TW201132711A - Pigment dispersion composition, colored photosensitive composition, color filter, method for producing color filter, liquid crystal display device and solid-state image sensor - Google Patents

Abstract

The invention provides a pigment dispersion composition, colored photosensitive composition using the same, color filter, method for producing color filter, liquid crystal device and solid-stage image sensor. The pigment dispersion composition contains (A) a pigment in which an average primary particle diameter is 10 to 30 nm, (B) a quinophthalone compound having at least one group selected from hydroxyl, carboxylic acid groups, sulfonate acid groups, amino group and a group of salt thereof, and (C) a solvent. The containing ratio of the (A) pigment and the (B) quinophthalone compound [(A): (B)] based on mass is in the range of (A):(B)= 85:15 to 10:90.

Description

[Technical Field] The present invention relates to a pigment dispersion composition, a coloring photosensitive composition containing the same, a color filter manufactured using the colored photosensitive composition, and the color filter a method for producing a sheet, a liquid crystal display device including the color filter, and a solid-state imaging device. [Prior Art] The color filter is produced by dispersing a pigment dispersion composition of an organic pigment or an inorganic pigment; The functional monomer, the photopolymerization initiator, the alkali-soluble resin, and other components are colored to form a photosensitive composition, and by using these, a colored pattern is formed by photolithography or the like. In recent years, color filters have been used in liquid crystal display devices (LCDs), and not only monitors, but also applications have expanded to televisions (TVs). With the tendency to expand in use, color filters are required to have high color characteristics in terms of chromaticity, brightness, contrast, and the like. Further, in a color filter used for an image sensor (solid-state imaging element), a substance having high color characteristics is similarly required. In response to the above-mentioned requirements, the pigment contained in the coloring photosensitive composition is dispersed in a finer state (good dispersibility). However, when the particle diameter of the pigment is made fine, the surface area of the pigment particles is increased, so that the cohesive force between the pigment particles is increased, and when the dispersibility of the pigment is insufficient, burrs are formed in the formed colored photoresist film. (fringe) (the jagged shape of the edge portion) or the surface unevenness may cause a problem that the color filter or the dimensional accuracy of the manufactured color filter is lowered and the contrast is remarkably deteriorated. It is more difficult to make the dispersion of 201132711 sex and contrast at a high level. In order to solve such problems, we have developed various pigment derivatives which promote dispersion stability. For example, it is proposed to use a quinophthalone compound to ensure the dispersibility of the pigment (see, for example, Patent Documents 1 and 2), and a fine pigment which can achieve a good contrast with respect to the pigment dispersion composition, and in the conditions described in Patent Document 1, There is a problem of insufficient 'dispersion'. Further, even in Patent Document 2, the fineness of the pigment is insufficient, and from the viewpoint of achieving a good contrast, the dispersion stability of the fine pigment is not sufficient. [PRIOR ART DOCUMENT] [Patent Document 1] Japanese Laid-Open Patent Publication No. JP-A-2002-179979 (Patent Document) [Problems to be Solved by the Invention] The subject of the present invention is a subject of the present invention. The object of the present invention is to provide a pigment-dispersed composition and a colored photosensitive composition containing the pigment-dispersed composition, wherein the fine pigment dispersion property and the contrast are both good and the brightness is improved. The pigment dispersion composition. Further, another object of the present invention is to provide a color filter which is a color filter having high color purity and high transmittance, and which is excellent in contrast and excellent in color characteristics by using the colored photosensitive composition of the present invention. In addition, the object of the present invention is to provide a liquid crystal display device using the color filter and having a bright image with high brightness and a solid-state imaging element excellent in color characteristics. [Means for Solving the Problem] As a result of the inventors' efforts, the present inventors first discovered that a pigment having an average primary particle diameter of 10 to 3 Onm and a quinophthalone compound having a specific substituent in the molecule are specified. The mass ratio is contained in the pigment dispersion composition in the solvent, and not only the contrast and the dispersibility are good, but further, in terms of effect, the pigment dispersion composition having improved brightness can be obtained by the excellent color characteristics of the quinophthalone compound. Thus, the present invention has been completed. That is, the means for solving the problem is as follows. &lt; 1 &gt; — A pigment dispersion composition characterized by containing (A) a pigment having an average primary particle diameter of 10 to 30 nm, and (B) having at least one selected from the group consisting of a hydroxyl group, a nicotinic acid group, a sulfonic acid group, and an amine group. And a quinophthalone compound of the salt group, and (C) a solvent of the (A) pigment and the (B) porphyrin compound in a mass-based ratio [(A): (B)] It is in the range of (Α):(Β) = 85··15 to 10··90. &lt;2&gt; The pigment dispersion composition of the item <1>, wherein the (Α) pigment and the (Β) quinoline yellow compound are based on a mass ratio ((Α): (Β)). Α): (Β) = range from 82:18 to 15:85. &lt;3&gt; The pigment dispersion composition of the item <1>, wherein the (Α) pigment and the (Β) quinoline yellow compound are based on a mass ratio ((Α): (Β)). Α): (Β) = range from 80:20 to 20:80. &lt;4&gt; The pigment dispersion composition of any one of <1> to <3>, wherein the 201132711 (A) pigment is selected from the group consisting of quinoline yellow pigments, isoporphyrin pigments, azo At least one of the group consisting of a metal complex, a metal phthalocyanine green pigment, a diketopyrrolopyrrole pigment, and an anthraquinone pigment. &lt;5&gt; The pigment dispersion composition of any one of <1> to <3>, wherein the (phantom pigment is selected from the group consisting of copper phthalocyanine pigment, zinc phthalocyanine pigment, azo nickel complex) A pigment-dispersed composition of any one of the above-mentioned items of the above-mentioned items, wherein the pigment is present in the pigment-dispersed composition of any one of the above-mentioned items. The pigment-dispersed composition according to any one of the above-mentioned items, wherein the (A) pigment is in an inorganic salt, a solvent, or the like. And a pigment dispersion composition according to the item <7>, wherein the pigment derivative is the (B) quinoline yellow compound. &lt;9&gt; The pigment dispersion composition according to any one of <1>, wherein the (B) quinophthalone compound is a compound represented by the following formula (1); R2 R1

(In the formula (1), each of X1 to X8 is independently a nitrogen atom, a chlorine 201132711 atom, or a bromine atom; ... to 114 each independently represent a hydrogen atom, -OCnH2n-Y, -S03CnH2n-Y , _S02NHCnH2n-Y, -C02CnH2n-Y, -NHCOCnH2n-Y, or -N(cnH2n-Y)2, not all of which are hydrogen atoms; η represents an integer from 0 to 20; Υ represents a hydrogen atom, -〇H, -S03H , -C02H, -C02-[NH4]+, -S〇3-[NH4]+, or -N(R5)2; R5 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. &lt;10&gt; - A color-sensitive photosensitive composition comprising (D) a polymerizable compound, (E) a photopolymerization initiator, and a pigment dispersion according to any one of items <1> to <9> Composition. &lt;11&gt; A method of producing a color filter, comprising: providing a coloring photosensitive composition such as the &lt;10&gt; item directly onto a substrate or forming a photosensitive film by directly or via another layer; a film forming step; a coloring pattern forming step of forming a colored pattern by sequentially performing pattern exposure and development on the formed photosensitive film. &lt;12&gt; A color filter comprising a colored pattern obtained by a method of producing a color filter of the item &lt;11&gt;. &lt;13&gt; A display device comprising a color filter of the item &lt;12&gt;. &lt;14&gt; A solid-state imaging element comprising a color filter of the item &lt;12&gt;. [Effect of the Invention] According to the present invention, there is provided a pigment-dispersed composition and a colored photosensitive composition containing the pigment-dispersed composition, wherein the pigment-dispersed composition is excellent in both contrast and dispersibility, and brightness can be improved. Further, by using the colored photosensitive composition of the present invention, it is possible to provide a color filter having a color pattern having high color purity and transmittance, good contrast, and high color characteristics, and using the color filter. A liquid crystal display device having a high-definition image and a solid-state imaging device having excellent color characteristics. [Embodiment] The preferred embodiment of the present invention is a pigment dispersion composition, a coloring photosensitive composition, and the like. The method of manufacturing the color filter and the color filter will be described in detail below. &lt;Pigment Dispersion Composition&gt; The pigment dispersion composition of the present invention contains: (A) a pigment having an average primary particle diameter of from 1 Torr to 3 Onm, and (B) having at least one selected from the group consisting of a hydroxyl group, a carboxylic acid group, and a sulfonic acid group. a quinophthalone compound having an amine group and a salt thereof, and (C) a solvent, and a content ratio of the (A) pigment to the (B) quinoline yellow compound [(A): (B)] is a mass The baseline is in the range of (A):(B) = 85:15 to 10:90. Hereinafter, each component constituting the pigment dispersion composition of the present invention will be described in detail. [(A) Pigment having an average primary particle diameter of from 1 Å to 30 nm] The coloring agent which can use the coloring composition of the present invention can be variously known from the prior art as long as the average primary particle diameter is from 1 nm to 3 Onm. Inorganic pigments and organic pigments are optionally selected for use. Representative pigments which can be used in the present invention are exemplified below. The red pigment which can be used in the present invention is exemplified by a general color filter -8 - 201132711. The use of: the red 1 pigment as a whole, specifically, for example, C. I. Pigment Red 1 ' • 2 ' 3, 4, 5 '6, 7, 9, 10, 1, 4, 17,: 22, 23, 31, 38, 41, 48:1, 4 8:2, 48:3, 48:4, 49, 4 9:1, 4 9:2 ' '52:1 , 52:2 , 5 3 : 1, 57 , :1 , 60:1 , 63:1 , 66 , 67 , 81 : 1, 8 1:2 , 8 1:3' 83 ' 8 18 ' 90 , 105 &gt; 11 2 , 1 1 9 , 122 , 123 , 144 , 146 , 149 , 150 &gt; 155 , 166 , 168 , 169 , 170 , 171 , 172 , 175 , 176 , 177 , 178 , 1 79 , 184 , 185 , 1 87 , 188 , 190 ' 200 , 202 ' 206 , 207 , 208 ' 209 , 210 '216 , 220 , 224 , 226 ' 242 , 246 ' 254 , 25 5 279, etc., but it is not particularly limited to these, and various red j pigments can be used. The yellow enamel pigment which can be used in the present invention can be exemplified by the yellow pigment used in the production of a usual color filter. Examples of such as C. I. Pigment Yellow 1, &gt; 2 ' 3 , 4 , 5 , 6 , 10 , 11 , 12 , 13 ' 14 ' 1 5 , 1 6 , 1 7 , 18 , 20 ' 24 , 3 1 , 3 2 , 34 , 35 ' 35:1' 36, 36:1, 37, 37:1, 40, '42, 43 , 53 &gt; 55, 60, 61, 62, 63, 65, 73 ' 74 , 77 , 81 , 83 , 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119' 120, 123, 125, 126, 127 , 128, 129 ' 137 ' 13 8 ' 139, 14 7 , 148, 150, 151, 152, 153 ' 154, 155, 156' 161, 162 &gt; 164 ' 166, 167, 168 ' 169, 170 ' 171 &gt 172, 173' 174, 175&gt; 176, 177 '179' 180, 18 1, 182, 185, 187, 188, 193, 194, 199, 2 13' 214, etc., but is not particularly limited to these, but may Use: Various yellow pigments 6 201132711 The green pigment which can be used in the present invention may, for example, be a whole of a green pigment used for the production of a usual color filter, and specifically, for example, CI Pigment Green 7, 10, 36, 37, 58, Japan Special 2 A halogenated zinc phthalocyanine pigment or the like described in Japanese Laid-Open Patent Publication No. 2004-70342, and the like, although not limited thereto, and various green pigments can be used. . Among the above pigments, it is preferably selected from the group consisting of quinoline yellow pigments, indoline pigments, and azo metal complexes in relation to the color characteristics of the (B) quinophthalone compound described later. Any one of the group consisting of a metal phthalocyanine green pigment, a diketopylpyrrolidium pigment, and an anthraquinone pigment may be used alone or in combination of two or more. The above quinoline yellow pigments include C·〗. Pigment Yellow 138; isoporphyrin pigments have 'CM• Pigment Yellow 139, 185; azo metal complexes have 'CI Pigment Yellow 150; Metal For phthalocyanine green pigments, there are CI pigment greens 7, 36, 58; diketopyrrolopyrrole pigments, ci pigment red 254, 255; bismuth pigments, CI. pigment red 177, etc. The 'very good' will be selected from halogenated copper phthalocyanine pigments (eg C.: [. Pigment Green 7, 36), zinc halide phthalocyanine pigments (eg CI Pigment Green 58), azo-type anthraquinone pigments The pigment of (for example, CI Pigment Yellow 150) and an isoindole pigment (for example, CI Pigment Yellow 139, 185) is used in combination with a porphyrin yellow compound having a specific functional group described later. In the case of the pigment used in the present invention, an average primary particle diameter of -10 - 201132711 l 〇 nm or more and 3 Onm or less is used. By using a pigment having an average primary particle diameter in the range, it is possible to obtain a coloring photosensitive composition for a color filter which is excellent in dispersibility stability or coloring power and has high brightness and high contrast. Further, in the present invention, the average primary particle diameter refers to the diameter of the longer one of the primary particles of the pigment constituting the aggregate on the two-dimensional image by the particles in the field of view of the transmission electron microscope. The mean 値 of the diameter (short diameter) of the shorter one is the average 値. The method for preparing a pigment having an average primary particle diameter of from 10 nm to 3 nm is not particularly limited, and may be a particle size-adjusted material in any of the above ranges, but can be easily suppressed. The crystal growth is carried out, and a relatively small pigment particle having a relatively small average primary particle diameter can be obtained. As a method of adjusting the pigment to the above average primary particle diameter, it is preferably treated by a solvent salt milling method (s, olvent salt milling). . The solvent salt milling treatment refers to a treatment in which a pigment, an inorganic salt, and an organic solvent are kneaded and ground. The pigment having a large particle size may be subjected to a solvent salt grinding method after dry grinding. In addition, in the case of the kneading and grinding of the pigment, it is preferable to coexist with the dye derivative in addition to the inorganic salt and the organic solvent in addition to the inorganic salt and the organic solvent. By coexisting with the coloring matter derivative, crystal growth during kneading and grinding can be suppressed, and a finer pigment can be obtained as compared with the case where the pigment derivative is not contained. Specifically, the pigment, the inorganic salt, the colorant derivative used in accordance with the desired enthalpy, and the organic solvent insoluble therein are placed in a kneader, and kneading and grinding are carried out therein. In the kneading machine at this time, for example, a pinch -11 - 201132711 machine or a mix-muller or the like can be used. In the above inorganic salt, a water-soluble inorganic salt can be suitably used, and an inorganic salt such as sodium chloride, potassium chloride or sodium sulfate is preferably used. Further, it is more preferable to use an inorganic salt having an average particle diameter of 0.5 to 50 μm. Such an inorganic salt can be easily obtained by finely pulverizing a usual inorganic salt. In the case of obtaining a pigment having an average primary particle diameter of from 10 nm to 30 nm, it is preferable that the ratio of the amount of the inorganic salt used to the amount of the pigment is higher in the solvent salt milling method. That is, the amount of the inorganic salt used is in terms of mass conversion, preferably 5 to 20 parts for 1 part of the pigment, and preferably 7 to 15 parts. In terms of the organic solvent, an organic solvent which can be obtained by suppressing the growth of crystals is preferably used. In the case of such an organic solvent, a water-soluble organic solvent such as diethylene glycol, glycerin, ethylene glycol, propylene glycol or liquid polyethylene glycol can be suitably used. , liquid polypropylene glycol, 2-(methoxymethoxy)ethanol, 2-butoxyethanol, 2-(isopentyloxy)ethanol, 2-(hexyloxy)ethanol, diethylene glycol monomethyl ether, Diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, Dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol, and the like. In this case, the amount of the water-soluble organic solvent to be used is not particularly limited, and it is preferably in the range of 0.01 to 5 parts by weight to 1 part by weight based on 1 part by mass of the pigment. The pigment derivative which is desired to coexist with the inorganic salt may be appropriately selected according to the type of the pigment to be kneaded and crushed, but may be exemplified by a porphyrin compound, a phthalocyanine compound, an anthraquinone compound or a quinacridone. -12 - 201132711 A derivative of a compound, a benzimidazolone compound or the like, which is preferably a derivative of a porphyrin yellow compound or a phthalocyanine compound, from the viewpoint of suppressing crystal growth and color tone. The amount of the pigment derivative to be used is not particularly limited, and it is preferably from 1 to 20 parts, preferably from 1 to 15 parts, per 100 parts by mass of the pigment. The temperature during the solvent salt milling method is preferably from 30 to 150 ° C, more preferably from 50 to 100 ° C. The solvent salt milling method is preferably 5 to 20 hours, more preferably 8 to 18 hours. In this case, a mixture containing a pigment, an inorganic salt, and an organic solvent as a main component may be obtained, but the organic solvent and the inorganic salt may be removed from the mixture, and the pigment may be washed and filtered by a solid substance as a main component as needed. By drying, pulverizing, etc., a powder of a pigment can be obtained, and the powder system is refined to have a specific average primary particle diameter. Any of washing with water and washing with warm water may be employed for washing after kneading and grinding. The number of washings can be repeated in the range of 1 to 5 times. In the case where the mixture of the water-soluble inorganic salt and the water-soluble organic solvent is used, the organic solvent and the inorganic salt can be easily removed by washing with water. In the above-mentioned drying after washing and washing, for example, heating and dehydration of the pigment and/or solvent removal may be carried out by heating at 80 to 120 ° C by a heating source provided in a dryer. Drying of the type or continuous type, etc., in the case of a dryer _ 'Generally there are box dryers, band dryers, spray dryers, and the like. -13 - 201132711 Further, the pulverization after drying is not an operation for increasing the specific surface area or reducing the average particle diameter of the primary particles, for example, when drying to a box dryer or a band dryer is used. In the case where the pigment is in the form of a lamp or the like, the pigment is decomposed and powdered, and examples thereof include a crucible, a hammer mill, a disk mill, a pin mill, and a jet honing. The crushing caused by the machine, etc. When the aspect ratio of the primary particles of the pigment of the present invention is further in the range of from 1 to 3, the viscosity characteristics are improved and the fluidity is higher in each application field. When the aspect ratio is required, as in the above, as in the case of obtaining the average particle diameter of the primary particles, the particles in the field of view are photographed by a transmission electron microscope or a scanning electron microscope. Next, for every 400 primary particles constituting the aggregate on the two-dimensional image, the average diameter of the longer diameter (long diameter) and the shorter diameter (short diameter) is obtained, and the enthalpy is calculated using the enthalpy . Further, in the case of using the pigment of the present invention, an average primary particle diameter of from 10 nm to 3 nm or less is required, but from the viewpoint of dispersion stability, it is more preferably an average primary particle diameter of l 〇 nm or more 2 8 nm or less, preferably l〇nm or more and 25 nm or less. The content of the pigment in the pigment dispersion composition of the present invention is selected according to the purpose, but generally, in the pigment dispersion composition, it is preferably from 5 to 30% by mass, from the viewpoint of obtaining a good contrast, to 8 More preferably in the range of up to 20% by mass. [(B) Quinoline yellow compound having at least one selected from the group consisting of a hydroxyl group, a carboxylic acid group, a sulfonic acid group, an amine group, and the like] ~ 14 - 201132711 The present invention is used The quinophthalone compound has at least one selected from the group consisting of a hydroxyl group, a carboxylic acid group, a sulfonic acid group, an amine group, and the like as a substituent in the molecule. These substituents may be directly bonded to the porphyrin yellow compound, and further, by the viewpoint of improved dispersibility, may be bonded via a linking group such as an alkyl group as needed. The quinophthalone compound having a specific substituent which can be used in the present invention can be obtained by, for example, the method described in paragraphs [〇〇15] to [0019] of JP-A-2003-167112. An example of the synthesis method of the quinophthalone compound used in the present invention is as follows: quinolin yellow pigment: 4,5,6,7-tetrachloro-2-[2-(4,5,6,7-tetrachloro- 2,3-Dihydro-1,3-di-oxy-1H-indol-2-yl)-8-quinolinyl]-1H-isoindole-1,3(21 €)-dione (丫 138) The sulfonation reaction is carried out by adding concentrated sulfuric acid, fuming sulfuric acid, chlorosulfonic acid, or a mixture thereof. The reaction solution is diluted with a large amount of water, or neutralized with a metal alkali aqueous solution or an aqueous amine solution, and the resulting suspension is filtered, washed with an aqueous washing solution, and dried. In the case where neutralization is not carried out, the obtained sulfonated derivative becomes an acid, and when it is neutralized, it becomes a salt. In the above-mentioned synthesis process, in the case of neutralization, it is preferred to use an aqueous amine solution as compared with the use of an aqueous alkali metal solution. In this case, when an alkali metal aqueous solution is used for neutralization, the alkali metal remains in the pixels of the color filter, which may cause a problem that adversely affects the electrical characteristics of the liquid crystal. In the case of the aqueous amine solution used for the neutralization, an aqueous solution of ammonia, -15 - 201132711 monoethanolamine or tetramethylammonium hydroxide (TMAH) can be used. However, the present invention is not particularly limited to these, and various aqueous amine solutions can be used. . Further specific examples of the appropriate quinophthalone compound of the present invention include a compound represented by the following formula (1):

(In the formula (1), X1 to X8 each independently represent a hydrogen atom, a chlorine atom or a bromine atom; and R1 to R4 each independently represent a hydrogen atom;

-OCnH2n-Y, -S〇3CnH2n-Y, -S〇2NHCnH2n-Y, -C〇2CnH2n_Y '-NHCOCnH2n-Y, or -N(CnH2n-Y)2; not all of them are hydrogen atoms; η means 0 to 20 An integer; Υ represents a hydrogen atom, -OH, -S03H, .-(:〇2ϋ, -C02_[NH4]+, -S〇r[NH4]+, or -N(R5)2; R5 represents a hydrogen atom or An alkyl group having 1 to 20 carbon atoms). Among the quinophthalone compounds represented by the formula (1), it is preferred that four or more of X1 to X8 are a chlorine atom or a bromine atom, and all of the X1 to X8 groups are chlorine atoms. From 1 to 3 of R1 to R4, it is preferred to introduce any of the above-mentioned substituents other than a hydrogen atom, and it is preferable to introduce one or two of them in the above position, particularly at the position of r2 or r3. The substituent Y to be introduced, the carboxylic acid group, the amine group and the like are preferably 'in the linking group to which the quinophthalone compound is bonded', and it is preferably 1 to 12 in terms of the number of carbon atoms n. An example of a suitable structure of a quinoline having a specific substituent which can be used in the present invention is as shown below, but the present invention is not a substitute for any one of the compounds of the sulfonic acid group and the substituent Y 1 to 6 These restrictions -17 201132711

-18 - 201132711

-19 - 201132711

H2n QeH12

One 20 — 201132711

-21 - 201132711

-22 - 201132711 The amount of the (B) quinophthalone compound to be added to the pigment dispersion composition of the present invention is required to be the ratio of the (A) pigment to the (B) porphyrin yellow compound [(A): (B) )], using the quality benchmark in the range of (a): (B) = 85:15 to 10:90. In other words, when the amount of the (B) porphyrin compound is too small, the pigment dispersion stabilization effect is not sufficiently exhibited with respect to the case where the (A) pigment is too small. On the other hand, when the amount of the quinoline yellow compound is too large, the pigment is caused. The polarity of the particle interface becomes too high, and there is a concern that the pigment dispersion stability is lowered. (A) Content ratio of the pigment to the (B) quinophthalone compound [(A): (B)] ' is preferably in the range of 82:18 to 15:85, and more preferably in the range of 80:20 to 20:80. 〇 [(C) Solvent] The pigment dispersion composition of the present invention further contains a solvent. As the solvent (C) which can be used in the present invention, the esters are, for example, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyrate butyrate Isopropyl ester, ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, methyl glycolate, ethyl hydroxyacetate butyl glycolate, methyl methoxyacetate, methoxy Ethyl 3-hydroxypropionate such as ethyl acetate, 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, Ethyl 2-hydroxypropionate, propyl 2-hydroxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, 2-ethoxy Methyl propionate, ethyl 2-ethoxypropionate, 2-oxo-2-methylpropane-23 - 201132711 methyl ester, ethyl 2-oxo-2-methylpropionate, 2-methoxy Methyl 2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, methyl pyruvate, ethyl pyruvate, propionate , ethyl acetate methyl acetate, ethyl acetate ethyl acetate, methyl 2-butoxybutyl acid, ethyl 2-oxobutanoate, etc.; ethers such as diethylene glycol dimethyl ether, tetrahydrofuran, Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl sarbuta acetate, ethyl sirolimus acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol Monobutyl ether, propylene glycol methyl ether acetate, propylene glycol diethyl ether acetate, propylene glycol propyl ether acetate, etc.; ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone, etc.; aromatic hydrocarbons There are, for example, toluene, xylene, and the like. Among these, 'methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl celecoxib acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, Methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol methyl ether acetate, and the like are preferred. The solvent may be used alone or in combination of two or more. The content of the solvent (C) in the pigment dispersion composition can be appropriately selected depending on the use of the pigment dispersion composition and the like. When the pigment dispersion composition is used in the coloring photosensitive composition to be described later, it may contain a solid content concentration of 5 to 50% by mass from the viewpoint of handleability, and the solid component contains: (A) a pigment, ( B) a quinophthalone compound, and a pigment dispersant used in combination as desired. [Other Ingredients] -24 - 201132711 In addition to the components (A) to (C), the pigment dispersion composition of the present invention can be used with various additive dispersants without impairing the effects of the present invention. The pigment dispersant which can be used in the pigment dispersion composition of the present invention is introduced into the sheet by the polymerization or copolymerization of the monomers represented by the following formula (i) '(ii) or (1)-2 The polymer compound of the repeating unit of the body is preferably R1 R3 r4r6

C=C ( i ) -2 r2I 0=&lt;r / 0-La-Lb-y〇-CmH2_9l.〇_A. \ 〇/〇 The above formula (i), formula (ii), and In formula (i)-2, R1 to R6 are each

The table is not an integer from 1 to i〇0. Such a compound is described in detail in the paragraphs [0021] to [0089] of JP-A-2009-256572, and the compounds described herein can be suitably used as a pigment dispersant in the present invention. As the pigment dispersant, in addition to the above compounds, for example, a well-known pigment dispersant or a surfactant can be suitably used. Specifically, 'a wide variety of compounds can be used, such as organic oxime polymer KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), (meth)acrylic (co)polymer Polyflow No. 75, Νο.90' Νο. 95 (Congrong Chemical Industry Co., Ltd.), W001 (Yushang Co., Ltd.) and other cationic surfactants; polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene ether ether, poly Nonionic surfactant such as oxyethylene octyl phenyl ether, polyoxyethylene decyl phenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid ester; W004 Anionic surfactants such as W005, W017 (Yushang); EFKA-46, EFKA-47, EFKA-47EA, EFKA polymer 100, EFKA polymer 400, EFKA polymer 401, EFKA polymer 450 (both BASF 曰 our company), Disperse Ayd6, Disper Ayd8, DisperAydl5, DisperAyd9100 (all manufactured by Sannopco) polymer dispersant; Solsperse 3000, 5000, 9000, 12000, 13240, 1 3940, 1 7000, 24000, 26000, 28000 and other Sο 1 sperse dispersants ( This Lubrizol (share) system; Adeca Pluronic L3 1, F38, L42, L44, L61 * L64, F68, L72, P95, F77, P84, F87, P94 &gt; LI 01, P103 &gt; F108, L121, P- 123 (Asahi Electronics Co., Ltd.) and Isonet S-20 (manufactured by Sanyo Chemical Co., Ltd.), Disperbykl 01, 103, 106, 108, 109, 111, 112, 116, 130, 140, 1 42 - 162, 1 63 _ 26 - 201132711, 164, 166, 167, 170, 171, 174, 176, 180, 182, 2000, 2001' 2050, 2150 (made by Byk). Other examples include an oligomer or a polymer having a polar group at a molecular terminal or a side chain such as an acrylic copolymer. In the case of preparing a pigment dispersion composition, in the case of using a pigment dispersant, it is preferable to add 1 to 100 parts by mass of the pigment dispersant with respect to (A) pigment 1 part by weight, and to add 3 It is better to 70. Further, the pigment dispersion composition of the present invention may be optionally added with (B) a quinophthalone compound having at least one selected from the group consisting of a hydroxyl group, a carboxylic acid group, a sulfonic acid group, an amine group and the salts, as required. Pigment derivatives. The pigment derivative is a compound in which a partial structure or a polar group having a dispersing agent and an affinity is introduced into the pigment as described above, by which the dispersing agent possessed by the compound and a partial structure having affinity, or introduced When a polar-based dye derivative is adsorbed on the surface of the pigment and used as a point of adsorption of the dispersing agent, the pigment can be dispersed as fine particles and dispersed in the pigment-dispersed composition, thereby preventing re-agglomeration of the pigment. It is extremely effective in contrasting color filters with high transparency. In terms of the content of the pigment dispersion composition of the pigment derivative, the mass conversion is preferably from 1 to 30 parts, more preferably from 3 to 20 parts, relative to 10 parts by mass of the pigment. When the content is within this range, good dispersion can be achieved while suppressing the viscosity to be low, and dispersion stability after dispersion can be improved, and excellent color characteristics with high transmittance can be obtained, and the color hardening of the present invention can be adjusted by using the above. When a color filter is produced, a color filter having high contrast -27 - 201132711 and good color characteristics can be obtained. - Modulation of Pigment Dispersion Composition - The modulation form of the pigment dispersion composition of the present invention is not particularly limited, but for example, a vertical or horizontal sand honing machine, a pin mill, a slit honing machine, and ultrasonic dispersion are used. The pigment, the pigment dispersant, and the solvent are obtained by microdispersion treatment of beads made of glass having a particle diameter of 0.01 to 1 mm, an oxidation pin, or the like. Before the bead dispersion, two rolls, three rolls, a ball mill, a trommel, a disper, a kneader, a co-kneader, a homogenizer, a blender, a single shaft or a two-axis are used. An extruder or the like can perform a kneading dispersion treatment while imparting a strong shearing force. In addition, the details of the kneading and dispersion are described in "Paint Flow and Pigment Dispersion" by T.C. Patton (published by John Wile and Sons, 1964). Since the pigment dispersion composition of the present invention has good pigment dispersibility and contrast, it can be used for various purposes necessary for coloring, but a colored photosensitive composition used for the production of a color filter can be suitably used. &lt;Coloring photosensitive composition&gt; The colored photosensitive composition of the present invention comprises: the pigment dispersion composition of the present invention as described above, (D) a polymerizable compound, (E) a photopolymerization initiator, and, as desired The alkali-soluble resin may contain other components as needed. Hereinafter, each component contained in the colored photosensitive composition of the present invention will be described in detail. -28 - 201132711 [Pigment Dispersion Composition] The colored photosensitive composition of the present invention is constituted by using at least one of the pigment dispersion compositions of the present invention. The pigment dispersion composition of the present invention constituting the colored photosensitive composition is as described above. In the content of the pigment dispersion composition in the colored photosensitive composition of the present invention, the content of the pigment is preferably in the range of 5 to 70% by mass based on the total solid content (mass) of the coloring photosensitive composition. It is more preferably in the range of 15 to 60% by mass. When the content of the pigment dispersion composition is within this range, it is used to ensure sufficient color density and excellent color characteristics. Further, in the colored photosensitive composition of the present invention, (B) a total of quinoline yellow compounds having a specific substituent as a function of the pigment (A) and the coloring agent contained in the pigment dispersion composition of the present invention The content of the amount is preferably from 5% by mass to 60% by mass, more preferably from 10% by mass to 55% by mass, most preferably from 15% by mass to 50% by mass based on the total amount of the solvent removed from the coloring photosensitive composition. By using the added amount within this range, a color filter excellent in color characteristics, high in contrast, and high in brightness can be obtained. [(D) Polymerizable Compound] The colored photosensitive composition of the present invention contains at least one of a polymerizable compound. The polymerizable compound which can be used in the present invention is an addition polymerizable compound having at least one ethylenically unsaturated double bond, and is selected from compounds having at least one 'preferably having two or more terminal ethylenically unsaturated bonds. . Such a compound group is widely known in the industrial field, and the present invention can be used without particular limitation. These have chemical forms such as monomers, prepolymers -29 - 201132711, i.e., dimers, trimers, and oligomers, or mixtures thereof, and such copolymers. In the case of the monomer and the copolymer thereof, an unsaturated carboxylic acid (for example, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.), or an ester thereof, may be mentioned. The guanamines are preferably esters of an unsaturated carboxylic acid with an aliphatic polyvalent alcohol compound, amides of an unsaturated carboxylic acid and an aliphatic polyvalent amine compound. Further, an unsaturated carboxylic acid ester having a nucleophile substituent such as a hydroxyl group, an amine group or a thiol group, or a guanamine and a monofunctional or polyfunctional isocyanate or epoxy may be suitably used. A reactant, a dehydration condensation reaction with a monofunctional or polyfunctional carboxylic acid, and the like. Further, in order to promote development, a compound having an organic acid group such as an alkylated oxy group or a carboxylic acid group in the structure may be suitably used. Further, an isocyanate group or an addition reaction product of an unsaturated carboxylic acid ester or an oxime amine having an electrophilic substituent such as an epoxy group with a monofunctional or polyfunctional alcohol, an amine or a thiol, A substituted carboxylic acid ester or a decylamine having a detachable substituent such as a halogen group or a tosyloxy group, and a substituted reactant of a monofunctional or polyfunctional alcohol, an amine or a thiol are also suitable. Further, in other examples, a compound group substituted with an unsaturated phosphonic acid, styrene, vinyl ether or the like may be used instead of the above unsaturated carboxylic acid. In the specific examples of the monomer of the ester of the aliphatic polyvalent alcohol compound and the unsaturated carboxylic acid, in the case of the acrylate, there are ethylene glycol diacrylate, triethylene glycol diacrylate, and 1,3-diacrylate. Butylene glycol ester, butylene glycol diacrylate, propylene glycol diacrylate, neopentyl glycol diacrylate, trimethylolpropyl triacrylate, trimethylolpropane tris(propylene methoxypropyl) - 30 - 201132711 Ether, trimethylolethyl triacrylate, hexanediol diacrylate I, 4-cyclohexanediol ester, tetraethylene glycol diacrylate, dipentaerythritol ester, neopentyl triacrylate Tetraol ester, dipentaerythritol neopentyl diaryl acrylate, sorbitol diamyl pentoxide, sorbitol tetraacrylate, pentaacrylate, sorbitol hexaacrylate, three (Propylene methoxyethyl) acid ester 'polyester acrylate oligomer, isotrihydrohydro acid EO modified ester, and the like. In terms of methacrylate, there are dimethacrylic acid extension, triethylene glycol dimethacrylate, trimethylol propyl trimethyl methacrylate, tris, trimethyl methacrylate, Ethylene glycol methacrylate, 13-butyl dimethacrylate dimethacrylate, neopentyl glycol dimethylene glycol methacrylate, neopentyl glycol tetramethacrylate Dipentaerythritol ester, sorbitan dimivalyl hexamethacrylate, sorbitol tetramethacrylate (oxy-2-hydroxypropoxy) 3-yl methacrylate Methyl methane (oxyethoxy methacrylate) phenyl] dimethyl methane or the like. In terms of itaconate, there are diammonium ethylene glycolate, diglycol ester, 1,3-butylene glycol diconazole, and 1,4-7 diisoconic acid dicone acid Glycol ester, neopentaerythritol diammonate, tetrasorbitol ester, and the like. In terms of crotonate, there are dibutyl phthalate, butyl crotonate, neopentyl glycol dibutyrate, dibar, dipropylene acrylate, neotriol, tripropylene sorbitol, iso-cyanide Butylene glycol triacrylate, methyl ethyl glycol ester, ester, trimethyl, dimethyl ester, trimethyl, bis [p-, bis-[-------------- Alcohol ester, sorbic acid di sorbate - 31 - 201132711 Sugar alcohol ester and the like. Examples of the isocrotonate include ethylene glycol diisocrotonate, neopentyl glycol diisocrotonate, and sorbitol diisocrotonate. In terms of the maleic acid ester, there are ethylene glycol malate, triethylene glycol dimalate, neopentyl glycol dimalate, sorbitan tetramalate, and the like. The structure of the above-mentioned polymerizable compound is used singly or in combination with the method of using the amount of addition, and can be arbitrarily set in accordance with the performance design of the final coloring photosensitive composition. For example, it may be selected from the following points. From the viewpoint of sensitivity, it is preferred that the structure has a large content of unsaturated groups per molecule, and in many cases, it is preferably two or more. Further, in order to increase the strength of the cured film, it is preferable to use a trifunctional or higher functional group, and further, different functional groups and different polymerizable groups (for example, acrylate, methacrylate, styrene compound, vinyl ether) are used. The method of adjusting the sensitivity and the intensity is also effective. In addition, the other components in the coloring photosensitive composition, for example, a miscibility with a binder polymer such as an alkali-soluble resin, a photopolymerization initiator, or the like, and a polymerizable compound are selected depending on the dispersibility of the pigment. It is an important factor, for example, the use of a low-purity compound or the use of two or more kinds of compounds can improve the mutual solubility. Further, in order to improve adhesion to a substrate or the like, a specific structure can be selected. The (D) polymerizable compound is preferably used in an amount of from 5 to 70% by mass, more preferably from 10 to 60% by mass, based on the nonvolatile component in the coloring photosensitive composition. Further, these may be used alone or in combination of two or more. In addition to -32 - 201132711, the method of using a polymerizable compound can be arbitrarily selected from the viewpoints of the size, resolution, finging property, refractive index change, and surface tackiness of the polymerization inhibition of oxygen. Appropriate Structure, Formulation, and Addition Amount [(E) Photopolymerization Initiator] The photosensitive resin composition of the present invention contains (E) a photopolymerization initiator. The (E) photopolymerization initiator may, for example, be an organohalogenated compound, an oxadiazole compound, a carbonyl compound, a ketal compound, a benzoin compound, an acridine compound, an organic peroxidic compound, an azo compound, or the like. A coumarin compound, an azido compound, a metallocene compound, a hexaarylbiimidazole compound, an organoboronic acid compound, a disulfonic acid compound, an oxime ester compound, a key salt compound, a mercaptophosphine (oxide) compound. In the case of the organic phosgenation compound, for example, "Bull Chem. Soc Japan" 42, 2924 (1969), US Patent No. 3,905,815, Japanese Patent Publication No. 46-4605, and Japanese Patent Laid-Open Japanese Patent Publication No. 48-3 62 8 1 , Japanese Patent Laid-Open No. 5 5 -3 20 7 0, Japanese Patent Laid-Open No. 60-2 3 97 3 6 , and Japanese Special Open 6 1 - 1 69 8 3 5 Japanese Gazette No. 6 1 - 1 6 9 8 3 7 , Japanese Unexamined Japanese Patent Publication No. 6 2 - 5 8 2 4 1 , Japanese Laid-Open Patent Publication No. 62-212401, and Japanese Patent Laid-Open No. 63- A compound described in, for example, Japanese Patent Publication No. Sho. No. Sho. No. Sho. No. Sho. No. Sho. No. Sho. No. Sho. Carbazole compound, s-three-pill compound-33 * 201132711. In the case of the S-tripper compound, it is preferred that at least one of the mono-, di- or tri-halogen-substituted methyl group is an S-tri-trap derivative bonded to the S-triple ring, and specifically, for example, 2, 4,6-gin (monochloromethyl)-s-three tillage, 2,4,6-gin (dichloromethyl)-s-three tillage, 2,4,6-gin (trichloromethyl)- S-tripper, 2-methyl-4,6-bis(trichloromethyl)-3-trimole, 2-n-propyl-4,6-bis(trichloromethyl)-3-trin, 2-(〇1,〇1,戸-trichloroethyl)_4,6-bis(trichloromethyl)-s-tripper, 2-phenyl-4,6-bis(trichloromethyl)- S-triterpene, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-trimole, 2-(3,4-epoxyphenyl)-4,6- Bis(trichloromethyl)-s-tripper, 2-(p-chlorophenyl)-4,6-bis(trichloromethyl)-s-tripper, 2-[1-(p-methoxybenzene) -2,4-butadiene]-4,6-bis(trichloromethyl)-s-three-plow, 2-styrene-4,6-bis(trichloromethyl)-s-triad , 2-(p-methoxystyrene)-4,6-bis(trichloromethyl)-s-tripper, 2-(p-isopropoxystyrene)-4,6-bis(trichloro) Methyl)-s-tripper, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triad 2-(4-naphthoxy)-4,6-bis(trichloromethyl)-s-three tillage, 2-phenylthio- 4,6-bis(trichloromethyl)-s- Tri-trap, 2-benzylthio-4,6-bis(trichloromethyl)-3-trimole, 4-(o-bromo-p-N,N-(diethoxycarbonylamino)-benzene Base)_2,6_bis(trichloromethyl)-s-three tillage, 2,4,6-gin(dibromomethyl)-s-three tillage, 2,4,6-paran (tribromomethyl) )-s - three tillage, 2-methyl-4,6-bis(tribromomethyl)-s-tripper, 2-methoxy-4,6-bis(tribromomethyl)-s-three Wells, etc. The oxadiazole compound may, for example, be 2-trichloromethyl-5-styrene-1,3,4-oxoxydiazole or 2-trichloromethyl-5-(cyanostyrene)-1. 3,4-Sideoxydiazole, 2-trichloromethyl-5-(naphthoquinone-1-yl)-1,3,4-oxyloxadiazole, -34 - 201132711 2·Dichloromethyl Base-5·(4-styrene)styrene_l,3,4-oxyloxadiazole and the like. As the compound, a benzophenone, a ketone, a 2-methyldibenone 3-methylbenzophenone, a 4-methylbenzophenone, a 2-chlorobenzophenone, and a bromine Benzophenone derivatives such as benzophenone; 2,2-dimethoxy-2-phenylethyl benzene, 2,2-diethoxyethyl benzene, 1-hydroxycyclohexyl benzene Ketone, α-hydroxy 2-methylphenylacetone, hydroxy-丨-methylethyl (p-isopropylphenyl) ketone decyl-1-(p-dodecylphenyl) ketone, 2-methyl - i- (4,-(methylthio)benzyl) 2 咐 丨 丨 两 两 ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ·1% 2,4,6-trimethylbenzylidene-diphenyl-phosphine oxide, trichloromethyl-(p-butylphenyl) ketone, 2-benzyl-2-dimethylamine Ethyl benzene derivative such as _4_morpholinyl (m〇rphoHn〇), butyl benzene, etc.; 9 oxo sulphate 2 ethyl 9-oxosulfonate π star, 2-isopropyl 9-oxygen Sulphur can sing, 2 _ chloro 9 _ oxysulfonate, 2,4-dimethyl 9 oxa sulphate, 2,4 • diethyl 9 oxa sulphate, 2, 4 _ different 9-oxosulfonium singer derivative such as propyl 9-oxosulfonate, and dimethylamine A benzoate derivative such as ethyl benzoate or ethyl p-ethylaminobenzoate. The ketal compound may, for example, be ket dimethyl ketal or benzyl-β-methoxyethyl ethyl acetal. The benzoin compound may, for example, be benzoin isopropyl ether, benzoin isobutyl ether, benzoin methyl ether or methyl phthalyl benzoyl benzoate. As the acridine compound, 9-phenyl acridine ' 9 -pyridyl acridine, 9-pyrazinyl acridine, 1,2-bis(9-acridinyl)ethane, 1, 3-di (9-Aridinyl) propane, 1,4-bis(9-acridinyl)butane, 1,5-bis(9-acridinyl)pentane, 1,6--35 - 201132711 II (9 - aridinoyl)hexane, 1,7-bis(9-acridinyl)heptane, anthracene, 8-:)9-yl)octane, 1,9-bis(9-acridinyl)decane '1,1〇_bis(9-acridinyl)癸1,1 1 -di(9-acridinyl)^--alkane, 1,1 2 -di(9-acridinyl)dodecane (9-Aridinoyl)alkane and the like. As the organic peroxidic compound, for example, trimethylcyclohexyl oxide, acetylacetone peroxide, I,1·bis(tertiarybutylper)-3,3,5-trimethylcyclohexane can be exemplified. Alkane, 1,1-bis(tri-butylperoxy)cyclohexane 2,2-bis(tertiary butylperoxy)butane, tertiary butyl hydroperoxide, cumyl gas Peroxide, diisopropylbenzene hydroperoxide, 2, methylhexane-2,5-dihydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, tertiary Cucumyl peroxide, a cumyl peroxide, 2,5-dimethyl-2,5-di(tertiary butylperoxy)hexane, 2,5-grass Oxalyl peroxide, peroxy benzoic acid, benzoyl peroxide, 2,4-dichlorobenzhydryl peroxide, diisopropyl peroxydicarbonate di-2-ethylhexyl peroxy Dicarbonate, di-2-ethoxyethyl peroxydiester, dimethoxyisopropyl peroxycarbonate, bis(3-methyl-3-methoxy)peroxydicarbonate, three Butyl peroxyacetate, tertiary butyl peroxyacetic acid (pivalate), tertiary butyl peroxy neodecanoate, tertiary butyl octanoate, three Butyl peroxylaurate, tert-butyl peroxycarbonate 3,3',4,4'-tetra-(tertiary butylperoxycarbonyl)benzophenone, 3,3',4,4,- Tetra-hexylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra-(p-isopropyl-peroxycarbonyl)benzophenone, carbonyl di(tertiary butylperoxydihydrogen) O-benzoic acid), carbonyl di(tri-hexylperoxydihydrodiphthalic acid), and the like. Acridine, ketone peroxyalkylene, diiso-5-dioxyammonium decyl decyl carbonate, butyl trimethyl peroxycarbonate, (trienyl dimethyl-36 - 201132711 azo compound, for example For example, an azo compound described in JP-A-81-18621. For the coumarin compound, for example, 3-methyl-5-amino-((3-trin-2-yl)amino group is exemplified. )-3-phenylcoumarin, 3-chloro-5-diethylamino-((s-trin-2-yl)amino)-3-phenylcoumarin, 3-butyl- 5-dimethylamino _((3_Tripan-2-yl)amino)-3-phenylcoumarin, etc. For the azide compound, a US patent 2 8 4 8 3 2 can be exemplified. The organic azide compound, 2,6-bis(4-azidoylidene)-4-ethyl described in the specification No. 8, the specification of the U.S. Patent No. 2 8 5 2 3 79 and the specification of U.S. Patent No. 2,940,853 Cyclohexanone (BAC-E), etc. Examples of the hexaarylbiimidazole compound include, for example, Japanese Patent Publication No. Hei 6-29285, U.S. Patent No. 3,479,185, the same as No. 4,311,783, and No. 4,62 2 , 2 8 6 and other instructions described in various instructions Specifically, 2,2'-bis(o-chlorophenyl)-4,4,5,5,-tetraphenylbiimidazole, 2,2'-bis(o-bromophenyl)) 4,4',5,5,-tetraphenylbiimidazole, 2,2,-bis(o-, p-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2, 2,-bis(o-chlorophenyl)-4,4',5,5'-tetrakis(m-methoxyphenyl)biimidazole, 2,2,_bis(〇,〇'_dichlorophenyl) -4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-nitrophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2 '-Bis(o-methylphenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-trifluorophenyl)_4,4,5,5'- Tetraphenylbiimidazole and the like. Examples of the organic borate compound include, for example, JP-A-621-143 044, JP-A-62-150242, JP-A-37-201132711, JP-A-9-188685, and JP-A-Hipping Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. Bulletin of the Gazette, etc., and Kunz, Martin "Rad Tech, 98. Proceeding April 19-22, 1 998, 〇 14 &amp; 8 〇", etc., organic borate, Japanese Patent Laid-Open No. Hei 6-l57623, Japanese special Japanese Patent Application Laid-Open No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. Japanese Patent Application Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. Special Kaiping 7-14〇589, Japan Special Kaiping 7-3 No. 6527 and Japanese Patent Laid-Open No. 7-29201 Patent Publication 4, etc. organoboron transition metal coordination complexes, etc. as specific examples. Examples of the disulfide compound include compounds described in JP-A-61-166544, and the specification of Japanese Patent Application No. 2001- 323-18. As the oxime ester compound, JCS Perkin 11 (1979) 1653-1660) can be exemplified. 'JCS Perkin 11 (1979) 156-162 &gt; Journal of Photopolymer Science and Technology (1 995) 202-232, Japanese Special 2 000- The compound described in the publication of the Japanese Patent Publication No. JP-A No. 2000-80068, and the compound described in JP-A-2004-534797. In terms of commercial products, it is preferably made by BASF Japan Co., Ltd. -38 - 201132711

Irgacure OXE-01, OXE-02, etc. Further, in the present invention, an oxime ester compound represented by the following formula (2) or (3) is preferred.

In the above formulae (2) and (.3), 1 and R2 each independently represent a monovalent substituent; X represents a monovalent substituent or a hydrogen atom; A represents a divalent organic group; and Ar represents an aryl group. Suitable specific examples of the oxime ester compound represented by the above formula are as follows. -39 - 201132711

-40 - 201132711

-41 - 201132711

201132711

Among these, in the stage of preparing the coloring photosensitive composition, it is easy to dissolve in a solvent, and the productivity is good, and the following are particularly suitable -43 - 201132711

SI Schlesinger, Photogr. Sci. Eng., 18, 387 (1974) 'TSBal et als Polymer, 2 1,42 3 (1 9 8 0), diazonium salt, US Patent No. 4,069, 〇55, 曰Bent The ammonium salt described in Japanese Laid-Open Patent Publication No. Hei 4-365049, the specification of U.S. Patent No. 4, No. 69, No. 55, and the specification of the specification of No. 4,069,056, the specification of European Patent No. 1, 4,143, and the United States Patent No. 339 Japanese Patent Publication No. 49, No. 41, No. 2, No. 1, the specification of the specification, Japanese Patent Application Laid-Open No. Hei. No. Hei. 201132711 The iodonium salt 'diaryl iodide salt' which can be suitably used in the present invention is preferably one or more of an electron-donating group such as an alkyl group, an alkoxy group or an aryloxy group, from the viewpoint of stability. Further, the form of another suitable onium salt is preferably a coumarin or an anthracene structure having one substituent of the triarylsulfonium salt, and an iodonium salt having an absorption of 300 nm or more. The hydrazine salt which can be suitably used in the present invention can be exemplified by the European Patent No. 3, 70, 693, the same as the specification of 3, 90, 2, 4, the same as the specification of 23, 5, 67, the specification of 297, 443, the specification of 297, 442. U.S. Patent No. 4,93 3,3,77, the same as No. 161,811, the same as No. 410,201, the same as No. 3, 9,049, 'the same as the 4,760,0 1 3 specification, the same as 4,734,444, the same as 2,833,827, The onium salt described in the specification of the German Patent No. 2,904,626, the specification of the specification No. 3,604,580, and the specification of the specification No. 3,604,581, is preferably replaced by an electron-withdrawing group from the viewpoint of stability sensitivity. The electron-withdrawing side is better than Hammett 値 greater than zero. As the appropriate electron-withdrawing group, a halogen atom, a carboxylic acid or the like can be exemplified. Further, as for other suitable onium salts, one of the substituents of the triarylsulfonium salt may have a coumarin, a lycopene structure, and an onium salt having an absorption of 300 nm or more. As the other suitable onium salt, a phosphonium salt having an allyloxy group or an arylthio group having an absorption of 300 nm or more can be exemplified as the triarylsulfonium salt. Further, as the key salt compound, JVCrivello et al, Macromolecules, 10(6), 1 307 (1 977), JVCrivello et al, J. Polymer Sci., Polymer Chem. Ed., 17, 1047 can be exemplified. (1979) Selenium-45 ~ 201132711 salt; CSWen et al, Teh, Proc. Conf. Rad. Curing ASIA, p478 Tokyo, Oct (1 9 8 8 ), the key salt of strontium salt, etc. Examples of the mercaptophosphine (oxide) compound include Irgacure 819, Darocure 4265, Dar o cu re Τ Ο Ο manufactured by BASF Japan. In terms of photopolymerization initiator, from the viewpoint of exposure sensitivity, it is selected from a trihalomethyl triterpenoid compound, a benzyl dimethyl ketal compound, an α-hydroxyketone compound, and an α-amino group. Ketone compound, mercaptophosphine compound, phosphine oxide compound, metallocene compound, anthraquinone compound, triallyl imidazole dimer, key compound, benzothiazole compound, benzophenone compound, acetamidine A compound of the group consisting of a benzene compound and a derivative thereof; a cyclopentadiene-benzene-iron complex compound and a salt thereof; a halogen methyl oxadiazole compound and a 3-aryl substituted coumarin compound are preferred. Further preferred are a trihalomethyl tritrap compound, an α-amino ketone compound, a mercaptophosphine compound, a phosphine oxide compound, an anthraquinone compound, a triallyl imidazole dimer, a key compound, and a diphenyl group. a ketone compound or an acetophenone compound, which is selected from the group consisting of a trihalomethyl tritrap compound, an α-amino ketone compound, an anthraquinone compound, a triallyl imidazole dimer, and a benzophenone compound. At least one of the compounds of the group is optimal. Specific examples of the other suitable photopolymerization initiators mentioned above include 4-[o-bromo-p-fluorene, fluorene-bis(ethoxycarbonyl)aminophenyl]-2,6-di(trichloromethyl). -s-three tillage). In addition, Irgacure-184, Irgacure-3 69, Irgacure-379, Irgacure-651, Irgacure-907, Irgacure-819 (above, manufactured by BASF Japan Co., Ltd.), may be mentioned as a commercially available product of a suitable photopolymerization initiator. _ 46 — 201132711

Darocure 4265, Darocure ΤΡΟ (above Merck), Adeca 1717 (made by Asahi Chemical Industry Co., Ltd.), 2,2'-bis(o-chlorophenyl)-4,5,4'-tetraphenyl-1,2' - Biimidazole (manufactured by Heijin Chemical Co., Ltd.), EABF (manufactured by H〇dgaya Chemical Co., Ltd.), and the like. The photopolymerization initiator used in the coloring photosensitive composition of the present invention may be used alone or in combination of two or more. Further, in the case of using an initiator having no absorption at the exposure wavelength, it is necessary to use a compound having absorption at the exposure wavelength as a sensitizer (s e n s i t i z e r). The content of the photopolymerization initiator is preferably in the range of 0.1% by mass to 20% by mass, more preferably 0.5% by mass to 15% by mass, particularly preferably 1% by mass, based on the total solid content in the coloring photosensitive composition layer. A range of 10% by mass. In this range, good sensitivity and pattern formation can be obtained. [Alkali-soluble resin] The color-sensitive photosensitive composition of the present invention preferably contains at least one of alkali-soluble resins. The alkali-soluble resin may be contained in the stage of adjusting the pigment dispersion composition, or may be divided and added in two steps of the adjustment of the pigment dispersion composition and the adjustment of the coloring photosensitive composition. In the case of the alkali-soluble resin, in the linear organic polymer, a molecule capable of promoting at least one alkali solubility (for example, a molecule having an acrylic copolymer or a styrene copolymer as a main chain) may be used (for example, Among the alkali-soluble resins of a carboxyl group, a phosphoric acid group, a sulfonic acid group or the like, it is suitably selected. Among them, those which are soluble in an organic solvent and developable as a weak aqueous alkali solution are more preferable. In the production of an alkali-soluble resin, a method such as a known radical polymerization method can be applied. The polymerization conditions of the temperature -47 - 201132711 degrees, the pressure, the type and amount of the radical initiator, the kind of the solvent, and the like when the alkali-soluble resin is produced by the radical polymerization method can be easily set by those skilled in the art. , the experimental conditions to be determined can be performed. In the above linear organic polymer, a polymer having a carboxylic acid in a side chain is preferred. For example, JP-A-59-446 No. 5, Tegong-zhao 5 4- 3 43 2 7 , Te Gong-zhao 58-12577, Te Gong-zhao 54-25957, JP-A-59-53836, and JP-A-Japan As described in each of the publications of No. 59-71048, a methacrylic acid copolymer, an acrylic copolymer, an itaconic acid copolymer, a crotonic acid copolymer, a maleic acid copolymer, and a partially esterified maleic acid may be mentioned. a copolymer or the like, an acidic cellulose derivative having a carboxylic acid in a side chain, a polymer addition anhydride having a hydroxyl group, and the like, and a (meth)acryloyl group or an allyl group may be exemplified as a side chain. A polymer polymer having an unsaturated bond site such as a group is preferred. Among these, a multicomponent copolymer composed of (meth)propionic acid phenylacetic acid/(meth)acrylic acid copolymer or benzyl (meth)acrylate/(meth)acrylic acid/other monomer is preferred. . Other than this, a copolymerized product of 2-hydroxyethyl methacrylate may also be mentioned. The polymer can be used in any amount. In addition to the above, a 2-hydroxypropyl (meth)acrylate/polyphenylene macromonomer/methacrylic acid ester/methacrylic acid copolymer described in JP-A-7-140654, Aromatic acid 2_trans-based _3_phenoxypropyl ester / polymethyl methacrylate macromonomer / methyl acrylate acid vinegar / methyl propylene acid copolymer, 2-hydroxyethyl methacrylate /Polyphenylene macromonomer / methacrylic acid -48 a 201132711 Methyl ester / methacrylic acid copolymer, methacrylic acid 2 - ethyl acetoacetate / polystyrene phenyl macromonomer / benzyl methacrylate / methacrylic acid copolymer and the like. * The specific constituent unit of the alkali-soluble resin, especially the copolymer of (meth)acrylic acid and other monomers copolymerizable with the (meth)acrylic acid, is preferably 0, which is copolymerizable with the (meth)acrylic acid. The other monomer aspect can be exemplified by (meth)acrylic acid alkyl ester, (meth)acrylic acid aryl ester, vinyl compound, and the like. Here, the hydrogen atom of the alkyl group and the aryl group may be substituted with a substituent.

Specific examples of the (meth)acrylic acid alkyl ester and the (meth)acrylic acid aryl ester include methyl (meth)acrylate, ethyl (meth)acrylate, and propyl (meth)acrylate. Methyl)butyl acrylate, isobutyl (meth)acrylate, amyl (meth)acrylate, hexyl (meth)acrylate, octyl (meth)acrylate, phenyl (meth)acrylate, benzyl acrylate Ester, toluene acrylate, naphthyl acrylate, cyclohexyl acrylate, and the like. The vinyl compound may, for example, be styrene, α-methylstyrene, vinyltoluene, glycidyl methacrylate, acrylonitrile, ethylene acetate, fluorene-vinylpyrrolidone or tetrahydrogen methacrylate. Anthracene ester, polystyrene macromonomer, polymethyl methacrylate macromonomer, CH2 = CR31R32 [here, R31 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms; and R32 represents a carbon number of 6 to 10 a hydrocarbon ring], CH2 = C(R31)(COOR33) [wherein R31 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms; and R33 represents an alkyl group having 1 to 8 carbon atoms or an aromatic group having 6 to 12 carbon atoms. Alkyl] and the like. These other monomers which can be copolymerized may be used alone or in combination of 2 - 49 - 201132711 or more. Other monomers which are suitably copolymerizable are selected from at least one of CH2 = CR31R32, CH2 = C(R") (COOR33), phenyl (meth) acrylate, benzyl (meth) acrylate and styrene. Particularly preferred is CH2 = CR31R32 and/or CH2 = C(R31)(COOR33). Each of R31, R32 and R33 is synonymous with the foregoing. In the coloring photosensitive composition, the content of the alkali-soluble resin is preferably It is preferably from 1 to 20% by mass, more preferably from 2 to 15% by mass, particularly preferably from 3 to 12% by mass, based on the total solid content of the composition. [Sensitizing dye] Used in the present invention The photosensitive resin composition is preferably added with a sensitizing dye, and is preferably improved in sensitivity. The exposure of the sensitizing dye absorbs a wavelength, thereby promoting the radical reaction of the polymerization initiator component. Or a polymerization reaction of the above-mentioned polymerizable compound. In the case of such a sensitizing dye, a dye or a pigment which is known to be a photosensitizing dye or dye, or absorb light and interact with a photopolymerization initiator can be used. Appropriate photosensitive light of the sensitizing dye of the present invention Examples of the coloring matter or dye include polynuclear aromatics (for example, lanthanum, cerium, and terphenyl), and guanidines (for example, fluorosceine, eosin, erythrosin, and rhodamine). B, rosebengal), anthocyanins (such as thiocarbocyanin, oxacarbonyl anthocyanins), merocyanine (such as merocyanine, carbonyl) Anthocyanins, thiazepines (eg, thionine, methylene blue, toluidine blue, acridines (eg acridine orange, chloroflavin) acridine-50 - 201132711 yellow aCriflavin), phthalocyanines (eg, phthalocyanine, metal phthalocyanine), porphyrins (eg, tetraphenylporphyrin, central metal-substituted porphyrin), chlorophyll (chl〇r〇phyl) (eg, chlorophyll, Chlorochlorophyllin (chl〇r〇phylHn), a central metal-substituted chlorophyll), a metal complex, an anthraquinone, (for example, a ruthenium), a tetragonal key system (for example, a four-pointed key system), etc. Appropriate, belonging to the following group of compounds, and can be exemplified by 3 50 to 45 Onm Large absorption wavelength pigments, such as 'polynuclear aromatics (such as strontium, barium, and triphenyl), can alpha (such as egg yellow, red, red erythro, rhodamine, rose), cyanine Nutrients (such as thiocarbocyanin, oxycarbocyanin), procyanidins (such as procyanidins, carbonyl anthocyanins), thiazides (such as sulfur, methylene blue, Toluidine blue), acridines (eg, acridine orange, chlorsulfurin, acriflavine), anthraquinones (eg, anthraquinone), tetraterpenoids (eg, a four-pointed key). (thiol compound) The thiol compound functions as a co-sensitizer or also has an effect of improving the adhesion to the substrate. The co-sensitizer has a function of further improving the sensitivity of the active radiation with respect to the sensitizing dye or the photopolymerization initiator, or suppressing polymerization inhibition by oxygen of the ethylenically unsaturated compound, and the like, and specifically, a thiol compound, specifically, Ethylene glycol dithiopropionate (EGTP), butanediol dithiopropionate (B DTP), trimethylolpropane thiol propionate (TMTP), neopentyl alcohol Deuterium (thiopropionate) (PETP), a hydrogenthiopropionic acid derivative such as THEIC-BMPA represented by the following formula; Ethylene-51 - 201132711 Alcohol dithioglycolate (egtg), dibutyl Alcohol dithioglycolate (BDTG), hexanediol dithioglycolate (hdtg), trimethylolpropane ginseng (thioglycolate) (TMTG), neopentyl pentoxide ( a thioglycolic acid derivative such as thioglycolate (PETG); 1,2-benzenedithiol, 1,3-benzenedithiol, 1,2-ethanedithiol, 1,3 - propane dithiol, 1,6-hexamethylene dithiol, 2,2'-(ethylenedithio)diethanethiol, intermediate-2,3-dihydrothiosuccinic acid, p-pair Toluene dithiol, m-xylene dithiol The mercaptans; bis (mercapto ethyl) ether, etc. The hydrogen sulfides. These may be used alone or in combination of two or more.

I HSC2H4C00C2H4^ ^c2h4ococ2h4sh

QsssQ 0 = Q hsc2h4cooc2h4n The thiol compound used in the present invention is preferably represented by the following formula ()

Wide N A2 y~SH (I:

I

R Formula (wherein R represents a hydrogen atom, an alkyl group, or an aryl group; and A2 represents an atomic group which forms a heterocyclic ring with N = CN. _ 52 _ 201132711 In the formula (I), R represents an alkyl group, or An aryl group; the alkyl group may, for example, be a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, and a linear chain having 1 to 12 carbon atoms and 3 to 12 carbon atoms; The branched form and the cyclic alkyl group having 5 to 10 carbon atoms are more preferable, and specific examples thereof include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group and fluorene group. Base, fluorenyl, undecyl, dodecyl, thirteen, hexadecyl, octadecyl, icosyl, isopropyl, isobutyl, secondary butyl, tert-butyl, isopentyl , neopentyl, 1-methylbutyl, isohexyl, 2-ethylhexyl, 2-methylhexyl, cyclohexyl, cyclopentyl, 2-norbornyl, etc. In addition to the monocyclic structure, one to three benzene rings may be used to form a condensed ring, and a benzene ring may form a condensed ring with a 5-membered unsaturated ring. Specific examples thereof include a phenyl group and a naphthyl group. Sulfhydryl, phenanthryl, sulfhydryl, An acenaphthenyl, fluorenyl, etc., wherein phenyl and naphthyl are more preferred. Further, in the formula (I), A2 represents an atomic group which forms a heterocyclic ring with N = CN. The atom constituting the atomic group may, for example, be a carbon atom, a nitrogen atom, a hydrogen atom, a sulfur atom or a selenium atom. Further, the hetero ring formed by A2 and N=CN may further have a substituent. The substituent which can be introduced may be the same as the substituent which can be introduced into the above alkyl group or aryl group. Further, the thiol compound is more preferably a compound of the following formula (II) or formula (III)-53. - 201132711 Shown.

In the formula (II), R1 represents an aryl group; and X1 represents a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, or an aryl group. In the formula (III), R2 represents an alkyl group or an aryl group; and the X1 group has the same meaning as X1 of the formula (II). In the general formulae (Π) and (III), a halogen atom, a chlorine atom, a bromine atom or an iodine atom is preferred from the viewpoint of a halogen atom. In the general formulae (II) and (III), the alkyl group and the alkyl group represented by R in the formula (I) are also the same in the appropriate ranges. Further, the aryl group in the general formulae (π) and (in) is the same as the aryl group represented by R in the formula (I), and the appropriate range thereof is also the same. Each of the groups in the formulae (II) and (III) may further have a substituent, and the substituent is exemplified as a substituent which can be introduced into the alkyl group or the 'aryl group represented by R of the formula (I). the same. In the general formulae (II) and (III), X1 is more preferably a hydrogen atom' from the viewpoint of solubility of propylene glycol monomethyl ether acetate (hereinafter, suitably referred to as PGMEA). In the formula (II), R1 is preferably a phenyl group, which is most preferable from the viewpoint of sensitivity and PGMEA solubility. -54 - 201132711 In the formula (III), R2 is preferably a methyl group, an ethyl group, a phenyl group or a benzyl group, from the viewpoint of sensitivity and PGMEA solubility. Among the general formulae (Π) and (III), the compound represented by the formula (ΠΙ) is most preferable from the viewpoint of solubility of PGME A. These thiol compounds can be synthesized by the method described in J. Appl. Chem., 34, 2203-2207 (1961). In the coloring photosensitive composition of the present invention, the compound represented by the formula (I) may be used singly or in combination of two or more kinds thereof, and may be selected from the compound represented by the formula (II). The compound represented by the formula (ΠΙ) and the compound selected from the two may also be used in combination. The content of the thiol compound in the coloring photosensitive composition is preferably from 0.1 to 5.0% by mass, more preferably from 0.2 to 4% by mass, based on the total solid content of the composition. When it is in this range, it is preferable because the polymerizability is not impaired. [Solvent] The colored photosensitive composition of the present invention can be suitably prepared by using a solvent together with the above components. The solvent may, for example, be an ester such as ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate or isopropyl butyrate. Ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, methyl glycolate, ethyl hydroxyacetate, butyl glycolate, methyl methoxyacetate, ethyl methoxyacetate , butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, and 3-hydroxypropionic acid alkyl esters such as methyl 3-hydroxypropionate and ethyl 3-hydroxypropionate (for example) 3-methoxypropionic acid methyl-55 - 201132711 ester, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate), and 2-hydroxypropane 2-hydroxypropionic acid alkyl esters such as methyl ester, ethyl 2-hydroxypropionate, and propyl 2-hydroxypropionate (for example, methyl 2-methoxypropionate, 2-methoxypropionic acid Ester, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-oxo-2-methylpropanoate, 2-oxo- Ethyl 2-methylpropionate, methyl 2-methoxy-2-methylpropanoate, ethyl 2-ethoxy-2-methylpropionate) And methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetate, ethyl acetate, methyl 2-oxobutanoate, ethyl 2-oxobutanoate, etc. : Ethers such as diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl stilbene acetate, ethyl stilbene acetate, diethylene glycol Monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol methyl ether acetate, propylene glycol diethyl ether acetate, propylene glycol propyl ether acetate, etc.; ketones, such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone, etc.; aromatic hydrocarbons such as toluene, xylene, and the like. Among these, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl celecoxib acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, Methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol methyl ether acetate, and the like are suitable. The solvent may be used singly or in combination of two or more. [Other components] The colored photosensitive composition of the present invention may contain a fluorine compound-56-201132711 organic compound, a heat-resistant polymerization agent, a colorant, another chelating agent, a polymer compound other than an alkali-soluble resin, and an interface. Various additives such as an active agent, an adhesion promoter, an antioxidant, an ultraviolet absorber, and an anti-agglomerating agent. Hereinafter, the preferred components will be described. &lt;Fluorine-based organic compound&gt; By containing a fluorine-based organic compound, liquid characteristics (especially fluidity) as a coating liquid can be improved, and uniformity of coating thickness or liquid-saving property can be improved. That is, the interfacial tension between the substrate and the coating liquid is lowered, and the wettability to the substrate is improved, and the coating property to the substrate is improved. Therefore, in the case where a film of several μm is formed in a small amount of liquid, uneven thickness can be performed. The viewpoint of film formation with a small uniform thickness is extremely effective. The fluorine-containing organic compound preferably has a fluorine content of from 3 to 40% by mass, more preferably from 5 to 30% by mass, particularly preferably from 7 to 25% by mass. When the fluorine content is within this range, it is extremely effective from the viewpoint of coating thickness uniformity or liquid-saving property, and the solubility in the composition is also good. Examples of the fluorine-based organic compound include megafac F171, the same F 1 72 ', F173, F177, F141, F142, F143, F144, R30, and F4 3 7 (above, DIC). System), FLUORADE FC430, with FC431, with FC171 (above Sumitomo '3M (share) system), Safron S-382, with SC-101, with SC-103, with SC-104, with SC-105, with SC1068, Same as SC-381, same as SC-383, same as S393, and KH-40 (above, Asahi Glass Co., Ltd.). The fluorine-based organic compound is particularly effective in preventing uneven coating or thickness when the coating film formed by coating is thinned by -57 - 201132711. Further, slit coating which is liable to cause liquid flow is also effective. The fluorine-based organic compound is preferably added in an amount of from 0.001 to 2.0% by mass, more preferably from 0.005 to 1.0% by mass, based on the total mass of the pigment dispersion composition or the coloring photosensitive composition. &lt;Thermal polymerization initiator&gt; The colored photosensitive composition of the present invention is also effective in containing a thermal polymerization initiator. Examples of the thermal polymerization initiator include various azo-based compounds and peroxide-based compounds, and examples of the azo-based compound include azobis compounds, and examples of the peroxide-based compounds include ketones. Peroxide, ketal, hydroperoxide, dialkyl peroxide, dimercapto peroxide, peroxyester, peroxydicarbonate, and the like. &lt;Intermediate Active Agent&gt; In the colored photosensitive composition of the present invention, it is preferable to use various kinds of surfactants from the viewpoint of improving coatability, and it is also possible to use nonionic, cationic or anionic agents. A variety of surfactants. Among them, a fluorine-based surfactant having a perfluoroalkyl group as a nonionic surfactant is preferred. Specific examples of the fluorine-based surfactant include a megafac (registered trademark) series manufactured by DIC Co., Ltd., and a Fluorad (registered trademark) series manufactured by 3M Company. In addition to the above, specific examples of the coloring photosensitive composition and the additive include a chelating agent such as glass or alumina; an itaconic acid copolymer, a crotonic acid-58-201132711 copolymer, and a maleic acid copolymer. , partially esterified maleic acid copolymer, acidic cellulose derivative, acid anhydride added to a polymer having a hydroxyl group, alcohol soluble nylon, benzene formed from bisphenol A and epichlorohydrin An alkali-soluble resin such as an oxy-resin; a surfactant such as a non-ionic, a cationic or an anionic group; in particular, a phthalocyanine derivative (commercial product EFKA-745 (manufactured by Morishita Sangyo Co., Ltd.)): organic Alkane polymer KP 341 (manufactured by Shin-Etsu Chemical Co., Ltd.), (meth)acrylic (co)polymer Polyflow No. 75, ]^〇.90, ? 〇.95 (manufactured by Kyoeisha Oil & Fat Chemical Co., Ltd.), a cationic surfactant such as '^001 (manufactured by Yusei Co., Ltd.); examples of other additives, etc., for example, A deca P 1 ur ο nic L 3 1, F38, L42, L44, L61, L64, F68, B 72, P95, F77, P 84 , F87 ' P94 ' L101 ' P103, F108, L121, P-123 (Asahi Corporation) ) and Isonet S-20 (manufactured by Sanyo Chemical Co., Ltd.); 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, alkoxybenzophenone, etc. An ultraviolet absorber; and an anti-agglomerating agent such as sodium polyacrylate. In the case where the alkali solubility of the uncured portion is promoted and the developability of the colored photosensitive composition is further improved, the organic carboxylic acid is preferably contained in the colored photosensitive composition, preferably having a molecular weight of 1 Å or less. The addition of a low molecular weight organic carboxylic acid. Specifically, for example, an aliphatic monocarboxylic acid such as formic acid, acetic acid, propionic acid, butyric acid, valeric acid, pivalic acid, caproic acid, diethylacetic acid, heptanoic acid, octanoic acid or the like can be exemplified: Oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pemelilic acid, suberic acid, azelaic acid (azelaic _ 59 - 201132711 acid), azelaic acid, tridecanedioic acid (brassiic acid), methylmalonic acid, ethylmalonic acid, dimethylmalonic acid 'methyl succinic acid, tetramethyl succinic acid, citraconic acid, etc.; aliphatic carboxylic acid; (tricarballylic acid) 'a fatty acid such as aconitic acid, camphoronic acid, etc.; benzoic acid, tolylmethyl phthalate, cuminic acid, 2,3-xylene An aromatic monocarboxylic acid such as hemelitic acid or 1,3,5-tritoic acid; tannic acid, isophthalic acid, terephthalic acid, trimellitic acid, trimesic acid An aromatic polycarboxylic acid such as 1,2,3,5-benzenetetracarboxylic acid (mellophanic acid) or pyromellitic acid; phenylacetic acid Hydrogenated aconic acid, hydrogen cinnamic acid, mandelic acid, phenyl succinic acid, acane acid, cinnamic acid, methyl cinnamate, cinnamic acid preester, cinnamylidene acid (coumalic acid), a carboxylic acid such as unbellic acid. (Thermal crosslinkable compound) The thermally crosslinkable compound in the present invention means a compound which is thermally crosslinked with a carboxyl group of an alkali-soluble resin, and by crosslinking by heat, a crosslinking density can be increased, and color formation can be achieved. The chemical resistance of the cured film is improved. The thermocrosslinkable compound to be used in the present invention may, for example, be a bisphenol A type, a cresol novolac type, a biphenyl type or an alicyclic epoxy compound epoxy compound, but may also be used to represent melamine. A compound which is a heat crosslinkable compound such as a compound. Specific examples of the epoxy compound, such as bisphenol A type, except Epotohto YD-1 1 5 'YD-118T, YD-127, YD-1 28 ' YD-1 34 -60 ~ 201132711 , YD-8125, YD -7011R, ZX-1059, YDF-8170, YDF-170, etc. (above Dongdu Chemical), Denacol EX-1101, EX-1102, EX-1103, etc. (above Nagase Chemicals), Plaxel GL-6 GL- 62. G1 (H, G102 (manufactured by Daicel Chemical Co., Ltd.) may also be exemplified by similar bisphenol F type and bisphenol S type. Alternatively, Ebecryl 3 700, 3 70 1, 600 (above) Epoxy acrylate such as Daicel UCB. In the case of the cresol novolak type, Epotohto YDPN-638, YDPN-701 'YDPN-702, YDPN-703, YDPN-704, etc. (above Dongdu Chemical Co., Ltd.), Dena.col EM-125 or the like (the above Nagase chemical conversion system) and a biphenyl type may, for example, be 3,5,3',5'-tetramethyl-4,4'diepoxypropylbiphenyl or the like. Examples of the alicyclic epoxy compound include Celloside 202 1, 208 1 , 208 3, 205 5, Epolead GT-301, GT-302, GT-401, GT-403, and EHPE-3 150 (above Daicel) Chemical system] 'Santoto ST-3000, ST-4000 , ST-5 08 0, ST-5100, etc. (above Dongdu Chemical Co., Ltd.), etc. In addition, it can also be used as an amine-type epoxy resin in the skeleton of Epotohto YH-434, YH-434L, and bisphenol A type epoxy resin. A glycidyl ester modified by a dimer acid, etc. Among these heat-crosslinkable compounds, an alicyclic epoxy compound or a novolak type epoxy compound represented by the following formula (I) is preferred. The epoxy equivalent is particularly suitable from 150 to 220. For this material, Celloside 2021, 2081, 2083 ' 2085, Epolead GT-301, GT-302, GT-401, GT-403, EHPE-3150 manufactured by Daicel Chemical Co., Ltd. can be used. DIC company Epiclon N-660, N-665, N-670, N-673, N-680, N-690, N-695-61 - 201132711, N-685-EXP, N-672-EXP, N- 655-EXP-S, N-865, N-865-80M, YDCN-701, YDCN-7 02, YDCN-7 03, YDCN-704, YDCN-704L, etc. can be used for warehouse g, Celloside202 1, 2 08 3, 208 5, EHPE-3150, Epiclon N-660, N-6 6 5, N-6 70, N-673, N-680, N-690, N-6 9 5, YDCN-704L, etc. are particularly suitable.

In the formula, 1 is an integer of 5 to 100, and R each independently represents a hydrogen atom or a methyl group. The composition of the present invention may contain two or more kinds of polyfunctional epoxides. The content of the hardening composition of the polyfunctional epoxy compound of the present invention is preferably from 2 to 20% by mass, more preferably from 3 to 1% by mass, based on the total solid content of the pigment-removing component. When the content is within this range, the film is excellent in solvent resistance. Further, when it is too large, the quality of the color filter is impaired by the yellow color after baking, and when it is too small, the NMP resistance is deteriorated. &lt;Heat Resistant Polymerization Agent&gt; In the coloring photosensitive composition of the present invention, it is preferred to further add a heat-resistant polymerization agent, for example, hydroquinone, p-methoxyphenol, di-tertiary butyl-p-methylhydrazine, Gallic phenol, tertiary butyl catechol, benzoquinone, 4,4,-thiobis(3-methyl-62 - 201132711 -6-tridecanoic acid), 2,2'-methylene bis (4) - Methyl-6-diylbenzimidazole or the like is useful. The colored photosensitive composition of the present invention contains (D) a polymerizable compound initiator (preferably with alkali solubility) in the pigment dispersion composition of the foregoing. The resin and the solvent are required to be prepared by mixing an additive such as a surfactant. <Color filter and method for producing the same> The method for producing a color filter of the present invention, which is characterized by the coloring of the present invention The coloring pattern forming step of forming a colored pattern by direct patterning on a photosensitive film formed by a photosensitive film formed on a substrate and forming a photosensitive film, thereby obtaining the coloring pattern forming step of the colored pattern Color-hardening composition is characterized by dispersibility, contrast, and clarity Improved color pattern color filter. The color filter of the present invention uses the above-described optical composition, and the other layers such as an undercoating layer and a adhesion improving layer on a substrate such as glass. The film (coloring pattern) is produced. Hereinafter, a method for producing the hair piece is exemplified, and the coloring photosensitive composition of the present invention is composed, for example, in the order of the steps (formation of the coloring photosensitive composition layer). , the layer of which is provided on the substrate and forms the photosensitive composition of butanol), the 2-hydrogen sulfide of the invention, and (E) photopolymerization, which may be included according to the number: The layer forming step; in the exposing and developing, the manufacturing method, the coloring of the coloring matter of the present invention having a pigment, or the coloring of the coloring by the undercoating. Directly or via its layers. -63 _ 201132711 The application of the photosensitive composition can be carried out by a usual method, and it is preferably applied by a coating method such as spin coating, slit coating, flow casting coating, or roll coating. Drying (prebaking) of the film by the colored photosensitive composition of the present invention provided on a substrate (preferably coated), using a hot plate, an oven, etc., at a temperature ranging from 50 to 140 ° C, at 10 It is carried out under conditions of 300 seconds. Film is provided on the substrate by providing the colored photosensitive composition of the present invention

The formation of I is generally from 0.3 to 5.0 μm, preferably from 0.5 to 3.5 μm, and most preferably from 1.0 to 2.5 μm, in terms of the dry thickness of the film. (Pattern Exposure) Next, in the formed photosensitive composition layer, the pattern is exposed by a predetermined mask pattern or the like. The exposure region is hardened by exposure of the pattern. At this time, in terms of radiation used for exposure, ultraviolet rays such as g-line, h-line, i-line, and j-line are preferable. (Development) A colored pattern (for example, a colored pixel) can be formed by developing and removing the uncured portion with a developing solution after pattern exposure. As will be described later, the coloring patterns are formed in order of respective colors (for example, three colors or four colors), and a color filter having colored pixels of three colors or four colors can be obtained. In the development, the unhardened portion after exposure is dissolved in the developer, and only the hardened portion remains. In terms of development temperature, it is usually 20 to 30 ° C and the development time is 20 to 90 seconds. In the case of the developer, the film of the coloring photosensitive composition is dissolved in the uncured portion, and any one may be used as long as it does not dissolve the hardened portion. Specifically, a combination of various organic solvents or an alkaline aqueous solution can be used. The organic solvent may, for example, be exemplified by the solvent described above when the pigment dispersion composition of the present invention or the coloring photosensitive composition is prepared. The alkaline aqueous solution may, for example, be sodium hydroxide, barium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium silicate, sodium methyl silicate, ammonia water, ethylamine, diethylamine or dimethylethanolamine. Alkaline compounds such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, choline, pyrrole, piperidine, 1,8-diazabicyclo-[5,4,0]-7-undecene are dissolved It is an alkaline aqueous solution having a concentration of 0.001 to 10% by mass, preferably 〇·〇1 to 1% by mass. Further, in the case where an alkaline aqueous solution is used as a developing solution, it is generally washed with water (rinsing) after development. After the development, the remaining developer is washed and removed, and after drying, it is usually subjected to heat treatment at a temperature of 100 to 250 ° C (post-baking). The post-baking is used to cause the hardening to become a complete heating after development, usually by heating at about 200 ° C to 250 ° C (hard baking). The post-baking treatment is performed by using a hot plate or a convection oven (hot air circulation dryer), a high-frequency heating machine, or the like, and coating the film after development as in the above conditions, for continuous or batch Processing. By repeating the above operations in accordance with the desired number of tones, and repeating each color _ 65 - 201132711 in order, a color filter can be formed which is formed by a cured film of a plurality of colors. The best color filter can be produced by the above steps. By using the colored photosensitive composition of the present invention, the color filter used in the liquid crystal display element or the solid-state imaging element can be produced with less difficulty in process, high quality, and low cost by being produced by the above steps. For the substrate on which the colored pattern is formed, for example, an alkali-free glass, a soda glass, a pyrex (registered trademark) glass, a quartz glass, and a transparent conductive film to be used for a liquid crystal display device or the like, or a solid-state imaging device. A photoelectric conversion element substrate to be used, for example, a germanium substrate or the like, and a plastic substrate. On these substrates, a black strip that isolates each pixel is typically formed. In the plastic substrate, at least one layer selected from the group consisting of a gas barrier layer and a solvent resistant layer is preferred on the surface thereof. A gas barrier layer, a solvent resistant layer, or the like may be mentioned as the other layer in the case where a coloring photosensitive composition is provided on the substrate via another layer. The color filter of the present invention has a colored pattern formed by using the colored curable composition of the present invention. However, the coloring curable composition is excellent in dispersibility and contrast of the (A) pigment, and the brightness is improved. Therefore, in order to form a coloring pattern excellent in hue, it can be suitably used for a liquid crystal display element, and it is suitable for a liquid crystal display element or the like which requires an excellent color tone. That is, the color filter of the present invention is preferably applied to a liquid crystal display element. &lt;Liquid Crystal Display Element&gt; The liquid crystal display element of the present invention is provided with the color filter of the present invention, which is a product of 66-201132711. More specifically, an alignment film is formed on the inner surface side of the color filter, and is opposed to the electrode substrate, and the liquid crystal is sealed by filling the gap portion to obtain a panel of the liquid crystal display element of the present invention. According to the aspect of the present invention, it is possible to provide a color filter having less color unevenness and high contrast, which is provided with a colored pattern which can suppress generation of color unevenness caused by aggregation of a pigment and which is excellent in contrast and improved in brightness. By using the color filter, a liquid crystal display element having high-grade colored pixels can be provided. &lt;Solid-based imaging element&gt; The solid-state imaging element of the present invention comprises the color filter of the present invention. According to the present invention, it is possible to provide a solid-state imaging device which is excellent in color characteristics. The configuration of the solid-state imaging device is not particularly limited as long as it has a color filter and functions as a solid-state imaging device, and may be, for example, the following. The composition. The structure is formed on a support, and has a transfer electrode: it is composed of a plurality of photodiodes and polyfluorenes constituting a light receiving region of a CCD image sensor (solid-state imaging device); and has a light shielding film. In the photodiode and the transfer electrode, only tungsten or the like in which the light receiving portion of the photodiode is opened is provided; and the device protective film is provided on the light shielding film to cover the entire light shielding film and the photodiode light receiving portion. The formed tantalum nitride or the like is formed; and has a color filter attached to the protective film of the device. _ 67 — 201132711 Furthermore, on the protective layer of the device, it is also possible to have a light collecting means (for example, a microlens or the like, the same below) or a color filter under the color filter (on the side close to the support). The light sheet has a configuration of light collecting means and the like. [Examples] The present invention is further illustrated by the examples, but the present invention is not limited to the examples below. In addition, "%" and "part" are quality benchmarks unless otherwise stated. (Synthesis Example 1: Synthesis of (B) Quinoline Yellow Compound (1)) Quinoline Yellow Pigment (4,5,6,7-tetrachloro-2-[2-(4,5,6,7 -4) Chloro-2,3-dihydro-1,3-di-oxy-1H-indol-2-yl)-8-quinolinyl]-1H-isoindole-1, 3 (2 Η)- Ketone) (Paliotol yellow K096 1 HD, manufactured by BASF Corporation) 10 g - While stirring, 130 g of fuming sulfuric acid (25% S03) at 15 ° C was placed. After stirring for 3 hours, it was added to 250 g of ice. After standing for 30 minutes, the resulting suspension was filtered, and the obtained product was washed with water (50 ml). The product was added to 330 ml of water, and an aqueous ammonia solution was added until the pH was changed to 7 to neutralize with an aqueous ammonia solution. Thereafter, 75 g of ammonium chloride was added, and the mixture was stirred at 80 ° C for 3 minutes, and the precipitate which precipitated was filtered at 60 ° C. The obtained wet crystals were washed with water and dried at 80 ° C to obtain 17 g of an ammonium salt of a sulfonate yellow derivative sulfonate (1). The ammonium salt (1) of the quinone yellow derivative sulfonate is heat-treated at 180 ° C for 3 hours to obtain a quinoline yellow derivative sulfonate (2) having an ammonium salt removed [B (B) of the present invention has The quinophthalone compound (1) of a specific substituent: the following structure] 1 6 g (yield 94%). -68 - 201132711

(Synthesis Example 2: (B) Synthesis of Quinoline Yellow Compound (2)) In the chloroform, oxalyl chloride (manufactured by Wako Pure Chemical Industries, Ltd.) 2.2 g, N, N-dimethyl group was added under ice cooling. Indoleamine (manufactured by Wako Pure Chemical Industries, Ltd.) 1 mL of the sulfinyl yellow derivative sulfonate (2) [(B) quinoline yellow compound (1)] obtained in Synthesis Example 1 in 10 g at 50 ° C Stir for 2 hours. The reaction mixture was added to water at 150 ml, and the precipitated crystals were filtered to obtain a sulfonic acid chloride compound (3) [(B) a quinophthalone compound (2) having a specific substituent of the present invention: The following structure] 7.4 g. (yield 7 2 %)

-69 - 201132711 (Synthesis Example 3: Synthesis of (B) Quinoline Yellow Compound (3)) 6-chloro-1-hexylamine (manufactured by Rare Chemicals Co., Ltd.) 9.9 g was added to chloroform under ice cooling in Synthesis Example 2. The obtained quinoline sulfonate chloro compound (3) (5.0 g of the quinophthalone compound (3) having a specific substituent of the present invention (B) was stirred at room temperature for 2 hours. The reaction mixture was added to 150 mL of water, and the precipitated crystals were filtered, washed with water, and dried under reduced pressure to obtain a sulfonic acid decylamine alkyl chloride compound (4) [(B) quinine having a specific substituent of the present invention Phosphate yellow

(3): 4.3 g of the following structure. (yield 76%) CI

(Synthesis Example 4: (B) Synthesis of Quinoline Yellow Compound (4)) Quinoline Xanthosulfonamide Chloride Compound (4) obtained in Synthesis Example 3 [(B) Quinoline Yellow having a specific substituent of the present invention To 43 g of the compound (3)], excess water and anhydrous sodium sulfite (manufactured by Kanto Chemical Co., Ltd.) were added, and the mixture was heated at 18 ° C for 12 hours in an autoclave. After allowing to cool, the crystals were filtered to obtain sulfonamide alkylsulfonic acid compound (5) [. (B) quinolinyl compound (4) having a specific substituent of the present invention, 3.7 g. (yield 82%) -70 - 201132711 h〇3s

HN

Cl

Cl 0 (Synthesis of Synthesis Example 5·_(Β)quinoline yellow compound (5)) Triethylamine (manufactured by Wako Pure Chemical Industries, Ltd.) was added to methylene chloride under ice cooling.

*S and 4-chloro-1-butanol (manufactured by Tokyo Chemical Industry Co., Ltd.) 7. 7 g of quinoxazinsulfonylalkylsulfonic acid compound (5) obtained in Synthesis Example 4 (B) of the present invention has a specific substituent The quinoline yellow compound (4)] was stirred at room temperature for 2 hours at 5_0 g. The reaction mixture is added to a water filtration solution of 15 mL mL to obtain a chlorine-based compound salt-expanding compound (6) [(B) a porphyrin yellow compound (5) having a specific substituent of the present invention] 3. 8 g. (yield 6 9 %) -71 - 201132711

Λ/-〇ι

Cl Q| (Synthesis Example 6: Synthesis of (B) quinophthalone compound (6)) The quinoline yellow chloroalkyl sulfonate compound (6) obtained in Synthesis Example 5 [(B) of the present invention has a specific substitution In 3.8 g of the quinoline yellow compound (5), an excess amount of water and anhydrous sodium sulfite (manufactured by Kanto Chemical Co., Ltd.) were added, and the mixture was heated at 180 ° C for 12 hours in an autoclave. After allowing to cool, the crystals were filtered, washed with water, and dried under reduced pressure to obtain 3.2 g of the sulfonic acid compound (7) (the (B) quinoline compound (6) having a specific substituent of the present invention). (yield 80%) ho3s

Cl Cl (Synthesis Example 7: Synthesis of hydrazine compound i) First, Compound A was synthesized by the following scheme. -72-201132711 Ethylcarbazole (100.Og, 512.512 mol) was dissolved in 260 ml of chlorobenzene, and after cooling to 〇 ° C, aluminum chloride (70.3 g, 0.527 mol) was added. Then, o-tolyl chloride (81.5 g, 〇. 527 mol) was added dropwise over 40 minutes, the temperature was raised to room temperature, and stirred for 3 hours. Then, after cooling to 0 ° C, aluminum chloride (75.1 g, 0.563 mol) was added. 4-Chlorobutyryl chloride (79.4 g, 0.563 mol) was added dropwise over 40 minutes, warmed to room temperature, and stirred for 3 hours. A mixed solution of 156 ml of a 35 mass% hydrochloric acid aqueous solution and 3 92 ml of distilled water was cooled to 〇 ° C, and the reaction solution was dropped. After the precipitated solid was suction-filtered, it was washed with distilled water and methanol, and recrystallized from acetonitrile to obtain Compound A having the following structure (structure: yield: 1 64.4 g, yield 77%).

Next, using Compound A, Compound B was synthesized in the following scheme. Compound A (20.0 g, 47.9 mmol) was dissolved in 64 ml of tetrahydrofuran (hereinafter referred to as THF), and 4-chlorobenzenethiol (7.27 g, 50.2 mmol) and sodium iodide (0.7 g, 4.79 mmol) were added. Then, sodium hydroxide (2.0 g, 50.2 mmol) was added to the reaction liquid of -73 - 201132711, and the mixture was refluxed for 2 hours. Then, after cooling to 〇 ° C, a sodium methoxide 28% methanol solution (manufactured by Nippon Shokubai Co., Ltd.: 81^1-28) (11.18, 5 7.4 mm 〇l) was dropped over 20 minutes, and the temperature was raised to room temperature. And stirred for 2 hours. Then, after cooling to 0 °C, isoamyl nitrite (6.73 g '57.4 mmol) was added dropwise thereto over 20 minutes, and the mixture was heated at room temperature and stirred for 3 hours. The reaction solution was diluted in 120 ml of acetone, and the aqueous solution of 01N hydrochloric acid cooled to 0 was dropped. The precipitated solid was suction filtered and washed with distilled water. Then, it was recrystallized from acetonitrile to obtain Compound B (the following structure: yield: 170 g, yield: 64%).

Next, using Compound B, a ruthenium compound 1-74 was synthesized by the following scheme. 1-201132711 Compound B (18.0 g, 32.4 mmol) was dissolved in 90 ml of N-methylpyrrolidone, and triethylamine (3.94 g, 38.9 was added). Mm). Then, after cooling to 〇 ° C, ethyl ruthenium chloride (3. 〇 5 g, 38.9 mmol) was added dropwise thereto over 20 minutes, and the mixture was heated to room temperature and stirred for 2 hours. The reaction liquid was poured into 150 ml of distilled water cooled to 〇 ° C, and the precipitated solid was suction-filtered, washed with 200 ml of isopropyl alcohol cooled to 〇 ° C, and dried to obtain a ruthenium compound U having the following structure. The yield was 19.5 g and the yield was 9 9%).

Compound B

The structure of the obtained hydrazine compound 1 was identified by NMR. (^-NMR 400MHz CDC 13): 8 . 8 6 (s, 1 Η), 8.6 0 (s , 1 Η), 8 . 3 1 (d, lH, J = 8_0Hz), 8.8 1 (d, lH, J = 8.0 Hz), 7.5 1- 7.24 (m.l0H), 7.36 (q, 2H, 7.4 Hz), 3.24 - 3.13 (m, 4H), 2.36 (s, 3H), 2.2 1 (s, 3H), 1.50 (t, 3H, 7.4 Hz). (Preparation of fine pigments: Preparation of pigment (P-1)) A zinc halide phthalocyanine pigment (FASTGEN A110, manufactured by DIC Corporation) 100 weight 75 201132711 parts by volume, sodium sulfate 200 parts and 600 parts of diethylene glycol were placed in a double-arm type kneader and kneaded for 5 hours. The above mixture was poured into water (1 000 ml), and after removing the solvent and the inorganic salt, it was dried in an oven to obtain a fine pigment (P-1). The average primary particle diameter of the obtained pigment was observed by TEM, and the particle diameter was 2 3 n m. (Preparation Example 2 of Micronized Pigment: Production of Pigment (P-2)) The zinc halide phthalocyanine pigment used in the preparation example 1 was changed to an azo nickel complex pigment (E4GN-GT manufactured by Lanxess Co., Ltd.). The fine pigment (P-2) was obtained in the same manner as in Preparation Example 1 except for the other. The average primary particle diameter of the obtained pigment was observed by TEM, and the particle diameter was 20 nm. (Preparation Example 3 of Micronized Pigment: Preparation of Pigment (P-3)) The halogenated zinc phthalocyanine pigment used in the preparation example 1 was changed to copper phthalocyanine green pigment CI Pigment Green 36 (Rionol manufactured by Toyo Ink Co., Ltd.) Other than Green 6 YK), the fine pigment (P-3) was obtained in the same manner. The average primary particle diameter of the obtained pigment was observed by TEM, and the particle diameter was 21 nm. (Preparation of the fine pigments: Preparation of the pigment (P-4)) The halogenated zinc phthalocyanine pigment used in the preparation example 1 was changed to the isoporphyrin yellow pigment CI Pigment Yellow 139 (manufactured by BASF Japan) Other than the preparation example 1 of the "Paliotol" yellow D1819), the fine pigment (P-4) was obtained. The average primary particle diameter of the obtained pigment was observed by TEM, and the particle diameter was 2 6 n m. (Example 1). Preparation of Pigment Dispersion Composition (d-1) -76 - 201132711 (A) 9.2 parts of pigment (P-1) obtained in the above Preparation Example 1 as a pigment, Pigment (P-2) 3.5 (B) 2.3 parts of the compound (4) as a quinophthalone compound, 9.0 parts of Solsperse 24000GR (manufactured by Lubrizol Co., Ltd.) as a dispersing agent, and (C) propylene glycol monomethyl ether acetate as a solvent (hereinafter referred to as After mixing 6 parts of PGMEA), the pigment dispersion composition (d-Ι) was obtained by dispersing for 3 hours using a sand honing machine. When the viscosity of the obtained pigment dispersion composition was measured by an E-type viscometer, it was very stable at 9·2 mPa «S, and it was confirmed that good dispersion stability was obtained (Examples 2 to 18). Pigment dispersion composition (d- Preparation of 2 to d-18) In addition to the pigment and quinophthalone compound used in the preparation of the pigment dispersion composition (d-Ι), the pigments and quinoline yellow compounds shown in Tables 1 to 2 below are changed. Then, a pigment dispersion composition (d-2 to d-18) was obtained in the same manner as in the preparation example of the pigment dispersion composition (d-1). Further, the viscosity of each of the pigment dispersion compositions was measured in the same manner as in Example 1. As a result, the expressions of Table 1 (Examples 19 to 24) were prepared by dispersing the pigment dispersion composition (d-19 to d-24). In the preparation of the pigment dispersion composition (d-Ι), the pigment and the quinoline yellow compound were changed to the pigments and quinophthalone compounds shown in the following Tables 1 to 2, and the amount of the dispersant Solsperse 24000GR was changed to 7.2 parts. The pigment dispersion composition (d-19 to d-24) was obtained in the same manner as in the preparation example of the pigment dispersion composition (d-Ι), except that the amount of the solvent (PG) was changed to 77. -77 - 201132711 Further, the viscosity of each of the pigment dispersion compositions was measured in the same manner as in Example 1. The results are shown in Table 1. (Comparative Examples 1 to 4) Preparation of Pigment Dispersion Composition (d-25 to d-28) In addition to the preparation of the pigment dispersion composition (d-Ι), the pigment and the quinoline yellow compound were changed to the following Table 1 In the same manner as the preparation example of the pigment dispersion composition (d-Ι), the pigment dispersion composition (d-25 to d-28) was obtained in the same manner as the pigment and the quinophthalone compound shown in Table 2. Further, the viscosity of each of the pigment dispersion compositions was measured in the same manner as in Example 1. The results are shown in Table 1. (Comparative Examples 5 to 8) Preparation of Pigment Dispersion Composition (d-29 to d-32) In addition to the preparation of the pigment dispersion (d-Ι), the pigment and the quinoline yellow compound were changed to the following Table 1 to The pigment and the porphyrin compound shown in Table 2 were prepared by changing the amount of the dispersant Solsperse 24000GR to 7.2 parts, (D) changing the solvent PGMEA to 77.8 parts, and other pigment dispersion composition (d-;!). In the same manner, a pigment dispersion composition (d-29 to d-32) was obtained. Further, the viscosity of each of the pigment-dispersed compositions was measured in the same manner as in Example 1. The results are shown in Table 1. (Comparative Example 9) Preparation of Pigment Dispersion Composition (d-33) In addition to the preparation of the pigment dispersion composition (d-1 3), the pigment (p-4) was replaced with a non-micronized treatment. A pigment dispersion composition (d-33) was obtained in the same manner as in the preparation example of the pigment dispersion composition-78-201132711 (dl), except that the porphyrin-based yellow pigment CI Pigment Yellow 139 (average primary particle diameter: 48 nm) was used. The viscosity of the obtained pigment dispersion composition is measured by an E-type viscosity meter, which is 31.2 mP a -79 - 201132711 [I 撇 initial viscosity (mPa * s) (N as 00 σ\ σ\ Bu Os rH ro Os 00 10.7 rn x&gt;&lt;N o VO 00 v〇14.0 11.3 丨10.5 卜σ\ 10.1 00 TH inch: OO oo 12.4 o 00 OO (B) porphyrin yellow compound 00 1·^ (Ν (Ν Ά CN v 〇oo 1-H CN (N VO oo (N (Ν Ό Ό oo (N 00 &lt; N (N VO iS (8) pigment 2 m (N (Ν 00 寸 1 I 1 1 m (N (N 00 inch m ( N CN OO inch 00 00 *—H 1 1 1 1 1 1 (8) Pigment 1 v〇s V〇σ\ v〇&lt;N oo fN s V〇VO vo VO v〇s CS OO jn (N OO OO material ( B) Quinoline yellow compound Compound (4) Compound (4) Compound (4) Compound (4) Compound (4) Compound (4) Compound (4) Compound (4) Compound (4) Compound (4) Compound (4) Compound (4) 4) Compound (4) Compound (4) Compound (4) Compound (4) Compound (6) Compound (1) Compound (4) Compound (4) Compound (4) Compound (4) Compound (4) Compound (4) (A) Pigment 2 ( N ώ (N PU (Ν Lη (Ν cL 1 1 1 1 P-2 cs ώ &lt;N p!h (N pi Oh Oh CL, CN pi &lt;N 1 1 1 1 1 1 (A) Pigment 1 fH »—Η ρ!η ^-Η P-2 P-2 P-2 P-2 r〇ώ ro cL pi F—Η pi H ώ cL cn pi CO Oi Cn pi pigment dispersion composition CN T3 &quot;ώ i〇T3 卜 TJ 00 On -ύ d-10 d-11 d-12 d-13 d-14 d-15 d-16 d-17 d-18 d-19 D-20 d-21 d-22 d-23 d-24 Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 Example 9 Example 10 Example 11 Example 12 Example 13 Example 14 Example 15 Example 16 Example 17 Example 18 Example 19 Example 20 Example 21 Example 22 Example 23 Example 24 201132711 [一漱] Initial viscosity (mPa - s) 55.0 43.9 51.0 44.6 44.6 38.2 41.3 38.0 31.2 Conversion ratio (mass basis) (B) Quinoline yellow compound in ο *0 o (A) Pigment 2 ON CN 1 1 1 1 1 1 CO &lt;N (A) Pigment 1 ON 92.5 &lt;3\ § On 92.5 Material (B) Quinoline Yellow Compound Compound (4) Compound (4) Compound (4) Compound (4) Compound (4) Compound (4) Compound (4) Compound (4) Compound ( 4) (A) Pigment 2 CS (N 1 1 1 1 1 1 Pigment Yellow 139 (A) Pigment 1 ρ!η P-2 & Nt rn 1 Ph pigment dispersion composition d-25 d-26 d-27 d-28 d-29 d-30 d-31 d-32 d-33 Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparison Example 5 Comparative Example ό Comparative Example 7 Comparative Example 8 Comparative Example 9 201132711 It is apparent from Tables 1 to 2 that the pigment dispersion composition of the present invention, (A) the pigment and (B) the quinoline yellow compound having a specific substituent The balance of the blending amount is appropriate, regardless of the type of the pigment, and all of them are low in viscosity and good in dispersibility and dispersion stability. Further, as shown in Examples 17 and 18, the (B) quinophthalone compound is preferably a compound having a structure within the scope of the present invention, and the dispersion stability is also good. On the other hand, it is understood that the pigments of Comparative Example 9 in which the ratio of the pigment (A) to the (B) quinophthalone compound is outside the range of the present invention and the pigment having an average primary particle diameter outside the range of the present invention The dispersed composition is a substance having high viscosity and poor dispersion stability. (Example 25) Preparation of colored photocurable composition (R-1) By mixing the components described in the following compositions, a colored photocurable composition (R-1) can be obtained. - Composition _ Pigment Dispersion Composition (d-1) 10.74 parts of pigment dispersion composition (d-5) 3.65 parts of alkali-soluble resin (Allyl-MA/MAA = 8 0/2 0 Mw. 3 0,000) 0.25 part of polymerizable compound Aronics Μ-5 1 0 (manufactured by Toagosei Co., Ltd.) 1.33 parts of polymerization initiator IRGACUREOXE01 (manufactured by BASF Japan) 0.37 parts of surfactant megafac F-5 54 (manufactured by DIC Corporation) 〇.1 part of propylene glycol monomethyl ether acetate Ester (PGMEA) 8.65 parts - 82 - 201132711 3-ethoxypropionate ethyl ester (EEP) 5.00 parts (Examples 26 to 47, Comparative Examples 10 to 17) Colored photocurable composition (R-2 to R-) 32) The coloring was obtained in the same manner as in Example 25 except that the type of the pigment dispersion used in the colored photocurable composition (R-1) was changed to the pigment dispersions shown in the following Tables 3 to 6. Photocurable composition (R_ 2 to R-3 2). Further, in the following Tables 3 to 6, the formulated pigment dispersion composition is referred to as "dispersion 1" and "dispersion 2", and the symbols of the pigment dispersion composition used are described. The evaluation of the colored photocurable composition obtained in Examples 25 to 5 was carried out based on the following criteria. The results are shown in Tables 3 to 6. (Evaluation of contrast and lightness) The coloring photosensitive composition (color resist liquid) was applied to a glass substrate (manufactured by EAGLE2000, manufactured by Corning Co., Ltd.) of 100 mm x 100 mm so that the film thickness after drying was 2·0 μm, at 90 ° C. The oven is dried for 100 seconds (prebaking). Thereafter, the mask was exposed at 60 mJ/cm 2 (illuminance: 20 mW/cm 2 ), and the exposed coating film was treated with an alkali developer CDK-1 (manufactured by Fuji Film Electronic Materials Co., Ltd.) in an aqueous solution (25 ° C). ) Spread for 60 seconds in a spray. Thereafter, it was sprayed with pure water in a spray form, and the developing solution was washed, and the substrate was heated in a baking oven for 30 minutes (after baking) to prepare a colored photosensitive composition on the surface of the glass substrate. A substrate for measurement of a colored layer. (Lightness: Y値) -83 - 201132711 The chromaticity of the obtained substrate was measured by MCPD-2000 (manufactured by Otsuka Electronics Co., Ltd.), and the brightness was judged by γ値. The larger the number, the higher the brightness is judged to be good. (Comparative) The obtained substrate was sandwiched between two polarizing plates, and BM-5A made of T〇pCon (strand) was used to measure the brightness of the two deflecting plates when the deflection axes were parallel and the brightness at the time of orthogonality. The luminance obtained by dividing the luminance in parallel with the luminance at the time of orthogonal (= luminance in parallel/luminance in orthogonal) is used as an index for evaluation comparison. 84_201132711 [ε ϊ Evaluation results comparison 23000 23500 22500 23000 22500 22800 1 '23000 23200 23300 22000 16100 17000 Chromaticity 57.0 57.3 i 57.7 58.1 56.5 56.7 57.0 57.3 58.2 57.9 56.4 56.6 0.599 0.599 0.599 0.599 0.599 0.599 0.599 0.599 0.599 0.599 0.599 0.599 X 0.280 0.280 0.280 0.280 0.280 0.280 1 0.280 0.280 0.280 0.280 0.280 0.280 m M gsi Rong f chain &lt;ίπ 譃g Way - S photosensitive composition (B) ratio 00 (N v〇oo oo &lt;N dispersion 2 3.60 3.52 ; 3.44 3.39 1.50 1.42 1.34 1.26 3.52 3.52 3.60 3.60 Dispersion 1 10.69 | 10.77 10.85 10.9 10.69 10.77 10.85 10.9 10.77 10.77 10.69 10.69 β R gs I 1 1 ^ I s mushroom | | Departure 1 魆® Dispersion 2 (B) Ratio 00 00 00 00 oo 00 00 00 00 00 00 00 Dispersion 1 (B) Ratio oo &lt;N VO 00 (N in o Dispersion 2 d-19 ... 1 d-19 d-19 d-19 D-19 d-19 d-19 d-19 d-19 d-19 d-19 d-19 Dispersion 1 &lt;N CO T3 d-13 d-14 d-15 d-16 d-17 d-18 D-25 d-26 Rl R-2 ώ R-4 R-5 R-6 R-7 R-8 R-9 R-10 R-ll R-12 Example 25 Example 26 Example 27 Implementation 28 Example 29 Example 30 Example 31 Example 32 Example 33 Example 34 Comparative Example 10 Comparative Example 11 201132711 [Inch 漱] Comparison of evaluation results 22000 22300 23000 15300 15700 Chromaticity 57.2 57.3 57.6 56.5 56.4 &gt;. 0.599 0.599 0.599 0.599 0.599 X 0.280 0.280 0.280 0.280 0.280 ^ S ss 8· | If si I 1 Seven sky ϊ ® S g Photosensitive composition (B) Ratio 〇〇ο m Dispersion 2 3.65 3.73 3.89 3.49 3.57 Dispersion 1 10.74 10.66 10.5 10.9 10.82 y Iff and ΛΛ 擗 擗 B &lt;(ra S s I loose chain &lt;π m 翠谥u 魅一分散物 2 (9) ratio dispersion 1 (B) ratio 00 CN in o dispersion 2 1 ^0 X3 v〇v〇&quot;0 Dispersion 1 d-19 d-20 1 1 d-21 d-29 d-30 R-13 R-14 R-15 R-16 R-17 Example 35 Example 36 Implementation Example 37 Comparative Example 12 Comparative Example 13 201132711 [5 ϊ Comparison of evaluation results 21900 22300 22000 16300 16600 Color 57.0 | 57.7 58.2 56.5 56.5 &gt;&gt; 0.599 0.599 0.599 1 0.599 0.599 0.280 0.280 1 0.280 0.280 0.280 ^ SS遄If is 1 2 δ 1 ® photosensitive composition (Β) ratio b &lt;;^1 inch dispersion 2 3.69 3.78 On cn 3.57 3.57 Dispersion 1 10.7 10.61 10.49 ! 10.82 10.82 擗 擗 M &lt;ID ss 松松链&lt;ίπ 谥舾Φ 荽GONG 1 Charm 5 Disperse 2 j (B ) Ratio CN ^ Ti Dispersion 1 (B) Ratio VO VO Dispersion 2 - ό 00 i d-27 d-28 Dispersion 1 d-19 d-19 d-19 1 d-19 d-19 R-18 R-19 R-20 R-21 R-22 Example 38 Example 39 Example 40 Comparative Example 14 Comparative Example 15 201132711 [9撇] Comparison of evaluation results 25000 25200 25700 25500 25600 26000 26100 17000 17500 Chromaticity 56.0 : 56.1 56.4 56.1 1 56.5 56.7 57.2 55.5 55.7 0.599 0.599 0.599 0.599 0.599 0.599 0.599 0.599 0.599 X 0.280 0.280 0.280 I 0.280 0.280 0.280 0.280 0.280 0.280 ^ S ss If ^ 15 g δ | ® ® S&quot; Photosensitive composition (B) ratio CN in Cs 卜〇〇o (N Dispersion 2 3.65 3.73 3.89 V〇rn 3.52 3.44 3.39 V〇cn 分散 Dispersion 1 10.74 10.66 10.5 10.69 10.77 10.85 10.9 10.69 10.69 , 撒诹0 &lt;ΙΠ S g 1 蓉链4 〇玄存1 Gong Meiyi Disperse 2 (B) Ratio 00 〇〇〇〇 〇〇Dispersion 1 (9) Ratio 00 &lt;N (N \〇(N 00 (N Dispersion 2 VO T3 vo Τ3 vo -6 d-22 1 d-22 d-22 d-22 V〇T3 Dispersion 1 d -22 d-23 d-24 Os T3 d-10 d-11 d-12 d-31 d-32 R-23 R-24 R-25 R-26 1 R-27 R-28 R-29 R-30 R-31 Example 41 Example 42 Example 43 Example 44 Example 45 Example 46 Example 47 Comparative Example 16 Comparative Example 17 201132711 It is apparent from Tables 3 to 6 that the coloring photosensitive composition containing the pigment dispersion composition of the present invention In Examples 25 to 47 of the composition, a good color hardening layer (corresponding to a coloring pattern of a color filter) was obtained in both brightness and contrast. On the other hand, it was found that the colored cured film obtained by using the colored photosensitive composition of Comparative Examples 1 to 8 (Comparative Examples 10 to 17) was inferior in brightness and contrast. (Examples 48 to 59) Preparation of coloring photocurable composition (R-32 to R-43) In addition to the pigment dispersion composition used in the color-light-curable composition of Example 36 (R14), polymerizability The components other than the compound and the solvent were changed to the materials described in the following Table 7, and the colored photocurable compositions (R_32 to R-43) were obtained in the same manner. The results of the evaluation of the colored curable composition in the same manner as in Example 25 are described in the following Table 7. -89 - 201132711 [Di Bao] Comparison of evaluation results 22300 22300 22400 22300 22100 22300 22300 22300 22300 22400 22300 22300 Chromaticity 57.3 57.3 57.2 57.3 57.0 57.2 56.8 57.0 57.2 56.9 57.0 0.599 0.599 0.599 0.599 0.599 0.599 0.599 1 0.599 0.599 0.599 0.599 0.599 0.599 X 0.280 0.280 0.280 0.280 I 0.280 0.280 1- 0.280 0.280 0.280 0.280 0.280 0.280 0.280 Coloring photosensitive composition prescription additive 4 ! 0.14 Additive 3 〇 0.11 Additive 2 0.11 Additive 1 0.22 0.22 0.22 0.22 0.22 0.22 0.22 0.22 0.22 Polymerization initiator 6 0.06 0.06 0.06 0.03 0.04 0.04 0.04 Polymerization initiator 5 0.28 0.28 0.28 0.14 0.19 0.19 0.19 Polymerization initiator 4 0.20 0.20 0.20 0.10 0.14 0.14 0.14 Polymerization initiator 3 0.37 0.18 Polymerization initiator 2 0.37 0.18 Polymerization initiator 1 0.37 0.37 0.37 0.37 0.28 0.18 Alkali Soluble Resin 0.44 0.22 _1 0.32 0.32 0.03 0.14 0.01 0.22 0.22 0.03 0.03 0.03 0.03 R-14 R-32 R-33 R-34 R-35 R-36 R-37 R-38 R-39 R-4 0 R-41 R-42 R-43 Embodiment 12 Embodiment 48 Embodiment 49 Embodiment 50 Embodiment 51 Embodiment 52 Example 53 Example 54 Example 55 Example 56 Example 57 Example 58 Example 59 06 - 201132711 In addition, the details of each component described in Table 7 are as follows. Polymeric compound: Aronics M-510 Alkali-soluble resin: (Allyl-MA/MAA = 80/20 Mw.30, 〇〇〇) Initiator 1: IRGACURE OXE01 (manufactured by BASF Japan) Initiator 2: IRGACURE OXE02 (BASF Initiator 3··肟 compound (1) (obtained in Synthesis Example 7) Initiator 4: B-CIM, initiator of Hodogaya Chemical Co., Ltd. 5: Compound of the following structure (1〇) Agent 6: N-phenylhydrothiobenzimidazole Additive 1: Oxygen azo (Azoxy) Anisole Additive 2: Adecastab AO-60 Additive 3: Adecastab LA-52 Additive 4: EHPE-3150 Surfactant: Megafac F-554

Compound (10) As shown in Table 7, it is understood that the color-sensitive photosensitive composition (R-3 2 to R-43) of the present invention can form a lightness and a good contrast even in a different polymerization initiator or additive. The colored cured film is extremely useful for forming a colored pattern of a color filter. (Comparative Example 1 8) -91 - 201132711 Preparation of Colored Photocurable Composition (R-44) In addition to the kind of pigment dispersion used in the colored photocurable composition (R-1), Table 3 above is used. The colored photocurable composition was obtained in the same manner as in Example 29 except that the pigment dispersion composition (d-13) shown in Example 9 was changed to the pigment dispersion composition (d-3 3) used in Comparative Example 9. (R_44). The colored curable composition (R-44) was evaluated in the same manner as in Example 25. As a result, the chromaticity (X, y, Y) of the substrate and the comparison were as follows. x: 0.280, y: 0.599, Υ: 56·0, comparison 11200 In the comparison of Example 48 to Example 59 and Comparative Example 18, it is understood that the average primary particle diameter of the pigment used is Comparative Example 1 outside the scope of the present invention. The color hardening film of 8 is poorly contrasted. (Example 60) [Production of color filter] 1. Formation of coloring curable composition layer The coloring curable composition (R-3) containing the pigment obtained above was used as a photoresist liquid, and black was set at 550 mm x 650 mm. The glass substrate of the matrix was subjected to slit coating under the following conditions, and then vacuum dried (66 Pa) and prebake (9 (TC 1 sec)) to form a colored curable composition coating film (color hardening property) Composition layer) (Gap coating condition) Clearance of opening end of coating head: 1〇〇μιη Coating speed: 1 50mm/sec Clearance between substrate and coating head: 15〇μπι -92 - 201132711 Coating thickness (dry thickness) : 2 μιη Coating temperature: 2 3 ° C 2. After exposure and development, a coloring curable composition layer was exposed to a pattern at 60 mJ/cm 2 using a proximity exposure machine (manufactured by Hitachi High-Technologies Corporation, LE 5 565A). A 1000% aqueous solution (25 ° C) of an inorganic developer (trade name: CD K-1, manufactured by Fuji Film Electronic Materials Co., Ltd.) was set at a spray pressure of 0.2 MPa to complete the coloring and hardening composition layer after exposure. Developed for 60 seconds and is pure Washing 〇 3. Heat treatment 'Pure pure water is sprayed on the colored curable composition layer, and the developer is rinsed, followed by heating in an oven at 23 ° C for 30 minutes (post-baking). a green coloring pattern is formed on the surface. 4. The red and blue coloring patterns are formed, and then a blue coloring hardening composition (CB-9500L; Fujifilm electronic material) is used to form a colored pattern. A red color-curing composition (CR-9500L, manufactured by Fuji Film Electronic Materials Co., Ltd.) forms a colored pattern, and ITO is deposited by using a photopolymerizable composition (CSP-3210L: Fujifilm Electronic Materials Co., Ltd.) A spacer was formed, and a color filter (1) having green, red, and blue colored patterns (pixels) was obtained on the substrate. (Comparative Example 19) Except that in Example 60, it was used as a photoresist. The colored curable composition (R-3) was changed to the colored curable composition (Ri 1)-93 - 201132711 used in Comparative Example 10, and a colored pattern was formed in the same manner to obtain a color filter (2). Performance evaluation Price) In the 550mm x 650mm substrate, measure the chromaticity of the green pixel portion at the 12 points (each referred to as coordinates (1) to (12)) shown in Fig. 1, where y値[(maximum 値)-(minimum値)]=yrange is used as an indicator for color unevenness evaluation. In addition, the coordinates are as shown in Table 8 below. [Table 8] Coordinates XY (1) 100 325 (2) 2 17 325 (3) 3 3 4 325 (4) 450 325 (5) 275 100 (6) 275 164 (7) 275 228 (8) 275 292 (9) 27 5 3 56 (1〇) 275 420 (11) 275 484 (12) 275 550 here It is known that the color unevenness of the color filter (1) obtained in Example 60 is yrange = 〇.〇〇2, and it can be confirmed as a color filter having a uniform color characteristic of -94 - 201132711. Next, when the color unevenness of the color filter (2) of Comparative Example 19 was evaluated, it was yrange = 0.010, which was a film having unevenness in color unevenness. (Comparative) The obtained color filter (1) and color filter (2) were sandwiched between two polarizing plates, and the deflection axis of the two deflecting plates was measured using BM-5A manufactured by Topcon. The luminance in parallel and the luminance in the orthogonal direction are obtained by dividing the luminance in parallel by the luminance in the orthogonal direction (= luminance in parallel/luminance in quadrature) as an index for evaluation comparison. The color filter (1) obtained in Example 60 and the color filter (2) obtained in Comparative Example 19 were evaluated by the above methods, and the respective comparisons were 45 〇 0, 36 〇 0. From this, it was confirmed that the color filter (1) of the present invention is extremely excellent in contrast. &lt;Liquid Crystal Display Element&gt; When the color filter (1) obtained in Example 60 is incorporated in a liquid crystal display element, it is confirmed that the liquid crystal display element, color characteristics, and contrast are excellent. [Simplified illustration] Fig. 1 In the color unevenness test, a plan view showing the coordinates at the colorimetric measurement in a 550 mm x 650 mm substrate. [Main component symbol description] 4nr No 0 • 95 -

Claims (1)

201132711 VII. Patent application scope: 1. A pigment dispersion composition characterized by containing (A) a pigment having an average primary particle diameter of 10 to 30 nm, and (B) having at least one selected from the group consisting of a hydroxyl group, a carboxylic acid group, and a sulfonic acid group. a quinoline yellow (quin〇Phthal〇ne) compound of the amine group and the salt of the salt, and (C) a solvent, the ratio of the (A) pigment to the (B) quinoline yellow compound using a mass basis [ A): (B) is in the range of (A): (B) = 85:15 to 1 0:90. 2. The pigment dispersion composition of claim 1, wherein the content ratio of the (A) pigment to the (B) quinoline yellow compound by mass basis [(A): (B)] is in (A) :(B) = range from 82:18 to 15:85. 3. The pigment dispersion composition of claim 1, wherein the content ratio of the (A) pigment to the (B) porphyrin compound by mass basis ((A): (B)) is (A) : (B) = the range of 80:20 to 20:80. 4. The pigment dispersion composition of claim 1, wherein the (A) pigment is selected from the group consisting of quinoline yellow pigments At least one of a group consisting of a pigment, an azo complex, a metal phthalocyanine green pigment, a diketone oxime, a ruthenium pigment, and an anthraquinone pigment. The pigment dispersion composition % of the item, wherein the (Α) pigment is at least selected from the group consisting of copper phthalocyanine pigments, zinc phthalocyanine pigments, azo-based anthraquinone pigments, and isoporphyrin pigments. A pigment dispersion composition according to the first aspect of the invention, wherein the (Α) pigment is a k-kneaded material in the presence of an inorganic salt and a solvent. a pigment dispersion composition in which the 丨Α) 颜-96 - 201132711 is present in the presence of inorganic salts, solvents, and pigment derivatives Treated pigment was kneaded. 8. The pigment dispersion composition of claim 7, wherein the pigment derivative is the (B) quinoline yellow compound. 9. The pigment dispersion composition of claim 1, wherein the (B) quinoline yellow compound is a compound represented by the following formula (1), R2 R1 X7 V (In the formula (1), X1 to X8 each independently represent a hydrogen atom, a chlorine atom, or a bromine atom; and R1 to R4 each independently represent a hydrogen atom, -〇CnH2n-Y, -S03CnH2n-Y -S02NHCnH2n-Y, -C02CnH2n-Y '-NHCOCnH2n-Y, or -N(CnH2n-Y)2, not all of which are hydrogen atoms; n represents an integer from 〇 to 20; Υ represents a hydrogen atom, -〇H,- S03H, -C02H, -co2_[nh4]+, -so3 - [nh4]+, or -N(R5)2; R5 represents a hydrogen atom or an alkyl group having 1 to 2 carbon atoms. a colored photosensitive composition characterized by containing (D) a polymerizable compound '(E) a photopolymerization initiator, and, as in the patent application No. 1 to 9, any one of -97 - 201132711 Pigment dispersion composition. 11. A method of producing a color filter, comprising: providing a photosensitive film of a photosensitive film directly or via another layer to a colored photosensitive composition according to claim 10 of the patent application; a forming step; a coloring pattern forming step of forming a colored pattern by sequentially performing pattern exposure and development on the formed photosensitive film. A color filter comprising a colored pattern obtained by the method of producing a color filter according to the first aspect of the patent application. A display device comprising a color filter as in claim 12 of the patent application. A solid-state photographic element which is provided with a color filter as in claim 12 of the patent application. -98 -