JP3130217B2 - 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 for producing an optical color filter used for a liquid crystal color display, a video camera and the like, and a color filter using the coloring composition. More specifically, the present invention 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 formed by arranging two or more kinds of fine bands (stripe) of different hues in parallel or intersecting on the surface of a transparent substrate such as glass, or arranging fine pixels in a constant vertical and horizontal direction. It consists of those arranged in. The pixel size has a fine shape of several tens to several hundreds of microns, and is arranged in a predetermined order for each hue. For this reason, various methods have been proposed for the production of color filters. Since color filters require high transparency, a method of coloring with a dye, which is generally called a dyeing method, is performed.
For example, a photosensitive material to be dyed is applied to a substrate such as glass, followed by pattern exposure of one filter color, then unexposed portions are washed away in a developing process, and the remaining pattern portions are filtered. A color filter can be manufactured by sequentially repeating the operation of dyeing with a dye for all filter colors. This method uses a dye and therefore has a high transmittance because of the use of a dye, and the optical properties of the color filter are very excellent. However, there is a limit in light resistance, heat resistance, and the like, and a coloring material having excellent resistance and high transparency is desired. Was.

Therefore, instead of dyes, organic pigments having excellent light fastness and heat resistance have been used. For example, in a color filter having three primary colors of blue, green and red 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, generally, copper phthalocyanine blue pigment having excellent resistance is used, but since it is difficult to obtain a sufficient spectrum with only a single copper phthalocyanine, the spectrum is adjusted by mixing a violet pigment. As for green, phthalocyanine green, which has excellent resistance, is generally used. However, similar to blue, a single green pigment alone cannot provide sufficient spectral characteristics. I am adjusting. Also, as for red, there is no single pigment having sufficient absorption in a wide wavelength range from 400 nm to 600 nm, and 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. In general, a type using a twisted nematic (TN) type liquid crystal, which performs display by performing the operation, is used. Color display is enabled by providing a color filter between the two polarizing plates. In general, a color filter in which an organic pigment is dispersed has a degree of polarization controlled by the liquid crystal due to light scattering by the pigment particles. There is a problem of disturbing. That is, there is a phenomenon in which light leaks when light must be blocked (OFF state), and transmitted light attenuates when light must be transmitted (ON state). The ratio of the brightness on the display in the ON state and the OFF state is called a contrast ratio. In particular, it is known that yellow and orange pigments significantly reduce this contrast ratio (Ueki, et al, Proceedi).
ngof the 7th Conference on Color Tehnology, pp. 89
-98 (1990)).

The present inventors have focused on improving the transparency and contrast ratio by making the primary particles of a pigment used in a coloring composition for a color filter finer, and have reached the present invention. In ordinary paints and inks, the transparency generally increases as the degree of dispersion of the pigment is increased. However, in ordinary dispersing machines such as sand mills, three-roll mills, and ball mills, the transparency increases when the primary particles are dispersed. Will not go up. The dispersing process using a normal dispersing machine is a process in which the secondary particles, which are aggregates of the primary particles of the pigment, are mainly loosened to obtain a dispersion close to the primary particles. Requires that the primary particles be finer.

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

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

[0008]

SUMMARY OF THE INVENTION It is an object of the present invention 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 in various resistances.

[0009]

That is, the present invention provides at least a part of an organic pigment, a water-soluble inorganic salt (A), and a water-soluble organic solvent (B) which does not substantially dissolve (A). After mechanically kneading the rosin or rosin derivative (C) (hereinafter, this step is referred to as salt milling),
By dispersing the treated pigment obtained by removing (A) and (B) in a transparent resin, a color filter having a high contrast ratio and a coloring composition for a color filter used therefor are provided.

More specifically, the above salt milling is at least partially dissolved in a small amount of water-soluble organic solvents (B) and (B) as a wetting agent in a mixture of an organic pigment and a water-soluble inorganic salt (A). After adding rosin or rosin derivative (C) and kneading strongly with a kneader or the like, the mixture is poured into water and stirred with a high-speed mixer or the like to form a slurry. Next, this slurry is filtered, washed with water, and dried if necessary, to obtain a treated pigment that is fine and has little aggregation of the pigment during drying. When the pigment is dispersed in an oily varnish, the treated pigment before drying (called a filter cake) can be dispersed in an oily varnish while removing water by a method generally called flushing. When dispersing in a water-based varnish, the treated pigment does not need to be dried, and the filter cake can be directly dispersed in the varnish. In addition, the pigment is dried and agglomerated by adding an alkali-soluble resin dissolved in an aqueous alkali solution to the above slurry, thoroughly stirring and mixing, and then neutralizing with an aqueous acidic solution such as hydrochloric acid or sulfuric acid to deposit the resin on the pigment, or Prevention can also be achieved by adding an aqueous solution of a water-soluble polyvalent metal salt such as calcium or barium chloride to precipitate the resin and deposit it on the pigment.

The treated pigment is dispersed in an ordinary dispersing machine such as a sand mill or a three-roll mill together with a transparent resin for forming a color filter, a solvent and, if necessary, a dispersant. )
As compared with the case where a pigment is used, a coloring composition for a color filter in which the pigment is finely dispersed is obtained. The organic pigments used in the present invention are described below with a color index (C.I.).
Show 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 process can be performed by mixing, for example, a mixture of pigments having different hues, such as a green pigment and a yellow pigment, or a red pigment and an orange pigment or a yellow pigment, can be used.

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. As for 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, it is necessary to determine the ratio in terms of both processing efficiency and production efficiency, but it is preferable to use 1 to 10 times the weight ratio of the inorganic salt to the pigment. The organic solvent (B) is not particularly limited as long as it is water-soluble and does not dissolve the inorganic salt (A). However, the temperature rises during salt milling, and the solvent is easily evaporated. 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 rosin or rosin derivative (C) should preferably be solid at room temperature, insoluble in water, and at least partially soluble in the water-soluble organic solvent (B) used as a wetting agent during salt milling. . When a dried pigment is used, the rosin or rosin derivative (C) used is preferably solid at room temperature. It is possible to perform salt milling using a resin that is liquid at room temperature, but it is not preferable because the treated pigment causes blocking during drying and becomes difficult to disperse, but the flushing method and the aqueous dispersion described above are used. Obtainable. However, when salt milling is performed using two or more kinds of resins in combination, the treated pigment may be dried and used if a partially liquid resin is used and the mixture is solid at room temperature.

A color filter is manufactured by dispersing a pigment in a photopolymerizable or photocrosslinkable medium to form a colored resist material, pattern-exposing a coating film of the colored resist material, and removing an unexposed portion with a developing solution. Although the method is widely used, in the case of using this method, the amount of processing is limited because a resin insoluble in a developing solution adversely affects development.
Therefore, in this case, it is preferable that the rosin or the rosin derivative (C) is dissolved in the developer. Recently, an organic solvent is rarely used as a developing solution due to environmental problems, and an alkali developing solution is generally used. Rosin or a rosin derivative is an alkali-soluble resin.

[0015]

In addition to the above compounds, additives such as a dispersant and a plasticizer at the time of salt milling and inorganic pigments such as calcium carbonate, barium sulfate and silica which are generally used as extenders may be used in combination. The coloring composition for a color filter of the present invention may be prepared by dispersing the colorant that has been subjected to the salt milling treatment together with a transparent resin and a solvent, if necessary, or mechanically kneading the colorant with the transparent resin in advance and then dissolving the solvent. Or by adding and dispersing a resin solution.
The colorant and the transparent resin are in a solid content ratio of 1: 4 to 1
It is blended at a ratio of 0: 1.

For dispersing the colorant in the transparent resin, various dispersing means such as a three-roll mill, a two-roll mill, a sand mill, and a kneader can be used. In order to improve the dispersion, various dispersing aids such as various surfactants and pigment derivatives 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. In addition, when storage stability is considered, a small amount of a stabilizer such as a polymerization inhibitor may be added. The transparent resin is 400 ~
The transmittance is 80% or more in the entire wavelength region of 700 nm,
Preferably, 95% or more of the resin is used. Transparent resins include thermosetting resins, thermoplastic resins, photosensitive resins,
Monomers, oligomers, and the like that form a coating film similar to a resin when cured by irradiation with radiation are used alone or in combination of two or more. When curing by ultraviolet irradiation, a photoinitiator or the like is used.

However, since high-temperature heating is performed in a later step in the production of the color filter, it is necessary to use a resin having high resistance even in the heat treatment. In addition, since a treatment with various solvents and chemicals is also performed in a later step, the formed image is required to have solvent resistance. Examples of thermosetting resin and thermoplastic resin 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 thereof include a polyimide resin, a benzoguanamine resin, a melamine resin, and a urea resin.

As the photosensitive resin, a (meth) acrylic compound, a carbonic acid resin or the like can be added to a linear polymer having a reactive substituent such as a hydroxyl group, a carboxyl group or an amino group 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 colored resist material generally comprises a pigment dispersed in a composition in which a thermosetting resin, a thermoplastic resin or a photosensitive resin is mixed with a monomer and a photoinitiator.

The monomers and oligomers that can be used in the colored resist material 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, penta Erythritol tri (meth) acrylate,
Hexa of caprolactone adduct of styrene, vinyl acetate, various acrylates, various methacrylates, acrylonitrile, dipentaerythritol hexa (meth) acrylate, tricyclodecanyl (meth) acrylate, dipentaerythritol hexa (meth) acrylate (Meth) acrylate, melamine (meth) acrylate, epoxy (meth) acrylate prepolymer and the like.

Examples of the photoinitiator include 4-phenoxydichloroacetophenone, 4-tert-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropane-1one, 1 -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 -methyldiphenylsulfide; 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 compounds such as carbazole photoinitiators and imidazole photoinitiators are used. Can be

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. A solvent is used in the coloring composition for a color filter in order to sufficiently disperse the coloring agent and to apply it to a glass substrate to have a thickness of 0.2 to 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 ketone, petroleum solvents and the like can be mentioned, and they are used alone or as a mixture.

By 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-developable type coloring resist agent and the like can be produced. it can. These printing inks, colored resist agents, and the like are subjected to centrifugal separation, sintering filter, membrane filter, or other means to obtain coarse particles of 5 μ or more, preferably 1 μ or more, more preferably 0.5 μ or more. Removed dust is manufactured. Since the printing ink can be patterned by simply repeating printing and drying, it is low cost and excellent in mass productivity as a color filter manufacturing method. Further, fine patterns having high dimensional accuracy and smoothness can be printed with the development of printing technology.

In order to perform printing, it is preferable that the composition be such that the ink does not dry and solidify on a printing plate or on a blanket. In addition, if the blanket swells or dissolves, the reproducibility of the pattern and the transparency of the blanket are reduced, which requires various precautions in selecting a solvent for the printing ink. Further, control of the fluidity of the ink on the printing press is also important, and the viscosity of the ink can be adjusted by a dispersant or extender. The above-mentioned solvent-developing or alkali-developing colored resist material is applied onto a transparent substrate by a coating method such as spray coating, spin coating, or roll coating. The dried film, if necessary, is 0.2 to 5 microns, and is exposed to ultraviolet light through a mask having a predetermined pattern, either in contact or non-contact. After that, the unexposed portion, that is, the uncured portion is removed by immersion in a solvent or an alkali developing solution or sprayed by spraying to form a pattern, and the same operation is repeated for other colors to produce a color filter. Further, in order to accelerate the polymerization of the resist material, heating can be performed if necessary.

In the 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, an antifoaming agent or a surfactant can be added. In order to increase the UV exposure sensitivity, the above-mentioned colored resist is applied and dried, and then a water-soluble or alkali-water-soluble resin such as polyvinyl alcohol or a water-soluble acrylic resin is applied and dried to form a film for preventing oxygen inhibition. Alternatively, ultraviolet exposure can be performed.

[0026]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below based on embodiments.
Prior to the embodiment, a method of measuring a contrast ratio will be described. FIG. 1 shows a conceptual diagram of the measuring device. The light emitted from the liquid crystal display backlight unit (7) is polarized by passing through the polarizing plate (6), and passes through the dried coating film (4) of the colored composition applied on the glass substrate (5). , And reaches the polarizing plate (3). Polarizing plate (6) and polarizing plate (3)
If the planes of polarization are parallel, light will pass through the polarizer (3), but if the plane of polarization is orthogonal, the light will pass through the polarizer (3).
Will be shut off. However, when the light polarized by the polarizing plate (6) passes through the coating film (4), scattering or the like by pigment particles occurs, and a part of the polarization plane is shifted. The amount of light transmitted through the polarizing plate (3) decreases, and when the polarizing plate is straight, a part of the light passes 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 plate is parallel to the brightness when the polarizing plate is orthogonal is called a contrast ratio.

Contrast ratio = Luminance in parallel / Luminance in orthogonal direction Therefore, when scattering occurs due to the pigment of the coating film (4), the luminance in the parallel state decreases and the luminance in the orthogonal direction increases. Therefore, the contrast ratio decreases. The luminance meter (1) is a color luminance meter BM-5A manufactured by Topcon Corporation,
As a polarizing plate, Sanritsu polarizing film LLC2-92-18 was used. At the time of the measurement, in order to block unnecessary light, the measurement was performed by applying a black mask (2) having a 1 cm square hole to the measurement portion. Next, in order to confirm the effects of the present invention, an example of the production of 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 parts were added, heated to 100 ° C., and at the same temperature, a mixture of the following monomer and thermal polymerization initiator was added dropwise 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. Thereafter, 2.0 parts of azobisisobutyronitrile was added to 50 parts of cyclohexanone.
The solution dissolved in the above portion was added, and the reaction was further continued for 1 hour to synthesize a resin solution.

A part of the resin solution is sampled and 180
The resin was heated and dried at 20 ° C. for 20 minutes to measure the non-volatile content, and cyclohexanone was added to the previously synthesized resin solution so that the non-volatile content was 20% to prepare a resin solution a. (Resin Solution Production Example b) A separable flask was charged with 600 parts of diethylene glycol monobutyl ether and 400 parts of ethylene glycol monobutyl ether, and epoxy resin (“Epicoat 1004” manufactured by Shell Chemical Co., Ltd.) was introduced at about 100 ° C. while introducing nitrogen gas. 600 parts were gradually added and dissolved, and the temperature was raised to 100 ° C. to produce a resin solution.
Next, several grams of the resin solution was precisely weighed, dried at 140 ° C. for 2 hours, and the nonvolatile content was measured. A mixed solution of 6/4 of diethylene glycol monobutyl ether / ethylene glycol monobutyl ether was added, and the nonvolatile content was 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 the present invention. The “part” in the embodiment
Represents "parts by weight". The symbol after the pigment name is the color index No. And, for example, “P.
ow 139 ”is“ CI Pigment Yel ”
low 139 ".

[0031]

Example 1 (Method for producing salt milled pigment) Yellow pigment (B
"Pariotor Yellow L1820" manufactured by ASF:
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, the mixture was poured into about 3 liters of warm water, 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 the solvent. The pigment was dried in a hot air oven at 60 ° C. for about 24 hours to obtain a salt milled pigment. (Production method of ink) 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 charged into a 140 ml mayonnaise bottle, and dispersed for 3 hours with a paint conditioner manufactured by Red Devil Co., Ltd. A dispersion ink was obtained. (Preparation of Ink Coating) The obtained ink is applied to a glass plate having a thickness of about 1 mm with a # 3 bar coater and dried in a 70 ° C. hot air oven for 20 minutes to form an ink coating having a thickness of about 1 μm. Obtained.

[0032]

[0033]

[0034]

Comparative Example 7 An ink coating film was obtained in the same manner as in Example 1 using the following treated pigment. "Pariotall Yellow L181
9 ", 250 g, sodium chloride 700 g and polyethylene glycol 300 (manufactured by Tokyo Chemical Industry Co., Ltd.) 320 g were charged into the kneader described in Example 1 and kneaded for 3 hours. This was subjected to the same operation as in Example 1 to obtain a salt-milled pigment containing no resin.

[0035]

[Example 2] "Palio Thor Yellow L1819" 250
g instead of orange pigment (“Lionol Orange B NEW” manufactured by Toyo Ink Mfg. Co., Ltd .: P. Orange 1
3) Salt milling treatment and ink formation were performed in the same manner as in Example 1 using 250 g to obtain an ink coating film.

[0036]

[Embodiment 3] "Palio Thoreau L1819" 250
A salt milling-treated pigment was produced in the same manner as in Example 1 except that 280 g of a red pigment (“Chromophthal Red A2B” manufactured by BASF: P. Red 177) was used instead of g.

[0037]

[Embodiment 4] "Palio Thoreau L1819" 250
g instead of g, a green pigment (“Lionol Green 6YK: P. Green 36” manufactured by Toyo Ink Mfg. Co., Ltd.) 280
Using g, a salt milled pigment was produced in the same manner as in Example 1 to obtain an ink coating film.

[0038]

Embodiment 5 "Palio Thoreau L1819" 250
280 g of blue pigment ("Lionol Blue E" manufactured by Toyo Ink Manufacturing Co., Ltd .: P. Blue 15: 6) instead of g
Was used to produce a salt-milled pigment in the same manner as in Example 1 to obtain an ink coating film.

[0039]

Embodiment 6 "Palio Thoreau L1819" 250
g instead of violet pigment ("Lionol Violet RL" P. Violet 2 manufactured by Toyo Ink Mfg. Co., Ltd.)
3) A salt milling-treated pigment was produced in the same manner as in Example 1 using 280 g to obtain an ink coating film.

[0040]

[Comparative Example 1] "Palio Thor 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 charged into a 140 ml mayonnaise bottle and dispersed for 3 hours with a paint conditioner manufactured by Red Devil Co., Ltd., thereby obtaining 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 "Lionol Orange B NEW" was used instead of "9".

[0042]

[Comparative Example 3] "Pariotor Yellow L181" of Comparative Example 1
In the same manner as in Example 1 except that “Chromophthal Red A2B” was used instead of “9”, an ink coating film was obtained.

[0043]

COMPARATIVE EXAMPLE 4 Comparative Example 1 of "Paliotol Yellow L181"
In the same manner as in Example 1 except that "Lionol Green 6YK" was used instead of "9", an ink coating film was obtained.

[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 "Lionol 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 “Lionol Violet RL” was used instead of “9”. The contrast ratio of the ink coating films of the above Examples and Comparative Examples was measured, and the following results were obtained. Contrast ratio Contrast ratio Example 1 160 Example 4 1660 Comparative example 1 48 Comparative example 4 950 Comparative example 7 123 Example 5 1840 Example 2 95 Comparative example 5 960 Comparative example 2 32 Example 6 220 Example 3 1300 Comparative example 6 110 Comparative Example 3 660

[0046]

Example 7 Using the inks obtained in the above examples, the following three kinds of alkali-developable colored resists were prepared. (Production of red resist) Ink obtained in Example 1 14.0 parts Ink obtained in Example 3 32.8 parts Resin solution a 7.8 parts NK ester ATMPTT (manufactured by Shin-Nakamura Chemical Co.) 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 was sufficiently stirred in a container and filtered with a 1 μm filter to produce a red resist. . (Preparation of green resist) Ink obtained in Example 1 10.5 parts Ink obtained in Example 4 34.5 parts Resin solution a 6.7 parts NK ester ATMPTT (manufactured by Shin-Nakamura Chemical Co.) 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 sufficiently stirred in a container and filtered through a 1 μm filter to produce a green resist. . (Preparation of blue resist) Ink obtained in Example 5 30.0 parts Ink obtained in Example 6 1.6 parts Resin solution a 19.1 parts NK ester ATMPTT (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 sufficiently stirred in a container and filtered through a 1 μm filter to produce a green resist. .

Next, each of the colored resists was applied on a glass substrate having a thickness of 1 mm by a spin coater so as to have a dry film thickness of 1.8 μm, and dried at 70 ° C. for 10 minutes. Further, a 5% aqueous solution of polyvinyl alcohol (manufactured by Kokusan Chemical Co., Ltd., molecular weight: about 500) is applied on the dried coating film to a thickness of 1 μm.
And dried at 70 ° C. for 20 minutes. next,
UV exposure through a mask having a 50 μm line and space stripe pattern (integrated light amount: 40 m
J), dipped in a 2% aqueous solution of sodium carbonate 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 are applied in the same manner, and the whole surface is exposed to the same amount of ultraviolet rays without using a mask.
After dipping for 2 seconds, washing with water and heating at 200 ° C. for 30 minutes, the contrast ratio was measured, and the following results were obtained. Red resist contrast ratio: 830 Green resist contrast ratio: 1380 Blue resist contrast ratio: 1200

[0049]

Example 8 A salt milling-treated pigment was dispersed in a 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 4 16.33 parts Dispersant 0.76 parts Precipitable barium sulfate 1.30 parts Diethylene glycol monobutyl ether 8. The mixture was mixed with 05 parts of ethylene glycol monobutyl ether (5.37 parts), kneaded well with a three-roll mill, and filtered through a 5 μm filter to prepare a green ink. Next, using a flatbed proof printing press, the green ink was applied onto an intaglio having a square pattern of 1 cm square at a plate depth of 10 μm, and excess ink was scraped off with a doctor. After transferring the ink on the intaglio to a blanket made of silicone rubber, the blanket was brought into contact with a glass substrate for a 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 form a film having a thickness of 2.0 μm.
Was produced. As a result of measuring the contrast of the obtained color filter, a value of 1150 was obtained.

[0050]

Comparative Example 8 A green color filter was prepared in the same manner as in Example 8 except that untreated pigments, namely, “Paliotor 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 having excellent durability and a high contrast ratio.

[Brief description of the drawings]

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

──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Makoto Sakakawa 1-1-1, Taito, Taito-ku, Tokyo Inside Toppan Printing Co., Ltd. (72) Inventor Tanata Hitoshi 1-5-1, Taito, Taito-ku, Tokyo Toppan printing Co., Ltd. in the examiner Yokoi KanShin (56) reference Patent Sho 60-129739 (JP, a) JP flat 5-43704 (JP, a) (58 ) investigated the field (Int.Cl. ⁷ , DB name) G02B 5/20-5/28 C08J 3/00-3/28

Claims (3)

(57) [Claims] An organic pigment , a water-soluble inorganic salt (A) , (A)
Water-soluble organic solvent which does not substantially dissolve the (B) and
Rosin or rosin-induced at least partially soluble in (B)
A colored composition for a color filter , wherein a treated pigment obtained by mechanically kneading a conductor (C) and removing (A) and (B) is dispersed in a transparent resin . 2. The method according to claim 1, wherein the organic pigment is a yellow pigment or
The coloring composition for a color filter according to claim 1, wherein the composition is an orange pigment . 3. A colored set according to claim 1, which is provided on a substrate.
A color filter in which multiple colors are arranged using a product .