JP2001011336A - Coloring composition and photosensitive coloring composition and color filter using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a coloring composition which has excellent light resistance, heat resistance and transparency and is useful for color filters by using a copolymer copolymerized with N-phenylmaleimide in a specific polymerization ratio. SOLUTION: This coloring composition contains a colored copolymer obtained by copolymerizing (A) a coloring monomer of formula I [R1 is a polymerizable group expressed by formula II (R2 is a 2 to 4C alkyl) or the like, H, a 1 to 8C alkyl or a hydroxyalkyl; X is an anion], (B) N-phenylmaleimide and (C) one or more other monomers, wherein the component B is copolymerized in an amount of 3 to 40 wt.% per 100 wt.% of the copolymer. The component C includes styrenic compounds and α,β-unsaturated mono- to poly-carboxylic acids. The objective composition preferably comprises the copolymer, a polyimide precursor and a solvent.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a coloring composition for a color filter and a photosensitive coloring composition used for a liquid crystal display, a color video camera and the like, and a color filter using the same.

[0002]

2. Description of the Related Art In a conventional method for producing a color filter, a dye and a pigment are used as a coloring agent. Typical production methods using a dye and a pigment as a coloring agent include a dyeing method and a pigment dispersion method, respectively.

The dyeing method is a method of forming a transparent pattern on a substrate and then immersing the substrate in an aqueous dye solution to dye the pattern. This production method is excellent in transparency because a dye is used as a pigment.

On the other hand, in the pigment dispersion method, a resin, a photosensitive agent,
A photosensitive coloring liquid containing a photopolymerizable monomer, a dispersant, a solvent and a pigment is used. A method of applying the photosensitive coloring liquid on a substrate, drying, exposing, and developing to form a pattern is a pigment dispersion method. In this production method, since a pigment is used as a coloring agent, heat resistance and light resistance are excellent.

[0005]

However, the above method is not without its problems. That is,
When a dye is used as a coloring agent, there is a problem that light resistance and heat resistance are inferior. Further, when a pigment is used as a coloring agent, the pigment has a large particle size, causing light scattering, and has problems in transparency, contrast, and color purity. The present invention has been made in order to solve the above problems, light resistance,
It is an object to provide a coloring composition for a color filter and a photosensitive coloring composition having excellent heat resistance and transparency, and a color filter using the same.

[0006]

In order to achieve the above object in the present invention, first, in claim 1, a dye monomer represented by the following general formula <Chemical Formula 5>, N-phenylmaleimide, A colored composition comprising a colored copolymer having a polymerization ratio of 3 to 40% by weight of N-phenylmaleimide with respect to 100% by weight of a copolymer obtained by polymerizing monomers. Offer things.

Embedded image (In the formula, each R ₁ independently represents a group selected from the polymerizable groups represented by the following <Chemical Formula 6>, a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a hydroxyalkyl group, and at least one is selected from among the polymerizable group represented by the following <of 6> .X ^- represents an anion).

Embedded image (In the formula, R ₂ represents an alkyl group having 2 to 4 carbon atoms.)

According to a second aspect of the present invention, there is provided a color filter using the coloring composition according to the first aspect.

Further, in claim 3, the following general formula <
The polymerization ratio of a copolymer obtained by polymerizing a dye monomer represented by Chemical formula 7>, N-phenylmaleimide, and another monomer is as follows:
N-phenylmaleimide 3 based on 100% by weight of copolymer
Provided is a photosensitive colored composition, characterized by using a colored copolymer in an amount of about 40% by weight.

Embedded image (In the formula, each R ₁ independently represents a group selected from the polymerizable groups represented by the following formulas, a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a hydroxyalkyl group, and at least One is selected from polymerizable groups represented by the following <Chemical formula 8>, wherein X ⁻ represents an anion.)

Embedded image (In the formula, R ₂ represents an alkyl group having 2 to 4 carbon atoms.)

According to a fourth aspect of the present invention, there is provided a color filter using the photosensitive coloring composition according to the third aspect.

[0010]

Embodiments of the present invention will be described below. The colored copolymer in the present invention is obtained from a polymerizable dye monomer described below. The colored copolymer is a copolymer of the dye monomer with N-phenylmaleimide and a monomer conventionally known as another monomer. Further, in order to adjust the hue, a copolymer obtained by combining two or more kinds of the polymerizable dye monomers of the present invention can be used. The production of the copolymer of the present invention can be easily carried out in water, in an organic solvent or without solvent using a conventionally known polymerization catalyst.

In the present invention, the polymerizable dye monomer is
In general formula <Formula 1>, R ₁Carbon source represented by
Examples of the alkyl group of the radicals 1 to 8 include methyl, ethyl and the like.
Propyl, isopropyl, butyl, sec-butyl, sec-butyl
Tributyl, isobutyl, amyl, tertiary amyl, hexyl
Le, heptyl, octyl, isooctyl, tertiary octyl
And 2-ethylhexyl, etc.,
Examples of the hydroxylalkyl group 8 include, for example,
Of the structure in which the hydrogen atom of the alkyl group is replaced with a hydroxyl group
Groups. In the chemical formula 2, R_TwoCharcoal represented by
Examples of the alkyl group having 2 to 4 element atoms include, for example, ethyl
, Trimethylene, tetramethylene and the like.

Further, in the polymerizable dye formula is monomeric <Formula 1> a compound represented by, X ^-, as the anion represented, for example, chlorine anion, bromine anion, iodine anion, fluorine anion Inorganic anions such as halogen anion, perchlorate anion, thiocyanate anion, phosphorus hexafluoride anion, antimony hexafluoride anion, boron tetrafluoride anion, benzenesulfonic acid anion, toluenesulfonic acid anion, trifluoromethanesulfone Organic anions such as organic anions such as acid anions, octyl phosphate anions, dodecyl phosphate anions, octadecyl phosphate anions, phenyl phosphate anions and nonylphenyl phosphate anions.

A typical example of the dye monomer represented by the above general formula <Formula 1> is the following general formula <Formula 9>.
However, the present invention is not limited at all by the following exemplified compounds. In the following examples, the dye monomer cations without anions are shown.

Embedded image

The copolymer of the present invention is characterized in that the polymerization ratio of N-phenylmaleimide is 3 to 40% by weight, more preferably 5 to 30% by weight. If the polymerization ratio of N-phenylmaleimide is 3% by weight or less, a sufficient effect on heat resistance cannot be obtained. On the other hand, when the content is 40% by weight or more, the transmittance at a short wavelength decreases, and the brightness decreases.

Well-known monomers used for synthesizing the copolymer of the present invention include styrene compounds and α, β
-Unsaturated mono- to polycarboxylic acids and esters, amides, imides or anhydrides thereof, for example, in the former, styrene, α-methylstyrene, hydroxystyrene and the like; in the latter, acrylic acid, methacrylic acid, Maleic acid, fumaric acid, itaconic acid, citraconic acid, mesaconic acid, 1-butyne-2,3,4-tricarboxylic acid and the like can be mentioned. Examples of the ester include methyl, ethyl, 2-hydroxyethyl, propyl, butyl, octyl, dodecyl, 2,2,6,6-tetramethyl-4-piperidyl of the α, β-unsaturated carboxylic acid,
1,2,2,6,6-pentamethyl-4-piperidyl,
Esters such as 2- [3- (2-benzotriazolyl) -4-hydroxyphenyl] ethyl are exemplified. Examples of the amide include methylamide, dimethylamide, ethylamide, diethylamide, propylamide, dipropylamide, butylamide, dibutylamide, hexylamide, octylamide, and phenylamide of the α, β-unsaturated carboxylic acid. Examples of the imide include maleimide, itaconimide, N-butylmaleimide, N-octylmaleimide, and N-phenylmaleimide.

In the case of copolymerizing the dye monomer of the present invention with a known monomer, the amount of the known monomer used is appropriately selected according to the intended use. It is in the range of 5 to 100,000 g for 100 g of body.

The coloring composition using the colored copolymer according to the present invention includes, for example, the colored copolymer according to the present invention, a polyimide precursor, and a solvent.

As the acid dianhydride for synthesizing the polyimide precursor, pyromellitic dianhydride, 3,3′4,
4'-benzophenonetetracarboxylic dianhydride, 2,
2 ', 3,3'-benzophenonetetracarboxylic dianhydride, 3,3'4,4'-biphenyltetracarboxylic dianhydride, 3,3'4,4'-diphenylsulfonic acid tetracarboxylic dianhydride , 4,4'-oxydiphthalic dianhydride, 2,3,5-tricarboxycyclopentylacetic dianhydride, 1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,2,3,4 -Cyclopentanetetracarboxylic dianhydride. These acid anhydrides can be used in combination of two or more.

The diamino compounds for synthesizing the polyimide precursor include 4,4'-diaminodiphenyl ether, 3,3'-diaminodiphenyl ether,
4'-diaminodiphenylmethane, 3,3'-diaminodiphenylmethane, 4,4'-diaminodiphenylsulfone, 3,3'-diaminodiphenylsulfone, paraphenylenediamine, metaphenylenediamine, 3,3 '
-Diaminobenzophenone, 4,4'-diaminobenzophenone, 1,4-bis (4-aminophenoxy) benzene, 1,3-bis (3-aminophenoxy) benzene, bis- (4-aminophenyl) tetramethyldisiloxane and so on. These diamino compounds may be used in combination of two or more.

As the solvent, methanol, ethanol, toluene, xylene, ethyl cellosolve, ethyl cellosolve acetate, methyl cellosolve, methyl cellosolve acetate, diglyme, cyclohexanone, ethylbenzene, isoamyl acetate, n-amyl acetate, propylene glycol monomethyl ether (acetate), Propylene glycol monoethyl ether (acetate), diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, triethylene glycol, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, liquid polyethylene glycol, 1-methoxy-2
-Propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, ethyl lactate, ethyl ethoxypropionate and the like are used, and these solvents can be used in combination of two or more kinds.

A polyimide resin precursor obtained from the above-mentioned acid dianhydride and diamino compound is mixed with the above-mentioned colored polymer and solvent to form a paint, which is applied on a substrate by a method such as spin coating and dried. This makes it possible to form a coating on the substrate. Then, a photosensitive resin is applied on the film, a mask having a desired opening or a transparent portion is further overlapped, exposed through the mask, developed, and the film is partially exposed, and the exposed portion is exposed. By removing the film by etching, the film can be processed into a desired pattern with high accuracy. The precursor can be polymerized by performing a heat treatment after the patterning, and the substrate and the coating film can be firmly adhered to each other.

The photosensitive colored composition using the colored copolymer according to the present invention includes, for example, photosensitive colored composition (1)
Is a combination of the colored copolymer, resin, photopolymerizable monomer, photosensitive agent, and solvent according to the present invention, or the colored copolymer, resin, and photosensitive agent according to the present invention as the photosensitive colored composition (2). And a combination of solvents. Hereinafter, each is described in detail.

Examples of the resin of the photosensitive coloring composition (1) include (meth) acrylic resins, polyester resins, epoxy resins, phenolic compounds such as p-hydroxystyrene, and copolymers thereof.

The molecular weight of the resin adjusted as described above is
Preferably it is 3000-150,000, More preferably, it is 10,000-80000. Molecular weight 300
If it is 0 or less, sensitivity is insufficient, and if it is 150,000 or more, developability is reduced.

The photopolymerizable monomer of the above-mentioned photosensitive coloring composition (1) includes difunctional, trifunctional, and polyfunctional monomers. Examples of the bifunctional monomer include 1,6-hexanediol diacrylate and ethylene. Glycol diacrylate, neopentyl glycol diacrylate, triethylene glycol diacrylate, etc., as trifunctional monomers, trimethylolpropane triacrylate, pentaerythritol triacrylate, etc.,
Examples of the polyfunctional monomer include ditrimethylolpropane tetraacrylate and dipentaerythritol pentaacrylate. The addition amount of the photopolymerizable monomer is not particularly limited, but may be 20 to 15 of the binder resin.
0% by weight is preferred.

The photosensitive agent of the photosensitive coloring composition (1) includes a triazine compound, an acetophenone compound, a thioxanthone compound, a benzoin compound, a benzophenone compound, a diazo compound, and an azide compound. Examples of triazine compounds include 2,4,6-tris (trichloromethyl) -s-triazine and 2- (p-methoxystyryl) -4,6-bis (trichloromethyl).
-S-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4,6-bis (trichloromethyl) -s-
Triazine, 2- (p-chlorophenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4 ′
-Methoxy-1'-naphthyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (N-isoamyloxycarbonylmethyl-3'-carbazolyl) -4,6
-Bis (trichloromethyl) -s-triazine, 2-
(N- (2 "-methoxy-1" -methylethoxycarbonylmethyl) -3'-carbazolyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (N-cyclohexyloxycarbonylmethyl-3 ' -Carbazolyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methylthiophenyl) -bis (4,6
-Trichloromethyl) -s-triazine, 2- (4-methoxy-β-styryl) -bis (4,6-trichloromethyl) -s-triazine, 2- (3-chlorophenyl)
-Bis (4,6-trichloromethyl) -s-triazine and the like.

As the acetophenone-based compound, 4-phenoxydichloroacetophenone, 2-hydroxy-2
-Methyl-1-phenyl (4-dodecyl) propane-1
-One, 1-hydroxycyclohexyl-phenyl ketone, 2-methyl-2-morpholino (4-thiomethylphenyl) propan-1-one, and the like. Examples of the thioxanthone-based compound include 2-methylthioxanthone, 2-isopropylthioxanthone, 2,4-dimethylthioxanthone, and 2,4-diisopropylthioxanthone. Examples of the benzoin-based compound include benzoin isopropyl ether, benzoisobutyl ether, and benzyl dimethyl ketal.

Examples of the benzophenone-based compound include 4-benzoyl-4'-methyl-diphenyl sulfide,
3,3'-dimethyl-4-methoxybenzophenone and the like. Examples of the diazo compound include a formaldehyde condensate of p-diazodiphenylamine and hexafluorophosphate, tetrafluoroborate, perchlorate, paratoluenesulfonic acid, or 2-hydroxy-4-methoxybenzophenone-5- There are diazonium salts formed by reaction with sulfonic acids. As azide compounds, 4,4′-diazidostilbene, 4,4′-diazidobenzophenone, 4,4′-diazidochalcone,
There are 4,4'-diazidodiphenylmethane and p-phenylene bis-azide.

The photoinitiator as described above can be used together with a sensitizer. Such sensitizers include thioxanthones, xanthones, and the like.

The photoinitiator as described above has a solid content of 3%.
It is used in an amount of -20% by weight, preferably 5-15% by weight. If the amount of the photoinitiator is less than 3% by weight based on the solid content, a sufficient amount of acid and radical is not generated by exposure, and the sensitivity is lowered. On the other hand, when the content exceeds 20% by weight, the liquid stability becomes poor.

As the solvent of the photosensitive coloring composition (1), the same solvent as the coloring composition is used. However, since the solubility differs depending on the monomer composition of the resin, the photopolymerizable monomer, the photoinitiator, and the like, a solvent having a single or a plurality of solvent compositions is appropriately selected.

As described above, the photosensitive colored composition (1) using the colored copolymer according to the present invention is prepared by mixing a resin and a solvent in addition to the colored copolymer and the photosensitive material. It is a coloring composition. The photosensitive coloring composition (1) can be applied to a substrate by, for example, a spin coating method to form a coating. In addition, when the coating film formed is exposed to light, its solvent solubility decreases. For this reason, a mask having a desired opening or transparent portion is superimposed on the film, exposed through this mask, and developed with a developing solution, so that the film at the exposed portion is selectively left on the substrate to form a pattern. It is possible to

The resin of the photosensitive coloring composition (2) using the colored copolymer according to the present invention includes novolak resin, polyvinyl alcohol, polyvinyl alkyl ether, a copolymer of styrene and acrylic acid, and methacrylic acid. And alkyl esters, hydroxystyrene polymers, polyvinylhydroxybenzoates, polyvinylhydroxybenzals and the like.

The photosensitive agent of the photosensitive coloring composition (2) includes a 1,2-naphthoquinone compound. For example, 2,3,4-trihydroxybenzophenone and 1,
Ester of 2-naphthoquinonediazide-4-sulfonic acid, 2,3,4-trihydroxybenzophenone and 1,
Esters of 2-naphthoquinodiazide-5-sulfonic acid,
Ester of 2,3,4,4'-tetrahydroxybenzophenone and 1,2-naphthoquinonediazide-4-sulfonic acid, 2,3,4,4'-tetrahydroxybenzophenone and 1,2-naphthoquinonediazide-5-sulfone Acid esters, 2,2 ', 3,4,4'-pentahydroxybenzophenone and 1,2-naphthoquinonediazide-4
-Sulfonic acid esters, such as 2,2 ', 3,4,4'-pentahydroxybenzophenone and 1,2-naphthoquinonediazido-5-sulfonic acid.

As the solvent for the photosensitive coloring composition (2), the same solvent as the solvent for the photosensitive coloring composition (1) is used.

As described above, the photosensitive colored composition (2) using the colored copolymer according to the present invention is prepared by mixing a resin and a solvent in addition to the colored copolymer and the photosensitive material. It is a coloring composition. The photosensitive coloring composition (2) can be applied to a substrate by, for example, a spin coating method to form a coating. In addition, the solvent of the coating film formed is improved by exposing the coating film to light. For this reason, a mask having a desired opening or transparent portion is superimposed on the film, exposed through this mask, and developed with a developing solution, so that the film at the exposed portion is selectively left on the substrate to form a pattern. It is possible to

[0037]

The present invention will be described below in detail with reference to examples.

<Example 1> (Polymerization example) As the colored copolymer of the present invention, 30 g of a ClO ₄ ^- salt of a dye monomer represented by the general formula
Acrylamide-2-methylpropanesulfonic acid 13
g, 30 g of 2-hydroxyethyl methacrylate, 11 g of methacrylic acid, 16 g of N-phenylmaleimide and 4 g of 28% by weight aqueous ammonia, and 5 g of azobisisobutyronitrile as a polymerization catalyst. Allowed to react for hours. The solvent was distilled off, and the obtained copolymer (hereinafter, referred to as polymer A) had a number average molecular weight of 13,300 and a weight average molecular weight of 18,200.

The polyimide precursor was prepared as follows. Take 77.5 g of cyclohexanone in a three-necked flask. To this, 4,4'-diaminodiphenyl ether 9.
1 g and bis (3-aminopropyl) tetramethyldisiloxane 0.5 g are added with stirring at 50 ° C. and dissolved. Next, 12.9 g of 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride is added little by little, and the mixture is reacted at 50 ° C. for 3 hours.

(Preparation of Colored Composition) As the colored copolymer of the present invention, Polymer A was used, and 13.0 g of Polymer A was dissolved in 61.0 g of cyclohexanone. This was mixed with 22.0 g of a polyimide precursor to obtain a colored composition.

The obtained coloring composition was spin-coated (1.2 μm thick) and dried. Thereafter, the mixture was heated at 120 ° C. for 20 minutes, on which Microposit S1400 (manufactured by Shipley) as a positive resist was applied by spin coating, and heated at 100 ° C. for 10 minutes. Next, exposure was performed with a high-pressure mercury lamp using a mask having a pixel size of 30 μm × 100 μm (3 kW, 200 mJ / cm ² ). Thereafter, etching is performed with a developing solution (aqueous solution of 0.4% by weight of sodium hydroxide and 0.5% by weight of sodium carbonate), and the distaste is removed in ethylene glycol monomethyl ether acetate at 30 ° C. Heated for a period of time to fix the pattern. As a heat resistance test, the spectral transmittance was measured (OSP-SP200: OLYMPUS), and the color difference before and after post-baking is shown in Table 1. Table 2 shows the transmittance after post-baking. As a weather resistance test, the sample was exposed to a xenon lamp (100,000 lux), and the spectral change was measured. The results are shown in Table 3.

[0042]

[Table 1]

[0043]

[Table 2]

[0044]

[Table 3]

Example 2 Using a polymer A as a colored copolymer of the present invention, 2- (p-) was added to 20.6 g of a solution of the polymer A in cyclohexanone (solid content: 20% by weight).
(Methoxystyryl) -4,6-bis (trichloromethyl) -s-triazine 1.3 g, dipentaerythritol hexaacrylate 2.7 g, acrylic resin ((a) methacrylic acid 5.0 g, (b) hydroxyethyl methacrylate 3) 0.7 g, (c) 2.5 g of methyl methacrylate, and (d) 13.7 g of butyl methacrylate were dissolved in 74.8 g of ethyl cellosolve, and 0.3 g of azoisobutyronitrile was added under a nitrogen atmosphere. 3.2 g of a binder resin obtained from the reaction and 72.2 g of cyclohexanone were added, and the mixture was sufficiently stirred to obtain a photosensitive coloring composition A.

The photosensitive coloring composition A was spin-coated (1.2 μm thick) and dried. After prebaking at 70 ° C. for 20 minutes, exposure was performed using a mask having a pixel size of 30 μm × 100 μm (exposure amount: 200 mJ / cm ² ). Thereafter, the film was developed with a 1% by weight sodium carbonate solution, washed well with water, and then post-baked at 230 ° C. for 1 hour to fix the pattern. Various evaluations were performed in the same manner as in Example 1. The results are shown in Tables 1, 2 and 3.

Example 3 2,3,4-Trihydroxybenzophenone and 1,2-naphthoquinonediazide-5
Dissolve 3.0 g of esterified product of sulfonic acid in 39.5 g of ethyl cellosolve acetate, and 12.0 g of cresol novolak resin (weight average molecular weight 9000)
Is dissolved in 44.8 g of ethyl cellosolve acetate. 0.7 g of the above two solutions and p-toluenesulfonic acid
Was completely dissolved at 60 ° C. for 10 minutes. 100 g of this solution
Then, 30 g of Polymer A was dissolved under stirring to obtain a photosensitive colored composition B.

The photosensitive coloring composition B was spin-coated (1.2 μm thick) and dried. After prebaking at 70 ° C. for 20 minutes, exposure was performed using a mask having a pixel size of 30 μm × 100 μm (exposure amount: 200 mJ / cm ² ). Thereafter, the film was developed with a developing solution (aqueous solution of 0.4% by weight of sodium hydroxide and 0.5% by weight of sodium carbonate), washed well with water, and post-baked at 230 ° C. for 1 hour to fix the pattern. Various evaluations were performed in the same manner as in Example 1. The results are shown in Tables 1, 2 and 3.

Comparative Example 1 (Color Filter Using Pigment as Coloring Agent) An acrylic resin was diluted with ethyl cellosolve so that the resin concentration became 20%. The blue pigment C.I. I. Pig No. 8.91 g of purple pigment C.15.
I. Pig No. 0.09 g of 19 and 0.9 g of Solsperse (Zeneca Corporation: trade name) were added, and the mixture was sufficiently kneaded with a three-roll mill to produce a blue colored resin.

For 30 g of this blue colored resin, 24.205 g of an acrylic resin, 5.127 g of dipentaerythritol hexaacrylate, and 2- (4′-methoxy-1′-naphthyl) -4,6-bis (trichloromethyl ) 1.025 g of -s-triazine and 47.382 g of cyclohexanone were added and stirred well to obtain a photosensitive colored composition. A color filter was prepared from this photosensitive coloring composition in the same manner as in Example 2. Various evaluations were performed in the same manner as in Example 1. The results are shown in Tables 1, 2 and 3.

<Comparative Example 2> (Color filter using dye as colorant) 40% by weight of dimethylaminopropylacrylamide, 15% by weight of 2-hydroxyethyl methacrylate, 15% by weight of vinylpyrrolidone, 8% by weight of methyl methacrylate, methyl acrylate At least 12% by weight of dimethylaminoacrylamide and 10% by weight of dimethylaminoacrylamide are polymerized by a known solution polymerization method to obtain a polymer.

4,4′- is added to 10.0% by weight of this polymer.
0.2% by weight of diazide chalcone, bisazide compound 0.
6% by weight, 0.2% by weight of a silane coupler KBM603 (Shin-Etsu Chemical Co., Ltd.), 45.0% by weight of ethyl cellosolve, and 45.0% by weight of diethylene glycol diethyl ether were thoroughly stirred to obtain a photosensitive composition.

The photosensitive composition was spin-coated on a glass plate and dried. Thereafter, after prebaking at 60 ° C. for 20 minutes, exposure was performed using a mask having a pixel size of 30 μm × 100 μm. The exposure amount was 80 mJ / cm ² . Thereafter, development was carried out with a 0.05% by weight aqueous solution of polyethylene glycol noniphenol ether to form a pattern.
This glass plate was stained with a 0.1% solution of Blue43P (a color filter for Nippon Kayaku Co., Ltd.) at 60 ° C. for 10 minutes. Various evaluations were performed in the same manner as in Example 1. The results are shown in Tables 1, 2 and 3.

[0054]

As described above, the present invention has the following effects. That is, as a coloring material, a dye,
Since a polymerized dye is used instead of a pigment, a colored composition for a color filter, a photosensitive colored composition, and a color filter having excellent light resistance, heat resistance, and transparency can be provided.

Continued on the front page (51) Int.Cl. ⁷ Identification code FI Theme coat II (Reference) G02B 5/20 101 G02B 5/20 101 F term (Reference) 2H048 BA45 BA47 BA48 BB02 BB42 BB46 4J100 AB02R AB03R AB07P AB07R AF01P AJ02R AJ08R AJ09R AL03R AL04R AL05R AL08P AL08R AL09R AM15R AM43R AM48Q BA03R BA27P BC43P BC43R BC49P BC74R BC75R CA05 DA22 DA61 DA62 JA32

Claims (4)

[Claims] 1. The polymerization ratio of a copolymer obtained by polymerizing a dye monomer represented by the following general formula <1>, N-phenylmaleimide and another monomer is 100% by weight of the copolymer. A colored composition, characterized in that a colored copolymer having 3 to 40% by weight of N-phenylmaleimide is used. Embedded image (In the formula, each R ₁ independently represents a group selected from polymerizable groups represented by the following <Chemical Formula 2>, a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a hydroxyalkyl group, and at least one is selected from among the polymerizable group represented by the following <formula 2> .X ^-. is representative of the anion) ## STR2 ## (In the formula, R ₂ represents an alkyl group having 2 to 4 carbon atoms.) 2. A color filter using the coloring composition according to claim 1. 3. The polymerization ratio of a copolymer obtained by polymerizing a dye monomer represented by the following general formula (Chem. 3), N-phenylmaleimide and another monomer is 100% by weight of the copolymer. A photosensitive colored composition, characterized in that a colored copolymer having a N-phenylmaleimide content of 3 to 40% by weight is used. Embedded image (In the formula, each R ₁ independently represents a group selected from the polymerizable groups represented by the following chemical formula 4, a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a hydroxyalkyl group. one .X selected from polymerizable group represented by the following <formula 4> ^-. is representative of the anion) embedded image (In the formula, R ₂ represents an alkyl group having 2 to 4 carbon atoms.) 4. A color filter comprising the photosensitive coloring composition according to claim 3.