KR100579833B1 - Thermal Curable One-liqud Type Epoxy Resin Composition For Over-Coat - Google Patents

Thermal Curable One-liqud Type Epoxy Resin Composition For Over-Coat Download PDF

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KR100579833B1
KR100579833B1 KR1020030089006A KR20030089006A KR100579833B1 KR 100579833 B1 KR100579833 B1 KR 100579833B1 KR 1020030089006 A KR1020030089006 A KR 1020030089006A KR 20030089006 A KR20030089006 A KR 20030089006A KR 100579833 B1 KR100579833 B1 KR 100579833B1
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formula
group
resin composition
epoxy resin
anhydride
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KR20050055943A (en
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배유리
김영근
최숙영
차혁진
이재환
류미선
우승우
유권일
이수현
정용만
최범영
한철
김웅
정낙칠
김민지
최영수
정상협
최재록
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주식회사 삼양이엠에스
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Priority to PCT/KR2004/003221 priority patent/WO2005057285A1/en
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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
    • 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
    • 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
    • C08G59/68—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 catalysts used
    • C08G59/687—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 catalysts used containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • 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
    • G03F7/022—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
    • 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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/42—Stripping or agents therefor
    • G03F7/422—Stripping or agents therefor using liquids only
    • G03F7/425—Stripping or agents therefor using liquids only containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen

Abstract

본 발명은 열경화형 오버코트용 1액형 에폭시 수지 조성물에 관한 것으로서, 바인더 수지 100중량부; 잠재성 경화제 0.1 내지 100중량부; 및 에폭시기를 포함하는 실리콘계 화합물 0.1 내지 100중량부;를 함유하는 열경화형 오버코트용 1액형 에폭시 수지 조성물을 제공한다. 본 발명에 따른 열경화형 오버코트용 1액형 에폭시 수지 조성물은 우수한 저장 안정성을 나타내면서도 내열성, 투명성, 잔막율, 평탄화율 및 접착성이 양호하므로 TFT-LCD 등에 사용되는 칼라필터의 오버코트로서 유용하게 사용될 수 있다.The present invention relates to a one-component epoxy resin composition for thermosetting overcoat, comprising 100 parts by weight of a binder resin; 0.1 to 100 parts by weight of latent curing agent; And 0.1 to 100 parts by weight of a silicone-based compound including an epoxy group. The one-component epoxy resin composition for thermosetting overcoat according to the present invention exhibits excellent storage stability and can be usefully used as an overcoat for color filters used in TFT-LCDs because of its good heat resistance, transparency, residual film ratio, flattening ratio and adhesion. have.

Description

열경화형 오버코트용 1액형 에폭시 수지 조성물{Thermal Curable One-liqud Type Epoxy Resin Composition For Over-Coat}Thermo Curable One-liqud Type Epoxy Resin Composition For Over-Coat}

도 1은 오버코트가 형성된 TFT-LCD용 칼라필터 모식도이고,1 is a schematic view of a color filter for TFT-LCD having an overcoat formed thereon;

도 2는 실시예 1에 따른 열경화형 오버코트용 1액형 에폭시 수지 조성물의 열경화 후 열중량 분해도를 나타낸 그래프이고,Figure 2 is a graph showing the thermogravimetric decomposition after thermosetting of the one-component epoxy resin composition for thermosetting overcoat according to Example 1,

도 3은 실시예 1에 따른 열경화형 오버코트용 1액형 에콕시 수지 조성물의 열경화 후의 투명도를 나타낸 그래프이다.3 is a graph showing the transparency after thermosetting of the one-component epoxy resin composition for thermosetting overcoat according to Example 1. FIG.

♣ 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: 오버코트3: overcoat

본 발명은 TFT-LCD 등에 사용되는 칼라필터의 오버코트를 형성하기 위한 열경화형 1액형 에폭시 수지 조성물에 관한 것이다.The present invention relates to a thermosetting one-component epoxy resin composition for forming an overcoat of a color filter used in a TFT-LCD or the like.

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 UV type과 열경화 type의 두 종류가 있으나, 글래스가 대형화됨에 따라 uv 조사를 원 샷(one shot)으로 하기 어렵게 되었다. 따라서, 열경화 type의 오버코트(overcoat) 개발이 절실히 필요하게 되었다. 그러나 종래의 열경화형 오버코트는 2액형 에폭시 타입(epoxy type)으로서 저장 안정성의 문제로 인하여 사용 전에 바인더 용액(binder solution)과 경화액(hardner solution)을 혼합(mixing)한 후 수 시간 이내에 소모해야하는 공정상의 단점이 있다.Currently, there are two types of overcoat materials, UV type and thermosetting type, but as the glass is enlarged, it becomes difficult to make uv irradiation one shot. Therefore, there is an urgent need for the development of thermoset overcoats. However, the conventional thermosetting overcoat is a two-component epoxy type that requires consumption within several hours after mixing a binder solution and a hardener solution before use due to storage stability problems. There are disadvantages.

따라서, 본 발명이 이루고자 하는 기술적 과제는 전술한 문제점을 해결하여 우수한 저장 안정성을 나타내면서도 내열성, 투명성, 잔막율, 평탄화율 및 접착성이 양호하므로 TFT-LCD 등에 사용되는 칼라필터의 오버코트로서 유용하게 사용될 수 있는 열경화형 오버코트용 1액형 에폭시 수지 조성물을 제공하는데 있다.Accordingly, the technical problem to be solved by the present invention is to solve the above-mentioned problems, while exhibiting excellent storage stability and having good heat resistance, transparency, residual film ratio, flattening rate and adhesiveness, and thus are useful as an overcoat of color filters used in TFT-LCDs. It is to provide a one-component epoxy resin composition for thermosetting overcoat that can be used.

상기 기술적 과제를 달성하기 위하여 본 발명은 하기 화학식 1로 표시되는 바인더 수지 100중량부; 하기 화학식 2로 표시되는 화합물, 하기 화학식 3으로 표시되는 화합물, 하기 화학식 4로 표시되는 화합물, 하기 화학식 5로 표시되는 화합물, 하기 화학식 6으로 표시되는 화합물 및 하기 화학식 7로 표시되는 화합물로 이루어진 군으로부터 선택된 어느 하나 이상의 잠재성 경화제 0.1 내지 100중량부; 및 에폭시기를 포함하는 실리콘계 화합물 0.1 내지 100중량부;를 함유하는 것을 특징으로 하는 열경화형 오버코트용 1액형 에폭시 수지 조성물을 포함한다. The present invention in order to achieve the technical problem 100 parts by weight of the binder resin represented by the formula (1); A group consisting of a compound represented by formula 2, a compound represented by formula 3, a compound represented by formula 4, a compound represented by formula 5, a compound represented by formula 6, and a compound represented by formula 7 0.1 to 100 parts by weight of any one or more latent curing agents selected from; And 0.1 to 100 parts by weight of a silicone-based compound including an epoxy group; and a one-component epoxy resin composition for thermosetting overcoat.

Figure 112003046954960-pat00001
Figure 112003046954960-pat00001

상기 화학식 1에서, A는 에폭시기를 함유하는 모노머로서 글리시딜 아크릴레이트, 글리시딜 메타아크릴레이트, 글리시딜-알파-에틸 아크릴레이트, 글리시딜-알파-엔-프로필아크릴레이트, 글리시딜-알파-부틸아크릴레이트, 3,4-에폭시부틸 메타아크릴레이트, 3,4-에폭시부틸 아크릴레이트, 6,7-에폭시펩틸 메타아크릴레이트, 6,7-에폭시헵틸 아크릴레이트, 6,7-에폭시헵틸-알파-에틸아크릴레이트로 이루어진 군으로부터 선택된 어느 하나이고, B는 카르복실기를 함유하는 모노머로서 아크릴산 또는 메타아크릴산이고, C는 벤직메타아크릴레이트, 스티렌, 알파-메틸 스티렌, 이소보닐아크릴레이트, 이소보닐메타아크릴레이트, 하이드록시에틸 메타아크릴레이트, 디메틸아미노 메타아크릴레이트 및 아크릴 아미드로 이루어진 군으로부터 선택된 어느 하나이고, l, m 및 n은 A, B, 및 C의 몰수로서 각각 0.1-90 mol%, 0-70 mol% 및 0.1-90 mol%이다.In Formula 1, A is a monomer containing an epoxy group, glycidyl acrylate, glycidyl methacrylate, glycidyl-alpha-ethyl acrylate, glycidyl-alpha-ene-propyl acrylate, glycidyl Dyl-alpha-butylacrylate, 3,4-epoxybutyl methacrylate, 3,4-epoxybutyl acrylate, 6,7-epoxypeptyl methacrylate, 6,7-epoxyheptyl acrylate, 6,7- Epoxyheptyl-alpha-ethyl acrylate is any one selected from the group consisting of, B is a monomer containing a carboxyl group is acrylic acid or methacrylic acid, C is benzyl methacrylate, styrene, alpha-methyl styrene, isobornyl acrylate, Isobornyl methacrylate, hydroxyethyl methacrylate, dimethylamino methacrylate and acrylamide , l, m and n are the moles of A, B, and C, 0.1-90 mol%, 0-70 mol% and 0.1-90 mol%, respectively.

Figure 112003046954960-pat00002
Figure 112003046954960-pat00002

상기 화학식 2에서, R1은 알킬기 또는 아릴기이다. In Formula 2, R 1 is an alkyl group or an aryl group.

Figure 112003046954960-pat00003
Figure 112003046954960-pat00003

상기 화학식 3에서, R2는 알킬기 또는 아릴기이다. In Formula 3, R 2 is an alkyl group or an aryl group.

Figure 112003046954960-pat00004
Figure 112003046954960-pat00004

상기 화학식 4에서, R3 및 R4는 각각 아릴기이고,

Figure 112003046954960-pat00005
는
Figure 112003046954960-pat00006
이다.In Formula 4, R 3 and R 4 are each an aryl group,
Figure 112003046954960-pat00005
Is
Figure 112003046954960-pat00006
to be.

Figure 112003046954960-pat00007
Figure 112003046954960-pat00007

상기 화학식 5에서, R5, R6 및 R7은 서로 독립적으로 아릴기 또는 치환된 아릴기이고,

Figure 112003046954960-pat00008
는
Figure 112003046954960-pat00009
,
Figure 112003046954960-pat00010
,
Figure 112003046954960-pat00011
,
Figure 112003046954960-pat00012
, 및
Figure 112003046954960-pat00013
으로 이루어진 군으로부터 선택된 어느 하나이다.In Formula 5, R 5 , R 6 and R 7 are each independently an aryl group or a substituted aryl group,
Figure 112003046954960-pat00008
Is
Figure 112003046954960-pat00009
,
Figure 112003046954960-pat00010
,
Figure 112003046954960-pat00011
,
Figure 112003046954960-pat00012
, And
Figure 112003046954960-pat00013
Any one selected from the group consisting of.

Figure 112003046954960-pat00014
Figure 112003046954960-pat00014

상기 화학식 6에서, R8, R9, R10 및 R11은 서로 독립적으로 알킬기 또는 아릴기이고,

Figure 112003046954960-pat00015
는
Figure 112003046954960-pat00016
,
Figure 112003046954960-pat00017
,
Figure 112003046954960-pat00018
및
Figure 112003046954960-pat00019
으로 이루어진 군으로부터 선택된 어느 하나이다.In Formula 6, R 8 , R 9 , R 10 and R 11 are each independently an alkyl group or an aryl group,
Figure 112003046954960-pat00015
Is
Figure 112003046954960-pat00016
,
Figure 112003046954960-pat00017
,
Figure 112003046954960-pat00018
And
Figure 112003046954960-pat00019
Any one selected from the group consisting of.

Figure 112003046954960-pat00020
Figure 112003046954960-pat00020

상기 화학식 7에서, R12 및 R13은 서로 독립적으로 알킬기 또는 아릴기이다.In Formula 7, R 12 and R 13 are each independently an alkyl group or an aryl group.

본 발명의 열경화형 오버코트용 1액형 에폭시 수지 조성물에 있어서, 화학식 2로 표시되는 화합물로는 프탈릭 안하이드라이드, 테트라하이드로프탈릭 안하이드라이드, 헥사-하이드로프탈릭 안하이드라이드, 메틸테트라하이드로프탈릭 안하이드라이드, 메틸헥사하이드로프탈릭 안하이드라이드, 메틸 엔도메틸렌 테트라-하이드로프탈릭 안하이드라이드, 헥사클로로엔도메틸렌 테트라-하이드로프탈릭 안하이드라이드, 도데실 숙시닉 안하이드라이드, 트리-멜리틱 안하이드라이드 등을 단독으로 또는 이들을 혼합하여 사용할 수 있고, 화학식 3으로 표시되는 화합물로는 피로멜리틱 디안하이드라이드 또는 벤조페논 테트라-카르복실릭 엑시드 디안하이드라이드를 단독으로 또는 이들을 혼합하여 사용할 수 있고, 화학식 4 내지 화학식 7로 표시되는 화합물로는 디페닐 아이도니움 트리플루오로메탄 술포네니트, 디페닐 아이도니움 노나플루오로부탄 술포네이트, 디-(4-t-부틸벤젠)아이도니움 트리플루오로메탄 술포네이트, 트리페닐술포니움 트리풀루오로메탄술포네이트, 트리페닐술포니움 노나플루오로부탄술포네이트, 디페닐 4-메틸페닐 술포니움 트리플루오로메탄술포네이트, S-(2-나프탈렌카보닐메틸)테트라하이드로티오페니움 트리플루오로메탄술포네이트, 디메틸(4-나프톨)술포니움 트리플로오로메탄술포네이트, N-눅시니미딜 10-캠퍼술포네이트, N-(1,2,4,6-테트라하이드로프탈이미딜)-P-톨루엔술포네이트, N-(1,8-나프탈렌디카르복스이미딜)-10-캠퍼술포네이트, N-(1,8-나프탈렌카르복스이미딜)-p-톨루엔술포네이트 등을 사용할 수 있다.In the one-component epoxy resin composition for thermosetting overcoat of the present invention, the compound represented by the formula (2) is phthalic anhydride, tetrahydrophthalic anhydride, hexa-hydrophthalic anhydride, methyltetrahydro Talic anhydride, methylhexahydrophthalic anhydride, methyl endomethylene tetra-hydrophthalic anhydride, hexachloroendomethylene tetra-hydrophthalic anhydride, dodecyl succinic anhydride, tri-meli Tic anhydride and the like may be used alone or in combination thereof. As the compound represented by Formula 3, pyromellitic dianhydride or benzophenone tetra-carboxylic acid dianhydride may be used alone or in combination thereof. Can be, and the compound represented by the formula (4) As water diphenyl iodonium trifluoromethane sulfonite, diphenyl idonium nonafluorobutane sulfonate, di- (4-t-butylbenzene) idonium trifluoromethane sulfonate, triphenylsul Phenium trifluoromethanesulfonate, triphenylsulfonium nonafluorobutanesulfonate, diphenyl 4-methylphenyl sulfonium trifluoromethanesulfonate, S- (2-naphthalenecarbonylmethyl) tetrahydrothio Phenium trifluoromethanesulfonate, dimethyl (4-naphthol) sulfonium trifluoromethanesulfonate, N-Nuxinimidyl 10-camphorsulfonate, N- (1,2,4,6-tetrahydro Deamidyl) -P-toluenesulfonate, N- (1,8-naphthalenedicarboximidyl) -10-camphorsulfonate, N- (1,8-naphthalenecarboximidyl) -p-toluenesulfo Nate and the like can be used.

이하, 본 발명의 열경화형 오버코트용 1액형 에폭시 수지 조성물에 대하여 상세히 설명한다.Hereinafter, the one-component epoxy resin composition for thermosetting overcoat of the present invention will be described in detail.

본 발명의 열경화형 오버코트용 1액형 에폭시 수지 조성물은 상기 화학식 1로 표시되는 바인더 수지를 포함한다. 화학식 1에서 A 모노머는 접착력을 향상시키고, B 모노머는 에폭시 경화에 도움을 주어 경화시간을 단축 시키며, C 모노머는 필름의 내구성 향상에 도움을 준다. 이러한 화학식 1의 공중합체는 라디칼 중합 개시제와 용매 존재하에서 라디칼 반응으로 제조할 수 있다. 바람직하게는 화학식 1로 표시되는 바인더 수지 평균분자량은 2,000 내지 100,000이고, 분산도는 1.0 내지 5.0이며, 산도는 0 내지 400 KOHmg/g사이이고, 더욱 바람직하게는 평균분자량 5,000 내지 60,000, 분산도 1.6 내지 3.0, 산도는 0 내지150 KOHmg/g사이이다.The one-component epoxy resin composition for thermosetting overcoat of the present invention includes a binder resin represented by Chemical Formula 1. In the general formula (1) A monomer improves the adhesion, B monomer helps to cure the epoxy to shorten the curing time, C monomer helps to improve the durability of the film. The copolymer of Formula 1 may be prepared by radical reaction in the presence of a radical polymerization initiator and a solvent. Preferably the average molecular weight of the binder resin represented by the formula (1) is 2,000 to 100,000, the dispersion degree is 1.0 to 5.0, the acidity is between 0 to 400 KOHmg / g, more preferably the average molecular weight 5,000 to 60,000, dispersion degree 1.6 To 3.0, acidity is between 0 and 150 KOHmg / g.

또한, 본 발명의 열경화형 오버코트용 1액형 에폭시 수지 조성물은 총 수지 고형분을 기준으로 상기 화학식 2로 표시되는 화합물, 상기 화학식 3으로 표시되는 화합물, 상기 화학식 4로 표시되는 화합물, 상기 화학식 5로 표시되는 화합물, 상기 화학식 6으로 표시되는 화합물 및 상기 화학식 7로 표시되는 화합물로 이루어진 군으로부터 선택된 어느 하나 이상의 잠재성 경화제 0.1 내지 100중량부를 포함한다. In addition, the one-component epoxy resin composition for thermosetting overcoat of the present invention is a compound represented by the formula (2), a compound represented by the formula (3), a compound represented by the formula (4) based on the total resin solids, represented by the formula (5) It comprises a compound, a compound represented by the formula (6) and 0.1 to 100 parts by weight of any one or more latent curing agents selected from the group consisting of the compound represented by the formula (7).

상기 화학식 2로 표시되는 화합물은 디카르복실릭 엑시드 시클릭 안하이드라이드로서 프탈릭 안하이드라이드, 테트라하이드로프탈릭 안하이드라이드, 헥사-하이드로프탈릭 안하이드라이드, 메틸테트라하이드로프탈릭 안하이드라이드, 메틸헥사하이드로프탈릭 안하이드라이드, 메틸 엔도메틸렌 테트라-하이드로프탈릭 안하이드라이드, 헥사클로로엔도메틸렌 테트라-하이드로프탈릭 안하이드라이드, 도데실 숙시닉 안하이드라이드, 트리-멜리틱 안하이드라이드 등을 들 수 있고, 상기 화학 식 3으로 표시되는 화합물은 테트라카르복실릭 엑시드 디안하이드라이드로서 피로멜리틱 디안하이드라이드 또는 벤조페논 테트라-카르복실릭 엑시드 디안하이드라이드 등을 들 수 있는데, 이들은 모두 비이온성 타입의 잠재성 경화제이다. 또한, 화학식 4 내지 7로 표시되는 화합물은 엑시드 제너레이터 타입의 잠재성 경화제로서, 디페닐 아이도니움 트리플루오로메탄 술포네니트, 디페닐 아이도니움 노나플루오로부탄 술포네이트, 디-(4-t-부틸벤젠)아이도니움 트리플루오로메탄 술포네이트, 트리페닐술포니움 트리풀루오로메탄술포네이트, 트리페닐술포니움 노나플루오로부탄술포네이트, 디페닐 4-메틸페닐 술포니움 트리플루오로메탄술포네이트, S-(2-나프탈렌카보닐메틸)테트라하이드로티오페니움 트리플루오로메탄술포네이트, 디메틸(4-나프톨)술포니움 트리플로오로메탄술포네이트, N-눅시니미딜 10-캠퍼술포네이트, N-(1,2,4,6-테트라하이드로프탈이미딜)-P-톨루엔술포네이트, N-(1,8-나프탈렌디카르복스이미딜)-10-캠퍼술포네이트, N-(1,8-나프탈렌카르복스이미딜)-p-톨루엔술포네이트 등을 예시할 수 있다. 화학식 1로 표시되는 바인더 수지, 비이온성 타입의 잠재성 경화제 및 엑시드 제너레이터 타입의 잠재성 경화제의 종류와 조성을 적절히 조절하므로서 오버코트에서 요구되는 물성을 변화시킬 수 있다.Compound represented by the formula (2) is a phthalic anhydride, tetrahydrophthalic anhydride, hexa-hydrophthalic anhydride, methyltetrahydrophthalic anhydride as dicarboxylic acid cyclic anhydride , Methylhexahydrophthalic anhydride, methyl endomethylene tetra-hydrophthalic anhydride, hexachloroendomethylene tetra-hydrophthalic anhydride, dodecyl succinic anhydride, tri-melitic anhydride And the compound represented by the formula (3) include pyromellitic dianhydride or benzophenone tetra-carboxylic acid dianhydride as tetracarboxylic acid dianhydride. It is a latent curing agent of nonionic type. In addition, the compounds represented by the formulas (4) to (7) are late generator type latent curing agents, such as diphenyl idonium trifluoromethane sulfonite, diphenyl idonium nonafluorobutane sulfonate, and di- (4- t-butylbenzene) idonium trifluoromethane sulfonate, triphenylsulfonium tripulolomethanesulfonate, triphenylsulfonium nonafluorobutanesulfonate, diphenyl 4-methylphenyl sulfonium trifluor Romethanesulfonate, S- (2-naphthalenecarbonylmethyl) tetrahydrothiophenium trifluoromethanesulfonate, dimethyl (4-naphthol) sulfonium trifluoromethanesulfonate, N-nuxinimidyl 10- Camphorsulfonate, N- (1,2,4,6-tetrahydrophthalimidyl) -P-toluenesulfonate, N- (1,8-naphthalenedicarboximidyl) -10-camphorsulfonate, N- (1,8-naphthalenecarboximidyl) -p-toluenesulfonate, etc. It can be exemplified. The physical properties required in the overcoat can be changed by appropriately adjusting the type and composition of the binder resin represented by the formula (1), the latent curing agent of the nonionic type and the latent curing agent of the acid generator type.

또한, 본 발명의 열경화형 오버코트용 1액형 에폭시 수지 조성물은 총 수지 고형분을 기준으로 에폭시기를 갖는 실리콘계 화합물을 0.1 내지 100중량부 포함하는데, 이러한 실리콘계 화합물은 접착력을 향상시키고 경화 후 내열 특성을 향상시키는 효과가 있다. 에폭시기를 갖는 실리콘계 화합물로는 (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.In addition, the one-component epoxy resin composition for thermosetting overcoat of the present invention comprises 0.1 to 100 parts by weight of a silicone-based compound having an epoxy group based on the total resin solid content, such a silicone-based compound to improve the adhesion and heat resistance properties after curing It works. Examples of the silicone-based compound having an epoxy group include (3-glycidoxypropyl) trimethoxy (ethoxy) silane, (3-glycidoxypropyl) methyldimethoxy (ethoxy) silane, and (3-glycidoxyoxypropyl). ) Dimethylmethoxy (ethoxy) silane, 3,4-epoxybutyltrimethoxy (ethoxy) silane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxy (ethoxy) silane, etc. It is preferable to use.

위와 같은 조성 성분들은 용매에 첨가되어 사용되는데, 용매로는 바인더 수지, 잠재성 경화제 및 기타 첨가제와 상용성이 우수한 유기용매를 사용하는 것이 효과적이다. 상기와 같은 목적으로 사용되는 용제로는 에틸아세테이트, 부틸아세테이트, 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), ??-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 용매를 단독으로 또는 이들을 1종 이상 혼합하여 사용할 수 있다.The above composition components are used in addition to the solvent, it is effective to use an organic solvent excellent in compatibility with the binder resin, latent curing agent and other additives. The solvent used for the above purpose 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 formamide (DMF), N, N- Dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), ??-butyrolactone, diethyl ether, ethylene glycol dimethyl ether, diglyme, tetrahydrofuran (THF), methanol, ethanol, Select from propanol, iso-propanol, methyl (or ethyl) cellosolve, diethylene glycol methyl (or ethyl) ether, dipropylene glycol methyl ether, toluene, xylene, hexane, heptane, octane The may be used alone or mixed with them more than one solvent.

또한, 본 발명의 열경화형 오버코트용 1액형 에폭시 수지 조성물은 코팅성과 고형분 함량을 조절하기 위하여 점도를 2 내지 20 cps로 조절하는 것이 바람직한데, 이러한 범위로 점도를 조절하면 코팅 후 박막의 핀홀(pin-hole)이 없고 박막의 두께를 조절하는데 보다 유리하다. 더욱 바람직한 점도는 10 내지 15 cps이다.In addition, the one-component epoxy resin composition for thermosetting overcoat of the present invention preferably adjusts the viscosity to 2 to 20 cps in order to control the coating property and the solid content, and if the viscosity is adjusted in this range, the pinhole of the thin film after coating no holes, and more advantageous for controlling the thickness of thin films. More preferred viscosity is 10 to 15 cps.

본 발명의 열경화형 오버코트용 1액형 에폭시 수지 조성물에는 오버코트용 조성물에 통상적으로 사용되는 레벨링제, 소포제 등을 적정량 첨가할 수 있으며, 필요에 따라 계면활성제, 보존안정제, 증감제, 스트리에이션 방지제, 가소제 등의 상용성이 있는 첨가제를 더 첨가할 수 있다.The one-component epoxy resin composition for thermosetting overcoat of the present invention may be added with an appropriate amount of a leveling agent, an antifoaming agent or the like commonly used in the composition for overcoat, and if necessary, a surfactant, a storage stabilizer, a sensitizer, a striation inhibitor, a plasticizer. Additives, such as compatibility, can be added further.

이하, 본 발명을 구체적으로 설명하기 위해 실시예 및 비교예를 들어 상세하게 설명하기로 한다. 그러나, 본 발명에 따른 실시예들은 여러 가지 다른 형태로 변형될 수 있으며, 본 발명의 범위가 아래에서 상술하는 실시예들에 한정되는 것으로 해석되어져서는 안된다. 본 발명의 실시예들은 당업계에서 평균적인 지식을 가진 자에게 본 발명을 보다 완전하게 설명하기 위해서 제공되어지는 것이다.Hereinafter, the present invention will be described in detail with reference to Examples and Comparative Examples. However, embodiments according to the present invention can be modified in many different forms, the scope of the present invention should not be construed as limited to the embodiments described below. Embodiments of the present invention are provided to more completely explain the present invention to those skilled in the art.

<실시예><Example>

교반기가 설치되어 있는 반응혼합조에 하기 표 1 ~ 5에 기재된 성분과 조성에 다라 화학식 1로 표시된 바인더 수지 용액(A=glycidyl methacrylate, B=methacrylic acid, C=methyl methacrylate, 평균분자량=50,000, 분산도=2.5), 잠재성 경화제, 에폭시기를 포함하는 실리콘계 화합물 및 기타 첨가제를 순차적으로 첨가하고 용매를 가하여 상온에서 교반한다. 용매를 가하여 레지스트 조성물의 점도를 10 내지 15 cps로 조절한다. 용매의 첨가량 중에서 balance는 1kg에서 바인더수지, 잠재성경화제, 실란계에폭시화합물 및 첨가제를 합한 part를 제외한 나머지 part를 첨가하는 것을 의미한다.Binder resin solution (A = glycidyl methacrylate, B = methacrylic acid, C = methyl methacrylate, average molecular weight = 50,000, dispersion degree) according to the components and composition shown in Tables 1 to 5 in the reaction mixing tank equipped with a stirrer = 2.5), a latent curing agent, a silicone-based compound containing an epoxy group, and other additives are added sequentially, and a solvent is added and stirred at room temperature. Solvent is added to adjust the viscosity of the resist composition to 10-15 cps. In the amount of solvent added, the balance means to add the remaining part except the binder resin, the latent hardener, the silane epoxy compound and the additive part at 1 kg.

실시예 중 잠재성 경화제 I 내지 XXIII는 각각 프탈릭 안하이드라이드(I), 테트라하이드로프탈릭 안하이드라이드(II), 헥사-하이드로프탈릭 안하이드라이드(III), 메틸테트라하이드로프탈릭 안하이드라이드(IV), 메틸헥사하이드로프탈릭 안하이드라이드(V), 메틸 엔도메틸렌 테트라-하이드로프탈릭 안하이드라이드(VI), 헥사클로로엔도메틸렌 테트라-하이드로프탈릭 안하이드라이드(VII), 도데실 숙시닉 안하이드라이드(VIII), 트리-멜리틱 안하이드라이드(IX), 피로멜리틱 디안하이드라이드(X), 벤조페논 테트라-카르복실릭 엑시드 디안하이드라이드(XI), 디페닐 아이도니움 트리플루오로메탄 술포네니트(XII), 디페닐 아이도니움 노나플루오로부탄 술포네이트(XIII), 디-(4-t-부틸벤젠)아이도니움 트리플루오로메탄 술포네이트(XIV), 트리페닐술포니움 트리풀루오로메탄술포네이트(XV), 트리페닐술포니움 노나플루오로부탄술포네이트(XVI), 디페닐 4-메틸페닐 술포니움 트리플루오로메탄술포네이트(XVII), S-(2-나프탈렌카보닐메틸)테트라하이드로티오페니움 트리플루오로메탄술포네이트(XVIII), 디메틸(4-나프톨)술포니움 트리플로오로메탄술포네이트(XIX), N-눅시니미딜 10-캠퍼술포네이트(XX), N-(1,2,4,6-테트라하이드로프탈이미딜)-P-톨루엔술포네이트(XXI), N-(1,8-나프탈렌디카르복스이미딜)-10-캠퍼술포네이트(XXII) 및 N-(1,8-나프탈렌카르복스이미딜)-p-톨루엔술포네이트(XXIII)이다.The latent curing agents I to XXIII in the examples are phthalic anhydride (I), tetrahydrophthalic anhydride (II), hexa-hydrophthalic anhydride (III), and methyltetrahydrophthalic anhydride, respectively. Lide (IV), methylhexahydrophthalic anhydride (V), methyl endomethylene tetra-hydrophthalic anhydride (VI), hexachloroendomethylene tetra-hydrophthalic anhydride (VII), dodecyl Succinic anhydride (VIII), tri-melitic anhydride (IX), pyromellitic dianhydride (X), benzophenone tetra-carboxylic acid dianhydride (XI), diphenyl ironium Trifluoromethane sulfonite (XII), diphenyl idonium nonafluorobutane sulfonate (XIII), di- (4-t-butylbenzene) ironium trifluoromethane sulfonate (XIV), tri Phenylsulfonium Trifulouro Methanesulfonate (XV), triphenylsulfonium nonafluorobutanesulfonate (XVI), diphenyl 4-methylphenyl sulfonium trifluoromethanesulfonate (XVII), S- (2-naphthalenecarbonylmethyl) Tetrahydrothiophenium trifluoromethanesulfonate (XVIII), dimethyl (4-naphthol) sulfonium trifluoromethanesulfonate (XIX), N-Nuxinimidyl 10-camphorsulfonate (XX), N- (1,2,4,6-tetrahydrophthalimidyl) -P-toluenesulfonate (XXI), N- (1,8-naphthalenedicarboximidyl) -10-camphorsulfonate (XXII) and N- (1,8-naphthalenecarboximidyl) -p-toluenesulfonate (XXIII).

<비교예>Comparative Example

상기 실시예의 바인더 수지 대신 하기 화학식 8로 표시되는 바인더 수지를 사용하고, 조성물의 성분 및 함량을 표 6에 기재된 조성에 따라서 변화시킨 것을 제외하고는 실시예와 동일한 방법으로 제조하였다.Instead of the binder resin of the above embodiment, a binder resin represented by the following formula (8) was used, except that the composition and content of the composition were changed according to the composition shown in Table 6, and prepared in the same manner as in Example.

Figure 112003046954960-pat00021
Figure 112003046954960-pat00021

상기 화학식 8에서, n은 1 내지 10임.In Formula 8, n is 1 to 10.

이상의 실시예 및 비교예에 있어서 레지스트 조성물의 평가는 실리콘 웨이퍼 또는 유리판 등의 기판 위에서 실시하였으며, 레지스트 조성물의 열적특성조사, UV투과율, 잔막율, 저장안정성의 성능평가를 실시하였으며, 그 결과는 다음의 표 7에 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 the thermal properties, UV transmittance, residual film ratio, and storage stability of the resist composition were evaluated. It is shown in Table 7.

(1) 열적특성조사(1) Thermal characteristic investigation

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 composition, 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

조성물을 기판 위에 스핀 코터를 이용하여 500rpm의 속도로 20초간 도포한 후, 90℃에서 5분간 프리베이크(prebake)하고, 220℃에서 60분간 포스트베이크(postbake)를 실시하여 레지스트 막을 형성하고, UV를 투과하여 투과율을 측정하였다.The composition was applied onto the substrate using a spin coater at a speed of 500 rpm for 20 seconds, followed by prebaking at 90 ° C. for 5 minutes, and postbake at 220 ° C. for 60 minutes to form a resist film, followed by UV The transmittance was measured by passing through.

(3) 잔막율(3) residual film rate

조성물을 기판 위에 스핀 코팅후 prebake 한후의 두께와 post bake 후 형성된 막의 두께 비율(%)을 나타낸다.The thickness ratio of the thickness of the film formed after the post-baking and the thickness after prebake after the composition is spin coated on the substrate.

(4) 저장안정성(4) storage stability

조성물을 상온에서 한달간 방치한 후 점도 변화가 5 cps 이내에 들면, '우수'로 하고, 점도변화가 5cps 이상이면, '불량'으로 판정하였다. When the composition was left at room temperature for one month, if the viscosity change was within 5 cps, it was 'excellent', and if the viscosity change was 5 cps or more, it was determined as 'poor'.

(5) 접착력(5) adhesion

레지스트 패턴을 형성한 실리콘 웨이퍼의 라인 패턴을 100등분하고 테이프를 이용하여 수직방향으로 박리(peeling off) 시켜, 패턴이 박리되지 않은 것을 '우수'로 패턴의 박리가 인정되는 것을 '불량'으로 판정하였다.The line pattern of the silicon wafer on which the resist pattern is formed is divided into 100 parts and peeled off in a vertical direction using a tape, and it is judged as 'bad' that the peeling of the pattern is recognized as 'good' that the pattern has not been peeled off. It was.

실시예 (1Kg기준)Example (based on 1Kg) binder resin (g)binder resin (g) 잠재성 경화제 (g)Latent curing agents (g) silane계epoxy 화합물 (g) Silane epoxy compound (g) 첨가제 (g) Additive (g) 용매menstruum 1One 화학식 1 l=80,m=0,n=20 (200)Formula 1 l = 80, m = 0, n = 20 (200) II (50)50 (3-글리시드옥시프로필)트리메톡시(에톡시)실레인 (10)(3-Glycidoxyoxy) trimethoxy (ethoxy) silane (10) F계 surfactant (1)F-based surfactant (1) EEP (balance)EEP (balance) 22 IIII 33 IIIIII 44 IVIV 55 VV 66 VIVI 77 VIIVII 88 VIIIVIII 99 VIXVIX 1010 XX 1111 XIXI

실시예 (1Kg기준)Example (based on 1Kg) binder resin (g)binder resin (g) 잠재성 경화제 (g)Latent curing agents (g) silane계epoxy화합물 (g) Silane epoxy compound (g) 첨가제 (g) Additive (g) 용매menstruum 1212 l=90,m=0,n=10l = 90, m = 0, n = 10 화학식 1 (200)Formula 1 (200) I (50)I (50) (3-글리시드옥시프로필)트리메톡시(에톡시)실레인 (10)(3-Glycidoxyoxy) trimethoxy (ethoxy) silane (10) F계 surfactant (1)F-based surfactant (1) EEP (balance)EEP (balance) 1313 l=80,m=10,n=10l = 80, m = 10, n = 10 1414 l=70,m=20,n=10l = 70, m = 20, n = 10 1515 l=60,m=30,n=10l = 60, m = 30, n = 10 1616 l=50,m=40,n=10l = 50, m = 40, n = 10 1717 l=40,m=50,n=10l = 40, m = 50, n = 10

실시예 (1Kg기준)Example (based on 1Kg) binder resin (g)binder resin (g) 잠재성 경화제 (g)Latent curing agents (g) silane계epoxy 화합물 (g) Silane epoxy compound (g) 첨가제 (g) Additive (g) 용매menstruum 1818 l=10,m=0,n=90l = 10, m = 0, n = 90 화학식 1 (200)Formula 1 (200) I (50)I (50) (3-글리시드옥시프로필)트리메톡시(에톡시)실레인 (10)(3-Glycidoxyoxy) trimethoxy (ethoxy) silane (10) F계 surfactant (1)F-based surfactant (1) EEP (balance)EEP (balance) 1919 l=30,m=0,n=70l = 30, m = 0, n = 70 2020 l=50,m=0,n=50l = 50, m = 0, n = 50 2121 l=70,m=0,n=30l = 70, m = 0, n = 30 2222 l=90,m=0,n=10l = 90, m = 0, n = 10

실시예 (1Kg기준)Example (based on 1Kg) binder resin (g)binder resin (g) 잠재성 경화제 (g)Latent curing agents (g) silane계epoxy 화합물 (g) Silane epoxy compound (g) 첨가제 (g) Additive (g) 용매menstruum 2323 화학식 1 l=80,m=0,n=20 (200)Formula 1 l = 80, m = 0, n = 20 (200) (20)20 II (3-글리시드옥시프로필)트리메톡시(에톡시)실레인 (10)(3-Glycidoxyoxy) trimethoxy (ethoxy) silane (10) F계 surfactant (1)F-based surfactant (1) EEP (balance)EEP (balance) 2424 (40)40 2525 (60)(60) 2626 (80)(80) 2727 (100)(100)

실시예 (1Kg기준)Example (based on 1Kg) binder resin (g)binder resin (g) 잠재성 경화제 (g)Latent curing agents (g) silane계epoxy 화합물 (g) Silane epoxy compound (g) 첨가제 (g) Additive (g) 용매menstruum 2828 화학식 1 l=80,m=0,n=20 (200)Formula 1 l = 80, m = 0, n = 20 (200) XIIXII (20)20 (3-글리시드옥시프로필)트리메톡시(에톡시)실레인 (10)(3-Glycidoxyoxy) trimethoxy (ethoxy) silane (10) F계 surfactant (1)F-based surfactant (1) EEP (balance)EEP (balance) 2929 XIIIXIII 3030 XVIXVI 3131 XVXV 3232 XVIXVI 3333 XVIIXVII 3434 XVIIIXVIII 3535 XIXXIX 3636 XXXX 3737 XXIXXI 3838 XXIIXXII 3939 XXIIIXXIII

비교예 (1Kg기준)Comparative example (based on 1Kg) binder resin (g)binder resin (g) 잠재성 경화제 (g)Latent curing agents (g) silane계epoxy 화합물 (g) Silane epoxy compound (g) 첨가제 (g) Additive (g) 용매menstruum 1One 화학식 8 (200)Formula 8 (200) I I (20)20 (3-글리시드옥시프로필)트리메톡시(에톡시)실레인 (10)(3-Glycidoxyoxy) trimethoxy (ethoxy) silane (10) F계 surfactant (1)F-based surfactant (1) EEP (balance)EEP (balance) 22 (40)40 33 (60)(60) 4 4 (80)(80)

예Yes UV 투과율 (at 400nm,%)UV transmittance (at 400nm,%) 잔막율 (%)Residual Rate (%) 접착력Adhesion 저장안정성Storage stability 실시예1Example 1 9898 9595 우수Great 우수Great 실시예2Example 2 9797 9696 우수Great 우수Great 실시예3Example 3 9797 9595 우수Great 우수Great 실시예4Example 4 9797 9696 우수Great 우수Great 실시예5Example 5 9595 9494 우수Great 우수Great 실시예6Example 6 9696 9797 우수Great 우수Great 실시예7Example 7 9898 9595 우수Great 우수Great 실시예8Example 8 9595 9696 우수Great 우수Great 실시예9Example 9 9797 9494 우수Great 우수Great 실시예10Example 10 9797 9595 우수Great 우수Great 실시예11Example 11 9797 9595 우수Great 우수Great 실시예12Example 12 9898 9696 우수Great 우수Great 실시예13Example 13 9696 9797 우수Great 우수Great 실시예14Example 14 9696 9595 우수Great 우수Great 실시예15Example 15 9797 9696 우수Great 우수Great 실시예16Example 16 9797 9595 우수Great 우수Great 실시예17Example 17 9898 9696 우수Great 우수Great 실시예18Example 18 9696 9494 우수Great 우수Great 실시예19Example 19 9797 9797 우수Great 우수Great 실시예20Example 20 9898 9595 우수Great 우수Great 실시예21Example 21 9797 9696 우수Great 우수Great 실시예22Example 22 9797 9494 우수Great 우수Great 실시예23Example 23 9797 9595 우수Great 우수Great 실시예24Example 24 9595 9595 우수Great 우수Great 실시예25Example 25 9696 9696 우수Great 우수Great 실시예26Example 26 9898 9797 우수Great 우수Great 실시예27Example 27 9595 9595 우수Great 우수Great 실시예28Example 28 9797 9696 우수Great 우수Great 실시예29Example 29 9797 9595 우수Great 우수Great 실시예30Example 30 9797 9696 우수Great 우수Great 실시예31Example 31 9898 9494 우수Great 우수Great 실시예32Example 32 9696 9797 우수Great 우수Great 실시예33Example 33 9696 9595 우수Great 우수Great 실시예34Example 34 9797 9696 우수Great 우수Great 실시예35Example 35 9797 9494 우수Great 우수Great 실시예36Example 36 9898 9595 우수Great 우수Great 실시예37Example 37 9696 9595 우수Great 우수Great 실시예38Example 38 9797 9696 우수Great 우수Great 실시예39Example 39 9595 9797 우수Great 우수Great 실시예40Example 40 9797 9595 우수Great 우수Great 실시예41Example 41 9696 9696 우수Great 우수Great 비교예1Comparative Example 1 8585 8686 불량Bad 불량Bad 비교예2Comparative Example 2 8888 8888 불량Bad 불량Bad 비교예3Comparative Example 3 8989 8888 불량Bad 불량Bad 비교예4Comparative Example 4 8686 8787 불량Bad 불량Bad

상기 표 7에 나타난 바와 같이, 본 발명에 따라 화학식 1의 바인더와 화학식 2 내지 7의 잠재성 열경화제를 혼합하여 사용한 열경화형 오버코트용 1액형 에폭시 수지 조성물은 내열성, 투명성, 잔막율, 평탄성이 우수할 뿐만 아니라, 유리 표면과의 부착성이 개선되었으며, 저장안정성 또한 매우 양호한 것으로 판명되었다.As shown in Table 7, the one-component epoxy resin composition for thermosetting overcoat using a binder of Formula 1 and a latent thermosetting agent of Formulas 2 to 7 according to the present invention has excellent heat resistance, transparency, residual film ratio, and flatness. In addition, the adhesion to the glass surface was improved, and the storage stability was also found to be very good.

도 1은 오버코트가 형성된 TFT-LCD용 칼라필터 모식도를 나타낸 것이고, 도 2는 실시예 1에 의한 조성물의 열경화 후 오버코트 레지스트의 열중량 분해도로 325℃까지 안정한 열적 특성을 나타낸 그래프이고, 도 3은 실시예 1에 따른 열경화형 오버코트용 1액형 에폭시 수지 조성물의 열경화 후 열중량 분해도를 나타낸 그래프이다. 도 2 내지 3에 나타난 바와 같이, 실시예 1에 의한 조성물은 열경화 후 열적 안정성이 우수하며 400nm에서 98%이상의 투과율을 유지하는 것으로 나타났다. 1 is a schematic view showing a color filter for TFT-LCD having an overcoat, FIG. 2 is a graph showing stable thermal properties up to 325 ° C. by thermogravimetric decomposition of an overcoat resist after thermal curing of the composition according to Example 1, and FIG. 3. Is a graph showing the thermogravimetric decomposition after thermosetting of the one-component epoxy resin composition for thermosetting overcoat according to Example 1. As shown in Figures 2 to 3, the composition according to Example 1 was excellent in thermal stability after heat curing and maintained a transmittance of more than 98% at 400nm.

이상에서 살펴본 바와 같이 본 발명에 따른 열경화형 오버코트용 1액형 에폭시 수지 조성물은 우수한 저장 안정성을 나타내면서도 내열성, 투명성, 잔막율, 평탄화율 및 접착성이 양호하다. 또한, 바인더 수지의 구조나 잠재성 열경화제의 종류나 조성비 조성비를 변화시켜 오버코트에서 요구되는 물성을 조절하는 것이 가능하므로 TFT-LCD 등에 사용되는 칼라필터의 오버코트로서 유용하게 사용될 수 있다.As described above, the one-component epoxy resin composition for thermosetting overcoat according to the present invention exhibits excellent storage stability while having good heat resistance, transparency, residual film ratio, planarization rate, and adhesion. In addition, since the physical properties required in the overcoat can be adjusted by changing the structure of the binder resin, the type of the latent thermosetting agent, or the composition ratio composition ratio, it can be usefully used as an overcoat for color filters used in TFT-LCDs.

Claims (8)

하기 화학식 1로 표시되는 바인더 수지 100중량부;100 parts by weight of the binder resin represented by Formula 1; 하기 화학식 2로 표시되는 화합물, 하기 화학식 3으로 표시되는 화합물, 하기 화학식 4로 표시되는 화합물, 하기 화학식 5로 표시되는 화합물, 하기 화학식 6으로 표시되는 화합물 및 하기 화학식 7로 표시되는 화합물로 이루어진 군으로부터 선택된 어느 하나 이상의 잠재성 경화제 0.1 내지 100중량부; 및A group consisting of a compound represented by formula 2, a compound represented by formula 3, a compound represented by formula 4, a compound represented by formula 5, a compound represented by formula 6, and a compound represented by formula 7 0.1 to 100 parts by weight of any one or more latent curing agents selected from; And 에폭시기를 포함하는 실리콘계 화합물 0.1 내지 100중량부;를 함유하는 것을 특징으로 하는 열경화형 오버코트용 1액형 에폭시 수지 조성물; 0.1 to 100 parts by weight of a silicone compound containing an epoxy group; a one-component epoxy resin composition for thermosetting overcoat, characterized in that it comprises; <화학식 1><Formula 1>
Figure 112003046954960-pat00022
Figure 112003046954960-pat00022
 상기 화학식 1에서, A는 에폭시기를 함유하는 모노머로서 글리시딜 아크릴레이트, 글리시딜 메타아크릴레이트, 글리시딜-알파-에틸 아크릴레이트, 글리시딜-알파-엔-프로필아크릴레이트, 글리시딜-알파-부틸아크릴레이트, 3,4-에폭시부틸 메타아크릴레이트, 3,4-에폭시부틸 아크릴레이트, 6,7-에폭시펩틸 메타아크릴레이트, 6,7-에폭시헵틸 아크릴레이트, 6,7-에폭시헵틸-알파-에틸아크릴레이트로 이루어진 군으로부터 선택된 어느 하나이고, B는 카르복실기를 함유하는 모노머로서 아크릴산 또는 메타아크릴산이고, C는 벤직메타아크릴레이트, 스티렌, 알파-메틸 스티렌, 이소보닐아크릴레이트, 이소보닐메타아크릴레이트, 하이드록시에틸 메타아크릴레이 트, 디메틸아미노 메타아크릴레이트 및 아크릴 아미드로 이루어진 군으로부터 선택된 어느 하나이고, l, m 및 n은 A, B, 및 C의 몰수로서 각각 0.1-90 mol%, 0-70 mol% 및 0.1-90 mol%임;In Formula 1, A is a monomer containing an epoxy group, glycidyl acrylate, glycidyl methacrylate, glycidyl-alpha-ethyl acrylate, glycidyl-alpha-ene-propyl acrylate, glycidyl Dyl-alpha-butylacrylate, 3,4-epoxybutyl methacrylate, 3,4-epoxybutyl acrylate, 6,7-epoxypeptyl methacrylate, 6,7-epoxyheptyl acrylate, 6,7- Any one selected from the group consisting of epoxyheptyl-alpha-ethylacrylate, B is a carboxyl group-containing monomer, acrylic acid or methacrylic acid, C is benzmethacrylate, styrene, alpha-methyl styrene, isobornyl acrylate, Any one selected from the group consisting of isobornyl methacrylate, hydroxyethyl methacrylate, dimethylamino methacrylate and acrylamide , L, m and n are A, B, and each of 0.1-90 mol% as the number of moles of C, 0-70 mol% and 0.1-90 mol% Lim; <화학식 2><Formula 2>
Figure 112003046954960-pat00023
Figure 112003046954960-pat00023
 상기 화학식 2에서, R1은 알킬기 또는 아릴기임; In Formula 2, R 1 is an alkyl group or an aryl group; <화학식 3><Formula 3>
Figure 112003046954960-pat00024
Figure 112003046954960-pat00024
 상기 화학식 3에서, R2는 알킬기 또는 아릴기임; In Formula 3, R 2 is an alkyl group or an aryl group; <화학식 4><Formula 4>
Figure 112003046954960-pat00025
Figure 112003046954960-pat00025
 상기 화학식 4에서, R3 및 R4는 각각 아릴기이고,
Figure 112003046954960-pat00026
는
Figure 112003046954960-pat00027
임;In Formula 4, R 3 and R 4 are each an aryl group,
Figure 112003046954960-pat00026
Is
Figure 112003046954960-pat00027
being; <화학식 5><Formula 5>
Figure 112003046954960-pat00028
Figure 112003046954960-pat00028
 상기 화학식 5에서, R5, R6 및 R7은 서로 독립적으로 아릴기 또는 치환된 아릴기이고,
Figure 112003046954960-pat00029
는
Figure 112003046954960-pat00030
,
Figure 112003046954960-pat00031
,
Figure 112003046954960-pat00032
,
Figure 112003046954960-pat00033
, 및
Figure 112003046954960-pat00034
으로 이루어진 군으로부터 선택된 어느 하나임;In Formula 5, R 5 , R 6 and R 7 are each independently an aryl group or a substituted aryl group,
Figure 112003046954960-pat00029
Is
Figure 112003046954960-pat00030
,
Figure 112003046954960-pat00031
,
Figure 112003046954960-pat00032
,
Figure 112003046954960-pat00033
, And
Figure 112003046954960-pat00034
Any one selected from the group consisting of; <화학식 6><Formula 6>
Figure 112003046954960-pat00035
Figure 112003046954960-pat00035
 상기 화학식 6에서, R8, R9, R10 및 R11은 서로 독립적으로 알킬기 또는 아릴기이고,
Figure 112003046954960-pat00036
는
Figure 112003046954960-pat00037
,
Figure 112003046954960-pat00038
,
Figure 112003046954960-pat00039
및
Figure 112003046954960-pat00040
으로 이루어진 군으로부터 선택된 어느 하나임;In Formula 6, R 8 , R 9 , R 10 and R 11 are each independently an alkyl group or an aryl group,
Figure 112003046954960-pat00036
Is
Figure 112003046954960-pat00037
,
Figure 112003046954960-pat00038
,
Figure 112003046954960-pat00039
And
Figure 112003046954960-pat00040
Any one selected from the group consisting of; <화학식 7><Formula 7>
Figure 112003046954960-pat00041
Figure 112003046954960-pat00041
 상기 화학식 7에서, R12 및 R13은 서로 독립적으로 알킬기 또는 아릴기임.In Formula 7, R 12 and R 13 are each independently an alkyl group or an aryl group. 제1항에 있어서, 상기 화학식 1로 표시되는 바인더 수지의 평균 분자량이 2,000 내지 100,000이고, 분산도는 1.0 내지 5.0이고, 산도는 0 내지 400KOHmg/g인 것을 특징으로 하는 열경화형 오버코트용 1액형 에폭시 수지 조성물.According to claim 1, wherein the average molecular weight of the binder resin represented by the formula (1) is 2,000 to 100,000, the dispersion degree is 1.0 to 5.0, the acidity is 0 to 400KOHmg / g, the one-component epoxy for thermosetting overcoat Resin composition. 제1항에 있어서, 상기 화학식 2로 표시되는 화합물은 프탈릭 안하이드라이드, 테트라하이드로프탈릭 안하이드라이드, 헥사-하이드로프탈릭 안하이드라이드, 메틸테트라하이드로프탈릭 안하이드라이드, 메틸헥사하이드로프탈릭 안하이드라이드, 메틸 엔도메틸렌 테트라-하이드로프탈릭 안하이드라이드, 헥사클로로엔도메틸렌 테트라-하이드로프탈릭 안하이드라이드, 도데실 숙시닉 안하이드라이드 및 트리-멜리틱 안하이드라이드로 이루어진 군으로부터 선택된 어느 하나인 것을 특징으로 하는 열경화형 오버코트용 1액형 에폭시 수지 조성물.According to claim 1, wherein the compound represented by the formula (2) is phthalic anhydride, tetrahydrophthalic anhydride, hexa-hydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydro Talic anhydride, methyl endomethylene tetra-hydrophthalic anhydride, hexachloroendomethylene tetra-hydrophthalic anhydride, dodecyl succinic anhydride and tri-melitic anhydride It is either one, The 1-component epoxy resin composition for thermosetting overcoats. 제1항에 있어서, 상기 화학식 3으로 표시되는 화합물은 피로멜리틱 디안하이드라이드 또는 벤조페논 테트라-카르복실릭 엑시드 디안하이드라이드인 것을 특징으로 하는 열경화형 오버코트용 1액형 에폭시 수지 조성물.The one-component epoxy resin composition for thermosetting overcoat according to claim 1, wherein the compound represented by Chemical Formula 3 is pyromellitic dianhydride or benzophenone tetra-carboxylic acid dianhydride. 제1항에 있어서, 상기 화학식 4 내지 화학식 7로 표시되는 화합물은 디페닐 아이도니움 트리플루오로메탄 술포네니트, 디페닐 아이도니움 노나플루오로부탄 술포네이트, 디-(4-t-부틸벤젠)아이도니움 트리플루오로메탄 술포네이트, 트리페닐술포니움 트리풀루오로메탄술포네이트, 트리페닐술포니움 노나플루오로부탄술포네이트, 디페닐 4-메틸페닐 술포니움 트리플루오로메탄술포네이트, S-(2-나프탈렌카보닐메틸)테트라하이드로티오페니움 트리플루오로메탄술포네이트, 디메틸(4-나프톨)술포니움 트리플로오로메탄술포네이트, N-눅시니미딜 10-캠퍼술포네이트, N-(1,2,4,6-테트라하이드로프탈이미딜)-P-톨루엔술포네이트, N-(1,8-나프탈렌디카르복스이미딜)-10-캠퍼술포네이트 및 N-(1,8-나프탈렌카르복스이미딜)-p-톨루엔술포네이트로 이루어진 군으로부터 선택된 어느 하나인 것을 특징으로 하는 열경화형 오버코트용 1액형 에폭시 수지 조성물.According to claim 1, wherein the compound represented by Formula 4 to Formula 7 is diphenyl idonium trifluoromethane sulfonite, diphenyl idonium nonafluorobutane sulfonate, di- (4-t-butyl Benzene) Idonium trifluoromethane sulfonate, triphenylsulfonium tripulolomethanesulfonate, triphenylsulfonium nonafluorobutanesulfonate, diphenyl 4-methylphenyl sulfonium trifluoromethanesulfo Nate, S- (2-naphthalenecarbonylmethyl) tetrahydrothiophenium trifluoromethanesulfonate, dimethyl (4-naphthol) sulfonium trifluoromethanesulfonate, N-nuxinimidyl 10-camphorsulfonate , N- (1,2,4,6-tetrahydrophthalimidyl) -P-toluenesulfonate, N- (1,8-naphthalenedicarboximidyl) -10-camphorsulfonate and N- ( From the group consisting of 1,8-naphthalenecarboximidyl) -p-toluenesulfonate 1-component epoxy resin composition for thermosetting overcoat, characterized in that any one selected. 제1항에 있어서, 상기 에폭시기를 포함하는 실리콘계 화합물은 (3-글리시드옥시프로필)트리메톡시(에톡시)실레인, (3-글리시드옥시프로필)메틸디메톡시(에톡시)실레인, (3-글리시드옥시프로필) 디메틸메톡시(에톡시)실레인, 3, 4-에폭시부틸트리메톡시(에톡시)실레인 및 2-(3,4-에폭시시클로헥실)에틸트리메톡시(에톡시)실레인으로 이루어진 군으로부터 선택된 어느 하나 이상을 포함하는 것을 특징으로 하는 열경화형 오버코트용 1액형 에폭시 수지 조성물. The method of claim 1, wherein the silicon-based compound containing an epoxy group is (3-glycidoxy propyl) trimethoxy (ethoxy) silane, (3-glycidoxy propyl) methyl dimethoxy (ethoxy) silane, (3-glycidoxypropyl) dimethylmethoxy (ethoxy) silane, 3,4-epoxybutyltrimethoxy (ethoxy) silane and 2- (3,4-epoxycyclohexyl) ethyltrimethoxy ( A one-component epoxy resin composition for thermosetting overcoat, comprising at least one selected from the group consisting of ethoxy) silane. 제1항에 있어서, 점도가 2 내지 20cps이 되도록 용매를 더 첨가하는 것을 특징으로 하는 열경화형 오버코트용 1액형 에폭시 수지 조성물. The one-component epoxy resin composition for thermosetting overcoat according to claim 1, further comprising a solvent so as to have a viscosity of 2 to 20 cps. 제7항에 있어서, 상기 용매는 에틸아세테이트, 부틸아세테이트, 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 및 옥탄으로 이루어진 군으로부터 선택된 어느 하나 이상을 포함하는 것을 특징으로 하는 열경화형 오버코트용 1액형 에폭시 수지 조성물.The method of claim 7, wherein the solvent 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-dimethyl Acetamide (DMAc), N-methyl-2-pyrrolidone (NMP), γ-butyrolactone, diethyl ether, ethylene glycol dimethyl ether, diglyme, tetrahydrofuran (THF), methanol, ethanol, propanol, Iso-propanol, methyl (or ethyl) cellosolve, diethylene glycol methyl (or ethyl) ether, dipropylene glycol methyl ether, toluene, xylene, hexane, heptane and octane A one-component epoxy resin composition for thermosetting overcoat, characterized in that it comprises any one or more selected.
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