TW200806754A - Pigment dispersion composition, and colored photosensitive resin composition, photosensitive resin transcription material using it, and color filter, liquid crystal device , CCD device using them - Google Patents

Abstract

Provided is a pigment dispersion composition with low moisture content, which has organic pigment nano-particle containing stable dispersion property, nano-size and sharp peak of particle diameter distribution. Further, provided are a colored photosensitive resin composition, an ink-jet ink for color filter and a photosensitive resin transcription material using the said pigment dispersion composition, which has excellent stability and high contrast. Furthermore, provided are color filter, liquid crystal device and CCD device, which use that mentioned above, so as to perform excellent display characteristic of high contrast and stability. A pigment dispersion composition has organic pigment nano-particle and organic solvent is provided, which is characterized in that in the said organic pigment nano-particle, the particle ration of the primary particle size lower than 15 nm is less than 10 %; the particle ratio of the primary particle more than 60 nm is less than 10 %; and the moisture content is ranging from 0.01 mass% to 5 mass%.

Description

200806754 IX. OBJECTS OF THE INVENTION: TECHNICAL FIELD The present invention relates to a pigment dispersion composition, a color-sensitive photosensitive composition using the same, a photosensitive resin transfer material, and a color filter using the same, and a liquid crystal display. Device and CCD device. [Prior Art]

In recent years, the contest of small-sized particles has continued. In particular, the use of a pulverization method, a precipitation method, and the like, which is difficult to manufacture and to be downsized to a nanometer size (for example, a range of 10 to 1 〇〇 n m) is accelerated. Further, a particle system which is small in size to a nanometer size and which is monodisperse (in the present invention, a so-called monodispersity means that the particle diameter is uniform) is continuously being attempted. These nano-sized particle sizes are located between larger bulk particles, or smaller molecules or atoms, in areas other than the size of the past. It has been disclosed that such nano-sized microparticles lead to novel features that have not been anticipated until now. Moreover, if the monodispersity can be improved, the properties can be stabilized. For this reason, the possibility of having such nano-particles is expected in various fields, and the research department is becoming more and more popular in a wide range of fields such as biochemistry, new materials, electronic components, light-emitting display elements, printing, and medical treatment. The organic nanoparticle composed of an organic compound has high potential as a functional material because of its diversity of organic compounds. For example, polyamides are used in many fields, such as heat resistance, solvent resistance, and mechanical properties, and materials such as biochemical and mechanical virgin, which are excellent in electrical insulation. Therefore, the micronized polyimine, and the combination of the characteristics and shape of the 200806754 quinone imine, can be utilized in a wider range of fields. For example, a micronized polyimine is proposed as an additive for a toner for image formation (Patent Document 1). Further, in the case of observing an organic pigment in the organic nanoparticle, for example, a coating, a printing ink, a toner for electrophotography, an inkjet ink, a color filter or the like can be exemplified for use. These lines are now important compounds that cannot be lacking in life. Among them, pigments for inkjet inks and pigments for color filters are particularly preferable for high performance and practical use.

Regarding the color material of the ink for ink jet printing, a dye can be used in the past. However, dyes have problems in water resistance and light resistance. In order to improve these problems, pigments have been used. The image obtained by the pigment ink has an advantage of being excellent in light resistance and water resistance as compared with the image obtained by the dye-based ink. However, it is possible to dye the gap on the surface of the paper due to the size of the nanoparticle, and it is difficult to improve the monodispersity, and the adhesion to the paper is deteriorated. Further, with the increase in the number of pixels of the digital camera, the thinning of the color filter used in the optical element or the display element such as the CCD sensor is desired. Organic pigments are used in color filters. Since the thickness of the filter is mostly determined by the particle size of the organic pigment, it is desirable to produce a nanometer size and to be monodisperse and stable. The method for producing organic particles is a gas phase method (a method of sublimating a sample under an inert gas atmosphere to recover particles onto a substrate), and a liquid phase method (for example, by dissolving in a good solvent) The sample is injected into a stirred solvent or a temperature-controlled lean solvent to obtain a re-precipitation method of the microparticles), and the laser ablation method (in solution, by irradiating the dispersed sample with a laser and causing it to ablate) A method of refining particles). Further, there has been reported a manufacturing example in which the test is carried out in a desired size by the method of -7-200806754. In particular, the liquid phase method is obtained as a method for producing organic particles excellent in simplicity and productivity (see Patent Documents 2 and 3, etc.). The organic particles produced by the liquid phase method can adjust the precipitation conditions by the solvent type, the injection rate, the temperature, and the like to adjust the crystal form or the surface properties of the particles. Patent Document 3 describes the type of the poor solvent. An example of adjusting the crystal form of the quinacridone pigment. On the other hand, when the improvement of the particle dispersibility is observed, the dispersion of the conventional organic pigment is industrially carried out by various dispersing machines (a roll mill, a ball mill, a vertical I ball mill, etc.). In this case, there has been a case where the viscosity is increased by refining the particles. When the viscosity has risen, it is difficult to take out the system from the disperser, and it cannot be transported by the pipeline, and in the case of storage, it gels and becomes unusable. In order to solve such problems, it is not possible to add a dispersing agent which contributes to dispersion and a polymer which is dispersed and stabilized (see Non-Patent Document 1 and the like). In the organic pigment dispersion liquid for color filters, in order to improve the dispersibility, a polymer or Φ pigment dispersant capable of imparting essential alkali developability and dispersion stability in the production of a color filter is added ( For example, refer to Patent Document 4). However, in these methods, because the dispersion takes time and the viscosity has risen, it is not possible to meet the requirements. Although the use of the prepared pigment particles ' by the above liquid phase method has been reported to improve the dispersibility. However, all did not adequately respond to the requirements for monodisperse nanoparticle formation. For example, Patent Document 5 is a method of providing an aqueous dispersion, but there is no mention of providing a method as an organic solvent dispersion. The method disclosed in Patent Document 6 is only that the primary particle diameter is relatively large. Further, Patent Document 7 discloses that the specification of the particle size and distribution of the pigment is 200806754, but the moisture content is not considered, so that the preservation stability is deteriorated, and sufficient comparison cannot be obtained. Further, in Patent Document 8, the dispersant is disclosed only in terms of the water content, but the particle size is not considered, so that the storage stability is deteriorated and sufficient contrast is not obtained.

[Patent Document 1] Japanese Laid-Open Patent Publication No. JP-A No. Hei. No. Hei. No. Hei. [Patent Document 5] JP-A-2004-43776 (Patent Document 7) JP-A-2002-32821 (Patent Document 7) JP-A-2002-32821 No. [Non-Patent Document 1] Pigment Dispersion Technology - Surface Treatment and Dispersant Usage and Dispersibility Evaluation - Technical Information Association 1 9 9 9 SUMMARY OF THE INVENTION Problems to be Solved by the Invention An object of the present invention is to provide a dispersion An organic pigment nanoparticle having a high stability, containing a nanometer size and a sharp peak of a particle size distribution, and a pigment dispersion composition having a low water content; and the object thereof is to provide excellent stability and high contrast using the above pigment dispersion composition. The coloring photosensitive resin composition, the inkjet ink for color filters, and the photosensitive resin transfer material; and the purpose thereof is to provide a display having high contrast and excellent stability using them. Features of color film, liquid crystal display device and CCD device. Means for Solving the Problems The above problems were achieved by the following means. 200806754 (1) A pigment dispersion composition characterized by comprising a pigment dispersion composition of an organic pigment nanoparticle and an organic solvent, wherein a proportion of particles having a primary particle size of less than 15 nm in the above organic pigment nanoparticle is low The ratio of the particles exceeding 10% is less than 10% (number%), and the water content of the above composition is 0.01% by mass to 5% by mass. (2) The pigment dispersion composition according to (1) above, wherein the organic pigment particles are mixed by a solution of a dissolved organic pigment in a good solvent and a poor solvent of the organic pigment compatible with the solvent And formed nano particles. (3) The pigment dispersion composition according to the above (1) or (2), wherein the water content is 3% by mass or less. (4) The pigment dispersion composition according to the above (1) or (2), wherein the water content is 1% by mass or less. (5) The pigment dispersion composition according to any one of the above items (1) to (4) And a compound represented by the following formula (1): AR^rRLfp1) Formula (1) m [wherein R1 represents a (m + n) valent linkage group, and R2 represents a single bond or 2 a linking group of a valence, the A1 system is a hydrocarbon group selected from the group consisting of 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 monovalent organic group having a group consisting of an alkoxyalkyl group, an epoxy group, an isocyanate group, and a hydroxyl group, or a monovalent organic group containing an organic dye structure which may have a substituent or a hetero ring. In the formula, n of the A1 systems may be the same or different from each other. m represents the number of 1 to 8, η represents the number of 2 to 9, and -10- 200806754 m + η satisfies 3 to 10. The pigment dispersion composition of any one of the above-mentioned items (1) to (5), wherein the pigment dispersion composition is an inkjet ink. (7) A color-sensitive photosensitive resin composition comprising the pigment-dispersed composition according to any one of the above items (1) to (6), and a polyfunctional single having two or more ethylenically unsaturated double bonds Body, photopolymerization heuristics or photopolymerization heuristics. (8) A photosensitive resin transfer material which is characterized in that at least a photosensitive resin layer containing the colored photosensitive resin group as described in the above (7) is provided on the temporary support. (9) A color filter comprising the coloring photosensitive resin composition according to (7) above and/or the photosensitive resin transfer material according to (8) above. (10) A liquid crystal display device comprising the color filter according to (9) above. (1) The liquid crystal display device according to (10), wherein the liquid crystal display device is a VA method. (12) A CCD device characterized by comprising the color filter according to (9) above. EFFECTS OF THE INVENTION The pigment dispersion composition of the present invention can provide a color filter having a low water content and a high contrast ratio, including organic pigment nanoparticles having a high nanometer size and high dispersion stability. Further, the ink jet ink, the coloring photosensitive composition and the photosensitive resin transfer material containing the same exhibit stable performance, and the color filter having the above high contrast can be provided by using such a stable quality. -11- 200806754 Further, the color filter of the present invention has excellent stability, color purity and high contrast, and is excellent in weather resistance. The liquid crystal display device and the CCD device of the present invention using the color filter exhibit good blackness, good display reproducibility, and excellent display unevenness. [Embodiment] The best form of implementing the invention

The pigment dispersion composition of the present invention is characterized in that the organic pigment nanoparticle and the organic solvent are contained, and the proportion of the particles having a primary particle size of less than 15 nm in the organic pigment nanoparticle is less than 10% (% by number), and The ratio of the particles exceeding 60 nm is less than 10% (number%), and the water content is 质量·〇1% by mass to 5% by mass (hereinafter, when the ratio of the particles is only described in %, it is not particularly limited, and means number%). In the present invention, the proportion of the particles having a primary particle size of less than 15 n m is preferably less than 7%, more preferably less than 5%. When the ratio of the particles of less than 15 n m is more than 10%, the heat resistance and the light resistance may be deteriorated, which is not preferable. In the present invention, the ratio of the particles having a particle size of more than 60 nm is preferably less than 7% and more preferably less than 5%. When the ratio of the particles exceeding 60 nm above is 10% or more, there is a possibility that the contrast is lowered, which is not preferable. In the present invention, the water content is preferably 3% by mass or less, and 〇·〇 1% by mass to 3% by mass is preferably 1 part by mass. /. The following is better, 0_01% by mass to 1% by mass is particularly good. When the water content is more than 5% by mass, the stability is deteriorated and the performance is not good. Also, because the above water content is lower than 〇. 〇 1 mass. /. In order to dehydrate the solvent to be used, a very large energy cost is required. Therefore, when the water content is lower than 〇·〇 1% by mass, industrial production is not preferable. The organic pigment to be used in the present invention is not particularly limited as long as it can form particles by the re-precipitation method, and may be used singly, in plural, or in combination with a user. The organic pigment is not limited in the hue, and examples thereof include acenaphthoquinone, quinacridone, quinacridone oxime, hydrazine, fluorenone ketone, benzimidazolone, diazo condensate, and diazo. , azo, standard reduction blue, phthalocyanine, triarylcarbyl, dioxin, aminoguanidine, diketopyrrolopyrrole, thioindigo, isoindoline, isoindolinone, dermozone dye Or a mixture of pharmaceutically acceptable and blue ketone compounds, or a mixture thereof. More specifically, for example, C·丨·Pigment Red 1 90 (CI number 71140), CI·Pigment Red 224 (CI number 71127), C.丨. Pigment Violet 29 (CI·No. 71129), etc.茈Compound pigment, G"·Pigment Orange 43 (CI·No. 71105) #, or anthraquinone compound pigment such as 〇丄Pigment Red 194 ((:.1. No. 71100), C"·Pigment Violet 19 (C_I· No. 73900), CI Pigment Violet 42, C. 丨 Pigment Red 122 (C", number 7391 5), CI·Pigment Red 192, C_l·Pigment Red 202 (C"_ No. 73907), C·丨·Pigment Red 207 (CI number 73900, 73906), or 0 丄 Pigment Red 209 (0. 丨 _ number 7390 5) quinacridone compound pigment, C"·Pigment Red 206 (CI·No. 73900/73920), C·丨·Pigment orange 48 (CI number 7390 0/7 392 0), or 〇". Pigment orange 49 ((:.1. No. 73900/7392 0) and other quinophthalone oxime compound pigments, CI·Pigment Yellow 147 (蒽 垛蒽 compound pigment such as CI number 60645), phthalocyanone compound pigment such as CI Pigment Red.-13- 200806754 168 (C.I_No. 59300), C|•Pigment Brown 25 (C_I·No. 12510) , CI Pigment Violet 32 (c · 丨 No. 12517), c 丄 pigment 18〇(C·丨·number 21 290), c”·Pigment Yellow 181 (c·丨 number 1 1 7 7 7 ), CI _Pigment Orange 6 2 (C _ I · number ii 7 7 5), or c phthalocyanide compound pigment such as 丨Pigment Red 185 (C·丨.No. 1251 6), c•丨.Pigment Yellow 93 (C_L No. 20 710), (:.1. Pigment Yellow 94 ((3_丨) No. 2〇〇38), (:| Pigment Yellow 95 (〇.丨. No. 20034), (: 丄 Pigment Yellow 128 ((3_| number: 20037), C.l_ Pigment Yellow 166 (C_|. No. 20035), C·丨·Pigment orange ginseng 3 4 (C ·丨·number 2 1 1 1 5 ), C _ I _ Pigment orange 13 (〇丄 number 2111〇), 〇.1· Pigment orange 31 (: 丨. number 20050 ), 〇丄Pigment Red 144 (〇)|No. 20735), CI·Pigment Red 166 (c) No. 2〇73〇), c丨Pigment Red 220 (C_I_No. 20055), C”·Pigment Red 221 (CI ·Dimensions 20065), C"· Pigment Red 242 (C_I. No. 20067), C_l. Pigment Red 248, C"_Pigment Red 262, or CI Pigment Brown 23 (C·丨·No. 20040) Condensation compound pigment, CI Pigment Yellow 13 (c•丨 number 211〇〇), c.|·Pigment Yellow 83 (C”·No. 21108), or C”·Pigment Yellow 188 (CI No.) 21094) | A diazonium compound pigment, c丨 pigment red 187 (c•丨·number 12486), C_I. Pigment red 170 (c·丨 number 1 2475), c_丨 pigment yellow 74 (c丨 number 11714) , C.|_Pigment Yellow 15〇 (c丨 number 48545), c”·Pigment Red 48 (CI·Number 1 5865), c”·Pigment Red 53 (C·丨.No. 1 5585), c丄Pantant Tan An azo compound pigment such as 64 (C_丨·number 彳276彳) or c". Pigment Red 247 (c. 丨 number 15 915), (: _|_Pigment Blue 6〇 (〇丄号69800) Standard reduction blue compound pigment, c·丨·Pigment Green 7 (c 丨. No. 74260), Cl_Pigment Green 3e (C′′·No. 74265), Pigment Green 37 (c′_number 74255), Pigment Blue 16 a phthalocyanine compound pigment such as (C_I·number 741 00), C·丨·Pigment Blue 75 (CI-14-200806754 No. 74160·2), or 1 5 (C·I. No. 7 4 1 6 0) 〇_1.Pigment blue 56 (〇.1. No. 42 800), or (:_丨. Pigment blue 61 (().|. No. 42765:1), etc. Triaryl carbon gun compound pigment, pigment Dioxane compound pigment such as Violet 23 (CI·No. 51319) or CI·Pigment Violet 37 (C_I·No. 51345), C_L pigment 177 (Cj·number 653〇〇), etc., the female genus 醌 compound pigment, C. I. pigment red 2 5 4 (C · 丨. number 5 6 1 1 0 ), C. I · pigment red 2 5 5 (C · I · number 5 6 1 0 5 0 ), C _ I. Pigment Red 2 6 4, CI _ Pigment Red 272 (0_丨 _ pain code 561150), 0". Pigment Orange 71, or 〇.丨.Pigment orange 73 • The diketopyrrolopyrrole compound pigment, C. 丨·Pigment Red 88 (C·丨·No. 73312): #的余余化合物颜料, ci pigment 黄丨号56298),〇_ 1. Isoporphyrin compound pigment such as Pigment Orange 66 (〇.1 No. 4821 0), CI·Pigment Yellow 109 (C.I_No. 56284), or CI Pigment Orange 6 1 (C · L number 11 2 9 5 ) iso-polinone compound pigment, c · 丨. pigment orange 4 0 (C _ 丨. number 5 9 7 0 0 ), or C · I pigment red 2 1 6 (C _ 丨 · number 59710), such as a dermazone dye compound pigment, or a suitable chloroform compound pigment such as c. quinone pigment violet 31 (60010). Among them, a quinacridone 0 compound pigment, a diketopyrrolopyrrole compound pigment, a dioxin compound pigment, a phthalocyanine compound pigment, or an azo compound pigment is preferred, a diketopyrrolopyrrole compound pigment or two A cauterine compound pigment is preferred. Hereinafter, the diketopyrrolopyrrole compound pigment or the dioxo compound pigment will be described in further detail. C.LP.R.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 are enlarged by the color reproduction region. Therefore, try to use its color filter. However, the pigments of ^ can not cope with the requirements of purity or contrast of color -15-200806754. Even if it is obtained by the method of inkjet ink, bead dispersion, or salt honing described in JP-A-2003-336001, a good color filter cannot be obtained. 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. In the liquid crystal display device having the color filter, the blackness and the redness of the Φ are excellent, and the display unevenness is suppressed.

In the above diketopyrrolopyrrole compound pigment, C_I.PR254 (compound represented by the following formula (Z)), 255 (compound represented by the following formula (W)), and 264 (the following formula) The compound represented by (V) is preferred, and CJ.PR254 is more preferable from the viewpoint of absorption spectrum. Further, all of the commercially available persons such as Irgaphor Red B-CF, Cromophtal DPP Red BO, Irgazin DPP Red BO, and Microlen DPP RED BP can be used for C.I.P.R.254. For C.I.P.R. 255, Cromophtal Coral φ Red C, Irgazin DPP Red 5G, or the like can be used. C.I.P.R.264 can be used Hostapeperm Rubin D3B LP2615, Irgazin DPP Rubin TR

-16 200806754

The receiver's illustrate a cockroach compound pigment. In recent years, as a coloring agent for a blue pixel of a color filter, a color purity of a color filter can be improved by using, for example, c · I. P. B · 1 5 : 6. However, a light source such as a cold cathode tube which is often used for a light source of a liquid crystal display device emits a little light on the long-wave side of the blue light-emitting peak, and thus the chromaticity is inferior to NTSC. This problem can be improved by adding (e.g., about 5%) C · I _ P_ V_ 2 3, 3 7 as a representative dioxo compound pigment. On the other hand, although the color φ color filter of the high color purity is expected to improve the contrast and improve the display characteristics, the conventional bead dispersion method or the salt honing method is not satisfactory. On the other hand, according to the method for producing a pigment dispersion composition of the present invention, a dioxo compound pigment having a particle size distribution of a nano-sized pigment can be obtained. Further, it is also possible to form a dispersion of the dioxin-containing pigment microparticles excellent in stability over time. For this reason, the color filter system 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 degree of sharpness and blueness are excellent, and the reproducibility is excellent, and the display unevenness is suppressed. Further, C.I.P.V.23 can be used by all commercially available persons such as Cromofine Violet RE, Fastgen Super Violet BBL, Helio Fast Violet EB, Microlith Violet RL-WA, Sanyo Fast ▽ 1〇丨6161^. 0.110^.37 can be used (^〇〇1(^»^3 1 Violet B, Microlith Violet BA, etc.. In the pigment dispersion composition of the present invention, two or more organic pigments may be combined. Or a solid solution of an organic pigment. The organic pigments are, for example, azo dyes, cyanine dyes, merocyanine pigments, coumarin pigments, etc. Polymeric organic materials are, for example, polyacetylene and polyruthenium. In the present invention, the organic pigment nanoparticle is a solvent which is compatible with the above-mentioned good solvent and which is a poor solvent with respect to the organic pigment by dissolving the organic pigment in the organic pigment solution of the good solvent (hereinafter, The solvent may be formed by mixing [a poor solvent of an organic pigment] or simply referred to as a "lean solvent" (hereinafter, this method is also called "re-precipitation method", and contains the organic pigment obtained at this time. The dispersion of the nanoparticles is also referred to as "organic particle re-sinking liquid φ". Here, "good solvent" is a solvent/poor solvent having a large solubility to the ruthenium pigment. Solvent. Used in this In order to produce organic pigment nanoparticles, it is necessary to have sufficient solubility difference of organic pigments, and the solvents satisfying the requirements can be used in combination with each other. The poor solvent of the organic pigments is only required to dissolve the organic pigments. The solubility of the solvent-soluble organic pigment of the organic pigment is preferably 0.02% by mass or less, more preferably 0.01% by mass or less, and the solubility of the organic pigment to the poor solvent is preferably. There is no special -18·200806754 The lower limit of the ground is only 0.000001 mass in consideration of the organic pigment generally used. The solubility may also be the solubility in the case of being dissolved in the presence of an acid or a base. The compatibility between the good solvent and the poor solvent or the uniformity of the mixture is preferably 30% by mass or more, more preferably 50% by mass or more, based on the amount of the solvent dissolved in the poor solvent. The dissolution of the good solvent for the poor solvent There is no particular upper limit, and in fact, it can be mixed with each other in an arbitrary ratio, for example, an aqueous solvent (for example, water). Or hydrochloric acid, Φ sodium hydroxide aqueous solution), alcohol compound solvent, ketone compound solvent, ether compound solvent, aromatic solvent, carbon disulfide solvent, aliphatic solvent, nitron compound solvent, halogen compound solvent, ester compound solvent, ionic The liquid, the mixed solvent or the like is preferably an aqueous solvent, an alcohol compound solvent, a ketone compound solvent, an ether compound solvent, an ester compound solvent, or a mixture thereof, and 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 Φ, 1-methoxy-2-propanol, etc. The ketone compound solvent is, for example, acetone, methyl ethyl ketone or methyl isophthalate. Butyl ketone and cyclohexanone. Examples of the ether compound solvent include dimethyl ether, diethyl ether, tetrahydrofuran and the like. The aromatic solvent is exemplified by benzene, toluene and the like. The aliphatic compound solvent is, for example, hexane or the like. The nitronium compound solvent is, for example, acetonitrile or the like. Examples of the halogen-based compound solvent are methylene chloride, trichloroethylene, and the like. The solvent of the ester compound is, for example, ethyl acetate, ethyl lactate or 2-(1-methoxy)propyl acetate. The ionic liquid system is, for example, a 1-butyl-3-methylimidazole key and a salt of "6_." Next, a good solvent for dissolving an organic pigment will be described. -19- 200806754 The organic solvent is soluble because of a good solvent. The pigment is not particularly limited as long as it can be dissolved or uniformly mixed with the above-mentioned poor solvent. The solubility of the organic pigment in the solubility of the organic solvent is preferably 0.2% by mass or more, and 0.5% by mass or more. Preferably, the solubility of the organic pigment in the good solvent is not particularly limited, but it is actually 50% by mass or less in consideration of the organic pigment generally used. The solubility may also be dissolved in the presence of an acid or a base. Solubility. The preferred range of compatibility or uniform mixing of the poor solvent with the good solvent is as described above.

Examples of the 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, and aliphatic solvent. , a cerium nitrate solvent, a sulfonium 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 a mixture thereof, preferably an aqueous solvent, an alcohol compound solvent Φ, an ester compound solvent, an arsenic compound solvent or a guanamine compound solvent, an aqueous solvent, an arsenic compound solvent or hydrazine. The amine compound solvent is more preferred, and the sulfonium compound solvent or the guanamine compound solvent is particularly preferred. Examples of the hydrazine compound solvent include dimethyl hydrazine, diethyl hydrazine, hexamethylene fluorene, and cyclobutyl hydrazine. The indoleamine compound solvent is, for example, N,N-dimethylformamide, 1-methyl-2-pyrrolidone, 2-pyrrolidone, 1, 3-dimethyl-2-imidine diketone. , 2-pyrrolidone, ε-caprolactam, formamide, n-methylformamide, acetamide, Ν-methylacetamide, ν, Ν-dimethylacetamide, hydrazine -methylpropanamide, hexamethylphosphonium triamine, and the like. -20- 200806754 Further, the concentration of the organic pigment dissolved in the organic solvent of the good solvent is preferably such that the organic pigment is in a range of a saturated concentration of the good solvent or even about 1/100. The conditions for the preparation of the organic pigment solution are not particularly limited, and a range from atmospheric pressure to subcritical and supercritical conditions can be selected. 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 pigment of the present invention must be uniformly dissolved in a good solvent, and it may be dissolved in an acidic or alkaline state. In general, a pigment having a base which can be fundamentally decomposed in the molecule is basic, but it is acidic when it is not present in the basic dissociable group, and many of the molecules have a nitrogen atom which is easy to add a proton. For example, quinophthalone, diketopyrrolopyrrole, and a diazo condensed pigment are dissolved in an acidic state by a basic or phthalocyanine pigment. 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 or diazo. An organic base such as dicyclohexadecene (DBU) or a metal alkoxide is more inorganic than a lanthanide.

The amount of the base to be used is not particularly limited as long as the amount of the pigment can be uniformly dissolved. However, in the case of an inorganic base, it is preferably 1 to 30 moles per mole of the organic pigment, more preferably 1 (^25 molar equivalents, more preferably 1.0 to 20 mole equivalents. In the case of an organic base, preferably from 1 to 100 100 moles equivalent to the organic pigment, more preferably 5.0^ 〇〇 molar equivalents More preferably, it is 20 to 100 mole equivalents. The acid used in the case of acidic dissolution is an inorganic acid such as sulfuric acid, hydrochloric acid or phosphoric acid, or acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, or It is preferably an organic acid such as trifluoromethanesulfonic acid, and is preferably a mineral acid. Particularly preferred is a type of sulfuric acid. The amount of the acid used is a uniform amount of the organic pigment which is uniformly dissolved, and is not particularly limited. In the case where the excess amount of the base is used, it is preferably 3 to 500 mol equivalents, more preferably 10 to 500 mol equivalents, and more preferably 30, in the case of the inorganic acid and the organic acid. ~200 moles in the mixing of alkali or acid with organic solvents, as a good organic pigment When the medium is used, since the alkali or the acid is completely dissolved, a certain amount of water of φ or a solvent having a high solubility to a base or an acid such as a lower alcohol can be added to the organic solvent. The amount of water or lower alcohol is relative to The total amount of the organic pigment solution is preferably 50% by mass or less, and 30% by mass or less. Specifically, water, methanol, ethanol, η-propanol, isopropanol, butanol or the like can be used. The solvent condition at the time of particle production, that is, precipitation and formation of organic particles is not particularly limited, and a range from normal pressure to subcritical and supercritical conditions can be selected. The temperature at normal pressure is -30 to 100 °. C is preferred, -10 to 60 ° C is preferred, and 〇 ~ 30 ° C is particularly preferred.

When the organic pigment solution and the lean solvent are mixed, either one of them may be added and mixed, and the organic pigment solution may be added to the poor solvent to be mixed, and it is preferred that the poor solvent is stirred. The stirring speed is preferably 100 to 1 0000 rpm, 150 to 8000 rpm is preferred, and 200 to 6000 rpm is particularly preferred. The addition system may or may not use a pump. 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 pigment 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 preferred. /20~3/8 is especially good. -22- 200806754 The concentration of the organic particle re-sinking liquid is not particularly limited as long as it can form organic particles, and it is preferably in the range of 10 to 40000 mg with respect to the dispersion medium of 1 μm of the organic pigment nanoparticle. The range of 20~30000mg, especially the range of 50~25000mg. Further, the modulation scale at the time of formation of the organic pigment nanoparticle is particularly limited, and the preparation amount of the poor solvent is preferably from 1 to 2000 L, and the modulation scale of from 50 to 1,000 L is preferable. The particle size of the organic pigment nanoparticle is determined by the number of measurement methods to represent the average size of the group, but the more commonly used is the mode diameter indicating the largest distribution, and the central axis corresponding to the integral distribution curve. The mean diameter, various average diameters (quantity average, length average, area average, weight average, volume average, etc.), etc., are not particularly limited in the present invention, and the average particle diameter is referred to as a number average diameter. The average particle diameter of the organic pigment nanoparticle (primary particle) is a nanometer size, and the average particle diameter is preferably 1 nm to 1 μm, preferably 1 to 200 nm, more preferably 2 to 100 nm, and particularly preferably 5 to 80 nm. . Further, the particles formed by the method for producing a pigment dispersion composition according to the present invention may be a crystal growth particle, an amorphous particle, or a mixture thereof. Further, the index indicating the monodispersity of the particles 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 employed. In the method for concentrating organic pigment nanoparticles, the monodispersity of particles (primary particles) contained in the organic particle dispersion used, that is, Μν/Μη, is preferably 1_〇~2·0, 1.0. ~1·8 is preferred, and 1·0~1·5 is particularly good. The method for measuring the particle diameter of the organic pigment nanoparticle is, for example, a microscopic method, a gravimetric method, a light scattering method, a light blocking method, an electrical resistance method, an acoustic -23-200806754 method, a dynamic light scattering method, a microscopic method, and a dynamic method. Light scattering is particularly good. \ Microscope systems for microscopy such as scanning electron microscopes, transmission electron microscopes, etc. Examples of the particle measuring device by the dynamic light scattering method are Nanotrack UPA-EX1 50 manufactured by Nikkiso Co., Ltd., and DLS-7000 series manufactured by Otsuka Electronics Co., Ltd. Dynamic Light Scattering Photometer. The pigment dispersion composition of the present invention preferably contains a dispersant. The step of containing the dispersing agent in the pigment dispersion composition is not particularly limited, and it is preferable to add a dispersing agent to both the organic pigment solution and the lean solvent, or the dispersing agent solution may be used in other systems. The above two liquids are added at the time of formation of the organic nanoparticle. It is also possible to use a pigment particle or a pigment particle which has been subjected to surface treatment by a dispersant in advance, or a surface treatment which promotes adsorption of the dispersant. 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 another aggregation. The dispersing agent which can be used is, for example, an anionic, cationic, diionic, nonionic or pigment derivative of a low molecular weight or high molecular weight φ subdispersant. Further, the molecular weight of the polymer dispersant may be any one as long as it is soluble in the solution, and is preferably a molecular weight of 1.000 to 2,000,000, preferably 5,000 to 1,000,000, more preferably 10.000 to 500,000, and most preferably 10,000 to 100,000. . 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 methylallate, polyvinyl alcohol-partial butyralate, vinylpyrrolidone-vinyl acetate copolymer, polyethylene oxide/propylene oxide block copolymer, poly Acrylate-24-200806754, Polyethyl sulphate, poly(4- succinyl) salt, poly amide, polyamine salt, condensed naphthalene sulfonate, cellulose derivative, powder derivative Wait. Further, natural polymers such as alginate, gelatin, albumin, casein, arbor gum, toluene gum, and lignosulfonate can also be used. Among them, polyvinylpyrrolidone 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, December 2001 Φ issue). The anionic dispersant (anionic surfactant) may, for example, be an N-fluorenyl-N-alkyl taurate, a fatty acid salt, an alkyl sulfate salt, an alkylbenzene sulfonate or an alkyl group. Naphthalene sulfonate, dialkyl sulfosuccinate, alkyl phosphate salt, naphthalenesulfonic acid formalin condensate, polyoxyethylene alkyl sulfate salt, and the like. Among them, N-fluorenyl-N-alkyl taurates are preferred. The N-fluorenyl-N-alkyl taurate is preferably described in the specification of Japanese Patent Laid-Open No. Hei 3-2 73 06 7 . These anionic dispersing agents can be used singly or in combination of two or more.

Anthraquinone dispersant (cationic surfactant) contains a quaternary ammonium salt, an alkoxylated polyamine, an aliphatic amine polyglycol ether, an aliphatic amine, and is induced from an aliphatic amine and an aliphatic alcohol. Diamines and polyamines, imidazolines induced by fatty acids, and salts of such cationic substances. These polycationic 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 having an anionic group portion of the above anionic dispersing agent and a cationic group portion having a cationic dispersing agent in the molecule. The nonionic dispersing agent (nonionic surfactant) may, for example, be poly-25-200806754 oxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene fatty acid, sorbitan fatty acid ester, Polyoxyethylene sorbitan fatty acid ester, polyoxyethylene storage amine, glycerin fatty acid ester, and the like. Among them, polyoxyethylene compound 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 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 group-containing pigment dispersant when preparing an organic pigment solution which is dissolved in a good solvent. Here, the amine group may include a primary amino group, a secondary amino group, and a tertiary amino group, and the number of the amine groups may be one or plural. A pigment derivative compound having a substituent having 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, the compounds described in JP-A-2000-239554, 2003-96329, JP-A-2001-31 885, JP-A-H05-339949, and JP-A-5-72943 , but not subject to these restrictions. -26-200806754 The dispersing agent containing an amine group used in the method for producing a pigment dispersion composition of the present invention is not limited thereto, and may be selected from the following formulas (D1), (D3), and (D4). At least one of the compounds shown. <1 _ Compound represented by the formula (D1)> Formula (D1)

--ν=ν—X-Y

In the formula (D1), A represents a component which forms an azo dye with X-Y. The above A may be arbitrarily selected as long as it is a compound which forms an azo dye after coupling with a heavy-key compound. The specific examples of the above A are as follows, but the present invention is not limited thereto.

27- 200806754

In the formula (D1), X represents a group selected from a monovalent bond or a divalent linking group represented by a structural formula of the following formula (ί·) to (ν). -Q \CONH— (i) CONH— (ii) \S02NH - (iii) Ο— (V) ~〇-so2nh- (iv)

In the formula (D1), Y represents a group represented by the following formula (D2). Formula (D2) (GONH, Z-NR2i)a Η (1) In the formula (D2), Ζ represents a lower alkyl group. The lanthanide is represented by _(CH2)b-, but the b is an integer of 1 to 5, preferably 2 or 3. In the formula (〇2), 4'21 represents a lower alkylamino group or a 5- to 6-membered saturated heterocyclic group containing a nitrogen atom. In the case where the -NR21 is a lower alkylamine group, it is represented by an integer of _N(CrH^ + i)2'r series τρΜ~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 is preferably a heterocyclic group represented by the following structural formula -28-200806754.

Pyrrole steep ring Piper steep ring The above formula (D2)' and the -NRai system may each have a lower alkyl group and a thyloxy group as a substituent. In the above formula (D 2 ), a represents 1 or 2, and is preferably represented by 2. Specific examples of the compound represented by the above formula (D 1 ) are shown below, but the present invention is not limited by the specific examples. 200806754

3.

ΝΗ00^^〇_0 〇nhc(c2h as OOMH(CH2)2N(C2H5)2 €ΟΝΗ(ΟΗ^2Ν(〇2Η^2 5. Η

Nhcx5h-^H^^

°=<.上 il 9〇ch$ j^comtcH^rno^^ βΜΗΟΟΟΗ-Ν=Ν·Η^ )〉 ^^CONHtCHgJaMiCaH^

H

C〇m(CH2)2H{C^2 -CONHtCH^gNfCsH^

-30- 200806754

NHCOCH-N=N-<^^h-S02NHH^J COMH(CH2)3N(C She CONH(CH 〇2 called 2

1 0.

CONHiCHafeNtCaHsfc CONHtCHaJgNiCgHgb

CONHtCH^aNiCsH^ CONHtCH^sNCCgH^g

CONH(CH2)3N(CH3)2 CONH(CH2)3NCCHa)2

-31- 200806754 1 4·

;Η3 tfOCHa NHCOCH-M=l

pONH(CH2)2l^] CONHfCH^ 5. CONHtC^

dcHs ^CONH(CH2)aN^^

1 9.[〇=<

H

F00^ /?=^CONI NHCOCH-NH^(( ))~C〇NH-(()> ^-CONI «(CH^frKCH^a IH(CH2)5N(CHa)2 -32· 200806754

CONH(CH2)3N(C2Hs)2

twenty two·

CONH(CH2)3N(C2Hg)2

iM〇-conh-<Q COMH(CH2)3N(C2H5>2 CONH(CH2)3N(C2Hs)2 The compound represented by the formula (D1) can be described in, for example, JP-A-2000-239554 Synthesized by the method. <2. Compound represented by the formula (D3)> 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 quinophthalone compound dye, a dioxane compound dye, an anthraquinone D-dye compound dye, and an anthracene. An anthrone compound dye, an indanthrone compound pigment, a flavanone compound dye, a dermozone compound dye, an anthrone compound dye, an anthraquinone compound dye, and an organic pigment residue of a thioindigo compound pigment, among which A nitrogen compound dye or a di-33-200806754 anthraquinone compound dye is preferred, and an azo compound dye is preferred. X1 is not -CO-, -CONH-Y2-, -SO2NH-Y2", or -CH2NHCOCH2NH-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.

Rn and R12 are each independently substituted or unsubstituted alkyl or R11 and R12 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.

丫1 means -NH· or -0.

Zj represents a hydroxyl group or a group represented by the formula (D3a), or a case where n1 is 1 Zq may be -NH-Xi-Q. Ml represents an integer from 1 to 6, preferably from 2 to 3. N1 represents an integer from 1 to 4, preferably 1 to 2. General formula (D3a) / R11

Yr(CH2)-N

3 mi \ in the formula (D3a) ’ 丫3 Table TK-NH - or - Ο- ' ml, Rii, and R12 systems have the same meanings as in the formula (D3). More specifically, the compound represented by the formula (D3) is represented by, for example, the following formula. -34- 200806754

Rn

Q--CONH-(\ >-NH

Rii formula (D 3 — 1 ) ni formula (D 3 — 2)

•SOzNH

Q- R12 N NH(CH2)mr<-NHHO^N,

Ru

Rn = NH(CH2)^ -C chat OK: chat 乂 ^ fly ~ Rl«

-S〇zNH(CHz)sNH N CMCtQ〆if ,Rn

Rn

Ru general formula (D 3 -3) ni general formula (D 3 - 4)

-SOzNH servant H

Ru N^NH(CH2)nrN( ,Rn

Rit formula (D 3 - 5)

OH ni

Further, in the general formulae (D3-1) to (D3-6), Q, ml, n1 'Rn, and R1 2 are the same as those in the general formula (D 3 ). the meaning of. 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. -3 5- 200806754 (a)

Cu-Pc- (b) s learning 3n: ΝγΝ -C2H5 "c2h5

NH(CH2)gN /C2H5

(c)

H N=N CONH· NHCOCHCOCH3

1~3

NyNH(CH2)3<

C2H5 C2H5

NH(CH2)3N /C2h5 ^2h5 NHtT_2>3<::NYN ^C2H5 NH(CH2)3N, C2H5 (d)

.c2h5 (e)

Cu-Pc- P IB N^N丫 /C2H5 nh(ch2)3n, /C2H5 C0NH(CH2)2MH 1T〇ANANCgHs, c4h9 C4H9

NH-(CH2)3W' C2H5 -36 200806754

ΝΗ/γΝ_~5 GHs

(1) 2

The compound represented by the formula (D3) is, for example, an amine compound having R12 and an alcohol compound having Ru and R12, and reacting with a halogenated triple-trapped Φ substance, and reacting the dye compound with the obtained intermediate. And can get. In addition, the description of the specification of the special fair No. 5-72 943 can also be referred to. <3. Pigment Dispersant Containing Graft Copolymer> In the method for producing a pigment dispersion composition of the present invention, a graft copolymer having an amine group and an ether group is contained, and may be appropriately selected if necessary. Dispersing agent for other 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 (Mw) of the above graft copolymer is preferably -37 to 200806754 3000 to 10,000, preferably 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 temperature exceeds 100 Å, 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 a gel permeation layer method (carrier: tetrahydrofuran). The above graft copolymer system contains at least: (i) terminally having ethylenic unsaturation a polymerizable low polymer having a double bond, (ii) a monomer having an amine group and an ethylenically unsaturated double Φ bond, and (iii) a polymerizable monomer having an ether group, as a copolymer unit, and may be contained if necessary (iv) Other monomers are preferred as the copolymerization unit. The content of the above-mentioned 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 (iii) the polymerizable monomer having an ether group is preferably 1 to 70% by mass, preferably 5 to 60% by mass. The content of the above polymerizable low polymer is less than 15 mass. /. When the effect of φ as a dispersant is not obtained, the aggregation of the organic nanoparticles is not prevented, and when it exceeds 98% by mass, the ratio of the nitrogen-containing monomer is decreased and the adsorption capacity to the organic particles is lowered. The dispersion is not sufficient. When the content of the nitrogen-containing monomer is less than 1% by mass, the adsorption ability to organic 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 decreased. With the three-dimensional repellent effect as a dispersing agent, aggregation of organic particles cannot be sufficiently prevented. The content of the above polymerizable monomer having an ether group is less than 1 mass. /. In the case of producing a color filter or the like, the imaging suitability is insufficient, and it exceeds 70 mass. /. At the time, the ability as a dispersant -38-200806754 was reduced. ("Polymerizable low polymer The above polymerizable low polymer (hereinafter referred to as "macromonomer") is a low polymer containing a group having an ethylenically unsaturated double bond at the terminal. In the present invention, the above polymerizability is low. Among the polymers, it is preferable to contain only the above-mentioned base having an ethylenically unsaturated double bond only in one of both ends of the low polymer. In general, the above low polymer may have, for example, selected from a homopolymer or copolymer formed of at least one monomer of (methyl)propyl phthalate, hydroxyalkyl (meth) acrylate, styrene, acrylonitrile, vinyl acetate, and butadiene Among these, a homopolymer or copolymer of an alkyl (meth)acrylate, polystyrene, etc. is preferable. In the present invention, these oligomeric polymers may be substituted with a substituent which is a substituent. It is not particularly limited, and examples thereof include a halogen atom, etc. The group having the above ethylenically unsaturated double bond is preferably a (meth) acrylonitrile group, a vinyl group or the like, among which (meth) propylene is particularly preferable. The sulfhydryl group is particularly preferred. In the present invention, the above Among the polymerizable low polymers, a low polymer represented by the following formula (E6) is preferred. C—〇—R62—S—general formula (E 6) & 6 In the above formula (E6), 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 2 to 4 carbon atoms, preferably a phenyl group. a phenyl group having 1 to 4 carbon atoms or _C〇〇r64 (here, R64 means an alkyl group or a phenyl group which may be substituted by an alcoholic hydroxyl group having 1 to 6 carbon atoms or a halogen; 39-200806754 Or an arylalkyl group having 7 to 10 carbon atoms, a phenyl group or a -COOR64 (here, R64 means an alkyl group which may be substituted by an alcoholic hydroxyl group having 1 to 4 carbon atoms). q represents 20 ~200. The above polymerizable low polymer is poly-2-hydroxyethyl (meth) acrylate, polystyrene, poly (methyl) acrylate, poly(methyl) acrylate, poly (methyl) And isobutyl acrylate, copolymers thereof, and a polymer having a (meth) acrylonitrile group bonded to the molecular terminal. The polymerizable low polymer system may be commercially available or may be appropriate In the case of Φ, the commercially available product is, for example, a terminal methyl methacrylate polystyrene low polymer (Mn = 6000, trade name: AS-6, manufactured by East Asia Synthetic Chemical Industry Co., Ltd.), sheet Methyl methacrylate-based polymethyl methacrylate low polymer (Μη = 6Ό00, trade name: AA-6, manufactured by East Asia Synthetic Chemical Industry Co., Ltd.), end-end methyl propyl thiolated Butyl acrylate low polymer (Mn = 6000, trade name: AB-6, manufactured by East Asia Synthetic Chemical Industry Co., Ltd.), sheet end methacryl oxime polymethyl methacrylate / methyl propylene acid 2-hydroxyethyl ester low polymer (Μη = 7000, trade name: AA-71 4, East Asia Synthetic #学工业(股) Company), sheet end methacryloyl thiolated polybutyl methacrylate / A 2-hydroxyethyl acrylate low polymer (Mn = 7000, trade name: 70 7S, manufactured by East Asia Synthetic Chemical Industry Co., Ltd.), sheet end methacryl thiolated polyethyl methacrylate 2-ethylhexyl ester /2-Hydroxyethyl methacrylate low polymer (Mn = 7000, trade name: AY-707S, AY-71 4S, East Asian synthetic chemistry Industrial (share) company system, etc. In a preferred embodiment of the polymerizable low polymer in the present invention, for example, at least one selected from the group consisting of a polymer of an alkyl (meth)acrylate and a copolymer of an alkyl (meth)acrylate and polystyrene. A low polymer having a number average molecular weight of -40 to 200806754 of 1,000 to 20,000 and having a (meth) acrylonitrile group at the terminal. (ii) Amino group-containing monomer The above-described amine group-containing single system is preferably at least one selected from the group consisting of the compounds represented by the following formula (E2). H2c4^(NHRV2^(E2) 0 In the above formula (E2), R21 represents a hydrogen atom or a methyl group.

The alkylene group having a carbon number of 1 to 8 is particularly preferably an alkylene group having preferably 1 to 6 carbon atoms and an alkylene group having 2 to 3 carbon atoms. X2 represents -n(r23)(r24), ·Κ25Ν(Κ26) (Κ27). 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 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 425-1^(1^26)^27)# 5 is preferably an alkylene group having 2 to 6 carbon atoms, and 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 (i.e., corresponding to the monomers represented by the following general formulae (E3), (E4)) . In the present invention, among the monomers represented by the above formula (E2), at least one selected from the group consisting of any of the following formulae (E.3) and (E4) is preferred.

Nhr32-x3 Formula (E3) In the above formula (E3), R31 is synonymous with R21. R32 is synonymous with R22 〇 X3 is synonymous with X2. -41- 200806754

In the above formula (E4), R41 is synonymous with R21. X4 is synonymous with X2, -N(R43)(R44) (here, R43fR44 is synonymous with ruler 23 and ruler 24), or -R45-N(R46)(R47) (here, R45, r46 and r47) It is preferred that the lines are synonymous with rulers 25, R26 and R27, respectively. Specific examples of the monomer represented by the above formula (E2) are, for example, dimethyl (methyl meth) acrylamide, diethyl (meth) acrylamide, diisopropyl (methyl). Acrylamide, di-n-butyl (meth) acrylamide, di-isobutyl (meth) acrylamide, morpholino (meth) acrylamide, piperidino (methyl) propylene Indoleamine, N-methyl-2-piperidyl (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-(Ν,Ν·diethylamino)propyl(meth)acrylamide, 3-(anthracene, dimethylamino)propyl (meth) acrylamide, 1-( Ν,Ν-dimethylamino)-1,1-dimethylmethyl(meth) acrylamide, 6-(anthracene, fluorenyl-diethylamino)hexyl (meth) acrylamide ( The above aminoalkyl (meth) acrylamides and the like are preferred. (Mi) Polymerizable monomer having an ether group The 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).

In the above formula (E1), R11 represents a hydrogen atom or a methyl group. R12 represents an alkylene group having 1 to 8 carbon atoms. Among them, an alkylene group having a carbon number of 1 to 6 is particularly preferred, and a alkylene group having a carbon number of 2 to 3 is more preferably used. The X1 system represents _0 feet 13 or _000 feet 14. Here, R1 3 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. R14 represents an alkyl group having 1 to 18 carbon atoms. Moreover, m3 means 2 to 200, 5 to 100 is preferable, and 10 to 100 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, polybutylene Φ diol methacrylate, etc., these may be commercially available products, or Suitable for synthesizers. The commercially available product is, for example, methoxypolyethylene glycol methacrylate (trade name: NK ester M-40G, M-90G, M-230G (above, manufactured by Toago Chemical Co., Ltd.); Name: Bremer PME-100, PME_200, PME-400, PME-1 000, PME-2000, PME-4000 (above, manufactured by Nippon Oil & Fats Co., Ltd.), polyethylene glycol monomethacrylate (commodity) Name: Bremer PE-90, PE-200, ΡΈ-350, manufactured by Nippon Oil Co., Ltd., and polypropylene glycol monomethacrylate (trade name: Bremer • PP-500, PP-800, PP) -1 000, manufactured by Nippon Oil & Fats Co., Ltd., polyethylene glycol polypropylene glycol monomethacrylate (trade name · Bremer 70PEP-370B, manufactured by Nippon Oil & Fats Co., Ltd.), polyethylene glycol Butanediol monomethacrylate (trade name · Bremer 55 P£T-800, manufactured by Nippon Oil & Fats Co., Ltd.), polypropylene glycol polybutanediol monomethacrylate (trade name: Bremera - 5050, made by Japan Oils and Fats Co., Ltd.). (iv) Other monomers The above 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 selected as appropriate, for example, aroma. Group vinyl compounds (for example, styrene, α-methylstyrene, and vinyltoluene), alkyl (meth)acrylates (for example, methyl (meth)acrylate, ethyl (meth)acrylate, ( N-butyl acrylate and isobutyl (meth) acrylate, alkyl aryl (meth) acrylate (eg benzyl (meth) acrylate), glycidyl (meth) acrylate, carboxylic acid Vinyl esters (for example, vinyl acetate and vinyl propionate), vinyl cyanide (for example, (meth)acrylonitrile and α-chloroacrylonitrile), and aliphatic conjugated dienes (for example, 1, 3 - butadiene and isoprene), (meth)acrylic acid, and the like. Among these, Φ is particularly preferably an unsaturated carboxylic acid, an alkyl (meth)acrylate, an alkyl aryl (meth) acrylate or a vinyl carboxylate. The content of the other monomer in the above graft copolymer is preferably, for example, 5 to 70% by mass. 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 function as a dispersing agent cannot be sufficiently exhibited. Preferred specific examples of the above graft copolymer are, for example: (11) 3-(anthracene, fluorene-dimethylamino)propyl acrylamide/polyethylene glycol mono(Φmethyl) acrylate/end Methyl propylene thiolated poly(methyl) acrylate copolymer, (12) 3 —(Ν,Ν-dimethylamino)propyl acrylamide/polyethylene glycol mono(meth)acrylate/ Terminal methacryl oxime polystyrene copolymer, (13) 3-(anthracene, Ν-dimethylamino) propyl acrylamide / polyethylene glycol mono (meth) acrylate / (methyl ) methyl acrylate terminal methacryl oxime polystyrene copolymer, (14) 3-( Ν, Ν dimethylamino) propyl acrylamide / polyethylene glycol mono (meth) acrylate /terminal methacryloyl thiolated methyl (meth) acrylate and 44-200806754 copolymer of 2-hydroxyethyl methacrylate copolymer, (15) 3-(anthracene, dimethylamino) propyl Copolymer of acrylamide/polyethylene glycol mono(meth)acrylate/terminal methacryl oxime methyl methacrylate and 2-hydroxyethyl methacrylate copolymer, (16)3- (^1, didimethylamino group) Copolymer of acrylamide/polyethylene glycol mono(meth)acrylate/terminal methacryl oxime methyl methacrylate and 2-hydroxyethyl methacrylate copolymer, (17) 3-( Ν,Ν-dimethylamino)propyl acrylamide/polypropylene glycol mono(methyl methacrylate)/terminal methacryl oxime poly(methyl) acrylate copolymer, (1 8 ) 3 - (N,Ν_Dimethylamino)propyl acrylamide/polyethylene glycol polypropylene glycol mono(meth)acrylate/terminal methacrylic acid poly(methyl) acrylate copolymer, ' « (19) 3-(Ν,Ν-dimethylamino)propyl acrylamide/polyethylene glycol polybutane diol-(meth) acrylate/terminal methacryl oxime poly(methyl) Methyl acrylate copolymer,

(20) 3-(Ν,Ν-dimethylamino)propyl acrylamide/polypropylene glycol polybutane diol-(meth) acrylate/terminal methacrylic acid poly(methyl) acrylate Acid methyl ester 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), Me represents a methyl form (D4) -CH2-CH-^icH2.C--\/cH2*CH' CONHC3H6NMe2 / \ C02(C2H40)23Me / 丨| Λ 15 :20:65 (weight ratio)

CO2C2H4S \ C02Mey6〇 / c / The above graft copolymer is a component which forms each of the above copolymer units, and -45-200806754 is obtained by, for example, radical polymerization of 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. For the pigment dispersant containing the graft copolymer, reference is also made to the description of JP-A-2001-31885. In order to further improve the uniform dispersibility and storage stability of the organic particles, the content of the dispersant is preferably in the range of 0.1 〇〇〇 parts by mass, more preferably in the range of 1 to 50,000 parts by mass, based on 100 parts by mass of the pigment. More preferably, the range of 5 to 2 0 Φ mass parts. When the amount is less than 0.1 part by mass, the dispersion stability of the organic nanoparticle is not observed to be improved. 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 will be described, but the present invention is not limited thereto. (Manufacturing device example 1)

Fig. 1 is a view showing a preferred embodiment of the manufacturing apparatus used in the production of the pigment dispersion composition of the present invention. The organic material solution in Fig. 1 is continuously supplied into the container 11 through the supply pipe 14. Here, the container 11 contains a poor solvent 1 1 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 the manufacturing apparatus used in the production of the pigment dispersion composition of the present invention, and a mixing chamber (stirring area) is provided in the container 11 of the manufacturing apparatus of Fig. 1. 13 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 used for the mixing in the mixing chamber 13 for -46-200806754, so that 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). And make it convective. Fig. 3 is an enlarged partial cross-sectional view showing the mixing chamber 13 as 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), 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 11a, the area other than the mixing chamber 13 is outside the stirring field, also called the stirring field), a large amount of poor solvent Formed by connecting 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 circular hole. Further, the mixer 13 is provided with a stirring blade 12, and the agitating blade is attached to the rotating shaft 15 and rotated by the motor 16. By the rotation of the stirring blade 12, the lean solvent passes through the circular hole 18 and moves upward from the bottom toward the inside of the mixer 13 to cause frequent cyclic movement. 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 estimated to be an important operational factor for the size of droplets (droplets) at the time of mixing of the organic pigment solution. Further, the stirring crucible 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 by being allowed to stay in the mixing chamber 13 In the organic pigment solution, it is preferable to rapidly extract the generated organic pigment particles and rapidly discharge them to the outside of the mixing chamber 13 so as to form large particles without generating large particles. -47- 200806754 The stirring-blade 12 system can be used in any form for the above purpose, 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 7 and does not require an attachment such as a baffle, so that the mixing effect can be further improved. Fig. 4 is another embodiment of the manufacturing apparatus of Fig. 2, which is a mixer of two mixing blades (mixing stirring blade 19a, discharging agitating Φ blade 19b) in the mixing chamber: an enlarged partial section Figure. 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 mixing strength and circulation amount can be independently set to the desired state. . (Manufacturing Apparatus Example 2) Fig. 5 is a cross-sectional view showing another embodiment of the apparatus for producing the organic nanoparticles of the present invention. The medium organic material solution and the lean solvent medium are continuously supplied to the stirring tank 21a by the supply pipes 24a, 24b, respectively. The organic material particles generated in the stirring tank 21a are retained in the stirring tank 21a, combined with other organic material particles to form larger particles, and exposed to the organic material solution supplied from the supply pipes 24a, 24b to form The large particle but not the large particles are generated. The resulting organic material particle dispersion is quickly extracted from the discharge pipe 23. 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 stirring device 50 is provided with a liquid discharge tray having a liquid mixture port 32, 33 for causing an organic pigment solution and a poor solvent to flow in, and a mixed liquid for discharging the stirring process - 48 - 200806754 The cylindrical stirring tank 38 and the stirring blades 41 and 42 of the stirring means for controlling the liquid stirring state in the stirring tank 38 in the stirring tank 38 are driven. The agitation tank 38 is composed of a cylindrical groove body 39 that faces the center axis in the vertical 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 excellent in 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, 42 are disposed apart from each other in the upper and lower ends of the agitating grooves 38, and are rotationally driven in opposite directions to each other. Each of the agitation blades 41, 42 constitutes a magnetic air coupling C with an outer magnet 46 disposed on the outer side of the groove wall (sealing plate 40) of the agitation blades 41, 42 respectively. That is, each of the agitating blades 41 and 42 is connected to the respective outer magnets 46 by magnetic force, and each of the outer magnets 46 is rotationally driven by independent motors 48 and 49 to perform reverse rotation operations.

The pair of agitating blades 4 1 and 42 disposed oppositely 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 formed in the grooves 38. Different mixing streams. Therefore, the agitating flow formed by each of the agitating blades 41 and 42 collides with each other due to the difference in the flow direction, and the high-speed turbulent flow in the accelerating groove 38 is generated in the groove 38, and even if the flow in the groove 38 is prevented from being fixed, even When the rotation of the stirring blades 41 and 42 is increased, the rotation of the agitating blades 41 and 42 is prevented from rotating to form a cavity, and the inner circumferential surface of the agitation tank 38 can be prevented from being sufficiently stirred. The so-called unsuitable occurrence of a flowing fixed flow in the groove 38 occurs. Therefore, via high -49-

200806754 The rotation of the speed-up stirring blades 41, 42 can be easily extracted, and at this time, the flow of the liquid in the groove 38 can be prevented from fixing the insufficient liquid, and the deterioration of the treatment quality can be prevented. Further, the stirring blades 41 in the stirring tank 38 are coupled to the motor 48 disposed outside the stirring tank 38, and it is not necessary to insert the rotating shaft into the groove wall of the stirring tank 38, thereby forming a closed container structure in which the rotating shaft has no insertion portion. When the mixed liquid leaks out of the tank, it can also prevent the impurity from being mixed into the liquid in the tank 38 due to the rotation of the sealing liquid. 1 In the production of the pigment dispersion composition of the present invention, the manufacturing apparatus is not only batch type Mode, continuous flow machine pigment particles, and can also correspond to mass production. Moreover, since the ratio of the machine pigment particle dispersion is rapidly discharged, the ratio of the agitator material solution to the lean solvent liquid can be often determined from the start of the fixed production to the end of the production, and the dispersion organic material is fixed, and the monodisperse organic pigment particles can be stably produced. Further, the immobilization of the liquid in the tank and the sufficient dispersion of the organic pigment particles are prevented, and impurities such as an anti-skid liquid (sealing liquid) are mixed into the solution in the tank to produce monodisperse organic pigment particles. (Production Apparatus Example 3) As an alternative aspect of the production of the pigment dispersion composition of the present invention, a leaf household method having shearing force will be described. In the present invention, the shearing force is the stirring leaf-high processing speed, and the stirring and mixing are discharged, and the magnetic system 49 is connected by the magnetic gas 49. Therefore, since the stirring tank 38 can prevent the lubricating liquid for stirring ( Density > treatment quality. It can also be produced by using the above-described configuration, and the solubility can be solid. The discharge can be mixed with the rotating shaft. Runner can further stabilize the use of the device and stir the manufacturing of the organic pigment. -50-200806754 The shear force of the droplets (microdroplets) generated after the liquid is mixed into the poor solvent. The shape is not particularly limited as long as the high shear force can be applied, but generally, for example, a pulverizing blade, a turbine blade, a spiral blade, a Pf a lid ler blade or the like is preferably used. It is preferable that the dissolver blade, the turbine portion that can rotate, and the stirring portion, the emulsification, and the dispersing device that are provided with the agitating portion formed by the baffle portion having a slight gap around the position. It is a special agitating blade which has a function of forming a high shear force, and FIG. 7 is a front view schematically showing one example thereof, and the drawing substitute photo system is shown in Fig. 8. Fig. 9 is a view showing a device for agitating, emulsifying, and dispersing a stirring portion formed by a rotatable turbine portion and a baffle portion having a slight gap therebetween and fixed at a position, for example, Microtec Nition Co., Ltd. Physcotron, T_K homogenizing mixer manufactured by Special Machine Chemical Co., Ltd., ULTRA-TURRAX manufactured by IKA Co., Ltd. The stirring speed is different depending on the viscosity of the solvent, the temperature, and the type or addition amount of the active agent. It is preferably 100 to 10000 rpm, 150 to 8000 rpm, and particularly preferably 200 to 6000 rpm. If the number of rotation is too low, the stirring effect cannot be fully exerted. Conversely, if it is too high, bubbles are trapped in the poor solvent. In the method for producing a pigment dispersion composition of the present invention, the organic nanoparticle dispersion is capable of producing a color filter coating liquid on an industrial scale or for inkjet printing by performing desalting and concentration. Concentrate of the ink. Hereinafter, the concentration and the shrinkage 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 is added to the organic nanoparticle dispersion. a solvent, a method of extracting organic nano particles in the extraction solvent phase, and filtering the concentrated nanoparticle liquid of the concentrated extract by a filter or the like; a concentration method for sedimenting the organic nanoparticle by centrifugation; A method of desalting and concentrating by filtration; a method of concentrating a solvent by vacuum freeze-drying; a method of concentrating a solvent by heating or a reduced pressure, or the like, or using such a combination is particularly preferable. In the process of dispersing the composition with the low water content pigment of the present invention, the moisture content of the concentrated wet cake is usually 15% by mass to 95% by mass in the case where the aqueous dispersion is subjected to a concentration process. /. 30% by mass to 90% by mass is preferred, and 50% by mass to 855% by mass. /. It is better. When the moisture content of the wet cake is less than 15% by mass, the pigment particles form an irreversible aggregate, and there is a possibility that the pigment particles cannot be dispersed. Further, when the moisture content of the wet cake is more than 95% by mass, a large amount of the organic solvent system becomes necessary in the subsequent step. The solvent concentrate of the pigment can also be passed during the process of obtaining the pigment dispersion composition of the present invention having a low water content. The concentration of the pigment in the solvent concentrate is usually 10% by mass to 70% by mass, and 15% by mass to 60% by mass. /. Best, 20 quality. /. ~50% by mass is preferred. Further, the water content in the concentrate is preferably 50% by mass or less based on the pigment, and more preferably 30% by mass or less based on the pigment, and 10% by mass. /. The following is especially good. The water content can be measured by any of the well-known methods. In the present invention, the Karl Fischer's method (Experimental Chemistry Lecture 15 (below) Analytical Chemistry P241~) is used to determine the water content. . The concentration of the organic nanoparticles after concentration is preferably from 1 to 100% by mass - 52 to 200806754 and from 5 to 100% by mass, more preferably from 1 to 1% 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 solution, and it is actually 1% by mass or more in consideration of the solubility of the usual solvent. The solvent forming the interface after mixing and standing is preferably 0. 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). . In such a state, it is preferable that the organic agglomerated particles are wetted by the extraction solvent, and the organic solvent, such as water, can be easily removed by filtration or the like. The extraction solvent is preferably an ester compound solvent, an alcohol compound solvent, an aromatic solvent or an aliphatic solvent, an ester compound solvent, an aromatic azide solvent or an aliphatic compound solvent, and the ester compound solvent is preferably used. Very good. The ester compound solvent is, for example, 2-(1-methoxy)propyl acetate, ethyl acetate or 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 solvent may be a pure solvent formed from the above preferred solvent, or may be a mixed solvent composed of a plurality of solvents. The amount of the extraction solvent is not particularly limited if it is capable of extracting the organic nanoparticle. However, it is preferable to use a small amount of the organic solvent to be concentrated, and the extraction system is preferably a small amount of the organic nanoparticle dispersion-53-200806754. When it is represented by a volume ratio, when the organic Nai's particle dispersion is set to 10 〇, the extraction solvent to be added is preferably in the range of 1 to 100, more preferably in the range of 10 to 90, and 20 The range of ~80 is particularly good. When too much is too concentrated, it takes a lot of time. When the amount is too small, the extraction is insufficient and the nanoparticles are left 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 100 ° C and Φ 5 to 60 ° C. Any apparatus can be used as long as it is desirable to add or mix 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 ultrafiltration. Research Disclosure No. 1 0208 (1 972) > No. 13 122 (1975) and No. 16 351 (1977) are known. As 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) / φ P.275, which is selected for the processing of organic nanoparticles. On the particle dispersion, it is necessary to find an optimum condition for suppressing particle agglutination. Further, in addition to the method of dispersing the solvent due to the membrane permeation, there is a batch type in which the constant volume type and the discontinuity of the solvent are continuously added, and the constant volume type in which the desalination treatment time is relatively short is preferable. The solvent thus replenished may be pure water obtained by ion exchange or distillation, and the pure solvent may be mixed with a dispersant or a poor solvent of the dispersant, or may be directly added to the organic nanoparticle dispersion. In the first diagram, an example of the configuration of the device for performing ultrafiltration is shown. In Fig. 10, as shown in the figure, the apparatus has a tank 81 for storing organic nanoparticles, a pump 81 for circulating the dispersion in the tank 81, and a circulation pump 、. The pump 82 removes the by-produced inorganic salt in the introduced dispersion into the permeated water ultrafiltration module 83. The osmotic water system returns the separated dispersion to the storage tank 81 again, repeating the same operation until the by-produced inorganic salt is removed.

Until the intended purpose. Further, in the apparatus, a flow meter 84 for replenishing pure water for removing a solvent which is lost in permeated water as a pure water, and a permeated water for determining the amount of pure water replenishment is provided. The flow meter 85 for measurement. Further, a counter-washing pump 86 for introducing the ice for diluting the permeated water is provided. The ultrafiltration membrane system has been assembled as a module, such as a flat plate type, a spiral type, a cylindrical type, a hollow fiber type, and a hollow fiber type, such as Asahi Kasei (share), Daisil Chemical (share), and Toray (share). It is commercially available from Nitto Denko (shares), etc., from the viewpoint of total membrane area or detergency, it is preferably a spiral type or a hollow type. Further, the fractional molecular weight which is a critical index for forming a permeable membrane component must be determined depending on the molecular weight of the dispersing agent to be used, and it is more preferably 5,000 or more and 50,000 or less, and more preferably 5,000 or more and 15,000 or less. 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 include, for example, a nano filter, a super filter, and the like. Filtration by a filter removes the residual dispersion solvent, and the organic nanoparticles in the concentrated extract are further concentrated to form a concentrated nanoparticle liquid. The method of freeze-drying is not particularly limited, and any method that the manufacturer may utilize may be used. For example, a direct refrigerant expansion method, a repetitive freezing method, a heat medium circulation method, a triple heat exchange method, an indirect heating freezing method, -55-200806754, preferably a direct refrigerant expansion method, an indirect heating freezing method, and more preferably an indirect heating freezing method. method. In any of the above methods, it is preferred to freeze-dry after performing the pre-freezing. The conditions for pre-freezing are not particularly limited, but the freeze-dried sample must be generally frozen. The apparatus for indirect heating and freezing method is preferably, for example, a small freeze dryer, an FTS freeze dryer, a LYOVAC freeze dryer, an experimental freeze dryer, a freeze dryer for research, a triple heat exchange vacuum freeze dryer, and a single cooling. Freeze dryer, HULL freeze dryer, preferably small 0 freeze dryer, experimental freeze dryer, freeze dryer for research, single cooling freeze dryer, more preferably small freeze dryer, single Cooling freeze. Junction dryer. The freeze-drying temperature is not particularly limited, and is, for example, -1 9 & -4 ° C, preferably -120 to -20 ° C, more preferably -80 to -60 ° C. The pressure for freeze-drying is also not particularly limited, and the manufacturer may suitably select, for example, 0.1 to 3 5 Pa, preferably 1 to 15 Pa, more preferably 5 to 10 Pa. The freeze drying time is, for example, 2 to 48 hours, preferably 6 to 36 hours, more preferably about 16 to 26 hours. However, these conditions are suitable for the industry. For the freeze-drying method, for example, the manual of the preparation machine technology operation manual: the preparation of the preparation machinery technology research institute, the local library, ρ·120-129 (September 2000); vacuum operation manual··Japan Vacuum Technology Co., Ltd.编, 欧姆社, ρ·328_331 (1992); Freeze and Dry Research Society: Ito Takaji, No.15, ρ·82 (1 965), etc. The following is a description of centrifugal separation. The centrifugal separator used for the concentration of the separated organic nanoparticles is any one of the organic nanoparticle particles in the organic nanoparticle dispersion (or organic nanoparticle-56-200806754 concentrated extract). The apparatus may be used. The centrifugal separator may be, for example, a widely used apparatus, and may have, for example, a function of a crude distillation (a function of absorbing a supernatant layer during rotation, a function of discharging the system outside the system), or continuous discharge of solid matter continuously. Centrifugal separators, etc. The centrifugal separation conditions are preferably centrifugal force (indicating a centrifugal acceleration several times the acceleration of gravity) 50 to 1 0000, preferably 100-8000, and 150 to 6000. The temperature at the time of separation is preferably -1 to 80 ° C, preferably 5 to 70 ° C, and particularly preferably 0 to 60 ° C depending on the type of the solvent of the dispersion.

The following is a description of drying. The apparatus used for 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 concentrated 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 a solution, 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 1 〇〇 to 1 〇〇〇〇〇 Pa, 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. Regarding the concentration ratio, for example, when the concentration of the nanoparticles in the organic nanoparticle dispersion forming the raw material is 1, the concentration in the concentrated organic nanoparticle paste is preferably concentrated to about 100 to 3,000 times, more preferably 500. ~ 2000 times or so. In the method for producing a pigment dispersion composition of the present invention, the organic particles in an agglomerated state are dispersed by the above-mentioned concentration (in the present invention, the redispersion system-57-200806754 is used to improve the dispersion of particle agglomeration in the dispersion liquid. , also known as micro-dispersion). The organic particles contained in the concentrated organic particle liquid, such as the above-mentioned extraction solvent, centrifugal separation, and drying, are usually concentrated by condensation. In this case, in order to allow rapid filter filtration and to obtain a good dispersion state 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 micro-Φ particle formation, 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 weight average molecular weight of 1,000 or more are contained in the aggregated organic particle liquid, whereby the organic particles can be appropriately finely dispersed (in the present invention, agglomerated organic The particle liquid system specifies that the aggregated organic particles are contained in the liquid, that is, the dispersion, the concentrate, the paste, the slurry, and the like, as long as the aggregated organic particles are contained. Next, the polymer compound which can be preferably used in the method for producing a pigment dispersion composition of the present invention is described in detail (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 which can be preferably used in the pigment dispersion composition of the present invention is preferably a polymer compound having a mass average molecular weight of 100 or more and a polymer compound represented by the following formula (1). -58- 200806754

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, a hydrocarbon group having 4 or more carbon atoms, or an alkoxy group. A decyl group, an epoxy group, an isocyanate group, and a monovalent organic group having a group selected from a hydroxyl group, or a monovalent organic group containing an organic dye structure which may have a substituent or a hetero ring. η A1 systems can be the same or

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 '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 (-ΝΗ2) and a substituted imido group (-NHR8, __41(3)) The organic group (herein, 1^, [^, and 尺1()) each independently represent an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 or more and 20 or less carbon atoms, and an aromatic group having 7 or more carbon atoms and 7 or less carbon atoms. (Alkyl), a monovalent organic group having a fluorenyl group represented by the following formula (a υ), in the formula (a1), each of Ra1 and Ra2 independently represents an alkyl group having 1 to 20 carbon atoms and a carbon number of 6 or more An aryl group of 20 or less, an aralkyl group having 7 or more and 30 or less carbon atoms, and a monovalent organic group having a fluorenyl group represented by the following formula (a2); in the formula (a2), Ra3 and Ra4 are each independently 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 used.

-59- 200806754 -NHCONHR15 (herein, R15 represents a hydrogen atom, or an alkyl group having 1 to 20 carbon atoms, an aryl group having a carbon number of 6. or more and 20 or less, an aralkyl group having a carbon number of 7 or more and 30 or less), and the like. . The above-mentioned "monovalent organic group having a urethane group" is, for example, -NHCOOR16 or -OCONHR17 (here, R16 and R17 each independently represent an alkyl group having a carbon number of 20 and a carbon number of 6 or more and 20 or less. An aryl group, an aralkyl group having 7 or more and 30 or less carbon atoms, or the like. The above "group containing a group having a coordinating oxygen atom" is exemplified by a group having a acetylacetone 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, a phenyl group or a naphthyl group). And the like, and a aryl group (for example, a benzyl group) having a carbon number of 7 or more. At this time, there is no upper limit on the carbon number, and it is preferably 30 or less. The "group having an alkoxyalkylalkyl 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, 3-propylidenepropyl or the like. In the above, the above-mentioned 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, and the above organic dye structure or heterocyclic ring. The organic dye structure is not particularly limited. More specifically, the organic dye structure is, for example, a phthalocyanine compound, an insoluble couple _ 60 0 - 200806754 nitrogen compound, an azo lake compound (A ζ I ake compound), an anthraquinone compound, quinacridone. An anthrone compound, a dioxane compound, a diketopyrrolopyrrole compound, a nitrogen hydrazine compound, an anthrone compound, an indanthrone compound, a flavanone compound, an anthrone compound, an anthraquinone compound, a sulfonium compound, and the like. 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, sorghum, pyrimidine, pipe trap, three tillage, trimeric methyl aldehyde, isoporphyrin, iso-φ porphyrin, Benzimidazolone, amber imine, phthalimide, naphthyl imine, hydantoin, quinone, quinoline, oxazole, acridine, acridone, hydrazine, and the like. Further, the organic dye structure or heterocyclic ring may have a substituent, and examples of the substituent include an alkyl group having 1 to 20 carbon atoms such as a methyl group or an ethyl group, and a carbon number of 6 to 16 such as a phenyl group or a naphthyl group. An aryl group, a carbon having a carbon number of 1 to 6 such as a methoxy group, an ethoxy group or the like having a carbon number of 1 to 6 such as a group, an amine group, an anthracenyl group, a sulfonylamino group, a fluorenylamine group or an ethoxy group. Alkoxycarbonyl groups such as a halogen atom such as chlorine or bromine, 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 and a third group A carbonate group or the like such as a carbonate. Further, the above oxime 1 is preferably a monovalent organic group represented by the following formula (4).

In the above formula (4), hydrazine 1 represents a hydrocarbon 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 a carbon number of 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, -61- 200806754 R18 represents a single bond or an al-valent organic or inorganic Linkage. A1 indicates V~5, a1 B1 system may be the same or different. The B1 system is synonymous with the above A1 in the general formula (4), and the preferred embodiment is also the same. The above-mentioned provincial dye structure or heterocyclic ring system is, for example, a phthalocyanine compound, an insoluble azo compound, or an azo lake (Azo lake). a compound, an anthraquinone compound, a quinophthalone compound, a dioxin compound, a diketone 'pyrrolopyrrole compound, a nitrogen hydrazine compound, an anthrone compound, an indanthrone compound, a flavanone compound, a phenanthrone compound, An organic dye Φ structure such as a phenanthrene compound or a sulfonium compound, such as thiophene, furan, hydrazine, pyrrole 'pyrroline, piropyridine, dioxane, pyrazole, pyrazoline, pyrazolidine, imidazole, oxazole , thiazole, oxadiazole, triazole, thiadiazole, pyran, pyridine, piperidine, dioxane, gustoline, hydrazine trap, pyrimidine, pipe trap, three tillage, trimeric methyl aldehyde, isoporphyrin , iso D-pyridone, benzoxazolone, amber imine, phthalimide, naphthyl imine, hydantoin, hydrazine, quinoline, oxazole, acridine, acridine A heterocyclic ring of a ketone or an anthracene. Further, the organic dye structure or the heterocyclic ring may have a substituent. The substituted φ group 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 to 16 such as a phenyl group or a naphthyl group. a carbon number of a methoxy group such as an aryl group having a carbon number of 1 to 6 such as an aryl group, a hydroxyl group, an amino group, a carboxyl group, a sulfonylamino group, an N-thioguanamine group or an ethoxylated group; Alkoxycarbonyl group having a carbon number of 2 to 7 such as a halogen atom such as a halogen atom such as chlorine or bromine, a methoxycarbonyl group, an ethoxycarbonyl group or a cyclohexyloxycarbonyl group, a cyano group and a third butyl carbonate. Such as carbonate groups and the like. R18 represents a single bond or a 1+1 valent linkage, and a1 represents 1 to 5. The linking group R18 contains 1 to 1 carbon atoms, 1 to 10 nitrogen atoms, 0 to 50 oxygen atoms, 1 to 200 hydrogen atoms, and 〜20 to 20 carbon atoms. Sulfur-62- 200806754 A radical formed by an atom, which may be unsubstituted or substituted. R18 is preferably an organic linkage. Specific examples of R18 include, for example, the following structural units or a combination of the structural units. 4一巧一+ X 4-一§〇- 4一一一一一写(t-1) (t-2) (t-3) (t-4) (t-5) (t-6) ( T-7) (t-8) (t-9) (t-10)(t-11) (t-12)

(t-2〇) -OCN-^-6-n--N-6-CN——|-tl— -ό-Ν--(>c- (t-14) (t-15) (t -16) (t-17) (t-18) (t -19) -S=G——-6=8- HC=C--C-0--¢) (t-21) (t_22) ( t - 23) (t-24) (t-25) (t - 26)

(t-27) (t-28) (t-29) (t-30) (t-31) (t-32) (t-33) (t-34) In the case where R18 has a substituent, the substitution Examples of the group include an alkyl group having 1 to 20 carbon atoms such as a methyl group or an ethyl phenyl group, an aryl group having 6 to 16 carbon atoms such as a phenyl group or a naphthyl group, a hydroxyl group, an amine group, a carboxyl group, a sulfonylamino group and a N group. - a fluorenyloxy group having 1 to 6 carbon atoms such as a thiopurine group or an ethoxylated group; an alkoxy group having 1 to 6 carbon atoms such as a methoxy group or an ethoxy group; and a halogen atom such as chlorine or bromine; An alkoxycarbonyl group having 2 to 7 carbon atoms such as an oxycarbonyl group, an ethoxycarbonyl group or a cyclohexyloxycarbonyl group, or a carbonate group such as a cyano group or a t-butyl carbonate. In the above formula (1), r1 represents a (m + n)-valent linking group. The m + n system satisfies 3 to 10 °. The (m + n) valent linking group represented by the above R1 contains 1 to 100 carbon atoms of -63 to 200806754, one to ten nitrogen atoms, and 0 to The group formed by 50 oxygen atoms, one to two hydrogen atoms, and one to twenty sulfur atoms may be unsubstituted or substituted. It is preferred that R1 is an organic linking group. Specific examples of R1 include, for example, the structural unit of (t-1) (t-34) or a group (which can form a ring structure) composed of the structural unit. In the case where the above-mentioned linking group has a substituent, Examples of the substituent are an alkyl group having 1 to 20 carbon atoms such as a methyl group or an ethyl group, an aryl group having 6 to 16 carbon atoms such as a phenyl group or a naphthyl group, a hydroxyl group, an amine group, a carboxyl group or a sulfonylamino group. a fluorenyloxy group having 1 to 6 carbon atoms such as N-sulfur, amidino-based Φ or an ethoxylated oxy group, an alkoxy group having 1 to 6 carbon atoms such as a methoxy group or an ethoxy group, or a chlorine or bromine group. Alkoxycarbonyl group having a carbon number of 2 to 7 such as a halogen atom, a methoxycarbonyl group, an ethoxy ore group or a cyclohexyloxycarbonyl group; a carbonate group such as a cyano group or a tert-butyl carbonate; and the like. a single bond or a divalent linking group. R2 contains 1 to 100 carbon atoms, 1 to 10 nitrogen atoms, 0 to 50 oxygen atoms, and 1 to 200 hydrogen atoms, and The base of the sulfur atom of 〜2 may be unsubstituted or substituted, and R2 is preferably 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, 32, and 34, or a combination of the structural units. In the case where R2 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, or an aryl group having 6 to 16 carbon atoms such as a phenyl group or a naphthyl group. 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 carbon number of 1 to 6 such as 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; a third butyl carbonate; Carbonate groups and the like. -64- 200806754 In the above formula (1), m represents a b. (7) It is better to use i~5, and Bu3 is better, and 1~2 is especially good. Also, the η table is not 2 to 9. The η system is preferably 2 to 8, 2 to 7 is preferred, and 3 to 6 is preferred. In the above formula (1), Ρ1 represents a polymer compound residue, 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, a polymer or a copolymer derived from an ethylene-based monomer, an ester polymer, an ether polymer, a urethane polymer, a guanamine a polymer, an epoxy polymer, a polyoxymethylene polymer, and the like, or a copolymer (for example, comprising a polyether/polyurethane copolymer, a polyether/vinyl monomer) At least one selected from the group consisting of a copolymer of a polymer (which may be any of a random copolymer, a block copolymer, and a graft copolymer) is preferably selected from the polymerization of a vinyl monomer. At least one of a group consisting of a copolymer or an ester, an ester polymer, an ether polymer, a urethane polymer, and the like, or a modified or copolymer thereof is preferably a polymerization of a vinyl monomer. The substance or copolymer is particularly preferred. ® Further The above polymer bud is preferably dissolved 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 the dispersion is weak, and it is 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. (A2-r[Sb R3令-Rs-P2)y General formula (2) In the above formula (2), the A2 system is synonymous with A1 of the above formula (1), and has a form of -65-200806754 The preferred embodiment is also the same, and the specific example of the organic pigment structure is a phthalocyanine compound 'Azo lake compound, an anthraquinone compound, a dioxon compound, a diketopyrrolopyrrole compound, etc.佳'Heterocyclic is imidazole, triterpene, pyridine, piperidine, porphyrin, tri-negative, iso-porphyrin, isoindolinone, benzimidazolone, benzothiazole, amber imine, ortho-benzene Formamidine, naphthylimine, hydantoin, D-introduction|quinoline, azole, b-pyridine, acridone, anthracene, etc. are preferred. Further, it may have a substituent in the same manner as A1, and the substituent is the same as in the case of A1#. 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 linking group of (χ + y) valence represented by the above R3 includes 1 to 60 carbon atoms, 0 to 10 nitrogen atoms, one to 50 oxygen atoms, and one to 10,000 hydrogen atoms. The atom and the base of 0 to 20 sulfur atoms may be unsubstituted or substituted.

The linking group of the (χ + y) valence represented by 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, for example, the same structural units as described above or a combination of the structural units. Among these, a preferred embodiment (specific example (I) 7) in which the linking group represented by R3 is preferably an organic linking group and an organic linking group is as follows. However, the invention is not limited by these. -66- 200806754 (r-1) 〇 It •ch2 — ch2_c-o-ch2 ?l (r-2) (r-3)

^ ch2- o- c- ch2- c h2— h3c- CH2" ^ ch2- o- c- ch2- ch2— ooo I! ii —CHg-CO-CHgv.^^-pC-CHz— H3C - CHf ^CHfO Hen CH2—o ff H •CH2—CH2-NH-C-〇CH2,/CH2-〇-C-NH-CHfCH2-H3C-CHf, CHf 0- C- NH- CH2- CiV (r-4) 0 tl —GH2- ch2 - 〇- ό- 〇- ch2, HsC-CH^ Π Η Η ^ch2-oco-ch2-ch2-, CH2— ο - c- ο- ch2— c η2_ ii 2 2ο (r-5) (r-6)

Ch2-ch2

Ch2 - ch2, 丫"ch2 - ch2-o (r~7) ch2-ch2-no o,ch2-ch2-0丫V5 H o CH2-CH2- oc-- CH2-CH2, Nv|f N, CH2- CHf - ch2_ (r-8) (r-9)

-67- i? 200806754 (r-10) —gh2-ch2- C Let GH2, CH2-〇«HfCH2-—CH2-CH2-C^〇-CHr"C^cH2-e〇^C^cH2^CH2- 0 i? (Ml) A CH2 — O0_CH2, /CH2-〇-C-CH2- 2, c, L • CH2-C-〇_CHf, CH2- O-CH2-2 II ^ II o 0 (Bu 12) 3-C-NH--CH2-CH2-NH-5»〇CH2, /CH2-〇->nh-CH2-CH2_-CH2-CH2-NH-C-〇-CH^^ch2"0,-^ NH CHs CH2o o (M3) -ch2-ch2-〇•ch2- ch2- 〇-g' o

C-O- GH2- CH2 one 〇-CH2 one CSV

—CH2-CH2-〇-pan 0

C_〇-CH2-CH2_ C-〇-CHfCH2— tl » - CH,CH2, —CH2^cH^ -ch2-ch2-oc o (Bu 15) _cHrCH2,,CHrCH2- nW: ,CH2—CH2_ .ch2- Ch2-(r-16) —CH2-CH2-C-〇-CH2^ /0H2^°^C^CH2^C^2if Cargo 03⁄4- CHg- C- 0· CH2, c〆0-3⁄4- O 〇丨-CH 广, CH2- 〇-"CH2-CH2〆-CHg-CHg-C-〇2 2 II 0 o (Bu 17) CH2- G-〇CH2, /GH wide. , (10) a ΐ / CHg • CH2 — co - CHg'fCHfO "ch2- o II 0-C-CH2- 〇-c-ch2- o • CH2—C- O-CHf II 0 c~ch2-o Among the above, (r_1), (r-2), (r_10), (r-11), (r-16), from the viewpoint of availability of raw materials, easy synthesis, and solubility of various solvents. The base of (r-17) is better. Further, in the case where the above R3 has a substituent, the substituent is exemplified by an example of 68 to 200806754, such as a methyl group or an ethyl group having 1 to 20 carbon atoms, and a phenyl group, a naphthyl group or the like having 6 to 16 carbon atoms. An aryl group, a methoxy group having a carbon number of 1 to 6, a methoxy group, an ethoxy group, etc., a group having an amino group, an amine group, a sulfhydryl group, a sulfonylamino group, an N-thioguanamine group, an ethoxycarbonyl group or the like. Alkoxy group having 1 to 6 carbon atoms, a halogen atom such as chlorine or bromine, or a oxyalkyl group having 2 to 7 carbon atoms such as a methoxycarbonyl group, an ethoxylated ore group or a cyclohexyloxy ore group; A carbonate group such as a cyano group or a third butyl carbonate. 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 alkylene group, an extended aryl group, an extended aralkyl group, and the like. , -0_, _S_, _C( = 0)-, _N(Ri9)_, _S0_, -S02-, -C02-, ·Ν(Κ2()) 302-, or a combination of two or more of these 2 The valent group is a preferred example (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, branched alkyl group, an aralkyl group, and -0-, -C(=0)-, -N(R19)·, -S02·, -C02·, -N (R20)S〇2-(wherein R19 and R2() each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), or a combination of two or more of these groups is a Preferably, the linear, branched alkyl, aralkyl, and -〇-, -C(=0)-, -N(R19)- (the above R19 represents a hydrogen atom or a carbon number of 1~ It is particularly preferable that four alkyl groups, -C02- or a combination of two or more such groups are particularly preferred. The above R5 is a single bond or a linear, branched alkyl group, an aralkyl group, and ..., c(=0)-, -N(R19)-, -S〇2·, -C〇2 -, - 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. a straight chain, a branch of -69-200806754 alkyl, an aralkyl group, and -o-, -c(=0)-, -N(R19)- (the above R19 represents a hydrogen atom or carbon The number of 1 to 4 alkyl groups, -C02- or a combination of two or more such groups of divalent groups is particularly preferred. Further, 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 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 carbon number of 1 to 6 such as a methoxy group or an ethoxy group. Alkoxy group, halogen atom such as chlorine or bromine, methoxycarbonyl group, ethyl@oxycarbonyl group, cyclohexyloxycarbonyl group, etc. alkoxycarbonyl group having 2 to 7 carbon atoms, cyano group, and third butyl group A carbonate group or the like such as a carbonate. In the above formula (2), y represents 1 to 8, 1 to 5 is preferred, 1 to 3 is preferred, 1 to 2 is particularly preferred, and X is 2 to 9, 2 to 8 is preferred, 2 to 2 7 is preferred, and 3 to 6 is particularly preferred. Further, P2 in the formula (2) represents a polymer skeleton, and can be selected from general polymers and the like according to the purpose and the like. 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), ("_1 〇), (r, i 1 ), (ri 6) ), or (r_i 7) , R4 is a single bond, a straight chain, a branched alkyl group, an aralkyl group, -〇-, _〇(= 〇)-, -N(R19>-(the above R19 system) 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 such groups are combined, and R5 is a single bond, an ethyl group, a propyl group, or The linking group 'P2 represented by the following formula (s_a) or (s_b) is a polymer or copolymer of a vinyl monomer, a polymer, an ether polymer, or a urethane polymer. Or such a modified substance, y is 1 to 2, and X is a commercial compound of 3 to 6 is particularly preferable. Further, in the following group, -70-200806754 R21 represents a hydrogen atom or a methyl group, and 丨 represents 1 or 2 (sa) {? 〇ch2-ch-c-〇-ch2-ch-ch2~o-c4ch2^

R21 I

R OH (s-b) 0 f! —CH2-CH-C-〇-CH2~CH2—

The mass average molecular weight of the R21 polymer compound is 1,000 or more, preferably from 1,000 to 500,000 in terms of mass average molecular weight, preferably from 3,000 to 10,000, more preferably from 5,000 to 80,000, and particularly preferably from 7,000 to 60,000. When the mass average molecular weight is within the above range, the effect of introducing a plurality of functional groups to the polymer end is sufficiently exhibited, and exhibits excellent performance in terms of adsorption to a solid surface, cell formation energy, and interface activity. In particular, in the case where the polymer compound according to the present invention is used as a pigment dispersant, β can achieve good dispersibility and dispersion stability. The polymer compound represented by the above formula (1) (including those represented by the formula (2)) is not particularly limited, and can be synthesized by the following method or the like. Among the following methods, the synthesis method of 2 v 3, 4, 5 or the like is preferable, and the following synthesis methods of 3, 4, and 5 are particularly preferable in terms of ease of synthesis. The terminal is introduced into a polymer selected from a carboxyl group, a hydroxyl group, an amine group or the like, and has a plurality of functional groups (A1 or a base halogen in the above formula or a plurality of functional groups (in the above formula a method of performing a polymer reaction of a compound halide of /^ or 八2) or an isocyanate having a plurality of functional groups (A1^A2 in the above formula) -71-200806754. A method of performing a Michael addition reaction with a polymer of a carbon-carbon double bond and a thiol having a plurality of functional groups (A1 or A2 in the above formula) 3. Polymerization of introducing a carbon-carbon double bond at the terminal And a method of reacting a thiol having a plurality of functional groups (A 1 or A 2 in the above formula) in the presence of a radical generating agent. 4. introducing a plurality of thiol polymers at the end, and a method of introducing a functional group of carbon-carbon double bond Φ (A1 or A2 in the above formula) in the presence of a radical generating agent. 5. having a plurality of functional groups (A1 or A2 in the above formula) A thiol compound as a chain shifting agent, a method of radically polymerizing a vinyl monomer. In the above, the polymer compound (preferably the polymer compound represented by the formula (2)) used in the method for producing a pigment 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 shifting agent to facilitate radical polymerization.

A3-RLS^-R6-f-SH h Formula (3) In the above formula (3), R6, R7, A3, g, and h are respectively R3 and R4 in the above formula (2). A2, X, and y are synonymous, and the preferred aspects are also the same. The above vinyl single system is not particularly limited, and examples thereof include (meth) acrylates, butenoates, vinyl esters, maleic acid diester-72-200806754, and anti-butene. Acid diesters, itaconic acid diesters, (meth) acrylamides, vinyl ethers, esters of vinyl alcohol, styrenes, (meth)acrylonitrile, and the like are preferred. These examples are, for example, the following compounds. Examples of the above (meth) acrylates include methyl (meth) acrylate, (methyl > ethyl acrylate, η·propyl (meth) acrylate, isopropyl (meth) acrylate, ( N-butyl methacrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, η-hexyl (meth)acrylate, cyclohexyl (meth)acrylate, (methyl) Tert-butylcyclohexyl acrylate, 2_ Φethylhexyl (meth)acrylate, third octyl (meth)acrylate, dodecyl (meth)acrylate, octadecyl (meth)acrylate , (meth)acrylic acid ethyl ethoxide, (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, (methyl acrylate) 2-ethoxyethyl ester, 2-(2-methoxyethoxy)ethyl (meth)acrylate, 3-phenoxy-2-hydroxypropyl (meth)acrylate, (meth)acrylic acid Benzyl ester, diethylene glycol monomethyl ether (meth)acrylate, diethylene glycol monoethyl ether (meth)acrylate, triethylene glycol (meth)acrylate Methyl ether, triethylene glycol monoethyl ether (meth)acrylate, polyethylene glycol (meth)acrylic acid φ-methyl ether, polyethylene glycol monoethyl ether (meth)acrylate, (methyl) Bismuth acrylate-phenoxyethoxyethyl ester, nonylphenoxy polyethylene glycol (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyl hydroxyethyl (meth)acrylate, Trifluoroethyl (meth)acrylate, octafluoropentyl (meth)acrylate, perfluorooctyl (meth)acrylate, dicyclopentenyl (meth)acrylate, tribromobenzene (meth)acrylate The ester, tribromophenyl hydroxyethyl (meth)acrylate, etc. Examples of the butenoate are, for example, butyl crotonate, hexyl crotonate, etc. Examples of the above vinyl esters are exemplified by Vinyl acetate, ethyl-73-200806754 alkenyl ester, vinyl butyrate, vinyl methoxy acetate, ethylene benzoate, etc. Examples of the above maleic acid diesters are exemplified by Dimethyl maleate, diethyl maleate, dibutyl maleate, etc. Examples of the acid diesters include, for example, dimethyl fumarate, diethyl fumarate, dibutyl fumarate, etc. Examples of the above-mentioned itaconic acid diesters are, for example, clothes. Dimethyl benzoate, diethyl itaconate, dibutyl itaconate, and the like.

Examples of the above (meth) acrylamide are, for example, (meth) acrylamide, N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide, N-propyl. (Methyl) acrylamide, N-isopropyl (meth) acrylamide, N-n-butyl propylene decyl (methyl) decylamine, N-tert-butyl (meth) acrylamide, N-cyclohexyl (meth) acrylamide, N-(2-methoxyethyl) (meth) acrylamide, N, N-dimethyl (meth) acrylamide, hydrazine, hydrazine - Diethyl (meth) acrylamide, N-phenyl (meth) acrylamide, Ν-benzyl (meth) acrylamide, (meth) propylene sulfenyl, diacetone acrylamide Wait. Examples of the above benzene susceptor include styrene, methyl styrene, dimethyl styrene, trimethyl styrene, ethyl styrene, isopropyl styrene, butyl styrene, hydroxy styrene, Methoxystyrene, butoxyphen-2-ene, ethoxylated phenethyl hydrazine, chlorostyrene, dichlorostyrene, bromostyrene, chloromethylstyrene, to take off with acidic substances Hydroxystyrene, methyl benzoic acid methyl ester, and α-methylstyrene, which are protected by a protecting group (for example, t-Boc). Examples of the vinyl ethers include methyl vinyl ether, butyl vinyl ether, hexyl vinyl ether, and methoxyethyl vinyl ether. -74- 200806754 In addition to the above compounds, a (meth)acrylic nitrile or a vinyl-substituted heterocyclic group (for example, vinylpyridine, vinylpyrrolidone, vinylcarbazole, etc.), N· may also be used. Vinyl methamine, N-vinylacetamide, N-ethlylimidazole, 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, an addition reaction of a monomer containing an isocyanate group with a compound containing one hydroxyl group or a compound having a primary or secondary amine group, or a monomer containing a radical or containing a grade 1 or It is an addition reaction of a monomer of a 2-stage amine group with an isocyanate, etc., and can be suitably synthesized. The above vinyl single system can be polymerized by only one kind, and can also be copolymerized by using two kinds of soils. These free radical polymers can be polymerized by a general method and according to a usual method. It is obtained as a vinyl monomer. For example, by dissolving such a vinyl monomer and a chain shifting agent in a suitable solvent, a radical polymerization initiator is added thereto, and dissolved in a solution at about 50 ° C to 2 2 0 ° C. The method (solution polymerization method). An example of a suitable solvent to be used in the solution polymerization method is arbitrarily selected, for example, depending on the monomer used and the solubility of the resulting copolymer. For example: methanol, ethanol, propanol, isopropanol, 1-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. -75- 200806754 Also, free radical polyhesitizing agents can be used, for example, 2,2 '-azobis(isobutyronitrile) (eight, 181^), 2,2,-azobis-(2,4 An azo compound of '-dimethylvaleronitrile, a peroxide such as benzoyl peroxide, and a persulfate such as potassium persulfate or ammonium persulfate. 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 for 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 into Φ-hydrolysis, a method of directly reacting with NaSH, a method of reacting with CH3COSNa to carry out hydrolysis, etc.) 7. A compound having 3 to 10 chlorothio groups in a molecule having a functional group (A1 or A2 in the above formula), and having Method for performing an addition reaction of a compound having a functional group reactive with a thiol group. The "functional group reactive with a thiol group" of the above method 7 is exemplified by a mercapto halide, an alkyl halide, an isocyanate, and 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 φ 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 hydrogenthio groups in one molecule" is exemplified by the following compounds. -76- 200806754 (u-1 s

II

HS-CH2-GH2-co-CH2, /CH2-〇-C-CH2 — CH2-SH H3C-CHr, CH2-0-g-CH2-CH2-SH o QO in- 2 ) , Π k LJ HS^CH2 -C-〇-CH2, /CHf OC-CH2-SH h3g-ch2 ch2-oc-ch2-sho (u-3 ) ff

II HS-CH2-CHS- NH-CO· CH2, /CH2—0-C-NH-CHf CHf SH H3C-CHr, CH2-〇-Jj-NH-CH2-CH2-SH OOO (u- 4 ) Η II , HS-CH2-CH2 - OO0-CH2, c/CH2 - 〇-C, 〇-CH2-GH2 - SH H3OCHr, CH2-OC-〇CH2-CH2-SH II o (u-5 ) (uB )

Λ HS N SH

(pH2 — CH2 — SH

HS- CH2- CH2" N Y N ^CH2- CH2- SH O (u-7 )

O II CH2_ CH2_ N- c-o- CHf CH2 — SHVr° H 〇 • - IJ hs-ch2-ch2-o- c_n-ch2-ch, 丫, ch2-ch2, n-c 指 ch2—ch2-sh

H o

H (u-8 ) hs,CH2, (u-9 ) hs-CH2.c I ^ hsXH2"ch/

;z〇,ch2/CH2,sh hsXH2, o o ch2

Ch2^CH2vsh

K -77- 200806754 (u-10) o 〇II II HS-CH2-CH2-C-〇-CH2^c^CH2-〇-〇CH2-CH2-SH HS-CH2—CH2-jin-o-CHf, CH2-O-JJ-CH2-CH2-SH oooo II II HS-CH2-C-〇,CH2, c/CH2-〇-C-CH2-SH HS-CH2-〇〇-CHr" \CHf〇-C- CH2-SH 〇o (u-12) ί? HS- CH2-CH2-NH-CO- CH2> HS- GH2- CHg- NH-poor - 0· GHf 〇o II ,CH2 — 0- C- NH - CH2 — CH2— SH , ch2-oj-nh - ch2-ch2-sho (u-13) f?

HS - 〇vch2-◦-C s (iH4) hs-ch2-ch2-o-c*o

Oo-ch2 — ch2-sh C-〇-CH2-CH2 — SHo II II hs-ch2- ch2- O—C 丫 c·. - ch2- CH2 — SH /x1n^co-ch2-ch2~sh hs-ch2-ch2-o-co ch2-ch2-oc Δ c wo (u-15) HS secret ch2-ch2, /CH2-ch2—sh II 0 N/ N hs-ch2-ch2, human sense CH2-CH2-SH HS - CH2-CH2〆n, ch "ch2-sh (lHB)

II hs—ch2—ch2-c-och2

0 II

CH2— 0«H2- CH2 a SH

II

^CHr CH2- o- c- CH2- CHf SH HS—CH2-CH2—c-0-CH2,γch2-cT ^

HS- CH2— CH2- c- O-CH 广,CH2 - 0· c- CH2- CH2_ SH o o (u-17) o o

Ll II HS-CH2-C-0-CH2, /CH2-o-c-ch2-sh n ~ch2-o,och2-sh HS-CH2-C-O-CH2,zCH2-〇 Jl

HS-CH2-JJ-O-CHr, CH2-〇-Jj-CH2-SH oo Among the above, from the viewpoint of availability of raw materials, easy synthesis, and solubility of various solvents, (u_1), (U-2), (u-10), (u-11) -78-200806754, (u-1 6), (u-1 7) are preferred. 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 described below. (k-1) (k-2) (k-3) (k-4) Η〇2〇^^ ho2c^V^ co2h f^COzH co2h co2h H〇2c^y co2h (k-5) (k one 6) (k-7)

(卜 8) (k - 9) (卜1〇)

-79- 200806754

(k_17> (k-18) A (M9) h2n n(k-20)

Η H A^ (k-21) fork (k-22)

K (k-23)

o (k-24) (k-27) (k-28) ^sj/OGH3 j , H3CO j, 0CH3

9〇h3 OCH 3 (k-26)

Ik a 29) σ 〇 〇〇Hs

O (k-30) (k-31)

OCN (k-32)

^NCO

O o (Bu 33)

OH (k-34)<=l

OH

(fc- 35) OH

OH O 8 0 _ 200806754 (k-36) (k-37)

-81 200806754

(k-47) (k-48> (k-49) (k-50) (k- 51)

(k - 53⁄4 (k-56)

(k-60) (k a 59)

-82- 200806754

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 urea group, a urethane group, and having a radical of a ligand 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 The addition reaction product system can be, 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, At least one functional group of a urethane 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 The compound of the bond is obtained by dissolving it in a suitable solvent, adding a radical generator thereto, and adding it at about 50 ° C to 1 ° C (thiol reaction method). -83-200806754 An example of a preferred solvent used in the above method is, for example, "a compound having 3 to 1 unit of a hydrogenthio group in one molecule" and "having an acid group selected from the 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 at least a hydroxyl group One type of functional group, and a compound having a functional group (for example, a carbon-carbon double bond) capable of reacting with a hydrogenthio group, and a solubility of the generated radical addition reaction product are arbitrarily selected. For example: methanol, ethanol, propanol, isopropanol, 1-methoxy-2-0 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 generating agent, an epoxy such as 2,2 '-azobis(isobutyronitrile) (AIBN) or 2,2'-azobis-(2,4'-dimethylvaleronitrile) can be used. Nitrogen compounds, peroxides such as benzammonium peroxide, and persulphates such as potassium persulfate, ammonium persulfate, and the like.

Specific examples of the compound of the formula (1) which are preferably used in the method for producing a pigment dispersion composition of the present invention are as follows. However, the invention is not limited by any of the specific examples.

-CH2—. H2 — C-0-CH: CH2-(^-0-CH; :cC〇H^〇^CHr ch2-〇-c-ch2— ch2— 84· 200806754 r3= f? (C-3) —ch2— Ch2—co-ch2, —CH2-CH2^C-〇-CHr" o -CH2 — €H2.

Ch2-o-c-ch2—ch2-ch2-o-c-ch2-ch2-o ch2- o- c-ch2- ch2- HOaC^^Y^S-R3--H02c Jn (n=5, ra=1)

Co2ch2ch2〇h co2ch2ch2ch2ch3 (c-4) ho2c ηο2ο^Α& -R3- -s^rn • c〇2ch3 (n=5, m=1) O ft co - ch2, oo If I! CH2-CH2-C- 〇-CH2, p/CH2 — 〇-〇CH2-CH2- _CH2 — ch2*-CH2-CH2-CO-CH2 <h2_

f2-〇-C-CH2-O ch2- oc-ch2 - ch2- O •ch2— tt ¢-5) ch2 — ch2-co-ch2, 〆ch2-0-c-ch2-ch2-/CHf, CH2- 〇-C-CH2-CH2-CH〆2 2 g 2 2 H02C s H〇2C^s_Ra_.sf-Xr J n co2ch2ch2oh -CH2 — ch2—C-〇~CH2\ / -ch2-ch2-co- ch^ ""ch2-oc-ch2-ch2·oo (n=5, m=1) co2ch2ch2ch2ch3 (C-6) 广' ho2c ) ho2c - R3- n co2ch3· (n=5f m=1)

-CH2 — CH2-C-〇- CH2, /CH2—〇·〇ch2· .CHi ^ — CK2- 0- C- CH2"~ CH2· CH2-CH2-C-〇-CH2, c/CH2-Cr » CH2-CH2卞O-CHr, CH2-oc,ch2-ch2— o 85- 200806754 R3= •CH2 — ch2 — co- ch2, a ch2-oc-ch2-ch2- (c-7) _CH2- CH2-c - o- CH2, /CH2--CH2-CH2-C-〇-CHi^ ^CH2-〇-C-CH2-CH2· ch2~ 〇-〇- ch2— ch2-0 · o

Ho-po^〇A^s_ _r3_ _ OH I co2ch3 m (n=5,m=1) (C-8) ho3s -R3- -s^r H nc〇2ch3 -CH2-CH2- C-0-CH2 , -CH2—CH2- C- o- CH^" oo II CH2-CH2-C-0-CH2^^CH2-0-C-CH2-CH2-〆〇!广CH2-〇-g-CH2—CH2 ~ - ch2-o vch2-o- c- ch2-ch2-o 0 m (n=5, m=1) (C-9) one CH2-CH2 — C-〇-CH2, c/CH2-〇-C -CH2-CH2-i? /CHf,CH2-〇-C_CH2-CH2_-CH2-CH2~C-〇-CH2^ ^gh2-o ^ •ch2-ch2-go-ch^",ch2-o-good -ch2-ch2— oo •R3· co2ch3 (n=5, mFl) (c- io) , . ^Y^S-R3-一-CH2-ό-〇~ CH2, 〆CH2, 〇-0-CH广CH2*" R , CH2-OC-CH2-CHg- -ch2-ch2-co-ch2^^ Ch2-o^ » -〇Η2·~ΟΗ2~〇-〇~ΟΗ2^ CH2~ 0~C_CH2~CH2— oo sHr (n=5, m=1) C02CH2CH2CH2CH3 co2ch2ch2oh m -86- 200806754 _ ch2 — ch2- c - ό-ch2, one - GH2 - ΟΌ-CH2, /CH2 - O' -CH2-CH2-CO k ch2-oc-ch2-ch2- ^ ch2~ o~ c- ch2~ ch2~ , CH 〇-C -CH2-CH2- o

.R3· (n=5, m=1) co2ch3 i? (C-12) ((M3) (C-14) _ ch2-ch2 — co ch2, /CH2— ύ R3- (n=5, m= 1) (n=5r m=1) 'CH2-CH2-C-〇-CH2^^CH2-〇-C"CH2-CH2- 0-g- GHz- CH2 〆&, 〇CH2—CH2-C- 〇-CHf CH2 - 〇-C-CH2-CH2_

C〇2CH2CH2OH C02CH2CH2CH2CH3 R3= m

IJ-ch2-ch2 — co-ch2, 〆ch2-oc-ch2—ch2—i?, CH2-〇-C-CH2-CH--ch2-ch2-co-ch2, 〆ch2-o ···CH2- CH2-C-〇CHr, CH2~〇-j^CH2-CH2- oo —ch2-ch2-co-ch2> CC1 o

•-R3—(n=5, m=1) ti CH〆-CH2 - CH2—B-〇-CH2s^CH2-〇〆2 -CH2-CH2-Pan-O-CHf'CHs-O-therapy-CH2 - CH2. oo ch2-oc-ch2-ch2-ch2-oc-ch2-ch2-o C02C1 co2ch2ch2oh ;h2ch2ch2ch3 m •87- II200806754 «Μ 5) —R3- -s^r .ho2c n . . CO money(η =3, m=1) Ο II -CH2-CH2-C-〇-CH2>vc^ ch2- ch2- c- o- ch^, o ch2-oc-ch2 — ch2-'ch2-oc-ch2-ch2 -o (C-16) ooo HI! -ch2- ch2-co- ch2^ ^ ch2-o- c- ch2-ch2· CHi CH2, CH2— c- o- CH2, 〆ch2—cx —CH2 — CH2- C-〇-CHr" Λ〇Η2-〇«Η2-〇Η2_ CH2-0-C-CH2-CH2- HOiC^Y^S- —R3— \ COOH • η〇2〇- n L C02CH3 (n=5 ,m=1) (x:y=9:1) (C-17)

GH2-CH2-C-〇-CH2 v. CH2 - CH2—CO-CHf o CO2CH3J m CH2 — CH2—CO—Ch^v^/CHfO-C-Chb — CH2, /CHi - ch2-o , CH2-〇 -j^CH2-CH2· ch2-oc-ch2-ch2-〇-88- II200806754 (G-19) CH2—CH2 - C-〇CH2, c/CH2-〇-C-CH2—ch2-, CH2-ο -anti-CH2-CH2-o

(C-20)

-R3-- (n=5, nn=1) _CH2 — CH2 — C-0-CH2, /CHW -CH2—CH2-C-〇CHr", CH2-〇〇CH2-CH2·o b

Co2ch2ch2oh cq2ch2ch2gh2ch3 C〇2CH3, R3= hf? 〇CHCH2-CH2-C,0'CH2, c/CH2-〇-C-CH2-CH2-II /CHf yCHg-OC-CiV-aV -ch2-ch2-co -ch2^ ^ch2-o » *ch2-ch2-iso-o-cuf, ch2-o_anti-ch2-ch2- oom (C-21)

Oo = U II 〇CH2-CH2 — C-〇-CH2, c/CH2 - oc-ch2-ch2_ H /CHr" \cH2-〇-C-CH2-ch2_ CH2-CH2*-C-〇-CH2^ c^CH2-〇色CT2—CH2 — C-〇_CHf", ch2-o-och2-CH2—co2ch2ch2oh C02CH2CH2CH2CH3 m no (C-22)

R3= u a ch2-ch2-c-o-ch2, I? /CH〆 CH2-CH2-C Let CH2, fCH2-. CH2—CH2- C- o- CH^^CHz- oc-ch2-ch;oo CH2~ o~ c- ch2~ ch2_ oh2—oc-ch2-ch2_ o co2ch3. m -8 9 - 200806754 (C-23) -ch2 — ch2 — c- o- CH2\ 11 •CH2-CH2-〇〇-CH2, /CH2-〇-CH2—CH2-C-〇-CH^^CH2-〇*-C-CH2~CH2" ^ Ch2~ o~ c_ ch2~ch2~ ""ch2- o- c- ch2- qh2-o oo ►——R3- o (n=5, m=1)

C〇2〇H2CH2OH co2ch2ch2ch2ch3 m -ch2-chJ-o-oh_oh2-oXoh2-ch2-(C-24) cm, meaning (n=5, m=1) -GH2— GHz- ό· Ο- OH2, 〆GH2 — O -ch2-ch2-co-ch^c^ o „R3._s^S^ n C〇2 O2CH3. m ch2 - o- c - ch2—ch2-0 CH2-0-C-CH2-CH2— / 〇h2 〇(0-25)

.rls^T Ί co2ch3.

Ch2-*oc-ch2-ch2-ch2-oc-ch2-ch2-o r3:= u a CH2 - CH2 - c- 〇- ch2, i? ^CHf ch2~ch2-co-ch2^ ^ch2-o CH2 ~CH2~C-0-CH^ ^CHg-OC-CHz-CHs· oo (C-26)

(n=5, m=1)

II —ch2- ch2-. - o- CH2, c〆ch2- o 兮ch2-ch2·J! /CH; wrig— CHg- C- 〇-CH2, ^GHa—〇CHg-CHg-CO-CHr^^CHz-OC-CHa-CHa · O 〇CH2-OC-CH2-OH2-o co2ch2ch2oh co2ch2ch2ch2ch3 m -90- 200806754 r3= (c-27)

•R3· (G-28)

sW-r co2ch2ch2oh co2ch2ch2ch2ch3 (n=5f m=1) fl CH2-CH2-C-〇-CH2'v^CH2-〇- o 〆}[ /CHf-CH2-CH2 — CO-CH2, /CH2-〇丨2-CH2-CH2-〇-C-CH2-CH2--CH2*~CH2-C-〇-CH^^CH2-*-〇-C-*CH2-CH2-o oo co2ch3- r3= _ch2-ch2-芑,o-ch2. n {? CH2-CH2 — C-0-CH2, /CH2-〇-C-CH2-CH2- /CHf", CH2-〇-pan-CH2-CH2-CHz-0-CH2- CH2-汗令CHfo ch2-oc-ch2-ch2- oi? -CH2-CH2-C-〇-CH2\^CH2-〇-C-CH2-CH2- (C-29) _CH2—CH2-C-〇- CH2, -ch2 — ch2-oo_ch Factory o /CHf CH2-0- C-CH2-CH2- k IIo , ch2ch2—ch2—o —ch2 — o • R3. C〇2 :〇2ch3 (n=5, m= 1) ir (C-30) CH2 — CH2 — C-〇-CH2, /CH2 — o-ogh2 — ch2· ', ~-~c· o II yZHl -CH2 — CH2-C-〇-CH2, /CH2 -〇-ch2— ch2- ^οη2-ο- c- ch2~ch2·oo CH2-〇-C-CH2-CH2-

Co2ch2ch2oh co^ch2ch2ch2ch3 (n=5T m=1) m -91- 200806754 (C-31)

H -CH2- Ο CH2, r, Gfig_ 0- C- CH2—CHf , ch2-oc-ch2-ch2- /ΗΓ CHg_CH2~C~0~0H2>v_(^〇n2—^ CH2—CH2- Co- CHf, ch2- 0- c- ch2-ch2· ch2-o

O _ H, j〇: -R3- sun n co2ch3 m (n=5, m=1) R3= i? i? (C-32) • ch2— ch2- co- CH2, c〆ch2— o- c - ch2- ch2- ίΤ, ch2 — oc-ch2 — ch2- -CH2-CH2-C-〇-CH2, /CH2-. JJj ^H?-CH2-C-〇-CHr ^ 〇 H \ 〇 N /P . Politics - -R3 - -s^r4r n co2ch2ch2oh (n=5, m=1) co2ch2ch2ch2ch3 m ch2-o-c-ch2-ch2o (C-33)

II i?

——R3---CH2-CH2-C-〇-CH2^^CH2-〇-C-CH2-CH2- o II /CH2 -CH2-CH2-OOCH2, /CH2-〇*, ch2—ch2-C^ O-CHf, ch2-oc-ch2-ch2_o o ch2-o- c- ch2-ch2- co2ch3_ (n=4. 5, m=1.5) (C-34)

(n=4. 5f mFt. 5)

Ch2—ch2 — co-ch2 CH2-OH2-C-0-CH2 o ?ian ch2- ch2- c- o- CH2 V. ^ ch2- o- c- ch2- ch2- /CHf kcHa a 0_p-CH2-CH2 - , gh2-o , ch2- ο- ο ch2 — ch2 — oo

:ch2ch2oh co2ch2ch2ch2ch3 m -92- 200806754 (C-35)

夂' The polymer compound is preferably a polymer compound having an acidic group. A polymer compound having a carboxyl group is preferred, and (A) has a carboxyl group.

The copolymerized compound derived from at least one repeating unit derived from the compound of the group and (B) at least one repeating unit derived from the compound having a carboxylate group is particularly preferred. The above repeating unit derived from the compound having a carboxyl group (A) is preferably a repeating unit represented by the following formula (I), 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 (||), and a repeating unit represented by the following formula (IV) is preferred, from benzyl acrylate. The repeating unit derived from benzyl methacrylate, phenylethyl acrylate, phenylethyl methacrylate, 3-phenylpropyl acrylate or 3-phenylpropyl methacrylate is particularly preferred. -93- 200806754

(R2 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms; and R3 represents a group represented by the following formula (M1))

Formula (III) (FU is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a hydroxyl group, a hydroxyalkyl group having 1 to 5 carbon atoms, or an aryl group having 6 to 20 carbon atoms. FU and heart system Respectively represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. i represents a number of 1 to 5)

General formula (IV) (R7 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. FU is a group represented by the following formula (V))

The general formula (V) (Rg represents an alkyl group having 2 to 5 carbon atoms or an aryl group having 6 to 20 carbon atoms Rn and R11 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. j represents 1 to e. -94-200806754) Further, the ratio of the repeating unit derived from the compound having a carboxyl group to the repeating unit derived from the compound having the carboxylate group (B) is relatively The total number of repeating units in the repeating unit (A) is preferably from 3 to 40, and preferably from 5 to 35. In the method for producing a pigment dispersion composition of the present invention, the molecular weight of the polymer is not particularly limited, and means a 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 which is not particularly limited in advance 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 a solution in which the #solvent is dissolved in a coagulating organic particle liquid in a state in which the solvent is a citrus solvent; A method in which a solvent of the agglomerated organic particle liquid is dissolved and dissolved in a different solvent. In the case of adding the solution dissolved in the solvent, the concentration of the polymer compound is not particularly limited, and preferably 1 to 70% by mass, preferably 2 to 65% by mass, more preferably 3 to 60% by mass. . 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), At any point after the end of the steps, add 'and you can also combine them. In the method for producing a composition of the pigment dispersion of the present invention, the polymer compound having a mass average molecular weight of 1,000 or more can be contained in the composition as a binder described later, for example, after the concentrated organic particles are re-sinked, It is preferably added when the organic particles are finely dispersed and aggregated. When the amount of the polymer compound to be added is 100 parts by mass, the amount of the organic particles to be aggregated is preferably from 1 to 1,000 parts by mass, preferably from 5 to 500 parts by mass, preferably from 10 to 300 parts by mass. It is especially good. To:: Polymer compounds with a molecular weight of 1 000 or more are, for example, polyvinylpyrrolidone, poly, vinyl alcohol, polyvinyl methyl ether, polyethylene oxide, polyethylene glycol, polypropylene glycol, poly Acrylamide, vinyl alcohol-vinyl acetate copolymer, polyvinyl alcohol-partic acid acetal, polyvinyl alcohol-partial condensate, vinyl pyrrole sulphuric acid vinyl acetate copolymer, polyethylene oxide /propylene oxide block copolymer, polyamine, cellulose derivative, starch derivative, and the like. Further, natural high molecular 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 containing at least one repeating unit derived from a compound having a carboxyl group and at least one repeating unit derived from a compound having a carboxylate group, for example, JP-A-59-4461 In Japanese Unexamined Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. -96-200806754 General methacrylic acid copolymer, acrylic acid copolymer, itaconic acid copolymer, crotonic acid copolymer, maleic acid copolymer, partially esterified maleic acid copolymer, and the like. Further, a particularly preferred example is an acrylic-acrylic acid acrylate copolymer, a methacrylic acid-acrylic acid ester copolymer, an acrylic acid-methacrylic acid ester copolymer, and a methacrylic acid-acrylic acid described in the specification of U.S. Patent No. 4,139,391. A methacrylate copolymer, or a multicomponent copolymer of acrylic acid or methyl chlorophyllin, with acrylate or methacrylate, and other vinyl compounds.

Examples of the vinyl compound are, for example, styrene or substituted styrene (e.g., vinyl toluene, vinyl ethylbenzene), vinyl naphthalene or substituted vinyl naphthalene, acrylamide, methacrylamide, Acrylonitrile, methacrylonitrile, etc., preferably styrene. These polymer compounds may be used alone or in combination of two or more, and may be used in combination with a compound having a molecular weight of less than 1 Å. In the present invention, the dispersion of the organic nanoparticles is preferably 60% by mass or more, more preferably 65% by mass or more. The organic solvent system is not particularly limited, and may be appropriately selected from the general public. For example, an ester compound solvent, an alcohol compound solvent, an aromatic compound solvent, an aliphatic compound solvent, a ketone compound solvent, an ester compound solvent, or a ketone compound solvent is particularly preferred. These may be used alone or in combination of two or more. The ester compound solvent is, for example, 2-(1-methoxy)propyl acetate, ethyl acetate or 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 - 己院, 环己院, and the like. The ketone compound solvent is, for example, methyl ethyl ketone, acetone, cyclohexanone or the like. -97-200806754 [Pigment Dispersion Composition] Next, a description will be given of a state in which a pigment dispersion of the present invention or an organic pigment nanoparticle thereof is used for forming a composition, for example, a color filter or an inkjet ink. Further, the ink jet ink can be used as a general ink jet ink, such as inkjet ink for printing, in addition to inkjet ink for color filters. The organic nanoparticle system can be used, for example, in a state of being dispersed in a vehicle. Preferably, the color developing agent-based paint is a medium portion in which the pigment is dispersed in a liquid state, and is liquid-containing and includes a portion Φ (bonding agent) which is combined with the pigment to strengthen the coating film, and a component which dissolves and dilutes the composition. Organic solvent). In addition, the binder used in the formation of the nanoparticles in the present invention may be the same as or different from the binder used for the redispersion, and may be separately classified into a nanoparticle to form a binder and a redispersion bond. Agent. The organic nanoparticle 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% by mass based on the total amount of the organic nanoparticle of the dispersed composition. ～20 mass% is preferable, and 5 to 15 mass% is particularly preferable. In the case where the toner is dispersed by the above-described color developing agent, the amount of the binder and the dissolved and diluted component is appropriately determined depending on the type of the organic material, and the binder is 1~ with respect to the total amount of the dispersed composition. 30% by mass is preferred, 3 to 20% by mass is preferred, and 5 to 15% by mass is particularly preferred. It is preferable that the dissolved and diluted component is 5 to 80% by mass, and 10 to 70% by mass is preferable. In the above-mentioned concentrated and extracted nanoparticle liquid, as described above, since rapid filter filtration is possible, organic nai The rice particles are preferably agglomerated by concentration, and concentrated by centrifugation or drying to be agglomerated. -98- 200806754 A method of finely dispersing such agglomerated nanoparticles can be carried out, for example, by a method of dispersing ultrasonic waves or applying physical energy. The ultrasonic irradiation device to be used has a function of applying a supersonic wave of 10 kHz or more, and examples thereof include an ultrasonic homogenizer and an ultrasonic cleaner. When the liquid temperature rises during the ultrasonic irradiation, in order to cause thermal aggregation of the nanoparticles (for example, refer to "Pigment Dispersion Technology - Surface Treatment and Dispersion Usage and Dispersibility Evaluation -" Technical Information Association 1 999), the liquid temperature is set to 1 00 ° C is better, 5 ~ 60 ° C is better. The temperature control method is carried out according to the control of the temperature of the dispersion liquid 0, the temperature control of the temperature control layer of the temperature control dispersion liquid, and the like. In addition to the physical energy, the dispersing machine used for dispersing the concentrated organic nanoparticles is not particularly limited, and examples thereof include a kneader, a roll mill, a vertical ball mill, a super honing machine, and a high-speed dispersion. Dispersing machine for machine, homogenizer, sand mill, etc. Further, a high-pressure dispersion method or a dispersion method using fine particle beads is also suitable. A preferred method for producing a dispersed composition of an organic nanoparticle, wherein the coloring agent has a viscosity at 25 ° C of 10,000 mPa·s or more, preferably 100, after kneading and dispersing with a resin component. The kneading and dispersing treatment is carried out in a manner of a relatively high viscosity of 000 mPa*s or more, and then the viscosity after the addition of the solvent and the fine dispersion treatment is generally 1, 〇〇〇mPa·s or less, preferably 100 ÅPa·s or less. A method of relatively low viscosity is preferred, and a method of performing microdispersion 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 shear force of •99-200806754. Next, 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 oxidized by a glass having a particle diameter of 0.1 mm. The beads produced by chromium or the like are subjected to precise dispersion treatment. Furthermore, fine particle beads of 0.1 mm 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 kneading and dispersion are also described in "Paint Flow and Pigment Dispersion" by T.C. Patton (John Wiley / . a n d S ο n s 1964), and this method can also be used. <2> Example of Dispersant The organic nanoparticle-dispersed composition is intended to add a general pigment dispersant or a surfactant in order to improve the dispersibility of the organic nano-Φ particles. These dispersants use a wide variety of compounds, for example, 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 (Kyoei Kobe Oil Chemical Co., Ltd.) System), W00 1 (made by Yusho Co., Ltd.) and other cationic surfactants; polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octyl phenyl Nonionic surfactants such as ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilauro-100-200806754 acid ester, polyethylene glycol distearate, sorbitan fatty acid ester; Anionic interfacial activity agent such as W004, W005, W017 (manufactured by Yusho Co., Ltd.); EFKA-46, EFKA-47, EFKA-47EA, EFKA polymer 100, EFKA polymer 400, EFKA polymer 401, EFKA Polymer 450 (above Morihara Industry Co., Ltd.), DISPERSAID 6, DISPERSAID 8, DISPERS Polymer dispersant such as AID 15 and DISPERSAID 9100 (manufactured by Sanyo Chemical Co., Ltd.); Sorospas 3000, 5000

Various Sorospas dispersants (made by ZENECA Co., Ltd.) of 9000, 12000, 13240, 13940, 17000, 24000, 26000, 28000, etc.; ADEKAPLRONIC L31, F38, L42, L44, L61, L64, F68, L72 , P95, F77, P84, F87 > P 9 4, L 1 0 1 , P 1 0 3, F 1 0 8, L121, P-123 (made by Asahi Kasei Co., Ltd.) and 丨SONET S-20 ( Sanyo Chemical (share) company system). Further, the pigment dispersant described in JP-A-2000-239554, or the compound (C) described in JP-A No. 5-72943, or the compound of Synthesis Example 1 described in JP-A-2001-31885 Suitable for use. The compound represented by the dispersing agent [dispersion phase] used in the formation of the organic nanoparticle at the time of redispersion can also 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. Further, the Mv/Mn of the particles after redispersion is preferably 1·0 to 2·0, preferably 1. 〇 to 1.8, and preferably 1.0 to 1.5. The organic pigment nanoparticle contained in the pigment dispersion composition of the present invention or the colored photosensitive resin composition described later is a so-called nanometer size of 101-200806754 (for example, t〇~1 〇〇nm) fine particle diameter. 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. Further, since the organic pigment nanoparticles contained in the pigment-dispersed composition and the colored photosensitive composition can be finely and uniformly dispersed in a highly uniform manner, a high coloring density can be exhibited in a thin film thickness, for example, ' Thin layering of color filters and the like. Further, in the pigment-dispersed composition and the colored photosensitive resin composition, a pigment containing a clear color tone and a high coloring power is contained in β, and is used as an image forming material for producing a color sample (col orp roof) or a color filter. It is excellent. In the case of the alkaline developing solution used for the exposure and development of the colored image formation, the pigment dispersion composition and the colored photosensitive resin composition are those which are soluble in the alkaline aqueous solution as a binder (adhesive agent). ), and can also respond to environmental requirements.

Further, an organic solvent having a moderate drying property can be used as a solvent for the Φ pigment dispersion composition and the coloring photosensitive resin composition (dispersion medium for the pigment), 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-pigment nanoparticle, (b) binder, and (c) two or more ethylenically unsaturated bonds. The polyfunctional monomer and (d) photopolymerization initiator or photopolymerization initiator are used to describe the respective components of the colored photosensitive resin composition of the present invention. (a) Organic Pigment Nanoparticles The method for producing organic pigment nanoparticles has been described in detail. -102·200806754 The content of the machine pigment nanoparticle is 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), 3 to 90 The mass% is preferably 20% to 80% by mass, more preferably 25% to 60% by mass. 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 pigment nanoparticle (pigment particle) which functions as a coloring agent is preferably a particle diameter 〇·ι // m or less, particularly preferably a particle diameter of 0.08 // m or less. Further, it can also be used in combination with a general pigment 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 Å or more as described above. The content of the binder is generally 15 to 50% by mass, preferably 20 to 45% by mass based on the total solid content of the colored photosensitive resin composition. 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) A polyfunctional monomer having two or more ethylenically unsaturated double bonds or a low polymer. A polyfunctional compound having two or more ethylenically unsaturated double bonds contained in the colored photosensitive resin composition of the present invention. A monomer or a low polymer which has two or more ethylenically unsaturated double bonds and which can be added to a polymerized monomer or a low polymer by light irradiation. Such a monomer and a low polymer may, for example, be a compound having at least one addition-polymerizable ethylenically unsaturated group in a molecule and a boiling point of 100 ° C or more at normal pressure. In this example, for example, dipentaerythritol hexa(meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, and phenoxy (meth) acrylate Functional C-103- 200806754 enoate or monofunctional methacrylate; polyethylene glycol di(meth)acrylic acid m, polypropylene glycol di(meth)acrylate, trimethylolethane triacrylate, three Hydroxymethylpropane tri(meth)acrylate, trimethylolpropane dipropionate, neopentyl glycol di(meth)acrylate, pentaerythritol tetrakis(methyl)propanate, pentaerythritol III Methyl) acrylate, dipentaerythritol hexa(meth) acrylate, dipentaerythritol penta (meth) acrylate, hexanediol di(meth) acrylate, trimethylolpropane tris(propylene methoxy propyl Ether, tris(propenyloxyethyl)trimeric isocyanate, tris(propyleneoxyethyl)cyanate glycerol, tris(meth)acrylate; in trimethylolpropane or glycerol Addition of polyfunctional alcohols to epoxy decane or propylene oxide , The (meth) acrylated like those polyfunctional acrylate or polyfunctional methacrylate. Further, the following describes the addition of polyfunctional alcohols as described in the general formulae (1) and (2) of JP-A-10-0-6986; The (meth)acrylated compound after ethylene oxide or propylene oxide is suitable. In addition, the amine methacrylate acrylates described in JP-A-48-41, 708, JP-A-59-60, and JP-A-51-371-93 Polyester acrylates described in JP-A-48-641, JP-A-49-431, and JP-A-52-3490, and reaction product rings of epoxy resin and (meth)acrylic acid A polyfunctional acrylate or methacrylate such as an oxy acrylate. 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 Β" described in Japanese Laid-Open Patent Publication No. Hei 11-1 33600. -104· 200806754 These monomers or low polymers (monomer or low polymer are preferably used with a molecular weight of 200 to 1 00) may be used alone or in combination of two or more. The total solid content of the resin composition 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 of 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, a photopolymerization heuristic system) a mixture of a photopolymerization initiation function found by a combination of a plurality of compounds, as described in the specification of U.S. Patent No. 2,637,660, the pheno- gamma aldehyde compound disclosed in the specification of U.S. Patent No. 2,448,828. An ether compound, an aromatic auxin compound substituted by an α-hydrocarbon described in the specification of U.S. Patent No. 2,725,251, a polynuclear ruthenium compound described in the specification of the U.S. Patent No. 30,461, and the specification of U.S. Patent No. 2,591,758, U.S. Patent No. The combination of the triaryl imidazole dimer and the oxime-amine Φ ketone described in the specification of No. 3549367, the benzothiazole compound and the trihalomethyl-S- described in Japanese Patent Publication No. 5 1 - 4 8 5 1 6 The trihalogenated methyl oxadiazole compound described in the specification of the trihalogenated methyl-three-till compound described in the specification of U.S. Patent No. 4,213,976, the disclosure of which is incorporated herein by reference. Things, etc. Particularly preferred are trihalomethyl-S-tripper, trihalomethyloxadiazole and triarylimidazole dimer. In addition, " " Polymeric Heuristic Agent C" described in Japanese Laid-Open Patent Publication No. Hei 11-133600, or 1-phenyl-1,2-propanedione-2-(ο-B) Oxycarbonyl) hydrazine, fluorenyl-benzylidene-4,-(phenylhydrocarbyl)benzimidyl-hexyl-105-200806754 ketone oxime, 2,4,6-trimethylphenylcarbonyl-di Phenylphosphine oxide, hexafluorophosphoryl-trialkylphenyl scale salt is 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 heuristic agents are used, the display characteristics, particularly the unevenness of display, may be less than the content of the photopolymerization heuristic or photopolymerization heuristic system with respect to the total solid content of the colored photosensitive resin composition. It is preferably 0.5 to 20% by mass, preferably 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) '[Solvent] In the colored photosensitive resin composition of the present invention, an organic solvent may 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 propionate φ Ester, isopropyl butyrate, ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, methyl glycolate, ethyl hydroxyacetate, butyl glycolate, methoxyacetic acid 3-methyl ester, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-hydroxypropionate, ethyl 3-hydroxypropionate, etc. Alkyl hydroxypropionates; 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 Methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, 2-oxy-2-methylpropionic acid-106- 200806754 methyl ester, 2-oxy-2-methylpropionic acid Ethyl ester, methyl 2-methoxy-2-methylpropanoate, ethyl 2-ethoxy-2-methylpropionate, pyruvic acid Methyl ester, ethyl pyruvate, propyl pyruvate, methyl acetate, ethyl acetate, methyl 2-hydroxybutyrate, 2-ethyl butyrate, etc.; ethers, such as diethylene glycol Methyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol-ethyl. Ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, propylene glycol methyl ether acetate, etc.; ketones, such as methyl ethyl ketone, A Alkyl isobutyl ketone, cyclohexanone, cyclohexanone, 2-heptanone, 3-heptanone, etc.; aromatic hydrocarbons such as toluene, Φ xylene, and the like. Among these solvents, etc., 3-ethoxyxopropionate methyl ester, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, butyl acetate, 3-methyl Methyl oxypropionate, 2-heptanone, cyclohexanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol methyl ether acetate, etc. are preferred as the solvent of the present invention. . These solvents may be used singly or in combination of two or more. Further, a solvent having a boiling point of from 18 ° C to 250 ° C may be used as needed. These high boiling solvents are as exemplified below. Diethylene glycol monobutyl ether, diethylene glycol Φ-ethyl ether acetate, diethylene glycol monoethyl ether, 3,5,5-trimethyl-2-cyclohexen-1-one, butyl Lactic acid ester, dipropylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol diacetate, propylene glycol-η-propyl ether acetate, diethylene glycol diethyl ether, 2- Ethylhexyl acetate, 3-methoxy-3-methylbutyl acetate, Τ-butyrolactone, tripropylene glycol methyl ethyl acetate, dipropylene glycol-n-butyl acetate, propylene glycol Phenyl ether acetate, 1,3-butylene glycol diacetate. The content of the solvent is from 10 to 9.5 mass based on the total amount of the resin composition. /. It is better. -107-200806754 [Surfactant] In the color filter that can be used in the past, the color of each element is increased in order to achieve high color purity, and the unevenness of the thickness of the element is considered as color. The problem of both. Therefore, 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 preferable that Φ contains a suitable surfactant in the colored photosensitive resin composition. The interfacial active agent disclosed in Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. 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 group, di-tert-butyl-p-cresol, gallic phenol, and third butyl group. Hydroquinone, benzoquinone, 4,4'-thiobis(3-methyl-6-t-butylphenoxy), 2,2'-methylenebis(4-methyl-6- Tributylphenoxy), 2-hydrothiobenzimidazole, phenothiazine, and the like. The content of the thermal polymerization inhibitor is 1 mass based on the total amount of the resin composition. /. The following is better. [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 coloring photosensitive resin composition, and the particle diameter is 〇·1 μm or less, particularly -108-200806754 0.0 8 μm or less. It is better. Specifically, S, a dye, or a pigment can be suitably used in the color material described in Japanese Patent Publication No. 2005-1771, [0038], or in JP-A-2005-361447 [0068] to [0072]. The pigment described in Japanese Unexamined Patent Publication No. Hei No. Hei. No. Hei. 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. [UV absorber]

The colored photosensitive resin composition of the present invention may optionally contain an ultraviolet absorber. In addition to the compound described in JP-A-H05-72724, for example, salicylate-based, benzophenone-based, benzotrimethane, cyanoacrylate-based, nickel-chelating agent, and hindered Amines and the like. Specifically, for example, phenyl salicylate, 4-tert-butylphenyl salicylate, 2,4-di-tert-butylphenyl-3',5'-dihydroxybenzoic acid Ester, 4-tert-butylphenyl salicylate, 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-n-octyloxy Benzophenone, 2-(2'-φhydroxy-5'-methylphenyl)benzotriazole, 2_(2'-hydroxy-3'_t-butyl-5'-methylphenyl )-5-chlorobenzotriazole, ethyl-2-cyano-3,3-diphenyl acrylate, 2,2'-hydroxy-4-methoxybenzophenone, nickel dibutyl Dithiocarbamate, bis(2,2,6,6-tetramethyl-4-pyridine)-sebacate, 4-t-butylphenyl salicylate, phenyl salicylate, 4-hydroxy·2,2,6,6-tetramethylpiperidine B condensate, succinic acid-bis(2,2,6,6-tetramethyl-4-piperidinyl)-ester, 2-[ 2-hydroxy-3,5-bis(α,α-dimethylbenzyl)phenyl]-2indole-benzotriazole, 7-{[4-chloro-6-(diethylamino)_5 _Triso-2-yl]amino}-3-phenylcoumarin. The content of the ultraviolet ray absorbing agent is 5% by mass or less based on the total amount of the resin composition, and 109-200806754 is 隹. In addition, the coloring photosensitive resin composition of the present invention may contain, in addition to the above-mentioned additives, an "adhesive aid" described in JP-A-11-133600, or other additives. [Coating film of the coloring photosensitive resin composition] The component contained in the coating film of the coloring photosensitive resin composition of the present invention is the same as that of the above-mentioned [coloring photosensitive resin composition]. Further, the thickness of the Φ film to be used for the coloring photosensitive resin composition of the present invention can be appropriately determined depending on the use thereof, and preferably 〇5~5·0μπι is preferably 1.0 to 3.0 pm. 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 heuristic agent or a photopolymerization heuristic agent. (slit nozzle)

In addition, 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 is formed by a slit nozzle having a slit-like hole. Coating is preferred. Specifically, it is preferable to use the publications of JP-A-2004-89851, JP-A-2004-1 7043, JP-A-2003-1 70098, JP-A-2003-1 64787, and JP-A-2003-1 0767. A slit-shaped nozzle and a slit coater described in Japanese Laid-Open Patent Publication No. 2001-791 No. The coating method of the coloring photosensitive resin composition applied to the substrate is excellent in spin coating from the viewpoint of being able to apply a film of 1 to 3 μm with high precision from -110·200806754, and producing the color filter. The middle system is widely used. However, in recent years, with the increase in the size and mass production of the liquid crystal display device, the manufacturing efficiency and the manufacturing cost are further improved, and it is more suitable for the slit coating of the wide-area substrate coating than the spin coating. Used in the production of color filters. Further, even from the viewpoint of the so-called liquid-saving property, the slit coating system is superior to spin coating, and a uniform coating film 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 having a width corresponding to the width of the rectangular substrate is generally maintained at a clearance of from 10 to several hundred micrometers with respect to the substrate. A coating method in which a coating liquid supplied from a slit is applied to a 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 of liquid than spin coating, (2) reduction of washing treatment due to non-scattering of the coating liquid, and (3) scattering of liquid components that are not mixed into the coating film, (4) Since the start time is not started by the rotation, it is possible to shorten the tact time during the flow-through operation and (5) to apply the coating to 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 desired for the reduction of the amount of the coating liquid. In the slit coating, since a large-area coating film can be applied from a long distance by spin coating, when the coating liquid is discharged from a wide slit outlet, it is necessary to maintain a certain degree of relative relationship between the coater and the object to be coated. 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 each of the coating liquids supplied from the slit of the coating head to the coating liquid of the substrate are particularly required to cover the entire coating width and remain constant. When the liquid property of the coating liquid such as fluidity or viscoelastic property is insufficient, coating unevenness is likely to occur, and it is difficult to maintain a constant coating thickness in the coating width direction, and finally there is a problem that it is difficult to obtain a uniform coating film. . As described above, in order to obtain a coating film which is not uneven and uniform, most of the attempts have been made to improve the fluidity and viscoelastic properties of the coating liquid. However, it has been proposed to reduce the molecular weight of the polymer or to select a polymer excellent in solubility in a solvent as described above, or to select a solvent of Φ for controlling the evaporation rate, or to use a surfactant or the like. None of the above problems have been sufficiently improved. [Photosensitive Resin Transfer Material] Next, the photosensitive resin transfer material of the present invention will be described. 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 The configuration of the integrated film may be, for example, a structure in which a temporary support/thermoplastic resin layer/intermediate layer/photosensitive resin layer/protective film is laminated, and the color transfer material of the present invention can be used by using the foregoing The coloring photosensitive resin composition of the invention is provided with a photosensitive resin. (Temporary Support) In the photosensitive resin transfer material of the present invention, the temporary support system has flexibility and does not cause significant deformation, shrinkage or elongation under pressure, pressure or heat. necessary. Examples of such temporary supports include polyethylene terephthalate film, cellulose triacetate film, polystyrene film, polycarbonate film, etc., especially 2-axis extended polyethylene terephthalate. Diester films are particularly preferred. -112-200806754 (The thermoplastic resin layer) The component to be used in the thermoplastic resin layer is preferably selected from the organic polymer material described in JP-A No. 5-77.2, and is selected from the Vicat Vicat method ( Specifically, the organic polymer material having a softening point of about 8 〇 ° C or less is particularly preferable according to the method for measuring the softening point of the polymer of the American Material Testing Method ASTM D1 235. 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 Φ ester and saponified product thereof, polyvinylidene chloride, vinylidene chloride copolymer, polystyrene, styrene-ene and (meth) acrylate or saponified product thereof Vinyl toluene copolymer, poly(meth)acrylate, butyl (meth)acrylate, such as styrene copolymer, polyvinyl toluene, vinyl toluene and (meth) acrylate or its saponified product Poly(fluorene) copolymers such as vinyl acetate (meth) acrylate copolymer, vinyl acetate copolymer nylon, copolymerized nylon, N-alkoxymethylated nylon, N-dimethyl aminated nylon An organic polymer such as an amine resin.

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 coating of a plurality of coating layers and storage after coating. The intermediate layer is preferably an oxygen barrier film described in the "Separation Layer" or the aerobic blocking function described in Japanese Patent Publication No. Hei 5-72724. In this case, the sensitivity during exposure and the time load of the exposure machine can be reduced. Further, it is preferable that the oxygen barrier film exhibits low oxygen permeability, dispersion or dissolution in water or an alkaline aqueous solution, and can be appropriately selected from a conventional one. Among these, -11 3 - 200806754 is a combination of polyvinyl alcohol and polyvinylpyrrolidone. (Protective film) It is preferable to provide a thin protective film on the photosensitive resin layer in order to protect it from contamination or damage at the time of storage. 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 on a temporary support by coating a coating liquid (coating solution for a thermoplastic resin layer) in which a thermoplastic resin layer additive is dissolved and drying to provide a thermoplastic resin layer, followed by thermoplasticity. An intermediate layer forest solution composed of a 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 the thermoplastic resin layer 0 and the intermediate layer are provided on the temporary support, and a sheet in which the photosensitive resin layer is provided on the protective film, and the intermediate layer and the photosensitive resin layer are brought into contact with each other may be prepared. 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 joining methods are made by fitting each other. In the photosensitive resin transfer material of the present invention, the thickness of the photosensitive resin layer is preferably 1.0 to 5_0 μm, preferably 1.00 to 4·0 μηη, and 1.0 to 3·0 μητι. Further, it is not particularly limited, but the preferred film thickness of the other layers is -114-200806754. Generally, the temporary support 15~1〇〇μπι, the thermoplastic resin layer 2~3〇μΓΠ, the intermediate layer 〇·5~ 3·0μηη, protective film 4~40μητν. 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 polarizing axis and perpendicular thereto (refer to "The 7th Color Optical Conference, 512 Color Display 10_4" size TFT-LCD in 1990. Use color filters, planting wood, Xiaoguan, Fuyong, Shanzhong, etc.). Color filter The so-called high contrast system combines with liquid crystal to produce a bright and dark distinction. It is a very important performance in the liquid crystal display instead of CRT. The color filter of the present invention is used as a TV, from F 10 The monochromatic chromaticity of each of the light source, red (R), green (G), and blue (B) is different from that described in the following table (hereinafter, referred to as "target chromaticity" in the present invention). (ΔΕ) is preferably within a range of 5, more preferably within 3, and within 2 within a particularly good system. -115- 200806754 X y YR 0.656 0.336 21.4 G 0.293 0.634 52.1 B 0.146 0.088 6.90 The chromaticity in the present invention is determined by a microspectrophotometer (Olympus Optical Φ company; OSP 00 or 200) The F10 source is calculated as a result of 2 degrees of view, and is represented by 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, the method of forming the photosensitive resin layer 0 on the 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 above-described method. A photosensitive resin transfer material, a method of attaching it by a laminator, or 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, in which the above-mentioned [coloring photosensitive resin composition is particularly used) The slit coater described in the section of the coating film is suitable. Further, the preferred embodiment of the slit coater is 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 to 3.0 μm, preferably 1.0 to 2.5 μm, and particularly preferably 1.5 to 2.5 jjm. (b) The photosensitive resin transfer material of the present invention is attached to the substrate to be described later by the laminator by attaching the photosensitive resin transfer material of the present invention to the substrate to be described later, and the heated or/or pressurized roller or plate It is attached by pressing or heating. Specifically, the layer #压 described in Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. In the case of a low foreign matter, it is preferable to use the method described in JP-A-7-11-5755. 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]. '(Substrate) In the present invention, the substrate on which the color filter is formed is, for example, a transparent substrate, a soda lime glass plate having a cerium oxide film on its surface, a low expansion glass #, an alkali-free glass, a quartz glass plate, or the like. In the case of a glass plate or a plastic film, 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 is particularly good (oxygen interrupting film). In the case where the photosensitive resin layer is formed by coating with the colored photosensitive resin composition -117-200806754, an oxygen blocking film can be further provided on the photosensitive resin layer, whereby exposure can be improved. Sensitivity. 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 0.5 to 3 · 0 μm. (Exposure and development) 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 passed through and exposed from above the mask, and then imaged. The liquid is subjected to development, 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 and used as long as it is irradiated with light (for example, 365 nm, 405 nm, 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 mentioned. The exposure amount is usually about 5 to 200 mJ/cm 2 , preferably about 10 to 1 〇〇 mJ/cm 2 . Further, the above-mentioned developing liquid system is not particularly limited, and a general developing liquid such as those described in JP-A-5-72 2724 can be used. Further, it is preferable that the developing solution can perform a dissolution type development of the photosensitive resin layer. For example, a compound having a pKa of 7 to 13 is preferably contained in a concentration of 5 to 5 mol/L. Further, a small amount of an organic solvent which is miscible with water is added. 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, ε-caprolactone, γ-butyrolactone, dimethylformamide, dimethylacetamide, six Methylphosphoniumamine, ethyl lactate, methyl lactate, ε-hexyl-118-200806754 lactam, N-methylpyrrolidone and the like. The concentration of the organic solvent is preferably 〇·1 mass% to 30 mass%. Further, a general surfactant may be further added to the above developing solution. The concentration of the surfactant is preferably 0.01% by mass to 10% by mass. For the development method, a method such as squeezing development, spray development, spray and rotary development, immersion development, or the like can be used. Here, the above-described shower development will be described, and the uncured portion can be removed by spraying and blowing the developing liquid onto the exposed photosensitive resin layer. Further, Φ is preferably performed by spraying an alkaline liquid having a low solubility on the photosensitive resin layer before the development, and removing the thermoplastic resin layer, the intermediate layer, and the like. Further, it is preferable to spray the detergent or the like after the development, and to remove the development residue by wiping with a brush or the like. The liquid temperature of the developing liquid is preferably 20 ° C to 40 ° C, and the pH of the developing liquid is preferably 8 to 13. Further, in the case of producing the color filter of the present invention, as described in Japanese Laid-Open Patent Publication No. Hei No. Hei. No. Hei. The object is formed by forming a pedestal, forming a transparent electrode thereon, and then overlapping and dividing the protrusions for alignment to form a spacer, thereby reducing the cost. In the case where the overlapping coloring photosensitive resin composition is applied in this order, the film thickness is finally thinned each time in order to flatten the coating liquid. For this reason, it is preferable to overlap the four colors of Κ(black)*R*G*B and to overlap the protrusions for the division and alignment. On the other hand, when a transfer material having a thermoplastic resin layer is used, in order to keep the thickness constant, the overlapping colors are preferably 3 or 2 colors. Further, the size of the susceptor is preferably from 119 to 200806754, and it is preferable that the photosensitive resin layer is deformed to maintain a constant thickness, and it is preferably 25 μm or more and 30 μm or more. [Liquid crystal display device] The color filter of the present invention which is excellent in contrast is used in the liquid crystal display device of the present invention, and the sharpness of black compactness or the like is excellent. A liquid crystal display device that is a large screen such as a display for a personal computer or a television screen can be suitably used. % [CCD device]

The CCD device of the present invention comprises a color filter produced by using the above pigment nanoparticle. Hereinafter, the CCD device of the present invention will be described in detail. The 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, and a weak alkaline aqueous solution. These linear organic polymer polymers are side-locked with a polymer of a carboxylic acid, for example, JP-A-59-4461, JP-A-54-34327, JP-A-58-1 2577, and JP-A 54-25957 The methacrylic acid copolymer, the acrylic acid copolymer, the itaconic acid copolymer, the butenoic acid copolymer, and the butene group described in the specification of JP-A-59-53836, JP-A-59-7 1 0 48 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 for the polymerization of a hydroxyl group, the addition of an acid anhydride, and the like. In particular, among these, a benzyl (meth)acrylate/(meth)acrylic acid copolymer, a benzyl (meth)acrylate/(meth)propanoic acid/and a multicomponent copolymer with other monomers are used. Suitable. Further, 2-hydroxyethyl methacrylate, polyvinylpyrrolidone, polyethylene oxide, polyvinyl alcohol or the like is also useful as a water-soluble polymer. 120-200806754 Further, a 2-propyl propyl (meth) acrylate/polystyrene macromonomer/benzyl methacrylate 7 methacrylic acid copolymer described in JP-A-7-1-40654 , 2-hydroxy-3-phenoxypropyl acrylate/polymethyl methacrylate macromer/benzyl methacrylate/methacrylic acid copolymer' 2-hydroxyethyl methyl acrylate/polystyrene Macromonomer/methyl methacrylate/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 preferably from 5 to 90% by mass, more preferably from 1 to 60% by mass based on the total mass of the composition Φ. 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 at most 1 〇〇 ° C under normal pressure. A compound having at least one addition-polymerizable ethylenically unsaturated ' group and a boiling point of 1 oo ° C or more at normal pressure may, for example, be polyethylene glycol mono(meth)acrylate or polypropylene glycol ( Methyl) acrylate, phenoxy (meth) propylene glycerate, monofunctional acrylate or methacrylate; polyethylene glycol II. (methyl) propyl acrylate, trimethylol Ethane tri(meth)acrylate, neopentyl glycol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetras(tetra)(meth)acrylate, dipentaerythritol hexa(methyl) Acrylate, hexanediol (meth) acrylate, trimethylolpropane tris(propylene methoxypropyl) ether, tris(propylene methoxyethyl) trimer isocyanate, in glycerol or trimethylol A polyfunctional alcohol such as ethane is added to ethylene oxide or propylene oxide, and then subjected to (meth)acrylic acid esterification, Japanese Patent Publication No. 48-41 708, Japanese Patent No. 50-6034, and Japanese Patent Laid-Open No. 51- The urethane acrylates described in each of the publications No. 371, No. 93-200806754, JP-A-48-64183, A polyfunctional acrylic acid such as an epoxy acrylate such as a polyester acrylate or a reaction product of an epoxy resin and (meth)acrylic acid described in each of JP-A-49-431-91 and JP-A-52-30490 Ester or methacrylate. Further, it is also possible to use the Japanese Society of Associations Vo I. 20, No. 7, and pages 300 to 308 as photocurable monomers and low polymers. Further, a compound represented by the following formula (B-1) or (B_2) or a formula (B_1) can also be used.

CH2-〇-(B)nX CH2-〇-(B)nX X-(9)Π—OCH2,〒.CH:r Ο - CH2—CH2-〇- (H CH2-〇-{B)n—X CH2-〇 -(B>n-X formula.-

X-(B)m_ C—CH2- O- (B)nr-X CH2-〇m {In the formulas (曰-1) and (B-2), the B series independently represent _(CH2CH20)_

Any of &_(ch2ch(ch3)o)_; X each independently represents any one of an acryloyl group, a methacryloyl group, and a hydrogen atom, and in the formula (B-1), an acrylonitrile The total of the base and the methacryl fluorenyl group 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 each η In total, it is 3 to 24; m is an integer of 〇~6, and the total of each m is 2-16}. If the polymerizable monomer can be irradiated with radiation, a coating film having adhesion can be obtained. Can be used in any ratio. The amount used is usually from 5 to 90% by mass, preferably from 10 to 50% by mass, based on the total solid content of the composition. Coloring agent -122- 200806754 The coloring agent may be used by mixing one or more of various dyes, inorganic pigments or organic pigments which have been conventionally known. The dye system is not particularly limited, and a well-known dye used as a conventional color filter can be used. For example, Japanese Patent Publication No. Sho 64-9040 No. 3, JP-A-64-911-02, JP-A No. Hei 1-94301, JP-A-6-11614 U.S. Patent No. 5,567,920, U.S. Patent No. 5,505,950, U.S. Patent No. 5,567, 920, U.S. Patent No. 5, 567, 207, pp. 5, 333, 207, pp. No. 6-351, No. 6-351, No. 6-51, No. 5, No. 6-51, No. 5, No. 6 -1 9482 A pigment disclosed in No. 8 and the like. As the chemical structure, a pyrazole azo system, an anilino azo system, a triphenylmethane system, an anthracene system, a benzylidene group, an oxaphthalocyanine system, a pyrazolone, a triazole azo system, or a pyridinium can be used. A dye such as an azo 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, ruthenium, and the like. And a composite oxide of the above metals. The organic pigment may, for example, be C·L Pigment Yellow 11, 24, 31, 53, 83, 85, 99, 1 08, 1 09, 1 1 0, 1 38, 1 39, 1 50, 1 51, 1 54, 1 67,1 85, C· I. Pigment Orange 36,38,43,71, C·I. PigmentRed 1 0 5, 1 22, 1 49, 1 50, 1 55, 1 71, 1 75, 1 76, 1 77, 209, 224, 242, 254, CI Pigment Violet 19, 23, -123- 200806754 ue 1,2,15,

32, 39 ' C. I. PigmentBlu igment Green 7,36,37, C·I. Pigment I· Pigment Black 1,7, carbon black, etc. 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 or in combination with at least one of a diterpene yellow pigment or an isoporphyrin yellow pigment. For example, the lanthanoid pigments are, for example, C _ I · Pigment Red 彳 7 7 , 茈 颜料 pigments such as c 丨 颜料·Pigment Red 5 5 Φ, from the point of color reproducibility, with C.T • The mixture of Pigment Yellow 83 or C丄 Pigment Astragalus 39 is good. The mass ratio of the red pigment to the yellow pigment is 1 〇〇: 5 〜 1 〇〇: 5 〇 is good. Within this range, it is preferable to suppress the light transmittance of 4 〇 0 nm to 5 〇〇 nm and to improve the color purity. The green pigment is a halogenated phthalocyanine pigment alone or a mixture of a diazo yellow pigment, a phthalocyanine yellow dye or an isoporphyrin yellow pigment, for example, "C", Pigment Green 7, 3, 3 7 is preferably mixed with c _ 丨 _ pigment yellow 8 3, 1 3 8 , 1 3 9 . The mass ratio of the green pigment to the yellow pigment is preferably φ 100:5 to 1 00:1 00. Within this range, light transmittance of 4 〇〇 to 45 〇 nm can be suppressed, and good color purity can be obtained. The color-controlling pigment may be used alone or in combination with a dioxin-based violet pigment. For example, it is preferable to mix C·丨_pigment blue 1 5 : 6 and c. L pigment violet 2 3 . The mass ratio of the color-control pigment to the purple pigment is preferably 1 〇 〜 〜 〇 〇 : 5 〇. Within this range, light transmittance of 40 〇 n m to 420 nm can be suppressed, and color purity can be improved. Further, the above-mentioned pigments may be obtained by dispersing a finely dispersed powder such as an acrylic resin, a maleic acid resin, a vinyl chloride-vinyl acetate copolymer, and an ethyl cellulose-124-200806754 resin. The pigment is processed to produce a pigment-containing photosensitive resin which is excellent in dispersibility and dispersion stability. Further, the pigment for the black matrix is preferably carbon, titanium oxide or iron oxide alone or in combination with carbon and oxidized. The mass ratio is preferably in the range of 100:5 to 100:40. The long-wavelength light transmittance in this range is small, and the dispersion stability is also good. The solvent solvent is, for example, an ester such as ethyl acetate, n-butyl acetate, isobutyl β acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, Ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, methyl acetate, ethyl hydroxyacetate, butyl glycolate, methyl methoxyacetate, methoxyacetate a 3-hydroxypropionic acid alkyl ester such as ester, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-hydroxypropionate or ethyl 3-hydroxypropionate; Methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 2-hydroxypropionate, 2- Ethyl hydroxypropionate, propyl 2-hydroxypropionate, methyl 2-methoxy@propylpropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, 2-ethoxyl Methyl propionate, ethyl 2-ethoxypropionate, 2-oxy-2-methylpropionic acid - . -* . * Methyl ester, ethyl 2-oxy-2-methylpropionate, 2 Methyl methoxy-2-methylpropanoate, ethyl 2-ethoxy-2-methylpropanoate, methyl pyruvate, ethyl pyruvate, acetone Propyl ester, ethyl acetate methyl acetate, ethyl acetate ethyl acetate, methyl 2-hydroxybutyrate, ethyl 2-hydroxybutyrate, etc.: ethers, such as diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol Methyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol Butyl ether 'propylene glycol methyl ether acetate, propylene glycol ethyl-125-200806754 ether acetate, propylene glycol propyl ether acetate, etc.; ketones, such as methyl ethyl ketone, cyclohexanone, 2-glycol Ketone, 3-heptanone, etc.; aromatic hydrocarbons such as toluene, xylene, and the like. 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 in the composition. /. More than 70% to 90% by mass. These solvents may be used singly or in combination of two or more. Sensitizers can be used more. Specific examples thereof include, 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-9,10-fluorene, 2_t-butyl-9,10-fluorene, 2,6-dichloro-9,10 - hydrazine, benzoin, dibenzylideneacetone, ρ-(dimethylamino)phenyl phenylacetate, ρ-(-methylamino)phenylmethylstyrylone, benzene A benzothiazole-based compound of Φ is described in JP-A-51-48 51-6. The above-mentioned main components and other additives which are required to be applied can be prepared by mixing and dispersing using various mixers and dispersers. A general manufacturing method for manufacturing a color filter for a CCD device will be described later. The step of applying and drying the composition (color resist liquid) of the present invention onto the substrate, and the step of pattern-extracting the obtained dried coating film by a stepper or the like are sequentially performed. The step of developing, followed by the step of heat-treating, 'repeated the above steps sequentially for each color (3 colors or 4 colors) and produces a hardened film 'to obtain a color filter. More specifically, the above-mentioned curable composition is applied onto a suitable substrate by a rotator, and the film thickness during drying is generally 〇1 to 5 μηι, and preferably applied to 0.2 to 2 μΓΠ. It was placed in an oven at 85 ° C 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 light receiving image. Wafer formed by solid-state imaging device such as CCD, BBD, CID, BASIS, etc., compact image sensor using thin film semiconductor, liquid crystal display surface, color electrophotography, photoreceptor, electrochromic (EC) A substrate or the like of the display device. 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 thinly coating a substrate with a decane coupling agent or the like, or a decane coupling agent may be contained in advance in the hardening composition. 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. 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 a color resist is applied to the step, 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 to form a transparent planarizing film -127-200806754 preferably 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 dry under reduced pressure, indirect heat drying using high-temperature air, or the like, and direct heating drying (about 80 to 140 ° C, 50 to 200 seconds) by a hot plate or the like. Further, in order to make the pattern obtained after development sufficiently cured and to form a permanent film having improved mechanical strength, post-baking was performed. 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 0.5 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. The feature of the present invention is particularly remarkable in the manufacture of color filters for image sensors using one of the line spectra of mercury lamps from the appropriate side of the step, not to mention the use of LCDs. be usable. 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. -128- 200806754 Polymeric Heuristics 'Polymer heuristics can use general photopolymerization heuristics. 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 acylation ether described in the specification, the aromatic acylo compound substituted by the α-hydrocarbon described in the specification of U.S. Patent No. 2,72, 2, 521, and the description of the specification in U.S. Patent Nos. 3,046,1,27 and 2,951,758. The combination of a triallyl imidazole dimer/P-aminophenyl ketone described in the specification of U.S. Patent No. 3,549,367, and a benzothiazole compound/three described in Japanese Patent Publication No. Sho 51-48516 Halomethyl-s-three tillage compounds and the like. The content of the photopolymerization initiator (including the above-mentioned general photopolymerization initiator) in the negative-type curable composition containing the dye, and the solid content (mass) of the radical polymerizable monomer are 〇·〇1 to 5 0% by mass is preferable, and 1 to 30% by mass is preferable, and 1 to 20% by mass is particularly preferable. When the content is in the above range, φ does not undergo sufficient polymerization and hardening, and polymerization is difficult to proceed, the polymerization rate is increased, the molecular weight is lowered, and the film strength is also weakened. Further, in the above photopolymerization-inducing agent, a sensitizer and a photosensitizer can be used, and specific examples thereof include benzoin, benzoin methyl ether, 9-fluorenone, 2-chloro-9-oxime. Ketone, 2-methyl-9-fluorenone, 9-fluorenone, 2-bromo-9-fluorenone, 2-ethyl-9-fluorenone, 9,10-fluorene, 2-ethyl-9 , 10-蒽醌, 2-tert-butyl-9,10-fluorene, 2,6-dichloro-9,10-fluorene, xanthone, 2-methylxanthone, 2-methyl Oxyxanone, 2-ethoxyxanone, thioxanthone, 2,4-129-200806754 diethylthioxanthone, acridone, 10-butyl-2-chloroacridone , benzophenone, dibenzylideneacetone, P-(dimethylamino)phenylstyryl ketone, p-(dimethylamino)phenyl-p-methylstyrylone, diphenyl Ketone, P-(dimethylamine.yl)benzophenone (or mischrone), P-(diethylamino)benzophenone, benzofluorenone, etc., or special public 51-4851 The benzothiazole-based compound described in the publication No. 6, Tinuvi n 1130, the same 40 0, and the like. [Examples] Hereinafter, the present invention will be described in further detail based on examples, but the present invention is not limited thereto. (Example 1)

In dimethyl sulfoxide 1 0 0 0 ml, sodium methoxide 28% methanol solution 33.3 m pigment CI·Pigment Red 254 (trade name Irgaphor Red BT-CF Ciba Specialty Chemicals Co., Ltd.) 100 g, Polyvinylpyrrolidone 1 50g to prepare pigment solution A. Further, water containing 1 ml/min of hydrochloric acid 16 ml of water was prepared as a poor solvent. Here, 'the temperature is controlled at 18 ° C, and the precision chemical of Japan is used in 1 000 ml of water of a poor solvent which is stirred at 500 rpm by Fujisawa Pharmaceutical Co., Ltd., GK-0222-1 0 type Lamodo mixer. The company made np-kX-500 large-capacity pulseless pump, and injected 100 ml of pigment solution A at a flow rate of 1 〇〇 ml/min to form organic pigment particles to prepare pigment dispersion A. The obtained pigment dispersion liquid A was obtained by using a KOKU SAN (Function) Η12 type centrifugal filter and a P89C type filter cloth made of Kawana Co., Ltd., and concentrated at 4000 rpm for 90 minutes to obtain a dispersion (as a dispersion). A). After adding 50.0 m of ethyl lactate to 16.0 g of the above-mentioned pigment nanoparticle preparation paste, the dissolver was centrifuged at 1,500 rpm for 60 minutes, and then the FP-010 type filter manufactured by Sumitomo-130-200806754 Electric Fine Polymer Co., Ltd. was used. Filtration to obtain a paste-like concentrated pigment liquid A (nano pigment concentration: 30% by mass) [Preparation of pigment dispersion composition] The above paste was used to prepare a pigment dispersion composition A having the following composition. A 21· 3 g of pigment dispersant A (the above dispersant, exemplified compound 7.) 0.6 g of the polymer compound C-16 used in the present invention 3.2 g of 1-methoxy-2-propyl acetate 45.3 g

The pigment dispersant A was synthesized in accordance with JP-A-2000-239554. The pigment dispersion composition A having the above composition was dispersed by a honing machine M-50 (manufactured by Eiger Japan Co., Ltd.) using chromium oxide particles having a diameter of 0.65 mm at a peripheral speed of 9 m/s for one hour. The obtained pigment dispersion composition A was measured by using Nanotrack UPA-EX150 manufactured by Nikkiso Co., Ltd., and the result was an average particle diameter of .31 nm, and the ratio of particles having a particle size distribution of less than 15 nm was 5%. The ratio of particles exceeding 0 6 On m is 7%. (Example 2) The same procedure as in Example 1 except that the pigment dispersion liquid obtained in Example 1 was concentrated by a H-112 centrifugal filter manufactured by KOKUSA N (manufacturing), and changed to 50 〇 O rpm. The pigment dispersion composition B was prepared. (Example 3) When the pigment dispersion liquid A obtained in Example 1 was concentrated by a H-112 type centrifugal filter manufactured by KOKUS AN, it was changed to 5 rpm and 300 minutes. The pigment dispersion composition -131-200806754 C was prepared in the same manner as in Example 1. (Comparative Example 1) In the case of concentrating the pigment dispersion liquid obtained in Example 1 with a H-112 centrifugal filter manufactured by KOKUSAN Co., Ltd., it was changed to 3400 rpm for 10 minutes, and completely the same as Example 1. Similarly, the pigment dispersion composition D was prepared (Comparative Example 2) The pigment dispersion composition E having the following composition was prepared as described below. Pigment (Pigment Red 254) 6.4 g Sodium chloride 6 4.0 g Compound C -1 6 3.2g obtained in the present invention

Powder of sodium chloride, pigment (pigment red 2 54) in a solution of 1-methoxy-2-propyl acetate, and the above-mentioned compound C-1 6 used in the present invention are fed into a two-arm type kneader , knead at 10 ° C for 10 hours. After kneading, 500 parts by mass of a 1% hydrochloric acid aqueous solution at 80 ° C was taken out, stirred for 1 hour, filtered, and washed with water to remove sodium chloride and a solvent, and then dried at 65 ° C for 14 hours, and then pulverized, and 1 g was pulverized with respect to the pulverized φ substance. 2.4 g of mixed 1-methoxy-2-propyl acetate was added. The above-mentioned pigment composition was dispersed by an electric honing machine M-50 (manufactured by Eiger Japan Co., Ltd.) using chromium oxide particles having a diameter of 0.65 mm at a peripheral speed of 9 m/s. A pigment dispersion composition E was obtained. The treatment was carried out in the same manner as in Example 1. The particle diameter measured was a number average particle diameter of 5 3 n m, the ratio of particles having a particle size distribution of less than 15 nm was 18.8%, and the ratio of particles exceeding 60 nm was 24%. (Comparative Example 3) A pigment dispersion composition-132-200806754 F was produced in the same manner as in Comparative Example 2 except that the drying conditions after filtration and washing in Comparative Example 2 were changed to 80 ° C for 48 hours. Measurement] The obtained pigment dispersion compositions A to F were each applied onto a glass substrate to have a thickness of 2 μm to prepare a sample. A polarizing plate made of a three-wavelength polarizing plate (a polarizing plate manufactured by Sanritsu Co., Ltd.) is used in a three-wavelength cold cathode tube light source (FWL18EX-N manufactured by Toshiba LITEC Co., Ltd.). This sample was placed between LC2-2 and 5), and the amount of transmitted light when it was parallel to the polarization axis was measured, and the ratio of the transmitted light was compared. (Refer to "The 7th color Φ color optical conference in 990, 512 color display" 1〇.4" size is 1-1^0 with color filters, Ueki, Xiaoguan, Fuyong, Shanzhong, etc.). The chromaticity was measured using a color luminance meter (ΒΜ-5 manufactured by TOPCON Co., Ltd.). Two polarizing plates, a sample, and a color brightness meter are disposed at a position of 13 mm from the backlight, and a cylinder having a diameter of 11 mm and a length of 20 mm is disposed from a position of 40 mm to 60 mm. The light system was irradiated with a measurement 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 40 mm. The measurement angle φ of the color luminance meter is set to 2 °. In the state where the sample is not provided, the brightness of the two polarizing plates is set to 1280 cd/m 2 when the polarizing plate is placed in parallel Nicols, and the sample is irradiated with a high-pressure mercury lamp of 90 mW/cm 2 . In hours, the color difference before and after the irradiation is set as an indicator of light resistance. Further, the chromaticity system of the present invention was measured by a microspectrophotometer (manufactured by Olympus Optical Co., Ltd.; OSP 100 or 200), and was calculated as a result of 2 degrees of field of view of the F10 light source, and was calculated by the xyz color system. xyY値 indicates. Further, the difference in chromaticity is expressed by the color difference of the La#b# color system. The smaller the color difference, the better. -133- 200806754 The comparison of the samples obtained from the pigment dispersion compositions A to F and the results of the light resistance were as shown in Table 1.

[Table 1] Water content (%) Ratio of particle size below 15 nm (%) Ratio of particle size exceeding 60 nm (%) Comparative Remarks Pigment Dispersion Composition A 4.5 5 7 12000 Pigment Dispersion Composition of the Invention B 2.2 5 7 16500 The present invention Pigment Dispersion Composition C 0.6 5 7 17000 Pigment Dispersion Composition of the Invention D 7.0 5 7 9500 Comparative Example Pigment Dispersion Composition E 6.8 18 24 6400 Comparative Example Pigment Dispersion Composition F 0.7 18 24 7200 Comparison As shown in Table 1, The pigment dispersion composition of the invention exhibited very excellent contrast and light resistance as compared with the comparative example. (Example 4-1) The pigment dispersion composition A was mixed with other components of the following Table 2 to prepare a coloring photosensitive resin composition for color filter A ° [Table 2] Component content (parts by mass) -g material dispersion composition A__________ 44.5 propanol monomethyl ether acetate.., 7.6 methyl ethyl ketone 37 binder-1 ____-- 0.7 DPHA liquid ____ 3,8 2-dichloro 5-(p-styrylstyrene oxime 0.12 2,4-bis(trichloromethyl)-6-[4,-(N,N-diethoxycarbonylmethyl)0-female-3 -Bromophenyl]-s·Triad _____ 0.05 phenothiaquinone---- 0.01 Surfactant 1 _______ 0.06

<Binder 1> ^•Polymer (benzyl methacrylate/methylpropanoic acid/methyl propyl acetonate = random copolymer of 38/25/37 molar ratio, 4 力 in Lizi ) 27-mass -134- 200806754 • Propylene glycol monomethyl ether acetate 7 3 parts by mass <DPHA1>" • Dipentaerythritol hexaacrylate (polymerization inhibitor MEHQ5 00 ppm, Japan Chemicals Co., Ltd.) System, trade name: KAYARAD DPHA) 76 parts by mass • Propylene glycol monomethyl ether acetate 2 4 parts by mass < surfactant 1> • The following compound 1 30 parts by mass

• Methyl ethyl ketone 7 〇 parts by mass Compound 1 —(CH2-CH)4〇— -iCH2-CH)x—(CH2-CH)y--

〇=C 〇=c 0=C

OCH2CH2CnF2n+1 0(P0)7H 0(EO)7H fn = 6, x = 55, y = 5,

Mw=33940NMw/Mn=2. 55 P〇: propylene oxide, EO: ethylene oxide. In addition to the pigment dispersion composition B~F, in place of the pigment dispersion composition A, in the same manner as above, The coloring photosensitive resin composition for modulating the color filter is applied to the glass substrate by a spin coater using a coloring photosensitive composition for color filter production, and dried at 100 ° C for 2 minutes. A film having a thickness of about 2 μm is formed. Subsequently, the film was exposed to light under a nitrogen stream using an ultrahigh pressure mercury lamp, and then developed with a 1% aqueous sodium carbonate solution. The comparison of the R component of each of the obtained films and the light resistance were measured in the same manner as in the above [Comparative measurement], as shown in Table 3 below. 135-200806754 [Table 3] Comparative Light Resistance (Color Difference) Remarks Colored resin composition A 10500 1.9 Colored resin composition B 15000 2.0 of the present invention Colored resin composition C 16200 1.7 of the present invention Colored resin composition D 9000 of the present invention 3.9 Comparative Example Colored resin composition E 5800 4.6 Comparative Example Colored resin composition F 6500 3.5 Comparison As shown in Table 3, the colored photosensitive resin composition of the present invention exhibited very excellent contrast and light resistance as compared with the comparative example.

(Example 4-2) [Production of Color Filter (Production by Application Using Slit Nozzle)] [Formation of Black (K) Image] After washing the alkali-free glass substrate with a UV cleaning device Wash the brush with a detergent and then wash it with ultrapure water. The substrate was heat-treated at 120 ° C for 3 minutes to stabilize the surface and surface conditions. After cooling the substrate and adjusting the temperature to 23 ° C, the φ glass substrate coating machine (manufactured by FAS, Inc., trade name: MH-1 600) having a slit nozzle was used to apply the coating described in Table 4 below. The colored photosensitive resin composition K1 composed of the composition is composed. Thereafter, the film was dried in a VCD (vacuum drying apparatus; manufactured by Tokyo Ohka Kogyo Co., Ltd.) for 3 seconds, and the solvent of the dried portion was made to have no fluidity of the coating layer, and then prebaked at 120 ° C for 3 minutes to obtain a film. Photosensitive resin layer having a thickness of 2·4 μηΐ Κ1 〇-136· 200806754 [Table 4] Composition κ (parts by mass) 25 Propyl alcohol monomethyl ether acetate 8.0 Methyl ethyl ketone 53 1 2 ' " 9.1 1醌 monomethyl ether ~~ " 0.002 DPHA liquid 2,4-di(trichloromethyl)-6_[4,-(1\1,1\1-diethoxycarbonyl Amino-3'-bromophenyls-three tillage 0.16 surfactant 1 : 0.044

Exposing the mask surface in a state where the substrate and the mask (the quartz exposure mask having the portrait pattern) are vertically erected by a proximity type exposure machine (manufactured by Hitachi High-Tech Electronics Co., Ltd.) having an ultrahigh pressure mercury lamp The distance from the photosensitive resin layer was set to 200 μm, and pattern exposure was performed at an exposure amount of 300 mJ/cm 2 . Then, pure water is sprayed by a shower nozzle to uniformly wet the surface of the photosensitive resin layer K1, and then the KOH-based developing solution (containing KOH, nonionic surfactant, trade name: CD K-1, Fujifilm Electronics) The company made a film at 80 ° C for 80 seconds, and sprayed the image with a flat nozzle pressure of 0.0 4 Μ P a to obtain a patterned image. Thereafter, the ultrapure water was continuously sprayed at a pressure of 9.8 MPa by the ultrahigh pressure washing nozzle, and the residue was removed to obtain a black (K) image K. Thereafter, heat treatment was continued at 220 ° C for 30 minutes. [Formation of Red (R) Pixels] The colored photosensitive resin composition R1 composed of the composition described in Table 5 below is formed on the substrate on which the image K is formed, and is formed in the same manner as the above-described black (K) image. The step of forming a pixel R that completes the heat treatment. The film thickness of the photosensitive resin layer R1 and the coating amount of the pigment (C.LP_R.254 and -137-200806754 CHR.177) are as follows. Photosensitive resin film thickness (μπι) 1.60 Pigment coating amount (g/m2) 1.0 0 C_I_P.R.254 coating amount (g/m2) 0.80 C.im77 coating amount (g/m2) 0.20 [Table 5] Composition content (Parts by mass) R Pigment Dispersion A 40 R Pigment Dispersion 2 (C.LP.R. 177) 4.5 Propylene Glycol Monomethyl Ether Acetate 7.6 Methio Ethyl Ketone 37 Adhesive Agent - 0.7 0.7 DPHA Solution 3.8 2- Trichloromethyl-5-(p-styrystyryl)-1,3,4-oxadiazole 0.12 2,4-bis(trichloromethyl)·6-[4'-(Ν,Ν -diethoxycarbonylmethyl)amino-3'-bromophenyl]-s-tripper 0.05 phenothimethicone 0.01 surfactant 1 0.06

[Formation of Green (G) Pixel] On the substrate on which the image K and the pixel R are formed, the colored photosensitive resin composition G1 composed of the composition described in Table 6 below is used to be black (K) The same steps are formed in the image to form the pixel G which is subjected to the heat treatment. The film thickness of the photosensitive resin layer G1 and the coating amount of the pigments (C·丨_P.G.36 and C.I.P.Y.150) are as follows. Photosensitive resin film thickness (pm) 1.60 Pigment coating amount (g/m2) 1.9 2 CIPG36 coating amount (g/m2) 1.34 CIP_Y_1 50 coating amount (g/m2) 0.58 -138- 200806754 [Table 6] Composition Content. (mass parts) G pigment dispersion 1 (C_LP.G· 36) 28 丫 pigment dispersion 1 (CIRY. 150) 15 propylene glycol monomethyl ether acetate 29 methyl ethyl ketone 26 cyclohexanone 1.3 Adhesive-2 2.5 DPHA liquid 3.5 2-trichloromethyl-5-(p-styrystyryl)-1,3,4·oxadiazole 0.12 2,4-bis(trichloromethyl)- 6-[4'-(N,N-bisethoxycarbonylmethyl)amino-3'-bromophenyl]-s-tripper 0.05 phenothiazine trap 0.01 surfactant 1 0.07 [blue (B) pixel Formation of the coloring photosensitive resin composition B 1 composed of the composition described in the following Table 7 on the substrate on which the image K, the pixel R, and the pixel G are formed, and the formation of the black (K) image In the same step, the pixel B on which the heat treatment is completed is formed to obtain the color filter A of interest.

The film thickness of the photosensitive resin layer B1 and the coating amount of the pigment (C.I.P.B. 15:6 and C.I.P.V.23) are as follows. Photosensitive resin film thickness (pm) 1.60 Pigment coating amount (g/m2) 0.7 5 0·Ι·Ρ_Β·1 5:6 coating amount (g/m2) 0.705 C".P_V.23 coating amount (g/ M2) 0.045 -13 9- 200806754 [Table π 糸 and component content (parts by mass) B Pigment Dispersion 1 (CIPB15:6) 8.6 ΒPigment Dispersion 2 (σΐ·Ρ·Β·15:6 + CIPV23 15 propylene glycol monomethyl ether acetate 28 methyl ethyl ketone 26 binder-3 17 DPHA liquid 4.0 2-trichloromethyl-5-(p-styrystyryl)-1,3,4 -oxadiazole 0.17 phenothiazine trap 0.02 surfactant 1 0.06

Here, the preparation of the colored photosensitive resin compositions Κ1, R1, G1, and Β1 described in the above Tables 4 to 7 will be described in further detail. For the production of the colored photosensitive resin composition Κ1, first, the bismuth pigment dispersion 1 and propylene glycol monomethyl ether acetate in the amounts described in Table 4 were weighed and mixed at a temperature of 24 ° C (± 2 ° C). And stirring at 150 rpm for 10 minutes, and then weighing the amount of methyl ethyl ketone, binder 2, hydroquinone monomethyl ether, DPHA liquid, 2,4-bis(trichloromethyl)- 6_[4'-(1\1,1\1-bisethoxycarbonylmethyl)amino-3'-bromophenyl]-s-triad, surfactant 1, sequentially at temperature 2 5 It was added at °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 following components is as follows. Pigment Dispersion 1> • Carbon black (trade name: Nipex 35, manufactured by Degussa Japan Co., Ltd.) 1 3.1 parts by mass • Dispersant (Compound 2J below) 0.65 parts by mass • Polymer (benzyl methacrylate) / methacrylic acid = 72/28 molar ratio -140 - 200806754 random copolymer, molecular weight 37,000) 6_72 parts by mass • propylene glycol monomethyl ether acetate 79_53 parts by mass

® <Binder 2> • Polymer (benzyl methacrylate/methyl propylene acid = 78/22 mole ratio random copolymer, molecular weight 38,000) 27 parts by mass • Propylene glycol mono- phthalate acetic acid 73 parts by mass of the colored photosensitive resin composition R1 was produced by first weighing the R pigment dispersion A, the R pigment dispersion 2, and the propylene glycol monomethyl ether acetate in the amounts shown in Table 5 at a temperature of 24°. C (±2 ° C) was mixed and stirred at 150 rpm for 10 minutes. Then, the amount of methyl ethyl ketone, binder, 1, 〇?^^, 2-trichloro of the amount described in Table 5 was taken. Methyl-5-0-styrylstyryl-1,3,4-oxadiazole, 2,4-bis(trichloromethyl)-6-[4'-(叱1^双ethoxy Alkylcarbonyl)amino-3'-bromophenyl]-s-three tillage, phenothiazine trap, added sequentially at a temperature of 24 ° C (± 2 ° C), and stirred at 150 rpm for 30 minutes, Further, the amount of the surfactant 1 described in Table 5 was weighed and added at a temperature of 24 ° C (± 2 ° C) and stirred at 30 rpm for 5 minutes, and filtered by nylon mesh #200. Further, among the compositions described in Table 5, the R pigment dispersion a is Example 1 The pigment dispersion composition A similar embodiment is obtained for that composition as follows based -141-200806754 modulated parts by mass. <R Pigment Dispersion A> • Paste-like concentrated pigment liquid A (CJ.PR254) of Example 1 23 parts by mass • Dispersant (the above compound 2J) 0.8 parts by mass • Polymer (benzyl methacrylate/A) Acrylic acid = 72/28 molar ratio random copolymer, molecular weight 30,000) 8 parts by mass • Propylene glycol monomethyl: ether acetate 68: _ 2 parts by mass < R pigment dispersion 2 >

Red A2B, Ciba special 18 parts by mass • CIP_R.1 77 (trade name: Cromophtal special chemical (stock) company) • Polymer (benzyl methacrylate / methacrylic acid = 72/28 molar ratio of random) Copolymer, molecular weight 30,000) 12 parts by mass • Propylene glycol monomethyl ether acetate 70 parts by mass The coloring photosensitive resin composition G 1 was produced by first weighing the amount of the G pigment dispersion 1 described in Table 6. Y pigment dispersion 1, propylene glycol monomethyl ether acetate, mixed at a temperature of 24 ° C (± 2 ° C), and stirred at 150 rpm for 10 minutes, and then, the amount of methyl groups described in Table 6 was evaluated. Ethyl ketone, cyclohexanone, binder 2, DP Η A solution, 2-trichloromethyl-5 (p-styrystyryl)-1,3,4-oxadiazole, 2,4 - bis(trichloromethyl)-6-[4'-(indenyl bisethoxycarbonylmethyl)aminobromophenyl s-triazine, phenothiazine trap at a temperature of 24 ° C (± 2 Add sequentially at °C) and stir at 150rPm for 30 minutes. Again, add the amount of surfactant 1' listed in Table 6 at a temperature of 24 °C (±2 force) and stir at 30 rpm. Minutes, filtered by nylon mesh #200 Also obtained, in the composition described in Table 6, G 1 based pigment dispersion so -142- "trade name: GT-2" 200806754 by Fujifilm Electronic Materials (Unit) manufactured by. Y pigment Dispersion 1 is "trade name: CF YELLOW EX3393" manufactured by Kosei Co., Ltd. In the preparation of the colored photosensitive resin composition B1, first, the amount of the B pigment dispersion 1, B pigment dispersion 2, and propylene glycol monomethyl ether acetate in the amounts described in Table 7 were weighed at a temperature of 24 ° C (±2). °C), and stirred at 150 rpm for 10 minutes, then weighed the amount of methyl ethyl ketone, binder 3, DPHA solution, 2-trichloromethyl-5 as described in Table 2-5. · (ρ-styrylstyryl)-1,3,4-Φ oxadiazole, phenothiazine, added at a temperature of .25 °C (±2 °C) at a temperature of 40 ° C ( Stir at 150 rpm for 30 minutes at ±2 ° C), and then weigh the amount of surfactant 1 described in Table 2-5, add at a temperature of 24 ° C (± 2 ° C) and stir at 30 rpm. In the composition described in Table 7, among the compositions described in Table 7, the B pigment dispersion 1 was used under the trade name "CF" by the company. BULE EX3357". In the B pigment dispersion 2, "trade name: CF BULE • EX3383" manufactured by Yuki Co., Ltd. was used. The composition of the binder 3 is as follows. <Adhesive 3 > • Polymer (benzyl methacrylate/methylpropionic acid/methyl methacrylate = random copolymer of 36/22/42 molar ratio, molecular weight 38,000) 2 7 mass 73 parts by mass of propylene glycol monomethyl ether acetate were used instead of the concentrated pigment liquids obtained in Examples 2 and 3 and Comparative Examples 1 to 3 (hereinafter, simply referred to as "concentrated pigment liquids B to F"). The R pigment dispersions B to F were prepared by using the concentrated pigment liquid A of the R pigment dispersion A. Further, in contrast to -143-200806754, the method for producing the color filter A described above is performed in the same manner as the color pigment filter B except that the R pigment dispersions B to F are used instead of the R pigment dispersion A, respectively. F. The results of measurement of contrast and light resistance in the same manner as in the above [Comparative measurement] for each color filter are shown in Table 8. [Table 8]. Comparative Light Resistance (Color Difference) Remarks Color Filter A 1 0000 1.9 Color Filter B 1 4500 of the Invention 2.0 Color Filter of the Invention c 1 5 4 0 0 1.7 Color Filter D of the Present Invention 1 8500 3.9 Comparative Example Color Filter E 5 3 0 0 4.6 Comparative Example Color Filter F 5 7 00 3.5 Comparative Example From the above results, it is known that the color filter of the present invention is compared with the comparative example. Very high contrast and lightfastness. The degree to which the color difference will be different for two or more different viewers. Moreover, through long-term use (for example, one year or more), the difference is that the difference is large and a significant difference is formed on the display screen. The color filters of the present invention are all highly contrasted and are good color ® filters. On the other hand, the color filter of the comparative example has a low contrast ratio and is a grade which cannot satisfy the practically required level. (Example 4-3) [Production and evaluation of liquid crystal display device] A liquid crystal display device was produced using the color filters A to F, and the display characteristics were evaluated. (Formation of ITO electrode) The glass substrate formed by the color filter is placed in a sputtering apparatus, and at 100, ITO (indium tin oxide) having a thickness of 1,300 Å is completely vacuum-deposited, and then -144-200806754 240°. C was annealed for 90 minutes to crystallize the ITO to form a chitin 0 transparent electrode. (Formation of a spacer) A spacer is formed on the above-described 丨τ transparent electrode by the same method as the spacer formation method described in [Example 1] of JP-A-2004-240335. (Formation of Liquid Crystal Alignment Control Protrusion) The liquid crystal alignment control projection is formed on the I ΤΌ transparent electrode formed of the spacer described above 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.) is disposed at a distance of 1 〇〇 # m from the surface of the photosensitive resin layer, and the irradiation energy is utilized by the ultra-high pressure mercury lamp through the reticle. '15 0mJ/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, the liquid crystal alignment of the photosensitive resin layer having the desired shape can be obtained on the color filter side substrate by removing the unnecessary portion (exposure portion) of the photosensitive resin layer by φ. The substrate for a liquid crystal display device formed by the protrusions is controlled. Then, the substrate for a liquid crystal display device formed by the projection of the liquid crystal alignment device was baked at 230 ° C for 30 minutes to form a liquid crystal alignment control projection which was cured on the substrate for a liquid crystal display device. <Formulation of a coating solution for a positive photosensitive resin layer • Positive type FH-2413F) Photoresist (53 parts by mass of Fujifilm Electronic Materials Co., Ltd.) 145-200806754 • Methyl ethyl ketone: 46.7 parts by mass • M Egafa GF · 7 8 0 F (manufactured by Dainippon Ink Chemicals Co., Ltd.): 质量.〇4 parts by mass (manufacture of liquid crystal display device) The substrate for liquid crystal display device obtained above is further provided with An alignment film formed of an amine. Subsequently, a phase is disposed around the pixel group surrounding the color filter. When the position of the black matrix frame is printed, the sealing agent of the epoxy resin is printed, and φ drops the liquid crystal for the MVA mode. After bonding to the opposite substrate, the bonded substrate is heat-treated to harden the sealant. On both sides of the thus obtained liquid crystal cell, a polarizing plate HLC2-2 5 18 manufactured by Sanritsu Co., Ltd. is attached. Next, a backlight of a three-wavelength cold cathode tube light source (FWL1 8EX-N manufactured by Toshiba UTEC Co., Ltd.) was formed, and the polarizing plate was placed on the side of the back surface of the liquid crystal cell to form a liquid crystal display device. Comparison In the liquid crystal display device using the color filter of the present invention, the liquid crystal display device using the color filter of the present invention has been confirmed to have excellent black compactness and redness, and exhibits excellent display characteristics without display unevenness. (Example 5·1) t [Production of Color Filter (Production of Multilayer Photosensitive Resin Transfer Material)] [Production of Photosensitive Resin Transfer Material] Using a slit nozzle, the following formula H1 The thermoplastic resin layer was coated with a coating liquid and dried to a polyethylene terephthalate film temporary support having a thickness of 75 μm. Then, it was made up of the following formula 所1 -146-200806754 The layer is coated with a coating liquid and dried. The colored photosensitive resin composition K1 is applied and dried, and a thermoplastic resin layer having a dry film thickness of 14.6 μm and a dry film thickness of 1 are provided on the temporary support. · 6 μ m of intermediate layer, a photosensitive resin layer with a dry film thickness of 2.4 μm, and a rolled protective film (thickness 12 pm polypropylene film). A thermoplastic resin layer, an intermediate layer (oxygen blocking film) and black (K) photosensitive resin layer of the photosensitive resin integrally

Transfer material K1 〇 <Coating liquid for thermoplastic resin layer: Formulation Η 1 > • Methanol 1 1 _ 1 part by mass • Propylene glycol monomethyl ether acetate 6.36 parts by mass • Methyl ethyl ketone 52.4 parts by mass • Methyl methacrylate/2-ethylhexyl acrylate/benzyl methacrylate/methacrylic acid copolymer (copolymerization composition ratio (mole ratio) = 5 5/11_7/4_5/28.8, molecular weight: 90,000 , Tg: about 70 ° C) 5_8 3 halo parts • styrene / acrylic acid copolymer (copolymerization composition ratio (mole ratio) = 63 / 37 molecular weight: 10,000, Tg: about 1 〇〇 ° C) 13.6 mass A compound obtained by dehydration condensation of bisphenol A and pentaethylene glycol monomethacrylate 2 equivalents (manufactured by Shin-Nakamura Chemical Co., Ltd., trade name · 2,2-bis[4-(methacryl oxime) Oxypolyethoxy)phenyl]propane) 9.1 parts by mass • The above surfactant 1 〇 _ 5 4 parts by mass < coating solution for intermediate layer: formulation Ρ 1 > • PVA2 05 (polyethyl alcohol) , Kuraray Co., Ltd., Lane Degree = 88%, degree of polymerization 5 5 〇) 3 2 · 2 parts by mass • Polyvinylpyrrolidone (ISP · Japan Co., Ltd., κ_30) -147-200806754 14.9 parts by mass. 5.2 parts by mass of distilled water. 429 parts by mass of methanol. Next, the colored photosensitive resin composition K1' used for the production of the photosensitive resin transfer material K1 is changed to In the same manner as described above, a photosensitive resin transfer was carried out in the same manner as described above except for the following colored photosensitive resin compositions R1 〇1, G1 01 and B1 01 which are composed of the compositions described in Tables 9 to 11. Materials R1 0 1 , G 1 0 1 and B 1 0 1 . Further, the preparation methods of the colored photosensitive resin compositions R 1 〇 1 , G 1 0 1 and B 1 0 1 are respectively prepared according to the above-described methods of preparing the colored photosensitive resin compositions R1, G1 and Β1. [Table 9]

R1 01 Composition (parts by mass) R Pigment Dispersion A _—— 40 R Pigment Dispersion 2 (CIRR· 177) 4.5 Propyl Alcohol Monomethyl Ether Acetate 7.6 Methyl Ethyl Ketone 37 Adhesive - 1 _—— 0.8 DPHA liquid — 4.4 chloromethyl-5-(p-styrystyryl)-1,3,4-oxadiazole 0.14 2,4-bis(trichloromethyl')- 6-[4' -(N,N-bisethoxycarbonylmethyl)amino-3-3-bromophenyl]_s·two-well 0.06 phenothiazine trap 0.01 additive 1 0.52 surfactant 1 0.06 -148- 200806754 Table 1 ο]

G1 01 Composition --- Content (temporary portion) 5 Pigment Dispersion 1 (CIPGr36) ^ ^ — 28 "Caries Dispersion 1 (CIPY Factory 150)~' ^ ^ 15 + Propyl Alcohol Methyl Ether Acetate - ^ ^ - 29 " ¥ Ketyl Ethyl Ketone: ^~^ — 26 1 Hexanone — -~^ — 1.3 ^Centrant-2 ' 3.0 Tpha Liquid ' ^ —-- — 4.3 ^ Dichloromethyl-5-(p-styrylstyrene~' 0.15 ^4-bis(dichloromethyl)-6-[4'^(Ν,Ν-^Γoxybromophenyl)-s -Three wells 0.06 ~mmm ~-- 〇〇1 Surfactant 1 ' ~~~— 〇〇7 [Table 11] B1 0 1 Composition content (parts by mass) 8 6 ~^Pigment dispersion 1 (CIRB· 15 : 6) '-- B pigment dispersion 2 (CIRB· 15 : 6 + CIPV· 23) ^ ~— 15 Propyl alcohol monomethyl ether acetate ~~ 28 methyl ethyl ketone ^ — 26 Bonding Agent-3 ' - 18 5 DPHA liquid - 4.3 2-dichloromethyl-5·(ρ-styrystyryl)-1,3,4-oxo-~--- 0.17 phenothiazine trap--- 〇〇2 Surfactant 1 ''-0 06 In addition, among the compositions described in Table 9, the additive 1彳 is a phosphate-based special active agent (manufactured by Nanben Chemical Co., Ltd.) Product name: HI PLAAD ED 1 5 2). [Formation of black (K) image] The alkali-free glass substrate is sprayed with a glass detergent liquid adjusted to 25 ° C, and it is blown for 20 seconds. Nylon hair rotating brush, -149- 200806754 and washed with pure water spray, by spraying decane coupling solution (N - β (aminoethyl) r - aminopropyl trimethoxy decane 〇 - 3 mass % aqueous solution, trade name: ΚΒ 603 603, manufactured by Shin-Etsu Chemical Co., Ltd.) and blown for 20 seconds, and washed with pure water. The substrate was preheated at 1 基板. After heating at ° C for 2 minutes, it was sent to a laminator. After the protective film of the photosensitive resin transfer material K 1 was peeled off, it was passed through a laminator (manufactured by Hitachi Industrial Co., Ltd. (Lamicll type)) at the above 100 t The heated substrate was laminated at a rubber roll temperature of 130 ° C, a linear pressure of 100 N/cm 2 , and a transfer speed of 2.2 m/min. After the temporary support was peeled off from the interface with the thermoplastic resin layer, the ultrahigh pressure mercury lamp was used. Proximity exposure machine (Hitachi Hi-Tech Electronic Engineering Co., Ltd.) In the state in which 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 is set to 200 μηη, and the exposure amount is 70 mJ/cm 2 . Pattern exposure. Next, a triethanolamine-based developing solution (containing 2.5% of triethanolamine, containing a nonionic surfactant, containing a polypropylene-based antifoaming agent, trade name: T-PD 1 ', manufactured by Fuji Photo Film Co., Ltd.) 30 °C50 seconds, and spray imaging with a flat nozzle pressure 〇 _ 04 M Pa to remove the thermoplastic resin layer and the intermediate layer, continue to use sodium carbonate imaging solution (containing 0.06 mol / liter of hydrogen carbonate) Sodium, the same concentration of sodium carbonate, 1% sodium dibutylnaphthalene sulfonate, an anionic surfactant, antifoaming agent, stabilizer, trade name: T-CD1, manufactured by Fuji Photo Film Co., Ltd., at 29 ° C For 30 seconds, spray development was performed with a cone nozzle pressure 〇 1 5 Μ P a , and a photosensitive resin layer was developed to obtain a patterned image. -150-200806754 After that, continue to use a detergent (containing phosphate, citrate, nonionic surfactant, antifoaming agent, stabilizer, trade name "T-s D 1 (made by Fuji Photo Film Co., Ltd.)", Or a sodium carbonate/phenoxy oxyethylene surfactant, trade name "T-SD2 (made by Fuji Photo Film Co., Ltd.)), at 33 ° C 2 sec., with cone nozzle pressure (K02 MPa spray) Residue removal by a rotating brush with nylon hair to obtain a black (K) image. Subsequently, the substrate is further lighted from the side of the resin layer by using an ultrahigh pressure mercury lamp at 5000 m J / cm 2 After the post-exposure, the film was heat-treated at 220 ° C for 15 minutes. The substrate forming the image K was washed with a brush and washed with pure water as described above, and then sent to the substrate for preheating without using a decane coupling solution. [Formation of Red (R) Pixel] Using the above-described photosensitive resin transfer material R 1 0 1 , a red (R) pixel R which is subjected to heat treatment is obtained in the same procedure as the above-described photosensitive resin transfer material K 1 . Among them, the exposure amount is set to 40mJ/cm2, which is displayed by sodium carbonate. The film thickness of the photosensitive resin layer R1 〇1 and the coating amount of the pigments (CIPR_254 and C.丨.PR177) are as follows. Photosensitive resin Film thickness (μηη) 2.00 Pigment coating amount (g / m2) 1.0 0 C_ 丨.PR254 coating amount (g/m2) 0.8 0 CIPR1 77 coating amount (g/m2) 0.20

The substrate on which the image K and the pixel R are formed is washed by a brush or a pure water spray as described above, and then sent to a substrate preheating apparatus without using a decane coupling liquid. [Formation of Green (G) Pixels] Using the photosensitive resin transfer material G 1 〇1 described above, a green (G) pixel which is subjected to heat treatment is obtained in the same procedure as the above-described photosensitive -151 - 200806754 resin transfer material R101. Among them, the exposure amount was set to 40 mJ/cm 2 , and the development system by the sodium carbonate-based developing solution was set to 34 ° C for 45 seconds. The coating thickness of the photosensitive resin layer GH 01 and the coating amount of the pigment (C"_P.G.36 & C KP Y·5 〇) are as follows: photosensitive resin film thickness (μηη) 2.00 Pigment coating Amount (g/m2) 1.92 C_I.PG36 coating amount (g/m2) 134 C, LP_Y.i5〇 coating amount (g/m2) 0.5 8

The substrate on which the image K, the pixel R, and the pixel G are formed is washed by a brush and pure water as described above, and then sent to the substrate preheating apparatus without using a decane coupling liquid. [Formation of Blue (B) Pixel] The above-described photosensitive resin transfer material B 1 0 1 is used in the same manner as the above-described photosensitive resin transfer material R 1 0 1 to obtain a blue (B) pixel which is subjected to heat treatment. B. The exposure amount was set to 30 mJ/cm2, and the development system by the sodium carbonate-based development φ liquid was set to 36 ° C for 40 seconds. The film thickness of the photosensitive resin layer B1 01 and the coating amount of the pigments (C. 丨·Ρ·15:6 and C.LP.V.23) are as follows. Photosensitive resin film thickness (μητ〇2.00 pigment coating amount (g/m2) 0.75 C". P.B_1 5:6 coating amount (g/m2) 0.7 05 CIPV23 coating amount (g/m2) 0.045 This pixel will be formed R, the substrate of the pixel G' pixel B, and the image K are baked at 240 ° C for 50 minutes to obtain a color filter Α 1. -152- 200806754 With respect to the above-described method of manufacturing the color filter A1, The R pigment dispersion A was changed to the R pigment dispersions B to F, and the color filters B1 to F1 were prepared to obtain contrast and chromatic aberration of the obtained color filters A 1 to F 1 , and the same procedure as in Example 4-2 was carried out. (Embodiment 5-2) [Production and Evaluation of Liquid Crystal Display Device] Using the color filters A1 to F1, Φ was used as a liquid crystal in the same manner as in Example 4-3. When the display device was evaluated and the display characteristics were evaluated, the effects of the present invention were similarly found. (Example 6) [Production of liquid crystal display device having different display modes] MVA method was used in the above Examples 4-3 and 5-2. In the liquid crystal display device, a liquid crystal display device was produced using the same color filter and in the following manner. Making device PVA mode liquid crystal display

On the R pixel, the G pixel, the B pixel, and the black matrix of the color filter substrate obtained above, a transparent electrode of ITO (Indium Tin Oxide) is formed by sputtering. Next, according to Example 1 of JP-A-2000-64921, a spacer is formed on the ITO 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, the liquid crystal curing liquid is applied to the periphery of the pixel group surrounding the color filter, and the liquid crystal curing liquid is applied to the black matrix outer frame by a dispersing agent, and the PVA mode liquid crystal is dropped. After bonding to the counter substrate, the bonded substrate is subjected to UV irradiation, and then heat-treated to cure the sealant. On both sides of the liquid crystal cell thus obtained, a polarizing plate HLC2-2518 manufactured by San Ritsu Co., Ltd. was attached. Next, FR1112H (a wafer-type LED manufactured by Stall) and a DG1112H (a wafer-type LED manufactured by Stella) of a green (G) LED are used as blue. (B) LED 1111 H (wafer type LED manufactured by Stall), which is configured to form a side light mode backlight, and the polarizing plate is disposed on the side of the back surface of the liquid crystal cell. A liquid crystal display device is formed. When the same evaluations as in Examples 4-3 and 5-2 were carried out using this display device, the effects of the present invention were similarly found. • Manufacture of liquid crystal display device for IPS mode On the R pixel, G pixel, and B pixel and black matrix of the color filter substrate obtained above, IOT (Indium Tin Oxide, indium tin oxide) is formed by sputtering. Transparent electrode. Next, according to Example 1 of JP-A-2006-64921, a spacer is formed on the ITO film formed as described above and φ with respect to the upper portion of the black matrix. On the color filter substrate to which the spacer was attached, the polyimide was coated and rubbed 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. In other words, the TFT substrate for 丨Ps in which the TFT and the comb-type pixel electrode (conductive layer) are arranged is used as the driving side substrate, and the surface on the side where the pixel electrode or the like of the TFT substrate is provided is obtained from The surface on the side on which the colored pixel layer of the color filter substrate is formed is disposed to face each other, and has a gap formed by the spacer formed by the above -154-200806754 and is fixed. A liquid crystal material is sealed in the gap, and a liquid crystal layer having an image display is provided. On both sides of the liquid crystal cell thus obtained, a polarizing plate (1 3 2 2 2 518 made of 3 3 ^ 1 Å) was attached. Next, a backlight of the cold cathode tube was formed, and the polarizing plate was disposed in the liquid crystal. A liquid crystal display device was formed on the side of the back surface of the cell. When the same evaluation as in Examples 4-3 and 5-2 was carried out using the display device, the degree was smaller than the above, but the same was found in comparison with the comparative example. Effects of the Invention (Embodiment 7)

[Production of CCD Device] (Production of Pigment Dispersion Liquid for CCD) According to the formulation described below, the concentrated pigment liquid A' obtained in Example 1 was used to prepare a pigment dispersion liquid (1) · · Green G, (2) · · · Blue b, (3) • •• Red R 〇 pigment dispersion (1), CIPG36 90 parts by mass 25 parts by mass • CIPG7

• CIPY1 39 40 parts by mass • PLAAD ED1 51 20 parts by mass (made by Nanben Chemical Co., Ltd.) • 25 parts by mass of benzyl methacrylate/methacrylic acid copolymer (copolymerized molar ratio 70: 30, weight average molecular weight) 30,000) • Propylene glycol monomethyl ether acetate 6 2 5 parts by mass (2)·Ο.Ι.Ρ.Β.15:6 125 parts by mass • CIPV2 3 2 5 parts by mass -155- 200806754 • PLAAD ED1 51 40 parts by mass (manufactured by Nanben Chemical Co., Ltd.) • 25 parts by mass of benzyl methacrylate/methacrylic acid copolymer (copolymerized molar ratio 70:30, weight average molecular weight 30,000) • Propylene glycol monomethyl ether B 785 parts by mass of ester (3)·concentrated pigment dispersion A 235 parts by mass

• Compound C -1 used in the present invention 6. 60 parts by mass • 25 parts by mass of benzyl methacrylate/methacrylic acid copolymer (copolymerized molar ratio 70:30, weight average molecular weight 30,000) • Propylene glycol 750 parts by mass of methyl ether acetate (modulation of colored resin composition)

Each of the pigment dispersion liquids obtained as described above was uniformly mixed with the following composition in an amount of 200 parts by mass in each of the mixers to adjust the coloring resin composition for color filters for each color. <Composition> • 35 parts by mass of acrylic acid ester/methacrylic acid copolymer (copolymerized molar ratio = 70/30, weight average molecular weight: 30,000) • Dipentaerythritol pentaacrylate 38 parts by mass • Propylene glycol monomethyl ether Acetic acid ester 120 parts by mass • Propionate ethyl-3-ethoxy ester 40 parts by mass • Halogenated methyl triad system heuristic agent 4 parts by mass (photopolymerization heuristic product name TAZ1 07 Green Chemical Co., Ltd.) -156- 200806754 (Production of color filter and CCD device) The following composition was mixed with a stirrer to adjust the photoresist for flattening film [composition] • 165 parts by mass of acrylate/methacrylic acid copolymer ( Copolymerized molar ratio = 70/30, weight average molecular weight 30,000) • Dipentaerythritol pentaacrylate 65 parts by mass • Propylene glycol monomethyl ether acetate 138 parts by mass

• Ethyl 3-ethyl ethoxylate. 123 parts by mass • 3 parts by weight of a halogenated methyl triad system heuristic agent (photopolymerization infusion product name: 071 07 Green Chemical Co., Ltd.) The planarization is uniformly applied to the 6-inch wafer on which the photodiode is formed with a photoresist. Further, in the spin coating, the surface of the coating film after coating is applied at a temperature of 100 ° C for 120 seconds, and the number of coating rotations is adjusted so as to have a film thickness of about 1.5 μm. The coating film was cured by placing it in an oven at 22 ° C for 1 hour to form a planarizing film in such a manner that the surface of the formed photodiode was similarly coated on the twin crucible. Then, in the order of the respective colors G, R, and B, 100 parts by mass of the coloring resin composition for a color filter is applied onto the planarizing film with respect to the photoresist liquid adjusting formulation for 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 carried out by using a 2 μηι mask pattern, using an i-line segmenter, 157-200806754 (stepper) (trade name: FPA-3000i5+, manufactured by Canon), at 500 mJ/cm2. In addition, the alkali imaging system uses a 40% by mass aqueous solution of an organic alkaline developing solution (trade name: CD·200, manufactured by Fujifilm Electronic Materials Co., Ltd.), and is stirred at room temperature for 60 seconds. After the image, the spray was spun for 20 seconds and rinsed with pure water, and then washed 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 to the hot plate at a surface temperature of 200 ° C for 5 minutes.

The CCD device obtained as described above is mounted on a digital camera, and the image of a standard color chart with a gray scale attached to the KODAK is observed on the screen under the same light source. Reproduction portrait. (Example 8) [Production of ink-jet ink] Example 1 of JP-A-2002-201 387, according to the following formulation, the ruthenium pigment was dispersed in composition A to prepare R ink 1, and G φ was similarly modulated. Ink 1, B ink 1. Then, with respect to the method of producing the R ink 1, except that the pigment dispersion composition B to F is used instead of the pigment dispersion composition A of the R ink 1, the R inks 2 to 6 are produced in the same manner. -158- 200806754 [Table 12] Composition content (parts by mass) R ink 1 R ink 2 R ink 3 R ink 4 R ink 5 R ink 6 G ink 1 B ink 1 pigment dispersion composition A A pigment dispersion composition B 54 pigment dispersion composition C 54 pigment dispersion composition D 54 pigment dispersion composition E 54 pigment dispersion composition F 54 G pigment (C.IP.G·36) 5.0 B pigment (CI PB · 15:6) 5.0 Polymer dispersant (Soros Pass 24000 by AVECIA) 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 Adhesive (benzyl methacrylate-methacrylic acid copolymer) 3.0 3,0 3.0 3.0 3.0 3.0 3.0 3.0 Dipentaerythritol pentaacrylate 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 Tripropylene glycol diacrylate 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 2-Methyl small [4-(methylthio)phenyl]-2-carboline Detoxene 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 Diethylene glycol monobutyl ether acetate, 29.9 dyn/cm 46 46 46 46 46 46 81 81 81 For the mixing of the components in Table 12 above, the pigment and The polymer dispersant is put into a part of the solvent and enters Mixing, using a three-roll mill and a bead stirred to obtain a pigment dispersion. On the other hand, the other φ compounding component is supplied to the residual portion of the solvent, and stirred to be dissolved and dispersed 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 by a dissolver to prepare an inkjet ink. [Pixel formation] The above-described body 1, G ink 1, and B ink 1 are made of a piezoelectric type head, and first, ink is dripped around the concave portion of the light-shielding partition wall as described below. The color filter of the present invention is obtained as follows, with a nozzle density of 25 to 4 mm and 150 nozzles per nozzle, which has 318 nozzles in the direction of 2 nozzle rows. The 1 /2 mode of the nozzle spacing was staggered to be fixed by fj, and 300 drops were dropped on the substrate every 25.4 mm in the nozzle arrangement direction. 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 nozzle is controlled by the piezoelectric driving signal applied to the head, so that each droplet can be discharged 6 to 42 pi. In this embodiment, the glass substrate is conveyed at a position 1 mm below the head. Nozzle. In. The transport speed can be set in the range of 50 to 200 mm/s. Moreover, the piezoelectric driving frequency can be up to 4.6 KHz, and the amount of dripping can be controlled by such a setting. In this embodiment, the coating amounts of the respective pigments of R, G, and B are controlled to be 1.1, 1.8, 0.75 g/m2, the conveying speed, and the driving frequency, so that the inks of R, g, and B are dripped to correspond. The recesses of 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 manufactured by Nichia Chemical Co., Ltd. This LED emits ultraviolet light having a wavelength of 365 nm from a single chip, and emits light of about 1 〇〇 mw from the wafer by energizing a current of about 50 mA. A plurality of them are arranged at intervals of 7 mm, and a power of 〇3 W/cm 2 is obtained on the surface. The time from the drip to the exposure and the exposure time may be changed depending on the transport speed of the medium and the distance between the head and the LED transport direction. In this embodiment, after being shot, it is dried at 100 degrees for 10 minutes, and then exposed: the distance between the light and the conveying speed is set, and the exposure energy on the medium can be adjusted to 〇·〇1 to 15 J/cm2. between. In the present embodiment, the entire exposure energy is adjusted according to the transport speed of -160-200806754. These exposure powers and exposure energies were measured using a tidal current mechanism radiation spectrometer URS-40D using a 値 integral of a number between 220220 nm and 400 nm. The light-shielding partition walls and the respective pixels were completely cured together by baking the dripped glass substrate in an oven at 230 ° C for 30 minutes. Then, with respect to the method of manufacturing the R ink 1, the color filter sheets 2 to 6 are produced in the same manner except that the R inks 2 to 6 are used instead of the R ink 1 respectively. The contrast of the respective color filters was carried out in the same manner as in the above [Comparative Measurement], and the results of the measurements are shown in Table 13 below. [Table 1 3] Contrast color difference (ΔE) Remark ink 1 4 7 0 0 0.2 Ink 2 2100 0.1 Inventor 3 5800 0.2 Ink 4 4900 0.8 Inventive ink 5 3100 0.7 Comparative example Ink 6 3 40 0 0.9 Comparative Example

[Production of Liquid Crystal Display Device] A liquid crystal display device was produced using the color filter produced as described above, and the display characteristics were evaluated. (Formation of a ruthenium electrode) A glass substrate formed of a color filter is placed in a sputtering apparatus, and ITO (indium tin oxide) having a thickness of 1,300 Å is vacuum-deposited at 1 〇〇1 at 2 40 ° C. Annealing was performed for 90 minutes to crystallize the ITO to form a 丨TO transparent electrode. (Formation of a spacer) A spacer is formed on the above-mentioned ιτ transparent electrode by the same method as the spacer formation method of -161 to 200806754 described in [Example 1] of JP-A-2004-240335. (Formation of Liquid Crystal Alignment Control Protrusion) The liquid crystal alignment control projection is formed on the 丨TO transparent electrode formed of the spacer described above 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 (Hitachi Hi-Tech Engineering Co., Ltd.) is disposed at a distance of 100 Å / m from the surface of the photosensitive resin layer, and the photomask is passed through the ultra-high voltage. The mercury lamp is exposed to the vicinity by using an irradiation energy of 150, mJ/cm2. Thereafter, the aqueous solution of 2 to 38% of tetramethylammonium argon 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, the liquid crystal alignment control of the photosensitive resin layer having the desired shape can be obtained on the color filter side substrate. A substrate for a liquid crystal display device formed by protrusions.

Then, the substrate for a liquid crystal display device formed by the projection of the liquid crystal alignment device was baked at 230 ° C for 30 minutes to form a liquid crystal alignment control projection which was cured on the substrate for a liquid crystal display device. <Forming liquid formulation for positive photosensitive resin layer> • Positive photoresist (FH-241 3F manufactured by Fujifilm Electronic Materials Co., Ltd.): 53·3 parts by mass. • Methyl ethyl ketone: 46.7 parts by mass _ Megafac F-780F (manufactured by Dainippon Ink Chemicals Co., Ltd.): 0.04 parts by mass - 162 - 200806754 (Production of liquid crystal display device) . . . . . . . . . An aligning film made of polyfluorene. Subsequently, after sealing the epoxy resin sealant at a position corresponding to the black matrix outer frame provided around the pixel group surrounding the color filter, and simultaneously dropping the MVA mode liquid crystal to the opposite substrate, The bonded substrate is heat treated to harden the sealant. On both sides of the liquid crystal cell thus obtained, a polarizing plate #HLC2-2518 manufactured by Sanritsu Co., Ltd. was attached. Next, a backlight of a three-wavelength cold cathode tube light source (FWL18EX-N manufactured by Toshiba LITEC Co., Ltd.) was formed, and the polarizing plate was placed 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 filter of the present invention has confirmed that the black compactness and the redness of the redness are excellent with respect to the comparative example. From the above, it is understood that the effects of the present invention are not only remarkable, but also a larger effect can be obtained by the centrifugal separation conditions in the production step or by the relatively simple means of strengthening drying.

Fig. 1 is a cross-sectional view schematically showing a preferred embodiment of a manufacturing apparatus for producing a pigment dispersion composition of the present invention. Fig. 2 is a cross-sectional view schematically showing another preferred embodiment of a manufacturing apparatus for producing a pigment dispersion composition 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 as another embodiment of the manufacturing apparatus of Fig. 2, partially in section. -163- 200806754 Fig. 5 is a cross-sectional view schematically showing another preferred embodiment of a manufacturing apparatus for producing a pigment dispersion composition of the present invention. Fig. 6 is a cross-sectional view showing still another preferred embodiment of a manufacturing apparatus for producing a pigment dispersion composition of the present invention. Fig. 7 is a front elevational view schematically showing an example of a dissolver stirring blade for producing 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 formed by a turbine portion that can be rotated and a baffle portion that is fixed by a small gap in the periphery of the organic nanoparticle of the present invention. Sectional view. Fig. 1 is a view showing an example of the configuration of one of the ultrafiltration devices for producing the organic nanoparticles of the present invention. [Description of main component symbols] 11 container 11a liquid tank (solvent) 12 stirring blade 13 mixing chamber 14 supply pipe 14a supply pipe opening portion 1 rotating shaft 1 6 motor 17 housing (mixing chamber wall) 18 holes (circular hole) -164- 200806754 19a, 19b mixing blade 2Ί container (stirring tank outer wall) 21a stirring tank 22 stirring blade 23 discharge tube 24a, 24b supply tube.

25 rotating shaft 50 agitating device 32, 33 supply port 36. discharge port 40 sealing plate 41, 42 agitating blade 46 outer magnet 48, 49 motor 61 disk portion 62 blade 63 rotating shaft 74 rotatable turbine portion 75 is fixed The baffle portion 81 accommodates the container of the dispersion 82 the circulation pump 8 3 ultrafiltration mode II. 84 the supplementary pure water measurement flow meter 8 5 the permeate water measurement flow meter 86 reverse direction cleaning pump-165-

Claims (1)

200806754 X. Patent application scope: 1. A pigment dispersion composition characterized in that it contains a pigment dispersion composition of an organic pigment and a rice particle and an organic solvent, wherein the organic pigment nanoparticle is once The proportion of particles having a particle size of less than 15 nm is less than 10% (number%), and the proportion of particles exceeding 60 nm is less than 10% (number%), and the water content of the above composition is 0.01% by mass to 5 The pigment dispersion composition of claim 1, wherein the organic pigment nanoparticle is obtained by dissolving an organic pigment in a solution of a good solvent, and the above organic pigment compatible with the solvent. The pigment dispersion composition of the first or second aspect of the invention, wherein the water content is 3% by mass or less. 4_If the patent application is the first or the second item The pigment dispersion composition, wherein the water content is 1% by mass or less. ' 5. The pigment dispersion composition according to claim 1 or 2, which contains '.... ·,:: · 1) the combination shown ' In the formula, 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 having a basic nitrogen atom. a group consisting of a group consisting of a ureido group, a urethane group, a group having a coordinating oxygen atom, a hydrocarbon group having 4 or more carbon atoms, an alkoxy group, an epoxy group, an isocyanate group, and a hydroxyl group a monovalent organic group, or a monovalent organic group containing an organic dye structure which may have a substituent or a heterocyclic ring, wherein 'n' of A1 -166-200806754 may be the same or different from each other, and m means 1 to 8 The number η represents a number of 2 to 9 'm + n is 3 to 1 满足, and Ρ 1 is a polymer compound residue>. 6 - a colored photosensitive resin composition characterized by comprising a pigment dispersion composition according to claim 1 of the patent application, a polyfunctional monomer having two or more ethylenically unsaturated double bonds, and a photopolymerization heuristic or Photopolymerization heuristic system. A photosensitive resin transfer material characterized in that at least a photosensitive resin layer containing the colored photosensitive resin composition of claim 6 is provided on a temporary support. Φ 8. The pigment dispersion composition of claim 1 or 2, wherein the pigment dispersion group is an inkjet ink. A color filter characterized by using the colored photosensitive resin composition of claim 6 and/or the photosensitive resin transfer material of claim 7 of the patent application. 1 〇 _ A liquid crystal display device characterized by having a color filter as in the ninth application of the patent application. 1 1 The liquid crystal display device of claim 10, wherein the liquid crystal display device is a VA mode. A C C D device characterized by having a color filter as in claim 9 of the patent application. -167-