JP3277101B2 - Coloring composition for color filter and color filter - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a coloring composition used for manufacturing a color filter used in a reflection type color liquid crystal display device, and a color filter using the coloring composition.

[Prior art]

[0002] A color filter is a filter in which two or more types of fine bands (stripe) of 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 arrangement. It consists of what you did. Since the pixel size is as fine as several tens to several hundreds of microns and is arranged neatly in a predetermined arrangement for each hue, various methods for producing a color filter have been conventionally proposed. Since high transparency is required for the color filter, it has been manufactured by a method of coloring using a dye, which is generally called a dyeing method. For example, a photosensitive material to be dyed is applied to a substrate such as glass, followed by pattern exposure of one filter color, and then the unexposed portion is removed in a developing step, and the remaining pattern portion is removed by the filter color. A color filter can be manufactured by sequentially repeating the operation of dyeing with a dye for all filter colors.

Conventionally, a color liquid crystal display device using a color filter is provided with an illuminating device called a backlight on the back surface of the display device due to a demand for brightness of a screen. However, this backlight consumes much more power than the driving power of the liquid crystal, and it is not practical because a battery or a battery-powered portable device consumes the battery in several hours. Therefore, in a portable color liquid crystal display device, in order to suppress power consumption, it is necessary to obtain a color display screen with sufficient brightness under natural light or room light by using a so-called reflection type liquid crystal display device without using a backlight. There is. In order to make the screen brighter, studies have been made on the driving method of the liquid crystal, the structure of the liquid crystal cell, and the like. However, as for the color filter, a material that is brighter and has higher color purity than ever before is desired.

On a color filter used in a color liquid crystal display device, a transparent electrode for driving the liquid crystal is generally formed by vapor deposition or sputtering, and an alignment film for aligning the liquid crystal in a certain direction is formed thereon. Have been. In order to sufficiently obtain the performance of the transparent electrode and the alignment film, it is generally necessary to form the transparent electrode and the alignment film at a high temperature of 200 ° C. or higher, preferably 250 ° C. or higher. Color filters using dyes are excellent in terms of transparency, but are inferior in heat resistance, so that formation of transparent electrodes and alignment films on the color filters must be performed at less than 200 ° C. The performance of the transparent electrode and the alignment film was poor, and the display performance was limited. In addition, color filters using dyes have poor light fastness and are not suitable for use outdoors.

[0005] Therefore, instead of dyes, pigments having excellent light fastness and heat resistance have been used, and most of currently manufactured color filters use organic pigments. However, color filters using pigments are generally inferior in transparency and color purity to those using dyes, and improvements have been strongly desired.

[0006]

DISCLOSURE OF THE INVENTION The present invention relates to a color filter used in a reflection type color liquid crystal display device which has excellent heat resistance and light resistance and has a color purity equal to or higher than that of a color filter produced by a dyeing method. It is intended to provide a coloring composition for use and a color filter.

[0007]

That is, the present invention provides a coloring composition comprising a pigment represented by the following general formula dispersed in a transparent resin medium, wherein the pigment is a water-soluble inorganic salt:
After mechanically kneading with a water-soluble organic solvent that does not substantially dissolve the inorganic salt and a rosin-modified maleic resin that is at least partially dissolved in the water-soluble organic solvent, the inorganic salt and the water-soluble organic solvent are removed. Provided is a coloring composition for a color filter, wherein the coloring composition is a pigment.

Embedded image (In the formula, M ²⁺ represents a metal element selected from Ba, Ca, Sr and Mn.) In the present invention, a pixel of at least one color is formed on a transparent substrate by using the coloring composition. A color filter characterized by the following.

The color filters used in color liquid crystal display devices are generally red (R), green (G), and blue (B) additive color mixing types. (Nikkei Micro Devices, June 1994, p. 47) using a color filter composed of two colors of cyan (C) and red (R). The coloring composition of the present invention is particularly effective for forming a red color of these color filters, is excellent in heat resistance and light resistance, and has a color purity equal to or higher than that of a color filter produced by a dyeing method. Is obtained.

[0009]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Specific examples of the pigment represented by the above general formula include C.I. I. P
imagment Red 48: 1, 48: 2, 48: 3
And 48: 4. The metallized lake M ²⁺ is a metal element selected from barium, calcium, strontium and manganese. The pigment represented by the above general formula can be obtained by diazotizing 4-chloro-6-amino-m-toluenesulfonic acid, coupling with β-oxy-naphthoic acid, and then raked with the above metal.

The transparency of the pigment represented by the above general formula varies depending on the production method, and various products are marketed. However, it is necessary to select a product as transparent as possible for a color filter. As a method for producing a transparent pigment, a so-called mixed coupling method in which a base or a part of a coupler used in a coupling reaction is used in combination with another compound having a similar structure, or a method called a so-called mixed coupling, or two or more types of laked metals are used. A method of mixing and rake is effective.

In order to further improve the transparency of the pigment,
The pigment is mechanically kneaded with a water-soluble inorganic salt, a kneader or the like together with a water-soluble organic solvent that does not substantially dissolve the inorganic salt and a resin that is at least partially dissolved in the water-soluble organic solvent, and then the inorganic salt is washed with water. And remove the water-soluble organic solvent,
At the same time that the primary particle diameter of the pigment is reduced, a resin is deposited on the surface of the pigment to prevent pigment aggregation, thereby providing a pigment having good redispersibility. (Hereinafter, this pigment treatment method is called salt milling).

The inorganic salt used for salt milling is not particularly limited as long as it is water-soluble, but it is preferable to use salt (sodium chloride) in terms of cost. Regarding the mixing ratio of the inorganic salt and the pigment, the higher the ratio of the inorganic salt to the pigment, the higher the fineness efficiency, but the smaller the processing amount of the pigment at one time. Therefore, from the viewpoint of both processing efficiency and production efficiency, it is preferable to use the inorganic salt in a weight ratio of 1 to 10 times the pigment.

The organic solvent used for salt milling is not particularly limited as long as it is water-soluble and does not dissolve water-soluble inorganic salts. However, the temperature rises during salt milling, and the solvent is easily evaporated. A high boiling point solvent is desirable from the viewpoint of safety. For example, 2-methoxyethanol, 2
-Butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, diethylene glycol, 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, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, low molecular weight polypropylene glycol and the like are used.

The resin used for salt milling needs to be at least partially dissolved in the above water-soluble organic solvent, and is preferably solid at room temperature and insoluble in water, and a rosin-modified maleic resin is used. The rosin-modified maleic acid resin is preferably used in the range of 5 to 100% by weight based on the pigment. Some commercially available pigments already contain a rosin-modified maleic resin, but in this case, it is not necessary to add the rosin-modified maleic resin during the salt milling treatment.

At the time of salt milling, in addition to the above compounds, additives such as a pigment dispersing aid and a plasticizer or inorganic pigments such as calcium carbonate, barium sulfate and silica which are generally used as extenders may be used in combination. . In order to adjust the hue, the pigment represented by the above general formula and a yellow pigment may be mixed and subjected to a salt milling treatment.

Hereinafter, examples of yellow pigments for adjusting the hue used in the coloring composition of the present invention are shown by color index (CI) numbers. C. I. Pigment
Yellow 1, 3, 12, 13, 14, 16, 1
7, 24, 55, 60, 65, 73, 74, 81, 8
3, 93, 95, 97, 98, 100, 101, 10
4, 106, 108, 109, 110, 113, 11
4, 116, 117, 119, 120, 126, 12
7, 128, 129, 138, 139, 150, 15
1, 152, 153, 154, 156, 175.

For dispersing the pigment or the salt-milled pigment in the transparent resin medium, various dispersing means such as a three-roll mill, a two-roll mill, a sand mill and a kneader can be used. Further, in order to improve the dispersion, various surfactants and a dispersion aid such as a derivative of a pigment can be appropriately added. The dispersing aid is excellent in dispersing the pigment and has a large effect of preventing re-aggregation of the pigment after dispersion, so that a color filter having excellent transparency can be obtained.

The transparent resin medium has a visible light range of 400 to 7
The transmittance is preferably 80% or more, and more preferably 95% or more in the entire wavelength region of 00 nm. As the transparent resin medium, a thermosetting resin, a thermoplastic resin, a photosensitive resin, a monomer or an oligomer which forms a coating film similar to the resin when cured by irradiation with radiation, or a mixture of two or more kinds thereof is used. . When curing is performed by ultraviolet irradiation, a photoinitiator or the like is used. The transparent resin medium is generally a composition in which a thermosetting resin, a thermoplastic resin, or a photosensitive resin is mixed with a monomer and a photoinitiator. Note that a high-temperature heating process is performed in a later step of manufacturing a color filter, and thus, it is necessary to use a resin having high resistance in the heating process as a medium. In addition, since treatment with various solvents and chemicals is also performed in a later step, it is necessary to use a resin having good solvent resistance and chemical resistance as a medium.

Examples of the thermosetting resin and thermoplastic resin include butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, and polyvinyl acetate. , Polyurethane resin, phenol resin, polyester resin, acrylic resin, alkyd resin, styrene resin, polyamide resin, rubber resin, cyclized rubber, epoxy resin, celluloses, polybutadiene, polyimide resin, benzoguanamine resin, melamine resin, urea Resins.

As the photosensitive resin, a (meth) acrylic compound, a silicone resin, and a linear polymer having a reactive substituent such as a hydroxyl group, a carboxyl group, or an amino group can be added via an isocyanate group, an aldehyde group, or an epoxy group. A resin into which a photocrosslinkable group such as an acid is introduced is used. Also used is 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. Can be

The monomers and oligomers include (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, pentaerythritol tri (meth)
Acrylate, styrene, vinyl acetate, various acrylates, various methacrylates, acrylonitrile, dipentaerythritol hexa (meth) acrylate, tricyclodecanyl (meth) acrylate, dipentaerythritol hexa (meth) acrylate adduct of caprolactone Hexa (meth) acrylate, melamine (meth) acrylate, epoxy (meth) acrylate prepolymer, and the like.

Examples of the photoinitiator include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropane-1one, -Hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1- (4-
Acetophenone-based photoinitiators such as morpholinophenyl) -butan-1-one; benzoin-based, benzophenone-based photoinitiators such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzyl dimethyl ketal; benzophenone; benzoyl Benzoic acid, methyl benzoylbenzoate,
4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4 '
Benzophenone-based photoinitiators such as -methyldiphenyl sulfide; thioxanthone-based photoinitiators such as thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, and 2,4-diisopropylthioxanthone; 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-
Compounds such as triazine photoinitiators such as (piperonyl) -6-triazine and 2,4-trichloromethyl (4′-methoxystyryl) -6-triazine and carbazole photoinitiators and imidazole photoinitiators are used. .

The above photoinitiators may be used alone or as a mixture of two or more. As sensitizers, α-acyloxime ester, acylphosphine oxide, methylphenylglyoxylate, benzyl, 9,10-phenanthrene Quinone, camphorquinone, ethylanthraquinone,
4,4′-diethylisophthalophenone, 3,3 ′,
4,4'-tetra (t-butylperoxycarbonyl)
Compounds such as benzophenone and 4,4'-diethylaminobenzophenone can also be used.

The coloring composition for a color filter is used in order to sufficiently disperse a pigment and to form a pigment on a glass substrate in an amount of 0.2 to 0.2.
A solvent is used for coating to a thickness of 5 microns. As the solvent, for example, 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, ethanol, isopropyl alcohol, butanol, isobutyl Examples thereof include ketones and petroleum solvents, which are used alone or as a mixture.

Using the coloring composition for a color filter of the present invention, a printing ink for gravure offset, an offset printing ink without water, an ink for silk screen printing, a solvent developing type or an alkali developing type coloring resist material and the like can be produced. it can. These printing inks, colored resist material, etc., by means of centrifugal separation, sintering filter, membrane filter and the like, coarse particles of 5μ or more, preferably 1μ or more coarse particles, more preferably 0.5μ or more coarse particles and It removes mixed dust and manufactures.

The method for producing a color filter using the printing ink described above can be patterned simply by repeating printing and drying, and is therefore low in cost and excellent in mass productivity. Furthermore, since a fine pattern having high dimensional accuracy and smoothness can be printed due to the development of printing technology, a highly accurate color filter can be manufactured. In the case of this method (printing method), it is important to control the fluidity of the ink on the printing press, and the viscosity of the ink can be adjusted by a dispersant or extender.

As a method for producing a color filter with higher precision than the above printing method, a photosensitive resin medium (called a colored resist material) in which a pigment is dispersed is uniformly applied to a transparent substrate such as a glass plate, and then a photomask is applied. A color filter is widely manufactured by a so-called photolithography method in which pattern exposure is performed with ultraviolet rays through an unexposed portion, and an unexposed portion is washed away with a solvent or an aqueous alkaline solution to obtain a desired pattern. Such a solvent-developed or alkali-developed colored resist material is applied onto a transparent substrate by an application method such as spray coating, spin coating, or roll coating.

Solvents are rarely used for development due to environmental problems, and alkali development is now mainstream. As the alkali developer, an aqueous solution such as sodium carbonate or caustic soda is used, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used. Further, an antifoaming agent or a surfactant can be added. In order to increase the UV exposure sensitivity, after applying and drying the above colored resist material, a water-soluble or alkali-water-soluble resin,
For example, after applying and drying a polyvinyl alcohol, a water-soluble acrylic resin, or the like to form a film for preventing polymerization inhibition by oxygen, ultraviolet light exposure can be performed.

As a method of producing a color filter using a pigment, there are other methods such as an electrodeposition method and a transfer method, and the coloring composition of the present invention can be used in any method.
The electrodeposition method is a method of producing a color filter by using a transparent conductive film formed on a transparent substrate and forming a colorant on the transparent conductive film by electrophoresis of colloid particles. The transfer method is a method in which a color filter layer is previously formed on the surface of a peelable transfer base sheet, and the color filter layer is transferred to a desired transparent substrate.

[0030]

EXAMPLES Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited thereto. In the examples, parts and% represent parts by weight and% by weight, respectively. Prior to the examples, a method for producing the salt-milled pigment used in the examples and the synthesis of the acrylic resin used as the transparent resin medium will be described.

(Salt milling of pigment) Red pigment ("Bright Red G2X" manufactured by Toyo Ink Mfg. Co., Ltd.):
C. I. Pigment Red 48: 1) 250
g, sodium chloride 700 g, rosin-modified maleic resin (“Marquid No. 31” manufactured by Arakawa Chemical Co., Ltd.) 107
g and 160 g of polyethylene glycol (“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, the mixture is poured into about 3 L of warm water,
The mixture was stirred for about 1 hour with a high-speed mixer while heating to about 80 ° C. to form a slurry, and then filtered and washed with water to remove sodium chloride and polyethylene glycol.
Dried in a hot air oven for about 24 hours to process pigment (hereinafter, referred to as
"PR48: 1 salt milled product").

Next, instead of the red pigment, a yellow pigment ("Pariotor Yellow D1819" manufactured by BASF) was used:
C. I. Pigment Yellow 139) to obtain a yellow pigment (hereinafter referred to as “PY139 salt milled product”).

Further, a red pigment widely used as a pigment for a color filter (“Chromophthal Red A2B” manufactured by BASF: CI Pigment Red)
In the same manner, salt milling treatment was performed using 177) to obtain a red treated pigment (hereinafter, referred to as “PR177 salt milled product”).

(Synthesis of Acrylic Resin) A reaction vessel is charged with 800 parts of cyclohexanone, heated to 100 ° C. while injecting nitrogen gas into the vessel, and a mixture of the following monomer and thermal polymerization initiator is added at the same temperature for 1 hour. The polymerization reaction was performed by dropping. 60.0 parts of styrene 60.0 parts of methacrylic acid 65.0 parts of methyl methacrylate 65.0 parts of butyl methacrylate 10.0 parts of azobisisobutyronitrile 10.0 parts After dropping, the mixture was further reacted at 100 ° C. for 3 hours, and then reacted with azobis. A solution prepared by dissolving 2.0 parts of isobutyronitrile in 50 parts of cyclohexanone was added, and the reaction was further continued at 100 ° C. for 1 hour to synthesize a resin solution. After cooling to room temperature,
About 2 g of the resin solution was sampled, dried by heating at 180 ° C. for 20 minutes to measure the nonvolatile content, and cyclohexanone was added to the previously synthesized resin solution so that the nonvolatile content was 20% to prepare an acrylic resin solution. .

Example 1 (Preparation of Pigment Dispersion) In a 140 ml mayonnaise bottle, 150 g of 2 mm-diameter steel beads, PR48: 1 salt milled product 10.0
g, dispersing aid (“SOLSPERS 24000” manufactured by ICI)
GR "), 0.7 part of the above acrylic resin solution, 35 parts of cyclohexanone and 42 parts of cyclohexanone were dispersed in a paint conditioner for 3 hours. Next, 73.2 g of the above acrylic resin solution and 13.2 g of cyclohexanone were added to 60 g of the dispersion from which the steel beads had been separated, and the mixture was uniformly stirred and mixed to obtain a red pigment dispersion (hereinafter referred to as "PR48: 1 salt milling product dispersion"). ").

(Formation of Colored Resist) A mixture having the following composition was uniformly stirred and mixed, and then filtered through a 1 μm filter to prepare an alkali-developed colored resist material. PR48: 1 Salt milling product dispersion 8.4 parts Acrylic resin solution 21.0 parts Monomer ("NK ester ATMPT" manufactured by Shin-Nakamura Chemical Co.) 5.4 parts Photoinitiator ("Irgacure 907" manufactured by Ciba Geigy) 0.3 parts Sensitizer ("EAB-F" manufactured by Hodogaya Chemical Co., Ltd.) 0.2 parts Cyclohexanone 64.7 parts

(Preparation of Coated Substrate and Measurement of Chromaticity) 100
The above colored resist material was coated on a glass substrate having a size of 100 mm × 1.1 mm and a thickness of 1.1 mm using a spin coater at 500 rpm.
m, 1000 rpm, 1500 rpm, 2000 rpm
4 types of coated substrates having different film thicknesses were obtained by coating at a rotation speed of.
Next, after drying at 70 ° C. for 20 minutes, ultraviolet exposure was performed using an ultra-high pressure mercury lamp with an integrated light amount of 150 mJ. After exposure, the film was heated at 200 ° C. for 1 hour and allowed to cool, and then cooled using a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.).
The chromaticity (Y, x, y) at 65 light sources was measured. X when the Y value is 70.0 from the chromaticity measurement results of four sets of each resist
And y were determined, and the dominant wavelength and color stimulus purity at this time were determined from the xy chromaticity diagram of the CIE color system. Table 1 shows the results.

Comparative Example 1 (Preparation of Pigment Dispersion) In a 140 ml mayonnaise bottle, 150 g of steel beads having a diameter of 2 mm and a red pigment ("Bright Red G2X" manufactured by Toyo Ink Mfg. Co., Ltd .: CI Pigment Re)
d 48: 1) 7.0 g, a dispersing aid (“Sol Spurs 24000GR” manufactured by ICI) 0.7 g, the above acrylic resin solution 40.0 g, and cyclohexanone 30.0 g were added, and the mixture was dispersed with a paint conditioner for 3 hours. Next, 73.2 g of the acrylic resin solution and 13.2 g of cyclohexanone were added to 60 g of the dispersion from which the steel beads had been separated.
Was added and uniformly stirred and mixed to prepare a red pigment dispersion (hereinafter referred to as "PR48: 1 untreated product dispersion").

(Preparation of colored resist material) PR48: PR4 was used instead of the salt milled product dispersion.
Using the 8: 1 untreated product dispersion, a colored resist material was produced in the same manner as in Example 1. (Preparation of Coated Substrate and Measurement of Chromaticity) A coated substrate was prepared in the same manner as in Example 1, and the Y value was 7
X and y at 0.0 were determined. Table 1 shows the results.

(Preparation of Color Filter) 100 mm × 1
On a glass substrate having a thickness of 00 mm and 1.1 mm, the above colored resist material was dried to a thickness of 1.0 μm using a spin coater.
m and dried with a hot air drier at 70 ° C. for 20 minutes to remove the solvent. Next, a line and space photomask having a thickness of 100 μm is adhered to the dried coating film,
Ultraviolet exposure was performed using an ultra-high pressure mercury lamp with an integrated light amount of 150 mJ. After the exposure, the film was immersed in a 2% aqueous solution of sodium carbonate for about 1 minute, washed with running water, air-dried, and heated at 200 ° C. for 1 hour to produce a striped color filter.

(Evaluation of Color Filter) The chromaticity of the color filter was measured using a microspectrophotometer (“OS
P-SP100 "). After the color filter is heated at 250 ° C. for 1 hour, the chromaticity is similarly measured with a microspectrophotometer, and the color difference from the initial chromaticity (ΔEab)
Was evaluated for heat resistance. Similarly, a polarizing plate was attached to the glass surface of a separately prepared color filter, and light was irradiated from the polarizing plate side using a xenon fade meter, and the chromaticity change after 500 hours was measured to improve light resistance. evaluated. Table 2 shows the results.

[Examples 2 to 5] (Preparation of Pigment Dispersion) A yellow pigment dispersion (hereinafter, referred to as “P48”) was prepared in the same manner as in Example 1 except that a PY139 salt milling product was used instead of the PR48: 1 salt milling product. "PY139 salt milled product dispersion"). (Preparation of Colored Resist Material) In the same manner as in Example 1 except that the PR48: 1 salt milling product dispersion and the PY139 salt milling product dispersion having the following compositions were used instead of 8.4 parts of the PR48: 1 salt milling product dispersion. By the above method, a colored resist material containing 3%, 6%, 8%, and 10% of the yellow pigment in all the pigments was prepared.

PR48: 1 PY139 Salt milled product dispersion Salt milled product dispersion Example 2 8.15 parts 0.25 parts Example 3 7.90 parts 0.50 parts Example 4 7.73 parts 0.67 parts Example 5 7.56 parts 0.84 part (Preparation of coated substrate and chromaticity measurement) A coated substrate was prepared in the same manner as in Example 1, and the Y value was 7
X and y at 0.0 were determined. Table 1 shows the results.

Comparative Example 2 A dyeable photosensitive resin (aqueous solution obtained by adding ammonium bichromate to low molecular weight gelatin to impart photosensitivity) was spin-coated on a glass substrate of 100 mm × 100 mm, 1.1 mm thick. Coating was performed with a coater to form a coating film having a dry film thickness of about 1 μm. Ultraviolet rays were exposed through a photomask having a stripe pattern in the same manner as in Example 1, and the unexposed portions were developed with water and dissolved and removed to obtain a striped relief pattern. Next, it was immersed in a 0.01% aqueous solution (prepared at 50 ° C., pH = 5.0 with acetic acid) of a red dye (“Suminol First Red B Conc” manufactured by Mitsubishi Chemical Corporation) for 2 minutes to form a relief pattern. Staining was performed. Then
The dye was fixed by dipping in an aqueous tannic acid solution and an aqueous tartar solution to produce a red color filter. The obtained color filter was evaluated in the same manner as in Example 1, and the results shown in Tables 1 and 2 were obtained.

Comparative Example 3 (Preparation of Pigment Dispersion) A red pigment dispersion (hereinafter referred to as “PR177”) was prepared in the same manner as in Example 1 using a PR177 salt milling product instead of a PR48: 1 salt milling product. Salt milled product dispersion "). (Preparation of Colored Resist Material) A mixture having the following composition was uniformly stirred and mixed, and then filtered through a 1 μm filter to prepare an alkali development type colored resist material. PR177 Salt milling product dispersion 7.3 parts PY139 salt milling product dispersion 1.1 parts Acrylic resin solution 21.0 parts Monomer ("NK ester ATMPT" manufactured by Shin-Nakamura Chemical Co.) 5.4 parts Photoinitiator (Ciba Geigy) (Irgacure 907) 0.3 parts Sensitizer (Hodogaya Chemical "EAB-F") 0.2 parts Cyclohexanone 64.7 parts (Preparation of coated substrate and chromaticity measurement) Same as in Example 1. A coated substrate is prepared by the method described in
X and y at 0.0 were determined. Table 1 shows the results.

[0046]

[Table 1]

[0047]

[Table 2]

[0048]

According to the present invention, it is possible to provide a red color filter which is high in color purity and excellent in various resistances and is most suitable for a reflection type color liquid crystal display device.

──────────────────────────────────────────────────続 き Continuation of the front page (72) Inventor Akio Haneda 1-5-1, Taito, Taito-ku, Tokyo Toppan Printing Co., Ltd. (72) Inventor Toru Sugimura 1-5-1, Taito, Taito-ku, Tokyo 5-1-1 Toppan printing Examiner in a corporation, Yasumasa Yokoi (56) References JP-A-6-174909 (JP, A) JP-A-7-198930 (JP, A) JP-A-5-61196 (JP, A) JP-A-7 -13016 (JP, A) JP-A-7-113015 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) G02B 5/20-5/28

Claims (3)

(57) [Claims] 1. A coloring composition comprising a pigment represented by the following general formula dispersed in a transparent resin medium , wherein the pigment is
Water-soluble inorganic salt, water-soluble that does not substantially dissolve the inorganic salt
At least partially dissolved in an organic solvent and the water-soluble organic solvent
Kneading with rosin-modified maleic resin
After removing the inorganic salt and the water-soluble organic solvent.
A coloring composition for a color filter, comprising: Embedded image (In the formula, M ²⁺ represents a metal element selected from Ba, Ca, Sr and Mn.) 2. A pigment represented by the general formula:
The coloring composition requiring a color filter according to claim 1, wherein a yellow pigment is used in an amount of not more than% by weight. 3. A color filter comprising at least one color pixel formed on a transparent substrate using the coloring composition according to claim 1 or 2.