KR20170087301A - Photosensitive resin composition and color filter using the same - Google Patents

Photosensitive resin composition and color filter using the same Download PDF

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KR20170087301A
KR20170087301A KR1020160007114A KR20160007114A KR20170087301A KR 20170087301 A KR20170087301 A KR 20170087301A KR 1020160007114 A KR1020160007114 A KR 1020160007114A KR 20160007114 A KR20160007114 A KR 20160007114A KR 20170087301 A KR20170087301 A KR 20170087301A
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formula
weight
binder resin
repeating unit
unit represented
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KR101863248B1 (en
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이인재
최세영
이창률
한규석
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삼성에스디아이 주식회사
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators

Abstract

(A-1) a polymer comprising a repeating unit represented by the following formula (1), a repeating unit represented by the following formula (2), a repeating unit represented by the following formula (3), a repeating unit represented by the following formula An acrylic binder resin; (A-2) carcass binder resin; (B) a photopolymerizable monomer; (C) a photopolymerization initiator; (D) a colorant; And (E) a solvent, and a color filter manufactured using the same.
[Chemical Formula 1]

Figure pat00060

(2)
Figure pat00061

(3)
Figure pat00062

[Chemical Formula 4]
Figure pat00063

[Chemical Formula 5]
Figure pat00064

(In the above Chemical Formulas 1 to 5, each substituent group is as defined in the specification.)

Description

TECHNICAL FIELD [0001] The present invention relates to a photosensitive resin composition, and a color filter using the same. BACKGROUND ART [0002]

The present invention relates to a photosensitive resin composition and a color filter using the same.

Recently, as the spread of the large-screen liquid crystal display device has expanded, a demand for a new performance enhancement for the liquid crystal display device has been increasing. Among the components of the liquid crystal display device, the color filter is the most important color realizing device. Research is continuing.

In addition, in the case of a large-screen liquid crystal display device, the colorant concentration of the photosensitive resin composition is increased in manufacturing a color filter in order to increase the color purity. In order to increase productivity and yield in the production process, a photosensitive resin composition having a low developing speed and excellent sensitivity .

The color filter using the photosensitive resin composition can be produced by coating three or more kinds of hues on a transparent substrate mainly by a dyeing method, an electrodeposition method, a printing method, a pigment dispersion method and the like. Recently, a pigment dispersion method is widely used.

On the other hand, in a color filter made of a pigment type photosensitive resin composition, there is a limit in that the luminance and the contrast ratio are lowered due to the pigment particle size and the aggregation of the pigment particles. In order to overcome such limitations, attempts have been made to use a dye-type photosensitive resin composition which does not form particles or has a dye having a very small primary particle diameter relative to the pigment dispersion. However, the dye-type photosensitive resin composition is difficult to commercialize due to its weak heat resistance, light resistance and chemical resistance.

One embodiment is to provide a photosensitive resin composition having excellent color characteristics and adhesion.

Another embodiment is to provide a color filter manufactured using the photosensitive resin composition.

(A-1) a repeating unit represented by the following formula (1), a repeating unit represented by the following formula (2), a repeating unit represented by the following formula (3), a repeating unit represented by the following formula An acrylic binder resin containing a repeating unit to be a repeating unit; (A-2) carcass binder resin; (B) a photopolymerizable monomer; (C) a photopolymerization initiator; (D) a colorant; And (E) a solvent.

[Chemical Formula 1]

Figure pat00001

(2)

Figure pat00002

(3)

Figure pat00003

[Chemical Formula 4]

Figure pat00004

[Chemical Formula 5]

Figure pat00005

In the above Chemical Formulas 1 to 5,

R 1 to R 7 are each independently a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

R 8 is a substituted or unsubstituted C 11 to C 20 alkyl group,

L 1 is a substituted or unsubstituted C 1 to C 5 alkylene group,

n is an integer of 0 or 1;

The repeating unit represented by the formula (1) is contained in an amount of 10 to 30% by weight based on the total amount of the acrylic binder resin, the repeating unit represented by the formula (2) is contained in an amount of 10 to 30% 3 is contained in an amount of 10 to 30% by weight, the repeating unit represented by the formula (4) is contained in an amount of 5 to 25% by weight, the repeating unit represented by the formula (5) By weight to 35% by weight.

The repeating unit represented by the formula (1) is contained in an amount of 15 to 25% by weight, the repeating unit represented by the formula (2) is contained in an amount of 15 to 25% by weight based on the total amount of the acrylic binder resin, 3 is contained in an amount of 15 to 25 wt%, the repeating unit represented by the formula (4) is contained in an amount of 10 to 20 wt%, the repeating unit represented by the formula (5) is contained in an amount of 20 wt% To 30% by weight.

The acrylic binder resin may have a weight average molecular weight of 3,000 g / mol to 30,000 g / mol.

The acrylic binder resin may have an acid value of 100 mgKOH / g to 140 mgKOH / g.

The cadmium binder resin may include a repeating unit represented by the following formula (6).

[Chemical Formula 6]

Figure pat00006

In Formula 6,

R 11 and R 12 are each independently a hydrogen atom or a substituted or unsubstituted (meth) acryloyloxyalkyl group,

R 13 and R 14 are each independently a hydrogen atom, a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group,

Z 1 is a single bond, O, CO, SO 2 , CR 7 R 8 , SiR 9 R 10 (wherein R 7 to R 10 are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group) Is any one of the linking groups represented by formulas (6-1) to (6-11)

[Formula 6-1]

Figure pat00007

[Formula 6-2]

Figure pat00008

[Formula 6-3]

Figure pat00009

[Formula 6-4]

Figure pat00010

[Formula 6-5]

Figure pat00011

(In the above Formula 6-5,

R a is a hydrogen atom, an ethyl group, C 2 H 4 Cl, C 2 H 4 OH, CH 2 CH = CH 2 or a phenyl group.

[Formula 6-6]

Figure pat00012

[Formula 6-7]

Figure pat00013

[Formula 6-8]

Figure pat00014

[Formula 6-9]

Figure pat00015

[Chemical Formula 6-10]

[Chemical Formula 6-11]

Figure pat00017

Z 2 is an acid anhydride residue,

m1 and m2 are each independently an integer of 0 to 4;

The cadmium binder resin may have a weight average molecular weight of 500 g / mol to 50,000 g / mol.

The cadmium binder resin may have an acid value of from 100 mgKOH / g to 140 mgKOH / g.

The acrylic binder resin and the cadmium binder resin may be contained in a weight ratio of 0.2: 1 to 20: 1.

The coloring agent may include a pigment.

The pigments may include green pigments, yellow pigments or combinations thereof.

The photosensitive resin composition comprises 0.5 to 10% by weight of the acrylic binder resin (A-1); 0.1 to 10% by weight of the (A-2) cadmium-based binder resin; 1 to 10% by weight of the photopolymerizable monomer (B); 0.1 to 10% by weight of the photopolymerization initiator (C); 10% to 50% by weight of (D) the colorant; And (E) the solvent balance.

The photosensitive resin composition may include malonic acid; 3-amino-1,2-propanediol; A silane-based coupling agent comprising a vinyl group or (meth) acryloxy group; Leveling agents; Fluorine surfactants; A radical polymerization initiator; Or a combination thereof.

Another embodiment provides a color filter manufactured using the photosensitive resin composition.

Other aspects of the present invention are included in the following detailed description.

The photosensitive resin composition is excellent in developability and adhesion, and has high luminance characteristics while realizing a high resolution of a pattern, and thus can be usefully used for a color filter.

1 to 7 are optical microscope photographs of a pattern in a specimen produced by coating, exposing and developing the photosensitive resin composition according to Examples 1 to 4 and Comparative Examples 1 to 3 independently.

Hereinafter, embodiments of the present invention will be described in detail. However, it should be understood that the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

Unless otherwise specified herein, "substituted" means that at least one hydrogen atom is replaced by a halogen atom (F, Cl, Br, I), a hydroxy group, a C1 to C20 alkoxy group, a nitro group, a cyano group, An ester group, an ether group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a C1 A C2 to C20 alkenyl group, a C2 to C20 alkynyl group, a C6 to C30 aryl group, a C3 to C20 cycloalkyl group, a C3 to C20 cycloalkenyl group, a C3 to C20 cycloalkynyl group, a C2 to C20 heterocycloalkyl group, a C2 to C20 heterocycloalkyl group, To C20 heterocycloalkenyl groups, C2 to C20 heterocycloalkynyl groups, C3 to C30 heteroaryl groups, or combinations thereof.

Also, unless otherwise specified herein, "hetero" means that at least one heteroatom of N, O, S, and P is included in the formula.

&Quot; (Meth) acrylic acid "refers to both" acrylic acid "and" methacrylic acid " "It means both are possible.

Unless otherwise defined in the chemical formulas in this specification, when no chemical bond is drawn at the position where the chemical bond should be drawn, it means that the hydrogen atom is bonded at the above position.

In the present specification, the cadmium resin means a resin in which at least one functional group selected from the group consisting of the following formulas (6-1) to (6-11) is contained in the main backbone of the resin.

Also, unless otherwise specified herein, "*" means the same or different atom or moiety connected to the formula.

The photosensitive resin composition according to one embodiment comprises (A-1) a repeating unit represented by the following formula (1), a repeating unit represented by the following formula (2), a repeating unit represented by the following formula (3) An acrylic binder resin containing a repeating unit represented by the following formula (5); (A-2) carcass binder resin; (B) a photopolymerizable monomer; (C) a photopolymerization initiator; (D) a colorant; And (E) a solvent.

[Chemical Formula 1]

Figure pat00018

(2)

Figure pat00019

(3)

Figure pat00020

[Chemical Formula 4]

Figure pat00021

[Chemical Formula 5]

Figure pat00022

In the above Chemical Formulas 1 to 5,

R 1 to R 7 are each independently a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

R 8 is a substituted or unsubstituted C 11 to C 20 alkyl group,

L 1 is a substituted or unsubstituted C 1 to C 5 alkylene group,

n is an integer of 0 or 1;

In order to improve the color characteristic (for example, luminance, etc.) of the color filter, it is general to improve the pigment in the photosensitive resin composition. However, when the pigment is improved, the conventional process can not be used as it is, and even when the conventional process is used as it is, the effect of improving the color characteristic is insignificant.

However, the acrylic binder resin in the photosensitive resin composition according to one embodiment contains the repeating units represented by the above Chemical Formulas (1) to (5) to control the developability of the pattern while ensuring high heat resistance and high luminance characteristics, A binder resin is further included to increase the adhesion of the pattern to realize a fine pattern, to have a high resolution, and to secure a high transmittance.

Each component will be described in detail below.

(A-1) Acrylic binder resin

The photosensitive resin composition according to one embodiment contains the repeating unit represented by the formula (1), the repeating unit represented by the formula (2), the repeating unit represented by the formula (3), the repeating unit represented by the formula (4) And a binder resin containing a repeating unit that is a repeating unit.

For example, in the above Chemical Formulas 1 to 5,

R 1 may be a hydrogen atom, R 2 may be a hydrogen atom or a substituted or unsubstituted C 1 to C 5 alkyl group, each of R 3 to R 5 may independently be a substituted or unsubstituted C 1 to C 5 alkyl group, R 6 and R 7 may each independently be a hydrogen atom, and R 8 may be a substituted or unsubstituted C 11 to C 18 alkyl group.

The repeating unit represented by the formula (1) is contained in an amount of 10 to 30% by weight, for example, 15 to 25% by weight based on the total amount of the acrylic binder resin, and the repeating unit represented by the formula (2) The repeating unit represented by the formula (3) is contained in an amount of 10 to 30% by weight, for example, 15 to 25% by weight, and the repeating unit represented by the formula (4) The repeating unit represented by the formula 5 is contained in an amount of 15 to 35% by weight, such as 20 to 30% by weight, and the repeating unit represented by the formula 5 is contained in an amount of 5 to 25% by weight, such as 10 to 20% .

When the repeating units represented by the above formulas (1) to (5) are included in the above-mentioned weight range in the acrylic binder resin, the heat resistance, brightness and developability can be all improved. That is, the weight range (content range) of the repeating units represented by the above Chemical Formulas 1 to 5 can be improved by improving the heat resistance, luminance and developing property of the color filter while using the conventional process as it is without improving the coloring agent such as pigment Can be an optimal combination.

The acrylic binder resin may have a weight average molecular weight of from 3,000 g / mol to 30,000 g / mol, such as from 5,000 g / mol to 20,000 g / mol, such as from 8,000 g / mol to 15,000 g / mol.

The acrylic binder resin may have an acid value of 100 mgKOH / g to 140 mgKOH / g.

When the acrylic binder resin according to one embodiment has a weight average molecular weight and an acid value within the above range, the developability and the adhesion of the pattern formed are excellent when the pattern is realized.

The acrylic binder resin may be contained in an amount of 0.5 wt% to 10 wt%, for example, 1 wt% to 5 wt% with respect to the total amount of the photosensitive resin composition. When the acrylic binder resin is contained within the above range, the color filter has excellent brightness, heat resistance, and developability, and is improved in crosslinkability and excellent surface smoothness.

(A-2) Carometer  Binder resin

The photosensitive resin composition according to one embodiment may contain, in addition to an acrylic binder resin containing the repeating units represented by the above Chemical Formulas 1 to 5, other binder resins generally used in the production of a photosensitive resin composition such as a cadmium-based binder resin .

The cadmium binder resin may include a repeating unit represented by the following formula (6).

[Chemical Formula 6]

Figure pat00023

In Formula 6,

R 11 and R 12 are each independently a hydrogen atom or a substituted or unsubstituted (meth) acryloyloxyalkyl group,

R 13 and R 14 are each independently a hydrogen atom, a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group,

Z 1 is a single bond, O, CO, SO 2 , CR 7 R 8 , SiR 9 R 10 (wherein R 7 to R 10 are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group) Is any one of the linking groups represented by formulas (6-1) to (6-11)

[Formula 6-1]

Figure pat00024

[Formula 6-2]

Figure pat00025

[Formula 6-3]

Figure pat00026

[Formula 6-4]

Figure pat00027

[Formula 6-5]

Figure pat00028

(In the above Formula 6-5,

R a is a hydrogen atom, an ethyl group, C 2 H 4 Cl, C 2 H 4 OH, CH 2 CH = CH 2 or a phenyl group.

[Formula 6-6]

Figure pat00029

[Formula 6-7]

Figure pat00030

[Formula 6-8]

Figure pat00031

[Formula 6-9]

Figure pat00032

[Chemical Formula 6-10]

Figure pat00033

[Chemical Formula 6-11]

Figure pat00034

Z 2 is an acid anhydride residue,

m1 and m2 are each independently an integer of 0 to 4;

The cadmium-based binder resin may include a functional group represented by the following formula (7) in at least one of the two terminals.

(7)

Figure pat00035

In Formula 7,

Z 3 may be represented by the following formulas (7-1) to (7-7).

[Formula 7-1]

Figure pat00036

(Wherein R b and R c are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, an ester group or an ether group).

[Formula 7-2]

Figure pat00037

[Formula 7-3]

Figure pat00038

[Chemical Formula 7-4]

Figure pat00039

[Formula 7-5]

Figure pat00040

Wherein R d is O, S, NH, a substituted or unsubstituted C1 to C20 alkylene group, a C1 to C20 alkylamine group or a C2 to C20 alkenylamine group.

[Formula 7-6]

Figure pat00041

[Formula 7-7]

Figure pat00042

Examples of the cationic binder resin include fluorene-containing compounds such as 9,9-bis (4-oxiranylmethoxyphenyl) fluorene; Benzene tetracarboxylic dianhydride, naphthalene tetracarboxylic dianhydride, biphenyl tetracarboxylic dianhydride, benzophenone tetracarboxylic dianhydride, pyromellitic dianhydride, cyclobutanetetracarboxylic dianhydride, perylenetetracarboxylic dianhydride , Tetrahydrofuran tetracarboxylic acid dianhydride, tetrahydrophthalic anhydride and the like; Glycol compounds such as ethylene glycol, propylene glycol, and polyethylene glycol; Alcohol compounds such as methanol, ethanol, propanol, n-butanol, cyclohexanol and benzyl alcohol; Propylene glycol methyl ethyl acetate, and N-methyl pyrrolidone; Phosphorus compounds such as triphenylphosphine; And an amine or an ammonium salt compound such as tetramethylammonium chloride, tetraethylammonium bromide, benzyldiethylamine, triethylamine, tributylamine, benzyltriethylammonium chloride, or the like.

In the case of the cadmium-based binder resin, the developability is low and it is difficult to control the developability of the pattern when the color filter is manufactured using the photosensitive resin composition containing the cadmium-based binder resin. However, the photosensitive resin composition according to one embodiment can contain the above-mentioned acrylic binder resin together with the cationic binder resin to control the developability of the pattern.

Furthermore, when the cationic binder resin is used together with the acrylic binder resin described above, a photosensitive resin composition having excellent adhesion and high resolution and high brightness characteristics can be obtained.

The weight average molecular weight of the cationic binder resin may be from 500 g / mol to 50,000 g / mol, such as from 3,000 g / mol to 30,000 g / mol. When the weight average molecular weight of the cationic binder resin is within the above range, pattern formation is good without residue in the production of a color filter, no loss of film thickness during development, and good patterns can be obtained.

The cadmium binder resin may have an acid value of from 100 mgKOH / g to 140 mgKOH / g.

The above-mentioned acrylic binder resin and the cation binder resin may be contained in a weight ratio of 0.2: 1 to 20: 1, for example, in a weight ratio of 0.2: 1 to 19: 1. When the acrylic binder resin and the cadmium binder resin are included in the weight ratio range, the luminance can be minimized and high luminance can be realized.

The cadmium binder resin may be contained in an amount of 0.1% by weight to 10% by weight, for example, 0.1% by weight to 5% by weight based on the total amount of the photosensitive resin composition. When the cadmium binder resin is contained within the above range, the adhesion of the pattern and the high resolution are excellent when the color filter is manufactured.

(B) Photopolymerization  Monomer

The photopolymerizable monomer may be a monofunctional or polyfunctional ester of (meth) acrylic acid having at least one ethylenically unsaturated double bond, and the monofunctional or polyfunctional ester may be used in combination.

Since the photopolymerizable monomer has the ethylenically unsaturated double bond, sufficient polymerization is caused during exposure in the pattern formation step, whereby a pattern having excellent heat resistance, light resistance and chemical resistance can be formed.

Specific examples of the photopolymerizable monomer include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, neopentyl glycol Acrylate such as di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, bisphenol A di (meth) acrylate, pentaerythritol di (Meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (meth) acrylate, dipentaerythritol di Acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy (meth) acrylate, ethylene glycol Furnace there may be mentioned methyl ether (meth) acrylate, trimethylolpropane tri (meth) acrylate, tris (meth) acrylate such as oxyethyl phosphate, novolak epoxy (meth) acrylate, or a combination thereof.

A commercially available product of the photopolymerizable monomer is exemplified as follows. The (meth) acrylic acid is one example of a polyfunctional ester, such as doah Gosei Kagaku Kogyo's (primary)社Aronix M-101 ®, the same M-111 ®, the same M-114 ®; KAYARAD TC-110S ® and TC-120S ® from Nihon Kayaku Co., Ltd.; Osaka yukki the like Kagaku Kogyo (main)社of V-158 ®, V-2311 ®. The (meth) transfer function of an example esters of acrylic acid are, doah Gosei Kagaku Kogyo (Note)社of Aronix M-210 ®, copper or the like M-240 ®, the same M-6200 ®; KAYARAD HDDA ® , HX-220 ® and R-604 ® from Nihon Kayaku Corporation; Osaka yukki the like Kagaku Kogyo Co., Ltd. of 社V-260 ®, V- 312 ®, V-335 HP ®. Examples of the tri-functional ester of (meth) acrylic acid, doah Gosei Kagaku Kogyo (Note)社of Aronix M-309 ®, the same M-400 ®, the same M-405 ®, the same M-450 ®, Dong M -7100 ® , copper M-8030 ® , copper M-8060 ® and the like; Nippon Kayaku (Note)社of KAYARAD TMPTA ®, copper DPCA-20 ®, ® copper -30, -60 ® copper, copper ® -120 and the like; Osaka yukki Kayaku high (primary)社of V-295 ®, copper ® -300, -360 ® copper, copper -GPT ®, copper -3PA ®, and the like copper -400 ®. These products may be used alone or in combination of two or more.

The photopolymerizable monomer may be treated with an acid anhydride to give better developing properties.

The photopolymerizable monomer may be contained in an amount of 1 wt% to 10 wt%, for example, 5 wt% to 10 wt% with respect to the total amount of the photosensitive resin composition. When the photopolymerizable monomer is contained within the above range, the photopolymerizable monomer sufficiently cures upon exposure in the pattern formation step, is excellent in reliability, and is excellent in developability in an alkaline developer.

(C) Light curing Initiator

The photopolymerization initiator may be an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, a triazine-based compound, or an oxime-based compound.

Examples of the acetophenone compound include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, pt Dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropane-1 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one.

Examples of the benzophenone compound include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis (dimethylamino) benzophenone, '-Bis (diethylamino) benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.

Examples of the thioxanthone compound include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2- Chlorothioxanthone and the like.

Examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.

Examples of the triazine-based compound include 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -Dimethoxystyryl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) (Trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) (Trichloromethyl) -6-styryl-s-triazine, 2- (naphtho-1-yl) - 4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxynaphthol-1-yl) -Bis (trichloromethyl) -6- (4-methoxystyryl) -s-triazine, and the like. .

Examples of the oxime compounds include O-acyloxime compounds, 2- (O-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione, 1- -9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone, O-ethoxycarbonyl- Can be used. Specific examples of the O-acyloxime-based compound include 1,2-octanedione, 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholin- -1-one, 1- (4-phenylsulfanylphenyl) -butane-1,2-dione-2-oxime- 1-one oxime-O-acetate, 1- (4-phenylsulfanylphenyl) -butan-1-one oxime -O-acetate, and the like can be used.

The photopolymerization initiator may be a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound, or a nonimidazole compound in addition to the above compounds.

The photopolymerization initiator may be used in combination with a photosensitizer that generates a chemical reaction by absorbing light to be in an excited state and transferring its energy.

Examples of the photosensitizer include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, dipentaerythritol tetrakis-3-mercaptopropionate and the like .

The photopolymerization initiator may be contained in an amount of 0.1 wt% to 10 wt%, for example, 0.1 wt% to 5 wt% with respect to the total amount of the photosensitive resin composition. When the photopolymerization initiator is contained within the above range, photopolymerization sufficiently occurs upon exposure in the pattern formation step, and the decrease of the transmittance due to the unreacted initiator can be prevented.

(D) Colorant

The photosensitive resin composition according to one embodiment includes a colorant, and the colorant may include a pigment, a dye, or a combination thereof. For example, the colorant may include a pigment.

The above-mentioned pigments can be used both as organic pigments and / or inorganic pigments.

The pigment may include a red pigment, a green pigment, a blue pigment, a yellow pigment, and the like. For example, the pigment may include a green pigment, a yellow pigment, or a combination thereof.

When the colorant comprises a green pigment (or green pigment dispersion) and a yellow pigment (or yellow pigment dispersion), the content of the green pigment (or green pigment dispersion) is greater than the content of the yellow pigment (or yellow pigment dispersion) . For example, the green pigment (or green pigment dispersion) and the yellow pigment (or yellow pigment dispersion) may have a weight ratio of 2: 1 to 5: 1 such as 2: 1 to 4: 1, such as 2: 1 to 3: . When the green pigment (or the green pigment dispersion) and the yellow pigment (or the yellow pigment dispersion) do not have the weight ratios in the above range, the color characteristics and the luminance are lowered.

Examples of the red pigment include C.I. Red pigment 254, C.I. Red pigment 255, C.I. Red pigment 264, C.I. Red pigment 270, C.I. Red pigment 272, C.I. Red pigment 177, C.I. Red pigment 89 and the like.

Examples of the green pigment include C.I. Green pigment 58, C.I. Green pigment 36, C.I. Halogen-substituted copper phthalocyanine pigments such as green pigment 7 and the like.

Examples of the blue pigments include C.I. Blue pigment 15: 6, C.I. Blue pigment 15, C.I. Blue pigment 15: 1, C.I. Blue pigment 15: 2, C.I. Blue pigment 15: 3, C.I. Blue pigment 15: 4, C.I. Blue pigment 15: 5, C.I. Blue pigment 16, and the like.

Examples of the yellow pigments include C.I. Yellow pigments 139 and the like, C.I. Quinophthalone-based pigments such as yellow pigment 138 and the like, C.I. And yellow complex pigments such as yellow pigment 150 and the like.

These pigments can be used singly or in combination of two or more thereof, but are not limited to these examples.

A dispersant may be used together with the photosensitive resin composition to disperse the pigment. Specifically, the pigment may be surface-treated beforehand with a dispersant, or a dispersant may be added together with the pigment when the photosensitive resin composition is prepared.

As the dispersing agent, a nonionic dispersing agent, an anionic dispersing agent, a cationic dispersing agent and the like can be used. Specific examples of the dispersing agent include polyalkylene glycols and esters thereof, polyoxyalkylene, polyhydric alcohol ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonic acid salt, carboxylic acid ester, carboxylic acid Salts, alkylamide alkylene oxide adducts, and alkylamines. These may be used singly or in combination of two or more.

DISPERBYK-161, DISPERBYK-160, DISPERBYK-161, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-160 and DISPERBYK-160 of BYK Co., -166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001 and the like; EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400 and EFKA-450 of EFKA Chemical Co., Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse24000GR, Solsperse 27000, Solsperse 28000 from Zeneka; Or Ajinomoto's PB711 and PB821.

The dispersant may be contained in an amount of 0.1 to 15% by weight based on the total amount of the photosensitive resin composition. When the dispersant is contained within the above range, the dispersibility of the photosensitive resin composition is excellent, and therefore, the stability, developability and patternability of the light-shielding layer are excellent.

The pigment may be used by pretreatment using a water-soluble inorganic salt and a wetting agent. When the pigment is used in the pretreatment, the primary particle size of the pigment can be reduced.

The pretreatment may be performed by kneading the pigment with a water-soluble inorganic salt and a wetting agent, and filtering and washing the pigment obtained in the kneading step.

The kneading may be carried out at a temperature of 40 to 100 DEG C, and the filtration and washing may be performed by washing the inorganic salt with water, etc., followed by filtration.

Examples of the water-soluble inorganic salt include, but are not limited to, sodium chloride and potassium chloride. The wetting agent acts as a medium through which the pigment and the water-soluble inorganic salt are uniformly mixed to easily pulverize the pigment. Examples of the wetting agent include ethylene glycol monoethyl ether, propylene glycol monomethyl ether, diethylene glycol monomethyl ether and the like Alkylene glycol monoalkyl ethers; And alcohols such as ethanol, isopropanol, butanol, hexanol, cyclohexanol, ethylene glycol, diethylene glycol, polyethylene glycol, glycerin polyethylene glycol and the like. These may be used singly or in combination of two or more thereof.

The pigment after the kneading step may have an average particle diameter of 30 nm to 100 nm. When the average particle diameter of the pigment is within the above range, it is possible to effectively form a fine pattern with excellent heat resistance and light resistance.

Specifically, the pigment may be used in the form of a pigment dispersion including the dispersant and a solvent described later, and the pigment dispersion may include a solid pigment, a dispersant, and a solvent. The solid pigment may be included in an amount of 10% by weight to 15% by weight based on the total amount of the pigment dispersion.

The colorant (for example, a pigment dispersion) may be contained in an amount of 10% by weight to 50% by weight, for example, 20% by weight to 40% by weight based on the total amount of the photosensitive resin composition. When the colorant (for example, pigment dispersion) is contained within the above-described range, it has excellent brightness, color reproducibility, pattern curability, heat resistance and adhesion.

(E) Solvent

The solvent may be a material that has compatibility with the binder resin, the photopolymerizable monomer, the photopolymerization initiator, and the colorant but does not react.

Examples of the solvent include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisobutyl ether, methylphenyl ether and tetrahydrofuran; Glycol ethers such as ethylene glycol methyl ether, ethylene glycol ethyl ether and propylene glycol methyl ether; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate and diethyl cellosolve acetate; Carbitols such as methylethylcarbitol, diethylcarbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether and diethylene glycol diethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate; Aromatic hydrocarbons such as toluene and xylene; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl- ; Saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate and isobutyl acetate; Lactic acid alkyl esters such as methyl lactate and ethyl lactate; Hydroxyacetic acid alkyl esters such as methylhydroxyacetate, ethylhydroxyacetate and butylhydroxyacetate; Alkoxyalkyl esters such as methoxy methyl acetate, methoxy ethyl acetate, methoxy butyl acetate, ethoxy methyl acetate, and ethoxy ethyl acetate; 3-hydroxypropionic acid alkyl esters such as methyl 3-hydroxypropionate and ethyl 3-hydroxypropionate; 3-alkoxypropionic acid alkyl esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate and methyl 3-ethoxypropionate; 2-hydroxypropionic acid alkyl esters such as methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate and propyl 2-hydroxypropionate; 2-alkoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate and methyl 2-ethoxypropionate; 2-hydroxy-2-methylpropionic acid alkyl esters such as methyl 2-hydroxy-2-methylpropionate and ethyl 2-hydroxy-2-methylpropionate; 2-alkoxy-2-methylpropionic acid alkyl esters such as methyl 2-methoxy-2-methylpropionate and ethyl 2-ethoxy-2-methylpropionate; Esters such as 2-hydroxyethyl propionate, 2-hydroxy-2-methyl ethyl propionate, hydroxy ethyl acetate and methyl 2-hydroxy-3-methyl butanoate; Or ethyl pyruvate. Examples of the ketone acid esters include N-methylformamide, N, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N, N-dimethylacetamide Benzyl alcohol, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, Ethyl benzoate, diethyl oxalate, diethyl maleate,? -Butyrolactone, ethylene carbonate, propylene carbonate, phenyl cellosolve acetate, etc. These may be used alone or in combination of two or more.

In view of the miscibility and reactivity of the solvent, glycol ethers such as ethylene glycol monoethyl ether and the like; Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; Esters such as 2-hydroxyethyl propionate; Diethylene glycol such as diethylene glycol monomethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate can be used.

The solvent is contained in an amount of 30% by weight to 80% by weight, for example 40% by weight to 80% by weight, such as 40% by weight to 70% by weight, such as 40% by weight to 60% by weight, based on the total amount of the photosensitive resin composition . When the solvent is contained within the above range, a coating film excellent in coating property of the photosensitive resin composition and excellent in flatness can be obtained.

(F) Other additives

The above-mentioned photosensitive resin composition may contain at least one selected from the group consisting of malonic acid, malonic acid, and malonic acid, in order to prevent spots and spots upon application, to improve the leveling performance, 3-amino-1,2-propanediol; Silane coupling agents; Leveling agents; Fluorine surfactants; A radical polymerization initiator; Or a combination thereof, and the like.

Examples of the silane coupling agent include trimethoxysilylbenzoic acid,? -Methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane,? -Isocyanatopropyltriethoxysilane,? -Glycidoxypropyltrimethoxysilane, and? - (3,4-epoxycyclohexyl) ethyltrimethoxysilane. These may be used singly or in combination of two or more.

Examples of the fluorine-based surfactant, BM Chemie Corporation BM-1000 ®, BM-1100 ® , and the like; Mecha Pack F 142D ® , Copper F 172 ® , Copper F 173 ® , Copper F 183 ® and the like manufactured by Dainippon Ink & Chemicals Incorporated; M. Sumitomo Co., Inc. Pro rod FC-135 ®, the same FC-170C ®, copper FC-430 ®, the same FC-431 ®, and the like; Asahi Grass Co., Inc. Saffron S-112 ®, the same S-113 ®, the same S-131 ®, the same S-141 ®, the same S-145 ®, and the like; Toray Silicone Co., Ltd.'s SH-28PA ®, ® -190 copper, may be a commercially available product such as copper -193 ®, SZ-6032 ®, SF-8428 ®.

The content of the additive can be easily adjusted according to desired properties.

The photosensitive resin composition may further include an epoxy compound to improve adhesion with the substrate.

Examples of the epoxy compound include a phenol novolak epoxy compound, a tetramethylbiphenyl epoxy compound, a bisphenol A type epoxy compound, an alicyclic epoxy compound, or a combination thereof.

The epoxy compound may be contained in an amount of 0.01 to 5 parts by weight, for example, 0.1 to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the epoxy compound is contained within the above range, the adhesive property, heat resistance, and chemical resistance are excellent.

Another embodiment provides a color filter manufactured using the above-described photosensitive resin composition.

A method of manufacturing the color filter is as follows.

The above-mentioned photosensitive resin composition is coated on the glass substrate by a suitable method such as spin coating, roller coating, spray coating or the like to a thickness of 0.5 占 퐉 to 10 占 퐉, for example, to form a resin composition layer.

Then, light is irradiated to form a pattern necessary for the color filter on the substrate on which the resin composition layer is formed. As the light source used for the irradiation, UV, electron beam or X-ray can be used. For example, UV of 190 nm to 450 nm, specifically 200 nm to 400 nm, can be irradiated. A photoresist mask may be further used in the above irradiation step. After the step of irradiating in this manner, the resin composition layer irradiated with the light source is treated with a developing solution. At this time, the non-exposed portions in the resin composition layer are dissolved to form a pattern necessary for the color filter. By repeating such a process according to the number of necessary colors, a color filter having a desired pattern can be obtained. In addition, when the image pattern obtained by development in the above step is heated again or cured by actinic ray irradiation or the like, crack resistance, solvent resistance and the like can be improved.

Hereinafter, preferred embodiments of the present invention will be described. However, the following examples are only a preferred embodiment of the present invention, and the present invention is not limited by the following examples.

(Preparation of acrylic binder resin)

Synthetic example  1 to Synthetic example  14

After adding 2 g of AIBN as a initiator to a 100 ml beaker, the polymerization monomers shown in the following Tables 1 and 2 were added in the proportions shown in the following Table 1 and Table 2 in order so that the sum of the polymerization monomers would be 40 g And stirred for 30 minutes. Thereafter, 70 g of PGMEA was charged into a 250 ml glass reactor equipped with a condenser, and the temperature of the system was elevated to 85 캜. The prepared monomer solution was added dropwise to the reactor for 3 hours. After further reaction at the same temperature for 6 hours, the temperature was lowered to room temperature and the reaction was terminated. The reaction was carried out under a nitrogen atmosphere.

(Unit: wt%) The monomer for polymerization Synthesis Example 1 Synthesis Example 2 Synthesis Example 3 Synthesis Example 4 Synthesis Example 5 Synthesis Example 6 Synthesis Example 7 Methacrylic acid 20 20 20 20 20 20 20 Isobonyl acrylate 20 - - 10 10 - 5 Isobonyl methacrylate - 20 - 10 - 10 5 Tricyclodecanyl methacrylate - - 20 - 10 10 10 Cyclohexyl methacrylate 20 20 20 20 20 20 20 N-Phenyl maleimide 15 15 15 15 15 15 15 Lauryl acrylate 25 25 25 25 25 25 25 Weight average molecular weight
(Mw, g / mol) 8,500 9,100 8,900 10,300 10,100 10,500 10,800 Acid value
(mgKOH / g) 110 115 110 112 116 112 110

(Unit: wt%) The monomer for polymerization Synthesis Example 8 Synthesis Example 9 Synthesis Example 10 Synthesis Example 11 Synthesis Example 12 Synthesis Example 13 Synthesis Example 14 Methacrylic acid 10 20 20 20 20 20 20 Isobonyl acrylate 5 30 - - 10 10 - Isobonyl methacrylate 5 - 30 - 10 - 10 Tricyclodecanyl methacrylate 10 - - 10 - 10 10 Cyclohexyl methacrylate 20 15 15 20 10 25 15 N-Phenyl maleimide 20 10 10 20 20 5 20 Lauryl acrylate 30 25 25 30 30 30 35 Weight average molecular weight
(Mw, g / mol) 10,900 8,800 8,870 9,000 10,200 10,300 10,600 Acid value
(mgKOH / g) 82 112 111 111 110 115 112

(Preparation of photosensitive resin composition)

Example  1 to Example  14 and Comparative Example  1 to Comparative Example  3

The photosensitive resin compositions according to Examples 1 to 14 and Comparative Examples 1 to 3 were prepared with the compositions shown in Tables 3 and 4 below using the following components.

Specifically, the content of the photopolymerization initiator was precisely measured, the solvent was then added, and the mixture was sufficiently stirred (more than 30 minutes) until the photopolymerization initiator was sufficiently dissolved. To this, an acrylic binder resin, a cadmium binder resin and a photopolymerizable monomer were added sequentially, followed by stirring for about 1 hour. Then, a colorant (pigment dispersion) was added, and other additives were added thereto, and finally the entire composition was stirred for 2 hours or more to prepare a photosensitive resin composition.

The specifications of each component used in the production of the photosensitive resin composition are as follows.

(A-1) Acrylic binder resin

(A-1-1) The acrylic binder resin of Synthesis Example 1

(A-1-2) The acrylic binder resin of Synthesis Example 2

(A-1-3) The acrylic binder resin of Synthesis Example 3

(A-1-4) The acrylic binder resin of Synthesis Example 4

(A-1-5) The acrylic binder resin of Synthesis Example 5

(A-1-6) The acrylic binder resin of Synthesis Example 6

(A-1-7) The acrylic binder resin of Synthesis Example 7

(A-1-8) The acrylic binder resin of Synthesis Example 8

(A-1-9) The acrylic binder resin of Synthesis Example 9

(A-1-10) The acrylic binder resin of Synthesis Example 10

(A-1-11) The acrylic binder resin of Synthesis Example 11

(A-1-12) The acrylic binder resin of Synthesis Example 12

(A-1-13) The acrylic binder resin of Synthesis Example 13

(A-1-14) The acrylic binder resin of Synthesis Example 14

(A-1-15) Acrylic binder resin (SKY-095, Samsung SDI)

(A-2) Carometer  Binder resin

(V259ME, NSSC) (weight average molecular weight: 5,000 g / mol, acid value: 110 mgKOH / g)

(B) Photopolymerization  Monomer

Photopolymerizable monomer (DPHA)

(C) Light curing Initiator

(C-1) oxime initiator 1 (BASF, OXE-01)

(C-2) Oxime initiator 2 (BASF, OXE-02)

(D) Colorant

(D-1) Green pigment dispersion (ENF, G58)

(D-2) Yellow pigment dispersion for coloring (ENF, Y138)

(E) Solvent

Propylene glycol monomethyl ether acetate (PGMEA)

(F) Other additives

Fluorine-based surfactant (DIC, F-554 (using 10% diluent))

(Unit: wt%) Kinds Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 Example 9 Example 10 Example 11 Example 12 Example 13 Example 14 (A-1) Acrylic binder resin A-1-1 3.70 - - - - - - - - - - - - - A-1-2 - 2.285 - - - - - - - - - - - - A-1-3 - - 0.91 - - - - - - - - - - - A-1-4 - - - 4.34 - - - - - - - - - - A-1-5 - - - - 3.05 - - - - - - - - - A-1-6 - - - - - 3.43 - - - - - - - - A-1-7 - - - - - - 1.52 - - - - - - - A-1-8 - - - - - - - 3.81 - - - - - - A-1-9 - - - - - - - - 4.00 - - - - - A-1-10 - - - - - - - - - 4.11 - - - - A-1-11 - - - - - - - - - - 4.15 - - - A-1-12 - - - - - - - - - - - 4.19 - - A-1-13 - - - - - - - - - - - - 4.24 - A-1-14 - - - - - - - - - - - - - 4.28 A-1-15 - - - - - - - - - - - - - - (A-2) Cathode binder resin 0.87 2.285 3.66 0.23 1.52 1.14 3.05 0.76 0.57 0.46 0.42 0.38 0.33 0.29 (B) a photopolymerizable monomer 8.70 8.70 8.70 8.70 8.70 8.70 8.70 8.70 8.70 8.70 8.70 8.70 8.70 8.70 (C) a photopolymerization initiator C-1 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 C-2 0.11 0.11 0.11 0.11 0.11 0.11 0.11 0.11 0.11 0.11 0.11 0.11 0.11 0.11 (D) Colorant D-1 26.40 26.40 26.40 26.40 26.40 26.40 26.40 26.40 26.40 26.40 26.40 26.40 26.40 26.40 D-2 11.80 11.80 11.80 11.80 11.80 11.80 11.80 11.80 11.80 11.80 11.80 11.80 11.80 11.80 (E) Solvent 47.90 47.90 47.90 47.90 47.90 47.90 47.90 47.90 47.90 47.90 47.90 47.90 47.90 47.90 (F) Other additives 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 Total 100 100 100 100 100 100 100 100 100 100 100 100 100 100

(Unit: wt%) Kinds Comparative Example 1 Comparative Example 2 Comparative Example 3 (A-1) Acrylic binder resin A-1-1 - 4.57 - A-1-2 - - - A-1-3 - - - A-1-4 - - - A-1-5 - - - A-1-6 - - - A-1-7 - - - A-1-8 - - - A-1-9 - - - A-1-10 - - - A-1-11 - - - A-1-12 - - - A-1-13 - - - A-1-14 - - - A-1-15 - - 3.7 (A-2) Cathode binder resin 4.57 - 0.87 (B) a photopolymerizable monomer 8.70 8.70 8.70 (C) a photopolymerization initiator C-1 0.5 0.5 0.5 C-2 0.11 0.11 0.11 (D) Colorant D-1 26.40 26.40 26.40 D-2 11.80 11.80 11.80 (E) Solvent 47.90 47.90 47.90 (F) Other additives 0.02 0.02 0.02 Total 100 100 100

Rating 1: Color characteristics  evaluation

Coating was carried out at rpm at which a certain thickness could be exhibited for each of the photosensitive resin compositions obtained in Examples 1 to 14 and Comparative Examples 1 to 3 by using a coating machine (Mikasa, Opticoat MS-A150) Pre-baking was carried out on a hot-plate. Thereafter, the entire surface was exposed using an exposure machine (Ushio, HB-50110AA) under an exposure condition of 50 mj / cm 2 , and baking was performed at 230 캜 for 20 minutes in an oven condition to complete the preparation of the test piece. The color characteristics (chromaticity coordinates, luminance (Y) and contrast ratio (CR)) were measured using an MCPD 3000 apparatus before and after the oven baking, and the results are shown in Table 5 below.

Gx Gy Luminance (Y) Contrast Ratio (CR) Example 1 0.2773 0.578 62.40 14600 Example 2 0.2775 0.578 62.42 14200 Example 3 0.2778 0.578 62.46 14500 Example 4 0.2771 0.578 62.37 14300 Example 5 0.2773 0.578 62.42 14700 Example 6 0.2777 0.578 62.49 14400 Example 7 0.2774 0.578 62.41 14300 Example 8 0.2771 0.578 62.36 14100 Example 9 0.2772 0.578 62.35 14000 Example 10 0.2771 0.578 62.36 14100 Example 11 0.2771 0.578 62.34 13900 Example 12 0.2773 0.578 62.38 14000 Example 13 0.2771 0.578 62.36 14100 Example 14 0.2770 0.578 62.34 13800 Comparative Example 1 0.2770 0.578 62.30 13100 Comparative Example 2 0.2770 0.578 62.31 13700 Comparative Example 3 0.2773 0.578 62.28 12900

Evaluation 2: Developability , Development speed and adhesion evaluation

Coating was carried out at rpm at which a certain thickness could be exhibited for each of the photosensitive resin compositions obtained in Examples 1 to 14 and Comparative Examples 1 to 3 by using a coating machine (Mikasa, Opticoat MS-A150) (15 DEG C to 25 DEG C) for 30 minutes. Subsequently, pattern exposure was carried out using a pattern mask under exposure conditions of 50 mj / cm 2 using an exposure machine (Ushio, HB-50110AA), development was carried out with a Na 2 CO 3 dilution (X20) developer at a pressure of 2.0 kgf, The resultant was washed with water under pressure, and the developability and development speed were observed. The results are shown in Table 6 below. The adhesion of the pattern during development was observed through an optical microscope, and the results are shown in FIGS. 1 to 7. FIG.

Developability Development speed (sec) Example 1 Soluble 22 Example 2 Soluble 20 Example 3 Soluble 18 Example 4 Soluble 23 Example 5 Soluble 23 Example 6 Soluble 20 Example 7 Soluble 22 Example 8 Soluble 27 Example 9 Soluble 26 Example 10 Soluble 26 Example 11 Soluble 24 Example 12 Soluble 23 Example 13 Soluble 23 Example 14 Soluble 24 Comparative Example 1 Soluble 15 Comparative Example 2 Soluble 31 Comparative Example 3 Insoluble 24

(Including repeating units represented by the above formulas (1) to (5) in a specific content range) through the above Tables 5, 6 and 7, In Examples 1 to 14 using the acrylic binder resin and the cadmium-based binder resin, as well as the color characteristics such as luminance and contrast ratio, as well as the developability and the adhesion, compared with the cases of Comparative Examples 1 to 3 can confirm. Particularly, in Comparative Example 1, the developing speed is too fast, the adhesion is reduced, and all or a part of the pattern tends to fall off. In Comparative Example 2, the developing speed is too slow to cause residue, whereas Examples 1 to 14 It can be seen that it has an appropriate development speed and can have excellent adhesion without generating residue.

It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims. As will be understood by those skilled in the art. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.

Claims (14)

(A-1) a polymer comprising a repeating unit represented by the following formula (1), a repeating unit represented by the following formula (2), a repeating unit represented by the following formula (3), a repeating unit represented by the following formula An acrylic binder resin;
(A-2) carcass binder resin;
(B) a photopolymerizable monomer;
(C) a photopolymerization initiator;
(D) a colorant; And
(E) Solvent
: ≪ EMI ID =
[Chemical Formula 1]
Figure pat00043

(2)
Figure pat00044

(3)
Figure pat00045

[Chemical Formula 4]
Figure pat00046

[Chemical Formula 5]
Figure pat00047

In the above Chemical Formulas 1 to 5,
R 1 to R 7 are each independently a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R 8 is a substituted or unsubstituted C 11 to C 20 alkyl group,
L 1 is a substituted or unsubstituted C 1 to C 5 alkylene group,
n is an integer of 0 or 1;
The method according to claim 1,
With respect to the total amount of the acrylic binder resin,
The repeating unit represented by Formula 1 is contained in an amount of 10% by weight to 30% by weight,
The repeating unit represented by Formula 2 is contained in an amount of 10 to 30% by weight,
The repeating unit represented by the formula (3) is contained in an amount of 10 to 30% by weight,
The repeating unit represented by the formula (4) is contained in an amount of 5 wt% to 25 wt%
The repeating unit represented by the formula (5) is contained in an amount of 15 to 35% by weight
.
3. The method of claim 2,
With respect to the total amount of the acrylic binder resin,
The repeating unit represented by Formula 1 is contained in an amount of 15 to 25% by weight,
The repeating unit represented by Formula 2 is contained in an amount of 15 wt% to 25 wt%
The repeating unit represented by the formula (3) is contained in an amount of 15 to 25% by weight,
The repeating unit represented by Formula 4 is contained in an amount of 10 to 20% by weight,
The repeating unit represented by the general formula (5) is contained in an amount of 20 to 30% by weight
.
The method according to claim 1,
Wherein the acrylic binder resin has a weight average molecular weight of 3,000 g / mol to 30,000 g / mol.
The method according to claim 1,
Wherein the acrylic binder resin has an acid value of 100 mgKOH / g to 140 mgKOH / g.
The method according to claim 1,
Wherein the cationic binder resin comprises a repeating unit represented by the following formula (6): < EMI ID =
[Chemical Formula 6]
Figure pat00048

In Formula 6,
R 11 and R 12 are each independently a hydrogen atom or a substituted or unsubstituted (meth) acryloyloxyalkyl group,
R 13 and R 14 are each independently a hydrogen atom, a halogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
Z 1 is a single bond, O, CO, SO 2 , CR 7 R 8 , SiR 9 R 10 (wherein R 7 to R 10 are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group) Is any one of the linking groups represented by formulas (6-1) to (6-11)
[Formula 6-1]
Figure pat00049

[Formula 6-2]
Figure pat00050

[Formula 6-3]
Figure pat00051

[Formula 6-4]
Figure pat00052

[Formula 6-5]
Figure pat00053

(In the above Formula 6-5,
R a is a hydrogen atom, an ethyl group, C 2 H 4 Cl, C 2 H 4 OH, CH 2 CH = CH 2 or a phenyl group.
[Formula 6-6]
Figure pat00054

[Formula 6-7]
Figure pat00055

[Formula 6-8]
Figure pat00056

[Formula 6-9]
Figure pat00057

[Chemical Formula 6-10]
Figure pat00058

[Chemical Formula 6-11]
Figure pat00059

Z 2 is an acid anhydride residue,
m1 and m2 are each independently an integer of 0 to 4;
The method according to claim 1,
The cadmium binder resin has a weight average molecular weight of 500 g / mol to 50,000 g / mol.
The method according to claim 1,
Wherein the cationic binder resin has an acid value of 100 mgKOH / g to 140 mgKOH / g.
The method according to claim 1,
Wherein the acrylic binder resin and the cation binder resin are contained in a weight ratio of 0.2: 1 to 20: 1.
The method according to claim 1,
Wherein the coloring agent comprises a pigment.
11. The method of claim 10,
Wherein the pigment comprises a green pigment, a yellow pigment, or a combination thereof.
The method according to claim 1,
The photosensitive resin composition
0.5 to 10% by weight of the (A-1) acrylic binder resin;
0.1 to 10% by weight of the (A-2) cadmium-based binder resin;
1 to 10% by weight of the photopolymerizable monomer (B);
0.1 to 10% by weight of the photopolymerization initiator (C);
10% to 50% by weight of (D) the colorant; And
The amount of the solvent (E)
.
The method according to claim 1,
The photosensitive resin composition may include malonic acid; 3-amino-1,2-propanediol; Silane coupling agents; Leveling agents; Fluorine surfactants; A radical polymerization initiator; Or a combination thereof. ≪ / RTI >
A color filter produced by using the photosensitive resin composition of any one of claims 1 to 13.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190052879A (en) * 2017-11-09 2019-05-17 동우 화인켐 주식회사 A binder resin, a colored photo resist composition, a display partition wall structure comprising the same and a self-luminous display device comprising the same
KR20210110523A (en) * 2019-11-19 2021-09-08 세명대학교 산학협력단 InDel Markers for Discrimination of Cynanchum wilfordii and Cynanchum auriculatum and Method for Use thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190052879A (en) * 2017-11-09 2019-05-17 동우 화인켐 주식회사 A binder resin, a colored photo resist composition, a display partition wall structure comprising the same and a self-luminous display device comprising the same
KR20210110523A (en) * 2019-11-19 2021-09-08 세명대학교 산학협력단 InDel Markers for Discrimination of Cynanchum wilfordii and Cynanchum auriculatum and Method for Use thereof

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