TW201222151A - Coloring resin composition for color filter, color filter and uses thereof - Google Patents

Abstract

This invention relates to a coloring resin composition containing a pigment compound represented by the following formula (1) (in this formula, R1 to R4 respectively independently represents hydrogen atom, C1-C30 alkyl group, phenyl group or benzyl group, R5 to R17 respectively independently represents hydrogen atom, halogen atom, C1-C6 alkyl group, substituted or unsubstituted amino group, the anion part Z<SP>-</SP> represents halogenoalkyl sulfonylimide anion, halogenoalkyl sulfonylmethyl anion or halogenoalkyl sulfonate anion, the respective halogenoalkyl group respectively independently represents C1-C10 alkyl group substituted by 3 to 6 halogen atoms.), a binder resin, a solvent, a polymerization initiator and a hardener, and a color filter having a cured article layer of the coloring resin composition, whereby the coloring resin composition of this invention can provide a high-quality blue pixel for color filter having good contrast and excellent thermal resistance.

Description

201222151 VI. Description of the Invention: [Technical Profile of the Invention] The colored resin composition of the present invention relates to a colored resin composition formed by using the colored resin composition, and a color filter and a color filter (Color Filter) formed using the colored resin composition. And an electronic display device such as a liquid crystal display device, a photographic element (CCD, CMOS), or an organic EL display formed using the color glazing sheet. [Prior Art] A liquid crystal display element such as a liquid crystal display (LCD) represented by a pen &amp; type computer, a liquid crystal television or a mobile phone, or a photographic element used as an input device such as a digital camera or a color copying machine (CCD) Colorization of CM〇s) requires a color filter. For the method of manufacturing the color filter used in such liquid crystal display devices or solid-state sensing elements, although there is a wood color method, Electrodeposition, printing, pigment dispersion, etc., but in recent years, the pigment dispersion method has become mainstream. As for the method of patterning, a photochromic technique is used as a representative, and a color filter is formed by using a mixture of a photosensitive resin composition and a pigment dispersion. Recently, a method of forming a color filter by directly applying a colored ink to a substrate without passing through a photomask by an ink jet printer has been carried out. Improvements in color purity, chroma, brightness, and skew ratio of the characteristics required for color filters are particularly important. By increasing the brightness, it is possible to suppress the amount of light in the backlight, and it is also possible to reduce the consumption of electric power. Therefore, it is also an essential technology in the environment. In order to increase the color purity of the color filter, it is necessary to increase the content of the coloring pigment or to select a pigment having a preferred spectral waveform. On the other hand, in order to increase the brightness, it is necessary to increase the transmittance. Therefore, 323585 4 201222151 is required to reduce the concentration of the pigment or to make the film thickness thin. A method of performing so-called fine particle formation of a pigment in order to achieve the opposite characteristics. Even if the microparticle resistance or dispersion stability is limited, the current state of appearance is that even if the brightness is improved, there is no way to balance the tolerance. In order to solve these problems, a color filter 4 using a dye is used as another route. When the dye is used, there is an advantage in that the color purity and brightness which are not achieved by the color are achieved, or since the light b is suppressed by the moon b, the contrast can be improved. However, for televisions and the like, it is necessary to have a light-resistant or heat-resistant display body, but in particular, the indigo dyes are significantly inferior in resistance to pigments. For example, 'in the following Patent Documents 1 and 2', there is a report on the use of a tris-based methane, and a delta substance in a color-developing film. However, the ammonium salt of the triphenylmethane-based compound described herein is remarkably inferior in light resistance or heat resistance, and does not reach the level of use. Although the phthalphthalein (Cyanine) dye is well known and has excellent resistance (Patent Document 3), since this color characteristic is not a ochre color but a generally reddish Cyan color tone, it cannot be formed into a vivid color. Helmet color. Among the color filters, a colored resin composition containing a bright blue halogen and having a high degree of reliability and excellent color resistance is required, but it is almost unutilized. Therefore, it is ardently demanding a high-quality color filter which is a bright blue color of the next generation. [PRIOR ART DOCUMENT] Patent Document 1: Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. [Problem to be Solved by the Invention] The object of the present invention is to provide a blue color filter having excellent contrast color characteristics and excellent heat resistance. Color pigment. [Means for Solving the Problem] As a result of careful study of the above-mentioned problems, the present inventors have found that in the blue color of the color filter, 'by using a specific salt containing a specific triphenylmethane compound The colored resin composition of the color material compound can solve the above problems, and the present invention has been completed. That is, the present invention relates to the inventors described in the following (1) to (17). (1) A colored resin composition for a color filter comprising a color material compound represented by the following formula (1), a binder resin, a solvent, a polymerization initiator, and a curing agent.

(wherein, 仏 to R4 each independently represent a hydrogen atom, an alkyl group of C1 to C30, a phenyl group or a benzyl group, and each of the cores to Rl7 independently represents a hydrogen atom, a halogen atom, an alkyl group of C1 to C6, a substitution or not Substituted amine group. The anion moiety Z-1 is represented by 323585 6 201222151, and the halogenated carboxylic acid methylate is anionic from each other to the C10 alkyl group independently. The acyl group is continuously substituted with the basal imino anion or the halogenated sulfonate anion 3 to 6 halogen atoms. The colored resin composition for the color light sheet described in the above (1) is 'polymerized' (4) 丨 is photopolymerization (4) silk polymerization initiator. (3) The colored resin composition for a color filter as described in the above (1) or (2) wherein 'Z' is bis(trifluoromethyl)sulfonyl quinone imine anion, ginseng (trifluoromethyl)% armor A carboxylate anion, or a trifluoromethanesulfonate anion. (4) The colored resin composition for a color filter according to any one of the above (1) to (3), wherein at least one of them is a halogen atom. (5) The coloring resin composition for a color filter according to any one of the above (1) to (3) wherein at least one of fluorene to Rn is an alkylamine group. (6) The colored resin composition for a color filter according to any one of the above-mentioned (12), wherein the metal ugly pigment or the following formula is contained (2) either or both of the color material compounds,

X3 (wherein Rla to R6a each independently represent a hydrogen atom, a halogen atom, a C1 to C12 alkyl group, a C1 to C12 alkoxy group, a nitro group, a carboxyl group or an alkoxycarbonyl group. Y to Y4 each independently represent a hydrogen atom, a C1 to C12 alkyl group, an aryl group. χ1 7 323585 201222151 to X4 independently represent a hydrogen atom, a C1 to ci2 alkyl group, a C1 to cl2 mi atom, an exact group, a phenoxy group, a thiol group, Oxygen number, sulfo group, amine group, anion moiety z-table * (tetra) group (iv) an imine anion, a halogen lysine anion, or a halogen-based heteroaion anion 'each (four) group is independently 3 to 6 a C1 to C10 alkyl group substituted by 4 atoms). (7) A colored resin composition for a color filter according to (6) above, which contains a metal phthalocyanine pigment. (8) The colored resin composition for a color filter as described in the above (6), which contains a metal (tetra) pigment and a color material compound represented by the formula (2). (9) A color filter comprising the cured resin layer of the coloring resin composition according to any one of the above (1) to (5), or the colored resin for any of the above (1) to (5) In the composition, a cured layer of a coloring resin composition for a color filter of either or both of the metal talon pigment or the coloring material compound represented by the following formula (2) is added, and the compound (2)

323585 8 201222151 alkyl, Cl to C12 alkoxy, alkaloid, silk, aerobic groups. Υι 匕 独立 独立 氢 氢 氢 氢 氢 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 Oxyl, fluorenyl, oxyxan, contiguous, amine hetero. Anion separation material sub-quiet ion, (4) (four) base anion, or (four) base lye salt; sub, each (four) county is independently 3 to 6 from the original c

C10 alkyl). I. Light sheet (10) A color display device as described in (9) above (9) A solid-state image sensing element, a color filter. (10) The colored tree for a color light-slicing sheet according to the above (2), wherein each of UR4 in the formula (1) is independently a hydrogen atom or the low-linking group 〇1 to C4 are each independently a hydrogen atom or a ur. a lower alkyl group, each of Ri3 to Rn is independently a hydrogen atom, a halogen atom, or a C1 to C3 alkylamino group, and the C1 to C3 alkyl group of the di C1 to C3 alkylamino group may be unsubstituted or may also be Substituted atomic or cyano substituted, z_ is a bis (trimethane) continuation quinone imine anion, ginseng (trifluoromethyl) continuation of methylated anion, or trifluoromethanesulfonate anion . θ (13) The coloring resin for a color filter according to (10) above, wherein at least one of 'R5 to R12' in the formula (1) is: a calcination group, the other is a hydrogen atom, and at least i of R1 to R1 Is a function atom, ^ He is a hydrogen atom. And a colored resin composition for a color light-sensitive sheet according to any one of the above-mentioned items (1) to (5), (12), and (13), wherein, in the formula (1), Z - is a fluoromethyl) sulfonium methide anion. (15) The colored resin composition for a color filter according to any one of the above (6), wherein, in the formula (2), z- is a double ( Tris-methyl) 3⁄4醯-indenyl anion, ginseng (tri-methyl) ruthenium anion, or trifluoromethanesulfonate anion. (16) The colored resin composition for a color filter according to the above (15), wherein 'Rla to R6a' in the formula (2) are each independently a hydrogen atom, and each of Y4 is independently a hydrogen atom or C1 to The alkyl group of C4, and 1 to Χ5 are each independently a hydrogen atom or a carboxyl group. The colored resin composition for a color filter according to any one of the above-mentioned (6), (12) and (13), wherein, in the formula (2) and (2), Both of them are ginseng (trifluoromethyl) sulfonium methide anions. [Effect of the Invention] The colored resin composition for color filters of the present invention (also referred to as the colored resin composition of the present invention or the resin composition of the present invention) can provide sharp contrast characteristics in heat resistance and the like. Excellent color filters with high quality blue halogen. [Embodiment] The colored resin composition of the present invention contains a binder resin, a solvent, a polymerization initiator (for example, a photopolymerization initiator, or a thermal polymerization initiator), a hardener, and a color compound compound as needed. 'It may contain various coloring compounds such as other pigments or anthraquinone dyes, surfactants, thermosetting agents, and various additives such as polymerization inhibitor 323585 10 201222151 and UV absorbers. The components other than the specific color material compound can be used without particular limitation, and are not limited thereto. The method for producing a halogen using the colored resin composition of the present invention is mainly a photolithography method and an ink jet method. The former is an image using a photopolymerization initiator. A photosensitive resin composition excellent in the latter, and the latter is a thermosetting resin composition which does not necessarily require a photopolymerization initiator. The specific color material compound used in the present invention is a specific salt of a triphenylmethane compound represented by the above formula (1). In the above formula (1) to R4, as the alkyl group of C1 to C30, for example, methyl, ethyl, propyl, isopropyl, butyl, 1-methylpropyl (secondary Butyl), isobutyl, pentyl, ethylidene propyl, methyl butyl, cyclopentyl, hexyl, 1-methylpentyl, ethyl ethyl butyl, cyclohexyl, hydroxypropyl, 2-sulfoethyl, Carboxyethyl, cyanoethyl, methoxyethyl, ethoxyethyl, butoxyethyl, trifluoromethyl, pentafluoroethyl, 2-heptyl, heptyl, octyl, decyl , fluorenyl, eleven-burning, twelve-burning, thirteen-burning, fourteen-competition, base, fifteen-burning base, sixteen-burning base, seventeen-burning base, eighteen-burning base, nineteen-burning base, Arachidyl, decyl, heneicosyl, bismuth, 廿三院, 廿四烧基, 廿五院基, 廿hexyl, 廿heptylene, 廿八Alkyl, perylene nonaalkyl, triacontyl, isoheptyl, isooctyl, isodecyl, isodecyl, is undecyl, isododecyl, isotridecyl, Isotetradecyl, isopentadecyl, isohexadecyl, Heptadecyl, iso-octadecyl, iso-dodecyl, iso-arachiyl, iso-eicosyl, isodecyl monoalkyl, isodecyl dialkyl, 11 323585 201222151 isoindole trisyl, isoindole Four-hospital base, different 廿 廿 * 基 基, 廿 廿 烧 、, isodecyl heptadecyl, isodecyl octadecyl, isodecyl pentylene, iso- 30 decyl, 丨-methyl hexyl, 1-B Heptyl, methylheptyl, 1-cyclohexylethyl, 1-heptyloctyl, 2-decylcyclohexyl, nonylcyclohexyl, 4-methylcyclohexyl, 2,6-dimethylcyclo Hexyl, 2, dinonylcyclohexyl, 3, dimethylhydrazine cyclohexyl, 2,5-didecylcyclohexyl, 2,3-dimercaptocyclohexyl, 3,3,5-trimethylcyclohexyl, 4-tertiary butylcyclohexyl, ethylhexyl, 1-goldenyl, 2-adamantyl and the like. When the formula (1) is a phenyl group or a benzyl group, the substituents may be substituted. As the substituent, '(i) may be exemplified by (i) methyl group, ethyl group, propyl group, isopropyl group, (ii) butyl group, isobutyl group, tert-butyl group, pentyl group or the like (C1 to C5) alkane. (iii) a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or a ruthenium atom, (iv) a acid group, (v) a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a tertiary butoxide (C1 to C6) alkoxy group '(vi) via hydroxy group (C1 to C5) alkyl group (vii) methoxyethyl group, ethoxy group B a hydroxy (C1 to C5) alkoxy group such as a ethoxy group, a ethoxypropyl group, a butoxyethyl group or the like (C1 to C5), a (C1 to C5) alkyl group, (viii) a 2-hydroxyethoxy group, (ix) alkoxy (Cl to C5) alkoxy groups such as 2-methoxyethoxy, 2-ethoxyethoxy, etc., and (x) 2-sulfoethyl, carboxyethyl, cyano A (C1 to C3) alkyl group substituted by a sulfo group, a carboxyl group or a cyano group such as an ethyl group (except for an ethyl group). With respect to the ideal group among Ri to R4 of the formula (1), each may independently be a hydrogen atom or a (C1 to C6) alkyl group. In a preferred embodiment, both h and only 2 are 〇^ to (:6) alkyl, or either one is a hydrogen atom and the other is a (C1 SC6) urinary UR4 and both are RjR2 The same situation for both. 323585 12 2〇1222151 R5 to Rn in the formula (1) 'For the Cl to C6 alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group are exemplified. , cyclopentyl, hexyl, cyclohexyl, hydroxypropyl, 2~sulfoethyl, carboxyethylcyanoethyl, methoxyethyl, ethoxyethyl 'butoxyethyl, difluoro Methyl, pentafluoroethyl, and the like. In the case of R5 to Rn of the formula (1), the substituted or unsubstituted amino group may be an unsubstituted amino group or an alkyl group. Among them, an alkylamine group is preferred, and any one of an anthracene group or a diamide group is used. In the case of the alkyl group in the pyrene group, it is the same as the alkyl group in the above-mentioned oxime to R4, but is an unsubstituted C1 to C6 alkyl group, a C1 to C6 alkyl group or a cyano C1 to C6 alkyl group. good. In the case of the alkyl group, a dimethylamino group, a diisobutylamino group or a dicyanoethylamino group is preferred. Rs to Rn of the formula (1) are each independently a hydrogen atom; a gas atom; a C1 to C6 alkyl group which may be substituted with a chaotic group (ideally, an early substitution by a cyano group or a low level of a C1 to C6) The alkylamino group is more preferably an early or a C1 to C4 lower alkylamino group which may be substituted by a cyano group; or an unsubstituted ci to a C6 alkyl group (ideally an unsubstituted C1 to C4 lower alkyl group) More preferably, it is better. It is preferred that at least one of R5 to Rn in the formula (1) is a halogen atom (preferably a gas atom) or an alkyl group. In this case, the remaining groups may be any of the foregoing groups other than a halogen atom or an alkyl group, but these are each independently a hydrogen atom or a C1 to C4 lower alkyl group, and a hydrogen atom of 7 to 11 The situation is better. In the case of Rs to Ri? of the formula (1), it is preferable that Rs to Ru are independently, 323585 13 201222151 虱^ or C1 to C4 low fluorenyl groups, in the case of 匕 to ^ or Four are C1 to C4 lower alkyl groups, and the remaining groups are hydrogen atoms. This special case 'in terms of Rl3 to Rn, each independently, is atomic, CUC4, or cyano group substituted:: or diterpene to C4 lower alkylamino group, preferably R&quot To the heart, two are tooth atoms (preferably gas atoms), and others are hydrogen atoms. Examples of the atom in the above formula (1) include a fluorine atom, a gas atom, a desert atom, and an atom. In the above formula (1), the anion moiety z represents a halogen group, an anthracene anion anion, an alkylsulfonium methide anion, or an alkylsulfonate anion, and each i-alkyl group is independently a C1 to C10 alkyl group substituted with 3 to 6 tooth atoms. The fluorine atom is preferred for the tooth atom of the group. The desirable Z- may, for example, be a bis(trifluoromethyl)sulfonylphosphonium imide, a hexamethylenesulfonylsulfonate anion or a trifluoromethylsulfonium anion. Among them, the ruthenium (trifluoromethyl) hydrazine methide anion is more preferable. One of the desirable compounds represented by the above formula (1) may, for example, be a compound having at least one of Rn (preferably at least one of the core to the heart) is an i atom. Further, as for one of the other desirable compounds represented by the above formula (1), at least one of R5 to Rn (preferably at least i of Rl7 is preferred) is an alkylamine which may be substituted by a cyano group. a compound which is preferably a mono- or di-C1 to C4 alkylamino group which may be substituted by a cyano group. 14 323585 201222151 In the ideal compound of the above formula (1), z- is bis(trifluoromethyl)sulfonyl imine anion, hexamethylenetrifluorosulfonate anion, or trifluoromethyl More preferably, the sulfonate anion. In the above formula (1), as one of the preferred compounds, Ri and R4 each independently represent a hydrogen atom or a lower alkyl group of (Cl to C4) (ideally, all of ruthenium to R4 are hydrogen. An atom, or a hydrazine and one of R 2 and R 3 and R 4 is a hydrogen atom, and the other is a lower alkyl group (C1 to C 4 )), and each of R 5 to R 12 is independently a hydrogen atom or a lower alkane of (ci to C 4 ) a base (ideally at least one, more preferably 2 or 4 is a lower alkyl group of C1 to C4 and the other is a hydrogen atom), and Ru to R1 are each independently a hydrogen atom or a halogen atom (a chlorine atom is preferred) Or, a (C1 to C4) lower alkylamino group, the C1 to C4 lower alkyl group of the di(ci to C4) lower alkylamino group may be unsubstituted or substituted by a halogen atom or a cyano group. Z- is bis(trifluoromethyl)sulfonyl quinone imine anion, ginseng (difluoromethyl) sulfonyl anion, or trifluoromethanesulfonate anion (by trifluoromethyl) A compound of the sulfonium methide anion is preferred. In the compound, at least one of hydrazine to Rlz (preferably 2 or 4) is a lower alkyl group of C1 to C4, the other is a hydrogen atom, and at least one 疋i atom of Ri3 to Ri7 (in 1 or 2) It is preferably a halogen atom, more preferably the halogen atom is a gas atom, and a compound other than a hydrogen atom is more preferable. In the case of a more preferred compound, all of the ruthenium to L is a hydrogen atom, or a ruthenium and one of R2 and R3 and I are a hydrogen atom, and the other is a (C1 to C4) lower alkyl group (in the case of B). The base is good), Rs to Ri2 are, 匕 and 匕. Two or four of R5, R8, R1G and ru are (C1 to C4) lower alkyl (preferably methyl) 'others are hydrogen atoms, and one or two of the heart to the heart are halogen atoms. , 323585 15 201222151 疋 milk atom, the other is a hydrogen atom, z—is a double (tri-gas methyl) wall anthraquinone anion, ginseng (tri-gas methyl) 醯 基 基 基 基 基 基 or 乱 甲基 甲基 续a salt anion, a compound having two ginseng (trifluoromethyl) groups. In the case of the most ruthless compound, all of the m is a hydrogen atom, or the sputum and the sufficiency - the hydrogen atom, the other is the ethyl group, the second is the 2 or ", the heart And four of Rn are other compounds in which one or two hydrogen atoms are chlorine atoms, and the ruthenium atom 'Z is a ginseng (trifluoromethyl) 醯p-based anion is preferred. One or two of the halogen atoms are halogen atoms (the chlorine atom is in the form of a binary atom, and it is preferred that either one of R13 or R17 is a tooth atom (the gas atom R14 or both the core and Rn is a self atom (with a chlorine atom) The most preferred compound is the compound 16 in the following table. Specific examples of the color material compound represented by the formula (1) are shown in Table i, but the invention is not limited thereto. 323585 16 201222151 Table 1 Compound No. General formula (Substituent R of U Ί 1 anion moiety z - 1 2 3 4 s 6 7 8 9 10 11 12 13 14 IS 16 17 Me Me Me Me HHHHHHHHHH NMe: HH a 2 He lie Me He HHHHHHHHHH NHe2 HH 0 3 Me Me Me Ve HHHHHHHHHH NHe2 HH r 4 η-Βϋ n-Bu n-Bu n-Bu HHHHHHHHHHN (n-Bu); HH a S n-Bu n-Bu n-Bu n-Bu HHHHHHHHHH NMez HH a 6 Me EtCN He EtCN HHHHHHHHHH NHe2 HH a 7 n-Bu n-Bu n-Bu n-Bu HHHHHHHHHHN(Ph)* HH a 8 EtCN EtCN EtCN EtCN HHHHHHHHHH NHe2 HH a 9 n-Bu n-Bu n-Bu n-Bu HHHHHHHH Cl H NMez HH a 10 Bz Bz Bz Bz HHHHHHHHHH (EtCN) 2 HH a 11 EtCN EtCN EtCN EtCN HHHHHHHHHHN(EtCN)2 HH a 12 Me He He He HHHHHHHHHH NMe{ H He a 13 Et Et Et Et HHHHHHHHHHN(i-Bu), HH a 14 Et Et Et Et HHHHHHHHHHN(EtCI), HH a 15 HHHH Me HH Me H Me Me H Cl HHH Cl a 16 Et H Et H He HHHH Me HH Cl HHHH a 17 HHHH Me HH Mr H Me Me H Cl Cl HHH a 18 n-Bu n-flu n-Bu n-Bu HHHHHHHHHHN(EtCN); HHU · a Table 1 'The numbering in the substituent R term is represented by the code corresponding to R17, respectively. 'M represents methyl, Et represents ethyl, n-Bu represents n-butyl, i-Bu represents isobutyl, and EtCN is cyano. Ethyl, EtCl is a gas ethyl group, Bz is a benzyl group, Ph is a phenyl group, and an alkylamine group of Rl5 is used. Substituents on the amine group are also defined. Further, the case where z- is α, the case where the gin (tri-methyl)sulfonium methide anion is represented by the case of bis(trifluoromethyl)phosphonium imine anion '7 represents a trifluoromethyl group. In the present invention, the metal phthalocyanine pigment described later is used together with the color material compound of the formula (1) in combination with the color material compound represented by the formula (1). Sexual view: For a good situation, one of the good aspects. As for the metal phthalocyanine viol^ 〇 α Pigment Blue 15 : 6 * Pigment 10 et 23 and other steel phthalocyanine pigments are good in hue or resistance, and are preferred. 323585 17 201222151 In the present invention, the color material compound represented by the above formula (2) is used together with the color material compound of the formula (1) or together with the color material compound of the formula (1) and the above metal phthalocyanine compound. The pattern used together is also one of the good aspects. In the coloring matter compound represented by the above formula (2), Rla to R6a each independently represent a hydrogen atom, a halogen atom, a C1 to C12 alkyl group, a C1 to C12 methoxy group, a nitro group, a slow group, or a pyrocarbonyl group. It is preferable that all of R, a to 1^ are hydrogen atoms. Υι to Y4 are each independently a hydrogen atom, a Ci to C12, and a C1 to C12 alkyl group (preferably a π to C4 alkyl group) or both of Y3 and Y4 and Y4 and Y4. ) is better. Χι to each independently represent a hydrogen atom, a C1 to C12 alkyl group, a C1 to C12 alkoxy group, a halogen atom, a nitro group, a phenoxy group, a carboxyl group, an alkoxycarbonyl group, a formammine group, a sulfo group, or Aminesulfonyl, χ1 to Xs may be the same or different. The anion moiety Z- represents a halogen-based quinone imine anion, a thiol anion, or a (tetra) sulfonate anion, each of which is independently substituted by 3 to 6 (four) atoms (Qian Xuan The C1 to C10 alkyl group is preferably a C1 to C10 alkylsulfonium methide anion substituted with 3 to 6 halogen atoms (preferably a chlorine atom). In the case of the tooth atom of the formula (2), The same may be mentioned as described in the above formula (1). Examples of the alkyl group of the formula (2) include a methyl group, an ethyl group, a n-propyl group, a group, a n-butyl group, and the like. Secondary butyl, tertiary butyl ', isobutyl, positive di-hexyl: n-octyl, ethylhexyl, cyclohexyl, etc. C1 to C12, such as ^ 丨 and ., these alkyl groups may have a substituent ' For the substituent, σ 'bovine. 3⁄4 ethyl, hydroxypropyl, hydroxybutyl, 2-sulfoethyl, 323585 3 18 201222151 carboxyethyl, cyanoethyl, methoxyethyl, Ethoxyethyl, butoxyethyl, difluoromethyl, pentafluoroethyl, aminemethanyl, carboxyl, etc. In the case of the alkoxy group of the formula (2), The alkoxy group of the C1 to C12 alkyl group having the same alkyl group, and the alkoxycarbonyl group may also be a group having an alkoxycarbonyl group of a C1 to C12 alkyl group. In the case of the aryl group of the formula (2), For example, an aromatic hydrocarbon residue such as a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a benzyl group or a benzoyl group; an η ratio bite group, a 0-pyrene group, a pyrimidinyl group, a quinolyl group, an isoquinoline group; An aromatic heterocyclic residue such as an aryl group, a fluorenyl group, an indolenyl group, an imidazolyl group, a carbazolyl group, a thienyl group, a furyl group, etc. These aryl groups may have a substituent, and in the case of the substituent For example, an alkyl group, an alkoxy group, a halogen atom, a sulfo group, a carboxyl group, an alkoxycarbonyl group, an amine fluorenyl group, a cyano group, etc. may be mentioned. The anion moiety z- of the color material compound represented by the formula (2) It is the same as that described in the formula (1), and specific examples thereof include bis(trifluoromethylsulfonyl)% mercaptoquinone anion and ginseng (trifluoromethyl)sulfonium methylation. It is preferably a ruthenium, a difluoromethyl phthalate anion, a nonafluorobutyl phthalate anion or the like, and particularly preferably a hexamethylene sulfonium sulfonate anion. In the preferred coloring material compound represented by the formula (2), Ria to Rea are all hydrogen atoms, and either Y2 or Y3 and Y4 are either C1 to C12 alkyl groups (preferably C1 to Any one of C4 alkyl to Χ5 is a carboxyl group, an alkoxycarbonyl group (preferably a C1 to C4 alkoxycarbonyl group) or a carboxamide (preferably a benzylaminocarbonyl group or a carboxylic acid group) a compound substituted with a C1 to C4 lower leuminocarbonyl group, a hydrogen atom, and a Z is a ruthenium (trimethylene) sulfonate anion. 323585 19 201222151 More preferably (2) In the case of the color material compound shown, Rla to R6a are all hydrogen atoms, 丫! All of Y4 are a compound of Cl to C4 alkyl group (preferably ethyl), X! is a carboxyl group, X2 to X5 are a hydrogen atom, and Z is a sulfhydryl sulfonate anion. Specific examples of the color material compound represented by the formula (2) are shown in Table 2-1 and Table 2-2 below, but the present invention is not limited thereto. 20 323585 201222151 Table 2_1 Compound No. 2-1 Η 丫 Et, 丫, Γ〇丫, f^Et „3c Renren jAACH, 〇2StS〇2CF3 Jv^COOEt S02CF3 2-2 Η H H3CAAjAACh3 F3〇〇2s.e .so2CF3 2-3 Et Et F3C02S, g/S02CF3 Jv.CC)0H S02CF3 U 2-4 Et Et Already, 丫, 1^0 丫, T^Et F^OjS^Q^SOjCF, Jyc〇〇h 2- 5 ff Ε*^ΝΝιΓ%ν〇Ύ^Ύ&quot;Ν&quot;Ει F3C02S, g/S02CF, Jv^COOEt S02CF3 u 2-6 Et Et F3C02S, g/S02CF3 /J^COOEt u 2-7 f ^ Ε,ΝΎ ^Υ〇Ύ^Ύ^Ει F3C02S, g/S02CF3 Jv.CC)OMe S02CF3 cx 21 323585 201222151 Table 2-2 Compound Number Chemical Formula 2-8 Et Et f3co2s^so2cf3 Jx^CONH-^~^ S02CF3 2-9 Η H Ε,ΝΎ^Τ〇丫~ f3co2s^so2cf3 Jv^COOEt SO2CF3 CT 2-10 Η H Et^NY^Y°'V^Y&gt;N®Et f3co2s^so2cf3 S02CF3 0 2-11 V ?Hj ^丫, !^ 丫~f&quot;N:CH3 F3CO2Sx0xSO2CF3 X^COOEt SO2CF3 u 2-12 HaCA^A^ky F3C02S, g/S02CF3 J^/COOEt S02CF3 u 2-13 Et Et Εί^γ-γ°γγ&lt; F3C02S, g /S02CF3 XONH V S02CF3 ac 22 323585 η 201222151 Formula (1) or formula (2) used in the colored resin composition of the present invention ) The color material compounds shown, for example, can be obtained by the known synthesis method of "Theory of Manufacturing Dye Chemistry" (pp. 373 to 375) issued by Hiroshi Hiroshi at the company. It is synthesized by purchasing a commercially available product in which an anion moiety is a chlorine anion, and adding a corresponding salt or acid to perform salt exchange. In the present invention, in the case of synthesizing a color material compound by salt exchange, for example, a color material compound in which an anion portion is a gas anion is dissolved in a reaction solvent [for example, water, methanol, ethanol, isopropanol, acetone, A water-soluble polar solvent such as N,N-dimercaptocarbamide (hereinafter abbreviated as DMF) or N-mercapto-2-pyrrolidone (hereinafter abbreviated as NMP), and these solvents may be used singly or in combination. In the case, a corresponding salt or acid of about 0.5 to 3 equivalents is added, and the mixture is stirred at a predetermined temperature (for example, 0 to 10 ° C), and is easily obtained by taking out the precipitated crystal. The total solid content of the colored resin composition of the present invention (refers to the total amount of solid components composed of a color material compound, a binder resin, a curing agent, etc. other than the dissolution, j. The same definition is used hereinafter.) The content ' of the color material compound represented by the above formula (1) contained in 100 parts by mass is preferably from 2 to 30 parts by mass, more preferably from 3 to 3 parts by mass, based on 0.1 to 60 parts by mass. Further, in the case of the total solid content of the colored resin composition of the present invention, the coloring matter compound of the formula (1) contains 2 to 10% by mass, more preferably 3 to 1% by mass, of the color of the present invention. The resin composition is more preferable. When the content of the coloring material compound represented by the above formula (1) is too large, there is a problem that precipitation or aggregation occurs. The adhesion to the substrate is lowered due to insufficient hardening. When the content is too small, sufficient color purity is not obtained in terms of color characteristics.

S 323585 23 201222151 The tendency. When the solubility of the coloring material compound represented by the above formula (1) with respect to the colored resin composition is low, it may be the same as the pigment of the optional component described later, and a dispersing agent or a dispersing aid may be used in order to disperse. The color material compounds represented by the above formula (1) may be used alone or in combination of two or more. Also, other dyes or pigments may be mixed. Further, since the present invention relates to blue strontium, it is desirable to use a combination of a known blue dye or a violet dye, or a blue pigment or a violet pigment, etc., especially with the aforementioned metal phthalocyanine pigment (preferably It is one of the desirable aspects of the coloring resin composition of the present invention which is a copper phthalocyanine pigment or/and a coloring material compound represented by the above formula (2). The content of the aforementioned metal phthalocyanine pigment (preferably copper phthalocyanine pigment) or the content of the color material compound represented by the above formula (2) is 0 to 30 in the total solid content of the colored resin composition of the present invention, respectively. About % by mass. The total of the color material compounds represented by the above formula (1) is usually about 2 to 60% by mass, preferably about 10 to 30% by mass. When a metal phthalocyanine pigment (preferably a copper phthalocyanine pigment) is used in combination, the content thereof is usually from about 5 to 30% by mass in the total solid content of the colored resin composition of the present invention, and is from 7 to 20% by mass. good. Further, when the coloring compound of the formula (2) is used in combination, the content thereof is usually from about 0.5 to 10% by mass, preferably from 1 to 7% by mass, based on the total solid content of the colored resin composition of the present invention. The binder resin used in the present invention is preferably a resin having the following properties. That is, (i) for the dispersion stability of pigments or water-insoluble dyes, it has a function as a dispersing agent or a dispersing aid, 24 323585 201222151, when j1 is used in the photolithography method, it can be dissolved in the manufacture of color filters. Alkaline developing solution used in the development processing step of the film /*···, *

Ul1) a polymerization initiator (for example, a photopolymerization initiator or/and, a, a poly-δ initiator) contained in the coloring agent of the present invention in order to form a finer fine pattern. And a hardening agent (for example, a polymerizable monomer, a specific photopolymerizable monomer, or a thermopolymerizable monomer, etc.) has excellent hardening characteristics at the same time. The coloring resin composition of the present invention obtained by blending the binder resin with a polymerization initiator (for example, a photopolymerization initiator or a thermal polymerization initiator) and a polymerizable monomer (photopolymerizable single) contained therein The material or the thermal polymerizable monomer), the coloring material compound of the formula (1), and the pigment dispersion liquid have good compatibility, and it is necessary to have stability such as precipitation or aggregation during storage or use. When the colored resin composition of the present invention is used in the ink jet method, since it is not necessary to determine the solubility, it is preferable to select a resin having good compatibility with other color material compounds or additives. As the binder resin, a known resin can be used. Desirably, an ethylenically unsaturated monomer having a lysine group as described later is also referred to as a conjugate of a silk-containing money and a monomer or a phase-containing unsaturated monomer, or may be Copolymers of ethylenically unsaturated monomers, a total of other aromatic unsaturated monomers having an aromatic nonyl group or an aliphatic fluorenyl group (hereinafter also referred to as other unsaturated monomers), good. Further, in the case where the polymer has a side chain or a terminal having an epoxy group, it is also possible to use a epoxide-added epoxy acrylate resin in a step of 323585 25 201222151. The above-mentioned monomers and the like used in the production of the binder resin may be used singly or in combination of two or more kinds, and may also be used as a binder resin. The above-mentioned carboxyl group-containing unsaturated monomer which can be used in the present invention can be exemplified by (i) acrylic acid, mercaptopropionic acid, crotonic acid, α-gas acrylic acid, cinnamic acid, etc. Unsaturated monocarboxylic acids; (ii) unsaturated dicarboxylic acids (anhydrides such as maleic acid, maleic anhydride, fumaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, and mesaconic acid) (iii) an unsaturated polyvalent carboxylic acid (anhydride) having a valence of 3 or more; (iv) 2-(indenyl)propenyloxyethyl hexahydrofuric acid, 2-(indenyl) phthalate Propylene decyloxyethyl-2-hydroxypropyl ester, 2-propenyl decyloxyethyl-2-ylidylethyl ugly acid, and the like. These ethylenically unsaturated monomers having a carboxyl group may be used singly or in combination of two or more. Among these, (meth)acrylic acid is preferred. The above-mentioned hydroxyl group-containing unsaturated monomer which can be used in the present invention can be exemplified by 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, or (decyl)acrylic acid. 3-hydroxypropyl ester, 4-hydroxybutyl (meth)acrylate, 3-hydroxybutyl (▼) acrylate, 5-hydroxypentyl (meth) acrylate, (meth) acrylate 4_ Hydroxypentyl ester, 3-hydroxypentyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 5-hydroxyhexyl (meth)acrylate, 4-hydroxyhexyl (meth)acrylate, C1-C8 diol (mono)(methyl) such as 5-hydroxy-3-methyl-pentyl methacrylate, cyclohexane-L dimethanol-mono(meth) acrylate 26 323585 201222151 C Glycolic acid vinegar; glycerin monomethacrylic acid material C3 to (3) acrylic acid vinegar; (methyl) acrylic acid called ethyl ethyl oxoethyl hydrazine, polyethyl hydrazine (methyl) propylene vinegar, poly Propylene glycol mono(methyl)propoxylate propylene glycol) monohydroxy acrylate and other hydroxyl-terminated polyalkane early (mercapto) acrylate vinegar (to poly (^ To (tetra) diol mono (▼-based) propyl vinegar vinegar is preferred) and the like contains (meth) propyl acetoacetate. These thiol-unsaturated monomers having a thiol group can be used alone. Two or more kinds are used. In the case of the ethylenically unsaturated monomer having a &amp; group, it is preferred to use the above-mentioned (meth) propyl acetoacetate containing a thiol group, and a hydroxy group C1 to C6 (methyl). Further, the acrylate is more preferable. Further, as the other unsaturated monomer, for example, styrene, α-methylstyrene, o-vinyltoluene, m-vinyltoluene, p-ethylene Aromatic vinyl compounds such as toluene, o-styrene styrene, m-chlorostyrene, p-chlorostyrene, p-methoxyethylidene; methyl (meth) acrylate, (meth) acrylate Base ester, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, (methyl) ) secondary butyl acrylate, secondary butyl (meth) acrylate, benzyl (meth) propyl phthalate, p- cumyl phenoxy ethane (Meth)acrylate, 2-methyl-3-phenoxypropyl (meth)acrylate, o-phenylphenol epoxypropyl ether (mercapto) acrylate, o-phenylphenol (A) An unsaturated carboxylic acid ester such as an acrylate hydroxyethylate or a phenoxyethyl (meth)acrylate (preferably a C1 to C4 alkyl ester of a phenyl group containing a phenyl group) is more preferably a Phenyl or phenoxy-substituted (mercapto)acrylic acid C1 to C4 alkyl vinegar, (mercapto) propyl acetoate cyclopentyl | (, thiol) propyl 323585 27 201222151 cyclohexyl ester, (曱Trisylcyclohexyl acrylate acrylate (norcapto)acrylic acid norbornyl ester, (meth)acrylic acid norbornyl decyl ester, (fluorenyl) phenyl norbornyl ester, (decyl) acrylate Basenorbornyl ester, (fluorenyl) isobornyl acrylate, borneol (meth) acrylate, menthyl (meth) acrylate, methacrylate (meth) acrylate (meth) Fenchyl (meth)acrylate), adamantyl (meth) acrylate, dimethyl alkane Base ester, tricyclo[5. 2. 02, 6] 癸-8-yl ester, (fluorenyl) acrylic acid tricyclo[5. 2. 1. 02, 6] 癸-4- a compound containing an alicyclic skeleton such as a methyl ester, a cyclodecyl (meth) acrylate, a 2-(indenyl) propylene methoxyethyl hexahydrophthalic acid or a tributyl butyl (meth) acrylate (It is preferably a (meth)acrylic acid Sa containing a C5 to C10 aliphatic ring, and a (meth)acrylic acid of a C5 to C10 aliphatic ring is preferred; methoxypolyethylene glycol Monodecyl acrylate, lauryloxy polyethylene glycol mono(meth) acrylate, octyloxy polyethylene glycol polypropylene glycol mono(meth) acrylate, nonyl phenoxy polyethylene glycol monoacrylate , alkyl-terminated polyalkylene glycol mono(meth)acrylates such as nonylphenoxy polypropanol monoacrylate, allyloxy polyethylene glycol_polypropylene glycol mono(meth)acrylate (from C1 to C10 alkyl terminal poly C2 to C4 alkanediol (meth) acrylate is preferred; 2-aminoethyl acrylate, 2-aminoethyl methacrylate, 2-aminopropyl acrylate, Methacrylic acid 2_ Alkyl propyl ester of unsaturated carboxylic acid such as propyl propyl ester, 3-aminopropyl acrylate or 3-aminopropyl methacrylate (based on C1 to C4 alkyl (meth) acrylate) (preferably); glycidyl acrylate, glycidyl methacrylate, (meth)acrylic acid 3,4 ring 323585 28 201222151 oxybutyl ester, (meth)acrylic acid (3, 4-epoxy Cyclohexyl)methyl (f-)acrylic acid 4, butyl butyl acrylate, propyl acrylate, etc., unsaturated propyl vinegar (with (oxy) (meth) oxime ci to (3) aliphatic (methyl) Acrylic acid is good); Ethylene diacetate sulphur vinegar, Ding Yu Chu E women's sputum, sulphuric acid sulphur vinegar and other New Zealand 酉 酉 category, acid group: fine, hexenyl ethyl test, thin Propyl epoxide propyl, carbamide, epoxide, propylene propylene, acrylonitrile, methyl methacrylonitrile, dicyandiamide, stalk Hybrid; (10) _, Μ = 醯 H gas (iv) decylamine, hydrazine _ phenyl mala _, =: lysine, Ν _ (meth) propylene thiol hydroxy, f propyl amide, base Ethyl)methyl hydrazine (= ethyl 5 unsaturated hydrazine or unsaturated quinone imine; U-丁二:,:: aliphatic conjugated diene such as arsenic lactide, a thin, formazan, polymethyl methacrylate, polypropylene: guangben, polyacrylic acid The other ends of the high-chain of n-butyl ester, polyfluorene (tetra)-n-butyl ester, polymethacryloyl group or monomethyl propyl group may have other unsaturated monomers such as monopropene oxime, which may be mono- (mac-), etc. . Among these, it is used in the case of other than unsaturated or mixed. In the case of a phenyl group C1 to oxime and an early body, the ideal one is: an aliphatic ring containing a (methyl) dimethyl group: a group c, a wide range, containing; ^ to a cl〇C4 glycerol (Mejyl* to The CIO is condensed at the end of the C2 to the carboxylic acid ===...1 to (4)-based (meth) propyl ester. It is better than the (meth) acrylate such as the earth (methyl) phthalate. (. (Methyl) acrylate 323585 29 201222151, etc., which may be substituted by a phenyl group or a (meth) acrylate group containing a CCl to a C4 alkyl group. It is a (meth) acrylate which can be substituted with a phenyl group to a C4 alkyl group. Most preferably, it is a benzyl acrylate. Further, it is also possible to use a polymerization in which a further double bond is further introduced into a side chain of the copolymer. For example, a maleic anhydride moiety of a copolymer of styrene, ethylene, acrylic acid, acrylate, or acrylamide copolymerizable with maleic anhydride, and an acrylic acid vinegar having an alcoholic hydroxyl group such as hydroxyethyl acrylate. Or a compound having an epoxy group such as a glycidyl methacrylate, which is reacted and half-esterified, and an acrylic acid, an acrylate, and a compound obtained by reacting a hydroxyl group of a copolymer of an acrylate having an alcoholic hydroxyl group such as hydroxyethyl acrylate with acrylic acid, etc. Further, a polyurethane resin or a polyamide or a polyimide resin may also be used. , polyester resin, commercially available ACA_200M (manufactured by Daicel Co., Ltd.), ORGA-3060C Osaka Organic Chemical Co., Ltd., Αχ3 (manufactured by Sakamoto Co., Ltd.), UXE-3024C Pharmacy (stock) company), UXE-3000C Nippon Chemical Co., Ltd., ZGA-287HC Nippon Chemical Co., Ltd., TCR-1338H (Nippon Chemical Co., Ltd.), ZXR- 1722H (manufactured by Nippon Kayaku Co., Ltd.), ZFR-1401H (manufactured by Nippon Kayaku Co., Ltd.), and ZCR-1642 (manufactured by Nippon Kayaku Co., Ltd.). The binder resin contained in the colored resin composition of the present invention is a copolymer of (meth)acrylic acid (preferably methacrylic acid) and a copolymer copolymerizable with the monomer (meth) An acrylic copolymer resin is preferred, and a copolymer of (meth)acrylic acid (preferably methacrylic acid) and a (fluorenyl) acrylate compound (hydroxyl-containing (meth) acrylate) is also preferred [also known as Methyl) acrylic acid-(meth) acrylate copolymer]. As the copolymer of the binder resin, 323585 30 201222151 preferably has an acid value of 10 to 300 ng KOH/g) or/and a copolymer having a hydroxyl group of 1 Å to 2 Torr (mg KOH/g). It is preferably a copolymer having an acid value of up to mo (mgKOH/g), more preferably from about 1 Å to about 200 (mgKOH/g). The molecular weight may be any function as a binder resin, and the weight average molecular weight (Mw) (in terms of polystyrene) is usually about 2〇〇〇4_00, preferably about 3,000 to 100%, and 5〇〇. It is better to use around 8,000 to 40,000. The ratio of the (meth)acrylic acid-(indenyl)acrylic acid-g-copolymer is not particularly limited, but considering the _image-like material, the mass ratio ratio = base) propionate: a copolymerizable monomer (to曱基) (4) : Good) is 1:0.5 to 1:1 〇, with m illusion: about 5 is good, and the above (曱基) A glycerin is a compound, and the above-mentioned a acrylate, and the foregoing diester. In the case of the (fluorenyl) acrylate compound, it is preferably substituted with a (meth) propylene group containing a propylene aliphatic ring or the above. [Methyl)propene" is intended to be a more preferred (meth)acrylic acid (meth)acrylic acid and a styrene-acrylic copolymer which can be substituted with a styrene acrylate (by sulfhydryl) The benzyl acrylate is preferably a (meth) propyl acetoic acid and a C5 to C10 aliphatic acrylate or a (meth) copolymer which may be copolymerized only by the two, such as methacrylate 0 to 20% by mole, from 〇 to 1 〇 耳 含有 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 The term "(indenyl)acrylic acid" or the like refers to the use of acrylic acid or mercaptoacrylic acid, or both. For example, (meth) acrylate means the use of acrylate or/and methacrylate. In general, when the pigment composition of the present invention contains a pigment, the resin composition of the present invention preferably contains a dispersing agent, or a dispersing agent and a dispersing aid. a pigment having a good sorption property for a pigment In the present invention, it is preferable to use a pigment in combination with a pigment, for example, a technique of dispersing a pigment using a pigment-based dispersant is known as Patent Document 4 mentioned above. A method of mixing a sulfonate of a pigment or a metal salt thereof with a pigment, or a method of mixing a substituted aminomethyl derivative with a pigment, etc., is known as a technique. The resin-based dispersant also has a non-polar nonionic system. However, it is generally a polymer resin having an acid value, an amine value, or the like which imparts good pigment sorption properties, and examples thereof include an acrylic resin, a polyamine phthalate resin, a polycarboxylic acid, a polyamide resin, and a polyester resin. In the specific example, for example, ED211 (manufactured by Nanben Chemical Co., Ltd.), Ajisper RTMPB821 (manufactured by Ajinomoto Fine-Techno Co., Ltd.), SolsperseRTM 71000 (made by Avecia Co., Ltd.), etc. In the resin composition of the invention, the content of the dispersant is from about 0 to 30% by mass, preferably from 0 to 20% by mass, based on the total solid content. The binder resin used in the present invention A commercially available product may be used or may be synthesized. When the binder resin is produced, it is necessary to use a polymerization initiator. Specific examples of the polymerization initiator used in the synthesis of the copolymer include: 32 323585 g 201222151 α' α —Azobis(isobutyronitrile), 2, 2,-azobis(2-methylbutyronitrile), peroxyoctyl S-second butyl vinegar (t_butyl per〇Xy〇Ct〇 Ate), peroxydi-2-butyl, benzyl peroxide, methyl ethyl ketone, etc. The use ratio of the polymerization initiator is 100 parts by mass relative to the total amount of all monomers used in the copolymer synthesis. In the case of 0.01 to 25 parts by mass, it is preferred to use an organic solvent described below for the synthesis copolymerization. The organic solvent is preferably one having sufficient solubility for a monofunctional monomer or a polymerization initiator to be used. The reaction temperature at the time of synthesizing the copolymer is preferably from 5 Torr to 12 Torr, particularly preferably from 80 to 100 °C. Further, the reaction time is preferably from 丨 to 6 〇, more preferably from 3 to 20 hours. The copolymer as the binder resin is preferably a copolymer having an acid value of 10 to 3 Å (mg KOH/g) or/and a hydroxyl group of 1 Å to 200 (mg KOH/g), and an acid value or a The base price decreases in the following cases. The weight average molecular weight (Mw) of the copolymer is preferably from 2,000 to 400,000, more preferably from 3 Torr to looooo. When the weight average molecular weight is below, or 400,000 or more, the sensitivity and development properties are lowered. In the present invention, the binder may be used alone or in combination of two or more. The content of the binder resin in the present invention is usually from 0.5 to 99 parts by mass, preferably from 5 to 50 parts by mass, per 100 parts by mass of the total solid content of the colored resin composition. In this case, the content of the binder resin is less than 5 parts by mass, _developing property is lowered, or problems such as ink adhesion contamination or film residue occur in areas other than the halogen component. The hardener used in the present invention may be exemplified by radical polymerization 323585 33 201222151. In the case where the monomer is a monomer, the case where the material is hardened is a specific example of an epoxy resin, other melamine hardeners, etc. There may be mentioned (meth)acrylic acid 2, ethyl ethyl brewing, (meth)acrylic acid propyl propyl vinegar, (meth)acrylic acid 2-ethylhexyl vinegar, ethylene glycol di(meth)acrylic acid vinegar, Diethylene glycol di(meth)acrylate, triethylene glycol (decyl) acrylate, tetraethylene glycol (mercapto) acrylate vinegar, tri-propyl propyl propyl trimethacrylate, neopentyl Tetraol bis(indenyl) acrylate, neopentyl alcohol tris (acid vinegar, neopentyl alcohol tetrakis(yl) acrylate, dipentaerythritol hexa-4 (comparable)

Acrylic, glycerin (meth) acrylate, di(meth)acrylic acid: A-type epoxy ester, di(meth)acrylic acid bisphenol F-type epoxy ester, bis(methylamide) acrylic acid double (4) type epoxy vinegar, ethoxylated trimethyl methacrylate III (methacrylic acid vinegar, propane trimethyl methacrylate tris(methyl) acrylate vinegar, ethoxylated glycerol bis(indenyl) acrylate, Tris(meth)acrylate, bis(hydroxy)propane tetra(indenyl)acrylate, pentoxide tetrakis(meth)acrylate, 9,9-double [4] -(2-Acryloxyethoxy) base], KAYARADrtmRP-1〇4〇 (manufactured by Nippon Kayaku Co., Ltd.), KAYARADrtmDPCA-30 (manufactured by Nippon Kayaku Co., Ltd.), UA_33H ( New Nakamura Chemical Industry Co., Ltd., UA-53H (manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), M-8060C East Asia Synthetic Co., Ltd.); for thiol-based polymerization monomers: TEMPIC (堺Chemical Industry Co., Ltd.), ΤΜΜΡ (堺 堺 堺 公司 公司 公司 ΡΕΜΡ ΡΕΜΡ ΡΕΜΡ 、 、 、 、 、 、 、 DP DP DP DP DP DP DP DP DP DP DP DP DP DP DP堺Chemical Industry Co., Ltd.); In terms of epoxy resin: NC-6000, NC-3000, EOCN-1020, XD-1000, ΕΡΡΝ-501Η, BREN-S of 曰本化药(股) , NC-7300 L'Daicel Chemical Co., Ltd. Products CELL0XIDE 34 323585

201222151 2021P, EHPE3150, CYCLOMER M100, EPOLEAD PB3600, Japan Epoxy Resin Co., Ltd. EPIK0TErtm828, EPIKOTERTM YX8000, EPIKOTErtmYX4000, Sila-aceRTMS510 (CHISSO), TEPIC (Chemical Industry Co., Ltd.) The melamine hardening agent may, for example, be methylolated melamine or Mw-30 (manufactured by Sanwa Chemical Co., Ltd.). These may be used alone or in combination of two or more. As the desirable polymerizable monomer as the hardener, a polyfunctional (meth) acrylate compound is preferable, and a 3- to 6-functional (meth) acetoacetate compound is more preferable. The 3 to 6-functional (meth) acrylate compound may, for example, be neopentyl alcohol tri- or tetra (meth) acrylate or di-n-pentaerythritol (tri-hexamethyl) acrylate. The specific enthalpy is preferably from 1 to 80 parts by mass, preferably from 10 to 6 parts by mass, more preferably from 20 to 60 parts by mass, based on the total solid content of the colored resin composition. It may be 5 to 3 parts by mass depending on the case. The pigment which can be used in combination in the coloring resin composition of the present invention is preferably one having a spectral characteristic suitable for a color filter, and may be appropriately selected from among dyes, organic pigments, and inorganic (IV), and may be used alone or in combination according to requirements. More than one kind to use. The content of these is 〇 to 6 () parts by mass in the total solid content of 1 GG parts by weight of the composition, preferably from 0 to plus parts by mass, and from 5 to 30 parts by mass. good. The various pigments and dyes of these are described in detail below. As far as the organic pigments which can be used in combination in the present invention, as long as the spectroscopic characteristics of the *color calendering sheet are available, there is no limitation, and the age can be listed as follows: • brewing system, ugly crystal system, triphenyl group Totsuka s soil, stupid and imidazolidone, 323585 35 201222151 喧. Quinacridone, azo chelate, azo, iso- cylinone, isoindolinone, pyronthrone, 彀蒽^ (indathronehf, ®° i^(anthrapyrimidine)$,:,;|:· 蒽Inlay: S brewing i (dibromoanthanthrone), 蒽 _ (zhang 13¥8111±1'0116), 茈, 紫 酮 (mouth 61411〇116 a pigment such as a quinophthalone system, a thioindigo system, a dioxazine system, a °|:nY_(quinacridone) system, a dibenzoxanthene (xanthene) system, or the like; A lake dye, a dyed lake pigment, etc., which are insolubilized with a respective precipitating agent such as an acid dye, a basic dye, a direct dye, etc. More specific color index, for example, a pigment blue l , 1 : 2 , 9 , 14 , 15 , 15 : 1 , 15 : 2 , 15 : 3 , 15 : 4 , 15 : 6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36 , 56 , 56 : 1 , 60 , 61 , 61 : 1 , 62 , 63 , 66 , 67 , 68 , 71 , 72 , 73 , 74 , 75 , 76 , 78 , 79 ; pigment violet 1 , 1 ·· 1, 2, 2: 2, 3, 3: 1, 3 ·· 3, 5, 5 : 1, 14, 15, 16, 19, 23, 25, 27, 29, 3, 32, 37, 39, 42, 44, 47, 49 , 50; pigment violet (pigment vi〇let) 3, 4, 27, 39, etc. Especially the color or tolerance of metal phthalocyanine pigments such as pigment blue 15 : 6 or pigment violet 23 The inorganic pigment which can be used in combination in the present invention is not particularly limited, and examples thereof include a composite metal oxide pigment, carbon black, black low-grade titanium oxide, titanium oxide, barium sulfate, and zinc oxide. Lead sulfate, chrome yellow, iron oxide, ultramarine blue, Prussian blue, oxidized complex, recorded white, iron black, wrong dan, zinc sulphide, cadmium yellow, cadmium red, zinc 'manganese violet, cobalt violet, barium sulfate, magnesium carbonate, etc. 323585 36 201222151 Metal oxides, metal sulfides, sulfates, metal hydroxides, metal carbonates, etc. The dyes which can be used in combination in the present invention are not particularly limited, and examples thereof include acid dyes, basic dyes, direct dyes, and sulfur dyes. , anthraquinone dyes, naphthol dyes, reactive dyes, disperse dyes, and the like. Any one may be dissolved in an organic solvent, but a dye which is insoluble in an organic solvent can be suitably used as a dispersion. The aforementioned dye which is insoluble in an organic solvent can be modified by a conventionally modified method. For example, it is known that, in the case of an acid dye or a basic dye, an organic amine compound (for example, n-propylamine, ethylhexylpropionamide, etc.) is reacted to be converted into an amine salt dye, or the same sulfonic acid group is the same organic The amine compound is reacted to be modified into a sulfonamide-based dye or the like. These amine modified dyes can also be used in the colored resin composition of the present invention. For a specific dye, the color index, for example, may be exemplified by solvent blue (so 1 vent b une) 2, 3, 4, 5, 6, 23, 35, 36, 37, 38, 43, 48, 58 , 59 , 67 , 70 , 78 , 98 , 102 , 104 ; basic blue 7 ; acid blue 80 , 83 , 90 ; solvent purple purple dye 8 , 9 : purple 4 , 5, 14; alkaline purple 10 and so on. The photopolymerization initiator added to the coloring resin of the present invention used in the photographic method is preferably one having a sufficient sensitivity to ultraviolet rays emitted from an ultrahigh pressure mercury lamp generally used as an exposure light source. A photopolymerizable photoinitiator, a photoacid generator or a photobase generator used in an ion-polymerizable resin. In terms of photopolymerization, a polymerization accelerator called a sensitizer which is hardened with less exposure energy can be used in combination of 37 323585 201222151. The photopolymerization initiator which can be used is not particularly limited. Specific examples thereof include benzil, benzoin ethyl ether, benzoin butyl ether, benzoin propyl ether, and diphenyl. Anthrone, 3,3,-dimethyl-4-methoxybenzophenone, benzamidine benzylic acid, benzammonic acid ester ester, 4-benzylindolyl-4,-mercaptodiphenyl sulfide , benzyl dimethyl ketal, bismuth 2-butoxyethyl decyl vinegar, chlorothioxanthone, methyl ketone 4 ketone, ethyl oxime _, isopropyl thioxanthene Ketone, dimethyl thioxanthone, diethyl thioxanthone, diisopropyl thioxanthone, dinonylaminomethyl benzylate, 1-(4-dodecylphenyl)-2- Hydroxy-2-methylpropane-1-ketone, hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-indolin-1-phenylpropan-1-one, i-isopropylphenyl)_2-hydroxyl _2_Methylpropanol*-1-one, benzyl benzoyiformate), 2-methyl-1-(4-methylthienyl)_2-morpholinopropane-丨-ketone, 2-benzyl Base 2_didecylamino-l-(4-morpholinylphenyl)-butanone-oxime, 2,4-bis(trichloromethyl) 6-(4-methoxyphenyl)- 1, 3, 5-s-triterpene, 2, 4, 6-para-(trimethane)-l,3,5-s-trisole, 2,4-bis(tribromoindolyl)-6-( 4,-methoxyphenyl)-1,3,5-3-trimorphine, 2,4,6-para-(tribromoindolyl)-1,3,5_3_trisole, 2'4-double (dimethyl sulfhydryl;)-6_(1,3_benzodioxol-5-yl)-1,3,5-s-triterpene, benzophenone, benzamidine benzyl, hydrazine _(4-phenylthiophenyl)butane-1,2-dione-2-indole-0-benzylate, i-(4-methylthiophenyl)butane-1,2- Diketo-2-indole-indole-acetate, hydrazine-"monomethylthiophenyl"butane-butanone-0-acetate, 4,4'-bis(diethylamino) Benzophenone, p-monomethylammonic acid isoamyl ester, p-dimethylaminobenzyl acid ethyl ester, 2,2-bis(fluorenyl-phenyl)-4, 4,, 5, 5' _tetraphenyl hydrazine, 2, _biimidazole, weight 323585 38 201222151 Azide naphthoquinone initiator. Or commercially available KAYACURErtmDMBI, KAYACURErtmBDMK, KAYACURErtmBP-100, KAYACURErtmBMBI, KAYACURErtmDETX-S, KAYACURErtmEPA (all in Japan Chemical Pharmaceutical Co., Ltd., DAR0CURErtm1173, DAR0CURErtm1116 (all manufactured by Merck Japan Co., Ltd.), IRGACURErtm907, IRGACURE RTM 369, IRGACURErtm379EG, IRGACURErtmOXE-01, IRGACURErtmOXE-02, IRGACURErtmPAG103 (IRGACURE is a Ciba Specialty Chemicals Co., Ltd.), TME-Trimorph (made by Sanwa Chemical Co., Ltd.), Biimidazole ( Black gold chemical (share) company system), 3 Ding anti-110, 3 Ding feet-1 (all are 跎邛6 chemical (share) company system) and so on. In the case of a thermosetting resin composition used in an inkjet method or the like, a thermal polymerization initiator is generally used, and a photopolymerization initiator may be used in combination as needed. The thermal polymerization initiator may be an azo compound or an organic peroxide, and for example, 2, 2, azobisisobutyronitrile, 2, 2'-azobis (2) may be mentioned. , 4~ dimethyl valeronitrile), 2, 2'-azobis(2-methylbutyronitrile), di-butyl peroxide, dibenzyl hydrazine peroxide, cumene peroxy neodecanoate Ester and the like. These polymerization initiators may be used alone or in combination of two types as needed. When the total solid content of the colored resinous composition is regarded as 1 part, the content of the polymerization initiator is 0.5 to 50 parts by mass, preferably 1 to 25 parts by mass, more preferably 1 to 10 parts. Parts by mass.

S is an organic solvent used in the present invention, and it is possible to use a binder resin, a photopolymerizable monomer, a photopolymerization initiation W, etc., which are suitable for the composition of the colored resin composition, and has sufficient solvency, and In the synthesis of the resin, a monofunctional monomer or a polymerization initiator such as 39 323585 201222151 is used, and the solvent is also sufficiently soluble. Further, it is possible to use a dispersion which can maintain dispersion stability even when a pigment dispersion is prepared. The organic solvent used in the present invention is not particularly limited as long as it can be used. Specific examples include benzene such as benzene, toluene, and diphenylbenzene; ceramides such as methyl stilbene, ethyl 赛路苏, and butyl 赛路苏; thiopyranyl acetate and ethyl acetate Cersulfuron, butyl sulphate, etc.; propylene glycol monoalkyl ether acetate such as propylene glycol monodecyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate a propionate such as methyl methoxypropionate, ethyl decyl propionate, decyl ethoxy propionate or ethyl ethoxy propionate; decyl lactate, ethyl lactate, butyl lactate, etc. Lactic acid esters; diethylene glycols such as diethylene glycol monomethyl ether and diethylene glycol monoethyl ether; acetates such as decyl acetate, ethyl acetate and butyl acetate; dimethyl ether, Ethers such as ethyl ether, tetrahydrofuran, and dioxane; ketones such as acetone, mercaptoethyl ketone, mercaptobutyl ketone, and cyclohexyl ketone; alcohols such as decyl alcohol, ethanol, butanol, isopropanol, and benzyl alcohol class. As the solvent, it is usually exemplified by a combination of a ketone solvent and an acetate, and more preferably a ketone solvent and a propylene glycol monoalkyl ether acetate. These may be used alone or in combination of two or more. Further, the amount of the organic solvent to be used is preferably from 40 to 10,000 parts by mass, more preferably from 100 to 1,000 parts by mass, per 100 parts by mass of the total solid content of the colored resin composition. An example of the desired composition ratio of the colored resin composition of the present invention is shown below. 40 323585 201222151 Meanwhile, the content ratio is a ratio of the mass ratio (%) S/solid content contained in the total solid content (full solid fraction) of the composition of the present invention, in addition to the solvent, the above formula (1) The coloring matter compound is 3 to 30%, the binder resin is 5 to 50%, and the hardener is 1 to go%. The pigment other than the color material compound of the formula (1) is 〇 to 60% and the polymerization initiator is 丨 to托%, preferably 2 to 10% of the color material compound represented by the above formula (1), 1 to 50% of the binder resin, and 20 to 50% of the colorant compound of the formula (1) 60% and polymerization initiator 1 to 1%. The solvent content in the ideal colored resin composition is about 100 to 1000% by mass (about 1 to 1 Å by mass) based on the total amount of the solid content. Further, the viscosity of the colored resin composition of the present invention is δ from the viewpoint of coating or the like, and the viscosity at 25 C is about 8 to 20 mP · s, more preferably about 1 15 to 15 mP · s. The colored resin composition of the present invention comprises the above-mentioned binder resin, hardener, photopolymerization initiator, specific color material compound, organic solvent, by a dissolver or a homomixer (h) 〇momixer) and other people make it. X, other pigments or dyes may be added as needed: When the pigment is added or the dye is low in solubility, a suitable dispersing agent is pre-dispensed, and a dispersing machine such as a paint shaker is used as: Or the dye dispersion is added to the residual coloring tree, and the colored resin composition of the present invention is mixed, and various additives such as a filler, a surfactant, and a thermal polymerization inhibitor can be added as needed. , secret promoters, antioxidants, ultraviolet absorbers, anti-agglomerating agents, and the like. also,

S 323 585 41 201222151 The coloring tree composition of the present invention ' can be precisely filtered by a filter or the like in order to remove foreign matter or the like after sputum preparation. Next, a method of preparing a color filter having the cured layer from the colored resin composition of the present invention will be described. First, the colored resin composition of the present invention is applied to a substrate such as a glass substrate or a ruthenium oxide plate by a spin coating method, a roll coating method, a slit and a spin-on and spin coating method, and a mold coating method. A method such as a die coating method or a bar coating method is applied to a film thickness of 〇.丨 to 2〇//m, preferably 疋 is applied to 0.5 to the next, and if necessary, it is dried in a reduction chamber or the like. For example, drying under reduced pressure at a temperature of 23 to 15 (TC, 1 to 60 minutes, preferably at a temperature of 60 to 120 ° C, for 1 to 1 minute). The film is pre-baked by a furnace, etc., and then irradiated with radiation (for example, an electron beam or an ultraviolet ray by a predetermined mask parttern) by a general photolithography method. Ultraviolet light is preferred, and the aqueous solution of the surfactant, the aqueous alkali solution, or the mixed aqueous solution of the surfactant and the alkaline agent is used for image development. The development methods include: dipping method, spray method, shower method, stirring slurry. The paddle method, the ultrasonic imaging method, or the like may be combined. The unirradiated portion is removed by development, washed with water, and then subjected to a post-baking treatment, for example, at a temperature of 13 〇 to 300 C for '1 to 120 minutes, preferably at a temperature of 150 to 25 CTC, for 1 to 30 minutes. By this post-baking treatment, a halogen obtained from the colored cured film of the present invention is obtained. Color enamel film. In the above interface Agent, use may be stretched polyethylene ethyl group

42 323585 S 201222151 Alkyl ether, polyoxyl extension base, etc. Further, in the case of the test, a carbonic acid such as sodium carbonate or potassium carbonate, a hydrazine oxide such as sodium hydroxide or argon, a diethanolamine, a tetramethylammonium hydroxide or the like may be used. In the present invention, it is preferred to use an aqueous solution containing both an assay and a surfactant. The development is usually from 1 Torr to 50 ° C, preferably at a treatment temperature of from 20 to 40 ° C, usually from 30 to 600 seconds, preferably from 30 to 120 seconds. A color filter having a cured layer of the colored resin composition of the present invention is used as a color filter suitable for use as a solid-state image sensing element used in a liquid crystal display device, an organic EL display, a digital camera, or the like. sheet. The color filter has a patterned blue pixel formed of a cured product of the colored resin composition of the present invention prepared as described above. In the display device of the present invention, the liquid crystal display device is produced by, for example, a structure in which a backlight, a polarizing film, a display electrode, a liquid crystal, an alignment film, a common electrode, a color filter of the present invention, a polarizing film, and the like are laminated in this order. Further, the organic EL display is produced by forming the color filter of the present invention on either or both of the multilayer organic light-emitting elements. Moreover, the solid-state image sensing element is provided, for example, by placing a color filter and a photo sheet layer of the present invention on a Si 1 icon wafer provided with a migration electrode and a photodiode. And making. [Examples] Hereinafter, the present invention will be described in more detail based on examples, but the present invention is not limited to the examples. Further, in the examples, "%" means "% by mass" unless otherwise specified. Synthesis Example 1 43 323585 201222151 5 g of Basic Violet 3 (decomposition temperature: 205 ° C, manufactured by Tokyo Chemical Industry Co., Ltd.) of the following formula (100) was dissolved in 500 g of water, and stirred in 10 g of DMF. A solution of the planing salt lg in which the trifluoromethane methane methide was dissolved was added. After stirring for 3 hours, the precipitated crystals were obtained by filtration, washed with water and dried to give crystallized compound 2 (triaryl decane compound of the present invention) (1.2 g). Decomposition temperature: 240 ° C Maximum absorption wavelength: 598 nm (cyclohexanone). Formula (100)

Synthesis Example 2 Reaction Formula

Add 2,6-dichlorobenzaldehyde (4.2 舀, 0.02111〇1), 2,6-dimercaptoaniline (6.4 g, 0.04 mol), urea (0., 0.005 mol) to 60% The intermediate product was obtained by reacting the mixed solution at 105 ° C for 2.5 hours. Here, 14 ml of water, tetrachlorobenzene (i. chloranil) (5.9 g, 0.02 mol) was added, and further reacted at 100 ° C for 6 hours. The activated carbon filtration and the silica gel filtration of the method of the general method of 44 323585 201222151 were carried out to obtain a compound 1〇1 (3.5 g, 36%). Synthesis Example 3 Compound 101 (2·〇g, 〇.〇〇5 mol) was dissolved in a mixed solution of 150 ml of water and 40 ml of f-alcohol, and while stirring, a dimethyl benzene was dissolved in 1 ml of MF. 4克的溶液。 The methic acid salt was added. After heating and stirring at 40 °C for 3 hours, the precipitated crystals were obtained by filtration, washed with water and dried to give 2. 〇g of crystalline compound 15 (triarylmethane compound of the invention) (absorption maximum: 619 nm). Synthesis Example 4 Reaction Formula

Add 2-chlorobenzaldehyde (5.0 g, 0.04 mol), N-ethyl-2-methylaniline (10. lg, 0.07 mol), urea (0.4 g, 0. Olmol) to 60% In 50 ml of an aqueous acid solution, the mixed solution was reacted at 105 ° C for 3 hours to synthesize an intermediate product. Here, 16 ml of water and chlorani 1 (8·7 g ’ 〇·4mo 1) were added to further react at 100 C for 8 hours. The activated carbon was filtered, and the mixture was filtered to give a compound 102 (7.4 g, 52%). Synthesis Example 5 Compound 102 (3.0 g of 0.008 mol) was dissolved in a mixed solution of 150 ml of water and 45 323585 201222151 40 ml of decyl alcohol, and a trifluorodecane was dissolved in 1 ml of DMF while being disturbed. A solution of 2.4 g of the cerium base planing salt was added. After heating and stirring at 40 °C for 3 hours, the precipitated crystals were obtained by filtration, washed with water and dried to give 2.0 g of crystalline compound 16 (triarylmethane compound of the present invention, absorption maximum: 624 nm). Synthesis Example 6 Reaction Formula

In 204. 3 g of DMF in ice-cold, slowly add phosphorus oxychloride (55.4 g, 0.36 mol), stir for 30 minutes, and slowly add N,N-dicyanoethylaniline. (60. 0g, 0. 30mol). Thereafter, it was heated to 90 ° C and disturbed for 4 hours. After completion of the reaction, the reaction solution was poured into ice water for neutralization, and the mixture was extracted with ethyl acetate. Then, the solvent was evaporated under reduced pressure to give 63.5 g of Compound 103. Synthesis Example 7 'Reaction formula 46 323585 201222151

NCs^^i^^^CN

(103) (104) N,N-Dibutylaniline (24.64g, 0.12mol), urea (1. 08g '0.06mol), compound 103 (13. 64g, 0.06mol), concentrated sulfuric acid (3., 0.06 mol) was dissolved in 60 ml of isopropanone, and heated under reflux for 10 hours. After completion of the reaction, the solvent was removed under reduced pressure to give Compound 104. Synthesis Example 8 Reaction Formula

The compound 104 obtained in the above Synthesis Example 7 was added to a solvent of 600 ml of hot water and 100 ml of methanol and concentrated hydrochloric acid (5 ml, 0.16 mol), and after stirring at 80 ° C for a short time, sodium carbonate was added thereto. While maintaining the pH at 2.0, 150 ml of a 34% aqueous solution of ferric chloride was slowly added dropwise. After the completion of the dropwise addition, the mixture was stirred at the same temperature for 2 hours, and then returned to the room temperature. 47 323585 201222151 Synthesis Example 9 The compound 1〇5 (3. 〇3g, 〇〇〇46m〇1) obtained in Synthesis Example 8 was dissolved in a mixed solution of 50 ml of water and 40 ml of methanol, and stirred while stirring. The solution of the cerium salt of the trifluorodecane 锍 methoxide dissolved in 2 ml of DMF was added. After stirring for 3 hours, the precipitated crystals were obtained by filtration, washed with water and dried to give 4.36 g of crystalline compound 18 (absorption maximum: 585 nm), and decomposition temperature: 247 Ϊ. Synthesis Example 10 In a 100 ml beaker, 'Rhodamine B (manufactured by Tokyo Chemical Industry Co., Ltd.) ig, water 2 〇g was placed in a formula (1〇6), and stirred at room temperature for 30 minutes. . Here, a solution of the grazing salt lg of the trioxane quinone methide (TFSM) dissolved in 1 ml of DMF was dropped, and stirred for 3 hours. The precipitated dye was collected by filtration, washed with water and dried to obtain TFSM salt (Compound 2-3) of Zhengjiahong B, 0.7 g. Maximum absorption wavelength: 560nm (cyclohexene J). Formula (106)

Synthesis Example 11 (Synthesis of a binder resin (copolymer)) In a 500-ml four-necked flask, 16 g of methyl ethyl ketone, 10 g of decyl acrylate, 33 g of benzyl methacrylate, and α, α'- were added. 1 g of azobis(isobutyronitrile) was stirred while stirring nitrogen gas into the ship for 30 minutes. Thereafter, 323585 48 201222151 was warmed to 8 (TC, stirred at 80 to 85 ° C for 4 hours. After the reaction was finished, 'cooled to room temperature to obtain a colorless transparent uniform copolymer solution. This was in isopropanol and water. 1: 1 Precipitation in the mixed solution 'Filtering, taking out the solids 'drying' to obtain the copolymer (A). The obtained copolymer (A) is converted into a polystyrene weight average molecular weight of 18000 'acid value is 152. Example 1 Copolymer of the binder resin (A) 5.4 g, Kayarad RTM DPHA (trade name, dipentaerythritol hexaacrylate) as a photopolymerizable monomer

6g, a photopolymerization initiator, Irgacure 907 (manufactured by Ciba Specialty Chemicals Co., Ltd.) 1. 5g, and KayacureRTMDETX-S (manufactured by Sakamoto Chemical Co., Ltd.) 6 g, 0.6 g of the compound 2 of Synthesis Example 1, 20 g of cyclohexanone as a solvent, and 8.6 g of propylene glycol monomethyl ether acetate were mixed to obtain a colored resin composition of the present invention. Related Examples 2 to 6 are as described below. (Example 2) A colored resin composition of the present invention was obtained in the same manner as in Example 1 except that the compound 2 of Synthesis Example 1 was changed to the compound 15 of Synthesis Example 3. (Example 3) A colored resin composition of the present invention was obtained in the same manner as in Example 1 except that the compound 2 of the synthesis example 1 was changed to the compound 16 of the synthesis example 5. (Example 4) A colored resin composition of the present invention was obtained in the same manner as in Example 1 except that the compound 2 of Synthesis Example 1 was changed to the compound of Synthesis Example 9 49 323585 201222151 18 . Example 5 (i) CIPigment bluel5 · 6/AjisperRTM PB821/ SolsperseRTM 5000/PGMEA= 15· 0/6· 0/1. 0/78. 0 (mass halo ratio) composition ratio after mixing, add 〇. A 3 mm zirconia bead (400 g) was treated with a paint shaker for 60 minutes, and a pigment dispersion 1 was obtained by filtration. Further, in the above, C. I. Pigment bluel 5 : 6 is a copper pigmented pigment,

Ajisper RTMPB821 (trade name, Ajinomoto Fine-Techno Co., Ltd.) and Solsperse RTM 5000 (trade name, manufactured by Lubrizol Co., Ltd., Japan) are dispersants. PGMEA is propylene glycol monodecyl ether. Also, the RTM table is attached to the trademark. (ii) In the colored resin composition of Example 3, 19 g of the pigment dispersion liquid 1 obtained above was further added to obtain a colored resin composition of the present invention. Example 6 In the colored resin composition obtained in (ii) of Example 5, the compound 2-3 of the synthesis example 10 (color material compound of the formula (2)) 〇.6g was further added to obtain the coloring resin composition of the present invention. Things. Comparative Example 1 The same procedure as in Example 1 was carried out except that the compound 2 (〇6 g) in Example 1 was changed to 19 g of the pigment dispersion liquid 1 obtained in the above (1) of Example 5, instead of the compound 2 ( 〇6g), a comparative resin composition containing 19 g of pigment component 50 323585 201222151 Dispersion 1 was obtained. Comparative Example 2 A coloring resin composition for comparison was obtained in the same manner as in Example 1 except that the compound 2 of Synthesis Example 1 was changed to the conventional violet dye Basic Violet 3. (Example 7) The above-mentioned color resin composition (Examples 1 to 6 and Comparative Examples 1 and 2) was applied onto each of the respective glass substrates to obtain a glass substrate having a coating film of each of the colored resin compositions. Each of the glass substrates was prebaked under conditions of 8 Torr for 10 hours, and then exposed through a photomask to harden the exposed portions. Next, the exposed portion was developed in an aqueous alkali solution containing a surfactant, and after washing with water, it was at 200. (: heating in the middle to obtain a color filter of the present invention having a cured layer of the same pattern as the photomask. The pattern of the obtained color filter has a line spacing (llne and space) resolution of 5#m angle, It is confirmed that there is no residue, peeling of the pixels, etc. Evaluation of the test heat resistance and the evaluation of the color filter (the substrate for the evaluation of the cured layer) 2 is applied to the glass substrate in the same manner as described above, and the order is made. The royal exposure was prepared by performing a culture treatment at 200 ° C for 5 minutes to obtain a color filter having any vivid color characteristics. The evaluation was performed as follows. Heat resistance: a The evaluation substrate obtained above, The spectral transmittance of the evaluation substrate before and after the treatment was measured at 20 (TC for 40 minutes) by a spectrophotometer "Island III 51 323585 201222151 φ 津 株式会社 UV-3150". The measured spectral transmittance was measured. The chromaticity in the ochre system was calculated, and the chromatic aberration (AEab) before and after the heat treatment was calculated and evaluated. Comparison: Placed between two polarizing plates of a comparison meter (CT-1 manufactured by 壸坂Motorium Co., Ltd.) Above assessment For the substrate, the ratio of the luminance value (cd/cm2) when the two polarizing plates are parallel to the luminance value (cd/cm2) when perpendicular (the luminance value in parallel/the luminance value in the vertical direction) is calculated and compared. The evaluation results of the properties are shown in Table 3, and the evaluation results of the comparison are shown in Table 4. Table 3 Evaluation results of heat resistance Δ Eab Example 1 9.4 Example 2 4. 6 Example 3 1.5 Example 4 11.6 Example 5 2. 0 Implementation Example 6 1.4 Comparative Example 2 51. 7 52 323585 201222151 Table 4 Comparison of Evaluation Results Contrast Example 2 15000 Example 3 15600 Example 5 10500 Example 6 10000 Comparative Example 1 8500 It can be seen from the evaluation results of Table 3 that the present invention is implemented. Examples 1 to 6 showed good results as compared with Comparative Example 2 of the conventional dye, and the resistance of the color material compound of the present invention was greatly improved. Examples 5 and 6 mixed the pigment in the dye of the present invention, but in particular The insoluble matter and the like are in the absence of precipitation, and the state is also good, which suggests that the dye-based color material compound of the present invention has a wide range of applicability. Further, from the comparative evaluation results of Table 4, it is understood that the pigment phase of Comparative Example 1 is obtained. Than, real Examples 2, 3, 5, and 6 all showed good results. In particular, Examples 2 and 3 are the results of only the dye, showing a significant improvement in the contrast of the pigment. Therefore, the colored resin composition of the present invention can be confirmed. It has applicability as a color filter for the next generation. [Industrial Applicability] From the above, the colored resin composition of the present invention using a specific dye-based color material compound has a clear and excellent color filter. The film characteristics (resistance, contrast, etc.) can be obtained with high-quality, highly reliable color filter elements. Further, since it can be used in good mixing with pigments depending on the application, it exhibits wide applicability and is therefore highly industrially valuable. 53 323585 201222151 [Simplified illustration] None. [Main component symbol description] None. 54 323585 〇

Claims (1)

201222151 VII. Patent application scope: 1. A colored resin composition for a shirt color filter, which comprises a color material compound, a binder resin, a solvent, a polymerization initiator, and a hardener as shown in the following formula: 1) (wherein, Ri to R4 each independently represent a hydrogen atom, an alkyl group of C1 to C30, a phenyl group or a benzyl group, and 匕 to R1T each independently represent a hydrogen atom, a halogen atom, an alkyl group of C1 to C6, a substitution or not Substituted amine group; an anion moiety is a haloalkylsulfonyl quinone imine anion, a haloalkylsulfonium methide anion, or a haloalkyl sulfonate anion, each of which is independently 3 through C1 to C10 alkyl groups substituted by 6 tooth atoms). 2. The colored resin composition for a color filter according to claim 1, wherein the polymerization initiator is a photopolymerization initiator or a thermal polymerization initiator. 3. The colored resin composition for a color filter according to claim 2, wherein z- is bis(trifluoromethyl)sulfonyl quinone imine anion, ginseng (trifluoromethyl) continued醯Methylate anion, or trifluoromethyl sulfonate continued 323585 1 201222151 acid salt anion. 4. The colored resin composition for color filters according to claim 3, wherein at least one of ruthenium to Rl7 is a halogen atom. 5. The colored resin composition for a color filter according to claim 3, wherein at least one of ruthenium to Rl7 is an alkanoamine group. 6. A colored resin composition for a color filter according to any one of claims 1 to 5, which is a metal phthalocyanine pigment or a formula (2) Any one or both of the color material compounds shown, (2) 丫1 ～ γ3 (wherein Rla to Rea each independently represent a hydrogen atom, a halogen atom, an alkyl group of Cl to C12, an alkoxy group of C1 to C12, a nitro group, a carboxyl group, or an alkoxycarbonyl group; and Yi to γ4 each independently represent a hydrogen atom. , C1 to C12 alkyl, aryl; 乂! to Χ5 each independently represent a hydrogen atom, a C1 to C12 alkyl group, a C1 to C12 alkoxy group, a halogen atom, a nitro group, a phenoxy group, a carboxyl group, an alkane An oxycarbonyl group, a sulfo group, an amine sulfonyl group; an anion moiety Ζ 1 represents a haloalkyl sulfonyl quinone imine anion, an alkyl sulfonium methide anion, or a haloalkyl sulfonate anion, each alkoxy group It is a Cl to CIO alkyl group which is independently substituted by 2 323585 201222151 3 to 6 halogen atoms). 7. The colored resin composition for a color filter according to claim 6, wherein the metal phthalocyanine pigment is contained. 8. The colored resin composition for a color filter according to claim 6 which contains a metal phthalocyanine pigment and a color material compound represented by the formula (2). A color filter having a cured layer of the colored resin composition according to any one of claims 1 to 5, or any one of claims 1 to 5 of the patent application. In the colored resin composition, the coloring resin composition contains a metal phthalocyanine pigment or a colored resin composition for color filter of either or both of the color material compounds of the following formula (2). Hardened layer, formula (2) 丫1 % R4a Ϊ3 (wherein Rla to Rh each independently represent a hydrogen atom to a C12 alkyl group, a C1 to C12 alkoxy group, a nitroxide group; 丫! to Y4 each independently represent a hydrogen atom alkyl group, an aryl group; and Xii Xs each Independently represents a hydrogen group, a C1 to C12 alkoxy group, a tooth atom, a halogen atom, a C1 &amp; nitro group, a fluorenyl group, an alkane atom, a C1 to C12 hydrogen atom, C1 to ^? Nitro, phenoxy, 323585 3 201222151 Rebel, aerobic group, agglomerate, or amine hydrazine; anion moiety z- represents a halogen-based sulfonyl alkoxide anion, _alkylsulfonium methide An anion, or i-based sulfonate anion 'each alkyl group is a C1 to C10 alkyl group independently substituted with 3 to 6 tooth atoms). 10. A display device comprising a color filter as described in claim 9 of the patent application. 11. A solid-state image sensing device comprising a color filter as described in claim 9 of the patent application. 12. The colored resin composition for a color filter according to Item 2, wherein, in the formula (1), each of 匕 to L is independently a hydrogen atom or a C1 to C4 lower alkyl group; Rlz each independently a hydrogen atom or a C1 to C4 lower alkyl group 'Ru to Rn are each independently a hydrogen atom, a halogen atom, or a di C1 to C3 alkylamino group, and a C1 to C3 alkylamino group C1 to The C3 alkyl group may be unsubstituted or may be substituted by a halogen atom or a cyano group, and Z&quot; is a bis(trifluoromethyl) hydrazinyl imine anion, a ginseng (trifluoromethyl) sulphide methide An anion, or a tri-anthracene anion. 13. The colored resin composition for a color filter according to claim 12, wherein, in the formula (1), at least one of R5 to Re is a lower alkyl group of Cl to C4, and the other is a halogen atom. At least one of Rn is a halogen atom, and the other is a hydrogen atom. 14. The colored resin composition for a color filter according to any one of the items of the present invention, wherein, in the formula (1), Z_ is a ginseng (trifluoromethyl group). Sulfonium methide anion. 15. The composition for coloring a color filter 4 323585 ^ 201222151 according to claim 6, wherein in the formula (2), Z- is bis(trifluoromethyl)sulfonyl ruthenium imine An anion, a ginseng (trifluoromethyl) sulfonium methide anion, or a trifluorosulfonyl sulfonate anion. 16. The colored resin composition for a color filter according to claim 15, wherein, in the formula (2), Rla to R6a are each independently a hydrogen atom, and ¥! to Y4 are each independently a hydrogen atom. Or C1 to C4 alkyl, and! Each of Χ5 is independently a hydrogen atom or a carboxyl group. 17. The colored resin composition for a color filter according to claim 6, wherein in the formulas (1) and (2), both of them are ginseng (trifluoromethyl)sulfonate. Mercapto anion. s 5 323585 201222151 IV. Designated representative map: (1) The representative representative of the case is: There is no schema in this case. (2) A brief description of the symbol of the representative figure: None. 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: One (1) 3 323585