JPH063521A - Radiation sensitive composition for color filter - Google Patents

Abstract

PURPOSE:To provide the radiation sensitive compsn. for color filters which is used for forming the color filters to be used for color liquid crystal display devices and image pickup tube elements, etc., more specifically the radiation sensitive compsn. for the color filters from which the color filters having the surface of coating films possessing a uniform thickness and excellent smoothness and having excellent transparency can be produced with excellent yield. CONSTITUTION:This radiation sensitive compsn. is formed by dissolving or dispersing [A] a pigment, [B] a binder polymer and [C] a radiation sensitive compd. into [D] an org. solvent. This org. solvent [D] is a solvent which has 100 to 200 deg.C b. p. under ordinary pressure and 0.5 to 10.0mmHg vapor pressure at 20 deg.C and contains >=50wt.% at least one kind of esters, ethers or ketones.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a radiation-sensitive composition for a color filter for forming a color filter used for a color liquid crystal display device, an image pickup tube device, etc.
More specifically, the present invention relates to a radiation-sensitive composition for a color filter, which has a coating film surface excellent in smoothness and can produce a color filter excellent in transparency with an excellent yield.

[0002]

Conventionally, to manufacture a color filter using a radiation-sensitive composition, a glass substrate having a SiO ₂ film or the like formed on the surface thereof to prevent elution of sodium ions is conventionally used. The light-shielding layer is formed into a desired pattern, and the radiation-sensitive composition is applied onto the light-shielding layer with a spin coater to form a coating film. The coating film is heated (prebaked) to dry, and then dried. Pixels of each color are obtained by exposing and developing the formed coating film (hereinafter sometimes referred to as a dry coating film).

In the dry coating film thus formed on the substrate, the difference in film thickness between the central part and the peripheral part is 0.2.
In some cases, the thickness is more than μm, or striations may occur, which makes it difficult to obtain a dry coating film having a uniform film thickness. Furthermore, about 3
Fine irregularities of 0 to 500 Å (angstrom) were sometimes formed, and the obtained dry coating film was sometimes inferior in surface smoothness. If the coating film formed by the spin coater has a film thickness difference or fine irregularities are formed on the surface of the dried coating film, the color filter obtained by developing the dried coating film is inferior in transparency. Become.

Therefore, when a color filter is formed on the surface of a substrate, a radiation-sensitive composition for a color filter which can form a dry coating film having a uniform film thickness and an extremely smooth surface has been developed. Is desired.

[0005]

As a result of research in view of the above-mentioned conventional techniques, the present inventor has found that a pigment, a binder polymer, and a radiation-sensitive compound are dissolved or dispersed in a specific organic solvent. The dried coating film obtained by applying the radiation-sensitive composition for a filter on the surface of a substrate by a spin coater and then drying the film has a small difference in film thickness between the central portion and the peripheral portion and is excellent in surface smoothness. This has led to the completion of the present invention.

That is, the radiation-sensitive composition for a color filter according to the present invention comprises a pigment [A], a binder polymer [B] and a radiation-sensitive compound [C] dissolved or dispersed in an organic solvent [D]. , The organic solvent [D]
However, the boiling point at normal pressure (hereinafter, simply referred to as “boiling point”) is 100 to 200 ° C., and the vapor pressure at 20 ° C. (hereinafter, simply referred to as “vapor pressure”) is 0.05 to 10.0 mmHg.
Is a solvent containing at least one kind of ester, ether or ketone which is 50% by weight or more.

The radiation-sensitive composition for color filters may contain an additive [E], if necessary.

[0008]

DETAILED DESCRIPTION OF THE INVENTION The radiation-sensitive composition for color filters according to the present invention will be specifically described below.

The radiation-sensitive composition for color filters according to the present invention comprises a pigment [A], a binder polymer [B],
And [C] the radiation-sensitive compound are dissolved or dispersed in a specific [D] organic solvent.

The respective components will be described in detail below. [A] Pigment In the present invention, an organic pigment or an inorganic pigment is used as the pigment [A].

Examples of such organic pigments include dyes or pigments that are insoluble in water or organic solvents, and specifically, the color index CI (The Society of Dyers a
Compounds classified as Pigment (published by nd Colorists) are listed.

Examples of the inorganic pigment include metal compounds such as metal oxides and metal complex salts. Specifically, iron, cobalt, aluminum, cadmium, lead, copper, titanium,
Examples thereof include metal oxides or complex oxides such as magnesium, chromium, zinc and antimony.

More specifically, examples of the pigment [A] include compounds having the following color index CI numbers. CIPigment Yellow 24, CIPigm
ent Yellow 31, CIPigment Yellow 53, CIPigment
Yellow 83, CIPigment Orange 43, CIPigment Re
d 105, CIPigment Red 149, CIPigment Red 176,
CIPigment Red 177, CIPigment Violet 14, CIPi
gment Violet 29, CIPigment Blue 15, CIPigment
Blue 15: 3, CIPigment Blue 22, CIPigment Blue
28, CIPigment Green 15, CIPigment Green 25,
CIPigment Green 36, CIPigment Brown 28, CIPi
gment Black 1, CI Pigment Black 7, etc.

In the present invention, the pigment [A] is usually contained in an amount of 10 to 100 relative to 100 parts by weight of the binder polymer [B].
It is used in an amount of 0 parts by weight, preferably 20 to 500 parts by weight.

[B] Binder Polymer In the present invention, as the binder polymer [B], a copolymer of an acid monomer [B-1] and a comonomer [B-2] copolymerizable with the acid monomer is preferably used. To be

The acid monomer [B-1] used when forming such a binder polymer [B] has at least one carboxylic acid in the molecule (for example, unsaturated monocarboxylic acid, Saturated dicarboxylic acid etc.)
Unsaturated carboxylic acids or unsaturated sulfonic acids having at least one or more sulfonic acid in the molecule are mentioned.
Specific examples of the unsaturated carboxylic acid include (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid and fumaric acid.

Specific examples of unsaturated sulfonic acids include isoprene sulfonic acid and styrene sulfonic acid. These may be used alone or in combination.

Specific examples of the comonomer [B-2] include aromatic vinyl compounds such as styrene, α-methylstyrene and vinyltoluene, methyl (meth) acrylate, ethyl (meth) acrylate and butyl (meth) acrylate. , 2-hydroxyethyl (meth) acrylate,
Unsaturated carboxylic acid alkyl esters such as benzyl (meth) acrylate, unsaturated carboxylic acid aminoalkyl esters such as aminoethyl acrylate, unsaturated carboxylic acid glycidyl esters such as glycidyl (meth) acrylate, vinyl acetate, vinyl propionate and other carboxylic acids. Acid vinyl ester, (meth) acrylonitrile,
Vinyl cyanide compounds such as α-chloroacrylonitrile, aliphatic conjugated dienes such as 1,3-butadiene, 2-methyl-1,3-butadiene and isoprene, polystyrene having a (meth) acryloyl group at each terminal, polymethyl (meth) ) Acrylics, polybutyl (meth) acrylates, macromonomers such as silicones, and the like.

These may be used alone or in combination. When forming the binder polymer [B], the acid monomer [B-1] is preferably 15% by weight to 50% by weight based on 100% by weight of the total monomers.
In an amount of% by weight, more preferably 20% to 40% by weight
Used in an amount of.

Specific examples of the binder polymer [B] include benzyl methacrylate / methacrylic acid / styrene copolymer, methyl methacrylate / methacrylic acid / styrene copolymer, benzyl methacrylate / methacrylic acid / polystyrene macromonomer. Examples thereof include copolymers and methyl methacrylate / methacrylic acid / polystyrene macromonomer copolymers.

The binder polymer [B] containing a constitutional unit derived from such an acid monomer [B-1] is
Shows alkali solubility. In particular, the binder polymer [B] obtained by using the acid monomer [B-1] in the amount as described above.
Has excellent solubility in an alkali developing solution and is unlikely to generate undissolved substances, and is unlikely to cause scumming or film residue on the non-pixel portion substrate. Further, the binder polymer [B] does not dissolve excessively in the alkali developing solution, has excellent adhesion to the substrate, and can form color pixels that are hard to drop from the substrate.

The binder polymer [B] used in the present invention preferably has a polystyrene-reduced weight average molecular weight measured by gel permeation chromatography (GPC; THF as a carrier) of 10,0.
0 to 500,000, more preferably 20,0
It is from 00 to 300,000.

The binder polymer [B] having such a molecular weight is unlikely to cause scum (floating dust) around the color pixels during development, can form pixels having sharp pattern edges, and can be formed on the non-pixel portion substrate. The undissolved material is unlikely to remain, and scumming and film residue are less likely to occur. Further, when such a binder polymer [B] is used, the development time under which the development can be performed under the optimum conditions becomes long, and the so-called development time margin increases.

[C] Radiation Sensitive Compound The radiation sensitive compound [C] used in the present invention generates radicals (active molecule fragments) such as carbene and nitrene to react when irradiated with radiation, and undergoes tertiary reaction with the binder polymer. It is a compound that forms an original crosslinked structure. Usually, a three-dimensional crosslinked structure is formed by the following two types of reaction systems.

(I) Radicals such as carbene and nitrene, which are liberated by irradiating the radiation-sensitive compound with radiation, act on the binder polymer and the like to induce a chain reaction of double bonds to form a three-dimensional crosslinked structure. (Ii) Radicals such as carbene and nitrene liberated by irradiating molecules such as radiation-sensitive compounds with C--C bonds or C-bonds in the binder polymer.
-A compound that inserts into an H bond and bonds to form a three-dimensional crosslinked structure.

The binder polymer [B] is entangled during the three-dimensional crosslinking reaction by the reaction system (i),
Alternatively, it reacts with the radiation-sensitive compound [C] in the reaction system of (ii) to form a crosslinked structure and is insolubilized.

In the present invention, the term "radiation" is used as a concept including ultraviolet rays, electron beams, X-rays and the like. Specific examples of the radiation-sensitive compound [C] include a photopolymerization initiator, a photopolymerizable monomer, a photopolymerizable oligomer, and a photocrosslinking agent.

Examples of the above photopolymerization initiator include carbonium compounds such as diacetyl and benzoin, azo compounds such as azobisisobutyronitrile, diazonium and azide compounds or azide compounds, and organic sulfur compounds such as mercaptan disulfide. And peroxides such as ether peroxide and carboxylic acid peroxide.

More specifically, 2-hydroxy-2-methyl
-1-Phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4-
(2-Hydroxyethoxy) phenyl- (2-hydroxy-2-
Propyl) ketone, 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl (4-methylthiophenyl) -2-morpholino-1-propan-1-one, 2-benzyl-2- Dimethylamino-1- (4-morpholinophenyl) -butan-1-one, benzophenone, 4,4'-bis (dimethylamino) benzophenone, 4,4'-bis (diethylamino) benzophenone,
2,4-diethylthioxanthone, 3,3-dimethyl-4-methoxybenzophenone, 4-azidobenzaldehyde, 4-azidoacetophenone, 4-azidobenzalacetophenone,
Azidopyrene, 4-diazodiphenylamine, 4-diazo-
4'-Methoxy-diphenylamine, 4-diazo-3-methoxy-diphenylamine, benzyl (also known as dibenzoyl), benzoinchinoisobutyl ether, N-phenyl
-Thioacridone, triphenylpyrylium perchlorate and the like.

Among these, 2,2-dimethoxy-2-phenylacetophenone and 2-benzyl-2-dimethylamino-1- (4
-Morpholinophenyl) -butan-1-one, 2-methyl- (4
-Methylthiophenyl) -2-morpholinopropan-1-one and 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one are preferred.

Examples of the photopolymerizable monomer or photopolymerizable oligomer include trimethylolpropane triacrylate, pentaerythritol triacrylate, trisacryloyloxyethyl phosphate, pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate. Of polyfunctional acrylates and oligomers thereof.

Of these, pentaerythritol triacrylate, dipentaerythritol hexaacrylate, and trimethylolpropane triacrylate are preferable.

Specific examples of the photocrosslinking agent include diazidochalcone 2,6-bis (4'-azidobenzal) cyclohexanone, 2,6-bis (4'-azidobenzal) -4-methylcyclohexanone, 1,3- Bis (4'-azidobenzal) -2-propanone,
1,3-bis (4'-azidocinnamylidene) -2-propanone, 4,
Examples include 4'-diazidostilbene and antimony dichromate.

In the present invention, the above-mentioned photopolymerization initiator, photopolymerizable monomer, photopolymerizable oligomer or photocrosslinking agent can be used alone or in combination as the radiation-sensitive compound. It is preferable to use the agent together with a photopolymerizable monomer or a photopolymerizable oligomer.

The radiation-sensitive compound [C] is usually added in an amount of 5 to 100 parts by weight of the binder polymer [B].
It is used in an amount of 500 parts by weight, preferably 20 to 200 parts by weight.

When the photopolymerization initiator is used in combination with the photopolymerizable monomer or photopolymerizable oligomer, it is usually
0.01 to 200 parts by weight of a photopolymerization initiator with respect to 100 parts by weight of a photopolymerizable monomer or photopolymerizable oligomer,
Preferably, it is desirable to use it in an amount of 1 to 120 parts by weight.

Radiation-sensitive compound [C] used in the present invention
Further contains a polymer compound having a functional group capable of functioning as a photopolymerization initiator, a photopolymerizable monomer or photopolymerizable oligomer, a photocrosslinking agent or a sensitizer as described above in the main chain or side chain. May be.

Specific examples of such a polymer compound include a condensate of 4-azidobenzaldehyde and polyvinyl alcohol, a condensate of 4-azidobenzaldehyde and a phenol novolac resin, and a polymer of 4-acryloylphenyl cinnamoyl ester. Alternatively, copolymers, 1,4-polybutadiene, 1,2-polybutadiene and the like can be mentioned.

[D] Organic Solvent The organic solvent [D] used in the present invention has a boiling point of 100 to.
It is necessary to contain at least one kind of esters, ethers or ketones having a vapor pressure of 0.05 to 10.0 mmHg at 200 ° C. in an amount of 50% by weight or more.

Specific examples of such esters, ethers or ketones include the following compounds. Saturated aliphatic monocarboxylic acid alkyl esters such as -n-butyl acetate and isobutyl acetate, lactic acid esters such as methyl lactate and ethyl lactate, oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate and butyl oxyacetate, Alkoxyacetic acid alkyl esters such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate and ethyl ethoxyacetate, 3-oxypropionic acid alkyl esters such as methyl 3-oxypropionate and ethyl 3-oxypropionate , 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate and other 3-alkoxypropionic acid alkyl esters, methyl 2-oxypropionate, 2-oxypropionate Ethyl acidate, 2 -2-Oxypropionic acid alkyl esters such as propyloxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate 2-alkoxypropionic acid alkyl esters such as methyl 2-oxy-2-methylpropionate,
2-oxy-2-methyl-2-propionate and other 2-oxy
-2-Methylpropionate alkyl esters, 2-methoxy-2-methylpropionate methyl, 2-ethoxy-2-methylpropionate ethyl and other 2-alkoxy-2-methylpropionate alkyloxymonocarbonates Acid alkyl esters, ketone acid esters such as ethyl pyruvate, methyl cellosolve acetate, ethyl cellosolve acetate, cellosolve acetate such as diethyl cellosolve acetate, dichloroethyl ether,
Ethers such as n-butyl ether, diisoamyl ether and methylphenyl ether, carbitols such as methylethyl carbitol, diethyl carbitol, diethylene glycol methyl ethyl ether, diethylene glycol dimethyl ether and diethylene glycol diethyl ether, cyclohexanone, methyl-n-propyl ketone , Methyl-n-butyl ketone, methyl-n-amyl ketone, 2-heptanone and other ketones.

These may be used alone or in combination. In the present invention, the ester, ether or ketone contained in the organic solvent [D] has a boiling point of 100 to 200 ° C. as described above, but among them, the boiling point is 130 to 190 ° C. Is more preferable.

The above-mentioned ester, ether or ketone has a vapor pressure of 0.05 to 10.0 mmHg, more preferably 0.1 to 5.0 mmHg. Specific examples of preferred organic solvents among these are ethyl lactate, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, ethyl 2-ethoxypropionate, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol dimethyl ether,
Diethylene glycol diethyl ether, propylene glycol monomethyl ether acetate, etc. may be mentioned.

The organic solvent [D] used in the present invention contains at least one of the above-mentioned esters, ethers or ketones in the organic solvent in an amount of 50% by weight or more, preferably 70% by weight. Contained in.

Solvents other than the above-mentioned esters, ethers or ketones contained in the organic solvent [D] used in the present invention are the above-mentioned pigment [A] and binder polymer [B].
There is no particular limitation as long as it is a solvent capable of dissolving or dispersing the radiation-sensitive compound [C].

When the organic solvent [D] contains a solvent having a boiling point of more than 200 ° C. in an amount of more than 50% by weight, the organic solvent [D] will be sufficient when the coating film formed by coating is prebaked. It may remain in the dry coating film without evaporating, and the surface of the dry coating film may become sticky to cause sticking, which may lower the heat resistance of the dry coating film. If a large amount of the organic solvent [D] remains in the dried coating film,
SiO ₂ in the dried film of the glass substrate in particular surface during development
It may peel off from the glass substrate having the film.

On the other hand, when the organic solvent [D] contains a solvent having a boiling point of less than 100 ° C. in an amount of more than 50% by weight,
It becomes difficult to apply the radiation-sensitive composition evenly and uniformly, and thus it becomes difficult to obtain a dry coating film having excellent surface smoothness.

In the present invention, such an organic solvent [D] is used.
Is usually 100 to 10,000 parts by weight, preferably 500 to 50 parts by weight with respect to 100 parts by weight of the binder polymer [B].
Used in an amount of 00 parts by weight.

The radiation-sensitive composition for color filters according to the present invention may contain an additive [E], if necessary. Specific examples of the additive [E] include a filler, another polymer compound, a surfactant, an adhesion promoter, an antioxidant, an ultraviolet absorber, an anticoagulant, and another sensitizer. To be

More specifically, fillers such as glass and alumina, other polymer compounds such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether and polyfluoroalkyl acrylate, nonionic, cationic and anionic compounds. Surfactants such as vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane,
N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane and other adhesion promoters, 2, Antioxidants such as 2-thiobis (4-methyl-6-t-butylphenol) and 2,6-di-t-butylphenol, 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5 -UV absorbers such as chlorobenzotriazole and alkoxybenzophenone, anti-aggregation agents such as sodium polyacrylate, benzophenone, 4,4'- Scan (diethylamino) benzophenone, organic dye sensitizer that absorbs light of a wavelength 200~490nm such nitropyrene the like.

The above components [A], [B], which form the radiation-sensitive composition for a color filter according to the present invention,
[C] and [E] are dissolved or dispersed in the organic solvent [D].

When the radiation-sensitive composition for a color filter according to the present invention as described above is used, the organic solvent is sufficiently evaporated in the prebaking step, and a large amount of the organic solvent remains in the obtained dried coating film. There is no. Therefore, the surface of the dry coating film does not become tacky and sticking does not occur. Further, since a large amount of the organic solvent does not remain in the dry coating film, the dry coating film does not peel off from the substrate during development and heat resistance does not deteriorate.

In particular, when the radiation-sensitive composition for a color filter according to the present invention containing a specific organic solvent as described above is used, it can be evenly and uniformly coated on a glass substrate by a spin coater. Therefore, when using the radiation-sensitive composition for a color filter according to the present invention,
A dry coating film having a uniform film thickness and a surface with excellent smoothness can be formed without causing striation, and the obtained dry coating film has excellent adhesion to the substrate. ing.

By subjecting such a dried coating film to alkali development, a color filter excellent in transparency can be obtained. As described above, when the radiation-sensitive composition for a color filter according to the present invention is used, a color filter having an excellent transparency can be produced with an excellent yield.

In the present invention, when a pixel is formed using the radiation-sensitive composition for a color filter, the developer is an inorganic alkali such as sodium carbonate, potassium hydroxide or sodium carbonate, or tetramethylammonium hydroxide. It is preferable to use an alkaline solution such as an organic alkali.

[0055]

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

[0056]

Example 1 A light-shielding layer having a desired pattern was formed on the surface of a soda glass substrate on which a SiO ₂ film for preventing elution of sodium ions was formed. The composition 1 was applied to a desired thickness (1.5 μm) by a spin coater, and the obtained coating film was prebaked at 80 ° C. for 10 minutes to obtain a dried coating film.

[0057]

[Table 1]

The obtained dried coating film was measured with a stylus type film thickness measuring device (manufactured by TENCOR, alpha-step 100). As a result, the film thickness was 1.45 to 1.50 μm, and the in-plane variation of the film thickness was observed. The range (membrane pressure difference) was 0.05 μm or less, and the membrane surface roughness (unevenness) was about 100 Å. This dry coating film was excellent in transparency. There was no striation.

Then, the dried coating film was exposed to ultraviolet rays of 400 mj / cm ^{2 with} a high pressure mercury lamp through a photomask and then immersed in a 0.05% sodium carbonate aqueous solution for development to obtain 100 μm × 100 μm red pixels. It was

When the formed color pixels were observed with a differential polarization microscope, it was confirmed that the surface had high smoothness, which was preferable as a color filter.

[0061]

Comparative Example 1 Drying was carried out in the same manner as in Example 1 except that the radiation sensitive composition 2 containing diethylene glycol monoethyl ether (boiling point 202 ° C., vapor pressure 0.13 mmHg) was used as the organic solvent. A coating film was obtained.

[0062]

[Table 2]

The obtained dried coating film was measured in the same manner as in Example 1, and as a result, the film thickness was 1.42 to 1.60 μm.
The in-plane variation range of the film thickness was 0.18 μm, and the film surface roughness (unevenness) was about 500 Å. This dry coating film had no transparency.

Exposure and development were carried out in the same manner as in Example 1 to obtain red pixels of 100 μm × 100 μm. When the formed color pixels were observed with a differential polarization microscope, it was found that the surface smoothness was not so high, and it was not preferable as a color filter.

[0065]

Comparative Example 2 Methyl ethyl ketone (boiling point 79.6 ° C., vapor pressure 71.2 mmHg) as an organic solvent in Example 1
A dried coating film was obtained in the same manner as in Example 1 except that the radiation-sensitive composition 3 for a color filter containing was used.

[0066]

[Table 3]

The obtained dried coating film was measured in the same manner as in Example 1, and as a result, the film thickness was 1.26 to 1.61 μm.
The in-plane variation range of the film thickness was 0.35 μm, and the film surface roughness (unevenness) was about 600 Å.

The dried coating film was not transparent. Also, striations have occurred. Further, exposure and development were carried out in the same manner as in Example 1 to obtain red pixels of 100 μm × 100 μm.

When the formed color pixels were observed with a differential polarization microscope, it was found that the surface smoothness was not so high, and it was not preferable as a color filter.

[0070]

Example 2 In Example 1, propylene glycol monomethyl ether acetate (boiling point 1
Radiation-sensitive composition 4 containing 40 ° C. and a vapor pressure of 3.5 mmHg)
A dried coating film was obtained in the same manner as in Example 1 except that was used.

[0071]

[Table 4]

The dry coating film thus obtained was measured in the same manner as in Example 1, and as a result, the film thickness was 1.50 to 1.59 μm.
The in-plane variation range of the film thickness was 0.09 μm or less, and the film surface roughness (unevenness) was about 200 Å.

The dried coating film was excellent in transparency and did not cause striation. Then, in the same manner as in Example 1, the dried coating film was exposed and then developed, and 100 μm ×
A 100 μm blue pixel was obtained.

When the formed color pixels were observed with a differential polarization microscope, it was confirmed that the surface had high smoothness, and it was preferable as a color filter.

[0075]

Example 3 A dried coating film was obtained in the same manner as in Example 1 except that the radiation sensitive composition 1 for color filter was replaced with the radiation sensitive composition 5 for color filter.

[0076]

[Table 5]

The dry coating film thus obtained was measured in the same manner as in Example 1, and as a result, the film thickness was 1.50 to 1.59 μm.
The in-plane variation range of the film thickness was 0.09 μm or less, and the film surface roughness (unevenness) was about 200 Å.

The dried coating film was excellent in transparency and did not cause striation. Then, after exposing in the same manner as in Example 1, it is developed to 100 μm × 100 μm.
m red pixels were formed.

When the formed color pixel was observed with a differential polarization microscope, it was confirmed that the surface had high smoothness, and it was preferable as a color filter.

[0080]

Comparative Example 3 Dry coating was carried out in the same manner as in Example 1 except that the radiation sensitive composition 1 for color filters shown in Table 6 was used instead of the radiation sensitive composition 1 for color filters. A film was obtained.

[0081]

[Table 6]

The dried coating film obtained in the same manner as in Example 1 could not be sufficiently dried by prebaking at 80 ° C. for 10 minutes, and tack (stickiness of coating film surface) was observed. . Therefore, the prebaking condition was changed to 90 ° C. for 10 minutes to obtain a dry coating film. The film thickness is 1.48 to 1.
50 μm, variation range within the film thickness is 0.18 μm
And the surface roughness (unevenness) of the film was about 400Å.

A coating film having no transparency was obtained. Also, striations have occurred. In addition, exposure and development were performed in the same manner as in Example 1 to form 100 μm × 100 μm green pixels.

When the formed pixels were observed with a differential polarization microscope, it was found that the surface smoothness was not so high, and it was not preferable as a color filter.

[0085]

Example 4 Dry coating was carried out in the same manner as in Example 1 except that the radiation sensitive composition for color filter 7 shown in Table 7 was used instead of the radiation sensitive composition for color filter 1. A film was obtained.

[0086]

[Table 7]

The obtained dried coating film was measured in the same manner as in Example 1, and as a result, the film thickness was 1.47 to 1.53 μm,
The in-plane variation range of the film thickness was 0.06 μm or less, and the film surface roughness (unevenness) was about 200 Å.

The dried coating film was excellent in transparency and did not cause striation. Then, after exposing in the same manner as in Example 1, it is developed and 100 μm × 100 μm.
Of green pixels.

When the formed color pixels were observed with a differential polarization microscope, it was confirmed that the surface had high smoothness, and it was preferable as a color filter.

[0090]

Example 5 A dried coating film was obtained in the same manner as in Example 1, except that the radiation-sensitive composition 8 for color filter was used instead of the radiation-sensitive composition 1 for color filter. .

[0091]

[Table 8]

The obtained dried coating film was measured in the same manner as in Example 1, and as a result, the film thickness was 1.62 to 1.69 μm.
The in-plane variation range of the film thickness was 0.10 μm or less, and the film surface roughness (unevenness) was about 200 Å.

The dry coating film was excellent in transparency and did not cause striation. Then, the dry coating film is exposed in the same manner as in Example 1 and then developed to 100 μm.
× 100 μm green pixel was formed.

When the formed color pixels were observed with a differential polarization microscope, it was confirmed that the surface had high smoothness, and it was preferable as a color filter.

[0095]

Comparative Example 4 Dry coating was carried out in the same manner as in Example 1 except that the radiation sensitive composition 1 for color filters shown in Table 9 was used in place of the radiation sensitive composition 1 for color filters. A film was obtained.

[0096]

[Table 9]

The obtained dried coating film was measured in the same manner as in Example 1, and as a result, the film thickness was 1.68 to 1.71 μm.
The in-plane variation range of the film thickness was 0.30 μm, and the film surface roughness (unevenness) was about 400 Å.

The dry coating film had no transparency. Also, striations have occurred. In addition, exposure and development were performed in the same manner as in Example 1 to form 100 μm × 100 μm green pixels.

When the formed color pixels were observed with a differential polarization microscope, it was found that the surface smoothness was not so high, and it was not preferable as a color filter.

[0100]

As described above, when the radiation-sensitive composition for a color filter according to the present invention is used, it can be uniformly and evenly coated on a substrate to form a coating film without causing striation. can do. When the radiation-sensitive composition for color filters according to the present invention is used, a dry coating film can be obtained without leaving a large amount of organic solvent in the coating film.

The dry coating film formed from the radiation-sensitive composition for a color filter according to the present invention has a uniform film thickness and a smooth surface, and has excellent adhesion to a substrate. There is.

By using the radiation-sensitive composition for a color filter according to the present invention as described above, a color filter having an excellent transparency can be produced with an excellent yield.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Nobuo Bessho 2-11-24 Tsukiji, Chuo-ku, Tokyo Japan Synthetic Rubber Co., Ltd.

Claims (1)

[Claims] 1. A pigment, [B] binder polymer and [C] radiation-sensitive compound are dissolved or dispersed in an organic solvent [D], and the organic solvent [D] has a boiling point at normal pressure. Esters having a vapor pressure of 100 to 200 ° C and a vapor pressure of 0.05 to 10 mmHg at 20 ° C,
A radiation-sensitive composition for a color filter, which is a solvent containing at least one kind of ethers or ketones in an amount of 50% by weight or more.