TW201000570A - Method for producing fine organic pigment, fine organic pigment and fine organic pigment coloring composition - Google Patents

Abstract

To provide a method for producing a fine organic pigment being usful for obtaining a coloring film, a fine organic pigment according to the method and a fine organic pigment coloring composition using the fine organic pigment, wherein the above coloring film is useful as a color filter for liquid crystal television, and is a film sheet with low retardation, excellent viewing angle dependence, and high transparence. According to the method for producing fine organic pigment, the method is characterized in that subjecting the organic pigment, a water-soluble inorganic salt, a water-soluble organic solvent and a resin (A) exhibiting a solubility above 1 part by weight relative to 100 parts by weight of the water-soluble organic solvent under 25 DEG C, to a mechanical kneading following by removing water-soluble salt and water-soluble organic solvent in water, wherein the resin (A) comprises amino or/and quaternary ammonium group.

Description

201000570 VI. Description of the Invention: [Technical Field to Which the Invention Is Provided] The object of the present invention is to provide a method for producing a fine organic pigment.

A fine organic pigment coloring composition. Further, the object of the present invention is to provide an offset printing ink, a gravure ink, an ink for inkjet printing, a resist for color filters and an ink, and a fine organic pigment coloring composition for a coating. [Prior Art] It is known in organic pigments, for example, that: by selecting suitable reaction conditions, it is possible to obtain a sub-on the other hand, such as 锢酤 貊 貊 , , , , , Γ Γ Γ Γ 如The finely sized pigment particles can be obtained, and the 10,000-sided surface, such as a copper phthalocyanine green pigment, is a pigment which is formed by extremely fine agglomeration formed during the synthesis by particle growth and granulation in the following steps. . Moreover, copper phthalocyanine blue pigments or diketones are known. Billow: Each of the pigments is a pigment which is large in size and uneven in shape during the synthesis, and is formed into a pigment by micronization and granulation in the following V steps. The dry pulverization method is a method in which coarse crude pigment particles are processed into a pigment by a ball mill, a grinding mill, and a grind scale, and the crude pigment particles are used as a pigment. In the current widely used method, there is a solvent-salt. Grinding method, dry pulverization method, and the like.

321118 3 201000570, a pigmented polyethylene glycol and other high-purity water-soluble = second-class mechanical grinding to make a pigment, 3, '· work soil δ machine with μ two dus up to juice By adhering to the amount of solvent, it is a compact mass (cluster), and the desired fineness of the pigment can be obtained by treatment at any temperature. sheet. Examples of the use of the high-fine-grain pigment include a color filter color filter in a color liquid crystal display device, in which two or more different colors are placed on the surface of the transparent substrate in four rows or in a cross arrangement; or (4) (4) It is made up of flat and pixels arranged in a fixed length and width. High contrast and transparency can be achieved by using two fine pigments. From the beginning of the device, however, it is difficult to obtain a stable dispersion when the pigment particles of high fineness are dispersed in, for example, the main body. To: = Highly viscous by the agglomeration of paste particles, etc., and then exhibits thixotropic: 〇P1C). Such a dispersion of the degree of the rise, poor fluidity, bowing = color, = problems in manufacturing operations and various values of the product. The formation of the filter zone of the enamel light-receiving sheet is usually carried out by dispersing the pigment in a colored composition containing = on a moon-permeable substrate such as a glass. At this time, if a high viscosity and poor fluidity are used, it is not preferable because the coating property is poor, the leveling property is poor, and the coating film is not obtained. Further, the color calender sheet formed by using the dispersion in which the pigment particles are agglomerated is clearly contrasted. 321118 4 201000570 It is desired that the pigment residue does not agglomerate and stabilize the fine particles, and is in a property. In order to carry out the use of a color liquid crystal display device in a large screen television or monitor, in addition to contrast, transparency, and the like, the viewing angle characteristics are also important items, and the technology for wide viewing angle is promoted. In general, a polymer film has birefringence, and when birefringence is large, polarized light is formed by a refractive index difference in a direction parallel to the film surface and a direction perpendicular to the film surface. Since the retardation greatly increases the retardation value of the color filter and causes a phase difference in the transmitted light, the viewing angle dependence becomes large and the display characteristics are lowered. In particular, it is known that the retardation value of the polymer film is increased by causing the polymer film 3 to have a crystal having a large retardation value. The diketopyrrolopyrrole pigment is refined by a solvent-salting method or the like, and particularly, the retardation value (positive value) is remarkably increased, and the viewing angle characteristics are deteriorated. Therefore, in order not to increase the retardation value of the diterpene pigment, the retardation value, the transparency, and the like, it is necessary to make it fine. When the tianke ketone pigment is used as a material of a color filter, it may be used in combination with a pigment having a large retardation value or a dispersion thereof. Therefore, it is necessary to lower the delay value of the sputum itself. Patent Document 1 discloses a technique for reducing the retardation value of a colored film. The colored film is a material pixel having an average refractive index of 16 Å or more and 1.90 or less and an absolute value of the birefringence of G.Ql or less. High color film. Patent Document 2 discloses a method for reducing a retardation value by causing a compound having two or more planar structure groups in a colored film to further contain a retardation-reducing particle having a lindenyl group or a pendant group of 321118 5 201000570 compound. Technology. Patent Document 3 discloses an organic pigment, a water-insoluble resin, an inorganic inorganic salt, and a water-soluble organic solvent. The technique disclosed in Patent Document 4 discloses a second, a bismuth, a pigment, a pigment, The insoluble inorganic salt Μ water-soluble solvent machine = the technique of mechanical kneading, and it is described that a resin type dispersing agent can be used. 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 [Document 4] Japanese Laid-Open Patent Publication No. 2001_22〇52〇 [Summary of the Invention] [The object of the present invention is to provide a fine organic pigment coloring composition, which is based on the lack of the prior art. The fine organic pigment η: in the manufacturing method of the present invention, the fine pigmented organic pigment is coated with a film-like color film in a pigmented carrier and a non-aqueous solvent.佶 ,, η, 日 &, the person with high visibility. The value is low, and the ❹ dependence is excellent and transparent [the means to solve the problem] This λ λ knowledge type evil system related to the manufacture of a kind of fine organic pigment = The method is characterized in that: the organic _, the water-soluble inorganic salt, the water-hybrid organic granule and the resin are mechanically kneaded to obtain a kneaded composition, and after the absence, the water-inorganic salt and the water-soluble organic solvent are removed in the water, wherein , Jane 321118 6 201000570 Fat (4) The method for producing the above-mentioned fine (four) pigments in the case of hunger with respect to the water-organic _ per iqq ^ degree of 1 part by weight or more and containing an amine group and/or a quaternary ammonium group 4 I, the embodiment of the present invention In particular, the resin (Α) is an acrylic resin. The method of the invention is related to the coating method of the above-mentioned fine organic pigments, wherein the acrylic resin is randomly polymerized. Acrylic resin.

One embodiment of the invention is a method for preparing a fine organic pigment, wherein the resin is insoluble in propylene glycol monomethyl (tetra)acetate. The embodiment of the present invention relates to a method for producing the above-mentioned fine organic pigment, wherein the 'organic pigment is at least one selected from the group consisting of diketones and tons of 2 machine pigments, and quinophthalone organic pigments' Organic pigments grouped in phthalocyanine organic pigments and indigo organic pigments. One embodiment of the present invention relates to a fine organic pigment whose protection system is obtained according to the above-described production method. One embodiment of the present invention relates to a fine organic pigment coloring composition characterized in that it contains the above fine organic pigment and pigmented body. Further, an embodiment of the present invention relates to a fine organic pigment coloring composition described above, characterized in that it contains a nonaqueous solvent. [Effect of the Invention] When the fine organic pigment coloring composition of the present invention is applied to a film, the fineness of the pigment and the pigment is high and the retardation value is low, so that a color film having high transparency and excellent viewing angle dependency can be obtained. By this, it is possible to provide a color 7-21118201000570 filter which exhibits an excellent effect of exhibiting a few colors and having low viewing angle dependence in a liquid crystal television or the like. [Embodiment] [Formation for Carrying Out the Invention] The fine organic pigment of the present invention is obtained by mixing an organic inorganic salt and a water-soluble organic solvent (A), water-soluble, and then removing a water-soluble inorganic hydrazine in water to obtain a kneaded composition. , used in the kneading composition; ; f cold organic solvent. The organic pigments used are at least one, and the organic materials are organic pigments, and the organic pigments are used. Since the two pigments and the phthalocyanine organic pigments have =, - the wells have two clear materials and the organic pigments of the charm f / group. Excellent light resistance and stagnation resistance. _巴<Yanke, with specific examples of coloring materials, ketones and organic pigments, and 唬, from time to time, can be listed as Γ r D.

Red 254, 255, 264 or 272 to ..LPlgment 73 or 81, etc. ‘ * LPlgment Orange 71 > 啥駄 _ organic pigments are general and heat resistant.啥_•有: (4)-„Special examples of Gynecology Organic Yankee are indexed by pigment index. 5 Tiger watches are not %, such as: CIP coffee ntYeii〇wm, etc. Photosynthetic organic pigments are purple organic pigments with excellent The heat resistance of the second (four) organic pigment is exemplified by a pigmented crystal two-sheet... such as: αί.ρ1Μ or 37. db phthalocyanine organic pigment is an organic pigment of blue or green, which has excellent light. H and heat resistance. Specific examples of the blue phthalocyanine-based organic pigments are represented by the number of the pigments 51, and examples thereof include (1) 仏 版 ( (1)!, 8 321118 201000570 体 2 4 colors: 2: J 2: green The phthalocyanine-based organic pigments are 丨i冢5丨 compiled from time to time, such as: 匚

Green 7, 36 or 58 and so on. _ U^ment: The water-soluble inorganic salt used is a pulverization aid = when the pigment is pulverized by the high hardness of the inorganic salt, and the 夂 particles are refined. As long as it is dissolved in water, _ 嶋 嶋 can be listed as: salt (chlorine butterfly two: and:: zinc bismuth, calcium chloride, chlorinated town or a mixture of these, etc., autumn: It is advisable to use sodium chloride. The mixture of the water and the salt of the mixed group of silk scarves has a better range of weight and can be selected according to the hardness of the target. When the amount is more than ==, the micronization and the whole grain are easy to carry out. However, in the 3G double-weighted chemical mixture, the amount of pigment treatment is large, so the productivity is high and the particle diameter of the water/inorganic salt is not particularly limited, but the volume reference is ^(medlumpartlcie Slze) (10)) should be i to 50_. When the coffee is 50% or less, the amount of the crude organic pigment used for miniaturization is relatively short. When the D50 is 1/m or more, the water can be used as a low-energy (IV) water inorganic salt. The particle size of the water-soluble inorganic salt can be determined by using a dry form and a particle size distribution analyzer. / Τ 混 混 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The degree of dissolution of the industrial washing and removal is due to the temperature rise of the kneading composition # X 卜, the state of the kneading, so in terms of safety, the solvent is used as the high-foam solvent, and the solvent is Examples include = base) W, 2-butyryl alcohol, 2-(isopentyloxy)ethanol, 2-(hexyloxy J ethanol, diethylene glycol, diethylene glycol monomethicone, diethylene glycol Monobutyl ether, triethylene glycol, diuret B ~ diol, lactulol, dipropylene, propylene glycol monomethyl ether, dipropylene glycol monoethyl sulphate, low molecular weight polypropylene glycol, local amine "bite, tetrahydrogen Oral ketone, dioxane, methanol, ethanol, ri-propanol, isobutanol, n-butanol, ethylene glycol, ", propylene glycol monomethyl acetate, ethyl acetate, isopropyl acetate, acetone, Methyl ethyl hydrazine, - mercapto decylamine, dimethyl sub-milling or methyl ketone ketone, etc. In addition, two kinds may be mixed as necessary. The solvent is used. The amount of the water-soluble organic solvent in the kneading composition is not particularly limited, and is expected to be 3 to 4% by weight in the kneaded composition, and can be composed of the amount of the water-insoluble inorganic salt and the kneading composition. The hardness of the material is selected. Water-soluble organic = When the agent is insufficient, the kneaded composition cannot be agglomerated and cannot be energized. Therefore, it is difficult to maintain a stable operation due to the refinement or the kneading composition being too hard. Further, when the addition is excessive, the kneading composition is too soft and it is difficult to obtain the desired fineness and the entire particle size. The resin (A) used in the kneading composition is kneaded at 25 ° C for the composition. The solubility of the water-soluble organic solvent used per one part by weight of the water-soluble organic solvent is preferably 1 or more, and the solubility is preferably 3 parts by weight or more. The solubility is 321321318 10 201000570 parts by weight or more, due to the water-soluble organic solvent Since the compatibility is high and the resin is uniformly adsorbed on the surface of the pigment, it is easy to obtain desired micronity and a decrease in retardation value, etc. Further, the resin (A) must have an amine group selected from a group of a 4- to ammonium salt group, which has an affinity for an organic pigment by the presence of the group, and further has effects such as fineness and birefringence. The amine group is selected from the group consisting of a primary amine group and two The functional group of the group of the amine group and the tertiary amine group, wherein the resin (A) is preferably a tertiary amine group or a tertiary ammonium salt group. Here, the 'quaternary ammonium salt salt is as follows: 1) or the following formula (2): General formula (1): -iu-κ 八nr) (In the general formula (1), U is independent of each other, and the number of carbon atoms is from 9 to 9 The neonuclear group; the hydrogen atom of the heart, the county with a carbon number of 丨9 or the calcination group of Wei i to 9; Z1 _ atom, R4SQ3_ or R4〇s〇3_; the base of the base Wei 1 to 2Q Or benzene having a carbon number of 1 to 20 (2): = number Γ to Γ R5 and R2 are each independently, a number of 1 to 9 or a (four) wire; R7 is a carbon number of 1 to 6 (4) to 5 For better, 1 to 3 is better. The main skeleton of Shu Yue (A) is not particularly limited. The acrylic resin refers to an ethylenic:-: dilute acid-based resin-based ethylenic non-fresh monomer as a "base or mercapto propylene sulfonium & knife" and optionally with the aforementioned 321118 201000570 (5) When the fine organic pigment of the present invention is used as a fine substance to exhibit the characteristics as a color filter, the resin used in the coloring composition of the fine organic pigment is used as the resin of the coloring composition. And the composition of the fine organic pigments 着 ' ^,, 'Guy. Because the resin (4) is expected to be acrylic acid resin. In the second money, therefore the amine-based acrylic tree furnace by " The amine body of the body and/or the salt base of the fourth grade may be used. Preferably, the amine and the other 6 ship residues, and the amino group are used. Examples of the unsaturated monomer may be exemplified by a bis-group-ethylenically unsaturated monomer and a 4(10) unsaturated monomer. Examples of the ethyl-unsaturated monomer having a -amino group may be exemplified by: (M)acrylic acid N,N-:methylaminoethyl 3, (methyl) propyl, n, n-diethylaminoethyl vinegar, M, methacrylic acid N, N_: methylamino propyl vinegar or (methyl) acrylic acid N, N-diethylamino propyl vinegar and the like, π-based acrylic acid vinegar containing N, N-diamine Or Ν, Ν-methylaminoethyl (τ) acrylamide, ν, diethylaminoethyl (f) propylamine, hydrazine, hydrazine dimethylaminopropyl (methyl) Acrylamine or hydrazine, hydrazine-diethylaminopropyl (methyl) propyl acetoacetate, etc., containing # ν, ν - 二烧月* based (meth) acrylamide, etc. Preferably, ruthenium (meth) acrylate or hydrazine-dimethylaminoethyl ester is preferred. Examples of the ethyl sulphate having a quaternary ammonium salt group and a monomer are exemplified by the above ethylene having a tertiary amino group. For the addition of the unsaturated monomer to the leveling agent, 321118 12 201000570 Examples of the leveling agent can be exemplified by: mercaptosulfuric acid such as dimercaptosulfuric acid, diethylsulfonic acid or propylsulfuric acid; Or a benzene acetoacetate and other ASg 'gas-fired, m-chlorine or chlorinated hospitals such as burning base gas; desert meth, Mo-burn or feed system, etc.; or ketone chloride or sulfhydryl side. Anti-glycans of ethylenically unsaturated monomers with secondary amine groups and 4-staged agents Generally, it can be carried out by dropping into a solution of an ethylenically unsaturated monomer having an amine group below the amine group, and the degree of the fourth-order reaction is about the following. It is to make the ethylene monomer 4 匕Ά ' to about 3 (TC below the best 'reaction time is about i to 4 hours. ... In addition, the fourth-stage agent can also use a burnt oxygen sulfhydryl halide. The oxycarbonylalkyl dentate is represented by the following formula (3): General formula (3): z -r-co〇R9 (In the formula (3), 'Z2 is a halogen such as gas or bromine, preferably (4); R8 is Carbon number 1, = 1 to 5 is preferred, i to 3 is better); R9 is a lower alkyl group having a carbon number of 6 to 1 (preferably 1 to 3). The external/, ethyl-containing ethylenically unsaturated monomer and the m-based alkyl group i 1 should be such that the above-mentioned 4-staged agent is not related to the amine base. After the same reaction is carried out, it can be obtained by using _9 water == into a shiproot ion (-(10)-). Thereby, an ethylenically unsaturated monomer having a beetroot structure and having a 4-stage ammonium salt group can be obtained. - The other monomer of the ethylenic acid monomer may be listed as a monomer other than the (4) acid monomer and the propylene 321118 13 201000570 olefinic monomer. In the present application, it is described as "(meth)acrylonitrile", "(meth)acrylic acid", "(meth)acrylic acid", "(meth)acrylic acid ester", "(meth)acrylic acid In the case of acid oxy or "(meth) acrylamide", unless otherwise specified, it is expressed as "acryloyl sulfhydryl and / or (meth) acryl thiol", "acrylic acid and / or (A) "Acrylic", "acrylic and/or (meth)acrylic", "acrylate and / or (meth) acrylate", "acryloxy" and / or (meth) acryloxy" or "Acrylamide and / or (meth) acrylamide". Examples of the acrylic monomer include methyl (meth)acrylate, ethyl (meth)propionate, (meth)acrylic acid, and isopropyl (meth)propionate. N-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl acrylate (meth) acrylate, 2-ethylhexyl acrylate (meth) acrylate, cyclohexyl (meth) acrylate , stearyl (meth) acrylate, lauryl (meth) acrylate, tetrahydrofuran (meth) acrylate, isobornyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) acrylate Ester, phenyloxyethyl (meth) acrylate, phenoxy diethylene glycol (f) acrylate, oxypropylene glycol (meth) acrylate or ethoxylated polyethylene acetyl (7) acrylate (meth) acrylate such as alcohol ester, or (meth) acrylamide, N, N-dimethyl (meth) propylene feamine, N, N-diethyl (f-) acrylamide, n - (meth) propylene phthalamide such as isopropyl (meth) propylene, diacetone (methyl) acetoacetate or acrylonitrile. Further, an ethylenically unsaturated monomer having a carboxyl group can also be used. Examples of the ethylenically unsaturated monomer having a carboxyl group include, for example, acrylic acid, methacrylic acid, ε-caprolactone addition acrylic acid, ε_caprolactone addition methyl propyl 14 3211) 8 201000570 enoic acid One or more selected from the group consisting of isaconic acid, maleic acid, fumaric acid, and crotonic acid. Further, an ethylenically unsaturated monomer having a hydroxyl group can also be used. Examples of the ethylenically unsaturated monomer having a 'crosslinking group' may, for example, be 2 or 3-hydroxypropyl (meth)acrylate (meth)acrylic acid, 2 or 3 or 4 in (meth)acrylic acid. (Meth)acrylic acid (tetra) vinegar such as hydroxybutyl ester or cyclohexanedimethanol mono(meth)acrylate. In addition, it is also possible to use poly(methyl)acrylic acid or a poly(meth)acrylic acid obtained by addition polymerization of the above (meth)acrylic acid to a acetonitrile, epoxy epoxide, and/or epoxy butyl hydrazine. Poly(acrylic acid) obtained by forming (poly) r-pental vinegar, (poly), and/or (poly) 12-base stearic acid.丨 乂 η η η η η η η η η η η η η η η η η η η η The ethylenically unsaturated mono-system containing a phosphate acid-based group can be obtained, for example, by reacting the above-mentioned oxime-containing reading and monomer recording with an acidifying agent such as pentaoxane (tetra) or polycarboxylic acid. Examples of the monomer other than the above-mentioned acrylic acid-based monomer include styrene such as a-f-phenylphenidene; ethylethyl _, n-propyl ethoxide, isopropyl galenium, n-butyl butyl Ethyl acetate such as dilute or isobutyl ethane, vinyl acetate such as vinyl acetate or vinyl propionate, and the above-mentioned monomers other than the acrylic monomer. The precursor of the above-mentioned acrylic monomer is transferred to the resin (1) used in the present invention (4), and the living anionic polymerization is carried out by the (four) sub-polymerization, the active cationic polymerization, and the living radical polymerization (four). ^二自^ 321118 35 201000570 base polymerization or living radical polymerization is preferred. For the living radical polymerization method, a polymerization initiator is preferably used. For the polymerization agent, for example, an azo compound and an organic peroxide can be used. Examples of the compound include, for example, azobisisobutyronitrile, 2, 2, even: = (2-methylbutyronitrile), and u'-azobis(cyclohexaneb carbonitrile & Azobis(2,4-dimethylvaleronitrile), 2, 2'-azobis(2,4-didecylmethylvaleronitrile), dimethyl 2, 2,monoazodi(2) - methacrylic acid), 4, 4, nitrogen di(4-cyanovaleric acid), 2,2'-azobis(2-hydroxymethylpropionitrile) or 2,2,-azobis [ 2-(2 ten sitting scare _2-base) propyl hydrazine], etc. Examples of organic peroxides include, for example, benzoic acid benzoic acid, benzoic acid benzene acid, third butyl vinegar, chloroperoxy cumene, Diisopropyl sulphate dihydrate, di-n-diester diperoxide diperoxide diperoxydicarbonate di(2-ethoxyethoxy vinegar), peroxy neodecanoic acid third: ester: peroxypivalic acid third Butyl ester, peroxidic (3, 5, 5 - trimethylhexane), di(tetra)peroxide or diethyl peroxide. These polymerization initiators may be used singly or in combination of two or more. It should be 4 150 ° C, with 50 to 1 1 (ΤΓ太φ /土. e - 〇C is more 仏' reaction time should be 3 to 30 hours, to 5 to 2 0 hours is more preferable. The living radical polymerization method can suppress the side reaction caused by the radical polymerization, especially the growth system of the polymerization, and thus can easily synthesize the polymer or the molecular weight of the resin. You can adapt to the point of the early body by using the atomic transfer radical polymerization method with the organic compound or the sulfonium isomer as the initiator and the transition metal complex as the catalyst. The point-origin radical polymerization method which can be adapted to the polymerization temperature of the existing equipment can be carried out according to the method described in the following reference [to 8 16 321118 201000570, etc. (Reference 1) Fukuda et al., Prog. Polym·Sci 2004, 29, 329 (Reference 2) Maty jaszewski et al., Chem. Rev. 2001, 101, 2921 (Reference 3) Maty jaszewski et al. 'J. Am. Chem. Soc. 1995, 117, 5614 (Reference 4) Macromolecules 1995, 28, 7901, Science, 1996, 272, 866 (Reference 5) W096/030421 (Reference 6) W097/018247 (Reference 7) Japanese Patent Laid-Open No. Hei 9-208616 (Reference 8) In the above polymerization, it is preferred to use a solvent (this) There is also a case called a solvent.) The solvent is not particularly limited, but for example, ethyl acetate, n-butyl acetate, isobutyl acetate, toluene, xylene, acetone, hexane, mercaptoethyl group can be used. , cyclohexanone, propylene glycol monoterpene acetate, dipropylene glycol monoterpene ether acetate, ethylene glycol monoethyl acetate, ethylene glycol monobutyl & oxime acetate, diethylene glycol monoethyl acetate Vinegar or diethylene glycol monobutyl bond acetic acid and so on. These polymerization solvents may be used in combination of two or more kinds. Further, in the resin (Α) to which the present invention is applied, a method of producing a fourth-order ammonium salt as a functional group is carried out by copolymerizing not only the above-mentioned ethylenically unsaturated monomer having a quaternary ammonium salt group as a monomer component. In addition, the ethylenically unsaturated monomer having a tertiary amino group as a monomer component may be copolymerized to obtain an acrylic resin having a tertiary amino group, and then reacted with the above-mentioned fourth-stage agent. 321118 37 201000570 The amount of the amine group and the quaternary ammonium salt group present in the resin (A) to which the present invention is applied is not particularly limited, but the sum of the amine value of the resin and the ammonium salt value of the fourth grade is 1 to 300 mgKOH/g. Preferably, it is preferably from 10 to 200 mgKOH/g. When the sum of the amine value and the grade 4 ammonium salt value is 1 mgKOH/g or more, the effect is remarkable, and when it is 300 mgKOH/g or less, the compatibility in the fine organic pigment coloring composition is high and becomes low viscosity. Further, the structure of the amine group is not particularly limited, and it can be used by substituting various functional groups. The molecular weight of the resin (A) used in the present invention is not particularly limited, but the converted weight average molecular weight measured by gel permeation chromatography (GPC: Gel Permeation Chromatogrpahy) is preferably from 1,000 to 500,000, more preferably from 5,000 to 15,000. . The resin (A) used in the present invention is preferably one having a solvent which is insoluble in the coloring composition of the fine organic pigment. According to this, a high-contrast ratio fine organic pigment coloring composition can be obtained. The resin (A) is preferably one which is insoluble in an ester solvent having a molecular weight of from 118 to 13 3, and more preferably propylene glycol monoterpene ether acetate having a molecular weight of 132.16. The resin (A) used in the present invention can obtain a fine organic pigment and a fine organic pigment coloring composition even if a resin obtained by block polymerization is used, and a resin obtained by random polymerization which is easy to prepare by the method can be obtained in the same manner. A fine organic pigment and a fine organic pigment coloring composition. The block polymerization refers to a method in which only a certain monomer is polymerized in advance, and other monomers are separately polymerized, and blocks of the respective polymers are separately prepared and then reacted. 18 321118 201000570 The amount of resin (4) in the kneading composition is not limited to organic pigments! The parts by weight are preferably 〇. 〇1 to 1 ^, but only relative to 3.4. The amount of the resin (1) is "!": the upper layer of the 〇 〇 03 03 can be refined, and the viscosity is better in the composition of the fine organic pigment. Further, when the compatibility between the micro (A) and the pigment carrier is adjusted (1), and the solubility of the resin is high, it is preferable to limit the amount of the resin (1) to a minimum to fall = matter: t influence 'other-side, phase (four) When it is time to increase: the tree exerts a decentralized effect. In the = composition can be used together: a variety of resins, dispersion aids = take = _, surfactants and other additives; in the organic pigment molecules lead to use = = pigment derivatives; or generally as a physical job And he (four) 钡 and - milk cut and other inorganic pigments. It can also be filled with other pigments and processed to adjust the color tone. = is 'In order to prevent the crystal growth of organic pigments and crystal transfer sub-efficiently to produce fine organic pigments, it is advisable to make the mixing group = pigment street organism, brewing derivative, π-phase derivative or tri-morphine: raw: two less — a derivative. Each of the above derivatives may have an substituent in the organic pigment or window, or an acidic substituent or an oximeimine group.苴中为==二其: The same structure of the organic pigment of ΓΓ is the effect of the extremely::::: organism, because the pigment derivative of the pigment which inhibits the growth of the pigment is introduced into the organic pigment, the substitution of the substituent 321118 19 201000570 It is better to use the color of the pigment used, such as the amount of color added. The organic coloring matter also contains a coloring aromatic polycyclic compound which is not usually called color. For the pigment derivative, it is possible to use the Japanese Patent Publication No. 52-132031, the Japanese Patent Publication No. 54-62222, the Japanese Patent Laid-Open No. 5(4), or the Japanese Special Coffee No. 6(8). . A pigment derivative that is particularly broadly detectable, because of the pigment = use. These may be used alone or in combination of two or more. The large pigment is thus a compound of the m(4) material. General formula (4): ^

A'B (In the general formula (4), A is an organic pigment residue or an entangled imine F group.) Soil, β is an intellectual substituent, and an acid is taken in the formula (4) to form a hydrazine such as a diketone. Pyrrole. Examples of the organic pigments of the specific groups such as arsenic and bismuth residues include azo-based pigments such as azo; copper, disazo or polyphthalocyanine pigments, and amine groups (IV). , Yin Dan g with the same, You m [Min ° Ding, Huang Shizhen, bite Ming pigments, · two ah:: or onion ketone and other onions, pigments; cut enamel pigments, · different, Duo Luo, = 'Money pigments' · flower pigments; sulfur pigments; stupid and snails; stalks of pigments; 啥 (4) complex pigments, etc., thresh (threne) pigments or metal formula (4) , β 认 ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( (

Substituent shown by CH 2' (ίο) /R10 N: η R11 R<2

,cH~CH x~N\ Vr16

C\H CH_ R14

X

N

R 17

N N-

Q

[In the general formulae (5) to (7), CH2NHCOCH2-CH2NHS02CH2-X is -S〇2-, ~c〇-, -CH2-, or direct bonding; Y is -NH-, ~0- or direct bond n is an integer from 1 to 10; υ1 is mNR' or a direct bond; R and R are each independently a hydrogen bond, a carbon group having a substituent of from 1 to 36, and a carbon number which may have a substituent a dilute group of 2 to 36, which may have a phenyl group having a substituent of 21 321 Π 8 201000570, · an alkylene group which may have a substituent or an extended aryl group which may have a substituent; R and Rn are each independently a hydrogen atom; Carbon number with substituents! a filament of up to 30, a dilute group having a carbon number of 2 to 3 Å having a substituent, or a F-containing body, and containing a nitrogen, oxygen or sulfur atom, and having a heterocyclic ring; and RH and R13 are each independently a hydrogen atom, a cal group having a carbon number of i to 2 Å having a substituent, a carbon number 2 to another alkenyl group which may have a substituent, and an exoaryl group having 6 to 2 carbon atoms which may have a substituent; R16 And a hydrogen atom, an alkyl group having 1 to 2 carbon atoms which may have a substituent, an alkenyl group having 2 to 20 carbon atoms which may have a substituent; R17 is a substituent represented by the above formula (5) or a compound of the above formula (6) (4) a substituent, a substituent, a substituent represented by the above formula (5) or a substituent represented by the above formula (6)]. The amine component used for forming the substituent represented by the general formulae (5) to (7) may, for example, be: amine-ethylamine, methylethylamine, N,N-ethylisopropylamine, hydrazine, hydrazine-ethylpropyl butyl Amine, N,N-methylisobutylamine, n,n-butylethylamine, face, Le Dibutylethyl f, diisopropylamine, dipropylamine, n,n-second butyl propyl hydrazine, butylamine , 2nd butanamine, diisobutyl HN-isobutyl-second dibutyl, decylamine, diisoamylamine, dihexylamine, dicyclohexylamine, di &amp; ethylhexyloctylamine, N, N-decyl octadecylamine, didecylamine, di-propylamine, N,N-soil, 2-mercaptopropylamine ruthenium hexylamine, dioleylamine, distearylamine, 321118 22 201000570 N,N- Dimethylaminomethylamine, N,N-didecylaminoethylamine, N,N-dimethylaminopentylamine, N,N-dimethylaminobutylamine, hydrazine, hydrazine-diethyl Ethylaminoethylamine 'Ν, Ν-diethylaminopropylamine, hydrazine, hydrazine-diethylaminohexylamine, hydrazine, hydrazine-diethylaminobutylamine, hydrazine, hydrazine-diethylamino Pentylamine, ν, Ν-dipropylaminobutylamine, hydrazine, hydrazine-dibutylaminopropylamine, hydrazine, hydrazine-dibutylaminoethylamine, hydrazine, hydrazine-dibutylaminobutylamine, Ν, Ν-diisobutylaminopentanamine, ν, Ν-fluorenyl-laurylaminopropylamine, hydrazine, hydrazine-ethyl-hexylaminoethylamine, hydrazine, hydrazine bis distearylamine Amine, f N, monooleylaminoethylamine, N,N-distearrylamamine, picidine, 2-indolylpiperidine, 3-methylpiperidine, 4-methylpiperidine, 2,4-Dimethylpiperidine, 2,6-dimercaptopiperidine, 3,5-dimercaptopiperidine, 3-piperidinemethanol, piperidinic acid, methyl 4-piperidinecarboxylate, 4 _ piperidinic acid ethyl ester, 2-piperidinyl alcohol, pyrrolidine, 3-hydroxypyrrolidine, N-aminoethylpiperidine, N__aminoethyl 4-methyl piperidine, N-amino B Basomomorpholine, aminopropylpiperidine, N-aminopropyl-2-hydrazinopiperidine, hydroxypropyl-4-methylpiperidine, f-aminopropyl-N-methyl d well, N-butyl π-bottom oxime, N-mercapto-high π-bottomin, 丨_cyclopentyl t-till, 1-amino-4-mercaptopiperidin or bucyclopentylpiperidin. —S03M / i ——COOM/i R18

[In the above general formulae (8) to (i〇), 23 321118 201000570 Μ is a hydrogen atom, a _ sub, a _ sub u sub, a (four) sub or a samar atom; i is a valence of ruthenium; d; 9, R 2 ° and Each of r is independently a hydrogen atom, a vinyl group having 1 to 36 carbon atoms which may have a substituent, a phenyl group or a polyoxyl group having a substituent having 2 to 36 carbon atoms which may have a substituent. The amine component used to form the sulfonic acid amine salt of the formula (1) can be any one of the first, second, third or fourth grade amines. Examples of the primary amine include, for example, hexylamine having a side chain, heptylamine, octylamine, decylamine, decylamine, decylamine, dodecylamine (i.e., laurylamine), tridecylamine, and thirteen amines. : hexadecylamine, heptadecylamine, octadecylamine, pentadecylamine or twentieth: and an amine, or an unsaturated amine corresponding to the above saturated amine carbon number. Examples of the secondary amine include, for example, dioleylamine or distearylamine. Examples of the tertiary amine include dimethyloctylamine, dimethylguanamine, dimethyl laurylamine, dimethylstearylamine, dilauryl monomethylamine or trioctylamine. Soil and amine can be as follows: monomethyl dilauryl ammonium chloride, dimethyl di oil ir yttrium ammonium 1 1-2 dimethyl fluorenyl chloride (tetra), dimethyl dioctyl chlorinated money, - hard Ruthenium-based emulsification record, dimethyl distearyl chloride record, three

= vaporized ammonium, trimethyl hexafluoride, triterpene octadecyl; I female monodecyl lauryl tetradecyl ammonium chloride or dimethyl hexadecane decyl ammonium hydride Wait. In the case of the f, R'R2D and r21 of the earth-earth formula (10), examples of the stretching group include, for example, a polyoxy-extension ethyl group or a polyoxy-extension base group, and a milk α, The blending amount of the pigment derivative in the east and the resultant is preferably from 1 to 30 parts by weight, more preferably from 5 to 20 parts by weight, per 100 parts by weight of the organic pigment 321118 24 201000570. When the amount of the derivative is 1 part by weight or more, the effect of addition is easily obtained, and if it is 30 parts by weight or less, the remaining derivative has no effect on dispersion. 01重量份为0. 01。 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 01 02重量份更优选。 Examples of the apparatus for mechanically kneading the kneaded mixture include a kneader, a planetary agitator, a three-arm planetary mixer (tri-mix; manufactured by Inoue Co., Ltd.), a two-axis roller, a triaxial roller, a multi-axis roller, and an extrusion. (Extruder), KRC kneading machine (manufactured by Kurimoto Iron Works Co., Ltd.), or kneading extrusion-extracting machine (MIRACLE KCK; manufactured by Asada Iron Works Co., Ltd.), etc., are not particularly limited as long as they can impart efficiency to the kneaded material. Mechanical shear force, whether intermittent or continuous. The temperature at which the kneaded mixture is mechanically kneaded is not particularly limited, but it is preferably treated at 20 to 80 ° C, and more preferably at 30 to 65 ° C. Under the mixing conditions of 20 ° C or more and 80 ° C or less, it is not necessary to reduce the amount of the kneaded material treatment or to reduce the viscosity of the kneading mixture; and it is not necessary to use these treatments in combination, that is, it is easy to control the pulverization and miniaturization of the organic pigment particles. The speed and the crystal growth rate of the organic pigment particles can be obtained to obtain the desired fineness. The fine organic pigment after the kneading is treated according to the usual method. Namely, the kneaded composition is treated with water or an aqueous solution of an inorganic acid and filtered, washed with water to remove the water-soluble inorganic salt and the water-soluble organic liquid to separate the fine organic pigment. Specifically, the fine organic pigment after the kneading is put into water and stirred for 25 321118 201000570, which is a water liquid. Then, the liquid is filtered, washed with water, and the inorganic salt and the water-soluble organic solvent are preferred.衣1^ Put fine organic pigments.哕笙 v. Repeatedly on the evening. Inorganic acid water A ' For example: Contains hydrochloric acid, sulfuric acid, item 'acid, column = (four) _ such as: high-speed surface machine. The fine pigment can be directly used in a pulverized state and used in a powder state. Army "II: The average particle size of fine organic pigments is preferably ~3 to 3 〇nm or less, and more preferably 2 〇nm or less. Flat =, 5 nm or more is preferred. The average primary particle size of the pigment is greater than the upper limit. : When it is less than the lower limit, it is difficult for the pigment to become _ ^ to maintain the stability of the coloring composition, and to ensure the liquidity of the method of calculating the particle size and the secondary particle size. For example, a dental material electron microscope (the fine organic pigment photographed by photographing is used to obtain the projected area of each particle by image processing, etc., and the diameter of the circle of the product is calculated. The diameter and the L number of the circle of each particle are calculated. The obtained value can be used as the average-secondary particle size. I The obtained fine organic_ is used as a fine organic coloring composition. The field organic coloring composition contains a fine organic pigment and a pigment carrier. System month: fine organic pigment coloring composition The pigment contained in the pigment dispersion is composed of a resin, a precursor thereof or the like. The resin has a penetration rate of 4 (10) to 7 in the visible field of the visible light, preferably 95. More than % Preferably, the resin 匕',, the plastic resin, the thermosetting resin, and the active energy ray-curable tree 321118 26 201000570 ====:==- relative to 100 parts by weight of the fine organic pigment in the fine organic coloring composition, The t-material carrier may be used in an amount of from 30 to 0.4 parts by weight, preferably from 60 to 450 parts by weight. Further, when the mixture of the resin and its precursor is used as a pigment carrier, it is relative to the micro-pigment in the fine organic coloring composition. (10) parts by weight, the resin may be used in an amount of 2 to 4 parts by weight, preferably 50 to 250 parts by weight. Further, 'with respect to the fine organic coloring composition, the fine organic pigment (10) parts by weight, the resin precursor It can be used in an amount of 10 to 300 parts by weight, preferably 1 to 2 parts by weight. Examples of the thermoplastic resin include: bismuth, styrene-maleic acid copolymer, chlorinated polyethylene, chlorine Polypropylene, polyethylene, vinyl chloride-acetate (tetra) copolymer, polyacetate, polyamine, i-resin, polyacetate, propylene glycol, alkyd, poly Phenylacetone resin, polyamine tree曰, rubber enamel resin, cyclized rubber resin, cellulose, polyethylene (HDPE, LDPE), polybutadiene or polythylene imide grease, etc. Examples of thermosetting resins include epoxy resin and benzene. Hydrazine, resin, maleic acid resin, rosin modified fumaric acid resin, melamine tree glutinous rice, gland resin or age resin, etc. a polymer having a reactive substituent such as a slow base such as a ruthenium γ, and a (fluorenyl)acrylic acid compound or cinnamic acid having an isocyanate group, an acid group or a lactam-based t-reactive substituent, and then Photocrosslinking basics such as acrylonitrile or styryl may also be used: linearity of anhydrides containing styrene-maleic acid needle copolymer or α321118 27 201000570-olefin-maleic anhydride copolymer The polymer is obtained by semi-esterification of a (meth)acrylic compound having a hydroxyl group such as a hydroxyalkyl (meth) enoate. Examples of the monomer and oligomer of the resin precursor include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, and isopropyl (meth)acrylate. Butyl acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, isoamyl acrylate, octyl (meth)acrylate, (meth)acrylic acid Isooctyl ester, 2-ethylhexyl (meth)acrylate, cetyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, (methyl) tridecyl acrylate, isomyristyl (meth) acrylate, stearyl (meth) acrylate or isostearyl (meth) acrylate, linear or branched alkyl acrylate ;^ cyclohexyl (meth)acrylate, t-butylcyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentaoxy(ethyl)acrylate, (methyl) Dicyclopentyl acrylate, dicyclopentyloxyethyl (meth)acrylate or isobutyl (meth)acrylate Ester (yl) acrylate cyclic ester; &amp; fluoroalkyl acrylate; (methyl) propylene oxime modified polydimethyl oxalate (triethyl methacrylate), (methyl) Octafluoropentyl acrylate, perfluorooctyl ethyl (meth) acrylate or tetrafluoropropyl (mercapto) acrylate (fluorenyl) (polyoxymorphic macromonomer); (fluorenyl) acrylic acid Tetrahydrofuran methyl ester or (meth)acrylic acid, methyl methacrylate, 8 28 201000570 -3- oxetane g, etc. (meth) propylene (tetra) having a heterocyclic ring; (F-based) acrylate acid ester, Methyl) propyl acetophenoxy phenoxyacetate, phenoxy ethoxylate (E) diacetate (meth) acrylate vinegar, (meth) acrylic acid p-cumyl phenoxy acetoacetate, p-cumyl phenoxy ethoxylate (meth) acrylates having an aromatic ring such as ethylene glycol (meth) acetoacetate or decyl phenoxy polyethylene glycol (meth) acrylate; (meth) acrylic acid 2 -Methoxy ethoxy, (methyl) propyl benzoate 2 - ethoxy acetoacetate, 3-methoxybutyl (meth) acrylate, 2 - methoxypropyl (methyl) propyl acrylate Diethylene glycol monomethyl ether (A Acrylate, diethylene glycol monoethyl ether (meth) acrylate, triethylene glycol monomethyl ether acrylate, triethylene glycol monoethyl ether (methyl) propionate, diethylene glycol _2_ethylhexyl acrylate (meth) acrylate, dipropylene glycol monomethyl ether (meth) acrylate, tripropylene glycol mono (meth) acrylate, polyethylene glycol monolauryl ether (meth) propylene oxime (poly) glycerol monoalkyl base (meth) acrylates; (mercapto) acrylic acid, acrylic acid dimerization , 2_(indenyl) propylene oxiranyl ethyl phthalate, 2-(indenyl) propylene methoxy propyl phthalate, 2_(meth) propylene oxiranyl ethyl hexahydro phthalate , 2-(indenyl) propylene methoxypropyl hexahydrophthalate, ethylene oxide modified succinic acid (mercapto) acrylate, stone-rebel ethyl (meth) acrylate or ω-carboxyl polymerization a (carboxyl) acrylate having a carboxyl group such as caprolactone (mercapto) acrylate; 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, (methyl) Acetate 2-butyl butyl, 4-hydroxybutyl (meth) acrylate, 2-propenyl ethoxyethyl 2-hydroxyethyl phthalate, diethyl 2 29 321118 201000570 alcohol Early i methyl) acrylate, dipropylene glycol mono (meth) acrylate, polyethylene glycol j (meth) acrylate, propylene glycol mono (meth) acrylate, polypropylene glycol mono &gt; (sub) acrylate , polybutylene glycol mono (T-based) acrylate, poly(ethylene glycol-propylene glycol) mono (meth) acrylate 'poly(ethylene glycol-butanediol) acrylate), poly(ethylene glycol-butyl a diol having a hydroxyl group (meth) acrylate such as bis(meth) acrylate (propanol-butanol) mono(methyl) acrylate or (meth) acrylate; Glycol diyl acrylate, diethylene glycol di(meth) acrylate, diethylene glycol di(meth) acrylate, polyethylene glycol bis(indenyl) propylene hydrazine, propylene Alcohol bis(indenyl) acrylate 'dipropylene glycol di(meth) propylene oxime propanol mono(methyl) propyl fine acid g, poly propylene Di(methyl)di-stained S-ion (Ethyl alcohol-propylene glycol) di(methyl) acrylate, poly(ethylene glycol-butanediol) di(meth)acrylate, poly(propylene glycol-butyl) Alcohol) bis(indenyl) acrylate, polybutylene glycol di(meth) acrylate, hydrazine, 3-butanediol di(meth) acrylate, neopentyl glycol bis(indenyl) acrylate, hydrazine , 6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate or ethyl, 2-butyl-propylene glycol bis(indenyl)acrylate, etc. Diol bis(indenyl) acrylates; one is L-mercapto-cyclopentanyl bis(methyl) acrylate, trans-tris-mercaptoacetic acid neopentyl glycol di(meth) acrylate, stearic acid Acid-modified pentaerythritol di(meth)acrylate, ethylene oxide modified bisphenol A type di(meth)acrylate, propylene oxide modified bisphenol A type di(indenyl) acrylate, butylene oxide Alkyne modified bisphenol A type bis(indenyl) acrylate, epoxy modified bisphenol p type bis(indenyl) acrylate, propylene oxide modified bisphenol F type II (fluorenyl) Sour vinegar, 321118 30 201000570 Epoxy butane modified bisphenol F type bis(indenyl) acrylate, zinc diacrylate, Ethylene ethoxide modified glycerin triacetate or glycerol Acetic acid g is equivalent to bis(indenyl) acrylate; monomethylaminoethyl (meth) acrylate acid, diethylaminoethyl (meth) acrylate, dimethylaminopropyl a (meth) acrylate having a tertiary amino group such as (meth) acrylate or diethylamino propyl (meth) acrylate; tris(methyl) acrylate, trimethylolpropane Tris(fluorenyl) acrylate, pentaerythritol tri(meth) acrylate, pentaerythritol tetra(meth) acrylate vinegar, pentaerythritol penta (meth) acrylate g or dipentaerythritol hexa (meth) acrylate, etc. Functional multifunctional polyfunctional (meth) acrylates; glycerol diglycidyl Sul-(meth) acrylic acid adduct, glycerol diglycidyl ether-(mercapto) acrylate adduct, polyglycerol poly Glycidyl ether __(indenyl)acrylic acid adduct, 1,6-butanediol diglycidyl ether, alkyl epoxidized ether (Methyl) Acrylic Acid Additive, Allyl Glycidyl Ethyl) Acrylic Acid Additive, Phenylglycidyl Ethyl-(Indenyl) Acrylate Additive, Phenyl Ethylene Ethylene Methyl) Acrylic acid adduct, bisphenol A type diglycidyl ether-(meth)acrylic acid adduct, propylene oxide modified bisphenol A type diglycidyl ether-(meth)acrylic acid adduct, bisphenol F-type diglycidyl-(meth)acrylic acid adduct, epichlorohydrin-modified decanoic acid-(meth)acrylic acid adduct, epichlorohydrin-modified hexahydrophthalic acid-(fluorenyl) Acrylic acid adduct, ethylene glycol diglycidyl ether mono(indenyl) acrylate adduct, polyethylene glycol diglycidyl ether _(mercapto) acrylate adduct, propylene glycol diglycidyl ether - ( Acryl group) acrylic acid adduct, polypropylene glycol diglycidyl ether-(meth)acrylic acid adduct, novolac type epoxy resin _(mercapto) acrylic acid adduct, nonylphenol novolak type epoxy resin (fluorenyl) acrylic acid addition 321118 31 201000570 or epoxy resin _ (methyl) acrylic acid adducts and other epoxy (meth) acrylate esters; Modified trimeric isocyanate, (meth) propylene sulfhydryl amide polyglycolic acid, (methyl) acrylonitrile modified polycarb, (meth) acrylate modified melamine, (methyl a (meth) acrylonitrile-based modified resin oligomer such as a propylene-based modified poly-wei, a (meth) propylene-based modified butadiene-based or a (meth) propylene-based modified rosin; Ethylene such as ethylene, α-methylstyrene, vinyl acetate, vinyl (meth)acrylate or allyl (meth)acrylate; hydroxyethyl vinyl ether, ethylene glycol divinyl ether or pentaerythritol triethylene Ethylene such as ether; (mercapto) acrylamide, hydrazine-methyl (meth) propylamine or hydrazine ethoxylate; or acrylonitrile. These may be used alone or in combination of two or more. In the organic pigment coloring composition of the present invention, a photopolymerization initiator or the like may be added when the composition is cured by ultraviolet light irradiation. A photopolymerization initiator which can be used, and examples thereof include 4-phenoxy 'chlorophenyridinium, 4_t-butyl-2-diphenenzamine, diethoxyacetophenone, and bu (4) -isopropylphenylhydroxy-2-methylpropane + ketone, 1-methylcyclohexyl (tetra), 21-yl Idimethylamino]-(4_n-morphinylphenyl)-butylate + thief 2-methyl - acetophenone photopolymerization initiator such as H4_(methylthio)phenyl]-2+morpholinylpropan-1-one; benzoin, benzoin oxime _, stupid ruthenium ether, styrene a benzoin photopolymerization initiator such as isopropyl ether or a stilbene dimethyl ketal; 321118 32 201000570 dicumyl ketone, benzhydryl benzoic acid, benzoyl benzoyl phthalate, 4 Diphenyl fluorenone photopolymerization initiator such as monophenyl benzophenone, hydroxy dibenzophenone, propylene dibenzophenone or 4-benzylidene-4,-decyl diphenyl sulfide a thioxanthone photopolymerization initiator such as thioxanthone, 2-oxythioxanthone, 2-methylthioxanthone, isopropylthioxanthone or 2,4-diisopropylthioxanthone; '4,6-Dichloro-S-trimium, 2-phenyl__4,6-bis(trichloroindenyl)_s_ three-pronged, 2-(p-methoxyphenyl)_4,6-bis (trichloro) Base)-s_trisole, 2__(p-Iphenyl)-4,6-bis(trichloromethyl)-s-trione, 2-piperidin-4,6-bis(trichloromethyl)- S-triterpene, 2,4-bis(trichloromethyl)_6-styryl_3_three tillage 2 (na-1-yl)-4,6-bis (tri-methyl)^ one three! ;! Well, 2_(4_曱-oxy-naphthalen-1-yl)-4,6-bis(trichloromethyl)-s_triterpene, 2,4_trichloromethyl January pepper base 6哄 or 2, 4-dimethylmethyl (4,-)-g-triterpene and other triterpene photopolymerization initiator; ▲ which acid (borate) is a photopolymerization initiator; Or, an imidazole-based photopolymerization initiator, etc. The photopolymerization initiator may be used in an amount of 5 to 2 parts by weight based on 10 parts by weight of the fine organic pigment in the coloring composition. The photopolymerization initiator may be used singly or in combination of two or more kinds, and the following sensitizers U oxy §, phosphine oxide, and benzoic acid formic acid 1 may be used together. Base-9 with phenanthrene, dereliction of duty, ethyl onion, 4 4, - 3'3, 4, 4, hydrazine (t-butylperoxy) di-, 4, 4 ethylamine Base two stupid g turn The sensitizer may be used in an amount of 0.1 to 60 parts by weight based on 100 parts by weight of the photopolymerization initiator in the composition of 321118 33 201000570. The fine organic pigment coloring composition of the present invention may be solvent-developed or It is adjusted in the form of an alkali-developable color resist. The color resist is obtained by dispersing a pigment in a pigment carrier containing a thermoplastic resin, a thermosetting (IV) H-recording line curable resin, and a monomer. One or two or more kinds of the above fine organic pigments are used together with a photopolymerization initiator as necessary to simultaneously use a triaxial light grinder, a two-axis roll grinder, a sand mill, a kneader or a grinder in a pigment carrier ( AttritQr) and other dispersing means can be used, and the fine organic pigment coloring composition of the invention can also disperse several kinds of the above fine organic pigments in a carrier and mix them to prepare a fine organic pigment dispersed in a pigment carrier. When appropriate, the type (4) dispersant, surfactant, and pigment derivative are dispersed to help disperse the help of the (4) dispersion. The pigment after dispersing the pigment is large. Therefore, when using a dispersing aid, the pigment carrier When the colored composition is made into a colored film, the basin is transparent =. The phase f is in the coloring composition of the pigment (10) parts by weight, and the dispersion aid is good. Use it! It is from 0.1 to 40 parts by weight. .1 to 30 parts by weight of the sowing, what is to prevent the aggregation of the fine organic pigments, and to maintain the fineness of the organic pigments, and the excellent function of the catastrophic / political, evil, and the use of such organisms Micro-organic '-the color film' is suitable as a dispersing aid. Color, degree 321118 201000570 The resin type added to the fine organic pigment coloring composition of Shuming is a powder. The pigment affinity part with adsorption pigment characteristics, and the part that is compatible with the pigment, and plays a role in the rhyme. Disperse in the function of the pigment carrier. Examples of the phthalocyanine pigment dispersing agent include, for example, polyethylene, polyaminocarboxylic acid, dimethicone, polyether, morpholine, polyoxyl or the like. ^The affinity part of the heart can be enumerated as H minus, Wei Ke, can: its base, recorded, amine group, 4 rhodium base or aramid base, etc., and ethylene oxide, poly ring Oxygen polymer conversion. n (4) The hydrophilic portion such as the weight of the ruthenium and the pigment (pigment) carrier may be, for example, a long-chain shinny chain, a polyethylene chain, a polyether chain or a polyester chain. Examples of the resin-based pigment dispersant include: styrene-maleic acid liver copolymer, olefin-maleic anhydride copolymer, poly(methyl) acrylate, styrene-(meth)acrylic acid copolymer , (methyl acrylate acid) propylene sulphuric acid vinegar copolymer, (meth) acrylic acid - polyethylene tererene baked macromonomer copolymer, Wei ester group containing acrylic resin, containing aromatic Resin-based acrylic resin, polystyrene (tetra) salt, _acid copolymer, methyl cellulose, anthraquinone or alginate resin such as methionine 7 or alginate a nonionic resin type pigment dispersant such as polyvinyl alcohol, poly(tetra) polyamine, polypropylamine or polymer powder; or 321118 35 201000570 polyethyleneimine, (meth)acrylic acid amine ester copolymer, a reaction product of polyisobutate ezozoline, a polyurethane having an amine group, a poly(lower alkylenimine) and a polyester having a free radical, or a cationic resin pigment dispersant such as chitin . These may be used alone or in combination of two or more. Commercially available resin type pigment dispersants may be, for example, Disperbyk-101, 103, 107, 108, 110, m, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, 170, 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 20CU, 2020, 2090, 2091, 2164 or 2163; or Anti-Terra-U, 203 or 204; or BYK-P104, P104S or 220S; Or Lactimon or Lactimon-WS; or resin-based pigment dispersant manufactured by BYK, such as Bykumen; SOLSPERSE-3000, 9000, 13240, 13650, 13940, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32600, 34750 '36600, 38500, 41000, 41090 or 53095, etc. Resin type pigment dispersing agents manufactured by Lubrizo 1 Co., Ltd.; or, EFKA-46, 47, 48, 452, LP4008, 4009, LP4010, LP4050, Resin type pigment dispersant manufactured by Ciba Specialty Chemicals Co., Ltd., such as LP4055, 400, 401, 402, 403, 450, 451, 453, 4540, 4550, LP4560, 120, 150, 1501, 1502 or 1503 , but not Set to such, may be used any of a resin-type pigment dispersant, and the like which may be used alone or in combination of two or more. The surfactant may, for example, be: polyoxyethylene alkyl ether sulfate, sodium laurylbenzenesulfonate, styrene - 36 321118 201000570 alkaline salt of acrylic acid copolymer, sodium stearate, * diphenyl ether dicarboxylate , anionic interfacial activity of lauryl sulfate monoglycolic acid = alkanolamine, lauryl sulfate, stearic acid monoethanolamine, sodium stearate, sodium sulphate, styrene-acrylic acid copolymer monoethyl lauryl ether phosphate Agent;—$♦ oxyethylene alkyl polyoxyethylene oleyl ether, polyoxyethylene uranyl monophenyl ether, polyoxyethylene alkyl ether phosphate, ^ vinyl fluorenyl 4 oxyethylene sorbitol Non-ionic interfacial compound grade 4 salt or other epoxy epoxide addition surfactants of vinegar or polyethylene glycol monolaurate; morphine and terpenoid alkyl dimethylamine The acetic acid beet test and the like beneficiary test and other amphoteric surfactants. These may be used alone or in combination with the fine organic pigment coloring composition of the nucleus, which may contain a diterpene fine organic pigment which is sufficiently dispersed in the pigment carrier and which is formed on a transparent substrate such as a substrate to make the film thickness after drying 〇2 to 5# m, the color film can be easily formed. The non-aqueous solvent may, for example, be: trichloropropane-butadiene, 3-butanediol, ;|% __, D-monoacetate, 1,4-dioxane, 2 ~heptanone, methyl^,3-propanediol, 3,5,5-tridecyl-2-cyclohexene-butanone, methyl-methylhexano-, 3-ethoxypropionate ethyl ester, 3~ Methyl-;[,3-y-alcohol, 3-methoxy-3-indolyl d-butanol, acetic acid 3-methoxy-3-ylbutyl group, 3-galvanyl-metamol, Door-to-diethylbenzene, m-dichlorobenzene, N,N-.-r-milylbutanol, 3-methoxybutyl acetate, 4~g- _, B 37 321118 201000570 Amine, Ν'N - dimethylformamide, n-butanol, n-butylbenzene, n-propyl acetate, N-methyl. Pyrrolidone, o-xylene, o-chloromethyl, o-diethylbenzene, o-dichlorobenzene, p-chlorofbenzene, p-diethylbenzene, second butylbenzene, third Butylbenzene, r-butyrolactone, isobutanol, isophorone, ethylene glycol diethyl ether, ethylene glycol t-butyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl Ether, ethylene glycol monoethyl ether acetate, ethylene glycol mono-telebutyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monopropyl ether, Ethylene glycol monohexyl H, ethylene glycol monomethyl scale, ethylene glycol monomethyl (tetra)acetic acid vinegar, isobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, two Glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol = butyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, Cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropyl=alcohol methyl-acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl^dipropylene glycol monopropyl Base shout, dipropylene glycol monothiol scale, diacetone alcohol, triacetin, tripropyl Glycol monobutyl ether, tripropylene glycol monomethyl ether, propane=alcohol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol single Propyl ether, propylene glycol monomethyl test, propylene glycol monomethyl-acetic acid I, propylene glycol monomethyl = propionic acid, feed, methyl isobutyl ketone, methyl cyclohexanol, n-pentyl acetate, acetic acid N-butyl ester, isoamyl acetate, isobutyl acetate, propyl acetate or dibasic acid ester, etc., may be used alone or in combination of two or more. The solvent may be used in an amount of 800 to 4000 parts by weight, preferably 1000 to 2500 parts by weight, based on 100 parts by weight of the pigment dispersion and the pigment in the coloring composition. 38 321118 201000570 In addition, the fine organic pigment of the present invention is colored: a storage material which stabilizes the viscosity of the composition over time; the agent can be exemplified by a ruthenium group, or a diethyl group. The fourth; 隹 2 organic acids; the above-mentioned organic acid methyl vinegar; the first: butyl coke age and other catechu _; triphenyl lining Benjilin and other organic phosphines; or sulphites Wait. The fine organic pigment in the composition of 4 戍 100 μ color may be used in an amount of G. 1 to 10 parts by weight. = The fine organic pigment coloring composition of Ming can be modulated according to the type of concave two = two printing ink, ink for screen printing, and solvent color developing agent. The coloring resist is obtained by dispersing the fine organic pigment of the present invention in a composition of = 'dgagon, a monomer and/or an oligomer, and a photopolymerization initiator. The binder resin is known from the group consisting of a thermoplastic resin, a recording (four), and a photosensitive resin, and is at least one containing a solvent-soluble resin. Adjusting the alkali-developing coloring resistance as a fine organic pigment coloring composition, dispersing the fine organic pigment of the present invention in a composition containing a binder, a photopolymerization initiator, and an organic solvent, or The fine organic pigment of the invention is dispersed in a composition containing a phoenix and a solvent, and is adjusted into a fine organic fine body, and the dispersion and the monomer and/or oligomer and the photopolymerization initiator are further dispersed. Mix and modulate. From the viewpoint of the color characteristics of the coating film, the dispersion stability of the pigment, and the ease of formulation adjustment 321118 39 201000570, the adjustment of the latter is limited to this. 1 The soil dispersion is a feedstock dispersion which itself is a micro-organic pigment of the invention and contains a portion of the monomer and/or oligomerization. The (4) (iv) fat and/or money are adjusted for mixing. The total amount of the solid content of the fine organic pigment coloring composition is based on (10 parts by weight). The fine organic pigment is contained in an amount of 5 to 7 ounces by weight, preferably 20 to 50% by weight. Further, in the fine organic pigment coloring composition of the present invention, a dye may be contained in a range in which heat resistance is not lowered for color adjustment. σ, the fine organic pigment coloring composition of the present invention removes coarse particles of m or more (preferably ^) or more, preferably G.5//, by means of centrifugation, smashing filtration, membrane transition, and the like. The present invention is described in more detail below with reference to the examples, but the scope of the present invention is not limited to the following examples. "Parts and "%" mean "parts by weight" and "weight. %."

(Measurement method) 〇J <The particle size of the pigment> First, an image was obtained by photographing the pigment-subparticles with a transmission electron microscope (manufactured by Sakamoto Electronics Co., Ltd.). Further, the image analysis type particle size distribution measurement software (manufactured by M0UNTECH Co., Ltd.) calculates the area of the projection of each particle of the image 4 〇 321118 201000570, and divides the sum of the projected areas of the particles by the number of particles, thereby calculating the average of the pigment particles. Grain search. <Amine value of resin> The amine value of the resin was determined by potentiometric titration using a 0.1 N aqueous hydrochloric acid solution, and converted to the equivalent of potassium hydroxide. The amine value of the following resin solution indicates the amine value of the solid content. <4 grade salt value of resin> The grade 4 ammonium salt of the resin is 5% potassium chromate water-soluble night as an indicator, and is determined by titration with a 0.1 N aqueous solution of silver nitrate, and converted to potassium hydroxide. The 4-grade ammonium salt value of the following resin solution represents the solid ammonium salt value of the solid form. <Acid Value of Resin> The acid value of the resin was determined by potentiometric titration using a 0.1 N potassium hydroxide•ethanol solution. The acid value of the resin solution described below represents the acid value of the solid component. <Weight Average Molecular Weight of Resin (A)> The weight average molecular weight of the resin (A) is measured by gel permeation chromatography (GPC; manufactured by Tosoh Corporation). When the resin having an amine group is dissolved in tetrahydrofuran, the compound having triethylamine added to tetrahydrofuran is used as an elution solvent, and the TSK-GEL Super Multipore HZ-M 2 string column manufactured by Tosoh Corporation is used as a standard. When it is insoluble in tetrahydrofuran and soluble in 50/50 solvent of methanol/water, the TSK-GELG5000PWxl-CP column manufactured by Tosoh Corporation is used and converted in standard polyethylene oxide. And measured. <Weight Average Molecular Weight of Acrylic Resin> The weight average molecular weight of the acrylic resin used as the binder resin is 321118 41 201000570 (Mw) is a gel permeation chromatography apparatus (GPC; manufactured by Tosoh Corporation) equipped with an RI detector Determination. In the GPC measurement, a TSKgel column (manufactured by Tosoh Corporation) was used, and THF was used as a developing solvent and measured in terms of standard polystyrene. <Method for Forming Colored Film> The colored film was formed by using a fine organic pigment coloring composition, and the number of rotations was arbitrarily changed by a spin coater to a dry film thickness of 2.0/m. After coating, it was dried in a hot air oven at 80 ° C for 30 minutes. <Comparative> The polarizing plates are respectively superposed on both sides of the substrate on which the color film is formed, so that the polarization axes of the two polarizing plates are parallel to each other, and the brightness of the light passing through the polarizing plate and the light passing through the other polarizing plate (Lp) ) Measured with a luminance meter. Next, the polarizing plates superposed on both sides of the substrate are arranged such that the polarization axes of the two polarizing plates are perpendicular to each other, and the backlight is incident from one polarizing plate side, and the brightness (Lc) of the light passing through the other polarizing plate is used for brightness. Measurement. The comparison value Lp/Lc was obtained using the obtained measured luminance value. The measurement is performed in the normal direction of the substrate. In addition, both of the polarizing plates used "NPF-SEG1224DU" (manufactured by Nitto Denko Corporation). The brightness meter was measured using "BM-5A" (manufactured by Topcon Corporation) under the condition of a 2° field of view. Further, the higher the contrast, the more excellent the transparency of the colored film (coloring composition). <Half-peak width> The dried pigment was pulverized with an 80 mesh metal mesh and subjected to X-ray measurement. The X-ray diffraction spectrum was measured under the following conditions. Device: Rigaku Ultima2001 42 321118 201000570 . X-ray source: CuK α • Voltage: 40kV • Current. 40πιΑ • Measurement range: 5. 0° to 35. 0°. Step angle: 0. 01° The results of this measurement are as follows The conditions were subjected to data processing to obtain a half-width (Α20 °). Here, the half width is a Bragg angle value defined by the peak width of the intensity position which is 1/2 of the intensity of the X-ray diffraction intensity in any peak of 2 Θ °. The quinacone pigment is 2. Θ ° 11. 0 to 13. 7 °, 24. 5 to 27. 0 °, 27. 0 to 29. 3 °; the second cultivating pigment 2 θ ° 4. 0 To 0. 0°, 8. 0 to 12. 0°, 15. 5 to 18. 5°, 24. 5 to 27. 5 °; phthalocyanine pigment 2 Θ ° 5. 0 to 12. 7 °; halogenated The copper phthalocyanine pigment is 20 ° 15. 5 to 18. 3 °, 21. 6 to 22. 7 ° connected straight line as the bottom line (base 1 ine), background removal. After the data is processed, the maximum intensity in each range is selected to obtain the half width. When there is a complex peak, the % &lt; average is taken as the half width. The half-peak width and salt as determined here should be considered to correspond to the size of the particles. That is, when the half ridge is wide, the particles are small. &lt;retardation The elliptically polarized light is incident from the normal direction of the substrate on which the color film is formed and the azimuth of 45°, and the spectroscopic Ellipsometer "M-220" is used for the transmitted light system. The JASC0 Corporation manufactures a wavelength range of 575 to 635 nm for a red substrate, 535 to 560 nm for a green substrate, 410 to 520 nm for a blue substrate, 535 to 635 ηπι for a yellow base 43 321118 201000570, and 410 to 520 nm for a purple substrate. In the case of ', △ (in nm) per 1 nm. At this time, it is obtained by calculating the area (unit: nm2) of the domain formed by the spectrum of Δ in the respective wavelength ranges. When the light transmission has a phase difference and the viewing angle characteristics are inferior, it is preferably 3 Å or less, more preferably 2 Å or less. <Resin Synthesis Method> [Synthesis Example 1] A thermometer, a stirrer, a distillation tube, and a cooler are provided. 62.4 parts of acetophenone was fed into a four-piece separable flask and heated to 75 C under a nitrogen stream. On the other hand, 19.5 parts of methacrylate was fed into a dropping funnel, and methyl propylene was added. a portion, a portion of methacrylic acid 12-ethylhexyl ester, 11.7 parts, diethylene glycol monomethacrylate (made in Japan / manufactured by Yuesei Co., Ltd., trade name: Blenmer PE_9 〇) 7.8 parts, 27 3 parts of dimethylaminoethyl methacrylate, 4,7 parts of azobis(2,4-di-pentyl valeronitrile) and 15.6 parts of acetophenone, which are evenly distributed. On a four-piece separable flask, it took 2 hours to drip. After 2 hours of dripping, the solid fraction confirmed that the polymerization yield was above and the weight average molecular weight (Μ&quot; was Π30, cooled to 5[rc. 22 parts of sulfhydryl chloride and 22.0 parts of ethanol were added, and after reacting for 5 hours at 5 (TC), the temperature was raised to 80 ° C for 12 hours, and then reacted for 2 hours. Thereafter, 15 parts of diethylene glycol was added. The pressure was reduced at 100 ° C, ethanol and methyl ethyl ketone were distilled off, and the solvent was replaced with diethylene glycol. Thus, a resin solution having a resin component of 4% by weight was obtained (amine value: 3 mg K0H/g, grade 4) The ammonium salt value was 97 mgK〇H/g. [Synthesis Example 2] 321118 44 201000570 A four-port split burner equipped with a thermometer, a stirrer, a distillation tube, and a cooler. 80 parts of ethyl ketone was fed in and heated to a temperature of nitrogen. On the other hand, 2 parts of methyl methacrylate, 10 parts of n-butyl methacrylate, and 2 - methacrylic acid were fed into the dropping funnel. 5 parts of hexyl hexyl ester, 16 parts of PE-90 by Ble, Kayamer PM-21 (manufactured by Nippon Kayaku Co., Ltd.: ε-caprolactone 1 molar added to 2-hydroxyethyl methacrylate phosphate)丨〇 Parts, 25 parts of dimethylaminoethyl methacrylate, 6 parts of 2, 2'-azobis(2,4-dimercapto, valeronitrile) and 2 parts of acetophenone, which are evenly distributed. The four-piece split flask was taken in for 2 hours. After the completion of the dropwise addition for 2 hours, the solid content was confirmed to be 98% or more, and the weight average molecular weight (3) was 732 Å, and it was cooled to 5 CTC. On the other hand, 13 parts of benzyl chloride and 13.8 parts of ethanol were added, and the mixture was reacted at 50 ° C for 2 hours, and then heated to 80 ° C for 1 hour, and then allowed to react for 2 hours. The resin solution was concentrated and replaced with ethylene glycol monoterpene ether acetate to obtain a resin solution 2 having a solid content ratio of 5 〇% by weight (amine value: 29 mgKOH/g, grade 4 ammonium salt value: 62 mgKOH/g) . I. [Synthesis Example 3] In a four-necked flask equipped with a thermometer, a stirrer, a distillation tube, and a cooler, 80 parts of ethyl ketone, 92.0 parts of butyl acrylate, and Sparteine were fed. 8 parts and 1.9 parts of ethyl isobutyrate bromide were heated to 4 (TC) under a nitrogen stream, and 1 part of cuprous chloride was added, and the temperature was raised to the temperature. (After 3, polymerization was started. After 3 hours of polymerization, The polymerization solution was used as a sample, and the polymerization yield was confirmed to be more than 95% by weight and the weight average molecular weight (Mw) was 6860. The dimethylaminoethyl methacrylate was added to the oxime portion and MEK20. After 0 hours, the polymerization was further carried out. After 2 hours, the solid content of the polymerization solution was 321118 45 201000570, and it was confirmed that the polymerization (4) was 97% or more, and it was determined that the polymerization was carried out by the polymerization of the arsenic. Ρ ϋ 228 228 ϋ 杨 杨 ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ ϋ After 6 parts, stir 3. The ion exchange resin and the adsorption _ call the polymerization touch _ into the fine resin solution and Glycol monomethyl substituted purpose _ § acetate to give a solid content ratio of 50 weight lost of the resin solution was 29 3_ call is OmgKOH / g). Female solitary [Synthesis Example 4], in a four-necked flask equipped with a thermometer, a secret H, a steaming crane tube and a cooler, were fed with ethylene glycol monomethyl ether acetate § 8Q and heated to 9 under a nitrogen stream ( TC. On the other hand, 40 parts of methyl acetonate methyl vinegar, 37 parts of n-butyl decyl acrylate, 10 parts of methyl acrylate, and Placcel FM5 (made by Daicel Chemical Industry Co., Ltd.) were fed into the dropping funnel. : £ — caprolactone 5 molar addition to 2-hydroxyethyl methacrylate) 1 part, dimethyl methacrylate acetate, 3.0 parts, 2, 2'-azo double (2, 6 parts of 4-dimethylvaleronitrile) and 20 parts of diol monomethyl ether acetate' were uniformly placed on a four-necked flask and dripped for 2 hours. After stirring at the same temperature for 2 hours, From the solid content, it was confirmed that the polymerization yield was 98% or more and the weight average molecular weight (M w ) was 6790, and then an appropriate amount of ethylene glycol monomethyl ether acetate was added to obtain a solid content ratio of 50% by weight. Resin solution 4 (amine value: iimgK〇H/g, grade 4 ammonium salt value: OmgKOH/g) [Synthesis Example 5] 321118 46 201000570, equipped with a 'dish meter agitator, a distillation tube, and But the four-port lacquer-type burnt view is fed into the B-reserved field; ^, Beiyi; ^ early (four) B (four) 80 parts and the dish is raised to 90C under nitrogen flow. On the other hand, feed into the dropping funnel A 40 parts of acrylic acid, 2 parts of n-butyl methacrylate, methyl propyl hydrazine, methyl acrylate 2 - 30 parts of acetonitrile, 2, 2, _ azo double (2, 6 parts of 4_ dimethyl valeronitrile and 2 parts of ethylene glycol monomethyl vinegar acetate, so that the device is hooked in the four-port separation type, and the remaining part is dripped for 2 hours. At the same temperature after the end of the drop The lining continued for 2 hours, and the solid content was confirmed to be above the above and the average molecular weight (MW) was 7 _, and then an appropriate amount of diol monomethyl-acetic acid was added to obtain a solid content ratio of 5 g. % by weight of the resin cold liquid 5 (amine value: 〇mgKOH/g, grade 4 recorded salt value: QmgK〇H/g) [Synthesis Example 6] Four nozzles equipped with a thermometer, a stirrer, a distillation tube, and a cooler The methacrylate was fed with methyl methacrylate 19.5 parts, n-butyl methacrylate 15. The mixture was fed with methyl methacrylate in a dropping funnel. 6 copies '曱2份和2,4,_ azobis(2,4-dimethylpentanenitrile) 4.7 parts and 2,6 parts of 2-ethylhexyl acrylate, 27.3 parts of diammonium methacrylate 6 parts of ethyl ketone was homogenized, and the apparatus was placed on a four-necked flask and it took 2 hours to drip in. After 2 hours from the end of the dropwise addition, it was confirmed from the solid content that the polymerization yield was 98% or more and the weight average molecular weight ( Mw) is 7380, cooled to 50 ° C. Add 20.0 parts of benzyl chloride and 22.0 parts of ethanol, and react at 50 ° C for 2 hours, then heat up to 80 ° C for 1 hour. And let it react for 2 hours. Thereafter, 150 parts of diethylene glycol was added to remove ethanol and ethyl ketone at 1 ° C and under reduced pressure, and the solvent was replaced with diethyl 2 473 Π 8 201000570 alcohol. In this manner, Resin 6 (having an amine value of 3 mg K0H/g and a 4-grade ammonium salt value of 97 mgKOH/g) having a resin component of % by weight was obtained. [Synthesis Example 7] An ethidium ketone 57 was fed into a four-necked flask equipped with a thermometer, a stirrer, a distillation tube, and a cooler, and the temperature was raised to 751: under a nitrogen stream. In another aspect, 14.3 parts of methyl methacrylate, 10.7 parts of n-butyl methacrylate, and 2 parts of 2-ethylhexyl methacrylate are fed into the dropping funnel. 7 parts, methacrylic acid 6 parts of methylaminoethyl ester, 4. 2 parts of 2, 2,-azobis(2,4-dimethylvaleronitrile) and 14.3 parts of methyl ethyl ketone, which were uniformly placed on a four-piece separable flask and consumed. Instilled in 2 hours. Two hours after the completion of the dropwise addition, the solid content was confirmed to be 98% or more and the weight average molecular weight was 7090, and it was cooled to 5 Torr. To this, benzyl chloride 28. 7 parts and ethanol 28.7 parts were added at 5 Torr. After the reaction was carried out for 2 hours, the temperature was raised to 80 ° C over 1 hour, and the reaction was allowed to proceed for 2 hours. Thereafter, 150 parts of diethylene glycol was added, and ethanol and ethyl ketone were distilled off under reduced pressure and under reduced pressure, and the solvent was replaced with diethyl diol. In this manner, a resin/liquid mixture 7 having a resin component of 4% by weight (an amine value of 5 mg K0H/g and a 4-grade ammonium salt value of i27 mgKOH/g) was obtained. [Synthesis Example 8] 62 parts of methyl ethyl ketone was fed into a four-necked flask equipped with a thermometer, a stirrer, a distillation tube, and a cooler, and the temperature was raised to π C under a nitrogen stream. On the other hand, 9.8 parts of methyl methacrylate, 6.6 parts of n-butyl methacrylate, 6.6 parts of 2-ethylhexyl methacrylate, hexyl methacrylate Base ethyl ester 42·7 parts, 2,2,-azobis(2,4-dimethylvaleronitrile) 4·7 parts and acetophenone oxime 3·丨 part, make it uniform after 321118 48 201000570 The four-piece split flask was taken in for 2 hours. Two hours after the completion of the dropwise addition, the solid content was confirmed to be 98% or more, and the weight average molecular weight (3) was 6480, and it was cooled to 耽. For this, 4 parts of sulfhydryl chloride and 22.0 parts of ethanol were added at 50. After the reaction was carried out for 2 hours, the temperature was raised to 8 Gt in a small amount of time, and the reaction was further carried out for 2 hours. Thereafter, diethylene glycol 150 was added, and ethanol and methyl ethyl ketone were distilled off under a reduced pressure of 1 〇〇 c, and diethyl ether was used instead of the solvent. Thus, a resin solution 8 having an resin component of 4% by weight (an amine value of 3 mgKOH/g and a 4-grade ammonium salt value of 152 mgK〇H/g) was obtained. [Synthesis Example 9] 62.4 parts of methyl ethyl ketone was fed into a four-port separation type with a thermometer, a stirrer, a steaming tube, and a cooler, and the temperature was raised to Η °c under a nitrogen stream. On the other hand, in the dropping funnel, 6 2 parts of methyl methacrylate, 3 parts of methyl methacrylate, 3 parts of 2-ethylhexyl methacrylate, and methacrylic acid were fed. 7 parts of dimethylaminoethyl vinegar, 4,2, _ azobis(2 4 dimethyl dimethyl nitrile) 4.7 parts, and 2.2 parts of methyl ethyl b, which were evenly distributed in a four-piece split flask It took 2 hours to drop people. Two hours after the completion of the dropping, the solid content was confirmed to be 98% or more, and the weight average molecular weight (five) was 7H0, and it was cooled. 39.2 parts of sulfhydryl chloride and 39.2 parts of ethanol were added thereto, and after reacting for 2 hours at 5 (rc), the temperature was raised for 1 hour, and the reaction was further carried out for 2 hours. Thereafter, diethylene glycol (10) was added. HKTC; and the reduction of fresh bribe ethanol and A (10), and the use of diethyl ether solvent. In this way, the resin component is (four) amount of resin Lok 9 (amine value of 3mgK〇H / g, grade 4 ammonium salt value of 174) [Synthesis Example 10] 321118 49 201000570 108.9 parts of isopropanol was fed into a four-necked flask equipped with a sub-meter, a stirrer, a distillation tube, and a cooler, and the temperature was raised under a gas stream. Prepare 2,2,-azobis(2,4-dimercapto valeronitrile) for 5 parts of the starter solution of methyl ethyl ketone. Then, feed methacrylic acid into the dropping funnel. §19.5 parts, n-butyl methacrylate, 156 parts of 2-ethylhexyl thioglycolate, oxyethyl dimethyl hexamethylammonium methacrylate 49 parts of 3 parts and 2 parts of decyl alcohol were homogenized, and the dropping funnel was placed on a four-necked flask and dropped for 2 hours. When asked, the initiator solution was 1/13 every 10 minutes. The amount was added to the flask, and the addition of 13 times was carried out. After 2 hours, the solid content was confirmed by the solid content. The fact that the polymerization yield was more than J coffee was added. , isopropanol and methyl ethyl hydrazine, and diethylene glycol instead of ruthenium as 2 to obtain a resin component of 4% by weight of the resin solution (pure GmgKGH / g, grade 4 ammonium salt value of 97mg / g) [Synthesis Example 11] = four parts of a thermometer, a stirrer, a steaming tube, and a cooler; the flask was fed with 93. 9 parts of isopropanol and heated to 75 C under a nitrogen stream. Prepared in another container. 2, 2, evenly dissolved in methyl bromide, starting from T-valeronitrile. 5 Feeding methyl propyl ester = C::, 2-ethylhexyl methacrylate in the dropping funnel, A Acetyloxy-trimethyl chloride II, deodorizer / 〇 3 〇. 6 parts, make it uniform, then put the drop hopper four parts and methanol 36.1 parts ' 2 hours ^ read into the separation flask At the same time as the consumption of the person, the initiator solution (4)

32U1S 50

I 201000570 was added to the flask and added 13: owed. Two hours after the completion of the dropwise addition, the fact that the polymerization yield was 98% or more was confirmed from the solid content. To this, 150 parts of diethylene glycol was added and methanol, isopropyl alcohol, and methyl bromide were distilled off under reduced pressure, and diethylene glycol was used instead of the solvent. In this manner, a resin solution 11 having a resin component of 9% by weight (an amine value of 〇mgK〇H/g and a 4-grade ammonium salt value of 97 mgKOH/g) was obtained. [Synthesis Example 12] „ 93 parts of isopropanol was fed into a four-necked flask equipped with a thermometer, a stirrer, a distillation tube, and a cooler, and the temperature was raised to °°c under a nitrogen stream. Prepared in another container. 2,2' _Azobis(2,4-difluorenyl valeronitrile) 5 parts of the initiator solution dissolved in 2G of methyl ethyl ketone. Thereafter, 24 to 6 parts of methyl methacrylate were fed into the dropping funnel. , 19.7 parts of n-butyl methacrylate, 2-ethylhexyl 19-7 parts of acrylonitrile, 36.0 parts of decyl propylene methoxytrimethylammonium chloride, and 36 parts of decyl alcohol, which are made uniform. Drip leak = 裴 placed on a four-necked flask and took 2 hours to drip in. Drop in the same amount, add 1 / 13 of the starter solution to the flask every ίο minutes, a total of 13 - people After the hour of the end of the instillation, the solid content was confirmed to be the above by the solid content. The UQ part of the diethylene glycol was added and 1 (10) was added. Under the decompression and decompression, the methanol, isodip, and hydrazine were removed. And replacing the solvent with diethylene glycol. In this way, a resin solution 丨2 having a resin component of 40% by weight was obtained (the amine value was OmgKOH/g, and the 4-stage ammonium salt value was 97 mgK〇H/ g) <Preparation of Acrylic Resin Solution> 800 parts of propylene glycol monoethyl ether acetate was fed into the reaction solution, and nitrogen gas was injected into the vessel while heating to 1 Torr. At the same temperature, time-consuming 53 32 Π 18 0,00 parts of methacrylic acid, 85.0 parts of methacrylic acid ester, 85.0 parts of butyl methacrylate, and 2,2'-azobisisobutyronitrile i〇. The polymerization reaction was carried out. After the dropwise addition, the reaction was further carried out at 100 Torr for 3 hours, and then 2.0 parts of azobisisobutyronitrile dissolved in 5 parts of propylene glycol monoethyl ether acetate was added, and the reaction was continued at 10 (rc). An acrylic resin solution having a weight average molecular weight (Mw) of 40,000 was obtained. <Pigment Derivative> The pigment represented by the following formula (14) to the "Pigment Street Biosystem" used in the Example was used. Derivatives . Diketo-α α ratio slightly pigment derivative 321118 52 201000570 Formula (11):

• 啥I too 1 homologous pigment derivative General formula (12):

• Benzo-flavored π-sodium ruthenium pigment derivatives General formula (13):

〇•Copper phthalocyanine pigment derivative 53 321118 4 201000570 Formula (14):

Cu-Pc-SO,

CH snoring

Ah5 c2h5

Cu-Pc: copper phthalocyanine residue • Diterpenoid pigment derivative (15):

[Example 1] A kneaded material of the following composition was placed in a 15,000-volume three-arm planetary mixer (Tri-mix), and kneaded at a processing temperature of 40 ° C at a revolution of i9 rpm and a rotation of 57 rpm. hour. . ketone group 嘻 吼 吼 颜料 ( (c, l.pigment Red 254; Ciba Specialty Chemicals "IRGAFOR RED B-CF") 450 parts H1 parts 4500 parts 714 parts • resin solution 1 • sodium chloride • Diethylene glycol (DEG) The above-obtained kneaded material was taken out from a 30,000 parts of a 70% 1% sulfuric acid solution. After being stirred for 1 hour, it was filtered, washed with water and dried to: 321118 54 201000570 After crushing, 彳Each of the fine diterpene bases P is bitten and each of the pigments 1 is bitten. Next, the mixture of the following composition containing the obtained fine diketopyrrolopyrrole pigment was uniformly stirred, and then oxidized wrong beads having a diameter of 1 mm were used, and after being dispersed for 5 hours in a bead pure towel, the mixture was filtered to obtain a red fine Organic Pigment Dispersion 1. , 0 parts, 1.0 part, 40. 0 parts, 50 parts, 0 parts, finely divided, bismuth and fluorene pigment 1. Diketopyrrolopyrrole pigment derivative, acrylic resin solution, propylene glycol monomethyl ether Acid ester (PGMAc) The mixture of the following composition containing the obtained red fine organic pigment dispersion 丨 is stirred and mixed to be uniform, and then filtered by a 1//1] filter to prepare a red fine organic pigment composition. (Red alkaline developing resist material 45. 0 parts 15.0 parts • Red fine organic pigment dispersion 1 • Propanes acid resin solution II by methyl propyl triacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.) Νκ ESTER ATMPTj ) 9.0 parts of photopolymerization initiator 2-mercapto-2-N-morpholinyl (4-sulfonylphenyl)propan-1-one ("IRGACURE 907" manufactured by Ciba Specialty Chemicals Co., Ltd.) 2 0 parts. Sensitizer 4, 4,-bis(diethylamino)dibenzophenone ("EAB-F" manufactured by Japan Hodogaya Chemical Industry Co., Ltd.) 0. 2 parts. Propylene glycol monoterpene ether acetate 28 8 parts [Cell 2] 321118 55 201000570 The kneaded material of the following composition is put into a 15000-volume three-arm planetary mixer. The number of rotations at 9 rpm and rotation at 57 rpm was 35. (Processing by > &gt; 6 hours of mixing under fullness. • One ketone group 各 each. Biha pigment (C. i.pigment Red 254; Ciba Specialty Chemicals Co., Ltd. Manufacture "IRGAFOR RED B-CF") 450 parts, 90 parts, 4500 parts, 720 parts, Resin solution 2, sodium chloride, ethylene glycol, and the thus obtained kneaded material was treated in the same manner as in the Example to obtain a fine diketopyrrole. And pyrrole pigment 2. Next, in addition to the fine diketone ratio, each of the pigments 1 is a fine diketone group. The same treatment as in Example i is carried out instead of the bismuth bismuth pigment 2 to prepare a red fine The organic pigment knife body 2 was further prepared as the red fine organic pigment composition 2 except for the red fine organic pigment dispersion 2 for the red fine organic pigment dispersion 丨. Type resist material [Example 3] In addition to changing the amount of the resin solution 2 to 45 parts: 2: the same treatment, to obtain fine, (4) doubling pigment 3: in addition to the fine diketopyrrolopyrrolo · Except for each pigment 3, carried out and implemented; Fine organic pigment dispersion 3, in addition to: In addition to the second principle, the organic pigment dispersion 3 is sprinkled with spear, L, and workmanship in the same manner as in the example: where the machine pigment dispersion 1 is , red fine organic pigment composition 321118 56 201000570 material 3 (red alkaline development type resist material 3). [Example 4] Apricot a ', the input amount of the tree / valley liquid 2 was changed to 18 parts In addition, the same treatment as in the case of Example 2 was carried out, and each of the fine dicynys of the same base was obtained and the pigment was present. Then, in the same manner as in the example, except that the fine di-g is the same as the base pair and the pigments 1 are replaced by the fine di-n-based 哎Z-yield ratio of each of the pigments 4, the red fine organic pigment dispersion 4 is formed. In addition, the red fine organic pigment composition 4 (red) was prepared by the same treatment as the red fine organic pigment dispersion in the red fine, the machine surface, and the knife release body 4, in the same manner as in the case of the fine example 1. Alkaline development type resist material 4). [Example 5] A mixing machine of the following composition was put into a 15000-volume three-arm planetary agitator to knead at a temperature of 35 t for 6 hours at a revolution of i9rPm and a rotation of 57 rpm. . Binqing base material and pigment (C l pig job t (four) (5) Chemical company made "iRGAF0R RED B_CF") 45 〇 • resin solution 3 ” shirt, 71 parts • gasification sodium. 465 parts of ethylene glycol side part will be the result of the kneading The same treatment as in Example i was carried out:: fine diketone scaly ruthenium pigment 5. Next, in addition to the fine dimethylene p-substance pigment i, a fine di-based fluorenyl (4) pigment: ^ The same treatment as in Example 1 was carried out to prepare a red fine organic pigment knives 5'. In addition to the red fine organic pigment dispersion 5 replaced by the red fine organic pigment dispersion 5, the same treatment as in Example 进行 was carried out except for the red fine organic pigment dispersion 1 of 321118 57 201000570 A red fine organic pigment composition 5 (red alkaline developing resist material 5) was prepared. [Comparative Example 1] A kneaded material of the following composition was placed in a 15,000-volume three-arm planetary mixer to revolve 19 rpm. The rotation number of the rotation of 57 rpm is 35. The mixing is carried out for 6 hours at the temperature of the household. 450 parts 90 parts 4500 parts 810 parts • two s synthropyrrolopyrrole pigments (CIPigment Red 254; manufactured by Ciba Specialty Chemicals Co., Ltd.) IRGAFOR RED B-CF") NaCl. 4 • • of ethylene thus obtained was kneaded in common with the embodiment in Example Shu Li, to give a fine diketopyrrolo-pyrrole pigment 6. Next, in addition to the fine diketone 2 17 than the Luoluobi pigment 1 with a fine diketone σ bilox and _ σ each pigment 6 replaced by ten, the same treatment as in Example 1, into a red fine In addition to the red fine organic pigment dispersion 1 in place of the red fine organic pigment dispersion 1, the treatment with the first embodiment was carried out to prepare a red fine organic pigment composition 6 (red). Alkaline Explicit Agent 6) [Comparative Example 2] Kneading at a temperature of 6 hours. The kneaded material of the following composition was placed in a three-arm planetary mixer of 15 〇 (10) capacity, and rotated at a revolution of 19 rpm and a rotation of 57 rpm. 4〇°c where 321118 58 201000570 • Diketone-based piroxime. 嘻 pigment (CIPigment Red 254; Ciba Specialty Chemicals “IRGAFOR RED B-CF”) 450 parts • Resin solution 5 9 (H Distillation: 4,500 parts of sodium chloride. 800 parts of diethylene glycol The kneaded product thus obtained was subjected to the same treatment as in Example 1 to obtain a fine diketopyloxazepine pigment 7. Next, in addition to the fine di-g-gram Pyrrolopyrrole pigment 1 is substituted with fine diketopyrrolopyrrole pigment 7 In the same manner as in Example 1, the red fine organic pigment dispersion 7 was prepared, and the red fine organic pigment dispersion 7 was replaced with the red fine organic pigment dispersion 7 in the same manner as in Example 1. In the same treatment, a red fine organic pigment composition 7 (red alkaline developing resist 7) was prepared. [Comparative Example 3] A kneaded machine of a composition of the following composition was put into a 20,000-volume double-arm pinch machine (double arm) In kneader), the mixture was kneaded at a temperature of 35 rpm for 6 hours at a rotation speed of 30 rpm. Diketopyrrolopyrrole pigment (CI Pigment Red 254; "ICGAFOR RED B-CF" manufactured by Ciba Specialty Chemicals Co., Ltd.) 810 parts. 90 parts of diketopyrrolopyrrole pigment derivative. 9000 parts of sodium chloride. Ethylene glycol 1980 parts The kneaded product thus obtained was subjected to the same treatment as in Example 1 to obtain a fine diketone tylindole. ° ϋ ϋ ϋ 颜料 颜料 ϋ ϋ ϋ ϋ ϋ ϋ ϋ 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 321 Dispersion 8 'again' except The red fine organic_composition 8 (red alkali base material 8) was prepared by the same treatment as in the example except that the red fine organic pigment dispersion 8 was used instead of the red fine organic pigment dispersion i. [Comparative Example 4] The kneaded material of the following composition is put into a 2 (10) (10) capacity part of a two-arm pinch machine, and the scale is rotated at a treatment speed of 3 rpm at a treatment temperature of the muscle for 6 days. • The base material is called a pigment Red 254. ; Ciba in 900 parts of 9000 parts of 1800 parts of the same treatment, in addition to fine diketone

The company manufactures "IRGAFOR RED B-CF: Sodium Chloride. Ethylene Glycol. The kneaded material thus obtained is subjected to the example to the fine diketopyrrolopyrene. σ Each pigment 9., ^ ^ Call, W 1 machine The lake is the same as the base. The biluo pigment I is made into a fine red organic pigment dispersion 9 by the same treatment as in the first embodiment, and the red fine organic pigment dispersion is prepared. The pigment dispersion 9 was treated in the same manner as in Example i except for the red fine organic pigment dispersion 丨 to prepare a red fine organic pigment composition 9 (red test;

Reagent 9). HIM

[Comparative Example 5] A mixture of the following components containing the fine diketone groups obtained in Comparative Example 3 was uniformly (4), and then an oxidized error of 32] il8 60 201000570 beads of diameter 丨 was used in a bead mill. After 5 hours of dispersion, the fine organic pigment dispersion 10 was colored at 5 // m. The filter is filtered to form a red, fine diketopyrrolopyrrole pigment 8 9. 0 parts • diketone σ ratio p and σ ratio lanthanide pigment derivative 1. 0 parts. resin solution 1 1. 0 parts • Acetate resin solution 39.0 parts • propylene glycol monomethyl ether acetate (PGMAc) 50. 0 parts, in addition to red fine organic pigment dispersion ίο instead of red fine organic pigment dispersion 1 In the same manner as in Example 1, a red fine organic pigment composition 10 (red positive development type resist material 10) was prepared. [Comparative Example 6] A kneaded material of the following composition was placed in a three-arm planetary mixer of 1500 G capacity, and kneaded at a temperature of 35 ° C for 6 hours at a revolution of 19 rpm and a rotation number of 57 rpm. • Diketopylpyrazine® pigment (CIPigment Red 254; “ICGAFOR RED B-CF” manufactured by Ciba Specialty Chemicals) 450 parts • AJISPER PB821 (made by Ajinomoto Fine-Techno); a copolymer containing a polycaprolactone-based basic functional group, an amine value of 10 mgKOH/g, an acid value of 17 mg K0H/g, 45 parts, 4,500 parts of sodium chloride, 810 parts of ethylene glycol, and the thus obtained kneaded material The same treatment as in Example 1 gave a fine diketopyrrolopyrrole pigment 10. Next, in addition to the fine diketone group 61 321 Π 8 201000570 ^ and ^ each pigment 1 to fine Mu 4 - (1) base than 嘻 Asia. The same treatment as in Example 1 is used instead of the pigment 10, and the dispersion is η, and the dispersion is η, and in addition to the red fine organic pigment, it is replaced by the red fine organic pigment dispersion u. = color is fine organic pigment dispersion! In the same manner as in Example i, the treatment was carried out to prepare a red fine organic pigment composition 16 red resist material 11).匕Nen I,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, Materials 1 to 11) 'Measure the average particle diameter of each difficulty and the retardation value, respectively, and show the results in Table 1 ^ [Example 6] The kneaded material of the following composition was put into a three-arm planetary mixer of 15 〇〇〇 capacity. (manufactured by Inoue Works Co., Ltd.), with a revolution of 19 rpm, a rotation of 5 扦 (10) = a number of revolutions of 60. (: Mixing for 12 hours at the treatment temperature. Quinone pigment (c. L Pigment Yellow 138; manufactured by BASF)

Paliotol Yellow K0961HD") 441 parts. Benzimidazolone-based pigment derivative 9 parts 'Resin solution 1 126 parts•4500 parts of sodium carbonate. 1246 parts of diethylene glycol 120,000 parts by weight of 1% sulfuric acid solution at 70 °C The kneaded product obtained above was taken out and stirred for 1 hour, and then filtered, washed with water, dried, and pulverized to obtain a fine quinacridone pigment 1. Next, the mixture of the above-mentioned fine quinacridone pigment 1 obtained as described above, and the mixture of the group 62, 丨18 201000570, was uniformly stirred, and then dispersed in a mill for 5 hours, and then the pigment dispersion 1 was obtained.份••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••••• Acrylic resin solution ▲ 7.0 parts • propylene glycol monomethyl ether acetate δyv 36. 8 parts, in addition to yellow fine organic pigment dispersion 丨 instead of red:: with: pigment dispersion 1, proceed with Example 1 The same treatment: a finer fine organic pigment composition 1 (yellow alkaline developing resist 1). [Example 7] A kneaded product of the following composition was placed in a three-arm planetary mixer (manufactured by Inoue Seisakusho Co., Ltd.) in a capacity of 15 rpm, and the mixture was rotated at 19 rpm, and the number of revolutions of 57 was rotated at 6 (the treatment temperature of TC was a hour). "Paliotol Yeu〇w K0961HD") 441 parts • Benzomidazolone-based pigment derivative 9 parts • Resin solution 6 123 parts • Gasification sodium 4500 parts • Diethylene glycol 1241 parts • Antimony pigment (C·I Pigment Yellow 138; The product obtained by BASF was subjected to the same treatment as in Example 6 to obtain a fine fluorenone pigment 2. Next, except that the fine ketone pigment 1 was replaced with the fine quinacridone pigment 2 'The same treatment as in Example 6 was carried out, 63 321118 201000570 to prepare a yellow fine organic pigment dispersion 2, and further, in addition to the yellow fine organic pigment dispersion 2 instead of the red sinensis, the 丨*′′′ In addition to the fine organic pigment dispersion 1, the same treatment as in Example 1 was carried out, and it was made into a vapor-colored organic pigment group spot 2 (yellow alkaline developing type resist material 2). [Example 8] The kneaded material of the following composition is put into 15_容In the three-arm line (manufactured by Inoue Manufacturing Co., Ltd.), the revolution was carried out for 19 hours, the rotation was 57 rpm = the number of rotations was 6 (the treatment temperature of TC was mixed for 12 hours. BASF produced 441 parts, 9 parts, 123 parts, 4500 parts, 1217 parts. Treatment, quinacridone pigment (CIpigment fairy (10) "Paliotol Yeii〇wk 〇 961HD"). Benzophenazolidone pigment derivative • Resin solution 7 • Chlorinated sodium • Diethylene glycol 6 to micro-faced coffee *3. Next, the second, the same, the same as in Example 6 except that the fine quinacridone pigment was replaced by the material:: gamma 3:: yellow fine organic pigment dispersion 3 Furthermore, the organic pigment dispersion 3 replaces the red Luo + /, the color shouting fine a generation, the work color imitation fine organic pigment fraction is the same as the embodiment i:: 1 outside the 'object V ώ θ s color fine organic Pigment Composition 3 (Vapor Color Alkali Development Resist Material 3). Wind [Example 9] The kneaded material of the following composition was injected into a three-arm row mixer C (manufactured by Inoue Co., Ltd.) In the hall of the hall, the u-transfer 19 rpm, the rotation of 57r (10), the kneaded material thus obtained is carried out with the example &qu Ot;if m t. I _ 321118 64 201000570 The number of revolutions is kneaded for 12 hours at a treatment temperature of 60 ° C. • Pig·ketone pigment (CI Pigment Ye 1 low 138; “Paliotol Yeii〇w K0961HD” by BASF) 441 parts. Benzimidazolone-based pigment derivative 9 parts • Resin solution 8 124 parts • Copper chloride 4500 parts. Diethylene glycol 1268 parts The kneaded product thus obtained was subjected to the same treatment as in Example 6 to obtain fine quinine. Anthrone pigment 4. Next, the same treatment as in Example 6 was carried out except that the fine quinacridone pigment oxime was replaced with the fine quinacridone pigment 4 to prepare a yellow fine organic pigment dispersion 4, in addition to the yellow fine organic pigment dispersion. (4) The yellow fine organic pigment composition 4 (yellow alkali developing resist material 4) was prepared in the same manner as in Example 1 except that the red fine organic pigment dispersion 丨 was replaced. [Example 10] A kneaded material of the following composition was placed in a 15 (10) 〇 capacity three-prong machine (manufactured by Inoue Seisakusho Co., Ltd.), and revolved by a revolution of 19 rPra, a rotation of 57 &lt; T rotation number at a treatment temperature of 6 (TC) 138 ' 138 ' BASF manufactures 441 parts 9 parts 125 parts 45 parts 1166 parts of ketone pigments (CIPigment Yellow "Palioto1 Yellow K0961HD") • Stupid and imidazolidone pigment derivatives • Resin solution 9 • Chlorine Sodium Hydroxide-Ethylene Hydrazine 32Hl8 65 201000570 The kneaded product thus obtained was subjected to the same treatment as in Example 6 to the dextro ketone pigment 5. Next, in addition to the fine sage pigment: the pigment 5 was replaced with 'Example and Example' The same procedure as in Example 1 was carried out in the same manner as in Example 1 except that the red fine organic pigment dispersion k was replaced with the organic pigment dispersion 5 instead of the organic pigment dispersion 5. Yellow fine organic pigment ^ [Example 11] The kneaded material of the lower composition was put into 15 〇〇〇 BASF company to make 441 parts, 9 parts, 110 parts of milk, 00 parts, 1102 parts, and the same treatment, which was produced by Sakai Onsho Co., Ltd. Revolution The teacher's rotation -5= The number of rotations is 1 hour for 12 hours at the processing temperature of ah. #7咖之.Quinone ketone pigment (c.Lplgment Yeu(10)138

Paliotol Yell〇w K0961HDj ) . Benzimidazolone-based pigment derivative ‘Resin solution 10 • Sodium chloride • Diethylene glycol Example to fine σ quinine ketone heterogeneous # ., , . , 枓6. In addition to the fine quinacles g and the pigment == substitution, the implementation and the implementation of the heart, in addition to the yellow fine and the embodiment! In addition to the fine organic pigment dispersion 1, the color treatment, a yellow yellow fine organic pigment composition, the scallops and scalp-type cephalic resists 6). The kneaded material thus obtained was subjected to a three-arm planetary mixer (manufactured by Inoue Seisakusho Co., Ltd.) having a composition of the following composition in an amount of 32 ΪΠ 8 66 201000570 [Example 12], and was revolved at 19 rpm and rotated 57. The number of revolutions was kneaded for 12 hours at a treatment temperature of 60 °C. 〇w 138 ; Made by BASF) 441 parts 9 parts 110 parts 4500 parts 1054 parts • Anthrone pigments (Cl pigment Yell “Paliotol Yen〇w K0961HD”. Benzimidazolone pigment derivatives • Resin solution 11 • Gasification Na 2 Diethylene Glycol The thus obtained kneaded material was subjected to the same treatment as in Example 6 to obtain a fine quinophthalone pigment 7. Next, except that the fine quinophthalone pigment oxime was replaced with the fine quinacridone pigment 7 In the same manner as in Example 6, the yellow fine organic pigment dispersion 7 was prepared, and the same treatment as in Example 1 was carried out except that the yellow fine organic pigment dispersion 7 was replaced with the yellow fine organic pigment dispersion 1. The yellow fine organic pigment composition 7 (yellow alkaline developing type resist material 7) was prepared. [Example 13] A kneaded material of the following composition was placed in a 15,000-volume three-arm planetary mixer (manufactured by Inoue Co., Ltd.). 'Mixed for 12 hours at a processing temperature of 60 ° C with a revolution of 19 rpm and a rotation of 57 rpni. • CI ment 酉 酮 颜料 颜料 (CI Pigment Yellow 138 ; "Paliotol Yellow K0961HD" manufactured by BASF 9 parts•Resin solution 12 110 parts 67 321118 201000570 4500 parts • Gasification nano-diethylene glycol 1053 parts: The obtained kneaded material was subjected to the same treatment as in Example 6 to obtain fineness. The same procedure as in Example 6 was carried out except that the fine quinacridone pigment 1 was replaced with the microquinone ketone pigment 1, to prepare a yellow fine organic pigment dispersion 8, which was dispersed in addition to the yellow fine organic pigment. The body 8 was replaced with the red fine organic pigment dispersion, and the same treatment as in Example 1 was carried out to prepare a yellow fine organic pigment composition 8 (yellow alkaline developing type resist material 8). [Example 14] In the three-arm planetary mixer (manufactured by Inoue Seisakusho Co., Ltd.), which is placed in a capacity of 15 〇〇〇 in the winter, the mixture is rotated at a processing temperature of 60 ° C at a revolving speed of 57 rpm and a rotation speed of 57 rpm. Hour. Quinone pigment (C. L Pigment Yell (10) 138; "Paliotol YelI〇w K〇961HD" manufactured by BASF) 405 parts of benzimidazolone-based pigment derivative • Disperbyk-2000 (Japan gram chemistry (Βγκ一Chemie) company Manufactured; modified acrylic block copolymer, amine value 4mgK〇H/g, 4-grade ammonium hydrochloric acid value 90mgKOH/g) 1〗 iw 八•Sodium chloride 4500 parts The kneaded material thus obtained was subjected to the example 6 The same treatment gave the fine quinacridone pigment 9. Next, the same treatment as in Example 6 was carried out except that the fine quinacridone pigment i was replaced with the fine quinacridone pigment 9, and 321] 18 68 201000570 was prepared into a yellow fine organic pigment dispersion 9, and further,

The same treatment as in Example 1 was carried out, and in addition to the yellow fine organic pigment dispersion 1, a yellow fine organic pigment composition 9 (yellow alkaline development type resist material 9) was obtained. [Comparative Example 7] A kneaded product of the following composition was placed in a three-arm planetary mixer (manufactured by Inoue Seisakusho Co., Ltd.) in a capacity of 15 Torr (10), and the number of revolutions of the coffee machine was rotated at 19 rpm, and the number of rotations of the rotation of the coffee was 6 (the processing temperature of TC was 12). Hour. Quinoneone pigment (Cl Pigment Yell〇w 138; "Paliotol Yeii〇w K0961HD" by MSF) 441 parts 9 parts 4500 parts 1305 parts. Benzimidazolone-based pigment derivatives • Chlorinated steel will be so The kneaded material was subjected to the same treatment as in Example 6 to obtain a fine quinacridone pigment. Then, the same treatment as in Example 6 was carried out except that the fine quinophthalone pigment oxime was replaced with the fine quinacridone pigment 1 〇. , a yellow fine organic pigment dispersion was prepared, and the same treatment as in Example 1 was carried out except that the yellow fine organic pigment dispersion 10 was used instead of the red fine organic pigment dispersion i to prepare a yellow fine organic The pigment composition was 1 〇 (yellow alkali-developing resist material 丨 0). [Comparative Example 8] A kneaded product of the following composition was placed in a three-arm planetary mixer (manufactured by Inoue Seisakusho Co., Ltd.) in a capacity of 15 〇 (10). The number of rotations at 19 rpm and rotation at 57 rpm was kneaded for 12 hours at a treatment temperature of 60 ° C. 69 321118 201000570 . Quinone pigment (c· LPigment Yellow 138; BASF company "Palioto1 Yellow K0961HD") 441 copies ^. Stupid And imidazolidone-based pigment derivative 9 parts 77 • J0NCRYL 682 (manufactured by BASF, Japan; stupid ethyl-propanoid acid, acid value: 238 mg K0H/g) 112 parts..., • 4,500 parts of gasified steel. 1305 parts of the diol was subjected to the same treatment as in Example 6 to obtain a fine quinacridone pigment n. Next, in addition to the fine quinacridone pigment, the fine quinacridone pigment 11 was used instead of In the same manner as in Example 6, a yellow fine organic pigment dispersion u was prepared, and the same treatment as in Example 1 was carried out except that the yellow fine organic pigment dispersion 11 was replaced by the + fine red organic pigment dispersion 1 , made of yellow micro (four) machine _ composition 11 (yellow alkaline development type resist material 丨 1).

The half-width of the fine quinacridone pigments 1 to U produced by the method of the above examples, the contrast of the yellow alkali-developable resist materials 丨 to n, and the retardation values were measured and shown in Table 2. [Example 15] The three-armed planetary stirring was performed by a Toyo Ink printing at 57 rpm. 407 parts of 51 parts. The kneaded material of the following composition was put into a 15 〇〇 () capacity mixing machine (manufactured by Inoue Seisakusho Co., Ltd.), and rotated at 19 rpm. The number is kneaded for 6 hours at a treatment temperature of 10 (TC). • Copper halide phthalocyanine pigment ("Lionol green 6γκ" manufactured by CI Pigment Green) • Resin solution 1 32Π18 70 201000570 . Chloroside side part • Diethylene glycol 902 parts The above-mentioned corpse kneaded material was taken out from 32 parts by volume of a 1% sulfuric acid aqueous solution at 70 ° C. After being stirred for 1 hour, it was filtered, washed with water, dried in a dry furnace: and pulverized to obtain a fine copper phthalocyanine. Green pigment i. The obtained ray diffraction measurement (CuKal ray) is a copper halide phthalocyanine green pigment having a peak at a Bragg angle 2θ (allowable range of 0.2 degrees) = 22.3 degrees. Next, the resulting fine letter will be contained. The mixture of the composition of the copper phthalocyanine green pigment 1 was uniformly stirred, and then dispersed in a bead mill for 5 hours using an oxidized wrong bead having a diameter of 1 mm, and then filtered by a 5 - gauge to prepare a vapor-dried organic pigment dispersion 1 Do 9 parts, 1 part, 15 parts, 49 parts. .fine _ copper phthalocyanine pigment. copper phthalocyanine pigment derivative • acrylic resin solution. propylene glycol monomethyl ether acetate, in addition to green fine organic pigment dispersion 丨 instead of red = organic pigment dispersion 丨The same treatment as in Example , was carried out to form a green fine organic pigment composition (green anion-developing resist material 1). '[Example 16] 'The kneaded material of the following composition was put into 15000 parts by volume. In the three-arm chopping machine (manufactured by Inoue Seisakusho Co., Ltd.), the mixing was performed for 6 hours at the processing temperature of the failure. ^57 Coffee. Deuterated copper phthalocyanine pigment (c. LPigment Green 36; Toyo Ink 321118 71 201000570 405 parts 203 parts 4500 parts 635 parts "Lionol green βγκ" manufactured by the company) • Resin solution 1 • Gasification of sodium diethylene glycol The kneaded material thus obtained was treated in the same manner as in Example 15 to obtain a fine _ Copper phthalocyanine green pigment 2. The obtained pigment was subjected to xenon ray diffraction (CuKal ray) as a functionalized copper phthalocyanine green pigment having a special peak at a Bragg angle tolerance range of 2 degrees) = 22.3 deg. Then, the green fine organic pigment dispersion 2 was prepared in the same manner as in Example 15 except that the fine copper phthalocyanine green pigment 1 was replaced with the fine copper halide phthalocyanine green pigment 2. In addition, the green fine organic pigment composition 2 (green alkaline developing type resist material) was prepared by the same treatment as in Example 1 except that the green fine organic pigment dispersion 2 was used instead of the red fine organic pigment dispersion 丨. 2). [Comparative Example 9] A kneaded product of the following composition was placed in a three-arm planetary mixer (15 rpm, manufactured by Inoue Seisakusho Co., Ltd.), and kneaded for 12 hours at a processing temperature of 60 ° C at a revolution of 19 rpm and a rotation of 57 rpm. . Copper Phosphorus Indigo Pigment (CI Pigment Green 36; "Lionol green 6YK" manufactured by Toyo Ink Manufacturing Co., Ltd.) 450 •, • Gasification of sodium 4500 parts B. The kneaded material thus obtained was subjected to the same treatment as in Example 15 to obtain Fine copper halide phthalocyanine green pigment 3. The obtained pigment was subjected to xenon ray diffraction measurement 321118 72 201000570 (Cukal ray) as a copper halide phthalocyanine green pigment having a peak at a Bragg angle of 2β (a tolerance range of 2 degrees &gt; 22. 3 degrees. Next, in addition to finely halogenating The copper phthalocyanine green pigment 1 was treated in the same manner as in Example 15 except that the fine copper halide phthalocyanine green pigment 3 was replaced, and a green fine organic pigment dispersion 3 was obtained. Further, in addition to the green fine organic pigment dispersion 3 The green fine organic pigment composition 3 (green green development type resist material 3) was prepared in the same manner as in Example 1 except that the red fine organic pigment dispersion 丨' was used. The measurement was carried out according to the method of the above example. The half-width of each green pigment, the contrast of the green alkali-developing resist material, and the retardation value are shown in Table 2. [Example 17] - A kneaded material of the following composition was put into a kneading machine of 3000 parts by volume (Inoue • Manufactured by the manufacturer, mixing for 6 hours at a treatment temperature of 2,500 rPm at a treatment temperature of 70 T: . ε type copper phthalocyanine pigment (CI Pigment Blue 15 : 6 ; manufactured by Toyo Ink Manufacturing Co., Ltd.) Ue Ε") 123 parts • Resin solution 1 27 parts • Sodium chloride 1364 parts • Diethylene glycol 213 parts From the 7 0 C 1% sulfuric acid aqueous solution 8 7 0 0 parts of the middle part, the above kneaded material is taken out, 1 After heating and stirring for an hour, filtration, washing with water, drying, and pulverization were carried out to obtain a fine phthalocyanine pigment 1. The obtained pigment was measured by ray diffraction (Cukal ray) at a Bragg angle of 2 &lt; 9 (allowable range ± 〇. 2 degrees 9 1 degree ε-type copper phthalocyanine pigment having the strongest peak. 321118 73 2〇l〇0〇57〇 Next, the resulting mixture was uniformly stirred, and dispersed in a mill for 5 hours, followed by an organic pigment dispersion. 1. The following group of fine ε-type copper phthalocyanine pigment oxime uses an oxidized wrong bead of 1 mm in diameter, and is filtered by a m filter in bead 5 to prepare a blue fine 123 parts 1 part 10 parts 31 parts • fine e-type copper Cyanine pigment 1 'copper phthalocyanine pigment derivative ・acrylic resin solution propylene glycol monoterpene ether acetate, in addition to blue fine organic pigment dispersion i instead of red fine organic pigment dispersion 1 Example i the same treatment: made of blue fine The pigment composition 4 was not i (blue alkaline developing type resist material [Comparative Example 10], and the kneaded product of the following composition was put into a kneading machine (manufactured by Inoue Seisakusho Co., Ltd.) of 3 (10) 0 parts by volume. Mixing for 6 hours at the processing temperature of 7th generation. 136 parts of 1364 parts and 224 parts of type 5 copper phthalocyanine pigment ("Lionol blue E" manufactured by CI Pigment Co., Ltd. chlorinated steel diethylene glycol from 70 C of 1% sulfuric acid aqueous solution 8600 The kneaded product obtained above was taken out from the middle portion, and after stirring for 1 hour, the mixture was filtered, washed with water, dried, and dried to give a fine indigo pigment 2. The obtained pigment is subjected to helium ray diffraction (Cukal ray) at a Bragg angle of 2) 9 (allowable range ± 0.2 degrees) =

32II1S 74 201000570 9. The ε-type copper phthalocyanine pigment with the strongest peak at 1 degree. Next, the same treatment as in Example 17 was carried out except that the fine copper enanthin green pigment i was replaced with the fine copper ruthenium cyanine green pigment 2 to prepare a Xue fine fine organic pigment dispersion 2. In addition, the blue fine organic pigment composition 2 (blue alkaline developing type) was prepared by the same treatment as in Example 1 except that the blue fine organic pigment dispersion 2 was used instead of the red fine organic pigment dispersion 1. Resistive material 2). The fine copper phthalocyanine pigment oxime produced by the method of the above example and the half-width wide and blue alkali-developing resist material of 2 (the comparison of 2 and the retardation value are shown in Table 2). [Example 18] • The kneaded material of the following composition was put into a kneading machine of 3,000 parts by volume (manufactured by Inoue Co., Ltd.) in the number of rotations of 24.5 rpm at 6 (Γ (: processing temperature for 6 hours). Purple pigment (CI Pigment Vi0丨et 23; Sumitomo Chemical Co., Ltd. "Sumitone Fast Violet RL base") 123 parts. Resin solution l (solid content ratio of 5 〇 wt%) Parts • 1364 parts of sodium chloride • Diethylene glycol 249 parts of the kneaded material obtained by removing the above-mentioned 80% (10) parts of a 1% sulfuric acid aqueous solution at 70 ° C, and after mixing for 1 hour, the mixture was filtered, washed with water, and dried to be pulverized to obtain a fine diterpene violet pigment enamel. The mixture of the following composition containing the obtained fine bismuth cultivating violet pigment was uniformly stirred, and then the oxidized wrong beads having a diameter of 1 mm were used, and dispersed in a purple fine organic machine for 5 hours in a bead mill 321118 75 201000570, and then 5 /αιη filter, pigment dispersion 1. 10 parts 1 part 40 parts 48 parts • De: fine diterpene violet pigment 1 • Diterpenoid 1:1 well purple pigment derivative • Acrylic resin solution • Propylene glycol monoterpene ether acetate, in addition to purple The fine organic pigment dispersion was replaced with the red micro = organic pigment dispersion ' except that the same treatment as in Example , was carried out, and a fine organic pigment composition of one color (purple alkaline developing resist 1) was obtained. Example 11] A kneaded product of the following composition was placed in a kneading machine (manufactured by Well Manufacturing Co., Ltd.) of 3,000 parts by volume, and kneaded at 6 (rpm treatment temperature) for 6 hours at a rotation number of 24.5 rpm. Pigment (C, I. Pigment Violet 23; Sumitomo Chemical Co., Ltd.; "Sunutone Fast Violet RL base") 136 parts • 1364 parts of sodium gasification • 259 parts of diethylene glycol The same kneaded material was obtained as in Example 6. The treatment was carried out to a fine diterpene violet pigment 2. Then, in the same manner as in Example 18 except that the fine diterpene violet pigment was replaced with the fine di-purine pigment 2, a purple fine organic pigment dispersion was prepared. 2. In addition, there are subtle colors In addition to the red fine organic pigment dispersion, the organic pigment dispersion 2 was treated in the same manner as in the example to prepare a purple fine organic ruthenium 32J1I8 76 201000570 material composition 2 (purple alkaline development type resist material 2) 2: = The fine diterpene violet pigment 1 and the peak peak, purple alkaline developing resist material i and 2 produced by the method of the example are shown in Table 2. For comparison and extension, in the method of the application examples and the comparative examples, the ketone oxime propylene glycol monomethyl ether acetate or the diethyl diol was summarized in Table 3 when the pigment was refined. The resin (A) of the present invention is a resin solution of 1 to 3, 6 to Disperbyk-2000 sold. ^And the city &lt;solubility of the resin to the organic solvent>. When the liquid is dissolved in the thief before the synthesis of triethylene glycol, the second is the solid resin, 'is directly used, such as the tree month ^ j similarly The organic solvent is evaporated to obtain the fortune. The solid resin is taken in 1 part of 'T.. Methyl Ether _ or Diethyl W propyl-%. 5 shovel is used to make the body become 10 parts. In the middle, after knowing, set it to 1〇〇t: Cooling to hunger, JL·v “Remove the 钟ι 9πη after the preservation of the clock. Spec1 1〇 Specrowave D.—The polar array visible spectrophotometry In the measurement, the solubility in each wavelength of the solution in the wavelength = _ cell is 1 Å. The solubility of the resin is 1 Å. The 透光 ◦ : : : : : : : : : : : : : : : : : : : : : : : : : : : : :: Light transmittance is not full _ or there is still undissolved resin 321118 77 201000570 [Table 1] Fine pigment micronization particle size half peak width Pigment composition contrast retardation value Resin solution (nm) (-) Resistive material (-) ( Nm2) Example 1 Resin Solution 1 DPI has 24 0.84 Red 1 6050 18 Example 2 Resin Solution 2 DP2 has 26 0.81 Red 2 58 20 8 Example 3 Resin solution 2 DP3 has 25 0.79 red 3 5440 14 Example 4 Resin solution 2 DP4 has 24 0.83 red 4 6340 17 Example 5 Resin solution 3 DP5 has 26 0.78 red 5 5020 14 Comparative Example 1 Resin solution 4 DP6 has 29 0.80 red 6 4890 66 Comparative Example 2 Resin solution 5 DP7 has 29 0.80 Red 7 4250 35 Comparative Example 3 - DP8 No 23 0.88 Red 8 6740 80 Comparative Example 4 - DP9 No 33 0. 76 Red 9 3670 50 Comparative Example 5 Resin solution 1 DP8 No 23 0.88 Red 10 6510 69 Comparative Example 6 AJISPER PB821 DP10 has 28 0.79 red 11 4140 16 DP ··fine diketopyrrolepyrrole pigment red: red fine organic pigment composition (red developable resist Reagent material) 78 321118 201000570 [Table 2] Resin solution Fine pigment refinement with or without half-peak width Pigment composition Comparative retardation value Resin (-) Resistive material (-) (run2) Example 6 Resin solution 1 XP1 has 0.97 yellow 1 9200 -480 Example 7 Resin solution 6 XP2 has 0.97 yellow 2 9560 - 510 Example 8 Resin solution 7 XP3 has 1. 03 yellow 3 8880 -390 Example 9 Resin solution 8 XP4 has 1.03 yellow 4 8220 -470 Example 10 Resin solution 9 XP5 has 1.07 yellow 5 8530 -470 Example 11 Resin solution 10 XP6 has 0.96 yellow 6 9480 -500 Example 12 Resin solution 11 XP7 has 0.95 yellow 7 9670 -480 Example 13 Resin solution 12 XP8 has 0.95 yellow 8 9620 -530 Example 14 Disperbyk-2000 XP9 has 1.01 yellow 9 9380 -490 Comparative Example 7 - XP10 No. 0. 94 Yellow 10 8050 -390 Comparative Example 8 JONCRYL 682 XP11 has 0. 90 Yellow 11 7300 -450 Example 15 Resin solution 1 PG1 has 0.57 green 1 8440 -20 Example 16 Resin solution 2 PG2 has 0.71 green 2 8670 -110 Comparative Example 9 - PG3 No. 0. 51 Green 3 7670 30 Example 17 Resin solution 1 PB1 There are 0.60 blue 1 8590 20 Comparative Example 10 - PB2 No 0.52 Blue 2 7880 90 Example 18 Resin solution 1 DV1 has 0.83 purple 1 3310 -850 _Comparative Example 11 A DV2 No 0.78 Purple 2 3110 -770 XP : Fine quin Ketone pigment; PG: fine copper halide phthalocyanine green pigment; PB: fine ε-type copper phthalocyanine blue pigment; DV: fine bismuth purple pigment yellow: yellow fine organic pigment composition (yellow-developing resistive material) ) Color: green fine organic pigment composition (green alkaline developing type resist material) Blue: blue fine organic pigment composition (blue developable resist type resisting material) Purple: purple fine organic pigment composition (purple base) Resin-type resist material) 79 321118 201000570 [Table 3] Resin enamel resin structure amine value 4 grade ammonium salt value amine + ammonium hydrochloric acid value soluble acrylic acid random system mgK0H / g mgKOH / g mgKOH / g mgKOH / g PGMAc DEG resin solution 1 〇〇3 97 100 0 X 〇 resin solution 2 〇〇29 62 91 18 X 〇 resin solution 3 〇 block system 29 0 29 0 X 〇树月之溶液4 〇〇11 0 11 85 〇 X Resin Solution 5 〇〇0 0 0 85 〇〇Resin Solution 6 〇〇3 97 100 0 X 〇Resin Solution 7 〇〇5 127 132 0 X 〇Resin Solution 8 〇〇3 152 155 0 X 〇Resin Falling 9 〇 〇3 174 177 0 X 〇 resin falling liquid 10 〇〇0 97 97 0 X 〇 resin solution 11 〇〇0 97 97 0 X 〇 resin solution 12 〇〇0 97 97 0 X 〇Disperbyk-2000 〇 block system 4 90 94 0 X 〇AJISPER PB821 X Grafting system 10 0 10 17 〇X J0NCRYL 682 〇 〇0 0 0 238 〇〇PGMAc ··propylene glycol monoterpene ether acetate DEG: diethylene glycol In Table 1, propylene glycol monoterpene ether acetate was used by using a solvent which is insoluble in the fine organic pigment composition shown in Table 3. The fine organic pigments of Examples 1 to 5 in which the resin was made fine and refined, and the fine organic pigments of Examples 1 to 5 were smaller than Comparative Examples Ϊ, 2, and 6, and it was found to be more fine. The fine organic pigment compositions of Examples 1 to 5 have a high contrast and a low retardation tendency as compared with Comparative Examples}, 2 and 4. Further, Comparative Examples 3 and 5 are high-contrast, but exhibit a large retardation value as compared with Examples 1 to 5, and thus their viewing angle dependence is inferior. Obviously, when (4) is prepared by adding each of the resins having the structures and properties described in the fine money pigments of the present invention as in Examples 丨 to 5, it is possible to provide (iv) excellent compatibility, high contrast, and fineness. Second, Bilo. Bilo pigments and red fine mechanical pigments. Ψ W # by using a fine organic pigment which is insoluble in the dispersion of the dispersion (4) shown in Table 3, and the fine organic pigments of each of which are higher than the comparative example 7 and the retardation:::=large Therefore, the fine organic pigment of the present invention having a fine particle size and contrast is prepared by adding the resin as in Examples 6 to 18 to make a fine organic:, and the structure and properties described in the object are high and the display characteristics are _=, , , , P can provide excellent viewing angle dependence and color composition. 'Good fine organic pigments and organic pigments

22U1S 81

Claims (1)

201000570 VII 1. Shen 3 Qing patent scope: : species = organic pigment manufacturing method, its characteristics are: will be "Guangling inorganic salt, water-soluble organic solvent II, Yiji heart tr' composition, and then removed in water The water-soluble slanting organic (4), the towel, and the fat-replenishing (A) are those having a solubility of 1 part by weight per 100 parts by weight of the two parts, and having a base of the amine group and the quaternary ammonium salt group in 25 parts by weight. Shen: The manufacturing method of the fine organic _ of the patent feu, the resin (A) is an acrylic resin. &quot; 申 'patent la® item 2 of the method for producing fine organic pigments, its grease'. The acrylic resin which is synthesized by random polymerization of the upper acrylic resin is a method for producing a propionic acid tree which is synthesized by random polymerization. 4. The method for producing the resin is to dissolve in the propylene glycol monoterpene ether acetic acid. , . . : 1 = 1 / 4 of the range of items 1 to 4 of the fine organic pigments 2 &quot; where 'organic pigments are at least one selected from the diketones and each: and each organic pigment, money_organic pigment 2, 6 ^ New (four) organic pigments are grouped into piety. A fine organic pigment obtained by a method for producing a fine organic pigment according to any one of the above-mentioned claims. .= 重微!!Organic_Coloring composition, which is characterized by containing a fine organic pigment and a pigment carrier of the application. t 1 Concentrate on the pigmentation composition of the fine organic pigment of item 7, which contains a non-aqueous solvent. &quot;321118 82 201000570 III. English abstract: To provide a method for producing a fine organic pigment being usful for obtaining a coloring film, a fine organic pigment according to the method and a fine organic pigment coloring composition using the fine organic pigment, The above coloring film is useful as a color filter for liquid crystal television, and is a film sheet with low retardation, excellent viewing angle dependence, and high transparence. According to the method for producing fine organic pigment, the method is characterized in that Subjecting the organic pigment, a water-soluble inorganic salt, a water-soluble organic solvent and a resin (A) exhibiting a solubility above 1 part by weight relative to 100 parts by weight of the water-soluble organic solvent under 25〇C, To a mechanical kneading following by removing water-soluble salt and water-soluble organic solvent in water, the resin (A) with amino or/and quaternary ammonium group. 4, 4 曰疋 representative map · This case has no schema (1) The representative representative map of this case is: () map. (2) A brief description of the symbol of the representative figure: 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: This case is not represented by the chemical formula 321118 2 201000570 Patent description of the invention 丨 you.: -6, 'Γ〇 L_——...— (The format and order of this manual are not subject to change, please do not fill in the ※ part) ※Application number: [}&lt;? shirt name CAB ^io ^2006,01) φ-^ Invention name: (Chinese/English) Method for producing fine organic pigments, fine organic pigments and fine organic pigments. ※Application date: w ^ ※Working PC classification: (10)% (2006.01) C〇?LX C2006.01) METHOD FOR PRODUCING FINE ORGANIC PIGMENT, FINE ORGANIC PIGMENT AND FINE ORGANIC PIGMENT COLORING COMPOSITION 2. SUMMARY OF THE INVENTION The present invention provides a method for producing a fine organic pigment for obtaining a colored film, a fine organic pigment obtained according to the method, and the use of the fine organic a fine organic pigment coloring composition of a pigment, wherein the colored film is used as a color filter for a liquid crystal television, and Delay, and viewing angle dependence is excellent in high transparency of the film. The solution is a method for producing a fine organic pigment which is characterized in that an organic pigment, a water-soluble inorganic salt, a water-soluble organic solvent, and the water-soluble organic solvent are each at 25 ° C. 〇〇 by weight of the resin (A) having a solubility of 1 part by weight or more, and the resin (... containing an amine group or/and a quaternary ammonium salt group, after mechanical kneading, removing water-soluble inorganic substances in water Salt and water-soluble organic solvent. 321118 1 201000570 6. Technical Field of the Invention The object of the present invention is to provide a method for producing a fine organic pigment, a fine organic pigment obtained according to the method, and a The fine organic pigment coloring composition of the fine pigment. Further, the object of the present invention is to provide an offset printing ink, a gravure printing ink, an ink for printing ink, a color, a resist for a light-sensitive sheet, an ink, and a coating material. Fine organic pigment coloring composition. [Prior Art] It is known in organic pigments, for example, that azo pigments are selected by appropriate reaction strips during synthesis. On the other hand, a finely sized pigment particle can be obtained. On the other hand, a copper phthalocyanine green pigment is formed by the formation of a fine: agglomerated particles are grown and granulated by particles in the following steps. Further, it is known that, for example, a copper phthalocyanine blue pigment or a diketopyrrolopyrazole pigment is used, and coarse and unevenly shaped particles which are formed during the synthesis are formed into a pigment by micronization and granulation in the following steps. A method of using coarse crude pigment particles as a pigment, and a method widely used at present, a solvent-salt grinding method, a dry pulverization method, etc. The dry pulverization method is to pass coarse crude pigment particles through a ball mill, a grinder, and a vibration mill. A method in which the machine is pulverized by dry method to form a pigment, and the production efficiency per unit energy is better than that of the solvent-salt grinding method. However, the particle size is mostly jagged and the cohesive force between the particles is extremely strong, so that only It is possible to obtain a large aggregate of a large number of fine primary particles combined with a strong force. Therefore, although the dry pulverization method has been studied for various improvement methods, However, it is not easy to obtain pigments of the south quality. 3 321118 201000570 On the other hand, the solvent-salt grinding method is to use coarse crude pigment particles in inorganic salts such as sodium chloride or sodium sulfate with ethylene glycol and diethylene glycol. A method of forming a pigment by mechanical grinding in a kneader or the like in the presence of a highly viscous water-soluble organic solvent such as polyethylene glycol. When kneading, the kneaded material becomes a compact mass by adjusting the amount of the solvent (圑The pigment having a desired fineness can be obtained by treatment at an arbitrary temperature and time. Examples of the use of the high fineness pigment are, for example, a color filter. The color filter is used in a color liquid crystal display device. A fine strip (strip) of two or more different hue is arranged in parallel or in a cross on a surface of a transparent substrate such as glass; or a fine pixel is arranged in a fixed length and width. High contrast and transparency of a color liquid crystal display device can be achieved by using a high fineness pigment. However, it is generally difficult to obtain a stable dispersion when the high-fineness pigment particles are dispersed in a pigment carrier such as a varnish. Such a dispersion tends to be highly viscous due to aggregation of pigment particles and the like, and thus exhibits thixotropicity. Such a viscosity increase in the dispersion and poor fluidity may cause problems in the manufacturing operation of the color filter and various problems in the value of the product. For example, the formation of a filter region of a color filter is usually carried out by applying a pigmented composition obtained by dispersing a pigment to a carrier containing a monomer and a resin onto a transparent substrate such as glass. In this case, when a colored composition having a high viscosity and a poor fluidity is used, a coating film having a uniform film thickness cannot be obtained due to poor coatability and poor leveling property, which is not preferable. Moreover, the color filter formed by using the dispersion in which the pigment particles are agglomerated has a markedly reduced contrast. Therefore, 4 321118 201000570 It is desirable that the pigment-based particles do not aggregate and stabilize the fine particles, and are properties that are easy to handle. In order to carry out the use of a color liquid crystal display device for a large-screen television or a monitor, in addition to contrast, transparency, and the like, the viewing angle characteristics are also important items, and the technology for wide viewing angle is promoted. In general, a polymer film has birefringence, and when birefringence is large, polarized light is formed by a refractive index difference in a direction parallel to the film surface and a direction perpendicular to the film surface. Since the retardation greatly increases the retardation value of the color filter and causes a phase difference in the transmitted light, the viewing angle dependence becomes large and the display characteristics are lowered. In particular, it is known that the retardation value of the polymer film is increased by including a crystal having a large retardation value in the polymer film. The diketopyrrolopyrrole pigments are refined by a solvent-salt polishing method or the like, and in particular, the increase in retardation value (positive value) is remarkable, and the viewing angle characteristics are deteriorated. Therefore, in order not to increase the retardation value of the bispyrrolopyrrole pigment and to improve contrast, transparency, and the like, it is necessary to make it fine. When a quinophthalone pigment is used as a material of a color filter, there is a case where a pigment having a large retardation value or a dispersion thereof is used in combination. Therefore, it is necessary to lower the retardation value of the quinophthalone pigment itself. Patent Document 1 discloses a technique for reducing a retardation value of a colored film which is used for a pixel and which is a colored polymer having an average refractive index of 1.60 or more and 1.90 or less and an absolute value of the birefringence of 0.01 or less. film. Patent Document 2 discloses a method of reducing a retardation value by including a compound having two or more planar structure groups in a colored film, and further containing a retardation-reducing particle having a quinolyl group or a group of 5321118 201000570 compound. technology. Patent Document 3 discloses a technique of mechanically kneading an organic pigment, a water-insoluble synthetic resin, a water-soluble inorganic salt, and a water-soluble organic solvent. Patent Document 4 discloses a technique of mechanically kneading a diketopyrrolopyrrole pigment, a dye derivative, a water-soluble inorganic salt, and a water-soluble organic solvent, and it is described that a resin type dispersant can be used. [Patent Document 1] Japanese Laid-Open Patent Publication No. 2000-187114 [Patent Document 3] JP-A-7-13016 [Patent Document 4] [Problem to be Solved by the Invention] An object of the present invention is to provide a fine organic pigment coloring composition which is created in view of the disadvantages of the prior art, the fine organic pigment The coloring composition is obtained by coating a colored pigment composed of a pigment carrier or a non-aqueous solvent in a film form, and the coloring film obtained by the method of the present invention has a high contrast, a low retardation value, and a viewing angle dependency. Excellent and transparent. [Means for Solving the Problem] An embodiment of the present invention relates to a method for producing a fine organic pigment, characterized in that an organic pigment, a water-soluble inorganic salt, a water-soluble organic solvent, and a resin (A) are mechanically kneaded. Obtaining a kneaded composition, and then removing the water-soluble inorganic salt and the water-soluble organic solvent in water, wherein the 321118 201000570 resin (A) has a solubility of 1 part by weight per 100 parts by weight of the water-soluble organic solvent at 25 ° C Above and containing an amine group and / or a grade 4 ammonium base. An embodiment of the present invention relates to a method for producing the above fine organic pigment, wherein the resin (A) is an acrylic resin. An embodiment of the present invention relates to a method for producing the above fine organic pigment, wherein the acrylic resin is an acrylic resin synthesized by random polymerization. An embodiment of the present invention relates to a method for producing the above fine organic pigment, wherein the resin (A) is insoluble in propylene glycol monomethyl ether acetate. An embodiment of the present invention relates to a method for producing the above fine organic pigment, wherein the organic pigment is at least one selected from the group consisting of diketopyrrolopyrrole-based organic pigments, quinophthalone-based organic pigments, and diterpene-based organic pigments. And organic pigments in groups of phthalocyanine organic pigments. One embodiment of the present invention relates to a fine organic pigment which is characterized by the above-described production method. An embodiment of the present invention relates to a fine organic pigment coloring group V 'substance' characterized by containing the above fine organic pigment and a pigment carrier. Further, an embodiment of the present invention relates to the above-mentioned fine organic pigment coloring composition characterized by containing a nonaqueous solvent. [Effect of the Invention] When the fine organic pigment coloring composition of the present invention is applied to a film, the fineness of the pigment is high and the retardation value is low, so that a color film having high transparency and excellent viewing angle dependency can be obtained. By this, it is possible to provide a color 7·321118 201000570 filter which exhibits an excellent effect of exhibiting vivid colors and low viewing angle dependence in a liquid crystal television or the like. [Embodiment] [Formation for Carrying Out Invention] The fine organic pigment of the present invention is an organic pigment inorganic salt and a water-soluble organic solvent: water-soluble and then water-soluble inorganic salt and east composition are removed in water. The organic pigments used in the materials are at least one. The organic porphyrin of the squama, the organic pigment, the Wei (four), the genus of the genus and the phthalocyanine organic pigment, the diketopyrrolopyrrole organic pigment is red, and the three different colors are light. Sex and heat resistance. Two-two == Specific example "When the color index number is expressed", there are Guangyanke, such as 254, 255, 264 or 272, and ^ such as C.I.PW posted nt 73 or 81. ^ment Orange 71 ^ The same organic pigments are yellow... with heat resistance. (4) The list of organic pigments can be listed as: for example, entyeu〇wi3=index' is a part of the organic pigment system purple ^ $ right - light and clear. Organic pigments have excellent resistance to Μ _ R± The specific examples of organic pigments are indexed by pigments: Cyanine organic pigments are blue or green organic pigments, which have excellent properties, 1 lifetime and richness. Specific examples of the blue phthalocyanine-based organic pigments are represented by a pigment index number, and examples thereof include: α U—Η: Bu 321118 8 201000570 2, 3, 4, 5, 6, 16 or 17; Specific examples of the cyanine-based organic pigments are represented by a pigment index number, and examples thereof include CI Pigment Green 7, 36 or 58. The water-soluble inorganic salt used in the kneading composition functions as a pulverization aid, and the salt is pulverized by the high hardness of the inorganic salt during salt milling to refine the primary particles of the pigment. It is not particularly limited as long as it is dissolved in water, and examples thereof include: salt (sodium chloride), potassium chloride, sodium sulfate, zinc chloride, calcium chloride, magnesium chloride or a mixture thereof. However, in terms of price, sodium chloride is preferred. The amount of the water-soluble inorganic salt in the kneading composition is not particularly limited, but is preferably in the range of 1 to 30 times by weight, more preferably in the range of 5 to 20 times by weight, depending on the weight of the pigment, and may be selected depending on the hardness of the object. . When the weight is 1 or more times, the refining and the granules are easily carried out, and when the weight is 30 times or less, the amount of the pigment to be processed in the kneaded material is large, so that the productivity is high and industrialization is facilitated. The particle size of the water-soluble inorganic salt is not particularly limited, but the volume-based medium particle size (D50) is preferably from 1 to 50/zin. When the D50 is 50/m or less, the processing time for the miniaturization of the crude organic pigment is short, and when the D50 is 1 // m or more, the water-soluble inorganic salt can be obtained with low energy. The particle size of the water-soluble inorganic salt can be determined by using a dry form laser diffraction particle size distribution analyzer. The water-soluble organic solvent used in the kneading composition is used to add an organic pigment, a resin (A), and a water-soluble inorganic salt to a uniform mass, and it is expected that the organic pigment can be freely mixed with water or cannot be mixed. Freely mixed but with 9 321118 201000570 has a degree of solubility that can be removed by industrial washing. Further, at the time of kneading, since the temperature of the kneading composition rises and the water-soluble organic solvent is easily evaporated, it is preferable to use a high-boiling solvent for safety. Specifically, examples of the water-soluble organic solvent include 2-methoxyethanol, 2-butoxyethanol, 2-(isopentyloxy)ethanol, 2-(hexyloxy)ethanol, and diethylene glycol. , diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monoterpene ether, liquid polyethylene glycol, 1-decyloxy-2 -propanol' 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monodecyl ether, dipropylene glycol monoethyl ether, low molecular weight polypropylene glycol, aniline, pyridine, tetrahydrofuran, dioxane, decyl alcohol, ethanol, iso Propyl alcohol, n-propanol, isobutanol, n-butanol, ethylene glycol, propylene glycol, propylene glycol monomethyl ether acetate, ethyl acetate, isopropyl acetate, acetone, mercaptoethyl ketone, dimercaptopurine Indoleamine, dimercapto or p-N-decylpyrrolidone. In addition, it is also possible to mix two or more solvents as necessary. The amount of the water-soluble organic solvent in the kneading composition is not particularly limited, but it is desirably 3 to 40% by weight in the kneaded composition, and can be selected depending on the amount of the water-soluble inorganic salt and the hardness of the kneaded composition. When the water-soluble organic solvent is insufficient, since the kneading composition cannot be agglomerated and energy cannot be supplied, it is difficult to refine or the kneaded composition is too hard to maintain a stable operation state. Further, when the amount is excessively added, the kneading composition is too soft and it is difficult to obtain the desired fineness and the entire particle size. The resin (A) used in the kneading composition needs to have a solubility of 1 part by weight or more per 100 parts by weight of the water-soluble organic solvent used in the kneading composition at 25 ° C, and the solubility is 3 parts by weight or more. Better. When the solubility is 1 10 321118 201000570 or more by weight, the resin is uniformly adsorbed on the surface of the pigment due to its high compatibility with the water-soluble organic solvent, so that the desired fineness and the retardation value can be easily obtained. Further, the resin (A) must have a group selected from an amine group and a quaternary ammonium salt group. Salty enhances the affinity for organic pigments by the presence of these groups, and further exhibits effects such as fineness and birefringence. The amine group means a functional group selected from the group consisting of a primary amine group, a secondary amine group, and a tertiary amine group. Among them, the resin (A) is preferably a tertiary amine group or a tertiary ammonium salt group. Here, the 4-grade ammonium salt is represented by the following general formula (1) or the following general formula (1): -N+(-R))(-R2)(-^3) . 21- (in the formula (1) Each of U is independent, is a base of carbon number i to 9 or a base of carbon to 9; R3 is a hydrogen atom, a carbon number of i to 9 or a carbon number of 1 to 9 Agglomerated; Z1 is a halogen atom, R4s〇 "or r4〇s〇3_; R is a hospital base having a carbon number of i to 20 or may have a carbon number of 1 to 2 Torr.) General formula (2): - N+(-R5)(-R6)(-r7-c〇〇-) (In the formula (2), R5 and R2 are each independently, and are a group having a carbon number of 1 to 9 or a carbon number of 1 to 9. The base of the R7 is a carbon number of 丄 to 6 (1 to $1 to 3 is more preferably). The ',, 'the main skeleton of the earth is not limited, but acryl The acid-based resin-based (10)-based resin refers to a monomer having an acryloyl group or a methacrylic acid-based unsaturated monomer as an essential component, and if necessary, an ethylenically unsaturated monomer other than the above-mentioned 321118 11 201000570. And when using the fine organic pigment crop of the present invention to exhibit the characteristics as a color filter === into a fine organic It is preferable that the resin of the coloring composition is the same. It is preferable to use an acrylic resin for the coloring composition of the fine organic pigment in the Japanese, because the resin (4) is (4) (four) and the brain is desired. The amino group has a propyl group, as long as a part or all of the monomer has an amine group and/or a quaternary ammonium salt group. Preferably, for example, a meringue monomer having an amine moiety is used. Examples of the ethylenically unsaturated monomer having an amine group in the case of copolymerization with other ethylidene residues and monomers include, for example, an ethylenically unsaturated monomer having a tertiary amino group, and a salt having a 4-stage ammonium salt group. Examples of the ethylenically unsaturated monomer having a secondary amine group include, for example, N,N-dimethylaminoethyl (meth)acrylate, N,N-diethyl (meth)acrylate Aminoethyl ester, (mercapto)acrylic acid N,N-dimethylaminopropyl vinegar or (meth)acrylic acid N,N-diethylaminopropyl ester, etc. containing N,N-dialkylamino group (meth) acrylates; or N,N-di-aminoethyl (meth) acrylamide, N,N-diethylaminoethyl (meth) propylene Si amine, N , N-dimethylamine a propyl (meth) propylamine or a N,N-ethylaminopropyl (mercapto) acrylamide or the like (meth) acrylamide containing n, n-diamine Etc. Among them, N,N-dimethylaminoacetic acid (meth)acrylate is preferred. Examples of the ethylenically unsaturated monomer having a 4-stage ammonium salt group include, for example, the above-mentioned secondary amine. The ethyl ether unsaturated monomer addition 4 leveling agent is 0 321118 12 201000570 Examples of the 4 leveling agent can be exemplified by: sulphuric acid such as dipropyl sulphate or sulphuric acid; Benzoquinone, chloroethene, chloropropene I, octane, etc. (4) Ethylene, Acrylic or Mosin-based desert; or Ethylene-unsaturated monomer with or without a tertiary amine group and 4 General systems (4) The amine group can be carried out in a solution of the quaternary unsaturated monomer of the quaternary amine group. The temperature at the time of the reaction is about the order or less, and when the ethylene monomer is subjected to the four-stage reaction, it is preferably about 咐 or less, and the reaction time is about m hours. &quot; In addition, the grade 4 agent can also use the hospital oxygen base group. The oxygen-burning rotenyl halide-based halide is represented by the following formula (3). General formula (3): z2-r8~coor9 (in general formula (3), z2 is chlorine or desert, and bromine is preferred; r8 is carbon number i to 6 (preferably 1 to 5, to More preferably to 3; the r9 is a lower alkyl group having a carbon number of 6 to 1 (preferably 1 to 3).) An ethylenically unsaturated monomer having a tertiary amino group and a hospital oxygen-sintering base. The reaction of the compound (4) is carried out in the same reaction as the above-mentioned 4-staged agent in the silk-based alkyl halide of the silk-shirt Moh-cho, and then converted to a carboxylate ion by hydrolysis of -(3)(10)9 (n. Further, an ethylenically unsaturated monomer having a carboxybetaine structure represented by the formula (3) and having a quaternary ammonium salt group can be obtained. Other ethylenically unsaturated monomers can be exemplified by an acrylic monomer and a propylene 321118 201000570. A monomer other than the olefinic acid monomer. In the present application, it is described as "(meth)acrylonitrile", "(meth)acrylic acid plant" (meth)acrylic acid, "(meth)acrylate "(.) (meth) acryloxy" "(meth)acrylic acid amine", unless otherwise specified, is expressed as "acrylic acid base and / (Methyl) propylene base, "acrylic acid and / or (fluorenyl) propyl benzoate", "acrylic acid and / or (T-based) acrylic acid", "acrylate" and / or (A "Acrylate", "acryloxy" and/or (meth)acryloxy" or acrylamide and/or (fluorenyl) acrylamide. Examples of acrylic monomers are as follows: Ethyl (meth) acrylate, (meth) acrylonitrile, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, (meth) acrylate Butyl ester, (butyl) (meth) acrylate, 2-ethylhexyl acrylate, (τ) hexahexyl acrylate, (methyl) propyl benzoate, (meth) acrylate Laurel vinegar, (meth) propylene tetrahydrofurfuryl ester, isobornyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) acrylate, (mercapto) acrylate Phenoxyethyl ester, phenoxy diethylene glycol (meth)acrylate, methoxypolypropylene glycol (meth) acrylate or (fluorenyl) Acetyl ethoxypolyethylene glycol ester or the like (fluorenyl) acrylate, or (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, diacetone (meth) acrylamide or acryl hydrazinomorphyl (meth) acrylamide. An ethylenically unsaturated monomer containing a mercapto group is used. Examples of the ethylenically unsaturated monomer having a carboxyl group include, for example, acrylic acid, methacrylic acid, ε-caprolactone addition acrylic acid, and ε_caprolactone addition.曱基丙14 321118 201000570 One or more selected from the group consisting of enoic acid, isaconic acid, maleic acid, fumaric acid and crotonic acid. Further, an ethylenically unsaturated monomer having a hydroxyl group can also be used. Examples of the hydroxyl group-containing ethylenically unsaturated monomer may be exemplified by 2-(hydroxy)ethyl acrylate, 2 or 3-hydroxypropyl (meth) acrylate, or 2 or 3 (meth) acrylate. Or a hydroxyalkyl (meth) acrylate such as 4-hydroxybutyl ester or cyclohexanedimethanol mono(meth)acrylate. Further, a polyether mono(methyl) acrylate such as the above-mentioned (meth)acrylic acid-based Ss addition polymerization epoxy bromide, propylene bromide, and/or butyl bromide may be used. Or polyester (mono)(meth)acrylic acid obtained by adding (poly)r-valerolactone, (poly)ε-caprolactone and/or (poly)12-hydroxystearic acid. Further, an ethylenically unsaturated monomer containing a hydrazine acid group may also be used. The ethylenically unsaturated single system containing a phosphate group can be obtained, for example, by reacting a hydroxyl group of the above-mentioned hydroxyl group-containing ethylenically unsaturated monomer with a phthalic acid esterifying agent such as phosphorus pentoxide or polyphosphoric acid. Examples of the monomer other than the acrylic monomer may, for example, be styrene such as phenethyl hydrazine or α-methyl styrene; ethyl ethene, n-propyl ethoxylate, isopropylethylene hydride, and positive Butyl ethoxylate _ or isobutyl acetonate and other berry women; vinyl acetate vinegar, ethyl vinegar and other fatty acid vinyl esters. The above monomers other than the acrylic acid-based body may be used in combination with the above-mentioned propylene-glycol-based monomer. As a method of obtaining the resin (Α) to which the present invention is applied, a conventional method such as anionic polymerization, living anionic polymerization, cationic polymerization, living cationic polymerization, radical polymerization, and living radical polymerization can be used. Among them, free 32111S 15 201000570-based polymerization or living radical polymerization is preferred. For the living radical polymerization method, a polymerization initiator is preferably used. As the polymerization initiator, for example, an azo compound and an organic peroxide can be used. Examples of the azo compound include, for example, 2, 2'-azobisisobutyronitrile, 2, 2, azobis(2-methylbutyronitrile), and 1,r-azobis(cyclohexane). Carbonitrile), 2, 2, azobis(2,4-dimethylvaleronitrile), 2, 2'-azobis(2,4-dimercapto-4~methoxyvaleronitrile), two Indenyl 2,2,-azobis(2-methylpropionate), 4,4,monoazo, (4-cyanovaleric acid), 2,2,-azobis(2-hydroxyl) Propionitrile or 2, 2, azo-[2-(2-imidazolin-2-yl)propane]. Examples of the organic peroxides include, for example, benzamidine peroxide, tert-butyl peroxybenzoate, hydroperoxy = cumene, diisopropyl peroxydicarbonate, di-n-propane diperoxide曰Peroxydicarbonate di(2-ethoxyethyl ester), peroxy neodecanoic acid third I hydrazine, peroxypivalic acid tert-butyl ester, peroxidation (3,5,5-trimethylhexyl) ,), dipropene peroxide or diethyl peroxide. These polymerization initiators may be used singly or in combination of two or more. The reaction temperature is preferably from sen to 150 C ', preferably from 50 to ii 〇 °c; the reaction time is preferably from 3 to 3 Torr, preferably from 5 to 20 hours. The living radical polymerization method can suppress the side caused by the general radical polymerization, and should be especially produced in a 75-growth growth system, so that it is easy to synthesize an infill polymer or a resin having a uniform molecular weight. &quot;In the atomic transfer radical polymerization method using organic dentate or sulfonium sulfonate as a starting agent and using == as a catalyst, it is suitable for early (point, can be adapted to the polymerization temperature of existing equipment) The earth atom transfer radical polymerization method can be carried out according to the methods described in the following References 1 to 321118 16 201000570, etc. (Reference 1) Fukuda et al., Prog. Polym. Sci. 2004, 29, 329 (Reference 2) Maty Jaszewski et al. 'Chem. Rev. 2001, 101, 2921 (Reference 3) Maty jaszewski et al. 'J. Am. Chem. Soc. 1995, 117, 5614 (Reference 4) Macromolecules 1995, 28, 7901, Science, 1996, 272, 866 (Reference 5) W096/030421 (Reference 6) WO97/018247 (Reference 7) Japanese Laid-Open Patent Publication No. Hei 9/8616 (reference No. 8). There is also a case called solvent.) Although the solvent is not special, it can be used as follows: acetic acid, n-butyl acetate, isobutyl acrylate, toluene, diphenylbenzene, acetone, hexane, Methyl ethyl ketone % ketone, propylene glycol monomethyl ether acetate Dipropylene glycol monoterpene ether acetic acid di "alcohol monoethyl acetate", ethylene glycol monobutyl methacrylate, diethylene bis 2 ester or diethylene glycol monobutyl sulphate acetate, etc. These polymeric solvents 叮 &amp; In the case of the above-mentioned (4) 蚵A), the 4' which is a functional group is a soil and a chemical method, and it is not only the copolymerization of the above-mentioned:::diyl sulfhydryl unsaturated monomer as a monomer component. In addition, the amine-saturated monomer upgrading agent can also be obtained by the amount of the amine group and the fourth-order ammonium group present in the resin (A) to which the present invention is applied, and the above-mentioned 4 321118 17 201000570. There is no particular limitation, but the sum of the amine value of the resin and the ammonium salt value of the fourth grade is preferably from 1 to 300 mgKOH/g, more preferably from 10 to 200 mgKOH/g, and the sum of the amine value and the ammonium salt value of the grade 4 is at 1 mgKOH/ When it is more than g, it exhibits a remarkable effect. When it is 300 mgKOH/g or less, the compatibility with the fine organic pigment coloring composition is high and becomes low viscosity. Further, the structure of the amine group is not particularly limited and can be substituted with various functional groups. The molecular weight of the resin (A) used in the present invention is not particularly limited, but The converted weight average molecular weight measured by gel permeation chromatography (GPC: Gel Permeation Chromatogrpahy) is preferably from 1,000 to 500,000, more preferably from 5,000 to 15,000. The resin (A) used in the present invention is preferably one having a solvent which is insoluble in the coloring composition of the fine organic pigment. According to this, a fine organic pigment coloring composition having a high Contrast Ratio can be obtained. The resin (A) is preferably one which is insoluble in an ester solvent having a molecular weight of from 118 to 133, and more preferably propylene glycol monoterpene ether acetate having a molecular weight of 132.16. The resin (A) used in the present invention can obtain a fine organic pigment and a fine organic pigment coloring composition even if a resin obtained by block polymerization is used, and a resin obtained by random polymerization which is easy to prepare by the method can be obtained in the same manner. A fine organic pigment and a fine organic pigment coloring composition. The block polymerization refers to a method in which only a certain monomer is polymerized in advance, and other monomers are separately polymerized, and blocks of the respective polymers are separately prepared and then reacted. 1 重量。 0. 03至0. 3。 0 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 The parts by weight are more preferred. When the amount of the resin (A) is 0.1 part by weight or more, the effect of refining can be easily obtained, and when it is at most 1. part by weight, the viscosity can be preferably improved in the fine organic pigment coloring composition. Further, it is preferred to adjust the amount of the resin (A) in accordance with the compatibility of the resin (A) and the pigment carrier. That is, when the compatibility is high, the amount of the resin (A) should be kept to a minimum to reduce the influence on the physical properties of the pigment carrier. On the other hand, when the compatibility is high, the amount of the resin (A) should be increased to fully exert the dispersion effect. . The kneading composition can be used in combination: various additives such as a resin, a dispersing aid, a plasticizer, a dispersing agent, and a surfactant; a pigment derivative of a compound in which a substituent is introduced into an organic pigment molecule; or generally used as a body pigment. Inorganic pigments such as calcium carbonate, barium sulfate and cerium oxide. Other pigments can also be mixed and processed to adjust the color tone. In particular, in order to prevent crystal growth of organic pigments and crystal transfer&gt; and to efficiently produce fine organic pigments, it is preferred that the kneading composition contains a pigment derivative, an anthracene derivative, a bite ketone derivative or the like. At least one derivative of the cultivated derivative. Each of the above derivatives is a compound which introduces a basic substituent, an acidic substituent or a ruthenium methyl group into an organic pigment, anthraquinone, acridone or three tillage. The quinone imine methyl group may also have a substituent. Among them, a pigment derivative, particularly a pigment derivative having a structure similar to that of a finely divided organic pigment, is preferable because it has an extremely high effect of suppressing crystal growth of a pigment. Here, the pigment derivative is a compound in which a substituent is introduced into an organic dye. 19 321118 201000570 The color of the ΓΤ pigment is preferably, and if the amount is small, it may be =:?=. The organic pigment also contains a naphthene knife, which is not usually called a pigment, and a polycyclic compound. For the pigment derivative, it is possible to use the Japanese special 曰 曰 林 h / 、 、 、 、 日本 52 52 52 52 52 52 52 52 52 52 52 52 52 52 54 54 54 54 54 54 54 54 54 54 54 54 54 54 54 54 54 54 54 54 The main reason for the effect is that it can be used alone or in combination of two or more types. The pigment derivative is a compound represented by the following formula (4): (4). In the formula (4), hydrazine is an organic ray 4 is a basic substituent or a quinone. methyl. Taking the organic odor of the organic pigment residue of the formula (4) and the pigment; azo 'bisazo (da-: ugly i-type phthalocyanine or gold-free phthalocyanine, etc.) Based on onion, diamine-based, onion, onion, indanthrone, onion, ketone, etc., onion, ketone, etc.; = material; two duck pigment; (four) pigment; ^ = material; a pigment; an isolone-based pigment; a diphenyl benzoate ketone-based pigment; a threon-based complex-based pigment, etc. The hydrazine, hydrazine or i-type substituent may be exemplified by the following formula (5) The substituent which is not a compound of the formula (7), and the acidic substituent may, for example, be a substituent represented by the formula (9) or the formula (10) in the following formula: 321118 20 201000570 H. /R10 \r11 X2 wide CH-CH / \ X N, N~R16 ch-ch R14 \15 [In the general formulae (5) to (7), X is -S〇2 CO CH2-, -CMHCOCfL·---CH2NHSG2CH2- or direct bonding; Y is -NH-, -0- or direct bonding; η is an integer of 1 to 10; γ1 is a 22-z-NRt or a direct bond; R22 and R23 are each independently a hydrogen atom, may have a substituent of an alkyl group having 1 to 36 carbon atoms, and may have a substituent. Alkenyl group having 2 to 36 carbon atoms, 21 321118 201000570 phenyl group having a substituent; z being a stretching group which may have a substituent or a aryl group which may have a substituent, and R and R are each independently a hydrogen atom An alkyl group having a carbon number of a substituent} to 30, an alkenyl group having 2 to 3 carbon atoms which may have a substituent, or a Ri- or Rn---containing a nitrogen, oxygen or sulfur atom, a heterocyclic ring which may have a substituent; R, R, R14 and R15 are each independently a hydrogen atom, a decyl group having 1 to 20 carbon atoms which may have a substituent, and an alkenyl group having 2 to 2 carbon atoms which may have a substituent a aryl group having 6 to 20 carbon atoms which may have a substituent; κ] 6 is a hydrogen atom, an alkyl group having a carbon number of 丨 to 2〇 which may have a substituent, and a carbon number of 2 to 20 which may have a substituent Base R17 is a substituent represented by the above formula (5) or a substituent represented by the above formula (6), and 'Q is a hydroxyl group, an alkoxy group, a substituent represented by the above formula (5) or the above formula (6) Substituents shown]. The amine component used for forming the substituent represented by the general formulae (5) to (7) may, for example, be diamine, diethylamine, methylethylamine, hydrazine, hydrazine-ethylisopropylamine or hydrazine-B. Propylamine, hydrazine, hydrazine-methylbutylamine, hydrazine, hydrazine-mercaptoisobutylamine, hydrazine, hydrazine-butylethylamine, hydrazine-tert-butylethylamine, diisopropylamine, dipropylamine, hydrazine , Ν-second butyl propylamine, dibutylamine, di-second butylamine, diisobutylamine, hydrazine, hydrazine-isobutyl _ second butylamine, monoamylamine, diisoamylamine, dihexylamine, Dicyclohexylamine, bis(2-ethylhexyl)amine, dioctylamine, hydrazine, decyl decyl octadecylamine, decylamine, diallylamine, hydrazine, hydrazine-ethyl-1,2-di Propylamine, ν, ν-mercaptohexylamine, dioleylamine, distearylamine, 321118 22 201000570 N,N-dimethylaminoguanamine, N,N-didecylaminoethylamine, N, N-dimercaptoamine pentaamine, N,N-dimethylaminobutylamine, N,N-diethylaminoethylamine, N,N-diethylaminopropylamine, n,N-di Ethylaminohexylamine, N,N-diethyl: butylamine, N,N-diethylaminopentylamine, n,n-dipropylaminobutylamine, N'N-dibutyl Aminopropylamine, n,N-dibutylaminoethylamine, N,N-dibutylaminobutylamine, N,N-diisobutylaminopentylamine, N,N-methyl-Lauryl Aminopropylamine, N,N-ethyl-hexylaminoethylamine, N,N-distearate aminoethylamine, hydrazine, hydrazine-dioleylaminoethylamine, n,N-distearyl Aminobutylamine, piperidine, 2-methylpiperidine, 3-methylpiperidine, 4-methylpiperidine, 2,4-dimercaptopiperidine, 2,6-methyl-methyl trace 3, 5-Dimethyl π chen, 3- σ Chen sterol, ^ 曱 曱 、, 4-piperidinecarboxylic acid oxime ester, 4-piperidinecarboxylic acid ethyl ester, 2-piperidine ethanol, pyrrolidine, 3-hydroxypyrrolidine, N-aminoethylpiperidine, N-aminoethyl-4-indolylpiperidine, N-aminoethylmorpholine, N-aminopropylpiperidine, N-amino group Propyl-2-methylpiperidine, N-aminopropyl-4-indolylpiperidine, N-aminopropylmorpholine, N-methylpiperidin, N-butylpiped, N-A Base height piper, 1-cyclopentyl tour, 1-amino-4-indolyl π 哄 or 1-cyclopentyl guanidine. —S03M / i —~COOM/ ί r18 [In the above formulas (8) to (10), 23 321118 201000570 Μ is a hydrogen atom, a #5 atom, a copper atom, a recorded atom, a violent atom or a argon atom; i is a valence of hydrazine; R18, R19, R2 And R21 are each independently a hydrogen atom, an alkyl group having 1 to 36 carbon atoms which may have a substituent, an alkenyl group having 2 to 36 carbon atoms which may have a substituent, a phenyl group or a polyoxyalkylene group which may have a substituent base]. The amine component used to form the sulfonic acid amine salt of the formula (10) may be any one of the first, second, third or fourth grade amines. Examples of the primary amine include, for example, hexylamine having a side chain, heptylamine, octylamine, decylamine, decylamine, undecylamine, dodecylamine (i.e., laurylamine), tridecylamine, tetradecylamine, and ten. a saturated amine such as pentaamine, hexadecylamine, heptadecylamine, octadecylamine, pentadecanamide or hexaamine; or an unsaturated amine corresponding to the above saturated amine carbon number. Examples of the secondary amine include, for example, dioleylamine or distearylamine. Examples of the tertiary amine include dimercaptooctylamine, dimethyl decylamine, dimethyl laurylamine, dimercaptostearylamine, dilauryl monodecylamine or trioctylamine. The fourth-grade amine may, for example, be dinonyl dilauryl ammonium chloride, dimethyl dioleyl ammonium chloride, dinonyl dimercapto ammonium chloride, dimercapto dioctyl ammonium chloride, or tridecyl. Stearyl ammonium chloride, dimethyl distearyl ammonium chloride, trimethyl decyl ruthenium chloride, tridecyl hexadecyl ammonium chloride, tridecyl hexadecanthyl ammonium chloride, two Mercapto lauryl tetradecyl ammonium chloride or dimethyl cetyl octadecyl ammonium chloride. When any of R18, R19, R2° and R21 in the formula (10) represents a polyoxyalkylene group, examples thereof include a polyoxyalkylene group or a polyoxyalkylene group. The blending amount of the pigment derivative in the kneaded composition is, in terms of 100 parts by weight of the organic pigment, 1 part by weight, and more preferably 5 parts by weight. The amount of He’s creatures is 2 〇 钕 , , , , , , , , , , , , , , , 里里 injuries are easy to 獾妲&gt; force σ 彰 effect, such as in 30 parts by weight. Don't get a sizzle. When the inside is under, the remaining reading bio-scores ^ especially the quinuca line system yellow addition amount, compared to the organic color, and the pigment mixture in the micro-fineification of the pigmentation street creatures. 02 parts by weight is more preferred. Machine, planetary _ device, oil company made Bu: (four) / - 仃 ^ mixing machine (8) - 仏: Inoue production. ^Two-axis parent, multi-axis roll, extruder (Extruder), KRC kneader (made by Kurimoto Iron Works Co., Ltd.) or training extruder (MIRACLE KCK; manufactured by Asada Iron Works Co., Ltd.), etc., there is no special P艮System 'mixed material _ good mechanical shear force # 'one batch or continuous can be used. The temperature of the kneaded mixture (9) is specially designed for mechanical training, but it is better to treat it at 20 to Wei, which is better. Under the conditions of 20 ° C or more and 80 ° C or less, θ 姑 主 主 主 主 主 , , , , , , , , , 主 主 主 θ θ θ θ θ θ θ θ θ θ θ θ θ θ θ θ θ θ θ θ θ θ θ θ θ θ ^,, does not need speed and crystal growth rate of organic pigment particles, but: mash and make fine and fine. Nothing can be obtained where needed. The fine organic pigments after mixing are processed according to the usual method. . That is, the composition is treated with water or an aqueous solution of inorganic acid and washed with water to remove water-soluble inorganic salts and water-soluble organic liquids; Specifically, the fine organic mash after the kneading is put into water, and the slurry is granulated, and then the slurry is filtered and washed with water to remove the water-soluble inorganic salt and the water-soluble organic solvent. Making fine organic pigments. These steps can be repeated multiple times. The aqueous solution of the inorganic acid is not particularly limited, and examples thereof include an aqueous solution containing a mineral acid such as hydrochloric acid, sulfuric acid, nitric acid or phosphoric acid. For the stirring, for example, a high speed mixer can be used. For filtration, for example: a filter press. The fine pigment can be used directly in a wet state, or can be used in a powder state after being dried and pulverized. The average primary particle diameter of the obtained fine organic pigment is preferably 40 nm or less, more preferably 30 nm or less, and particularly preferably 20 nm or less. The average primary particle diameter is preferably 5 nm or more. When the average primary particle diameter of the pigment is larger than the upper limit, the transparency of the colored film or the like is lowered. When the amount is less than the lower limit, the pigment is difficult to disperse, and it becomes difficult to maintain the stability of the colored composition and ensure fluidity. Further, examples of the method for calculating the primary particle diameter are as follows. The image of the fine organic pigment photographed by a transmission electron microscope (T E Μ) is subjected to image processing or the like to obtain a projected area of each particle, and a diameter corresponding to a circle of the projected area is calculated. The calculated value of the sum of the diameters of the circles of the respective particles divided by the number can be used as the average primary particle diameter. The obtained fine organic pigment can be used as a fine organic pigment coloring composition. The fine organic pigment coloring composition contains a fine organic pigment and a pigment carrier. The pigment-supporting system contained in the fine organic pigment coloring composition of the present invention comprises a fine organic pigment-dispersed product composed of a resin, a precursor thereof or a mixture thereof. In the whole wavelength range of 400 to 700 nm in the visible light region, the resin preferably has a transmittance of 80% or more, more preferably 95% or more. Resin 26 321118 201000570 includes a thermoplastic resin, a thermosetting resin, and an active energy ray-curable tree, which includes a monomer or oligomer which is hardened by active energy ray irradiation to form a resin, which may be used alone or in combination. Two or more types are used. The fine organic pigment in the fine organic pigment coloring composition 1 It is known that the pigment carrier can be used in an amount of 30 to 7 parts by weight, preferably 60 to 45 parts by weight. Further, when a mixture of a resin and a precursor thereof is used as a pigment carrier, the amount of the fine organic pigment is about 2 parts by weight, and the amount of the fine organic pigment is 2 parts to the average, 50 to 25, relative to the fine organic pigment coloring composition. It is better to weigh 1 part. Further, the resin precursor can be used in an amount of 10 to a weight n U with respect to the fine organic pigment parts by weight of the fine organic pigment coloring composition.  It is better. .  The thermoplastic resin may, for example, be a butyl ketone, a styrene-maleic acid copolymer, a chlorinated ethylene, a chlorinated polypropylene, a polychloroethylene, a propylene-vinyl acetate copolymer, a polyvinyl acetate vinegar, Polyurethane vinegar resin, polyester resin, acrylic resin, alkyd resin, polystyrene resin, polyamide resin, oak resin, cyclized rubber resin, cellulose, polyethylene ( HDPE, LDPE) 'Polybutadiene or polyaniline resin. Examples of the thermosetting resin include an epoxy resin, a benzoate amine resin, a rosin-modified maleic acid resin, a rosin-modified fumaric acid resin, a melamine resin, a urea resin, and a discretionary wax. Active energy ray-curable resin: it has a reaction with a residual group, a slow base or a base; the polymer having a substituent has a reaction with an isocyanate group, a trans group or a methoxy group; The (meth)acrylic acid compound or cinnamic acid 321118 27 201000570 The reaction 're-introduces (fluorenyl) acryl-based or styryl group and other photocrosslinkable groups. Further, a linear polymer containing an anhydride such as a styrene-maleic acid copolymer or an α-olefin-maleic anhydride copolymer may be used to have a hydroxyalkyl (meth) acrylate or the like having a thiol group. The (meth)acrylic acid compound is obtained by semi-finishing. .   Examples of the resin and the oligomer of the resin are as follows: methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, ( Butyl methyl methacrylate, isobutyl ketone (meth) acrylate, tributyl ketone (meth) acrylate, isobutyl vinegar, octyl methacrylate, (A) Base) isooctyl acrylate, 2-ethylhexyl acrylate (meth) acrylate, amide vinegar (meth) acrylate, (methyl) propylene rare earth citrate, (methyl) propyl acetoacetate (Methyl)-acrylic acid laurel vinegar, (meth)acrylic acid tri-filament, (meth)acrylic acid isotonic acid, (meth) acrylic acid stearic acid or (meth)acrylic acid Straight bond or branched alkyl acrylate such as stearin; Acrylic ring (IV) - 酉, (meth)acrylic acid dicyclopentan vinegar 'W-based) propylene dicyclopentoxide, (?) acrylic acid Cyclopentene g, (methyl) = ethyl acetonate or (yinyl) acrylic acid, pentyl fine ester; Acetyl propylene: triamter ethyl ester, (mercapto) acrylic acid octane pentoxide, (acrylic acid fluoride; private methyl) tetrafluoropropyl propyl acrylate (methyl) propylene Oxygen-modified polydiphenyl-based oxy-oxygen (Juxi Xioxin 321118 28 201000570 molecular monomer); (F-based) tetrahydrogen methacrylate or (meth)acrylic acid 3_甲美一3 - Heterocyclic (fluorenyl) acrylates such as oxetane; (meth)acrylic acid vinegar, phenoxyethyl methacrylate, phenoxy polyethylene glycol (meth) acrylate Vinegar, (meth)acrylic acid p-cumylphenoxyethyl ester, p-cumylphenylhydrazine polyethylene glycol (meth) acrylate or nonylphenoxy polyethylene glycol (meth) propylene Sour vinegar # (meth) acrylate with aromatic ring; 2-methoxyethyl (meth) acrylate, 2- ethoxyethyl (meth) acrylate, 3-methyl oxy) Butyl ester, (meth)acrylic acid 2-methoxypropyl ester, diethylene glycol monoterpene ether (mercapto) acrylate, diethylene glycol monoethyl ether (meth) acrylate, triethylene glycol monomethyl ether( Acrylate, triethylol monoethyl ether (meth) acrylate, diethylene glycol mono-2-ethylhexyl (meth) acrylate, dipropylene glycol monomethyl ether (meth) acrylate, tripropylene glycol Mono (indenyl) acrylate, polyethylene glycol monovalent alkyl ether (mercapto) acryl oxime 酉 S or polyethylene glycol soap hard fat-based mystery (indenyl) acrylic acid g (poly) Glycol monoalkyl ether (mercapto) acrylates; (meth)acrylic acid, acrylic acid dimer, 2-(indenyl) propylene oxiranyl ethyl phthalate, 2-(indenyl) propylene oxime Propyl phthalate, 2-(methyl) propylene methoxyethyl hexahydro styrene, 2-(indenyl) propylene methoxy propyl hexahydro phthalate, ethylene oxide a (meth) acrylate having a carboxyl group such as a succinic acid (mercapto) acrylate, a stone-carboxyethyl (meth) acrylate or an ω-reactive polycaprolactone (mercapto) acrylate; (Mercapto) 2-hydroxyethyl acrylate, 2-hydroxypropenyl (hydroxy) 29 321118 201000570 ester, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate (Mercapto) 2-propoxyethyl 2-hydroxyethyl acrylate, diethylene glycol mono (meth) acrylate, dipropylene glycol mono (meth) acrylate vinegar, polyethylene glycol single (A Acrylate, propylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, polytetramethylene glycol mono(meth)acrylate, poly(ethylene glycol-propylene glycol) mono(meth)acrylic acid Ester, poly(ethylene glycol-butanediol) mono(meth)acrylate, poly(ethylene glycol-butanediol) mono(meth)acrylate, poly(propylene glycol-butanediol) mono(methyl) Acrylate (meth) acrylates such as acrylate or (meth)acrylic acid glycerin, etc.; ethylene glycol di(meth)acrylate, diethylene glycol di(?) , bismuth acrylate, diethylene glycol di(meth) acrylate, polyethylene glycol bis(indenyl) propylene hydrazine, propylene glycol di(meth) acrylate, dipropylene glycol di(meth) propylene酉 酉曰, dipropanol di (meth) acrylate, polypropylene glycol di (meth) acrylate, poly (ethylene glycol - propylene glycol) bis (indenyl) acrylate, poly (ethylene diterpenoid - Butylene glycol) di(meth)acrylate, poly(propylene glycol-butanediol) di(meth)acrylate, polybutylene glycol di(meth)acrylate, U-butanediol di(methyl) Acrylate, neopentyl glycol bis(indenyl) acrylate, hexanediol di(meth) acrylate, L 9-nonanediol di(meth) acrylate or 2-ethyl-2-butyl - (poly) alkanediol di(meth) acrylates such as propylene glycol di(indenyl) acrylate; one is methyl-cyclopentanyl bis(indenyl) acrylate, and the thioglycolic acid Alcohol di(meth) acrylate, stearic acid modified pentaerythritol di(indenyl) acrylate, ethylene oxide modified double A type di (Yue-yl) acrylate,% propylene oxide modified bisphenol A di (Yue-yl) acrylate, butylene oxide modified 3211J8. 30 201000570 Bisphenol A type di(meth) acrylate, ethylene oxide modified bisphenol F type di(meth) acrylate, propylene oxide modified bisphenol F type di(meth) acrylate, i Oxygen butadiene-modified double-checked F-type di(meth)acrylic acid I, zinc diacrylate, % oxyethane modified phosphoric acid triacrylate or di(meth)propionic acid such as glycerol di(decyl) acrylate Esters; diammonium ethyl (mercapto) acrylate, diethylaminoethyl (meth) acrylate from hydrazine, monomethylaminopropyl (meth) acrylate or diethylaminopropyl (Meth) acrylates having a tertiary amino group such as (meth) acrylate; tris(meth)acrylate, trishydroxypropylpropane tris(methyl)propene oxime, quaternary phosphonium a trifunctional or higher polyfunctional group such as tetraol tris(methyl)propionate vinegar, pentaerythritol tetra(meth) acrylate, dipentaerythritol penta(indenyl) acrylate or dipentaerythritol hexa(meth) acrylate )Acrylates;' • Glycerol Diacetone - (Meth) Acrylate Additive, Glycerol Diepoxide An ether-(meth)acrylic acid adduct, a polyglycerol polyglycidyl-_(meth)acrylic acid adduct, a 1,6-butanediol diglycidyl ether-(mercapto)acrylic acid adduct, , a epoxidized propylene-bonded _(fluorenyl) acrylate adduct, a propyl propylene propylene _ (meth) acrylate adduct, a phenyl epoxidized ether - (meth) acrylate adduct, Benxi Epoxide-(methyl)propionic acid adduct, double-prepared type A diepoxypropane-(meth)acrylic acid adduct, epoxidized and modified double-checked type A bicyclic Oxypropyl-(indenyl)acrylic acid adduct, bisphenol F-type digoxypropyl ether-(meth)acrylic acid adduct, epichlorohydrin modified tantalic acid-(meth)acrylic acid adduct, Epoxy chloropropene-modified hexaphthalic acid-(meth)acrylic acid adduct, ethylene glycol diglycidyl ether-(meth)acrylic acid adduct, polyethylene glycol diglycidyl ether-( Methyl) acrylic acid adduct, propylene glycol diglycidyl ether-(meth)acrylic acid adduct, 31 321118 201000570 polypropylene glycol diglycidyl ether _(meth)acrylic acid adduct, novolac epoxy resin -(Meth)acrylic acid adduct, A A novolac type epoxy resin-(meth)acrylic acid adduct or other epoxy resin-(meth)acrylic acid-added epoxy (meth)acrylate; (meth)acrylonitrile-based modified Trimeric isocyanate, (meth) propylene fluorenyl glutamate, (meth) propylene fluorenyl modified polyester, (meth) propylene fluorenyl modified melamine, (meth) acrylonitrile Modified (meth) propylene group modified | polybutylene or (meth) acrylonitrile modified rosin (meth) propylene fluorenyl modified resin oligomers; X benzene , such as α-methyl styrene, vinyl acetate, vinyl (meth) acrylate or allyl (meth) acrylate; good ethyl vinyl ether, ethylene glycol divinyl ether or pentaerythritol triethyl An oxime such as oxime ether (meth) acrylamide, hydrazine-hydroxymethyl (meth) acrylamide or hydrazine-vinylcarbamide; or 'acrylonitrile. These may be used alone or in combination of two or more. In the organic pigment coloring composition of the present invention, a photopolymerization starting material may be added when the composition is irradiated with ultraviolet rays to harden. A photopolymerization initiator which can be used, and examples thereof include: ^ #phenoxy monoacetophenone, 4-t-butyl-2-diacetophenone, diethoxyphenylethyl _, bu (4- Isopropyl phenyl-2-indenylpropanone-dioxadi-S-cyclohexylbenzene®, 2-mdimethylamino+(4-Ν-?琳^^^^ or ^曱基-卜曱Thionyl thiol]-2^-,, 'Tupropane-Ι-g equivalent acetophenone photopolymerization initiator; 321118 32 201000570 Benzene, benzoin methyl ether, benzoin ether, benzene a benzoin photopolymerization initiator such as isopropyl ether or benzyl dimethyl ketal; benzophenone, benzhydrazinobenzoic acid, methyl benzoylbenzoate, 4-phenyl a benzophenone photopolymerization initiator such as benzophenone, hydroxybenzophenone, acrylated benzophenone or benzoquinone-4, fluorenyl diphenyl sulfide, (iv) ketone, 2 a thioxanthone photopolymerization initiator such as a chloranil side, a 2-methyl ketone, an isopropyl hydrazine or a 2,4-diisopropyl thioxanthone; a 2'4,6-dichloro- 5-triphthyl, 2-phenyl-4,6-bis(trioxanemethyl)_^_ three tillage, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)_s- Sancha, 2 gas p-tolyl)-4,6-bis(trichlorofyl)triazine, 2_piperonyl bis (tris-f-group)-s-three-well, 2,4-bis(trichloromethyl) _6—styrene-based Mitsui 2 (naphthalen-1-yl)-4,6-bis(trichloromethyl)_s_tritium, 2_(4-methoxy-cai-buji)-4, 6- Bis(trichloromethyl)-s-trimorphine, 2, 4-trimethylmethyl_piperonyl-6-dia or 2,4-trisylmethyl (4,+6-three-equivalent, etc.) a photopolymerization initiator; a vinegar (bGrat (10) photopolymerization initiator; a photopolymerization initiator; or an imidazole photopolymerization initiator, etc.), relative to the fine organic pigment 100 in the coloring composition. The photopolymerization initiator may be used in an amount of 5 S 2 GG by weight, preferably 10 to 150 parts by weight, and 2 or more kinds of photopolymerization initiators may be used alone or in combination of two or more. Break the knowledge. α _. Gas-based vinegar, tyrosylphosphine oxide, methyl benzyl benzoate ~9, 10 - phenanthrenequinone, camphorquinone, ethyl hydrazine, 4, 4, - 33 321118 201000570 = = Gang, 3'3, a compound such as _肆(t-butylperoxycarbonyl)dibenylhydrazine or 4,4-diethylaminobenzophenone, relative to 1 part by weight of the photopolymerization initiator in the composition, Sensitization is 0. 1 to 60 parts by weight. In the case of use, the fine organic pigment coloring composition of the present invention can be adjusted in accordance with the color resist type of the developing type. Color 2 agent (4) A pigment containing a ruthenium thermoplastic resin, a thermosetting resin or an active energy ray-curable resin and an early pigment carrier. One or two or more kinds of the above fine organic pigments are polymerized with necessary light, and a three-axis roll mill, a two-axis roll mill, a sand mill, a kneader or a grinder (attritGr) is used in the pigment carrier. And various kinds of dispersing means can be prepared and the fine organic pigment coloring composition of the present invention can also disperse and grow the d, ® organic pigments in the pigment carrier towel and mix them to prepare the fine organic pigment dispersed in the pigment carrier. In the meantime, it is possible to suitably use a dispersion of a pigment-type pigment dispersant, a surfactant, and a pigment derivative to facilitate dispersion of the pigment by the dispersing aid and to prevent the effect of dispersing the pigment: When using a dispersing aid to disperse a pigment in a pigment carrier to form a colored film, a transparent phase is used! The pigment (10) parts by weight in the coloring composition is 0 in the dispersion aid.  1 to 40 parts by weight, and 〇.  1 to 30 parts by weight Ma Jia. In addition, the pigment derivative is excellent in the function of preventing aggregation of the fine organic pigment and maintaining the fine dispersion state of the organic pigment, and can be produced by using a fine organic pigment coloring composition derived from the 321118 34 201000570. The color film with contrast and color purity is suitable as a dispersing aid. The resin type pigment dispersant added to the fine organic pigment coloring composition of the present invention has a pigment affinity site which adsorbs pigment characteristics, and a function which is mixed with the pigment and allows the pigment to be stably dispersed in the pigment carrier. The resin type pigment dispersant may, for example, be a polyethylene-based, polyaminocarbamate if'm polymer system, (iv) an oxygen system or a composite ruthenium polymer. Examples of the affinity of the pigment include a polar group such as a carboxyl group, a hydroxyl group, a phosphoric acid group, a phosphate group, a sulfonic acid group, a hydroxyl group, an amine group, a 4- to ammonium group or a phosphonium group, and an ethylene oxide or polyepoxy group. A hydrophilic polymer chain such as propane or such a composite system. The site compatible with the pigment (pigment) carrier may, for example, be a long-chain alkyl chain, a polyethylene chain, a polyether chain or a polyester chain. Examples of the resin type pigment dispersant include: styrene-maleic anhydride copolymer, olefin-maleic anhydride copolymer, poly(meth)acrylate, styrene-(meth)acrylic acid copolymer, (fluorenyl)acrylic acid -(mercapto)acrylic acid ester copolymer, (meth)acrylic acid-polyethylene macromonomer copolymer, acrylic acid resin containing phosphoric acid base, acrylic resin containing aromatic carboxyl group, polystyrene sulfonate An anionic resin type pigment dispersant such as acrylamide-(indenyl)acrylic acid copolymer, carboxymethyl cellulose, polyamino phthalic acid ester having carboxyl group, furfural condensate of naphthalenesulfonate or sodium alginate 35 321118 201000570 Nonionic resin pigment dispersant such as polyvinyl alcohol, polyalkylene polyamine, polypropylene decylamine or polymer starch; or polyethyleneimine, aminoalkyl (meth) acrylate copolymer, poly A reaction product of ethylene imidazoline, a polyamino phthalate having an amine group, a poly(lower alkyleneimine), a polyester having a free carboxyl group, or a cationic resin type pigment dispersant such as chitin. These may be used alone or in combination of two or more. Commercially available resin type pigment dispersants may be, for example, Disperbyk-101, 103, 107, 108, 110, 11 Bu 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, 170, 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 20 (Π, 2020, 2090, 209, 2164 or 2163; or Anti-Terra-U, 203 or 204; or BYK-P104, P104S or 220S; or Lactimon or Lactimon-WS; or resin-based pigment dispersant manufactured by BYK, such as Bykumen; SOLSPERSE-3000, 9000, 13240, 13650, 13940, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, Resin type pigment dispersant manufactured by Lubrizol Co., Ltd., 31845, 32000, 32500, 32600, 34750, 36600, 38500, 41000, 41090 or 53095; or, EFKA-46, 47, 48, 452, LP4008, 4009, LP4010, LP4050 , LP4055, 400, 4 (U, 402, 403, 450, 451, 453, 4540, 4550, LP4560, 120, 150, 15 (U, 1502 or 1503, etc., Ciba Specialty Chemicals) Type pigment dispersant, etc., but is not limited to these, Any resin type pigment dispersant may be used, and these may be used singly or in combination of two or more. 36 321118 201000570 The surfactant may be exemplified by: polyoxyethylene sulphate, lauryl sulphate, styrene-acrylic acid copolymerization The secret salt, hard fat _, silk correction, burning base two fine two continued _, lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, hard acid monoethanolamine, sodium stearate, Anionic surfactants such as monoethanolamine or polyoxyethylene ether alkyl ether phosphate of lauryl sulfide, styrene-propylene copolymer; polyoxyethylene oil test, polyoxyethylene laurate, polyoxygen A non-ionic surfactant such as squama, sulphate, polyoxyethylene sulphate, polyoxyethylene (tetra) anhydride, mono-hardy sulphate (IV) or polyethylene glycol monolaurate; Or a cationic surfactant such as the epoxy Ethylene adduct; a burnt-based mercaptoacetate beet test or the like; or an amphoteric surfactant such as a base. These may be used alone or in combination of two or more. The fine organic pigment coloring composition of the present invention may contain a non-aqueous solvent, whereby the fine organic pigment is sufficiently dispersed in the pigment carrier and is coated on a transparent substrate such as a surface substrate to make the film thickness of the dry test 0. . 2 # m can easily form a color film. Examples of the nonaqueous solvent include trichloropropane, U-butanediol, butylene glycol diacetate, L 4 dioxane, 2-heptanone, 2-mercapto-1,3_hex-3 , 5, 5-trimethyl-2-cyclohexene-butanone, 3, 3, 5-trimethylcyclo-3-methyl-yl-ethyl ester' methyl-1,3-butanediol, 3 Methoxylate 1-butanol, 3-methoxy-3-mercaptobutyl acetate, 3-methoxy 37 321118 201000570 butanol, 3-methoxybutyl acetate, 4-heptanone, -xylene, m-diethylbenzene, m-dichlorobenzene, N,N-dimercaptoacetamide, N,N-dimethyldecylamine, n-butanol, n-butylbenzene, acetic acid N-propyl ester, N-decyl pyrrolidone, o-diphenylbenzene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, second butyl Benzene, tert-butylbenzene, 7-butyrolactone, isobutanol, isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene Alcohol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol mono-telebutyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene Alcohol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, ethylene glycol monodecyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene Alcohol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, two Ethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl Ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether , propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monodecyl ether, propylene glycol monomethyl ether acetate, propylene glycol monodecyl ether propionic acid酉, benzyl alcohol, mercapto isobutyl ketone, nonylcyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate Ethyl ester, propyl acetate or dibasic acid ester, etc., may be used alone or in combination of two or more. The solvent may be used in an amount of from 800 to 4000 parts by weight, preferably from 1,000 to 2,500 parts by weight, based on 100 parts by weight of the pigment dispersion and the pigment in the coloring composition of 38 321118 201000570 parts. Further, the fine organic pigment coloring composition of the present invention may contain a storage stabilizer for stabilizing the viscosity of the composition over time. Examples of the storage stabilizer include tertiary amines such as 4-methylammonium chloride or diethylhydroxyamine such as benzyltrimethylammonium chloride; organic acids such as lactic acid or oxalic acid; and methyl esters of the above organic acids; a catechol such as tributyl pyrocatechol; an organic phosphine such as triphenylphosphine, tetraethylphosphine or tetraphenylphosphine; or a phosphite. The storage stabilizer can be used in an amount of 0 parts by weight based on 100 parts by weight of the fine organic pigment in the fine organic pigment coloring composition.  1 to 10 parts by weight. The fine organic pigment coloring composition of the present invention can be prepared in accordance with the type of ink for gravure offset printing, ink for waterless offset printing, ink for screen printing, solvent development type or development type coloring resist. The development-type coloring resist is obtained by dispersing the fine organic pigment of the present invention in a composition containing a binder resin, a monomer and/or an oligomer, a photopolymerization initiator, and an organic solvent. The binder resin is one or more selected from the group consisting of a thermoplastic resin, a thermosetting resin, and a photosensitive resin, and is a resin containing at least a solvent. When the alkali-developing type coloring resist is adjusted as a fine organic pigment coloring composition, the fine organic pigment of the present invention is dispersed in a resin containing a binder, a monomer and/or an oligomer, a photopolymerization initiator, and an organic solvent. In the composition, or first, the fine organic pigment of the present invention is dispersed in a composition containing a binder resin and an organic solvent to be adjusted into a fine organic pigment dispersion, and the dispersion and the monomer and/or oligomerization are further And the photopolymerization start 39 321118 201000570 agent mixed, you can prepare. It is limited to the color characteristics of the soil film, the dispersion stability of the pigment, and the convenience between the formulation adjustments. ^(4) The method of the touch is better than 1 and the material dispersion is: the pigment dispersion itself is a microscopic organic pigment of the invention, and may contain a part of the monomer and/or oligomerization ▲ ', as appropriate Part of the binder resin and/or organic solvent is mixed during the adjustment of the coloring resist. The proportion of the fine organic pigment based on the total amount of the solid content of the fine organic pigment coloring composition is preferably from 5 to 7 g% by weight, more preferably from 20 to 50% by weight. Further, in the fine organic pigment coloring composition of the present invention, a dye may be contained in a range in which heat resistance is not lowered for color adjustment. , 〇α The fine organic pigment coloring composition of the present invention is removed by centrifugation, Tingjie filtration, and membrane overfeeding means to remove the above coarse particles (preferably coarse particles of ^ / zm or more). It is better for coarse particles above 5yffl) and dust. [Examples] The present invention will be more specifically described by the following examples, but the scope of the invention is not limited to the examples below. In addition, "parts and "%" in the examples mean "parts by weight" and "% by weight", respectively. (Measurement method) <Particle size of the pigment> First, the image analysis type particle size distribution measurement software (M0UNTECH) was obtained by taking a photographic electron microscope (made by Nippon Electronics Co., Ltd.) at 321118 40 201000570 The projected area of each particle of the obtained image is obtained by dividing the sum of the projected areas of the particles by the number of particles, thereby calculating the average particle diameter of the pigment particles. <Amine value of resin> The amine value of the resin was determined by potentiometric titration using a 甩0·1 Ν aqueous hydrochloric acid solution, and converted to the equivalent of potassium hydroxide. The amine value of the following resin solution indicates the amine value of the solid content. <4 grade salt value of resin> The grade 4 ammonium salt value of the resin is 5% potassium chromate aqueous solution as an indicator, with 0. After the titration of 1 Ν silver nitrate aqueous solution is obtained, it is converted into potassium pentoxide: when - 罝. The 4-grade ammonium salt value of the following resin solution represents the solid ammonium salt value of the solid form. <Acid value of resin> The acid value of the resin is 0. 1 Ν potassium hydroxide • ethanol solution and determined by potentiometric titration. The acid value of the resin solution described below represents the acid value of the solid component. <The weight average molecular weight of the resin ( \)> The weight average molecular weight of the resin (Α) was measured by gel permeation chromatography (GPC's manufactured by Tosoh Corporation). When measured by GPC, it has an amine group, and it is used as a solvent for the addition of triethylamine to tetrahydrofuran, and TSK-GEL Super manufactured by Tosoh Corporation is used. Multip〇reHZ-M 2 string, measured in standard polystyrene, is insoluble in tetrahydrogen cough and soluble in 50/50 solvent of sterol/water, then TSK-made by Tosoh Corporation GELG5000PWxl-CP column and measured in standard poly Ethylene bromide conversion. 41 321118 201000570 <Weight Average Molecular Weight of Acrylic Resin> The weight average molecular weight (Mw) of the acrylic resin used as the binder resin is a gel permeation chromatograph (GPC; manufactured by Tosoh Corporation) equipped with an RI detector. Determination. In the GPC measurement, a TSKgel column (manufactured by Tosoh Corporation) was used, and THF was used as a developing solvent and measured in terms of standard polystyrene. <Method for Forming Colored Film> The film was formed by using a fine organic pigment to color the composition, and the number of rotations was arbitrarily changed by a spin coater to make the film thickness of the dried film 2.  0//m. After coating, it was dried in a hot air oven at 80 ° C for 30 minutes. <Comparative> Separate the polarizing plates on both sides of the substrate of the color film of the former, so that the polarization axes of the two polarizing plates are parallel to each other, and the brightness of the light passing through the polarizing plate and the light passing through the other polarizing plate (Lp) is measured by a luminance meter. Next, the polarizing plates superposed on both sides of the substrate are arranged such that the polarization axes of the two polarizing plates are perpendicular to each other, and the backlight is incident from one polarizing plate side, and the brightness (Lc) of the light passing through the other polarizing plate is used for brightness. Measurement. The comparison value Lp/Lc was obtained using the obtained measured luminance value. The measurement is performed in the normal direction of the substrate. In addition, both of the polarizing plates used "NPF-SEG1224DU" (manufactured by Nitto Denko Corporation). In the luminance meter, the brightness was measured under the condition of a 2° field of view using "leg-5A" (manufactured by Topcon Corporation). Further, the higher the contrast, the more excellent the transparency of the colored film (coloring composition). <Half-peak width> The dried pigment was pulverized with an 80 mesh metal mesh and subjected to X-ray measurement. 42 321118 201000570 X-ray diffraction spectrum was measured according to the following conditions. . Device: Rigaku uitima2001. X-ray source: CuK ο: . Voltage: 40kV. Current: 40mA. Measuring range: 5.  0° to 35.  0. • Step angle: 0.  01. As a result of the measurement, data processing was carried out under the following conditions to obtain a half width (Δ2 Θ °). Here, the half width is defined as any 2θ. In the peak, a Bragg angle value defined by the peak width of the intensity position at which the intensity of the X-ray diffraction intensity is 1/2 is obtained. 2 θ Ί1 of the quinophthalone pigment.  〇 to 13.  7. , 24·5 to 27.  0. 27.  0 to 29.  3; 2 θ of the two H phthalocyanine pigment. 4.  0 to 7.  0. ,8.  〇 to 12.  0°, 15. 5 to 18. 5. ,twenty four.  5 to 27.  5. 2 phthalocyanine pigments. 5· 0 to 12.  7. ; copper halide phthalocyanine pigment 2 (9. 15.  5 to 18. 3 21.  6 to 22.  The 7 connected lines are used as the bottom line (base 1 ine) for background removal. After the data is processed, the maximum intensity in each range is selected to obtain the half width. When there are complex peaks, the average value is taken as the half width. The half-peak width and salt as determined here should be considered to correspond to the size of the particles. That is, when the half width is large, the particles are small. <retardation> The normal direction and inclination 45 of the substrate on which the color film is formed. The azimuth is incident on the elliptically polarized light, and the spectroscopic Ellipsometer "M-220" (manufactured by JASC0 43321118 201000570 Corporation, Japan) is used for the penetrating light system, and the green substrate is 575 to 635 nm on the red substrate. In the wavelength range of 535 to 560 nm, the blue substrate is 41 〇 to 520 nm, the yellow substrate is 535 to 635 nm, and the purple substrate is 41 〇 to 520 nm, Δ (in nm) per 1 nm is measured. When this a = ,, it is obtained by calculating the area (unit: nm2) of the domain formed by the spectrum of Δ in the respective wavelength ranges. If the retardation value is increased, the transmitted light produces a phase difference and indicates that the viewing angle is inferior. Therefore, it is preferably 30 or less, more preferably 2 Å or less. <Synthesis Method of Resin> [Synthesis Example 1] Ethyl ketone 62 was fed into a four-necked flask equipped with a thermometer, a stirrer, a distillation tube, and a cooler. 4 parts were heated to 75 c under a nitrogen stream. On the other hand, in the dropping funnel (droppingfunnel) fed thiol methacrylate 19.  5 parts, n-butyl methacrylate 11.  7 parts, thioglycolic acid 2-ethylhexanoic acid 11. 7 parts, diethylene glycol monomethyl acrylate vinegar (manufactured by 曰本油月曰, trade name: Blenmer PE-go)?  8 parts, dimethylaminoethyl methacrylate 27. 3 parts, 2,2,-azobis(2,4-di-2-pentyl nitrile)  Seven parts and 1.5 parts of methyl ethyl ketone were placed in a four-piece split flask and consumed for two hours. After the completion of the dropwise addition for 2 hours, the solid content was confirmed to be 98% or more and the weight average molecular weight (Mw) was 7,130, and it was cooled to 50 °C. In this regard, additional gangue chlorine 22.  0 parts, ethanol 22. Part G was allowed to react at 5 G ° C for 2 hours, and then heated to 8 (TC, i, and reacted for 2 hours in i hours. Thereafter, 15 parts of diethylene glycol was added, and the pressure was reduced at (10) C. The crane removes ethanol and methyl ethyl hydrazine, and replaces the solvent with diethylene glycol. In this way, the resin component is obtained by weighting the tree 321118 44 201000570 fat solution 1 (amine value 3mgK0H/g, grade 4 ammonium salt value) 97 mgK〇H/g) [Synthesis Example 2] 8 parts of methyl ethyl ketone was fed into a four-part sinter with a thermometer, a stirrer, a distillation tube, and a cooler, and the temperature was raised under a nitrogen stream. Feeding decyl methacrylate, 1 part by weight of n-butyl methacrylate, 5 parts of 2-ethylhexyl methacrylate, 16 parts of PE-90, Kayamer PM-21 (Japanese medicine) Made by the company: ε_caprolactone 1 molar added to 2-hydroxyethyl methacrylate phosphate) 10 parts, dimethylaminoethyl methacrylate 25 parts, 2, 2,-azo double (2 6 parts of 4_dimercapto valeronitrile and 2 parts of methyl ethyl ketone, which were evenly distributed and placed on a four-piece split flask and took 2 hours to drip in. After 2 hours of instillation, From the solid-column, it was confirmed that the polymerization yield was 98% or more, and the weight average molecular weight (Mw) was condensed to 5 〇〇C.  8 parts, 13 parts of ethanol, and reacted at 5 (TC for 2 hours, then heated to other C' for 1 hour, and reacted for 2 hours. The resin solution was concentrated, and the solvent was replaced with ethylene glycol mono The vinegar acetate was used to obtain a resin solution 2 having a solid content ratio of Μ% by weight (amine value: 29 mg K0H/g, 4 铋 瞒 * * 4, and 铋 salt value: 62 mg KOH/g). [Synthesis Example 3] 80 parts of methyl ethyl ketone were fed into a four-piece separate flask equipped with a thermometer, a stirrer, a sputum, a sputum, a sputum, a smelter, and a cooler.  0 parts, Sparteine 2.  8 parts and ethyl brominated butyl isobutyrate 1. 9 parts and the temperature was raised to 4 (TC. Into the sulphide steel) under a nitrogen stream]] 8 孔 丄 J丄·丄份 'heated to 75. Deag start polymerization. After 3 hours of polymerization' using the polymerization solution as a sample, The solid content of the polymerization confirmed the fact that the polymerization yield was 95% or more η tongue θ Κ ° and the reset average molecular weight (Mw) was 321118 45 201000570 6860, and the addition of decyl methacrylate was added. 0 copies and MEK20.  0 parts were further polymerized. After 2 hours, the solid content of the polymerization solution was confirmed to be 97% or more, and the mixture was cooled to room temperature and the polymerization was stopped. 100 parts of the obtained resin solution was diluted with 100 parts of ethyl ketone, 60 parts of a cation exchange resin "Diaion PK228LH (manufactured by Mitsubishi Chemical Corporation)" was added, and the mixture was stirred at room temperature for 1 hour, and then "Kyoward 500SN" as a neutralizing agent was added. (manufactured by Kyowa Chemical Industry Co., Ltd.)" 6 parts and stirred for 30 minutes. The cation exchange resin and the adsorbent are removed by filtration to remove the residue of the polymerization catalyst. Further, the resin solution was further concentrated and the solvent was substituted with ethylene glycol monomethyl ether acetate to obtain a resin solution 3 having a solid content ratio of 50% by weight (amine value: 29 mg K0H/g, and fourth-order ammonium salt value: OmgKOH/g). [Synthesis Example 4] An ethylene glycol monoterpene ether acetate fraction was fed into a four-port separation furnace equipped with a thermometer, a stirrer, a distillation tube, and a cooler, and the temperature was raised to 90 ° C under a nitrogen stream. On the other hand, 40 parts of methyl methacrylate, n-butyl methacrylate, 1 part of methacrylic acid, and Placcel FM5 (made by Daicel Chemical Industry Co., Ltd.: ε_caprolactone 5) were fed into a dropping funnel. Moen-added 2-hydroxyethyl methacrylate) 1 part by weight, decyl methacrylate.  〇part, 2, 2'-azobis(2,4-dimethylvaleronitrile) 6 parts and ethyl alcohol monomethyl ether acetate 2 〇 份 'make it evenly after the device is installed in four separate liters It took 2 hours to drip in. After continuously stirring at the same temperature for 2 hours, it was confirmed that the polymerization yield was 98% or more and the weight average molecular weight (Mw) was 6790, and then an appropriate amount of ethylene glycol monomethyl ether acetate was added to obtain a solid form. A resin solution 4 having a ratio of 50% by weight (amine value nmgK〇H/g, 4 46 321118 .   The 201000570 grade ammonium salt value is OmgKOH/g). [Synthesis Example 5] 80 parts of ethylene glycol monomethyl ether acetate was fed into a four-necked flask equipped with a thermometer, a stirrer, a distillation tube and a cooler, and the temperature was raised to 90 ° C under a nitrogen stream. On the other hand, 40 parts of methyl methacrylate, 20 parts of n-butyl methacrylate, 10 parts of methacrylic acid, 30 parts of 2-hydroxyethyl methacrylate, 2, 2' - were fed into the dropping funnel. 6 parts of azobis(2,4-dimethylvaleronitrile) and 20 parts of ethylene glycol monoterpene ether acetate were uniformly placed in a four-part separable flask and dropped in 2 hours. After the completion of the dropwise addition, the mixture was continuously stirred at the same temperature for 2 hours, and the solid content was confirmed to be 98% or more and the weight average molecular weight (Mw) was 7050, and then an appropriate amount of ethylene glycol monoterpene ether acetate was added. Further, a resin solution 5 having a solid content ratio of 50% by weight (an amine value of 0 mgKOH/g and a 4-grade ammonium salt value of 0 mgKOH/g) was obtained. [Synthesis Example 6] Methyl ethyl ketone 62 was fed into a four-necked flask equipped with a thermometer, a stirrer, a distillation tube, and a cooler.  4 parts were heated to 75 ° C under a nitrogen stream. i' On the other hand, the oxime methacrylate was fed into the dropping funnel 19.  5 parts, n-butyl methacrylate 15.  6 parts, 2-ethylhexyl methacrylate 15.  6 parts, diammonium ethyl methacrylate 27. 3 parts, 2,2'-azobis(2,4-dimethylpentanenitrile) 4.  7 parts and acetophenone 15. Six parts were allowed to stand evenly and placed on a four-part separable flask and dropped for 2 hours. Two hours after the completion of the dropwise addition, the solid content was confirmed to be 98% or more and the weight average molecular weight (Mw) was 7,380, and the mixture was cooled to 50 °C. Add benzyl chloride to this.  0 parts and ethanol 22.  After 0 hours of reaction at 50 ° C for 2 hours, the temperature was raised to 80 ° C when 1 small 47 321118 201000570 was used, and the reaction was further carried out for 2 hours. Thereafter, 150 parts of diethylene glycol was added, and ethanol and ethyl ketone were distilled off at 100 ° C under reduced pressure, and the solvent was replaced with diethyl diol. In this manner, a resin solution 6 having a resin component of 40% by weight (an amine value of 3 mg K0H/g and a 4-grade ammonium salt value of 97 mg K0H/g) was obtained. [Synthesis Example 7] Ethyl ketone was fed into a four-necked flask equipped with a thermometer, a stirrer, a distillation tube, and a cooler.  0 parts and the temperature was raised to 75 ° C under a nitrogen stream. On the other hand, the methyl methacrylate was fed into the dropping funnel.  3 parts, n-butyl methacrylate 10.  7 parts, 2-ethylhexyl methacrylate 10.  7 parts, diammonium methacrylate.  6 parts, 2, 2'-azobis(2,4-dimercapto valeronitrile) 4.  7 parts and acetophenone 14. Three portions were allowed to stand evenly and placed on a four-piece separable flask and dropped for 2 hours. Two hours after the completion of the dropwise addition, the solid content was confirmed to be 98% or more and the weight average molecular weight (Mw) was 7090, and the mixture was cooled to 50 °C. Add benzyl chloride to this.  7 parts and ethanol 28.  After 7 hours of reaction at 50 ° C for 2 hours, the temperature was raised to 80 ° C over 1 hour, and the reaction was further carried out for 2 hours. Thereafter, 150 parts of diethylene glycol was added, and ethanol and ethyl ketone were distilled off at 100 ° C under reduced pressure, and the solvent was replaced with diethyl diol. In this manner, a resin solution 7 having a resin component of 40% by weight (an amine value of 5 mgKOH/g and a 4-grade ammonium salt value of 127 mgKOH/g) was obtained. [Synthesis Example 8] Methyl ethyl ketone 62 was fed into a four-necked flask equipped with a thermometer, a stirrer, a distillation tube, and a cooler.  4 parts were heated to 75 ° C under a nitrogen stream. On the other hand, the methyl methacrylate was fed into the dropping funnel.  8 parts, n-butyl methacrylate 6.  6 parts, 2-ethylhexyl methacrylate 6.  6 parts, 48 321118 201000570 diammonium methacrylate 42.  7 parts, 2, 2,-azobis(2,4-dimercapto valeronitrile) 4.  Seven parts and 13 parts of methyl ethyl ketone were evenly distributed, and the apparatus was placed on a four-piece split flask and dropped in 2 hours. Two hours after the completion of the dropwise addition, the solid content was confirmed to be 98% or more and the weight average molecular weight (Mw) was 6,480, and it was cooled to 5 (rc. benzyl chloride was added thereto.  4 parts and ethanol 22.  0 copies, at 5〇. (: After reacting for 2 hours, it was heated to 8 CTC for 1 hour, and then allowed to react for 2 hours. Thereafter, 150 parts of diethylene glycol was added and the mixture was distilled at 1 Torr. Ethyl ketone was replaced with diethylene glycol, and a resin solution 8 having a resin component of 4% by weight (an amine value of 3 mgKOH/g and a quaternary ammonium salt value of 152 mgK0H/g) was obtained. ] Feeding methyl ethyl ketone 62 in a separate flask equipped with a thermometer, stirrer, distillation tube and cooler.  4 parts were heated to 75 c under a nitrogen stream. On the other hand, methyl methacrylate was fed into the dropping funnel. } parts, n-butyl methacrylate 3.  Oxime, 2-ethylhexyl methacrylate  Oxime, dimethylaminoethyl methacrylate 48. 7 parts, 2,2' _ azobis(2,4-dimethylvaleronitrile) 4.  7 parts and methyl ethyl ketone 12. Two parts, which were made uniform, were placed on a four-piece split flask and took 2 hours to drip. Two hours after the completion of the dropwise addition, the solid content was confirmed to be 98% or more and the weight average molecular weight (10) was about 7,140, and the temperature was lowered to the order. Add a base gas to this.  2 parts and ethanol 39.  2 copies, at 50. After the reaction was carried out for 2 hours, the temperature was raised to 8 Gt in an hour, and the reaction was allowed to proceed for 2 hours. Thereafter, U0 portion of diethylene glycol was added and ethanol and methyl ethyl ketone were distilled off at 100 t; and under reduced pressure, and the solvent was replaced with diethyl diol. In this manner, a resin having a resin component of 4% by weight was obtained. 321118 49 201000570 Lok 9 (an amine value of 3 mg K〇fI/g, a 4-grade ammonium salt value of 174 mgK〇H/g). [Synthesis Example 10] In a four-port split flask equipped with a thermometer, a scrambler, a steaming crane, and a cooler, the difference was given to (4) (10). 9 parts were heated to 75 c under a nitrogen stream. In a separate container, 2 parts of 2,2,-azobis(2,4-difluorenyl valeronitrile) was prepared and dissolved in a starting solution of 2 parts of methyl ethyl ketone. Thereafter, a methyl methacrylate methacrylate was fed into the dropping (four) bucket.  5 parts, 15 6 parts of n-butyl methacrylate, methyl: 2' ethylhexyl olefin. 6 parts, methacryloxyethyl dimethyl sulphate chloride 49. Three parts and 211 parts of methanol were placed, and the dropping funnel was placed on a four-necked flask and dripped for 2 hours. At the same time, 1/13 of the amount of the starter solution was added to the flask every ίο minutes, :, 』, and 13-person. Two hours after the completion of the dropping, the fact that the polymerization yield was 98% or more was confirmed from the solid content. To this, 15 parts of diethylene glycol was added and 纟 (10). ◦ 减 减 减 下 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤 鹤g7mgK〇H/g). [Synthesis Example 11] Isopropyl alcohol was prepared in a four-necked flask equipped with a thermometer, a stirrer, a steam tube, and a cooler. 9 parts and heated to 75 L under nitrogen flow in a separate container to prepare 2,2,-azobis(2,4-dimethylvaleronitrile) 5 ^ gluten in the starting agent of methyl ethyl -2- () Solution. Thereafter, methyl methacrylate n was fed into the dropping funnel. i parts, n-butyl methacrylate (1) parts, 2 acrylic acid ^ ethylhexg | 11; 1 part 'mercapto acrylic acid vinegar parts, earth propylene oxy dimethyl ammonium chloride 36.  1 part and methanol 36.  1 part, 321118 50 201000570 After making it, the dropping (four) bucket was placed on a four-piece split flask and it took 2 hours to drip. While instilling, an amount of 1/13 of the initiator solution was added to the flask every 10 minutes for a total of 13: owed. Two hours after the completion of the dropwise addition, the fact that the polymerization yield was 98% or more was confirmed from the solid content. To this, 150 parts of diethylene glycol was added, and decyl alcohol, isopropanol, and methyl ethyl ketone were distilled off under reduced pressure and reduced pressure to replace the solvent with diethylene glycol. In this manner, a resin solution 11 having a resin component of, for example, a weight % (an amine value of 〇mgK〇H/g and a 4-grade ammonium salt value of 97 mgKOH/g) was obtained. [Synthesis Example 12] 93 parts of isopropanol was fed into a four-necked flask equipped with a thermometer, a stirrer, a distillation tube and a cooler, and the temperature was raised to a pore °c under a nitrogen stream. Prepare 2,2'-azobis (2,4-dimethyl ketone) in a separate container. Dissolve the initiator solution in 2 parts of methyl ethyl ketone. Then, feed the sulfhydryl group into the dropping funnel. Acrylate acrylate 24.  6 parts, n-butyl methacrylate 19.  7 parts, 2-ethylhexyl methacrylate 19.7 parts, mercaptopropenyloxy-trimethylammonium chloride 36. 0 parts and 36 parts of methanol were evenly distributed, and the dropping apparatus was placed on a four-piece split flask and dropped in 2 hours. At the same time as the dropwise addition, the amount of the initiator solution was added to the flask every 10 minutes, and the addition was carried out 13 times. Two hours after the end of the dropwise addition, the fact that the polymerization yield was 98% or more was confirmed from the solid content. To this, diethylene glycol ι 5 parts were added, and methanol, isopropyl alcohol, and methyl ethyl ketone were distilled off under the conditions of &apos;, and, and diethylene glycol was used instead of the medium. In this manner, a resin solution having a resin component of 4% by weight was obtained: a value of 0 mg/g, and a 4-grade ammonium salt value of 97 mg K0H/g). Amine <Preparation of Acrylic Resin Solution> 51 321118 201000570 Into the reaction solution, 800 parts of propylene glycol monoethyl ether acetate was fed, and while nitrogen fluoride was injected into the container, it was heated to 1, and it was dripped in 1 hour at the same temperature. Acrylic acid 80.  Oxime, decyl acrylate 85.  Oxime, butyl methacrylate 85. 0 parts and 2, 2,-azobisisobutyronitrile 10. A mixture of 0 parts was subjected to polymerization. After the dropwise addition, the reaction was carried out for 3 hours at 1 〇〇c&gt;c, and azobisisobutyronitrile was dissolved in 5 parts of propylene glycol monoethyl ether acetate.  The mixture was further reacted at 0 °' for 1 hour to obtain an acrylic resin solution having a weight average molecular weight (Mw) of 40,000. <Pigment Derivative> The pigment derivative used in the examples is a dye derivative represented by the following formula (1丨) to (15). • Diketopyrrolopyrrole pigment derivative 52 321118 201000570 Formula (11): • Anthrone-based pigment derivatives General formula (12): .Benzamidazolone-based pigment derivative % General formula (13): • Copper emenee pigment derivative 53 321118 4 201000570 Formula (14) z Cu-Pc : copper phthalocyanine residue • dye derivative of the second B or the like. General formula (15): [Example 1] A kneaded product of the following composition was placed in a 15,000-volume three-arm planetary mixer (Tri-mix), and kneaded at a treatment temperature of 40 ° C for 8 hours at a revolution of 19 rpm and a rotation of 57 rpm. Diketone-based pyrrolo-n-pyroloic pigment (CI Pigment Red 254; "IgbaFOR RED B-CF" manufactured by Ciba Specialty Chemicals Co., Ltd.) 450 parts * Resin solution 1 141 parts * 4,500 parts of sodium chloride · 2 Alcohol (DEG) 714 parts The above-obtained kneaded material was taken out from a 30,000 parts of a 1% sulfuric acid solution at 70 ° C, and after being stirred for 1 hour, it was filtered, washed with water, dried, and pulverized at 54 321118 201000570 to obtain a fine diketone. The base σ is more than D and the pigment 1 is. Next, the mixture of the following composition containing the obtained fine diketopyrrolopyrrole pigment was uniformly stirred, and then oxidized cerium beads having a diameter of 1 mm were used, and dispersed in a bead mill for 5 hours, and then treated with 5 // in i The filter was filtered to prepare a red fine organic pigment dispersion 1.份份的丙酮含曱酯 acetate (0 parts • acrylic resin solution 40. 0 parts. propylene glycol monoterpene ether acetate (1. 0 parts • diketone π) PGMAc) 50. 0 parts The mixture of the following composition containing the obtained red fine organic pigment dispersion 1 was stirred and mixed to be uniform, and then filtered by a 1/zm filter, left 丄, _ 々Λΐι/ I. - UU -4-c· Ο/Ί Λ— _L, »L/_ 1 / Λ _ Μ ΥΚ LT 曰/ -rtil ttr-» 七Τ ϊ 聚 聚 取? Gongba? Tian Lingweiyan Tpf? And wind sweat? 7丄,? Gong Ba Yu Wang chooses the page color to the wide and wild π I). • Red fine organic pigment dispersion I 45. 0 parts. Acrylic resin solution 15. 0 parts • Trioxin propane triacrylate ("ESTER ΑΤΜΡΤ" manufactured by Shin-Nakamura Chemical Co., Ltd.) 9. 0 parts • Photopolymerization start Agent 2-mercapto-2-1^-morphinyl (4-indolylthiophenyl)-propyl-butanone ("ICGACURE 907" manufactured by Ciba Specialty Chemicals Co., Ltd.) 2·0 parts•sensitizer 4, 4'-bis(diethylamino)benzophenone ("EAB-F" manufactured by Hodogaya Chemical Industry Co., Ltd.) 0. 2 parts. Propylene glycol monoterpene ether acetate 28.8 parts [Example 2] 55 321118 201000570 The kneaded material of the following composition was placed in a three-arm planetary stirring apparatus of 15 () (10) capacity parts and kneaded at a rpm of 19 rpm and a rotation number of 57 rpm at a temperature of 35 ° C for β hours. 254; Cibafine 450 parts 90 parts 4500 parts 720 parts. Diketopyrrolopyrrole pigment (c. I pigment Red Chemical Company "IRGAFOR RED B-CF") • Resin solution 2 • Chlorinated sodium • Ethylene The alcohol thus obtained was subjected to the same treatment as in Example , to a fine diketone base and finely divided. "In addition to the fine two ^ ° ratio slightly depends on 1 with a fine two base material and pigment 2 instead of:: divergence; and the same treatment, made of red fine organic pigment 7 fine organic pigment dispersion 1 In addition, the same as the implementation of 1 = 2) made of red fine organic fine 4 composition 2 (red (four) development type resistance [Example 3] Shi 2 = liquid 1 _ changed to 45 copies, into _ ^ 5, to the fine diketopyrrolopyrrole pigment 3, the fine two shouting pigments] in addition to the fine material 3, the same as the implementation of the ί, organic pigments r3, and then Red finely carried out and implemented; except for the fine axial dispersion 1 and the same treatment as the one made of red fine organic pigment 321118 56 201000570 3 (red positive development resist 3 ). 4) The same treatment as in Example 2 was carried out except that the amount of the resin solution 2 was changed to 180 parts, and the fine diketone group π ratio p was obtained in a ratio of σ to each of the pigments 4. Next, in addition to the fine diketone group The pyrrolopyrrole pigment 1 is replaced by a fine diketopyrrolopyrrole pigment 4, In the same manner as in Example 1, the red fine organic pigment dispersion 4 was prepared, and the same treatment as in Example 1 was carried out except that the red fine organic pigment dispersion 4 was replaced with the red fine organic pigment dispersion 4. Red fine organic pigment composition 4 (red developable resist material 4). [Example 5] The kneaded material of the following composition was placed in a 15000-volume three-arm planetary mixer at a revolution of 19 rpm and a rotation of 57 rpm. The number of rotations was kneaded for 6 hours at a treatment temperature of 35 ° C. • Diketopyrrolopyrrole pigment (CI. Pigment Red 254; "ICGAFOR RED B-CF" manufactured by Ciba Specialty Chemicals Co., Ltd.) 450 parts. Resin solution 3 71 parts • 4,500 parts of sodium chloride, 765 parts of ethylene glycol, and the thus obtained kneaded material was subjected to the same treatment as in Example 1 to obtain a fine diketopyrrolopyrrole pigment 5. Next, in addition to the fine diketopyrrolopyrrole The pigment 1 was replaced with the fine diketopyrrolopyrrole pigment 5, and the same treatment as in Example 1 was carried out to prepare a red fine organic pigment dispersion 5, in addition to being finely red organic The material dispersion 5 was replaced with 57 321118 201000570 red fine organic pigment dispersion 1 and subjected to the same treatment as in Example 1 to prepare red fine organic pigment composition 5 (red developable resist material 5). Example 1 A kneaded product of the following composition was placed in a 15,000-volume three-arm planetary spoiler, and kneaded at a processing temperature of 35 ° C for 6 hours at a revolution of 19 rpm and a rotation of 57 rpm. A 吼 吼 吼嘻 吼嘻 吼嘻 pigment (dpigment 254; Ciba Specialty Chemicals made "I'RGAFOR RED B-CF") 450 parts 90 parts 4500 parts 810 parts • resin solution 4 • chlorinated steel. Glycol will The kneaded product thus obtained was subjected to the same treatment as in Example , to obtain a fine diketopyrrolopyrrole pigment 6. Then, in addition to the treatment of the fine diketopyrrolopyrrole pigment oxime with the fine diketopyrrolopyrrole pigment 6, the same procedure as in Example 进 was carried out to prepare a red fine organic pigment dispersion 6, in addition to The red fine organic pigment composition 6 (red alkaline developing material 6) was prepared by the same treatment as in Example 之外 except that the red fine organic pigment dispersion 6 was used instead of the red fine organic pigment dispersion 1. [Comparative Example 2] A kneaded material of the following composition was placed in a three-arm planetary mixer of a capacity of 15 Torr, and kneaded at a temperature of 1 rpm and a rotation of 57 rpm at a temperature of 4 Torr for 6 hours. 321118 • 58 201000570 • Diketopyrrolopyrrole pigment (CIPigmeni: Red 254; “IgbaFOR RED B-CF” by Ciba Specialty Chemicals) 450 parts • Resin solution 5 90 parts. Sodium chloride 4500 parts. 800 parts of ethylene glycol The thus obtained kneaded product was subjected to the same treatment as in Example 1 to obtain a fine diketopyrrolopyrrole pigment 7. Next, the same treatment as in Example 1 was carried out except that the fine diketopylpyrazole pigment 1 was replaced with the fine diketopipylidene 11 fluorene pigment 7 to prepare a red fine organic pigment dispersion 7 Further, in the same manner as in Example 1, except that the red fine organic pigment dispersion 7 was used instead of the red fine organic pigment dispersion 1, a red fine organic pigment composition 7 was prepared (red invisible developing resist) Material 7). [Comparative Example 3] A kneaded product of the following composition was placed in a double arm kneader of a capacity of 2,000 parts and kneaded at a temperature of 35 ° C for 6 hours at a temperature of 35 rpm. • Diketo η piroxan n 嘻 pigment (CIPigment Red 254; Ciba Specialty Chemicals Co., Ltd. “IRGAFOR RED B-CF”) 810 parts • Diketone η Biha and π piroxime pigment derivative 90 Parts: 9000 parts of sodium chloride. A mixture of the thus obtained kneaded material was subjected to the same treatment as in Example 1 to obtain a fine diketopyrrolopyrrole pigment 8. Next, the same treatment as in Example 1 was carried out except that the fine diketone group 321118 59 201000570 pyrrolopyrrole pigment 1 was replaced with the fine diketopyrrolopyrrole pigment 8, and a red fine organic pigment dispersion 8 was prepared. The red fine organic pigment composition 8 (red alkaline developing resist material 8) was prepared by the same treatment as in Example 1 except that the red fine organic pigment dispersion 8 was used instead of the red fine organic pigment dispersion 1. . [Comparative Example 4] A kneaded product of the following composition was placed in a two-arm kneader of 20,000 parts by volume, and kneaded at a treatment temperature of 35 ° C for 6 hours at a rotation number of 30 rpm. • Diketone oxime and hip hop pigment (CI Pigment Red 254; “IgbaFOR RED B-CF” by Ciba Specialty Chemicals) 900 parts • 9000 parts of sodium chloride • 1800 parts of ethylene glycol The same treatment as in Example 1 was carried out to obtain a fine diketopyrrolopyrrole pigment 9. Next, the same treatment as in Example 1 was carried out except that the fine diketopyrrolopyrrole pigment 1 was replaced with the fine diketopyrrolopyrrole pigment 9, and a red fine organic pigment dispersion 9 was obtained, in addition to The red fine organic pigment dispersion 9 was treated in the same manner as in Example 1 except that the red fine organic pigment dispersion 9 was replaced with the red fine organic pigment dispersion 9 to prepare a red fine organic pigment composition 9 (red positive development type resist material 9). [Comparative Example 5] A mixture of the following composition containing the fine diketopyrrolopyrrole pigment 8 obtained in Comparative Example 3 was uniformly mixed, and then dispersed in a bead mill using a oxidization error of 60 mm 321118 201000570 beads of 1 mm in diameter. After 5 hours, the mixture was passed through a 5 (four) wire to prepare a red fine organic pigment dispersion 10. 9. 0 parts 1.0 parts 1. 0 parts 39. 0 parts 50. 0 parts • fine diketo oxime 11 each bismuth pigment 8 • diketopipyrrolopyrazine pigment derivative • resin solution 1 • acrylic acid Resin solution: propylene glycol monomethyl ether acetate (PGMAc) In addition to the red fine organic pigment dispersion 1 代# generation red fine organic pigment dispersion 1, the same treatment as in Example i was carried out to make red The fine organic pigment composition was 1 Å (red alkaline developing resist 10). [Comparative Example 6] A kneaded product of the following composition was placed in a three-arm planetary mixer of 15,000 parts by volume, and kneaded at a temperature of 351 for 6 hours at a revolution of 19 rpm and a rotation number of 57 rpm. . Diketopipyrrolopyrrole pigment (CI Pigment Red 254; "IgcoFOR RED B-CF" manufactured by Ciba Specialty Chemicals Co., Ltd.) 450 parts. AJISPER PB821 (Ajinomoto Fine-Techno); a lactone-based basic functional group copolymer having an amine value of 10 mgKOH/g, an acid value of 17 mgKOH/g) 45 parts, sodium chloride 4,500 parts, and ethylene glycol 810 parts. The kneaded product thus obtained was subjected to Example 1 The same treatment gave a fine diketopyrrolopyrrole pigment 1 〇. Next, the same treatment as in Example 1 was carried out except that the fine diketone group 61 321118 201000570 pyrrolopyrrole pigment 1 was replaced with the fine diketopyrrolopyrrole pigment 10, and a red fine organic pigment dispersion 11 was prepared. The same treatment as in Example 1 was carried out except that the red fine organic pigment dispersion π was used instead of the red fine organic pigment dispersion 1 to prepare a red fine organic pigment composition 11 (red inspective resist material 11) . The fine diketopyrrolopyrrole pigments 1 to 10 and the red fine organic pigment composition 11 (red alkaline developing resist materials 1 to 11) produced by the method of the above examples were respectively subjected to measurement of the average particle diameter of each pigment. , contrast, and delay values are shown in Table 1. [Example 6] A kneaded product of the following composition was placed in a 15,000-volume three-arm planetary mixer (manufactured by Inoue Seisakusho Co., Ltd.), and kneaded at a processing temperature of 60 ° C for 12 hours at a revolution of 19 rpm and a rotation of 57 rpm. • Cyclohexanone pigment (CI Pigment Yellow 138; “Paliotoi Yellow K0961HD” by BASF) 441 parts. Benzo sigmazone derivative 9 parts • Resin solution 1 126 parts • Chlorinated steel 4500 parts • Two 1246 parts of ethylene glycol The above-obtained kneaded product was taken out from a 32000 parts of a 1% sulfuric acid solution at 70 ° C, and after stirring for 1 hour, it was filtered, washed with water, dried, and pulverized to obtain a fine quinacridone pigment 1. Next, the mixture of the following group 63321118 201000570 containing the obtained fine quinacridone pigment 1 was uniformly stirred, and then dispersed in a bead mill for 5 hours using a cerium oxide bead having a diameter of 1 mm, and filtered at 5 /zm. The device was filtered to prepare a yellow fine organic pigment dispersion 1. • Fine ketone pigment 1 5. 3 parts • Quinone ketone derivative 1.0 part • Acrylic resin solution 7. 0 parts • Propylene glycol monoterpene ether acetate 36.8 parts, in addition to yellow fine organic pigment The dispersion 1 was replaced with the red fine organic pigment dispersion 1 and subjected to the same treatment as in Example 1 to prepare a yellow fine organic pigment composition K-yellow-developing resist material 1) 实施 [Example 7] The kneaded product of the composition was placed in a three-arm planetary mixer (manufactured by Inoue Seisakusho Co., Ltd.) of 15,000 parts by volume, and kneaded at a processing temperature of 60 ° C for 12 hours at a revolution of 19 rpm and a rotation of 57 rpm. • Brewing ketone pigment (CI Pigment Yellow 138; “Paliotol Yellow K0961HD” by BASF) 441 parts • 9 parts of benzoxanthone ketone pigment derivative • Resin solution 6 123 parts • 4,500 parts of chlorinated steel • The thus obtained kneaded material was subjected to the same treatment as in Example 6 to obtain a fine quinacridone pigment 2. Next, the same treatment as in Example 6 was carried out except that the fine quinacridone pigment 1 was replaced with the fine quinacridone pigment 2, and 63 321118 201000570 was prepared into a yellow fine organic pigment dispersion 2, and further, in addition to yellow fine organic The pigment dispersion 2 was replaced with the red fine organic pigment dispersion 1 in the same manner as in Example 1 to prepare a yellow fine organic pigment composition 2 (yellow-developing resist type resist 2). [Example 8] A kneaded product of the following composition was placed in a 15,000-volume three-arm planetary mixer (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at a treatment temperature of 60 ° C for 12 hours at a revolution of 19 rpm and a rotation of 57 rpm.查 献 ketone pigment (C. I· Pigment Yellow 138; “Paliotol Yellow K0961HD” by BASF) 441 parts • Benzo- ketone ketone pigment derivative 9 parts • Resin solution 7 123 parts • Chlorinated sodium 4500 Diethylene glycol 1217 parts The kneaded product thus obtained was subjected to the same treatment as in Example 6 to obtain a fine quinophthalone pigment 3. Next, the same treatment as in Example 6 was carried out except that the fine quinacridone pigment 1 was replaced with the fine quinacridone pigment 3 to prepare a yellow fine organic pigment dispersion 3, in addition to the yellow fine organic pigment dispersion. 3 The same treatment as in Example 1 was carried out, except that the red fine organic pigment dispersion 1 was replaced, to prepare a yellow fine organic pigment composition 3 (yellow-developing resist type material 3). [Example 9] A kneaded product of the following composition was placed in a 1500-Q volume three-arm planetary mixer (manufactured by Inoue Seisakusho Co., Ltd.), and kneaded at a processing temperature of 60 ° C at a revolution of 19 rpm, a rotation speed of 57 rpm, 64.321118, 201000570. 12 hours. . 啥酉 ketone pigment (C· I· Pigment Ye 1 low 138; “Paliotol Yellow K0961HD” by BASF) 441 parts • Benzopyrene ketone ketone pigment derivative 9 parts • Resin solution 8 124 parts • Chlorination 4,500 parts of diethylene glycol 1268 parts The kneaded material thus obtained was subjected to the same treatment as in Example 6 to obtain a fine quinacridone pigment 4. Next, the same treatment as in Example 6 was carried out, except that the fine quinacridone pigment 1 was replaced with the fine quinacridone pigment 4, to prepare a yellow fine organic pigment dispersion 4, in addition to the yellow fine organic pigment dispersion. 4 The same treatment as in Example 1 was carried out, except that the red fine organic pigment dispersion 1 was replaced, to prepare a yellow fine organic pigment composition 4 (yellow-developing resist-type resist 4). [Example 10] A kneaded product of the following composition was placed in a 15,000-volume three-arm planetary mixer (manufactured by Inoue Seisakusho Co., Ltd.), and kneaded at a processing temperature of 60 ° C for 12 hours at a revolution of 19 rpm and a rotation of 57 rpm. Mouth I: Pig ketone pigment (CI Pigment Yellow 138; "Paliotol Yellow K0961HD" by BASF) 441 parts • Benzene σ rice brewing 1 series pigment derivative 9 parts • Resin solution 9 125 parts. Chlorinated steel 4500 parts Diethylene glycol 1166 parts 65 321118 201000570 The kneaded material thus obtained was subjected to the same treatment as in Example 6 to the fine facial ketone pigment 5. Next, the same treatment as in Example 6 was carried out to form a yellow fine organic pigment dispersion 5 in addition to the fine ketone pigment: ^ ketone ketone pigment 5, and further, in place of the yellow fine organic pigment knives 5 instead of red In addition to the fine organic pigment dispersion i, the same treatment as in Example 1 was carried out to prepare a yellow fine organic pigment composition 5 (yellow alkaline developing resist 5). [Example 11] The following group of scales were placed in a three-arm planetary mixer (manufactured by Inoue Seisakusho Co., Ltd.) in a "fresh rotation of 19 rpm, rotation &amp; (10) square rotation at 60 ° C. Mix for 12 hours at temperature. BASF manufactures 441 parts, 9 parts, 110 parts, 4500 parts, 1102 parts of quinophthalone pigments (c. [Pigment YeU(10)138"Paiiotoi Yen(10) K〇961HD") • Benzimidazolone-based pigment derivatives • Resin solution 10 • Chlorinated steel • Diethylene glycol The thus obtained kneaded material was subjected to the same treatment as #6 to obtain a fine ketone ketone pigment 6. Next, a yellow fine organic pigment dispersion 6 was prepared in the same manner as in Example 6 except that the fine nicoxone pigment i was replaced with the fine ketone ketone pigment 6, and further, in addition to the yellow micro-organic pigment dispersion 6 In addition to the red fine organic paving dispersion, carry out the real off! In the treatment of the marriage, a yellow fine organic pigment composition 6 (yellow-developing resist material 6) was prepared. 321118 66 201000570 [Example 12] A kneaded material of the following composition was placed in a three-arm planetary scrambler (manufactured by Inoue Seisakusho Co., Ltd.) of a capacity of 1,500, and the number of revolutions at a revolution of 19 rpm and a rotation of 57 rpm was 60 ° C. At the processing temperature, knead for 12 hours. • Pig 酉 酉 酮 颜料 ( (CI Pigment Yellow 138; "Paliotol Yellow K0961HD" by BASF) 441 parts • Benzomidazolone pigment derivative 9 parts • Resin solution 11 110 parts • Chlorinated sodium 4500 parts • Diethylene The kneaded product thus obtained was subjected to the same treatment as in Example 6 to obtain a fine quinophthalone pigment 7 in an amount of 1054 parts. Next, the same treatment as in Example 6 was carried out except that the fine quinacridone pigment 1 was replaced with the fine quinacridone pigment 7, to prepare a yellow fine organic pigment dispersion 7, in addition to the yellow fine organic pigment dispersion. In the same manner as in Example 1, except that the red fine organic pigment dispersion 1 was replaced, a yellow fine organic pigment composition 7 (yellow-developing resist type resist 7) was obtained. [Example 13] A kneaded product of the following composition was placed in a 15,000-volume three-arm planetary mixer (manufactured by Inoue Seisakusho Co., Ltd.), and kneaded at a treatment temperature of 60 ° C for 12 hours at a revolution of 19 rpm and a rotation of 57 rpm. . Pig 酉 酮 酮 酮 ( (CI Pigment Yellow 138; "Paliotol Yellow K0961HD" made by BASF) 9 parts • Resin solution 12 110 parts 6.7 321118 201000570 4500 parts 1053 parts • Sodium chloride • Diethylene glycol will be so The kneaded material was subjected to the same treatment as in Example 6 to obtain a fine quinacridone pigment 8. Next, the same treatment as in Example 6 was carried out except that the fine quinacridone pigment 1 was replaced with the fine quinacridone pigment 8, to prepare a yellow fine organic pigment dispersion 8, in addition to the yellow fine organic pigment dispersion. In the same manner as in Example 1, except that the red fine organic pigment dispersion 1 was replaced, a yellow fine organic pigment composition 8 (yellow-developing resist type material 8) was obtained. [Example 14] A kneaded product of the following composition was placed in a 15,000-volume three-arm planetary mixer (manufactured by Inoue Seisakusho Co., Ltd.), and kneaded at a processing temperature of 60 ° C for 12 hours at a revolution of 19 rpm and a rotation of 57 rpm. . Pig g g 太 ( CI (CI Pigment Yellow 138; "Paliotol Yellow K0961HD" by BASF) 405 parts • Benzo sigma sigma ketone pigment derivative 8 parts • Disperbyk-2000 (Japan BYK-Chem Manufactured by Chemie); modified acrylic block copolymer with amine value of 4mgK0H/g, grade 4 ammonium chloride value of 90mgKOH/g) 110 parts • 4500 parts of sodium chloride • 1035 parts of diethylene glycol The kneaded material was subjected to the same treatment as in Example 6 to obtain a fine quinophthalone pigment 9. Next, the same treatment as in Example 6 was carried out except that the fine quinacridone pigment 1 was replaced with the fine quinacridone pigment 9, and 68 321118 201000570 was prepared as a yellow fine organic pigment dispersion 9'. The organic pigment dispersion 9 was replaced with the red fine organic pigment dispersion 1 in the same manner as in Example 1 to obtain a yellow fine organic material = outer material, and material 9 (yellow green development type resist material 9). , the material, and the three-armed planetary agitation 57rPm of [Comparative Example 7] was put into a 15000-capacity mixing machine (manufactured by Inoue Seisakusho Co., Ltd.) to revolve 19 rpm and rotate at 6 (TC). Mixing for 12 hours at the treatment temperature. BASF produces 441 parts of 9 parts of 45 parts of UOS quinacridone pigment (CIPigment Yellow 138 "Paliotol Yeii〇w K0961HD") Benzimidazolone-based pigment derivative • Sodium chloride • Diethylene glycol The kneaded material thus obtained was subjected to the same treatment as in Example 6 to obtain a fine quinacridone pigment 10. Next, the same treatment as in Example 6 was carried out except that the fine quinacridone pigment was replaced with the fine quinacridone pigment 10 to prepare a yellow fine organic pigment dispersion 10, and in addition to the yellow fine organic pigment dispersion. In the same manner as in Example 1, except that the red fine organic pigment dispersion 1 was replaced, a yellow fine organic pigment composition 10 (yellow alkaline developing resist 10) was obtained. [Comparative Example 8] A kneaded product of the following composition was placed in a 15000-volume three-arm planetary mixer (manufactured by Inoue Seisakusho Co., Ltd.), and the number of revolutions at a revolution of 19 μm and a rotation of 57 rpm was kneaded at a treatment temperature of 6 (TC for 12 hours). 69 321118 201000570 . Port i: West ketone pigment (CI Pigment Yellow 138; "Paliotol Yellow K0961HD" manufactured by BASF) 441 parts. Benzomethoxone pigment derivative 9 parts. J0NCRYL 682 (manufactured by BASF Corporation, Japan; Styrene-acrylic copolymer, acid value: 238 mg K0H/g) 112 parts • 4500 parts of sodium chloride • 1305 parts of diethylene glycol The kneaded product thus obtained was subjected to the same treatment as in Example 6 to obtain fine quinacridone. Pigment 11. Next, the same treatment as in Example 6 was carried out except that the fine quinacridone pigment 1 was replaced with the fine quinacridone pigment 11, and a yellow fine organic pigment dispersion 11 was obtained, and further, in addition to yellow fine organic The pigment dispersion 11 was replaced with the red fine organic pigment dispersion 1 and subjected to the same treatment as in Example 1 to prepare a yellow fine organic pigment composition 11 (yellow developability type resist) Material 11) The half-width of the fine quinacridone pigments 1 to 11 produced by the method of the above examples, and the comparison of the yellow-experiment-developing resist materials 1 to 11 and the retardation values were measured and shown in Table 2. Example 15 A kneaded product of the following composition was placed in a 15,000-volume three-arm planetary mixer (manufactured by Inoue Seisakusho Co., Ltd.), and kneaded at a processing temperature of 100 ° C for 6 hours at a revolution of 19 rpm and a rotation of 57 rpm. Sii Cyanine Pigment (CI Pigment Green 36; "Lionol green 6YK" manufactured by Toyo Ink Manufacturing Co., Ltd.) 407 parts • Resin solution 1 51 parts 70 321118 201000570 • Sodium chloride 4280 parts. Diethylene glycol 902 parts by 70 ° C The above-obtained kneaded material was taken out from 32,000 parts of a 1% sulfuric acid aqueous solution, and after being stirred for 1 hour, it was filtered, washed with water, dried, and pulverized to obtain a fine copper halide phthalocyanine green pigment 1. The obtained pigment was subjected to X-ray diffraction measurement. (CuKa 1 ray) is a copper halide phthalocyanine green pigment having a peak at a Bragg angle of 2 Θ (allowable range ± 0.2 degrees) = 22.3 degrees. The gasified wrong beads of the color pigment 1 are made into a green micro-join The mixture containing the obtained fine copper halide phthalocyanine green composition was uniformly stirred, and then dispersed in a bead mill for 5 hours using a diameter of 1 coffee, and then the fine organic pigment dispersion 1 was filtered with a 5/m filter. Copper Halide Phthalocyanine Pigment • Copper Phthalocyanine Pigment Derivative • Acrylic Resin Solution • Propyl Alcohol Precise Acetate G. In addition to dispersing 15 parts of green fine organic pigments, 49 parts 1 instead of red &amp; / fine organic pigments In the same manner as in Example 1, the green fine organic pigment composition 1 (green alkaline portion, 1) was prepared in the same manner as in Example 1. Developing Retardant Material [Example 16] A kneaded material of the following composition was placed in a two-rpm rpm mixer (manufactured by Inoue Seisakusho Co., Ltd.), and processed at a rpm of 19 rpm, from a comet» rotation number. Mix for 6 hours at temperature. Ink Road: Copper Halide Phthalocyanine Pigment (c. I. Pigment Green 36; Toyo Yin Gong 118 71 201000570 company "Lionol green 6YK") • Resin Solution 1 • Na 2 Glycol 405 203 parts 4500 parts of 635 parts of the kneaded material thus obtained were subjected to the same treatment as in Example 15 to obtain a fine copper halide phthalocyanine green pigment 2. The obtained pigment was subjected to X-ray diffraction measurement (CuKal ray) as a copper halide phthalocyanine green pigment having a special peak at a Bragg angle of 20 (allowable range ± 0.2 degrees) = 22.3 degrees. Then, the green fine organic pigment dispersion 2 was prepared in the same manner as in Example 15 except that the fine copper halide phthalocyanine green pigment 1 was replaced with the fine copper halide phthalocyanine green pigment 2. Further, in the same manner as in Example 1, except that the green fine organic pigment dispersion 2 was used instead of the red fine organic pigment dispersion 1, a green fine organic pigment composition 2 (green green development type resist material) was produced. 2). [Comparative Example 9] A kneaded product of the following composition was placed in a 15000-volume three-arm planetary mixer (Tri-mix; manufactured by Inoue Seisakusho Co., Ltd.), and kneaded at a processing temperature of 60 ° C at a revolution of 19 rpm and a rotation of 57 rpm. 12 hours. Copper halide phthalocyanine pigment (CI Pigment Green 36; "Lionol green 6YK" manufactured by Toyo Ink Manufacturing Co., Ltd.) 450 parts. 4500 parts of sodium chloride. 6 7 5 parts of diethylene glycol. The kneaded material thus obtained was carried out and implemented. In the same manner as in Example 15, a fine copper halide phthalocyanine green pigment 3 was obtained. The obtained pigment was subjected to X-ray diffraction. 72 321118 201000570 (Cukal ray) is a dendritic green pigment with a peak at a Bragg angle of 2 Θ (allowable range ± 0.2 degrees) = 22. 3 degrees. Then, the green fine organic pigment dispersion 3 was prepared in the same manner as in Example 15 except that the fine copper halide enantiomer green pigment 1 was replaced with the fine copper halide phthalocyanine green pigment 3. Further, the same treatment as in Example 1 was carried out except that the green fine organic pigment dispersion 3 was used instead of the red fine organic pigment dispersion 1, to prepare a green fine organic pigment composition 3 (green green development type resist material) 3). The half-width of each green pigment prepared by the method of the above example, the contrast of the green-developing resist-type resist, and the retardation value were measured and shown in Table 2. [Example 17] A kneaded product of the following composition was placed in a kneading machine (manufactured by Inoue Seisakusho Co., Ltd.) of 3,000 parts by volume, and kneaded at a treatment temperature of 70 ° C for 6 hours at a rotation number of 24.5 rpm. .ε copper phthalocyanine pigment (CI Pigment Blue 15 : 6; manufactured by Toyo Ink and Manufacture, "Lionol blue Ε") 123 parts. 1 27 parts of tree wax solution. 1364 parts of sodium chloride • 213 parts of diethylene glycol The kneaded product obtained above was taken out from 8700 parts of a 1% sulfuric acid aqueous solution at 70 ° C, and after stirring for 1 hour, the mixture was filtered, washed with water, dried and pulverized to obtain a fine phthalocyanine pigment 1. The obtained pigment was subjected to X-ray diffraction measurement (Cukal ray) as an ε-type copper phthalocyanine pigment having the strongest wave temple at a Bragg angle of 2 &lt; 9 (allowable range ± 0.2 degrees) = 9.1 degree. 73 321118 201000570 Next, the mixture containing the obtained fine ε-type copper phthalocyanine pigment was uniformly mixed, and then dispersed for 5 hours in an oxidized bead 2 mill having a diameter of 1 mm, and then formed into a ramme view. = Machine Pigment Dispersion 1. ^ Fine color has 123 parts 1 part 10 parts 31 parts • Fine ε type copper phthalocyanine pigment 1 'Copper phthalocyanine pigment derivative · Acrylic resin solution. Propylene glycol monomethyl ether acetate 'except for blue fine organic pigment The dispersion i was replaced with the fine organic pigment dispersion 1, and the same treatment as in Example 1 was carried out. The blue fine organic pigment composition 丨 (blue-developable development type resist material [Comparative Example 10] Kneading machine with a small volume of 0 parts (the upper and lower scales = the rotation number of Shiqing is at the processing temperature of 6; Toyo Ink | 136 parts, 1364 parts, 1 type of carnation pigment (GIPig fine tBluel5 company made "Li〇noi blue" E") • 224 parts of sodium chloride, “1% sulfuric acid aqueous solution _ part of the middle part of the solution, take out the above-mentioned 1 chemical compound' after 1 hour capture, 捭 捭 and Yu Xin #, fine, wash, The fine phthalocyanine pigment 2 was dried. The obtained pigment was subjected to a Ravine angle of 2 u (the allowable range of 〇. 2 degrees) 3Z1118 74 201000570 9. 1 degree ε-type copper phthalocyanine pigment having the strongest wave life. Next, in addition to the fine copper phthalocyanine green pigment 1 as fine copper phthalocyanine The blue fine organic pigment dispersion 2 was prepared in the same manner as in Example 17 except that the color pigment 2 was replaced, and the blue fine organic pigment dispersion 2 was replaced by the blue fine organic pigment dispersion 2 instead of the red fine organic pigment dispersion 1. The same treatment as in Example 1 was carried out to prepare a blue fine organic pigment composition 2 (blue developable resist material 2). The fine copper phthalocyanine pigments 1 and 2 produced by the method of the above examples were measured. The comparison of the half width of the peak width, the blue basic opaque resist materials 1 and 2, and the retardation value are shown in Table 2. [Example 18] A kneaded material of the following composition was put into a kneading machine of 3000 parts by volume (in the well In the manufacturing facility, the mixture was kneaded at a treatment temperature of 60 ° C for 6 hours at a rotation number of 24.5 rpm. • CI Pigment Violet 23 (Sumitone Fast Violet RL base manufactured by Sumitomo Chemical Co., Ltd.) 123 Resin solution 1 (solid content ratio is 50 weight / 〇) 27 parts. Sodium chloride 1364 parts. Diethylene glycol 249 parts The above-obtained kneaded material is taken out from 8800 parts of a 1% sulfuric acid aqueous solution at 70 ° C, After 1 hour of heat and stirring, filter After washing with water, drying, and pulverization, fine diterpene violet pigment 1 is obtained. Next, a mixture of the following composition containing the obtained fine diterpene violet pigment 1 is uniformly stirred, and then zirconia beads having a diameter of 1 mm are used in the bead mill. 75 321118 201000570 After 5 hours of slashing in the machine, a purple fine pigment dispersion 1 was prepared by a 5&quot;m 遽 device. .Micro 2 _ 紫紫 pigment 1 1 〇. 噚 噚 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫 紫The same treatment as in Example ' was carried out except for the fine organic pigment dispersion ,, and a purple fine organic pigment composition #1 (purple alkaline development type resist material 1) was obtained. [Comparative Example 11] A kneaded product of the following composition was placed in a kneading machine (manufactured by Inoue Seisakusho Co., Ltd.) having a capacity of 3 Q00, and the number of rotations at m5 rpm was kneaded at 6 (the processing temperature of rc for 6 hours; manufactured by Sumitomo Chemical Co., Ltd.) 136 parts. 1364 parts. Diterpene violet pigment (C·I. Pigment violet; 23 "Sumitone Fast Violet rl base"; 259 parts of sodium chloride The kneaded product thus obtained was subjected to the same treatment as in Example 6 to obtain a fine diterpene. 0. Violet pigment 2. Then, the same treatment as in Example 18' was carried out except that the fine diterpene violet pigment i was replaced with the fine diterpene violet pigment 2, and a purple fine organic pigment dispersion 2 was obtained. In addition to replacing the red fine organic pigment dispersion j with the purple fine organic pigment dispersion 2, the same treatment as in the example! was carried out to prepare a purple fine organic pigment 321118 76 201000570 material composition 2 (purple alkaline display &amp; ^Q type resist material 2). Comparison of the above-mentioned example, the half width of 4 2 'think material', the fine two "Don't purple pigment 1 and ', 11 development type resist material 1 and 2 And the delay value In the above examples, the resins used in the propylene glycol mixture are summarized in Table 3. In the method of the comparative example, the solubility of UO in the early stage of the pigmentation of the U-acetic acid vinegar or diethylene glycol Shuyue (A) is resin solution 1 to 3, 6 to 12, and Disperbyk-20〇〇 of the commercially available product. <Solubility of Solvents to Organic Solvents> The tree 1 to 12 series will be replaced by The solution of the pre-diethylene glycol in the synthesis is reduced in ethanol at 100 C to obtain a solid resin obtained by evaporating ethanol and acetophenone. In the case of a commercially available resin, if it is a solid resin, it is directly used; At the same time, the organic solvent was evaporated in the same manner to obtain a solid resin. Each of the solid resin was taken in 1 part, and an organic solvent (propylene glycol mono-, methyl ether acetate or diethylene glycol) was added to make the whole 10 parts, in an oscillator. After 5 minutes of treatment, it was stored in an oven set to i〇〇°c for 30 minutes, then taken out and cooled to 25 C'. Then it was measured in Biospect's spectrawave S1200 (diode array visible spectrophotometer). Each in the cell The liquid is at a wavelength of 6〇〇nmi, and the solubility of the resin is evaluated. Soluble “〇”: the transmittance is above 90%, and the “X” is not dissolved: the light transmittance is less than 90% or the undissolved resin still exists 321118 77 201000570 [Table l] When the fine pigment of the resin solution is refined, there is a particle size, a half-peak width, a pigment composition, a retardation value, no resin (nm) (-) a resist material (-) (nm2). Example 1 Resin solution 1 DPI 24 0.84 Red 1 6050 18 Example 2 Resin solution 2 DP2 has 26 0.81 red 2 5820 8 Example 3 Resin solution 2 DP3 has 25 0. 79 Red 3 5440 14 Example 4 Resin solution 2 DP4 has 24 0.83 red 4 6340 17 Example 5 Resin solution 3 DP5 had 26 0. 78 Reference color 5 5020 14 Comparative Example 1 Resin solution 4 DP6 Yes 29 0.80 Red 6 4890 66 Comparative Example 2 Resin solution 5 DP7 Yes 29 0.80 Red 7 4250 35 Comparative Example 3 - DP8 None 23 0.88 Red 8 6740 80 Comparative Example 4 - DP9 No 33 0. 76, Red 9 3670 50 Comparative Example 5 Resin Solution 1 DP8 None 23 0.88 Red 10 6510 69 Comparative Example 6 AJISPER PB821 DP10 has 28 0. 79 Red 11 4140 16 DP : fine diketopyrrole Rhodium Pigment Red: Red Fine Organic Pigment Composition (Red Verifiable Development Resist Material) 78 321118 201000570 [Table 2] 'When the resin pigment fine pigment is refined, there is no half-peak width pigment composition contrast delay value tree month (- _Resistant (-) (nm2) Example 6 Resin solution 1 XP1 has 0. 97 Yellow 1 9200 -480 Example 7 Resin solution 6 XP2 has 0. 97 Yellow 2 9560 - 510 Example 8 Resin solution 7 XP3 1. 03 Yellow 3 8880 -390 Example 9 Resin solution 8 XP4 There is 1. 03 Yellow 4 8220 -470 Example 10 Resin solution 9 XP5 Yes 1. 07 Yellow 5 8530 -470 Example 11 Resin solution 10 XP6 Yes 0 96. Yellow 6 9480 -500 Example 12 Resin solution 11 XP7 has 0. 95 yellow 7 9670 -480 Example 13 Resin solution 12 XP8 has 0. 95 yellow 8 9620 -530 Example 14 Disperbyk-2000 XP9 has 1.01 yellow 9 9380 -490 Comparative Example 7 — XP10 No. 0. 94 Yellow 10 8050 -390 Comparative Example 8 J0NCRYL 682 XP11 has 0. 90 Yellow 11_ 7300 -450 Example 15 Resin Solution 1 PG1 has 0. 57 Green 1 8440 -20 Implementation Example 16 Resin solution 2 PG2 has 0. 71 green 2 8670 - 110 Comparative Example 9 - PG3 No 0.51 Green 3 7670 30 Example 17 Resin Solution 1 PB1 has 0. 60 Blue 1 8590 20 Comparative Example 10 - PB2 No 0.52 Blue 2 7880 90 Example 18 Resin Solution 1 DV1 has 0.83 Purple 1 3310 -850 Comparative Example 11 — DV2 No. 0. 78 Purple 2 3110 -770 XP : Fine ugly ketone pigment; PG : Fine copper halide phthalocyanine green pigment; PB : Fine ε type copper phthalocyanine blue pigment; DV: Fine bismuth cultivating purple pigment yellow: yellow fine organic pigment composition (yellow-exposure developing resist material) Green: green fine organic pigment composition (green-identifying developing resist) blue: blue fine organic pigment Composition (blue alkaline developing type resist material) Purple: purple fine organic pigment composition (purple alkaline developing type resist material) 79 321118 201000570 [Table 3] Resin eucalyptus wax taurine value 4 grade salt value Amine + recorded hydrochloric acid soluble propylene. Acidic random system mgKOH / g mgKOH / g mgKOH / g mgKOH / g PGMAc DEG resin solution 1 〇〇 3 97 100 0 X 〇 resin solution 2 〇〇 29 62 91 18 X 〇 Resin solution 3 〇 block system 29 0 29 0 X 〇 resin solution 4 〇〇11 0 11 85 〇X resin solution 5 〇〇0 0 0 85 〇〇 resin solution 6 〇〇3 97 100 0 X 〇 resin solution 7 〇〇5 127 132 0 X 〇 resin Solution 8 〇〇3 152 155 0 X 〇 resin solution 9 〇〇3 174 177 0 X 〇 resin solution 10 〇〇0 97 97 0 X 〇 resin solution 11 〇〇0 97 97 0 X 〇 resin solution 12 〇〇0 97 97 0 X 〇Disperbyk-2000 〇 block system 4 90 94 0 X Ό AJISPER PB821 X graft system 10 0 10 17 〇X J0NCRYL 682 〇〇0 0 0 238 〇〇PGMAc: propylene glycol monomethyl ether acetate DEG: In the diethylene glycol table 1, the example 1 to the pigment 80 321118 201000570 which is insoluble in the resin of the propylene glycol monoterpene ether acetate which is insoluble in the solvent of the fine organic pigment composition shown in Table 3 is used. The fine organic pigment of 5, which has a particle diameter smaller than those of Comparative Examples 1, 2, and 6, is more fine. The fine organic pigment compositions of Examples 1 to 5 have a high contrast and a low retardation tendency as compared with Comparative Examples 1, 2 and 4. Further, Comparative Examples 3 and 5 are high-contrast, but exhibit a large retardation value as compared with Examples 1 to 5, and thus their viewing angle dependence is inferior. Obviously, when a pigment is prepared by adding a resin having the structure and properties described in Examples 1 to 5 of the fine organic pigment composition of the present invention, it is possible to provide excellent viewing angle dependence, high contrast, and good display characteristics. A fine diketopyrrolopyrrole pigment and a red fine organic pigment composition. In Table 2, Examples 6 to 14, 15 to 16, 17, and 18 were obtained by using a pigment which is insoluble in a resin of propylene glycol monoterpene ether acetate which is insoluble in the dispersion solvent shown in Table 3 and made fine. The fine organic pigments each had a larger half-width than the comparative examples 7 to 8, 9, 10, and 11, so that the particle diameter was fine, the contrast was high, and the retardation value was low. Obviously, it is possible to provide a fine organic pigment by adding a resin having the structure and properties described in the fine organic pigment composition of the present invention as described in Examples 6 to 18, thereby providing excellent viewing angle dependence and high contrast. And a fine organic pigment exhibiting good characteristics and an organic pigment coloring composition. 81 321118 201000570 Invention patent specification 丨你.:-6,'Γ〇L_——...— (The format, order of this manual is not to be changed, please do not fill in the ※ part) ※Application number: [}&lt;? Name of the shirt CAB ^io ^2006,01) φ-^ Name of the invention: (Chinese / English) Manufacturing method of fine organic pigment, fine organic pigment and fine organic pigment coloring composition ※Application date: w ^ ※Working PC classification: (10) % (2006.01) C〇?LX C2006.01) METHOD FOR PRODUCING FINE ORGANIC PIGMENT, FINE ORGANIC PIGMENT AND FINE ORGANIC PIGMENT COLORING COMPOSITION 2. SUMMARY OF THE INVENTION The present invention provides a method for producing a fine organic pigment for obtaining a colored film a fine organic pigment obtained by the method, and a fine organic pigment coloring composition using the fine organic pigment, wherein the colored film is used as a color filter for a liquid crystal television, and has low retardation and viewing angle dependence A film with excellent properties and high transparency. The solution is a method for producing a fine organic pigment which is characterized in that an organic pigment, a water-soluble inorganic salt, a water-soluble organic solvent, and the water-soluble organic solvent are each at 25 ° C. 〇〇 by weight of the resin (A) having a solubility of 1 part by weight or more, and the resin (... containing an amine group or/and a quaternary ammonium salt group, after mechanical kneading, removing water-soluble inorganic substances in water To provide a method for producing a fine organic pigment being usful for obtaining a coloring film, a fine organic pigment according to the method and a fine organic pigment coloring composition 321118 1 201000570 Using the fine organic pigment, the above coloring film is useful as a color filter for liquid crystal television, and is a film sheet with low retardation, excellent viewing angle dependence, and high transparence. According to the method for producing fine organic pigment, The method is characterized in That subjecting the organic pigment, a water-soluble inorganic salt, a water-soluble organic solvent and a resin (A) exhibiting a solubility above 1 part by weight relative to 100 parts by weight of the water-soluble organic solvent under 25 °C To a mechanical kneading following by removing water-soluble salt and water-soluble organic solvent in water, the resin (A) with amino or/and quaternary ammonium group. IV. Designated representative figure: No case in this case (1) The specified representative map is: the () graph. (2) A brief description of the symbol of the representative figure: 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: This case is not represented by the chemical formula 321118 2 201000570 The patent scope of the seven patents: 1. A fine organic pigment The manufacturing method is characterized in that the organic pigment, the water, the glutamic inorganic salt, the water-soluble organic solvent, and the resin (A) are mechanically reduced, and the water-soluble inorganic salt and the water-soluble organic solvent are removed in the water towel. And +, the resin U) is one in which the solubility of the muscle I per 100 parts by weight of the water-soluble organic solvent is 1 part by weight or more and contains a base selected from the group consisting of an amine group and a quaternary ammonium salt group. 2. If you apply for a patent scope! A method for producing a fine organic pigment, wherein the resin (A) is an acrylic resin. The method for producing a fine organic pigment according to the second item of the patent application, wherein the acrylic resin is a method for producing a fine organic pigment which is synthesized by random polymerization and is synthesized by a random acid. Medium 'Resin (A) is not soluble in propylene glycol monomethyl acetate. Among the fine organic pigments of the /, - the middle - item, the coffee material is at least one selected from the group consisting of diketone-based organic pigments: = broadly organic to pigments, characterized by: - obtained by the method of manufacturing the fine organic pigment of the ancient withdrawal. 6, Tiantian organic pigment coloring composition, its characteristics. Her organic pigments and pigment carriers. In the seventh item of the patent scope of the application, the addition of a non-solvent organic pigment coloring composition, 321118 82 201000570 III, English abstract: To provide a method for producing a fine organic pigment being usful for obtaining a coloring film, a fine Organic pigment according to the method and a fine organic pigment coloring composition using the fine organic pigment, wherein the above coloring film is useful as a color filter for liquid crystal television, and is a film sheet with low retardation, excellent viewing angle dependence, and High-transparence. According to the method for producing fine organic pigment, the method is characterized in that subjecting the organic pigment, a water-soluble inorganic salt, a water-soluble organic solvent and a resin (A) exhibiting a solubility above 1 part by Weight relative to 100 parts by weight of the water-soluble organic solvent under 25 °C, to a mechanical kneading following by removing water-soluble salt and water-soluble organic solve Nt in water, the resin (A) with amino or/and quaternary ammonium group. IV. Designated representative map: There is no schema in this case (1) The representative representative figure in this case is: (). (2) A brief description of the symbol of the representative figure: 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: This case does not represent the chemical formula 321118 2