JP2002372779A - Resist for color filter and method for producing color filter - Google Patents

Abstract

PROBLEM TO BE SOLVED: To form a color resist film excellent in uniformity of film thickness without causing a break in a film during coating by using a color resist for a color filter excellent in storage stability. SOLUTION: In the resist for a color filter containing a pigment, a polymer, a monomer or an oligomer, a photopolymerization initiator and a solvent, the solvent is a mixed solvent and contains at least an alcoholic compound.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a color filter resist and a method for manufacturing a color filter using the same.

[0002]

2. Description of the Related Art At present, a pigment dispersion method is mainly used for producing a color filter used in a liquid crystal display device or the like. Examples of the pigment dispersion method include a photosensitive acrylic method and a non-photosensitive polyimide method. As an example of a color resist for a pigment dispersion method color filter (hereinafter referred to as a “color resist”) used in the manufacture of a pigment dispersion method color filter,
A description will be given of a photosensitive color resist (photosensitive acrylic method) having an acrylic polymer, an acrylic polyfunctional monomer or oligomer, a photopolymerization initiator, a diluting solvent, and a coloring pigment as constituents (for example, JP-A-8-2).
No. 20341).

The production of a color filter using a photosensitive color resist having an acrylic polymer, an acrylic polyfunctional monomer or oligomer, a photopolymerization initiator, a solvent, and a coloring pigment as constituents is disclosed in, for example, JP-A-8-220341. This is performed by the following steps. First, a photosensitive color resist is applied on a substrate, and a cycle of pattern exposure, pattern development, baking and heating is repeated for the required number of colors to obtain a colored coating pattern.

[0004] As a method of applying a color resist to a substrate, there are a spin coating method, a roll coating method, a bar coating method, a die coating method and the like. The spin coating method is widely used for coating a photoresist on a semiconductor wafer, and forms a coating film by dropping a color resist on the center of the surface of a rotating substrate. For color filter applications, see, for example,
It is disclosed in JP-A-10-107767. The coating film obtained by the spin coating method is described in, for example, JP-A-6-34.
As disclosed in JP-A-8023 and JP-A-7-261378, by making the rheological properties of the color resist into Newtonian, the film thickness can be made uniform with high accuracy over the entire range of the substrate. When the color resist is non-Newtonian or has a high viscosity, a thick portion is formed at the center of rotation, and the uniformity of the film thickness is reduced. In addition, the amount of color resist used to obtain a desired film thickness is extremely large, which is uneconomical. In addition, the color resist may adhere to the edge and the back surface of the substrate, or the color resist scattered in the apparatus may be gelled or solidified, which may result in poor process stability, poor cleanliness, and reduced yield. .

[0005] The roll coating method is a method of transferring a color resist to a substrate via a rubber roll, and is capable of coating a long coating material or a roll-shaped wound coating material. it can. However, since the color resist is sequentially sent from the pan to the application roll and then to the substrate, the time required for the color resist to be exposed to air is long, so that not only the color resist easily undergoes deterioration due to moisture absorption, but also foreign matter is easily mixed therein. . If foreign matter enters,
When the color resist is non-Newtonian or has a high viscosity, the leveling property is poor, so that a streak is generated in the substrate moving direction with foreign matter as a protrusion.

The bar coating method is a method of applying a color resist to a substrate using a bar in which a thin wire is wound around a rod, and is disclosed in Japanese Patent Application Laid-Open No. 2-280881 and the like. In this method, since the wire wound on the rod is in direct contact with the substrate, when the color resist is non-Newtonian or has a high viscosity, the leveling property is poor and traces of the wire remain. The die coating method is a method of forming a coating film on a substrate by moving a die for discharging a color resist from a slit relatively to the substrate, and is disclosed in Japanese Patent Application Laid-Open No. 7-8894. This method has an advantage that the usage rate of the discharged color resist is extremely high, and since the color resist liquid supply path is sealed until the color resist is discharged from the slit, the quality of the coating film can be maintained high. It is a coating method. However, when the viscosity of the color resist is too high or when an attempt is made to form a thin wet film, a defect that a streak occurs in the substrate moving direction is likely to occur. On the other hand, if the viscosity of the color resist is too low, the thickness of the coating end portion tends to be large. Therefore, it is preferable to control the viscosity of the color resist used in the die coating method within an appropriate range. In order to change the viscosity of the color resist, it is conceivable to control the solid component concentration of the color resist.However, the range in which the viscosity of the color resist can be controlled by changing the solid component concentration is narrow, and the desired viscosity may not be obtained. Many.

A general color resist is a solvent in which propylene glycol monomethyl ether acetate (hereinafter referred to as "P
GMEA ”). P
Since the viscosity of GMEA was as low as 1.1 cp, when PGMEA was used as a solvent, the viscosity of a color resist prepared with a desired solid component concentration was as low as about 3 cp, and did not reach the desired color resist viscosity for the die coating method.

[0008]

SUMMARY OF THE INVENTION The present invention has been made in view of the above-mentioned circumstances, and has as its object the purpose of the present invention is to provide good coatability, no occurrence of drying unevenness, and a high level No film breakage, excellent dispersion stability,
An object of the present invention is to provide a color resist having high transparency, contrast, and surface smoothness.

[0009]

To solve the above-mentioned problems, the present invention has the following arrangement. (1) A color filter resist containing a pigment, a polymer, a monomer or an oligomer, a photopolymerization initiator, and a solvent, wherein the solvent is a mixed solvent and contains at least an alcohol compound. (2) The resist for a color filter according to (1), wherein the alcohol compound is 3-methoxy-3-methyl-1-butanol. (3) The mixed solvent comprises at least 3-methoxy-3-methyl-1-butanol and propylene glycol monomethyl ether acetate.
The resist for a color filter according to the above. (4) A method for producing a color filter, comprising using the resist for a color filter according to any one of (1) to (3). (5) A method for producing a color filter, comprising applying the color filter resist according to any one of (1) to (3) onto a substrate by a die coating method.

[0010]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The components of the present invention will be described below.

A color resist has at least one or more functional groups, and ion or radical generated by irradiating a photoinitiator with a curing energy beam causes ionic polymerization or radical polymerization to increase the molecular weight or crosslink. What consists of a monomer or oligomer which forms a structure is used. The functional group referred to here is a vinyl group,
An atomic group or a bonding mode that causes a reaction such as a carboxyl group or a hydroxyl group.

Examples of such monomers and oligomers include epoxy acrylate, urethane acrylate, polyester acrylate, polyether acrylate,
Acrylic type such as silicon acrylate and non-acrylic type such as unsaturated polyester / styrene type and polyene / styrene type are exemplified. Among them, acrylic type is preferable from the viewpoint of curing speed and a wide range of selection of physical properties.

An acrylic resin will be described as an example of a resin for a photosensitive color resist. Generally, the acrylic resin has a structure containing at least an acrylic polymer, an acrylic polyfunctional monomer or oligomer, and a photopolymerization initiator in order to impart photosensitivity.

Hereinafter, a case where an acrylic resin is used as a typical example of a photosensitive color resist will be described in detail.

Acrylic polymers that can be used include:
Although there is no particular limitation, a copolymer of an unsaturated carboxylic acid and an ethylenically unsaturated compound can be preferably used. Examples of unsaturated carboxylic acids include, for example, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, maleic acid, fumaric acid, vinyl acetic acid, and acid anhydride.

These may be used alone or in combination with other copolymerizable ethylenically unsaturated compounds. Specific examples of the copolymerizable ethylenically unsaturated compound include methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, isopropyl acrylate, n-propyl methacrylate, and methacrylic acid. Isopropyl, n-butyl acrylate, n-butyl methacrylate, s-acrylate
ec-butyl, sec-butyl methacrylate, iso-butyl acrylate, iso-butyl methacrylate, tert-butyl acrylate, tert-butyl methacrylate,
N-pentyl acrylate, n-pentyl methacrylate,
Unsaturated carboxylic acid alkyl esters such as 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, benzyl acrylate and benzyl methacrylate; fragrances such as styrene, p-methyl styrene, o-methyl styrene, m-methyl styrene and α-methyl styrene Aromatic vinyl compounds, unsaturated carboxylic acid aminoalkyl esters such as aminoethyl acrylate, glycidyl acrylate, unsaturated carboxylic acid glycidyl esters such as glycidyl methacrylate, vinyl acetate, carboxylic acid vinyl esters such as vinyl propionate, acrylonitrile, methacrylonitrile, vinyl cyanide compounds such as α-chloroacrylonitrile; aliphatic conjugated dienes such as 1,3-butadiene and isoprene; acryloyl groups at the terminals; Or macromonomers such as polystyrene, polymethyl acrylate, polymethyl methacrylate, polybutyl acrylate, polybutyl methacrylate, and polysilicone having a methacryloyl group, but are not limited thereto.

The use of an acrylic polymer having an ethylenically unsaturated group added to the side chain is preferred because the sensitivity during processing is improved. Examples of the ethylenically unsaturated group include a vinyl group, an allyl group, an acryl group, and a methacryl group. As a method for adding such a side chain to an acrylic (co) polymer, when the acrylic (co) polymer has a carboxyl group or a hydroxyl group, an ethylenically unsaturated compound having a glycidyl group in these groups is used. Or an addition reaction of acrylic acid or methacrylic acid chloride. In addition, a compound having an ethylenically unsaturated group can be added using isocyanate. Examples of the ethylenically unsaturated compound having a glycidyl group and acrylic acid or methacrylic acid chloride include glycidyl acrylate, glycidyl methacrylate, glycidyl α-ethyl acrylate, crotonyl glycidyl ether, glycidyl ether crotonic acid, glycidyl isocrotonate. Ether, acrylic acid chloride, methacrylic acid chloride and the like can be mentioned.

Examples of the polyfunctional monomer include bisphenol A diglycidyl ether (meth) acrylate, poly (meth) acrylate carbamate, modified bisphenol A epoxy (meth) acrylate, adipic acid 1,6-hexanediol (meth) acrylic acid Ester, phthalic anhydride propylene oxide (meth) acrylate, trimellitate diethylene glycol (meth) acrylate, rosin-modified epoxy di (meth) acrylate, alkyd-modified (meth) acrylate or oligomer such as tripropylene glycol di ( (Meth) acrylate, 1,6-hexanediol di (meth) acrylate, bisphenol A diglycidyl ether di (meth) acrylate, trimethylolpropane tri (meth) Acrylate, pentaerythritol tri (meth) acrylate, triacrylformal, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate. These can be used alone or in combination. In addition, the following monofunctional monomers can also be used in combination. For example, ethyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, hydroxyethyl (meth) acrylate, n-butyl methacrylate, glycidyl methacrylate, lauryl ( Meth) acrylate, stearyl (meth) acrylate, isobornyl (meth) acrylate, etc.
A mixture of two or more of these, a mixture with another compound, or the like is used. By selecting and combining these polyfunctional and monofunctional monomers and oligomers, it is possible to control the sensitivity and processability characteristics of the resist. In particular, a methacrylate compound is preferable to an acrylate compound for increasing hardness, and a compound having three or more functional groups is preferable for increasing sensitivity. Further, melamines, guanamines and the like can be preferably used instead of the acrylic monomers.

The photopolymerization initiator is not particularly limited.
Known ones can be used, for example, benzophenone, N,
N'-tetraethyl-4,4'-diaminobenzophenone, 4-methoxy-4'-dimethylaminobenzophenone, 2,2-diethoxyacetophenone, benzoin,
Benzoin methyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, α-hydroxyisobutylphenone, thioxanthone, 2-chlorothioxanthone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl]-
2-morpholino-1-propane, t-butylanthraquinone, 1-chloroanthraquinone, 2,3-dichloroanthraquinone, 3-chloro-2-methylanthraquinone, 2-ethylanthraquinone, 1,4-naphthoquinone, 9,10-fe Nantraquinone, 1,2-benzanthraquinone, 1,4-dimethylanthraquinone, 2-
Phenylanthraquinone, 2- (o-chlorophenyl)
And -4,5-diphenylimidazole dimer. Further, other acetophenone-based compounds, imidazole-based compounds, benzophenone-based compounds, thioxanthone-based compounds, phosphorus-based compounds, triazine-based compounds, and inorganic photopolymerization initiators such as titanates can also be preferably used. Further, it is preferable to add a sensitizing aid such as p-dimethylaminobenzoic acid ester since the sensitivity can be further improved. Further, two or more of these photopolymerization initiators can be used in combination.

The amount of the photopolymerization initiator to be added is not particularly limited, but is preferably 2 to 2 with respect to the total solid content of the resist.
It is 30% by weight, more preferably 5 to 25% by weight, further preferably 10 to 20% by weight. In the color resist of the present invention, the resin component and the colorant containing at least the pigment are usually in a weight ratio of 1: 9 to 9: 1, preferably 2: 8 to 8: 2, more preferably 3: 7 to 8: 2. It is used by mixing in the range of 7: 3. If the amount of the resin component is too small,
Adhesion of the colored film to the substrate becomes poor, and if the amount of the pigment is too small, the degree of coloring becomes a problem. In addition, in the resist, from the viewpoints of coatability, drying property, etc., the solid content concentration of the resin component and the pigment is 5 to 25% by weight, preferably 10 to 23% by weight, more preferably 15 to 20% by weight.
Use in the range of weight%.

As the solvent in the color resist used in the present invention, a solvent that dissolves the resin to be used can be used. Examples of the diluting solvent for dissolving the acrylic resin include amide polar solvents such as N-methyl-2-pyrrolidone, N, N-dimethylacetamide, N, N-dimethylformamide, β-propiolactone, γ-butyrolactone, Lactones such as γ-valerolactone, δ-valerolactone, γ-caprolactone, ε-caprolactone, methyl cellosolve, ethyl cellosolve, methyl carbitol, ethyl carbitol, propylene glycol monoethyl ether, dipropylene glycol methyl ether, propylene glycol Ethylene glycol or propylene glycol derivatives such as n-butyl ether, or PGMEA, propylene glycol diacetate, ethyl acetoacetate, methyl-3-
Aliphatic esters such as methoxypropionate, 3-methyl-3-methoxybutyl acetate, and 3-methoxybutyl acetate; and methanol, ethanol, n-propyl alcohol, isopropyl alcohol, and 3-methyl-2-butanol. Alcohols,
It is also possible to use aliphatic alcohols such as 3-methyl-3-methoxybutanol and ketones such as cyclopentanone and cyclohexanone.

Therefore, as the solvent for the color resist used in the present invention, it is preferable to use a single solvent or a mixed solvent of two or more kinds of solvents in which the resin used is dissolved, as appropriate. In this case, PGMEA (propylene glycol monomethyl ether acetate) is preferably used as the main solvent because of its good safety, wettability, and solubility. It is also possible to use a poor solvent for the resin used as a secondary solvent. Examples of the solvent containing the alcohol compound of the present invention include alcohols such as methanol, ethanol, n-propyl alcohol, isopropyl alcohol, and 3-methyl-2-butanol;
Aliphatic alcohols such as 3-methyl-3-methoxybutanol can be used. As preferred solvents, aliphatic alcohols are desirable. Above all, 3-methyl-3
-Methoxybutanol is preferred because its viscosity is as high as 5.5 cp. If the proportion of the solvent comprising the alcohol compound in the whole solvent is less than 5% by weight, the thickness of the coating end portion becomes large due to insufficient viscosity of the color resist, and the uniformity of the film thickness tends to be reduced. When the ratio of the solvent composed of the alcohol compound to the entire solvent exceeds 80% by weight, the viscosity of the color resist is too large, and stripes are likely to be generated during the application of the color resist. It is preferable that the solvent composed of the alcohol compound accounts for 5 to 80% by weight of the entire solvent. 5
Since the viscosity of the color resist does not increase even after being stored for one month in an environment of ° C., it is more preferable that the solvent composed of the alcohol compound accounts for 5 to 50% by weight of the entire solvent. Since the viscosity of the color resist does not increase even when stored in a 5 ° C. environment for 4 months, it is more preferable that the solvent composed of the alcohol compound accounts for 5% by weight or more and less than 25% by weight of the entire solvent.

As the pigment in the color resist used in the present invention, as a red pigment, ColorIndex No.
Pigment Red 9, 97, 122, 123, 149,
168, 177, 180, 192, 215, 254 and the like, and as a green pigment, Color Index No.
Pigment Green 7, 36, etc., and blue pigments such as C
color Index No. Pigment Blue 15:
3, 15: 4, 15: 6, 21, 22, 60, 64 and the like, and as a yellow pigment, Color Index No. Pigment Yellow 20, 24, 86, 93, 109, 1
10, 117, 129, 138, 139, 150, 15
3 etc. are violet pigments such as Color Ind.
ex No. Pigment Violet 19, 23, 2
9, 30, 37, 40, 50, etc., as the orange pigment, Color Index No. Pigment Oranges 36, 43, 51, 55, 59, 61 and the like, and Color Index No. Pigment Black 7 and the like, carbon black, metal oxides and the like can be used. These pigments may be used alone or in combination of two or more. Further, as a dispersant to stabilize the dispersion of the pigment, a pigment intermediate, a derivative,
Intermediates and derivatives of dyes, "Solsperse", "EFK
Known materials such as a polymer dispersant such as A "can be used.

To the color resist used in the present invention, a surfactant may be added for the purpose of improving the coating property and the drying property of the colored film. The amount of the surfactant is usually 0.001 to 10% by weight of the pigment, preferably 0.1 to 10% by weight.
0.01 to 1% by weight. If the addition amount is too small, the coating properties,
There is no effect of improving the drying property of the colored coating, and if it is too large, the physical properties of the coating become poor. Specific examples of the surfactant include ammonium lauryl sulfate, anionic surfactant such as polyoxyethylene alkyl ether triethanolamine sulfate, stearylamine acetate, cationic surfactant such as lauryl trimethyl ammonium chloride, lauryl dimethylamine oxide, Amphoteric surfactants such as lauryl carboxymethylhydroxyethyl imidazolium betaine, nonionic surfactants such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, sorbitan monostearate, and silicones whose main skeleton is polydimethylsiloxane Surfactants and the like. In the present invention, the surfactant is not limited to these, and one or more surfactants can be used. In addition to the surfactant, an adhesion improver, a curing accelerator and the like can be added.

An example of the manufacturing method of the present invention will be described. As a method of applying a color resist on a substrate, there are a spin coater, a bar coater, a blade coater, a roll coater, a die coater, a method of applying to a substrate by a screen printing method, a method of immersing a substrate in a solution, and a method of applying a solution to a substrate. Various methods, such as spraying, can be used. As the substrate, a transparent substrate such as soda glass, non-alkali glass, and quartz glass, and a semiconductor substrate such as silicon and gallium-arsenic are usually used, but are not particularly limited thereto. When applying a resist on a substrate, treating the substrate surface with an adhesion aid such as a silane coupling agent, an aluminum chelating agent, or a titanium chelating agent can improve the adhesion between the colored film and the substrate. it can.

For example, after applying a red color resist on a transparent substrate by the above-described method, air drying, heat drying,
A color resist coating film is formed by vacuum drying or the like. In the case of heating and drying, it is preferable to use an oven, a hot plate, or the like, and perform the heating at 50 to 180 ° C. for 1 minute to 3 hours. In the case of a photosensitive color resist, an oxygen blocking film may be formed on the color resist coating film. Subsequently, a mask is placed on the film, and ultraviolet light is irradiated using an exposure device. Next, the development or etching of the color resist coating film, and if necessary, the photoresist coating film or the oxygen barrier film is performed with a developer containing a nonionic surfactant.

The developer used in the present invention includes water, an alkaline solution, an organic solvent, and a mixture thereof. The alkaline substance used in the alkaline developer is not particularly limited. For example, inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium silicate, sodium metasilicate, aqueous ammonia, ethylamine, n- Primary amines such as propylamine; secondary amines such as diethylamine and di-n-propylamine; tertiary amines such as triethylamine and methyldiethylamine; tetraalkylammonium hydroxide such as tetramethylammonium hydroxide (TMAH) , Quaternary ammonium salts such as choline, alcoholamines such as triethanolamine, diethanolamine, monoethanolamine, dimethylaminoethanol, diethylaminoethanol, pyrrole, piperidine, 1,8-dia Bicyclo [5,4,0]
-7-undecene, 1,5-diazabicyclo [4,3,
Organic alkalis such as cyclic amines such as 0] -5-nonane and morpholine.

The concentration of the alkaline substance is from 0.01% by weight to 50% by weight. Preferably from 0.05% by weight to 1%
0% by weight, more preferably 0.1 to 1% by weight. When the developer is an aqueous alkaline solution, the developer may be ethanol, γ-butyrolactone, dimethylformamide,
A water-soluble organic solvent such as N-methyl-2-pyrrolidone may be appropriately added.

Examples of the organic solvent for the organic solvent developer include amide polar solvents such as N-methyl-2-pyrrolidone, N, N-dimethylacetamide, N, N-dimethylformamide, β-propiolactone, γ- Lactones such as butyrolactone, γ-valerolactone, δ-valerolactone, γ-caprolactone, ε-caprolactone,
Methyl cellosolve, ethyl cellosolve, methyl carbitol, ethyl carbitol, ethylene glycol or propylene glycol derivatives such as propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, ethyl acetoacetate, methyl
Aliphatic esters such as 3-methoxypropionate and 3-methyl-3-methoxybutyl acetate; aliphatic alcohols such as ethanol and 3-methyl-3-methoxybutanol; and ketones such as cyclopentanone and cyclohexanone. Is mentioned. Among these developers, water or an aqueous solution of an alkaline aqueous solution is preferable from the viewpoint of working environment and waste developer treatment.

The developing system employs an immersion method, a spray method, a paddle method or the like, but is not particularly limited. After development or etching, the unnecessary photoresist film and oxygen barrier film are removed as necessary. After the development, a washing step with pure water or the like may be appropriately added.

The coating film pattern of the obtained color resist is then subjected to a heat treatment to become a patterned red filter. The heat treatment is usually performed in air, in a nitrogen atmosphere,
It is carried out continuously or stepwise at a temperature of 450 ° C., preferably 180 to 350 ° C. for 0.5 to 5 hours.

In addition, a color filter for a liquid crystal display device can be manufactured by forming a colored pattern using a color resist of green, blue or the like and, if necessary, a black color resist. Here, the patterning order of each color resist is not limited.

After the manufacturing method of the present invention, a protective film and a transparent conductive film can be formed on the pixel.

[0034]

EXAMPLES The present invention will now be described specifically with reference to examples, but the present invention is not limited to these examples.

Example 1 Color Index No. Pigment Blue 1
10.0 g of 5: 6 was weighed, and in 50 g of PGMEA, 7000 using a homogenizer using zirconia beads.
30.0 g of methyl methacrylate / methacrylic acid copolymer resin powder, 30.0 g of pentaerythritol tetramethacrylate as a polyfunctional monomer, 36915.0 g of "Irgacure" as a photopolymerization initiator were added to a pigment dispersion dispersed at 30 rpm for 30 minutes. 75.0 g in 375 g of a photosensitive resin solution (solid component concentration: 20 wt%) composed of 165 g of PGMEA and 135 g of 3-methyl-3-methoxybutanol (MMB) (20 wt% of MMB concentration in the mixed solvent)
Add 135g of color resist for color filter
Produced. The viscosity of the prepared color resist was 1
It was 0 cp. After that, the viscosity of the resist did not change even when stored for 4 months in an environment of 5 ° C. The prepared color resist was applied on an alkali-free glass substrate by a die coating method so that the film thickness after the heat treatment became 2 μm. The coating speed was 3 m / min. Thereafter, a heat treatment was performed at 80 ° C. for 15 minutes to obtain a color resist coating film.
At this time, no film breakage occurred during the application of the color resist. The film thickness of the color resist coating film was 2 μm at the center of the substrate, while the film thickness at the coating end portion was 2.2 μm, and the film thickness uniformity was good. Further, a predetermined area is exposed through a negative mask, and “Emulgen” A-60 (HLB12.8, polyoxyethylene derivative) (manufactured by Kao Corporation) is developed as a nonionic surfactant in a 0.2% diethylaminoethanol aqueous solution. The patterning substrate was obtained by immersion and development with shaking for 90 seconds in an alkali developing solution added with 0.1% of the total amount of the solution, followed by washing with pure water. By holding the obtained patterned substrate at 200 ° C. for 30 minutes in a hot air oven, the acrylic resin was cured, and the blue width was 50 μm.
m stripe pattern was obtained.

Example 2 Color Index No. Pigment Blue 1
10.0 g of 5: 6 was weighed, and in 50 g of PGMEA, 7000 using a homogenizer using zirconia beads.
30.0 g of methyl methacrylate / methacrylic acid copolymer resin powder, 30.0 g of pentaerythritol tetramethacrylate as a polyfunctional monomer, 36915.0 g of "Irgacure" as a photopolymerization initiator were added to a pigment dispersion dispersed at 30 rpm for 30 minutes. Photosensitive resin solution (solid component concentration: 20% by weight) to which 165 g of PGMEA, 67.5 g of 3-methyl-3-methoxybutanol (MMB) (10% by weight of MMB concentration in the mixed solvent) and 67.5 g of 3-methoxybutyl acetate were added. ) Add 75.0g out of 375g,
135 g of a color resist for a color filter was produced. The viscosity at the time of production of the produced color resist was 8 cp. After that, the viscosity of the resist did not change even when stored for 4 months in an environment of 5 ° C. The prepared color resist was applied to a non-alkali glass substrate by a die coating method so that the film thickness after the heat treatment became 2 μm. The coating speed was 3 m / min. Thereafter, a heat treatment was performed at 80 ° C. for 15 minutes to obtain a color resist coating film. At this time,
No film breakage occurred during the application of the color resist. The thickness of the color resist coating is 2 μm at the center of the substrate.
On the other hand, the film thickness at the coating end portion was 2.2 μm, and the film thickness uniformity was good.

Example 3 Color Index No. Pigment Blue 1
10.0 g of 5: 6 was weighed, and in 50 g of PGMEA, 7000 using a homogenizer using zirconia beads.
30.0 g of methyl methacrylate / methacrylic acid copolymer resin powder, 30.0 g of pentaerythritol tetramethacrylate as a polyfunctional monomer, 36915.0 g of "Irgacure" as a photopolymerization initiator were added to a pigment dispersion dispersed at 30 rpm for 30 minutes. 162.5 g of PGMEA, 3-
Methyl-3-methoxybutanol (MMB) 137.5
g (an MMB concentration of 25% by weight in the mixed solvent) was added to 375 g of a photosensitive resin solution (solid component concentration: 20% by weight).
5.0 g were added to prepare 135 g of a color resist for a color filter. The viscosity of the produced color resist at the time of production was 16 cp. Thereafter, the viscosity of the resist did not change even when stored for 1 month in an environment of 5 ° C.
When stored for 4 months in an environment of ℃ C, the viscosity of the resist is 18
cp, and the stability was slightly lowered as compared with Examples 1 and 2. The prepared color resist was applied on an alkali-free glass substrate by a die coating method so that the film thickness after the heat treatment became 2 μm. The coating speed was 3 m / min. Thereafter, a heat treatment was performed at 80 ° C. for 15 minutes to obtain a color resist coating film. At this time, no film breakage occurred during the application of the color resist. The film thickness of the color resist coating film was 2 μm at the center of the substrate, while the film thickness at the coating end portion was 2.2 μm, and the film thickness uniformity was good.

Example 4 Color Index No. Pigment Blue 1
10.0 g of 5: 6 was weighed, and in 50 g of PGMEA, 7000 using a homogenizer using zirconia beads.
30.0 g of methyl methacrylate / methacrylic acid copolymer resin powder, 30.0 g of pentaerythritol tetramethacrylate as a polyfunctional monomer, 36915.0 g of "Irgacure" as a photopolymerization initiator were added to a pigment dispersion dispersed at 30 rpm for 30 minutes. 75.0 g in 375 g of a photosensitive resin solution (solid component concentration: 20% by weight) to which 220 g of PGMEA and 140 g of 3-methyl-3-methoxybutanol (MMB) (40% by weight of MMB concentration in the mixed solvent) were added.
Add 135g of color resist for color filter
Produced. The viscosity of the prepared color resist was 2
It was 0 cp. After that, the viscosity of the resist did not change even when stored for 1 month in an environment of 5 ° C., but when stored for 4 months in an environment of 5 ° C., the viscosity of the resist increased to 32 cp, and the stability was slightly poor. Met. The prepared color resist was applied to a non-alkali glass substrate by a die coating method so that the film thickness after the heat treatment became 2 μm. The coating speed was 3 m / min. Thereafter, a heat treatment was performed at 80 ° C. for 15 minutes to obtain a color resist coating film. At this time, no film breakage occurred during the application of the color resist. The thickness of the color resist coating film was 2 μm at the center of the substrate, while the thickness at the coating end portion was 2.2 μm.
μm, and the film thickness uniformity was good.

Example 5 Color Index No. Pigment Blue 1
10.0 g of 5: 6 was weighed, and in 33 g of PGMEA and 17 g of 3-methyl-3-methoxybutanol (MMB), 700 g of zirconia beads and a homogenizer were used.
30.0 g of methyl methacrylate / methacrylic acid copolymer resin powder was added to the pigment dispersion dispersed at 0 rpm for 30 minutes,
30.0 g of pentaerythritol tetramethacrylate as a polyfunctional monomer, 15.0 g of “Irgacure” 369 as a photopolymerization initiator, and 300 g of MMB (70% by weight of MMB in a mixed solvent) (a photosensitive resin solution) %) 75.0 g of 375 g was added to prepare 135 g of a color resist for a color filter. The viscosity of the prepared color resist was 23.
cp. Thereafter, when the resist was stored for one month in an environment of 5 ° C., the viscosity of the resist increased to 34 cp, and the stability was slightly poor. The prepared color resist was applied to a non-alkali glass substrate by a die coating method so that the film thickness after the heat treatment became 2 μm. The coating speed was 3 m / min. Thereafter, a heat treatment was performed at 80 ° C. for 15 minutes to obtain a color resist coating film. At this time, no film breakage occurred during the application of the color resist. The film thickness of the color resist coating film was 2 μm at the center of the substrate, while the film thickness at the coating end portion was 2.2 μm, and the film thickness uniformity was good.

Example 6 Color Index No. Pigment Blue 1
Weigh 10.0 g of 5: 6 and weigh 16.5 g of PGMEA.
33.5 g of methyl-3-methoxybutanol (MMB)
And a methacrylic acid / methacrylic acid copolymer resin powder 3 in a pigment dispersion liquid dispersed at 7000 rpm for 30 minutes using a homogenizer using zirconia beads.
0.0 g, 30.0 g of pentaerythritol tetramethacrylate as a polyfunctional monomer, 15.0 g of "Irgacure" 369 as a photopolymerization initiator, 300 g of MMB
7% in 375 g of a photosensitive resin solution (solid component concentration: 20% by weight) to which (an MMB concentration of 85% by weight in the mixed solvent) was added.
5.0 g were added to prepare 135 g of a color resist for a color filter. The viscosity of the prepared color resist was 29 cp. Thereafter, when the resist was stored for one month in an environment of 5 ° C., the viscosity of the resist increased to 39 cp.
The prepared color resist was applied to a non-alkali glass substrate by a die coating method so that the film thickness after the heat treatment became 2 μm. The coating speed was 3 m / min. Then 80
Heat treatment at 15 ° C. for 15 minutes gave a color resist coating film. At this time, film breakage occurred during the application of the color resist. The film thickness of the color resist coating film was 2 μm at the center of the substrate, while the film thickness at the coating end portion was 2.2 μm, and the film thickness uniformity was good.

Comparative Example 1 Color Index No. Pigment Blue 1
10.0 g of 5: 6 was weighed, and in 50 g of PGMEA, 7000 using a homogenizer using zirconia beads.
30.0 g of methyl methacrylate / methacrylic acid copolymer resin powder, 30.0 g of pentaerythritol tetramethacrylate as a polyfunctional monomer, 36915.0 g of "Irgacure" as a photopolymerization initiator were added to a pigment dispersion dispersed at 30 rpm for 30 minutes. 75.0 g of 375 g of a photosensitive resin solution (solid component concentration 20% by weight) to which PGMEA 300 g was added was added to prepare 135 g of a color resist for a color filter. The viscosity of the prepared color resist was 3 cp. The prepared color resist was applied to a non-alkali glass substrate by a die coating method so that the film thickness after the heat treatment became 2 μm. Coating speed is 3
m / min. Thereafter, a heat treatment was performed at 80 ° C. for 15 minutes to obtain a color resist coating film. At this time, although film breakage did not occur at the time of application of the color resist, the thickness of the color resist coating film was 2 μm at the central portion of the substrate, whereas the film thickness at the application end portion was 6 μm. The film thickness uniformity was significantly poor.

[0042]

According to the present invention, there is provided a color filter resist containing a pigment, a polymer, a curing agent and a solvent, wherein the solvent is a mixed solvent and contains at least an alcohol compound. Thus, it is possible to form a color resist coating film having excellent coating film thickness uniformity and excellent storage stability of the color resist.

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Claims (5)

[Claims] 1. A color filter resist containing a pigment, a polymer, a monomer or oligomer, a photopolymerization initiator, and a solvent, wherein the solvent is a mixed solvent and contains at least an alcohol compound. Resist. 2. The method according to claim 1, wherein the alcohol compound is 3-methoxy-3.
2. The resist for a color filter according to claim 1, wherein the resist is -methyl-1-butanol. 3. The resist for a color filter according to claim 2, further comprising propylene glycol monomethyl ether acetate. 4. A method for producing a color filter, comprising using the resist for a color filter according to claim 1. 5. A method for producing a color filter, comprising applying the color filter resist according to claim 1 onto a substrate by a die coating method.