TW200904907A - Method for producing organic nano-pigment particle aggregate and organic nano-pigment particle nonaqueous dispersed substance, colour photosensitive resin composition containing the said dispersed substance, and color filter using it - Google Patents

Abstract

The purpose of the present invention relates to that when the organic nano-pigment aqueous dispersed substance is phase-transferred to organic nano-pigment nonaqueous dispersed substance, corresponding to the process for temporally producing aqueous paste by flushing method representatively, namely, corresponding to the complex process such as filtration using filter which needs a lot of time, a method for manufacturing the aggregate from the nano-pigment particle of the organic nano-pigment particle aqueous dispersed substance, which can be easily filtered, is provided. The solution of the present invention provides a process for producing organic nano-pigment particle aggregate, which the reaction of the organic nano-pigment particle with at least one organic low molecular compound with molecular weight of 1000 or less and at least one organic high molecular compound with molecular weight of 1000 or more is carried out to make the organic nano-pigment particle aggregated, and than isolated.

Description

200904907 IX. Description of the invention: [Technical field to which the invention pertains] The invention relates to a method for preparing a non-aqueous dispersion of organic nanoparticles, which is obtained by converting an aqueous dispersion of organic nano pigment particles into a non-aqueous medium. . More specifically, the present invention relates to a non-aqueous dispersion of organic nano pigment particles which is an organic nano pigment particle in an aqueous dispersion of organic nano pigment particles which has been previously difficult to filter, which is easily agglomerated. The body 'is isolated by a filtration operation and redispersed in a non-aqueous medium. [Prior Art] In recent years, efforts to reduce the size of particles have been progressing. In particular, it is difficult to produce a small size to a nanometer size (e.g., a range of 10 to 100 nm) using a pulverization method, a precipitation method, or the like, in progress. Further, attempts have been made to reduce the size to a nanometer size and to have a monodispersity (in the present invention, monodispersity means a degree of uniformity of particle diameter). Such nano-sized micro-particles are located between the larger total particles and the smaller molecules or atoms, and are unprecedented in size areas, and are pointed out to be able to perform unpredictable new characteristics. Moreover, if the monodispersity can be improved, the characteristics of the nanoparticle can be stabilized, and the possibility of such nanoparticles is expected in various fields, in biochemistry, novel materials, electronic components, A wide range of fields, such as light-emitting display elements, printing, and medical care, are actively being researched. In particular, organic nanoparticles composed of organic compounds have high potential as functional materials because of the diversity of organic compounds. For example, '200904907 is a widely used material because it has chemical and mechanical stability such as heat resistance, solvent resistance, and mechanical properties, and is excellent in electrical insulation. Further, the polyimine is finely divided and the properties and shapes of the combined polyimine are gradually being utilized in a wider range of fields. For example, there is a proposal (Patent Document 1) for the use of a micronized polyimine as an additive for a powder toner for image formation. Further, among the organic nanoparticles, examples of the organic pigment include coatings, printing inks, toners for electrophotography, inkjet inks, and color filters. These are now important compounds that are indispensable in life. Among them, those which require high performance and are particularly important in practical use are pigments for inkjet inks and pigments for color filters. In the case of a coloring agent for inkjet ink, a dye has been conventionally used, but since there is a problem in water resistance or light resistance, in order to improve this problem, a pigment has been gradually used. When the image obtained by using the pigment ink is compared with the image obtained by using the dye-based ink, the image has excellent light resistance and water resistance. However, since it is difficult to mention the monodispersity to be the nanometer size of the void which can penetrate the surface of the paper, the adhesion to paper is poor. Further, with the increase in the number of pixels of a digital camera, it is desirable that the color filter used for an optical element such as a CCD (Charge Coupled Device) sensor or a display element can be thinned. Color filters use organic pigments. Because the thickness of the filters is quite dependent on the particle size of the organic pigments, it is desirable to be able to produce microparticles of nanometer size and monodisperse and stable. Regarding the production method of the organic particles, there are a gas phase method (a method of sublimating a sample under an inert gas atmosphere of 200,904,907 to recover particles on a substrate), and a liquid phase method (for example, by injecting a sample dissolved in a good solvent, injection has been controlled). a weak solvent for stirring conditions or a temperature to obtain a microparticle reprecipitation method, a laser ablation method (a method of ablating a laser by irradiating a laser to a sample dispersed in a solution to make the particles finer) research. Further, there have been reports of attempts to produce a manufacturing example of a desired size and monodispersion by such methods. In particular, the liquid phase method has been paid attention to because it is a method for producing organic particles excellent in simplicity and productivity (see Patent Documents 2 and 3). The organic particles prepared by the liquid phase method can adjust the precipitation conditions by the solvent type, the injection rate, the temperature, etc., and can adjust the crystal shape or the surface properties of the particles. Patent Document 3 discloses a type of weak solvent. An example of adjusting the crystal shape of the quinacridone pigment. On the other hand, in order to improve the dispersibility of the particles, the dispersion of the organic pigment in the related art is carried out industrially using various dispersing machines (roll mill, ball mill, vertical ball mill, etc.), but since the particles are refined, there will be The situation where the viscosity is excessively rising. When the viscosity is increased, it may be difficult to take out from the dispersing machine, it may not be transported by a pipe, and it may be gelled during storage and cannot be used. In order to solve such problems, a polymer which is dispersed and stabilized by dispersing agents which are dispersed is provided, but sufficient effects cannot be obtained (see Non-Patent Document 1 and the like). Further, in the case of the organic pigment dispersion liquid for a color filter, in order to improve the dispersibility, a polymer or pigment which can impart both the basic development property and the dispersion stability required for the production of the color filter is added. A dispersing agent (for example, refer to Patent Document 4). However, in such methods, it is not possible to fully meet the requirements because the dispersion takes time and the viscosity excessively rises. 200904907 Further reports have been made to improve the dispersibility by using pigment particles prepared by the liquid phase method described above. For example, the description of Patent Document 5 discloses an example in which a pigment particle aqueous dispersion is prepared by a liquid phase method. However, the method provided by this method is, at the end, an aqueous dispersion, and there is no mention at all of the method of providing the dispersion as an organic solvent. Patent Document 6 describes an example in which a pigment particle prepared by a liquid phase method is used as an organic solvent dispersion. The description of Patent Document 6 discloses that a pigment is dissolved in a basic compound and/or an alkaline solution, and then a neutral compound and/or an acidic compound or a neutral liquid and/or an acidic liquid are added by adding a liquid. A method of pigment precipitation. However, the organic pigment particles obtained by this method have a large primary particle diameter and cannot sufficiently respond to the requirement of fine particles. In the above-described liquid phase method, the nanoparticles are prepared so that a low molecular surfactant or a neutral water-soluble nonionic polymer compound is used in order to prevent aggregation of the nanoparticles. Therefore, even if the nanoparticles can be dispersed at a high concentration, the sub-additives used must have a large number of disadvantages, and in the case where the viscosity of the inkjet is low and the polymer compound content is extremely low, the techniques are directly applied. It is difficult. Further, in order to prepare a solvent system for phase transfer after preparing aqueous nanoparticles, a flushing method is known in which an aqueous slurry or an aqueous paste containing a pigment at a high concentration is produced, and a resin or a resin solution is added. Mix and stir and use a resin or resin solution to replace the moisture around the pigment. However, the shape in which the aqueous particles are strongly agglomerated at one time in the present method has a problem that the efficiency of resin coating is deteriorated and redispersion is difficult (for example, 'see Patent Documents 7 to 8 and the like). In addition, in the case of such a method, the aqueous paste is manufactured by the method of using a water-based paste to temporarily maintain the aqueous pigment particles, or to pass through the reactor under the condition of agglomerating the aqueous particles. But there is a problem that filtering takes a lot of time 'very inefficient and troublesome in the industry. Further, although a low molecular anionic or cationic surfactant or a dispersing agent can be used, there is a problem that the low molecular weight causes insufficient dispersion stability. Therefore, a technique has also been attempted (for example, refer to Non-Patent Document 2) in which aqueous particles are converted into an ionic liquid by a cationic polymer compound without passing through a filtration step. However, the method described in Non-Patent Document 2 is limited to low-concentration inorganic particles, and the organic pigment is not mentioned in Non-Patent Document 2, and there is also a case where the final dispersion medium is a non-volatile ionic liquid, The method described in Patent Document 2 is not suitable for industrial use. [Patent Document 1] Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. [Patent Document 5] Japanese Laid-Open Patent Publication No. JP-A No. 2000-239554 [Patent Document 5] JP-A-2004- 1 23 8 5 No. 3 [Patent Document 7] Japanese Patent Laid-Open Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. 6-161. [Non-Patent Document 1] Pigment Dispersion Technology - Surface Treatment and Dispersant Usage and Dispersibility Evaluation - Technical Information Association 1999 [Non-Patent Document 2] "small", 2006, Vol. 2, No. 7, pp. 879-883, pp. 200904907 [Disclosure] The present invention is directed to the above The object of the invention is to provide a method for preparing a non-aqueous dispersion of organic nano pigment particles by rinsing relative to converting an aqueous dispersion of organic nano pigment particles into a non-aqueous dispersion of organic nano pigment particles. The step of temporarily producing a water-based paste for the representative', that is, a step that requires a very long time, such as filter filtration, The nano pigment particles in the aqueous dispersion of the organic nano pigment particles are an aggregate that can be easily filtered, and are isolated and redispersed in a non-aqueous medium. The non-aqueous dispersion of the organic nano pigment particles can be efficiently obtained. . Further, a colored photosensitive resin composition obtained by using the above-described organic nano pigment particle dispersion and a color filter produced by the same are provided. [Means for Solving the Problem] The results of the present invention and the like are found to be added by A solution obtained by dissolving an organic low molecular compound and an organic polymer compound enables the organic nano pigment particles dispersed in an aqueous medium to be aggregated into an aggregate that is easy to filter 'separate the aggregate and redisperse it in a non-aqueous medium A non-aqueous dispersion of organic nano pigment particles can be obtained efficiently. The present invention has been completed based on such knowledge. The present invention has been achieved in accordance with the following means. [1] A method for producing an organic nano pigment particle agglomerate, characterized in that at least one organic low molecular compound having a molecular weight of less than 100 and at least one organic polymer compound having a weight average molecular weight of 1,000 or more are halved 200904907 Organic nano pigment particles dispersed in an aqueous medium act to segregate. [2] The method for producing an organic nano pigment particle agglomerate according to [1], wherein the organic compound and the organic polymer compound are dissolved by using a solvent mixed with the aqueous medium, and added to the water to be dispersed The organic nano pigment particles in an aqueous medium are condensed [3]. The above-described segregation of the organic nanoparticle pigment aggregates of [1] or [2] is carried out by filtration. [4] The method for producing an organic nano pigment particle according to any one of [1] to [3], which comprises the step of removing at least the remaining organic low molecule. [5] The method for producing an organic nano pigment particle according to any one of [1] to [4] wherein the organic nano pigment dispersed in the aqueous medium is mixed with a solution of an organic pigment dissolved in a good solvent, It is obtained by forming a nanometer-sized fine particle with a solvent compatible with a solvent and a medium of the above organic pigment-based weak solvent. [6] The method for producing an organic nano pigment particle according to any one of [1] to [5] wherein the average organic pigment particle has an average primary particle size of less than or equal to nanometer. [7] The method for producing an organic nano pigment particle according to any one of [6], wherein the average particle diameter of the aforementioned aggregate is 10000 nm [8] - a non-aqueous dispersion of organic nano pigment particles The feature is obtained by redispersing an organic neat particle agglomerate obtained by any one of [1] to [7] in a non-aqueous medium. After the collection, the low molecular media set is borrowed. $ method, its aggregate compound agglomerate particles, the above-mentioned good to make the aggregate 1 1 〇〇 aggregate above. Law, its rice pigment -11-

[9] The method for producing an organic nano pigment particle dispersion according to any one of [1] to [8] wherein the organic polymer compound is represented by the following formula (14), and the formula (11) (the aforementioned In the formula (11), A1 represents a hydrocarbon group selected from an acidic group, an atom-containing group, a urea group, a urethane group, a coordinating oxygen house carbon number of 4 or more, or an alkoxyalkyl group. The monovalent organic group of the epoxy group, the hetero- and hydroxy group, or the monovalent organic group which may have an organic colorant structure or a heterocyclic ring, and η A1 may also be different, and R1 represents (m + n) a linking group of valences, m + nj) 10' m represents an integer of 1 to 8, and η represents a single bond or a divalent bond of 2 to 9, and ρ1 represents a polymer residue formula ( 1 4) (+Z~GJ-)—Q—fR) v J\ (In the above formula (14), G - means -cocr, -S03-, -P(0)(0H)0·, or - 〇p(〇)(〇H)0·, J represents a two-valent single bond, Q represents a (m + 1) valent linkage, and R represents a high f residue ' Z + represents organic or inorganic a cation, m + 1 system means [1〇] such as [9] organic nano pigment particles non-aqueous fractionation ' The above-mentioned organic macromolecularization is used as a dispersing agent in a non-aqueous medium. The non-aqueous formula (11) or the basic nitrogen-based group, the cyanate-based substituent may be the same as $3, R2 )) -0S03' 'linked group or sub-compounds 3 to 6) The material of the sputum is directly made to 200904907 [11] A colored photosensitive resin composition characterized by containing organic nemesis such as [9] or [10] At least one of a non-aqueous dispersion (or aggregate) of a rice pigment particle, a binder, a monomer or oligomer, and a photopolymerization initiator or a photopolymerization initiator. [12] A color filter ' is characterized in that it is formed using the colored photosensitive resin composition of the item [11]. [Effects of the Invention] According to the production method of the present invention, organic nano pigment particle aggregates can be efficiently produced from an aqueous dispersion of organic nano pigment particles. Further, by using the organic nano pigment particle agglomerate, it is possible to easily convert and deflocate (re-disperse) the non-aqueous medium phase to efficiently produce an organic nano pigment particle non-aqueous dispersion on an industrial scale. . The process according to the present invention can produce an organic nanoparticle particle dispersion suitable for a color filter coating liquid or an inkjet ink and a dispersion thereof on an industrial scale. Further, the non-aqueous dispersion of the organic nano pigment particles of the present invention has excellent dispersibility and high contrast. The color filter using the same has a target color purity and high contrast. [Embodiment] The following describes the preparation of the organic nano pigment particles of the present invention. [Organic Pigment] The organic pigment which is produced by the method of producing the organic nano pigment particles of the present invention is not particularly limited as long as it can form particles by a liquid phase method, and may be used singly or in combination. The hue of the organic pigment is not limited, and examples thereof include hydrazine, peri none, quinacridone, quinophthalone oxime, hydrazine, fluorenone ketone, benzo-13-200904907 imipenone, and Diazo condensation, diazo, azo, standard reduction blue, phthalocyanine, triarylcarbyl, di Df, amino oxime, dioxopyrrolopyrrole, thioindigo, isoporphyrin, isoindole a ketone ketone, a pyridhen fluorenone or an isopurinone compound pigment, or a mixture thereof or the like. More details 'for example, c · ; [• pigment red 丨 9 〇 (c _ ;!. number 71140), CI pigment red 224 (CI number 7ll27), ci pigment purple 29 (CI number 7 1 1 2 9 ) 茈 compound pigment; c. I. Pigment orange 4 3 (C. I. No. 71105), or CI Pigment Red 194 (CI number 71100) and other purple ketone compound pigment; CI Pigment Violet 19 (C_I. No. 73900) , CI Pigment Violet 42, CI Pigment Red 122 (C_I. No. 73915), cI Pigment Red 192, CI Pigment Red 202 (CI No. 73907), CI Pigment Red 2〇7 (CI No. 739〇〇, 73906), or CI Pigment Red 209 (CI number 73905) quinophthalone compound pigment; CI Pigment Red 206 (CI number 739〇〇/73920), CI Pigment Orange 48 (CI number 73900/73920), or cI Pigment Orange 49 (CI number 73 900/73920) isoquinone oxime compound pigment; ci pigment yellow mvc.;!. No. 60645) 蒽醌 compound pigment; cI pigment red 168 (CI number 5 93 00) and other fluorenone oxime compound pigment; cI Pigment Brown 25 (0:···Number 12510), CI Pigment Violet 32 (CI number 12517), CI Pigment Yellow 180 ((3.1· No. 21290), CI Pigment Yellow Benzimidazolone compound pigment such as 181 (C.I_number i1777), cI pigment orange 62 (CI number 11775), or CI Pigment Red 185 (c·. number i25i6); CI Pigment Yellow 93 (CI number 207 1 0), CI Pigment Yellow 94 (cl number 20048), CI Pigment Yellow 95 (CI number 20034), CI·Pigment 寅 128 (CI number 20037), CI Pigment Yellow 166 (CI number 20035), CI Pigment Dial 34 (C .I_ No. 21115), C_I. -14- 200904907 Pigment Orange 13 (CI number 21 1 10), C_I. Pigment Orange 3 1 (CI. No. 20050), CI Pigment Red 144 (CI number 20735), CI Pigment Red 166 (CI number 2 0 73 0), CI Pigment Red 220 (CI number 2〇〇55), CI. Pigment Red 221 (C_I. No. 20065), C.I_Pigment Red 242 (CI number 200 67), CI Diuretic condensation compound pigment such as Pigment Red 248, CI Pigment Red 262, or c丄 Pigment 23 (C.I_No. 20060); cj. Pigment Yellow 13 (CI·No. 21100), CI Pigment Yellow 83 (CI Number) 211〇8), or c 丄Pigment Yellow 188 (C.I_No. 21094) and other diazo compound pigments; c·〗. Pigment Red 187 (C_I. No. 12486), CI Pigment Red 170 (CI·No. 12475) , CI·Pigment 74 (CI number 11714), CI Pigment Yellow 15〇 (CI. No. 4 8545) 'CI Pigment Red 48 (CI number 1 5 86 5 ), CI Pigment Red ((: 丄 number 15585), CI Pigment Orange 64 ( CI number 12760), or c.〗. Pigment red 247 (C.I_ number 15915) and other azo compound pigments; CI. Pigment blue 60 (CI number 69800) and other standard reduced blue compound pigment; cI pigment green 7 (CI No. 74260), Green 36 (CI number 7426 5 ), Green 37 (^• number 742 5 5), C_I. Pigment Blue 16 (CI number 74 1 00), C_I. Pigment Blue No. 74160: 2), CI Pigment Blue 15: 6 (CI number 74160), or phthalocyanine compound pigment such as CI Pigment Blue 15: 3 (CI number 74160); cI Pigment Blue 56 (CI number 42800), or CI Pigment Blue 61 (CI number 42765: 1), etc. Triarylcarbane compound pigment; CI pigment violet 23 (^. number 51319), or CI pigment violet 37 (CI number 51345) and other diterpenoid compound pigment; CI pigment red 177 (CI number 6 5 3 0 0) and other amines Base compound pigment; CI Pigment Red 254 (CI number 56110), CI Pigment Red 255 (CI number 5610150), CI Pigment Red 264, C.I_Pigment Red 272 (CI number 200904907 S61150), CI·Pigment Orange, or CI Pigment Orange 73 and other dioxopyrrolopyrrole pigments; C.1·Pigment Red 88 (c.l_number 73312) and other sulfur indigo compound pigments; Yellow 139 (c丨·number 5 62 9 8), c i. Pigment orange 66 (CI number 482 1 〇) and other isoporphyrin compound pigments; c丨·Pigment Yellow l〇9 (CI number 56248), CI. Pigment yellow 185 (ci number 5 629 〇), or CI pigment orange 61 (^. number 1 1 2 95) and other isoindolinone compound pigments; CI Pigment Orange 40 (0:". No. 5 97 〇〇), Or CI•Pigment Red 216 (c) number 5 97 1 0), etc. pyridindione (pyranthr〇n); c丄 pigment astragalus 3 8 (c丄戚59710) and other 嗤琳黄-based pigments, or ci • Isopurinone pigment such as Pigment Violet 31 (CI number 60 0 1 0). Among them, a quinophthalone compound pigment, a dioxopyrrolopyrrole compound pigment, a diterpene compound pigment, a phthalocyanine compound pigment, or an azo compound pigment is preferred, and a dioxopyrrolopyrrole compound pigment and a diterpene compound are used. The pigment is better. Since the pyrrolopyrrole compound pigment represented by CIPR254, 255, and 264 has an absorption region suitable for improving the purity of the red pixel color constituting the color filter, the color reproduction region can be enlarged, and it is attempting to utilize it for color filter. sheet. However, the previous pigments were unable to meet the requirements of color purity or contrast. For example, the ink for inkjet described in JP-A-2003-3 36001, which is obtained by a method of bead dispersion or salt milling, does not provide a good color filter. According to the process of the present invention, nanometer-sized dioxopyrrolopyrrole compound pigment fine particles can be obtained in a state in which the particle size distribution is sharp. Further, when the pigment fine particles are used in a color filter, the required color purity and high contrast can be achieved, and the light resistance is excellent, and the occurrence of precipitates can be suppressed. -16- 200904907 In the present invention, it is also possible to use a solid solution of two or more kinds of organic pigments or organic pigments in combination. [Preparation of aqueous dispersion of organic nano pigment particles] Next, the preparation of an aqueous dispersion of organic nano pigment particles will be described. In the 'organic nano pigment particle of the present invention, an organic pigment solution obtained by dissolving an organic pigment in a good solvent, and a solvent compatible with the above-mentioned good solvent and a weak solvent for an organic pigment (hereinafter, This solvent is called "a weak solvent of an organic pigment" or a case of a "weak solvent" (hereinafter referred to as a "weak solvent") (the following 'this method is also called a "re-precipitation method", and the machine-containing nano pigment obtained at this time is obtained. The dispersion of particles is referred to as "organic microparticle re-sinking". The weak solvent of the organic pigment is not particularly limited as long as it can be dissolved or uniformly mixed with a good solvent for dissolving the organic pigment. The weak solvent of the organic pigment is preferably 0. 02% by mass or less, more preferably 〇.% by mass or less. There is no particular lower limit for the solubility of the organic pigment in a weak solvent, and in consideration of the organic pigment generally used, it is practically 0.00000% by mass or more. The solubility may also be the solubility when dissolved in the presence of an acid or a base. Further, the compatibility or uniformity of the good solvent and the weak solvent is preferably 30% by mass or more, and more preferably 50% by mass or more, based on the amount of the solvent dissolved in the weak solvent. There is no particular upper limit for the amount of good solvent to be dissolved in a weak solvent, and mixing in any ratio is practical. The weak solvent is not particularly limited as long as it is an aqueous medium, and examples thereof include an aqueous solvent (for example, water 'or hydrochloric acid 'aqueous sodium hydroxide solution), an alcohol compound solvent, a ketone compound solvent, an ether compound solvent, and an aromatic compound solvent, -17-200904907 Carbon disulfide solvent, aliphatic compound solvent, nitrile compound solvent, halogen compound solvent, ester compound solvent, ionic liquid, mixed solvent thereof, etc., as aqueous solvent, alcohol compound solvent, ketone compound solvent, ether compound solvent, ester compound solvent Or a mixture of these is preferable, and an aqueous solvent, an alcohol compound solvent, or an ester compound solvent is more preferable. The alcohol compound solvent may, for example, be methanol, ethanol, isopropanol, n-propanol or 1-methoxy-2-propanol. The hydrazine compound solvent may, for example, be acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone. The ether compound solvent may, for example, be dimethyl ether, diethyl ether or tetrahydrofuran. Examples of the aromatic compound solvent include benzene, toluene, and the like. The aliphatic compound solvent may, for example, be hexane or the like. The nitrile compound solvent may, for example, be acetonitrile or the like. The halogen compound solvent may, for example, be dichloromethane or trichloroethylene. The ester compound solvent may, for example, be ethyl acetate or the like, ethyl lactate or 2-(b-methoxy)propyl acetate. Examples of the ionic liquid include a salt of 1-butyl-3-methylimidazole and PF6·. Next, a good solvent for dissolving the organic pigment will be described. The good solvent is not particularly limited as long as it can dissolve the organic pigment to be used and is compatible or uniformly mixed with the above-mentioned weak solvent. The solubility of the organic pigment in a good solvent is preferably 2% by mass or more, and more preferably 0.5% by mass or more. There is no particular upper limit on the solubility of the organic pigment in a good solvent. When considering an organic pigment which is usually used, it is practically 50% by mass or less. The solubility may also be the solubility when dissolved in the presence of an acid or a base. The preferred range of compatibility or uniformity of the weak solvent with the good solvent is as described above. -18- 200904907 The good solvent may, for example, be an aqueous solvent (for example, water or hydrochloric acid, an aqueous sodium hydroxide solution), an alcohol compound solvent, a guanamine compound solvent, a ketone compound solvent, an ether compound solvent, an aromatic solvent, or a carbon disulfide solvent. , an aliphatic solvent, a nitrile solvent, an anthraquinone solvent, a halogen compound solvent, an ester compound solvent, an ionic liquid, a carboxylic acid compound, a sulfonic acid compound, sulfuric acid, and the like, and an aqueous solvent or an alcohol compound a solvent, a ketone compound solvent, an ether compound solvent, an anthraquinone compound solvent, an ester compound solvent, a guanamine compound solvent, a carboxylic acid compound, a sulfonic acid compound, sulfuric acid or a mixed solvent thereof, preferably an aqueous solvent, an alcohol compound solvent, or the like The ester compound solvent, the sub-grinding compound solvent, the guanamine compound solvent, the carboxylic acid compound, the sulfonic acid compound, and the sulfuric acid are more preferable, and the Yafeng compound solvent, the guanamine compound solvent, the carboxylic acid compound, the sulfonic acid compound, and the sulfuric acid are particularly preferable. . The solvent of the hydrazine compound may, for example, be dimethyl hydrazine, diethyl hydrazine, hexamethylene fluorene or cyclobutyl boron. The guanamine compound solvent may, for example, be N,N-dimethylformamide, 1-methyl-2-pyrrolidone, 2-pyrrolidone or 1,3-dimethyl-2-imidazolidinone. 2-pyrrolidone, ε-caprolactam, formamide, Ν-methylformamide, acetamide, Ν-methylacetamide, hydrazine, hydrazine-dimethylacetamide, hydrazine- Methyl acrylamide, hexamethylphosphoric acid triamide, and the like. A solvent is a good solvent or a weak solvent depending on the type of organic material to be used. In the present invention, for a certain organic pigment, the good solvent and the weak solvent are not the same compound. Further, the concentration of the organic pigment solution obtained by dissolving the organic pigment in a good solvent is such that the saturated concentration of the organic pigment in the good solvent is -19-200904907 to a concentration of 1 / 1 〇〇 of the saturated concentration under the condition of dissolution. The range is good. The preparation conditions of the organic pigment solution are not particularly limited, and can be selected from the range of normal pressure to subcritical and supercritical conditions. The temperature at normal pressure is preferably -10 to 150 ° C, more preferably -5 to 130 ° C, and particularly preferably 0 to 100 ° C. The organic pigment of the present invention must be capable of being uniformly dissolved in a good solvent, and it is also preferable if it is soluble in acid or alkali. Usually, when a pigment having a group which can be largely dissociated in a molecule is used, basicity is used, and when a group which can be dissociated by alkali is not present in the molecule, but a large amount of nitrogen atom which easily adds a proton is used, acidity is used. . For example, quinophthalone, dioxopyrrolopyrrole, and a diazo condensed compound pigment can be dissolved using alkali, and a phthalocyanine compound pigment can be dissolved using an acid. The base used for dissolving with alkaline is an inorganic base such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide or barium hydroxide, or a trialkylamine or diazabicycloundecene. An organic base such as (DBU) or a metal alkoxide is preferably an inorganic base. The amount of the base to be used is such that the amount of the pigment can be uniformly dissolved, and is not particularly limited. The inorganic base is preferably 1.0 to 30 mol equivalents with respect to the organic material, and preferably 1.0 to 25 mol equivalents, preferably 1.0 to 20 The molar equivalent is better. The organic base is preferably 1. 〇~1 〇 〇 molar equivalents with respect to the organic material, preferably 5.0 to 100 mole equivalents, more preferably 20 to 100 mole equivalents. The acid to be used when dissolved by acidic is an inorganic acid such as sulfuric acid, hydrochloric acid or phosphoric acid, or an organic acid such as acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid or trifluoromethanesulfonic acid, preferably an inorganic acid. Sulfuric acid is especially preferred. The amount of the acid used is such that the amount of the pigment can be uniformly dissolved, and there is no particular -20-200904907 limit. The inorganic acid and the organic acid are preferably 3 to 5 molar equivalents, more preferably 10 to 500 mole equivalents, and more preferably 30 to 200 mole equivalents, relative to the organic material. When a base or an acid is mixed with an organic solvent to use a good solvent as an organic pigment, 'in order to completely dissolve a base or an acid, a solvent having a high solubility to a base or an acid such as water or a lower alcohol may be added to the organic solvent. . The amount of water or lower alcohol is preferably 50% by mass or less with respect to the total amount of the organic material solution, and more preferably 30% by mass or less. Specifically, water, methanol, ethanol, n-propanol, isopropanol, butanol or the like can be used. When the organic particles are produced, even if the particles are organic, the conditions of the weak solvent at the time of formation are not particularly limited, and the range from normal pressure to subcritical and supercritical conditions can be selected. The temperature at normal pressure is preferably -3 0 to 1 0 ° C, more preferably -1 0 to 60 ° C, and particularly preferably 0 to 30 ° C. The method of mixing the organic pigment solution with the weak solvent is not particularly limited, and it is preferred to add the organic pigment solution to the weak solvent and mix it. In this case, it is preferred to stir the weak solvent. The stirring speed is preferably 1 〇〇 to 1 〇〇〇 〇 rPm, more preferably 150 to 8000 rpm, and particularly preferably 200 to 6000 rpm. Pumps can be used when adding or not. Further, it may be added to the liquid or added outside the liquid, and it is preferably added in a liquid. Mixing ratio of organic pigment solution to weak solvent (good solvent/weak solvent ratio in organic nano pigment particle re-sinking liquid), volume ratio is preferably 1/5 〇~2/3 '1M0~1/2 Better' is better than 1/20~3/8. In the case where the 'organic nano pigment particle system is first dispersed in an aqueous medium', the aqueous medium at this time contains at least 60% by mass of the above-mentioned aqueous solvent, and it is preferable to contain 80% by mass or more. 200904907 If the organic nano pigment particles are capable of being formed, the concentration of the re-sinking liquid of the organic nano pigment particles is not particularly limited, and the organic pigment particles are preferably in the range of 10 to 40,000 mg with respect to 1 ml of the aqueous medium, and 20 The range of ~30000 mg is better than the range of 5〇~25000 mg. Further, the preparation scale when the organic nano pigment particles are produced is not particularly limited, and the mixing amount of the weak solvent is preferably 1 to 100 liters, and the modulation scale of 1 to 100 liters is more preferable. Regarding the particle diameter of the organic nano pigment particles, there is a method of expressing the average particle diameter of the group by counting the number of the particles, and it is commonly used in the center of the particle diameter and the equivalent integral distribution curve showing the largest distribution. The particle size, various average particle diameters (number average, length average, area average, mass average, volume average, etc.), etc. In the present invention, the average particle diameter refers to the number average particle diameter unless otherwise notified. The average particle diameter of the organic nano pigment particles (primary particles) is a nanometer size, and the average particle diameter is preferably from 1 nm to 1 μm, preferably from 1 to 200 nm, and from 2 to 100 nm. More preferably, it is especially good for 5~80 nm. Further, the particles formed by the process of the present invention may be crystalline particles or amorphous particles, or a mixture thereof. Further, in the present invention, the ratio (?v/?) of the volume average particle diameter (Mv) to the number average particle diameter (??) is used as an index indicating the monodispersity of the particles, unless otherwise notified. The monodispersity of the particles (primary particles) contained in the organic nano pigment particle dispersion used in the method for concentrating the organic nano pigment particles, that is, Μν/Μη is preferably 1.0 to 2.0. ~1.8 is better, with 1 · 0 ~ 1 · 5 is especially good. The method for measuring the particle diameter of the organic nano pigment particles includes a microscope-22 - 200904907 method, a gravimetric method "light scattering method, an optical isolation method, an electric resistance method, an acoustic method, a dynamic light scattering method, and a microscopic method, dynamic light scattering. The law is especially good. Examples of the microscope using the microscope method include a scanning electron microscope and a transmission electron microscope. Examples of the particle measuring device by the dynamic light scattering method include NANOTRACK UPA-EX150 manufactured by Nikkiso Co., Ltd., dynamic light scattering photometer DLS-7000 series manufactured by Otsuka Electronics Co., Ltd., and LB-400 manufactured by Horiba, Ltd. ( Either are the product names). When the aqueous dispersion of the organic nano pigment particles is prepared, it is preferred to contain a dispersant (hereinafter referred to as a dispersant for the aqueous dispersion). The step of containing the dispersing agent is not particularly limited. It is preferred to add a dispersing agent to both or both of the organic pigment solution and the weak solvent. Further, it is also preferable to add a dispersant solvent by forming an organic nano pigment particle together with the above two liquid systems. It is also preferred to use a surface-treated pigment particle previously applied by a dispersant. A surface treatment capable of promoting adsorption of the dispersant may also be applied to the pigment powder. The dispersant system (1) rapidly adsorbs on the surface of the precipitated pigment to form fine nanoparticles, and (2) has an effect of preventing the particles from agglutinating again. As the dispersant which can be used, a low molecular or polymeric dispersant such as an anionic, cationic, diionic, nonionic or pigment derivative can be used. Further, the amount of the low molecular weight or high molecular weight dispersant added is preferably from 1% by mass to 100% by mass based on the pigment to be dissolved. It is more preferably 50% by mass or more and 200% by mass or less. When the amount of addition is too small, there is a case where the effect of suppressing the growth and aggregation of the pigment particles is reduced, and when it is too large, problems such as an increase in viscosity and poor dissolution may occur. Hereinafter, the polymer dispersant will be described. -23 - 200904907 The molecular weight coefficient of the polymer dispersant has an average molecular weight of 1,000 or more and 200,000 or less, more preferably 3,000 or more and 40,000 or less. When the molecular weight is too small, the effect of suppressing the growth and aggregation of the pigment particles is small, and when it is too large, problems such as an increase in viscosity and poor dissolution may occur. Further, in the present invention, the polymer means a number average molecular weight of more than 100 Å. Specific examples of the polymer dispersant include polyvinylpyrrolidone, polyvinyl alcohol, polyvinyl methyl ether, polyethylene glycol, polypropylene glycol, polypropylene decylamine, and vinyl alcohol-vinyl acetate copolymerization. , polyvinyl alcohol - partial methyl acetal, polyvinyl alcohol - partial butyral acetal, vinyl pyrrolidone - vinyl acetate copolymer and polyethylene oxide / propylene oxide block copolymer, etc. Polyvinylpyrrolidone is preferred. Examples of the anionic species include polyacrylate, polyethylene sulfate, poly(4-vinylpyridine) salt, polyamine, polyallylamine salt, polybenzenesulfonate, condensed naphthalenesulfonate, and cellulose derivative. And starch derivatives. Among them, polyphenylsulfonate and condensed naphthalenesulfonate are more preferred. These anionic persons can be obtained by copolymerization with an anionic monomer, and may be not only an anionic monomer itself but also a copolymer of a nonionic monomer. Specific examples of the nonionic monomer include vinylpyrrolidone, styrene, naphthalene, styrylmethylpyrrolidone, vinylimidazole, vinylpyridine, acrylamide, and vinylamine. The cationic compound is particularly preferably a polymer compound having a 4- to ammonium moiety, and examples thereof include poly(methacryloxyalkylammonium salt), poly(methacryloxyarylammonium salt), and poly. (Acryloxyalkylammonium salt), poly(propylene oxime 200904907 aryl ammonium salt), and poly(dipropylpropyl saddle salt), etc. The polymer compound having a 4-stage ammonium moiety is of the following formula ( 1) A polymer compound having a cationic repeating unit as shown is preferred. General formula (1)

......8Ra (wherein R1 to R_3 each independently represent a fluorenyl group, a aryl group, or an aryl group. Any two of Ri, R2, and R3 may be bonded to each other, and may also contain an oxygen atom or a nitrogen atom. a heterocyclic ring of an atom and/or a sulfur atom. The X system represents a dentate atom or an organic or inorganic anion. The η system represents a natural number of 1 to 5. The A system represents a hydrogen atom or an alkyl group, and the L system represents a single bond or 2 a linking group of a valence or a tetravalent linking group which is further bonded to any two of Ri, R2 and R3. In the formula (1), the alkyl group represented by 1 to 113 is a substituted or unsubstituted linear chain. The alkyl group having a branched or cyclic shape is preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having a carbon number of 丨4. The aralkyl group-substituted or unsubstituted aralkyl group represented by R1 to R3 is preferably an aryl group-substituted or unsubstituted aryl group represented by R1 to R3, and an aralkyl group having 7 to 10 carbon atoms. The aryl group having a carbon number of 6 to 10 is preferred. The aralkyl group or the aryl group may each be a single ring or a double ring. The base is specifically methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, cyclopentyl, hexyl, cyclohexyl, -25 - 200904907 A group, an octyl group, a third octyl group, a 2-ethylhexyl group, a decyl group and a dodecyl group are preferred. Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl are particularly preferred. The square base is specifically a benzyl group, a 4-chlorol group, a 4-methyl group, a 4-butoxybenzyl group, a 4-methoxyl methoxyphenyl group, and a 4-hydroxybenzyl group. . The group consists of a benzyl group, a 4·chlorobenzyl group, a 4-methylbenzyl group and a 4-butoxy group. The aryl group is specifically preferably a phenyl group, a 4-chlorophenyl group, a 4-methylphenyl group, a 4-butoxyphenyl group or a 4-hydroxy group. Phenyl, 4-chlorophenyl, 4-methylphenyl and 4-butoxyphenyl are particularly preferred. When any two of R, R2 and R3 are bonded to each other to form a nitrogen-containing hetero ring having a 4-stage ammonium moiety, the heterocyclic ring is preferably a 4 to 6 membered ring. Further, the hetero ring may further contain an oxygen atom, a nitrogen atom and/or a sulfur atom. Examples of the heterocyclic ring include an imidazolium, a pyridyl key, an oxime azole, a thiazole gun, an imidazoline, an oazoline gun, and a thioporphyrin. The better things are the microphone, the π key, the key and the thiazole key. In the formula (1), X may be monovalent or polyvalent, and the halogen atom represented by X is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. Specific examples of the organic anion represented by X include a carboxylic acid anion, a sulfonate anion, an alkoxide, a benzenesulfonate anion, a naphthalenesulfonate anion, a naphthalene disulfonate anion, and an anthracene disulfonate anion. Specific examples of the inorganic anion represented by X include a tetrafluoroanion anion, a phosphorus hexafluoride anion, and a hydroxide. I'm satisfied! ! It is particularly preferred for organic or inorganic anions having a natural number of 1 to 2. In the formula (1), the alkyl group represented by A is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or t-butyl. Ethyl methyl, -26 - 200904907 is particularly preferred. In the formula (1), L represents a single bond or a divalent linking group' or a tetravalent linking group which is further bonded to any two of Ri, R2 and R3. The divalent linking group represented by L system contains a linking group of an aryl group or an aralkyl group. The aryl group or aralkyl group contained in the divalent linking group represented by 1 may be a single ring or a condensed ring. A 4-valent linking group which is a combination of any two of R!, R2 and Rs represented by L forms a heterocyclic group with an ammonium salt moiety in the formula (1). Specific examples of the divalent linking group represented by L are exemplified by a phenyl group, a naphthyl group, and the like, and the aralkyl group is represented by a phenylmethylene group or a naphthylmethylene group. Examples of the heterocyclic ring formed by any two of the bonded tetravalent linking groups and the ammonium salt moiety in the formula (1) include, for example, meringin, 11 to D key, carbazole key, thiazole, imidazoline. Guns, oxazoline guns, and thiazoline keys. Imidazolium, pyridinium, oxazolium and thiazole are used. Specific examples in which any two of R, R2, and R3 are linked to each other include a heterocyclic ring containing an oxygen atom, a nitrogen atom, or a sulfur atom, and the following formula (1) is shown. An example of a quotient molecular compound showing a cationic repeating unit. Examples thereof include polyvinylimilin sulfonium salts, polyvinylbenzimidazolinium salts, polyvinylpyridine salts, polystyryl imidazolium salts, and polystyrene. Methyl sulfonium iron salt, polystyryl pyridyl salt, polystyryl methylene iron strontium salt, polystyryl methylene oxazolinium salt, polystyrene Methylene thiazolium salts, polystyryl methylene thiazole salts, polystyrene methyl ammonium salts, 'polynaphthylmethylimidazolium salts, polynaphthyl imidazolium Keyline salts, polynaphthyl pyridinium salts, polycalyptyl -27 - 200904907 oxazolium salts, polynaphthylmethyloxazoline salts, polynaphthylylene Thiazole salts, polynaphthylmethylthiazolium salts and polynaphthylmethylidene salts. Among these, particularly preferred examples include polystyryl methylene-salt salicyl salts, polystyryl-methylene imidazoline gun salts, and polystyrene-ethylidene pyridyl phosphate salts. , polystyryl methylene carbazole gun salt, polystyryl methylene oxazoline iron salt, polystyryl methylene thiazole gun salt, polystyryl methylene thiazole gun salt and Polystyryl methylene ammonium salts. The polymer compound having a quaternary ammonium moiety used in the present invention is more preferably a polymer compound having a cationic repeating unit represented by the following formula (2). General formula (2)

In the formula (2), Ri to R3, X and η are synonymous with Ri to Κ·3, X and η of the above formula (1), and the preferred ranges are also the same. Further, the polymer compound having a quaternary ammonium moiety used in the present invention may be a random copolymer composed of a cationic repeating unit represented by the above formula (1) and another repeating unit. The polymerization ratio is preferably from 0. 1 to 〇 7. 7 mass% with respect to the polymer compound having the fourth ammonium moiety of the former -28 - 200904907, preferably from 0. 1 to 0.5% by mass. The copolymerization component may, for example, be a vinyl imidazoline salt, a vinylbenzimidazolium iron salt, a vinyl pyridylium salt, a styrylmethylene imidazolium salt, or a styrylmethylene imidazole.铛 铛 铛 salt, styryl pyridyl salt, styryl methylene oxazolium salt, styryl methylene oxazoline salt, styryl methylene thiazole salt, benzene Vinyl methylene thiazole salt, styryl methylene ammonium salt, naphthylmethyl imidazolium salt, naphthyl imidazolium salt, naphthyl pyridinium salt , naphthylmethyl carbazole key salt, naphthylmethyl oxazolinium salt, naphthylmethyl thiophene salt, naphthyl thiazole gun salt, naphthyl methylene Ammonium salts, pyrrolidone, styrene, naphthalene, styrylchloromethane, vinylimidazole, vinylpyridine, acrylamide, vinylamine, and the like. Styryl methylene imidazolium salts, styryl methylene imipenem iron salts, styryl methylene pyridinium salts, styryl methylene ammonium salts, pyrrolidone, Styrene, naphthalene, styrylchloromethane, vinyl quinone, vinyl pyridine, acrylamide, and vinyl decylamine are particularly preferred. Specific examples of the polymer/compound having a 4-stage ammonium moiety used in the present invention are shown below, but the present invention is not limited thereto. In the following specific examples, the polymer compound used in the present invention is a heavy stomach exemplified by polymerization. -29- 200904907

The polymer compound having the above-mentioned four-stage ammonium moiety can be produced by referring to "small", 2006, Vol. 2, No. 7, pp. 879-883. Further, natural polymer compounds such as alginate, gelatin, albumin, casein, gum arabic, tragacanthgum, and lignosulfonate can also be used. -30 - 200904907 These polymers can be used alone or in combination of two or more. These dispersants can be used singly or in combination. The dispersing agent used for the pigment dispersion is described in detail on pages 29 to 46 of "Pigment Dispersion Stabilization and Surface Treatment Technology and Evaluation" (Chemical Information Association, issued in December 2001). Hereinafter, a low molecular weight dispersing agent will be described. Examples of the anionic low molecular dispersant include N-fluorenyl-N-alkyl taurates, fatty acid salts, alkyl thioesters, alkyl propane sulfonates, alkylnaphthalene sulfonates, and dialkyl groups. Sulfonic acid succinate, alkyl phosphate salt, naphthalenesulfonic acid formalin condensate, polyoxyethylene alkyl sulfate salt, and the like. Among them, N-fluorenyl-N-taurate is preferred. The N-mercapto-N-taurate is preferably described in the specification of JP-A No. 3-273,067. These anionic dispersants may be used alone or in combination of two or more. The cationic dispersant comprises a quaternary ammonium salt, an alkoxylated polyamine, an aliphatic amine polyglycol ether, an aliphatic amine, a diamine derived from an aliphatic amine and an aliphatic alcohol, and a polyamine, and a fatty acid. Derived imidazoline and salts of such cationic materials. These cationic dispersants may be used alone or in combination of two or more. The two-ionic dispersing agent has a dispersing agent having an anionic group portion in the molecule and a cationic group portion of the above-mentioned cationic dispersing agent in the molecule in the molecule. Examples of the nonionic dispersant include polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, and polyoxyethylene sorbitan fatty acid ester. Polyoxyethylene alkylamine, glycerin fatty acid ester, and the like. Among them, polyoxyethylene alkyl aryl ether is preferred. These nonionic fractions -31 to 200904907 may be used alone or in combination of two or more. A pigment derivative-type dispersant is defined as a pigment derivative-type dispersant obtained by chemically modifying the matrix structure derived from an organic pigment of a proliferative substance, or by chemically modifying the pigment. A pigment derivative-type dispersant obtained by subjecting a pigmentation reaction to a precursor. For example, there are a sugar-containing pigment derivative type dispersant, a piperidinyl group-containing pigment derivative type dispersant, a naphthalene or anthracene-derived pigment derivative type dispersant, and a pigment derivative type having a functional group which bonds a pigment parent structure through a methyl group. a dispersant, a pigment mother structure chemically modified with a polymer, a pigment derivative type dispersant of a sulfonic acid group, a pigment derivative type dispersant having a sulfonamide group, and a pigment derivative type dispersant having an ether group Or a pigment derivative type dispersant having a carboxylic acid group, a carboxylate group or a carboxy guanamine group. In the production method of the present invention, it is preferred to coexist an amine-based pigment dispersant when preparing an organic material 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. It may be a pigment derivative compound in which a substituent having an amine group is introduced into the pigment skeleton, or a polymerization compound in which a monomer having an amine group is used as a polymerization component. Examples of such examples include those described in JP-A-2000-239554, JP-A-2003-96329, JP-A-2001-31885, JP-A No. Hei 10-3 3949, and JP-A-5-7 2943. The compound or the like is not limited thereto. [Organic Low Molecular Compound and Organic High Molecular Compound] In the present invention, at least one organic low molecular compound having a molecular weight of less than 1 000 (hereinafter, also referred to as a low molecular compound) and at least one weight are -32 - 200904907 The organic polymer compound having a molecular weight of 1,000 or more (hereinafter also referred to as a polymer compound) acts on the organic nano pigment particles dispersed in the aqueous medium to aggregate, and then the organic nanoparticles are aggregated and aggregated. In the present invention, the low molecular compound condenses the organic nano pigment particles. The polymer compound agglomerates the coagulated body formed by coagulation to form an aggregate of a size that is easy to filter. In the present invention, a low molecular compound and a high molecular compound are used in combination. When the low molecular compound is used, although the organic nanoparticle is coagulated, it cannot be a large aggregate, and even if it is filtered by a filter paper, the filter paper is squeezed, or even if filtration is used. Filtering also takes a long time to filter. Further, in the case of only a polymer compound, since the coagulated body itself hardly occurs, it cannot be filtered. In the aqueous medium in which the organic nano pigment particles are dispersed, the weak polymer of the polymer compound of the present invention is adsorbed to the above-mentioned coagulated body, and the polar coagulum is not dissolved in the aqueous medium, so that the coagulated body grows into Big agglomerate. The average particle size of the aggregate is preferably more than 1 000 nm, and the larger the better. There is no particular upper limit for the average particle diameter, and actually it is less than 1 000 000 nm. When the average particle size of the aggregate is too small, it takes a relatively long time for the segregation of the aggregate to form, and even if it is filtered, there is a situation in which the filter paper is squeezed and the mesh is clogged. When the average particle size of the aggregate is too large, there will be a problem that it takes a lot of time to redisperse. In the non-aqueous medium, the organic nano-pigment particles which have been adsorbed on the agglomerated low-molecular-weight compound or the polymer compound are subjected to filtration, washing described later, and redispersion (de-agglomeration) which will be described later. It is also possible to directly use as a dispersing agent (hereinafter, also referred to as a dispersion of a non-aqueous dispersion, 200904907), without re-adding a dispersing agent. In order to adjust the dispersibility, the dispersant may be newly added later, but it is preferably not added from the viewpoint of production cost. Furthermore, in the present invention, the organic nano pigment particles constituting the aggregate are aggregated in a state in which they are applied to a low molecular weight and a high molecular compound, and are aggregated without such a low molecular weight or a high molecular compound, for example, When a case where a hydrochloric acid or the like is aggregated, the subsequent redispersion is easy, and the organic nanoparticle is easily released to the primary particles, and the contrast is improved. The low molecular compound or the polymer compound may be directly added, and from the viewpoint of obtaining good filterability, the low molecular compound or the high molecular compound is preferably added by dissolving in a solvent. The solvent is capable of being mixed with the organic nano pigment particles and is capable of dissolving the low molecular compound or the polymer compound, and is not particularly limited as long as the low molecular weight compound or the polymer compound does not precipitate itself after the addition. Further, the solvent is such that the organic nano pigment particles do not aggregate or even redisperse even if they are agglomerated even if they are added to the aqueous dispersion of the organic nano pigment particles (even if no grinding or high speed is applied) It is preferred to stir the solvent of the floc which is also capable of redispersing the high shear force. The solvent may, for example, be an aqueous solvent (for example, water or hydrochloric acid, an aqueous sodium hydroxide solution), an alcohol compound solvent, a guanamine compound solvent, a ketone compound solvent, an ether compound solvent, an aromatic compound solvent, a carbon disulfide solvent, or an aliphatic compound solvent. , a nitrile compound solvent, an anthraquinone compound solvent, a halogen compound solvent, an ester compound solvent, an ionic liquid, and a mixed solvent thereof, and an aqueous solvent, an alcohol compound solvent, a ketone compound solvent, an acid compound solvent, an anthraquinone compound solvent, an ester The compound solvent and the guanamine compound-34-200904907 are preferably a solvent, a nitrile compound solvent or a mixed solvent thereof, and particularly preferably a ketone compound solvent, an ether compound solvent, a nitrile compound solvent or a mixed solvent thereof. The alcohol compound solvent may, for example, be methanol, ethanol, isopropanol, n-propanol or 1-methoxy-2-propanol. The ketone compound solvent may, for example, be acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone. The ether compound solvent may, for example, be dimethyl ether, diethyl ether or tetrahydrofuran. Examples of the aromatic compound solvent include benzene, toluene, and the like. The aliphatic compound solvent may, for example, be hexane or the like. The nitrile compound solvent may, for example, be acetonitrile or the like. The halogen compound solvent may, for example, be dichloromethane or trichloroethylene. The solvent of the ester compound may, for example, be ethyl acetate or the like, ethyl lactate or 2-(1-methoxy)propyl acetate. Examples of the ionic liquid include salts of 1-butyl-3-methylimidon and PF6·. The amount of the solvent to be used is not particularly limited as long as it can dissolve the low molecular compound or the polymer compound and can form an aggregate which is easy to be filtered, and it is preferable to use as much as possible in consideration of the trouble of production and the reduction in the cost of the raw material. When it is represented by mass ratio, when the aqueous dispersion of the organic nano pigment particles is 100, the solvent to be added is preferably in the range of 1 to 1 Torr, and more preferably in the range of 1 〇 to 7 Torr. The range of 20 to 70 is particularly good. If there are too many, there will be a situation in which the aggregate must have a relatively long settling time. When there are too few, the formation of the aggregates may be insufficient, and the aggregates may become difficult to settle. After the solvent is added, it is preferably stirred so as to be sufficiently mixed with the aqueous dispersion of the organic nano pigment particles. Stirring and mixing can be carried out using a usual method. The temperature at which the solvent is added and mixed is not particularly limited, and is preferably from 1 - 35 to 200904907 to 1 0 0 ° C, more preferably from 5 to 60 ° C. When the addition and mixing of the solvent can be carried out well in any of the steps, any apparatus can be used, for example, a device such as a stirring blade or a Raman multi-static stirrer can be used. Further, as described above, when the organic nano pigment particles in the aqueous dispersion of the organic nano pigment particles are aggregated in the present invention, the low molecular compound or the polymer compound of the present invention can be additionally contained. The step of containing the low molecular weight compound or the polymer compound of the present invention is not particularly limited, and a method of adding the low molecular weight compound or the polymer compound of the present invention together with the aqueous solution of the organic nano pigment particle in the solvent may be added. A method of adding the organic nano pigment particle aqueous dispersion to the aqueous dispersion of the organic nano pigment particles after the addition of the organic nanoparticle pigment particles may be more preferably carried out. Further, in this case, a low molecular compound and a polymer compound may be added separately, or a polymer compound may be added to the solvent and dissolved, and then added to the aqueous dispersion of the organic nano pigment particles, followed by direct addition. The method of the molecular compound may be a method of adding a solution obtained by dissolving a polymer compound after adding a low molecular compound to the aqueous dispersion of the organic nano pigment particles. Further, the amount of the low molecular weight and the high molecular compound to be added is preferably 10% by mass or more and 10% by mass or less based on the total amount of the pigment. It is more preferably 50% by mass or more and 200% by mass or less. When the amount of addition is too small, there is a case where the aggregation effect of the nanoparticles is small. When there is too much, there is a problem that the viscosity is likely to rise in the case of redispersion which will be described later. The ratio of the amount of the low molecular compound to the polymer compound to be added is not particularly limited. When the mass ratio is 1 in the polymer compound, the low molecular weight compound is preferably 1 to 50%, more preferably 10 to 3 Torr. -36- 200904907 Hereinafter, the organic low molecular compound will be described in more detail. The organic low molecular compound may, for example, be an anionic, cationic or nonionic low molecular compound. The low molecular compound to be used can be selected in accordance with the aqueous dispersion dispersing agent used in the preparation of the above aqueous dispersion of the organic nano pigment particles. For example, when the aqueous dispersion is nonionic (especially alkaline), the low molecular compound is preferably nonionic (particularly acidic), and when the dispersant of the aqueous dispersion is anionic, the low molecular compound is cationic. When the dispersant of the aqueous dispersion is cationic, the low molecular compound is preferably anionic. Among them, the aqueous dispersion is nonionic (especially alkaline) and the low molecular compound is more nonionic (especially acidic), and the aqueous dispersion is cationic and the low molecular compound is anionic. . In the case of a nonionic low molecular compound, particularly an acidic organic low molecular compound, the molecular weight is less than 1 〇〇〇, and a carboxylic acid, a sulfonic acid or a phosphoric acid compound having a valence of 1 or more is preferred. The pentad-5 carboxylic acid, acid extension, and dish acid compound are more preferred. Specific examples of the carboxylic acid include formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, heptanoic acid, caprylic acid, capric acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, and isobutyric acid. , 2-ethylbutyric acid, trimethylacetic acid, tert-butylacetic acid, 2-propylpentanoic acid, 2-ethylhexanoic acid, malonic acid, butylmalonic acid, dimethylmalonic acid, Diethyl malonic acid, succinic acid, glutaric acid 'propane tricarboxylic acid, 1,2,3,4-butane tetracarboxylic acid, cis-5, 8, 11, 14, 17- twenty carbon five Alkenoic acid, cis-4,7,10,13,16,19-hexadecahexosaenoic acid, benzoic acid, phenylacetic acid and 11-phenoxy eleventh acid. -37 - 200904907 The sulfonic acid may specifically be methanesulfonic acid, N-cyclohexyl-2-aminoethyl ortho-acid, N-cyclohexyl-3-aminopropionic acid, benzenesulfonic acid or the like. Specific examples of the phosphoric acid include dimethylphosphonic acid and methylene disaccharide gastric. The ionic low molecular compound is not particularly limited as long as the molecular weight 舄 is less than 1 Torr, and the anionic compound is preferably an anionic compound represented by the following formula (3). General formula (3)

Y+ 'DE (where D is the expression - COO·, -S03_, -0S03·, -Ρ(0)(〇Η)〇-, or ·〇Ρ(〇)(ΟΗ)〇\Ε indicates that An alkyl group, an aralkyl group, an aryl group or an alkoxy group having a substituent having a total carbon number of 1 〇 to 1 。. The γ system means an organic or inorganic cation. In the formula (3), the D system represents - COO , -S03·, -0S03·, ·Ρ(〇)(〇Η)0, or - 〇Ρ(0)(ΟΗ)〇-, to -SO,, -Ρ(0)(ΟΗ)〇-for In the formula (3), the lanthanoid group represents a substituted alkyl group, an aralkyl group, an aryl group or an alkoxy group having a total carbon number of 10 to 100, and has a substituent having a total carbon number of 20 to 50. More preferably, the alkyl group, the arylalkyl group, the aryl group or the alkoxy group. The alkyl group or the alkoxy group or the substituent group may be linear or branched, and each of the aralkyl group or the aryl group may be The monocyclic ring may also be a condensed ring. The alkyl group may specifically be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, cyclopentyl or hexyl. Further, cyclohexyl, heptyl, octyl, trioctyl, 2-ethylhexyl, decyl, dodecyl and octadecyl groups are preferred. It is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl-38 - 200904907, isobutyl, tert-butyl, pentyl, cyclopentyl, hexyl, cyclohexyl and heptyl. Specific examples of the alkyl group include a benzyl group and a naphthylmethylene group, and a benzyl group is particularly preferred. The aryl group may specifically be a phenyl group or a naphthyl group. The phenyl group is particularly preferred. The alkoxy group may specifically be exemplified. Methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, pentyloxy, cyclopentyloxy, hexyloxy, cyclohexyloxy , heptyloxy, octyloxy, trioctyloxy, 2-ethylhexyloxy, nonyloxy, dodecyloxy and octadecyloxy. methoxy, ethoxy, positive The propoxy group, the isopropoxy group, the n-butoxy group and the isobutoxy group are preferred. In the general formula (3), the organic cation represented by Y may be an imidazole key salt, a pyridyl key salt or a thiazole salt. The imidazoline salt, the thiazoline salt, and the oxazoline salt are preferably inorganic cations, and the inorganic cations include lithium ions, sodium ions, potassium ions, and the like. . the following, It shows the general formula (3) Specific examples of the compound shown anionic -39 - 200 904 907

--〇H Lignin--

)—^~Vf〇CH2CH2 }ocH2CH2CH2 —|~〇K n 〇 n〇3 ϋ

T) The molecular weight of these low molecular compounds may be as small as less than 1000. When it is more than 1 Torr, the properties of the polymer compound appear, and it is difficult to coagulate the nanoparticles. The lower limit 该 of the molecular weight is not particularly limited, and is usually 40 or more. Hereinafter, the polymer compound will be described in more detail. In a preferred embodiment, the dispersing agent of the aqueous dispersion of the organic nano pigment particles is nonionic, particularly alkaline, in the same manner as the low molecular compound, and the polymer compound is preferably nonionic, particularly acidic, and is water-based. The dispersing agent of the dispersion is cationic, and the polymer compound is preferably anionic. In the present invention, the weight average molecular weight of the polymer compound is preferably 1,000 or more. There is no special upper limit, preferably 3 000 000 or less, and preferably 300 000 or less. Specific examples of the polymer compound which can be used in the present invention include "Disperbyk-110 (acid group-containing copolymer), 130 (polyamide), 161, 162, 163, 164, 165, manufactured by BYK Chemie Co., Ltd. 166, 170 (polymer copolymer), "BYK-P104, P105 (high molecular weight unsaturated polycarboxylic acid), EFKA 4047, 4050, 4010, 4165 (polyurethane), EFKA43 3 0, 4340 (block copolymer), -40 - 200904907 4400, 4402 (modified polyacrylate), 5010 (polyester decylamine), 5765 (high molecular weight polycarboxylate), 6220 (fatty acid polyester) ΑΠΝΟΜΟΤΟ "AJISPARPB821, PB822" manufactured by FINETECHNO Co., Ltd., "FROLEN TG-710 (urethane oligomer)", "POLYFRON〇.50E, Νο·300" (pronounced acid copolymer) )", Nanben Chemical Co., Ltd. "DISPARON KS-860, 873SN, 874, #2150 (aliphatic polycarboxylic acid), #7〇〇4 (polyether ester), DA-703-50, DA-705, DA- 725", Kao Corporation "DEMOL RN, N (naphthalenesulfonic acid formalin polycondensate), MS, C, SN-B (aromatic sulfonic acid Fuma) Polycondensate)", "HOMO GENOL L-18 (polymer polycarboxylic acid)", "EMAGEN920' 93 0, 93 5, 9 8 5 (polyoxyethylene nonylphenyl ether)", "ACETAMINE86 (stearin) "Amine acetate"", manufactured by LUBRIZOL Co., Ltd. "SOLUSPARS 5 5 00 (graft type polymer), 1 3240 (polyester type amine), 3 000, 1 7000, 27000 (polymer having a functional part at the end) , 24000, 28000, 32000, 38500 (grafted polymer)", "Nikon KK 0 LT 1 0 6 (polyoxyethylene sorbitan monooleate), MYS-IEX (polyoxyethylene) manufactured by Nikko Chemical Co., Ltd. Monostearate) and the like. As the polymer compound of the present invention, a known polymer compound can be used singly or in combination of two or more kinds. Further, a well-known polymer compound may be used in combination with one or more kinds of polymer compounds described later, and 'a polymer compound which can be used alone. Hereinafter, the nonionic polymer compound will be described in more detail. The nonionic polymer compound is preferably represented by the following formula (丨n. 200904907 Formula (π) (A1 - RVRt) In the above formula (丨1), A1 represents a component selected from an acidic group and has a base of a basic nitrogen atom, a urea group, a urethane group, a group having a coordinating oxygen atom, a hydrocarbon group having a carbon number of 4 or more, an alkoxy sand group, an epoxy group, an isocyanate group, and a hydroxyl group The monovalent organic group 'or contains an organic coloring material structure which may have a substituent or a monovalent organic group of a heterocyclic ring. The n A1's may be the same or different. Specifically, A1 is not particularly limited to the above-mentioned "acidic" The monovalent organic group having a carboxylic acid group, a sulfonic acid group, a monosulfate group, a phosphoric acid group, a monophosphate group, or a boric acid group, for example, may have a monovalent organic group. Examples of the monovalent organic group of the nitrogen atom group include a monovalent organic group having an amine group (-NH2), and a monovalent organic group having a substituted amino group NHR8 and -NR11% (here) , r8, R9 and R1 are each independently represented by an alkyl group having 1 to 20 carbon atoms, and having a carbon number of 6 or more and 2 or less. Or an aralkyl group having a carbon number of 7 or more and 30 or less, and a monovalent organic group having a fox group of the following formula (al); in the formula (al), Ral and Ra2 are each independently represented An alkyl group having 1 to 20 carbon atoms, an aryl group having 6 or more carbon atoms, 20 or less, or an aralkyl group having 7 or more and 30 or less carbon atoms, and a mercapto group represented by the following formula (& 2) a monovalent organic group [in the formula (a2), Ra3 and each of them are independent

200904907 The above-mentioned "monovalent organic group having a ureido group" is, for example, -> (: 〇 > 1115 (herein, '1115 is an alkyl group having a hydrogen atom having 1 to 20 carbon atoms, and a carbon number of 6) The above-mentioned aryl group of 20 or less, or an aralkyl group having a carbon number of 7 or more and 30 or less. The above-mentioned "monovalent organic group having a urethane group" may, for example, be -NHCOOR16 or -0C0NHR17 ( Here, R16 and R17 each independently represent an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 or more carbon atoms, 20 or less aryl groups having a carbon number of 7 or more and 30 or less, and the like. The monovalent organic group having a "coordinating oxygen atom group" includes, for example, a group having a acetic acid pyruvic acid group, a group having a crown ether, etc. The above-mentioned "monovalent organic group having a hydrocarbon group having 4 or more carbon atoms" Examples of the group include an alkyl group having 4 or more carbon atoms (for example, an octyl group or a dodecyl group), an aryl group having 6 or more carbon atoms (for example, a phenyl group or a naphthyl group), and an aralkyl group having 7 or more carbon atoms. The base (for example, benzyl group, etc.), etc. There is no upper limit of the number of carbon atoms, and it is preferably 30 or less. The above-mentioned "monovalent organic group having an alkoxyalkyl group" is exemplified. The group having a trimethoxyalkyl group, a triethoxyalkyl group, and the like. The "group having an epoxy group" may, for example, be a group having a glycidyl group. The "group having an isocyanate group" may be mentioned. For example, the above-mentioned "isocyanic acid group" may, for example, be a 3-hydroxypropyl group. The above A1 is selected from a group containing an acidic group, a basic nitrogen atom, a urea group, and a carbon number. The monovalent organic group of the hydrocarbon group of 4 or more is preferred. Further, the above organic colorant structure or heterocyclic ring is not particularly limited, more specifically -43 -

200904907 The organic colorant structure may, for example, be a phthalocyanine compound, an insoluble complex, a soluble azo compound, a hydrazine compound, a quinacridone dioxane compound, a dioxopyrrolopyrrole compound, an anthrapyridine compound, Anthonythroline standard reduction blue compound, xanthone compound, purple ring ketone compound, thioindigo compound, and the like. Further, examples of the heterocyclic ring include thiophene oxime, pyrrole, pyrroline, pyrrolidine, dioxapentane, pyrazolopyran, imipenem, diterpene, thiazide, fluorene b, and triterpenoid. Thiadipyran, pyridine, piperidine, dioxane, porphyrin, hydrazine, pyrimidine, triterpene, trimeric methyl aldehyde, isoporphyrin, isoindolinone, benzoanisoleimide, hydrazine Imine, naphthyl imine, hydantoin, porphyrin, oxazolidine, acridine, acridone and hydrazine. Further, the above-mentioned organic colorant structure or heterocyclic ring may have a substituent group, for example, 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 naphthyl group, and a hydroxyl group. Alkoxy group having a carbon number of 1 to 6 such as an amine group, a carboxyl group, a sulfonium N-sulfonylamino group or an ethoxycarbonyl group; a halogen atom having a carbon number of 1 to 6 such as a methoxy group; A carbon group having 2 to 7 carbon atoms such as a methyl group, an ethoxycarbonyl group or a cyclohexyloxycarbonyl group, or a carbonate such as a cyano group or a third butyl carbonate. Further, it is preferable that the BU described A 1 to be a price represented by the following formula (4). General formula (4) azo compound, nitrogen dye complex, sulfonate, furan, pyroline, sedative, pipe trap, imidazole, hydrazine, quinine, the phenyl group, [amine group, base, B The glycosyloxy oxime is -44- 200904907. In the above formula (4), B1 represents a group containing a group selected from an acidic group, having a basic gas atom, a sulfhydryl group, an excipient carboxylic acid group, and having a complex property. a group of an oxygen atom, a hydrocarbon group of 4 or more carbon atoms, an alkoxyalkyl group, an epoxy group, an isocyanate group, and a hydroxyl group, or an organic colorant structure or a heterocyclic ring which may have a substituent, and R18 represents a single bond. Or an organic or inorganic linking group of the price of al. The al system indicates that 1 to 5' al B1 may be the same or different. The preferred embodiment of the group represented by the formula (4) is synonymous with the above a1, and preferably, the organic colorant structure or heterocyclic ring may, for example, be a phthalocyanine compound, an insoluble azo compound, or soluble. Azo compound, hydrazine compound, quinophthalone compound, diterpene compound, dioxopyrrole porphyrin compound, anthrapyridine compound, antihanthron compound 'standard reduction blue compound, yellow Examples of the organic colorant structure such as an anthrone compound, a purple ring ketone compound, an anthraquinone compound, and a thioindigo compound include, for example, thiophene, furan, xanthene, pyrrole, pyrroline, pyrrolidine, dioxolane, pyrazole, Pyridin, pyrazole, imidazole, dioxazole, thiazole, oxadiazole, triazole, thiadiazole, pyran, pyridine, piperidine, dioxazole, porphyrin, hydrazine, pyrimidine, pipe trap, Tri-trap, trimeric methyl aldehyde, isoporphyrin, isoindolinone, benzimidazole, amber imine, quinone imine, naphthyl imine, hydantoin, quinone, quinoline, Heterocycles such as carbazole, acridine, acridone and hydrazine. Further, the organic coloring material structure or the heterocyclic ring may have a substituent. The substituent may, for example, be an alkyl group having 1 to 20 carbon atoms such as a methyl 'ethyl group, or a carbon number of 6 to 16 such as a phenyl group or a naphthyl group. An aryl group, a hydroxyl group, an amine group, a residue, a sulfonylamino group, an N-sulfonylamino group, an ethoxylated group, a methoxy group having 1 to 6 carbon atoms, a methoxy group, a B-45 - 200904907 oxy group, etc. Alkoxy group having 1 to 6 carbon atoms, a halogen atom such as chlorine or bromine, a methoxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group or a cyclohexyloxycarbonyl group; an alkoxycarbonyl group having 2 to 7 carbon atoms; a cyano group; A carbonate group or the like such as a carbonate. R18 represents a single bond or a linkage of al + valence, and a system represents 1 to 5. The linking group R18 includes a group consisting of 1 to 100 carbon atoms, 〇~1 氮 nitrogen atoms, 0 to 50 oxygen atoms, 1 to 200 hydrogen atoms, and 〇~20 sulfur atoms, which may be unsubstituted, It may also have a more substituent. R18 is preferably an organic linking group. Specific examples of R18 include the following structural units or a combination of the structural units. Further, the linking group R18 may have the aforementioned substituent T. —έ-ο- I ^ ^ -^― ^- —(p— — (ί-1) (t-2) (t-3) (t-4) (t-5) (t-6) (t -7) (t-8) (t-9) (t-1〇) 4-ν- Η -〇〇-C~N_ 0 0 o -One NC—C*N—έέ—Ν—H -艮N- (t-13) (t-14) (t-15) (t-16) (t-17) (t-18) -G*N- H I——I —- ΗΗ>*^ϊ- —C*G (t-20) (t-21) (t-22) (t-23) (t-24) (t-25) (t-26) (t-19) ο Μ -s-

II Ο (t-11) (t-12) (t-27) (^28) (t-29) (t_30) (t-31) (t-32) (t-33) (t-34) In the above, when the substituent R18 is present, the substituent may, for example, be an alkyl group having 1 to 20 carbon atoms such as a methyl group or an ethyl group, or a carbon number such as a phenyl group or a naphthyl group-46-200904907 6 to 16 a carbon number of 1 to 6 such as a methoxy group, a methoxy group or an ethoxy group having a carbon number of 1 to 6 such as a hydroxyl group, an amino group, a carboxyl group, a sulfonylamino group, an N-sulfonylamino group or an ethoxycarbonyl group; Carbonic acid having a carbon number of 2 to 7 such as a halogen atom such as alkoxy group, chlorine or bromine, a methoxycarbonyl group, an ethoxycarbonyl group or a cyclohexyloxycarbonyl group, or a carbonic acid such as a cyano group or a butyl carbonate. Ester group and the like. In the above formula (11), R1 represents a (m + n)-valent linking group, and m + n represents 3 to 10. The (m + n)-valent linking group represented by the above R1 includes 1 to 100 carbon atoms, 0 to 10 nitrogen atoms, 0 to 50 oxygen atoms, 1 to 200 hydrogen atoms, and 0 to 20 sulfur atoms. The group to be formed may be unsubstituted or may have a more substituent. R1 is preferably an organic linking group. Specific examples of R1 include a structural unit of the above (t-Ι) to (t-34) or a group composed of a combination of the structural units (which may also form a ring structure). When the above-mentioned linking group has a substituent, the substituent may, for example, be 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 or an amine group. a carboxyl group having 1 to 6 carbon atoms such as a carboxyl group, a sulfonylamino group, an N-sulfonylamino group or an acetoxy group, a methoxy group such as a methoxy group such as a methoxy group or an ethoxy group, chlorine, bromine, etc. A carbonate having 2 to 7 carbon atoms such as a halogen atom, a methoxycarbonyl group, an ethoxycarbonyl group or a cyclohexyloxy group, a carbonate such as a cyano group or a t-butyl carbonate, or the like. R2 is a single bond or a divalent linking group 'R comprising 1 to 1 carbon atoms, 〇 10 nitrogen atoms, 0 to 50 oxygen atoms, 1 to 200 hydrogen atoms, and 0 to 20 The group 'constituted by the sulfur atom' may be unsubstituted or may have a more substituent. R2 is preferably an organic linking group. -47 - 200904907 Specific examples of R2 include the structural units of the above t-3, 4, 7 to 18, 22 to 26, 32, and 34, or a combination of the structural unit combinations. In the above, when R2 has a substituent, the substituent may, for example, be 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 or an amine group. Alkoxy group having a carbon number of 1 to 6 such as a carboxyl group, a carboxy group, a sulfonylamino group, an N-sulfonylamino group or an ethoxylated oxy group, a methoxy group such as a methoxy group, a methoxy group, an ethoxy group or the like And a carbonate such as a halogen atom such as bromine, a methoxycarbonyl group, an ethoxycarbonyl group or a cyclohexyloxycarbonyl group, or a carbonate such as alkoxycarbonyl group having a carbon number of 2 to 7 or a cyano group or a butyl carbonate. In the above formula (11), m represents an integer of 1 to 8. ! 1! It is better to use 1~5. It is better to use 1~3, and 1~2 is especially good. Further, the η system represents an integer of 2 to 9. η is preferably 2 to 8, more preferably 2 to 7, and particularly preferably 3 to 6. In the above formula (11), hydrazine 1 represents a polymer residue, and can be selected from a usual polymer or the like according to the purpose and the like. Among the polymers, the polymer skeleton is selected from a polymer or copolymer derived from an ethylene monomer, an ester compound polymer, an ether compound polymer, a urethane compound polymer, and a guanamine system. a compound polymer, an epoxy compound polymer, a lanthanide polymer, and the like, or a copolymer (for example, a polyether/polyurethane copolymer, a polyacid/vinyl monomer) At least one of the group consisting of a copolymer of a polymer (any of a random copolymer, a block copolymer, and a graft copolymer) is preferably a vinyl monomer or a copolymerized or ester compound. At least one of a group consisting of a polymer, an ether compound polymer, a urethane compound polymer, and the like, or a group of a total of -48 - 200904907 polymer, preferably a vinyl monomer Polymers or copolymers are particularly preferred. Further, the aforementioned polymer is preferably soluble in an organic solvent. When the affinity with an organic solvent is low, for example, when it is used as a pigment dispersant, affinity with a dispersing medium may be inferior, and a sufficient adsorption layer may not be secured for dispersion stabilization. Among the compounds represented by the above formula (1 1), a polymer compound represented by the following formula (12) is more preferable. JA2-Rl-sJ-R^S-R5~P2)y General formula (12) In the above formula (12), the A2 system is synonymous with A1 of the above formula (11), and the specific preferred embodiment thereof is the same Specific examples of the organic colorant structure are preferably a phthalocyanine compound, a soluble azo compound, an anthraquinone compound, a diterpene compound, a dioxopyrrolopyrrole compound, or the like, and the heterocyclic ring is an imidazole, a triazole, a pyridine, or a piperidine. Pyridine, porphyrin, triple trap, isoporphyrin, isoindolinone, benzimidazole, benzothiazole, amber imine, quinone imine, naphthyl imine, hydantoin, hydrazine, Salino, carbazole, acridine, acridone and anthraquinone are more preferred. Further, the substituent may have a substituent similarly to A1, and the substituent may be the same as in the case of A1. Further, 'A2 is preferably a monovalent organic group represented by the above formula (4)'. The details, specific examples, and preferred aspects of the organic group are the same. In the above formula (12), R3 represents a (x + y) valent linking group. The (x + y) valent linking group represented by the above R3 includes from 1 to 60 carbon atoms, 〇1 to 1 氮 nitrogen atom '〇~50 oxygen atoms, ι~100 hydrogen atoms, and 〇~20 sulfur -49 - 200904907 The group consisting of atoms may be unsubstituted or substituted. The (χ + y)-valent linking group represented by the above R3 is synonymous with the (m + n)-valent linking group of the above R1, and the preferred embodiment thereof is also the same. Further, specific examples include the same structural unit or a combination of the structural unit combinations. Among these, the linking group represented by R3 is preferably an organic linking group, and a preferred specific example of the organic linking group [specific examples (r-Ι) to (r-17)] is as follows. However, the present invention is not limited to this. -ch2-ch; 1—CHj ^CH^—OG—CH2~CH2—H3G^ri^NCH2-0-G-CH2~CH2- (Γ-1) 2Η2*·6~0. 9 CH2 CHi一(r -2) H3C3~Cti CH2-〇-〇-CH2— --ch2~ch2-nh· !-6h 0 (Γ一3) G-MH—CH2-CM2· N>f2-〇-G-NH-- CH2-CH2-

0—CHZ ^CHa-O (r-4) CHi.CH2-〇-〇-〇--CH2--CH2-—CH “CH2~0~~0-0~Cl HaO-Cfir'^CHj-OGO- CHz-CHs*

-50- 200904907 -ΟΗϋ-ΟΗϊ-^-Ο-Ο·^, CH2~0*^~CH2-CH2- ("】〇) Production ^HrO-^CHi- 丨丨)

Among the above, (r-1), (r-2), (r-ΙΟ), (r-1 1) from the viewpoints of solubility in raw materials and easiness of synthesis' in various solvents. The basis of (), (r-16) and (r_i7) is preferred. In the case where the above R3 has a substituent, the substituent may, for example, be 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 or an amine group. Alkoxy group having a carbon number of 1 to 6 such as a carboxyl group having 1 to 6 carbon atoms such as a carboxyl group, a sulfonylamino group, an N-sulfonylamino group or an acetoxy group; And a carbonic acid ester such as a halogen atom such as bromine, a methoxycarbonyl group, an ethoxylated fluorenyl group or a cyclohexyloxycarbonyl group having 2 to 7 carbon atoms such as alkoxycarbonyl group, a cyano group or a third butyl carbonate. In the above formula (12), 1^4 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 have a substituent, a linear, branched, or cyclic alkyl group, an aryl group, or an aralkyl group, 200904907 -Ο- , -S-, -C( = 0)-, -N(R19)-, -SO-, -S〇2_, -C〇2-, -N(R2C))S〇2-, or a combination of 2 The above-mentioned base group is preferably a divalent group (the above R19 and R2G each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms). Among them, an organic linking group is preferred. The aforementioned R4 is a linear or branched alkyl or aralkyl group, -〇_, -C(=0)-, -N(R19)-, -S〇2-, -C02-, -N (R20) SO2-(wherein R19 and R2<) each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), or a divalent group obtained by combining two or more of these groups is more preferable. a linear or branched alkyl or aralkyl group, -C(=0)-, -N(R19)- (wherein R19 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), or -C02-' or a combination of two or more of these groups is particularly preferred. The aforementioned R5 is a linear or branched alkyl or aralkyl group, -0-, -C(=0)-, -N(R19)-, -S02-, -C02-, -N (R20). S〇2-(wherein R19 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), or a divalent group obtained by combining two or more of these groups is more preferably a straight chain or a branched An alkyl group or an aralkyl group, -〇-, -C(= 〇)-, -N(R19)- (wherein R19 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), or -CO 2- The divalent group formed by combining two or more of these groups is particularly preferable. In addition, when R4 and R5 have a substituent, the substituent may, for example, be 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, or a hydroxyl group. Alkoxy group having a carbon number of 1 to 6 such as an amino group, a carbonyl group, a sulfonylamino group, an N-sulfonylamino group or an ethoxycarbonyl group, having a carbon number of 1 to 6, a methoxy group, an ethoxy group or the like; Alkoxycarbonyl group having a carbon number of 2 to 7 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 carbonate such as a -52 - 200904907 tributyl carbonate Wait. In the above formula (12), the term "y" indicates that 1 to 8' is preferably 1 to 5, more preferably 1 to 3, and particularly preferably 1 to 2. Further, the X system indicates 2 to 9, preferably 2 to 8, and more preferably 2 to 7. '3 to 6 is particularly preferable. Further, P2 in the formula (12) represents a polymer residue, and can be selected from a usual polymer or the like according to the purpose and the like. The preferred embodiment of the polymer is synonymous with P 1 of the above formula (1 1), and the preferred embodiment thereof is also the same. Among the polymer compounds represented by the above formula (12), particularly, R3 represents the specific examples (r-1), (r-2), (r-10), (r-ii), (r_16). Or (r-17), R4 represents a single bond, a straight chain, a branched alkyl group, an aralkyl group, -〇-, -S-, -C(=0)-, -N(R19)- (R19 and R2G each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), -C02-, or a divalent group obtained by combining two or more of these groups, and R5 is a single bond or a vinyl group. a propylene group, or a linking group represented by the following formula (sa) or (sb), a polymer or copolymer of a P2-based vinyl monomer, an ester compound polymerization, an ether compound polymer, or an urethane system A polymer or a modified product thereof is particularly preferable as a polymer compound having a y system of 1 to 2' x series 3 to 6. Further, in the following group, R21 is a hydrogen atom or a methyl group, and 1 is 1 or 2.

0 (sb) -CH2-CH-G-〇-CH2-CH2 - The polymer compound used in the process of the present invention has a mass of -53 - 200904907 of 1000 or more, and a mass average molecular weight of 3,000 to 100,000 is preferable. ~80000 is better, with 7000~60000 as the best. When the mass average molecular weight is within the above range, the effect of introducing a plurality of functional groups at the terminal of the polymer can be sufficiently exhibited, and the adsorption property to the solid surface and the gel particle formation performance can be exhibited. In particular, when the polymer compound of the present invention is used as a pigment dispersant, good dispersibility and dispersion stability can be achieved. The polymer compound represented by the above formula (11) (including the compound represented by the formula (12)) is not particularly limited, and can be synthesized by the following method. In the synthesis method described below, the synthesis method of the following 2, 3, 4, and 5 is more preferable from the viewpoint of the ease of synthesis, and the synthesis method of the following 3, 4, and 5 is particularly preferable. 1. a polymer having a functional group selected from a carboxyl group, a hydroxyl group, an amine group, or the like, an acid halide having a plurality of functional groups (A1 or A2 in the above formula), or a plurality of functional groups (described above) A method of polymerizing an alkyl halide of A1 or A2) or an isocyanate having a plurality of functional groups (A1 or A2 in the above formula). 2. A method of subjecting a polymer having a carbon-carbon double bond to a terminal to a methacryl addition reaction with a thiol having a plurality of functional groups (A1 or A2 in the above formula). 3. A method in which a polymer having a carbon-carbon double bond introduced at its end and a thiol having a plurality of functional groups (A1 or A2 in the above formula) are reacted in the presence of a radical generator. 4. A method of introducing a polymer of a plurality of thiols at a terminal and a functional group (A1 or A2 in the above formula) into which a carbon-carbon double bond is introduced, in the presence of a radical generator. -54-200904907 5. A method of radically polymerizing a vinyl monomer by using a thiol compound having a plurality of functional groups (factor or A in the above formula) as a chain transfer agent. The polymer compound (preferably a polymer compound not represented by the formula (1 2)) used in the production method can be synthesized, for example, by the method of any of the above 2, 3, 4, and 5, and is easy to synthesize. In particular, it is more preferably synthesized by the method of the above 5. More specifically, a method of performing radical polymerization using a compound represented by the following formula (13) as a chain transfer agent is preferred. RLS^-Rs 十 SH)h General formula (13) In the above formula (13), R6, R7, A3, g and h, each is in the above formula (12), R3, R4, A2, X and y is synonymous, and the preferred embodiment thereof is also the same. The vinyl monomer is not particularly limited, and examples thereof include (meth) acrylates, crotonates, vinyl esters, maleic acid diesters, and anti-butyl groups. Oleic acid diesters, itaconic acid diesters, (meth) acrylamides, vinyl ethers, esters of vinyl alcohol, benzene The above-mentioned compound is preferable to the above-mentioned (meth)acrylic acid ester, and the (meth)acrylic acid ester is exemplified by methyl (meth)acrylate and ethyl (meth)acrylate. (Methyl) n-propyl acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, (methyl) N-hexyl acrylate, cyclohexyl (meth)acrylate, t-butylcyclohexyl (meth)acrylate, 2-ethylhexa-55 - 200904907 (meth)acrylate, third octyl (meth)acrylate Ester, dodecyl (meth)acrylate, octadecyl (meth)acrylate, ethoxylated ethyl (meth)acrylate, phenyl (meth)acrylate, 2-hydroxyl (meth)acrylate Ethyl ester, 2-methoxyethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, 2-(2-methoxyethoxy)ethyl (meth)acrylate, ( 3-phenoxy-2-hydroxypropyl methacrylate, benzyl (meth) acrylate, diethylene glycol (meth) acrylate Monomethyl ether, diethylene glycol monoethyl ether (meth)acrylate, triethylene glycol monomethyl ether (meth)acrylate, triethylene glycol monoethyl ether (meth)acrylate, (meth)acrylic acid poly Ethylene glycol monomethyl ether, polyethylene glycol monoethyl ether (meth)acrylate,/5-phenoxyethoxyethyl (meth)acrylate, nonylphenoxy poly(meth)acrylate Ethylene glycol ester, nonylphenoxy polyethylene (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, (meth)acrylic acid Fluoroethyl ester, octafluoropentyl (meth)acrylate, perfluorooctyl (meth)acrylate, dicyclopentanyl (meth)acrylate, trifluorophenyl (meth)acrylate, and (methyl) Trifluorophenoxyethyl acrylate or the like. The crotonate may, for example, be butyl crotonate or hexyl crotonate. Examples of the vinyl esters include vinyl acetate, vinyl propionate, vinyl butyrate, methoxyvinyl acetate, and vinyl benzoate. The maleic acid diester may, for example, be dimethyl maleate, diethyl maleate or dibutyl maleate. Examples of the fumaric acid diester include dimethyl fumarate, diethyl fumarate, and dibutyl fumarate. Examples of the above-mentioned isonic acid diesters include dimethyl itaconate, diconic acid-56-200904907 diethyl ester, and dibutyl itaconate. The (meth) acrylamide may, for example, be (meth) acrylamide, N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide, N-propyl (A) Base acrylamide, N-isopropyl (meth) acrylamide, N-n-butyl (meth) acrylamide, N-tert-butyl (meth) acrylamide, N-cyclohexyl (Meth) acrylamide, N-(2-methoxyethyl)(methyl) acrylamide, N,N-dimethyl(meth) acrylamide, N,N-diethyl ( Methyl) acrylamide, N-phenyl (meth) acrylamide, N-benzyl (meth) acrylamide, (meth) acryl hydrazine, and diacetone acrylamide. Examples of the styrenes include styrene, methyl styrene, dimethyl styrene, trimethylstyrene, ethyl styrene, isopropyl styrene, butyl styrene, hydroxystyrene, and methoxy. Styrene, butoxy styrene, ethoxylated styrene, chlorostyrene, dichlorostyrene, bromostyrene, chloromethylstyrene, a group which can be deprotected by using an acidic substance (for example, the third B 〇 c, etc.) protected hydroxystyrene, methyl benzoate, and methyl styrene. Examples of the vinyl ethers include methyl vinyl ether, butyl vinyl ether, hexyl vinyl ether, and methoxyethyl vinyl ether. In addition to the above compounds, (meth)acrylonitrile, a vinyl-substituted heterocyclic group (for example, vinylpyridine, vinylpyrrolidone, vinylcarbazole, etc.), N-vinylformamide, N- may also be used. Vinyl acetamide, N-vinylimidazole and vinyl caprolactone. Further, in addition to the above compounds, for example, an ethylenic monomer having a functional group such as an amino carboxylic acid valerate group, a ureido group, a sulfonamide group, a phenol group or a brewed imino group can be used. A monomer having such a urethane group or a ureido group, for example, -57 - 200904907 can be appropriately synthesized by an addition reaction of an isocyanate group with a hydroxyl group or an amine group. Specifically, it is possible to carry out an addition reaction by a monomer containing an isocyanate group, a compound containing a hydroxyl group or a compound having a primary or secondary amine group, or by a monomer having a hydroxyl group or a grade 1 The monomer of the second-order amine group is subjected to an addition reaction with a monoisocyanate or the like and appropriately synthesized. The polymerization may be carried out using only one type of the above-mentioned vinyl monomer, or two or more types may be used in combination, and such a radical polymer can be obtained by polymerizing each of the equivalent vinyl monomers by a usual method in accordance with a usual method. For example, a method in which a vinyl monomer and a chain transfer agent are dissolved in a suitable solvent, a radical polymerization initiator is added thereto, and polymerization is carried out in a solution at about 50 to 220 ° C (solution polymerization method) ) can get. An example of a suitable solvent which can be used in the solution polymerization method can be arbitrarily selected in accordance with the solubility of the monomer to be used and the copolymer to be produced. For example, methanol, ethanol, propanol, isopropanol, i-methoxy-2-propanol, 1-methoxy-2-propyl acetate, acetone, methyl ethyl ketone, methyl isobutylene can be mentioned. Ketone, methoxypropyl acetate, ethyl lactate, ethyl acetate, acetonitrile, tetrahydrofuran, dimethylformamide, chloroform and toluene. These solvents may be used in combination of two or more kinds. Further, the radical polymerization initiator can utilize a compound such as 2,2'-azobis(isobutyronitrile) (AIBN), 2,2,-azobis-(2,4'-monomethylvaleronitrile) For example, peroxides of benzamidine peroxide and potassium persulfate, persulfate of ammonium persulfate, and the like. The compound represented by the above formula (13) can be more preferably used in the following manner from the viewpoint of ease of synthesis by the following method. 6. A method of converting a halogen compound having a plurality of functional groups (A1 or a2 in the above formula) into a thiol compound (a method of reacting with thiourea to carry out hydrolysis, and directly reacting with NaSH) ; reaction with CH3COSNa, hydrolysis method, etc.). 7. A method of subjecting a compound having 3 to 10 thiol groups in one molecule to a compound having a functional group (A1 or A2 in the above formula) and capable of reacting with a thio group . In the above method 7, the "functional group capable of reacting with a hydrogenthio group" may suitably be an acid halide, an alkyl halide, an isocyanate or a carbon-carbon double bond. The "functional group capable of reacting with a hydrogenthio group" is a carbon-carbon double bond, and the addition reaction is preferably carried out by a radical addition reaction. The carbon-carbon double bond is more preferably a 1-substituent or a 2-substituent from the reactivity with a thiol group. The following specific examples (18) to (34) of the "compound having 3 to 1 thiol group in one molecule" include the following compounds. -59- 200904907 HS-CHj-CHa·

, m〇\ HS-CHjt-G-O—CH2 〇 (υ-1δ) (U-19)

Ij-O-g-CHi-CHj-SH

SH 6-0—i •che xh2-

B-°T

(u-27) -CHrCHz-SH CH2-CH2-SH U-&-〇-CH2 ^^CH^-OG-CH2-SH (U-28) HS-CHZ HS-CH2~〇-〇-CH^ ^CHz-OGC^-SH° ά (u-30) -o-ch2-ch2-sh

.〇-ch2-ch2-sh

HS-CH2-CH2-NH~0-CHa,CH2-0-^-NH-CiHs-CHa-SH HS-CH^CHa-NH-0-0-013⁄4 CH2-〇-G-NH-CH2-CH2- SH ά 0 (u-29) O 0 HS ^CH2- SH HS-CHrCHfO-J^Y^-O-CHrCHrSH 0~CH2 CH; --CHrCH2~^~p (U-31) HS-CH2-* CH2~&-〇-CH2 ^CHg-OH^-Ci^-CHj-SH (U_33) HS-CHj-CiHj ^CHi-CH^-SH (jJ-32) HS-CHa-^-O-CHz^ _/CHr〇~^-CHz-SH HS-CHrCHy-oC, Hs-CHr〇)2-〇HS—CHj—C:

C

'NCH2-〇-〇H:H2-CHrSH 0 /h2 'CH2- .-(--O-CH, ,CH^—〇

-CH2-SH HS-CH2-CH2 jL Xm^CH2-CH2-SH HS-CHz-GOC; M2, ^/bnr HS-CHa Chf" \ , CH2-CH2-SH HS-C^-GO-CHr ^CHa -O-^-CHjr-SH (U~34) Among the above, from the viewpoint of the availability of raw materials and the solubility in various solvents, 'U -18', (U -19) ' (u -27 ), (U -28), (U -33), (U -34) 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 the following may be mentioned. -60 - 200904907

200904907

-62 - 200904907

-63 - 200904907

For example, the above-mentioned "a compound having 3 to 10 hydrogenthio groups in one molecule" and the above "selected from an acidic group, a group having a basic nitrogen atom, a urea group, a urethane group, and having a complex property" A radical addition reaction product is formed by a radical of an 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 having a carbon-carbon double bond compound For example, the above-mentioned "a compound having 3 to 10 thiol groups in one molecule" and the above "a group selected from an acidic group, a group having a basic nitrogen atom, a ureido group, a urethane group, and the like" can be used. 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 one functional group of a hydroxyl group and having a carbon-carbon double bond compound dissolved in a suitable solvent In this, a free radical initiator is added here at about 50 °C ~1 〇〇-64 - 200904907. (: obtained by a method of addition (thiol-olefin reaction method). An example of a preferred solvent used in the above method can be selected according to "a compound having 3 to 10 hydrogenthio groups in one molecule", From an acidic group, a group having a basic nitrogen atom, a urea group, a urethane group, a group having a coordinating oxygen atom, a hydrocarbon group having a carbon number of 4 or more, an alkoxyalkyl group, an epoxy group, an isocyanate group The solubility of at least one functional group in the hydroxyl group and a functional group (for example, a carbon-carbon double bond) capable of reacting with a hydrogenthio group, and the radical addition reaction product produced are arbitrarily selected. For example, methanol, ethanol, propanol, isopropanol, 1-methoxy-2-propanol, 1-methoxy-2-propyl acetate, acetone, methyl ethyl ketone, methyl isobutylene can be mentioned. Ketone, methoxypropyl acetate, ethyl lactate, ethyl acetate, acetonitrile, tetrahydrofuran, dimethylformamide, chloroform and toluene. These solvents may also be used in combination of two or more. The initiator can utilize, for example, 2,2'-azobis(isobutyronitrile) (AIBN), 2,2,-azo a compound of (2,4'-dimethylvaleronitrile), such as a peroxide of benzamidine peroxide and a persulfate of potassium persulfate or ammonium persulfate. -ΠΤΙ- _ suitable for use in the process of the present invention Specific examples of the compound represented by the formula (11) are shown below, but the present invention is not limited to these specific examples. -65 - 200904907

(C-1)

HOjC^Y^S HOsC

〇2〇Η3 (n=S. m=1) cWrCHr^-o-CHz^CHa~CT -CHz^QVgO-CHi^CHrO^-CHjrCHjr rO-b-Cy- ;H2-CHr Hs-OG-CHj- CHj·*· (C-2)

Hj-CHr* -66- 200904907

(ri=5, } (c*4>

'-CHrCHj^XH^CHaO^^CHrCHr Q ΧηΓκχ;η2-〇-〇-οη2-οηγ- -CHy-CHg-O-O CHj .CH2—U b

:02CW3 (n=5, »r=1) (C-7)

200904907

-68 - 200904907

(C-18) 200904907

(C-20)

(C-21) -70 - 200904907

200904907

R3: , -CHj-Ci -CHf :h7xh;

:H5 >CH2*i :M2 ^CHiH rO-〇-~CHrCHi-

R3- -CHjfCHjf?· -CH? CH; ^ y-O-6-CHj-CHy- O-CHj XH. o chSjhj DHrCHif-

/

R5- - -CHrCHrl-O-CI 3Hz-6-0-CH^,C xhtSci ;H? vCH3—CT lOXHarO^-CH^-CHr- ^-CHr CHrO-ft-CHrCHz- OHi-CHr- \ (n =5, m=1) (C-32)

[ C〇2〇Hs_

R·, ( -CHa-CHa-J -CHrCHjH "CHrCHi^-0-CH3^^CHr ZHrCHr :HrCHr- :HrCHr· (n=5. m^1) (C-33) -72 200904907

R;= ••CHjrCMjj—

-ch2-cm2-6-o -CHrCHr^-〇-CH7 '^KrO-g-CHa-CHj- (r»=4.5. (C-36)

Further, the polymer compound is preferably a polymer compound having an acidic group, and more preferably a polymer compound having a carboxyl group, and contains at least one repeating unit introduced from (A) a compound having a carboxyl group and at least 1 The (B) copolymerized compound of a repeating unit introduced from a compound having a carboxylate group is particularly preferred. The repeating unit introduced by the above (A) compound having a carboxyl group is preferably a repeating unit represented by the following formula -73 - 200904907 (I), and a repeating unit derived from acrylic acid or methacrylic acid is more preferable, the above (B) The repeating unit introduced by the compound having a carboxylate group is preferably a repeating unit represented by the following formula (II), and more preferably a repeating unit represented by the following formula (IV): benzyl acrylate or methacrylic acid The repeating unit introduced by the ester, phenylethyl acrylate, phenylethyl methacrylate, 3-phenylpropyl acrylate, or 3-phenylpropyl methacrylate is particularly preferred.

COOH General formula (I) (R! is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms)

Formula (II) (R2 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. R3 is a group represented by the following formula (ΠΙ)

General formula (III) (R4 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, a hydroxyl group, a hydroxyalkyl group having 5 to 5 carbon atoms, or an aryl group having 6 to 20 carbon atoms. Represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. The number of XI series 1 to 5) -74 - 200904907

(R? is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms; R8 is a group represented by the following formula (V))

General formula (V) (R9 is an alkyl group having 2 to 5 carbon atoms or an aryl group having 6 to 20 carbon atoms. Rio and Rm are a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. Y1 is 1 to 1) The number of 5) The ratio of the repeating unit introduced by (A) the compound having a carboxyl group to the repeating unit introduced by the above (B) compound having a carboxylate group, with respect to the repeating unit (A) The total number of repeating units, the number ratio is preferably 3 to 40%, preferably 5 to 35%. Further, the method for producing organic nanoparticles of the present invention contains a graft copolymer having an amine group and an ether group, and preferably contains a polymer compound of another component appropriately selected as necessary. The graft copolymer has at least an amine group and an ether group, and may contain other monomers or the like as a copolymerization unit. The mass average molecular weight of the aforementioned graft copolymer is preferably from 3,000 to 100,000, more preferably from 5,000 to 50,000. When the mass average molecular weight is too small at 200904907, it is impossible to prevent aggregation of the organic nanoparticles, and the viscosity may increase. When the temperature is too large, the solubility in an organic solvent may be insufficient, and the viscosity may increase. Further, the weight average molecular weight is a weight average molecular weight converted to polystyrene measured by a gel permeation chromatograph (carrier: tetrahydrofuran). The graft copolymer contains at least (a polymerizable oligomer having an ethylenically unsaturated double bond at the end, (ii) a monomer having an amine group and an ethylenically unsaturated double bond, and (iii) an ether group. The polymerizable monomer is preferably a copolymer unit, and it is preferable to contain (iv) another monomer as a copolymerization unit as necessary. The content of the copolymer unit in the graft copolymer is (i) the aforementioned polymerizability is low. The polymer is preferably 15 to 98% by mass, more preferably 25 to 90% by mass, and (ii) preferably 1 to 40% by mass of the monomer having an amine group is preferably 5 to 3 % by mass. (iii) The ether group-containing polymerizable monomer is preferably 1 to 70% by mass, more preferably 5 to 60% by mass. The content of the polymerizable oligomer is too small, and it may not be used as a dispersing agent. When the steric repulsion effect is obtained and the aggregation of the organic nanoparticles is not prevented, when the ratio of the polymerizable oligomer is decreased in excess, the adsorption capacity of the organic particles may be lowered and the dispersibility may be insufficient. When the ratio of the body is too small, there will be adsorption of organic particles. When the force is decreased, the dispersibility is insufficient, and when the amount of the polymerizable oligomer is decreased, the dispersing agent may not have a steric repellency effect, and the aggregation of the organic nanoparticles may not be sufficiently prevented. When the content of the polymerizable monomer is too small, the case where the color filter is insufficient in the production of the color filter may be insufficient. When the amount is excessive, the ability as a dispersing agent may be lowered. -76 - 200904907 (i) Polymerization Oligomer The polymerizable oligomer (hereinafter referred to as a "macromonomer") is an oligomer having a group containing a bivalent unsaturated double bond at the terminal. In the present invention, the foregoing The polymerizable oligomer preferably has a group containing only an ethylenically unsaturated double bond in the both ends of the oligomer. The polymerizable oligomer is usually selected, for example, from the group consisting of a separate polymer or copolymer of at least one of (meth)acrylic acid alkyl ester, hydroxyalkyl (meth) acrylate, styrene, acrylic acid, 'ethyl acetate, and butadiene, Etc., In the present invention, the oligomers may be substituted with a substituent, and the substituent is not particularly limited, and examples thereof include a halogen. The group having an ethylenically unsaturated double bond may, for example, be a (meth) acrylonitrile group or a vinyl group, and among these, a (meth) acrylonitrile group is preferred. In the above-mentioned polymerizable oligomer, an oligomer represented by the following formula (E6) is preferred. R61 _H2C = (!>-"〇~Re2-s_<ΟΗ2-^Η)ή - Η > 63 Formula (Ε6) In the above formula (Ε 6), R61 and R63 represent a hydrogen atom or a methyl group. R62 represents an alkyl group which may be substituted by an alcoholic hydroxyl group having a carbon number of 丨8. It is preferred to use an alkylene group having 2 to 4 carbon atoms. Y6 represents a phenyl group, a phenyl group having a carbon number of 1 to 4, and a phenyl group having a carbon number of 1 to 4, or -COOR64 (here, R64 means an alcohol which may be substituted with an alcoholic hydroxyl group having 1 to 6 carbon atoms or a halogen. The group, the phenyl group or the aryl group having a carbon number of 7 to 10 is preferably a phenyl group or a COOR 64 (here, the R64 group may be an alkyl group substituted with an alcoholic hydroxyl group of 1 to 4). The q system represents 20 to 200. Specific examples of the above polymerizable oligomer are poly(hydroxy)(meth)acrylate, polystyrene, poly(methyl) acrylate, poly(meth)acrylate, and poly(meth)acrylic acid. The isobutyl ester, a copolymer thereof or the like is preferably a polymer having a (meth) acrylonitrile group bonded to one of the molecular terminals. The polymerizable oligomer may be a commercially available product or may be a suitably synthesized product. The commercially available product may, for example, be a styrene-based polystyrene oligomer having one terminal (Mn = 6000, Trade name: AS-6, manufactured by East Asia Synthetic Chemical Industry Co., Ltd.), polymethyl acrylate oligomer methacrylated at one end (Mn = 6000, trade name: AA-6, East Asia Synthesis) Chemical Industry Co., Ltd.), a poly(n-butyl acrylate) oligomer methacrylate-based at one end (Mn = 60 〇〇, trade name: AB-6, East Asia Synthetic Chemical Industry Co., Ltd.) Methyl methacrylate-methyl methacrylate/2-hydroxyethyl methacrylate oligomer (Mn = 7000, trade name: AA-714, East Asia Synthetic Chemical Industry Co., Ltd.) )), methacrylic acid butyl methacrylate/2-hydroxyethyl methacrylate oligomer (Mn = 7000, trade name: 707S, East Asia Synthetic Chemical Industry Co., Ltd.) ))), a methyl propylene succinic acid 2-ethyl group Methacrylate / 2 - hydroxyethyl methacrylate oligomer (Mn = 7000, trade name: AY-707S, AY-714S, Toagosei Chemical Industry (shares) Corporation) and the like. -78 - 200904907 In a preferred embodiment of the polymerizable oligomer of the present invention, a polymer selected from the group consisting of alkyl (meth)acrylate and a copolymer of alkyl (meth)acrylate and polystyrene At least one oligomer having a number average molecular weight of from 1,000 to 20,000 and having a (meth) acrylonitrile group at the terminal. (U) Amine group-containing monomer The amine group-containing monomer may be, for example, at least one selected from the group consisting of compounds represented by the following formula (E2).

M-(NHR22)^2 General formula (E2) In the above formula (E2), R21 represents a hydrogen atom or a methyl group. R22 represents an alkylene group having 1 to 8 carbon atoms. Among them, an alkylene group having 1 to 6 carbon atoms is preferred, and an alkylene group having 2 to 3 carbon atoms is particularly preferred. X2 represents -N(R23)(R24) and -R25N(R26)(R27). Here, R23 and R24 are a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a phenyl group. R2 5 is an alkylene group having 1 to 6 carbon atoms, and R26 and R2 7 are a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a phenyl group. In the above, R23 and R24 of -N(R23)(R24) are preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a phenyl group, and R25 of _R25_N(R26)(r27) is a carbon number of 2 to 6 carbon atoms. The alkylene group is preferred, and R26 and R27 are preferably an alkyl group having a carbon number of i to 4. M2 and n2 represent 1 or 〇, with m2=l and n2 = l, or m2 = l and n2 = 0 (i.e., 'corresponding to the monomers of the following general formulae (E3), (E4)) . In the present invention, at least one selected from the group consisting of the following formula (E3) and (E4) is preferred among the monomers represented by the above formula (E2). -79 - 200904907 h2c=

Hr32-x3 Formula (E3) The above formula (E3)' R31 is synonymous with R21 of the formula (E2). R32 is synonymous with R22 of the formula (E2). The X3 system is synonymous with X2 of the formula (E2).

The above formula (E4)' R41 is synonymous with R21 of the formula (E2). X4 is synonymous with X2 of the general formula (E2), and -N(R43)(R44) (here, R43 and R44 are synonymous with R23 and R24 of the general formula (E2)). R45-N(R46)(R47) (wherein R45, R46 and R47 are each synonymous with R25, R26 and R27 of the formula (E2)). Specific examples of the monomer represented by the above formula (E2) include dimethyl (meth) acrylamide, diethyl (meth) acrylamide, diisopropyl (meth) acrylamide, Di-n-butyl (meth) acrylamide, diisobutyl (meth) acrylamide, morpholinyl (meth) acrylamide, piperidinyl (meth) acrylamide, N-methyl 2-pyrrolidinyl (meth) acrylamide and hydrazine, Ν-methylphenyl (meth) acrylamide (above (meth) acrylamide); 2- (Ν, Ν-二Methylamino)ethyl (meth) acrylamide, 2-(indole, hydrazine-diethylamino)ethyl (meth) acrylamide, 3-(indole, hydrazine-diethylamino)propyl (Meth) acrylamide, 3-(Ν,Ν_:methylamino)propyl(meth)acrylamide, 1-(Ν,Ν-dimethylamino)-1,1-dimethylmethyl (meth)acrylamide, 6-(anthracene, oxime diethylamino)hexyl (meth) acrylamide (the above amine-80 - 200904907 alkyl (meth) acrylamide), etc. It is better. (iii) Ether group-containing polymerizable monomer The ether group-containing polymerizable monomer may be at least one selected from the group consisting of the following formula (E1).

In the above formula (El), R11 represents a hydrogen atom or a methyl group. Ri2 is an alkylene group having 1 to 8 carbon atoms, preferably 1 to 6 alkylene groups, more preferably 2 to 3 alkylene groups. X1 represents -OR13 or - OCOR14. Here, R13 represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a phenyl group, or a carbon number! -18 alkyl substituted phenyl. R14 represents an alkyl group having 1 to is carbon. Further, m3 is 2 to 200, preferably 5 to 100, and particularly preferably 1 to 1 。. When the ether group-containing polymerizable monomer contains an ether group and is a polymerizable substance, it is not particularly limited, and may be appropriately selected from ordinary ones, and examples thereof include polyethylene glycol mono(meth)acrylate 'polypropylene glycol. Mono(meth)acrylate, polyethylene glycol polypropylene glycol mono(meth)acrylate, and polybutanediol monomethacrylate, which may be commercially available or may be appropriately synthesized. The commercially available product may be methoxy polyethylene glycol methacrylate (trade name: NK ESTER M-40G, M-90G, M-230G (above, manufactured by Toago Chemical Co., Ltd.); Name: BLENMER PME-100, PME-200, PME-400, PME-1000, PME-2000, PME-4000 (above, manufactured by Nippon Oil & Fats Co., Ltd.), polyethylene glycol monomethacrylate (trade name) :BLENMER PE-90, PE-200, PE-350, 曰本油(股) 公200904907 司), polypropylene glycol monomethacrylate (trade name: BLENMER PP-500, PP-800, PP-1000, Japan Oils and Fats Co., Ltd., polyethylene glycol polypropylene glycol monomethacrylate (trade name: BLENMER 70PEP-3 70B, manufactured by Sakamoto Oil Co., Ltd.), polyethylene glycol polybutanediol Methacrylate (trade name: BLENMER 5 5 PET-8 00, manufactured by Nippon Oil & Fats Co., Ltd.), polypropylene glycol polybutanediol monomethacrylate (trade name: BLENMER NHK-5050, Japanese fats and oils) (Company)), etc. (iv) Other monomers The aforementioned graft copolymer may further contain the aforementioned other monomers as copolymers. The other monomer is not particularly limited and may be appropriately selected according to the purpose, and examples thereof include an aromatic vinyl compound (for example, styrene, α-methylstyrene, and vinyltoluene) and an alkyl (meth)acrylate. (for example, methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate and isobutyl (meth) acrylate), alkyl aryl (meth) acrylate (for example, (Methyl) alkyl benzyl acrylate, glycidyl (meth) acrylate), vinyl carboxylate (eg, vinyl acetate and vinyl propionate), acrylonitrile (eg, (meth) acrylonitrile and Α-chloroacrylonitrile) and an aliphatic conjugated diene (for example, 1, 3-butadiene, isoprene, (meth)acrylic acid, etc. Among these, unsaturated carboxylic acid, (methyl) The alkyl acrylate, the alkyl aryl (meth) acrylate, and the vinyl carboxylate are preferred. The content of the other monomer in the graft copolymer is preferably, for example, 5 to 70% by weight. There is a situation in which it is impossible to control the physical properties of the coating film. When it is too large There is a case where the ability as a dispersing agent cannot be sufficiently exerted. Preferred examples of the above graft copolymer are -82 - 200904907 (11) 3-(N,N-dimethylamino)propyl acrylamide/polyethylene Glycol mono(meth)acrylate/terminal methacryl oxime poly(methyl) acrylate copolymer, (12) 3-(N,N-dimethylamino)propyl acrylamide/poly Ethylene glycol mono(meth)acrylate/terminal methacryl oxime polystyrene copolymer, (13) 3-(anthracene, fluorenyl-dimethylamino)propyl acrylamide/polyethylene glycol (Meth) acrylate / methyl (meth) acrylate terminal methyl propyl methacrylate polystyrene copolymer, (14) 3-(anthracene, Ν-dimethylamino) propyl acrylamide / poly a copolymer of a diol-(meth) acrylate/terminal methacryl thiolated methyl (meth) acrylate and a copolymer of 2-hydroxyethyl methacrylate, (15) 3-(Ν, Ν- Copolymer of dimethylamino)propyl acrylamide/polyethylene glycol mono(meth)acrylate/terminal methacryl oxime methyl methacrylate copolymer with 2-hydroxyethyl methacrylate , (16) 3-( , Ν-dimethylamino) propyl acrylamide / polyethylene glycol mono (meth) acrylate / terminal methacryl thiolated methyl methacrylate copolymer with 2-hydroxyethyl methacrylate Copolymer, (17) 3-(Ν,Ν-dimethylamino)propyl acrylamide/polypropylene glycol mono(meth)acrylate/terminal methacryl oxime poly(methyl) acrylate Copolymer, (18) 3-(Ν,Ν-dimethylamino)propyl acrylamide/polyethylene glycol polypropylene glycol mono(meth)acrylate/terminal methacryl oxime poly(methyl) Methyl acrylate copolymer, (19) 3-(Ν,Ν-dimethylamino)propyl acrylamide/polyethylene glycol polybutane-83 - 200904907 Alcohol mono(meth)acrylate/terminal methyl Acryl thiolated poly(methyl) acrylate copolymer, (20) 3-(anthracene, fluorenyl-dimethylamino) propyl acrylamide / polypropylene glycol polybutylene glycol mono(meth) acrylate / A terminal methacryl oxime poly(methyl) acrylate copolymer or the like. Among them, (1 1), (1 4), and (18) are preferable, and the compound represented by the following (D 4) is more preferable. In the formula (D 4), Me represents a methyl group. Formula (D4)

a : b : c = 15 : 20 : 65 (mass ratio) The graft copolymer can be obtained by polymerizing a radical in a solvent, for example, to obtain a component which is a unit of each of the above-mentioned polymer units. In the radical polymerization, a radical polymerization initiator can be used, and a chain transfer agent (for example, 2 thiolethanol and dodecylmercaptan) can be further used. The pigment dispersing agent containing a graft copolymer can be referred to the description of JP-A-2001 - 3 1 8 8 5 . In order to further improve the uniform dispersibility and storage stability of the organic particles, the content of the graft copolymer is preferably from 0.1 to 1,000 parts by mass, more preferably from 1 to 500 parts by mass, based on 100 parts by mass of the pigment. 20 parts by mass is more preferred. When it is less than 〇. 1 part by mass, there is a case where the dispersion stability of the organic nanoparticle cannot be observed. Further, the graft copolymer may be used singly or in combination of plural kinds. -84 - 200904907 In the process of the present invention, the molecular weight of the polymer means the weight average molecular weight unless otherwise specified. Examples of the method for measuring the molecular weight of the polymer include a chromatography method, a viscosity method, a light scattering method, and a sedimentation rate method. In the present invention, unless otherwise notified, conversion to polyphenylbenzene by gel permeation chromatography is used. The weight average molecular weight of ethylene. Hereinafter, an anionic polymer compound will be described. In the agglutination described above, a high molecular compound having at least one nonionic group can be added. The polymer compound is preferably a polymer compound having a weight average molecular weight of 1,000 or more and not represented by the following formula (14). General formula (1 4) (+Z~GJ-)—Q—(-R) (wherein G system represents -COO-, -S03_, -0S03·, -p(〇)(〇H)CT, or -0P(0)(0H)CT, J represents a divalent linking group or a single bond, Q represents a (m + 1) valent linking group, R represents a polymer compound residue, and z represents an organic or inorganic group The cation, m + 1 means 3 to 6). In the general formula (14), G represents -COO., -S03., _〇S〇3-, -Ρ(0)(0Η)0·, or _〇p(〇)(〇H)〇_, It is considered that _S〇3-, -0S03-, and -p(o)(〇H)cr are more preferable. When there are plural G, G may be the same anion group or different. In the general formula (14), the J system represents a divalent linking group, and is a straight chain, a branching extension base, a stretching base, and - 〇-, -C(=0)-, -S〇2-, -C〇2-, or a combination of two or more of these groups, preferably a divalent group, and a moiety bonded to Q in the formula (14) is preferably a sulfur atom. In the case of a substituent, the substituent may, for example, be 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. Alkoxy group having a carbon number of 1 to 6 such as an amino group, a carboxyl group, a sulfonylamino group, an N-sulfonylamino group, an ethoxycarbonyl group, or the like having a carbon number of 1 to 6 and a methoxy group, a methoxy group or an ethoxy group. A halogen atom having a halogen atom such as chlorine or bromine, a methoxycarbonyl group, an ethoxycarbonyl group or a cyclohexyloxycarbonyl group, or a carbonate having 2 to 7 carbon atoms such as alkoxycarbonyl group, a cyano group or a third butyl carbonate. In the general formula (14), the organic cation represented by Z may, for example, be an imidazole iron salt, a pyridine gun salt, a thiazolium salt, an imidazoline salt, a thiazoline salt, or a quinazoline salt. . Examples of the inorganic cation include lithium ions, sodium ions, and potassium ions. The Z system is preferably an inorganic cation. In the above formula (14), Q represents a (m+1)-valent linking group. m+Ι is not 3~6. The (m+1)-valent linking group represented by Q above includes a group consisting of 1 to 1 carbon atoms, 10 to 10 nitrogen atoms, 0 to 50 oxygen atoms, and 200 hydrogen atoms. It is unsubstituted or may have more substituents. Q is preferably an organic linker. Preferred specific examples of the organic linking group [exemplary compounds (r_丨) to (r-1 7)] are as follows. However, in the present invention, it is not subject to such restrictions. -86 - 200904907 丨2〇, -οη^οη2-6-ο-ci [—0~G— (Bu I)

〇 o -CH3 Each 0-CH2, ^CH2-〇 Each CHr (gate) -ΟήΓ ^CH H3C - c

—CH^-CKj-NH-d-O-CI

!*0-〇-CH2 xCHr-0-4-N (r-3) IjfOO—NHCHrGHj— _ch2-ch2_ 0 (Γ-4) ^H2-CH2-^>HK>«CHa^CH2-〇-GH3 -CHaH:H2— Η30-〇ίΓ ^η2-ο-9-ο«〇η2-〇η2-

Xx (Γ-5) CHa-CHr

(r-6)

^ch2 八^CHz

<r- 8) 6 ό

~ch2-ch2-—CHj—CH2-C K-ii) :Ha .CHj-O-4-CHj-CHj- —CHz-^-O-CHi ^ΟΗζ-Ο-ό-ΟΗί-

SriT^CHr-Og-CHi-CHr- <r 1〇) -CHz^o^Hf^cHz-oe-cHr- -"OV-CHa-NI —〇V>CIVNH~^0~CI -ch2- Ch2-〇-6. -CHrCHirO- H2-CH2^ CHrCHz*

(Γ-Ι3) N^N o ο (Γ-12) H—^-0-03⁄4^^CHi-OO-NH-CH,- ^〇Fj^XH2-(in the above formula (14), m series An integer of 1 to 5 is preferred. m is preferably 2 to 5, more preferably 3 to 5. Further, 1 is an integer of 1 to 5. 1 is preferably 1 to 4, and more preferably 1 to 3. In the above formula (14), R represents a polymer compound residue (polymer skeleton), and can be selected from a usual polymer or the like according to the purpose and the like. The molecular skeleton refers to a polymer structure having a number average molecular weight of 1000 or more. Among the polymers, the polymer skeleton is selected from a polymer or copolymer derived from a vinyl monomer, an ester compound polymer, or an ether compound polymer. , a urethane-based compound polymer, a guanamine-based compound polymer, an epoxy-based compound polymer, a lanthanide-based polymer, and the like, or a modified product thereof (for example, a polyether/polyamine group) a copolymer of a formate copolymer, a polymer of a polyether/vinyl monomer (any of a random copolymer, a block copolymer, and a graft copolymer)] One of the less preferred ones is a group consisting of a vinyl monomer or a copolymer, an ester compound polymer, an ether compound polymer, a urethane compound polymer, and a modified or copolymer thereof. At least one is preferable, and a polymer or a copolymer of a vinyl monomer is particularly preferable. Further, the polymer is preferably soluble in an organic solvent, and when the affinity with an organic solvent is low, for example, when it is used as a pigment dispersant. There is a case where the affinity with the dispersion medium is poor, and it is not possible to ensure a sufficient adsorption layer for the dispersion stabilization. The polymer compound used in the production method of the present invention has a weight average molecular weight of 1,000 or more, and a weight average molecular weight of preferably 3,000 to 100,000. It is more preferably 5,000 to 80,000, and particularly preferably 7,000 to 60000. When the weight average molecular weight is within the above range, the effect of introducing a plurality of functional groups at the end of the polymer can be sufficiently exerted, and the adsorption of the solid surface can be exerted. Properties, gel particle formation properties, excellent interfacial activity, can achieve -88-200904907 good dispersibility and dispersion stability. Especially When the polymer compound having an anionic group is used as a pigment dispersant when the organic nano pigment particles are re-dispersed, it is possible to achieve good dispersibility and dispersion stability. The formula (14) is high. The molecular compound is not particularly limited and can be synthesized by the following method. A method of radically polymerizing a vinyl monomer by using a thiol compound having a plurality of functional groups (G in the above formula) as a chain transfer agent More specifically, it is preferred to use a compound of the following formula (15) as a chain transfer agent and carry out radical polymerization. Formula (15) (+z_G_JtrQ^SH), Formula (15) In the above, G, J, Q, Z and m+1 are synonymous with G, J, Q, Z and m+1 of the above formula (14), and the preferred ranges are also the same. The vinyl monomer is not particularly limited, and examples thereof include (meth) acrylates, crotonates, vinyl esters, maleic acid diesters, fumaric acid diesters, and itaconic acid. Esters, (meth)acrylamides, vinyl ethers, esters of vinyl alcohol, styrenes, and (meth)acrylonitrile are preferred. The following compounds are mentioned as such an example. Examples of the (meth) acrylate include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, and (meth) acrylate. N-butyl ester, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, n-hexyl (meth)acrylate, cyclohexyl-89 - 200904907 ester, (meth)acrylic acid Tributylcyclohexyl ester, 2-ethylhexyl (meth)acrylate, third octyl (meth)acrylate, dodecyl (meth)acrylate, octadecyl (meth)acrylate, ( Ethyl methoxyethyl methacrylate, phenyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, (meth) acrylate 2 - Ethoxyethyl ester, 2-(2-methoxyethoxy)ethyl (meth)acrylate, 3-phenoxy-2-hydroxypropyl (meth)acrylate, benzyl (meth)acrylate , diethylene glycol monomethyl ether (meth)acrylate, diethylene glycol monoethyl ether (meth)acrylate, triethylene glycol (meth)acrylate Monomethyl ether, triethylene glycol monoethyl ether (meth)acrylate, polyethylene glycol monomethyl ether (meth)acrylate, polyethylene glycol monoethyl ether (meth)acrylate, (methyl) Cold-phenoxyethoxyethyl acrylate, nonylphenoxypolyethylene (meth)acrylate, nonylphenoxypolyethylene (meth)acrylate, dicyclopentanyl (meth)acrylate Ester ester, dicyclopentenyloxyethyl (meth)acrylate, trifluoroethyl (meth)acrylate, octafluoropentyl (meth)acrylate, perfluorooctyl ethyl (meth)acrylate, ( Methyl)dicyclopentanyl acrylate, trifluorophenyl (meth)acrylate, and trifluorophenoxyethyl (meth)acrylate. The crotonate may, for example, be butyl crotonate or hexyl crotonate. Examples of the vinyl esters include vinyl acetate, vinyl propionate, vinyl butyrate, methoxyvinyl acetate, and vinyl benzoate. Examples of the maleic acid diester include dimethyl maleate, diethyl maleate, and dibutyl maleate. Examples of the fumaric acid diester include dimethyl fumarate, diethyl fumarate, and dibutyl methacrylate. Examples of the above-mentioned isonic acid diesters include dimethyl meconate, diethyl ketone, and dibutyric acid. The (meth) propyl-90 - 200904907 olefinic amines may, for example, be (meth) acrylamide, N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide, N-propyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N-n-butyl (meth) acrylamide, N-tert-butyl (meth) hydrazine Amine, N-cyclohexyl (meth) acrylamide, N-(2-methoxyethyl) (meth) acrylamide, hydrazine, hydrazine-dimethyl (meth) acrylamide, hydrazine, Ν-Diethyl(meth) propylene decylamine, fluorene-phenyl (meth) acrylamide, hydrazine-benzyl (meth) acrylamide, (meth) propylene sulfhydryl, diacetone propylene Amidoxime and the like. Examples of the styrenes include styrene, methyl styrene, dimethyl styrene, trimethylstyrene, ethyl styrene, isopropyl styrene, butyl styrene, hydroxystyrene, and methoxy. Styrene, butoxy styrene, ethoxylated styrene, chlorostyrene, dichlorostyrene, bromostyrene, chloromethylstyrene, a group which can be deprotected by using an acidic substance (for example, the third Boc et al. Protected hydroxystyrene, methyl benzoate, and α-methyl styrene. Examples of the vinyl ethers include methyl vinyl ether, butyl vinyl ether, hexyl vinyl ether, and methoxy ethyl vinyl ether. The polymerization may be carried out using only one type of the above-mentioned vinyl monomer, or two or more types may be used in combination, and such a radical polymer can be obtained by polymerizing each of the equivalent vinyl monomers by a usual method in accordance with a usual method. For example, a method in which a vinyl monomer and a chain transfer agent are dissolved in a suitable solvent, a radical polymerization initiator is added thereto, and polymerization is carried out in a solution at about 50 to 220 ° C (solution polymerization method) ) can get. An example of a suitable solvent which can be used in the solution polymerization method can be arbitrarily selected in accordance with the solubility of the monomer used in the use of -91-200904907 and the copolymer to be produced. For example, methanol, ethanol, propanol, isopropanol, 1-methoxy-2-propanol, 1-methoxy-2-propyl acetate, acetone, methyl ethyl ketone, methyl isobutylene can be mentioned. Ketone, methoxypropyl acetate, ethyl lactate, ethyl acetate, acetonitrile, tetrahydrofuran, dimethylformamide, chloroform, toluene, dimethyl sulfoxide (DMSO), N,N-dimethyl Indoleamine (DMF), dimethylacetamide (DMAc) and N-methyl-2-pyrrolidone (NMP). These solvents may be used in combination of two or more kinds. Further, the radical polymerization initiator can utilize a compound such as 2,2'-azobis(isobutyronitrile) (AIBN) or 2,2'-azobis-(2,4'-dimethylvaleronitrile) For example, peroxides derived from benzoic acid peroxide and potassium persulfate, ammonium persulfate persulfate, and the like. Specific examples of the polymer compound represented by the above formula (14) are shown below, but are not limited thereto. -92- 200904907

F-2

NaQ3S

F-3

-93- 200904907

O OMe F - 7 ol o

0^χ0Μβ 〇^〇·^^ΌΗ F-8

-94 - 200904907

[ 〇 Na03S seven q = people _ · 1, ΟΜβ s people. F-10

rV 0 0 Na03S, /"·^ 八儿\r V0^ A〇-^r^〇^A,

〇A

Na03S F-12 [Isolation] Hereinafter, a method of isolating organic nanoparticles which are agglomerated will be described. First, before the separation, the agglomerated liquid is allowed to stand for 5 to 2 hours. Since the aggregates settle, it can be separated by the decantation of the upper clear liquid or by suction, and the segregation of the aggregate becomes easier. Further, by centrifugation instead of standing, the sedimentation of the aggregate may be faster and the time can be shortened. The isolation can be carried out by various methods, and filtration can be carried out by ultrafiltration, centrifugal filtration, filter paper or a filter. -95 - 200904907 The method used for desalting/concentrating of, for example, a silver halide emulsion by ultrafiltration can be applied. Publication Disclosure No. 1 020 8 (1 972), Νο·1 3 1 22 (1 975) and No. 1 6 3 5 1 (1 977) are known to be published. The important pressure difference or flow rate of the operating conditions can be selected by referring to the characteristic curve described in the "Machine Utilization Technology Manual", "Study on the Use of Membrane" (1978), p. 27 5, to treat the target organic nanoparticle dispersion. The most suitable conditions for suppressing particle agglutination must be found. Further, in order to replenish the solvent lost by the membrane permeation, there are a constant volume type in which the solvent is continuously added and a fractional method in which the intermittent addition is intermittently added, since the desalting treatment time is relatively short, and the constant volume type is preferred. When the solvent is replenished in this manner, pure water obtained by ion exchange or distillation may be used, or a dispersant or a weak solvent of a dispersing agent may be mixed in pure water, or may be directly added to the organic nanoparticle dispersion. The filter can use a device such as pressure filtration. Preferred filters include, for example, filter paper, a nano filter, an ultrafilter, and the like. When the organic nanoparticle is concentrated, a centrifugal separator by centrifugation is used, and if the organic nanoparticle in the organic nanoparticle dispersion (or the organic nanoparticle concentrated extract) can be precipitated, any device can be used. . The centrifugal separator may be, for example, a material having a skimming function (a function of sucking an upper clear layer during rotation and discharging it outside the system), or a continuous centrifugal separator that continuously removes solid components, in addition to a general-purpose apparatus. Centrifugal force of centrifugal separation conditions (representing the centrifugal acceleration of several times the gravitational acceleration), preferably 5 0~1 0 0 〇' is better than 1 0 〇~8 0 0 ' is better than 150~6000 . The temperature at the time of centrifugation depends on the solvent type of the dispersion, preferably -1 〇 to 80 °C, preferably -5 to 70 °C, and 0-96 - 200904907 to 6 0 °C. Very good. The segregated aggregate can be washed for desalination, dehydration, and removal of the remaining dispersant. The washing operation can be directly added with the washing liquid after the ultrafiltration, centrifugation, filter paper or filter filtration, or can be temporarily washed out, and then re-slurry in the washing liquid, by super Filtration, centrifugation, filter paper or a filter can be used for isolation, and the combination can be washed. Further, the washing is carried out not only after the above-described segregation, but also before the segregation. This can be achieved by allowing the agglomerated nano pigment particle dispersion to stand still, removing the upper clear liquid, adding the washing, and re-stabilizing. After re-slurrying, the upper clear liquid can be removed by standing and filtered, or directly passed through the furnace. When washing is carried out before the separation, since the aggregate is often wetted, not only the cleaning efficiency is increased, but also the redispersion described later is easier. The washing liquid is not particularly limited as long as it can achieve desalination, dehydration, and removal of the remaining dispersant or coagulant. Specific examples thereof include an aqueous solvent (for example, water, hydrochloric acid, or aqueous sodium hydroxide), and an alcohol. Compound solvent, guanamine compound solvent, ketone compound solvent, ether compound solvent, aromatic compound solvent, carbon disulfide solvent, aliphatic compound solvent, nitrile compound solvent, hydrazine compound solvent, _ _ compound solvent, vinegar compound solvent, ionic liquid The mixed solvent or the like is preferably an aqueous solvent, an alcohol compound solvent, a ketone compound solvent, an ether compound solvent, a nitrile compound solvent, an anthraquinone compound solvent, an ester compound solvent, a guanamine compound solvent, or a mixture thereof. More preferably, it is an aqueous solvent, an alcohol compound solvent, a vinegar compound solvent, and a nitrile compound solvent. -97 - 200904907 The agglomerate after washing may be directly redispersed as described later, or may be redispersed using a redispersion solvent (described later), or may be dried to form a powder of the organic nanoparticle dispersion. After taking out, it was redispersed. The method of freeze-drying is not particularly limited, and any method that the manufacturer can utilize can be employed. For example, a direct refrigerant expansion method, a refrigerating method, a heat medium circulation method, a triple heat exchange method, an indirect heating freezing method, a direct refrigerant expansion method, and an indirect heating freezing method are preferable, and an indirect heating freezing method is preferably used. . Either method is performed after preliminary freezing and then freeze-drying is preferred. The conditions for preliminary freezing are not particularly limited, and all samples subjected to freeze-drying must be frozen. Examples of the indirect heating and freezing method include a small freeze dryer, an FT S freeze dryer, a LYO VAC freeze dryer, an experimental freeze dryer, a freeze dryer for research, a triple heat exchange vacuum freeze dryer, and a single cooling type. Freeze dryer, HULL freeze dryer, small freeze dryer, experimental freeze dryer, freeze dryer for research, single-cooling freeze dryer, preferably small freeze dryer, single-cooling freeze dryer Better. The freezing and drying temperature is not particularly limited, for example, -1 9 (TC~-4 t, preferably -120 ° C to -20 ° C, and - 80 ° C to -6 (TC is more preferable. Freeze-dried The pressure is not particularly limited, and the manufacturer can appropriately select, for example, 〇. ;! 〜 3 5Pa, preferably 1 to 15 Pa, more preferably 5 to 1 OPa. Freeze drying time is, for example, 2 to 4 8 hours, 6 to 3 6 hours is preferred, and 1 6 to 2 6 hours is preferred. However, the manufacturer can appropriately select such conditions. For the freeze drying method, for example, reference can be made to the preparation machine technical manual: preparation machinery technical research conference, The Local Library, pp. 120-129 (September 2000): Zhen-98 - 200904907 Empty Handbook: Japan Vacuum Technology Co., Ltd., OHM Corporation, pp. 328-331 (1992); Freeze and Dry Research Conference Journal: Ito Takara, No. 15, pp. 82 (1965), etc. The organic nanoparticle is concentrated by using a device that is dried under reduced pressure, if the organic nanoparticle dispersion can be used (or The solvent in the organic nanoparticle concentrated extract) is not particularly limited, and may be, for example, a pan. a vacuum dryer and a rotary pump, or a device capable of heating and decompressing while stirring a liquid, a device capable of continuously drying by passing a liquid through a pipe that has been heated and decompressed, etc. Heating the decompression temperature to 30 ~230 ° C is better 'to 35 ~ 200 ° C for better ' 40 ~ 180 ° C is particularly good. Pressure under reduced pressure is preferably 1 〇〇 ~ l 〇〇〇〇〇 Pa, to 300 ~ More preferably, 90000Pa is more preferably 500 to 80,000 Pa. [Re-dispersion] According to the production method of the present invention, the organic nano pigment particles in an aggregated state can be finely dispersed as necessary (in the present invention, the fine dispersion means that the dispersion is dispersed) The aggregation of the particles in the liquid increases the degree of dispersion. The organic nano pigment particles obtained by the agglomeration can be quickly filtered by a filter, and a good dispersion state can be obtained again to be re-dispersed. It is preferable that the floc is formed to a certain extent. Therefore, when the degree of dispersion by a usual dispersion method is used, the micronization is not sufficient, and it is necessary to use a method with higher refining efficiency. Finely dispersing the nanoparticle. Agglutination For the method of the body, for example, a method of ultrasonic dispersion or a method of applying physical energy can be used. The ultrasonic irradiation device to be used is preferably a function capable of applying an ultrasonic wave of 10 kHz or more to -99 - 200904907, and For example, a supersonic wave homogenizer, an ultra-washer, etc. In the ultrasonic irradiation device, when the liquid temperature rises, the rice particles are thermally aggregated (see Non-Patent Document 1), and the liquid temperature is preferably 1 ° C. 5 to 60 ° C is more preferable. The temperature control method can be carried out by controlling the temperature of the dispersion and controlling the temperature adjustment for controlling the temperature of the dispersion. The dispersing machine to which the physical energy is applied to use the concentrated organic nanoparticles is not particularly limited, and examples thereof include a kneader, a machine, a vertical ball mill, an ultra-mill, a dissolver, a high-speed stirrer, and the like. Dispersing machine. Further, a dispersion method using high pressure fraction or microparticle beads may also be suitably employed. The preferred method for preparing the organic nanoparticle dispersion composition is to use a tree to divide the colorant into a specific viscosity of 25 to 10,000 mPa·s or more, preferably 100,000 mPa·s or more after the kneading and dispersing treatment. The method is characterized in that the mixture is subjected to a kneading and dispersing treatment, followed by adding a solvent, and the micro-treated viscosity is 1, and the micro-dispersion treatment is carried out in a manner of a lower viscosity than 〇〇〇mPa.s or less, preferably 100 mPa·. The machinery used in the redispersion treatment is a twin roll, a three roll, a trummel mill, a disperser, a kneader, a kneading extrusion homogenizer, a blender, a single shaft or a double shaft. An extruder or the like is dispersed while applying strong shear. Next, a solvent is added, mainly using a vertical or horizontal sanding disc type mill, a slit type mill, an ultrasonic disperser, a high pressure machine, etc., by using a glass having a particle diameter of 0.1 to 1 mm, Zirconium or the like is subjected to microdispersion treatment. Moreover, it is also possible to use an acoustic wave of 0.1 mm or less, and the Na-100 is dispersed by a roller when the control layer is dispersed, and the fat is f to a higher dispersion s; machine, boring machine, shear force; machine, partial pressure bead micro -100- 200904907 Particle beads for precise dispersion treatment. Further, after dispersing the main pigment and the auxiliary pigment, the two dispersions may be mixed and further subjected to dispersion treatment, and the main pigment and the auxiliary pigment may be subjected to dispersion treatment. Moreover, as for the details of dispersion, T. C. P a 11 ο η "Paint Flow and pigment Dispersion" (1964, John Wiley and Sons publication), etc. Use this method. For the purpose of improving the dispersibility of the organic nano pigment particles, a usual pigment dispersant and a surfactant may be added to the organic nano pigment particle dispersion composition. There are many types of compounds which can be used as such a dispersing agent, and examples thereof include an indigo derivative (commercial product EFKA-6745 (manufactured by EFCA)), SOLUSPARS 5 00 0 (manufactured by ZENECA Co., Ltd.); Alkyl polymer KP3 4 1 (manufactured by Shin-Etsu Chemical Co., Ltd.), (meth)acrylic (co)polymer POLYFRO Νο.75, Νο.90, Νο·95 (Kyoeisha Oil Chemical Industry Co., Ltd.) Cationic surfactants such as company) and W001 (made by Yusho Co., Ltd.); polyoxyethylene lauryl ether, polyoxyethylene stearate, polyoxyethylene oleyl ether, polyoxyethylene octyl phenyl ether, Non-ionic surfactants such as polyoxyethylene nonylphenyl ether, polyethylene glycol dilauryl ester, polyethylene glycol distearate, sorbitan fatty acid ester; W004, W005, W017 Anionic surfactants; EFKA-46, EFKA-47, EFKA-47EA, EFKA polymer 100, EFKA-400, EFKA-401, EFKA-450 (manufactured by Morishita Sangyo Co., Ltd.), DISPARSEID 6 DISPARSEID 8, DISP ARSEID 1 5 > DISPARSEID 9 1 00 (manufactured by S ANNOPCO) 200904907 Polymer dispersion [1]; SOLUSPARS 3000, 5000, 9000, 12000, 13240, 13940, 17000, 24000, 26000, 28000 and other various SOSOLPARS dispersions! l (ZENECA Co., Ltd.); ADEKAPRURONIC L31, F38, L42, L44, L61, L64, F68, L72, P95, F77, P84, F87 'P94, L101, P103 > F108, L121, P-123 (made by Asahi Kasei Co., Ltd.) and ISONET 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-5-72943, or the compound of Synthesis Example 1 described in JP-A-2001-31885 is also suitable. . In the organic nanoparticle-dispersed composition, the redispersed organic nanoparticles (primary particles) can be finely dispersed, and it is preferred to have a particle diameter of 1 to 200 nm and 2 to 100 nm. More preferably, it is especially good for 5~50nm. Further, the Mv/Mn of the redispersed particles is preferably 1.0 to 2.0, more preferably 1.0 to 1.8, and particularly preferably 1.0 to 1.5. According to the production method of the present invention, for example, the pigment particles contained in the organic nano pigment particle-dispersed composition or the colored photosensitive resin composition described later can be used, although it is a fine particle diameter of a nanometer size (for example, 10 to 100 nm). It can also be concentrated and redispersed. Therefore, when used in a color filter, the optical density is high, the uniformity of the surface of the filter is excellent, the contrast is high, and the noise of the image can be reduced. In addition, by dispersing the organic nano pigment particles in the composition and the finely and uniformly finely dispersing the machine pigment pigment particles contained in the coloring photosensitive composition, it is possible to exhibit a high coloring concentration in the thickness of the film, for example, Thinner layers such as color filters. -102-200904907 In addition, the composition of the machine-negative pigment particle-dispersing composition and the coloring sensitivity is excellent in the production of, for example, a color filter by containing a pigment which exhibits a vivid color tone and a high coloring power. Image forming material #. In addition, the alkaline developing solution used for the exposure and development of the colored image can be used as an organic liquid nanoparticle dispersion composition or a colored photosensitive resin composition in an aqueous solution. The binder can also adapt to environmental requirements. Further, the solvent used in the organic nano pigment particle-dispersing composition and the coloring photosensitive resin composition (dispersion medium for the pigment) can be an organic solvent having a moderate drying property, and can be satisfied in terms of drying after application. Claim. [Coloring photosensitive resin composition] The colored photosensitive resin composition of the present invention contains (a) organic nano pigment particles, (b) a binder, (a polymerizable monomer or oligomer, and (d) photopolymerization Initiator or photopolymerization initiator system. Each component of the colored photosensitive resin composition will be described below. (a) Organic Nano Pigment Particles The method for producing organic nano pigment particles is described in detail above with respect to the colored photosensitive resin composition. The total solid content (in the present invention, the total solid content means a total of the components other than the organic solvent), and the content of the organic nano pigment particles is preferably 3 to 90% by mass, and 20 to 80% by mass. Preferably, it is more preferably 25 to 60% by mass. When the amount is too large, the viscosity of the dispersion increases, and there is a problem in manufacturing suitability. When the amount is too small, the coloring power may be insufficient. The particle diameter of the functional fine particles is 〇. 1 μm - 103 - 200904907. The particle diameter is particularly preferably 〇·0.8 μm or less. The lower limit of the particle diameter 値 is not particularly limited 'the system and the aforementioned organic nano pigment particles (primary particles) The lower limit of the particle size is the same. The usual pigment can be combined for coloring. The pigment can be used as described above. In the present invention, the organic nanoparticle is used as the non-aqueous dispersion of the organic nano pigment particles described above. (b) Adhesive Coloring The adhesive for the photosensitive resin composition is preferably a polymer compound having a weight average molecular weight of 1,000 or more as described above, and an adhesive for the total solid content of the colored photosensitive resin composition. The content is usually 15 to 50 mass%, preferably 20 to 45 mass%. When the amount is too large, the viscosity of the composition becomes too high, which may cause problems in manufacturing suitability. There is a problem in the formation of a coating film. (c) Monomer or oligomer The monomer or oligomer contained in the colored photosensitive resin composition of the present invention has two or more ethylenic unsaturated groups. It is preferable that the double bond can be subjected to addition polymerization by irradiation with light. Examples of such monomers and oligomers include at least one ethylenically unsaturated group capable of addition polymerization in a molecule, and boiling. The compound is at least 100 ° C under normal pressure, and examples thereof include dipentaerythritol hexa(meth) acrylate, polyethylene glycol mono (meth) acrylate, and polypropylene glycol mono(methyl). a monofunctional acrylate or monofunctional (meth) acrylate such as acrylate and phenoxyethyl (meth)acrylate; polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate , trimethylolethane triacrylate, trimethylolpropane tri(meth)acrylate, trimethylolpropane diacrylate, neopentyl glycol di(meth)acrylate, neopenta-104 - 200904907 Alcohol tetra (meth) acrylate, neopentyl alcohol tri (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, Diol (meth) acrylate, trimethylolpropane tris(propylene methoxy propyl) ether, tris(propylene methoxy propyl) trimeric isocyanate, tris(propylene decyloxyethyl) trimer Cyanate ester, tris(meth)acrylate, trimethylolpropane or glycerol Polyfunctional acrylates or polyfunctional methacrylates polyfunctional alcohols Jiatian after ethylene oxide or propylene oxide (meth) acrylate obtained by esterifying the like. Further, a compound which can be suitably used is a (meth) acrylate after adding ethylene oxide or propylene oxide to a polyfunctional alcohol as described in the general formulae (1) and (2) of JP-A-10-62986. Compounded into a compound. In addition, the urethane urethanes described in Japanese Patent Publication No. Sho 48-41708, Japanese Patent Publication No. SHO-50-6034, and JP-A-53-37-193, and JP-A-48-641 Polyester acrylates described in the publication No. 83-43, JP-A-49-43 119, and JP-A-52-30490; epoxy acrylates of reaction products of epoxy resins and (meth)acrylic acid Polyfunctional acrylate or methacrylate. Among these, trimethylolpropane (meth) acrylate, neopentyl alcohol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and dipentaerythritol five ( Methyl) acrylate is preferred. Moreover, the "polymerizable compound B" described in JP-A No. 1 1 - 1 3 3 600 is also preferable. These monomers or oligomers (monomer or oligomer preferably having a molecular weight of 200 to 1,000) may be used singly or in combination of two or more kinds, and the total solid content of the colored photosensitive resin composition is usually 5 ~50% by mass, -105-200904907 It is preferably 1 0 to 40% by mass. When the amount is too large, the control of development is difficult, and there is a problem of manufacturing suitability. When too little, the hardening force at the time of exposure is not enough. (d) Photopolymerization Initiator or Photopolymerization Initiator System The photopolymerization initiator or photopolymerization initiator system contained in the inkjet ink for color filters of the present invention (in the present invention, the photopolymerization initiator system refers to A combination of a plurality of compounds to exhibit a polymerization initiation function of a photopolymerization initiation function, and a polyglycol compound disclosed in the specification of U.S. Patent No. 2,367,660, and an affinity ether compound described in the specification of U.S. Patent No. 208,828 The α-hydrocarbon-substituted aromatic cryptic compound described in the specification of U.S. Patent No. 27225 1 2, the specification of U.S. Patent No. 3,046,127, and the polycyclic benzoquinone compound described in the specification of No. 29 5 1 7 8 The combination of a triaryl imidazole dimer and a p-amino ketone described in the specification of the Japanese Patent Publication No. 3 5 4 9 3 6 7 and a benzothiazole compound and a trihalide group described in Japanese Patent Publication No. 5 1 -48 5 16 The bis-half-mole compound, the trihalomethyl-tri-trap compound described in the specification of U.S. Patent No. 4,239,850, and the trihalomethyloxadiazole compound described in the specification of U.S. Patent No. 4,221,976. Among them, a trihalomethyl-s-three-till compound, a trihalomethyl oxadiazole compound and a triaryl imidazole dimer are preferred. In addition, the "polymerization initiator C" described in JP-A-11-133600 or the phenyl-based 1-phenyl-1,2-propanedione-2-(o-ethoxy group) Carbonyl) hydrazine, hydrazine-benzylidene-4'-(benzohydrothio)benzyl-hexyl ketone oxime, 2,4,6-trimethylphenylcarbonyl-diphenylphosphonium oxide, six A fluorophosphonate trialkylphenyl money salt or the like is also preferred. These photopolymerization initiators or photopolymerization initiator systems may be used alone or in combination of two or more of -1 06 - 200904907, and it is preferred to use two or more kinds in combination. When at least two kinds of photopolymerization initiators are used, "good display characteristics are exhibited, and display unevenness is particularly small. The content of the photopolymerization initiator or the photopolymerization initiator system is usually from 0 to 20% by mass, preferably from 1 to 15% by mass, based on the total solid content of the coloring photosensitive resin composition for a color filter. When the amount is too large, the sensitivity is too high and control becomes difficult. When too little, the exposure sensitivity is too low. It is preferable to use ultraviolet rays such as g-line or i-line for the radiation that can be used for exposure. The irradiation amount is preferably 5 to 1500 mJ/cm2, more preferably 10 to 1000 mJ/cm2, and most preferably 10 to 500 mJ/cm2. (Other additives) [Solvent] In the colored photosensitive resin composition for a color filter 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 esters are, for example, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate. , ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, methyl hydroxyacetate, ethyl hydroxyacetate, butyl glycolate, methyl methoxyacetate, methoxyacetic acid Ethyl 3-hydroxypropionate such as ethyl ester, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-hydroxypropionate or ethyl 3-hydroxypropionate: Methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-hydroxypropionate, 2- Ethyl hydroxypropionate, propyl hydroxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, 2-methoxypropionic acid propyl-107-200904907 ester, 2 - Methyl ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-hydroxy-2-methylpropionate, ethyl 2-hydroxy-2-methylpropionate, 2-methoxy- Methyl 2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate , methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetate, ethyl acetate, ethyl 2-oxopropionate, ethyl 2-oxopropionate, etc.; Examples are, for example, diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl stilbene acetate, ethyl serosu acetate, diethylene glycol Monomethyl ether, propylene glycol methyl ether acetate, etc.; ketones such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, cyclohexanol, 2-heptanone, 3-heptanone, etc.; The aromatic hydrocarbons are, for example, toluene, xylene, and the like. Among these, in the present invention, methyl 3-ethoxypropionate, ethyl ethoxypropionate, ethyl celecoxib acetate, ethyl lactate, butyl acetate, 3-methyl is used. As the solvent, methyl oxypropionate, 2-heptanone, cyclohexanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol methyl ether acetate or the like is preferred. These solvents may be used singly or in combination of two or more. Further, a solvent having a boiling point of from 180 ° C to 250 ° C may be used as necessary. These high boiling solvents are as follows. There are diethylene glycol monobutyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether, 3,5,5-trimethyl-2-cyclohexene-1-one, lactic acid Ester, dipropylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol diacetate 'propylene glycol n-propyl ether acetate, diethylene glycol diethyl ether, 2-ethylhexyl Acid ester, 3-methoxy-3-methylbutyl acetate, r-butyrolactone, tripropylene glycol methyl ethyl acetate, dipropylene glycol n-butyl acetate 'propylene glycol phenyl ether acetate Ester and 1,3-butanediol diacetate. -108- 200904907 The solvent content is preferably from 1 〇 to 9.5 mass% based on the total amount of the resin composition. [Surfactant] In the conventional color filter, in order to achieve high color purity, the color of each pixel becomes thick, and there is a problem that the film thickness unevenness of the pixel is directly recognized by the color unevenness. Therefore, it is required to improve the film thickness variation when the photosensitive resin is formed (coated) having a direct influence on the film thickness of the pixel. In the color filter of the present invention or the transfer material using the coloring photosensitive resin composition of the present invention, uniform coating thickness can be controlled, and coating unevenness can be effectively prevented (color unevenness due to film thickness variation) In view of the above, it is preferred that the coloring photosensitive resin composition contains a suitable surfactant. The surfactants disclosed in Japanese Laid-Open Patent Publication No. 2003-337424, No. Hei. The mass % or less is preferred. [Thermal polymerization inhibitor] The colored photosensitive resin composition of the present invention preferably contains a thermal polymerization inhibitor. Examples of the thermal polymerization inhibitor include hydroquinone, hydroquinone monomethyl ether, p-methoxyphenol, di-tert-butyl-p-cresol, gallic phenol, tert-butyl phenol, benzoquinone, and 4 , 4'-thiobis(3-methyl-6-tert-butylphenol), 2,2'-methylenebis(4-methyl-6-tert-butylphenol), 2-hydrogen sulfur Benzimidazole, thiophene, etc. The content of the thermal polymerization inhibitor is preferably 1% by mass or less based on the total amount of the resin composition. -109-200904907 [Auxiliary use of dyes and pigments] The coloring agent (pigment) is added to the colored photosensitive resin composition as necessary to the extent that the effects of the present invention are not impaired. When a pigment is used for the colorant, it is preferably a coloring photosensitive resin composition for a uniform color filter. Therefore, it is preferably 0.1 μm or less, and more preferably 0.08 μm or less. In particular, the pigments described in JP-A No. 2005-17716, the pigments described in JP-A-2005-361447, and the pigments described in JP-A-2005-361447, No. 2005-17521 The coloring agent described in [0080] to [0088]. The total amount of the coloring photosensitive resin composition for the color filter is preferably 5% by mass or less based on the content of the auxiliary dye or pigment. [Ultraviolet absorbing agent] The ultraviolet absorbing agent can be composed of the colored photosensitive resin of the present invention as necessary. In addition to the compound described in JP-A-5-72724, the ultraviolet absorber may be a salicylate type, a diphenylbenzotriazole type, a cyanoacrylate type, a nickel clamp type or a hindered phenol. Benzyl phenyl acrylate, 4-tert-butyl phenyl sulphate di-third 4'-hydroxybenzoic acid 2,4-di-tert-butyl phenyl ester, butyl phenyl phenyl acrylate, 2, 4 -dihydroxydiphenyl ketone, 2-hydroxy-4-methoxy ketone, 2-hydroxy-4-n-octyloxydiphenyl ketone, 2-(2'-hydroxy-5'-methyl; benzotriene Oxazole, 2-(2'-hydroxy-3'-t-butyl-5'-methylphenyl)-5. triazole, ethyl 2-cyano-3,3-diphenylacrylate, 2, 2'-hydroxy-4_diphenyl ketone, nickel diphenyldithiocarbamate, bismuth azelaic acid (in the present hair |, coloring dispersion in the particle size is used to open or special opening or special opening relative to The use of the product includes a ketone system, a system, etc., 3,5,4-triphenyldiphenylphenyl)-chlorophenylhydrazine-methoxy 2,2,6,6--110- 200904907 Tetramethyl-4-pyridine), 4-tert-butylphenyl sulphate, phenyl sulphate, 4-hydroxy-2,2,6,6-tetramethylpiperidine condensate, amber Bis(2,2,6,6-tetramethyl-4-piperidyl) acid, 2-[2·hydroxy-3,5-biguanide, α-dimethylbenzyl)phenyl]-2H- Benzotriazole, 7-{[4-chloro-6-(diethylamino)-5-trin-2-yl]amino}-3-phenylcoumarin, and the like. The total amount of the coloring photosensitive resin composition for the color filter is preferably 5% by mass or less based on the total amount of the ultraviolet absorber. In addition, the coloring photosensitive resin composition of the present invention may contain, in addition to the above-mentioned additives, "adhesive aid" described in JP-A No. 1 1 - 1 3 3 0 0 0 0 or other additives. [Coating film of the coloring photosensitive resin composition] The component of the coating film obtained by using the coloring photosensitive resin composition of the present invention is the same as that of the "coloring photosensitive resin composition" item. Further, the thickness of the coating film obtained by using the colored photosensitive resin composition of the present invention can be appropriately determined depending on the use thereof, preferably from 0.5 to 5.0 μm, more preferably from 1.0 to 3.0 μm. By using the coating film of the coloring photosensitive resin composition of the present invention, it is possible to produce a polymer film having the polymer film by polymerizing the monomer or oligomer to form a polymer film of the coloring photosensitive resin composition. The filter (the production of the color filter is described later). The polymerization of the polymerizable monomer or the polymerizable oligomer can be carried out by photo-irradiation using (d) a photopolymerization initiator or a photopolymerization initiator system. <Color filter and its preparation method> Next, the color filter of the present invention and a method for producing the same will be described. The color filter of the present invention is characterized in that it has a -111-200904907 colored pattern which is formed by using the photocurable composition (colored photosensitive resin composition) of the present invention on a support. Hereinafter, the color filter of the present invention will be described in detail by the production method thereof (the method for producing a color filter of the present invention). The method of producing a color filter of the present invention is characterized in that the photocurable composition of the present invention is applied to a substrate directly or through another layer to form a photosensitive film (hereinafter referred to as "photosensitive film formation". Step)): performing a pattern exposure (exposure through a mask) on the formed photosensitive film (hereinafter, referred to as "exposure step"); and a step of forming a colored pattern after exposing the photosensitive film (hereinafter , referred to as "development step"). Hereinafter, each step of the method of producing the color filter of the present invention will be described. (Photosensitive Film Forming Step) In the photosensitive film forming step, the photocurable composition of the present invention is applied (provided) directly or on a substrate having another layer to form a photosensitive film. Examples of the substrate that can be used in the present process include soda lime glass, Pyrex (registered trademark) glass, quartz glass, and the like which adhere to the transparent conductive film, or solid-state imaging. A photoelectric conversion element substrate used for a device or the like is, for example, a germanium substrate or a complementary metal oxide film semiconductor (CMOS). These substrates also have a black matrix to isolate each pixel. Further, on these substrates, an undercoat layer (other layer) may be provided as necessary to improve adhesion to the upper layer, prevent diffusion of substances, or planarize the surface of the substrate. The coating method of the curable composition of the present invention is applied to a substrate, and various coating methods such as slit coating, inkjet coating, spin coating, cast coating, roll coating, and the screen coating method can be applied. The coating thickness of the photocurable composition is preferably 〇 丨 1 1 1 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 The drying (prebaking) of the photosensitive film coated on the substrate can be carried out in a plate, an oven, or the like at 5 Torr to 14 Torr. (:, drying is performed for 1 to 3 seconds (exposure step). The exposure step is performed by exposing the photosensitive film formed in the step of forming the photosensitive film through a photomask having a predetermined mask pattern. In this step, "the photosensitive film of the coating film is exposed through the mask of the plan". Only the radiation used when the coating film partially irradiated with light is hard-exposed is used to use g-rays, i-rays, or the like. The violet color is particularly preferable, and the irradiation intensity is preferably 5 mJ to 1500 mJ/cm2, more preferably 1000 mJ/cm2, and most preferably 10 mJ to 500 mJ/cm2. The color filter of the present invention is used for a liquid crystal display device. Preferably, it is preferably 5 to 200 mJ/cm 2 , more preferably 10 to 150 mJ/cm 2 , and most preferably 10000 mJ/cm 2 . The color filter of the present invention is used for solid-state imaging, and is 30 to 1500 mJ/cm 2 in the above range. Preferably, it is preferably 1000 mJ/cm 2 and more preferably 80 to 500 mJ/cm 2 (development step). Then, by performing an exposure step, the light in the exposure step is not dissolved in the aqueous alkali solution. Therefore, only the photo-hardened part of the liquid imaging system can When the photocurable composition of the uncured portion is not dissolved and the hardened portion is not dissolved, any material can be used. Specifically, it is determined by heat, and the external line is 10 0 to say 10 to 50. Membrane, can be used -113- 200904907 enough to use a combination of various organic solvents or alkaline aqueous solution. The development temperature is usually 20 ° C ~ 3 ° ° C 'development time is 20 ~ 90 seconds. The aforementioned organic solvent The above-mentioned solvent which can be used when preparing the pigment dispersion composition or the photocurable composition of the present invention is mentioned. The alkaline aqueous solution can be, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate or sand. Sodium, sodium metasilicate, ammonia, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, choline, pyrrole, piperidine, 1,8-dioxbicyclo An organic basic compound such as [5, 4, 0]-7-undecene is diluted with pure water to have a concentration of 0.001 to 10% by mass, preferably 〇·0 1 to 1% by mass. An aqueous solution is used as a developing solution. Further, a developing solution composed of such an alkaline aqueous solution is used. Usually, it is washed with pure water after development. In the development step, the remaining imaging liquid is removed by washing and dried by heating (post-baking). After post-baking imaging The heat treatment is performed to complete the hardening, and is usually performed by a heat hardening treatment at 100 ° C to 240 ° C. When the substrate is a glass substrate or a tantalum substrate, it is preferably 2001 to 240 t: at the above temperature. For the coating film after development, a heating method such as a hot plate or a convection oven (hot air circulation dryer) or a high-frequency heating machine is used, and it is necessary to carry out the heat of the mouth. The photo is repeated according to the 1ει g g, and the weight is the same as the number of the formula (M batch phase of the color separation step or the image of the image needs to be continued and the continuous method according to the step, the light of the exposed parts, the article The above-mentioned steps are as follows when the film is formed into a film mil. The shape of the film is filtered into a color group, and the phase of the color is formed into a hard light. #0 The dry thickness of the film is usually from 0.3 to 5.0 μm, preferably from 0.5 to 3.5 μm, and most preferably from 1.5 to 2.5 μm. The substrate may be, for example, a non-alkali used for a liquid crystal display element or the like. Glass, soda lime glass, Pyrex (registered trademark) glass, Pyrex (registered trademark) glass, quartz glass, and those which adhere to a transparent conductive film, or a solid-state imaging device. The photoelectric conversion element substrate is, for example, a germanium substrate, a plastic substrate, etc. A black matrix is usually formed on the substrates to isolate the pixels. The surface of the plastic substrate has a gas barrier layer and/or a solvent resistant layer. Preferably. The invention Use of the curable composition The above is mainly applied to the use of the pixels of the color filter, but needless to say, it can be applied to the black matrix provided between the pixels of the color filter. The black matrix is used in addition to this. In the photocurable composition of the invention, a black coloring agent such as carbon black or titanium black is added as a coloring agent, and in the same manner as in the above-described method of producing a pixel, pattern exposure, alkaline development, and further, subsequent The baking promotes hardening of the film to form. [Examples] <Example 1> [Preparation of aqueous dispersion of organic nanoparticle pigment particles] 45 parts by mass of CI Pigment Red 254 and 90 parts by mass of polyvinylpyrrolidone (K-25, manufactured by Wako Pure Chemical Industries, Ltd.) were added. 95 3 parts by mass of dimethyl hydrazine (DMSO) and stirred. To the solution, a 28% by mass sodium methoxy sodium carbonate solution (30 parts by volume) was added to prepare a pigment solution A. On the other hand, 4,00 parts by mass of water of 200904907 was adjusted as the pigment-insoluble solvent b. The aforementioned pigment-insoluble solvent B was at 30. (: Using the GK-0222-10 type Ramando static stirrer (trade name) manufactured by Fujisawa Pharmaceutical Co., Ltd., while stirring at 5,000 rpm, the NP-KX-5 00 made by Nippon Precision Science Co., Ltd. was used for the pigment-insoluble solvent b. The large-capacity pulse-free pump (trade name) was injected into the pigment solution a at a flow rate of 1 〇〇ml/min for 4 minutes and 4 seconds to crystallize the organic pigment nanoparticles to obtain an aqueous organic nano-aqueous dispersion. LB_4〇〇 (trade name) manufactured by Horiba, Ltd. was used and evaluated according to the dynamic light scattering method. 'The particle size of the niobium was used as the average particle diameter as an index of dispersibility. 'Because the dynamic light scattering method was also observed. The particles agglomerated twice, so the evaluation of the primary particles was also carried out by a transmission electron microscope. [Aggregation] In 200 parts by mass of acetone, 45 parts by mass of acetic acid of the nonionic low molecular compound was dissolved, and 3 parts by mass of non- C-1 of the ionic polymer compound, and adding 300 parts by mass of the above aqueous dispersion of the organic nanoparticle, and stirring for 5 hours. The gel was allowed to stand for 5 hours and observed by an optical microscope. After the body, the aggregate was allowed to settle and the upper clarified liquid was removed by decantation. [Isolation, washing, and drying] The above aggregates were collected by filtration paper (manufactured by ADVANTEC Co., Ltd., Νο·2), and the measurement was measured. The time required for the filtration was carried out. The collected solid was washed with 300 parts by mass of water and 200 parts by volume of methanol, and the obtained solid was slurried in 100 parts by volume of acetonitrile for 0.5 hour. The mixture was allowed to stand for 0.5 hour, and the upper clear liquid was removed by decantation. The obtained solid of -116-200904907 was vacuum dried overnight at room temperature. [Re-dispersion] by adding 1 part by mass of the organic pigment solid 4 parts by mass of the following non-aqueous solvent, 1-methoxy-2-propyl acetate, and ultrasonic wave homogenizer US system 歹U (trade name) manufactured by Nippon Seimitsu Co., Ltd. for ultrasonic irradiation for 3 hours' The organic nanoparticle nonaqueous dispersion liquid (hereinafter also referred to as pigment dispersion composition A) which is a non-aqueous solvent as a dispersing agent.

Nonaqueous solvent (S parity test) The obtained dispersion composition was subjected to the following evaluation. The results are shown in Table 1. (1) The average particle diameter of the aqueous dispersion of the organic nanoparticles was evaluated by dynamic light scattering method using LB-500 (trade name) manufactured by Horiba, Ltd., and the organic particle diameter was determined as the average particle diameter. The average particle size of the aqueous dispersion of rice particles. (2) Diameter of aggregate The diameter of the aggregate was measured by observing the aggregate using an optical microscope and using a scale which was additionally observed as a reference. The diameter of the aggregate referred to herein is defined as the diameter from the length ' of the end portion of the end of the aggregate and the length is the longest -117-200904907. The agglutination system referred to herein is a secondary particle in which primary particles which are invisible to the body are aggregated and grown to become secondary particles. (3) Filtration time A cloth suction filter funnel (Nutsche) having a diameter of 9 cm and a filter paper (FILTER PAPER Νο. 2 (trade name) manufactured by ADVANTEC Co., Ltd.) were used, and each gram of the pigment was measured by vacuum filtration using an aspirator. (4) Measurement of viscosity For the obtained dispersion composition, the viscosity of the pigment dispersion composition immediately after dispersion was measured using a Ε-type viscosity meter, and the pigment after one week after dispersion (at room temperature) was measured. The viscosity of the composition was 7/2, and the degree of adhesion was evaluated. Here, the low viscosity means good dispersibility and dispersion stability. (5) Comparative evaluation of the obtained pigment dispersion composition A, each of which became a thickness The sample was prepared by coating on a substrate in a 2 micron manner. The backlight module was provided with a diffusing plate using a 3-wavelength cold-tube light source (FWL18EX-N manufactured by Toshiba Light & Technology Co., Ltd.) in two polarized plates. The sample (the polarizer HLC2-2518 manufactured by SUNRIC Co., Ltd.) was placed between the sample and the amount of transmitted light when the polarizing axis was flat and perpendicular, and the ratio was used as a comparison (refer to "the 7th time in 1990"). Color optics conference, 512 colors 10.4 inch color filter for TFT-LCD, Ueki, Komatsu, Fuyong, Yamanaka, etc.) The color is measured using a color brightness meter (BM-5 manufactured by TOPCON Co., Ltd.). The position of the plate, the sample, and the color brightness meter is set to a polarizing plate at a position of 13 mm from the backlight plate, and a cylinder having a diameter of 11 mm and a length of 20 mm is set at a position of 40 mm to 60 mm, and the pair is set at 65 - 118- 200904907 Measurement of the measurement position at the millimeter position. The transmitted light was measured by a color brightness meter set at a position of 100 mm through a polarizing plate set at a position of 100 mm. The measurement angle of the color luminance meter was set to 2 °. The light amount of the backlight plate is set such that the brightness of the two polarizing plates is set to 1 280 cd/m 2 when the polarizing plates are placed in a state where the sample is not provided. <Example 2> The non-embodiment of the first embodiment The ionic low molecular compound was changed to nonionic 2-propyl valeric acid, and the same operation as in Example 1 was carried out. The obtained organic nanoparticle nonaqueous dispersion was also referred to as pigment dispersion composition B. Pigment dispersion composition B is carried out The same evaluation test as in Example 1 was carried out, and the results are shown in Table 1. <Example 3> The nonionic low molecular compound of Example 1 was changed to nonionic C -10, and the same procedure as in Example 1 was carried out. The non-aqueous dispersion of the obtained organic nanoparticle particles was also referred to as a pigment dispersion composition C. The same evaluation test as in Example 1 was carried out on the pigment 9 dispersion composition C, and the results are shown in Table 1. Example 4> The polyvinylpyrrolidone of Example 1 was changed to a cationic polymer dispersant C-5, and the nonionic low molecular compound was changed to an anionic low molecular compound E-3, and an anionic polymer was added. The compound was changed to the anionic polymer compound F-2, and the same operation as in Example 1 was carried out. The obtained organic nanoparticle non-aqueous dispersion is also referred to as a pigment dispersion composition D. The pigment dispersion composition D was subjected to the same evaluation as in Example 1 200904907 The results of the test are shown in Table 1. &lt;Example 5&gt; In Example 1, except that the nonionic polymer compound was changed to a nonionic methacrylic acid/benzyl methacrylate copolymer, the non-aqueous polymer compound of the organic nanoparticle non-aqueous dispersion was subjected to The same operation as in the first embodiment. The obtained organic nanoparticle non-aqueous dispersion is also referred to as a pigment dispersion composition E. The pigment dispersion composition e was subjected to the same evaluation test as in Example 1. The results are shown in Table 1. &lt;Example 6&gt; In Example 1, except that acetic acid was added as a nonionic low molecular compound to the nonaqueous dispersion of the organic nanoparticles, the C-1 of the nonionic polymer compound was dissolved in acetone and added. The same operation as in Example 1 was carried out except for the organic dispersion of the organic nanoparticles. The obtained nonaqueous dispersion of the organic nanoparticles is also referred to as a pigment dispersion composition F. The pigment dispersion composition F was subjected to the same evaluation test as in Example 1. The results are shown in Table 1. &lt;Example 7&gt; In Example 1, except that the non-ionic polymer compound C _ 1 was dissolved in acetone in the non-aqueous dispersion of the organic nanoparticle, and added to the aqueous dispersion of the organic nanoparticle, the addition was carried out. The same operation as in Example 1 was carried out except that acetic acid was used as the nonionic low molecular compound. The non-aqueous dispersion of the obtained organic nanoparticles was also referred to as a pigment dispersion composition G°, and the pigment dispersion composition G was subjected to the same evaluation test as in Example 1. The results are shown in Table 1. -120-200904907 &lt;Example 8&gt; The aggregate obtained in Example 1 was allowed to settle&apos; and the upper clear liquid was removed by decantation, and then 200 parts by mass of water was added and reslurryed for 0.5 hour. The mixture was allowed to stand for 0.5 hours to precipitate the dispersion, and the upper clarified liquid was removed by decantation. Further, 1 part by mass of methanol was added thereto, and the mash was further slurried for 5 hours. The mixture was allowed to stand for 0.5 hours to allow the dispersion to settle, and the upper clarified liquid was removed by decantation. Further, 1 part by mass of acetonitrile was added, and the slurry was further slurried for 0.5 hour. The mixture was allowed to stand for 5 hours to allow the dispersion to settle, and the upper clear liquid was removed by decantation. Subsequently, the same operation as in Example 1 was carried out. The obtained organic nanoparticle non-aqueous dispersion is also referred to as a pigment dispersion composition Η. The pigment dispersion composition Η was subjected to the same evaluation test as in Example 1, and the results are shown in Table 1. &lt;Comparative Example 1&gt; In the aqueous dispersion of organic nanoparticles prepared by the same operation as in Example 1, 64 parts by mass of hydrochloric acid was added to aggregate the nanoparticles, and a filter (made by ADVANTEC) was used. Η010Α047Α, trade name) was subjected to filter filtration, and the time required for the measurement was measured. The solid obtained by filtration and dried (1 part by mass) in the same manner as in Example 1 was added 1 part by mass of methacrylic acid/benzyl methacrylate copolymer, and 8 parts by mass of acetic acid 1-methyl Oxy-2-propyl ester, and ultrasonic wave homogenizer US series (trade name) manufactured by Nippon Seimitsu Co., Ltd. for ultrasonic irradiation for 3 hours' to obtain non-aqueous organic nanoparticles with the following non-aqueous solvent as a dispersing agent Dispersions. The obtained organic nanoparticle non-aqueous dispersion is also referred to as pigment dispersion composition I. The pigment dispersion composition I was subjected to the same evaluation test as in Example 1-121-200904907, and the results are shown in Table 1. &lt;Test Example 1> In the same manner as in Examples 1 to 8 and Comparative Example 1, an aqueous dispersion of nanoparticle (300 parts by mass) was operated, and acetone of 45 parts by mass of acetic acid was added, and optical display was used. The filter was filtered using a filter (manufactured by ADVANTEC Co., Ltd.), and the evaluation results required for the measurement were as follows. &lt;Reference Example 1&gt; An acetone (200 parts by mass) was prepared in the same manner as in Example 1, and acetone of 200 masses of acid was added thereto, and the filter was observed using an optical microscope (H010A047A manufactured by ADVANTEC). The filter was filtered and the time required for the measurement was as follows. The evaluation results are as follows. The organic nanoparticle water J of the aggregate H010A047A and the commercial product was observed by adding 200 parts by mass of dissolved micromirrors. After dissolving 45 parts by mass of the ethylene aggregate, it is filtered using the product name. -122-200904907 [Table 1] Pigment Dispersion Composition Organic Nanoparticles Aqueous Dispersion Average Diameter Aggregate Diameter Filtration Time (Pigment Per 1 g) Viscosity (cP) Comparative Example 1 A 22 nm 50 μm or more 1 minute 35 16000 Example 2 B 22 nm 100 μm or more 0.5 minute 24 18000 Example 3 B 22 nm 50 μm or more 1 minute 30 17000 Example 4 D 25 nm 100 μm or more 0.5 min 74 14000 Example 5 E 22 nm 100 μm or more 0.5 minute 120 12000 Example 6 F 22 nm 50 μm or more 1 minute 40 15000 Example 7 G 22 nm 50 μm or more 1 minute 32 16500 Example 8 Η 22 nm 50 μm or more 3 minutes 30 17000 Comparative Example 1 I 22 nm 5 μm degree 10 hours 153 11000 Reference Example 1 • 22 nm 5 μm 8 hours or more, according to the present invention, when the organic nanoparticle aqueous dispersion phase is transferred to the organic nanoparticle non-aqueous dispersion, the step of temporarily preparing the aqueous paste represented by rinsing, that is, filter filtration, etc. It takes a very long time and a troublesome step, and the nanoparticle in the aqueous dispersion of the organic nanoparticle becomes an aggregate which can be easily filtered, and is isolated and redispersed in a non-aqueous solvent, thereby providing an efficient and effective A non-aqueous dispersion of the obtained organic nanoparticle and a preparation method thereof. Further, it is possible to provide a non-aqueous dispersion of organic nanoparticles which is excellent in dispersibility and has high contrast and a process for producing the same. [Preparation of coloring photosensitive resin composition] In the pigment dispersion compositions A to I obtained in Examples 1 to 8 and Comparative Example 1, a component having the following composition was further added and stirred and mixed to prepare the coloring sensitivity of the present invention. Resin composition (color photoresist). -123- 200904907 [Composition] • Dipentaerythritol hexaacrylic acid resin · · 80 parts by mass • 4-[o-bromo-p-N,N-bis(ethoxycarbonyl)aminophenyl-2 , 6_bis(trichloromethyl)-S-dioxin (photopolymerization initiator) · · .30 parts by volume • methacrylic acid vinegar / methacrylic acid (= 70/30 [mr ratio] Copolymer (weight average molecular weight: 10, 〇〇〇) of propylene glycol monomethyl ether acetate solution (solid content 40 ° / °) ... 200 parts by mass. 1-methoxy-2-propanol acetate 490 parts by mass, the obtained photocurable composition (color resist liquid) was applied to a glass substrate (173, manufactured by CORNING Co., Ltd.) of 100 mm χίοο mm so that the color density index X 値 was 0.650. And dry in an oven at 90 ° C for 60 seconds (pre-bake). Subsequently, the coating film was fully exposed using 200 mJ/cm 2 (illuminance: 20 mW/cm 2 ), and the coating film was covered with a 1% aqueous solution of an alkaline developing solution CD K-1 (Fuji Film ELECTRONICS MATE RI ALS). Full and still 60 seconds. After standing still, sprinkle pure water in a spray to wash the developing solution. Then, the coating film after exposure and development as described above was subjected to an oven heat treatment (post-baking) at 220 ° C for 1 hour to form a colored resin film for a color filter on a glass substrate to produce a colored filter. Substrate (color filter). When the R component of each of the obtained films was measured in the same manner as in Example 1, the results are shown in Table 2 below. -124- 200904907

Sample comparison

Coloring photosensitive resin composition A coloring photosensitive resin composition B coloring photosensitive resin composition C coloring photosensitive resin composition D coloring photosensitive resin composition E coloring photosensitive resin composition F coloring photosensitive resin composition G coloring Photosensitive resin composition 着色 Colored photosensitive resin composition I 15000 Example 1 17500 Example 2 16700 Example 3 13500 Example 4 11500 Example 5 14500 Example 6 16000 Example 7 16000 Example 8 10000 Comparative Example 1 The color filter produced by using the colored photosensitive resin composition obtained by using the organic nanoparticle non-aqueous dispersion organic particles obtained according to the present invention showed a very excellent contrast as compared with the comparative example. [Simple description of the diagram] 〇 j \ \\ [Component symbol description] Sister. /\\\ -125-

Claims (1)

200904907 X. Patent application scope: 1. A method for preparing an organic nano pigment particle aggregate, which is characterized in that at least one organic low molecular compound having a molecular weight of less than 1 000 and at least one organic high having a weight average molecular weight of 1000 or more The molecular compound acts on the organic nano pigment particles dispersed in the aqueous medium to cause aggregation, and then is isolated. 2. The method for producing an organic nano pigment particle agglomerate according to claim 1, wherein the organic low molecular compound and the organic high molecular compound are dissolved by using a solvent mixed with the aqueous medium, and added to the The organic medium pigment particles dispersed in the aqueous medium are agglomerated in the aqueous medium. 3. The method of producing an organic nanoparticle particle agglomerate according to claim 1 or 2, wherein the isolating is carried out using filtration. The method of producing an organic nanoparticle particle agglomerate according to any one of claims 1 to 3, which comprises the step of removing at least the remaining organic low molecular compound. The method for producing an organic nano pigment particle agglomerate according to any one of claims 1 to 4, wherein the organic nano pigment particles dispersed in the aqueous medium are mixed and dissolved in a good solvent to obtain an organic pigment. The solution is obtained by combining a solution having compatibility with the good solvent and a medium of the organic pigment as a weak solvent to form fine particles having a nanometer size. The method for producing an organic nano pigment particle agglomerate according to any one of claims 1 to 5, wherein the organic nano pigment particles have an average primary particle diameter of 100 nm or less. The method of producing an organic nano pigment particle agglomerate according to any one of claims 1 to 6, wherein the aggregate has an average particle diameter of 1,000,000 nm or more. 8. A method for producing a non-aqueous dispersion of organic nano pigment particles, characterized in that the organic nano pigment particles isolated as described in any one of claims 1 to 7 are aggregated in a non-aqueous medium. Redistributed to get. The method for producing a non-aqueous dispersion of an organic nano pigment particle according to any one of claims 1 to 8, wherein the organic polymer compound is represented by the following formula (11) or formula (14), In the formula (11) m, in the formula (A), A1 represents a group having a group selected from an acidic group, having a basic nitrogen atom, a ureido group, a urethane group, and a coordinating oxygen atom. a monovalent organic group having a hydrocarbon group of 4 or more carbon atoms, an alkoxyalkyl group, an epoxy group, an isocyanate group or a hydroxyl group, or an organic coloring material structure or a heterocyclic ring containing a substituent The valence organic group, η Α1 may be the same or different, R1 represents a (π1 + η) valence linkage, m + n represents 3 to 10' m represents an integer from 1 to 8, and η represents 2 〜 An integer of 9 , R 2 represents a single bond or a divalent linking group, and pi represents a polymer residue. Formula (1 4) m I -127- 200904907 ' (In the formula (14), G_ represents - COO-, _S03·, -〇S03', -P(0)(OH)〇-, or _〇p(〇)(〇H)〇-, J system represents a divalent linking group or a single bond, Q system A linking group of (m + 1) valence, R represents a polymer compound residue, and Z + represents an organic or inorganic cation 'm + l means 3 to 6) ° 1 0. As claimed in claim 9 Organic nano pigment particles non-aqueous A method of producing a bulk material in which the organic polymer compound is directly used as a dispersing agent in a non-aqueous medium. 1 1. A colored photosensitive resin composition characterized by containing a non-aqueous dispersion of an organic nano pigment particle, a binder, a monomer or an oligomer, and a photopolymerization initiator according to claim 9 or 10 of the patent application. Or at least one of photopolymerization initiators. I2. A color filter characterized in that it is formed using a colored photosensitive resin composition as in item n of the patent application. -128- 200904907 VII. Designated representative map: (1) The representative representative of the case is: None. (2) A brief description of the component symbols of this representative figure: None. 8. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: