KR20170110335A - Colored photosensitive resin composition, color filter and image display device produced using the same - Google Patents

Abstract

TECHNICAL FIELD The present invention relates to a colored photosensitive resin composition, and more specifically, to an alkali-soluble resin; And a photocurable compound, wherein the alkali-soluble resin comprises a first cationic binder resin that is polymerized including a compound represented by the following formula (1) and a second cadmium-based binder resin that is polymerized by including a compound represented by the following formula Wherein the photopolymerizable compound comprises a first photopolymerizable compound having a molecular weight of 200 to 800 and a second photopolymerizable compound having a molecular weight of 100 to 400 in a weight ratio of 9: 1 to 1: 9 And a color filter and an image display device manufactured using the same.

Description

TECHNICAL FIELD [0001] The present invention relates to a colored photosensitive resin composition, and a color filter and an image display device using the same. BACKGROUND ART < RTI ID = 0.0 >

The present invention relates to a colored photosensitive resin composition, a color filter manufactured using the same, and an image display device.

BACKGROUND ART [0002] Color filters are widely used in various display devices such as an image pickup device and a liquid crystal display (LCD), and their application range is rapidly expanding. The color filter may be formed of three color patterns of red, green, and blue, or may be formed of three color patterns of yellow, magenta, and cyan, Lt; / RTI >

The coloring pattern of each of the color filters is generally formed using a colored photosensitive resin composition comprising a coloring agent such as pigment or dye, a binder resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent. The coloring pattern processing using the colored photosensitive resin composition is usually performed by a lithography process.

On the other hand, in recent years, color filters for various display devices including solid-state image pickup devices such as digital cameras have been required to have excellent developability, adhesion, and high sensitivity for improvement of processability and quality.

Specifically, recently, color filter materials are required to have high sensitivity, high reliability in pattern formation, and high color reproducibility with high transmittance. Accordingly, the pigment concentration of the colored photosensitive resin composition used for manufacturing the color filter is continuously increased, and a colored photosensitive resin composition having the same sensitivity and reliability at a low exposure dose is required in order to improve process productivity and yield. However, when a color filter is manufactured using a colored resin composition having a high contrast ratio or a high definition to improve development speed and sensitivity, unevenness or surface abnormality occurs in vacuum drying, and color filter defects frequently occur . This problem is further increased when the process time is shortened to increase the production amount of the color filter.

Korean Patent Publication No. 2000-0055254 (September 5, 2000)

An object of the present invention is to provide a colored photosensitive resin composition excellent in developability or adhesion and having a high developing speed.

The present invention also provides a color filter and an image display device manufactured using the above-mentioned colored photosensitive resin composition.

Specifically, it is an object of the present invention to provide a color filter and an image display device using the above-mentioned colored photosensitive resin composition and having excellent developing property or adhesion property and having a small surface roughness.

To achieve the above object, the colored photosensitive resin composition according to the present invention comprises an alkali-soluble resin; And a photocurable compound, wherein the alkali-soluble resin comprises a first cationic binder resin that is polymerized including a compound represented by the following formula (1) and a second cadmium-based binder resin that is polymerized by including a compound represented by the following formula Wherein the photopolymerizable compound comprises a first photopolymerizable compound having a molecular weight of 200 to 800 and a second photopolymerizable compound having a molecular weight of 100 to 400 in a weight ratio of 9: 1 to 1: 9 .

[Chemical Formula 1]

(2)

In formula (1)

이고,R1 and R2 are each independently

ego,

X is hydrogen, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group,

R3 is hydrogen or an alkyl group having 1 to 5 carbon atoms,

In formula (2)

이고,R4 and R5 are each independently

ego,

X is hydrogen, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group,

R6 is hydrogen or an alkyl group having 1 to 5 carbon atoms.

The present invention also provides a color filter made of the above-mentioned colored photosensitive resin composition and an image display device including the same.

The colored photosensitive resin composition of the present invention can provide a colored photosensitive resin composition excellent in developability or adhesion. Further, the colored photosensitive resin composition according to the present invention has an advantage of high developing rate.

The color filter and the image display device using the color photosensitive resin composition of the present invention have an advantage of being excellent in developability or adhesion, and having a small surface roughness.

Hereinafter, the present invention will be described in more detail.

When a member is referred to as being " on "another member in the present invention, this includes not only when a member is in contact with another member but also when another member exists between the two members.

Whenever a part is referred to as "including " an element in the present invention, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.

≪ Colored photosensitive resin composition &

An aspect of the present invention relates to an inkjet ink comprising an alkali-soluble resin; And a photocurable compound, wherein the alkali-soluble resin comprises a first cationic binder resin that is polymerized including a compound represented by the following formula (1) and a second cadmium-based binder resin that is polymerized by including a compound represented by the following formula Wherein the photopolymerizable compound comprises a first photopolymerizable compound having a molecular weight of 200 to 800 and a second photopolymerizable compound having a molecular weight of 100 to 400 in a weight ratio of 9: 1 to 1: 9 The present invention relates to a colored photosensitive resin composition.

[Chemical Formula 1]

(2)

In formula (1)

이고,R1 and R2 are each independently

ego,

X is hydrogen, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group,

R3 is hydrogen or an alkyl group having 1 to 5 carbon atoms,

In formula (2)

이고,R4 and R5 are each independently

ego,

X is hydrogen, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group,

R6 is hydrogen or an alkyl group having 1 to 5 carbon atoms.

Alkali-soluble resin

The alkali-soluble binder resin according to the present invention includes a first cadmium-based binder resin polymerized by including a compound represented by the following formula (1), thereby improving adhesion to a substrate and exhibiting excellent developing adhesion, thereby realizing a fine pattern for high resolution do.

[Chemical Formula 1]

이며, In the formulas, R 1 and R 2 are each independently

Lt;

X is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group, R3 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, preferably X is a hydroxyl group and R3 is a hydrogen atom or a methyl group.

The compound represented by the formula (1) can be synthesized using the following formula (3).

(3)

For example, the compound represented by the formula (3) is mixed with t-butylammonium bromide, heated and reacted with a solvent, an alkali aqueous solution is added dropwise, and the resulting epoxy compound is precipitated and separated. -Butylammonium bromide, acrylic acid, a phenol-based compound, and a solvent, and reacting them. However, the present invention is not limited thereto.

In addition, the alkali-soluble binder resin according to the present invention includes a second cadmium-based binder resin polymerized by including a compound of the following formula (2), thereby improving the adhesion with the substrate and providing a fine pattern for high resolution .

(2)

이며,Wherein R4 and R5 are each, independently,

Lt;

X is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group, R6 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, preferably X is a hydroxyl group, and R6 is a hydrogen atom or a methyl group.

The compound represented by the formula (2) can be synthesized using the following formula (4).

 [Chemical Formula 4]

For example, the compound represented by Chemical Formula 4 is mixed with t-butylammonium bromide and a solvent, followed by heating and reacting. Then, an alkali aqueous solution is added dropwise, and the resulting epoxy compound is precipitated and separated. -Butylammonium bromide, acrylic acid, a phenol-based compound, and a solvent, and reacting them. However, the present invention is not limited thereto.

The position of the hydroxyl group (-OH) in the formulas (3) and (4) is not particularly limited and may be, for example, 2-, 3- or 4- Lt; RTI ID = 0.0 > 1-up < / RTI >

As a result, depending on the position of the hydroxyl group (-OH) of the formula (3) or (4), the substitution positions of R1 and R2 in the above formula (1) or the substitution positions of R4 and R5 in the above formula (2) can be determined.

More specific examples of the compound represented by Formula 1 include 9,9-bis (3-cinnamic diester) fluorene, 9,9-bis (3-cinnamic diester) 3-cinnamoyl, 4-hydroxyphenyl) fluorene, 9,9-bis (glycidyl methacrylate ether) fluorene (9,9- 9,9-bis (3,4-dihydroxyphenyl) fluorene dicinnamic ester, 9,9-bis (glycidyl methacrylate ether) fluorene, , 6-diglycidyl methacrylate ether spiro (fluorene-9,9-xanthene), 9,9-bis (3- Allyl, 4-hydroxyphenylfluorene, 9,9-bis (4-allyloxyphenyl) fluorene, ) fluorene, and 9,9-bis (3,4-methacrylic diester) fluorene. And may be at least one selected, but is not limited thereto.

More specific examples of the compound represented by the formula (2) include 9,9-bis (3,4-methacrylic diester) xanthene, but the present invention is not limited thereto.

In one embodiment of the present invention, the acid value of the first cadmium-based binder resin or the second cadmium-based binder resin in the alkali-soluble binder resin may be 10 to 200 mgKOH / g, preferably 30 to 150 mgKOH / g It is good. When the acid value is in the range of 10 to 200 mgKOH / g, a sufficient developing rate can be ensured, and a fine pattern for high resolution can be realized.

In another embodiment of the present invention, the weight-average molecular weight of the first cationic binder resin or the second cationic binder resin in the alkali-soluble binder resin may be 1,000 to 30,000, preferably 1,500 to 10,000 good. When the weight average molecular weight is within the above range, the adhesiveness and developability can be improved.

In another embodiment of the present invention, the content of the alkali-soluble resin may be 1 to 40 parts by weight, preferably 5 to 20 parts by weight, based on 100 parts by weight of the colored photosensitive resin composition. When the content of the alkali-soluble resin is within the above range, there is an advantage that the solubility in a developing solution is sufficient and pattern formation is easy.

Photopolymerization  compound

The colored photosensitive resin composition according to the present invention comprises a photopolymerizable compound, wherein the photopolymerizable compound comprises a first photopolymerizable compound having a molecular weight of 200 to 800 and a second photopolymerizable compound having a molecular weight of 100 to 400 at a weight ratio of 9: 1: 9.

When the photopolymerizable compound contains two kinds of photopolymerizable compounds, that is, the first photopolymerizable compound according to the above molecular weight range and the second photopolymerizable compound within the above-mentioned weight ratio, appropriate photopolymerization reaction is induced and it is easy to form a pattern , There is an advantage that the developability is remarkably improved.

The photopolymerizable compound may be a monofunctional monomer, a bifunctional monomer, or a polyfunctional monomer, which is polymerized by the action of a photopolymerization initiator to be described later to enhance the strength of the pattern. Preferably, a monomer having two or more functional groups is used However, it is not limited as long as it is commonly used in the art.

The type of the monofunctional monomer is not particularly limited, and examples thereof include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate N-vinylpyrrolidone, and the like.

The type of the bifunctional monomer is not particularly limited and examples thereof include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) Glycol di (meth) acrylate, bis (acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di (meth) acrylate.

The type of the polyfunctional monomer is not particularly limited and includes, for example, trimethylolpropane tri (meth) acrylate, ethoxylated trimethylolpropane tri (meth) acrylate, propoxylated trimethylolpropane tri Acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, ethoxylated dipentaerythritol hexa (Meth) acrylate, propoxylated dipentaerythritol hexa (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and the like.

The photopolymerizable compound may be contained in an amount of 5 to 45 parts by weight, preferably 7 to 45 parts by weight, based on 100 parts by weight of the total solid content of the colored photosensitive resin composition. When the photopolymerizable compound is contained within the above range, the strength and smoothness of the pixel portion are improved. If the photopolymerizable compound is less than the above range, the strength may be somewhat lowered, and if it exceeds the above range, the viscosity may increase to some extent, which may be undesirable from a viewpoint of processability.

Light curing Initiator

The photopolymerization initiator can be used without particular limitation as long as it can polymerize the photopolymerizable compound. Specifically, the photopolymerization initiator is preferably selected from the group consisting of an acetophenone compound, a benzophenone compound, a triazine compound, a biimidazole compound, an oxime compound and a thioxanthone compound from the viewpoints of polymerization characteristics, initiation efficiency, absorption wavelength, availability, But not limited to, at least one compound selected from the group consisting of compounds.

Specific examples of the acetophenone-based compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 2-hydroxy- 1- [4- 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropane-1-one, 2-methylcyclohexyl phenyl ketone, 2-methyl-1- [4- (1-methylvinyl) phenyl] propane-1-one 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one.

Examples of the benzophenone compound include benzophenone, methyl 0-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3 ', 4,4'-tetra tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone, and the like.

Specific examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6 - (4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, (Trichloromethyl) -6- [2- (5-methylfuran-2- (4-methoxystyryl) -1,3,5-triazine, Yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (furan- , 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) ethenyl] -1,3,5-triazine, 2,4- ) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine.

Specific examples of the imidazole compound include 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbimidazole, 2,2'-bis (2,3- Phenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (alkoxyphenyl) , 2,2'-bis (2,6-dichlorophenyl) -4,4 ', 5,5'-tetra (trialkoxyphenyl) Imidazole compounds in which 4'5,5'-tetraphenyl-1,2'-biimidazole or phenyl groups at 4,4 ', 5,5' positions are substituted by carboalkoxy groups. Among them, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,3- , 2,2-bis (2,6-dichlorophenyl) -4,4'5,5'-tetraphenyl-1,2'-biimidazole is preferably used do.

Specific examples of the oxime compounds include o-ethoxycarbonyl-? -Oxyimino-1-phenylpropan-1-one and commercially available products such as Irgacure OXE 01 and OXE 02 from BASF.

Examples of the thioxanthone compound include 2-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4- .

The photopolymerization initiator may be contained in an amount of 0.1 to 40 parts by weight, preferably 1 to 30 parts by weight based on the total amount of the alkali-soluble resin and the photopolymerizable compound based on the total solid content of the colored photosensitive resin composition.

When the photopolymerization initiator satisfies the above range, the colored photosensitive resin composition is highly sensitized and the exposure time is shortened, which is preferable because productivity is improved and high resolution can be maintained. Further, there is an advantage that the strength of the pixel portion formed using the colored photosensitive resin composition and the smoothness of the surface of the pixel portion are improved.

The colored photosensitive resin composition according to the present invention may further comprise a photopolymerization initiation auxiliary besides the above-described photoinitiator.

When the colored photosensitive resin composition further contains the photopolymerization initiation auxiliary, there is an advantage that the sensitivity is further increased and the productivity is improved. The photopolymerization initiation assistant is not limited to those conventionally used in the art. For example, at least one compound selected from the group consisting of an amine compound, a carboxylic acid compound, and an organic sulfur compound having a thiol group is preferably used.

When the photopolymerization initiator is further used, it is contained in an amount of 0.1 to 40 parts by weight, specifically 1 to 30 parts by weight based on the total amount of the alkali-soluble binder resin and the photopolymerizable compound based on the total solid content of the colored photosensitive resin composition . When the content of the photopolymerization initiator is within the above range, the sensitivity of the colored photosensitive resin composition becomes higher, and the productivity of the color filter formed using the colored photosensitive resin composition can be improved.

In still another embodiment of the present invention, the colored photosensitive resin composition may further include at least one of a colorant, a photopolymerization initiator, a solvent, and an additive.

coloring agent

The colorant may include one or more pigments, and may further include one or more dyes.

The pigment may be an organic pigment or an inorganic pigment generally used in the art.

Examples of the organic pigment include various pigments used in printing ink, ink jet ink, etc. Specific examples thereof include water-soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, Anthanthrone pigments, indanthrone pigments, pravanthrone pigments, anthraquinone pigments, anthraquinone pigments, anthanthrone pigments, anthanthrone pigments, indanthrone pigments, indanthrone pigments, Pyranthrone pigments, diketopyrrolopyrrole pigments, and the like.

Examples of the inorganic pigments include metallic compounds such as metal oxides and metal complex salts. Specific examples of the inorganic pigments include metals such as iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony and carbon black Oxides or composite metal oxides. Particularly, the organic pigments and inorganic pigments may be specifically classified into pigments in the Society of Dyers and Colourists, and more specifically, those having a color index (CI) number Pigments, but are not limited thereto.

C.I. Pigment Yellow 13, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 180 And 185

C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, and 71

C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 208, 215, 216, 224, 242, 254, 255 and 264

C.I. Pigment Violet 14, 19, 23, 29, 32, 33, 36, 37 and 38

C.I. Pigment Blue 15 (15: 3, 15: 4, 15: 6, etc.), 21, 28, 60, 64 and 76

C.I. Pigment Green 7, 10, 15, 25, 36, 47 and 58

C.I Pigment Brown 28

C.I Pigment Black 1 and 7, etc.

These pigments may be used alone or in combination of two or more.

The exemplified C.I. Among the pigment pigments, C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, C.I. Pigment Yellow 185, C.I. Pigment Orange 38, C.I. Pigment Red 122, C.I. Pigment Red 166, C.I. Pigment Red 177, C.I. Pigment Red 208, C.I. Pigment Red 242, C.I. Pigment Red 254, C.I. Pigment Red 255, C.I. Pigment Violet 23, C.I. Pigment Blue 15: 3, Pigment Blue 15: 6, C.I. Pigment Green 7, C.I. Pigment Green 36, C.I. Pigment selected from Pigment Green 58 can be preferably used.

It is preferable to use a pigment dispersion in which the particle diameter of the pigment is uniformly dispersed. An example of a method for uniformly dispersing the particle diameter of the pigment includes a method of dispersing the pigment by adding a pigment dispersant. According to this method, a pigment dispersion in which the pigment is uniformly dispersed in a solution can be obtained.

Specific examples of the pigment dispersant include cationic surfactants, anionic surfactants, nonionic surfactants, amphoteric surfactants, polyester surfactants, and polyamine surfactants. These surfactants may be used alone or in combination of two or more.

The content of the pigment may be 10 to 75 parts by weight, specifically 15 to 75 parts by weight, based on 100 parts by weight of the total solid content in the pigment dispersion. When the content of the pigment satisfies the above range, it is preferable because the viscosity is low, the storage stability is excellent, and the dispersion efficiency is high, which is effective in increasing the contrast ratio.

The pigment dispersant is added for maintenance of deagglomeration and stability of the pigment, and any of those generally used in the art can be used without limitation. Specifically, it is preferable to contain an acrylate-based dispersant containing BMA (butyl methacrylate) or DMAEMA (N, N-dimethylaminoethyl methacrylate). In this case, it is preferable to apply the acrylate-based dispersing agent prepared by the living control method as disclosed in Korean Patent Publication No. 2004-0014311. DISCLOSURE OF THE INVENTION The acrylate- BYK-2000, DISPER BYK-2001, DISPER BYK-2070 and DISPER BYK-2150.

The acrylic dispersants exemplified above may be used alone or in combination of two or more.

As the pigment dispersant, other resin type pigment dispersants other than the acrylic dispersant may be used. The other resin type pigment dispersing agent may be a known resin type pigment dispersing agent, especially a polycarboxylic acid ester such as polyurethane, polyacrylate, unsaturated polyamide, polycarboxylic acid, polycarboxylic acid (partial) Amine salts of polycarboxylic acids, alkylamine salts of polycarboxylic acids, polysiloxanes, long chain polyaminoamide phosphate salts, esters of hydroxyl group-containing polycarboxylic acids and their modified products, or free ) Oil-based dispersants such as amides formed by reaction of a polyester having a carboxyl group with poly (lower alkyleneimine) or salts thereof; Soluble resin or water-soluble polymer compound such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylate ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol or polyvinylpyrrolidone; Polyester; Modified polyacrylates; Adducts of ethylene oxide / propylene oxide, and phosphate esters. DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK-160, BYK (trade name) 164, DISPER BYK-166, DISPER BYK-171, DISPER BYK-182, DISPER BYK-184; EFKA-4060, EFKA-4060, EFKA-4055, EFKA-4055, EFKA-4055, EFKA-4020, EFKA-4015, EFKA-4060, EFKA- 4330, EFKA-4400, EFKA-4406, EFKA-4510, EFKA-4800; SOLSPERS-24000, SOLSPERS-32550, NBZ-4204/10 from Lubirzol; Hinoact T-6000, Hinoact T-7000, Hinoact T-8000; available from Kawaken Fine Chemicals; AJISPUR PB-821, Ajisper PB-822, Ajisper PB-823 manufactured by Ajinomoto; FLORENE DOPA-17HF, fluorene DOPA-15BHF, fluorene DOPA-33, and fluorene DOPA-44 are trade names of Kyoeisha Chemical Co., In addition to the above acrylic dispersant, other resin type pigment dispersants may be used alone or in combination of two or more, and may be used in combination with an acrylic dispersant.

The amount of the dispersant may be 5 to 60 parts by weight, specifically 15 to 50 parts by weight based on 100 parts by weight of the pigment solid used. If the content of the pigment dispersant is within the above range, The pigment is easily atomized, and there is an advantage that problems such as gelation after dispersion can be prevented.

The dye can be used without limitation as long as it has solubility in an organic solvent. It is preferable to use a dye which has solubility in an organic solvent and can ensure reliability such as solubility in an alkali developing solution, heat resistance and solvent resistance.

Examples of the dye include acid dyes having an acidic group such as sulfonic acid and carboxylic acid, salts of an acidic dye and a nitrogen-containing compound, sulfonamides of an acidic dye and derivatives thereof, and azo, Based acid dyes and derivatives thereof.

Preferably, the dye is a compound classified as a dye in a color index (published by The Society of Dyers and Colourists), or a known dye described in a dyeing note (coloring yarn).

Specific examples of the dye include C.I. As solvent dyes,

C.I. Yellow dyes such as Solvent Yellow 4, 14, 15, 16, 21, 23, 24, 38, 56, 62, 63, 68, 79, 82, 93, 94, 98, 99, 151, 162, 163;

C.I. Red dyes such as Solvent Red 8, 45, 49, 89, 111, 122, 125, 130, 132, 146, 179;

C.I. Orange dyes such as solvent orange 2, 7, 11, 15, 26, 41, 45, 56, 62;

C.I. Blue dyes such as Solvent Blue 5, 35, 36, 37, 44, 59, 67 and 70;

C.I. Violet dyes such as solvent violet 8, 9, 13, 14, 36, 37, 47, 49;

C.I. Green dyes such as Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35 and the like.

C.I. Solvent dye having excellent solubility in an organic solvent. Solvent Yellow 14, 16, 21, 56, 151, 79, 93; C.I. Solvent Red 8, 49, 89, 111, 122, 132, 146, 179; C.I. Solvent Orange 41, 45, 62; C.I. Solvent Blue 35, 36, 44, 45, 70; C.I. Solvent violet 13 is preferred, and C.I. Solvent Yellow 21, 79; C.I. Solvent Red 8, 122, 132; C.I. Solvent orange 45, 62 is more preferable.

Also, C.I. As the acid dye,

CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112 , 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184 Yellow dyes such as 1,1,1,2,2,2,2,2,2,23,28, 240,242, 243,251 and the like, such as, for example, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, ;

CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44, 50, 51, 52, 57, 66, 73, 80, 87, 88 , 91, 92, 94, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 158, 176, 182, 183, 198, 206, 211, 215, 216, 217 , 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 195, 308, 312, 315, 316, 339, 341, 345, 346, 349 Red dyes such as 382, 383, 394, 401, 412, 417, 418, 422, 426;

Orange dyes such as C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;

CI Acid Blue 1, 7, 9, 15, 18, 23, 25, 27, 29, 40, 42, 45, 51, 62, 70, 74, 80, 83, 86, 87, 90, , 112, 113, 120, 129, 138, 147, 150, 158, 171, 182, 192, 210, 242, 243, 256, 259, 267, 278, 280, 285, 290, 296, 315, , 335, 340 and the like;

Violet dyes such as C.I. Acid Violet 6B, 7, 9, 17, 19, 66 and the like;

Green dyes such as C.I. acid green 1, 3, 5, 9, 16, 25, 27, 50, 58, 63, 65, 80, 104, 105, 106,

CI Acid Yellow 42, which is excellent in solubility in organic solvents in acid dyes; C.I. Acid Red 92; C. I. Acid Blue 80, 90; C.I. Acid Violet 66; C.I. Acid Green 27 is preferred.

As a C.I. direct dye,

CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129 , Yellow dyes such as 136, 138, and 141;

CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211 , 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250;

Orange dyes such as C.I. Direct Orange 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

CI Direct Blue 38, 44, 57, 70, 77, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113 , 114, 115, 117, 119, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 166, 167, 170, 171, 172, 173, 188, 189 , 190, 192, 193, 194, 196, 198, 199, 200, 207, 209, 210, 212, 213, 214, 222, 228, 229, 237, 238, 242, 243, 244, 245, 247, 248 , 250, 251, 252, 256, 257, 259, 260, 268, 274, 275 and 293;

Violet dyes such as C.I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

Green dyes such as C.I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79,

Also, C.I. As modatto dyes,

Yellow dyes such as C.I. Modatto Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

CI Modal Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 30, 32, 33, 36, 37, Red dyes such as 41, 43, 45, 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90, 94, 95;

CI Modanato Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, dyes;

CI Modanito Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 43, 44, 48, 49, 53, 61, 74, 77, 83, and 84;

Violet colored dyes such as C.I. Modanth violet 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53, 58;

Green dyes such as C.I. Modatto Green 1, 3, 4, 5, 10, 15, 19, 26, 29, 33, 34, 35, 41, 43,

These dyes may be used alone or in combination of two or more.

The content of the dye may be 0.5 to 80% by weight, preferably 0.5 to 60% by weight, more preferably 1 to 50% by weight based on the solid content in the colorant. When the dye is contained within the above range, the problem of lowering the reliability of elution of the dye by the organic solvent after the pattern formation can be prevented, and it is preferable since the sensitivity is excellent.

The content of the colorant may be 5 to 60 parts by weight, preferably 10 to 45 parts by weight based on 100 parts by weight of the total solid content of the colored photosensitive resin composition. When the colorant is contained within the above range, even if a thin film is formed, the color density of the pixel is sufficient, and the occurrence of residue can be prevented because the non-curing portion of the non-cured portion is not deteriorated. When the colorant is contained in an amount of less than 5 parts by weight, the color density of a pixel in the case of forming a thin film is somewhat insufficient, and the color separation performance as a color filter may be somewhat lowered. Can cause problems.

The solid content of the colored photosensitive resin composition in the present invention means the total content of the remaining components excluding the solvent from the colored photosensitive resin composition.

solvent

The solvent used in the conventional colored photosensitive resin composition may be used without particular limitation as long as it is effective in dissolving the other components contained in the colored photosensitive resin composition of the present invention. Specifically, at least one selected from the group consisting of ethers, aromatic hydrocarbons, ketones, alcohols, esters and amides can be used.

More specifically, examples of the solvent include ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether and ethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether , Diethylene glycol dialkyl ethers such as diethylene glycol dipropyl ether and diethylene glycol dibutyl ether, ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate, propylene glycol monomethyl ether acetate , Alkylene glycol alkyl ether acetates such as propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate and methoxypentyl acetate, aromatic hydrocarbons such as benzene, toluene, xylene and mesitylene, Ke , Ketones such as acetone, methyl amyl ketone, methyl isobutyl ketone and cyclohexanone, alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol and glycerin, ethyl 3-ethoxypropionate, 3- Esters such as methyl methoxypropionate, and cyclic esters such as? -Butyrolactone.

The solvent may be an organic solvent having a boiling point in the range of 100 ° C to 200 ° C in terms of coatability and dryness. Examples of the solvent include propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, ethyl lactate, , Ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, and the like.

The solvent may be used alone or in admixture of two or more, and may be contained in an amount of 50 to 90 parts by weight, specifically 55 to 85 parts by weight, based on the total amount of the colored photosensitive resin composition. When the solvent is contained within the above range, the coating property is improved when applied with a coating apparatus such as a roll coater, a skin coater, a slit and spin coater, a slit coater (die coater), or an ink jet.

additive

The additive may be optionally added, for example, other polymer compounds, a curing agent, a surfactant, an adhesion promoter, an antioxidant, an ultraviolet absorber and an anti-aggregation agent.

Specific examples of the other polymer compound include a curable resin such as epoxy resin and maleimide resin, a thermoplastic resin such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, polyurethane and the like .

The curing agent is used for deep curing and for increasing mechanical strength. Specific examples of the curing agent include an epoxy compound, a polyfunctional isocyanate compound, a melamine compound, and an oxetane compound.

Specific examples of the epoxy compound in the curing agent include bisphenol A epoxy resin, hydrogenated bisphenol A epoxy resin, bisphenol F epoxy resin, hydrogenated bisphenol F epoxy resin, novolak epoxy resin, other aromatic epoxy resin, alicyclic epoxy resin Alicyclic or aromatic epoxy compounds, butadiene (co) polymeric epoxides and isoprene (co) polymers other than the brominated derivatives, epoxy resins and brominated derivatives of these epoxy resins, glycidyl ester resins, glycidyl amine resins, (Co) polymer epoxides, glycidyl (meth) acrylate (co) polymers, and triglycidyl isocyanurate.

Specific examples of the oxetane compound in the curing agent include carbonates bisoxetane, xylene bisoxetane, adipate bisoxetane, terephthalate bisoxetane, cyclohexanedicarboxylic acid bisoxetane, and the like.

The curing agent may be used together with a curing agent in combination with a curing auxiliary compound capable of ring-opening polymerization of the epoxy group of the epoxy compound and the oxetane skeleton of the oxetane compound. The curing assistant compound includes, for example, polyvalent carboxylic acids, polyvalent carboxylic anhydrides, and acid generators. The polyvalent carboxylic acid anhydrides may be those commercially available as an epoxy resin curing agent. Specific examples of the above-mentioned epoxy resin curing agent include epoxy resin curing agents such as epoxy resins, epoxy resins, epoxy resins, epoxy resins, epoxy resins, epoxy resins, Manufactured by Japan Ehwa Co., Ltd.). The curing agents exemplified above may be used alone or in combination of two or more.

The surfactant may be used to further improve film-forming properties of the photosensitive resin composition, and a fluorine-based surfactant or a silicone-based surfactant may be preferably used.

Examples of the silicone surfactant include DC3PA, DC7PA, SH11PA, SH21PA and SH8400 from Dow Corning Toray Silicone Co., Ltd. and TSF-4440, TSF-4300, TSF-4445, TSF-4446 and TSF-4460 , And TSF-4452. Examples of the fluorine-based surfactant include Megapis F-470, F-471, F-475, F-482 and F-489 commercially available from Dainippon Ink and Chemicals, Incorporated. The above-exemplified surfactants may be used alone or in combination of two or more.

Specific examples of the adhesion promoter include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- Aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- ( 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3- 3-isocyanatopropyltrimethoxysilane, 3-isocyanatepropyltriethoxysilane, and the like. The adhesion promoters exemplified above may be used alone or in combination of two or more. The adhesion promoter may be contained in an amount of usually 0.01 to 10 parts by weight, preferably 0.05 to 2 parts by weight, based on the solid content of the colored photosensitive resin composition. Specific examples of the antioxidant include 2,2'-thiobis (4-methyl-6-t-butylphenol) and 2,6-di-t-butyl-4-methylphenol.

Specific examples of the ultraviolet absorber include 2- (3-tert-butyl-2-hydroxy-5-methylphenyl) -5-chlorobenzothiazole and alkoxybenzophenone.

Specific examples of the anti-aggregation agent include sodium polyacrylate and the like.

The additive may be used in an appropriate amount by those skilled in the art, so long as the effects of the present invention are not impaired. For example, the additive may be included in an amount of 0.01 to 1 part by weight, preferably 0.1 to 0.5 part by weight based on 100 parts by weight of the total of the colored photosensitive resin composition. When the additive is included in the above range, each additive can be provided with desired properties without impairing the effect of the present invention.

The method for producing the above-mentioned colored photosensitive resin composition is not limited thereto, but it can be produced, for example, by the following method.

The pigment in the colorant is mixed with a solvent and dispersed using a bead mill or the like until the average particle diameter of the pigment becomes about 0.2 μm or less. At this time, if necessary, a part or all of the pigment dispersant, the dye and the alkali-soluble resin may be mixed and dissolved or dispersed with the above-mentioned solvent. To the mixed dispersion thus obtained, the remainder of the alkali-soluble resin, the photopolymerizable compound, And other additives and solvents are added so as to have a predetermined concentration, the colored photosensitive resin composition according to the present invention can be prepared.

≪ Color filter and image display device >

Another aspect of the present invention relates to a color filter manufactured using the above-mentioned colored photosensitive resin composition.

Further, another aspect of the present invention relates to an image display apparatus including the color filter described above.

The image display apparatus of the present invention is provided with the above-described color filter, and a specific example thereof is a liquid crystal display, an OLED, a flexible display, and the like, but is not limited thereto.

Hereinafter, the present invention will be described in detail by way of examples to illustrate the present invention. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the above-described embodiments. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art. In the following, "%" and "part" representing the content are by weight unless otherwise specified.

Pigment dispersion preparation

<Pigment dispersion composition M1>

C.I. , 12.0 parts by weight of Pigment Blue 15: 6, 4.0 parts by weight of DISPERBYK-2001 (manufactured by BYK) as a pigment dispersant, 44 parts by weight of propylene glycol methyl ether acetate as a solvent and 40 parts by weight of propylene glycol methyl ether by means of a bead mill Followed by mixing / dispersing to prepare a pigment dispersion M1.

Synthesis of alkali-soluble resin

< Synthetic example  1: Synthesis of compound of formula (1)

A 3,000 ml three-necked round flask was charged with 364.4 g of 3 ', 6'-dihydroxyspiro (fluorene-9,9-xanthene) (3', 6 " And 0.4159 g of bromide were mixed and 2359 g of epichlorohydrin was added and reacted by heating at 90 DEG C. When 3,6-dihydroxy spiro (fluorene-9,9-chanthylene) was completely consumed by liquid chromatography After cooling to 30 DEG C, 50% NaOH aqueous solution (3 equivalents) was added slowly. When the epichlorohydrin was completely removed by analysis by liquid chromatography, the reaction solution was extracted with dichloromethane, washed three times with water, and the organic layer was dried with magnesium sulfate The dichloromethane was distilled off under reduced pressure and recrystallized using a dichloromethane / methanol mixture ratio of 50:50.

One equivalent of the thus synthesized epoxy compound, 0.004 equivalent of t-butylammonium bromide, 0.001 equivalent of 2,6-diisobutylphenol and 2.2 equivalents of acrylic acid were mixed and 24.89 g of solvent propylene glycol monomethyl ether acetate was added and mixed. The reaction solution was heated and dissolved at 90 to 100 ° C while air was blown at 25 ml / min. The reaction solution was completely dissolved by heating to 120 DEG C in a cloudy state. When the solution becomes transparent and the viscosity becomes high, the acid value is measured and stirred until the acid value becomes less than 1.0 mg KOH / g. It took 11 hours to reach the target price (0.8). After completion of the reaction, the temperature of the reactor was lowered to room temperature to obtain a colorless transparent compound of the formula (1).

< Synthetic example  2: Synthesis of compound of formula (2)

A 3,000 ml three-necked round-bottomed flask was charged with 364.4 g of 4,4 '- (9H-xanthene-9,9-diyl) diphenol (4,4' And 2359 g of epichlorohydrin were charged and reacted by heating at 90 占 폚. When the 4,4 '- (9H-xanthene-9,9-diyl) diphenol was completely consumed by liquid chromatography, the solution was cooled to 30 DEG C and 50% NaOH aqueous solution (3 equivalents) was slowly added. When the epichlorohydrin was completely exhausted, the reaction mixture was extracted with dichloromethane and then washed three times. The organic layer was dried over magnesium sulfate, and the dichloromethane was distilled off under reduced pressure. The dichloromethane-methanol mixture ratio was 50:50 And recrystallized.

One equivalent of the thus synthesized epoxy compound, 0.004 equivalent of t-butylammonium bromide, 0.001 equivalent of 2,6-diisobutylphenol and 2.2 equivalents of acrylic acid were mixed and 24.89 g of solvent propylene glycol monomethyl ether acetate was added and mixed. The reaction solution was heated and dissolved at 90 to 100 ° C while air was blown at 25 ml / min. The reaction solution was completely dissolved by heating to 120 DEG C in a cloudy state. When the solution becomes transparent and the viscosity becomes high, the acid value is measured and stirred until the acid value becomes less than 1.0 mg KOH / g. It took 11 hours to reach the target price (0.8). After completion of the reaction, the temperature of the reactor was lowered to room temperature to obtain a colorless transparent compound of formula (2).

< Synthetic example  3: Carometer  Synthesis of binder resin (b-1) &gt;

600 g of propylene glycol monomethyl ether acetate was added to and dissolved in 307.0 g of the compound of formula (1) in Synthesis Example 1, 78 g of biphenyltetracarboxylic acid dianhydride and 1 g of tetraethylammonium bromide were mixed and gradually heated to 110 to 115 And reacted for 4 hours. After disappearance of the acid anhydride group was confirmed, 38.0 g of 1,2,3,6-tetrahydrophthalic anhydride was mixed and reacted at 90 DEG C for 6 hours to polymerize with a cationic binder resin. The disappearance of the anhydride was confirmed by IR spectrum.

< Synthetic example  4 : Carometer  Synthesis of binder resin (b-2) &gt;

600 g of propylene glycol monomethyl ether acetate was added to and dissolved in 307.0 g of the compound of formula (2) in Synthesis Example 2, 78 g of biphenyltetracarboxylic dianhydride and 1 g of tetraethylammonium bromide were mixed and gradually heated to 110 to 115 And reacted for 4 hours. After disappearance of the acid anhydride group was confirmed, 38.0 g of 1,2,3,6-tetrahydrophthalic anhydride was mixed and reacted at 90 DEG C for 6 hours to polymerize with a cationic binder resin. The disappearance of the anhydride was confirmed by IR spectrum.

< Comparative Synthetic Example  One : Carometer  Synthesis of binder resin (b-3)

200 g of a THF (tetrahydrofuran) solution as a reaction solvent was charged into a 500 ml four-necked flask and maintained at 50 캜. 89 g of the compound represented by the general formula (5) was introduced and 44.5 g of the epiklohydrin solution represented by the general formula (6) was introduced at a rate of 5.25 g per minute using a dropping funnel and reacted for 1 hour and 30 minutes. At this time, n in the formula (6) was 1. 348 g of the bisphenol-based fluorene-type epoxy resin compound obtained by the reaction was charged into a 1000-mL reactor, 140.52 g of an acrylic acid solution was added, and the temperature was raised to 80 ° C to conduct the reaction. Thereafter, 13.5 g of tetraethylammonium bromide was slowly added thereto, and the reaction was allowed to proceed for 60 hours. 150 g of the above reaction product was placed in a reactor, and 180.5 g of anhydride (phthalic anhydride) and 348.8 g of anhydride (anhydrous pyromellitic acid) were added thereto and maintained at 120 ° C. At this time, 0.718 g of Fascat 4101 as a catalyst was slowly added thereto and reacted for 5 hours to prepare a binder resin.

[Chemical Formula 5]

[Chemical Formula 6]

Example  1 to 4 and Comparative Example  1 to 7

The colored photosensitive resin composition was prepared using the components and the content (unit: parts by weight, based on 100 parts by weight of the colored photosensitive resin composition) shown in Table 1 below.

division coloring agent Alkali-soluble resin Photopolymerizable compound Photopolymerization initiator solvent additive a-1 a-2 b-1 b-2 b-3 b-4 c-1 c-2 c-3 d e-1 e-2 f Example 1 25.0 - 10.1 - - - 2.0 3.0 - 1.0 21.3 37.5 0.1 Example 2 25.0 - - 10.1 - - 2.0 3.0 - 1.0 21.3 37.5 0.1 Example 3 22.5 0.3 10.2 - - - 2.0 3.0 - 1.0 21.3 39.6 0.1 Example 4 22.5 0.3 - 10.2 - - 2.0 3.0 - 1.0 21.3 39.6 0.1 Comparative Example 1 25.0 - - - 10.1 - 2.0 3.0 - 1.0 21.3 37.5 0.1 Comparative Example 2 25.0 - - - - 10.1 2.0 3.0 - 1.0 21.3 37.5 0.1 Comparative Example 3 25.0 - 10.1 - - - - 3.0 2.0 1.0 21.3 37.5 0.1 Comparative Example 4 25.0 - - 10.1 - - - 3.0 2.0 1.0 21.3 37.5 0.1 Comparative Example 5 25.0 - 10.1 - - - 5.0 - - 1.0 21.3 37.5 0.1 Comparative Example 6 25.0 - 10.1 - - - - 5.0 - 1.0 21.3 37.5 0.1 Comparative Example 7 22.5 0.3 10.2 - - - 5.0 - - 1.0 21.3 39.6 0.1 a-1: Pigment dispersion composition M1
a-2: CI Solvent Blue 44 (trade name: VALIFAST BLUE 2620)
b-1: Cathode binder resin of Synthesis Example 3 (cadmium-based binder resin of the present invention)
b-2: Cathode binder resin of Synthesis Example 4 (Cathode binder resin of the present invention)
b-3: The binder resin of Comparative Synthesis Example 1
b-4: Acrylic binder (benzylmethacrylate / N-phenylmaleimide / styrene / methacrylic acid) (molar ratio 55/9/11/25, Mw = 20,000, acid value 100 mgKOH / g)
c-1: 1,6-hexanediol diacrylate Mw = 226
c-2: KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd.) Mw = 524
c-3: Polyethylene glycol diacrylate Mw = 575
d: OXE-01 (manufactured by BASF)
e-1: Propylene glycol monomethyl ether acetate
e-2: Propylene glycol monomethyl ether
f: 3-methacryloyloxypropyltrimethoxysilane (Shinetsu)

Manufacture of color filters

A color filter was prepared using the colored photosensitive resin compositions prepared in Examples 1 to 4 and Comparative Examples 1 to 7. Specifically, each colored photosensitive resin composition was coated on a 2-inch glass substrate ("EAGLE XG" manufactured by Corning) by spin coating, and then placed on a heating plate and held at a temperature of 100 ° C for 3 minutes to form a thin film. Subsequently, a test photomask having a pattern for changing the transmittance in the range of 1 to 100% in a stepwise manner and a line / space pattern of 1 to 50 m was placed on the thin film, and the distance between the test photomask and the test photomask was set to 100 m. Respectively. At this time, the ultraviolet ray was irradiated at a light intensity of 100 mJ / cm ² using a 1 kW high pressure mercury lamp containing g, h and i lines, and no special optical filter was used. The ultraviolet irradiated thin film was immersed in a KOH aqueous solution of pH 10.5 for 2 minutes to develop. Thereafter, the glass plate coated with the thin film was washed with distilled water, blown with nitrogen gas, dried, and heated in a 200 ° C heating oven for 25 minutes to prepare a color filter. The film thickness of the produced color filter was 2.0 탆.

Experimental Example

(1) Developability

The permeability of the fishy pattern was measured and is shown in Table 2 below. The measurement standard when the transmittance of the unexposed portion is 100% is as follows.

?: Transmittance of 95% or more

?: Transmittance 80% or more and less than 95%

X: Transmittance less than 80%

(2) Development speed

The time taken for the unexposed area to completely dissolve in the developing solution at the time of development was measured.

○: 20 seconds or less

△: more than 20 seconds and less than 40 seconds

×: exceeding 40 seconds

(3) Pattern surface roughness

The resulting patterned surface was measured using an AFM (Atomic-force microscopy) instrument (XE-100, Park Systems).

○: Ra (average roughness) value below 2.0

?: Ra value exceeding 2.0 and not more than 3.0

X: Ra value exceeded 3.0

division Developability Development speed Pattern surface roughness Example 1 ○ ○ ○ Example 2 ○ ○ ○ Example 3 ○ ○ ○ Example 4 ○ ○ ○ Comparative Example 1 △ △ △ Comparative Example 2 △ △ △ Comparative Example 3 × × × Comparative Example 4 × × × Comparative Example 5 △ △ △ Comparative Example 6 × × △ Comparative Example 7 △ △ △

Claims (8)

Alkali-soluble resins; And
A photopolymerizable compound,
Wherein the alkali-soluble resin is at least one selected from the group consisting of a first cadosystem binder resin that is polymerized including a compound represented by the following formula (1) and a second cadoside binder resin that is polymerized to include a compound represented by the following formula / RTI &gt;
Wherein the photopolymerizable compound comprises a first photopolymerizable compound having a molecular weight of 200 to 800 and a second photopolymerizable compound having a molecular weight of 100 to 400 in a weight ratio of 9: 1 to 1: 9.
[Chemical Formula 1]

(2)

In formula (1)
R1 and R2 are each independently

ego,
X is hydrogen, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group,
R3 is hydrogen or an alkyl group having 1 to 5 carbon atoms,
In formula (2)
R4 and R5 are each independently

ego,
X is hydrogen, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group,
R6 is hydrogen or an alkyl group having 1 to 5 carbon atoms. The method according to claim 1,
Wherein the alkali-soluble resin is contained in an amount of 1 to 40 parts by weight based on 100 parts by weight of the total of the colored photosensitive resin composition. The method according to claim 1,
And the acid value of the first cadmium-based binder resin or second cadmium-based binder resin is 10 to 200 mgKOH / g. The method according to claim 1,
Wherein the first cadmium-based binder resin or the second cadmium-based binder resin has a weight average molecular weight of 1,000 to 30,000. The method according to claim 1,
Wherein the photopolymerizable compound is contained in an amount of 5 to 45 parts by weight based on 100 parts by weight of the total solid content of the colored photosensitive resin composition. The method according to claim 1,
A colorant, a photopolymerization initiator, a solvent, and an additive. A color filter produced by using the colored photosensitive resin composition according to any one of claims 1 to 6. An image display device comprising the color filter of claim 7.