TW200951185A - Organic pigment composition and producing method thereof, and colored photosensitive resin composition, color filter using the same - Google Patents

Abstract

The subject of the present invention is to provide an organic nanopigment particle non-aqueous dispersion which has good dispersity and dispersion stability. The organic nanopigment particle non-aqueous dispersion is produced by a method without complicated procedures by re-dispersing an organic nanopigment particle hydrophobic aggregate in a non-aqueous medium. Said hydrophobic aggregates can be efficiently obtained by separating organic nanopigment particles from an aqueous medium. Said organic nanopigment particles are made into non-aqueous aggregates. The solution to the subject is an organic pigment composition comprising a polymer compound having repeating unit represents by the following formula (1) and formula (2), and an organic fine particle: (wherein A1 represents hydrogen atom or methyl group; X1 represents a hetrocyclic ring bonding to the repeating unit by a carbon atom.)

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic pigment composition, a process for producing the same, a colored photosensitive resin composition using the same, and a color filter. [Prior Art] Only the organic pigments in the nanometer-sized particles can be examined, for example, coatings, inks, toners for electrophotography, inkjet inks, and color filter materials. Among them, those who are required to have high performance and are particularly important in practical use are pigments for inkjet inks and pigments for color filters. Regarding the production method of organic particles, there are a gas phase method, a liquid phase method, a laser ablation method, and the like. Among them, the liquid phase method is a method for preparing organic particles which are highly susceptible to the simplicity and productivity. Patent Document 1 describes an example in which a pigment particle aqueous dispersion is prepared by a liquid phase method. This method is in the final method of aqueous dispersion, and the provision of the organic solvent dispersion is not mentioned. Patent Document 2 describes an example in which an organic solvent dispersion is provided using pigment particles prepared by a liquid phase method. However, the primary particle diameter of the organic pigment particles obtained by this method tends to become large, failing to sufficiently respond to the requirement of micronization. With respect to the preparation of the nanoparticles by the liquid phase method described above, a low molecular surfactant and a neutral water-soluble nonionic polymer compound are used for the aggregation of the nanoparticles. Therefore, although the nanoparticles can be dispersed at a high concentration, a large amount of dispersing aid must be used. For example, those having a low viscosity of a polymer compound having a low viscosity of ink jet are difficult to directly adopt such techniques. -4- 200951185 In addition, in response to the requirement of phase shifting to a desired solvent system after preparing nanoparticles in an aqueous medium, it is known to prepare an aqueous slurry containing a high concentration of pigment, an aqueous paste, and a resin or resin solution. Mixing and stirring, replacing the moisture around the pigment with a resin or resin solution. However, in this method, since the particles are once strongly agglomerated in an aqueous medium, the efficiency of coating with a resin is poor, and it becomes difficult to redisperse (see, for example, Patent Documents 3 and 4). Further, in order to prepare a water-based paste, another method is a method in which nano pigment particles prepared in an aqueous solvent are directly filtered in a state of primary particles or agglomerated. However, the filtration is time consuming and industrially inefficient and complicated. Although a low molecular anionic or cationic surfactant can also be used as a dispersing agent, dispersion stability may be insufficient due to low molecular weight. There is also an attempt to use a cationic polymer compound to transfer a phase to an ionic liquid without a filtration step of an aqueous dispersion of particles (see, for example, Non-Patent Document 1). However, this method is aimed at low-concentration inorganic particles. The organic pigment ' is not mentioned and the final dispersion medium is a non-volatile ionic liquid, and the method described in Non-Patent Document 1 is not suitable for industrial use. Patent Document 5 discloses a method of performing an extraction operation on a non-aqueous medium by causing organic nano pigment particles to be aggregated in an aqueous medium. Then, the membrane filter is filtered to separate and then redispersed in a non-aqueous medium in the presence of an organic polymer. However, since the aggregate at the time of separation is hydrophilic, filtration is time consuming. Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. 2007-2623 No. 78 Non-Patent Document 1 "small", 2006, Vo 1. 2, No. 7, p. 879-883 SUMMARY OF THE INVENTION Problem to be Solved by the Invention An object of the present invention is to provide an organic pigment composition It contains nanometer-sized organic pigment particles and can be easily switched to hydrophobicity without complicated steps. An object of the present invention is to provide an organic pigment composition which exhibits high performance and which exhibits high performance when a color filter is produced, and a method for producing the same, and provides a colored photosensitive resin composition using the above composition, Color filter. Means for Solving the Problems The object of the present invention is achieved by the following means. [1] An organic pigment composition characterized by comprising a polymer compound having a repeating unit of the following formula (1) and/or a repeating unit of the formula (2); and an organic pigment fine particle:

Η

Η (1) (2) 200951185 (wherein A represents a hydrogen atom or a methyl group; X! represents a heterocyclic group which is bonded to the NH group by a carbon atom thereof). [2] The organic pigment composition according to [1], wherein the polymer compound further has a repeating unit of the following formula (3) and/or a repeating unit of the formula (4):

L, Y2 (wherein A2 represents no nitrogen atom or methyl group, Υι represents -NH-, -〇- or -S - ; L represents a single bond or a divalent linking group; Y2 represents a hydrogen atom or a basic group; , represents an unsaturated heterocyclic group having 1 or 2 nitrogen atoms). [3] The organic pigment composition according to [1] or [2], wherein the polymer compound further has a repeating unit of the following formula (5) and/or a repeating unit of the formula (6)

(wherein A3 and Α4 each independently represent a hydrogen atom or a methyl group; Ri represents a noisy group; R2 represents a hydrogen atom or an alkyl group; and Ri and R2 may be bonded to each other to form a ring structure group, and the ring structure group may also contain oxygen. An atom, a nitrogen atom or a sulfur atom; 1^3 and R4 each independently represent a hydrogen atom or an alkyl group; and R3 and R4 may be bonded to each other to form a ring structure group). [4] The organic pigment composition according to any one of [1] to [3] wherein the average particle diameter of the organic 200951185 pigment fine particles is in the range of 10 to 1 0 0 n m. [5] The organic pigment composition according to any one of [1] to [4] which is a dispersion in which the organic pigment fine particles are dispersed in a medium. [6] The organic pigment composition according to any one of [1] to [4] wherein the organic pigment microparticles are aqueous aggregates present in an aqueous medium. [7] In the aqueous agglomerate according to [6], a polymer compound having a mass average molecular weight of 1,000 or more is further present to form an organic pigment composition of a hydrophobic aggregate. [8] The hydrophobic aggregate as described in [7] is contained in a non-aqueous medium, and the aggregate is deagglomerated to form a redispersed organic pigment composition. [9] A colored photosensitive resin composition containing at least the organic pigment composition, the binder, the monomer or the oligomer, and the photopolymerization initiator or the photopolymerization initiator system as described in [8]. [10] A color furnace sheet using the colored photosensitive resin composition as described in [9]. [11] A process for preparing an organic pigment composition, which is characterized in that a solution of an organic pigment and a gastric molecular compound having a repeating unit of the following formula (1) and/or a repeating unit of the formula (2) is dissolved in a good solvent , mixing with the medium which is compatible with the good solvent and which is a poor solvent for the organic pigment 'generates the particles of the organic material: 200951185

Its carbon atom is bonded to the NH group). [12] The method for producing an organic pigment composition according to [11], wherein the polymer compound further has a repeating unit of the following formula (3) and/or a stomach complex unit of the formula (4):

For <y Υι L, y2 (3) u (wherein A2 represents a hydrogen atom or a methyl group; Yi represents -NH-, -O- or -S_; L represents a single bond or a divalent linking group; Y2 represents a hydrogen atom Or a basic group 'Zl represents an unsaturated heterocyclic group having 1 or 2 nitrogen atoms). [1 3] The method for producing an organic pigment composition according to [1 1 ] or [1 2] wherein the tubular molecular compound further has a repeating unit of the following formula (5) and/or a formula (6) · Repeating unit: 200951185

Deaf

I r3 (5) (6) (wherein A3 and A4 each independently represent a hydrogen atom or a methyl group represents an alkyl group; R2 represents a hydrogen atom or an alkyl group; and 1 and r2 may be bonded to each other to form a ring structure group, the ring structure group It may also contain an oxygen atom, a nitrogen atom or a sulfur atom; R3 and R4 each independently represent a hydrogen atom or an alkyl group; and r3 and r4 may be bonded to each other to form a ring structure group). Advantageous Effects of Invention The organic pigment composition of the present invention contains a nano-sized organic pigment micro and a specific polymer compound, and has a hydrophilicity which can be easily switched in accordance with the application or manufacturing, and the composition is easily switched without complicated steps. The superior S effect. Further, by using the organic pigment composition of the present invention, a colored photosensitive resin composition imparting desired properties can be obtained at an extremely high rate, and the color filter of the present invention using the present invention can be highly contrasted on a display device or the like. Play high performance. [Embodiment] Hereinafter, an organic pigment composition of the present invention will be described. The organic pigment used in the present invention is preferably formed by a liquid phase method, and may be used singly or in combination of plural or the like. The organic pigment is not limited to hue, and is, for example, anthraquinone, picone, quinacridone, quinacridone oxime, hydrazine, diindolone, benzimidazolone, bisazo condensation, disazo, azo, Indanthrone, indigo, triaryl cation, diterpene, amine 蒽-10- 200951185 醌, diketopyrrolpyrrole, thiopurine, isoporphyrin, isoindole copper pyridone or different A scorpion compound pigment, or a mixture thereof, and the like. More specifically, there are, for example, c. I. Pigment Red 19〇 (c 〖. No. 71140), CI Pigment Red 224 (CI No. mmc·〗Pigment 糸 29 (CI No. 71129) and other generic compound pigments, ci pigments (CI No. 71105) or CI Pigment Red Mqc·〗 No. 711〇〇), such as a purple ketone compound pigment, CI Pigment Violet 19 (CI No. 73 9 0 0), CI Pigment Violet 42, CI Pigment Red 122 (CI No. 73 9 1 5) ' C. 1_ Pigment Red 192, C_I. Pigment Red 202 (CI No. 7390 7), CI Pigment Red 207 (C.I_ No. 73900, 73906) or c I. Pigment Red 209 (CI No. 73 9 〇5) quinacridone compound pigment, CI Pigment Red 20 6 (CI No. 73 900/7 3 92 0), C, 〖Pigment Orange 48 ((:.1. No. 7390 0/7 3920) or (: .1. Pigment orange 49 ((: 1 No. 73900/73920), etc., pyridoxine quinone compound pigment, C. I·Pigment 147 (C_I. No. 60645), etc. 蒽醌 compound pigment, c. ί pigment Red 168 (CI No. 5 93 00) and other ketone compound pigments, c I. Pigment Brown 25 (CI No. 12510), CI Pigment Violet 32 (C. 丨 No. 12517), (:·! Pigment Yellow 180 ( (:]•No. 21290) C l Pigment Yellow 181 (CI No. 11777), CI·Pigment Orange 62 (CI No. 1 1 7 75) or C. 颜料. Pigment Red 185 (CI No. 12516), etc. Benzodime Compound Pigment, CL Pigment Yellow 93(C_I.No.2〇7l〇) c I·Pigment Yellow 94 (C., No. 2 003 8), CI Pigment Yellow 95 (c丨 No. 20034), C l Pigment Yellow i28 (CI•No. 2〇〇 37), C i Pigment Yellow 166 (C·丨. No. 2〇〇35), c·〗·Pigment Orange 34 (c〗 No. -11 - 200951185 Pigment Number Pigment Number Pigment 21115), C. 1_ Pigment Orange 13 ( CI No. 2111〇), cj Orange 31 (CI No. 200 5 0), CI Pigment Red 144 (cj 20735), CI Pigment Red 166 (CI No. 20730), c I Red 220 (C. 1_ No. 200 5 5 ), C·I. Pigment Red 221 (C. ! 20065), CI Pigment Red 242 (CI No. 20067), ci Red 248, CI Pigment Red 262 or CI Pigment Brown 23 (c. ! No. 2〇〇6〇) Bis-azo condensation compound pigment, CI Pigment Yellow i3 (CI No. 21 1 00), CI Pigment Yellow 83 (c. 丨 No. 21 1〇8) or c Summer Pigment Yellow I88 (CI No. 2 1 094) Nitrogen compound pigment, c-work pigment red lUK.! 〗 2486), C I. Pigment Red i7〇 (c Shu No. 1 2475), C.!. Pigment Yellow 74 (C I No. ιΐ7ΐ4), ^ Pigment Yellow 150 (C.I. No. 4854S ,. 8 5 4 5) 'cL Pigment Red 48 (CI No. 1 5 8 6 5 ), C. I. Pigment Red 5 3 ( 〇τ ^ ^ .I' No. 15585), c. I. Pigment Orange 64 (: .1. No. 12760) or an azo compound pigment such as ", MC, I. Pigment Red 247 (CI No. I59! 5), an indanthrone compound such as CI Pigment Blue 60 (CI No. 69800) Material 'C. !•Pigment Green 7 (c·〖.No. 74260), CI Pigment Green 36 L No. 74265), CI Pigment Green 3 7 (C _ I · No. 7 4 2 5 5 ), p • I Pigment Blue 16 (CI No. 74 1 00), C_I. Pigment Blue 75.1. No. 74160: 2) or 15 (CI No. 7416〇), such as indigo compound _ _ J neck 枓, c_ I. Pigment blue 56 (C. I, No. 42 800) or C.; [, pigment-one-g-m-v-v, octo-61 (CI number 42765: 1) and other two-party cation-based carbon compound pigments, c sr τ 姑, 丨, Step. Pigment Violet 23 (CI No. 51319 or C. I · Pigment Violet 3 7 (C. j Pigment ' No. 51345), etc. Two cultivating compounds c·Pigment red 177 fri • 1 · No. 6 5 3 0 0) Amine oxime 200951185 pigment, c. I. Pigment red 254 (c·〖..5611〇), ci pigment red 2 5 5 (c. I. No. 56 1 050), c· Pigment Red 264, c〗 Pigment Red 272 (C. i• No. 56115〇), c M Pigment Orange 71 or cz•Pigment Tan 7 etc. Pyrrolylpyrrole compound pigment, c.]·Pigment red 8 8 (CI No. 733 1 2), etc., thioindole compound pigment, c·〗 Pigment Yellow 139 (ci No. 5 629 8), c Pigment Orange 66 (CI number 4821〇) Isoproline porphyrin compound pigment, c. I. Pigment Yellow 1〇9 (C.; (. No. 56284) or CI Pigment Orange "(c". No. U 295) Ketone compound pigment, pyridone compound pigment such as CI Pigment Orange 40 (CI No. 5 9700) or c L Pigment Red 216 (C. 1_No. 597 1 0), or C_I. Pigment Violet 31 (CI No. 60010), etc. a sulphuricone compound pigment, wherein a quinacridone compound pigment, a diketopyrrolepyrrole compound pigment, a diterpene compound pigment, a phthalocyanine compound pigment or an azo compound pigment is preferably a 'diketopyrrolylpyrrole compound pigment Or a diterpenoid compound pigment is preferred. In the present invention, two or more organic pigments or organic pigment solid solutions may be used in combination. The organic pigment fine particles in the composition of the present invention can be produced by mixing an organic pigment solution obtained by dissolving an organic pigment in a good solvent with a solvent which is compatible with the good solvent and which is a poor solvent for the organic pigment. In the present invention, the organic pigment composition preferably contains a composition of the organic pigment fine particles and a specific molecular compound described later, and a dispersion of the organic pigment fine particles (hereinafter referred to as "re-sinking liquid") may be used. The invention comprises a powder composition of the organic pigment microparticles and the specific polymer compound, agglomerated composition-13-200951185, and a solid composition. In this case, the organic pigment composition may contain organic pigment particles and other components other than the specific polymer compound, and the specific polymer compound or the like may coexist independently of the organic pigment particles in the composition, or may be inhaled. Or adsorbed to pigment particles and coexist. The poor solvent of the organic pigment is not particularly limited as long as it can be dissolved or uniformly mixed with a good solvent for dissolving the organic pigment. The poor solvent of the organic pigment is preferably 0.02% by mass or less, more preferably 0.01% by mass or less, based on the organic pigment. There is no particular lower limit for the solubility of the organic pigment in the poor solvent, and it is considered that the organic pigment generally used is 0.000% by mass or more. This solubility may also be based on the solubility when dissolved in the presence of an acid or a base. Further, the compatibility or uniformity of the good solvent and the poor solvent is preferably 30% by mass or more, and more preferably 50% by mass or more, based on the poor solvent. For poor solvents, there is no special upper limit for the amount of good solvent to be dissolved, and in practice, it can be mixed at any ratio. The poor solvent is not particularly limited as long as it is an aqueous medium, and examples thereof include an aqueous solvent (for example, water or a hydrochloric acid 'aqueous sodium hydroxide solution), an alcohol compound solvent, a ketone compound solvent, an ether compound solvent, an aromatic solvent, and a carbon disulfide solvent. The aliphatic compound solvent, the nitrile compound solvent, the halogen compound solvent, the ester compound solvent, the ionic liquid, the mixed solvent thereof, the aqueous solvent, the alcohol compound solvent, the ketone compound solvent, the ether compound solvent, the ester compound solvent or a mixture thereof is preferably water-based. The solvent, the alcohol compound solvent or the ester compound solvent is more preferable. The alcohol compound solvent is, for example, methanol, ethanol, isopropanol, n-propanol, 1-methoxy-2-propanol or the like. The ketone compound solvent is, for example, acetone, methyl ethyl ketone, methyl-14-200951185 isobutyl ketone or cyclohexanone. The solvent of the ether compound is, for example, diether, tetrahydrofuran or the like. The aromatic compound solvent is, for example, a benzene or a compound solvent such as hexane or the like. Nitrile compound solvent: and so on. The halogen compound solvent is, for example, chloroform, dichloromethane, iodoform or the like. The ester compound solvent is, for example, ethyl acetate, methyl acetate, ethyl lactate or 2-(1-methoxy)propyl acetate. There are, for example, a 1-but-3-methine cation and a ρρ6_ salt. A good solvent is not particularly limited as long as it dissolves the organic pigment used and is miscible with the same or a uniform. The solubility of the organic pigment is preferably from 2% by mass to _% by mass or more based on the solubility of the organic material. The dissolution of organic pigments in good solvents! The organic pigments normally used are limited to 5 〇. This solubility may also be compared to the compatibility or uniformity of the poor solvent with the good solvent when dissolved in the presence of an acid or a base. The good solvent may, for example, be an aqueous solvent (for example, water or hydrochloric acid, a solution), an alcohol compound solvent, a guanamine compound solvent, a ketoether compound solvent, an aromatic solvent, a carbon disulfide solvent solvent, a nitrile compound solvent, an yttrium compound solvent, A halogen solvent, an ester compound solvent, an ionic liquid, a carboxylic acid compound, a mixed solvent of sulfuric acid, etc., an aqueous solvent, an alcoholated ketone compound solvent, an ether compound solvent, a bismuth compound solvent, a guanamine compound solvent, a carboxylic acid The compound, sulfonic acid or a mixture thereof is preferred, an aqueous solvent, an alcohol compound methyl ether, diethylbenzene or the like. The grease is preferably acetonitrile, tributyl ethoxide, butyl acrylate or lactic acid ionic liquid. The good solvent of the poor solvent is preferably 〇, and 〇·5 f is not particularly effective. The preferred range is as the former sodium hydroxide hydrate solvent, the aliphatic compound compound solution, the sulfonated compound solvent, the agent, the ester compound, the sulfur solvent, the esterified-15-200951185 compound solvent, the Yafeng compound solvent, The guanamine compound solvent, the carboxylic acid compound, the sulfonic acid compound, the sulfuric acid is more preferable, the sub-grinding compound solvent, the guanamine compound solvent, the carboxylic acid compound, the sulfonic acid compound, and the sulfuric acid are particularly preferable. The alcohol compound solvent is, for example, methanol, ethanol, isopropanol, n-propanol, 1-methoxy-2-propanol or the like. The ketone compound solvent is, for example, acetone, methyl ethyl ketone, cyclohexanone or the like. The ether compound solvent is, for example, dimethyl ether, diethyl ether, tetrahydrofuran or the like. The aromatic compound solvent is, for example, nifedipine, chlorobenzene or dichlorobenzene. The aliphatic compound solvent is, for example, hexane or the like. The nitrile compound solvent is, for example, acetonitrile or the like. The solvent of the hydrazine compound is, for example, dimethyl arsenite, dithidium pentoxide, hexamethylene sulfoxide, cyclobutyl hydrazine or the like. The halogen compound solvent is, for example, chloroform, dichloromethane, trichloroethylene, iodoform or the like. The ester compound solvent is, for example, ethyl acetate, butyl acetate, methyl lactate, ethyl lactate, 2-(1-methoxy)propyl acetate or the like. The ionic liquid is, for example, a salt of 1-butyl-3-methylimidazolium cation and PF6-. The guanamine compound solvent is, for example, N,N-dimethylformamide, 1-methyl-2-pyrrolidone, 2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, 2-pyrrolidine Ketone, ε-caprolactam, formamide, hydrazine-methylmethanoamine, ethanoamine, hydrazine-methylacetic acid amine, ν, Ν-dimethylacetamide, Ν-methyl propyl amide , hexamethylphosphoric acid amine and the like. The phthalic acid compound solvent is, for example, formic acid, acetic acid, chloroacetic acid, dichloroacetic acid, oxalic acid, trifluoroacetic acid, trichloroacetic acid, 2,2-dichloropropionic acid lylic acid or the like. The sulfonic acid compound is, for example, a methyl group; a sulfonic acid, p-toluenesulfonic acid, sulfuric acid, chlorosulfonic acid, trifluoromethanesulfonic acid or the like. Specific examples of good solvents and specific examples of poor solvents are common to the 'but not the same as good solvents and poor solvents' and the relationship between the organic pigments used. Solubility-16-200951185 is preferably higher than the solubility of the poor solvent. For example, the solubility is preferably 0.2% by mass or more, more preferably 0.5% by mass or more. There is no special upper limit for the difference in solubility between the solvent and the poor solvent, and it is practical to consider that the organic pigment generally used is 50% by mass or less. The concentration of the organic pigment solution in which the organic pigment is dissolved in the good solvent is preferably about 1/100 of the saturated concentration of the organic pigment in the good solvent at the time of dissolution. The preparation conditions of the organic pigment solution are not particularly limited, and the range from atmospheric pressure to subcritical and supercritical conditions can be selected. The temperature at normal pressure is -1 0 to 1 50. (: preferably, -5 to 1 30 ° C is more preferable, 〇~1 〇〇 °C is particularly preferred. In the present invention, the 'organic pigment is preferably dissolved under acidic or alkaline conditions. Generally, there is a base in the molecule. The pigment which is dissociable under the nature is basic, and the base which is not dissociated in the presence of a base is present. When a plurality of protons in the molecule are easily attached with a nitrogen atom, acid is used. For example, quinacridone or diketopyrolidyl The pyrrole and disazo condensed compound pigments are alkaline, and the indigo compound pigment is dissolved under acidic conditions. It is used for alkali-based lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide or hydrogen. An inorganic base such as cerium oxide, or an organic base such as a trialkylamine, a di-bicyclic oxime (DBU) or a metal alkoxide, preferably an inorganic base. The amount of the base used is such that the amount of the pigment is uniformly dissolved. No special restrictions 'but inorganic bases, relative to the organic material is 1. 〇 ~ 3 〇 molar equivalent is better ' 1.0 ~ 25 molar equivalents better, ι · 〇 ~ 2 〇 molar equivalents especially good. Organic base It is preferably 1.0 to 1 molar equivalent to the organic material, and 5.0 to 100 molar equivalents. ' 20~1〇〇 Moel equivalent is especially good. -17- 200951185 Acidic acid, sulfuric acid, hydrochloric acid or other inorganic acid' or acetic acid, difluoroacetic acid, oxalic acid, methanesulfonic acid or trifluoromethyl when dissolved under acidic conditions An organic acid such as sulfonic acid is preferred as the inorganic acid. Sulfuric acid is preferred. The amount of the acid to be used is not particularly limited as long as it can uniformly dissolve the amount of the organic pigment, but is excessively used in comparison with the base. The acid is preferably 3 to 5 molar equivalents relative to the organic material, preferably 〇~500 molar equivalent, preferably 30 to 2 molar equivalents. Mix the base or acid with an organic solvent. As a good solvent for organic pigments, it is a solvent that completely dissolves alkali or acid, and can add some water, lower alcohol, etc. in the organic solvent to have high solubility in the test or acid. The amount of water and lower alcohol is for organic materials. The total amount of the solution is preferably 5% by mass or less, more preferably 30% by mass or less. Specifically, water, methanol, ethanol, n-propanol, isopropanol, butanol or the like can be used. Poor solvent when precipitation and formation of organic particles The conditions are not particularly limited, and the range from atmospheric pressure to subcritical and supercritical conditions can be selected. The temperature under normal pressure is preferably -3 0 to 1 0 0 °C, -1 0 to 60. (: Better, 0 to 3 〇 ° C is particularly preferable. When the organic pigment solution and the poor solvent are mixed, it may be mixed by adding either of them, but it is preferable to add the organic pigment solution to the poor solvent and mix it. The poor solvent is preferably in a stirred state. The scavenging speed is preferably 100 to 100 rpm, more preferably 150 to 8000 rpm, and particularly preferably 2 to 6 OOO rpm. The pump may or may not be used when added. Adding liquid or adding liquid, adding liquid is preferred. Mixing ratio of organic pigment solution, liquid γ good solvent (good solvent in organic pigment microparticle re-sinking solution / not & Μ -18- 200951185 ratio) The volume ratio is preferably 1/5 0~2/3, and 1/4 0~1/2 3 / 8 is especially good. The aqueous medium contains at least 60% of the above aqueous solvent and contains 80% by mass or more. The organic pigment composition is, for example, as described above; the content of the organic pigment fine particles is not particularly limited, and 1000 ml of the organic pigment fine particles are preferably in the range of from 1 to 40000 mg in the range of from 30,000 to 30,000 mg, in the range of from 50 to 25,000 mg. The preparation scale of the organic pigment microparticles is not particularly poor. The mixing amount of the solvent is preferably 1 to 1 000 L. Regarding the particle size of the organic pigment particles, there is a method of borrowing the average size of the group, which is commonly used to indicate the mode diameter, which corresponds to the median diameter of the central axis of the integral distribution curve (quantity average, length average, area average, In the present invention, unless otherwise stated, the average particle diameter means that the average particle diameter of the organic pigment particles (primary particles) is preferably 200 nm, preferably 10 to 1 nm, and 10 to 80 nm. The particles may be crystalline particles or amorphous particles, also. In the present invention, the ratio (Mv/Mn) of the volume average average particle diameter (?η) is used as the index indicating the particle unless otherwise stated. The monodispersity of the (primary particles) used in the concentration method of the organic pigment particles, that is, the MWMn is preferably 1. 1 to 〜1_8, more preferably 1.0 to 1.5. More preferably, 1 / 2 0 ~ mass%, preferably a dispersion of a liquid, but preferably for a medium, particularly preferably in the range of 20. The limit is limited, but with the best value of 1~1 00L, the largest diameter of the cloth, the average average volume, and the average volume average diameter. Meter size, 1~ good. In the present invention, it is preferred that these mixed particle diameters (Mv) and the number of monodisperse dispersions of the particles -2.0 are preferred, 1. 0 -19- 200951185

The method for measuring the particle diameter of the organic pigment particles includes a microscopic method, a gravimetric method, a light scattering method, a light blocking method, an electric resistance method, an acoustic method, and a dynamic light scattering method, and is preferably a microscopic method or a dynamic light scattering method. Microscopes for microscopy include, for example, scanning electron microscopes, transmission electron microscopes, and the like. In the particle measurement device of the dynamic light scattering method, for example, NANOTRAC UPA-EX150 manufactured by Nikkiso Co., Ltd. is a dynamic light scattering photometer dlS-7000 series manufactured by Otsuka Electronics Co., Ltd., and LB·400, etc., manufactured by Horiba, Ltd. ). In the present invention, when the organic pigment fine particle-prepared dispersion liquid is precipitated, at least one of the organic pigment solution and the poor solvent may contain a dispersing agent. In this case, at least the organic pigment solution contains a dispersing agent (in the present invention, the dispersing agent added at the time of particle precipitation is simply referred to as "dispersing agent", and it is preferably distinguished from the hydrophobic dispersing agent described later). Dispersing agents which can be used are, for example, low molecular or polymeric dispersants of anionic, cationic, amphoteric, nonionic or pigment derivatives. The amount of the low molecular weight or high molecular weight dispersant added is preferably 10% by mass or more and 1,000,000% by mass or less based on the dissolved pigment. 10% by mass or more and 200% by mass or less are more preferable. When the amount of addition is too small, the effect of suppressing the growth and aggregation of the pigment particles is small, and if it is too large, problems such as an increase in viscosity and a poor dissolution tend to occur. In the present invention, when a dispersion of the organic pigment fine particles is prepared, at least one of the organic pigment solution and the poor solvent may contain a specific high molecular compound. At this time, it is preferred to contain a dispersant in at least the organic pigment solution. In the present invention, it is preferred that the specific polymer compound has a dispersant function. Here, the dispersing agent added at the time of particle precipitation is specifically referred to as "dispersing agent", and is distinguished from the dispersing agent for hydrophobicity described later. -20-200951185 In the present invention, the amount of the specific polymer compound having a dispersing agent function is preferably 10% by mass or more and 1% by mass or less, and more preferably 10% by mass or more based on the pigment to be dissolved. 200% by mass or less is more preferable. When the amount is too small, the effect of suppressing the growth of the pigment particles and the strong aggregation between the pigment particles is small, and if it is too large, the viscosity is increased and the dissolution is likely to occur. In the present invention, the molecular weight of the dispersant is preferably 1,000 or more and 200,000 or less by mass average molecular weight, more preferably 3,000 or more and 40,000 or less. When the molecular weight is too small, the effect of suppressing the growth of the pigment particles and the hard aggregation is small, and when it is too large, problems such as an increase in viscosity and a poor dissolution tend to occur. In the present invention, the molecular weight alone means a mass average molecular weight, and the mass average molecular weight is an average molecular weight in terms of polystyrene measured by gel permeation chromatography (carrier·tetrahydrofuran) unless otherwise stated. The above specific polymer compound is a polymer compound having a repeating unit of the following formula (1) and/or a repeating unit of the formula (2):

In the formula, Ai represents a hydrogen atom or a methyl group, and a hydrogen atom is preferred. Χι denotes a heterocyclic group bonded to the NH group by a carbon atom thereof. Preferred examples are uracil residues, thiouracil residues, cytosine residues, adenine-21 - 200951185 呤 residues, guanine residues, imipenoid residues, benzodiazepine residues, sputum residues Base, benzothiazepine residue, anthracene residue, benzopyrene residue, a sharp residue, a pyrimidine residue, a sorghum residue, a ruthenium residue, a triterpene residue, a ruthenium residue, Benzimidazolone residue, anthracene residue, porphyrin residue, piperidine residue, barbiturate residue, thiobarbital residue' are better urinary chelate residue, sulphonic steep residue , glandular residue, guanine D, residue, benzoic acid 11 residue, benzothiazepine residue, benzoxazole residue, stagnation residue, chelate D residue, scorpion Base, triterpenoid residue, benzimidazolone residue, barbiturate residue, thiobarbital residue. The repeating units of the general formulae (1) and (2) may be hydrophilic or hydrophobic. The interaction between the argon bond, the π·π interaction, and the dipole-dipole interaction with the organic pigment is good. The stronger these interactions, the more the adsorption rate of the dispersant increases toward the pigment, and the dispersion and dispersion stability in the non-aqueous medium increase. The repeating unit of the general formulae (1) and (2) is specifically exemplified below, but the present invention is not limited thereto. L1 to 20 are specific examples of the general formula (1), and L21 to 30 are specific examples of the general formula (2). -22- 200951185

The above specific polymer compound is preferably a polymer compound having a repeating unit of the following formula (3) and a repeating unit of the formula (4).

In the formula, a2 represents a hydrogen atom or a methyl group, preferably a hydrogen atom. Υι denotes -NH-, _〇, preferably -NH-, _0_. L represents a single bond or a divalent linking group. The divalent linking group is preferably an alkylene group having an alkyl group having 1 to 8 carbon atoms, an oxiranyl group or an oxypropylene group. Preferred examples of alkylene are methylene, ethyl, propyl, butyl, 2,2-dimethylpropyl, hexyl, heptyl, octyl, and especially carbon. The number of 2 to 4 is an extended ethyl group, a propyl group, a butyl group, and a 2,2-dimethyl propyl group. Y2 represents a hydrogen atom and a basic group. The basic group is a monoalkylamine or a dialkylamine, preferably a dialkylamine. Specific examples of the dialkylamines are dimethylamino, diethylamino, dipropylamino, dibutylamino, dihexylamino, di-2-ethenylamino, dioctylamino, diammonium. And a bis(dodecyl)amino group or the like, preferably a dimethylamino group, a diethylamino group, a dipropylamino group or a dibutylamine group. The oxime is an unsaturated heterocyclic ring which does not contain 1 to 2 nitrogen atoms, and preferably has an imidazole residue, a pyridine residue, a pyrimidine residue, a hydrazine residue, and particularly preferably an imidazole residue or a pyrazole residue. The repeating unit of the formula (3) or (4) may be either hydrophilic or hydrophobic, but is preferably a structure having a strong acid-base interaction with a dispersing agent for hydrophobicity to be described later. When the dispersing agent for hydrophobicity is acidic, the weight of the general formulae (3) and (4) is preferably -24 to 200951185, and the pKa system is preferably 6 or more. When the dispersing agent for hydrophobicity is alkaline, the repeating unit of the general formulae (3) and (4) is preferably inferior in performance, and PKa is preferably 5 or less. The stronger the interaction of these acids, the more the dispersion and dispersion stability in non-aqueous media. The repeating unit of the formula (3) '(4)' is specifically exemplified below, but the invention is not limited thereto. M1 to 6 are specific examples of the formula (3), and M7 to 9 are specific examples of the formula (4).

Μ*8 Μ-9 The above-mentioned specific polymer compound is preferably a polymer compound having a repeating unit of the following formula (5) and/or a repeating unit of the formula (6).

o^SrR4 R3 (8) Each is preferably a hydrogen atom -25- 200951185.

Ri represents an alkyl group. Preferred examples of the alkyl group of the heart include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. R2 represents a hydrogen atom or an alkyl group. Preferred examples of the alkyl group for R2 are a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group and an octyl group. Further, Ri and R2 may be bonded to each other to form a ring structure, and may also contain an oxygen atom, a nitrogen atom or a sulfur atom. The linking structure is an alkylene group, an oxiranyl group or an propylene oxide group, and an alkyl group is particularly preferred. The alkyl group has an extended ethyl group, a propyl group, a butyl group, a pentyl group, and more preferably a propyl group or a butyl group. R3 and R4 independently represent a hydrogen atom or an alkyl group. The alkyl group of R3 and R4 is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, decyl, dodecyl, methyl, ethyl, propyl. But butyl is better. R3 and R4 may be connected to each other to form a ring structure. The linking structure is preferably an alkylene group, an oxiranyl group, an propylene oxide group, an alkylene group or an oxirane group. The alkyl group is preferably a butyl group or a pentyl group. The oxiranyl group may be represented by -(CH2-CH2-〇-CH2-CH2)n-, and η is preferably 1 to 4, more preferably 1 to 2. The repeating unit of the general formulae (5) and (6) is preferably hydrophilic. The theoretical formula of the solubility parameter (SP値) proposed by Chongjin Junzhi is used.

Vol. 29, No. 6 (1993) 249~259) The date of the repeating order is preferably 20 Μ P a 1 /2 or more. Below this, the dispersant becomes a hydrophobic injection. In the aqueous medium in which the particles are formed, the pigment particles are strongly aggregated, and the aggregation is difficult to be resolved, and the dispersion in the non-aqueous medium is poor. The repeating unit of the general formulae (5) and (6) is specifically exemplified below, but the present invention is not limited to these. Specific examples of the general formula (5), N7~10 are general formulas of the general formula (6) -26-200951185.

o, N) 〇 <;t^) N-5 N-6

N-7 N~8 N-9 N-10 When the general formulae (1) and (2), (3) and (4), (5) and (6) are combined into one unit a, β, γ, The mass ratio of α, β, γ is α: β: γ = 〇.1~50: 0·1~ 60: 30~90, and the copolymerization is better, and the better one is: β: γ = 5~50: 5~ 40 = 30~90, which is appropriately selected to make the sum of up to 1〇〇. f. The dispersant can be obtained by polymerizing a monomer constituting the formulae (1) to (6), for example, by radical polymerization in a solvent. At the time of the radical polymerization, a free radical polymerization initiator can be used, and a chain transfer agent (e.g., 2-thioethanol and decathial) can be further used. It can also be synthesized by referring to the description of JP-A-2001-31885. The combination of the general formulae (1) to (6) is preferably a polymer compound having a repeating unit of the formula (1), a repeating unit of the formula (5), and a repeating unit of the formula (3); a polymer compound of the repeating unit of the formula (1), a repeating unit of the formula (6), and a repeating unit of the formula (3); a repeating unit of the formula (1); a repeating unit of the formula (5); a polymer compound of the repeating unit of the formula (4): -27-200951185; a polymer compound having a repeating unit of the formula (2), a repeating unit of the formula (5), and a repeating unit of the formula: The repeating unit of the formula (2), the repeating unit of the formula (6), and the polymer compound of the repeating unit of the formula (3) have a repeating unit of the formula (2) and a repeat of the formula (5) A polymer compound of a unit and a repeating unit of the formula (4). More preferably, the combination of the general formulae (1) to (6) is a polymer compound having a repeating unit of the formula (1), a repeating unit of the formula (5), and a repeating unit of the formula (3); a polymer compound of the repeating unit of the formula (2), a repeating unit of the formula (5), and a repeating unit of the formula (3); a repeating unit of the formula (1), a repeat of the formula (5) A polymer compound having a unit and a repeating unit of the formula (4); a polymer compound having a repeating unit of the formula (2), a repeating unit of the formula (5), and a repeating unit of the formula (4). Here, preferred examples of the combination of the general formulae (1) to (6) are as follows. -28- 200951185

(Mit) 0-1 0-2 0-3 0-4 0-5 -29- 200951185

0-7

(Lean ratio) Ο-β

\=J 0-9

-30- 200951185 /

0·15

0-16 0-17 0-18 -31- 200951185

0-22 (RS ratio) 0-23 In the present invention, an acid can be added to prepare an aqueous aggregate after the preparation of the re-sinking liquid (aqueous dispersion) of the organic pigment fine particles. Alternatively, an acid may be added to the poor solvent before the precipitation of the aqueous dispersion of the organic pigment fine particles, and the pigment solution may be added to the -32-200951185 to make the organic pigment fine particles a hydrophilic aggregate. It is preferred to obtain an aqueous agglomerate by adding an acid prior to the poor solvent. Here, the "aqueous aggregate" in the present invention means an agglomerate in which the aggregate or the surface of the organic pigment fine particles constituting the aggregate is covered with a hydrophilic dispersant. Here, when quantitatively distinguishing between pro-hydrophobicity, the solubility parameter (SP値) theoretical formula proposed by Oki Tsutomu is used (Japan Next Society) Vol_ 29, 1^〇.6 (1 993) 24 9~2 5 9 Item) When the calculation of the dispersant is 201?? & 1/2 or more, the dispersant is said to be hydrophilic. The hydrophilic aggregate is not particularly limited as long as the primary particles of the organic pigment particles are agglomerated by 2 or more particles, and usually the average particle diameter is about 5 μmη, and 0.04 to ΙΟμπι is preferable. The acid used to form the aqueous agglomerate is preferably acetic acid, hydrochloric acid, sulfuric acid or formic acid, more preferably acetic acid or hydrochloric acid. The pH of the aqueous dispersion at the time of formation of the aqueous agglomerate is not particularly limited as long as it can form agglomerates, preferably pH 1 to 6, and pH 2 to 4 is more preferable. The solid content of the aqueous agglomerate is actually substantially composed of a pigment, and the content of the pigment in the prepared liquid is, for example, 〇.〇 〇 4 to 4% by mass. This concentration is also the same as the non-aqueous aggregates described later. In the present invention, an organic polymer compound having a mass average molecular weight of 1,000 or more is coexisted with an aqueous agglomerate, and it is preferably a hydrophobic aggregate. (hereinafter, "organic polymer compound having a mass average molecular weight of 1,000 or more" or "organic polymer compound" or "dispersant for hydrophobicization".) In the present invention, organic pigment particles present in an aqueous medium are borrowed. After the hydrophobic agglomerates are prepared by adding at least one organic polymer compound having a mass average molecular weight of 100 or more, the organic nanoparticles can be aggregated. The organic nanoparticles present in the aqueous medium are directly treated with filter paper. -33- 200951185 Filtration also filters the filter paper, and filtering with the filter is also time consuming. As described above, the addition of an acid or a base to the poor solvent allows the organic pigment fine particles to be obtained as an aqueous aggregate at the time of preparation of the aqueous dispersion of the organic pigment fine particles. However, only this is because the hydrophilicity of the agglutination system does not form a large aggregate in the aqueous medium, and the filtration is also time consuming due to poor dehydration. Accordingly, in the present invention, it is preferred to add the organic polymer compound to make the aqueous agglomerate a non-hydrophilic agglomerate (hereinafter referred to as "hydrophobic aggregate"). The organic pigment fine particles can be made into a large aggregate in an aqueous medium by the addition of an organic polymer compound. By this means, the time required for filtration can be shortened, and the filterability can be greatly improved. In the present invention, "hydrophobic aggregate" means an aggregate in a state where the aggregate or the surface of the organic pigment fine particles constituting the aggregate is covered with a dispersing agent for hydrophobicization. In this case, when quantitatively referred to as pro-hydrophobicity, the solubility parameter (SP値) theoretical formula proposed by Oki Tsutomu (Japanese Society of Science and Technology Vol 29, No. 6 (1993) 249-259), dispersant When the enthalpy is less than 20 ΜP a 1 /2, the dispersant is said to be a dispersing agent for hydrophobicization. In the present invention, the organic polymer compound is preferably added to the aqueous dispersion containing the hydrophilic aggregate. The average particle size of the hydrophobic aggregate is preferably 10 μm or more, and the larger the better. Below 1 〇 μ m, the separation of the aggregate takes time, passes through the filter, plugs the filter paper or the filter. The so-called average particle diameter is the diameter of the aggregate measured by an optical microscope to observe the aggregate and compared with another standard scale for observation. This so-called diameter system measures the length between the ends of the aggregate, and the longest is defined as the diameter. In the present invention, the agglutination system collects two or more primary particles of the nanoparticles which are not visible to the naked eye, and the secondary particles are aggregated to become the second-34-200951185 secondary particles. In the present invention, a preferred organic polymer compound has a structural site having affinity for a non-aqueous medium (a repeating unit having a group having affinity for a non-aqueous medium) and a structural site having affinity for the organic pigment microparticle (having The repeating unit of the group having an affinity for the organic pigment fine particles) functions as a compound which disperses the organic pigment fine particles in a non-aqueous medium. The organic polymer compound acts on the hydrophilic aggregate, and the structural portion having affinity for the organic pigment fine particles is coated on the surface of the aqueous aggregate or on the surface of the organic pigment fine particles constituting the aggregate, and as a result, the aggregate or the particles are used for non-aqueous The medium is hydrophobized with an affinity structure. In the present invention, the organic polymer compound is adsorbed to the aggregated organic pigment particles. Therefore, after the steps of filtration, washing, redispersion, etc., the organic polymer compound can function as a dispersing agent directly in the non-aqueous medium, and it is not necessary to add a new dispersing agent. In order to adjust the dispersibility, it is also possible to add a new dispersant afterwards, but it is preferable not to add it from the viewpoint of manufacturing cost. In the present invention, the organic pigment fine particles constituting the aggregate are preferably agglomerated in a state in which the organic polymer compound is coated, and are not aggregated with such an organic polymer compound, and are more agglomerated than, for example, agglomerates such as hydrochloric acid. Re-dispersion after sputum is easier. 'Organic pigment particles are more easily deagglomerated into primary particles, and the contrast is increased. The organic polymer compound may be directly added, but it is preferably added to dissolve the organic polymer compound in a solvent in order to obtain good filterability. The solvent for dissolving the organic polymer compound can be mixed with the aqueous dispersion of the organic pigment microparticles to dissolve the organic polymer compound, and the organic polymer compound itself is not precipitated after the addition of -35 to 200951185, that is, there is no particular limitation. The solvent for dissolving the organic polymer compound is, for example, an aqueous solvent (for example, water or hydrochloric acid, an aqueous sodium hydroxide solution), an alcohol compound solvent, a guanamine compound solvent, a ketone compound solvent, an ether compound solvent, an aromatic solvent, a carbon disulfide solvent, or the like. Aliphatic compound solvent, nitrile compound solvent, hydrazine compound solvent, halogen compound solvent, ester compound solvent, ionic liquid, mixed solvent of these, etc., aqueous solvent, alcohol compound solvent, ketone compound solvent, ether compound solvent, yam compound The solvent, the ester compound solvent, the guanamine compound solvent 'nitrile compound solvent or a mixture thereof is preferred, and the ketone compound solvent 'ether compound solvent, nitrile compound solvent or a mixture thereof is particularly preferred. The alcohol compound solvent is, for example, methanol, ethanol, isopropanol, n-propanol, 1-methoxy-2-propanol or the like. The ketone compound solvent is, for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone or the like. The solvent of the ether compound is, for example, dicarboxylic acid, diethyl ether, tetrahydrofuran or the like. The aromatic compound solvent is, for example, benzene, toluene or the like. The aliphatic compound solvent is, for example, hexane or the like. The solvent of the nitrile compound is, for example, ethyl acesulfame or the like. The halogen compound solvent is, for example, dichloromethane, trichloroethylene or the like. The solvent of the vinegar compound is, for example, ethyl acetate, ethyl lactate, 2-(1-methoxy)propyl acetate or the like. The ionic liquid is, for example, a salt of 1-butyl-3-methionazole and a salt of PF6-. The amount of the solvent used for dissolving the organic polymer compound is such that the amount of the organic polymer compound which can be dissolved and the amount of the hydrophobic aggregate which can easily form a furnace is not particularly limited, and the complexity of the production and the reduction of the raw material cost are considered. It is better to use as few as possible. In the case of the mass ratio, when the aqueous dispersion of the organic pigment fine particles is 100, the solvent to be added is preferably in the range of 0 to 丨〇 0, preferably -36 to 200951185, and particularly preferably in the range of 0 to 70. Too much filtering can take a lot of time. After the organic polymer compound is added, it is preferably stirred in such a manner as to be sufficiently mixed with the aqueous dispersion of the organic pigment fine particles. Stirring and mixing can be carried out by a usual method. The temperature at which the organic polymer compound is added and mixed is not particularly limited, and is preferably 1 to 100 ° C, more preferably 5 to 60 ° C. The addition and mixing of the organic polymer compound can be carried out by any means, for example, a stirring blade or a Raymond mixer. The amount of the organic polymer compound to be added is preferably 10% by mass or more and 1,000,000% by mass or less, more preferably 50% by mass or more and 200% by mass or less based on the pigment. When the amount of addition is too small, the effect of the hydrophobicization (non-aqueousization) of the nanoparticles is small, and if it is too large, the problem of an increase in viscosity is likely to occur when redispersing. In the present invention, the mass average molecular weight of the organic polymer compound is preferably 1 〇〇〇 or more. Although there is no special upper limit, it is preferably 3,000,000 or less, and more preferably 300,000 or less. Specific examples of the organic polymer compound which can be used in the present invention are "Disperbyk-1 10 (acid group-containing copolymer), 130 (polyamide), 161, 162, 163, 164, 165, 166 manufactured by BYK / Chemie. 170 (polymer copolymer), "BYK-P104, P105 (high molecular weight unsaturated polycarboxylic acid), EFKA 4047, 4050, 4010, 4165 (polyurethane), EFKA43 3 0, 4 3 40 (" Block copolymer), 4400, 4402 (modified polyacrylate), 5010 (polyester decylamine), 5765 (high molecular weight polycarboxylate), 6220 (fatty acid polyester)", Ajinomoto Precision Technology Co., Ltd. "AZISPER PB821, PB822", "FLOREN TG-71 0 (urethane ester oligomer)", "POLYFLO No. 50E, No. 300 (propylene fluorene copolymer)" manufactured by Kyoei Chemical Co., Ltd., -37- 200951185 Nanben Chemical Co., Ltd. "DISPERON KS-860, 8 73 SN, 874, # 2 150 (aliphatic polycarboxylic acid), # 7004 (polyether ester), DA-7 0 3 -5 0, DA-705 ' DA -725", Kao Corporation "DEMORRN, N (naphthalenesulfonic acid formalin polycondensate), MS, C, SN-B (aromatic sulfonate fumarate polycondensate)", "HOMOGENO-L-1 8 (polymer polycarboxylic acid), "EMULGEN 920, 930, 935, 985 (polyoxyethylene phenyl ether)", "ACETAMIN86 (stearylamine acetate)", "SOLSPERS 55000" manufactured by LUPRIZOL Co., Ltd. Polymer), 13240 (polyesteramine), 3000, 17000, 27000 (polymer with functional portion at the end), 24000, 28000, 32000, 38500 (grafted polymer)", NIKKOL T106 (manufactured by Nikko Chemical Co., Ltd.) Polyoxyethylene sorbitan monooleate), MYS-IEX (polyoxyethylene monostearate), and the like. In the present invention, the known polymer compound may be used singly or in combination of two or more kinds as the organic polymer compound. It is known that the polymer compound may be used in combination with one or more of the organic polymer compounds described below, and the organic polymer compound described below may be used singly or in combination of two or more. The organic polymer compound is a polymer compound obtained by copolymerizing at least one of the following monomers (Α) to (D), or at least one of the monomers using (Α) to (D). The polymer compound of the formula (1) is preferred. General formula (1)

(In the formula (1), X represents a (Ι+m) valent linkage group, S represents a sulphide-38-200951185; and Y is a monomer of at least one of the monomers (A) to (B). The basis of the composition, Z is a group consisting of at least one of the monomers of (C) to (D); 1 + m is 3 to 10, 1 is 〇~1〇, m is 0 to 10 (A) a monomer containing at least one of an acidic group and a basic group (B) containing a nitrogen-containing heterocyclic monomer (C) containing a monomer having an affinity for a non-aqueous medium (D) a combination of monomers (A) to (D) containing an oligomer having affinity for organic pigment particles present in an aqueous medium, in combination (a), (C) or (B), (C) ) a component of (A), (B), (C), or (A), (C), (D), or (b), (C), (D) The combination is better, and the combination of the components (A), (B), (c), and (D) is particularly preferable. (A) The monomer having at least one of an acidic group and a basic group is a monomer having a hydroxy group, a sulfonic acid group, a phosphoric acid group, an amine group, a guanamine group, or a urea group, to obtain an organic polymer. It is preferred that the compound be adsorbed to the organic pigment particles via an acid-base interaction. Specifically, for example, but not limited to these. -39- 200951185 HOzC^^

H02C

A-1 A-2

A-8

H02C A -3 HOaC’^Y^ A_4 G02H wide C02H a-5 co2h

A-9 A-10 A-11 co2h

H02C A-6 co2h

A-12

A-14 -40- 200951185

O

NH H2N Jj A-15 A-20

A-21 J< A-16 f

HN N Fire H

(B) A monomer containing a nitrogen-containing heterocyclic ring, containing a benzimidazolone group, a benzimidazolyl group, a fluorenyl group, a uracil group, an acridinone group, a naphthoquinone group, a carbazolyl group, a pyridine Monomers such as imidazolyl, amber succinimide, benzopyrrolyl, etc., to obtain an organic polymer compound which can be adsorbed by hydrogen bonding interaction, van der Waals interaction, dipole-dipole interaction The construction of organic pigment particles is preferred. Specifically, for example, but not limited to these. -41 - 200951185

(c) The monomer having an oligomer having affinity for a non-aqueous medium is not particularly limited, and is preferably one which is soluble in a non-aqueous medium used for redispersion in a later embodiment, and has an organic substance in a non-aqueous medium. The dispersion of the pigment particles can be stabilized by the stereoscopic repulsive force. The single system of (C) comprises a polystyrene skeleton, a polymethyl propyl methacrylate skeleton, a polybutyl methacrylate skeleton, a polymethyl propylene acid 2 - an ethyl ester skeleton, a poly methacrylic acid 2-Ethylhexyl ester skeleton, polyethylene glycol backbone, polypropylene glycol skeleton, polycaprolactone skeleton is preferred 'containing polystyrene skeleton, -42- 200951185 polymethyl methacrylate skeleton, polyethylene glycol skeleton, Polypropylene glycol skeletons and polycaprolactone skeletons are particularly preferred. This monomer may be a commercially available product or may be a suitable synthesizer. Specifically, commercially available products include a polystyrene oligomer having a terminal methacrylic acid (Μ n = 6000, trade name: AS-6, manufactured by East Asia Synthetic Chemical Industry Co., Ltd.), and a terminal methacrylic acid. Deuterated polymethyl methacrylate oligomer (Mn = 6000, trade name: AA-6, manufactured by East Asia Synthetic Chemical Industry Co., Ltd.), low-end polybutyl methacrylate methacrylate Polymer (Mn = 6 000, trade name: AB-6, manufactured by East Asia Synthetic Chemical Industry Co., Ltd.), polymethyl methacrylate/2-hydroxyethyl methacrylate oligomerization at the end of methacrylic acid (Mn = 7000, trade name: AA-714, manufactured by East Asia Synthetic Chemical Industry Co., Ltd.), methacrylic acid butyl methacrylate/2-hydroxyethyl methacrylate oligomer Mn = 7000, trade name: 707S, manufactured by East Asia Synthetic Chemical Industry Co., Ltd.), 2-methylhexyl methacrylate/2-hydroxyethyl methacrylate oligomer (Mn) =7000, trade name: AY-707S, AY-714S, East Asian Synthetic Chemical Industry Co., Ltd.), methoxy polyethylene glycol methacrylic acid Ester (trade name: NK ester M-40G, M-90G, M-23 0G (manufactured by East Asia Synthetic Chemical Industry Co., Ltd.); trade name: BLENMER PME-100, PME-200 > PME-400, PME - 1 000, PME-2000, PME-4000 (above: 曰本油月()), polyethylene glycol monomethyl acrylate (trade name: BLENMERPE-90, PE-200, PE- 350, sakamoto grease (stock), polypropylene glycol monomethacrylate (trade name: BLENMER PP-500, PP-800, PP-1 000 > 曰本油(股)),

Polyethylene glycol polypropylene glycol monomethacrylate (trade name: BLENMER-43-200951185 70PEP-370B, manufactured by Nippon Oil & Fats Co., Ltd.), polyethylene glycol polytetramethylene glycol monomethacrylate (trade name) : BLENMER 55PET-800, manufactured by Nippon Oil & Fats Co., Ltd., polypropylene glycol polytetramethylene glycol monomethacrylate (trade name: BLENMER NHK-5050, manufactured by Nippon Oil & Fats Co., Ltd.). Specific examples of the synthetic product include 2-ethylhexyloxypolycaprolactone oligomer obtained by ring-opening polymerization of 2-ethylhexanol and ε-caprolactone, and a terminal of a methoxypolyethylene glycol polypropylene glycol random copolymer. An oligomer having a first amine group (trade name: Jeffamine 2 00 5, manufactured by HUNTSMAN Co., Ltd.), a butylene polypropylene glycol oligomer (manufactured by Aldrich Co., Ltd.), and the like, and reacted with (meth) propylene oxirane ethyl isocyanate. One of the ends has a polymerizable group of oligomers. The monomer of (D) containing an oligomer having affinity for the organic pigment microparticles present in the aqueous medium is not particularly limited to have an affinity for the organic pigment microparticles present in the aqueous medium, and for redispersion It is preferred that the non-aqueous medium has an affinity, that is, a structure having both a hydrophilic portion (a repeating unit having a hydrophilic group) and a hydrophobic portion (a repeating unit having a hydrophobic group). The single system is particularly suitable for both aqueous medium and non-aqueous medium, and can impart hydrophilic aggregate wettability to the organic pigment particles present in the aqueous medium, and can be used in a non-aqueous medium by stereoscopic repulsive force. The structure in which the dispersion of the organic pigment fine particles is stabilized is preferable. The monomer (D) used in combination with the monomer of (C) is not a monomer of (C), but is preferably a hydrophilic ratio (C). The single system of (D) contains a polystyrene skeleton, a polymethyl methacrylate skeleton, a polybutyl methacrylate skeleton, a polymethacrylic acid 2-ethyl ester skeleton, and a poly(methacrylic acid) 2-hydroxyl group. The ester skeleton, the polyethylene glycol skeleton, the poly-44-200951185 propylene glycol skeleton, and the polycaprolactone skeleton are preferred, and the polyethylene glycol skeleton, the polypropylene glycol skeleton, and the polycaprolactone skeleton are particularly preferable. This monomer may be a commercially available product or may be a suitable synthesizer. Specifically, commercially available products include methoxy polyethylene glycol methacrylate (trade name: NK ester M-40G, M-90G, M-230G (manufactured by Toagosei Chemical Co., Ltd.); ···BLENMERPME-100, PME-200, PME-400, PME-1000, PME-2000, PME-4000 (made by Japanese fats and oils), polyethylene glycol monomethacrylate (trade name: BLENMER PE) -90, PE-200, PE-350, manufactured by Sakamoto Oil Co., Ltd.), polypropylene glycol monomethacrylate (trade name: BLENMERPP-500, PP-800, PP-1000' manufactured by Nippon Oil & Fat Co., Ltd.) , polyethylene glycol polypropylene glycol monomethacrylate (trade name: BLENMER 70PEP-370B, manufactured by Nippon Oil & Fats Co., Ltd.), polyethylene glycol polytetramethylene glycol monomethacrylate (trade name: BLENMER 55PET) -800, manufactured by Nippon Oil & Fats Co., Ltd., polypropylene glycol polytetramethylene glycol monomethacrylate (trade name: BLENMERNHK-5050, manufactured by Sakamoto Oil Co., Ltd.). Specific examples of the synthetic product include an oligomer of a first amine group at one end of a methoxy polyethylene glycol polypropylene glycol random copolymer (trade name: Jeffamine 100, Jeffamine 2070, manufactured by HUNTSMAN Co., Ltd.), and methoxypolyethylene glycol polymerization. A propylene glycol oligomer (manufactured by Aldrich Co., Ltd.) or the like which reacts with (meth)acryloyloxyethyl isocyanate to obtain an oligomer having a polymerizable group at one terminal. In the polymer compound obtained by copolymerization of at least one of the monomers (A) to (D), the mass ratio is (A) : (B) : (C) : (D) = (〇.l~60) : (0~50) : (20~90) : (0~60) is better, these mass ratios are appropriate -45- 200951185 and the sum is 100. The polymer compound of the formula (1) is a mass ratio (Mohr ratio) (A): (B) : (C): (D) = (0. Bu 6): (0.1 to 5): (1) ~9): (1~6) is better. These mass ratios are appropriately selected so that the sum is equivalent to the (1+m) valence of X in the general formula (i). The polymer compound obtained by copolymerizing at least one of the monomers (A) to (D) can be obtained by radical polymerization of a monomer of (A) to (D), for example, in a solvent. In the radical polymerization, a radical polymerization initiator may be used, and a chain transfer agent (for example, 2-anthracene ethanol and dodecylmercaptan) may also be used. The pigment dispersant containing a copolymer can be synthesized by referring to the description of JP-A-2001-31885. A monomer compound of the formula (2) and (A) to (D) can be used by using at least one of the polymer compounds of the formula (1) in which the monomers (A) to (D) are synthesized. The method described in -26 2 3 7 8 is synthesized. General formula (2) (HSfxIsH) I m In the above formulae (1) and (2), X represents a (i+m)-valent linking group. 1+m is 3~10. The linking group of the (i+m) valence represented by X is a nitrogen atom of from 1 to 100, a nitrogen atom of from 0 to 10, and an oxygen atom of 0 to 5 Å. The group consisting of up to 200 hydrogen atoms and 0 to 20 sulfur atoms may further contain an unsubstituted or substituted group. X in the above formulas (1) and (2) is preferably a carbon atom of from -60 to 200951185 atoms, from 0 to 10 nitrogen atoms, and from 0 to 50 oxygen atoms. A radical consisting of one to 100 hydrogen atoms and 0 to 20 sulfur atoms. The linking group represented by X is preferably an organic linking group. A preferred specific example of the organic linking group [specific examples (r-Ι) to (r-17)] is as follows. However, the present invention is not limited to these.

-47 200951185

Among the above, '(r -1 ), ( r - 2 ), ( r - 1 0 ), ( r -1 1 ), from the viewpoints of difficulty in obtaining and synthesizing raw materials and solubility in various solvents, The basis of (r-16) and (r-17) is better. When the above X has a substituent, the substituent may have an alkyl group having 1 to 20 carbon atoms such as a methyl group or an ethyl group, an aryl group having 6 to 16 carbon atoms such as a phenyl group or a naphthyl group, and a hydroxyl group or an amine group. a methoxy group having 1 to 6 carbon atoms such as a carboxy group, a carboxy sulfonylamino group, an N-beanthine group or an ethoxylated group, and a carboxy group having 1 to 6 carbon atoms such as a methoxy group and an ethoxy group. A halogen atom such as an oxy group, a chlorine atom or a bromine group; an alkoxycarbonyl group having 2 to 7 carbon atoms such as a methoxycarbonyl group, an ethoxycarbonyl group or a cyclohexyloxycarbonyl group; or a carbonate group such as a cyano group or a tributyl butyl carbonate. The polymer compound obtained by copolymerizing at least one of the monomers (A) to (D), and the polymer of the formula (1) using at least one of the monomers (A) to (D) Specific examples of the compound are not limited thereto. Wherein Me represents a methyl group and Bu represents a butyl group. R represents - 〇-CO-CH2-CH2-, bonded to the S (sulfur atom) in the repeating unit. In the following specific examples, when each repeating unit is located at the end of the constituent polymer compound, the terminal of the repeating unit is substituted with a hydrogen atom. In P-9 to P-11, the number 値 indicated by the parentheses of the repeating unit indicates the mass ratio. -48 - 200951185

-49- 200951185

(^JOUI-e/o-UA/x (out of°«>2/0~/01 ΗΙΪ/0/β 200951185

olAli/o-/o-·" p/w· -51 - 200951185

-52- 200951185 The aggregate will settle, and the supernatant can be decanted, extracted and removed to make the aggregate easier to separate in the next. Further, by performing the centrifugal separation instead of standing, the aggregate may settle more quickly, and the time can be shortened. The separation method may be a variety of filtration methods, such as limit filtration, centrifugal separation, filtration with a filter paper, filter, and the like. By ultrafiltration, for example, a method for desalting/concentrating of a silver halide emulsion can be employed. Known Research Disclosure No. 10208 (1972),

The method described in No. 13 122 (1975) and No. 16 351 (1977). The important pressure difference and flow rate in the operation f % % can be determined by the technique curve described in the book "Your Film Utilization Technical Manual", fortunately published in the book (1 97 8 ), p27 5, and the target organic nanoparticle. The optimum conditions for suppressing unwanted agglutination of the particles must be found in the treatment of the dispersion. The method of replenishing the solvent lost through the film is a fixed-capacity type in which the solvent is continuously added and intermittently added in batches, and a constant volume type in which the desalination treatment time is relatively short is preferable. The solvent to be replenished is a pure water obtained by ion exchange or distillation, and a poor solvent such as a dispersant or a dispersant may be mixed in pure water, or may be directly added to the organic nanoparticle dispersion. When the filter is filtered, for example, a pressure filtration device can be used. Preferred filters include filter paper, nanofilters, ultrafilters, and the like. A centrifugal separator for centrifuging and concentrating organic nanoparticle particles can be used if any of the organic nanoparticle particles in the organic nanoparticle dispersion (or organic nanoparticle concentrated extract) is allowed to settle. Centrifugal separators include, for example, general-purpose devices and other types of decanting functions (continuously pumping the upper layer and rotating the outside of the system), and continuously discharging the solids continuously. -53-200951185 Separator. The centrifugal separation conditions are preferably 50 to 10,000 by centrifugal force (representing a centrifugal acceleration of several times the gravitational acceleration), and more preferably 100 to 8,000 '150 to 6,000. The temperature at the time of centrifugation depends on the kind of the solvent of the dispersion, preferably -1 〇 to 80 ° C, and more preferably -5 to 70 ° C. The separated aggregates are washed for desalination, dehydration, and removal of excess dispersant. The washing operation can be carried out by limiting filtration, centrifuging, filtering with filter paper and filter, and directly adding washing liquid to clean it. Once the aggregate is taken out, it is re-slurryed in the washing liquid, and then subjected to limit filtration, centrifugal separation, The mixture is separated by filtration through a filter paper, a filter, or the like, and may be washed in combination. Washing is not only carried out as described above after separation, but also before separation. The agglomerated nano pigment particle dispersion was allowed to stand, and the supernatant liquid was removed, and the washing liquid was added thereto, followed by slurry formation. After re-slurrying, it is allowed to stand, and the supernatant is removed. Filtration is also possible, but it can also be directly filtered. Washing before separation is because the aggregates are often wet, not only the cleaning efficiency is increased, but also the subsequent dispersion is easier. If the cleaning solution can achieve desalination, dehydration, excess dispersing agent, and removal of the aggregating agent, there is no particular limitation, specifically, an aqueous solvent (such as water, or hydrochloric acid, aqueous sodium hydroxide), an alcohol compound solvent, a guanamine compound solvent. , a ketone compound solvent, an ether compound solvent, an aromatic solvent, a carbon disulfide solvent, an aliphatic compound solvent, a nitrile compound solvent, an anthraquinone compound solvent, a halogen compound solvent, an ester compound solvent 'ionic liquid, a mixed solvent thereof, etc., preferably Examples of the aqueous solvent, the alcohol compound solvent, the ketone compound solvent, the ether compound solvent, the nitrile compound solvent, the hydrazine compound solvent, the ester compound solvent, the guanamine compound solvent or a mixture thereof, the aqueous solvent, the alcohol-54-200951185 compound solvent, the ester compound The solvent and the nitrile compound solvent are more preferable. In the separated hydrophobic aggregate, it is preferred to contain a dispersing agent or a dispersing agent for hydrophobicity in addition to the organic pigment fine particles. The dispersant is preferably present in an amount of 10% by mass or more and 100% by mass or less based on the total amount of the pigment. More preferably, it is 10 mass% or more and 200 mass% or less. Too little or too much of this amount is liable to cause problems such as poor dispersion in a non-aqueous medium. The dispersing agent for hydrophobicity is preferably coexisted in an amount of 1% by mass or more and 1,000,000% by mass or less based on the pigment. More preferably, it is 50% by mass or more and 200% by mass or less. If the amount is too small, the dispersion is poor, and if it is too large, the viscosity is likely to increase when redispersion occurs. When dispersing the organic pigment fine particles in a non-aqueous medium, the dispersing agent has a function of promoting and maintaining the hydrophobic dispersing agent adsorbed to the organic pigment fine particles. Therefore, when the amount of the dispersing agent is too small, the dispersing agent for hydrophobicity is detached from the fine particles of the organic pigment, and when it is redispersed in the non-aqueous medium, it is liable to be poorly dispersed. On the other hand, the dispersing agent is hydrophilic, and if the amount is too large, the dispersing agent for hydrophobicity becomes less than the dispersing agent. Therefore, the hydrophobizing effect in the aqueous medium becomes insufficient, and when it is redispersed in a non-aqueous medium, it becomes trapped in poor dispersion. In the case of a dispersing agent for hydrophobicity, when the amount is too small, the hydrophobicizing effect of the dispersing agent for hydrophobicity may be insufficient. On the other hand, there is a problem of poor dispersion in a non-aqueous medium. When the amount of the dispersing agent for hydrophobicity is too large, there is a possibility that the dispersing agent for hydrophobicity is not adsorbed to the organic pigment fine particles, and the viscosity may increase when redispersed. The separated agglomerates may be directly redispersed as described below. Alternatively, the solvent may be further dispersed (described later, and then redispersed after wetting). The organic nanoparticle dispersion powder may be dried and taken out and then redispersed. -55- 200951185 There are no special restrictions on the drying method, such as freeze drying and drying under reduced pressure. The method of freeze-drying is not particularly limited and can be used in the industry. For example, the refrigerant direct expansion method, the repeated freezing method, the heat medium circulation method, the triple heat exchange method, and the indirect heating and freezing method are preferably a refrigerant direct expansion method or an indirect heating freezing method, and more preferably an indirect heating and freezing method. In either method, it is preferred to carry out freeze-drying after pre-freezing. The conditions for pre-freezing are not particularly limited, but the sample to be freeze-dried must be completely frozen. The indirect heating and freezing method includes a small freeze dryer, an FTS freeze dryer, a LYOVAC freeze dryer, an experimental freeze dryer, a freeze dryer for research, a triple heat exchange vacuum freeze dryer, a single cooling freeze dryer, The HULL freeze dryer is preferably a small freeze dryer, an experimental freeze dryer, a freeze dryer for research, a single-cooling freeze dryer, and more preferably a small freeze dryer or a single-cooling freeze dryer. The temperature of the freeze-drying is not particularly limited, and is, for example, -190 to -4 ° C' is preferably -120 to -20. Hey, better - around 80~-60 °C. The pressure for lyophilization is also not particularly limited, and may be appropriately selected by the manufacturer, for example, from 0 to 1 to 3 5 P a , preferably from 1 to 15 Pa, and more preferably from 5 to 10 P a. The freeze-drying time is, for example, 2 to 4 8 hours, preferably 6 to 3 6 hours, and more preferably 1 to 6 to 6 hours. However, these conditions can be appropriately selected. The method of freeze-drying can be referred to, for example, the preparation machine technical manual: preparation machinery technology research institute edited by the local library, P. 120-129 (September 2000); vacuum manual: 曰本vacuum technology (shares), ohm company , P. 328-331 (1992); Freeze and Dry Research Society: Ito Takaji, No. 15' ρ·82 (1965) -56- 200951185 and so on. The apparatus for concentrating the organic nanoparticles by drying under reduced pressure is not particularly limited as long as the solvent of the organic nanoparticle dispersion (or organic nanoparticle concentrated extract) is evaporated. For example, a vacuum dryer and a rotary pump which are generally used can be heated and decompressed while stirring a liquid, and the liquid can be passed through a tube which is heated and decompressed to be continuously dried. The temperature under reduced pressure was heated to 30 to 2 30. (: is better, 3 5~2 0 0 °C is better, 40~180 °C is better. The pressure under decompression is preferably 1〇〇~l〇〇〇〇〇Pa, 300~90000Pa is better. Further, 500 to 80000 Pa is preferable. According to the production method of the present invention, if necessary, the organic pigment fine particles in an aggregated state can be finely dispersed (in the present invention, finely dispersed or redispersed means that the aggregation of particles in the dispersion is released. Further, in the present invention, it is preferred that the hydrophobic aggregate obtained by redispersion is in a non-aqueous medium. (The dispersion or the non-aqueous dispersion thus obtained.) The above non-aqueous medium means an aqueous medium other than the aqueous medium. The medium is preferably a ketone compound solvent, an ester compound solvent or an aromatic solvent. Specifically, it is methyl ethyl ketone, cyclohexanone, ethyl acetate, butyl acetate, 2-(1-methoxy)propyl acetate, and nitrate. Benzene, chlorobenzene, dichlorobenzene, preferably methyl ethyl ketone, cyclohexanone, 2-(1-methoxy) propyl acetate, chlorobenzene. In order to make the above-mentioned agglomerated organic pigment particles a good filter Dispersed state to agglomerate organic pigment particles to obtain redispersible The degree of flocculation is preferred. The flocculation refers to a collection of particles of weak agglomeration (soft agglomeration) which is redispersible. The above hydrophilic aggregates and hydrophobic aggregates are preferably composed of flocculated floccules. The pigment microparticles become floccules. The organic pigment microparticles precipitated in, for example, the water-57-200951185-series mixture can be separated from the medium by rapid filtration, etc. Then, the separated floccules (soft aggregates) are redispersed in a suitable medium. By making an organic solvent of a color filter, it is possible to efficiently produce an organic solvent-based pigment dispersion composition (non-aqueous dispersion composition), that is, when a mixed solvent of a good solvent and a poor solvent is an aqueous solvent, it can be made high. The efficiency is replaced by a third solvent composed of an organic solvent, and the dispersion medium (continuous phase) is switched. The degree of dispersion by the usual dispersing method is insufficient, and the method of miniaturization is more efficient. Such a strong agglomerated organic particle (in the present invention, agglomerated organic particles refer to an organic particle such as agglomerate, which is aggregated by a secondary force) is also called a primary particle size of nanometer size. In the present invention, the aggregated organic particle liquid contains an organic polymer compound having a mass average molecular weight of 1 〇〇〇 or more, thereby being a dispersion in which the organic particles are appropriately finely dispersed (in the present invention, the agglomerated organic particle liquid) It means that the liquid containing agglomerated organic particles can be a dispersion, a concentrate, a paste, a slurry, etc., if it contains agglomerated organic particles.) More specifically, by using the above organic polymer compound, Good fine dispersion (performance of uniform fine particle size) and dispersion stability (characteristic of maintaining uniform fine particle size for a long time) when a mixture of a good solvent and a poor solvent is precipitated, and switching the medium to be suitable for a color filter The organic solvent is maintained after redispersion, and a high-performance color filter can be realized. Moreover, the above-mentioned organic polymer compound does not interfere with the optical characteristics of the color filter, and interacts with the coloring property of the organic nano pigment particles. High performance in color filters. A method of finely dispersing such a nanoparticle aggregate can be carried out, for example, by a method of ultrasonic dispersion or a method of applying physical energy. -58- 200951185 The ultrasonic illuminating device used is preferably capable of applying ultrasonic waves of 1 〇 kHz, such as ultrasonic homogenizer, ultrasonic washing, and the like. When the liquid temperature rises during the ultrasonic irradiation, the nanoparticles generate heat (see Non-Patent Document 1), so that the liquid temperature is preferably 1 to 100 ° C, and 5 t is more preferable. The temperature control method can be carried out by controlling the temperature of the dispersion, controlling the temperature of the temperature adjustment layer of the temperature of the dispersion liquid, and the like. The dispersing machine for applying the physical energy to disperse the concentrated organic nanoparticles is not particularly limited, and there are, for example, a kneader, a roll mill, a ground super honing machine, a dissolver, a homogenizer, a sand mill, and the like. . High dispersion methods and dispersion methods using tiny beads are also suitable. The preferred method for preparing the organic nanoparticle dispersion is to disperse the colorant in a tree mixture to a viscosity of 10,000 mPa·s at 25 ° C after the knead dispersion treatment, and it is desirable to be more than 100,000 mPa·s, followed by It is preferred to add a solvent, a micro-dispersion treatment to a viscosity of 1,0 0 mP a · s after the fine dispersion treatment, and a lower viscosity method of desirably less than 100 mPa·s. Used in the re-dispersion treatment of the mechanical two-roller, the three-roller, the ball-spinning sieve, the disperser, the kneading machine, the kneading extruder, the homogenizer, the dad-single-axis and the twin-axis extruder, etc. Strong shear forces are dispersed. The solvent is added, mainly using a vertical or horizontal sand mill, a pin mill, a slit ultrasonic disperser, a high-pressure disperser, etc., and the beads are finely dispersed by a zirconia having a particle diameter of 0.1 to 1 mm. It is also possible to use 0.1mm micro beads for precise dispersion treatment. After dispersing and disposing the main pigment and the auxiliary pigment separately, mixing the net agglomeration of the two on the two to make the machine and the pressure-separation degree into the cylinder viscosity, the machine, the machine, the second, the machine [Glass, the following points -59- 200951185 Dispersion treatment of the dispersion, and dispersion of the main pigment and the secondary pigment. As for the details of the dispersion, T.c. Patton is "Paint Flow and

"Pigment Dispersion" (published by john Wiley and Sons, 1964), etc., can be used. The dispersible organic pigment microparticle dispersion can improve the dispersibility of organic pigment microparticles. Active agent. A variety of compounds can be used as these dispersants, such as indigo derivatives (commercial product EFKA-6745 (manufactured by EFKA)), S0LSPERS 5 000 (manufactured by ZENEKA); organic alkane polymer KP341 (Shin-Etsu Chemical Co., Ltd.), (meth)acrylic (co)polymer POLYFLOW No. 75, No. 90, No. 95 (Kyoeisha Oil Chemical Industry Co., Ltd.), W001 (Yushang Company) Cationic surfactants; polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene phenyl ether, polyethylene glycol dilaurate , non-ionic surfactants such as polyethylene glycol distearate and calylide, and anionic interfacial surfactants such as W 0 0 4, W 0 0 5, and W 0 1 7 (manufactured by Yusho Co., Ltd.) Agent; EFKA-46, EFKA-47, EFKA-47EA, EFKA Compound 100, EFKA polymer 400, EFKA polymer 401, EFKA polymer 450 (manufactured by Morishita Sangyo Co., Ltd.) DISPERSE AID 6' DISPERSE AID 8' DISPERSE AID 15, DISPERSE AID 9100 (made by SUNOPCO) Molecular dispersion! I; SOLSPERS 3 0 00 '5000, 9000, 12000' 13240, 13940, 17000, 24000, 26000, 28000 and other SOLSPERS dispersants (ZENEKA (share) system); ADEKAPLURONIC L31, F38, L42, L44, L61, L64, F68, L72, P95, F77, P84, F87, -60- 200951185 P94, L101, P103, F108, L121, Ρ·123 (Asahi Chemical Co., Ltd.) and ISONETS-20 (Sanyo Chemical Co., Ltd.) Further, the pigment dispersant described in JP-A-2000-239554, the compound (C) described in Japanese Patent Publication No. Hei 5-72943, and the synthesis example 1 described in JP-A No. 2001-38 8 85 The compound or the like is also suitable. The organic nanoparticle dispersion composition after redispersion is such that the organic nanoparticle (primary particle) can be finely dispersed, and the particle diameter can be up to 1 to 200 nm, 2 ~100nm is better, 5~50nm is especially good. The Mv/Mn of the re-dispersed particles is preferably 1.0 to 2.0, more preferably 1.0 to 1.8, and particularly preferably 1.0 to 1.5. According to the production method of the present invention, although the pigment particles are made to have a small particle size of a nanometer size (for example, 10 to 100 nm), they can be concentrated and redispersed, and can be formed, for example, as a dispersion composition of organic pigment particles, followed by coloring. A photosensitive resin composition. Therefore, when these compositions are used for a color filter, the optical density is high, the surface uniformity of the filter is excellent, the contrast is high, and image noise is small. In addition, since the organic pigment fine particles containing the organic pigment fine particle-dispersed composition and the colored photosensitive resin composition can be highly and uniformly dispersed finely, it is possible to exhibit a high coloring concentration with a low film thickness, and to form a thin layer such as a color filter. It becomes possible. The organic pigment fine particle-dispersed composition and the colored photosensitive resin composition contain a pigment which exhibits a vivid color tone and a high coloring power, and can be used as an image forming material excellent for producing, for example, a color proof or a color filter. For the exposure and development of the colored image, the development of the image -61- 200951185 liquid can be used in the organic nanoparticle dispersion composition, the coloring photosensitive resin composition using an alkaline aqueous solution soluble binder (Adhesive), which can also respond to environmental requirements. The solvent (the dispersion medium of the pigment) used for the organic pigment fine particle-dispersed composition and the colored photosensitive resin composition can be used to satisfy the drying requirements after application by using an organic solvent having appropriate drying properties. [Coloring photosensitive resin composition] The colored photosensitive resin composition of the present invention contains at least (a) an organic pigment composition, (b) a binder, (c) a monomer or oligomer, and (d) a photopolymerization initiator. Or a photopolymerization initiator system. Each component of the colored photosensitive resin composition of the present invention will be described below. (a) Organic Pigment Composition The method of preparing the organic pigment composition has been described in detail. The content of the organic nano pigment particles is preferably from 3 to 90% by mass based on the total solid content in the colored photosensitive resin composition (in the present invention, the total solid content is a total of the components other than the organic solvent), 20 to 80% by weight. The quality is better, 25 to 60 mass. /. Especially good. If the amount is too large, the viscosity of the dispersion rises, which may become a problem in manufacturing suitability. If it is too small, the tinting strength is insufficient. The organic nano pigment particles with coloring function have a particle size system of 〇 1 μπι or less, preferably 0.0 8 μιη or less. For coloring, it can also be used in combination with a usual pigment, and the pigment can be used as described above. In the present invention, the organic nanoparticle is preferably used as the non-aqueous dispersion of the above organic nanopigment. (b) Adhesive The binder in the coloring photosensitive resin composition is suitable for a polymer compound having a mass average molecular weight of 1 〇 〇 or more. The content of the binder is -62-200951185. The total solid content of the colored photosensitive resin composition is generally 15 to 50% by mass, preferably 20 to 45% by mass. If the amount is too large, the viscosity of the composition is too high, which is a problem in manufacturing suitability. If it is too small, there is a problem in the formation of a coating film. (c) a monomer or oligomer containing a monomer or oligomer of the colored photosensitive resin composition of the present invention, which is a monomer having two or more ethylenically unsaturated double bonds and addition polymerization by irradiation of light Or oligomers are preferred. Such a monomer or oligomer has at least one ethylenically unsaturated group which can be polymerized in the molecule, and has a boiling point of 100 ° at normal pressure (: a compound of ±. Examples thereof are dipentaerythritol six ( Monofunctional acrylates such as methyl acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, and phenoxyethyl (meth) acrylate, monofunctional (meth) acrylate Ester; polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, trimethylolethane triacrylate, trimethylolpropane tri(meth)acrylate, trishydroxyl Propane diacrylate, neopentyl glycol di(meth)acrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol six (a) Acrylate, dipentaerythritol penta (meth) acrylate, hexanediol di(meth) acrylate, trimethylolpropane tris(propylene oxypropyl) ether, tris(propylene oxy oxy) Isoisocyanate, tris(propylene oxyethyl) cyanurate, glycerol Acrylate; (meth)acrylated polyfunctional acrylate, polyfunctional methacrylate after addition of polyfunctional alcohol such as trimethylolpropane or glycerol to ethylene oxide or propylene oxide. The general formulae (1) and (2) described in JP-A-10-5886, after the polyfunctional alcohol is added with ethylene oxide or propylene oxide, -63-200951185 (methyl) The urethane acrylates described in JP-A-48-41708, JP-A-50-6034, and JP-A-53-313 Polyester acrylates described in JP-A-49-43191, JP-A-49-43191, and epoxy acrylates such as epoxy resin and (meth)acrylic acid. a multifunctional acrylate or methacrylate. Among them, 'trimethylolpropane tri(meth)acrylate, neopentyltetrakis(meth)acrylate, dipentaerythritol hexa(meth)acrylate, Dipentaerythritol penta (meth) acrylate is preferred. In addition, 'the right one has a special opening 11-1 3 3 60 "Polymerizable compound B" described in the publication No. 0. These monomers or oligomers (such as a monomer or oligomer having a molecular weight of 200 to 1) may be used alone or in combination of two or more. The content of the total solid content of the coloring photosensitive resin composition is generally 5 to 50% by mass '100 to 40% by mass. If the amount is too large, the control of the developing property is difficult, and the manufacturing property is improved. When the amount is too small, the hardening power is insufficient at the time of exposure. (d) Photopolymerization initiator or photopolymerization initiator system The photopolymerization initiator or photopolymerization initiator system contained in the coloring photosensitive resin composition of the present invention (in the present invention) The photopolymerization initiator refers to a compound which promotes photopolymerization initiation by a combination of a plurality of compounds. The ortho-polyketalobnyl compound disclosed in the specification of U.S. Patent No. 23,67,660, the specification of U.S. Patent No. 2,448,882 An aromatic oxime compound substituted with an alpha-hydrocarbon as described in the specification of U.S. Patent No. 2,72,225, and U.S. Patent No. 3,046, the disclosure of which is incorporated herein by reference. The polycyclic guanidine compound described in the specification of No. 2951758, the combination of the triarylimidazole dimer described in the specification of U.S. Patent No. 3,549,367 and the ketone, and the benzoic acid described in Japanese Patent Publication No. 51-48516 A thiazole compound and a trihalide-s-three-till compound, a trihalomethyl-tri-trap compound described in the specification of U.S. Patent No. 4,239,850, a trihaloformamide compound described in the specification of U.S. Patent No. 4,212,976, and the like. Trihalo-s-tripper, trihaloformamodiazole and triarylimidazole dimer are especially preferred. In addition, the "polymerization initiator C" described in JP-A No. 1 1 _ 1 3 3 600, and the 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl) of the oxime system are suitable.肟, 0-benzylidene- 4'-(benzoquinone)benzylidene-hexyl-ketooxime, 2,4,6-trimethylbenzenecarbonyl-diphenylphosphine oxide, hexafluorophosphorus-trialkylbenzene Salt and so on. These photopolymerization initiators or photopolymerization initiator systems may be used singly or in combination of two or more kinds, and it is especially preferable to use two or more types. The display characteristics can be reduced by using at least two kinds of photopolymerization initiators. The content of the photopolymerization initiator or the photopolymerization initiator system of the total solid content of the colored photosensitive resin composition is usually 0.5 to 20% by mass, preferably 1 to 15% by mass. If the amount is too large, the sensitivity is too high to control. If it is too small, the exposure sensitivity is too low. The radiation that can be used for exposure is particularly suitable for ultraviolet rays such as g-line or i-line. The irradiation amount is preferably 5 to 1 500 mJ/cm2, more preferably 10 to 1000 mJ/cm2, and most preferably 10 to 500 mJ/cm2 (other additives) [Solvent] The coloring photosensitive resin composition of the present invention, the above components In addition, -65- 200951185 有机 can use organic solvents. Examples of the organic solvent are not particularly limited 'with vinegar' such as ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate Ester, ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, methyl hydroxyacetate, ethyl hydroxyacetate, butyl glycolate, ethyl methoxyacetate, methoxyacetate Ester, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-hydroxypropionate, ethyl 3-hydroxypropionate, etc.; alkyl 3-hydroxypropionate; methyl 3-methoxypropionate, 3 -ethyl methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate, propyl 2-hydroxypropionate, Methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, 2-hydroxy-2 - methyl methyl propionate, ethyl 2-hydroxy-2-propionate, methyl 2-methoxy-2-propionate, ethyl 2-ethoxy-2-propionate, pyruvate, Ethyl pyruvate, propyl pyruvate, methyl acetate, ethyl acetate, methyl 2-hydroxybutyrate, ethyl 2-hydroxybutyrate Ethers such as diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, alpha-lusuacetate, cefixil acetate, diethylene glycol monomethyl Ether, propylene glycol methyl ether butyrate, etc.; ketones such as methyl ethyl ketone, methyl isobutyl ketone, hexanone, cyclohexanol, 2-heptanone, 3-heptanone, etc.; aromatic hydrocarbons such as toluene , xylene, etc. Among these solvents, '3-ethoxypropionic acid methyl acetonate, ethyl 3-ethoxy oxoacetate, ethyl celecoxib acetate, ethyl lactate, lactic acid butyl vinegar, methyl 3-methoxypropionate, 2 - Heptone, cyclohexanone, carbitol acetate, tetracarbitol acetate, propanol methyl ether acetate, etc. are preferred solvents in the present invention. These solvents may be used singly or in combination of two or more. If necessary, a solvent having a boiling point of 180 ° C to 250 ° C can be used. This wins; high boiling point -66- 200951185 Solvent can be exemplified as follows. Diethylene glycol monobutyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether, 3,5,5-trimethyl-2-cyclohexen-1-one, butyl lactate, dipropylene glycol Methyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol diacetate, propylene glycol n-propyl ether acetate, diethylene glycol diethyl ether, 2-ethylhexyl acetate, acetic acid 3_methoxy_3_A Butyl ester, γ-butyrolactone, tripropylene glycol methyl ethyl acetate, dipropylene glycol n-butyl acetate, propylene glycol phenyl ether acetate, 1,3-butylene glycol diacetate. The content of the solvent is preferably from 10 to 95% by mass based on the total amount of the resin composition. [Surfactant] The color filter used in the past is rich in color for achieving high color purity, and the film thickness unevenness of the pixel directly appears as a problem of color unevenness. Therefore, it is required to improve the film thickness variation in the formation (coating) of the photosensitive resin layer which directly affects the film thickness of the pixel. The color filter of the present invention or the transfer material using the colored photosensitive resin composition of the present invention can be controlled to a uniform film thickness, thereby effectively preventing the application of stains (color spots due to variations in film thickness). It is preferred that the coloring photosensitive resin composition contains an appropriate surfactant. The surfactant disclosed in Japanese Laid-Open Patent Publication No. 2003-337424, No. Hei. The content of the surfactant is preferably 5% by mass or less based on the total amount of the resin composition. [Thermal polymerization preventing agent] The colored photosensitive resin composition of the present invention is preferably a thermal polymerization preventing agent. The thermal polymerization inhibitor is, for example, hydroquinone, hydroquinone monomethyl ether, p-methyl-67-200951185 oxyphenol, di-tert-butyl-p-cresol, gallic phenol, tributyl catechol, benzoquinone, 4, 4 '-Sulphate (3-methyl-6-tributyl), 2,2'-methylenebis(4-methyl-6-tert-butylphenol), 2-indolyl benzopyrene, morphine Wait. The content of the thermal polymerization inhibitor is preferably 1% by mass or less based on the total amount of the resin composition. [Dye for use as a pigment] The coloring photosensitive resin composition of the present invention may be added with a coloring agent (dye or pigment) other than the above-mentioned coloring agent (pigment) as necessary. When the pigment in the colorant is used, it is preferable to uniformly disperse the pigment in the coloring photosensitive resin composition. Therefore, the particle size is preferably 0.1 μm or less, and particularly preferably 〇 8 Γ 8 μΓ or less. The dyes and pigments to be used are the pigments described in the above-mentioned, and the pigments described in JP-A-2005-361447 [0068] to [0072]. The coloring agent described in JP-A-2005-17521 [0080] to [0088]. The content of the dye or pigment to be used is preferably 5% by mass or less based on the total amount of the resin composition. [Ultraviolet absorber] The colored photosensitive resin composition of the present invention may contain an ultraviolet absorber if necessary. The ultraviolet absorbing agent is a compound described in JP-A-H05-72724, and a salicylate-based, diphenylketone-based, benzotriazole-based, cyanoacrylate-based, nickel-chelating-based, hindered phenol-based, etc. . Specifically, there are phenyl ruthenate, 4-tert-butylphenyl sulphate, 2,4-di-t-butylbenzene-3', 5'-di-third _4'-hydroxy benzoate, salicylic acid 4-t-butylphenyl ester, 2,4-dihydroxydiphenyl ketone, 2-hydroxy-4-methoxydiphenyl ketone, 2-hydroxy-4-n-octyloxydiphenyl ketone, 2-(2 Hydroxy-5'-tolyl)benzotriazole, 2-(2, hydroxy-3'-t-butyl-5'-tolyl)-5-chlorobenzotriazole, ethyl-2-cyano-3, 3 -di-68- 200951185 Phenyl acrylate, 2,2'-hydroxy-4-methoxydiphenyl ketone, nickel formate, bis(2,2,6,6-tetramethyl-4-pyridine) fluorene g tributyl phenyl ester, phenyl salicylate, 4-hydroxy-2,2,6,6-tetramethyleneic acid-bis(2,2,6,6-tetramethyl-4-pipedyl)-ester, 2-[2-dimethyltoluene)phenyl]-:2H-benzotriazole, 7-{[4-chloro-5-trin-2-yl]amino}-3-phenylincin . The ultraviolet ray is preferably 5% by mass or less based on the total amount of the resin composition. The colored photosensitive resin composition of the present invention may contain other additives such as those described in JP-A No. 1 1 - 1 3 3 3 0 0. [Coating film of the coloring photosensitive resin composition] The coloring photosensitive resin composition of the present invention is appropriately determined by using the coloring photosensitive resin composition of the present invention in the previous [coloring photosensitive resin composition] item. Preferably, the coloring photosensitive resin composition of the present invention comprises (c) a monomer or an oligomer polymerized to form a colored photosensitive polymer film, and the color thereof can be produced. Filter (color as described later). (d) Photopolymerization initiator or photopolymerization initiator system as a coloring initiator or a photopolymerization oligomer; <Color filter and preparation method thereof> Next, the color filter of the present invention and the invention thereof will be described The color filter is characterized by the photocurable composition of the present invention (coloring photosensitive tree dibutyldiamine dithiol ester, salicylic acid 4 - cultivating condensate, amber hydroxy-3,5- The content of the bis (α, α--6-(diethylamino) absorbent is I 0. The addition of the above-mentioned additive to the "adhesive aid" and the coating film are the same as described below. It is preferably 0 to 3.0 μm. The coating film is formed by polymerizing the color filter of the resin composition to be injected, and can be carried out by light action. The method has a fat composition on the holder -69 - Coloring pattern of 200951185. The color filter of the present invention is described in detail below by the manufacturing method thereof (manufacturing method of the color filter of the present invention). The color filter of the present invention is characterized in that it is included on the substrate directly or in the medium. The other layer imparts the photocurable composition of the present invention to form a photosensitive film a step (hereinafter referred to as "photosensitive film forming step" as appropriate), a step of exposing the formed photosensitive film pattern (exposure through a mask) (hereinafter referred to as "exposure step" as appropriate), and sensitization after exposure The step of forming a colored pattern by a film formation (hereinafter referred to simply as "development step"). Each step in the method of producing a color filter of the present invention will be described below. (Photosensitive film forming step) Photosensitive film forming step The photocurable composition of the present invention is applied (provided) directly or on a substrate having another layer to form a photosensitive film. The substrate which can be used in this step is, for example, soda glass for liquid crystal display elements, PYREX (registered) (trademark) glass, quartz glass, and those having a transparent conductive film attached thereto, such as a photoelectric conversion element substrate such as a photographic element, such as a germanium substrate, a complementary metal oxide semiconductor (CMOS), etc. These substrates are sometimes formed with isolation. Black stripes of pixels. If necessary, it is also possible to provide adhesion to the upper layer, prevent diffusion of substances, or planarize the surface of the substrate. The undercoat layer (other layer). The photocurable composition of the present invention is applied onto a substrate, and various coating methods such as slit coating, inkjet method, spin coating, cast coating, roll coating, and screen printing may be employed. The coating film thickness of the photocurable composition is preferably 0.1 to 1 0 μ Π1, 〇. 2 -70- 200951185 〜5μιη is better, 0_2~3μηι is particularly good. The photosensitive film coated on the substrate Drying (prebaking) can be carried out at a temperature of 50 ° C to 140 ° C for 10 to 300 seconds using a hot plate, an oven, etc. (Exposure step) The exposure step is a photosensitive film formed in the above-mentioned photosensitive film forming step. Exposing the mask with a specific mask pattern, that is, performing pattern exposure. f This step exposes the photosensitive film of the coating film through a specific mask pattern, and only the light is irradiated. The coating film is partially hardened. The radiation that can be used for exposure is preferably ultraviolet rays such as g-line or i-line. The irradiation amount is preferably 5 to 1500 mJ/cm2, more preferably 10 to 1 〇〇〇mj/cm2, and most preferably 10 to 500 mJ/cm2. In the case of the color filter-based liquid crystal display device of the present invention, the above range is preferably 5 to 200 mJ/cm2, more preferably 10 to 150 mJ/cm2, and most preferably 10 to 100 mJ/cm2. When the color filter of the present invention is a solid-state imaging device, f. is preferably 30 to 1500 mJ/cm 2 in the above range, more preferably 50 to 1000 mJ/cm 2 k., more preferably 80 to 500 mJ/cm 2 . (Dynamic Step) Next, the developing process is carried out, and the unexposed portion in the exposure step is dissolved in the developing liquid, leaving only the portion which is photohardened. The developing solution can be used if it dissolves the photohardenable composition film of the unhardened portion and does not dissolve the hardened portion. Specifically, a combination of various organic solvents and an aqueous alkaline solution can be used. The development temperature is usually 20 ° C to 30 ° C, and the development time is usually 20 to 90 seconds. -71 - 200951185 The organic solvent may be a solvent which can be used in the preparation of the pigment dispersion composition or the photocurable composition of the present invention. The alkaline aqueous solution such as 'sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium citrate, sodium metasilicate, aqueous ammonia, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, hydrogen Basic compounds such as tetraethylammonium oxide, choline, pyrrole, piperidine, 1,8-di-bicyclo-[5,4, fluorene]-7-undecene are diluted with pure water to a concentration of 〇. 〇〇1~ 1 〇% by mass 'better 0 _ 〇1 to 1% by mass of an aqueous alkaline solution. When a developing solution composed of such an alkaline aqueous solution is used, it is usually washed with pure water (washing) after development. After the development step, the remaining developer liquid is removed by washing, and dried and then subjected to heat treatment (post-baking). The post-baking is a heat treatment after the development of the hardening is completed, and is usually performed by a heat hardening treatment at 100 ° C to 240 ° C. When the substrate is a glass substrate or a ruthenium substrate, it is preferably 20 ° C to 2 4 in the above temperature range (TC is preferred. The post-baking treatment can be applied after development, using a hot plate, a convection oven (hot air) The above-mentioned conditions are carried out in a continuous or batch manner by a circulating dryer, a high-frequency heating machine, etc. The photosensitive film forming step, the exposure step, and the developing step (and when necessary) are repeated as needed. The heat treatment can be used to produce a color filter having a desired hue. When a film is formed on a substrate by applying a photocurable composition, the dry thickness of the film is generally 0.3 to 5_0 μηι, preferably 0-5 to 3.5 μm, and most preferably 1. 〇~2.5 μηι is the best. -72- 200951185 The substrate is, for example, an alkali-free glass, a sodium silicate, a PYRE X (registered trademark) glass, a quartz glass, or the like which is used for a liquid crystal display element. A photoelectric conversion element substrate for a solid-state imaging element, such as a germanium substrate, or the like, and a plastic substrate. Generally, black stripes are formed on the substrates to isolate the pixels. The plastic substrate has gas on the surface thereof. The barrier layer and/or the solvent-resistant layer [(the layer is preferred. The use of the photo-curable composition has mainly been explained by the use of the color filter pixel, and of course, it is also applicable to the color filter. A black matrix between pixels. A black matrix can be used, and a black coloring agent such as carbon black or titanium black is added to the photocurable composition of the present invention, and as the method for fabricating the above pixel, pattern exposure, alkali imaging, and then The baking is accelerated to form. EXAMPLES Hereinafter, the present invention will be described in more detail, but the present invention is not limited to this ifcb 〇 <Example 1 > [Modulation of Organic Nanoparticle Pigment Aqueous Dispersion] Adding CI Pigment Red 254 (45 parts by mass) and the aforementioned exemplified compound 〇_1 (45 parts by mass) were stirred in dimethyl sulfoxide (DMSO) (953 parts by mass), and a 26% by mass aqueous solution of tetramethylammonium hydroxide was added to the solution (45). In the case of the mass fraction), the pigment solution A was prepared. Further, acetic acid (7.6 parts by mass) was added to water (4000 parts by mass) to prepare a pigment-insoluble solvent B. The above-mentioned pigment-insoluble solvent B was 3 (TC-side was manufactured by Fujisawa Pharmaceutical Co., Ltd. GK-0222 -10 type Raymond mixer (trade name) was stirred at 50 rpm ' -73- 200951185 While injecting the pigment solution A at a flow rate of 1 00 mL/min by a large-capacity pulseless pump (trade name) of NP_KX_500 manufactured by Nippon Precision Science Co., Ltd. The pigment-insoluble solvent B' is injected for 4 minutes and 4 seconds to crystallize the organic nano pigment particles to obtain a hydrophilic aggregate of the organic nano pigment particles. [Addition of a dispersing agent for hydrophobicity] Formula (P) The compound (mass average molecular weight: 8 〇00) (3 parts by mass) is dissolved in acetone (200 parts by mass) as a dispersing agent for hydrophobicization, and is added to the hydrophilic aggregate dispersion of the above organic nanoparticles (300 mass) (Part)), stirring for 0.5 hours. After standing for 0.5 hours, the resulting hydrophobic aggregate was allowed to settle, and the supernatant was removed by decantation. Formula (P)

• /b/c/d = 10/1D/70/10

T

>=0

-74- 200951185 (Evaluation test) The following evaluation was performed on the obtained aggregate. The results are shown in Table 1. (1) The size of primary particles of the organic nano pigment particles constituting the aggregate was evaluated by a transmission electron microscope. (2) About 1 part by mass of the agglomerate was taken out, and the mixture was stirred in water/acetone (1:1 volume mixture, 100 parts by volume), left to stand for 5 hours, and the supernatant liquid was decanted. This operation was repeated 3 times, and the aggregate was suction-filtered using a filter paper (manufactured by ADVANTEC Co., Ltd., Νο·2), and vacuum-dried overnight. The dried pigment solid (100 parts by mass) was dissolved in DMSO (100 parts by volume), and the absorption spectrum was measured by UV-2500 (trade name, manufactured by Shimadzu Corporation) to determine the pigment content in the pigment solid. The mass ratio is the adsorption rate of the dispersant added. [Separation, Washing, and Drying] Filter the paper with the filter paper (8:8:1: (: company,: ^〇.2), filter the above agglomerate' with water (300 parts by mass). Drying at room temperature under vacuum - night. [Re-dispersion] The following non-aqueous solvent 1-methoxy-2-propyl acetate (Formula Q) (4 parts by mass) was added to the organic pigment solid (1 part by mass), and used. The US series (trade name) of the ultrasonic homogenizer manufactured by Nippon Seimitsu Co., Ltd. was subjected to ultrasonic irradiation for 3 hours to obtain a non-aqueous dispersion of organic nano pigment particles (pigment dispersion composition A) using a non-aqueous solvent as a dispersion medium. 75- 200951185 (Q)

(Evaluation test) (1) Comparative evaluation The pigment dispersion composition A obtained by coating was applied to a glass substrate to a thickness of 2 μm to prepare a sample. The backlight unit is provided with a diffusion plate using a 3-wavelength cold cathode tube light source (FWL18EX-N manufactured by Toshiba Optical Technology Co., Ltd.), and the sample is placed on two polarizing plates (SANRITSU polarizer HLC 2- 2 5 18) Measure the amount of transmitted light when the polarized axis is parallel and perpendicular, and compare the ratio (refer to "7th Color Optics Conference in 990, 512 colors display 10.4" size D?1'-1^彩色Use color filters, planting wood, Xiaoguan, Fuyong, Shanzhong, etc.). The chromaticity is measured using a color luminance meter (TOPCON (股) ΒΜ-5). The position of the two polarizing plates, the sample, and the color luminance meter is set at a position of 1 3 mm from the backlight, and a polarizing plate is set at a position of 13 mm from the backlight. A cylinder having a diameter of llmm and a length of 20 mm is disposed at a position of 40 mm to 60 mm, and light passing through the light is set at 6 For the measurement sample at the 5 mm position, the transmitted light was measured by a color luminance meter set at a position of 1000 mm through a polarizing plate set at a position of 1000 mm. Set the color luminance meter to a measurement angle of 2 °. The amount of light of the backlight is set such that the luminance of the two polarizing plates is set to a flat fj polarization when the sample is not set, and the luminance is up to i280 cd/m2. The same evaluation was carried out on the pigment dispersion composition A after one week, which was the stability of the period -76-200951185. (2) Visual evaluation The pigment dispersion composition A after one week was visually confirmed by the sample for comparative evaluation to confirm the presence or absence of scattering (whether or not). If there is no scattering (if transparent), the pigment particles are sufficiently dispersed in the non-aqueous medium. <Example 2> The above-exemplified compound 〇-1 of Example 1 was changed to 〇-3, and the operation as in Example 1 was carried out. The evaluation test of Example 1 was carried out with respect to the obtained non-aqueous dispersion of the organic nano pigment particles (pigment dispersion composition B). The results are shown in Table 1. <Example 3> The above-exemplified compound 〇 -1 of Example 1 was changed to 0 - 10 0, and the operation as in Example 1 was carried out. The evaluation test of Example 1 was carried out in the non-aqueous dispersion of the obtained organic nano pigment particles (pigment dispersion composition C). The results are shown in Table 1. <Example 4> The above-exemplified compound 0-1 of Example 1 was changed to 0-4' to carry out the operation as in Example 1. The evaluation test of Example 1 was carried out with respect to the obtained organic nano pigment particle non-aqueous dispersion (pigment dispersion composition D). The results are shown in Table 1. <Comparative Example 1> The above-exemplified compound 〇-1 of Example 1 was changed to polyvinylpyrrolidone (K-25 (trade name), manufactured by Wako Pure Chemical Industries, Ltd.), and organic pigment particles were prepared as in Example 1. Aqueous dispersion 'Use a filter (HO 1 AN 公司 HO Α Α Α Α Α Α Α Α Α Α 商品 商品 商品 商品 商品 商品 - - - - - - - - - - - -

Coloring photosensitive resin composition Comparative Remarks A 14000 Example 1 B 14000 Example 2 C 12500 Example 3 D 17000 Example 4 E 10000 Comparative Example 1 From the above results, it was found that the aqueous dispersion of the pigment composition of the present invention was used, and then The color filter was formed by coloring the photosensitive resin, and the comparison was higher than that of the comparative example. The above-exemplified compound 〇-1 of Example 1 is changed to a compound Ο-6, a compound Ο-7, a compound ◦-8, a compound Ο-9 〇-1 1, a compound 〇-1 2, a compound Ο-1. The compound Ο -1 4 ◦ -1 5 was subjected to the operation as in Example 1. As a result, it was confirmed that the effects of the pigment compositions A to D were obtained. [Simple description of the diagram] te. j \ w [Description of main component symbols] te 〇 制 制 制 0 0 0 0-2, compound ζ compound mouth with the aforementioned -80-

Claims (1)

200951185 VII. Patent application scope: 1. An organic pigment composition characterized by containing a polymer compound having a repeating unit of the following formula (1) and/or a repeating unit of the formula (2) and an organic pigment particle: (wherein A! represents a hydrogen atom or a methyl group; and Xi represents a heterocyclic group which is bonded to the NH group by a carbon atom thereof). 2' The organic pigment composition of claim 1, wherein the organic pigment fine particles have an average particle diameter of 10 to 100 nm. 3'% of the organic pigment composition of claim 1, wherein the high-dividing compound further has a repeating unit of the following formula (5) and/or a repeating unit of the formula (6): 〇^N-R4瞧r3 〇V, R2 (5) (8) (wherein A3 and A4 each independently represent a hydrogen atom or a methyl group; Ri represents an annoyance®; R2 represents a hydrogen atom or an alkyl group; and 1 and r2 may be linked to each other to form a -81- 200951185 Ring structure group, the ring structure group may also contain an oxygen atom, a nitrogen atom or a sulfur atom; R3 and R4 each independently represent a hydrogen atom or an alkyl group; and R3 and R4 may be bonded to each other to form a ring structure group). 4. The organic pigment composition of claim 3, wherein the organic pigment fine particles have an average particle diameter in the range of 10 to 10 nm. 5. The organic pigment composition of claim 1, wherein the polymer compound further has a repeating unit of the following formula (3) and/or a repeating unit of the formula (4): (wherein A2 represents a hydrogen atom or a methyl group; γιi represents -NH-, -0 - or -S-; L represents a single bond or a divalent linking group; Υ2 represents a hydrogen atom or a basic group; 2! represents 1 or Two nitrogen atom-unsaturated heterocyclic groups). 6. The organic pigment composition of claim 5, wherein the organic pigment fine particles have an average particle diameter in the range of 10 to 100 nm. 7. The organic pigment composition of claim 5, wherein the polymer compound further has a repeating unit of the following formula (5) and/or a repeating unit of the formula (6): -82- 200951185 0人N』4 I r3 (5) (6) (wherein A3 and A4 each independently represent a hydrogen atom or a methyl group iR! represents an alkyl group; R2 represents a hydrogen atom or an alkyl group; and 1 and R2 may be bonded to each other to form a ring structure. Further, the ring structure group may further contain an oxygen atom, a nitrogen atom or a sulfur atom; R3 and R4 each independently represent a hydrogen atom or an alkyl group; and R3 and R4 may be bonded to each other to form a ring structure group). 8. The organic pigment composition according to claim 7, wherein the organic pigment fine particles have an average particle diameter in the range of 10 to 100 nm. The organic pigment composition according to any one of claims 1 to 8, which is a dispersion in which the organic pigment fine particles are dispersed in a medium. The organic pigment composition according to any one of claims 1 to 8, wherein the organic pigment microparticles are aqueous agglomerates present in an aqueous medium. An organic pigment composition which is a hydrophobic aggregate formed by coexisting a high molecular compound having a mass average molecular weight of 10 Å or more in an aqueous aggregate as described in the first aspect of the patent application. 12. An organic pigment composition characterized in that a hydrophobic agglomerate according to item u of the patent application is contained in a non-aqueous medium, and the aggregate is deagglomerated and redispersed. 1 3 _ ~ coloring photosensitive resin composition containing at least the organic pigment composition, binder, monomer or oligomer as claimed in claim 12, and -83-200951185 3 . If the system is used as a primer to collect the light, or the film is light-filtered, the color is combined with the color, and the light is collected. It is made into the corpus of the corpus of the physique of the genus of the genus of the genus of the genus of the genus of the genus of the genus of the genus of the genus Η 良良&&· 重重式式或高式的剂元解单良复 The combination of the weight and the mixture of the 'solution liquid is not good and the element is dissolved in the solution Correct (2) A heterocyclic ring is shown in Table XI, or a hydrogen atom is shown in Table 1 1 (Formula A is bonded to an NH group by a carbon atom). 16. The method for producing an organic pigment composition according to the fifteenth aspect of the patent application, wherein the polymer compound further has a repeating unit of the following formula (3) and/or a repeating unit of the formula (4): AYt z, L, y2 (3) (4) (wherein A2 represents a hydrogen atom or a methyl group; Yi represents ·ΝΗ-, -〇- or -S-; L-84- 200951185 denotes a single bond or a divalent linking group; Υ2 denotes that the nitrogen shows an unsaturated impurity having 1 or 2 nitrogen atoms, as in the case of claim 15 or 16 of the patent application, wherein the polymer compound has a lower / or a repeating unit of the formula (6): r4 (5) (6) (wherein A3 and A4 each independently represent a hydrogen primordium; R2 represents a hydrogen atom or a nominee; and an I ring structure group, the ring structure group also It may contain _ sub: R3 and R4 each independently represent a hydrogen atom: mutually bonded to form a ring structure group). Atom or basic group; Z! Table ring base). The organic pigment composition is a repeating unit or a methyl group of the formula (5); Ri represents that the alkane and R2 are bonded to each other to form an atom, a nitrogen atom or a sulfur-depleted alkyl group; and R3 and R4-85-200951185 The designated representative map: (1) The representative representative of the case is: None. (2) A brief description of the symbol of the representative figure: Μ 〇 j\ \\ V. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: