TW200804533A - Organic nano-particle and its dispersion composition, and colored photosensitive resin composition and photosensitive resin transcription material comprising them, and color filter, liquid crystal device, CCD device using them - Google Patents

Abstract

Provided are an organic nano-particle which has nano-size and its particle distribution is sharp; and an organic nano-particle dispersion composition having stable and excellent dispersion property, flow behavior. Besides, provided are a color filter made of them, which has high contrast and perform excellent display property; a liquid crystal device and a CCD device by using them; and a colored photosensitive resin composition and a photosensitive resin transcription material by using them. An organic nano-particle which is consisting of organic material, its amount average particle size is 50 nm or less, and the ratio of (volume average particle size)/(amount average particle size) is 1.0~2.0.

Description

200804533 IX. Description of the Invention: [Technical Field to Which the Invention Is Applicable] The present invention relates to an organic nanoparticle from a re-precipitation method and a dispersion composition thereof. Furthermore, the color-sensitive photosensitive resin composition and the photosensitive resin transfer material containing the same, and the color filter, the liquid crystal display device, and the CCD device having sharp color tone and high tinting strength, and contrast are used. . [First technology]

Pigments are widely used in most fields because of their vivid color tone, high tinting strength, light fastness and the like. Among these pigments, in particular, those who are practically important are generally fine particles. It is obtained by preventing the aggregation of the pigment by miniaturization, and obtaining a vivid color tone and high coloring power. However, when the pigment is finely refined by a physical method such as salt honing, the dispersion of the pigment mostly exhibits high viscosity. For this reason, when the pigment dispersion liquid is prepared in an industrial scale, it becomes difficult to take it out from the disperser of the pigment dispersion liquid, and it cannot be conveyed by a line, and further gelatinizes during storage. In order to improve the pigment dispersion liquid or the color-sensitive photosensitive composition which is excellent in fluidity and dispersibility, it is known to surface-treat the organic pigment (for example, refer to Patent Documents 1 and 2) and to use various formulas. A dispersing agent (for example, refer to Patent Documents 3 and 4). Further, a method of obtaining a re-precipitation method of particles by injecting a sample dissolved in a poor solvent into a poor solvent is described in detail in Patent Documents 5 and 6. In the formation of such a pigment, for example, in the formation of a colored image for use in a coloring photosensitive composition, the layer derived from the coloring photosensitive composition is generally thin, and is required to be thin and exhibit a high coloring concentration. Therefore, for example, in the organic 200804533 solvent, the organic mouse system must be dispersed in a state of high or uniform fineness. However, the present state of the art is not capable of providing a pigment dispersion or a composition thereof which satisfies such requirements and has excellent dispersibility, fluidity and the like.

On the other hand, C.LP.R.254 is a representative pyrrolopyrrole pigment which has a suitable absorption region due to the improvement of the color purity of the red pixel constituting the color filter, and has a wide color reproduction region. For this reason, attempts have been made to utilize the pigment for color filters. However, conventional pigments cannot cope with the requirements of color purity or contrast. In addition, according to the method of the present invention, the inkjet ink, the bead dispersion, or the salt honing method described in Patent Document 6 does not provide a good color filter. [Patent Document 1] Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. [Problem to be Solved by the Invention] The object of the present invention is to provide a nanometer size and a steep peak of a particle size distribution. The organic nanoparticle, and the organic nanoparticle dispersion composition having stability, good dispersibility, and fluidity, and the coloring photosensitive resin composition and the photosensitive resin transfer material. Further, it is an object of the invention to provide a color filter which can produce high contrast and exhibit excellent display characteristics, and a liquid crystal display device and a c C D device using the same. 200804533 Means for Solving the Problem The above problems were achieved by the following means. (1) An organic nanoparticle characterized by being composed of an organic material having a number average particle diameter of 50 nm or less and (volume average particle diameter) / (number average particle diameter) of from 1.0 to 2.0. (2) The organic nanoparticle according to (1), wherein the organic material is an organic pigment. The organic nanoparticle according to the item (2), wherein the organic material is selected from the group consisting of an azo pigment, a phthalocyanine pigment, a quinophthalone pigment, and a porphyrin pigment. A group consisting of a cyanine pigment, a merocyanine pigment, a Fullerene pigment, a polycyclic aromatic pigment, and a polyacetylene pigment. (4) The organic nanoparticle according to (2) or (3), wherein the organic pigment is an organic pigment of red or purple. (5) The organic nanoparticle according to (4), wherein the organic pigment is a pyrrolopyrrole pigment. (6) The organic nanoparticle according to the item (5), wherein the pyrrole-sharp pigment is a diketopyrrolopyrrole pigment represented by the following formula (Z).

(7) The organic nanoparticle according to the item (5), wherein the pyridene pigment is a diketopyl succinct pigment represented by the following formula (W). 200804533

(8) The organic nanoparticle described in the item (5) wherein the fluorene-based pigment is a diketone group represented by the following formula (V).

(9) The organic nanoparticle as described in (4), wherein the material is a dioxan pigment. (10) The organic nanoparticle according to (9), wherein the pigment is C·I. Pigment Violet 3 7 . (11) The organic nanoparticle according to (9), wherein the pigment is C.I. Pigment Violet 23. (12) The organic nanoparticle according to any one of (1) to (11), which is prepared by dissolving a solution of the organic material in a good solvent and a solvent which is soluble in the above-mentioned organic material and which is a poor solvent. (13) The organic nanoparticle according to Item (12), wherein the poor solvent of the material is selected from the group consisting of an aqueous solvent, an alcohol solvent, a solvent, an AXene solvent, and an ester solvent, and the above The above-mentioned dioxin trap of the above-mentioned dioxins is a group consisting of a mixture of the above-mentioned organic ketone-based solvent and the like 200804533 in which a good solvent is mixed. (14) The organic nanoparticle according to the item (12) or (13), wherein the good solvent of the organic material is selected from the group consisting of an aqueous solvent, an alcohol solvent, a ketone solvent, an ether solvent, and an Azoene solvent. And an ester-based solvent, a guanamine-based solvent, and a mixture of such mixtures.

(15) An organic nanoparticle-dispersed composition comprising the organic nanoparticle according to any one of (1) to (14), and a polymer compound having a mass average molecular weight of 1,000 or more. (1) The organic nanoparticle dispersion composition according to the item (1), wherein the polymer compound is represented by the following formula (1). Formula (1) A1 - 吟R1 + P1 〔 [wherein R1 represents a (m + n) valent linking group, R2 represents a single bond or a divalent linking group, and A1 represents a group selected from an acidic group. a group having a basic nitrogen atom, a urea group, a carbamate group, a group having a coordinating oxygen atom, a hydrocarbon group having 4 or more carbon atoms, an alkoxyalkyl group, an epoxy group, an isocyanate group, and a hydroxyl group. A monovalent organic group constituting a group of the group, or a monovalent organic group containing an organic dye structure which may have a substituent or a heterocyclic ring. In the formula, n Α 1 series may be the same or different from each other. Ρ1 represents a polymer compound residue. m is not a number from 1 to 8, η is a number from 2 to 9, and m + n is from 3 to 10]. The organic nanoparticle dispersion composition according to the item (1), wherein the organic nanoparticle dispersion composition is an inkjet ink. (18) a color-sensitive photosensitive resin composition characterized by containing at least 200804533 as in any one of (1) (1), or as in (1 5) to (1 7) Any of the organic nanoparticle dispersion compositions, binders, monomers or oligomers, and photopolymerization heuristics or photopolymerization heuristics. (1 9) A photosensitive resin transfer material characterized by A photosensitive resin layer containing the colored light-emitting resin composition as described in the item (18) is provided on the temporary support.

(20) A color filter comprising the photosensitive resin composition according to the item (1) or the photosensitive resin transfer material according to the item (1). (21) A liquid crystal display device is characterized in that it has a color filter as recited in (20). The liquid crystal display device according to the item (21), wherein the liquid crystal display device is of a VA method. (23) A CCD device characterized by comprising the color filter according to (22). EFFECTS OF THE INVENTION The organic nanoparticle system of the present invention exhibits an excellent effect of a so-called nanometer size and a steep peak of the particle diameter distribution. Further, the organic nanoparticle-dispersed composition of the present invention and the ink-jet ink system using the same exhibit excellent effects of so-called stability and good dispersibility and fluidity. The organic nanoparticles of the present invention, the dispersion composition thereof, and the ink jet ink using the dispersion composition are incapable of controlling the aggregation due to heating and the monodispersity without deterioration, thereby controlling the particle diameter of the nanoparticles. The colored photosensitive resin composition of the present invention and the photosensitive resin transfer material, and the ink jet printing using the dispersion composition of the present invention have a high contrast. Further, by using the colored photosensitive resin composition, the photosensitive resin transfer material, or the ink jet ink, it is possible to provide a color filter which exhibits excellent display characteristics. Further, by using these, it is possible to stably provide a liquid crystal display device and a c C D device which have high contrast and exhibit excellent display characteristics. [Embodiment] BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. φ The organic material used in the organic nanoparticles of the present invention is not particularly limited as long as it can form particles by the re-precipitation method, and examples thereof include organic pigments, organic pigments, fullerenes, and polylinks. a polymer organic material such as acetylene or polyiminoimide, or an aromatic hydrocarbon or an aliphatic hydrocarbon (for example, an aromatic hydrocarbon or an aliphatic hydrocarbon having an orientation, or an aromatic hydrocarbon having a sublimation property or an aliphatic group) A particle, an organic pigment, an organic dye, or a tubular molecular organic material composed of a hydrocarbon or the like is preferable, and an organic pigment is particularly preferable. Further, the organic particles may be used singly, in plural, or in combination with a user. ^ The organic pigment system is not limited in color, for example, phenanthrenequinone, quinacridone, quinacridone oxime, hydrazine, fluorenone ketone, benzimidazolone, diazo condensate, diazo, or Nitrogen, standard reduction blue, phthalocyanine, triarylcarbenium, a aceton, amine hydrazine, diketopyrrolopyrrole, thiopurine, isoporphyrin, isoindolinone, dermozone dye or Alien and ketone compound pigments, or mixtures thereof, and the like. More specifically, 'for example: CJ·Pigment Red. No. 7114〇), C·丨·Pigment Red 224 (C·丨. No. 71127), c_丨·Pigment Violet 29 (0丄 number 71129), etc.茈Compound pigment, c•丨·Pigment Orange 43((^丨-11- 200804533)

No. 71105), or anthrone compound pigment such as Cl Pigment Red 194 (C_I·No. 71100), CI·Pigment Violet 19 (C_I·No. 73900), C.丨·Pigment Violet 42 and CI Pigment Red 122 (C) · Number 7391 5), C_丨·Pigment Red 192, C”·Pigment Red 202 (C·丨. No. 73907), C”_Pigment Red 2〇7 (C.I_No. 73900, 73906), or CI Pigment Red 209 (C_I·No. 73905) quinacridone compound pigment, CI Pigment Red 206 (C"·No. 73900/73920), CI Pigment Orange 48 (CI·No. 73900/73920), or c.l_吖 蒽醌 醌 醌 醌 颜料 49 颜料 颜料 49 49 49 49 49 49 49 49 49 49 49 49 168 168 168 168 168 168 168 168 168 168 168 168 168 168 168 168 168 168 168 168 168 168 168 168 168 168 168 168 168 168 168 168 Ketone ketone compound pigment, C. 颜料. Pigment Brown 2 5 (C. 丨. No. 1 2 5 1 0 ), C · I. Pigment Violet 32 (C_I_ No. 12517), C" _ Pigment Yellow 180 (C. I_ No. 21 290), 〇·Ι· Pigment Yellow 181 ((: 丄 number 11777), (: 丄 Pigment Orange 62 (〇.1. No. 11 775), or CI·Pigment Red 185 ((:·Ι· Benzimidazolone compound pigment of number 12516), C · I. pigment Yellow 9 3 (C · 丨 _ number 2 0 7 1 0 ), C. 颜料. Pigment Yellow 94 (C" · number 20048), CI · Pigment Yellow 95 (C _ number 20034), C_l. Pigment Yellow 128 ( C_I·number: 20037), C_I·Pigment Yellow 166 (C.丨·number 20035), CI Pigment Orange 34 (C·丨·No. 21115), C·丨·Pigment Orange 13 (C_I. No. 21110), C.l _Pigment Orange 31 (C_I_ number 20050), C_l·Pigment Red 144 (CL number 20735), CI·Pigment Red 166 (C”·No. 20730), c.l_Pigment Red 220 (CI·Number 20055), C · Pigment Red 221 (cl number 20065), C"·Pigment Red 242 (CI·No. 20067), CI Pigment Red 248, C_I·Pigment Red 262, or C·丨·Pigment Brown 23 (C丄#20060) The diazo condensation compound pigment, C_l·Pigment Yellow 13 (CI number -12-200804533 211〇〇>, CI·Pigment Yellow 83 (C_I·No. 21108), or Pigment Yellow 188 (C_I. No. 21 094) Diamine compound pigment, c. 丨 Pigment Red 187 (CL number 1 2486), ci Pigment Red 170 (C|• number 1 2475), CI·Pigment Yellow 74 (c"·Number 11714), CI· Pigment Yellow 15〇 (c·丨号 48545), C”·Pigment Red 48 (CI·Number 1 5865), C .|·Pigment red 53 (c ! number 1 5585), CI·Pigment orange 64 (C·丨·number 1 2760), or azo pigment pigment such as ch Pigment Red 247 (C.|·No. 15915), c |• 颜 φ material blue 60 (CI·6980000) standard reduction blue compound pigment, 丨·pigment green 7 (C_I·number 74260), c”. Pigment green 36 (c丨 number 74265), pigment green 37 (c. 丨 number 74255), pigment blue i6 (c. 丨 number 74100), CI·Pigment blue 75 (c.| number 74160: 2), or 15 (c 丨 · number 74460) phthalocyanine compound pigment , c_丨·Pigment Blue 56 (c•Bu number 42800), or C.|_Pigment Blue 61 (c•丨·No. 42765:1), etc. Triarylcarbyl compound pigment, CI·Pigment Violet 23 ( C.I_ No. 51319), or a dioxane compound pigment such as C_l_Pigment Violet 37 (C.|·No. 51 345), or an amine group such as c | φ Pigment Red 177 (CI number 653〇〇)醌 compound pigment, c_丨 pigment red 254 (CL number 5611〇), cl pigment red 255 ((:| number 561 050), C_I. pigment red 264, c·丨 pigment red 272 (c_丨 number 561 1 50 ), C_J·Pigment Orange 71, or a diketopyrrolopyrrole compound such as c丄Pigment Orange 73 Sulfur compound pigment such as c, 丨, pigment red 88 (c. 丨 number 7331 2), CJ. Pigment Yellow 139 (C|• number 56298), cl·Pigment Orange 66 (c.|. number 4821 〇 An isoindoline compound pigment such as an isoporphyrin compound pigment, C"·Pigment Yellow 109 (0". No. 56284), or c丄Pigment Orange 6i (c|. No. 1 1 295), C_l. Pigment orange 40 (0" -13- 200804533 number 59700), or Pienone dye compound pigment such as CI Pigment Red 216 (CI number 5971 0), or C"_Pigment Violet 31 (6001 0), etc. A suitable and ketone compound pigment. Among them, a quinophthalone compound pigment, a diketopyrrolopyrrole compound pigment, a dioxo compound pigment, a phthalocyanine compound pigment, or an azo compound pigment is preferred, a diketopyrrolopyrrole compound pigment or a dioxane Compound pigments are preferred.

The following is a further detailed description of the diketopyrrolopyrrole compound pigment or the dioxin compound pigment. C"·Pigment Red 2 54, 255, and 264 are typical pyrrolopyrrole compound pigments which have suitable absorption regions due to the improvement of the color purity of the red pixels constituting the color filter, and because the color reproduction region is enlarged So try to use its color filter. However, conventional pigments cannot cope with the requirements of color purity or contrast. A good color furnace cannot be obtained even if it is obtained by, for example, a method of inkjet inkjet bead dispersion or salt honing described in JP-A-2000-3130001. Light film. According to the present invention, a nano-sized pyrrolopyrrole compound pigment fine particle can be obtained in a state where the particle size distribution is steep. Further, when the pigment fine particles are used in a color filter, the desired color purity and high contrast can be achieved, and the light resistance is excellent, and the generation of the folded material can be suppressed. On the other hand, the liquid crystal display device having the color filter is excellent in black compactness and redness, and display unevenness is suppressed. In the above-mentioned diketopyrrolopyrrole compound pigment, in particular, CI··Pigment Red 254 (compound represented by the following formula (Z)), 255 (compound represented by the following formula (W)), and 264 ( The compound represented by the following formula (V) is preferable, c.|·Pigment-14- 200804533 Red 2 54 is more preferable from the viewpoint of absorption spectrum. In addition, C.I. Pigment Red 2 5 4 can use Irgaph 〇r R ed B-CF (Ciba Specialty Chemicals Co., Ltd.), Cromophtal DPP Red BO, Irgazin DPP Red BO' Microlen DPP RED BP, etc. For the pigment red 255, Cromophtal Coral RedC, 丨rgazin DPP Red 5G, etc., and Cl Pigment Red 264 can be used, such as Hostapeperm Rubin D3B LP2615, Irgazin DPP Rubin TR, etc. (all trade names).

Next, the dioxo compound pigment will be described. In recent years, most of the color filter blue pixel coloring agent system uses C · I _ Pigment Blue 1 5 : 6, thereby improving the color purity of the color filter. However, a light source such as a cold cathode tube which is often used for a light source of a liquid crystal display device has a small amount of light emission on the long-wave side of the blue light-emitting peak, and thus the chromaticity is inferior to NTSC. -15- 200804533 This problem can be improved by adding c.l. Pigment Violet 23, 37 as a representative dioxic compound pigment (for example, about 5%). However, the high-color-purity color filter is expected to improve the contrast and improve the display characteristics, but the conventional bead dispersion method or the salt honing method cannot achieve satisfactory results.

On the other hand, according to the present invention, a dioxic compound pigment having a particle size distribution of a nanometer size pigment can be obtained. Further, it is also possible to form a dispersion containing the pigment particles of the dioxo compound which is excellent in stability over time. For this reason, the color filter using the same has high color purity and high contrast, and is excellent in light resistance. Further, the liquid crystal display device having the color filter is black, and the blueness is excellent in reproducibility and reproducibility, and the display unevenness is suppressed. In addition, c_l·Pigment Violet 23 can use Cromofine Violet RE,

FastgenSuper Violet BBL ' Helio Fast Violet EB,

Microlith Violet RL-WA, Sanyo Fast Violet BLD, etc., C"_Pigment Violet 37 can be used with Cromophta I Violet B, Micro I ith Violet B-A, etc. (all trade names). The organic nanoparticles of the present invention may be used in combination of two or more kinds of organic pigments or solid solutions of organic pigments. Examples of the organic dye include azo dyes, cyanine dyes, merocyanine dyes, and coumarin dyes. The polymer organic material is, for example, polyacetylene or polyimine. In the present invention, the organic nanoparticle is an organic material solution in which an organic material is dissolved in a good solvent, and is compatible with the above-mentioned good solvent and a solvent which is a poor solvent for the organic material (hereinafter, the solvent is also referred to as "organic material". -16- 200804533

a poor solvent, or a so-called "lean solvent", which is mixed and produced (hereinafter, this method is also called "re-precipitation method", and the dispersion containing the organic nanoparticle obtained at this time is also called "Organic particles re-sinking"). Here, the "good solvent" is a solvent having a large solubility in an organic pigment, and the "lean solvent" is a solvent having a small solubility in an organic pigment. The good solvent and the poor solvent used in the present invention are required to have sufficient solubility of the organic pigment in order to form the organic pigment nanoparticle, and the solvents satisfying the requirements can be used in combination with each other. The poor solvent of the organic material is not particularly limited as long as it can be dissolved or uniformly mixed with a good solvent for dissolving the organic material. The solubility of the poor solvent organic material of the organic material is preferably 0.02% by mass or less, more preferably 0.01% by mass or less. The organic material has no lower limit on the solubility of the poor solvent, but in consideration of the organic material generally used, it is actually 0.000001% by mass or more. The solubility can also be the solubility in the case of dissolution in the presence of an acid or a base. Further, the compatibility between the good solvent and the poor solvent is uniform, and the amount of the solvent to be dissolved in the poor solvent is preferably 30% by mass or more, preferably 50% by mass or more. There is no particular upper limit for the amount of the solvent to be dissolved in the poor solvent, and it is practically possible to mix them at any ratio. Examples of the poor solvent include an aqueous solvent (for example, water, hydrochloric acid, aqueous sodium hydroxide solution), an alcohol compound solvent, a ketone compound solvent, an ether compound solvent, an aromatic solvent, a carbon disulfide solvent, an aliphatic solvent, and a nitrate compound solvent. a halogen compound solvent, an ester compound solvent, an ionic liquid, a mixed solvent thereof, or the like, an aqueous solvent, an alcohol compound solvent, a ketone compound solvent, an ether compound solvent, an ester compound solvent, or a mixture thereof. Preferably, it is preferably an aqueous solvent, an alcohol compound solvent or an ester compound solvent.

The alcohol compound solvent is, for example, methanol, ethanol, isopropanol, n-propanol or 1-methoxy-2-propanol. The solvent of the ketone compound is, for example, acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone. Examples of the ether compound solvent include dimethyl ether, diethyl ether, tetrahydrofuran and the like. Examples of the aromatic compound solvent include benzene, toluene, and the like. The aliphatic compound solvent is, for example, hexane or the like. The solvent of the cerium compound is, for example, acetonitrile or the like. The halogen compound solvent is, for example, dichloromethane or trichloroethylene. Examples of the ester compound solvent include ethyl acetate, ethyl lactate, and 2-(1-methoxy)propyl acetate. Examples of the ionic liquid system include a salt of 1·butyl-3-methylimidazole and PF6·. Next, a good solvent for dissolving the organic material will be described. The good solvent is not particularly limited as long as it can dissolve the organic material used and is compatible with or uniformly mixed with the above-mentioned poor solvent. The solubility of the organic φ material in the good solvent is preferably 0.2% by mass or more, and more preferably 0.5% by mass or more. The organic material has no particular upper limit on the solubility of the good solvent, and is actually 50% by mass or less in consideration of the organic material generally used. The solubility can also be the solubility in the case of dissolution in the presence of an acid or a base. The preferred range of compatibility or uniform mixing of the poor solvent and the good solvent is as described above. Examples of the good solvent include aqueous solvents (for example, water, hydrochloric acid, aqueous sodium hydroxide), alcohol compound solvents, guanamine compound solvents, ketone compound solvents, ether compound solvents, aromatic solvent, carbon disulfide solvent, -18 - 200804533 Aliphatic solvent, nitron compound solvent, yttrium compound solvent,

a halogen compound solvent, an ester compound solvent, an ionic liquid, a mixed solvent thereof, an aqueous solvent, an alcohol compound solvent, a ketone compound solvent, an ether compound solvent, an arsenic compound solvent, an ester compound solvent, a guanamine compound solvent, or the like The mixture is preferably a good, aqueous solvent, alcohol compound solvent, ester compound solvent, sub-grinding compound solvent or guanamine compound solvent, aqueous solvent, sulfonium compound solvent or guanamine compound solvent is more preferred, sulfonium compound solvent or The guanamine compound solvent is particularly preferred. The solvent of the Yafeng compound is, for example, dimethyl hydrazine, diethyl hydrazine, hexamethylene fluorene, and cyclobutyl sulphate. The solvent of the guanamine compound is, for example, N,N-dimethylformamide, 1-methyl-2-pyrrolidone, 2-pyrrolidone, 1, 3-dimethyl-2-imidazolidinedione, 2-pyrrolidone, ε-caprolactam, formamide, N-methylformamide, acetamide, hydrazine-methylacetamide, hydrazine, hydrazine-dimethylacetamide, hydrazine- Methyl acrylamide, hexamethylphosphonium triamide, and the like. Further, the organic material is dissolved in the concentration of the organic material solution of the good solvent, and φ is preferably in the range of about 1/100 of the saturated concentration of the organic solvent to the good solvent in the case of dissolution. The preparation conditions of the organic material solution are not particularly limited, and may be selected from a normal pressure to a boiling point of the solvent to a subcritical/supercritical condition of the solvent. The temperature under normal pressure is preferably -10 to 150 ° C, preferably -5 to 130 ° C, and particularly preferably 0 to 100 ° C. The organic material of the present invention must be uniformly dissolved in a good solvent, and it may be dissolved in an acidic or alkaline state. In the case of a pigment having a base which can be largely dissociated in the molecule, it is basic, but it does not exist in the base which can be dissociated by alkali. -19-200804533 In many cases, a nitrogen atom which is easy to add a proton is used in the molecule. For example, quinophthalone, diketopyrrolopyrrole, and a diazo condensed compound pigment are dissolved in a basic state, and a phthalocyanine compound pigment is dissolved in an acidic state.

Examples of the base used in the case of alkaline dissolution include an inorganic base such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide or barium hydroxide, or a trialkylamine 'diazo An organic base such as a bicycloundecene (DBU) or a metal alkoxide is preferably an inorganic base. The amount of the base to be used is not particularly limited as long as it can uniformly dissolve the organic material, but in the case of an inorganic base, it is preferably 1.0 to 30 mol equivalents, more preferably 1.0 to 25 mol equivalents relative to the organic material. More preferably, the system is 1.0 to 20 molar equivalents. In the case of an organic test, it is preferably 1.0 to 100 mole equivalents, more preferably 5 to 100 moles, and more preferably 20 to 1 mole equivalents with respect to the organic material. The acid used in the case of being dissolved in an acid is an inorganic acid such as sulfuric acid, hydrochloric acid or phosphoric acid, or an organic acid such as acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid or trifluoromethanesulfonic acid. Preferably, it is a mineral acid. Very good is sulfuric acid. The amount of the organic material to be uniformly dissolved by the lanthanum of the acid to be used is not particularly limited, but the excess amount is used more than the alkali. In the case of inorganic acids and organic acids, it is preferably from 3 to 500 mol equivalents, more preferably from 10 to 500 mol equivalents, more preferably from 30 to 200 mol equivalents, based on the organic pigment. When a base or an acid is mixed with an organic solvent and used as a good solvent for an organic material, -20-200804533, since alkali or acid is completely dissolved, a certain amount of water or a base or acid for a lower alcohol or the like can have high solubility. The solvent is added to the organic solvent. The amount of water or lower alcohol is preferably 50% by mass or less and 30% by mass or less based on the total amount of the organic material solution. Specifically, water, methanol, ethanol, η-propanol, isopropanol, butanol or the like can be used.

The conditions for the poor solvent in the production of the organic nanoparticles, that is, the precipitation of the organic nanoparticles, are not particularly limited, and the range of the normal pressure to the subcritical and supercritical conditions can be selected. The temperature under normal pressure is preferably -30 to 100 ° C, preferably -1 0 to 60 ° C, and preferably 0 to 30 ° C. When the organic material solution and the lean solvent are mixed, either of them may be added and mixed, but it is preferred to add the organic material solution to the poor solvent, and the poor solvent is preferably stirred. The stirring speed is preferably from 100 to 10,000 rpm, preferably from 1 5 0 to 8 0 0 0 r p m is preferably, and from 2 0 0 to 6 0 0 0 r p m is particularly preferable. The addition system may or may not be used. Further, it may be added to the liquid or may be added externally, and it is preferably added in a liquid. The mixing ratio of the organic material solution to the lean solvent (the ratio of the good solvent to the poor solvent in the organic particle re-sinking liquid) is preferably 1/50 to 2/3, preferably 1/40 to 1/2, and 1 is preferable. /20~3/8 is especially good. The concentration of the organic particle re-sinking liquid is not particularly limited as long as the organic particles can be formed, but the organic particles are preferably in the range of 10 to 40000 mg, more preferably in the range of 20 to 30000 mg, relative to the dispersion solvent of 1.00 m m I. , especially good range of 50~2 5000 mg. Further, the modulation scale at the time of generating the organic nanoparticles is not particularly limited, and the preparation amount of the poor solvent is preferably 1 〇 to 2 0 0 L, and the modulation is preferably -21 - 200804533 50 to 1 000 L. The scale is better.

The particle size of the organic particles is a method of expressing the average size of the group by the number of measurement methods, but the more commonly used is the mode diameter indicating the largest distribution, and the middle diameter corresponding to the integral distribution curve. The various average diameters (number average, length average, area average, weight average, volume average, etc.) and the like are not particularly limited in the present invention, and the average particle diameter is referred to as a number average diameter. The organic particles (primary particles) of the present invention have an average particle diameter of 50 nm or less (e.g., a crystal or an association of a size), preferably 40 nm or less, and preferably 30 nm or less. Further, the organic particles of the present invention may be crystalline particles, amorphous particles, or a mixture thereof. Further, the index indicating the uniformity of particles (monodispersity) is not particularly limited in the present invention, and the ratio (Μν/Μη) of the volume average particle diameter (Mv) to the number average particle diameter (?η) is used. The monodispersity of the organic nanoparticles (primary particles) of the present invention (in the present invention, the monodispersity is such that the particle diameters are uniform), that is, Μν/Μη is 1.0 to 2.0·1, 1· 0 to 1·8 is preferable, and 1_0 to 1.5 is preferable. The method for measuring the particle diameter of the organic particles is preferably a microscopic method, a weight method, a light scattering method, a light blocking method, an electric resistance method, an acoustic method, or a dynamic light scattering method, and is preferably a microscopic method or a dynamic light scattering method. Microscopes for microscopy are, for example, scanning electron microscopes, transmission electron microscopes, and the like. The particle measuring device of the dynamic light scattering method is, for example, Nanotrack UPA-EX1 50 manufactured by Nikkiso Co., Ltd., and DLS-7000 series (both trade names) manufactured by Otsuka Electronics Co., Ltd. The organic nanoparticle-dispersed composition of the present invention contains the above-mentioned organic -22-200804533 nanoparticle and a polymer compound having a mass average molecular weight of 10 Å or more (the polymer compound is described later).

The organic nanoparticle-dispersed composition of the present invention (containing an organic nanoparticle dispersion as a liquid composition) preferably contains a dispersant. The step of allowing the dispersant to be contained in the organic particle-dispersed composition is not particularly limited to the case where a dispersing agent is added to both or both of the organic material solution and the poor solvent to be contained. Further, the dispersant solution may be added to the other two systems when the organic nanoparticles are formed. It is also possible to use a pigment particle or a pigment particle which has been surface-treated in advance by a dispersing agent, or a surface treatment which promotes adsorption of the dispersing agent. The dispersant system (1) rapidly adsorbs to the surface of the precipitated pigment to form fine nanoparticles, and (2) has a function of preventing such particles from undergoing aggregation again. The dispersing agent which can be used is, for example, an anionic, cationic, diionic, nonionic or pigment derivative of a low molecular or high molecular dispersing agent. Further, the molecular weight of the polymer dispersant may be any one as long as it can be uniformly dissolved in the solution, and is preferably a molecular weight of 1,000 to 2,000,000 and 5,000 to 1, preferably 、, 〇〇〇, preferably 1,0,000 to 500,000. For better, 1 0,000~1 00,000 is especially good. Specific examples of the polymer dispersant include polyvinylpyrrolidone, polyvinyl alcohol, polyvinyl methyl ether, polyethylene glycol, polypropylene glycol, polypropylene decylamine, and vinyl alcohol-vinyl acetate copolymerization. , polyvinyl alcohol - partial methyl acetal, polyvinyl alcohol - partial butyral, vinyl pyrrolidone - vinyl acetate copolymer, polyethylene oxide / propylene oxide block copolymer, polyacrylic acid Salt, polyvinyl sulfate, poly(4-vinylpyridine) salt, polyamine, poly-23- 200804533

Allylamine salt, condensed naphthalenesulfonate, cellulose derivative, starch derivative, and the like. Further, natural polymers such as alginate, gelatin, albumin, casein, arbor gum, toluene gum, and lignosulfonate can also be used. Among them, especially the polyethyl bromide ketone is preferred. These polymers may be used alone or in combination of two or more. These dispersants can be used singly or in combination. The dispersing agent for pigment dispersion is described in detail on pages 29 to 46 of "Pigment Dispersion Stability and Surface Treatment Technology and Evaluation" (Chemical Information Association, Issued in January, 2001). The anionic dispersing agent (anionic surfactant) may, for example, be N-fluorenyl-N-homoyl taurate, fatty acid salt, hospital sulfate, sulfonate, alkyl naphthalene An acid salt, a dialkyl sulfosuccinate, a hospital phosphate salt, a naphthalenesulfonic acid formalin condensate, a polyoxyethylene hospital sulfate salt, and the like. Among them, N-fluorenyl-N-alkyl taurates are preferred. The N-fluorenyl-N-indenyl taurate is preferably described in JP-A-3-27736. These anionic dispersing agents may be used singly or in combination of two or more. The cationic dispersant (cationic surfactant) contains a quaternary ammonium salt, an alkoxylated polyamine, an aliphatic amine polyglycol ether, an aliphatic amine, and is induced by an aliphatic amine and an aliphatic alcohol. Amines and polyamines, imidazolines induced by fatty acids, and salts of such cationic materials. These cationic dispersing agents may be used singly or in combination of two or more. The two-ionic dispersing agent contains, in the molecule, a dispersing agent which has an anionic group portion of the above anionic dispersing agent and a cationic group portion having a cationic dispersing agent in the molecule pg. Nonionic dispersing agent (nonionic surfactant) can be used, for example, poly-24-200804533 oxyethylene alkyl ether, polyoxyethylene alkyl aryl, aryl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid Ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkylamine, glycerin fatty acid ester, and the like. Among them, polyoxyethylene alkyl aryl ether is preferred. These nonionic dispersing agents may be used singly or in combination of two or more.

The pigment derivative type dispersant is defined as a pigment derivative type dispersant which is produced by chemically modifying its main structure, which is induced by an organic pigment as a affi substance, or pigmented by a chemically modified pigment precursor. A pigment derivative-type dispersant obtained by the reaction. For example, a sugar-containing pigment derivative-type dispersant, a piperidinyl-based pigment derivative-type dispersant, a naphthalene or anthracene-inducing pigment derivative-type dispersant, and a pigment derivative having a functional group transmissive to a main structure of a pigment through a methylene group Material type dispersant, pigment main structure chemically modified by polymer, pigment derivative type dispersant having sulfonic acid group, pigment derivative type dispersing agent having sulfonamide group, pigment derivative type dispersion having ether group An agent or a pigment derivative-type dispersant having a carboxylic acid group, a carboxylate group or a carboxamide group. In the case of producing the pigment dispersion composition of the present invention, it is preferred to coexist with an amine-based pigment dispersant when producing an organic material solution dissolved in a good solvent. Here, the amine group includes a primary amine group, a secondary amine group, and a secondary amine group, and the number of the amine groups may be one or plural. A pigment derivative compound having a substituent of an amine group introduced into the pigment skeleton or a polymer compound having a monomer having an amine group as a polymerization component may be used. For example, JP-A-2000-239554, JP-A-2003-9.6329, JP-A-2001-31885, JP-A-10-339949, -25-

200804533 Special fair 5 - 7 2 9 4 The restrictions described in the bulletin. The female having the amine group used in the present invention is at least one selected from the group consisting of the following general formulae (D1) and (D3). < 1 • Compound represented by the formula (D 1 ) > Formula (D1)

A—N=N—X—Y In the formula (D1), the A system represents a compound and a component. The above A may be arbitrarily selected as long as it is a compound with a heavy carbonium. The above A_the invention is not subject to any limitation. The compound or the like is not limited thereto, and a compound represented by the formula (D4) (a specific example in which an azo dye is formed by forming an azo dye together) is as follows. As shown,

-26 - 200804533

In the formula (D1), X represents a group selected from a single bond or a divalent linking group represented by the structural formula of the following formulas (1) to (v).

CONH--CONH- Formula (i) Formula (ii) \S02NH-Formula (iii) -^Q-S02NH- ^-0- Formula (iv) Formula (v) -27- 200804533 In the formula (D1), Y The group represented by the following formula (D2) is represented. Formula (D2) (CONH-Z-NR^) In the formula (D2), Z represents a lower alkyl group. The Z system is expressed as -(Ch2;)|

However, the lanthanide indicates an integer of 1 to 5, preferably 2 or 3. In the formula (〇2), -NR21 represents a lower alkylamino group or a 5- to 6-membered saturated heterocyclic group containing a nitrogen atom. In the case where the -N R2 1 is a lower guanamine group, it is represented by _N(CrH2r + 1) 2, and r is an integer of 1 to 4, preferably 1 or 2. On the other hand, the -NR21 is a 5- to 6-membered saturated heterocyclic group containing a nitrogen atom, and a heterocyclic group represented by the following structural formula is preferred.

An alkoxy group is used as a substituent. In the above formula (D2), a represents 1 or 2, and preferably 2 is not 2. The following 'specific examples of the compound represented by the above formula (D1) are shown, but the present invention is not limited by the specific examples. -28 - 200804533

2.

〇CH3 C^OCHg ^^CONH(CH2}3N{Q2H5h 3. C〇NH(CH2feN(C2Hs)5>

H Λ COCH3 ^ρ=ςχ~ΟΟΝΗ(ΟΗ2)2Ν{〇2Η5)2 NHCOtH-N=M~(()〉 ^^CONHiCH^NiCaHsis 6. 5·

H mhcc&mQ1 CONHiCH^sNtCaHsJa CONH(CH2)3M(C2H5)2

Nhco^^mQ- CONH- -CONH<CH2)2NiC2H^2 -CONHtCH^sNiCgHsJg

C〇NH(CH2hN(C2H5fe CONH(CH2>3N(C2H5^ -29- 5338· Κ

NHC〇&Fanning

〇〇HH{CH2i^{C^0^ ;〇ΝΗ(〇Η^3Ν(〇2Η5Ϊ2 9. 〇 〇==(

Η 9〇C Bu NHCOCH^

^ 〇〇ΝΗ(〇Η2)5Ν(°2Η^2 CONH-^^c〇刺ch-n(C2H also 0· Hold Hc&aC=

CONH

CONHiCH^aN^H^ CONHiCH^sNCCaHsk 2.

NH<CH2)3M(CHa)2 €ΟΝΗ(ΟΗ2}3Ν(ΟΗ〇)2

-30- 200804533 4

yOCH3 C!— -NHCOCI pONH(CH2)2N^] ) vCONH(CH2)2N^] 5 dcH3 c pONH(CH2) CONH(CH2)s

Och3 H-N=l

CONI

rCONH(CHa)3N

CONH(CHg)3N 7. t!

H

NHCOCH^Ni^-^^-CONH

8. "V^hco&hti00^-, ^~conh<ch2 adjust C2Hs)2 1 9. H cK il

^och3 NHCOCH-N=

CONH C〇NH(CH纲CH^CONHiCH^gNiCH^a -31 200804533 2 0. θα:

CONH(CH2)3N(C2H5)2 CONHIG^bNCCaH^ OH CONH

CONHfCHgJaNtCgHsJg CONHICH^NiCsH^

It is synthesized by the method described in Japanese Patent Publication No. 2 0 00-2. <2. Compound represented by the formula (D3)>

In the general formula (D3), the Q system is selected from the group consisting of an anthraquinone compound dye, an azo compound dye, a phthalocyanine compound dye, a quinacridone compound dye, a di-11 trap compound dye, an alizarin pyrimidine compound dye, and an anthracene. Anthrone compound pigment, indanthrone compound pigment, flavanone compound pigment, dermoside compound pigment, anthrone compound pigment, anthraquinone compound pigment, and thioindigo compound-32-200804533 organic pigment residue of a pigment, wherein In particular, an azo compound dye or a dich compound dye is preferred, and an azo compound dye is preferred. Χι means -CO-, -conh-y2-, -so2nh-y2-, or -CH2NHC〇CH2NH-Y2, preferably -CO-, -CONH-Y2-.丫2 represents an alkylene group or an extended aryl group which may have a substituent, and particularly preferably a phenyl group, a methylphenyl group or a hexyl group, and a phenyl group is preferred.

R11 and R12 each independently substituted or unsubstituted alkyl or Ru and Ri 2 may form a heterocyclic group containing at least a nitrogen atom. Among them, a methyl group, an ethyl group, a propyl group or a pyridyl group containing a nitrogen atom is preferred, and an ethyl group is preferred.

Yi means -NH- or -0-.

The Zi system represents a hydroxyl group or a group represented by the formula (D3 a), or the case where n1 is 1, may be -NH-Xi-Q. Ml represents an integer of 1 to 6, preferably 2 to 3. N1 represents an integer of 1 to 4, preferably 1 to 2. General formula (D3a) y3-(ch2)-n^,^ - ........... • · I 1 -: · · nl2 In the formula (D3a), Y3 represents -NH- or - 0-, ml, Rn, and R12 have the same meanings as in the formula (D 3). More specifically, the compound represented by the formula (D3) is represented by, for example, the following formula. -33- 200804533

Further, in the general formulae (D3-1) to (D3-6), Q, ml, n1, Rt1, and R12 have the same meanings as those in the general formula (D3). Specific examples of the compound represented by the formula (D3) are listed below, but the present invention is not limited thereto. Further, in the formula, Cu-Pc means copper phthalocyanine. -34- 200804533 (a)

Cu-pc* ms〇2m

(h) Soot 1V (4) ΝγΝ \η5 C2H5

Cc) 2NHC〇CHzNh^^ NH(CH2)3N-C^ ΝγΝ 〇2Η5 〇=<

C〇NH-

Nh〇〇CHC〇ch3

ΝΗΎ"Νγ νη(〇η2)3ν^〇βΗ5 ΝψΝ , C2Hsnh(〇h2)sN^ C^a (e) 4ΗΎΝγΝΗ(ΟΗ^Κ〇2Ηδ N Q$Hg

Wh(ch2)3< c2hs C2^s

Cli-Pc·Q2H5 〇4H9-35- 200804533

CONH-

ΝΗη^γ NH(CH2)sN< C2H5 QH5 _(χ[c NH^NHCCH,)^;

QHS (f) ΝγΝ NH(CH; h)^N< C2H5 2

The compound represented by the formula (D3) is, for example, an amine compound having R12 and an alcohol compound having Rii and R12, and reacting with a halogenated triple-trap compound, and reacting the obtained intermediate with a dye compound. get. Further, the description of Japanese Patent Publication No. 5-72943 can also be referred to. <3. Pigment Dispersant Containing Graft Copolymer> In the case of producing the pigment dispersion composition of the present invention, a graft copolymer having an amine group and an ether group is contained, and other suitable selections may be used as needed. Dispersant of ingredients. The above graft copolymer is obtained by containing at least an amine group and an ether group, and may contain other monomers or the like as a copolymer unit. The weight average molecular weight (M w) of the above graft copolymer is preferably from -36 to 200804533 3000 to 1,000, and preferably from 5,000 to 50,000. When the weight average molecular weight (Mw) is less than 3,000, the aggregation of the organic nanoparticles is prevented and the viscosity is increased. When the weight exceeds 100,000, the solubility in the organic solvent is insufficient, and the viscosity is increased. Further, the weight average molecular weight is a polystyrene-equivalent weight average molecular weight measured by gel permeation chromatography (carrier: tetrahydrofuran).

The above graft copolymer contains at least: (i) a polymerizable low polymer having an ethylenically unsaturated double bond at its terminal, a monomer having an amine group and an ethylenically unsaturated double bond, and (iii) having an ether. The polymerizable monomer is preferably used as a copolymer unit, and if necessary, (iv) another monomer may be contained as a copolymerization unit. The content of the above graft copolymer in the copolymer unit, (i) the polymerizable low polymer is preferably 15 to 98% by mass, preferably 25 to 90% by mass, preferably (amino)-containing monomer. It is preferable that it is 1 to 40% by mass, preferably 5 to 30% by mass, and the (Mi) polymerizable monomer having an ether group is preferably 1 to 70% by mass, preferably 5 to 60% by mass. When the content of the polymerizable low polymer is less than 15% by mass, the three-dimensional repulsion effect as a dispersing agent cannot be obtained, and aggregation of the organic nanoparticles can not be prevented. When the content exceeds 98% by mass, the nitrogen-containing monomer The ratio is reduced and the adsorption ability to the organic pigment particles is lowered, and the dispersibility is insufficient. When the content of the nitrogen-containing monomer is less than 1% by mass, the adsorption ability of the organic pigment particles is lowered, and the dispersibility is insufficient. When the content is more than 40% by mass, the ratio of the polymerizable low polymer is reduced, and the amount of the polymerizable low polymer is not obtained. As a stereoscopic repelling effect of the dispersing agent, the aggregation of the organic pigment particles cannot be sufficiently prevented. When the content of the above-mentioned ether group-containing polymerizable monomer is less than 1% by mass, the developmental suitability of the color filter of the color-37-200804533 color filter or the first film is insufficient, and when it exceeds 70% by mass, it is dispersed. The ability of the agent is reduced. (i) Polymerizable low polymer The polymerizable low polymer (hereinafter referred to as "macromonomer") is a low polymer containing a group having an ethylenically unsaturated double bond at the terminal. Among the above polymerizable low polymers in the present invention, in particular, only two of the low polymers

One of the ends is preferably one containing the above-mentioned ethylenically unsaturated double bond. In general, the above low polymer may have, for example, at least one selected from the group consisting of alkyl (meth)acrylate, hydroxyalkyl (meth)acrylate, styrene, acrylonitrile, ethyl acetate, and butadiene. Among the homopolymers or copolymers formed of the monomers, etc., among them, a homopolymer or copolymer of an alkyl (meth)acrylate, polystyrene or the like is preferable. In the present invention, these oligomeric compounds may be substituted with a substituent, and the substituent is not particularly limited, and examples thereof include a halogen atom and the like. The group having the above-mentioned ethyl-unsaturated double bond is preferably, for example, a (meth)acryl fluorenyl group, a vinyl group or the like, and among them, a (meth) acrylonitrile group is particularly preferable. In the above-mentioned polymerizable low polymer of the present invention, the low polymer represented by the following general formula: E 6) is preferably 〇δ1 : ΙΛ formula (Ε6) - state change in the above formula (Ε6) R61 and R63 represent a hydrogen atom or a methyl group. R62 represents an alkylene group which may be substituted with an alcoholic hydroxyl group having 1 to 8 carbon atoms, and an alkylene group having a carbon number of 2 to 4 to 38 to 200804533. Y6 represents a phenyl group, a phenyl group having a carbon number of 1 to 4 alkyl groups, or -COOR (wherein R64 represents an alkyl group or a phenyl group which may be substituted with an alcoholic group or a crypto group having a carbon number of 6, Or an arylalkyl group having a carbon number of 7 to 1 (), a phenyl group or a -COOR64 (here, R64 means a group which may be substituted with an alcoholic group having 1 to 4 carbon atoms). q means 20 to 200.

The above polymerizable low polymer is poly-2-hydroxy(methyl)propionic acid ethyl ester, polystyrene, poly (methyl) methacrylate, poly(methyl) methacrylate, poly(methyl). It is preferred that the acrylic acid isobutyl ester, such a copolymer, and a polymer having a (meth) acrylonitrile group bonded to the terminal of the molecule are preferred. The polymerizable low polymer may be a commercially available product or may be a suitable synthesizer. 'This commercial product is, for example, a sheet-end methacryl-based polystyrene low polymer (Μη = 6 000, trade name: AS-6, manufactured by East Asia Synthetic Chemical Industry Co., Ltd., methacrylic acid thiolated polymethyl methacrylate low polymer (Mn = 6000, trade name: AA-6, East Asia Synthetic Chemical Industry Co., Ltd. )), methacrylofluorenyl poly-n-butyl acrylate low polymer (Mn=6000, trade name: AB-6, manufactured by East Asia Synthetic Chemical Industry Co., Ltd.), sheet end methacryl Thiolated polymethyl methacrylate / 2-hydroxyethyl methacrylate low polymer (Μ η = 70 〇〇, trade name: AA - 71 4 , manufactured by East Asia Synthetic Chemical Industry Co., Ltd.), tablets Methyl methacrylate methacrylate polybutyl methacrylate / 2-hydroxyethyl methacrylate low polymer (Mn = 7000, trade name: 707S, manufactured by East Asia Synthetic Chemical Industry Co., Ltd.), terminal methyl group Acryl thiolated polymethyl propylene succinic acid 2-ethylhexyl acrylate/methyl propyl succinic acid 2 - thioethyl ester Polymer (Mn = 7000, trade name: AY-707S, AY-71 4S, Toagosei Chemical Industry (shares) Corporation) and the like. -39- 200804533 Preferred examples of the above polymerizable low polymer in the present invention include, for example, a polymer selected from an alkyl (meth)acrylate, and a copolymer of an alkyl (meth)acrylate and polystyrene. At least one low polymer of the substance having a number average molecular weight of from 10,000 to 20,000 and having a (meth) acrylonitrile group at the terminal. (ii) Amino group-containing monomer The above-mentioned amine group-containing single system is preferably at least one selected from the group consisting of the compounds represented by the following formula (E2).

Pj21 : 逋 Formula (E 2) In the above formula (E2), R21 represents a hydrogen atom or a methyl group. R22 represents an alkylene group having 1 to 8 carbon atoms, and particularly preferably an alkylene group having 1 to 6 carbon atoms and an alkylene group having 2 to 3 carbon atoms are particularly preferred. X2 represents ·Ν(Κ23)(Ρ124), -R25N(R26)(R27). Here, R23 and R24 represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. R25 represents an alkylene group having 1 to 6 carbon atoms, and R26 and R27 represent a hydrogen atom, an alkyl group having 1 to 6 φ carbon atoms or a phenyl group. Among the above, R23 and R24 of _N(R23)(R24) are preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms or a phenyl group, and R25 of -R25-N(R26)(R27) is a carbon group. The alkylene group having 2 to 6 is preferably an alkyl group, and the R26 and R27 are preferably an alkyl group having 1 to 4 carbon atoms. M2 and n2 represent 1 or 〇, and m2 = 1 and n2 = 1, or m2 = 1 and n2 = 0 is preferable (i.e., corresponds to a monomer represented by the following formula (E3) or (E4)). In the present invention, among the monomers represented by the above formula (E2), at least selected from the monomers represented by any one of the following general formulae (E3) and (E4), the species is -40- 200804533 识 NHR3243 Formula (E 3) In the above formula (E3), the r31 system is synonymous with R21. R32 is synonymous with R22. The X3 system is synonymous with x2.

In the above formula (E4), R41 is synonymous with R21. X4 is synonymous with X2, Ν(Κ43)([^44) (here, R43 and R44 are synonymous with R23 and R24), or, -r45-n(r46)(r47) (here, R45, R46 And R47 is synonymous with R25, R26 and R27, respectively). Specific examples of the monomer represented by the above formula (E2) include, for example, dimethyl (meth) acrylamide, diethyl (meth) acrylamide, diisopropyl (meth) acrylamide, Di-n-butyl (meth) acrylamide, di-isobutyl (meth) acrylamide, morpholino (meth) acrylamide, piperidino (meth) acrylamide, N -methyl-2_piperidinyl(meth)acrylamide and N,N-methylphenyl(meth)acrylamide (above (meth) acrylamide); 2-(N,N -Dimethylamino)ethyl(meth)acrylamide, 2-(N,N-diethylamino)ethyl(meth)acrylamide, 3-(N,N-diethyl Amino)propyl(meth)acrylamide, 3-(N,M-dimethylamino)propyl(meth)acrylamide, 1-(N,N-dimethylamino)- 1,1-dimethylmethyl(meth)acrylamide, 6-(N,N-diethylamino)hexyl(methyl)propenylamine (above aminoalkyl(methyl)propene oxime) Amines and the like are preferred. (iii) Polymerizable monomer having an ether group -41-200804533 The above polymerizable single system having an ether group is preferably at least one selected from the group consisting of monomers represented by the following formula (E1).

An alkyl group having a carbon number of 1 to 8 is shown. Among them, an alkylene group having preferably 1 to 6 carbon atoms and an alkylene group having 2 to 3 carbon atoms are more preferable. X1 represents -OR13 or - OCOR14. φ Here, R13 represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a phenyl group, or a phenyl group substituted with an alkyl group having 1 to 18 carbon atoms. R1 4 represents an alkyl group having 1 to 18 carbon atoms. Further, m3 means 2 to 200, 5 to 1 00 is preferable, and 1 0 to 1 00 is particularly preferable. The polymerizable monomer having an ether group is not particularly limited as long as it has an ether group and is polymerizable, and may be appropriately selected from usual, and may, for example, be polyethylene glycol mono(meth)acrylate. , polypropylene glycol mono(meth)acrylate, polyethylene glycol polypropylene glycol mono(meth)acrylate φ ester, polybutane diol methacrylate, etc., which may be commercially available or may be Suitable for synthesizers. The commercially available product is, for example, methoxypolyethylene glycol methacrylate (NK ester M-40G, M-90G, M-230G (manufactured by East Asia Synthetic Chemical Industry Co., Ltd.); Bremer PME-100, PME-200, PME-400, PME-100 Ο, ΡΜΕ -2000, PM Ε-4 000 (made by Nippon Oil & Fats Co., Ltd.), polyethylene glycol monomethacrylate (Brayma PE-90, ΡΈ -200, PE-350 (manufactured by Nippon Oil & Fats Co., Ltd.), polypropylene glycol monomethacrylate (Brayma PP-500, PP-800, PP-1000 (manufactured by Nippon Oil & Fats Co., Ltd.)), poly Ethylene glycol polypropylene glycol monomethyl-42 « 200804533 based acrylate (Brayma 70PEP-370B (made by Nippon Oil & Fats Co., Ltd.)), polyethylene glycol polybutane diol-methacrylate (Brayma 55PET- 800 (manufactured by Nippon Oil & Fats Co., Ltd.), polypropylene glycol polybutanediol monomethacrylate (Bremer NHK-5050 (manufactured by Nippon Oil & Fats Co., Ltd.)), etc. (all trade names). (iv) other monomers

The above-mentioned graft copolymer may further include the above other monomers as a copolymer unit, and the other single system is not particularly limited, and may be appropriately selected depending on the purpose thereof, and examples thereof include an aromatic vinyl compound (for example, styrene, Α-methyl styrene and vinyl toluene), alkyl (meth) acrylate (for example, methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate and (a) Isobutyl acrylate (alkyl methacrylate) (for example, benzyl (meth) acrylate), glycidyl (meth) acrylate, vinyl carboxylate (for example, vinyl acetate and C Acid vinyl ester), vinyl cyanide (for example, (meth)acrylonitrile and α-chloroacrylonitrile), and aliphatic conjugated dienes (for example, 1,3-butadiene and isoprene), (Meth)acrylic acid, etc. Among these, an unsaturated carboxylic acid, an alkyl (meth)acrylate, an alkyl aryl (meth) acrylate, and a vinyl carboxylate are preferable. The content of the other monomer in the copolymer is, for example, 5 to 70 When the content ratio of the content is less than 5% by mass, the physical properties of the coating film cannot be controlled, and when it exceeds 70% by mass, the ability to act as a dispersing agent cannot be sufficiently exhibited. Preferred examples of the compound are, for example, (1 1 ) 3 - (indole, fluorenyl-dimethylamino)propyl acrylamide/polyethylene glycol mono-43-200804533 (meth) acrylate/end Methyl propylene thiolated poly(meth)acrylic acid _ 1 S 曰 copolymer, (12) 3-(N,N-dimethylamino)propyl acrylamide/polyethylene (meth) acrylate /terminal methacryl oxime polystyrene copolymer, (13) 3-(N,N-dimethylamino)propyl acrylamide / polyethylene glycol _ (meth) acrylate / (A Methyl acrylate terminal methacryl fluorenyl styrene copolymer,

(14) 3-(N,N-Dimethylamino)propyl acrylamide/polyethylene __(meth) acrylate/terminal methacryl oxime (meth) acrylate@@&amp ; Copolymer of 2-hydroxyethyl methacrylate copolymer, (15) 3-(叱卜dimethylamino)propyl acrylamide/polyethylene glycol-(meth)acrylate/terminal methyl Copolymer of acrylylated methyl methacrylate and 2-hydroxyethyl methacrylate copolymer, (16) 3-(anthraquinone-dimethylamino)propyl acrylamide/polyethylene glycol — (meth) acrylate / terminal methacryl thiolated methyl methacrylate and copolymer of 2-hydroxyethyl methacrylate copolymer, (17) 3_(Ν,Ν-dimethylamino group ) propyl acrylamide / polypropylene glycol mono (meth) acrylate / terminal methacryl oxime poly(methyl) acrylate@@ copolymer, (18) 3-(Ν, Ν-dimethylamino ) propyl acrylamide / polyethylene glycol polypropylene glycol mono (meth) acrylate / terminal methacryl oxime polymethyl (meth) acrylate copolymer, (19) 3- (Ν, Ν - dimethyl Amino) propyl acrylamide/polyethylene glycol Butanediol mono(meth)acrylate/terminal methacrylic acid poly(methyl)propene-44-200804533 methyl ester copolymer, (20) 3-(anthracene, fluorene-dimethylamino group Propyl acrylamide/polypropylene glycol polybutane diol-(meth) acrylate/terminal methacryl oxime poly(methyl) acrylate copolymer, and the like. Among them, a compound represented by the following formula (D4) is preferable, and (11), (14), and (18) are preferable. In the formula (D4), the formula (D4) M e represents a methyl group.

ChK -CH〇-CH- CONHC3H6NMe2 / \ C02(C2H40)23Me

a \ /b \ CO2C2H4S : 〇 = 15:20:65 (weight ratio) The above-mentioned graft copolymer is obtained by forming a component of each of the above copolymer units, for example, by radical polymerization in a solvent. In the radical polymerization, a radical polymerization initiator can be used, and a lock transfer agent (for example, 2-hydrothioethanol and dodecanethiol) can be further used. The pigment dispersing agent containing a graft copolymer can also be described in JP-A-2001-31885.

The content of the dispersant is preferably in the range of 0.1 to 1.0 part by mass, more preferably 1 to 5 0 0 in terms of the uniform dispersibility and storage stability of the organic pigment particles. The range of the parts by mass is more preferably in the range of 5 to 20 parts by mass. When the amount is less than 1 part by mass, the dispersion stability of the organic nanoparticle may not be observed. Further, the dispersing agent may be used singly or in combination of plural kinds. [Manufacturing Apparatus] A preferred embodiment of the manufacturing apparatus used in the production of the pigment dispersion composition of the present invention is described, but the present invention is not limited thereto (manufacturing apparatus example 1). Fig. 1 is a view showing a preferred embodiment of a manufacturing apparatus used in the production of the organic nanoparticle of the present invention. The organic material solution in Fig. 1 is continuously supplied into the container 1 1 by the supply pipe 14. Here, the container 1 1 contains a poor solvent 彳彳a, and a large amount of the poor solvent is continuously convected by stirring.

Fig. 2 is a schematic view showing another preferred embodiment of a manufacturing apparatus used in the production of the organic nanoparticle of the present invention, and a mixing chamber (stirring area) is provided in the container 1 1 of the manufacturing apparatus of Fig. 1 1 3 people. The mixing chamber 13 is placed under the liquid surface of the poor solvent, and the inside thereof is filled with the poor solvent. Further, a large amount of the poor solvent in the reaction vessel 11 is caused by the stirring action in the mixing chamber 13, and the inside of the mixing chamber 13 is continuously cut from the bottom to the top (in the direction of the arrow in the figure) to generate convection. Fig. 3 is an enlarged partial cross-sectional view showing the mixing chamber 13 which is an embodiment of the manufacturing apparatus of Fig. 2 in an enlarged manner. The organic material solution is supplied from the supply pipe 14 to the mixing chamber 13 . The mixing chamber 13 is composed of a housing 17 having a straight rectangular parallelepiped having a constant cross-sectional area. The upper end of the housing 17 is an open end (opening portion), and the lower end is provided with a circular hole 18 and the mixer 13 In the case of the poor solvent medium and the outside of the stirring zone (in the case of the composition in the figure, the poor solvent 1 1 a, the field other than the mixing chamber 13 is outside the mixing field, also known as the stirring outside field) The solvent is formed by connecting to each other. The organic material solution supply pipe 14 is disposed in a wall constituting the lower end of the casing 17 and opens toward the above-mentioned dome-shaped hole. Further, a stirring blade - 46 - 200804533 1 2 is provided in the mixer, and the rotating shaft 15 is attached to the stirring blade, and is rotated by the motor 16. By the rotation of the stirring blade 12, the lean solvent passes through the weir-shaped hole 18 and causes it to circulate frequently from the bottom toward the inside of the mixer 13. The agitating blades 12 provided in the mixing chamber 13 described above must produce a desired mixing strength in the mixing chamber. This mixed strength is presumed to be an important operating factor for the size of droplets (droplets) at the time of mixing of the organic pigment solution.

Further, the stirring blade 12 is selected to have a larger particle formed by combining the organic pigment particles generated in the mixing space with the other organic pigment particles, and being exposed to the mixing chamber 13 In the organic pigment solution, it is preferred that the organic pigment particles are quickly extracted and rapidly discharged to the outside of the mixing chamber 13 so as to form large particles without generating large particles. The agitating blade 12 can be used in any form to achieve the above object, and for example, a turbine type, a fan turbine type, or the like can be used. Further, the casing 17 is preferably constructed by a square cylinder as described above. By this means, the flow created by the stirring blade 1 2 disturbs the square of the casing 1 7 and does not require an attachment such as a baffle plate, so that the mixing effect can be further improved. Fig. 4 is a cross-sectional view showing an enlarged view of a mixer in which two mixing blades (mixing agitating blades 19a and discharging agitating blades 19b) are used in another embodiment of the manufacturing apparatus of Fig. 2; By providing two such agitating blades, the ability to control the mixing strength and the ability to discharge the generated organic pigment particles out of the mixer can be selected, and the mixed -47-200804533 intensity and circulation amount setting operation can be independently performed. Become the hope of hope. (Manufacturing device example 2)

Fig. 5 is a cross-sectional view showing another embodiment of a manufacturing apparatus for producing organic nanoparticle of the present invention. The medium organic material solution and the lean solvent medium are continuously supplied into the stirring tank 21a through the supply pipes 24a and 24b, respectively. The organic material particles generated in the stirring tank 2 1 a are retained in the stirring tank 1 1 a, combined with other organic material particles to form larger particles, and exposed to the organic materials supplied from the supply pipes 24a, 24b. In the solution, the generated organic material particle dispersion is quickly extracted from the discharge pipe 23 so as to form large particles without generating large particles. Fig. 6 is a cross-sectional view showing still another embodiment of the apparatus used in the manufacturing method of the present invention. In the manufacturing apparatus of Fig. 6, the agitation device 50 includes a cylindrical liquid supply port 32 having 33 liquid supply ports 32, 33 for injecting the organic pigment solution and the lean solvent, and a liquid discharge port 36 for discharging the mixed liquid. The agitation tank 38 and the pair of agitating blades 41 and 42 which are driven by the rotation in the agitation tank 38 to control the stirring state of the liquid in the agitation tank 38. The agitation tank 38 is composed of a cylindrical groove body 39' that faces the center axis in the up-and-down direction and a sealing plate 40 that blocks the upper and lower open ends of the groove body 39 to form a groove wall. Further, the agitation vessel 38 and the tank body 39 are formed of a non-magnetic material having excellent magnetic permeability. The two liquid supply ports 32, 33 are provided at positions close to the lower end of the tank body 39, and the liquid discharge port 36 is provided at a position close to the upper end of the tank body 39. Then, the pair of agitating blades 41 and 42 are disposed at opposite upper and lower ends in the agitation tanks 38 • 48 to 200804533, and are rotationally driven in opposite directions to each other. Each of the stirring blades 41 and 42 is configured to be a magnetic air coupling C with an outer magnet 46 disposed on the outer side of the groove wall (sealing plate 40) of the stirring blades 41 and 42, respectively. That is, the respective agitating blades 4 1 and 42 are connected to the respective outer magnets 46 ′ by magnetic force. The outer magnets 46 are rotationally driven by independent motors 48 and 49 to perform mutually reverse rotation operations.

The two pairs of agitating blades 41 and 42 disposed opposite each other in the groove 38 are formed by the arrows (X) of the broken lines in FIG. 6 and the arrows (Y) of the solid lines, and the respective inclinations are different in the grooves 38. Stir the flow. Therefore, the agitation flow formed by each of the agitation blades 41 and 42 collides with each other due to the difference in the flow direction, and the groove 38 generates a high-speed turbulent flow in the promotion groove 38, and the flow in the groove 38 is prevented from being fixed even in the flow. When the rotation of the agitation blades 4 1 and 42 is increased, the rotation of the agitation blades 4 1 and 42 is prevented from rotating to form a cavity, and the agitation is prevented from being carried out along the agitation tank 38. The so-called unsuitable occurrence of a fixed flow of flow in the groove 38 in the groove 38 occurs. Therefore, by the rotation of the high-speed stirring blades 41 and 42, the processing speed can be easily increased, and the flow of the liquid in the tank 38 can be prevented from being fixed and the liquid which is insufficiently stirred and mixed can be discharged, thereby preventing the processing quality. The reduction. Further, since each of the stirring blades 41 and 42 in the stirring tank 38 is coupled to the motors 48 and 49 disposed outside the stirring tank 38 by the magnetic coupling. C, it is not necessary to insert the rotating shaft into the stirring tank 3. In the groove wall of the tank 8, since the agitation tank 38 can form a closed container structure in which the rotating shaft has no insertion portion, it is possible to prevent the lubricating liquid (sealing liquid) for the rotating shaft from being disturbed while the mixture is prevented from leaking out of the mixing liquid. The impurities are mixed into the liquid in the tank 38 to reduce the quality of the treated product -49-200804533.

In the production of the organic nanoparticle of the present invention, the production apparatus having such a configuration can be used to produce organic pigment particles in a batch mode or a continuous flow rate, and can also be produced in large quantities. Further, since the produced organic pigment particle dispersion is quickly discharged, the ratio of the organic material solution to the lean solvent liquid supplied in the agitation tank can be constantly fixed. For this reason, the solubility of the dispersion organic material can be fixed from the start of manufacture to the end of manufacture, and the monodisperse organic pigment particles can be stably produced. In addition, the immobilization of the liquid in the tank is prevented, and the organic pigment particle dispersion which is insufficiently stirred and mixed is discharged, and impurities such as a lubricating fluid (sealing liquid) for rotating the shaft are prevented from being mixed into the solution in the tank, thereby further Monodisperse organic pigment particles are produced stably. (Production Apparatus Example 3) Another embodiment of the apparatus used in the production of the organic nanoparticles of the present invention will be described using a manufacturing apparatus in which a blade having a shearing force is used for stirring. The shearing force in the present invention is the shearing force of the droplets (droplets) generated by the stirring blade and the organic pigment solution mixed with the poor solvent. The shape of the stirring portion which can be used in the present invention is not particularly limited as long as it can carry out a high shearing force, and generally, for example, a pulverizing blade, a turbine blade, a spiral blade, a Pfaudleir blade, or the like can be mentioned. Preferably, it is preferably a stirring, emulsification or dispersing machine which is composed of a dissolver blade, a rotatable turbine portion, and a stirring portion formed by a baffle portion having a slight gap around it and fixed at a position. -50- 200804533 The dissolver blade is a special agitating blade having a function capable of forming a high shear force, and Fig. 7 is a schematic view schematically showing a case in the front view, which is shown in Fig. 8 in the photo series 7K.

Further, it is also possible to use a device having a stirring portion composed of a rotatable turbine portion and a baffle portion that is fixed at a slight gap around the ninth portion, and is stirred and emulsified. The dispersing machine is, for example, Physcotron manufactured by Microtec Nition Co., Ltd., Τ·Κ homogenizing mixer manufactured by Special Machine Chemical Co., Ltd., and ULTRA-TURRAX manufactured by IKA Corporation. The stirring speed is different according to the viscosity of the poor solvent, the temperature, the type of the surfactant or the amount of the surfactant, but preferably 1 〇〇 to 1 00 〇 Tpm, preferably 1 50 〜 8 000 rpm, 200. ~6000rpm is especially good. If the number of rotations is too low, the stirring effect will not be fully exerted. Conversely, if it is too high, bubbles will be trapped in the poor solvent and it is not preferable. By concentrating the organic nanoparticle dispersion composition of the present invention to form an organic nanoparticle concentration of 1 〇 to 1 相对 times the composition, the color filter coating liquid can be produced on an industrial scale or A concentrate suitable for inkjet inkjet. Hereinafter, the concentration method will be described. The concentration method is not particularly limited as long as it is a concentrated organic nanoparticle liquid. For example, a mixed extraction solvent is added to the organic nanoparticle dispersion, and the organic nanoparticle is extracted by concentration in the extraction solvent phase, and filtered. a method of filtering the concentrated nanoparticle liquid of the concentrated extract; a concentration method of sedimenting the organic nanoparticle by centrifugation; a method of desalting and concentration by ultrafiltration; and sublimating the solvent by vacuum freeze drying - 51-200804533 Concentration method; a concentration method of drying a solvent by heating or even decompression is preferable. Or use such combinations, etc. is particularly good. The concentration of the organic nanoparticle after concentration is 1 to 100 by mass. /. Preferably, it is preferably 5 to 100% by mass, more preferably 10 to 100% by mass. Hereinafter, a method of concentrated extraction will be described.

The extraction solvent used in the concentrated extraction is not particularly limited, but is not substantially mixed with a dispersion solvent (for example, an aqueous solvent) of the organic nanoparticle dispersion (in the present invention, substantially no mixing means compatibility) The content is preferably low, the amount of dissolution is preferably 50% by mass or less, and more preferably 30% by mass or less. There is no particular lower limit for the amount of the dissolution, but it is actually 1% by mass or more in consideration of the solubility of the usual solvent. It is preferred to form a solvent at the interface after mixing and standing. Further, the extraction solvent is preferably a solvent in which the organic nanoparticles are redispersed in an extraction solvent without causing weak agglomeration (a floc which can be redispersed even if a high breaking force such as honing or high-speed stirring is not applied). . If it is in such a state, it does not cause strong agglomeration which changes the particle size, and it is preferable to extract the solvent to wet the intended organic nanoparticle, and it is preferable to remove the dispersion solvent such as water by filter filtration or the like. . The solvent of the extraction solvent is preferably an ester compound solvent, an alcohol compound solvent, an aromatic compound solvent or an aliphatic compound solvent, an ester compound solvent, an aromatic compound solvent or an aliphatic compound solvent, and an ester compound solvent is particularly preferred. Examples of the ester compound solvent include 2-(1-methoxy)propyl acetate and ethyl acetate 'ethyl lactate. The alcohol compound solvent is, for example, n-butanol or isobutanol. Examples of the aromatic compound solvent include benzene, toluene, xylene, and the like. The aliphatic compound solvent is, for example, η-hexane or cyclohexane. Further, the extraction-52-200804533 solvent system may be a pure solvent formed from the above preferred solvent, or may be a mixed solvent composed of a plurality of solvents. If the amount of the extraction solvent is such that the organic nanoparticle can be extracted, it is not particularly limited. However, it is preferable to use a small amount of the organic solvent, and it is preferable to use a small amount of the organic nanoparticle dispersion. When it is represented by a volume ratio, when the organic nanoparticle dispersion is set to 1 Torr, the extraction solvent to be added is preferably in the range of 1 to 1 Torr, more preferably in the range of 10 to 90, and 20 to 80. The range is particularly good. Enrichment when too much

It takes a lot of time. When too little, the extraction is insufficient and the nanoparticles remain in the dispersion solvent. After the extraction solvent is added, it is preferred to carry out stirring and mixing in such a manner as to sufficiently contact the dispersion. A general method can be used for stirring and mixing. The temperature at which the mixed extraction solvent is added is not particularly limited, but is preferably 1 to 1 〇 〇 ° C and preferably 5 to 60 ° C. Any apparatus can be used as long as it is desirable to carry out the addition and mixing of the extraction solvent in each step, and for example, it can be carried out using a separatory funnel type apparatus. The method used in, for example, desalting/concentration of a silver halide emulsion can be applied depending on the case of exceeding cerium. R esearch D isc I 〇sure N o · 1 0 2 0 8 (1 9 7 2 ), No _ 1 3 1 2 2 (1 9 7 5 ) and No. 1 6 3 5 1 (1 9 7 7 ) is known. For the pressure difference or flow rate that is important for the operating conditions, please refer to the characteristic curve described in the book "Using the Membrane Utilization Technology Operation Manual" (1978), p2 75, for the purpose of processing the organic nanoparticle dispersion. In the above, it is necessary to find the optimum conditions for inhibiting particle agglutination. Further, in addition to the method of dispersing the solvent by the membrane, there is a batch type of constant-capacity and intermittent addition of a solvent continuously added, and a constant-capacity type -53-200804533 having a relatively short desalting time is preferable. The solvent thus replenished may be pure water obtained by ion exchange or distillation, and the poor solvent may be mixed with the dispersant or the dispersant in the pure water, or may be directly added to the organic nanoparticle dispersion composition.

Fig. 10 shows an example of the configuration of a device for performing ultrafiltration. In the figure, as shown in the figure, the apparatus has a storage tank 81 for accommodating organic nanoparticles, a circulation pump 82 for circulating the dispersion in the storage tank 81, and a pump 82 for circulation. The by-produced inorganic salt in the dispersion is removed as an ultrafiltration module 8 3 for permeating water. The permeate system returns the separated dispersion to the storage tank 81 again, and the same operation is repeated until the deuterated inorganic salt is removed to achieve the intended purpose. Further, the device is provided with a supplementary pure water measuring flow meter 84 for supplementing a certain amount of pure water as a solvent for the loss of permeated water, and is provided with a permeate water meter for determining the amount of pure water replenishment. Use flow meter 85. Further, a pump 86 for cleaning in the reverse direction for introducing water for diluting the permeate water is provided. The ultrafiltration membrane system has been assembled as a module, such as flat type, spiral type, cylindrical type, hollow type, hollow type, and fiber type, such as Asahi Kasei (share), Daisil Chemical (share), Toray (share) It is commercially available from Nitto Denko Electric Co., Ltd., but it is preferably a spiral type or a hollow type from the viewpoint of total membrane area or detergency. Further, the classification molecular weight which is a critical enthalpy index which can form a permeable membrane component must be determined according to the molecular weight of the dispersing agent to be used, but it is preferably 5,000 or more and 50 Å or less, and 5,000 or more and 15,000 or less. Better. In order to separate the dispersion solvent and the concentrated extract of the organic nanoparticle dispersion, it is preferred to filter with a filter. The device for filter filtration is, for example, a device that can be used for pressure filtration. Preferred filters are, for example, nanofiltration -54 -

200804533, super filters, etc. The removal of the solvent by the filter is carried out. It is preferred to concentrate the organic naphthalene in the extract to form a concentrated nanoparticle liquid. The method of freeze-drying is not particularly limited and any method that can be utilized. For example, the refrigerant direct expansion method, the heat medium circulation method, the triple heat exchange method, the indirect preferred refrigerant direct expansion method, the indirect heating freezing method, and the heating freezing method. In any of the above methods, it is preferred to carry out knot drying. Pre-frozen conditions are not particularly dry and the sample system must be generally frozen. The apparatus for indirect heating and freezing method is preferably a dryer, an FTS freeze dryer, a LYOVAC freeze-drying dryer, a freeze dryer for research, a triple dryer, a single-cooling freeze dryer, a HULL freeze-type freeze dryer, and an experiment. A freeze dryer, a 硏φ single-cooling freeze dryer, and a small freeze-drying dryer are more preferred. The freeze-drying temperature is not particularly limited to preferably -1 20 to -20 ° C, more preferably -80 to -60 ° C. 5 The force is also not particularly limited, and the manufacturer may preferably have 1 to 35 Pa, preferably It is 1 to 15 Pa, more preferably ί. The freeze drying time is, for example, 2 to 48 hours, more preferably about 16 to 26 hours. However, these items are selected. For the freeze-drying method, for example, filtration may be carried out, and the residual dispersed rice particles may be further concentrated. The manufacturer may use the method of repeated freezing, and the method of heating and freezing, and more preferably, the indirect pre-freezing and the freezing restriction are used, but the freezing is performed. For example, a small freeze-drying dryer, an experimental heat exchange vacuum freeze-drying dryer, preferably a freeze dryer, a dryer, a single-cooling type, for example, _1 90 to -4 〇 c, : right. The freeze-drying pressure is suitable for selection, for example, about 1 to 36 hours, preferably 6 to 36 hours, and the manufacturer can be suitable for the preparation of mechanical technology. -55-200804533 Manual: Preparation Machinery Technology Research Institute, Local Library , ρ·120-129 (September 2000); Vacuum Handbook: Japan Vacuum Technology Co., Ltd., OM, Ρ.32 8-331 (1992); Freeze and Dry Research Society: Ito Takaji He, No. 1 5 ^ ρ·82 (1965), etc. The following describes the centrifugal separation. Centrifugation used in the concentration of organic nanoparticles separated by centrifugation

The separator " can be used as long as it can sediment the organic nanoparticles in the organic nanoparticle dispersion (or organic nanoparticle concentrate). The centrifugal separator is, for example, a widely used apparatus, and may be, for example, a continuous centrifugation machine having a function of a crude distillation (a function of absorbing a supernatant layer or a discharge system during rotation) or a solid material continuously discharged. Centrifugal separation conditions are based on centrifugal force (representing the centrifugal acceleration several times the acceleration of gravity), preferably 5 0 ~ 1 0 0 0 0, 1 0 0~8 0 0 is preferred, 15 0~60 00 is particularly good. . The temperature at the time of centrifugation is preferably -1 to 80 ° C, preferably -5 to 70 ° C, and particularly preferably 〇 to 60 ° C depending on the type of the solvent of the dispersion. The following is a description of drying. The apparatus used in the concentration of the organic nanoparticles to be dried under reduced pressure is not particularly limited as long as it evaporates the solvent of the organic nanoparticle dispersion (or organic nanoparticle concentrate extract). For example, a vacuum dryer and a rotary pump which are widely used, or a device which can be heated and reduced in pressure while stirring, and a device which can be continuously dried by passing the liquid through a tube which is heated and decompressed can be used. The heating and decompression drying temperature is preferably 30 to 230 ° C, preferably 35 to 200 ° C, and particularly preferably 40 to 180 ° C. The pressure at the time of pressure reduction is preferably 100 to 100,000 Pa - 56 to 200804533, preferably 300 to 90,000 Pa, and particularly preferably 500 to 80,000 Pa. According to the concentration method as described above, the organic nanoparticle can be more efficiently concentrated from the organic nanoparticle dispersion. When the concentration of the nanoparticles in the organic nanoparticle dispersion liquid forming the raw material is set to 1, the concentration of the concentrated organic nanoparticle paste is preferably concentrated to about 1000 to 3000 times, more preferably. It is about 500 to 2000 times.

The organic nanoparticle dispersion composition of the present invention can be finely dispersed in an aggregated state of the organic nanoparticle by, for example, concentration. (In the present invention, the fine dispersion means that the particle agglomeration in the unfolding dispersion is improved. Dispersion) The organic particles contained in the concentrated organic nanoparticle dispersion by the above extraction solvent, centrifugation, drying, or the like are usually aggregated by concentration thereof to cause aggregation. In this case, in order to allow rapid filtration of the filter and to obtain a state of good dispersion again, it is preferred to be a floc which can be agglomerated at a redispersible degree. For this reason, the degree of dispersion by the general dispersing method is insufficient in terms of microparticulation, and a method of further increasing the efficiency of miniaturization is necessary. In the present invention, it is preferable that the organic particles such as agglomerated organic particles are aggregated by a secondary force, and the primary particles are so-called aggregated nanoparticles when the size is a nanometer. According to the method for producing an organic nanoparticle dispersion of the present invention, the polymer particles having a mass average molecular weight of 1,000 or more are contained in the aggregated organic particle liquid, and the organic particles can be appropriately finely dispersed (in the present invention, In the case where the agglomerated organic particles are contained in the liquid, the agglomerated organic particles are contained in the liquid, and even if it is a dispersion, a concentrate, or a paste, a slurry or the like, as long as it contains aggregated organic particles. Next, the polymer compound described above used in the pigment dispersion composition of the present invention (the "polymer compound" of the present invention is preferably an organic compound having a mass average molecular weight of 1,000 or more, and is not particularly specific. The upper limit is actually a mass average molecular weight of 500,000 or less, preferably 1,000,000 or less, more preferably 50,000 or less.

The polymer compound to be used in the organic nanoparticle-dispersed composition of the present invention is preferably a high molecular compound having a mass average molecular weight of 1,000 or more and a high molecular weight represented by the following formula (1). In the above formula (1), A1 represents an acidic group, a group having a basic nitrogen atom, a urea group, a carbamate group, a group having a coordinating oxygen atom, and a carbon number of 4 or more. A hydrocarbon group, an alkoxyalkyl group, an epoxy group, an isocyanate group, a monovalent organic group having a group selected from a hydroxyl group, or a monovalent organic group containing a φ organic dye structure which may have a substituent or a hetero ring. The η A1 lines may be the same or different. Specifically, the oxime 1 is not particularly limited, and the above-mentioned "monovalent organic group having an acidic group" is, for example, a carboxylic acid group, a sulfonic acid group, a monosulfate group, a phosphoric acid group, a monophosphate group, or a boric acid. A monovalent organic group such as a group. Further, the above "monovalent organic group having a group having a basic nitrogen atom" is, for example, a monovalent organic group having an amine group (-Ν2) and a substituted imido group (_NHR8, -NR9R1Q) The valent organic group (herein, R8, R9, and R10 each independently represent an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, -58 to 200804533, and an aralkyl having 7 or more carbon atoms and 30 or less carbon atoms. a monovalent organic group having a fluorenyl group represented by the following formula (a1): wherein the group of the formula (a1) and the group of the cores independently represent an alkyl group having a carbon number of 1 to 20, and a carbon number of 6 The aryl group having 20 or less of the above, the aralkyl group having 7 or more and 30 or less carbon atoms, and the monovalent organic group having a mercapto group represented by the following formula (a2), each of the Ra3 and Ra4 systems in the formula (a2) The alkyl group having 1 to 20 carbon atoms, the aryl group having 6 or more and 20 or less carbon atoms, and the aralkyl group having 7 or more and 30 or less carbon atoms are independently represented.

r01—N Ra3-HM

The above-mentioned "monovalent organic group having a ureido group" is, for example, -NHCONHR15 (here, R15 represents a hydrogen atom, or an alkyl group having a carbon number of 20, an aryl group having a carbon number of 6 or more and 20 or less, and a carbon number of 7 Above 30 or less aralkyl groups). The above-mentioned "monovalent organic group having a urethane group" is, for example, -NHCOOR16 or -〇CONHR17 (here, R16 and R17 each independently represent an alkyl group having 1 to 20 carbon atoms, and a carbon number of 6 or more and 20 The following aryl group, an aralkyl group having 7 or more and 30 or less carbon atoms, and the like. The above "group containing a group having a coordinating oxygen atom" is exemplified by a group having a acetyl ketone ligand group, a group having a crown ether, and the like. The "group having a hydrocarbon group of 4 or more carbon atoms" is, for example, an alkyl group having 4 or more carbon atoms (for example, an octyl group or a dodecyl group) or an aryl group having 6 or more carbon atoms (for example, 'phenyl group, naphthyl group, etc.). And an aralkyl group having 7 or more carbon atoms (for example, a benzyl group or the like). At this time, there is no upper limit for the carbon number, and it is preferably 30 or less. -59- 200804533 The above "alkyl group having an alkoxyalkyl group" is, for example, a group having a trimethoxycarbonylalkyl group, a triethoxyalkylene group or the like. The above "epoxy group-containing group" is, for example, a group having a glycidyl group or the like. The above "isocyanate group-containing group" is, for example, a 3-isocyanatepropyl group or the like. The above "group having a hydroxyl group" is, for example, a 3-hydroxypropyl group or the like.

Among the above, the above A1 is preferably a monovalent organic group selected from the group consisting of an acidic group, a group having a basic nitrogen atom, a urea group, and a hydrocarbon group having 4 or more carbon atoms. Further, the above organic dye structure or heterocyclic ring system is not particularly limited, and more specifically, the organic dye structure is, for example, a phthalocyanine compound, an insoluble azo compound, an azo lake compound (Azo lake compound), an anthraquinone compound, and quinine. Anthrone compound, dioxan compound, diketopyrrolopyrrole compound, hydrazine compound, fluorenone compound, indanthrone compound, flavanone compound, anthrone compound, hydrazine compound, thioindigo compound, etc. . Further, the heterocyclic ring is, for example, thiophene, furan, hydrazine, pyrrole, pyrroline, pyrrolidine, dioxane, pyrazole, pyrazoline, pyrazolidine, imidazole, oxazole, thiazole, oxadiazole, three Azole, thiadiazole, pyran, pyridine, piperidine, dioxane, gustoline, hydrazine trap, pyrimidine, pipe trap, triple trap, trimethylthio aldehyde, isoporphyrin, isoindolinone. Benzimidazolone, amber imine, phthalimide, naphthyl imine, hydantoin, quinone, quinoline, acridine, acridone, anthracene, and the like. Further, the above-mentioned organic dye structure or heterocyclic ring may have a substituent, and the substituent -60-200804533 is, for example, an alkyl group having 1 to 20 carbon atoms such as a methyl group or an ethyl group, and a carbon number of 6 or more such as a phenyl group or a naphthyl group. a decyloxy group having a carbon number of 1 to 6 such as an aryl group of 1-6, a hydroxyl group, an amine group, a carboxyl group, a sulfonylamino group, an N-thioguanamine group or an ethoxylated oxy group, a methoxy group, an ethoxy group or the like. Alkoxy group having 1 to 6 carbon atoms, a halogen atom such as chlorine or bromine, an alkoxycarbonyl group having 2 to 7 carbon atoms such as a methoxycarbonyl group, an ethoxycarbonyl group or a cyclohexyloxycarbonyl group; A carbonate group or the like such as tributyl carbonate. Further, the above-mentioned .A1 is preferably a monovalent organic group represented by the following formula (4).

In the above formula (4), B1 represents a group selected from an acidic group, a group having a basic nitrogen atom, a urea group, a carbamate group, a group having a coordinating oxygen atom, and carbon. a hydrocarbon group having 4 or more, an alkoxyalkyl group, an epoxy group, an isocyanate group, and a hydroxyl group, or an organic dye structure or a hetero ring which may have a substituent; R1 8 means a single bond or an a-valent organic or Inorganic linkage. A1 represents 1 to 5, and a1 B1 systems may be the same or different.

The B1 system is synonymous with the above A1 in the formula (4), and the preferred embodiment is also the same. The above organic dye structure or heterocyclic ring system is, for example, a phthalocyanine compound, an insoluble azo compound, or an azo lake compound (Azo lake) compound. , anthraquinone compound, quinophthalone compound, dioxan compound, diketopyrrolopyrrole compound, aziridine compound, anthrone compound, indanthrone compound, flavanone compound, anthrone compound, anthraquinone compound An organic dye structure such as a thioindigo compound, such as thiophene, furan, 卩ill comet, pyrrole, pyrroline, pyrrolidine, dioxane, pyrazole, pyrazoline, pyrazolidine, imidazole, oxazole, thiazole , oxadiazole, triazole, thiadiazole, pyran, pyridine, piperidine, dioxane, taste -61- 200804533 porphyrin, sorghum, pyrimidine, piperculosis, triterpene, arsenic Aldehyde, isoindolinone, isoindolinone 'benzimidazolone, amber imine, phthalimide 'naphthoquinone imine, hydantoin, 嗤胄' (four), 卩丫_ And (iv) a heterocyclic ring such as a ketone or an anthracene. Further, the above-mentioned organic dye structure or heterocyclic ring may have a substituent, and examples of the substituent include a fluorenyl group having 1 to 20 carbon atoms such as a methyl group or an ethyl group, and an aryl group having a carbon number such as benzoquinone or ruthenium. Alkane, an amine group, a carboxyl group, a sulfonylamine N-sulfuryl 0-female group, an alkoxy group having 1 to 6 carbon atoms, a methoxy group, an ethoxy group or the like having 1 to 6 carbon atoms a halogen atom such as an oxy group, a chlorine atom or a bromine group, a methoxycarbonyl group, an ethoxycarbonyl group or a cyclohexyloxycarbonyl group having a carbon number of 2 to 7 or a base group, an alkyl group or a dibutyl carbonate carbonate Etc. R18 represents a single bond or a 1+1 valent linkage, and ai represents 1 to 5. The linking group R18 is composed of 1 to 100 carbon atoms, 1 to 10 nitrogen atoms, 0 to 50 oxygen atoms, 1 to 20 hydrogen atoms, and 20 to 20 sulfur atoms. The group may be unsubstituted or substituted. R18 is preferably an organic linking group. Specific examples of R1 8 include, for example, the following structural units or a combination of the structural units. -62- 200804533

(t-1) (t-2) (t-3)

(t-4) (t-5) (t-6) (t-7) (t-8) (t-9) (t-10)(t_11) (t-12)

—SN 一一6*^1—一C*G— 6 k 1 (t-16) (t-17) (t -18) (tH9) Ο O 0 -o prepare g- 1 each Jj— (t- 13) (t-14) (t-15)

~G=N— -6=0--6=g- HC=C—(t-20) (t-21) (t-22) (t-23) (t - 24) -C=G- ( T-25) -0 (t a 26) ^ ^ -3⁄41 (t-27) (t-28) (t-29) (t-30) (t-31) (t-32) (t-33) (t-34) In the case where R1 8 has a substituent, the substituent is, for example, an alkyl group having 1 to 20 carbon atoms such as a methyl group or an ethyl group, and an aromatic group having a carbon number of 6 to 16 such as a phenyl group or a naphthyl group. a carbon number of a methoxy group, a methoxy group, an ethoxy group or the like having 1 to 6 carbon atoms such as a hydroxyl group, an amino group, a carboxyl group, a sulfonylamino group, an N-thioguanamine group or an ethoxylated Φ group. a halogen atom having an alkoxy group, a chlorine atom or a bromine group, an alkoxycarbonyl group having a carbon number of 2 to 7 such as a methoxycarbonyl group, an ethoxycarbonyl group or a cyclohexyloxycarbonyl group, a cyano group or a butyl butyl carbonate. Such as carbonate groups and the like. In the above formula (1), R1 represents a (m + n)-valent linking group. The m + n system satisfies 3 to 10 0. The (m + n) valent linking group represented by the above R1 includes 1 to 1 carbon atoms, 〇 10 carbon atoms, and 〇 50 particles. Oxygen atom, 1~2 〇0-63-

The base of the hydrogen atom of 200804533 and the sulfur atom of 20 to 20 may be unsubstituted and more substituted. It is preferred that R1 is an organic linking group. Specific examples of R1 include, for example, the above (t-1) to (t-34) or a combination of the structural unit (which can form a ring structure). In the case where R1 has a substituent, the substituent 'group is, for example, an alkyl group having 1 to 20 carbon atoms such as a methyl group, a 6 to 16 carbon group such as a phenyl group or a naphthyl group, a hydroxyl group, an amine group or a carboxyl group. a halogen atom having a carbon number of 1 to 6 such as a sulfonylamino group, an N-thioguanamine group or an ethyl group, a methoxy group such as a methoxy group such as a methoxy group or an ethoxy group; or a halogen atom such as chlorine or bromine; Alkoxycarbonyl group having a carbon number of 2 to 7 such as a methoxycarbonyl group, an ethoxy group or a cyclohexyloxycarbonyl group, or a carbonate group such as cyanotributyl carbonate. R2 represents a single bond or a divalent linking group. R2 is a group consisting of one carbon atom, one to ten nitrogen atoms, 0 to 50 oxygen atoms, one hydrogen atom, and 〇-20 carbon atoms. Has a substituent. It is preferred that R2 is an organic linking group. Specific examples of R2 include, for example, the structural units of the above t-3, 4, 7 to 18, 22 to 26, and 34, or a combination of the structural units. In the above case, when R 2 has a substituent, the substituent is an alkyl group having 1 to 20 carbon atoms such as a methyl group or an ethyl group, a 6 to 16 aryl group such as a phenyl group or a naphthyl group, a hydroxyl group or an amine group. Alkoxy group having 1 to 6 carbon atoms such as a carboxyl group, a carboxy group, a sulfonylamino group or a sulfonium amino group, and a methoxy group having a carbon number of 1 to 6 such as a methoxy group or an ethoxy group; A halogen atom such as a halogen atom, a methoxycarbonyloxycarbonyl group, a cyclohexyloxycarbonyl group or the like having 2 to 7 carbon atoms of alkoxycarbonyl group or a carbonate group such as a third butyl carbonate. It is also possible to construct a single, B, aryl oxy 1-6 ganban, the first ~ 00 ~ 200 卜 also 32 ^ example carbon number ^ base, carbon, B:, cyan-64-200804533 above the general formula (1) , m means 1 to 8. The m system is preferably 1 to 5, 1 to 3 is preferred, and 1 to 2 is particularly preferred. Also, η represents 2 to 9. The η system is preferably 2 to 8, 2 to 7 is preferred, and 3 to 6 is particularly preferred. In the above formula (1), Ρ1 represents a polymer compound residue (hereinafter also referred to as a polymer skeleton), and can be selected from a general polymer or the like according to the purpose thereof.

Among the polymers, especially when forming a polymer skeleton, it is selected from the group consisting of a polymer or a copolymer of a vinyl monomer, an ester polymer, an ether polymer, a urethane polymer, and a guanamine polymerization. , epoxy polymer, polyoxynized polymer, and the like, or copolymer (eg, a polymer comprising a polyether/polyurethane copolymer, a polyether/vinyl monomer) At least one selected from the group consisting of a copolymer or the like (which may be any of a random copolymer, a block copolymer, and a graft copolymer) is preferably selected from a polymer of a vinyl monomer or At least one of a group consisting of a copolymer, an ester polymer, an ether polymer, a urethane polymer, and a modified or copolymer thereof is preferably a polymer of a vinyl monomer or It is a copolymer that is particularly good. Further, it is preferred that the above polymer is soluble in an organic solvent. When the affinity with the organic solvent is low, for example, when it is used as a pigment dispersant, the affinity with a dispersing medium becomes weak, and it becomes impossible to ensure a sufficient adsorption layer which is dispersed and stabilized. Among the polymer compounds represented by the above formula (1), a polymer compound represented by the following formula (2) is particularly preferred. -65- 200804533

general formula

In the above formula (2), the A2 system is synonymous with A1 of the above formula (1), and its specific preferred embodiment is also the same. Specific examples of the organic dye structure are phthalocyanine compounds and azo lakes ( Azo lake) a compound, an anthraquinone compound, a dioxan compound, a diketopyrrolopyrrole compound, etc. are preferred. The heterocyclic ring is imidazole, triazole, pyridinium, piperidine, porphyrin, tri-farming, Isoporphyrin, isoindolinone, benzoquinone, benzothiazole, amber imine, phthalimide, naphthyl imine, hydantoin, quinone, quinoline, Carbazole, acridine, ketone, guanidine, and the like are preferred. Further, it may have a substituent similar to A1, and the substituent is the same as in the case of A1, and the preferred embodiment is also the same. Further, it is preferable that the A2 is a monovalent organic group represented by the above formula (4), and the details, specific examples, and preferred aspects of the organic group are the same. In the above formula (2), R3 represents a (x + y)-valent linking group. The (x + y)-valent linking group represented by the above R3 includes a carbon atom of 1 to 60 carbon atoms, a nitrogen atom of 〜1 to 〇φ, an oxygen atom of 〜50 atoms, and a ～1〇〇 group. The hydrogen atom and the sulphur atom of -20 atoms may be unsubstituted or substituted. The 7K (x + y) valent linking group of the above R3 is synonymous with the (m + n) valent linking group in the above r1, and the preferred aspects thereof are also the same. Further, specific examples are the same structural units as described above, or a combination of the structural units. In the above, a preferred embodiment (specific example to (r-17)) in which the linking group represented by 'R3 is an organic linking group and the organic linking group is preferred is as follows. However, the invention is not limited by these. -66- 200804533 (Μ) _ Ο II ch2 — ch2 — c-o - ch2, h3c-ch^ (r-2) i?

o II -CH2—〇-C~Ch!2-CH2· "ch2-oc-ch2-ch2-oo II —CH2 — C-〇-CH2, /CH2-〇»C-CH2—H3C-CHf, cri2 -〇-C-CH2— oo * o II II 42-CH2-NH-C-〇-CH2, /CH2-〇-C-NH-CH2-ch2- h3c-ch^ ^ch2-oc-nh-ch2- Ch2- 0 (r-4) _ i? f? CH2-CH2—〇-〇〇-CH2, /CH2-〇-〇〇, CJH2—CH2-h3c-ch 彡CH2- o- c- o- CH2- C Holt 2 2o (r-5) (r-6)

CHo-CHo— 〇γΝγ〇 ch2-ch2〆 Νγ n, ch2 - ch2-o (r-7) i? i? 〇γΝ

9h2 — ch2—n-c-o-ch2- H

O N N II _gh2-ch2-o-c-|^ch2-ch, 丫 "ch2-ch2-n-c-0-ch2- (r-8) (r-9) /CH2, 'CH2, CH2〆. ,

〇, CHrCH2 xCH2v

cTn,ch,CH2 II ^ O -67 200804533 (r-10) Ο ο _CH2-CH2-C-〇GH2, c/CH2-〇-C,CH2-CH: ,CH2 — CHf『CH2οο Η -ch2-c -och2, -CHp^CO-CH^ ^ II ζο αν π .g-ch2-gh2·ο 'c,CH2_〇-C-CH2- ^ch2-oc-ch2-ο (卜12) _ch2 - ch2- Nh-!^-och2. .CH2 — CH2- NH- c- O CH( II 2o i? ^ ch2-o- c^nh- ch2- ch2- v CHS- o- NH - CH2- CH2-o (M3 ) •ch2-ch2-o-co •ch2-ch2.

00 - ch2 — ch2- c-o-ch2-ch2 H ^o (Bu 14) • CH2—CH2—〇— —CH2- CH2-〇1

C-o-ch2-ch2-C - 〇-GH2-CH2_ 〇 -CH2-CHfO_9 0 (r-15) —CH2- GH2, n〆.七- _ch2-ch2, human 夂 _CH2-GHrN N N, ch2—CH2_GH2~ ch2-ch2— (r-16)

II i? .CH2—CH2-C-〇CH2, /CH2-〇-〇CH2-CH2, .CH2 〇-CH2-CH2-C-〇-CHr 2 2 " 2o ,CH factory CH2 —CH2,〆CHg - CH2- 『CH2— ch2- ch2-oc-ch2 — ch2- 2 2 2o (r-17) 0 II —ch2—c-och2,^ O >c II ^CHf ,GH 2 — C-0-CH2 /CH2-〇-ch2-co-ch^ ^ch2-oc-ch2-o oo II , gh2_o-och2- "CH2~O^C~CH2" o -68- 200804533 In the above, 'the availability of raw materials, From the viewpoints of easy synthesis and solubility in various solvents, the above (Π), (Bu 2), (r-1 0), (r-11), (r-16), (hl7) groups are used. It is better.

Further, in the case where the above R3 has a substituent, the substituent is, for example, an alkyl group having a carbon number of from 1 to 20 such as a methyl group or an ethyl group, or a hexene having a carbon number of from 6 to 16 such as a phenyl group or a naphthyl group. a carbon number of 1 to 6 having a carbon number of 1 to 6 such as a hydroxyl group, an amine group, a carboxyl group, a sulfonylamino group, a sulfonylamino group or an ethoxylated oxy group, a methoxy group, an ethoxy group or the like, and a carbon number of 1 to 6 a halogen atom such as an alkoxy group, a chlorine atom or a bromine group; an alkoxycarbonyl group having a carbon number of 2 to 7 such as a methoxycarbonyl group, an ethoxycarbonyl group or a cyclohexyloxycarbonyl group; a cyano group; a third butyl carbonate; Carbonate groups and the like. In the above formula (2), R4 and R5 each independently represent a single bond or a divalent linking group. The "divalent linking group" represented by the above R4 and R5 may, for example, be an unsubstituted or linear, branched or cyclic alkyl group, an aryl group or an aralkyl group. -0 -, - S -, - C ( = Ο Bu, -N ( R1 9) -, - S Ο -, -S02-, -C〇2 -, -N(R2G)S〇2-, or a combination Preferred examples of the divalent group of two or more of these groups (the above R19 and R2C) each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms). Among them, organic linking groups are preferred here. The above R4 is a linear or branched alkyl, aralkyl, -〇-, -C(=0)-, -N(R19)-, -S〇2-, -C02-,- N(R20)S〇2-(wherein R19 and R2G each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), or a divalent group in which two or more such groups are combined is preferred, Chain or branched alkyl, aralkyl, -〇-, -c(=0)-, -n(r19)- (the above r19 represents a hydrogen atom or a carbon number of alkyl groups), - C〇2-, or a combination of two 2-valent groups having such a group on -69-200804533 is particularly preferred. The above R5 is a single bond, a straight chain or a branched alkyl group, an aralkyl group, -0-, (:(=0), -N(R1 9)·, -S〇2-, -C02 -, -N(R20)SO2- (wherein R19 and R2Q each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), or a divalent group in which two or more of these groups are combined is preferable. Linear or branched alkyl, aralkyl, ·0-, -C( = 0)-, -N(R19)-

It is particularly preferable that R19 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, -C02-, or a divalent group having two or more of these groups. In the case where the above R4 and R5 have a substituent, the substituent is, for example, an alkyl group having 1 to 20 carbon atoms such as a methyl group or an ethyl group, or an aryl group having 6 to 16 carbon atoms such as a phenyl group or a naphthyl group. a carbon number of 1 to 6 of a hydroxyl group having 1 to 6 carbon atoms such as a hydroxyl group, an amine group, a carboxyl group, a sulfonylamino group, an N-thioguanamine group or an ethoxylated group, and a methoxy group or an ethoxy group. a halogen atom having an alkoxy group, a chlorine atom or a bromine group, an alkoxycarbonyl group having a carbon number of 2 to 7 such as a methoxycarbonyl group, an ethoxycarbonyl group or a cyclohexyloxycarbonyl group, a cyano group or a t-butyl carbonate. Such as carbonate groups and the like. In the above formula (2), y represents 1 to 8, 1 to 5 is preferred, 1 to 3 is preferred, and 1 to 2 is particularly preferred. Further, X represents 2 to 9, 2 to 8 is preferable, 2 to 7 is preferable, and 3 to 6 is particularly preferable. Further, P2 in the formula (2) represents a polymer skeleton, and can be selected from a general polymer or the like according to the purpose thereof. The preferred embodiment of the polymer is synonymous with P1 in the above formula (1), and the preferred aspects thereof are also the same. In particular, among the polymer compounds represented by the above formula (2), R3 is the above specific examples (r-1), (r-2), (Bu 1), (μ), (r-1 6) ), or ("-1 7), R4 is a single bond, a straight chain or a branched branch, an aralkyl group, -〇-, -70- 200804533 -C( = 0)-, -N (R19)-(the above R19 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), -C〇2-, or a divalent organic group in which two or more of these groups are combined, and R5 is a single bond, Ethyl, propyl, or a linking group of the following formula (s_a) or (s_b), P is a polymer or copolymer of an ethylenic monomer, an ester polymer, or an ether system A polymer, a urethane polymer, or the like, a polymer compound having a y of 1 to 2 and an X of 3 to 6 is particularly preferred. Further, in the following group, R21 represents a hydrogen atom or a methyl group, and | represents 1 or 2.

(s-a) i? i? CH2—〒H-C −〇-CH2-?H-CH2~〇 - C-(cH2tR21 OH 1 (s-b)

O

II —ch2-^h- c-o-ch2—ch2— R21

The mass average molecular weight of the polymer compound is 1,000 or more, and in terms of the mass average molecular weight, it is preferably from 100 to 50,000, preferably 0,0 0, preferably from 3,000 to 10,000. ~8000 0 is better, 7000~60000 is especially good. When the mass average molecular weight is within the above range, the effect of introducing a plurality of functional groups to the terminal end of the polymer is sufficiently exhibited, and exhibits excellent performance in terms of adsorption to a solid surface, cell formation energy, and interface activity. In particular, when such a polymer compound is used as a pigment dispersant, good dispersibility and dispersion stability can be achieved. The polymer compound represented by the above formula (1) (including those represented by the formula (2)) -71-200804533 is not particularly limited, and can be synthesized by the following method or the like. Among the following synthesis methods, the synthesis method of the following 2, 3, 4, and 5 is preferable, and the following synthesis methods of 3, 4, and 5 are particularly preferable.

a polymer obtained by introducing a terminal having a functional group selected from a carboxyl group, a hydroxyl group, an amine group, etc., with a fluorenyl halide having a plurality of functional groups (A1 or A2 in the above formula), or having a plurality of functional groups ( A method of polymerizing a compound of a compound of A1 or A2) or an isocyanate having a plurality of functional groups (A1 or A2 in the above formula) in the above formula. 2. A method of subjecting a polymer having a carbon-carbon double bond to a terminal to a molar addition reaction with a thiol having a plurality of functional groups (A1 or A2 in the above formula). 3. A method of reacting a polymer having a carbon-carbon double bond at its terminal with a thiol having a plurality of functional groups (A1 or A2 in the above formula) in the presence of a radical generator. 4. A method in which a polymer of a plurality of thiols is introduced at a terminal and a functional group (A1 or A2 in the above formula) into which a carbon-carbon double bond φ is introduced is reacted in the presence of a radical generator. A method of radically polymerizing a vinyl monomer as a chain shifting agent having a thiol compound having a plurality of functional groups (A1 or A2 in the above formula). In the above, the polymer compound (preferably the polymer compound represented by the formula (2)) contained in the organic nanoparticle dispersion composition of the present invention can be used, for example, in the above 2, 3, 4, and 5. The synthesis by either method is preferable, and it is preferable to synthesize by the method of the above 5 from the ease of synthesis. More specifically, a compound represented by the following formula (3) is used as a chain shift-72-200804533 to carry out radical polymerization to a preferred formula (3) \ /g \ *. · . Jf - ..... In the above formula (3), R6, R7, A3, g, and h are respectively R3, r4, a2, X' in the above formula (2) and y is synonymous, and its preferred aspect is also the same. The above vinyl single system is not particularly limited, and examples thereof include (meth) φ acrylates, butenoates, vinyl esters, maleic acid diesters, and fumaric acid diesters. Preferred are the class, the itaconic acid diester, the (meth) acrylamide, the class, the vinyl ether, the vinyl alcohol ester, the styrene, the (meth) acrylonitrile, and the like. These examples are, for example, the following compounds. Examples of the above (meth) acrylates include methyl (meth) acrylate, ethyl (meth) acrylate, η-propyl (meth) acrylate, isopropyl (meth) acrylate, (A) Base) n-butyl acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, η-hexyl (meth)acrylate, % cyclohexyl (meth)acrylate, (methyl) Tert-butylcyclohexyl acrylate, 2-ethylhexyl (meth)acrylate, third octyl (meth)acrylate, dodecyl (meth)acrylate, octadecyl (meth)acrylate , (meth)acrylic acid ethyl ethoxylate, phenyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-methoxyethyl (meth)propionate, (methyl) ) 2-ethoxyethyl acrylate, 2-(2-methoxyethoxy)ethyl (meth)acrylate, 3-phenoxy-2-hydroxypropyl (meth)acrylate, (methyl) Benzyl acrylate, diethylene glycol monomethyl ether (meth)acrylate, diethylene glycol monoethyl ether (meth)acrylate, triethylene glycol monomethyl (meth)acrylate , (meth)acrylic acid triethylene glycol monoethyl ether, (meth)acrylic acid polyethyl-73- 200804533 diol monomethyl ether, (meth)acrylic acid polyethylene glycol monoethyl ether, (methyl) Β-phenoxyethoxyethyl acrylate, nonylphenoxy polyethylene glycol (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentanyl hydroxyethyl (meth)acrylate, Trifluoroethyl (meth)acrylate, octafluoropentyl (meth)acrylate, perfluorooctyl (meth)acrylate, dicyclopentenyl (meth)acrylate, tribromobenzene (meth)acrylate Ester, tribromophenyl hydroxyethyl (meth)acrylate, and the like.

Examples of the above-mentioned butenoic acid esters include, for example, butyl crotonate, hexyl butenoate and the like. Examples of the vinyl esters include vinyl acetate, vinyl propionate, vinyl butyrate, vinyl methoxy acetate, ethylene benzoate, and the like. Examples of the above maleic acid diesters include, for example, dimethyl maleate, diethyl maleate, and dibutyl maleate. Examples of the above-mentioned fumaric acid diesters include, for example, dimethyl fumarate, diethyl fumarate, dibutyl fumarate and the like. Examples of the above itaconic acid diesters include, for example, dimethyl itaconate, diethyl itaconate, dibutyl itaconate and the like. Examples of the above (meth) acrylamide are, for example, (meth) acrylamide, hydrazine-methyl (meth) acrylamide, hydrazine-ethyl (meth) acrylamide, hydrazine-propyl (Meth) acrylamide, Ν-isopropyl (meth) acrylamide Ν 正-n-butyl propylene fluorenyl (methyl) decylamine, hydrazine-tert-butyl (meth) acrylamide, Ν-cyclohexyl (meth) acrylamide, Ν-(2-methoxyethyl) (meth) acrylamide, hydrazine, hydrazine-dimethyl (meth) acrylamide, hydrazine, hydrazine - Diethyl (meth) acrylamide, -74- 200804533 N-phenyl (meth) acrylamide, N-benzyl (meth) acrylamide, (meth) propylene sulfhydryl, two Acetone acrylamide and the like.

Examples of the above styrenes are, for example, styrene, methyl styrene, dimethyl styrene, trimethyl styrene, ethyl styrene, isopropyl styrene, butyl styrene, hydroxystyrene, Oxystyrene, butoxystyrene, ethoxylated styrene, chlorophenyl benzene, dichlorophenyl acetophenone, bromostyrene, chloromethyl styrene, deprotectable with acidic materials A hydroxystyrene, methyl benzoic acid methyl ester, and α-methyl styrene, which are protected by a base (for example, t-Boc or the like). Examples of the vinyl ethers include methyl vinyl ether, butyl vinyl ether, hexyl vinyl ether, and methoxyethyl vinyl ether. In addition to the above compounds, (meth)acrylonitrile, a vinyl-substituted heterocyclic group (for example, vinylpyridine, vinylpyrrolidone, vinylcarbazole, etc.) or fluorene-vinylformamide may also be used. , Ν-vinylacetamide, hydrazine-vinylimidazole, vinyl caprolactone, and the like. Further, in addition to the above compounds, a vinyl monomer having a functional group such as a urethane group, a ureido group, a sulfonamide group, a phenoxy group or an imido group may be used. A single system having such a urethane group or a ureido group can be suitably synthesized by, for example, an addition reaction of an isocyanate group with a hydroxyl group or an amine group. Specifically, it may be an addition reaction of a monomer containing an isocyanate group with a compound containing one hydroxyl group or a compound containing a primary or secondary amine group, or a monomer having a transbasic group or containing a grade 1 or The addition reaction of a monomer of a 2-stage amine group with an isocyanate can be suitably synthesized. The above vinyl single system can be polymerized by only one kind, and can also be copolymerized by using two or more kinds of -75-200804533. These free radical polymers can be obtained by a general method and according to a common method. It is obtained by polymerizing a corresponding vinyl monomer. For example, a vinyl radical monomer and a chain shifting agent are dissolved in a suitable solvent, and a radical polymerization heuristic agent is added thereto at about 5 Torr. 〇 Method of dissolving in solution at ~2 2 0 °C (solution polymerization method).

An example of a suitable solvent used in the solution polymerization method is arbitrarily selected, for example, depending on the solubility of the monomer to be used, and the copolymer to be produced. For example: methanol, ethanol, propanol, isopropanol, methoxy-2-propanol, 1-methoxy-2-propyl acetate, acetone, methyl ethyl ketone, methyl isobutyl ketone, Methoxypropyl acetate, ethyl lactate, ethyl acetate, acetonitrile, tetrahydrofuran, dimethylformamide, chloroform, toluene. These solvents can be used in combination of two or more. Further, as the radical polymerization initiator, for example, 2,2'-azobis(isobutyronitrile) (AIBN), 2,2'-azobis-(2,4'-dimethylvaleronitrile) can be used. An azo compound, a peroxide such as benzammonium peroxide, and a persulfate such as potassium persulfate, φ ammonium persulfate, and the like. The compound represented by the above formula (3) can be synthesized by the following method or the like, and from the viewpoint of ease of synthesis, the following method is preferred. 6. A method of converting a halide compound having a plurality of functional groups (A1 or A2 in the above formula) into a thiol compound (for example, a method of reacting with thiourea to carry out hydrolysis, and a method of directly reacting with NaSH, a method of reacting with CH3COSNa for hydrolysis, etc.) 7. A compound having 3 to 10 thiol groups in one molecule, and having a functional group (a1 or A2 in the above formula) and having a hydrogenthio group Reaction -76- 200804533 Method of Addition Reaction of Functional Group Compounds The "functional group reactive with hydrogen sulfide group" in the above method 7 is, for example, a mercapto halide, an alkyl halide, an isocyanate, a carbon-carbon double A key or the like is suitable. The "functional group reactive with a hydrogenthio group" is a carbon-carbon double bond, and the addition reaction is particularly preferably carried out by a radical addition reaction. The carbon-carbon double bond is preferably a 1-substituted or 2-substituted vinyl group from the viewpoint of reactivity with a hydrogenthio group.

The above-mentioned "compound having 3 to 10 thiol groups in one molecule" is exemplified by the following compounds. -77- 200804533 (u-i ) H il ^ 1 } HS-CH2-CH2-C- o- CH2v, c^CH2- o-c- ch2- ch2- sh H3C-CHf, CH2-. - row-CH2-CH2-SH ooo Cu- 2 ) 11 ii ^ L> hs-ch2-co-ch2, <ch2-oc-CH2-SH Η3〇-€Η^^ΟΗ2-〇-〇-〇Η2 -εΗ 0 (u- 3 )

II

If HS - CH2 -CH2—NH_C_0 - CH2, c/CH2-〇"C-NH,CH2-CH2-SH H3c-CH^ V"CH2-〇-C-NH-CH2-CH2-SH ooo {y-4 ) II HS-CH2-CH2-0_O0-CH2, c, CH2 - oc, o-ch2-ch2-sh H3OCHf", CH2-〇C-〇-CH2, CH2-SH o

(u- 5> SH Λ HS N SH (u-B ) ch2-ch2-sh N N HS-CH2-CH2, Ύ CH2-CH2-SH o (u^7 ) i?

Ch2- ch2- n- c-o- ch2- ch2- SH〇 °yV h 〇 HS-CH2-CH2-〇 - C-N - CH2-CH;fM%|fN,CH2-CH2-N-〇O^CH2—CHfSH

H

O

H (u-8 ) hs, CH2, CH2 (u- 9 ) HS4?h2 〇, Cf〇 HS, CH2"ch2> 0,

〇WCH2, Sh hsXH2

Ch,, sh 78- 200804533 (u-|〇) (ιΗ1) 0 〇ii ii hs-ch2 A CH2-C-0 A CH2, c^CH2 An oc-ch2-CH2-SH HS-CH2-CH2-Khan -. -CH^, CH2-O Khan-CH2-CH2-SH o o o o n HS- C H2 — c-O CH2, c〆 CH2 - o- c- CH2- SH US-. H2-C-〇-CHf, CH2-0C-CH2-SH oo (u -12) f? f? hs-ch2-ch2- nh-CO-CH2V. - ch2-oc-nh-ch2-ch2-sh hs - ch2- ch2- nh- co- ch^ ch2 - 0, p-NH,ch2 - ch2 - sh oo

(iH3) (u-U)

Hs_ch2-ch2-o - ϋ, hs-ch2_ch2-o - p 0

II

C-〇-CH2-CH2 — SH

C-0-CH2-CH2-SH o (u-15)

II II

HS-CH2-CH2-〇_CY〇, ^C-〇-CH2-CH2 — SH HS-CH2-CH2, /CH2-CH2-SH

C-O-CH Factory CH2-SH N^N

S hs-ch2-ch2, person A , ch2-ch2-SH hs-ch2_ch2〆 n^ch2-ch2-sh (『1B) o 0

II II

HS-CHfCHfC-O-Cl·^, /CH2-〇-C-CH2-CH2-SH

Hs-ch2-ch2 - o-f o —CH2 — ch2 — o — c 41 ^ II o

Ff / CH^, CH2- o- c- CH2- GH2- SH hs-ch2-ch2-c-o-ch2^ ^ch2-o

HS- CH2— CH2- JJ- OCHf" ~ CH2-〇- CJ- CH2- CH2_SH oo (u-17) i? i? fi HS_CH2- C-〇-CH2, c/CH2-〇-〇sh HS-CH2 —C-〇-CH2, c/CH2, CHf "CH2-〇-C*"CH2-SHo HS-CH2-CKHr 2 II 2o CH2 — OC — CH2 — SH II 2 o Among the above, from raw materials From the viewpoints of availability, ease of synthesis, and solubility of various solvents, (U-1), (U-2), (u-10), (u-11), -79-200804533 (u- 16), (u-17) is better. The compound having a functional group (A1 or A2 in the above formula) and having a carbon-carbon double bond is not particularly limited, and examples thereof are as follows. (kt) (k-2) (k -3) r^co2H co2h (k-4) co2h V ho2c^Nv^ ho2c^Y^ ho2c^ co2h co2h (k - 5) (k-6) (k-7 )

(k-8) (k-9) (k-10)

-80- 200804533 (k-17〉 (k-1S) (k-19)

o - 24) (k-25) (k-26) GO" (k-27) (k-28) (k-29) 々Si〆·3 H3CO", 〇CHs | OCHs 丨-〇CHs 〇0CH3 XT&quot ;". ~ o (k-30) (k-31) (k- 32) 0 OCN 八, 〇(k-33) (ic- 34) (k-35) 人八OH OH I OH 义^〇一Λ^οη Ο -81 - 200804533

(k-38) (k-39)

-82- 200804533 (k-47) (k-48) (k-49) (k-50) (k-51)

(k-55) (k -56)

(k - 59) (k-60)

-83- 200804533

For example, the above "a compound having 3 to 10 thiol groups in one molecule" and the above "having a group selected from an acidic group, having a basic nitrogen atom, a ureido group, a urethane group, and having a compound a radical of a terminal oxygen atom, a hydrocarbon group having 4 or more carbon atoms, an alkoxyalkyl group, an epoxy group, an isocyanate group, and at least one functional group of a hydroxyl group, and a compound having a carbon-carbon double bond For example, the above-mentioned "compound having 3 to 10 hydrogenthio groups in one molecule" and "having a group selected from an acidic group, having a basic nitrogen atom, a urea group, and an amine can be used. At least one functional group of a formate group, a group having a coordinating oxygen atom, a hydrocarbon group having 4 or more carbon atoms, an alkoxyalkyl group, an epoxy group, an isocyanate group, and a hydroxyl group, and having a carbon-carbon double bond The compound is dissolved in a suitable solvent, and a radical generator is added thereto to obtain a method of adding -84-200804533 at about 50 ° C to 100 ° C (thiol reaction method).

Examples of the preferred solvent used in the above method are, for example, "a compound having 3 to 10 thiol groups in one molecule" and "having an acidic group and having a basic nitrogen" At least one functional group of an atomic group, a urea group, a carbamate group, a group having a coordinating oxygen atom, a hydrocarbon group having 4 or more carbon atoms, an alkoxyalkyl group, an epoxy group, an isocyanate group, and a hydroxyl group; Further, the solubility of a compound capable of reacting with a hydrogenthio group (for example, a carbon-carbon double bond) and the solubility of the generated radical addition reaction product are arbitrarily selected. For example: methanol, ethanol, propanol, isopropanol, 彳-methoxy-2-propanol, 1-methoxy-2-propyl acetate, acetone, methyl ethyl ketone, methyl isobutyl Ketone, methoxypropyl acetate, ethyl lactate, ethyl acetate, acetonitrile, tetrahydrofuran, dimethylformamide, chloroform, toluene. These solvents can be used in combination of two or more kinds. Further, the 'radical generating agent system can use, for example, 2,2'-azobis(isobutyronitrile) (AIBN), 2,2,-azobis-(2,4,-dimethylvaleronitrile) Nitric acid bovine not such as peroxides of benzamidine peroxide, and persulfates such as potassium persulfate, persulfate, and the like. In the organic nanoparticle dispersion composition of the present invention, a specific example of the compound of the formula (the compound represented by υ) is shown below. However, the present invention is not limited by any of the specific examples. - 200804533 (C-1) ho2c· ho2c (n=5, m=1) co2ch3 —CH2 — CH2-C-〇, CH2, /CH2-0-C-CH2-CH2_ I? /CHr^, CH2- oc - CH2-GH2- -CH2~ CH2— C- 〇- CHg-K ^ CHg— 〇q ̄t-CH2-C, 〇-CHf*, CH2-0卞CH2-CH2—

O o -ch2~ ch2~c* 〇- ch2 /CHj l? (0-3) ch2-oc-ch2-ch2- ΌΗ2-〇- ch2_ CH2- ch2-『〇-CH 广,CH2-〇_『CH2 -ch2 _ a CH2—CH2 — 〇〇- CH2, 〆ch2_ o" -CB -----"/, o 0 (n=5, ra=1) o2ch2ch2oh C〇2CH2CH2CH2CH3 (C-4) ho2c H02C , Xs, -R3- _ n . 〇〇2ch3< m R3= 5? (n=5tnFl) —ch2—οη2— c- 〇- ch2 {? /CHi -ch2- ch2-c- o-ch2,〆ch2 -o -CH2-CH2-CO-CH^ ^CHz oo c-ch2-ch2- /CH2-〇-C-CH2-C , ch2-o-anti-ch2-ch2-o r3= (G-5) ho2c Ho2c^As. "*R^- n 1 co2ch2ch2oh (n=5, m=t) co2ch2ch2ch2ch3 _CH2-CH2—CO-CH: —ch2~ch2-co-ch^oow ch2-ch2 — co-ch2, / 〇ηΓ ch2-o < ^ ch2- o- c- ch2- ch2-, ch2-o-trans-ch2-ch2-CH2-〇-C-CH2-CH2-o o (C-6) ho2c ho2c

R3— '〇2CH3_

Ch2 — ch2—c_o_ch2, (n;5, ) -CH2-CH2~C-〇-CH2v ,CHf CH2-CH2- ～ch2 - oc-ch2 - ch2_ ACHf0... ΰ CH2-CH2-C- 0-CH2 ch2- O- c- cn2-ch2— f? oo 86- 200804533 (0-7) _ {? 0 H〇-Po^〇Ar^s. -R3- -s^r OH 1 n co2ch3 (n=5, m =1) (C-8) ho3sJ^nA^s· A R3- H n co2ch3_ (n=5, m=1) O 0 li il a CH2-CH2-C-〇-CH2, c/CH2_〇- CC:H2_CH2- Π /CHf, ch2—o-c_ch2—ch2- .CH2-CH2-〇O-CH2, c/CH2-〇^ CH2-CH2-gO-CHr \〇H2-〇-^*CH2-CH2 — oo a ch2 — CH2-C-〇CH2v^CH2-〇-C-CH2 — ch2-i? ^CHr'^CHz-OC-CHz-CHo- • ch2- ch2 - o o- ch2,< ch2- o 11 ,^C^CH2~〇- C-CH2-CH2-o o -CH2-CH2-C-0-CH2 o (C-9)

GH2-CH2 - CHH2, c/CH2-Cy CH2 — CH2-C-〇-CHr o

II -ch2-ch2—00- .OH; ch2-o-c-ch2~ch2-o o II .ch2-o-c-ch2-ch2-, ch2-o- c- ch2—ch2-o

Co2ch3· (n=5t m=t) R— " A CH2-CH2 — C-〇-CH2, /CH2-〇-C-CI^-CH2- f? ^CHj^ ^CH2~〇~ C- CH ?—CHo- (CHO) II o -CH2-CH2-C_〇-CH2, /CH2-〇" -ch2 — ch2-co”~ch2-〇-c-ch2—ch2- an r3 a-o

Cn—5, m—1) co2ch2ch2oh co2ch2ch2ch2ch3 -87- i?200804533 -ch2 - ch2 - c- ό-CH2, c〆ch2-o- c- ch2- ch2- ο Ί r • CH^—CH2 - c- 〇-〇η2, ^〇Η2—〇_-CH2-CH2-C-〇-CHr" o ch2 - oc-ch2-ch2-o CH2 — oc- CH2- CH Factory CH; o co2ch3 (n=5f m= l) (C-12) W^s_ — f? Π a ch2—ch2-co-ch2, 〆ch2-oc-ch2-ch2-f? /CHr ~CH2-〇-C-CH2-CH2--ch2— Ch2 — co-ch2,,ch2 — og -ch2-ch2~ c- ο-οηΓ" ^〇h2- oc-ch2~ ch2— oo r3_.sW^ co2ch2ch2oh C02CH2CH2CH2CH3 (n=5, mp1) (C-13)

Co2ch3 (n-5, nv-1) (C-14) (n=5, m=1) m II ' ch2- ch2- c- o- ch2, οηΓ c: ^ CH2-〇-C- CH2- CH2 ch2-ch2-co-ch2, 〆ch2-o〆ch2—ch2-good-o-ch broad, ch2 - oj^ch2-ch2_ oo CH2-〇-C-CH2~CH2-

II • gh2-o-E-ch2-ch2--CHfCHfC-O-CHs,. {? /CHf,CH2-〇-C-CH2—CH2_ -CH2 - CH2—C-0-CH2,^*CH2_0 ^ -CH2- CH2 - CO-CHf kcHz-O 卞CH2-CH2— ;ch2ch2oh co2ch2ch2ch2ch3 o - 88- 200804533 (C-15) Yang 2.八八八S ho2c (n=3, m=1) C〇2 o2ch3j II II •CH2 —CH2-C-〇-CH2, /CH2-〇-C-CH2-CH2--ch2-ch2-co-ch ^ ^ch2-oc-ch2-ch2- no iro (C-16) r3= i? f? a ch2 — ch2 — c- o- ch2, 〆ch2 — o- c- ch2-ch2- Π /CHf" CH2-〇-C-CH2-CH2 -ch2-gh2- co-ch2,<ch2-o » -QH2—CH2- C- O- CHr"^CH2-〇-C-CH2-CH2—O 0 HOsC^ ^Y^S- —R3— \ COOH . h〇2〇n • CO2CH3 . (n=5,m=1) (x:y=9:l) (C-18)

R—II CH2—CH2—c- o-CH2, OV If ^CH2 CH2-CHfC'0_CH2, ^CH2—0 co2ch3 <ch2- oH-ch2-ch2-, ch2, o-trans-ch2 - ch2- Oo -89- 200804533 (CH9)

-R3- (0-20)

(C-21)

• R3 – R – " a CH2. CH2 - ό- 〇- CHasί? -ch2-ch2-co-ch2^c^ch2-o -ch2—ch2 — good weaving o~ cuf" , ch2-o- p-ch2— ch2· oo ch2-oc-ch2 — ch2_ ch2*-oc-ch2-ch2-o C〇2CH2CH2QH cp2ch2ch2ch2ch3

CH2-CH2-C-〇-CH2 CH2 — CH2 — C-O-CHj o C〇2CH3· m

R3= ch2- ch2 — c- o-ch2,〆ch2- o* {? o II —ch2- ch2-c- och2, i? ^ ch2-o- c-ch2- gh2 ^CH^C^CH2-〇 -C-CH2-CH2-:c^CH2-〇11 ' ~ch2-og-ch2-ch2_o o —ch2- ch2- co- CH2,c〆ch2-oc- ch2- ch2-Q /CHf \CH2-〇 -C-CH2-CH2- __ o CH2 — CH2 — co-CHf o ch2-oc-ch2-ch2-o co2ch2ch2oh co2ch2ch2ch2ch3 (C-22)

R3= co2ch3> (n=5, m=1) ?lf? —ch2~ ch2~c- ο- ch2- o- c- ch2- ch2· η ^οηΓ"°^〇Η2-ο-ο-οΗ2- Ηη2- CH2 - CH2 - CO-Ch'eCHfO » ch2- ch2- c- o- oh^ ^ ch2- o- c- ch2- ch2— oo -90- 200804533 (C-23)

Η π°=<ΝΪ> I

(η=5, m=1) (C-24) —CH2 — CH2 — oo-ch2 , .Π /CH〆• CH2- CH2- C- Ο- CH2, 〆CH2- Ο -CH2-CH2~C- 〇-CH^ *^〇Η2-〇-(:-〇Η2*-〇Η2 oo CH2-〇-C-CH2~CH2-CH2-〇~〇-CH2-CH2-0 Η Η, s--r3 +s -η co2ch3_ (η=5, m=1) (C-25)

(C-26)

(n=5, m=1) C〇2CH2CH2OH co2ch2ch2ch2ch3, CH2-CH2-C, 〇-CH2, c/CH2-〇』-CH2-CH2- n /CH wide%ch2—o_c-ch2-ch2_ _CH2 - CH2 -C-〇-CH2, c/CH2-〇» -ch2-ch2-jin-O-CHf, ch2-o·pan-ch2-ch2— oo R — II (i 〇一ch2-CH2-CO-CH2 C〆ch2— o- c-ch2—ch2- 1? /CHf, CH2- a-C_CH2,CH2-,ch2-ch2-〇〇-CH2, c/CH2-〇^-CH2-CH2-O-CHf c ,ch2 - o-g_ ch2 - ch2— oom -91- 200804533 (C-27) P ' -R3- L^) jn . co2ch3·

-ch2-ch ch2, c: .ch2-oc-ch2-ch2-ch2-oc-ch2-ch2-CH2-CH2-C-〇-CH2v.c::.CH2-〇" ^ CH2*~〇_ C_CH2—ch2—o(G-28) i? o M—ch2—ch2—c-och2 o II .ch2-oc-ch2-ch2- /CH2 —ch2- ch2- c- o-ch2,〆ch2_ 0 - 0Η2-0Η2-0-0-0Η^ ^ch2~o~c-ch2-ch2-o o ch2- o- o- ch2- ch2-o

(n=5, of1) (C-29) •-R3

Co2ch2ch2〇h C02CH2CH2CH2CH3 «3 〇O R3= II " A CH2-CH2- C- 0- CH2, 〇〆ch2 - ch2— ch2· η /CHf", CH2-0-C-CH2-CH2- -CH2— CH2 - C*"0-CH2, ^CH2-o 11 -CH2-CH2-j^〇-CHf", GH2-〇-Boundary_CH2-. H2- o

Co2ch3- (n=5, m=l) o o f? (030)

Ch2-ch2-I^-o-ch2, CH2-CH2-C-〇-CH2 o (n=5T m=1) ch2- ch2- c- O CH2, c〆ch2- 〇- c- ch2—ch2 cuf ,ch2-oc-ch2-ch2-o

〇C ΟΗζ-ύ 〆 ch2-o-c-ch2—ch2-o co2ch2ch2oh co2ch2ch2ch2ch3 -92- 200804533 CC-31)

ο οπ 11 CH2-CH2-C:-〇-CH2, c/CH2-〇-C-CH2—CH2-〆, CH2-〇-C-CH2-CH2-o o ^ II /CHf ch2-ch2-oo- Ch2, ch2-o CH2—CH2-O0-CHf, ch2-o- c- ch2-ch2—oo (n=5, m=1) (0-32)

CH2-CH2 — c- o- CH2, /C h2- 0* CH2~CH2-C-〇-CHr o {? o II -ch2-*ch2-c-o-ch2 /CHr

(n-5, m-·1) ch2-o-q-ch2-ch2-o o ri -ch2 — o- c-ch2 — ch2_ , ch2 — o-c-ch2 — ch2- b co2ch2ch2oh C02CH2CH2CH2CH3 m (C-33)

II i?

R3--S· (n=4.5, m=1.5)—ch2-ch2-c-〇_ch2, 〆ch2-oc-ch2—ch2-j?/ΟηΓ", ch2-oc-ch2-ch2, CH2-CH2-C-〇CH2, c/CHz_0' ^-CH2 — GH2- co- CHJ-" \ ch2- o- c- ch2- ch2-oo co2ch3 (C-34) •ch2-ch2—

(n=4. 5, ΠΡ1.5) ch2—ch2-c-o-ch2 CH2~CH2-C-〇-CH2o c-o-ch2, CHf" CH2 — o

Ch2-o-c-ch2-oh2- o o II zCH2-〇-C-CH2 — ch2-, ch2-o-c-ch2-ch2-o co2ch2ch2ch2ch3 co2ch2ch2〇h m 93- II200804533 (C-35)

s^T C05

o2CH3J r3= o

Jl -CH2~ 〇~ C*" CH2~CH2~ "ch2-〇-c-ch2-ch2--ch2 — ch2—c-o- ch2, •CH2 — CH2 - C-O-CH

^CHZ*~ 〇_C~CH2~CH2~, ch2-oc-ch2-ch2- Further, the polymer compound is preferably a polymer compound having an acidic group and a polymer compound having a carboxyl group. (A) a copolymerized compound Φ derived from at least one repeating unit derived from a compound having a carboxyl group and (B) at least one repeating unit derived from a compound having a carboxylate group is particularly preferred. The repeating unit derived from the compound having a carboxyl group (A) is preferably a repeating unit represented by the following formula (丨), and a repeating unit derived from acrylic acid or methacrylic acid is preferred, and the above (B) is preferred. The repeating unit derived from the compound having a carboxylate group is preferably a repeating unit represented by the following formula (Π), and a repeating unit represented by the following formula (IV) is preferred, from benzyl acrylate, Benzyl methacrylate, phenylethyl acrylate, phenylethyl methacrylate, 3-phenylpropyl propionate, or 3-phenylpropyl methacrylate -94- 200804533

5 of the alkyl group (Ri means hydrogen atom or number of carbon atoms 1 ~

5 alkyl groups. R3 represents (R2 represents a hydrogen atom or a carbon atom number 1 to a group represented by the following formula (Ml))

Formula (III) (R4 represents a hydrogen atom, a hydroxyalkyl group having 1 to 1 atomic number of carbon atoms, or a 5 - 1 number of carbon atoms having 5 to 1 carbon atoms or a sub-hydrogen atom The table is divided into groups. The hydroxyl group, the aryl group: the base of the i alk.

R carbon and 5 /\ 逋•2 Η: c RICIc=lolR8 (R7 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. R8 represents a group represented by the following formula (V)) -95 - 200804533

(R9 represents an alkyl group having 2 to 5 carbon atoms or an aryl group having 6 to 20 carbon atoms. Ru and Rm represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. j represents a number of 1 to 5) The so-called (A) repeating unit derived from a compound having a carboxyl group, and the polymerization ratio of the repeating unit φ derived from the above (B) from a compound having a carboxylate group, with respect to the repeating unit (A) The total number of repeating units is preferably 3 to 40, and preferably 5 to 35. In the present invention, the molecular weight of the polymer is not particularly limited, and means the mass average molecular weight. The method for measuring the molecular weight of the polymer is, for example, a chromatography method, a viscosity method, a light scattering method, a sedimentation rate method, or the like. In the present invention, the mass average molecular weight measured by a chromatography method which is not particularly limited in definition is used. The polymer compound may be either water-soluble or oil-soluble, or may be water-soluble and oil-soluble. The method of adding the polymer compound may be a solution dissolved in an aqueous solvent or an organic solvent, or a solid state, or a combination thereof. The method of adding a polymer compound to a solution dissolved in a solvent is, for example, a method of adding in a state in which a solvent which is dissolved in an organic particle liquid is the same solvent as a solvent in which the organic particle liquid is agglomerated; The method in which the solvent of the particle liquid is dissolved and dissolved in a different solvent is added. In the case of adding in a solution dissolved in a solvent, the concentration of the polymer compound is not particularly limited, and it is preferably from 1 to 70% by mass, preferably from -96 to 200804533 2 to 65% by mass, preferably from 3 to 60% by mass. % is especially good. The addition of the polymer compound may be carried out (or before or after) when the organic nanoparticles are formed by the re-precipitation method, or before (or before and after) extraction or concentration, and when the aggregated organic particles are dispersed (after or after), Add any time after the end of the steps, or a combination of these. In the present invention, the quality is flat

The polymer compound having a molecular weight of 1 Å or more can be contained in the composition as a binder to be described later. For example, it is preferable to add the organic particles after the organic particles are re-sanded, and then to concentrate and concentrate the fine particles. When the amount of the polymer compound to be added is 1 part by mass, the amount of the organic particles to be aggregated is preferably 0. 1 to 1 0 0 parts by mass, preferably 5 to 500 parts by mass. 10 to 300 parts by mass is particularly good. The polymer compound having a molecular weight of 1,000 or more is, for example, polyvinylpyrrolidone, polyvinyl alcohol, polyvinyl methyl ether, polyethylene oxide, polyethylene glycol, polypropylene glycol, polypropylene decylamine, vinyl alcohol. - vinyl acetate copolymer, polyvinyl alcohol - partial methyl formate, polyvinyl alcohol - partial butyral acetal, vinyl pyrrolidone - vinyl acetate copolymer, polyethylene oxide / propylene oxide block Copolymers, polyamines, cellulose derivatives, starch derivatives, and the like. Further, natural macromolecular compounds such as alginate, gelatin, albumin, casein, gum arabic, toluene gum, and lignosulfonate can also be used. The polymer compound having an acidic group is, for example, polyvinylsulfuric acid or condensed naphthalenesulfonic acid. The polymer compound having a carboxyl group is, for example, polyacrylic acid, polymethacrylic acid, or a cellulose derivative having a carboxyl group in a side chain. The copolymerizable compound comprising (A) at least one repeating unit derived from a compound having a carboxyl group of -97 to 200804533 and (B) at least one repeating unit derived from a compound having a carboxylate group, for example, Japanese Patent Publication No. 59-4461, Japanese Patent Publication No. Sho 54-34327, Japanese Patent Publication No. Sho 58-1 2577, Japanese Patent Publication No. Sho 54-25957, JP-A-59-53836, and JP-A-59-71 048 A methacrylic acid copolymer, an acrylic copolymer, an itaconic acid copolymer, a butenoic acid copolymer, a maleic acid copolymer, a partially esterified butylene, as described in the publication.

Diacid copolymers and the like. Further, a particularly preferred example is an acrylic acid-acrylic acid ester copolymer, a methacrylic acid-acrylic acid ester copolymer, an acrylic acid-methacrylic acid ester copolymer, or a methacrylic acid described in the specification of U.S. Patent No. 4,139,391. A methacrylate copolymer, or a multi-component copolymer of acrylic acid or methacrylic acid, with an acrylate or methyl propionate, and with other vinyl compounds. Examples of the vinyl compound are, for example, styrene or substituted styrene (e.g., vinyl toluene, vinyl ethyl benzene), vinyl naphthalene or substituted φ vinyl naphthalene, acrylamide, methacrylamide Acrylonitrile, methacrylonitrile, etc., preferably styrene. These polymer compounds may be used singly or in combination of two or more kinds, and may be used in combination with a compound having a molecular weight of less than 1,000. In the present invention, the organic nanoparticle dispersion contains 60% by mass or more of an organic solvent, preferably 65 mass%. /. The above is preferred. The organic solvent is not particularly limited and can be suitably selected from the general public. For example, an ester compound solvent, an alcohol compound solvent, an aromatic solvent, an aliphatic solvent, a ketone compound solvent, an ester compound solvent, or a ketone compound solvent is -98-

200804533 Excellent. These may be used alone or in combination of two or more kinds of ester compounds, such as 2-(1-methoxy)propyl ethyl acetate or ethyl lactate. The alcohol compound solvent is, for example, n-butanol or the like. Examples of the aromatic compound solvent include benzene, toluene, and a dimethyl aliphatic solvent. For example, η-hexane or cyclohexane is used. The ketone solvent is, for example, methyl ethyl ketone, acetone or cyclohexanone. Next, the organic nanoparticle dispersion composition of the present invention, such as a color filter, an inkjet ink, or the like, will be described in detail. The ink jet ink is a general ink jet ink which can be used as an ink jet ink for printing a color ink as an ink jet ink for printing. The organic sub-system can be used, for example, in a state of being dispersed in a vehicle. The above-mentioned coating material is preferably a medium portion in which the pigment is dispersed in a liquid state, and includes a portion (adhesive agent) which bonds the reinforcing coating film with the above pigment to dissolve the diluted component (organic solvent). Further, in the present invention, the binder formed by the particles and the binder used for the redispersion may be different, and each of them may be distinguished as a nanoparticle to form a binder dispersing binder. The organic component concentration of the dispersed composition of the organic nanoparticle after re-dispersion is appropriately determined depending on the purpose, and is preferably 2 to 30, preferably mass%, and 4 to 20 mass, relative to the total amount of the dispersed organic nanoparticles. Good, 5~15 mass% is especially good. In the case where the toner is dispersed as described above, the amount of the binder and the dissolved and diluted component is appropriately determined depending on the type and the like, and it is preferably 1 to 30% by mass based on the total amount of the dispersion composition. 3 to 20% by mass is preferably 5 to 15, acetic acid, isobutyl hydrazine or the like. In addition, the compound is also a liquid crystal developer, which is the same as the nano-particle composition, and the nano-particle composition: % is the same as the extension pigment, and the bonding quality is -99-200804533. good. The dissolved diluent component is preferably from 5 to 80% by mass, preferably from 10 to 70% by mass. In the above-mentioned concentrated extracted nanoparticle liquid, as described above, since the rapid filter can be carried out, the organic nanoparticle is preferably agglomerated by concentration, and is subjected to centrifugation or drying. Concentrate to make it agglutinate.

As a method of finely dispersing these aggregated nanoparticles, for example, a method of dispersing by ultrasonic waves or a method of applying physical energy can be used. The ultrasonic irradiation device to be used is preferably a function capable of applying a supersonic wave of 1 kHz or more, and examples thereof include an ultrasonic homogenizer and an ultrasonic cleaner. When the liquid temperature rises during ultrasonic irradiation, in order to cause thermal agglomeration of the nanoparticles (see pigment dispersion technique - surface treatment and dispersant usage and dispersibility evaluation - Technical Information Association 1 999), the liquid temperature is set to 1 to 100 °. C is better, and 5 to 60 ° C is more preferable. The temperature control method is carried out according to the control of the temperature of the dispersion liquid, the temperature control of the temperature control layer of the temperature control dispersion, and the like. The dispersing machine used to disperse the concentrated organic nanoparticles in addition to the physical energy is not particularly limited, and examples thereof include a kneader, a roll mill, a vertical ball mill, a super honing machine, a dissolver, and the like. Homogenizers such as agitators, sanders, etc. Further, a high-pressure dispersion method or a dispersion method using fine particle beads may also be suitable. <1> Dispersion method A preferred method for producing an organic nanoparticle-dispersed composition, wherein the colorant is kneaded at 25 ° C and has a viscosity of 1 〇, 000 mPa·s or more after kneading and dispersing with a resin component Preferably, it is i〇〇, 〇〇〇mpa.s is higher than the viscosity of -100-200804533 to carry out the kneading and dispersing treatment, and then adding the solvent and the viscosity after the microdispersion treatment is generally 1,000 mPa·s or less. Preferably, a relatively low viscosity of 1.00 mPa·s or less is preferred, and a method of performing microdispersion treatment is preferred.

The mechanical system used in the mixing and dispersing treatment is a two-roll honing machine, a three-roll honing machine, a ball mill, a drum honing machine, a dispersing machine, a kneading machine, a kneading extruder, a homogenizer, a blending machine, The uniaxial and biaxial extruders are dispersed while imparting a strong shearing force. Secondly, a solvent is added, and a sand mill, a pin mill, a slit honing machine, an ultrasonic disperser, a high-pressure disperser, etc., which are mainly vertical or horizontal, are used, and the particle size is 〇 1 1 to 1 mm. The beads produced by glass, zirconia, etc. are subjected to precise dispersion treatment. Further, fine particle beads of 0 1 m or less can be used for precise dispersion treatment. Further, the kneading dispersion treatment may be omitted. In this case, the pigment, the dispersing agent or the surface treating agent is dispersed in the acrylic copolymer and the solvent of the present invention. Further, after dispersing the main pigment and the complementary pigment separately, the dispersion of the two pigments is mixed and further subjected to dispersion treatment, and the main pigment and the supplementary pigment may be dispersed and treated together. In addition, detailed descriptions of mixing and dispersing are also described in TC Patton's "Paint Flow and Pigment D ispersi ο η" (John W Π eyand S ο ns, 1946). This method can also be used. <2> Examples of Dispersing Agents in Organic Nanoparticle Dispersion Compositions' Purpose In order to improve the dispersibility of organic nanoparticles, a general pigment dispersant or interface can be added-101-200804533

Active agent. These dispersants use a wide variety of compounds, such as: phthalocyanine derivatives (commercial product EFKA-6745 (manufactured by EFCA)), Sorospas 5000 (manufactured by ZENECA Co., Ltd.); organic oxiranes Polymer KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), (meth)acrylic (co)polymer Polyflow Νο.75, Νο_90, Νο·95 (manufactured by Kyoeisha Oil Chemical Industry Co., Ltd.), WOO a cationic surfactant such as 1 (manufactured by Yusho Co., Ltd.); polyoxyethylene lauryl ether, polyoxyethylene stearyl decyl ether, polyoxyethylene oleyl ether, polyoxyethylene octyl phenyl ether, polyoxygen Nonionic surfactants such as vinyl nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid ester; VV0 04, W005, W017 ( Anionic surfactants manufactured by Yushang Co., Ltd.; EFKA-46, EFKA-47, EFKA-47EA, EFKA polymer 100, EF KA polymer 400, EFKA polymer 401, EF KA polymer

450 (manufactured by Morishita Industrial Co., Ltd.), DISPERSAID 6, DISPERSAID 8 , DISPERSAID 15 , DISPERSAID φ 9 1 0 0 (made by Sanyo Chemical Co., Ltd.), etc.; Soros Pass 3000, 5000, 9000, Various Sorospas dispersants (manufactured by ZENECA Co., Ltd.) of 12000, 13240, 13940, 17000, 24 000, 26000, 28000, etc.; ADEKAPLR〇NIC L31, F38, L42, L44, L61, L64, F68, L72 , P95, F77, P84, F87, P94, L101, P103, F10 8, L121, P-123 (made by Asahi Kasei Co., Ltd.) and ISONET S-20 (made by Sanyo Chemical Co., Ltd.). Further, the pigment dispersing agent described in JP-A-2000-239554, or the compound (C) described in JP-A-H05-72943, or the combination described in JP-A No. 2-01-83 8 102 - 200804533 The compound of Example 1 and the like are also suitable for use. The compound represented by the dispersing agent [dispersion phase] used in the formation of the organic nanoparticles during redispersion may be used again. In the organic nanoparticle dispersion composition, the redispersed organic nanoparticles (primary particles) can be formed into finely dispersed particles, and the particle diameter can be preferably 1 to 2 0 0 nm, 2 to 1 0 0 Nm is preferred, and 5 to 50 nm is particularly preferred. Moreover, the Μ v/Μη of the particles after redispersion is preferably 1.0 to 2.0, and 1·0 to 1_8 is preferred.

Good, 1. 0 ~ 1 · 5 is especially good. According to the present invention, for example, the pigment particles contained in the organic nanoparticle-dispersed composition or the colored photosensitive resin composition described later are so-called nanometer sizes (for example, 1 〇 to 1 〇〇 nm). However, it can still be concentrated and redispersed. For this reason, when used in a color filter, the optical density is high, the uniformity of the surface of the filter is excellent, the contrast is high, and the noise of the image can be reduced. In addition, since the organic nanoparticle contained in the organic nanoparticle-dispersed composition and the colored photosensitive composition can be finely dispersed uniformly and uniformly, a high coloring density can be exhibited in a thin film thickness, for example, A thin layer of a color filter or the like is formed. Further, the organic nanoparticle-dispersed composition and the colored photosensitive resin composition contain a pigment which exhibits a vivid color tone and a high coloring power, and is used as an image forming material for producing a color proof or a color filter, for example. It is excellent. Further, in the case of the alkaline developing solution used for exposure and development at the time of formation of the coloring image, the organic nanoparticle-dispersed composition and the colored photosensitive resin composition are used in combination with an alkali-soluble aqueous solution. Agent (bonding -103- 200804533), and can also respond to environmental requirements. Further, an organic solvent having a moderate drying property can be used as a solvent (dispersion medium for pigment) for the organic nanoparticle dispersion composition and the colored photosensitive resin composition, even from the point of drying after coating. Can meet their requirements. 'Coloring photosensitive resin composition> The colored photosensitive resin composition of the present invention contains at least ^ (a) organic

Nanoparticles, (b) binders, (c) monomers or low polymers, and (d) photopolymerization heuristics or photopolymerization heuristics. Hereinafter, each component of the colored photosensitive resin composition of the present invention will be described. (a) Organic Nanoparticles The method for producing organic nanoparticles has been described in detail. The content of the organic nanoparticles is based on the total solid content of the colored photosensitive resin composition (in the present invention, the total solid content is a total of the composition containing no organic solvent), preferably 3 to 90% by mass, 2 0 to 80% by mass is preferable, and 2 5 to 60% by mass is more preferable. When the amount is too large, the viscosity of the dispersion rises and there is a problem in that the manufacturing suitability is formed. When too little, the coloring power is insufficient. The organic nanoparticle (pigment fine particles) functioning as a colorant has a particle diameter of 0.1 # m or less, and particularly preferably a particle diameter of 〇 _ 08 / z m or less. Further, it can also be used in combination with a pigment used for coloring. For the pigment system, those described above can be used. (b) Adhesive The binder in the colored photosensitive resin composition is preferably a polymer compound having a mass average molecular weight of 1,000 or more as described above. The content of the binder is from 15 to 50 masses in general -104 to 200804533 with respect to the total solid content of the colored photosensitive resin composition. /. It is preferably 20 to 45 mass%. When the amount is too large, the viscosity of the composition is too high and there is a problem in manufacturing suitability. When there is too little, there is a problem in the formation of a coating film. (c) monomer or low polymer

The monomer or oligomer contained in the colored photosensitive resin composition of the present invention has two or more ethylenically unsaturated double bonds, and is preferably a monomer or a low polymer which can be subjected to addition polymerization by light irradiation. Such a monomer and an oligomer may, for example, be a compound having at least one addition-polymerizable ethylenically unsaturated group in the molecule and having a boiling point of 100 ° C or more at normal pressure. This example is, for example, dipentaerythritol hexa(meth) acrylate, polyethylene glycol mono (meth) propyl phthalate, polypropylene glycol mono (meth) acrylate, and phenoxy (meth) acrylate. Monofunctional acrylate or monofunctional methacrylate; polyethylene glycol di(meth) acrylate, polypropylene glycol di(meth) acrylate, trimethylol Z hospital triacetin ester, three armor Benzene tris(methyl)propane acrylate, tri-propyl propyl propane diacrylate, neopentyl glycol di(meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol tri (meth) acrylate Ester, dipentaerythritol hexa(meth) acrylate, dipentaerythritol penta (meth) acrylate, hexanol mono(methyl) propyl acrylate, tris-methyl propyl tris(propyl decyloxypropyl) Ether, tris(propylene methoxyethyl) tertylene isocyanate, tris(propylene decyloxyethyl) cyanurate, tris(meth)acrylate; in trimethylolpropane or glycerol Multi-official § alcohol addition to Epoxy Institute or Ethylene Acrylic Institute, after A polyfunctional acrylate or polyfunctional methacrylate such as a (meth) acrylated one. Further, as described in the general formulae (1) and (2) of JP-A-10-62986, after the polyfunctional alcohol is added to ethylene oxide or propylene oxide, -105-200804533 The acrylated compound is suitable. In addition, the urethane acrylates described in JP-A-48-41, 708, JP-A-2005-7093, and JP-A-51-37193 Polyester acrylates described in JP-A-43-431, JP-A-49-431, and JP-A-52-30490; epoxy acrylates such as epoxy resin and (meth)acrylic acid Multifunctional acrylate, methacrylate.

Among these, trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and dipentaerythritol penta(meth)acrylate are preferred. In addition, the "polymerizable compound B" described in Japanese Laid-Open Patent Publication No. Hei No. Hei. These monomers or low polymers (the monomer or the low polymer is preferably a molecular weight of 200 to 1,000) may be used singly or in combination of two or more kinds, and the total solid content of the colored photosensitive resin composition may be used. The content is generally 5 to 50% by mass, preferably 10 to 40% by mass. When the amount is too large, the viscosity of the composition is too high to cause a problem in manufacturing suitability. When the amount is too small, the hardening force at the time of exposure is insufficient. (d) a photopolymerization initiator or a photopolymerization initiator is a photopolymerization initiator or a photopolymerization initiator contained in the coloring photosensitive resin composition of the present invention (in the present invention, the photopolymerization heuristic system is called plural) A mixture of compounds and a mixture of photopolymerization initiation functions is found in, for example, a vicinal polyketal aldehyde compound disclosed in the specification of U.S. Patent No. 2,367,660, and a -106 - 200804533 as described in the specification of U.S. Patent No. 2,448,828.

The acetoin compound, the aromatic auxin compound substituted by the a-hydrocarbon described in the specification of U.S. Patent No. 272251, the specification of the U.S. Patent No. 30461 27 and the polynuclear ruthenium compound described in the specification of No. 2951 758, the US patent a combination of a triaryl imidazole dimer and a P-amino ketone described in the specification of No. 3,549,367, a benzothiazole compound and a trihalomethyl-s-three cultivating compound described in Japanese Patent Publication No. Sho 51-4851, The trihalogenated methyl-three-till compound described in the specification of U.S. Patent No. 4,429,850, and the trihalomethyloxadiazole compound described in the specification of U.S. Patent No. 4,221,976. Particularly preferred are trihalomethyl-S-trippers, trihalomethyloxadiazoles and triarylimidazole dimers. Further, the "polymeric heuristic agent C" described in JP-A-33600600 or the 1-phenyl-1,2-propanedione-2-(o-ethoxy group) as an anthraquinone may be mentioned. Carbonyl) hydrazine, hydrazine-benzylidene-4'-(phenylhydrothio)benzimidyl-hexyl-ketooxime, 2,4,6-trimethylphenylcarbonyl-diphenylphosphine oxide, six Fluorophosphoryl-trialkylphenyl scale salts are also suitable. These photopolymerization initiators or photopolymerization heuristics may be used singly or in combination of two or more kinds, and it is preferred to use two or more kinds thereof. When at least two kinds of photopolymerization initiators are used, the display characteristics, particularly the unevenness of display, may be less than the total solid content of the coloring photosensitive resin composition, and the content of the photopolymerization heuristic or photopolymerization heuristic system is generally It is preferably 5 to 2% by mass and 1 to 15% by mass. When the amount is too large, the sensitivity becomes too high and it is difficult to control. When the amount is too small, the exposure sensitivity is too low. (Other additives) -107 - 200804533 [Solvent]

In the colored photosensitive resin composition of the present invention, an organic solvent can be further used in addition to the above components. Examples of the organic solvent are not particularly limited, and examples thereof include esters such as ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, and butyl propionate. , isopropyl butyrate, ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, methyl glycolate, ethyl hydroxyacetate, butyl glycolate, methoxyacetate 3-hydroxyl of ester, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-hydroxypropionate, ethyl 3-hydroxypropionate Alkyl propionates; methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, 2-hydroxyl Methyl propionate, ethyl 2-hydroxypropionate, propyl 2-hydroxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate , 2-ethoxypropionic acid methyl ester, 2-ethoxypropionic acid ethyl ester, 2-oxopurin-2-methylpropionic acid methyl ester, 2-oxy-2-methylpropionic acid ethyl ester, 2 Methyl methoxy-2-methylpropanoate, ethyl 2-ethoxy-2-methylpropionate, methyl pyruvate, pyruvic acid , propyl pyruvate, methyl acetate methyl acetate, ethyl acetate ethyl acetate, methyl 2-hydroxybutyrate, ethyl 2-hydroxybutyrate, etc.; ethers, such as diethylene glycol dimethyl ether, tetrahydrofuran, B Glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, propylene glycol methyl ether acetate, etc. Ketones such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, cyclohexanone, 2-heptanone, 3-heptanone, etc.; aromatic hydrocarbons such as toluene, xylene, and the like. Among these solvents, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, butyl acetate, -108-200804533 3 'Methyl methoxypropionate, 2-heptanone, cyclohexanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol methyl ether acetate, etc.' as a solvent of the present invention It is better. These solvents may be used singly or in combination of two or more. Further, a solvent having a boiling point of from 180 ° C to 250 ° C may be used as needed. Such

The high boiling point solvent is as exemplified below. Diethylene glycol monobutyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether, 3,5,5-trimethyl-2-cyclohexen-1-one, butyl milk Acid ester, dipropylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol diacetate, propylene glycol-n-propyl ether acetate, diethylene glycol diethyl ether, 2-B Hexyl acetate, 3-methoxy-3-methylbutyl acetate, Y-butyrolactone, tripropylene glycol methyl ethyl acetate, dipropylene glycol-n-butyl acetate, propylene glycol benzene Ethyl ether acetate, 1,3-butanediol diacetate. The content of the solvent is preferably from 10 to 95% by mass based on the total amount of the resin composition. [Interacting Agent] In the color filter which can be used in the past, the color of each pixel is increased in order to achieve high color purity, and the unevenness of the thickness of the pixel film is considered to be a problem of color unevenness. For this reason, in the formation (coating) of the photosensitive resin layer which directly affects the film thickness of the pixel, the film thickness variation is required. In the color filter of the present invention or the photosensitive resin transfer material of the present invention, from the viewpoint of controlling the uniform film thickness and effectively preventing coating unevenness (color unevenness due to variation in film thickness), It is preferred that the colored photosensitive resin composition contains a suitable surfactant. The surfactants disclosed in Japanese Laid-Open Patent Publication No. Hei. No. 2003-337424, the entire disclosure of which is incorporated herein by reference. The content of the surfactant is preferably 5% by mass or less based on the total amount of the photoresist. [thermal polymerization inhibitor]

The colored photosensitive resin composition of the present invention preferably contains a thermal polymerization inhibitor. Examples of the thermal polymerization inhibitor are, for example, hydroquinone, hydroquinone monomethyl ether, P. methoxyphenoxy, di-tert-butyl-P-cresol, gallic phenol, and tert-butyl phthalic acid. Diphenol, benzoquinone, 4,4'-thiobis(3-methyl.6-t-butylphenoxy), 2,2'-methylenebis(4-methyl-6-third Butylphenoxy), 2-hydrothiobenzimidazole, phenothiazine, and the like. The content of the thermal polymerization inhibitor is preferably 1% by mass or less based on the total amount of the resin composition. [Dye and pigment for auxiliary use] In the colored photosensitive resin composition of the present invention, a coloring agent (dye, pigment) may be added in addition to the above-mentioned coloring agent (pigment) as necessary. In the case where a pigment is used in the coloring agent, it is desirable to uniformly disperse it in the colored photosensitive resin composition, and the particle diameter is preferably 〇·1 μm or less, particularly preferably 0.08 μm or less. Specifically, as the dye or the pigment, the color material described in JP-A-2005-1 771 6 [0038] to [0040], or JP-A-205-361-447 [0068] 72. The coloring agent described in JP-A-2005-17521 [0 08 0] to [0 088] is used as the pigment. The content of the auxiliary dye or the pigment is preferably 5% by mass or less based on the total amount of the resin composition. -110-200804533 [Ultraviolet absorber] The coloring photosensitive resin composition of the present invention may optionally contain an ultraviolet absorber. In addition to the compound described in JP-A No. 5-72724, for example, a salicylate type, a benzophenone type, a benzotriazole type, a cyanoacrylate type, a nickel chelating agent type, and a hindered amine are mentioned. Department and so on.

Specifically, for example, phenyl salicylate, 4-tert-butylphenylsalicylate, 2,4-di-t-butylphenyl, 3',5,-di·Ν4'_ Hydroxybenzoate, 4-tert-butylphenyl salicylate, 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2·hydroxy- 4· Η-octyloxybenzophenone, 2-(2'-hydroxy-5,methylphenyl)benzotriazole, 2-(2'-hydroxy-3,-tert-butyl-5'. Phenyl)-5-chlorobenzotriazole, ethyl-2-cyano-3,3-diphenylacrylate '2,2'-hydroxy-4-methoxybenzophenone, nickel Dibutyldithiocarbamate, bis(2,2,6,6-tetramethyl-4-pyridine)-sebacate, 4-tert-butylphenylsalicylate, salicylic acid Phenyl ester, 4-hydroxy-2,2,6,6-tetramethylpiperidine condensate, succinic acid-bis(2,2,6,6-tetramethyl-4-piperidinyl)-ester, 2 -[2-hydroxy-3,5-bis(a,a.dimethylbenzyl)phenyl]-2H·benzotriazole, 7-{[4·chloroyl·6·(diethylamino) ··5-Triso-2-yl]amino}-3-phenylcoumarin. The content of the ultraviolet absorber is preferably 5% by mass or less based on the total amount of the resin composition. In addition, the coloring photosensitive resin composition of the present invention may contain, in addition to the above-mentioned additives, an "adhesive auxiliary" described in JP-A No. 1 1 -1 3 3 0 0 0 or other additives. [Coating film of coloring photosensitive resin composition] In the coating film using the coloring photosensitive resin composition of the present invention -111- 200804533

The content of the component is the same as that of the above-mentioned [coloring photosensitive resin composition]. Further, the thickness of the coating film used in the coloring photosensitive resin composition of the present invention can be appropriately determined depending on the use thereof, and preferably 0.5 to 5.0 μη, preferably 1.0 to 3.0 μm. The coating film using the coloring photosensitive resin composition of the present invention is a polymeric film obtained by polymerizing (c) a monomer or a low polymer contained therein to form a colored photosensitive resin composition, and then producing a color filter containing the same. Light sheet (the production of the color filter is as described later). The polymerization of the polymerizable monomer or the polymerizable low polymer can be carried out by light irradiation to cause (d) a photopolymerization initiator or a photopolymerization initiator. (Slit-shaped nozzle) The coating film can be formed by applying and drying the colored photosensitive resin composition by a general coating method, but in the present invention, the portion of the discharge liquid has a slit-like cavity. It is preferable to apply the slit nozzle. Specifically, it is preferable to use the publications of JP-A-2004-89851, JP-A-2004-17 0, JP-A-2003-170098, JP-A-2003-1 64787, and JP-A-2003-1 0767. A slit nozzle and a slit coater described in Japanese Laid-Open Patent Publication No. JP-A-2002-791-63, and JP-A-2002-791. The coating method of applying a colored photosensitive resin composition to a substrate is excellent in spin coating from the viewpoint of uniformly and accurately applying a film of 1 to 3 μm, and is widely used in the production of a color filter. However, in recent years, with the increase in size and mass production of liquid crystal display devices, the manufacturing efficiency and the manufacturing cost have been further improved, and slit coating which is more suitable for coating of a wide-area and large-area substrate than spin coating has been adopted. Production of color filters -112- 200804533. Further, even from the viewpoint of so-called liquid repellency, the slit coating system is superior to spin coating, and a coating film of a uniform sentence can be obtained with a smaller amount of coating liquid.

The slit coating is a slit (gap) having a width of several tens of micrometers at the front end, and the coating head corresponding to the width of the rectangular substrate is generally kept at a clearance of several 〇 to several 1 μm from the substrate. The coating method in which the coating liquid supplied from the slit is applied to the substrate at a predetermined discharge amount while maintaining a relative speed at which the substrate and the coating head are fixed. The slit coating system has (1) less loss than the spin coating liquid, (2) less washing treatment due to the scattering of the coating liquid, and (3) scattering of the liquid component without being mixed into the coating film, (4) Since the start time is not started by the rotation, it is possible to shorten the tact time and (5) to facilitate the application of the large substrate, and the like. According to these advantages, the slit coating is suitable for the production of a color filter for a large-screen liquid crystal display device, and an advantageous coating method is also expected for the reduction of the amount of the coating liquid. In the slit coating system, since a large-area coating film can be applied from a very long distance by spin coating, it is necessary to maintain a certain degree of relative relationship between the coater and the object to be coated when the coating liquid is discharged from the wide slit outlet. speed. For this reason, it is required that the coating liquid used in the slit coating method has good fluidity. Further, in the slit coating, the conditions of the coating liquid supplied from the slit of the coating head to the substrate are particularly required to cover the entire coating width and remain constant. When the liquid properties such as fluidity or viscoelastic properties of the coating liquid are insufficient, coating unevenness is likely to occur, and it is difficult to maintain a coating thickness in the coating width direction, and there is a problem that it is difficult to obtain a uniform coating film. -113 - 200804533 The number of dissolved solutions

No.1 film layer temporary protection thin invention

In the above, in order to obtain a coating film which is not uneven and uniform, it is often attempted to improve the fluidity and viscoelastic properties of the coating liquid. However, in the case of the above, the molecular weight of the polymer is lowered, or a polymer excellent in solvent dissolving property is selected, or various selection media or a surfactant is used to control the evaporation rate, but any of the above is used. The questions have not been fully improved. [Photosensitive Resin Transfer Material] Next, the photosensitive resin transfer material of the present invention will be described. The photosensitive resin transfer material of the present invention is preferably formed by integrally molding a photosensitive resin transfer material described in JP-A-5-72724. The configuration of the integrated film may be, for example, a structure in which a support/thermoplastic resin layer/intermediate layer/photosensitive resin layer/film is laminated, and the color transfer material of the present invention can be colored by using the aforementioned color. A photosensitive resin composition is provided, and a photosensitive resin is provided. (Temporary support) In the photosensitive resin transfer material of the present invention, it is necessary to temporarily support the system, and it is not necessary to cause significant shrinkage or elongation in the case of pressurization, pressurization or heating. Examples of such temporary support are, for example, polyethylene terephthalate film, cellulose triacetate film, vinyl film, polycarbonate film, etc., especially in the case of 2-axis extended poly(ethylene glycol) film. . (The thermoplastic resin layer) The component to be used in the thermoplastic resin layer is preferably an organic polymer material described in JP-A No. 5-72724, which is preferably selected from Vicat Vicat-114 - 200804533.

The method (specifically, according to the method for determining the softening point of the polymer of ASTM D1235) has an organic polymer material having a softening point of about 80 ° C or less. Specifically, for example, a polyolefin such as polyethylene or polypropylene, an ethylene copolymer such as ethylene and vinyl acetate or a saponified product thereof, ethylene and acrylate or a saponified product thereof, polyvinyl chloride, and vinyl chloride are used. Vinyl chloride copolymer such as vinyl acetate and its saponified product, polyvinylidene chloride, vinylidene chloride copolymer, polystyrene, styrene and (meth) acrylate or saponified product thereof Styrene copolymer, polyvinyl toluene, vinyl toluene copolymer of (meth) acrylate or its saponified product, poly(meth) acrylate, butyl (meth) acrylate and acetic acid Poly (meth) acrylate resin such as vinyl ester copolymer, vinyl acetate copolymer nylon, copolymerized nylon, N-alkoxymethylated nylon, N-dimethylaminolated nylon Organic polymers such as. (Intermediate layer) In the photosensitive resin transfer material of the present invention, it is preferable to provide an intermediate layer in order to prevent mixing of components during storage of a plurality of coating layers and storage after coating. In the case of the intermediate layer, it is preferable to use an oxygen blocking film which is described as a "separating layer" and an aerobic blocking function in the Japanese Patent Publication No. 5-77.2, and in this case, the sensitivity at the time of exposure can be improved, and the exposure machine can be reduced. Time load and increased productivity. The oxygen barrier film is preferably one which exhibits low oxygen permeability, dispersion or dissolution in water or an alkaline aqueous solution, and can be appropriately selected from those skilled in the art. Among these, the combination is a combination of polyvinyl alcohol and polyvinylpyrrolidone. (Protective film) -115- 200804533 Above the photosensitive resin layer □ In order to protect against contamination or damage from storage, it is preferable to provide a thin protective film. The protective film may be composed of the same or similar material as the temporary support, but must be easily separated from the photosensitive resin layer. The protective film material is suitably made of, for example, crepe paper, polyolefin or a sheet of polytetrafluoroethylene. (Manufacturing method of photosensitive resin transfer material)

The photosensitive resin transfer material of the present invention is produced by coating a coating liquid (coating liquid for a thermoplastic resin layer) which dissolves a thermoplastic resin layer additive, and drying it to provide a thermoplastic resin layer, followed by thermoplasticity, on the temporary support. The intermediate layer material solution composed of the solvent in which the thermoplastic resin layer is not dissolved is applied onto the resin layer, and then the composition for the photosensitive resin layer can be coated, dried, and set by dissolving the solvent of the intermediate layer. Production. Further, a sheet in which a thermoplastic resin layer and an intermediate layer are provided on the temporary support, and a sheet in which a photosensitive resin layer is provided on the protective film may be prepared, and the intermediate layer and the photosensitive resin layer may be brought into contact with each other. Further, a sheet in which a thermoplastic resin layer is provided on the temporary support and a sheet in which a photosensitive resin layer and an intermediate layer are provided on the protective film may be prepared so that the thermoplastic resin layer and the intermediate layer are The methods of connecting are made to fit each other. In the photosensitive resin transfer material of the present invention, the film thickness of the photosensitive resin layer is preferably 1·0 to 5·0 μηι, and 1.0 to 4·0 μιτι is preferable, and 1·0 to 3·0 μηη is particularly preferable. Further, it is not particularly limited, but the preferred film thickness of the other layers is generally: temporary support 1 5~1 0 0 Μ m, thermoplastic resin layer -116-200804533 2~30μΓΠ, intermediate layer 〇.5~ 3. 〇Mm, protective film 4~40_. In addition, the coating in the above-described production method can be carried out by a general coating device or the like, and the coating device using the slit-shaped nozzle described in the above [Coating film for coloring photosensitive resin composition] is used in the present invention. It is preferable to carry out (slit coater). A preferred embodiment of the slit coater is the same as described above. [Color Filter]

The color filter of the present invention can be used as a comparatively superior one. The comparison of the present invention shows the ratio of the amount of transmitted light when the two polarizing plates are 'parallel to the polarization axis and perpendicular thereto (refer to "The 7th Color Optical Conference in 990, 512 Color Display 10.4" size TFT- LCD color filter, Ueki, Xiaoguan, Fuyong, Shanzhong, etc.). The so-called high contrast system of color filters produces a combination of light and dark when combined with liquid crystals, which is a very important performance for liquid crystal displays in place of CRTs. The color filter of the present invention is used as a television, and the monochromatic chromaticity system from each of the F1 xenon light source, the red (R), the green (G), and the blue (B) is described in the following table. The difference (ΔΕ) within the range of 5 (hereinafter, referred to as "target chromaticity" in the present invention) is preferably within 5, more preferably within 3, and even within 2. X y YR 0.656 0.336 21.4 G 0.293 0.634 52.1 B 0.146 0.088 6.90 -117- 200804533 The chromaticity in the present invention is determined by a microspectrophotometer (Olympus Optical Co., Ltd.; OSP100 or 200), F10 light source The result of the field of view is calculated by 2 degrees, expressed as xyY値 of the xyz color system. Further, the difference from the target chromaticity is expressed by the color difference of the La*b* color system. (Photosensitive resin layer)

The color filter of the present invention is formed by forming, exposing, and developing a photosensitive resin layer on a substrate, and repeating the method according to the number of colors. Moreover, it is also possible to form a structure in which the boundary is distinguished by a black matrix as needed. In the above-described production method, a method of forming the photosensitive resin layer on a substrate is exemplified by (a) a method of applying the above-described colored photosensitive resin composition by a general coating device or the like, and (b) using the aforementioned photosensitive layer. A resin transfer material, a method of attaching by a laminator, and the like. (a) When the color filter of the present invention is produced by coating with a coating device, a coating device for coloring the photosensitive resin composition can be a general coating device, and in particular, [coloring photosensitive resin] is used. The slit coater described in the section of the coating film of the composition is suitable. Further, preferred examples of the slit coater are the same as described above. Further, preferred examples of the slit coater are the same as described above. In the case where the photosensitive resin layer is formed by coating, the film thickness is preferably 1·0~3·0μηι, 1.0~2·5μιτι is preferable, and I′′~2·5μηι is particularly preferable. (b) The photosensitive resin transfer material of the present invention is applied by a laminator, and the photosensitive resin layer formed in a film form is applied to a substrate to be described later on a heated or/or pressurized roller or plate. Attached by pressing or heating. Specifically, it is described in Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. The laminating machine and the laminating method are preferred from the viewpoint of low foreign matter, and the method described in JP-A-7-11057 5 is used. In addition, the preferable film thickness in the case where the photosensitive resin layer is formed by the photosensitive resin transfer material of the present invention is the same as the preferred film thickness described in the section [Photosensitive resin transfer material].

(Flap) In the present invention, the substrate on which the color filter is formed is, for example, a conventional glass using a transparent substrate, a soda lime glass plate having a cerium oxide film on its surface, a low expansion glass, an alkali-free glass, or a quartz glass plate. Board, or plastic film, etc. Further, the substrate can be adhered to the colored photosensitive resin composition or the photosensitive resin transfer material by applying a pre-coupling treatment. The coupling treatment is preferably carried out by the method described in JP-A-2000-39033. Further, it is not particularly limited, and the film thickness of the substrate is generally from 700 to 1 2 0 0 μm, and from 500 to 11.0 μm. (Oxygen-blocking film) When the color filter of the present invention forms a photosensitive resin layer by application of a colored photosensitive resin composition, an oxygen blocking film can be further provided on the photosensitive resin layer. Thereby, the exposure sensitivity can be improved. The oxygen blocking film is, for example, the same as that described in the section (middle layer) of the above [photosensitive resin transfer material]. Further, it is not particularly limited, but the film thickness of the oxygen barrier film is generally 〇 5 to 3 · 0 μ m. (Exposure and development) -119- 200804533 A predetermined mask is placed above the photosensitive resin layer formed on the substrate, and then the mask, the thermoplastic resin layer, and the intermediate layer are exposed through the mask, and then exposed. The development is carried out with a developing solution, and the steps are repeated in accordance with the number of colors to obtain the color filter of the present invention.

Here, the light source to be exposed may be appropriately selected as long as it is irradiated with light (for example, 3 6 5 n m, 4 0 5 n m or the like) in the wavelength range in which the photosensitive resin layer can be cured. Specifically, for example, an ultrahigh pressure mercury lamp, a high pressure mercury lamp, a metal halide lamp, or the like can be given. The exposure amount is usually about 5 to 200 mJ/cm 2 , preferably about 10 to 1 μm/cm 2 . In addition, the above-mentioned developing liquid is not particularly limited, and a general developing liquid such as those described in JP-A-5-72724 can be used. Further, it is preferable that the developing solution can perform a dissolution type development reaction of the photosensitive resin layer. For example, a compound having a pKa of 7 to 13 is preferably contained in a concentration of 0.05 to 5 mol/L, and may be further added in a small amount. An organic solvent that is compatible with water. Examples of the organic solvent which is miscible with water include methanol, ethanol, 2-propanol, 1-propanol, butanol, diacetone alcohol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, and B. Glycol-n-butyl ether, benzyl alcohol, acetone, methyl ethyl ketone, cyclohexanone, caprolactone, γ-butyrolactone, dimethylformamide, dimethylacetamide, hexamethyl Phosphonium amide, ethyl lactate, methyl lactate, ε-caprolactam, Ν-methylpyrrolidone, and the like. The concentration of the organic solvent is preferably 〇.1% by mass to 30% by mass. Further, a general surfactant can be further added to the above developing solution. The concentration of the surfactant is 〇 . 〇 1 mass. /. ~1 〇% by mass is preferred. The way of visualization can be used for squeezing, spray imaging, spraying and rotating -120-

200804533 Method of developing image, immersion imaging, etc. Here, the above-described shower development will be described, and the unhardened portion can be removed by spraying the developing liquid onto the photosensitive #脂层 after exposure. It is preferred to spray the alkaline ruthenium having low solubility to the photosensitive resin layer before the development, and to remove the thermoplastic resin layer, the intermediate layer, and the like. Further, it is preferable to use a shower or the like to blow it, and to wipe it with a brush or the like, and to develop a residue. The liquid temperature of the developing liquid is preferably from 20 ° C to 40 ° C, and further preferably, the developing liquid is from 8 to 13. Further, in the production of the color filter of the present invention, the color-sensitive photosensitive resin which is formed by overlapping the color filters is disclosed in the specification of Japanese Patent Publication No. Hei. No. Hei. It is preferable to form a susceptor, to form a transparent electrode thereon, and then to overlap the divided protrusions to form a spacer, in order to reduce the cost. In the case where the overlapping coloring photosensitive resin composition is applied in order, the film thickness is finally thinned in order to flatten the overlapping of the coating liquid. For this reason, K (black). RGB has four colors and overlaps the protrusions for the alignment. On the other hand, when a transfer material having a thermoplastic resin layer is used, how to maintain a constant degree, the overlapping colors are 3 or 2 Color is better. Further, the size of the susceptor is preferably 9 mm or more, and more preferably 30 μm or more, from the viewpoint of preventing the photosensitive resin layer from being deformed and maintaining a constant thickness. [Liquid crystal display device] The liquid crystal display device of the present invention uses the contrast of the present invention: the other is the same as the one that is blown out, and the 5% is removed. good. I make the thickness of the ί layer, the color-121-200804533 color filter, and the clarity of black compactness is excellent. Among them, the color filter system VA of the present invention is particularly preferable. It is also possible to use a liquid crystal display device such as a large screen such as a display for a personal computer. [CCD device] The CCD device of the present invention comprises a color filter produced by using the pigment dispersion composition of the present invention. Hereinafter, the CCD device of the present invention will be described in detail.

(Alkali-Soluble Resin) The alkali-soluble resin used in the CCD device is preferably a linear organic polymer, a solvent soluble in an organic solvent, or a weak aqueous solution. These linear organic high molecular polymers are side-locked with a polymer of a carboxylic acid, for example, JP-A-59-4461, JP-A-54-34327, JP-A-58-12577, and JP-A 54-25957. A methacrylic acid copolymer, a acrylic acid copolymer, an itaconic acid copolymer, a butenoic acid copolymer, a maleic acid, as described in JP-A-59-538, No. 59-71 048 The diacid copolymer, the partially esterified maleic acid copolymer, and the like are similarly locked to the acid cellulose derivative having a carboxylic acid. Further, it is also useful as a polymer addition anhydride having a hydroxyl group. In particular, among them, benzyl (meth)propionate/(meth)acrylic acid copolymer, benzyl (meth)acrylate/(meth)acrylic acid/multimer copolymer with other monomers Things are suitable. Further, methylpropenic acid 2, transethyl ester, polyvinylpyrrolidone, polyethylene oxide, polyvinyl alcohol or the like is also useful as a water-soluble polymer. Further, 2-hydroxypropyl (methyl-122-200804533) acrylate/polystyrene macromonomer/benzyl methacrylate/methacrylic acid copolymer, acrylic acid 2-described in JP-A-7_1-40654 Hydroxy-3-phenoxypropyl ester/polymethyl methacrylate macromer/benzyl methacrylate/methacrylic acid copolymer, 2-hydroxyethyl methyl acrylate/polystyrene macromonomer/ Methacrylate

Methyl ester/methacrylic acid copolymer, 2-hydroxyethyl methyl acrylate/polystyrene macromonomer/benzyl methacrylate/methacrylic acid copolymer, and the like. The amount of the alkali-soluble resin added to the curable composition is 5 to 90% by mass based on the total mass of the composition. /〇 is better, and the best is 10~60% by mass. (Polymerizable monomer) The polymerizable single system is preferably a compound having at least one ethyl group which can be subjected to addition polymerization and an ethylenically unsaturated group having a boiling point of 100 ° C or higher at normal pressure. A compound having at least one addition-polymerizable ethylenically unsaturated group and a boiling point of 100 ° C or more at normal pressure may, for example, be polyethylene glycol mono(meth)acrylate or polypropylene glycol (a) Acrylate, phenoxy (methyl) Φ ethyl acrylate, monofunctional acrylate or methacrylate; polyethylene glycol di(meth) acrylate, trimethylolethane tris Acrylate, neopentyl glycol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, hexanediol Acrylate, trimethylolpropane tris(propylene methoxypropyl) ether, tris(propylcanthoxyethyl)trimeric isocyanate, polyfunctional alcohols such as glycerol or trimethylethane Addition of ethylene oxide or propylene oxide by (meth) acrylated, special public Zhao 48-41 708, special public Zhao 50-6 〇 34, such as special opening 5 1 - 3 7 1 9 3 The urethane acrylates described in the respective publications are -123 - 200804533 acid esters, special opening 48_64 Epoxy acrylate of a polyester acrylate, a reaction product of an epoxy resin and (meth)acrylic acid described in each of the publications No. 83, No. 83, No. 83-431, No. Sho. A multifunctional acrylate or methacrylate such as an ester. In addition, it can also be used as a photocurable monomer and a low polymer in "Sakamoto and then the association ～1丨^^^^^丄口^(10)-(8). (B-1) or a compound represented by (B-2). Formula (B-1)

Ch2-o-{B)„-x ch2-0-(B)„—X * I ; . - I........ .....

X

X-(B&gt;n-σαν 〒-CH2- 〇 - CH2-CH2-o- (B5n_CH^O-^n-X CH2-〇-(^n-X general formula (B*2&gt; ct

• (B)^ och2-C-CH2-d- X

In Cht-0-{B)n7-X {S(B-1), (B-2), B systems each independently represent -((^2(:1&quot;120)· and -(CH2CH(CH 3 Any one of 0)-; X each independently represents any one of an acryloyl group, a methacrylic group, and a hydrogen atom, and in the formula (B-1), an acryloyl group and a methacryl group The total of the thiol groups is 5 or 6, and in the formula (B-2), they are 3 or 4; the η series each independently represent an integer of 〇~6, and the total of each η is 3~24. And m is an integer of 〇~6, and the total of each m is 2 to 16}. The polymerizable monomer can be formed in any ratio as long as it can be irradiated with radiation to form a coating film having adhesiveness. The amount used is usually 5 to 90% by mass, preferably 10 to 50% by mass based on the total solid content of the composition. -124 - 200804533 (Colorant) The colorant is a dye which is conventionally known. One type or two or more types of inorganic pigments or organic pigments are used in combination.

The dye system is not particularly limited, and a well-known dye used as a conventional color filter can be used. For example, JP-A-64-90403, JP-A-64-91-01, JP-A-196-301, JP-A-6-11614, and JP-A No. 2,592,207, US Pat. Patent No. 56679, No. 20, No. 5, No. 5, 596, 950, No. 5, 768, 207, Japanese Patent Laid-Open No. Hei No. Hei. Pigment disclosed in -1,94,828 and the like. As the chemical structure, a pyrazole azo system, an anilino azo system, a triphenylmethane system, an anthracene system, a benzene system, an oxaphthalocyanine system, a pyrazolone, a triazole azo system or a pyridone group can be used. A dye such as a nitrogen system, a cyanine system, a phenothiazine system or a pyrazolopyrazole-based imine system. In particular, since the curable composition can be hardened at a relatively low temperature, it is possible to reduce the dye which is inferior to the heat resistance of the pigment or to further improve the durability of the cured film at a high temperature. Decomposition and other issues. The inorganic pigment is a metal compound represented by a metal oxide or a metal salt, and specific examples thereof include metal oxidation of iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, lanthanum, and the like. And the composite oxide of the above metal. The organic pigment is, for example, CL Pigment Yellow 11,24,31, 53,83,85,99,1 08,1 09,110,138,139,150,151,15-125-200804533 4.1 67,1 85 , C_l_ Pigment Orange 36, 38, 43, 71, Cl·Pigment Red 105.122.149.150.155.1 7Ί,1 75,1 76,1 77,20 9,224,242,254, Cl· Ageing Violet 19,23,32,39, Cl Pigment Blue 1.2.1 5,1 6,22,60,66,1 5:3,1 5:6, C_l·Pigment Green 7,36,37,Cl Pigment Brown 25,28,Cl·Pigment Black 1,7, Carbon black and so on.

These organic pigments can be used singly or in various combinations which enhance color purity. The specific examples are as follows. The red pigment may be used alone as a mixture of an anthraquinone pigment, an anthraquinone pigment, or at least one of them with a diazo yellow pigment or an iso D porphyrin yellow pigment. For example, the brewing pigments are exemplified by C I · Pigment Red 1 7 7 '! The pigment is, for example, c 丨·Pigment Red 155. From the viewpoint of color reproducibility, it is preferably mixed with C·I·Pigment Yellow 8 3 or C·丨·Yellow Yellow 139. The mass ratio of the red pigment to the yellow pigment is preferably from 100:5 to 100:50. In this range, it is preferable to suppress the light transmittance and enhance the color purity at 400 to 500 nm. The green pigment is used alone as a halogenated phthalocyanine pigment, or in combination with a disazo nitrogen phthaloid yellow pigment, a quinoline yellow yellow dye or an isoporphyrin yellow pigment, for example, c _ I · Pigment Green 7, 3 Mixing of 6, 7 and C _ I · Pigment Yellow 8 3, 1 38, 1 39 is preferred. The mass ratio of the green pigment to the yellow pigment is preferably from 1 0 0 5 to 1 0 0 · 1 0 0. In the vehicle, the light transmittance is suppressed at 400 to 500 η rn, and good color purity is obtained. The blue pigment may be used alone or in combination with a dioxin-based violet pigment, for example, a mixture of C 丨 丨. Pigment Blue 1 5 : 6 and c · I · Pigment Violet 23 is preferred. The mass ratio of blue pigment to purple pigment is preferably 100:04 〇〇:5〇. In this range, the light transmittance can be suppressed at 400 to 420 nm, and the color purity of -126-200804533 is improved. Further, the above pigments can be produced by using a powdery processed pigment which is finely dispersed such as an acrylic resin, a maleic acid resin, a vinyl chloride-vinyl acetate copolymer, or an ethyl cellulose resin. A pigment-containing photosensitive resin having good dispersibility and dispersion stability is obtained. Further, the pigment for the black matrix is preferably carbon, titanium oxide or iron oxide alone or in combination with carbon and titanium oxide. The mass ratio is preferably in the range of |100:5 to 10:0:40. The long-wavelength light transmittance in this range is small, and the dispersion stability is also good. (Solvent) Solvents are, for example, esters such as ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate , ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, methyl glycolate, ethyl hydroxyacetate, butyl glycolate, methyl methoxyacetate, methoxyacetic acid Ethyl ester, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, 3-methylpropionate, 3-ethyl propionate, etc. Class; methyl 3-methoxypropionate, ethyl 3-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, 2-ethoxyto Methyl propyl propionate, ethyl 2-ethoxypropionate, methyl 2-iodo-2-methylpropanoate, ethyl 2-oxy-2-methylpropionate, 2-methoxyl 2_Methyl propyl propionate, 2 _ ethoxy-2 _ methyl propionate ethyl ester, methyl pyruvate, ethyl pyruvate, pyruvate , ethylacetate methyl acetate, ethyl acetate ethyl acetate, 2_ methyl butyrate, -127- 200804533 ethyl 2-hydroxybutyrate, etc.: ethers, such as diethylene glycol dimethyl ether, tetrahydrofuran, ethylene Alcohol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, digan Alcohol monobutyl ether, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol propyl ether acetate, etc.; ketones, such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3_heptanone, etc.; aromatic hydrocarbons such as toluene, xylene

Among these, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, and butyl acetate are used. Preferably, the ester, methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol methyl ether acetate or the like is preferred. The amount of the solvent to be added is usually 60 to 90% by mass, preferably 70 to 90% by mass, based on the composition. These solvents may be used singly or in combination of two or more. Sensitizers can be used more. Specific examples thereof are, for example, 9-fluorenone, 2-chloro-9-fluorenone, 2-methyl-9-fluorenone, 9-fluorenone, 2-bromo-9-fluorenone, 2-ethyl -9-fluorenone, 9,10-fluorene, 2·ethyl-9,1 0_蒽醌, 2 -t-butyl- 9,10- fluorene, 2,6-dichloro-- 9, 10 - awakening, benzoin, diamethylene acetone, P-(methylamino)phenylstyryl ketone, P-(dimethylamino)phenyl-P-methylstyrylone A benzothiazole-based compound described in Japanese Patent Publication No. 51-48 51 No. The above-mentioned main components and other additives which are required to be used can be prepared by mixing and dispersing them by using various mixers and dispersers. A general manufacturing method for manufacturing a color filter for a CCD device is as described in the following -128-200804533. The step of applying and drying the composition (color resist liquid) of the present invention onto the substrate, the step of pattern-extracting the obtained dried coating film by an i-line stepper or the like, and the alkali after exposure are sequentially performed. In the step of developing, followed by the step of heat-treating, the above steps are repeated for each color (three colors or four colors) in sequence, and a hardened film is formed to obtain a color filter.

More specifically, the above-mentioned curable composition is applied to a suitable substrate by a rotator, and the film thickness at the time of drying is generally preferably applied to an oven of 2 to 2 μm at 85 ° C. Place in for 2 minutes to obtain a smooth coating film. The substrate system is not particularly limited, and examples thereof include a substrate of an electronic component such as a glass plate, a plastic plate, an alumina plate, and a ruthenium wafer for an image sensor, and a transparent resin plate, a resin film, a brown tube display surface, and a camera sensation. Wafer formed by a solid-state imaging device such as a light-receiving surface, CCD, BBD, CID, or BASIS, an adhesive image sensor using a thin film semiconductor, a liquid crystal display surface, a photoreceptor for color electrophotography, and an electrochromic (EC) display The substrate of the device, etc. Further, in order to improve the adhesion between the substrate and the color filter layer, it is preferable to apply a high-density treatment. Specifically, a pattern of a curable composition may be formed by applying a thin layer of a decane coupling agent or the like to the substrate in advance, or a decane coupling agent may be contained in the curable composition in advance. Further, in the case where there is a step on the substrate, the curable composition of the present invention can be applied by coating a flattening film for smoothing the coating surface on the substrate. For example, an image sensor such as a CCD is composed of a photoelectron conversion unit (photodiode) that generates electrons based on the amount of received light on the substrate, and a read gate portion for outputting electrons generated therefrom. 129- 200804533

When the read gate portion is irradiated, the cause of the noise is that the correct information is not output. Therefore, the upper portion of the read gate portion is formed with a light shielding film layer, and the photodiode portion having and without the light shielding film layer is formed. A situation in which a step is generated. When the color resist is applied to the step difference and the color filter is directly formed, the image becomes dark due to the length of the optical path, and the light collection property is also deteriorated. In order to improve them, the purpose is to compensate for the step, and it is preferable to form a transparent planarizing film between the CCD and the color filter. The material of the planarizing film is, for example, a photocurable photoresist liquid, an acrylic or epoxy resin, or the like. After the photocurable composition is applied, in order to obtain a dried coating film in which the solvent evaporates, prebaking is usually performed. The prebaking method is dried under reduced pressure, indirectly heated by high-temperature air or the like, and directly dried by a heating plate or the like (about 80 to 140 ° C, 50 to 200 seconds). Further, post-baking is carried out in order to sufficiently harden the pattern obtained after development and form a permanent film having improved mechanical strength. For example, when a three-color color filter is manufactured, the initially formed pattern is subsequently coated with a photoresist of another color, and then subjected to exposure and development twice. At this time, post-baking was performed so as not to mix with the applied photoresist liquid and without pattern defects due to exposure or development. This post-baking is carried out in the same manner as in the prebaking, and is carried out at a high temperature for a long period of time according to the conditions of the prebaking. For example, in the case of indirect heating by an oven, about 180 to 250 ° C, for about 5 to 2 hours, by direct heating of the hot plate, about 180 to 250 ° C for about 2 to 10 minutes. The light source for exposure is not particularly limited, and may be, for example, an i-line of a light source mercury lamp which is associated with pattern formability and which has a remarkable effect. In the manufacture of a color filter for an image sensor using one of the line spectra of a mercury lamp from the appropriate side of the step, the feature is particularly remarkable, not to mention in the LCD. It can also be used. The developing liquid used in the development of the curable composition is not particularly limited, and a conventionally known developing liquid can be used. Among them, an organic alkali-based developing liquid of a quaternary ammonium salt such as tetramethylammonium hydroxide (T oxime) can be preferably used for the purpose of the present invention.

(Polymering Initiator) A polymeric photoinitiator can be used as a polymerization initiator. Specifically, for example, a vicinal polyketal aldehyde-based compound described in the specification of U.S. Patent No. 2,367,660, an α-carbonyl compound described in the specification of U.S. Patent Nos. 2,367,661 and 2,367,670, and a specification of U.S. Patent No. 2,448,828 The acetoin compound described in the specification, the aromatic acylo compound substituted by the α-hydrocarbon described in the specification of U.S. Patent No. 2,722,51, the polynuclear ruthenium compound described in the specification of U.S. Patent Nos. 3,046,127 and 2,951,758, and the U.S. Patent. The combination of the triallyl imidazole dimer/ρ-aminophenyl ketone described in the specification of Japanese Patent Publication No. 3,549,367, the benzothiazole compound/trihalomethyl-s described in Japanese Patent Publication No. Sho 51-48 51-6 - Triterpenoid compounds and the like. The content of the photopolymerization-inducing agent (including the above-mentioned general photopolymerization initiator) in the negative-type curable composition containing the dye is 0.01 to 50% by mass based on the solid content (mass) of the radical polymerizable monomer. Preferably, 1 to 30% by mass is preferred, and 1 to 20% by mass is particularly preferred. When the content is in the above range, sufficient polymerization hardening is not performed, and polymerization is difficult to proceed. The polymerization rate of poly-131-200804533 becomes large, the molecular weight is lowered, and the film strength is also weakened. Further, among the above photopolymerization initiators, a sensitizer and a photosensitizer can be used. Specific examples thereof include benzoin, benzoin methyl ether, 9-fluorenone, 2-chloro-9-fluorenone, 2-methyl-9-fluorenone, 9-fluorenone, 2-bromo 9-fluorenone, 2-ethyl-9-fluorenone, 9,10-fluorene, 2-ethyl-9,10-fluorene, 2-tert-butyl-9,10-fluorene, 2,6-Dichloro-9,10-anthracene, xanthone, 2-methylxanthene

Ketone, 2-methoxyxanthone, 2-ethoxyxanthone, thioxanthone, 2,4-diethylthioxanthone, acridone, 10-butyl-2-chloroacridine Ketone, benzoin, dibenzylideneacetone, P-(dimethylamino)phenylstyryl ketone, P-(dimethylamino)phenyl-P-methylstyrylone, diphenyl Ketone, P-(dimethylamino)benzophenone (or mischrone), P-(diethylamino)benzophenone, benzofluorenone, etc., or special public 51-4851 A benzothiazole compound or the like described in the publication No. 6, Tinuvin 1130, the same 400, and the like. Hereinafter, the present invention will be described in further detail based on examples, but the present invention is not limited thereto. [Examples] Example 1 &lt;Preparation of Pigment Dispersion A&gt; In a dimethyl sulphide (manufactured by Wako Pure Chemical Industries, Ltd.) 1 〇〇〇m|, sodium methoxide 20% methanol solution 3 3.3 m I was added, Pigment C · | _Pigment red 2 5 4 (丨rgaph 〇r R ed BT-CF, trade name, Ciba special chemical (stock) system) 5〇g, and polyethylene base ratio slightly ketone (K-30, The product name, manufactured by Wako Pure Chemical Co., Ltd.), 〇〇.g, to prepare pigment solution A. Further, 1 (7) 〇 | / 1 hydrochloric acid (manufactured by Wako Pure Chemical Industries, Ltd.) of 16 m I of water 1 〇 〇 〇 m I ' was prepared as a poor solvent. • 132- 200804533 Here, the temperature is controlled at i δ °c, and the mixture is stirred at 50 Or pm by a G Κ - 0 2 2 2 - 1 0 Lamodo mixer (trade name, manufactured by Fujisawa Pharmaceutical Co., Ltd.). In 1000 ml of water of a poor solvent, a NP-KX-500 type large-capacity pulseless pump (trade name, manufactured by Nippon Precision Chemical Co., Ltd.) was used, and 100 ml of pigment solution A was injected at a flow rate of 100 m|/m in to form a pigment solution A. Organic pigment particles to prepare pigment dispersion A. This pigment dispersion uses Nanotrack

UPA-EX150 (trade name, manufactured by Nikkiso Co., Ltd.) was used to measure the number average particle diameter Μ η and the monodispersity (M v / Μ η ). The results are shown in Table 1 below. Example 2 &lt;Preparation of Pigment Dispersion Liquid Hydrazine&gt; Example 1 was changed except that the temperature of the poor solvent in Example 1 was changed to 40 ° C, and the injection flow rate of the pigment solution A was changed to 130 m l/m in The pigment dispersion B was prepared in the same manner. The number average particle diameter and monodispersity of the prepared pigment dispersion liquid B were measured in the same manner as in Example 1. The results are shown in the following Table 1 / Example 3 &lt;Preparation of Pigment Dispersion C&gt; Except that the injection flow rate of the above pigment solution A in Example 1 was changed to 7 5 m I / mi η, and Example 1 The pigment dispersion C was prepared in the same manner. The number average particle diameter and monodispersity of the prepared pigment dispersion liquid C were measured in the same manner as in Example 1. The results are shown in Table 1 below. Example 4 &lt;Preparation of Pigment Dispersion D&gt; The pigment dispersion liquid D was prepared in the same manner as in Example 1 except that the temperature of the above-mentioned poor solvent in Example 1 was changed to 35 °C to -133-200804533. The number average particle diameter and monodispersity of the prepared pigment dispersion liquid D were measured in the same manner as in Example 1. The results are shown in Table 1 below. Example 5 &lt;Preparation of Pigment Dispersion E&gt;

The pigment dispersion liquid ε was prepared in the same manner as in Example 1 except that the injection flow rate of the above pigment solution A in Example 1 was changed to 1 30 m l/m i η. The number average particle diameter and monodispersity of the prepared pigment dispersion liquid were measured in the same manner as in Example 1. The results are shown in Table 1 below. Comparative Example 1 &lt;Preparation of Pigment Dispersion F&gt; 45.3 g of 1-methoxy-2-propyl acetate was stirred, and Pigment CI Pigment Red 2 54 (lrgaphor Red BT-CF, trade name, Ciba Special Chemicals) )) 6.4 g of polyvinylpyrrolidone 12_8 g to obtain a mixed solution. Then, this mixed liquid was subjected to dispersion treatment at a peripheral speed of 9 m/s for 9 hours using an electric honing machine M-50 (trade name, manufactured by Eiger Japan Co., Ltd.) using zirconium oxide particles having a diameter of 〇65 mm to obtain pigment dispersion. Composition F. The number average particle diameter and monodispersity of the prepared pigment dispersion liquid F were measured in the same manner as in Example 1. The results are shown in Table 1 below. Comparative Example 2 &lt;Preparation of Pigment Dispersion G&gt; The pigment dispersion liquid G was prepared in the same manner as in Comparative Example 1, except that the dispersion treatment time in Comparative Example 1 was changed from 9 hours to 8 hours. The number average particle diameter of the prepared pigment dispersion liquid G and the degree of dispersion of 134 - 200804533 were measured in the same manner as in Example 1. The results are shown in Table 1 below. Comparative Example 3 &lt;Preparation of Pigment Dispersion Liquid Hydrazine&gt; The pigment dispersion liquid η was prepared in the same manner as in Example 1 except that the injection flow rate of the above-mentioned pigment solution Α was changed to 30 ml/m in Example 1. The amount of ruthenium and the degree of monodispersity of the prepared pigment dispersion liquid were measured in the same manner as in Example 1. The results are shown in Table 1 below.

&lt;Preparation of Pigment Dispersion I&gt; The pigment dispersion liquid was prepared in the same manner as in Comparative Example 1, except that the dispersion treatment time in Comparative Example 1 was changed from 9 hours to 4 hours. The number average particle diameter and the single-dispersion of the prepared pigment dispersion liquid I were measured in the same manner as in Example 1. The results are shown in Table 1 below. -135- 200804533 Table Embodiment Example 2

Dispersion A Number average particle diameter Mn [nm] 33 Monodispersity (M v / Μ η ) 32 Example 3 ----_____ Example 4 Example 5 Comparative Example Comparative Example 1 Comparative Example 3 Comparative Example 4

Is dispersion B

@Dispersion C

Dispersion D

Dispersion E jjgL Dispersion F Dispersion G ϋ Dispersion Η Dispersion 32 79 50 47 29 45 108 95 31 1 .92 .31 2.45 2.10 .35 3.27 Example 6~1 〇, Comparative Example 5~8 &lt; Preparation of Pigment Dispersion Compositions A to I &gt; [Preparation of Pigment Dispersion Composition A]

To the prepared pigment dispersion A (pigment particle concentration of about 0.05% by mass), 2-(1-methoxy)propyl acetate 500 mb was added to 25. (: 1 minute, stirred at 500 rpm, and allowed to stand for 1 day, and the pigment particles were extracted as a concentrated extract in the 2-(1-methoxy)propyl acetate phase. The concentrated extract of the above extracted pigment particles was used. Filtration was carried out using a FP-01 0 type filter (trade name, Sumitomo Electric Fine P〇|Ymer Co., Ltd.) to obtain a paste-like concentrated pigment liquid A (pigment particle concentration: 3 〇 mass%). The pigment liquid A' was concentrated to prepare a pigment-dispersed composition A of the following composition: 136-200804533. The following pigment dispersant A was synthesized according to JP-A-2000-239554. The above-mentioned paste-like concentrated pigment liquid A 21.3 g of pigment dispersant A 〇.6 g (exemplified compound of the compound represented by the above formula (D1)) 7. methacrylic acid / benzyl methacrylate copolymer 15.8 g

(copolymerized molar ratio 28/72, weight average molecular weight: 30,000, 40% 1-methoxy-2-propyl acetate solution) 1-methoxy-2-propyl acetate (manufactured by Wako Pure Chemical Industries, Ltd.) 42.3 g In the same manner as the pigment dispersion liquid A and the pigment dispersion composition A, the pigment dispersion liquid A was changed to the pigment dispersion liquid A and the pigment dispersion composition B to prepare a concentrated pigment dispersion liquid B to I and a pigment dispersion composition B. |. [Preparation of Membrane Sample AH] The pigment dispersion composition AH of the above composition was used by an electric honing machine M-50 (trade name, manufactured by Eiger Japan Co., Ltd.), and zirconia particles having a diameter of 〇65 mm were used at a peripheral speed. 9 m/s was stirred for 1 hour to serve as a sample pigment liquid AH. A film sample was prepared to evaluate the performance of the sample pigment liquid. The sample pigment liquid AH obtained as described above was applied onto a 75 mm x 75 mm glass substrate by a spin coater 1H-D7 (trade name, manufactured by Mikasa Co., Ltd.), and dried by drying on a hot plate at 1 ° C for 2 minutes to prepare. Membrane sample AH. [Measurement of Contrast] A polarizing plate is provided in a three-wavelength cold cathode tube light source -137-200804533 (FWL18EX-N, trade name, manufactured by Toshiba LITEC Co., Ltd.) as a backlight unit. (HLC2-251 8. Product name, Sanli

The membrane sample produced was placed between (Sanritsu) Co., Ltd., and the amount of transmitted light when it was parallel to the polarizing axis and perpendicular was measured, and the ratio was compared (refer to Ueki, Komatsu, Fuyong's mountain, "51 2-color display 1 0·4" color filter for TFT-LCD", 7th Color Optics Conference (1990), etc.). Chroma

The measurement was performed using a color luminance meter (BM-5 manufactured by TOPCON Co., Ltd.). 2 polarizing plates, film samples, and color brightness meter are placed at a position 13 mm from the backlight, and a cylinder with a diameter of 1 1 mm and a length of 20 mm is placed from a position of 40 mm to 60 mm. The light system was irradiated with a film sample set at a position of 65 mm, and the transmitted light was measured by a polarizing plate set at a position of 1 mm and measured by a color luminance meter set at a position of 400 mm. The measurement angle of the color luminance meter is set to 2°. The amount of light in the backlight is set such that the brightness of the two polarizing plates when placed in parallel Nicols is 1280 c d/m 2 in a state where no sample is set. The measurement results of the film samples A to 丨 were as shown in the following Table 2 (the number average particle diameter and the monodispersity shown in Table 1 are also shown in the corresponding sample). 138- 200804533 Table 2 Number average particle diameter Μ n [nm] Monodispersity (Mv/Mn) Comparative Example 6 Film sample A 33 1.32 1 7000 Example 7 Film sample B 32 1.79 1 2000 Example 8 Film sample c 50 1.31 1 2000 Example 9 Membrane sample D 47 1.92 11000 Example 1 Membrane sample E 2 9 1.31 1 9000 Comparative Example 5 Membrane sample F 32 2.4 5 8000 Comparative Example 6 Membrane sample G 45 2.10 8500 Comparative Example 7 Membrane sample Η 1 08 1 .35 4000 Comparative Example 8 Membrane sample I 95 3.27 1000

As is apparent from the results of Table 2, the film samples of the examples 6 to 10 showed a high contrast with respect to the film samples FH of Comparative Examples 5 to 8, and exhibited good display characteristics of φ. Furthermore, the film sample was heated at 220 ° C for 30 minutes to prepare film samples J to R, and an optical microscope (MX-50, trade name, manufactured by Olympus Co., Ltd.) was used at a magnification. The presence or absence of precipitates in the surface of each film sample was observed at 500 times. The results are shown in Table 3 below (the number average particle diameter and monodispersity shown in Table 1 are also shown in the corresponding sample). -139 - 200804533 Table 3 Number average particle diameter Mn [nm] Monodispersity (Mv/Mn) Presence or absence of film sample J 33 1.32 No precipitation and uniformity Film sample K 32 1.79 of the present invention No precipitation and uniform examples of the invention Film sample L 50 1.31 No precipitation and uniform film sample of the present invention 1. 47 1.92 No precipitation and uniform film sample of the invention Ν 29 1.31 No precipitation and uniform film sample of the invention 〇32 2.45 Precipitated film sample Ρ 45 2.10 There was a comparative sample film sample Q 108 1.35 No precipitation and uniform comparative film sample R 95 3.27 Precipitated comparative example

From the results of Table 3, it is apparent that among the film samples Ο to R of the comparative example, the samples 0, P, and R in which the monodispersity of the pigment particles exceeds 2.0 are observed in the in-plane, and the precipitate is observed. The film samples J to ISI of the present invention have no precipitates and can form a uniform surface state. Example 1 1 Except that in Examples 1 to 10 and Comparative Examples 1 to 8, the pigment red 254 used for the production of the pigment dispersion liquid AH and the film samples A to R was changed to the pigment violet 23, respectively, and Example 1 to A film sample was produced in the same manner as in Comparative Examples 1 to 8. When the obtained film sample was used for measurement, observation, and presence or absence of a precipitate, the film sample of the present invention exhibited good performance as compared with the comparative example. Example 1 2 -140 - 200804533 &lt;Production of Color Filter&gt;

[Production of photosensitive resin transfer material K1 J

The coating liquid for a thermoplastic resin layer composed of the following formulation Η 1 was applied and dried to a polyethylene terephthalate film temporary support having a thickness of 75 μm by a slit nozzle. Next, the coating liquid for an intermediate layer composed of the following formulation Ρ1 was applied and dried. Further, a resin composition κ having a light-shielding property, which is composed of the composition described in the following Table 4, was applied and dried, and a thermoplastic resin layer having a dry film thickness of 15 μm was provided on the temporary support. An intermediate layer having a film thickness of 1.6 μm and a light-shielding resin layer having a dry film thickness of 2·4 μm were dried to roll the protective film (thickness 12 μπΊ polypropylene film). In this manner, a photosensitive resin transfer material in which a temporary support, a thermoplastic resin layer, an intermediate layer (oxygen barrier film), and a light-shielding resin layer are integrated is prepared, and the sample name is set as a photosensitive resin transfer. Material Κ 1. (Coating liquid for thermoplastic resin layer: Formulation Η1) • Methanol · 1 1 · 1 part by mass • Propylene glycol monomethyl ether acetate 6_4 parts by mass • Methyl ethyl ketone 52.4 parts by mass • Methyl methacrylate/acrylic acid 2-ethylhexyl ester / 5.83 parts by mass of benzyl methacrylate/methacrylic acid copolymer (copolymerization composition ratio (mole ratio) = 55/11.7/4.5/28.8, molecular weight = 10 禺, Tg = 70 °C) • Styrene/acrylic copolymer (copolymerization composition ratio (mole ratio) = 63/37, molecular weight = 10,000, Tg and 100 °C) 3.6 parts by mass • 141-200804533 • 2,2-double [ 4-(Methethyloxypolyethoxy)phenyl]propane (manufactured by Shin-Nakamura Chemical Co., Ltd.) 9.1 parts by mass • Surfactant 1, 0.54 parts by mass * Surfactant 1 (Megafac F-780 The composition of -F (trade name, Dainippon Ink Chemical Industry Co., Ltd.)) is as follows. • C6F13CH2CH2〇C〇CH = CH2 : 40 parts, H(OCH(CH3)CH2)7OCOCH = CH2: 55 parts, and H(OCH2CH2)7OCOCH = CH2: 5 parts copolymer (molecular weight 30,000) 30 parts by mass • 70 parts by mass of methyl ethyl ketone (coating solution for intermediate layer (oxygen barrier layer) · Formula FM) • Polyvinyl alcohol (PVA 205, trade name, manufactured by Kuraray Co., Ltd.), degree of roadway = 8 8 %, degree of polymerization 5 5 〇) 3 2 _ 2 parts by mass • Polyvinylpyrrolidone (PVP, K-30, trade name, 14.9 parts by mass, 4 2 9 parts by mass, 524 parts by mass of ISP, Japan) )Company system) Methanol distilled water-142- 200804533 Table 4 Composition K content (parts by mass) K pigment dispersant 1 (carbon black) 25 Propylene glycol monomethyl ether acetate 8.0 Methyl ethyl ketone 5 3 Adhesive agent-1 9.1 Awakening a ' _ base acid 0.002 D Ρ Η A liquid 4.2 2,4-di(trichloromethyl)-6-[4-(indole diethoxycarbonylmethyl)amino-3-bromobenzene Base]-s-triple 0.1 0.1 surfactant 1 0.044

Here, the preparation of the light-shielding resin composition K1 described in the above Table 4 will be described. The resin composition K1 having a light-shielding property can be obtained by first weighing the K pigment dispersion 1 and propylene glycol monomethyl ether acetate in the amounts shown in Table 4, and mixing at a temperature of 24 C (± 2 C). And spoiled at i5 rpm for 10 minutes, and then weighed the amount of methyl ethyl ketone, binder 1, hydroquinone monomethyl ether, DPHA liquid, 2,4 - bis (trichloro) described in Table 4. Methyl)-6-[4'-(N,N-diethoxymethylmethyl)amino-3,-bromophenyl]-s·three tillage, surfactant 1, sequential temperature It was added at 25 ° C (± 2 ° C) and was obtained by stirring at 150 rpm for 30 minutes at a temperature of 40 ° C (± 2 ° C). Further, among the compositions described in Table 4, the composition of the K pigment dispersion 彳, the viscous-143-200804533, the binder 1 and the D Ρ Η A liquid are as follows. Further, the surfactant 1 is the same as the surfactant 1 used in the coating liquid Η 1 for the above thermoplastic resin layer. (Κ pigment dispersion 1) • Carbon black (SpecialBlack 250, trade name, manufactured by Degussa Co., Ltd.) 1 3 · 1 part by mass • The above pigment dispersant Α 〇 · 65 parts by mass

• Polymer (benzyl methacrylate / methacrylic acid = 72/28 molar ratio random copolymer, molecular weight 37,000) 6.72 parts by mass • Propylene glycol monomethyl ether acetate 79.53 parts by mass (adhesive agent) 1) • Polymer (benzyl methacrylate/methacrylic acid = 78/22 molar ratio random copolymer, molecular weight 40,000) 27 parts by mass • Propylene glycol monomethyl ether acetate 73 parts by mass (DPHA solution) • Dipentaerythritol hexaacrylate (containing polymerization inhibitor MEHQ 500ppm, manufactured by Nippon Kayaku Co., Ltd., trade name: KAYARAD DPHA) 76 parts by mass • Propylene glycol monomethyl ether acetate 24 parts by mass (with light-shielding property) Formation of the partition wall] The alkali-free glass substrate was sprayed with a glass detergent liquid adjusted to 25 ° C, and while being blown for 20 seconds, it was washed with a rotating brush having nylon hair and washed with pure water. After the net, by spraying a decane coupling solution (Ν-β-(aminoethyl)-γ-aminopropyl dimethoxy sand pot 0_3 mass% aqueous solution, commercial-144-200804533 name: KB M603, Shin-Etsu Chemical Industry Co., Ltd.) and boasted for 20 seconds for pure water spray washing . The substrate was heated at 1 〇 ° C for 2 minutes with a substrate preheating device. After peeling off the protective film of the photosensitive resin transfer material K1, it was glued to the substrate heated at 100 ° C for 2 minutes using a Lamic II type laminator (manufactured by Hitachi, Ltd., trade name). Roller temperature 130. 〇, line pressure 1001^/〇 1712, conveying speed 2.2111/min, and lamination.

After the temporary support is peeled off, a proximity exposure machine (manufactured by Hitachi High-Tech Electronics Co., Ltd.) having an ultrahigh pressure mercury lamp is used, and the substrate and the mask (the quartz exposure mask having the portrait pattern) are vertically erected. The distance between the exposure mask surface and the thermoplastic resin layer was set to 200 μm, and the pattern exposure was performed at an exposure amount of 100 mJ/cm 2 . The mask shape was a lattice shape and the radius of curvature of the lobe on the side of the partition wall having the light-shielding property was 0.6 pm in the portion corresponding to the boundary line between the pixel and the light-shielding partition wall. Next, in a triethanolamine-based developing solution (containing 2:5% of triethanolamine, containing a nonionic surfactant, and containing a polypropylene-based antifoaming agent, trade name: T-PD1, manufactured by Fuji Photo Film Co., Ltd.) At 50 ° C, spray development was carried out at a flat nozzle pressure of 0_04 M Pa to remove the thermoplastic resin layer and the intermediate layer (oxygen barrier layer). After that, continue to use sodium carbonate imaging solution (containing 0.06 mol / liter of sodium bicarbonate, the same concentration of sodium carbonate, 1% of sodium dibutylnaphthalene sulfonate, anionic surfactant, defoamer, stability Agent, trade name: T-CD1, manufactured by Fuji Photo Film Co., Ltd.), spray-developing at 29 ° C for 30 seconds, with a cone nozzle pressure of 0-1 5 MPa, and developing a resin having a light-shielding property to obtain -145 - 200804533 To the patterned pattern partition wall (the partition pattern with shading). After that, continue to use a detergent (containing a phosphate, a citrate, a nonionic surfactant, an antifoaming agent, a stabilizer, and a product name "T-SD1 (trade name, manufactured by Fuji Photo Film Co., Ltd.))". At 20 ° C, the residue was removed by spraying with a rotating brush having nylon wool by a cone nozzle pressure 〇 02 M Pa to obtain a partition having a light-shielding property. Subsequently, the substrate is further irradiated with light of 500 m J/cm 2 from the side of the resin layer using an ultrahigh pressure mercury lamp.

After the post exposure, heat treatment was carried out at 250 ° C for 50 minutes. [Milling water repellency treatment] Subsequently, plasma water repellency treatment was carried out according to the following method. The above-mentioned substrate on which the light-shielding partition wall was formed was subjected to plasma water repellency treatment using a cathode coupling type parallel plate type plasma processing apparatus under the following conditions. Gas used: CF4 gas flow rate: 80 sccm Pressure: 40 Pa RF power: 50 W Processing time: 30 sec [Preparation of inkjet ink for color filter] Example 1 of JP-A-2002-201 387, with the following The formulation shown in Table 5 is used to modulate the ink. -146- 200804533 Table 5 Component Content (parts by mass) R Ink 1 G Ink 1 B Ink 1 Concentrated Pigment A (C.LRR. 254) 14 One G Pig (CIPG· 36) _ 5.0 A B Pigment (CXP.B· 15 ·· 6) A _ 5,0 polymer dispersant (Sorospas 24000 manufactured by AVECIA) 2.0 2.0 2.0 Adhesive (methyl propyl acrylate-methacrylic acid copolymer) 3.0 3.0 3.0 Dipentaerythritol pentaacrylate 2.0 2.0 2.0 Tripropylene glycol diacrylate 5.0 5.0 5.0 2-Methyl-1-[4-(methylthio)phenyl]·2-flavored propanone 2.0 2.0 2.0 II Glycol monobutyl ether acetate (29.9 dyn/cm) — ........... _ 7 72 81 81 Ink viscosity at the time of injection (mPa · s) 15 10 10 Printing at the time of injection Ink surface tension (mN/m) 26 21 21

&lt;Viscosity&gt; The viscosity of the ink is determined by an E-type viscometer (RE80L, trade name, manufactured by Toki Sangyo Co., Ltd.) at 25 ° C, using a gyrator 1 ° 34, XR 24, and measuring time of 2 minutes. Under the conditions, it is measured. &lt;Surface tension&gt; The surface tension of the ink was measured by a surface tension meter (FACE SUFACE TENSIOMETER CBVB-A3, trade name, manufactured by Kyowa Scientific Co., Ltd.) at a measurement temperature of 23 °C. With respect to the mixing of the components of the above Table 5, first, the pigment and the polymer dispersing agent were placed in a part of the solvent, mixed, and the mixture was shaken with a bead mill using three rolls to obtain a pigment dispersion liquid. On the other hand, the other -147 - 200804533 compounding ingredients were put into the residual portion of the spirulina and stirred to dissolve and disperse 'to obtain a binder solution. Then, the pigment dispersion liquid was added to the binder solution in a small amount, and the mixture was sufficiently stirred with a dissolver to prepare an inkjet ink for color filter. In addition, the concentrated pigment liquid A in the preparation of the above-described R ink 1 is changed to the concentrated pigment liquid B, and the R inks 2 to 9 are modulated in the same manner as in the R ink 1.

The R ink 1, G ink 1, and β ink 1 obtained as described above were subjected to a piezoelectric nozzle. First, ink was dripped around the concave portion of the light-shielding partition wall as described below. Then, as described below, the color filter 1 is obtained. Further, the color filters 2 to 9 are modulated in the same manner as the color filter 1 except that the R ink 1 in the modulation of the color filter 1 is changed to the R inks 2 to 9. The nozzle has 318 nozzles per 25_4 mm and 150 nozzle densities, which are fixed by 1 /2 of the nozzle spacing φ in the direction of the two nozzle rows, and arranged in the nozzle arrangement direction on the substrate. Drip 300 drops per 25.4mm. The nozzle and the ink are controlled by circulating warm water in the nozzle to control the vicinity of the discharge portion to be 50 ± 0.5 °C. The ink discharged from the head is controlled by the piezoelectric driving signal applied to the head, so that each drop can be discharged 6 to 42 pi. In this embodiment, the glass substrate is conveyed while being placed at a position 1 mm below the head. Drip. The transport speed can be set in the range of 50 to 200 mm/s. Further, the piezoelectric driving frequency can be up to 4.6 KHz, and the amount of dripping can be controlled by such setting. -148- 200804533 In this embodiment, the conveying speed and the driving frequency are controlled such that the coating amounts of the respective pigments of R, G, and B are 1.1, 1_8, and 0.7 5 g/m2 to drip the inks of R, G, and B. To the recess corresponding to the desired R, G, B.

The dripped ink is transferred to the exposure portion, and exposure is performed by an ultraviolet light emitting diode (UV-LED). In the present embodiment, the UV_LED system uses NCCU033 (trade name) manufactured by Nichia Corporation. This LED emits light of about 650 nm from a single wafer, and emits light of about 100 mW from the wafer by energizing a current of about 500 mA. A plurality of them are arranged at intervals of 7 mm to obtain a power of 0.3 W/cm 2 on the surface. The time from exposure to exposure and the exposure time may vary depending on the transport speed of the medium and the distance between the head and the direction in which the LED is transported. In the present embodiment, after the shot, it was allowed to dry at 1 Torr for 1 , minutes, followed by exposure. The exposure energy on the medium can be adjusted between 0.01 and 15 J/cm2 depending on the distance and the setting of the conveying speed. In this embodiment, the exposure energy is adjusted in accordance with the transport speed. The measurement of the exposure power and the exposure energy was carried out by using a sea tide electric radiation spectrometer URS-40D (trade name), and using a 値 integral of a wavelength between 22.0 nm and 400 nm. The glass substrate after the dropping was baked in an oven at 230 ° C for 3 〇 minutes, and the light-shielding partition walls and the respective pixels were completely cured together to form a color filter. Example 1 3 [Production of Liquid Crystal Display Element] Liquid crystal display devices were produced as follows using filters 1 to 9, respectively. -149 - 200804533 (Formation of ITO electrode) A glass substrate formed of a color filter was placed in a sputtering apparatus, and a crucible of 1 300 Å (indium tin oxide) was vacuum-deposited at 100 ° C at 240 ° C. c was annealed for 90 minutes to crystallize ITO to form an ITO transparent electrode. (formation of spacers)

A spacer is formed on the ITO transparent electrode produced as described above by the same method as the spacer formation method described in [Example 1] of JP-A-2004-240335. (Formation of liquid crystal alignment control projections) The liquid crystal alignment control projections are formed on the I TO transparent electrode formed of the spacers by using the coating liquid for a positive photosensitive resin layer described below. However, the exposure, development, and baking steps utilize the following methods. A proximity exposure machine (manufactured by Hitachi High-Tech Electronics Co., Ltd.) was disposed at a distance of 1 〇〇Mm from the surface of the photosensitive resin layer, and the irradiation energy was 150 mJ by the ultra-high pressure mercury lamp through the reticle. /cm2 makes it adjacent to the exposure. Thereafter, the aqueous solution of 2.38% tetramethylammonium hydroxide was continuously sprayed on the substrate at 33 °C for 30 seconds while developing the image by a shower type developing device. In this case, by removing the unnecessary portion (exposure portion) of the photosensitive resin layer, it is possible to obtain a liquid crystal alignment control for forming a photosensitive resin layer having a desired shape on the color filter side substrate. A substrate for a liquid crystal display device in which protrusions are formed. Then, the substrate for a liquid crystal display device formed by the liquid crystal alignment control projections is baked at 23 ° C for 3 minutes to be cured on the liquid crystal alignment control on the liquid crystal-150-200804533 display device substrate. Protrusions are formed. (Formulation of coating liquid for positive photosensitive resin layer) • Positive photoresist (FH_2413F, trade name, manufactured by Fujifilm Electronic Materials Co., Ltd.) 53.3 parts by mass • Methyl ethyl ketone 46.7 parts by mass

• Megafac F-780F (trade name, manufactured by Dainippon Ink Chemical Industry Co., Ltd.) 〇 . 〇 4 parts by mass

(Production of Liquid Crystal Display Device) An alignment film made of polyimine was further provided on the substrate for a liquid crystal display device obtained above. Subsequently, at the position corresponding to the outer frame of the light-shielding partition provided around the color filter group, the epoxy resin sealant is printed, and the MVA form liquid crystal is dropped, and the opposite substrate is attached. After the combination, the bonded substrate is heat treated to harden the sealant. On both surfaces of the liquid crystal cell thus obtained, a polarizing plate (HLC 2-2518, trade name, manufactured by San. Ritsu Co., Ltd.) was attached. Next, a backlight of a three-wavelength cold cathode tube light source (FWL1 8EX-N, trade name, manufactured by Toshiba LITEC Co., Ltd.) is formed, and the polarizing plate is disposed on the side of the back surface of the liquid crystal cell to form a liquid crystal display device. . The liquid crystal display device using the color filters 1 to 5 of the present invention is superior to the display device using the color filters 6 to 9 in the comparative example. It is known that the blackness and the redness are excellent. Example 1 4 - 151 - 200804533 [Production of liquid crystal display device of PVA mode and IPS mode] (Production of liquid crystal display device for PVA mode) R pixels, G pixels, and B of the color filter substrate obtained as described above On the pixel and the black matrix, a transparent electrode of ITO (Indium Tin Oxide) is further formed by sputtering. Next, according to Example 1 of JP-A-2006-64921, a spacer is formed on the I TO film formed as described above with respect to the upper portion of the black matrix.

Further, a glass substrate as a counter substrate is prepared, and a pattern for PVA mode is applied to the transparent electrode of the color filter substrate and the counter substrate, and an alignment film made of polyimine is further provided thereon. . Subsequently, a sealing agent for the ultraviolet curable resin is applied to the periphery of the pixel group surrounding the color filter, corresponding to the position of the black matrix outer frame, and the liquid crystal for PVA mode is dropped to the opposite substrate. After bonding, the bonded substrate is subjected to UV irradiation, and then heat-treated to cure the sealant. A polarizing plate (HLC2-2518, trade name, manufactured by Sanritsu Co., Ltd.) was attached to both surfaces of the liquid crystal cell thus obtained. Next, a red (R) wafer type LED (FR1112H, trade name, manufactured by Stella), green (G) wafer type LED (DG1112H, trade name, Staley), blue ( B) A wafer-type LED (DB1112H, trade name, manufactured by Stella) and which constitutes a backlight of a side light type, and the polarizing plate is disposed on the back side of the liquid crystal cell to be fabricated to produce a liquid crystal display device. (Production of liquid crystal display device for I PS mode) On the R pixel, the G pixel, the B pixel, and the black matrix of the color filter substrate obtained above, 丨TO (Indium -152-) was formed by sputtering.

200804533

Transparent electrode of Tin Oxide, indium tin oxide. Next, in the first embodiment of the publication of J 20 0 6-6 4921, a spacer is formed on the portion formed above with respect to the upper portion of the black matrix. On the color filter substrate with the spacer obtained above, ruthenium was subjected to a rubbing treatment to form an alignment film. Further, a liquid crystal display element is produced by combining a driving side substrate and a liquid crystal material with respect to the color filter substrate obtained as described above. Preparing a T FT substrate in which a TFT and a comb-shaped pixel electrode (conductive layer) are arranged to serve as a driving side substrate, a surface on a side where the pixel of the T FT substrate is disposed, and a color filter pixel obtained as described above and a color filter The surfaces on the side on which the layers are formed are disposed in opposite directions, and the spacers formed are formed to be fixed. A liquid crystal layer having an image display is provided in the gap. On both sides of the liquid thus obtained, a polarizing plate (HLC2-2518, trade name (Sanritsu)) was attached. Next, a backlight constituting the cold cathode tube is disposed, and the polarizing plate is disposed on the side of the back surface of the liquid crystal cell to form a display device. The liquid crystal display device using the color filter of the present invention is known to be excellent in both blackness and red in any mode of the 丨PS, and in particular, the redness in the PVA mode is a preferred embodiment. 1 5 &lt;Production of CCD device 1&gt; [Production of pigment dispersion liquid for CCD] The green (G) pigment dispersion liquid (1) was prepared according to the following formulation, and the ITO film was coated and coated. The IPS electrode and the like have a PVA clarity difference depending on the liquid crystal cell unit and the Sanli. , Blue (Β) -153- 200804533 Item dispersion (2), red (R) pigment dispersion (3). Pigment Dispersion (1 ) • c. I · PG36 • CI.PG7 • CIPY_ 1 39 90 parts by mass 25 parts by mass 4 parts by mass • PLAAD ED151 (trade name, nanben chemical (manufactured)) 20 parts by mass • benzyl methacrylate/methacrylic acid copolymer 2 parts by mass

(copolymerized molar ratio 70:30, weight average molecular weight 30,000) • propylene glycol monomethyl ether acetate 625 parts by mass pigment dispersion (2 ) • CI PB15: 6 125 parts by mass • c·丨· Ρ· V_23 25 parts by mass • PLAAD ED1 51 (trade name 'Nanmoto Chemicals Co., Ltd.) 40 parts by mass • Benzyl methacrylate/methacrylic acid copolymer 25 parts by mass (copolymerized molar ratio 70:30, weight average molecular weight) 30,000) • Propylene glycol monomethyl ether acetate 785 parts by mass of pigment dispersion (3) • Pigment dispersion composition A 650 parts by mass • Dispersant (exemplified compound C-16) 40 parts by mass • Benzyl methacrylate / 25 parts by mass of methacrylic acid copolymer (copolymerized molar ratio 70:30, weight average molecular weight: 3 禺) • propylene glycol monomethyl ether acetate 335 parts by mass [Production of coloring photosensitive resin composition for CC D] Each of the pigment dispersion liquids obtained above was uniformly mixed with the following composition in a blender in an amount of from 200 parts by mass to 154 to 200804533 to adjust the coloring photosensitive resin composition for c CD for each color. &lt;Composition&gt; • 35 parts by mass of benzyl acrylate/methacrylic acid copolymer (copolymerized molar ratio = 70/30, weight average molecular weight: 30,000) • Dipentaerythritol pentaacrylate 38 parts by mass • Propylene glycol monomethyl ether 120 parts by weight of acetate

• 40 parts by mass of ethyl-3-ethoxylate propionate • Halogenated methyl tri-grain-based healing agent (photopolymerization heuristic) 4 parts by mass (TAZ1 07, trade name, green chemical (share) system) Production of Filter and CCD Device] The following composition was mixed with a stirrer to prepare a photoresist for planarizing film. [Composition] • Benzyl acrylate/methacrylic acid copolymer 165 parts by mass (copolymerized molar ratio = 70/30, weight average molecular weight 30,000) • Dipentaerythritol pentaacrylate 65 parts by mass • Propylene glycol monomethyl ether 138 parts by mass of acetate • 123 parts by mass of ethyl-3-ethoxylate propionate/halogenated methyl tri-trap heuristic (photopolymerization heuristic) 3 parts by mass (TAZ1 07, trade name, green chemistry ( The resulting planarization photoresist was uniformly applied to a 6-inch germanium wafer forming a photodiode by spin coating. Further, in the spin coating, when the surface temperature of the coating film after coating is 100 ° C for 120 seconds, the number of coating rotations is adjusted so that the film thickness is about -155 - 200804533, and then 22 The coating film was cured by being placed in an oven at 0 ° C for 1 hour to form a planarizing film in such a manner that the formed photodiode surface was similarly coated on the tantalum wafer.

Then, in the order of the respective colors G, R, and B, the photoresist composition for the flattening film is adjusted, and 1 〇〇 by mass of the CCD colored resin composition is applied onto the planarizing film and dried. Prebaking, pattern exposure, alkali development, rinsing, hardening and drying (post-baking) to form a colored resin film, and a color filter is formed on a wafer with a photodiode. Further, the pattern exposure was performed through a 2 μm mask pattern using an i-line stepper (FPA-3000i5+, trade name, manufactured by Canon), at 500 m J /cm 2 . In addition, the alkali imaging system uses a 40% by mass aqueous solution of an organic alkaline developing solution (CD-2000, trade name, Fujifilm Electronic Materials Co., Ltd.), and is stirred at room temperature for 60 seconds, and then rotated. Spray for 20 seconds and rinse with pure water, then rinse with pure water. Subsequently, the water droplets were blown off with high-temperature air, and the substrate was naturally dried to obtain a pattern, and then post-baking treatment was applied on a hot plate at a surface temperature of 20,000 ° C for 5 minutes. &lt;Production of CCD devices 2 to 9&gt;

The CCD devices 2 to 9 were produced in the same manner except that the pigment dispersion composition A in the production of the CCD device 1 was changed to the pigment dispersion composition. &lt;Evaluation&gt; The CCD device obtained as described above is mounted on a digital camera, at -156 - 200804533

Under the same light source, when the image of the standard color chart with the gray scale attached to the KODAK is observed on the screen, the CCD devices 1 to 5 of the present invention are more versatile than the CCD devices 6 to 9. Brightly reproduced portraits. BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 is a cross-sectional view schematically showing a preferred embodiment of a manufacturing apparatus used for producing the organic nanoparticles of the present invention.

Fig. 2 is a cross-sectional view showing another preferred embodiment of a manufacturing apparatus used for producing the organic nanoparticle of the present invention. Fig. 3 is a partially enlarged cross-sectional view showing a mixing chamber as an embodiment of the manufacturing apparatus of Fig. 2, partially by section. Fig. 4 is a partially enlarged cross-sectional view showing a mixing chamber of another embodiment of the manufacturing apparatus of Fig. 2, partially by section. Fig. 5 is a cross-sectional view schematically showing another preferred embodiment of the manufacturing apparatus used for producing the organic nanoparticles of the present invention. Fig. 6 is a cross-sectional view showing still another preferred embodiment of the manufacturing apparatus used for producing the organic nanoparticle of the present invention. Fig. 7 is a front view schematically showing an example of a dissolver stirring blade used in the production of the organic nanoparticles of the present invention. Fig. 8 is a pictorial representation of the dissolver agitating blade of Fig. 7. Fig. 9 is a schematic view showing an example of a stirring portion for manufacturing the organic nanoparticle of the present invention, which is composed of a rotatable turbine portion and a baffle portion having a slight gap around it. Sectional view. -157-200804533 Fig. 10 is an explanatory view showing a configuration example of one of the ultrafiltration devices used in the production of the organic nanoparticles of the present invention. [Main component symbol description]

11 Container 11a Liquid tank (solvent) 11b Liquid level 12 Stirring blade 13 Mixing chamber 14 Supply tube 14a Supply tube opening 15 Rotary shaft 16 Motor 17 Housing (mixing chamber wall) 18 Hole (圚-shaped hole) 1 9a, 1 9b Mixing blade 21 container (stirring tank outer wall) 2 1a Stirring tank 22 Stirring blade 23 Discharge pipe 24a, 24b Supply pipe 25 Rotary shaft 50 Stirring device 3 2, 33 Supply port 36 Discharge port - 158 - 200804533

40 dense 41,42 stir 46 outside 48,49 horse 61 round 62 leaf 63 spin 74 can 75 through 81 close 82 pass 83 super 84 fill 85 through 86 reverse sealing plate mixing blade magnet to disk part of the shaft rotating shaft turbine Immobilized baffle part of the dispersion of the container ring with the pump filter module filled with pure water meter with the flow meter water meter with the flow meter direction washing pump

-159-

Claims (1)

200804533 X. Patent application scope: 1 _ An organic nanoparticle' is characterized by an organic material, the number average particle diameter is 50 nm or less, and (volume average particle diameter) / (quantitative average particle diameter) is 1 · 0 ~2.0. 2. The organic nanoparticle according to claim 1, wherein the organic material is an organic pigment. 3 · The organic nano particles as claimed in item 2 of the patent scope, wherein the above organic The pigment is selected from the group consisting of an azo pigment, a phthalocyanine pigment, a quinophthalone pigment, a porphyrin pigment, a cyanine pigment, a merocyanine pigment, a fullerene pigment, and a polycyclic ring. A group consisting of an aromatic pigment and a polyacetylene pigment. 4 _ The organic nanoparticle according to claim 2 or 3, wherein the organic pigment is a red or purple organic pigment. 5. The organic nanoparticle of claim 4, wherein the organic pigment is a pyrrolopyrrole pigment. 6. The organic nanoparticle according to claim 5, wherein the pyrrolopyrrole pigment is a diketopyrrolopyrrole pigment represented by the following formula (Z), (Z) 7. The organic nanoparticle according to claim 5, wherein the pyrrolopyrrole pigment is a diketopyrrolopyrrole of the following formula (W) -160-200804533 8. The organic nanoparticle according to item 5 of the patent application, wherein the above-mentioned sleepy% pyrrole pigment is a diketopyrrolopyrrole represented by the following formula (V). Material, ', 9. The organic nanoparticle of claim 4, wherein the organic pigment is a dioxin pigment. 1 0. The organic nanoparticle according to claim 9, wherein the dioxo pigment is C.J. Pigment Violet 37. 1 1 The organic nanoparticle according to claim 9, wherein the dioxic pigment is C.I. Pigment Violet 23. 1. The organic nanoparticle according to any one of claims 1 to 3, which is a solution which dissolves the above organic material in a good solvent and is compatible with the above-mentioned good solvent, and for the above organic material The organic solvent prepared by mixing the solvent of the poor solvent is as follows: 13. The organic solvent of the organic material of the patent application No. 12 of the above-mentioned patent No. -161 - 200804533 is selected from the aqueous solvent and the alcohol solvent. A group consisting of a ketone-based solvent, an ether-based solvent, an anthraquinone-based solvent, an ester-based solvent, and a mixture thereof. 1 . The organic nanoparticle of claim i, wherein the good solvent of the organic material is selected from the group consisting of an aqueous solvent, an alcohol solvent, a ketone solvent, an ether solvent, a flavonoid solvent, and an ester system. A group of a solvent, a guanamine-based solvent, and a mixture of these. The organic nanoparticle dispersion composition of the invention is characterized in that it comprises an organic nanoparticle as in the first item of the patent application, and a polymer compound having a mass average molecular weight of 1 〇〇 〇 or more. 16. The organic nanoparticle-dispersed composition according to claim 15 wherein the polymer compound is represented by the following formula (1): wherein R1 represents (m + n) a linking group of a valence, R 2 represents a single bond or a divalent linking group, and A 1 represents a group selected from an acidic group having a basic nitrogen atom, a urea group, a urethane group, and a coordination group. a monovalent organic group of a group of a group having a carbon atom number of 4, a group of carbon atoms of 4 or more, an alkoxy group, an epoxy group, an isocyanate group, and a group of a hydroxyl group, or an organic group having a substituent a dye structure or a monovalent organic group of a heterocyclic ring; wherein, η of the A1 groups may be the same or different from each other, P 1 represents a polymer compound residue, m represents a number of 1 to 8, and η represents 2 to 9 The number, m + n system satisfies 3~10]. -162- 200804533 1 7. A color-sensitive photosensitive resin composition containing at least an organic nanoparticle as in the first aspect of the patent application or an organic nanoparticle dispersion as disclosed in claim 15 or 16. Compositions, binders, monomers or oligomers, and photopolymerization heuristics or photopolymerization heuristics. 1 8 . Dispersion composition of organic nanoparticles in the case of patent application No. 15 or 16. And the organic nanoparticle dispersion composition is an inkjet inkjet. A photosensitive resin transfer material characterized in that a photosensitive resin layer containing the colored photosensitive resin composition of claim 17 of the patent application is provided on a temporary support. A color filter comprising a photosensitive resin composition as claimed in claim 7 or a photosensitive resin transfer material according to claim 19 of the patent application. 2 1 - A liquid crystal display device characterized by having a color filter as in claim 20 of the patent application. The liquid crystal display device of claim 21, wherein the liquid crystal display device is of a VA mode. A CCD device characterized by having a color filter as in claim 22 of the patent application. -163-