TW201235365A - Colored resin composition - Google Patents

Abstract

The invention provides a colored resin composition for use in a color filter, the colored resin composition containing a color material compound, a binder resin, a solvent, a polymerizing initiator and a curing agent, and a color filter having a cured article of the colored resin composition. The color material compound is represented by the following general formula (1) Wherein R2 and R15 to R18 represent respectively independently a hydrogen atom, C1 to C30 alkyl group, phenyl group or benzyl group; R1 and R3 to R14 represent respectively independently a hydrogen atom, a halogen atom, and a C1 to C12 alkyl group. X- represents a halogeno alkyl sulfonylimide anion, a halogenoalkyl sulfonyl methide anion, or a halogenoalkyl sulfonate anion, each halogeno alkyl group respectively independently a C1 to C10 alkyl group substituted by 3 to 6 halogen atoms. The colored resin compound exhibits excellent storage stability even if it contains a metallic phthalocyan in a pigment, and is suited for use in colorfilter pixels having a bright color feature and excellent durability against heat.

Description

201235365 VI. Description of the Invention: [Technical Field of the Invention] This is a coloring resin composition for forming a blue halogen, using the color calender formed by the use of the color filter, and using a color filter. An electronic display device such as a liquid crystal display device, a photographic element (CCD, CMGS), or an organic EL display device. [Prior Art] f is a liquid crystal display element such as a liquid aa display (LCJ) represented by a notebook computer, a liquid crystal television or a mobile phone, or a digital camera, or an input device such as a color-to-printer or the like. The colorization of the photographic elements (CCD, CMOS) used is necessarily a color filter. As a method of producing such a color filter used in a liquid crystal display device or a solid-state imaging device, although there are a dyeing method, an electrographic method, a printing method, a pigment dispersion method, etc., in recent years, it has become pigment-dispersed. Law is the mainstream. As a method of patterning represented by photolithography, a photosensitive resin composition and a pigment dispersion are used to form a color light-emitting sheet. Recently, a method of forming a color filter by directly applying a colored ink to a substrate without using a photomask by means of an ink jet printer is being carried out. Among the characteristics required for color filters, it is particularly important to improve color purity, color, brightness, and contrast. By increasing the brightness, it is possible to suppress the amount of light in the backlight and to reduce the power consumption, so it is also a necessary technique on the ring. In order to increase the color purity of the color filter and increase the content of the colored pigment, it is necessary to select a pigment having a better spectral shape. On the other hand, it is necessary to increase the transmittance because of the increase in brightness. On the contrary, it is necessary to reduce the concentration of the pigment by 4 323582 201235365 or to make the film thickness thin. In order to achieve the opposite characteristics, there is a limit to the tolerance or dispersion stability of the so-called fine particles of the pigment. Therefore, the current situation is that even if the brightness is not improved, the method seeks both brightness and tolerance. The situation of the person. As a way to solve these problems, a color filter using a dye is reviewed. If a dye is used, it can have a color purity and brightness which cannot be achieved by a pigment, or can suppress light scattering because there is no particle, so that the advantage of contrast can be improved. However, it is necessary to have long-term reliability for televisions and the like. The display body must have light resistance or heat resistance. However, dyes, especially blue dyes, are significantly worse than the pigments in terms of tolerance. For example, in Patent Documents 1 and 2 below, reports on color filters using a triphenylmethane-based compound are reported. However, the tris-based methane-based compound described herein is remarkably deteriorated in light resistance or heat resistance, and has not reached a practical level. Although the phthalocyanine dye is well known and has excellent tolerance to the patent document 3), since the color characteristic is not blue, in general, it is a reddish cyan color tone, and thus it is impossible to form a vivid blue enamel. Prime. Among the i-color filters, a coloring resin composition which is a bright blue element which is indispensable in the present state and which contains a coloring material having a high reliability and is highly practical, can hardly be put into practical use. Therefore, it is a high-grade color filter that seeks to have a distinctive color characteristic as a next generation and is highly tolerant. [Prior Art Document] (Patent Document) Patent Document 1: Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. [Problem to be Solved by the Invention] An object of the present invention is to provide a color filter having vivid color characteristics, excellent heat resistance and the like. [Means for Solving the Problems] As a result of intensive studies to solve the above problems, the inventors of the present invention have found that the above-mentioned problems can be solved by using a colored resin composition containing a specific color material compound in the color filter of the color filter. The present invention has been completed. That is, the present invention relates to the following (1) to (12). (1) A colored resin composition for a color filter comprising: a color material compound, a binder resin, a solvent, a polymerization initiator, and a curing agent represented by the following formula (1);

(wherein R 2 and R 15 to R 18 each independently represent a hydrogen atom, an alkyl group of C1 to C30, a phenyl group or a benzyl group, and hydrazine and R3 to Rm each independently represent a hydrogen atom, a halogen atom, a C1 to C12 alkyl group. Γ represents haloalkyl 6 323582 201235365 sulfonium imine anion, haloalkyl sulfonate anion or haloalkyl sulfonate anion, each haloalkyl is independently substituted with 3 to 6 halogen atoms C1 to C10 alkyl). (2) The colored resin composition for a color filter according to the above (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 the above (1) or (2), wherein the oxime of the formula (1) is a bis(trifluoromethylsulfonyl) imide anion, a ginseng ( A trifluoromethylsulfonyl) anthracenide anion or a trifluorosulfonylsulfonate anion. (4) The colored resin composition for a color filter according to any one of (1) to (3), wherein, in the formula (1), R2 and R15 to Rl8 are each independently C1 to C4. Alkyl; 匕 and 匕 to R14 are all 氲 atoms. (5) The colored resin composition for a color filter according to any one of the above (1), wherein the metal phthalocyanine pigment or the color material represented by the following formula (2) is further contained. Either or both of the compounds,

χ£ χ. White 6a

(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 benzyl group, a carbonyl group or an alkoxycarbonyl group. 丫! to Y4 each independently represent A hydrogen atom, an alkyl group or an aryl group of C1 to C12 7 323582 201235365. Each of 1 to 5 independently represents a hydrogen atom, a C1 to C12 alkyl group, a ci to C12 alkoxy group, a halogen atom, a nitro group, a phenoxy group. a group, a carboxyl group, an alkoxycarbonyl group, a sulfonic acid group, an amine sulfonyl group. The anion moiety Γ represents a halogenated anion anion anion, a dentate group hydrazine methide anion or an i alkyl sulfonate anion, Each of the dentate alkyl groups is independently a C1 to (10:10) group which is substituted with 3 to 6 tooth atoms. (6) A colored resin composition according to the above (5), which contains a metal ugly pigment pigment (7) The colored resin composition for a color filter according to the above (5), which contains a metal phthalocyanine pigment and a color material compound represented by the formula (2). (8) As described in (5) above (7) A colored resin composition for a color filter according to any one of the preceding claims, wherein, in the formula (2), all of Ru to R6a are hydrogen Atom, 1 to Y4 are all C1 to C4 alkyl groups, [is a carboxyl group, ^ to X5 is a hydrogen atom 'X is a ginseng (trifluoromethyl aryl) methide anion. (9)-Colored calendering sheet' A cured layer having the colored resin composition according to any one of the above (1) to (4), or a compound having a metal phthalocyanine pigment or a coloring matter compound represented by the following formula (2) The cured layer of the colored resin composition for a color calender sheet according to any one of the above (1) to (4),

S 323582 δ 201235365

(wherein Ru to R6a each independently represents a hydrogen atom, a halogen atom, an alkyl group of Cl to C12, an alkoxy group of C1 to C12, a nitro group, a fluorenyl group or an alkoxycarbonyl group. 丫! to Y4 each independently represent a hydrogen atom, a C1 to C12 alkyl group, an aryl group. Χι to Xs each independently represent a hydrogen atom, a C1 to C12 alkyl group, a C1 to C12 alkoxy group, a tooth atom, a nitro group, a phenoxy group, a carboxyl group, Alkoxycarbonyl, sulfonic acid, amine sulfonyl. Anion moiety X - represents ii alkyl sulfonium imine anion, dentate plastyl hydride anion or calcination anion anion, each tooth The base is a C1 to C10 alkyl group independently substituted with 3 to 6 atoms. (10) The color filter according to the above (9), wherein, in the formula (1), 匕 and the core to Rls are each independently a C1 to C4 alkyl group; and R1 and ruthenium to Ru are each a hydrogen atom. X is a ginseng (trifluoromethylsulfonyl) methide anion. In the formula (2), all of Rea are hydrogen atoms, 1 to γ4 are all C1 to C4 alkyl groups, Χι is a carboxyl group, and X2 to Xs are The hydrogen atom, ruthenium, is a ruthenium (trifluoroindolyl) methide anion. (11) A display device to which the color film of the above (9) or (10) is attached. (12) A solid-state photographic element is attached to a color filter of 323582 9 201235365 as described in (9) or (10) above. [Effect of the Invention] The colored resin composition for a color filter 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 color having excellent color characteristics and heat resistance. Filter pixels. Further, the colored resin composition for a color filter has excellent storage stability even if it contains a metal phthalocyanine pigment. [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 specific color material compound, and Various additives such as a coloring material compound such as a pigment or a dye, a surfactant, a thermosetting agent, a polymerization inhibitor, and an ultraviolet absorber may be contained as needed. The components other than the specific coloring material and the substance can be used without particular limitation, and are not limited thereto. As a method for producing a halogen product using the colored resin composition of the present invention, it is preferable to use a photolithography method and an inkjet method, and it is excellent in the use of a silk-initiating agent. The photosensitive resin composition 'the latter is a thermosetting resin composition which does not require a silking starter. The aforementioned specific color material compound used in the present invention is represented by the above formula (1). R2 and Rl5 of the formula (1) are described in the center, and examples of the alkyl group of C1 to C30 include methyl group, ethyl group, propyl group, isopropyl group, butyl group, and methyl group 10 323582 201235365 propyl group (secondary Butyl), isobutyl, pentyl, 1-ethylpropyl, 1-methylbutyl, cyclopentyl, hexyl, 1-methylpentyl, 1-ethylbutyl, cyclohexyl, thiol Propyl, 2-supply acid ethyl, stearyl ethyl, nitroethyl, decyloxyethyl, ethoxyethyl, butoxyethyl, trifluoromethyl, pentafluoroethyl, 2 -heptyl, heptyl, octyl, decyl, decyl, eleven, didecyl, thirteen, tetradecyl, fifteen, fifteen, heptadecyl , 18-base, 19-burning, arachyl, eicosy 1, heneicosyl, bismuth, 廿三院, 廿四烧基, 廿五烧基,廿六院基,廿七烧基,廿八炫基, 廿九烧基, triacontyl, isoheptyl, isooctyl, isodecyl, isodecyl, iso-decene Second courtyard base, different thirteen courtyard bases, different fourteen courtyard bases, different fifteen bases, different Hexadecyl group, iso-heptadecyl group, iso-octadecanyl group, iso-heptadecyl group, iso-arachiyl group, iso-eicosyl group, isodecyl monoalkyl group, isoindole dialkyl group, isoindole trialkyl group , 廿 廿 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四 四_Ethylheptyl, 1-methylheptyl, 1-cyclohexylethyl, 1-heptyloctyl, 2-decylcyclohexyl, 3-mercaptocyclohexyl, 4-methylcyclohexyl, 2, 6-Dimethylcyclohexyl, 2,4-didecylcyclohexyl, 3,5-didecylcyclohexyl, 2,5-dimethylcyclohexyl, 2,3-didecylcyclohexyl, 3, 3,5-trimethylcyclohexyl, 4-tributylcyclohexyl, 2-ethylhexyl, 1-adamantyl, 2-adamantyl, etc., wherein C1 to C6 alkyl is preferred, In the case of a case, a C1 to C4 alkyl group is preferred. In R2 and R15 to R18 of the formula (1), the phenyl group or the benzyl group may have a substituent. Examples of the substituent include a mercapto group, an ethyl group, a propyl group, and an iso 11 323582 201235365 propyl group and butyl group. (C1 to C5) alkyl group such as isobutyl, tert-butyl, pentyl or the like; halogen atom such as fluorine atom, gas atom, bromine atom or iodine atom; sulfonic acid group; methoxy group, ethoxy group, propoxy group a (C1 to C6) alkoxy group such as a hydroxy group, a hydroxypropyl group or the like; a hydroxy group (C1 to C5) alkyl group; a methoxy group; Base ethyl, ethoxypropyl, butoxyethyl, etc. ((:1 to C5) alkoxy (C1 to C5) alkyl; 2-hydroxyethoxy and the like (ci to C5) alkoxy Alkoxy group (ci to C5) alkoxy group; 2-hydroxyethyl, decylethyl, cyanoethyl, etc. R1 and Ris to Rie' are each independently a C1 to C6 alkyl group, and a C1 to C4 alkyl group is more preferred depending on the case. Ri and 仏 to R of the formula (1) "In the case of the C1 to C12 alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, or the like may be mentioned. Butyl, isobutyl, pentyl, cyclopentyl, hexyl, cyclohexyl, propyl, 2-nonoleylethyl, stilbene ethyl, cyanoethyl, decyloxyethyl, ethoxy Ethyl, butoxyethyl, trifluoromethyl, pentafluoroethyl, etc. As the formula (1) and hydrazine to Ru' are each independently a hydrogen atom, a chlorine atom, or an unsubstituted C1 to C12 alkane The base is preferably more preferably a hydrogen atom. Examples of the tooth atom in the formula (1) include a gas atom, a gas atom, a bromine atom or an iodine atom. The 'anion moiety' in the above formula (1) (_ indicates _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ The halogen atom in the group is preferably a fluorine atom. Preferred examples thereof include a bis(trifluoromethylsulfonyl)imide anion, a hydrazide (trifluoromethyl hydrazide anion or a trisole methyl rhein anion. Among them, a thiophanate (trifluoromethyl fluorenyl) anthracene anion is preferred. One preferred compounds shown in 1) include such as: Formula

(1) In '' and 1' to R18 are each independently C1 to C4 alkyl, 匕 and L to R" white is a hydrogen atom 'X is a bis(difluoromethyl sulfhydryl) imine anion, ginseng (trifluoro A compound of a methionate anion or a trifluoromethyl sulphonate anion, more preferably; f is a compound of a ruthenium (trifluoromethyl bis-yl) methide anion. Specific examples of the color material compound represented by the formula (1) are shown in the Table, but the present invention is not limited thereto. Table 1

In the table, the substituent R represents a number corresponding to R1 to R18, respectively, and represents a methyl group for Me, an ethylene group for Et, an isobutyl group for i-Bu, a benzene group for Ph, and a cyclohexyl group for CH. Further, χ--"is a sulfhydryl anion of ginseng (trifluoromethylsulfonyl), and represents a bis(trifluoromethylsulfonyl)imide anion when it is stone, and represents a tri-I methyl group when it is 7. Further, in the present invention, a compound of the formula (1) can be used in combination with the compound of the formula (1): 'Rla to Rea each independently represent a hydrogen atom, a halogen atom, and a C1 to C12 alkane. The alkoxy group, the nitro group, the fluorenyl group and the alkoxy group Ik group 'Rla to Rea of the C1 to C12 group are preferably a hydrogen atom. The γι to γ4 each independently represent a hydrogen atom, a C1 to C12 yard group, Any one of aryl ' Υι and γ 2 or 丫 3 and Υ 4 or both of C 1 to C 12 alkyl groups (preferably ci to C 4 alkyl groups) is preferred. Senses 1 to X 5 each independently represent hydrogen. Atom, a thiol group of C1 to C12, a oxy group of Cl to C12, a halogen atom, a nitro group, a phenoxy group, a thiol group, an alkoxycarbonyl group, a sulfonic acid group, or an amine sulfonyl group, meaning! to \5 They may be the same or different. The anion moiety X· represents a t-alkylsulfonimide anion, a haloalkylsulfonyl anion or a t-alkyl sulfonate. The ion, each haloalkyl group is a C1 to C10 alkyl group which is independently substituted with 3 to 6 functional atoms. The tooth atom of the formula (2) may be the same as those described in the above formula (1). (2) A C1 to C12 alkyl group or a C1 to C10 alkyl group, and examples thereof include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a secondary butyl group, and a tertiary butyl group. Isobutyl, n-pentyl, n-hexyl, n-octyl, 2-ethylhexyl, cyclohexyl, etc. These alkyl groups may have a substituent, and as such a substituent, for example, a hydroxyethyl group, Hydroxypropyl, benzylidene, 2-sulfonylethyl, carboxyethyl, cyanoethyl, decyloxyethyl, ethoxyethyl, butoxyethyl, trifluoromethyl, five A fluoroethyl group, a carbamoyl group, a thiol group, etc. The alkoxy group of the C1 to C12 of the formula (2) may be exemplified as an alkyl group exemplified as the alkyl group of the above C1 to C12. Atom of oxygen atom 14 323582

201235365 based. In the case of the alkoxy group, the alkoxy group which is an oxycarbonyl group (_〇c〇_ group) to the alkyl group exemplified as the alkyl group of the above-mentioned Cl to C12 is also exemplified. Examples of the aryl group of the formula (2) include aromatic ketone residues such as a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a benzyl group, and a benzoxyl group; a π ratio biting group, and a pyrazyl group. An aromatic heterocyclic residue such as a pyrimidinyl group, a quinolyl group, an isoquinolyl group, a pyrrolyl group, a fluorenyl group, a oxime group, a sulphate group, a thienyl group, a thiol group, etc. The aryl group may have a substituent, and examples of the substituent include an alkyl group, an alkoxy group, a halogen atom, a sulfonic acid group, a carboxyl group, an alkoxycarbonyl group, an aminomethyl fluorenyl group, a cyano group and the like. The anionic moiety χ- of the coloring matter compound of the formula (1) and the formula (2) contained in the colored resin composition of the present invention represents a tine alkylsulfonimide anion, a t-alkyl sulfonate. a quinone methide anion or an _alkyl alkoxide anion, each of which is a C1 to C10 alkyl group each independently substituted with 3 to 6 halogen atoms. As a tooth atom in the tooth alkyl group, a fluorine atom Preferably, as a specific example of hydrazine, a bis(trifluoromethylsulfonyl)imide anion, a ginseng (trifluoromethylsulfonyl)methyl group An anion, a difluoroantrylsulfonate anion, a nonafluorobutanesulfonate anion, etc., particularly preferably a hexamethylenesulfonylsulfonyl methide anion. Preferred as the formula (2) The color material compound may, for example, be that all of L to Rea is a hydrogen atom, Y2 or any of Y3 and Y4 or both are C1 to C12 alkyl groups (preferably C1 to C4 alkyl groups), χυι匕Either carboxy, alkoxycarbonyl (preferably Cl to C4 alkoxycarbonyl) or carboxam i de (preferably benzylamine carbonyl or may have been substituted by 323582 15 201235365 a compound having a Cl to a C4 lower alkylamine carbonyl group, the other being a hydrogen atom, and X is a ruthenium (trifluoromethylsulfonyl) ruthenium anion. More preferably, the color material compound represented by the formula (2), It is exemplified that all of Ru to R6a are hydrogen atoms, and all of 丫1 to Υ4 are C1 to C4 alkyl groups (preferably ethyl), and carboxy!, X2 to X5 are argon atoms, and X- is argon (trifluoromethane). A compound of a sulfonyl group methide anion. Specific examples of the color material compound represented by the formula (2) are shown in Table 2-1 below. And Table 2-2, but the present invention is not limited to this. 16 323582

S 201235365 Table 2-1 Compound No. Chemical Formula 2-1 Η Η E, SrWV^Et F3C〇2s^so2cf, J\.COOEt S02CF3 u 2 — 2 Η H HlC Person into iAAch,. %辉F, ^JfCOOEt 2 — 3 ψ Ψ F3C02S, g/S02CF3 Jn^cooh so2cf3 u 2-4 Et Et Et, NY, T〇丫F3COzS^0^SO2CF3 ^J^COOH u 2-5 Et Et Εΐ^ Νγ^γ°γ^γΝ®Εί F3C02S,g/S02CF3 J\.COOEt S02CFj u 2-6 f* Et'Y"丫0 丫丫n?ei f3co2s^©^so2cf3 dr— 2-7 ff B^YY °YYH%t K^yK^J F3C02S, g/S02CF3 J^^COOMe S02CFs u 17 323582 201235365 Table 2-2 Compound No. Chemical Formula 2-8 Et Et f3co2s^so2cf3 Jv^CONHH^~^ S02CF3 2-9 Η H Ε^ΝΥ^Γ"°Ύ^ΤΝ"Εί F3C02Svg^S02CF3 Jx^COOEt S02CFj 2-10 Η H Ε,ΝΎ"Ύ〇Ύ^Ύ^Β F3C02S, g/S02CF3 so2CF3 0 2 — 1 1 H CH3 JyWY Heart F3C02S, g/S02CF3 Jv^COOEt S02CF3 .u 2-12 H h;ywyn ' H3CJ^AyJ\^J F3C02S, g/S02CF3 Jv^COOEt S02CF3 2-13 ff; Et^NY^T°Y^TM" Et ΙΙ^ΛγΛ^ f3co2s^so2cf3 ^C0NH-Lh3 S〇2CF3· 18 323582 201235365 The color material compound used in the coloring resin composition of the present invention, for example, 'by Hiroshi Fumiya issued by the company Known synthesis described in "Theory of Manufacturing Dye Chemistry" (pp. 373-375) The method can be obtained, and a commercially available product of an anion moiety χ-chloride anion can be purchased, and a corresponding salt or acid is added to synthesize by salt exchange. When the color material compound of the present invention is synthesized by salt exchange, for example, a color material compound in which an anion moiety is a chlorine anion is dissolved in a reaction solvent [for example, water, methanol, ethanol, isopropanol, acetone, hydrazine, etc. A water-soluble polar solvent such as Ν_dimercaptocarboxamide (hereinafter referred to as DMF) or fluorenyl-mercapto-2-pyrrolidone (hereinafter abbreviated as hydrazine), and these solvents may be used singly or in combination. In the middle of the present invention, a salt or an acid of about 5 to 3 equivalents is added, and the mixture is stirred at a predetermined temperature (for example, 〇 to 1 Torr), and is easily obtained by taking out the precipitated crystal. The total solid content of the resin composition (refers to the total amount of solid content composed of a color material compound, a binder resin, a hardener, etc., except for a solvent. The same definition is used hereinafter.) 1 part by mass The content of the color material compound represented by the above formula (1) is preferably from 1:1 to 1 part by mass, more preferably from 1 to 30 parts by mass, still more preferably from 3 to 3 parts by mass. Further, depending on the occasion Preferably, in the total solid content of the colored resin composition of the present invention, the color material compound containing the formula (1) is 1 to 1% by mass, preferably 2 to 10% by mass, preferably 3 to 1%. The coloring resin composition of the present invention is preferably about 3% by mass, more preferably about 3 to 8% by mass. When the content of the coloring material compound represented by the formula (1) is too large, precipitation or aggregation occurs, or the curing is insufficient. And caused a close relationship with the substrate 323582 19 201235365 sexual decline. When the solubility of the coloring material compound of the above formula (1) to the colored resin composition is low, the coloring material compound of the above formula (1) is the same as the pigment of the optional component described later, and a dispersing agent may be used. The dispersing aid or the like may be dispersed, and the coloring material compound represented by the above formula (1) may be used in combination of two or more kinds, or may be used singly or in combination with other dyes or pigments. It is a combination of blue (four) or violet (violet) dyes, or blue pigments or violet pigments, which are expected to be used together with blue pigments, especially the aforementioned gold brain pigment pigments (preferably copper). The phthalocyanine content) or/and the coloring material compound of the above formula (2) is used in combination with the colored resin composition of the present invention, and the metal ugly pigment pigment (preferably the steel chlorocyanin content) or the aforementioned The f-shaped knife t' of the colored resin composition of the present invention containing the coloring material of the formula (2) has a G-to-30% by mass. The mouth S of the color material 30^ shown in the above formula (1) 'usually 2 to 6 〇 mass% The right is preferably about 10 to 30% by mass. When the hair is an ugly pigment pigment (preferably copper phthalocyanine), the content is in the total solid content of the mass% left color resin composition, usually When 5 to 30 is combined with i, 7 i % W4% °, and in the color material of the formula (2), the total solid content of the colored resin composition of the present invention is a, 3, and is preferably about 5 to 10% by mass, preferably about 5 to 10% by mass. For the mass of::: Ming:: The binder resin used has the following (1) Dispersion stability for dispersion of pigment or water-insoluble dye, 323582 20 201235365 as dispersant or dispersion (ii) When using the photolithography method, it can be dissolved in the alkaline developing solution used in the development processing step when manufacturing the color filter; (111) in order to form a finer finer a pattern, a polymerization initiator (for example, a photopolymerization initiator or/and a thermal polymerization initiator) and a hardener (for example, a polymerizable monomer) contained in the colored resin composition of the present invention, more specifically The photopolymerizable monomer, or the thermally polymerizable monomer, etc.) have good hardening properties. 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) or a polymerizable monomer (for example, photopolymerization) contained therein The structural monomer such as the monomer or/and the thermopolymerizable 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 ink-jet resin composition of the present invention is an ink-jet method, since it is not necessary to have a particular alkali solubility, a resin having good compatibility with other color material compounds or additives can be selected. As the binder resin, a known resin can be used. It is preferred to have more than one county/or reduced ethylenically unsaturated monomer (hereinafter referred to as containing the residue and monomer of the county or containing a silk to saturate the individual polymer, or may be mixed with the A total of (10) other copolymers of a group of a hydrocarbon group or a aliphatic hydrocarbon group (which is another non-fresh monomer), which is usually called a polymer. (4) Further, it can be used in such a polymer. The side chain or the terminal has an epoxy group 323582 21 201235365 'Additional acrylate epoxy acrylate resin, etc. The above-mentioned monomers used in the manufacture of the binder resin are used alone or in combination 2 Further, it may be used as a binder resin. Examples of the unsaturated monomer containing the above-mentioned retarding group which can be used in the present invention include (i) acrylic acid, mercaptoacrylic acid, and crotonic acid. , α • chloroacrylic acid, cinnamic acid and other unsaturated monocarboxylic acids; (ii) maleic acid, maleic anhydride, fumaric acid, itaconic acid, itaconic acid, citraconic acid , citraconic acid needle, mesaconic acid, etc. are not saturated Carboxylic acid (needle); (iii) trivalent or higher unsaturated polycarboxylic acid (anhydride); (iv) 2-(indenyl)propenyloxyethyl hexahydrophthalic acid, 2-hydroxypropyl 2-(meth)acryloyloxyethyl phthalate, 2-propenyl methoxyethyl-2-hydroxyethyl arsenate, etc. The ethylidene unsaturated monomer having such a thiol group may be used alone or Two or more kinds are used in combination. Among them, (meth)acrylic acid is preferred. The unsaturated monomer containing the above-mentioned hydroxyl group which can be used in the present invention can be exemplified by (meth)propionic acid 2- Ethyl ethyl ester, (mercapto) hydroxypropyl acrylate, 3-hydroxypropyl (meth) acrylate, 4-butyl butyl (meth) acrylate, 3-butyl butyl (meth) acrylate , (methyl) acrylic acid 5 - ketone S, (methyl) propyl benzoic acid 4- via valeric acid, (meth) acrylic acid 3 - pentyl vinegar, (methyl) propylene succinic acid 6 - hexyl hexyl ester, (meth) acrylic acid 5 - thiophene acrylate, 4-hydroxy-3-indolyl-pentyl methacrylate, 5-hydroxy-3-indolyl-pentyl (meth) acrylate Hexyl-1,4-dimethanol-mono(indenyl)acrylic acid 32 3582 22 201235365 Cl to C8 diol (mono) (meth) acrylate such as ester; C3 to C6 triol (mono or di) (fluorenyl) acrylate vinegar such as glycerol monomethacrylate Soil based) acrylonitrile 2-(2-superethylethyl) ethyl acetonate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, poly (ethylene glycol - Propylene glycol) methacrylic acid S is a terminally-polymerized diol mono(methyl) acrylate vinegar (preferably poly-C1 to C4 diol diol mono(meth) acrylate), etc. Methyl acrylate. The ethylenically unsaturated monomer having such a hydroxyl group may be used alone or in combination of two or more kinds. As the ethylenically unsaturated monomer having a _ group, it is preferred to use the above-mentioned (meth)acrylic acid acetal, and the hydroxy C1 to C6 (meth) acrylate is more preferable. The hydroxyl group-containing monomer (preferably containing a hydroxyl group-containing (meth) acrylate) may also be used as a copolymerization with the above-mentioned carboxyl group-containing unsaturated monomer (preferably (meth)acrylic acid). Monomer use. Further, examples of the other unsaturated monomer include styrene 'α-methylstyrene, o-vinyl anthracene, m-glycine toluene, p-vinylstyrene, and o-styrene. , an aromatic vinyl compound such as m-chlorostyrene, p-chlorostyrene, p-methoxystyrene; methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate Ester, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, butyl (meth) acrylate, butyl (meth) acrylate, (Methyl) benzyl acrylate, p-isopropylphenylphenoxyethylene (meth) acrylate, (methyl) acrylate 2-amino-3-phenoxypropyl vinegar, o-phenyl Condensed glycerol (meth) acrylate, o-phenyl hydrazine (meth) acrylate via ethyl ethoxide, (meth) acrylic acid phenoxy vinegar, etc. Base 23 323582 201235365 C1 to C4 alkyl (meth) acrylate is preferred; (meth) acrylate cyclopenta vine, (mercapto) acrylic acid Hexyl ester, tridecylcyclohexyl (decyl) acrylate, decyl (meth) acrylate, decyl decyl decyl acrylate, phenyl (meth) acrylate, (methyl) Acrylate cyanohydrin, methacrylate, decyl acrylate, menthyi Acrylyl acrylate, diammonium (meth) acrylate, tricyclo [5· 2. ι·〇2,6] dec-8-yl = (fluorenyl) acrylate, tricyclo[5 · 2· h 〇 2, 6] 十_4_曱 base = (fluorenyl) acrylate, (fluorenyl) decyl acrylate, 2_(meth) propylene decyl oxyethyl hexahydrophthalic acid, ( a compound containing an alicyclic skeleton such as tributyl butyl cyclohexyl methacrylate (preferably a (cyclo) acrylate containing a C5 to Cl 〇 aliphatic ring, and a C5 to C10 aliphatic ring (meth) acrylate Ester is more preferred; methoxy polyethylene glycol monodecyl acrylate, lauryl oxy polyethylene glycol mono (meth) acrylate, octyloxy polyethylene glycol polypropylene Mono (meth) acrylate, nonyl phenoxy polyethylene glycol monoacrylate, nonyl phenoxy polypropylene glycol mono acrylate, ally loxy polyethylene glycol - polypropylene glycol Alkyl-terminated polyalkylene glycol mono(mercapto) acrylate such as (meth) acrylate (preferably C1 to C10 alkyl terminal poly C2 to C4 alkanediol (fluorenyl) acrylate vinegar); acrylic acid 2 -Aminoethyl ester, 2-aminoethyl methacrylate, 2-aminopropyl acrylate, 2-aminopropyl methacrylate, 3-aminopropyl acrylate, 3-methacrylic acid Aminoalkyl ester of an unsaturated carboxylic acid such as aminopropyl propyl ester (more preferably an amine C1 to C4 alkyl (meth) acrylate); glycidyl acrylate, glycidyl methacrylate, ) 3, 4_ epoxybutyl acrylate, (3, 4-epoxycyclohexyl) methyl (meth) acrylate, 4 323 582 24 201235365 hydroxybutyl (F-) acrylate glycidyl ether and other unsaturated Glycidyl carboxylate (e.g., a (meth) acrylate containing an epoxy group, and a C1 to C6 month aliphatic (meth) acrylate containing an epoxy group It is better); vinyl acetate, vinyl propionate, vinyl butyrate, vinyl benzoate and other vinyl carboxylates; ethylene methyl hydrazine, ethyl hydrazine, mysteryl propyl glycidin scale, An unsaturated ether such as propylene glycol glycidyl ether; a vinyl cyanide compound such as acrylonitrile, methacrylonitrile, chloroacrylonitrile or vinyndene; propenylamine, methacrylamide, α- Chloropropenylamine, N-Phenylmaleiniide, N-cyclohexylmaleimide, N_(mercapto) phthalimide, N-( Unsaturated guanamine or unsaturated quinone imine such as 2-hydroxyethyl) acrylamide, N-(2-hydroxyethyl)methacrylamide or maleimide; hydrazine, 3-butadiene, Aliphatic conjugated diene compounds such as isoprene and chloropentadiene; polystyrene, polydecyl acrylate, decyl acrylate, n-butyl acrylate, polymethacrylic acid Butane vinegar, polyoxin, etc. have macromolecular monomers of monoacryloyl fluorenyl or monomethacryl fluorenyl at the end of the polymer molecular chain (posting (10) San ⑽ lights and the like. These other unsaturated monomers may be used singly or in combination of two or more. Among these, as the other unsaturated monomer, a (meth)acrylic acid containing a C5 to C1 aliphatic ring, a C1 to C1 aliphatic ring, and a C1 are preferred. To C10 alkyl terminal poly C2 to C4 alkanediol ^ methyl) propylene, amine C1 to C4 alkyl (meth) propionate vinegar, and 3 epoxy group (meth) acrylate vinegar ( Methyl)propionic acid. More preferably, it is a phenyl-substituted Cl to C4 alkyl (meth) acrylate or a (meth) acrylate vinegar containing a C5 to C10 month aliphatic ring, and more preferably Benzene 25 323582 201235365 base substituted Cl to C4 alkyl (meth) acrylate. The best is the acrylic festival. Further, a polymer in which an unsaturated double bond is further introduced into a side chain of the copolymer can also be used. For example, a maleic anhydride moiety of a copolymer copolymerizable with maleic anhydride, such as styrene, acetonitrile, acrylic acid, propylene glycol, or acrylamide, and an alcohol having hydroxyethyl acrylate a semi-esterified compound which reacts with an epoxy group-containing acrylate such as a hydroxy acrylate or a glycidyl acrylate, and an acrylate having an alcoholic hydroxyl group such as acrylic acid, acrylate or hydroxyethyl acrylate. a hydroxyl group of a copolymer, a compound which reacts with acrylic acid, and the like. Further, a polyurethane resin, a polyamide, a polyimide resin, a polyester resin, a commercially available ACA-200M (manufactured by Diacel Co., Ltd.), and a 〇RGA-3060 (manufactured by Osaka Organic Chemical Co., Ltd.) can also be used. ), AX3-BM02 (made by Nippon Shokubai Co., Ltd.), UXE-3024 (made by Nippon Kayaku Co., Ltd.), UTE-3000C Nippon Chemical Co., Ltd., ZGA-287H (Japanese Chemicals) (share) company system), TCR-1388H (manufactured by Nippon Kayaku Co., Ltd.), ZXR-1722H (manufactured by Nippon Kayaku Co., Ltd.), ZFR-1401H (manufactured by Nippon Kayaku Co., Ltd.), ZCR -1642C Nippon Chemical Co., Ltd.). As the binder resin contained in the coloring resin composition of the present invention, (meth)acrylic acid which is a copolymer of (mercapto)acrylic acid (preferably mercaptoacrylic acid) and a monomer copolymerizable therewith A copolymer resin is preferred, preferably a copolymer of (meth)acrylic acid (preferably methacrylic acid) and a (mercapto) acrylate compound (hydroxy(meth)acrylate) (also known as Mercapto) acrylic acid-(fluorenyl) acrylate copolymer]. The copolymer of the binder resin has an acid value of 10 to 300 (rogKOH/g) or/and a hydroxyl group of 10 323582.

A copolymer of S 201235365 to 200 (mgKOH/g) is preferred. More preferably, the acid value is from 50 to 250 Å, preferably from about 100 to 200. As long as the molecular weight can function as a binder resin, the weight average molecular weight (Mw) (in terms of polystyrene) is usually about 2,000 to 400,000, preferably about 3,000 to 100,000, preferably about 5,000 to 70,000. It is better to be around 8,000 to 40,000. The ratio of the two monomers in the (meth)acrylic acid-(fluorenyl) acrylate copolymer is not particularly limited, but in view of developmental properties and the like, the mass ratio is (meth)acrylic acid: a copolymerizable monomer ( Preferably, the (fluorenyl) acrylate is 1: 〇·5 to 1:10, preferably about 1:1 to 1:5. Further, the (meth) acrylate compound may, for example, be a (meth) acrylate having a mercapto group as described above, and a (meth) acrylate other than the above. As the (meth) acrylate compound, a (meth) acrylate having a C5 to C10 aliphatic ring or a C to C4 alkyl (meth) acrylate which may be substituted with the above phenyl group is preferred, Mercapto) benzyl acetate is preferred. As a preferred (fluorenyl) acrylic acid ~ (mercapto) acrylate copolymer, (mercapto) acrylic acid and phenyl substituted C1 to C4 alkyl (fluorenyl) acrylate (by (meth) propyl a copolymer of benzyl diester is preferred or a copolymer of (meth)propanol and a C5 to C10 aliphatic cyclo(methyl)propionate, or may be composed of only two The copolymer may be in the range of no effect (for example, 〇 to 20 mol%, preferably 〇 to 10 mol%, and 〇 to 5 mol% is a better range) may also contain other copolymerization components. . Meanwhile, the expression "(meth)acrylic acid" or the like in the present invention means the use of acrylic acid or mercaptoacrylic acid, or both. For example, (曱基) 27 323582 201235365 Acrylate is the use of acrylate or / and methacrylate. Generally, when the pigment is dispersed, a dispersing agent or a dispersing aid is used. Therefore, when the resin 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. As the dispersant, a dye-based dispersant having a good absorbing property to a pigment, a resin-based dispersant, or a surfactant, etc., in the present invention, it is preferred to use the pigment in combination. For example, a technique of dispersing a pigment using a pigment-based dispersant is known as a method of mixing a pigment continuator of the above-mentioned Patent Document 4 or a metal salt thereof with a pigment, or mixing a substituted amine fluorenyl derivative with a pigment. The method and the like are known as techniques. The resin-based dispersant may be a non-polar nonionic one, but has a 13⁄4 molecular resin such as an acid value or an amine valence which imparts good pigment sorption properties, and generally, for example, a polyacrylic resin , polyurethane resin, polycarbonate, polyamide resin, polyester resin, and the like. Specific examples thereof include ED211 (manufactured by Nanmoto Chemical Co., Ltd.), Ajisper RTMPB821 (manufactured by Ajinomoto Fine Techno Co., Ltd.), and Solsperse RTM71000 (manufactured by Avecia Co., Ltd.). In the resin composition of the present invention, the content of the dispersant is preferably from 0 to 30% by mass, preferably from 0 to 20% by mass, based on the total solid content. The binder resin (copolymer) used in the present invention may be a commercially available product 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, for example, α,α'-azobis(isobutyronitrile), 2,2'-azobis(2-methylbutyronitrile). , tertiary butyl peroxyoctanoate (t-butylperoxyoctoate), di-tertiary butyl 28 323582 201235365 based peroxide, benz〇yi peroxide, methyl ethyl ketone peroxide. The use ratio of 100 parts by mass of the total of the polymerization initiator in the total of the monomers used in the copolymer synthesis is from 1 to 25 parts by mass. Further, in the case of synthesizing a copolymer, it is preferred to use an organic solvent described below. The organic solvent is preferably one having a sufficient solubility with respect to the monofunctional monomer or polymerization initiator used. The reaction temperature at the time of synthesizing the copolymer is preferably from 50 to 120 ° C, particularly preferably from 80 to 10 (TC. Further, the reaction time is preferably from 1 to 60 hours, more preferably from 3 to 20 hours. The copolymer of the resin is preferably a copolymer having an acid value of 10 to 3 Å (mg KOH/g) or/and a hydroxyl group of 10 to 200 (mg KOH/g), and the acid value or the valence of the hydroxyl group is 10 or less. The developer may have a weight average molecular weight (Mw) of preferably from 2,000 to 400,000, more preferably from 3,000 to 100,000. The weight average molecular weight is below 2 ' or more than 400,000 is sensitivity and imaging. In the present invention, the binder resin may be used alone or in combination of two or more. The content of the binder resin in the present invention is usually 〇 with respect to 100 parts by mass of the total solid content of the colored resin composition. 5 to 99 parts by mass, preferably 5 to 50 parts by mass. In this case, when the content of the binder resin is less than 5% by mass, the alkali developability may be lowered, or an area other than the pixel portion may be formed. The texture may cause problems such as contamination or film residue. As the hardener used in the present invention, it may be listed. For example, calendering or thermal polymerization of monomers during radical polymerization, epoxy resin during ion hardening, and other melamine hardeners, etc. Specific examples of such are: (meth) propylene 323582 29 201235365 acid 2 -hydroxyethyl ester, 2-hydroxypropyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, ethylene glycol di(decyl) acrylate, diethylene glycol bis(indenyl) acrylate , triethylene glycol (meth) acrylate, tetraethylene glycol (mercapto) acrylate, trishydroxypropyl propane tris(decyl) acrylate, neopentyl diol di(decyl) acrylate, neopentyl Tetrahydrin tri(indenyl) acrylate, neopentyltetrakis(mercapto) acrylate, dipentaerythritol hexa(meth) acrylate, glycerol (mercapto) acrylate, bisphenol A ring Oxydi(meth)acrylate, bisphenol F-type epoxy bis(indenyl) acrylate, bisphenol quinone-type epoxy bis(indenyl) acrylate, ethoxylated trihydroxymercaptopropane (fluorenyl) acrylate, propoxylated trimethylolpropane tris(decyl) acrylate, ethoxylate Tris(meth)acrylate, ethoxylated tris(decyl)acrylate, di-trimethylolpropane tetrakis(meth)acrylate, ethoxylated pentaerythritol tetrakis(曱) Acrylic acid S, 9,9-bis[4-(2-acryloxyethoxy)phenyl] acrylate compound. As a commercial product, for example, KAYARADRTM RP-1040C Japanese chemical (share) company), KAYARADRTM DPCA-30 (manufactured by Nippon Kayaku Co., Ltd.), UA-33H (manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), UA-53H (manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) A (mercapto) acrylate compound sold under the trade name of M-8060 (manufactured by Toago Corporation). In addition, examples of the thiol-based polymerization monomer include TEMPIC (manufactured by Sigma Chemical Industry Co., Ltd.), TMMP (manufactured by Sigma Chemical Industry Co., Ltd.), and PEMP (manufactured by Sigma Chemical Industry Co., Ltd.). DPMP (made by 堺Chemical Industries Co., Ltd.) specializes in 'products. Further, examples of the epoxy resin include: manufactured by Nippon Kayaku Co., Ltd.

3〇323582 S 201235365 NC-6000, NC-3000, EOCN-1020, XD-1000, EPPN-501H, BREN-S, NC-7300L, Daicel Chemicals CELLOXIDE 2021P, EHPE3150, CYCLOMER-MIOO, EP0RID0 PB3600 Products such as EPIC0ATRTM828, EPICOATRTMYX8000, EPICOATRTMYX4000, Sila_aceRTMS 510 (manufactured by Chisso Co., Ltd., and TEPICC Chemical Industry Co., Ltd.) are available from Japan Epoxy Resin Co., Ltd. Further, as the melamine curing agent, for example, methylolated melamine or Mw-30 (manufactured by Sanwa Chemical Co., Ltd.) may be mentioned. These can be used singly or in combination of two or more. As the preferred polymerizable monomer as the hardener, a polyfunctional (mercapto) acrylate compound is preferred, and a 3 to 6 functional (meth) acrylate compound is more preferred. Examples of the 3 to 6-functional (fluorenyl) acrylate compound include neopentyl alcohol tri- or tetra(indenyl) acrylate or dipentaerythritol di-hexa-(fluorenyl) acetoin. . The content of these is '1 to 80 parts by mass, preferably 10 to 60 parts by mass, preferably 2 to 60, in the 100 parts by mass of the total solid content of the colored resin composition, and, depending on the case The difference may be 5 to 30 parts by mass. "The pigment which can be used in combination in the colored resin composition of the present invention is preferably one having a suitable color separation property in a color filter, and the dye, the organic pigment and the inorganic pigment are Φ w. Appropriate selection may be used alone or in combination of two or more depending on the demand. +楚#人θ 丄 ^ Use. This special combination has 0 to 60 mass parts in the total solid content of the colored resin composition, and 0 to 3 〇 I is better than the case, and 5 to 3 () Quality is good. These pigments and dyes are specifically described below. 31 323582 201235365 The organic pigment which can be used in combination in the present invention is not particularly limited as long as it has suitable spectral characteristics in the color filter, and examples thereof include a lanthanoid system, a phthalocyanine system, and a triphenylmethane system. Benzimidazolidinone, quinacr idone, azo chelate, azo, isoindole, isoindolinone, pyrazolone, 吲Indazolone, pyrimidine, dibromanthanthrone, flavanthrone, lanthanum, perinone, quinophthalone, sulfur Thio(thioindigo), dioxazine, quinacridone, xanthene, etc.; acid dyes, basic dyes, direct dyes, etc. are insolubilized with separate precipitants Lake pigment, dyed lake pigment, and the like. More specific color index (c〇1〇r

Index), for example, Pigment biue 1 : 2, 9, 14, 15, 15 : Bu 15 : 2, 15 : 3, 15 : 4, 15 : 6, 16, 17, 19, 25 , 27, 28, 29, 33, 35, 36, 56, 56: 1, 60, 61, 61: Bu 62, 63, 66, 67, 68, 7 Bu 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 Bu 32, 37, 39, 42, 44, 47, 49, 50; Pigment Violet 3, 4, 27, 39, etc. In particular, the pigment Μ 15 : 6 or the pigment violet 23 # shows that the blue metal phthalocyanine pigment is a hue or a tolerance, etc., and is not particularly limited as the inorganic saccharide which can be used in combination in the present invention, for example, For example: composite metal oxide pigment, carbon black, black titanium oxide (titanium suboxide), titanium oxide, barium sulfate, zinc white (zinc oxide), 323582 32 201235365 lead sulfate, chrome yellow lead, red iron oxide ( Colcothar), ultramarine, ferric hexacyanoferrate, chromium oxide, antimony white, iron black, lead dan, zinc sulphide, cadmium yellow, cadmium red, zinc, manganese violet, cobalt violet, barium sulfate Metal oxides such as magnesium carbonate, metal sulfides, sulfates, metal hydroxides, metal carbonates, and the like. The dye which can be used in combination in the present invention is not particularly limited, and examples thereof include an acid dye, an inert dye, a direct dye, a sulfur dye, a vat dyestuff, a naphthol dye, a reactive dye, a disperse dye, and the like. Among them, those which are soluble in an organic solvent are preferred, but a dye which is insoluble in an organic solvent is suitably used as a dispersion. The above dyes which are insoluble in an organic solvent can also be modified by a conventional modification method. It is known, for example, in the case of an acid dye or a basic dye, to reform an organic amine compound (for example, n-propylamine, ethylhexylpropionate, etc.) to an amine salt dye, or to make the same organic amine in a sulfonic acid group thereof. The compound reaction is modified to a dye having a sulfonamide group or the like. These amine-modified dyes can also be used in the colored resin composition of the present invention. As the specific dye, examples of the color index include solvent blue: 2, 3, 4, 5, 6, 23, 35, 36, 37, 38, 43, 48, 58, 59, 67, 70, 78, 98, 1〇2, 1〇4; basic blue 7; acid blue 80, 83, 90; solvent purple as purple dye 8, 9: purple 4, 5, 14; basic violet (basic violet) 10 and so on. The photopolymerization initiator added to the coloring resin of the present invention used in photographic imaging is in an ultraviolet ray emitted from an ultrahigh pressure mercury lamp used as an exposure light source of 323582 33 201235365. For example, a radically polymerizable photoradical initiator, a photooxygen generator used in an ionic curable resin, or a photobase generator may be mentioned. In terms of photopolymerization, a component of a polymerization accelerator called a sensitizer which is hardened by less exposure energy can be used in combination. The photopolymerization initiator which can be used is not particularly limited, and specific examples thereof include benzil (benzi 1), benzoin ether, benzoin butyl ether, benzoin propyl ether, and diphenyl benzoate. Benzophenone, 3,3'-dimethyl-4-methoxybenzophenone, benzoylbenzoic acid, benzalkonium ester esterate, 4-> brewing base~*4 _Methyl-phenyl sulfide, decyldidecyl condensate, 2-butoxyethyl-4-methylaminobenzyl acid g, chloro-β-beta ketone, methyl succinone, B Thiophenone, isopropylthioxanthone, dimethylthioxanthone, diethylthioxanthone, diisopropylthioxanthone, dimethylaminomethyl benzylate, 1-(4-ten Dialkylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-indolyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl)-2-hydroxy-2-methylpropanone-1-one, me thy 1 benzoyl formate, 2-methyl-1-(4- Methyl stearyl)- 2-morpholine (propioniino) propane-i-ketone, 2-benzyl-2-didecylaminomorpholine phenyl)-butanone_ι, 2, 4-double (trichloromethyl)-6-(4-methoxy Phenyl)-1,3,5-s-triterpene, 2,4,6-paraxyl (trichloromethyl)-l,3,5-s-trin, 2,4-bis(tribromofluorenyl) a 6-(4,-methoxybenzyl)-l,3,5-s-triazine, 2,4,6-paran (tribromomethyl)-1,3,5-s-three tillage, 2,4-bis(trichloromethyl)-6-(1,3-benzodioxol-5-yl)-l,3'5-s-triphthyl, benzophenone, benzamidine Acid ester, 丨_(4-phenylsulfonylamino)butylate-1,2-dione-2-ethyl-O-benzyl ester, ι_(4-methylbenzamide 323582 34 201235365 . Alkane-1,2-dione-2-indole-0-acetate, 1-(4-methylsulfonylphenyl)butan-1-oneindole-0-acetate, 4, 4'-double (diethylamino)benzophenone, p-dimethylammonium benzate, ethyl p-dimethylamine benzylate, 2,2'-bis(indolyl-phenyl)-4 , 4',5,5'-tetraphenyl-1,2'-biimidazole, diazonaphthylquinone initiator, or commercially available KAYACURERTM DMBI, KAYACURERTM BDMK, KAYACURERTM BP-100 , KAYACURERTMBMBI, KAYACURERTMDETX-S, KAYACURERTMEPA (all manufactured by Nippon Kayaku Co., Ltd.), GR0CURERTM1173, GR0CURERTM1116C are all Merck Japa n (share) company), IRGACURERTM 907 ' IRGACURERTM 369 ' IRGACURERTM 379EG > IRGACURERTMOXE-Ol , IRGACURERTMOXE-02 , IRGACURERTMPAG103C and above IRGACURE for Ciba Specialty Chemicals), TME-Sanken (Sanhe Chemical Co., Ltd.), joint Mi Mi (manufactured by Heijin Chemical Co., Ltd.), STR-110, STR-1 (all manufactured by Respe Chemical Co., Ltd.), and the like. 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 if necessary. Examples of the thermal polymerization initiator include an azo compound or an organic peroxide. Examples thereof include 2, 2'-azobisisobutyronitrile and 2,2'-azobis (2, 4-di). Mercapto valeronitrile, 2, 2'-azobis(2-mercaptobutyronitrile), di-tertiary butyl peroxide, dibenzyl hydrazine peroxide, cumyl peroxy neodecanoate Peroxyneodecanoate) and so on. These polymerization initiators may be used singly or in combination of two or more kinds as necessary. When the total solid content of the colored resin composition is regarded as 1 part by mass, the content of 35 323582 201235365 is 〇·5 to 50 parts by mass, preferably from i to 25 parts by mass, more preferably 1 to 10 parts by mass. b. The organic solvent used in the present invention may have a sufficient dissolving power for a binder as a constituent of the colored resin composition, a photopolymerizable monomer, a photopolymerization, a starter, etc., and a binder resin. The monofunctional monomeric monomer starting material in the synthesis also has sufficient dissolving power. H can be used in the preparation of the (iv) dispersion. The organic solvent used in the present invention can be used as long as it can be used. limit. Specific examples can be exemplified by: benzene, toluene, dip, stupid:,,,, road sulph (methyUeliQSQlve), sei sui sui, dingsai 箸 =; acetic acid, acesulfame, acetic acid, cecas, acetic acid Heart 驮赛赛璐 esters; propylene glycol monodecyl ether acetate, propylene glycol 'acid butyl ethene propylene glycol monobutyl group private: ^ member, methoxypropionic acid W, methoxypropionic acid B 0 Within the ethoxy group: propionate such as ethyl ethoxypropionate; methyl lactate, yttrium b = acid butyl glycerine, etc.; diethylene glycol mono-f-group, diethylene glycol: 2. Diethylene glycols; decyl acetate, ethyl acetate, butyl acetate; anthracene, dimethyl ether, diethyl ether, tetrahydrofuran, dioxane 2, methyl ethyl _, methyl butyl Ketone, cyclohexyl ketone, etc.; a = alcohol, butanol, isopropanol, benzyl alcohol and the like. Further, as a preferred one, it is preferable to use, for example, a ketone solvent and a ketone solvent and a propylene glycol monomethanol. One or two of these may be used alone or in combination of two or more. Further, there is a 323582 36 201235365 • The amount of the solvent to be used is 1 part by mass, preferably 40 to 10,000 parts by mass, more preferably 100 to 1,000 parts by mass, based on the total solid content of the colored resin composition. One example of a preferred composition ratio of the colored resin composition of the present invention is shown below. In the meantime, the content ratio is a mass ratio (%) contained in the total solid content (full solids) of the colored resin composition of the present invention. The content ratio of the solid content, the color material compound represented by the above formula (1) is 3 to 3 (U, 5 to 5 % by weight of the binder resin, and the curing agent i to, the coloring matter other than the coloring material compound of the formula (1) is 〇 Up to 60%, and the polymerization initiator is 1 to 2^5%, preferably 2 to ι% of the coloring matter compound of the above formula (1), 1 to 50% of the binder resin, and 20 to _ hardener , the dye yttrium other than the color material compound of the formula (1), and the polymerization initiator i to 1% by mass. The solvent content of the preferred coloring resin composition is 100 to 1000% by mass based on the total amount of the solid content. The viscosity of the colored resin composition of the present invention is from the viewpoint of coating, etc., and the viscosity at 25 C is about 8 to 2 〇 mp.s, more preferably 15 mP. The colored resin composition of the present invention is a binder resin, a photopolymerization initiator, a specific color material compound, an organic solvent, etc., a dissolver or a homomixer (h〇). Momixer) can be made by mixing and mixing. In addition, other pigments or dyes can be added as needed. In the case of pre-dispensing a suitable powder, a dispersion of a colored resin composition is preferably prepared by dispersing a paint shaker or the like to prepare a pigment or a dispersion of the dye. The colored resin composition of the present invention is preferably mixed. Additives can be added as needed. Additives such as fillers, surfactants, thermal polymerization inhibitors, sputum "foot-feeding agents, antioxidants, UV absorbers, anti-agglomerating agents, etc. In order to remove foreign matter or the like after the preparation, the composition may be precisely filtered by a filter or the like. Description of the method for producing a color filter having the cured layer First, the coloring resin composition of the present invention is applied to the glass. On the substrate such as the substrate or the gas separation substrate, a method such as a spin coating method, a roll coating method, a slit and spin, a die coating method, or a bar coating method is used to make the thickness of 0.1 to The coating method of 20 is preferably 〇 5 to 5 "螟 next, if necessary, drying in a decompression chamber, etc. For example, 111 temperature 23 to 15 (TC ' for 1 to 60 minutes, compared It is dried at a temperature of 6 〇 120 ° C for 1 to 1 〇 minutes, and further pre-baked in a hot plate, a clean oven, etc. to form a film, and then passed through a general-like method. The reticle pattern illuminates the radiation (for example, the electron beam is outside the green line, and the ultraviolet ray is preferred), and the surfactant aqueous solution, the water test is purple, or the interface activity is mixed with water (4), which is immersed and immersed. The crushing method, the spray method, the shower method, the paddle method, the super type method, the image method, etc., or any one of them may be combined by eight to remove the unirradiated knife by the image, and rinsed with water. After that, a post-baking treatment is performed. 3 π processing. The post-baking treatment, for example, at a temperature of 130 to 30 (TC, 1 to 1?n8 & 5 ocn〇1 minutes, preferably at a temperature of 150 to 25 (TC, 1 to 30 minutes)仁 y τ 卜 仃 仃 仃 仃 仃 仃 仃 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 323 Ethyl ether, etc. Carbonic acid such as sodium carbonate or potassium carbonate; hydrogen peroxide oxidation test; diethanolamine, tetramethylammonium hydroxide X 卩 makes Xiao Zhizhi 卩 φ ☆ off 13⁄4 of the aqueous solution is preferred. It is carried out at a treatment temperature of from 1 G to 耽, preferably from 20 to the shoe, usually from 30 to _ second, preferably from 3 () to the conditioned time. The color of the cured layer having the colored resin composition of the present invention should be The light sheet can be used as a color filter useful in a solid-state imaging element used in a liquid crystal display I, an organic EL display, a digital camera, etc. The color light-emitting sheet has a copy prepared as described above. A blue halogen pattern composed of a cured product of the inventive colored resin composition. The liquid crystal display device is formed 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 sequentially laminated. The organic EL display is fabricated on or under the multilayer organic light-emitting element to form the color light-receiving sheet of the present invention. Further, the solid-state imaging element is provided with a transport electrode and a photodiode, for example. The color filter layer of the present invention is provided on a wafer, and then a microlens is laminated. [Embodiment] Hereinafter, the present invention will be described in more detail by way of examples, but the present invention and 323582 39 201235365 is not limited to the examples. In the examples, "%" means "% by mass" unless otherwise specified. Synthesis Example 1 Reaction formula

4克,0. 02摩尔。 4, 4'-bis(diethylamino)benzoquinone (5. Og, 0.02 mol), 1-mercapto-2-phenyl-1H-indole (3.2 g, 0.02 mol The mixed solution of phosphorus oxychloride (4.7 g, 0.03 mol) dissolved in toluene (10 ml) was heated and stirred at 100 ° C for 10 hours. After cooling to room temperature, water was added and the mixture was separated, and the organic layer was concentrated under reduced pressure to afford compound 100 (7.5 g, 95%). Synthesis Example 2 Compound 100 (1.0 g, 0.003 mol) was dissolved in 10 ml of water and 50 ml of decyl alcohol, and while dissolving the mixed solution, 1.7 g of a planing salt of ginseng-three-desulfurized sulphide was added. Solution in DMF 1 ml. After stirring at room temperature for 3 hours, the precipitated crystals were obtained by filtration, washed with water and dried to give crystals of compound K (the triaryl decane compound of the invention) (1. 4 g, 54%). Synthesis Example 3 Rhodamine B (manufactured by Tokyo Chemical Industry Co., Ltd.) lg and water 20 g of the following formula (101) were placed in a 100 ml beaker, and stirred at room temperature for 30 minutes. A solution of 40 323582 201235365 diced salt lg of gins-trifluoromethane oxime methide (TFSM) dissolved in DMF 1 ml was added thereto, and the mixture was stirred for 3 hours. The TFSM salt of rosin B (Compound 2-3) was 0.7 g. Maximum absorption wavelength: 560 nm (cyclohexanone).

Synthesis Example 4 (Synthesis of binder resin (copolymer)) In a 4 G 〇ml four-necked flask, fluorenyl ethyl ketone 16 〇 g 曱 曱 丙烯酸 曱 曱, benzyl methacrylate 33 g, α, α was poured. '-Azobis(isobutyronitrile) k ' While stirring, nitrogen gas was introduced into the flask for 30 minutes. After that, the temperature was raised to 80 ° C and maintained at 80 to 85. (: stirring for 4 hours. After the reaction was terminated, it was cooled to room temperature to obtain a colorless transparent and uniform copolymer solution. These were precipitated in a 1:1 mixture of isopropyl alcohol and water, filtered, and the solid fraction was taken out. This was dried to obtain a copolymer (A) of mercaptoacrylic acid and benzyl methacrylate. The weight average molecular weight of the obtained copolymer (A) in terms of polystyrene was 18,000, and the acid value was 152. Example 1 Copolymer of the binder resin (A) 5. 4 g, Kayarad RTM DPHA (trade name, dipentaerythritol hexaacrylate, manufactured by Nippon Kayaku Co., Ltd.) as a photopolymerizable monomer, as photopolymerization Starting agent

Irgacure RTM 907 (manufactured by Ciba Specialty Chemicals) 1.5 g, and Kayacure RTM DETX-S (manufactured by Nippon Kayaku Co., Ltd.) 0. 6g, 〇. 6g of 41 323582 201235365 Compound 2 of Example 2, as a solvent ring 20 g of ketone and 8.6 g of propylene glycol monomethyl ether acetate (PGMEA) were mixed to obtain a colored resin composition of the present invention. Example 2 C. I· Pigment bluel5 : 6 (copper phthalocyanine pigment) / Aj isupaRTM PB821 / SolsperseRTM 5000 / PGMEA (solvent) = 15. 0/6. 0/1 · 0/ 78. 0 (mass ratio After the composition ratio was mixed, 400 g of 〇.3_锉 beads was added, and the mixture was treated with a paint shaker for 60 minutes, and the zirconium beads were removed by filtration to obtain a pigment dispersion liquid 1. Into the colored resin composition of the present invention obtained in Example 1, 19 g of the pigment dispersion liquid 1 was added to obtain a colored resin composition of the present invention containing a copper phthalocyanine pigment. Example 2 In the colored resin composition obtained in Example 2, Compound 2-3 (TFSM salt of Rose Bengal B) obtained in Synthesis Example 3 was added in an amount of 0.6 g to obtain a copper phthalocyanine pigment and a formula (2). A colored resin composition of the present invention of a color material compound. Comparative Example 1 A colored resin composition of Comparative Example 1 was obtained in the same manner as in Example 1 except that the compound 1 in Example 1 was changed to the conventional blue dye Basic Blue 7. Each of the colored resin compositions (Examples 1 to 3 and Comparative Example 1) obtained above was applied to each of the respective glass substrates. After the obtained coated substrate was prebaked under conditions of 8 〇 ° C x 100 seconds, the exposed portion was hardened by exposure through a patterned mask. Second, in the presence of surfactants, water solubility 42 323582

201235365 ‘In-liquid imaging, after washing with water, heating at 200 ° C to obtain a color filter with a halogen pattern. The obtained color filter had an resolution of a line and a space of 5 vm, and it was confirmed that there was no residue, peeling of halogen, or the like. Evaluation of heat resistance The substrate for evaluation of heat resistance was produced by full exposure without using a patterned exposure mask as described below. That is, the resin compositions of the respective examples and the resin compositions of the comparative examples were respectively applied to the respective glass substrates in the same manner as described in the above Examples, and the resin composition was applied by total exposure. Light hardening of matter. Next, baking was performed at 200 C for 5 minutes, and a color filter (evaluation substrate) having a clear blue characteristic was produced. The following evaluation test was carried out using the known evaluation substrate. Each of the evaluation substrates obtained above was measured for the spectral transmittance of the evaluation substrate before and after the treatment of 20 (TC for 120 minutes t treatment) by a spectrophotometer "Shimadzu Corporation UV-3150". The chromaticity in the XYZ color system of the transmittance was calculated, and the color difference (ΔEab) before and after the heat treatment was calculated and evaluated. Table 3 shows the evaluation results of the heat resistance. Table 3 Evaluation results of heat resistance △ Eab Example 1 7. 5 Example 2 --------- 3. 2 Example 3 111""" ·---- _ 2. 5 Comparative Example 1 48. 7 43 323582 201235365 Color Filter I As a result of the evaluation, it is understood that the color difference between the 彳L and the color enamel of Comparative Example 1 obtained in the prior art (4) is significantly smaller than that of the light sheet obtained in the first to third embodiments of the present invention, and the display is also small. In the resin composition, it is known that the heat-resistant property of the present invention containing the color material compound of the formula (1) is improved, and an excellent color light-receiving sheet can be obtained. Both of the pigments have a color material compound of the formula (1) and copper. The color of the scented phthalocyanine compared to the use of only the human::2 coloring resin composition The coloring material compound of the coloring material composition of the first embodiment contains the (1) more excellent heat resistance, and further, the coloring material compound of the musk, the copper phthalocyanine pigment, and the formula (2) The color filter of the colored resin composition of Example 3 has more excellent heat resistance. 〃 The color resin compositions of Examples 2 and 3 contain a copper phthalocyanine pigment, but insoluble components and the like. It does not precipitate and the storage stability of the resin composition is also good. The coloring resin composition of the present invention containing the coloring matter compound of the dyeing formula (1) described above has wide applicability as a color filter in the next generation. The coloring resin composition for a sheet is very useful. [Industrial Applicability] The coloring resin composition of the present invention containing the coloring matter compound of the dyeing formula (1) described above has a color filter suitable for the next generation. The characteristics of the sheet, the resin composition can obtain a high-quality, highly reliable color filter pixel, and can be used in combination with the pigment because of the corresponding use.

44 323582 S 201235365 - This resin composition has a wide range of applicability and is industrially available. [Simplified illustration] None [Main component symbol description] None 45 323582

Claims (1)

201235365 VII. Patent application scope: 1. A colored resin composition for a color filter containing a color material compound, a binder resin, a solvent, and a polymerization initiator as shown in the following formula (1). And hardener, In the formula, '匕 and heart to R1S each independently represent a hydrogen atom, a C1 to C30 alkyl group, a phenyl group or a benzyl group, and fluorene and fluorene each independently represent a hydrogen atom, a halogen atom, or a C1 to C12 alkyl group; Χ- represents a haloalkylsulfonimide anion, a t-alkylsulfonium methide anion or a haloalkylsulfonate anion' each from an alkyl group independently substituted with 3 to 6 halogen atoms to C1 to C10 alkyl. 2. The colored resin composition for a color filter according to Item 1, wherein the polymerization initiator is a photopolymerization initiator or a thermal polymerization initiator. 3. The coloring resin for color calendering sheets described in the above-mentioned patent scope of the invention, wherein the hydrazine of the formula (1) is a bis(trismethylmethyl) anion anion, a ruthenium (III) Methyl hydrazino) methide anion or trifluoromethyl sulphonate anion. 4: The coloring resin group 1 323582 201235365 for a color filter according to the first aspect of the invention, wherein R2 and R15 to r18 in the formula (1) are independent C1 to C4 alkyl groups; And R3 to Ru are all hydrogen protopors. 5. A colored resin composition for a color filter according to any one of claims 1 to 4, wherein the compound contains a phthalocyanine pigment or is killed by the following formula (2) Either or both of the color material compounds, 丫1 R3a Pi® 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; and 丫1 to Y4 each independently represent hydrogen An atom, a C1 to C12 alkyl group, an aryl group; Χι to X5 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, and an alkyl group. An oxycarbonyl group, a sulfonic acid group, an amine sulfonyl group; an anion moiety X represents an i-alkyl group, an anthracene anion, a dentate sulfonate anion or an i-alkyl sulfonate anion, each of which is independently alkyl The C1 to C10 alkyl group is substituted with 3 to 6 halogen atoms. 6. The colored resin composition according to claim 5, wherein the metal phthalocyanine pigment; T is contained. 7. The coloring resin for the filter for consumption according to the fifth section of the patent application is 323582 201235365. a composition comprising a metal phthalocyanine pigment and a color represented by the formula (2). 8. The color (four) composition according to the application of the invention, wherein m in the formula (2) is all gas =: to Y4 All are C1 to C4 alkyl groups, Xl is a county, heart to Χ5 is a hydrogen atom, and X is a ginseng (trifluoromethylsulfonyl) ruthenium anion. A color filter comprising a cured layer of a colored resin composition according to any one of claims 4 to 4, or a composite containing a metal phthalocyanine pigment or the following formula (2) Or a hardened layer of a colored resin composition for a color light sheet according to any one of the above-mentioned items of the present invention, (wherein Rla to Rea each independently represent a hydrogen atom, a halogen atom, an alkyl group of C1 to C12, an alkoxy group of C1 to C12, a nitro group, a carboxyl group, or an alkoxycarbonyl group; and Υι to Y4 each independently represent hydrogen Atom, C1 to C12, aryl; Χι to Χδ each independently represent a hydrogen atom, a C1 to C12 alkyl group, a C1 to C12 alkoxy group, a tooth atom, a nitro group, a phenoxy group, a carboxyl group, an alkane An oxycarbonyl group, a sulfonic acid group, or an amine sulfonyl group; an anion moiety X- represents a functional group, a hydrazine imine anion, a sulfonyl sulfonyl group 3 323582 S 201235365 an anion or a tooth alkyl sulfonate Anion, each tooth alkyl group is a C1 to C10 alkyl group independently substituted with 3 to 6 tooth atoms. 10. For example, the color grading sheet described in claim 9 wherein the formula (1) and the core to Ris are independent C1 to C4 bases; h and h to Ru are all hydrogen atoms, and r is a reference. (Trifluoromethyl continuation base) a formazan anion. In the formula (2), all of Rla to Rea are gas atoms, all of which are Cl to C4, Χι is (4), & χ X- is ginseng (trifluoro Methyl hydrazino) hydrazide anion. ‘,, '11 Atom’ 11. A display device that is attached to the patented range of color filters. The color of the film is connected to the color of the film. The picture is attached to the color filter of the patent range. 323582 201235365 ^ IV. Designated representative figure: (1) The representative figure of the case is: () . (There is no picture in this case) - (2) Simple 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: 3 323582