compositions shown in Table 1 were obtained.

【Table 1】

In addition, in Table 1, "A2-1 ¹⁾ " is prepared by mixing and dispersing propylene glycol monomethyl ether acetate in an amount described in the column "E-1 ³⁾ " in advance. . The column "E-1 ²⁾ " shows the total content of propylene glycol monomethyl ether acetate. In Table 1, each component has the following meanings. The resin (B) represents parts by mass in terms of solid content. Compound (I): Compound (Aa-1) Compound (I): Compound (Aa-33) Compound (I): Compound (Aa-8) Compound (I): Compound (Aa-4) Compound (I): Compound (Aa-5) Compound (I): Compound (Aa-44) Compound (I): Compound (Aa-48) Anthraquinone Dye (Ad): Ad-1: CI Solvent Blue 45 (Savinyl Blue RS; manufactured by Clariant Corporation) ) Pigment (A2): A2-1: CI Pigment Blue 15: 6 Resin (B): B-1: Resin B1 Polymerizable compound (C): Dipentaerythritol hexaacrylate (Kaplak (registered trademark) DPHA; Nippon Kayaku Co., Ltd.) Polymerization initiator (D): D-1: N-benzyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (IRGACURE (Registered trademark) OXE 01; manufactured by BASF; O-fluorenyl oxime compound) Solvent (E): E-1: Propylene glycol monomethyl ether acetate solvent (E): E-2: 4-hydroxy-4- Methyl-2-pentanone leveling agent (F): polyether modified silicone oil (TORAY SILICONE SH8400; manufactured by Toray Dow Corning Co., Ltd.)

The colored curable resin compositions of Examples 8 to 14 and Comparative Example 1 obtained as described above were evaluated.

<Preparation of colored pattern> A 5 cm square glass substrate (EAGLE 2000; manufactured by Corning Corporation) was applied with a coloring curable resin composition by spin coating, and then pre-baked at 100 ° C for 3 minutes to obtain a coloring composition layer. . After allowing to cool, the distance between the substrate on which the colored composition layer was formed and the photomask made of quartz glass was 100 μm, using an exposure machine (TME-150RSK; manufactured by TOKON Co., Ltd.) in an atmosphere of 150 mJ / cm ² The exposure amount (based on 365nm) was irradiated with light. As the photomask, a photomask in which a 100 μm line and gap pattern was formed was used. The coloring composition layer after light irradiation was immersed and developed at 24 ° C for 60 seconds in an aqueous developing solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide. After washing with water, it was performed in an oven at 230 ° C. After 20 minutes of baking, a colored pattern was obtained.

<Film Thickness Measurement> The obtained colored pattern was measured for film thickness using a film thickness measuring device (DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd.).

<Colorimetric Evaluation> The coloring pattern obtained was measured using a colorimeter (OSP-SP-200; manufactured by Olympus Co., Ltd.), and the characteristic function of the C light source was used to measure the color of the XYZ color system of CIE. The xy chromaticity coordinates (x, y) and the stimulus value Y. The larger the value of Y, the higher the brightness. The results are shown in Table 2.

【Table 2】

It was confirmed that the coating film obtained using the colored curable resin composition of the example showed high brightness. From this, it can be seen that the colored coating film and colored pattern obtained from the colored curable resin composition of the present invention can be used as a high-brightness color filter, and a liquid crystal display device including the color filter has excellent display characteristics. Industrial availability

According to the colored curable resin composition of the present invention, a color filter with high brightness can be formed. This color filter can be used as a color filter used in display devices such as liquid crystal display devices, organic EL devices, electronic paper, and solid-state imaging devices.

Claims (4)

A compound represented by formula (I): In formula (I), R ¹ to R ⁴ independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, and the saturated -CH ₂ -contained in the hydrocarbon group may be replaced by -O-, -CO-, or -NR ^11- . R ¹ and R ² may form a ring containing a nitrogen atom together, and R ³ and R ⁴ may form a nitrogen atom together. R ⁶ and R ⁷ independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R ¹¹ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms or an aralkyl group having 7 to 10 carbon atoms, but The compound represented by the formula (I) satisfies at least one of the necessary conditions (i) to (vi): (i) R ¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM, and R ² to R ⁴ At least one of them is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, and -COOM contained in one molecule is one, (ii) R ¹ and R ³ are 6 to 10 carbon atoms having -COOM An aromatic hydrocarbon group of 10, (iii) R ¹ is an aromatic hydrocarbon group having 6 to 10 carbon atoms having -COOM, R ³ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COOM, and (iv) R ¹ is having- COOM is a saturated hydrocarbon group having 3 to 20 carbon atoms, and R ³ is a carbon number having -COOM 1 to 20 saturated hydrocarbon groups, (v) R ¹ is a saturated hydrocarbon group having 1 to 20 carbons which may have a substituent, R ² is an aromatic hydrocarbon group having 6 to 10 carbons having -COOM, (vi) R ¹ and R ² is a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. At least one of R ³ and R ⁴ is an aromatic hydrocarbon group having 6 to 10 carbon atoms in -COOM. In (vi), M represents a hydrogen atom, Na ⁺ , K ⁺ , or ⁺ N (R ¹² ) _{4. The} four R ¹² may be the same or different. R ¹² represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or Aralkyl with 7 to 10 carbon atoms. A colored curable resin composition comprising the compound according to claim 1, a resin (B), a polymerizable compound (C), and a polymerization initiator (D). A color filter formed from the colored curable resin composition according to claim 2. A display device including the color filter according to claim 3.