JPH08179111A - Colored composition for color filter and color filter - Google Patents

Abstract

PURPOSE: To obtain a colored composition for producing an optical color filter to be used for liq. crystal color display, video camera, etc., and to obtain a color filter using the composition. CONSTITUTION: The colorant is an org. pigment. The org. pigment, a water-soluble inorg. salt A and a water-soluble org. solvent B wherein the A is not substantially dissolved are mechanically kneaded, and the A and B are removed to obtain a treated pigment to be used as the colored composition for a color filter. The color filter is formed by using the composition.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a coloring composition for producing an optical color filter used for liquid crystal color displays, video cameras and the like, and a color filter using this coloring composition. More specifically, it relates to a coloring composition for a color filter for forming a pattern portion generally called a stripe filter or a matrix filter.

[0002]

2. Description of the Related Art A color filter is one in which fine bands (stripe) of two or more different hues are arranged in parallel or intersecting on the surface of a transparent substrate such as glass, or fine pixels are arranged in a constant vertical and horizontal directions. It is made up of those placed in. The pixel size is a minute shape of several tens to several hundreds of microns, and moreover, it is arranged in order in a predetermined order for each hue. For this reason, various methods have been conventionally proposed for manufacturing color filters. Since a color filter is required to have high transparency, a dyeing method, which is generally called a dyeing method, is used.
For example, a dyeable photosensitive material is applied to a substrate such as glass, and then pattern exposure of one filter color is performed, then the unexposed portion is washed off in a developing process, and the remaining pattern portion is exposed to the filter color. A color filter can be manufactured by sequentially repeating an operation of dyeing with a dye for all filter colors. This method has a high transmittance because it uses a dye, and the optical characteristics of the color filter are very excellent, but there are limits to light resistance, heat resistance, etc., and a coloring material with excellent resistance and high transparency is desired. It was

Therefore, instead of dyes, organic pigments having excellent light resistance and heat resistance have come to be used. For example, in a color filter in which three primary colors of light of blue, green, and red are arranged on a transparent substrate. In general, it is difficult to obtain a spectral spectrum as a color filter using only a single pigment, and it is necessary to adjust using two or more pigments. For blue, copper phthalocyanine blue pigment, which has excellent resistance, is generally used, but it is difficult to obtain a sufficient spectrum with only a single copper phthalocyanine, so the spectrum is adjusted by mixing violet pigment. Regarding green, phthalocyanine green, which has excellent resistance, is generally used. However, as with blue, a single green pigment alone does not provide sufficient spectral characteristics. I am adjusting. As for red, there is no single pigment that has sufficient absorption in a wide wavelength range of 400 nm to 600 nm. Therefore, the spectrum is adjusted by adding a yellow pigment and / or an orange pigment.

In a liquid crystal display, a liquid crystal layer sandwiched between two polarizing plates controls the degree of polarization of light passing through the first polarizing plate, and controls the amount of light passing through the second polarizing plate. A type using twisted nematic (TN) type liquid crystal, which performs display by doing so, is the mainstream. A color filter is provided between the two polarizing plates to enable color display. Generally, a color filter in which an organic pigment is dispersed has a polarization degree controlled by the liquid crystal due to light scattering by pigment particles. There is a problem of being disturbed. That is, there is a phenomenon in which light leaks when light must be blocked (OFF state), and transmitted light is attenuated when light must be transmitted (ON state). The brightness ratio on the display in the ON state and the OFF state is called the contrast ratio, and it is known that the yellow and orange pigments significantly reduce the contrast ratio (Ueki, et al, Proceedi).
ngof the 7th Conference on Color Tehnology, pp. 89
-98 (1990)).

The present inventors have paid attention to the fact that the transparency and the contrast ratio are improved by making the primary particles of the pigment used in the coloring composition for the color filter finer, and arrived at the present invention. In ordinary paints and inks, transparency is generally improved by increasing the dispersibility of pigments, but in ordinary dispersers such as sand mills, three-roll mills, and ball mills, even more transparent when primary particles are dispersed. Will not rise. The dispersion process using an ordinary disperser is a process that mainly loosens the secondary particles, which are aggregates of the primary particles of the pigment, to obtain a dispersion in a state close to the primary particles. To further improve transparency, Needs to make the primary particles finer.

[0006] The high speed sand mill is excellent in making fine particles of the pigment, and depending on the pigment, it is possible to make the primary particles fine, but in this case, a very large amount of energy is required.
As a means for making the primary particles finer, a method is known in which a pigment dissolved in a strong acid such as concentrated sulfuric acid or polyphosphoric acid is put into cold water or ice water to precipitate the pigment as fine particles. The pigments that can be used are remarkably limited in terms of solubility and stability of the pigment in a strong acid. In addition, since the pigment finely divided by this method causes strong secondary agglomeration when dried, it is generally very difficult to redisperse the primary particles.

As another method, there is known a method in which a pigment and a solid resin are heated and kneaded strongly with a two-roll or kneader. However, since pigments generally grow crystals at high temperatures, this method reaches the end point when the mechanical crushing force and the crystal growth are in equilibrium, and there is a limit to the miniaturization of pigments.

[0008]

SUMMARY OF THE INVENTION An object of the present invention is to solve the above-mentioned problems and to provide a coloring composition for a color filter and a color filter having a high contrast ratio and excellent durability.

[0009]

That is, the present invention provides a coloring composition for a color filter comprising a transparent resin and a colorant dispersed therein, wherein the colorant is an organic pigment, and the organic pigment is a water-soluble inorganic salt ( After mechanically kneading (A) and (A) with a water-soluble organic solvent (B) that does not substantially dissolve (hereinafter, this step is referred to as salt milling), (A) and (B)
By using a treated pigment obtained by removing the above, a color filter having a high contrast ratio and a coloring composition for a color filter used therefor are provided. Further, by using a treated pigment in which a resin (C) which is at least partially dissolved in (B) during salt milling is used, a colored composition for a color filter and a color filter having a higher contrast ratio can be provided.

More specifically, the salt milling is more specifically carried out by adding a small amount of a water-soluble organic solvent (B) as a wetting agent to a mixture of an organic pigment and a water-soluble inorganic salt (A), and kneading with a kneader or the like. After that, the mixture is put into water,
Stir with high speed mixer etc. to make slurry. Next, this slurry is filtered, washed with water, and optionally dried to obtain a finely divided pigment. When dispersed and used in an oil-based varnish, it is possible to disperse the treated pigment before drying (called a filter cake) in the oil-based varnish while removing water by a method generally called flushing. Further, when dispersed in an aqueous varnish, the treated pigment does not need to be dried, and the filter cake can be directly dispersed in the varnish. Further, by using the resin (C) which is at least partially soluble in the organic solvent (B) at the time of salt milling, it is possible to obtain a finer treated pigment with less aggregation of the pigment during drying. As a method for preventing dry agglomeration, an alkali-soluble resin dissolved in an aqueous alkali solution is added to the above slurry, sufficiently mixed with stirring and then neutralized with an acidic aqueous solution such as hydrochloric acid or sulfuric acid to deposit the resin on the pigment, or calcium chloride. Alternatively, it is possible to prevent dry aggregation by adding an aqueous solution of a water-soluble polyvalent metal salt such as barium chloride to deposit the resin and deposit it on the pigment.

The treated pigment is dispersed together with a transparent resin and a solvent for forming a color filter and, if necessary, a dispersant in an ordinary disperser such as a sand mill or a three-roll mill to obtain untreated (no salt milling). )
As compared with the case of using a pigment, a coloring composition for a color filter in which the pigment is finely dispersed can be obtained. The organic pigments used in the present invention are shown below in color index (CI).
Indicate by number. C. I. Pigment Blue 1,1: 2,1: x, 9: x, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 5, 15: 6, 16, 24, 24: x, 56, 60, 61, 62 C.I. I. Pigment Green 1,1: x, 2,2: x, 4,7,10,36 C.I. I. Pigment Orange 2, 5, 13, 16, 17: 1, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 59, 60, 61, 62, 64 C.I. I. Pigment Red 1,2,3,4,5,6,7,9,10 14,17,22,23,31,38,41,48: 1,48: 2 48: 3,48: 4,49, 49: 1, 49: 2, 52: 1, 52: 2, 53: 1, 57: 1, 60: 1, 63: 1, 66, 67 81: 1, 81: 3, 81: x, 83,88 , 90, 112, 119, 122, 123, 144, 146, 149, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 200. , 202, 206, 207, 208, 209, 210, 216, 224, 226, C.I. I. Pigment Violet 1,1: x, 3,3: 3,3: x, 5: 1,19,23,27,32,42 C.I. I. Pigment Yellow 1,3,12,13,14,16 17,24,55,60,65,73,74,81,83,93,95,97,98,100,101,104,106,108,109. , 110, 113, 114, 116, 117, 119, 120, 126, 127, 128, 129, 138, 139, 150, 151, 152, 153, 154, 156, 175 These pigments may be used alone or in combination of two or more. The salt milling treatment can be performed, but pigments having different hues such as green pigment and yellow pigment, red pigment and orange pigment, or yellow pigment can also be mixed and treated.

The inorganic salt (A) used here is not particularly limited as long as it is water-soluble, but it is preferable to use salt (sodium chloride) from the viewpoint of cost. Regarding the mixing ratio of the inorganic salt and the pigment, the higher the amount ratio of the inorganic salt to the pigment is, the higher the micronization efficiency is, but the treatment amount of the pigment per one time becomes small. Therefore, it is necessary to determine the amount ratio from both aspects of treatment efficiency and production efficiency, but it is preferable to use the inorganic salt in a weight ratio of 1 to 10 times with respect to the pigment. The solvent is not particularly limited as long as it is an organic solvent (B), water-soluble and does not dissolve the inorganic salt (A), but the temperature rises during salt milling and the solvent easily evaporates. High boiling solvents are preferred. For example, 2-methoxyethanol, 2-butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene Glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, low A molecular weight polypropylene glycol or the like is used.

The resin (C) is preferably solid at room temperature,
It must be water-insoluble and at least partially soluble in the water-soluble organic solvent (B) used as the wetting agent during salt milling. Natural resin, modified natural resin, synthetic resin, synthetic resin modified with natural resin Etc. are used. When using the dried treated pigment, the resin (C) used is preferably solid at room temperature. Although salt milling can be performed using a liquid resin at room temperature, it is not preferable because the treated pigment causes blocking during drying and is difficult to disperse. However, the flushing method and the aqueous dispersion described above are not preferable. Can be obtained. However, when two or more kinds of resins are used together for salt milling, the treated pigment may be dried and used even if a part of the liquid resin is used and the mixture is solid at room temperature.

A typical natural resin is rosin,
Modified natural resins include rosin derivatives, fibrin derivatives,
Examples include rubber derivatives, protein derivatives and oligomers thereof. Examples of the synthetic resin include epoxy resin, acrylic resin, maleic acid resin, butyral resin, polyester resin, melamine resin, phenol resin, polyurethane resin and the like. Examples of synthetic resins modified with natural resins include rosin-modified maleic acid resins and rosin-modified phenolic resins. . A method for producing a color filter by dispersing a pigment in a photopolymerizable or photocrosslinkable medium to form a colored resist material, pattern-exposing the coating film of the colored resist material, and removing the unexposed portion with a developer is known. Although widely used, when used in this method, the amount of processing is limited because the resin insoluble in the developer adversely affects the development. Therefore, in this case, it is preferable that the resin (C) be dissolved in the developing solution. Recently, an organic solvent is rarely used as a developing solution due to environmental problems, and an alkaline developing solution is generally used. As the alkali-soluble resin, a (meth) acrylic resin containing (meth) acrylic acid, a rosin resin, or a maleic acid resin is used. However, it has been confirmed that the developability is not affected even if the alkali-insoluble resin is selected so that the nonvolatile content is 10% by weight or less, preferably 5% by weight or less.

The above-mentioned (meth) acrylic resin is a copolymer of monomers of acrylic acid, methacrylic acid and their esters, alone or in a mixture, and is a radical polymerization of 60 mol% or less of styrene, vinyl acetate, maleic anhydride and the like. Also included are copolymers with soluble monomers. However, a three-dimensionally crosslinked polymer such as a copolymer with a polyfunctional monomer has poor solubility, and is not suitable for the present invention. As the maleic acid resin, those having an acid value of 40 to 160 are used, and in the case of alkali development, those having an acid value of 80 or more are preferable from the developability when the colored composition is used.

In addition to the above compounds, additives such as dispersants and plasticizers and inorganic pigments such as calcium carbonate, barium sulfate and silica, which are generally used as extender pigments, may be used in combination during salt milling. The color filter coloring composition of the present invention, if necessary, the salt milling-treated colorant is dispersed together with a transparent resin and a solvent, or the colorant is mechanically kneaded in advance with the transparent resin and then the solvent. Or, it is manufactured by adding and dispersing a resin solution.
The colorant and the transparent resin have a solid content ratio of 1: 4 to 1
It is blended in a ratio of 0: 1.

Various dispersing means such as a three roll mill, a two roll mill, a sand mill and a kneader can be used to disperse the colorant in the transparent resin. Further, in order to improve the dispersion of these, various auxiliary agents such as various surfactants and pigment derivatives can be added as appropriate. Since the dispersion aid is excellent in dispersing the pigment and has a great effect of preventing reaggregation of the pigment after the dispersion, a color filter having excellent transparency can be obtained. In addition, if storage stability is taken into consideration, a small amount of stabilizer such as polymerization inhibitor may be added. The transparent resin is 400 ~ in the visible light range.
80% or more of transmittance in the whole wavelength range of 700 nm,
Preferably 95% or more of resin is used. As the transparent resin, thermosetting resin, thermoplastic resin, photosensitive resin,
Monomers, oligomers and the like which cure upon irradiation with radiation to form a coating film similar to a resin are used alone or in combination of two or more. A photoinitiator or the like is used when curing is performed by ultraviolet irradiation.

However, since a high temperature heating process is performed in the subsequent step of manufacturing the color filter, it is necessary to use a resin having good resistance also in the heating process. Further, in the subsequent steps, treatment with various solvents and chemicals is also carried out, so that solvent resistance of the formed image is also required. Examples of thermosetting resins and thermoplastic resins include butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene,
Polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyurethane resin, phenol resin,
Polyester resin, acrylic resin, alkyd resin, styrene resin, polyamide resin, rubber resin, cyclized rubber, epoxy resin, celluloses, polybutadiene,
Examples include polyimide resin, benzoguanamine resin, melamine resin, urea resin and the like.

As the photosensitive resin, a linear polymer having a reactive substituent such as a hydroxyl group, a carboxyl group, an amino group or the like is added to a (meth) acryl compound or a cinnamon compound via an isocyanate group, an aldehyde group or an epoxy group. A resin in which a photocrosslinkable group such as an acid is introduced is used. A half ester of a (meth) acrylic compound having a hydroxyl group such as a hydroxyalkyl (meth) acrylate of a linear polymer containing an acid anhydride such as a styrene maleic anhydride copolymer or an α-olefin maleic anhydride copolymer is also used. To be The colored resist material is generally composed of a pigment in which a thermosetting resin, a thermoplastic resin or a photosensitive resin is mixed with a monomer and a photoinitiator.

Monomers and oligomers that can be used for the colored resist material are (meth) acrylic acid,
2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, (meth) acrylamide, vinyl acetate, N-hydroxymethyl (meth) acrylamide, polyethylene glycol di (meth) acrylate, penta Erythritol tri (meth) acrylate,
Styrene, vinyl acetate, various acrylic acid esters, various methacrylic acid esters, acrylonitrile, dipentaerythritol hexa (meth) acrylate, tricyclodecanyl (meth) acrylate, dipentaerythritol hexa (meth) acrylate caprolactone adduct hexa ( Examples thereof include meth) acrylate, melamine (meth) acrylate, and epoxy (meth) acrylate prepolymer.

As the photoinitiator, 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1 -Hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1- (4-
Acetophenone photoinitiators such as morpholinophenyl) -butan-1-one, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoinone such as benzyl dimethyl ketal, benzophenone photoinitiators, benzophenone, benzoyl Benzoic acid, benzoyl methyl benzoate,
4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4 '
-Benzophenone-based photoinitiators such as methyldiphenyl sulfide, thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, thioxanthone-based photoinitiators such as 2,4-diisopropylthioxanthone, 2, 4,6-trichloro-s
-Triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl ) -4,6-Bis (trichloromethyl) -s-triazine, 2-pipenyl--4,6
-Bis (trichloromethyl) -s-triazine, 2,4
--- Bis (trichloromethyl) -6-styryl s-triazine, 2- (naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxy-naphth-1- Yl) -4,6-bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl-
Used by triazine photoinitiators such as (piperonyl) -6-triazine and 2,4-trichloromethyl (4′-methoxystyryl) -6-triazine and compounds such as carbazole photoinitiators and imidazole photoinitiators. To be

The above photoinitiators may be used alone or in admixture of two or more, and as the sensitizer, α-acyloxime ester, acylphosphine oxide, methylphenylglyoxylate, benzyl, 9,10-phenanthrene may be used. Quinone, camphor quinone, ethyl anthraquinone,
4,4'-diethylisophthalophenone, 3,3 ',
4,4'-Tetra (t-butylperoxycarbonyl)
Compounds such as benzophenone and 4,4′-diethylaminobenzophenone can also be used. A solvent is used in the coloring composition for the color filter in order to sufficiently disperse the coloring agent and to coat the glass substrate so as to have a film thickness of 0.2 to 5 μm. Examples of the solvent include cyclohexanone, ethyl cellosolve acetate, butyl cellosolve acetate, 1-methoxy-2-propyl acetate, diethylene glycol dimethyl ether, ethylbenzene, ethylene glycol diethyl ether, xylene, ethyl cellosolve, methyl-n amyl ketone, propylene glycol monomethyl ether toluene, methyl ethyl ketone. , Ethyl acetate, methanol,
Examples include ethanol, isopropyl alcohol, butanol, isobutyl ketone, petroleum-based solvents, etc., which may be used alone or in combination.

By using the color filter coloring composition of the present invention, a gravure offset printing ink, a waterless offset printing ink, a silk screen printing ink, a solvent developing type or alkali developing type colored resist agent, etc. can be produced. it can. These printing inks, colored resist agents, etc. are coarse particles of 5 μm or more, preferably 1 μm or more, more preferably 0.5 μm or more, and mixed by centrifugal separation, a sintering filter, a membrane filter or the like. It is manufactured by removing dust. Since the printing ink can be patterned by simply repeating printing and drying, it is a low cost and excellent in mass productivity as a method of manufacturing a color filter. Furthermore, the development of printing technology enables printing of fine patterns with high dimensional accuracy and smoothness.

For printing, it is preferable that the composition is such that the ink does not dry and solidify on the printing plate or on the blanket. Further, if the blanket swells or dissolves, the reproducibility of the pattern and the transparency thereof are deteriorated, so various cautions are required in selecting the solvent for the printing ink. Furthermore, it is important to control the fluidity of the ink on the printing machine, and it is possible to adjust the ink viscosity with a dispersant or extender pigment. The solvent-developing or alkali-developing colored resist material is applied on a transparent substrate by a coating method such as spray coating, spin coating or roll coating. The dried film, if necessary, has a thickness of 0.2 to 5 μm and is exposed to ultraviolet light through a mask having a predetermined pattern in a contact or non-contact manner. After that, an unexposed portion, that is, an uncured portion is removed by dipping or spraying in a solvent or an alkaline developer to form a pattern, and the same operation is repeated for other colors to manufacture a color filter. Furthermore, in order to accelerate the polymerization of the resist material, heating can be performed if necessary.

At the time of development, an aqueous solution of sodium carbonate, caustic soda or the like is used as an alkali developing solution, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used. Further, a defoaming agent or a surfactant can be added. In order to increase the ultraviolet exposure sensitivity, after the above-mentioned colored resist agent is applied and dried, a water-soluble or alkaline water-soluble resin such as polyvinyl alcohol or water-soluble acrylic resin is applied and dried to form a film for preventing oxygen inhibition. , UV exposure can also be performed.

[0026]

EXAMPLES The present invention will be described below based on examples.
Prior to the examples, a method of measuring the contrast ratio will be described. FIG. 1 shows a conceptual diagram of the measuring device. The light emitted from the backlight unit for liquid crystal display (7) passes through the polarizing plate (6) and is polarized, and passes through the dry coating film (4) of the coloring composition applied on the glass substrate (5). , Reaches the polarizing plate (3). Polarizing plate (6) and polarizing plate (3)
If the planes of polarization are parallel, the light passes through the polarizing plate (3), but if the planes of polarization are orthogonal, the light is polarizing plate (3).
To be shut off. However, when the light polarized by the polarizing plate (6) passes through the coating film (4), scattering due to pigment particles and the like causes a partial deviation of the polarization plane. The amount of light transmitted through the polarizing plate (3) is reduced, and when the deflecting plate is orthogonal, some light is transmitted through the polarizing plate (3). This transmitted light is measured as the brightness on the polarizing plate, and the ratio of the brightness when the polarizing plates are parallel to the brightness when it is orthogonal is called the contrast ratio.

Contrast ratio = luminance when parallel / luminance when orthogonal Therefore, when scattering occurs due to the pigment of the coating film (4), the luminance when parallel decreases and the luminance when orthogonal increases. Therefore, the contrast ratio becomes low. The luminance meter (1) is a color luminance meter BM-5A manufactured by Topcon Corporation,
As the polarizing plate, Sanritsu polarizing film LLC2-92-18 was used. At the time of measurement, a black mask (2) with a 1 cm square hole was applied to the measurement portion in order to block unnecessary light. Next, in order to confirm the effect of the invention, an example of producing a resin solution for dispersing the treated pigment is shown below. (Resin solution production example a) Cyclohexanone 80 was placed in a reaction vessel.
0 part was added, the mixture was heated to 100 ° C., and a mixture of the following monomers and a thermal polymerization initiator was added dropwise at the same temperature over 1 hour to carry out polymerization.

Styrene 60.0 parts Methacrylic acid 60.0 parts Methyl methacrylate 65.0 parts Butyl methacrylate 65.0 parts Azobisisobutyronitrile 10.0 parts After dropping, the mixture was further reacted at 100 ° C. for 3 hours. Then, add 2.0 parts of azobisisobutyronitrile to 50 parts of cyclohexanone
What was dissolved in 1 part was added and the reaction was continued for 1 hour to synthesize a resin solution.

A portion of the resin solution is sampled and 180
The resin solution a was prepared by heating and drying at 0 ° C. for 20 minutes to measure the nonvolatile content, and adding cyclohexanone to the previously synthesized resin solution so that the nonvolatile content was 20%. (Resin Solution Production Example b) 600 parts of diethylene glycol monobutyl ether and 400 parts of ethylene glycol monobutyl ether were placed in a separable flask, and an epoxy resin (“Epicoat 1004” manufactured by Shell Chemical Co., Ltd.) was introduced at about 100 ° C. while introducing nitrogen gas. 600 parts was gradually added and dissolved, and the temperature was raised to 100 ° C. to produce a resin solution.
Next, a few grams of the resin solution was precisely weighed, dried at 140 ° C. for 2 hours to measure the nonvolatile content, and a mixed solution of 6/4 of diethylene glycol monobutyl ether / ethylene glycol monobutyl ether was added to give a nonvolatile content of 35%. To obtain a resin solution b.

Next, the present invention will be described in more detail with reference to examples, but the following examples do not limit the scope of rights of the present invention. In addition, "part" in the embodiment
Represents "parts by weight". The symbol after the pigment name is the color index No. , For example, “P. Yell
ow 139 "is" C.I. Pigment Yel "
low 139 ”.

[0031]

Example 1 (Method for producing salt milling-treated pigment) Yellow pigment (B
"Pariotor Yellow L1820" manufactured by ASF: P.
Y. 139), 700 g of sodium chloride, hydrogenated rosin ester ("Ester gum HP" manufactured by Arakawa Chemical Co., Ltd.) 10
7 g and 160 g of polyethylene glycol 300 (manufactured by Tokyo Chemical Industry Co., Ltd.) were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded for 3 hours. Next, this mixture is poured into about 3 liters of warm water, stirred for about 1 hour with a high speed mixer while heating at about 80 ° C. to form a slurry, and then filtered and washed with water to remove sodium chloride and solvent, It was dried in a hot air oven at 60 ° C. for about 24 hours to obtain a salt milled pigment. (Ink production method) 3 g of salt milled pigment, 0.1 g of dispersant, 9 g of varnish, 12 g of cyclohexanone and 70 g of glass beads having a diameter of 2 mm were placed in a 140 ml mayonnaise bottle and dispersed for 3 hours with a paint conditioner manufactured by Red Devil Co., A dispersed ink was obtained. (Preparation of ink coating) The obtained ink is coated on a glass plate with a thickness of about 1 mm with a # 3 bar coater and dried in a hot air oven at 70 degrees for 20 minutes to form an ink coating with a thickness of about 1 micron. Obtained.

[0032]

Example 2 An ink coating film was obtained in the same manner as in Example 1 except that the following treated pigments were used in place of the salt milled pigments of Example 1 "Pariotor Yellow L1819" 250 g, sodium chloride 700 g, sucrose. 107 g of the derivative (“Monopet SB” manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) and 160 g of polyethylene glycol 300 (manufactured by Tokyo Chemical Industry Co., Ltd.) were charged into the kneader described in Example 1 to produce a treated pigment by the same operation, and formed into an ink to form a coating film. Was produced.

[0033]

Example 3 An ink coating film was obtained in the same manner as in Example 1 except that ethyl cellulose (“T-10” manufactured by Hercules Co., Ltd.) was used instead of “Monopet SB” in Example 2.

[0034]

Example 4 An ink coating film was obtained in the same manner as in Example 1 using the following treated pigments. "Pariotor Yellow L181
250 g of 9 ", 700 g of sodium chloride and 320 g of polyethylene glycol 300 (manufactured by Tokyo Kasei) were charged into the kneader described in Example 1 and kneaded for 3 hours. This was treated in the same manner as in Example 1 to obtain a salt-milled pigment containing no resin.

[0035]

[Example 5] "Pariotor Yellow L1819" 250
Instead of g, an orange pigment (“Rionol Orange B NEW” manufactured by Toyo Ink Mfg. Co., Ltd .: P. Orange 1
3) Using 250 g, salt milling treatment and ink formation were carried out in the same manner as in Example 1 to obtain an ink coating film.

[0036]

[Example 6] "Pariotor Yellow L1819" 250
A salt milled pigment was produced in the same manner as in Example 1 by using 280 g of a red pigment (“Chromophtal red A2B” manufactured by BASF: P. Red 177) instead of g to obtain an ink coating film.

[0037]

[Embodiment 7] "Pariotor Yellow L1819" 250
280 instead of g green pigment ("Ryonor Green 6YK: P. Green 36" manufactured by Toyo Ink Mfg. Co., Ltd.)
A salt-milled pigment was produced in the same manner as in Example 1 using g to obtain an ink coating film.

[0038]

[Embodiment 8] "Pariotor Yellow L1819" 250
280 g of blue pigment instead of g ("Rionol Blue E" manufactured by Toyo Ink Mfg. Co., Ltd .: P. Blue 15: 6)
A salt-milled pigment was produced in the same manner as in Example 1 to obtain an ink coating film.

[0039]

[Embodiment 9] "Pariotor Yellow L1819" 250
Violet pigment instead of g ("Rionol Violet RL" P. Violet 2 manufactured by Toyo Ink Mfg. Co., Ltd.
3) Using 280 g, a salt milled pigment was produced in the same manner as in Example 1 to obtain an ink coating film.

[0040]

[Comparative Example 1] "Pariotor Yellow L1819" 2.1
g, "ester gum HP" 0.9 g, dispersant 0.1 g,
9 g of varnish, 12 g of cyclohexanone and 70 g of glass beads having a diameter of 2 mm were placed in a 140 ml mayonnaise bottle and dispersed in a paint conditioner manufactured by Red Devil Co. for 3 hours to obtain an ink coating film in the same manner as in Example 1.

[0041]

[Comparative Example 2] "Pariotor Yellow L181 of Comparative Example 1
An ink coating film was obtained in the same manner as in Example 1 except that "Rionol Orange B NEW" was used instead of "9".

[0042]

[Comparative Example 3] "Pariotor Yellow L181 of Comparative Example 1
An ink coating film was obtained in the same manner as in Example 1 except that "chromophthal red A2B" was used instead of "9".

[0043]

[Comparative Example 4] "Pariotor Yellow L181 of Comparative Example 1
An ink coating film was obtained in the same manner as in Example 1 except that "Rionol Green 6YK" was used instead of "9".

[0044]

[Comparative Example 5] "Pariotor Yellow L181 of Comparative Example 1
An ink coating film was obtained in the same manner as in Example 1, except that "Rionol Blue E" was used instead of "9".

[0045]

[Comparative Example 6] "Pariotor Yellow L181 of Comparative Example 1
An ink coating film was obtained in the same manner as in Example 1, except that "Rionol Violet RL" was used instead of "9". The contrast ratios of the ink coating films of the above Examples and Comparative Examples were measured and the following results were obtained. Contrast Ratio Contrast Ratio Example 1 160 Example 7 1660 Comparative Example 1 48 Comparative Example 4 950 Example 2 145 Example 3 150 Example 8 1840 Example 4 123 Comparative Example 5 960 Example 5 95 Example 9 220 Comparative Example 2 32 Comparative Example 6 110 Example 6 1300 Comparative Example 3 660

[0046]

[Embodiment 10] Using the inks obtained in the above embodiments,
The following three types of alkali development type colored resists were produced. (Preparation of red resist) Ink obtained in Example 1 14.0 parts Ink obtained in Example 6 32.8 parts Resin solution a 7.8 parts NK ester ATMPT (Shin-Nakamura Chemical Co., Ltd.) 3.9 Part Irgacure 907 (manufactured by Ciba Geigy) 0.4 part EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) 0.7 part Anon 34.5 parts were sufficiently stirred in a container and filtered with a 1 μm filter to prepare a red resist. . (Production of green resist) Ink obtained in Example 1 10.5 parts Ink obtained in Example 3 34.5 parts Resin solution a 6.7 parts NK ester ATMPT (manufactured by Shin-Nakamura Chemical Co., Ltd.) 3.8 Part Irgacure 907 (manufactured by Ciba Geigy) 0.4 part EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) 0.7 part Anon 37.0 parts were thoroughly stirred in a container and filtered with a 1 μm filter to prepare a green resist. . (Preparation of blue resist) Ink obtained in Example 8 30.0 parts Ink obtained in Example 9 1.6 parts Resin solution a 19.1 parts NK ester ATMPT (manufactured by Shin-Nakamura Chemical Co., Ltd.) 3.9 Part Irgacure 907 (manufactured by Ciba Geigy) 0.4 part EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) 0.7 part Anon 37.0 parts were thoroughly stirred in a container and filtered with a 1 μm filter to prepare a green resist. .

Next, each colored resist was applied onto a glass substrate having a thickness of 1 mm by a spin coater so that the dry film thickness was 1.8 μm, and dried at 70 ° C. for 10 minutes. Furthermore, a 5% aqueous solution of polyvinyl alcohol (produced by Kokusan Kagaku Co., Ltd .: a molecular weight of about 500) was applied onto the dry coating film to give a dry film thickness of 1 μm.
And was dried at 70 ° C. for 20 minutes. next,
UV exposure (accumulated light amount: 40 m
After J), it was dipped in a 2% sodium carbonate aqueous solution for 50 seconds, washed with water, and heated at 200 ° C. for 30 minutes to reproduce a good pattern having a line width accuracy of ± 1 μm or less.

Further, a colored resist and polyvinyl alcohol were applied in the same manner, and the entire surface was exposed to the same amount of ultraviolet rays without using a mask, and then 50% in a 2% sodium carbonate aqueous solution.
The following results were obtained by measuring the contrast ratio of what was dipped for 2 seconds, washed with water, and heated at 200 ° C. for 30 minutes. Red resist Contrast ratio: 830 Green resist Contrast ratio: 1380 Blue resist Contrast ratio: 1200

[0049]

Example 11 Next, resin treated pigment 7 and comparative treated pigment 2
Was dispersed in the resin solution b by the following method to prepare an intaglio offset ink. Resin solution b 63.95 parts Salt milled pigment of Example 1 4.88 parts Salt milled pigment of Example 7 16.33 parts Dispersant 0.76 parts Precipitating barium sulfate 1.30 parts Diethylene glycol monobutyl ether 8. 05 parts of ethylene glycol monobutyl ether (5.37 parts) were mixed, thoroughly kneaded with a three-roll mill, and then filtered through a 5 μ filter to prepare a green ink. Next, using a flatbed proof press, the above green ink was applied onto an intaglio plate having a square pattern of 1 cm square with a plate depth of 10 μm, and excess ink was scraped off with a doctor. After the ink on the intaglio plate was transferred to a silicon rubber blanket, the blanket was brought into contact with the glass substrate for the color filter, and the ink on the blanket was transferred to the glass substrate. The obtained pattern was heated at 180 ° C. for 2 hours to produce a green color filter having a film thickness of 2.0 μm. As a result of measuring the contrast of the obtained color filter, a value of 1150 was obtained.

[0050]

[Comparative Example 7] A green color filter was prepared in the same manner as in Example 11 except that untreated pigments, that is, "Pariotor Yellow D1819" and "Lionol Green 6YK" were used, and the contrast ratio was measured. As a result, a value of 220 was obtained.

[0051]

According to the present invention, it is possible to manufacture a color filter which is excellent in various resistance and has a high contrast ratio.

[Brief description of drawings]

FIG. 1 shows a conceptual diagram of an apparatus for measuring contrast ratio.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Katsuhito Miura 2-3-13 Kyobashi, Chuo-ku, Tokyo Toyo Inki Manufacturing Co., Ltd. (72) Makoto Sakagawa 1-1-5 Taito, Taito-ku, Tokyo Toppan Printing Co., Ltd. (72) Inventor Tani Hata 1-5-1 Taito, Taito-ku, Tokyo Toppan Printing Co., Ltd.

Claims (5)

[Claims] 1. A color filter coloring composition comprising a transparent resin and a colorant dispersed therein, wherein the colorant is an organic pigment, and the organic pigment contains water-soluble inorganic salts (A) and (A). A colored composition for a color filter, which is a treated pigment obtained by mechanically kneading with a water-soluble organic solvent (B) which is substantially insoluble and then removing (A) and (B). 2. The water-soluble organic solvent (B), wherein the organic pigment does not substantially dissolve the water-soluble inorganic salts (A) and (A).
2. A color filter according to claim 1, which is a treated pigment obtained by mechanically kneading with (C) which is at least partially soluble in (B) and then removing (A) and (B). Coloring composition. 3. The coloring composition for a color filter according to claim 2, wherein the resin (C) is a natural resin and / or a natural resin derivative. 4. The coloring composition for a color filter according to claim 1, wherein the organic pigment is a yellow pigment and / or an orange pigment. 5. A color filter in which a plurality of colors are arranged on a substrate, which is obtained by using the coloring composition for a color filter containing at least one kind of the treated pigment according to claim 1, 2.