KR100483373B1 - Resist Composition For Over-Coat - Google Patents
Resist Composition For Over-Coat Download PDFInfo
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- KR100483373B1 KR100483373B1 KR10-2000-0038041A KR20000038041A KR100483373B1 KR 100483373 B1 KR100483373 B1 KR 100483373B1 KR 20000038041 A KR20000038041 A KR 20000038041A KR 100483373 B1 KR100483373 B1 KR 100483373B1
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- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
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- 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
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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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
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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
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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
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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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
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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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
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Abstract
본 발명은 오버코트용 레지스트 조성물에 관한 것으로, 바인더 수지, 다기능 모노머, 광개시제, 실리콘계 첨가제 및 유기용제 등을 주성분으로 하여 총 수지고형분의 0.1 내지 3중량%에 해당하는 공지된 광증감제, 열중합 금지제, 레벨링제, 소포제 등의 성분을 혼합한 조성물을 첨가하여 제조되는 고내열성, 고투명성, 고잔막율, 고평탄화율 및 패턴안정성을 갖는 오버코트용 레지스트 조성물을 제공하기 위한 것이다. 본 발명에 의한, 오버코트용 레지스트 조성물은 바인더 수지의 구조나 다기능 모노머의 조성비를 변화시켜 오버코트에서 요구되는 물성을 조절하는 것이 가능하고 또한, 본 발명에서 제조된 오버코트용 레지스트 조성물은 자외선에 의해 경화하고 알칼리 현상액으로 현상하여 패턴 형성이 가능하며, 우수한 내열성과 투명성, 잔막율, 평탄화율 및 패턴안정성을 용이하게 실현하여 TFT-LCD의 칼라필터의 오버코트에 사용할 수 있는 효과가 있다.The present invention relates to a resist composition for overcoat, comprising a binder resin, a multifunctional monomer, a photoinitiator, a silicone-based additive, an organic solvent, etc. as a main component, a known photosensitizer, thermal polymerization prohibition, corresponding to 0.1 to 3% by weight of the total solid content The present invention provides a resist composition for overcoat having high heat resistance, high transparency, high residual film ratio, high flattening rate, and pattern stability prepared by adding a composition comprising components such as a leveling agent and an antifoaming agent. The resist composition for overcoat according to the present invention can control the physical properties required in the overcoat by changing the structure of the binder resin or the composition ratio of the multifunctional monomer, and the resist composition for overcoat prepared in the present invention is cured by ultraviolet rays. It is possible to develop a pattern by developing with an alkaline developer, and to easily realize excellent heat resistance, transparency, residual film ratio, flattening ratio and pattern stability, which can be used for overcoat of color filter of TFT-LCD.
Description
본 발명은 오버코트용 레지스트 조성물에 관한 것으로, 보다 상세하게는 바인더 수지, 다기능 모노머, 광개시제, 실리콘계 첨가제 및 유기용제 등을 주성분으로 하여 총 수지고형분의 0.1 내지 3중량%에 해당하는 공지된 광증감제, 열중합 금지제, 레벨링제, 소포제 등의 성분을 혼합한 조성물을 첨가하여 제조되는 고내열성, 고투명성, 고잔막율, 고평탄화율 및 패턴안정성을 갖는 오버코트용 레지스트 조성물에 관한 것이다.The present invention relates to a resist composition for overcoat, and more particularly, known photosensitizers corresponding to 0.1 to 3% by weight of the total solid content, mainly comprising binder resins, multifunctional monomers, photoinitiators, silicone additives, organic solvents, and the like. The present invention relates to a resist composition for overcoat having high heat resistance, high transparency, high residual film ratio, high flattening rate and pattern stability, which is prepared by adding a composition containing components such as a thermal polymerization inhibitor, a leveling agent, and an antifoaming agent.
TFT-LCD는 가장 성장 속도가 빠른 평판표시소자의 하나로 앞으로 표시소자 시장을 주도해 나가리라고 생각된다. 이러한 TFT-LCD의 대면적화를 위해서는 현재 사용되고 있는 유리의 대형화가 수반되며 이에 따른 칼라필터 층의 평탄화가 해결되어야만 한다. 따라서 TFT-LCD의 대면적화를 이루기 위해서는 칼라필터층의 평탄화를 위한 오버코트 재료의 개발이 필수적이다. TFT-LCD is one of the fastest growing flat panel display devices and is expected to lead the display device market in the future. The large area of the TFT-LCD is accompanied by the enlargement of the glass currently used and the flattening of the color filter layer has to be solved accordingly. Therefore, in order to achieve a large area of the TFT-LCD, it is essential to develop an overcoat material for flattening the color filter layer.
현재 오버코트 재료는 TFT-LCD용 컬러필터 레지스트를 그대로 사용하고 있으며 그 칼라필터 레지스트에는 주로 아크릴계 수지를 기본으로 사용하고 있어 뛰어난 코팅성을 갖는 반면, 경화 후 부피 수축이 발생하여 칼라필터층 위에 오버코트 할 경우 경화 도막의 두께 차이가 크게 되며, 이에 따라 평탄화 또한 감소하는 문제가 발생할 뿐만 아니라 방향족 치환기를 포함하지 않은 아크릴계 바인더의 경우에는 경화 후 오버코트의 유리전이온도가 낮아져서 여러 가지 기계적 물성이 저하되는 문제가 있었다. 또한 방향족 치환기를 포함하고 있는 아크릴계 수지의 경우 광경화 후 시간이 지남에 따라 레지스트 막이 유색화(有色化)됨에 따라 오버코트의 투명도가 떨어지게 됨으로서 최종적으로 TFT-LCD의 성능을 저하시키는 문제가 있었다. Currently, the overcoat material uses the color filter resist for TFT-LCD as it is, and the color filter resist mainly uses acrylic resin as the base, and has excellent coating property.However, when overcoat on the color filter layer due to volume shrinkage after curing, The difference in the thickness of the cured coating film becomes large, and thus, the flattening also decreases, and in the case of the acrylic binder containing no aromatic substituent, the glass transition temperature of the overcoat is lowered after curing, thereby deteriorating various mechanical properties. . In addition, in the case of an acrylic resin including an aromatic substituent, the transparency of the overcoat is degraded as the resist film is colored after the photocuring with time, thereby degrading the performance of the TFT-LCD.
본 발명은 상기와 같은 종래기술의 문제점을 해결하기 위한 것으로, 방향족기 대신에 벌키(bulky)한 지환족 구조를 갖는 아크릴계의 바인더 수지를 사용하여 수지의 유리전이 온도를 높여 내열성을 향상시키고 투명성을 유지할 수 있음을 확인하고 본 발명을 완성하게 되었다. The present invention is to solve the problems of the prior art as described above, using an acrylic binder resin having a bulky alicyclic structure instead of an aromatic group to increase the glass transition temperature of the resin to improve heat resistance and transparency It was confirmed that it can maintain and the present invention was completed.
결국 본 발명은 상기한 바인더 수지와 다기능 모노머, 광개시제, 실리콘계 첨가제 및 유기용제 등을 주성분으로 하여 총 수지고형분의 0.1 내지 3중량%에 해당하는 공지된 광증감제, 열중합 금지제, 레벨링제, 소포제 등의 성분을 혼합한 조성물을 첨가하여 제조되는 고내열성, 고투명성, 고잔막율, 고평탄율 및 패턴안정성을 갖는 오버코트용 레지스트 조성물을 제공하는 것을 목적으로 한다.After all, the present invention is a known photo-sensitizer, thermal polymerization inhibitor, leveling agent, which corresponds to 0.1 to 3% by weight of the total resin solid based on the binder resin, a multifunctional monomer, a photoinitiator, a silicone additive, an organic solvent, etc. An object of the present invention is to provide a resist composition for overcoat having high heat resistance, high transparency, high residual film ratio, high flatness and pattern stability prepared by adding a composition containing components such as an antifoaming agent.
또한 본 발명은 고내열성, 고투명성, 고잔막율, 고평탄화율 및 패턴안정성을 갖는 오버코트용 레지스트 조성물에 사용할 수 있는 바인더 수지의 구조 및 이의 조성비를 제공하는 것을 목적으로 한다.It is another object of the present invention to provide a structure of a binder resin that can be used in a resist composition for overcoat having high heat resistance, high transparency, high residual film rate, high flattening rate and pattern stability, and a composition ratio thereof.
본 발명의 또 다른 목적은 고내열성, 고투명성, 고잔막율, 고평탄화율 및 패턴 안정성을 갖는 오버코트용 레지스트 조성물에 사용할 수 있는 다기능 모노머 및 이의 조성비를 제공하는 것이다. Still another object of the present invention is to provide a multifunctional monomer that can be used in an overcoat resist composition having high heat resistance, high transparency, high residual film ratio, high flattening rate, and pattern stability, and a composition ratio thereof.
본 발명의 또 다른 목적은 고내열성, 고투명성, 고잔막율, 고평탄화율 및 패턴 안정성을 갖는 오버코트용 레지스트 조성물에 사용할 수 있는 광 개시제 및 이의 조성비를 제공하는 것이다. It is still another object of the present invention to provide a photoinitiator and a composition ratio thereof that can be used in a resist composition for overcoat having high heat resistance, high transparency, high residual film ratio, high flattening ratio, and pattern stability.
본 발명의 또 다른 목적은 고내열성, 고투명성, 고잔막율, 고평탄화율 및 패턴 안정성을 갖는 오버코트용 레지스트 조성물에 사용할 수 있는 에폭시기를 포함하는 실리콘계 화합물을 제공하는 것이다It is another object of the present invention to provide a silicone-based compound comprising an epoxy group that can be used in a resist composition for overcoat having high heat resistance, high transparency, high residual film rate, high flattening rate and pattern stability.
또한, 본 발명은 바인더 수지와 상용성이 우수한 유기용제를 제공하는데 그 목적이 있다.Another object of the present invention is to provide an organic solvent having excellent compatibility with binder resins.
이하, 본 발명을 더욱 상세히 설명하면 다음과 같다.Hereinafter, the present invention will be described in more detail.
본 발명의 목적을 달성하기 위한 오버코트용 레지스트 조성물은 하기의 일반식1로 표시되는 바인더 수지에 총수지 고형분의 5 내지 95중량%에 해당하는 다기능 모노머를 첨가하고, 총 수지 고형분의 0.1 내지 50중량%의 광개시제; 총 수지 고형분의 0.1내지 10중량%의 에폭시기를 포함하는 실리콘계 화합물; 총 수지 고형분의 0.1 내지 3중량%에 해당하는 공지된 광증감제, 열중합금지제, 소포제, 레벨링제 등의 성분을 혼합한 조성물; 및 용매를 첨가하여 제조되는 것을 특징으로 한다.In the resist composition for overcoat for achieving the object of the present invention, a multifunctional monomer corresponding to 5 to 95% by weight of the total resin solids is added to the binder resin represented by the following general formula 1, 0.1 to 50% by weight of the total resin solids % Photoinitiator; Silicone-based compound containing 0.1 to 10% by weight of the epoxy group of the total resin solids; A composition in which components such as a known photosensitizer, a thermal polymerization inhibitor, an antifoaming agent, and a leveling agent corresponding to 0.1 to 3% by weight of the total resin solids are mixed; And by adding a solvent.
본 발명에서 사용할 수 있는 바인더 수지는 다음 일반식1의 구조로 카르복시산이 포함된 모노머와 이중결합을 가지고 있는 모노머의 조합으로 되어 있는 공중합체를 사용하는 특징이 있다.The binder resin that can be used in the present invention is characterized by using a copolymer composed of a combination of a monomer having a double bond and a monomer containing a carboxylic acid in the structure of the general formula (1).
[일반식1][Formula 1]
여기서, X는 수소원자 또는 메틸기이고, Y1은 2개 내지 16개의 탄소원자를 갖는 알킬기 또는 하이드록시알킬기를 나타내며, Y2는 다음의 화학식(Ⅰ) 내지 화학식(XX)을 나타낸다.X represents a hydrogen atom or a methyl group, Y 1 represents an alkyl group or a hydroxyalkyl group having 2 to 16 carbon atoms, and Y 2 represents the following formulas (I) to (XX).
화학식(Ⅰ) 내지 화학식(XX) 중에서, R1은, 수소 또는 메틸기이고, R2는 1 내지 10의 탄소원자를 보유한 알킬렌 그룹이고, R3는 1 내지 10의 탄소원자를 보유한 탄화수소의 잔류 그룹이고, R4는 수소 또는 메틸기이고, R5는 1 내지 10의 탄소원자를 보유한 알킬렌 그룹이며, 그리고 k는 0 또는 1 내지 10의 정수이다.In formulas (I) to (XX), R 1 is hydrogen or a methyl group, R 2 is an alkylene group having 1 to 10 carbon atoms, R 3 is a residual group of hydrocarbon having 1 to 10 carbon atoms , R 4 is hydrogen or a methyl group, R 5 is an alkylene group with from 1 to 10 carbon atoms, and k is an integer of 0 or 1 to 10.
상기 일반식1로 표시되는 바인더 수지인 공중합체의 평균분자량은 2,000 내지 50,000이고, 분산도는 1.0 내지 5.0이며, 산도는 30 내지 400 KOHmg/g사이로 조절되어야 하며, 바람직하게는 바인더 수지인 공중합체의 평균분자량은 5,000 내지 40,000으로, 분산도는 1.6 내지 3.0으로, 산도는 50 내지150 KOHmg/g사이로 조절하는 것이 상기 오버코트용 레지스트 조성물을 유리판에 회전 도포한 후 마스크를 이용하여 자외선을 조사하고 알칼리 현상액으로 현상하면 원하는 패턴을 갖는 박막을 제조할 수 있으며, 현상 후 잔사 등의 결함을 보이지 않고 우수한 평탄화율을 유지할 수 있다. 또한 상기 일반식1에서 Y1에는 2개 내지 16개의 탄소원자를 갖는 알킬기 또는 하이드록시알킬기 에서 선택된 1종을 사용하여 접착력의 향상에 도움을 주며, Y2에는 벌키(bulky)한 지환족 구조를 첨가하여 오버코트 재료를 기판 위에 코팅하고 용매를 휘발한 후 남아있는 코팅막의 잔막율을 향상시키는 효과가 있다.The average molecular weight of the copolymer of the binder resin represented by the general formula (1) is 2,000 to 50,000, the dispersion degree is 1.0 to 5.0, the acidity should be adjusted between 30 to 400 KOHmg / g, preferably the binder resin The average molecular weight of is 5,000 to 40,000, the dispersion degree is 1.6 to 3.0, the acidity is adjusted to 50 to 150 KOHmg / g to apply the overcoat resist composition to the glass plate after rotating the ultraviolet irradiation using a mask and alkali By developing with a developer, a thin film having a desired pattern can be produced, and excellent flattening ratio can be maintained without showing defects such as residue after development. In addition, in Formula 1, Y 1 helps improve adhesion by using one selected from an alkyl group or a hydroxyalkyl group having 2 to 16 carbon atoms, and a bulky alicyclic structure is added to Y 2. By coating the overcoat material on the substrate and the solvent is volatilized there is an effect of improving the residual film ratio of the remaining coating film.
일반적으로 바인더 수지는 라디칼 반응으로 제조되는데 방향족기가 포함된 모노머, 카르복시산이 포함된 모노머 및 이중결합을 가지고 있는 모노머의 조합으로 되어 있는 공중합체이다. 바인더 수지에서 방향족기의 조성이 증가하면 내열성이 증가하고 또한 이중결합 부분의 조성이 증가해도 내열성 및 패턴 안정성 향상에 도움을 준다. 그러나 상기 일반식 1의 바인더 수지는 측쇄에 아크릴기와 카르복시산을 함유하는 아크릴 공중합 수지로 일반적인 바인더 수지와는 달리 방향족기를 포함하지 않으면서도 내열성을 갖는 구조로 되어 있다. 즉, 내열성 향상에는 도움을 주지만 투명성이 떨어지는 방향족기 대신에 아크릴기 내에 벌키(bulky)한 지환족기를 포함시켜 수지의 유리전이온도를 높여 내열성을 유지할 수 있도록 한다. 다기능 모노머는 공지된 감광성 조성물에 사용하는 에틸렌성 불포화 결합을 갖는 중합성 화합물로 에틸렌글리콜디(메타)아크릴레이트, 에틸렌옥사이드기의 수가 2 내지 14인 폴리에틸렌글리콜디(메타)아크릴레이트, 트리메틸올프로판디(메타)아크릴레이트, 트리메틸올프로판트리(메타)아크릴레이트, 펜타에리스리톨트리(메타)아크릴레이트, 펜타에리스리톨테트라(메타)아크릴레이트, 프로필렌옥사이드기의 수가 2 내지 14인 프로필렌글리콜디(메타)아크릴레이트, 디펜타에리스리톨펜타(메타)아크릴레이트, 디펜타에리스리톨헥사(메타)아크릴레이트 등의 다가 알콜과 α,β-불포화 카르복시산를 에스테르화하여 얻어지는 화합물; 트리메틸올프로판트리글리시딜에테르아크릴산 부가물, 비스페놀 A 디글리시딜에테르아크릴산 부가물 등의 글리시딜기 함유 화합물에 (메타)아크릴산을 부가하여 얻어지는 화합물; β-히드록시에틸(메타)아크릴레이트의 프탈산디에스테르, β-히드록시에틸(메타)아크릴레이트의 톨루엔 디이소시아네이트부가물 등의 수산기 및 에틸렌성 불포화 결합을 갖는 화합물과 다가 카르복시산과의 에스테르 화합물 또는 폴리이소시아네이트와의 부가물; 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 부틸(메타)아크릴레이트, 2-에틸헥실(메타)아크릴레이트 등의 (메타)아크릴산알킬에스테르 중에서 선택된 하나 또는 둘 이상을 혼합하여 사용하는 것이 효과적이다.In general, the binder resin is a copolymer prepared by a radical reaction, which is a combination of a monomer containing an aromatic group, a monomer containing a carboxylic acid, and a monomer having a double bond. Increasing the composition of the aromatic group in the binder resin increases the heat resistance and helps to improve the heat resistance and pattern stability even if the composition of the double bond portion increases. However, the binder resin of the general formula 1 is an acrylic copolymer resin containing an acrylic group and a carboxylic acid in the side chain, and unlike the general binder resin, the binder resin has a structure having heat resistance without containing an aromatic group. In other words, it helps to improve the heat resistance, but instead of containing an aromatic group having a low transparency, it contains a bulky alicyclic group in the acrylic group to increase the glass transition temperature of the resin to maintain the heat resistance. The multifunctional monomer is a polymerizable compound having an ethylenically unsaturated bond used in a known photosensitive composition. Ethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate having 2 to 14 ethylene oxide groups, and trimethylolpropane Di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, and propylene glycol di (meth) having 2 to 14 propylene oxide groups Compounds obtained by esterifying polyhydric alcohols such as acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate and α, β-unsaturated carboxylic acid; Compounds obtained by adding (meth) acrylic acid to glycidyl group-containing compounds such as trimethylolpropanetriglycidyl ether acrylic acid adduct and bisphenol A diglycidyl ether acrylic acid adduct; ester compounds of a compound having a hydroxyl group and an ethylenically unsaturated bond, such as a phthalic acid diester of β-hydroxyethyl (meth) acrylate, a toluene diisocyanate adduct of β-hydroxyethyl (meth) acrylate, or a polyhydric carboxylic acid, or Adducts with polyisocyanates; It is preferable to use one or two or more selected from (meth) acrylic acid alkyl esters such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate and 2-ethylhexyl (meth) acrylate. effective.
삭제delete
상기의 에틸렌성 불포화 결합을 갖는 중합성 화합물인 다기능 모노머와 바인더 수지의 조성을 적절히 조절함으로써 고내열성, 고투명성, 고평탄화율 및 패턴안정성을 유지할 수 있는 오버코트용 레지스트 조성물을 제조하는 것이 가능하다.By appropriately adjusting the composition of the multifunctional monomer and the binder resin, which are polymerizable compounds having an ethylenically unsaturated bond, it is possible to produce a resist composition for overcoat that can maintain high heat resistance, high transparency, high flattening rate and pattern stability.
또한, 광개시제로는 통상적으로 아세토페논계나 벤조페논계를 사용하는데 광개시제 자체가 색을 가지면 투명성을 저하시키는 작용을 하므로 노광 시 사용하는 파장대에서 적절한 감도를 갖고 광개시제 자체에 색을 갖지 않는 것을 사용함으로써 고투명성을 실현할 수 있다. 일반적으로 아크릴계 다기능 모노머를 사용하는 가교 반응에서 광개시제는 사용하는 자외선의 파장에 맞추어서 사용되는데 가장 널리 사용되는 자외선 파장인 수은 램프는 310∼420nm 영역의 파장을 가지므로 이 파장 영역에서 라디칼을 발생하는 광개시제를 사용한다.As photoinitiators, acetophenone-based or benzophenone-based compounds are generally used. When the photoinitiator itself has a color, it acts to reduce transparency. Thus, by using a photosensitive initiator having appropriate sensitivity in the wavelength range used and having no color in the photoinitiator itself, High transparency can be achieved. In general, the photoinitiator is used according to the wavelength of the ultraviolet rays used in the crosslinking reaction using the acrylic multifunctional monomer. Since the mercury lamp, which is the most widely used ultraviolet ray, has a wavelength in the range of 310 to 420 nm, a photoinitiator that generates radicals in this wavelength range Use
광개시제로는 Irgacure 369, Irgacure 907, EPD/BMS 혼합계 등의 벤조페논계와 트리아진계를 사용하는 것이 바람직하다. 예를 들면 벤조페논, 페닐비페닐케톤, 1-히드록시-1-벤조일시클로헥산, 벤질, 벤질디메틸케탈, 1-벤질-1-디메틸아미노-1-(4-모폴리노-벤조일)프로판, 2-모폴릴-2-(4-메틸머캅토)벤조일프로판, 치오잔톤(thioxanthone), 1-클로로-4-프록시치오잔톤, 이소프로필치오잔톤, 디에틸치오잔톤, 에틸안트라퀴논, 4-벤조일-4-메틸디페닐설파이드, 벤조인부틸에테르, 2-히드록시-2-벤조일프로판, 2-히드록시-2-(4-이소프로필)벤조일프로판, 4-부틸벤조일트리클로로메탄, 4-페녹시벤조일디클로로메탄, 벤조일포름산메틸, 1,7-비스(9-아크리디닐)헵탄, 9-n-부틸-3,6-비스(2-모폴리노-이소부틸로일)카바졸, 2-메틸-4,6-비스(트리클로로메틸)-s-트리아진, 2-페닐-4,6-비스(트리클로로메틸)-s-트리아진, 2-나프틸-4,6-비스(트리클로로메틸)-s-트리아진 등이 있다.As a photoinitiator, it is preferable to use benzophenone series and a triazine system, such as Irgacure 369, Irgacure 907, and an EPD / BMS mixed system. Benzophenone, phenylbiphenyl ketone, 1-hydroxy-1-benzoylcyclohexane, benzyl, benzyldimethyl ketal, 1-benzyl-1-dimethylamino-1- (4-morpholino-benzoyl) propane, 2-morpholinyl-2- (4-methylmercapto) benzoylpropane, thioxanthone, 1-chloro-4- hydroxythioxanthone, isopropyl thioxanthone, diethyl thioxanthone, ethyl anthraquinone, 4-benzoyl 4-methyldiphenylsulfide, benzoin butyl ether, 2-hydroxy-2-benzoylpropane, 2-hydroxy-2- (4-isopropyl) benzoylpropane, 4-butylbenzoyltrichloromethane, 4-phenoxy Cybenzoyldichloromethane, methyl benzoyl formate, 1,7-bis (9-acridinyl) heptane, 9-n-butyl-3,6-bis (2-morpholino-isobutyloyl) carbazole, 2 -Methyl-4,6-bis (trichloromethyl) -s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2-naphthyl-4,6-bis ( Trichloromethyl) -s-triazine and the like.
투명성을 높이며 dose량을 최소화하기 위해서 벤조페논계나 트리아진계의 광개시제를 단독 또는 혼합하여 사용하며 총수지 고형분에 대하여 0.1 내지 50중량%를 사용하는 것이 보다 효과적이다.In order to increase the transparency and minimize the dose, it is more effective to use benzophenone-based or triazine-based photoinitiators alone or in combination and 0.1 to 50% by weight based on the total resin solids.
에폭시기를 갖는 실리콘계 첨가물은 ITO 전극과 접착력을 향상시키고 경화 후 내열 특성을 향상시키는 효과가 있으며 (3-글리시드옥시프로필)트리메톡시(에톡시)실레인 (3-글리시드옥시프로필)메틸디메톡시(에톡시)실레인, (3-글리시드옥시프로필) 디메틸메톡시(에톡시)실레인, 3, 4-에폭시부틸트리메톡시(에톡시)실레인, 2-(3,4-에폭시시클로헥실)에틸트리메톡시(에톡시)실레인 등을 사용하는 것이 바람직하다.Silicone-based additives having an epoxy group have the effect of improving adhesion to the ITO electrode and heat resistance properties after curing, and (3-glycidoxypropyl) trimethoxy (ethoxy) silane (3-glycidoxypropyl) methyldimeth Oxy (ethoxy) silane, (3-glycidoxypropyl) dimethylmethoxy (ethoxy) silane, 3,4-epoxybutyltrimethoxy (ethoxy) silane, 2- (3,4-epoxy It is preferable to use cyclohexyl) ethyl trimethoxy (ethoxy) silane and the like.
바인더 수지에 사용되는 유기 용제는 바인더 수지, 다기능 모노머 및 기타 화합물을 첨가·혼합하여 용해하는데 사용할 뿐 만 아니라 우수한 코팅성과 투명한 박막을 얻기 위해 사용하는 것으로 바인더 수지, 다기능 모노머 및 기타 화합물과의 상용성이 우수한 유기 용제를 사용하는 것이 효과적이다. 사용되는 용제로는 에틸아세테이트, 뷰틸아세테이트, 메틸메톡시프로피오네이트, 에틸에톡시프로피오네이트(EEP), 에틸락테이트, 프로필렌글리콜메틸에테르아세테이트(PGMEA), 프로필렌글리콜메틸에테르, 프로필렌글리콜프로필에테르, 메틸셀로솔브아세테이트, 에틸셀로솔브아세테이트, 디에틸렌글리콜메틸(또는 에틸)아세테이트, 아세톤, 메틸이소부틸케톤, 시클로헥사논, 디메틸포룸아미드(DMF), N,N-디메틸아세트아미드(DMAc), N-메틸-2-피롤리돈(NMP), γ-부틸로락톤, 디에틸에테르, 에틸렌글리콜디메틸에테르, 디글림, 테트라하이드로퓨란(THF), 메탄올, 에탄올, 프로판올, 이소-프로판올, 메틸(또는 에틸)셀로솔브, 디에틸렌글리콜메틸(또는 에틸) 에테르, 디프로필렌글리콜메틸에테르, 톨루엔, 크실렌, 헥산, 헵탄, 옥탄 중에서 선택된 한 개 또는 두 개 이상을 혼합한 용매를 사용한다.The organic solvent used in the binder resin is used not only to add and mix the binder resin, the multifunctional monomer and other compounds to dissolve it, but also to obtain excellent coating properties and a transparent thin film, and is compatible with the binder resin, the multifunctional monomer and other compounds. It is effective to use this excellent organic solvent. The solvent used is ethyl acetate, butyl acetate, methyl methoxy propionate, ethyl ethoxy propionate (EEP), ethyl lactate, propylene glycol methyl ether acetate (PGMEA), propylene glycol methyl ether, propylene glycol propyl ether , Methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol methyl (or ethyl) acetate, acetone, methyl isobutyl ketone, cyclohexanone, dimethyl formumamide (DMF), N, N-dimethylacetamide (DMAc ), N-methyl-2-pyrrolidone (NMP), γ-butyrolactone, diethyl ether, ethylene glycol dimethyl ether, diglyme, tetrahydrofuran (THF), methanol, ethanol, propanol, iso-propanol, One or two selected from methyl (or ethyl) cellosolve, diethylene glycol methyl (or ethyl) ether, dipropylene glycol methyl ether, toluene, xylene, hexane, heptane and octane To use a solvent mixture.
또한, 상기의 오버코트용 레지스트 조성물은 코팅성과 고형분 함량을 조절하기 위하여 점도를 2 내지 20 cps로 조절하는 것이 효과적이며, 바람직하게는 5 내지 15 cps가 되도록 조절하는 것이 코팅 후 박막의 핀홀(pin-hole)이 없고 박막의 두께를 조절하는데 보다 유리하다.In addition, the resist composition for overcoat is effective to adjust the viscosity to 2 to 20 cps in order to control the coating property and the solid content, preferably to adjust to 5 to 15 cps pinhole (pin-) of the thin film after coating no holes) and more advantageous for controlling the thickness of thin films.
본 발명의 오버코트용 레지스트 조성물에는 필요에 따라 계면활성제, 보존안정제, 증감제, 스트리에이션 방지제, 가소제 등의 상용성이 있는 첨가제를 함유할 수 있다.The resist composition for overcoat of this invention can contain compatible additives, such as surfactant, a storage stabilizer, a sensitizer, a striation inhibitor, a plasticizer, as needed.
이하 실시예 및 비교예에 의하여 본 발명을 보다 구체적으로 설명하고자 한다. 이들 실시예는 오로지 본 발명을 설명하기 위한 것으로, 본 발명의 요지에 따라 본 발명의 범위가 이들 실시예에 국한되지 않는다는 것은 당업계에서 통상의 지식을 가진 자에게 자명할 것이다. Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples. These examples are only for illustrating the present invention, and it will be apparent to those skilled in the art that the scope of the present invention is not limited to these examples according to the gist of the present invention.
대표적인 오버코트용 레지스트 조성물의 제조예: 자외선 차단막과 교반기가 설치되어 있는 반응혼합조에 일반식 1로 표시된 바인더 수지 용액과 다기능 모노머인 디펜타에리트리톨 헥사/펜타-아크릴레이트(알드리치사)를 첨가하고, 광개시제인 Irgacure 907, (3-글리시드옥시프로필)트리메톡시(에톡시)실레인, 총 수지 고형분의 0.1 내지 3중량%에 해당하는 공지된 광증감제, 열중합금지제, 소포제, 레벨링제 등의 성분을 갖는 조성물을 순차적으로 첨가하고 상온에서 교반한 후 용매를 가하여 레지스트 조성물의 점도를 5 내지 15 cps로 조절한다. Representative preparation example of a resist composition for overcoat : A binder resin solution represented by the general formula (1) and dipentaerythritol hexa / penta-acrylate (Aldrich Co., Ltd.), which are multifunctional monomers, are added to a reaction mixing tank provided with a sunscreen and a stirrer. Irgacure 907, a photoinitiator, (3-glycidoxyoxy) trimethoxy (ethoxy) silane, a known photosensitizer, a thermal polymerization inhibitor, an antifoaming agent, a leveling agent, etc. corresponding to 0.1 to 3% by weight of the total resin solids The composition having the component of was added sequentially and stirred at room temperature, and then the solvent was added to adjust the viscosity of the resist composition to 5 to 15 cps.
실시예 중 바인더 수지는 일반식(1)과 화학식(Ⅰ) 내지 화학식(XX)을 사용한 예를 화학식(1-Ⅰ) 내지 화학식(1-XX)로 표시하였는데, 구입처는 일본국 다이셀 화학공업주식회사(Daicel Chemical Industries. LTD)이고, 각 바인더 수지의 분자량은 약 17000, 분산도는 약 2.0, 산도는 110~120이었다.In the examples, the binder resin is represented by the general formula (1) and the formula (I) to the formula (XX) represented by the formula (1-I) to formula (1-XX). Ltd. (Daicel Chemical Industries. Ltd.), the molecular weight of each binder resin was about 17000, the dispersity was about 2.0, and the acidity was 110 to 120.
대표적인 오버코트용 레지스트 조성물의 비교예: 다음의 일반식2를 사용한 것 이외에는 실시예와 동일한 조성 및 방법으로 오버코트용 레지스트 조성물을 제조하였다.[일반식2] Comparative Example of Representative Overcoat Resist Composition : An overcoat resist composition was prepared in the same composition and method as in Example, except that the following General Formula 2 was used.
삭제delete
여기서, p는 0 < p/p+q ≤ 1 이고, q는 0 < q/p+q ≤ 1이며, r은 (1-p-q)이다.Where p is 0 <p / p + q ≦ 1, q is 0 <q / p + q ≦ 1 and r is (1-p-q).
(1kg 기준) (1 kg standard)
용매의 첨가량 중에서 balance는 1kg에서 바인더수지, 다기능모노머, 실란계에폭시화합물, 광개시제 및 첨가제를 합한 part를 제외한 나머지 part를 첨가하는 것을 의미한다. In the amount of solvent added, the balance means to add the remaining parts except for the part including the binder resin, the multifunctional monomer, the silane epoxy compound, the photoinitiator and the additive at 1 kg.
삭제delete
이상의 실시예 및 비교예에 있어서 레지스트 조성물의 평가는 실리콘 웨이퍼 또는 유리판 등의 기판 위에서 실시하였으며, 레지스트 조성물의 열적특성조사, UV투과율, 잔막율, 패턴 형성 등의 성능평가를 실시하였으며, 그 결과는 다음의 표1과 표2에 나타내었다. In the above Examples and Comparative Examples, the resist composition was evaluated on a substrate such as a silicon wafer or a glass plate, and performance evaluations of thermal properties, UV transmittance, residual film ratio, pattern formation, and the like of the resist composition were performed. Table 1 and Table 2 below.
(1) 열적특성조사(1) Thermal characteristic investigation
오버코트용 레지스트 조성물의 열적 성질을 평가하기 위해 본 발명에서는 열중량분석기(Thermogravimetric analysis: TGA)를 이용하여 열분해 온도를 측정하였으며, 초기무게의 5%가 감소되는 온도를 초기분해 온도로 하여 비교하였다.In order to evaluate the thermal properties of the resist composition for overcoat, the pyrolysis temperature was measured using a thermogravimetric analysis (TGA), and the temperature at which 5% of the initial weight was reduced was compared as the initial decomposition temperature.
(2) UV투과율(2) UV transmittance
레지스트 조성물을 기판 위에 스핀 코터를 이용하여 500rpm의 속도로 20초간 도포한 후, 60℃에서 30초간 프리베이크(prebake)하고, 350nm에서 20초간 경화한 후, 110℃에서 60초간 포스트베이크(postbake)를 실시하여 레지스트 막을 형성하고, UV를 투과하여 투과율을 측정하였다.The resist composition was applied onto the substrate using a spin coater at a speed of 500 rpm for 20 seconds, then prebaked at 60 ° C. for 30 seconds, cured at 350 nm for 20 seconds, and then postbaked at 110 ° C. for 60 seconds. Was carried out to form a resist film, and the transmittance was measured by transmitting UV.
(3) 잔막율(3) residual film rate
오버코트용 레지스트 조성물을 기판 위에 스핀 코팅한 후의 두께와 용매를 제거한 후 형성된 막의 두께 비율(%)을 나타낸다.The thickness after the spin coating of the resist composition for overcoat on the substrate and the thickness ratio of the film formed after removing the solvent are shown.
(4) 패턴 형성(4) pattern formation
레지스트 패턴을 형성한 실리콘 웨이퍼를 라인 패턴의 수직방향에서부터 절단하고, 패턴의 단면 방향에서 전자현미경으로 관찰한 결과를 나타낸다. 패턴 사이드 벽(side wall)이 기판에 대하여 80도 이상의 각도로 세워져 있고, 막이 감소되지 않은 것을 '양호'로 하고, 막의 감소가 인정된 것을 '막감'으로 판정하였다.The silicon wafer in which the resist pattern was formed is cut from the vertical direction of the line pattern, and the result observed by the electron microscope in the cross-sectional direction of the pattern is shown. The pattern side wall was erected at an angle of 80 degrees or more with respect to the substrate, and it was determined that the film was not reduced as 'good', and that the reduction of the film was recognized as the 'film'.
상기 표1과 2에서 알 수 있듯이, 본 발명의 일반식1을 바인더수지로 사용한 오버코트용 레지스트 조성물은 내열성, 투명성, 잔막율, 평탄성이 우수할 뿐만 아니라, 패턴안정성 또한 매우 양호한 것으로 판명되었다.As can be seen from Tables 1 and 2, the resist composition for overcoat using the general formula 1 of the present invention as a binder resin was found to be not only excellent in heat resistance, transparency, residual film ratio, and flatness, but also excellent in pattern stability.
도1은 일반식 1로 표시되는 바인더 수지로 사용하는 오버코트용 레지스트 조성물을 TFT-LCD에서 칼라필터의 오버코트로 사용한 모식도를 보인 것이다. 도2는 실시예 25에 의한 레지스트 조성물의 자외선 경화 후 오버코트 레지스트의 열중량 분해도로 255℃까지 안정한 열적 특성을 나타내고, 도3은 실시예 25에 의한 레지스트 조성물의 자외선 경화 후 오버코트 레지스트로서 Irgacure907의 광개시제를 사용하였을 경우 400nm에서 98%이상의 투과율을 유지하는 것으로 나타났다. 그리고 도4는 실시예25에 의한 레지스트 조성물의 패턴형성 사진으로 우수한 패턴 형성성을 나타냈다.FIG. 1 shows a schematic view of using a resist composition for overcoat used as a binder resin represented by the general formula (1) as an overcoat of a color filter in a TFT-LCD. FIG. 2 shows stable thermal properties up to 255 ° C. by thermogravimetric decomposition of an overcoat resist after UV curing of the resist composition of Example 25, and FIG. 3 shows a photoinitiator of Irgacure907 as an overcoat resist after UV curing of the resist composition of Example 25. When used, it was found that the transmittance of 98% or more was maintained at 400 nm. 4 shows excellent pattern formation in the pattern formation photograph of the resist composition according to Example 25. FIG.
이상에서 살펴본 바와 같이 본 발명에 의하면, 일반식 1을 바인더 수지로 사용하는 오버코트용 레지스트 조성물은 바인더 수지의 구조나 다기능 모노머의 조성비를 변화시켜 오버코트에서 요구되는 물성을 조절하는 것이 가능하고 또한, 본 발명에서 제조된 오버코트용 레지스트 조성물을 자외선에 의해 경화하고 알칼리 현상액으로 현상하여 패턴 형성이 가능하며, 우수한 내열성, 투명성, 잔막율, 평탄성 및 패턴안정성을 용이하게 실현하여 TFT-LCD의 칼라필터의 오버코트에 사용할 수 있는 효과가 있다.As described above, according to the present invention, the resist composition for overcoat using the general formula 1 as the binder resin can control the physical properties required in the overcoat by changing the structure of the binder resin and the composition ratio of the multifunctional monomer. The overcoat resist composition prepared in the present invention can be cured by ultraviolet rays and developed with an alkaline developer to form a pattern, and can easily realize excellent heat resistance, transparency, residual film ratio, flatness and pattern stability to overcoat the color filter of TFT-LCD. There is an effect that can be used for.
제1도는 오버코트를 사용한 TFT-LCD용 칼라필터 모식도1 is a schematic view of a color filter for TFT-LCD using an overcoat
제2도는 자외선 경화 후 오버코트 레지스트의 열중량분해도2 is a thermogravimetric decomposition of the overcoat resist after UV curing
제3도는 자외선 경화 후 오버코트 레지스트의 투명도3 shows the transparency of the overcoat resist after UV curing
제4도는 오버코트용 레지스트 조성물의 패턴 사진4 is a pattern photograph of a resist composition for overcoat
♣ 도면의 주요 부분에 대한 부호의 설명 ♣♣ Explanation of symbols for the main parts of the drawing ♣
1: 칼라필터 2: 블랙매트릭스1: color filter 2: black matrix
3. TFT-LCD의 칼라필터의 오버코트용 레지스트 조성물의 사용처3. Use of resist composition for overcoat of color filter of TFT-LCD
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|---|---|---|---|---|
| WO1995002313A1 (en) * | 1993-07-06 | 1995-01-19 | Kabushiki Kaisha Toshiba | Heat dissipating sheet |
| JPH08194107A (en) * | 1995-01-17 | 1996-07-30 | Mitsubishi Chem Corp | Color-filter picture forming material and production of color filter |
| KR970005056A (en) * | 1995-07-31 | 1997-02-19 | Control Chemical Sprayer | |
| KR19980015678A (en) * | 1996-08-23 | 1998-05-25 | 한형수 | Pigment dispersion photoresist composition for color filter |
| KR0143859B1 (en) * | 1994-07-26 | 1998-07-01 | 박홍기 | Photosensitive resin composition for liquid crystal display color filters |
| JP2000081508A (en) * | 1998-06-30 | 2000-03-21 | Sumitomo Chem Co Ltd | Color filter, its production and photosensitive coloring composition |
| KR20000027191A (en) * | 1998-10-27 | 2000-05-15 | 홍영인 | Resist compound for insulating thin film and manufacturing method thereof |
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Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995002313A1 (en) * | 1993-07-06 | 1995-01-19 | Kabushiki Kaisha Toshiba | Heat dissipating sheet |
| KR0143859B1 (en) * | 1994-07-26 | 1998-07-01 | 박홍기 | Photosensitive resin composition for liquid crystal display color filters |
| JPH08194107A (en) * | 1995-01-17 | 1996-07-30 | Mitsubishi Chem Corp | Color-filter picture forming material and production of color filter |
| KR970005056A (en) * | 1995-07-31 | 1997-02-19 | Control Chemical Sprayer | |
| KR19980015678A (en) * | 1996-08-23 | 1998-05-25 | 한형수 | Pigment dispersion photoresist composition for color filter |
| JP2000081508A (en) * | 1998-06-30 | 2000-03-21 | Sumitomo Chem Co Ltd | Color filter, its production and photosensitive coloring composition |
| KR20000027191A (en) * | 1998-10-27 | 2000-05-15 | 홍영인 | Resist compound for insulating thin film and manufacturing method thereof |
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