WO2008081045A1 - Composition and method for stripping organic coatings - Google Patents

Composition and method for stripping organic coatings Download PDF

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Publication number
WO2008081045A1
WO2008081045A1 PCT/EP2008/050080 EP2008050080W WO2008081045A1 WO 2008081045 A1 WO2008081045 A1 WO 2008081045A1 EP 2008050080 W EP2008050080 W EP 2008050080W WO 2008081045 A1 WO2008081045 A1 WO 2008081045A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
organic coating
stripping
coating according
mixtures
Prior art date
Application number
PCT/EP2008/050080
Other languages
English (en)
French (fr)
Inventor
Kuo-Chen Su
Shen-Hung Tu
Li-Ying Wang
Original Assignee
Basf Se
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Basf Se filed Critical Basf Se
Priority to JP2009543488A priority Critical patent/JP2010514875A/ja
Publication of WO2008081045A1 publication Critical patent/WO2008081045A1/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D9/00Chemical paint or ink removers
    • C09D9/005Chemical paint or ink removers containing organic solvents
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26Processing photosensitive materials; Apparatus therefor
    • G03F7/42Stripping or agents therefor
    • G03F7/422Stripping or agents therefor using liquids only
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26Processing photosensitive materials; Apparatus therefor
    • G03F7/42Stripping or agents therefor
    • G03F7/422Stripping or agents therefor using liquids only
    • G03F7/425Stripping 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
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/70Microphotolithographic exposure; Apparatus therefor
    • G03F7/708Construction of apparatus, e.g. environment aspects, hygiene aspects or materials
    • G03F7/70908Hygiene, e.g. preventing apparatus pollution, mitigating effect of pollution or removing pollutants from apparatus
    • G03F7/70916Pollution mitigation, i.e. mitigating effect of contamination or debris, e.g. foil traps
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/70Microphotolithographic exposure; Apparatus therefor
    • G03F7/708Construction of apparatus, e.g. environment aspects, hygiene aspects or materials
    • G03F7/70908Hygiene, e.g. preventing apparatus pollution, mitigating effect of pollution or removing pollutants from apparatus
    • G03F7/70933Purge, e.g. exchanging fluid or gas to remove pollutants
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F9/00Registration or positioning of originals, masks, frames, photographic sheets or textured or patterned surfaces, e.g. automatically
    • G03F9/70Registration or positioning of originals, masks, frames, photographic sheets or textured or patterned surfaces, e.g. automatically for microlithography
    • G03F9/7096Arrangement, mounting, housing, environment, cleaning or maintenance of apparatus

Definitions

  • the present invention relates to a composition for stripping an organic coating, and in particular, to a composition for stripping an organic coating used as a protective film or an insulating film of liquid crystal displays and semiconductor devices and a stripping method using the same.
  • An etching process can be considered one of the most important steps of a lithographic process in the liquid crystal display and semiconductor industries.
  • an element pattern on a photoresist mask is transferred onto a photoresist by the lithographic process. Then, the ultimate goal for transferring the whole pattern onto a thin film is achieved by the etching process. This film that undergoes lithography and etching will become a part of liquid crystal displays or semiconductor elements.
  • an organic coating of a polyimide (PI) precursor is typically formed on a glass substrate with metal electrodes, followed by a patterned photoresist mask formed on the organic coating.
  • PI polyimide
  • the exposed organic coating is etched, and a photoresist-stripping liquid is utilized on the glass substrate to remove the photoresist mask, so as to form an etched polyimide precursor.
  • the polyimide precursor is heated to form a polyimide coating.
  • Polyimide is a widely used, heat-resistant plastic which can be used as an insulating coating and can prevent oxidization of the metal layer on the substrate.
  • a conventional method for stripping the etched organic coating from a glass substrate uses dangerous alkaline liquid, such as a heated sodium hydroxide aqueous solution or a hydrazine aqueous solution.
  • alkaline liquid such as a heated sodium hydroxide aqueous solution or a hydrazine aqueous solution.
  • the use of alkaline liquid can completely remove the organic coating, the treatment time has to be well controlled.
  • some glass substrate will be dissolved by the alkaline liquid, resulting in the corrosion of the metal layer.
  • the present invention provides a composition for stripping an organic coating, which can safely and effectively remove the organic coating from a glass substrate without damaging the surface of the metal substrate.
  • the present invention further provides a method for stripping an organic coating, comprising contacting a metal substrate comprising the organic coating with the composition for stripping an organic coating to remove the organic coating from the substrate without damaging the surface of the metal substrate.
  • FIG. 1 shows an etched polyimide on the substrate.
  • FIG. 2 shows the polyimide in FIG. 1 cleaned by a conventional composition.
  • FIG. 3 shows the polyimide in FIG. 1 cleaned by the composition of Embodiment 1 of the present invention.
  • a composition of the present invention for stripping an organic coating comprises about 5 wt% to about 90 wt% of a polar solvent, about 0.01 wt% to about 50 wt% of an alkaline compound, and about 100 ppm to about 15 wt% of a metal corrosion inhibitor, based on the total weight of the composition.
  • the organic coatings that can be effectively removed by the composition for stripping an organic coating of the present invention include, but are not limited to, a polyimide coating and a coating formed by the resins of acrylic, novolac, epoxide or polyvinyl alcohols, preferably a polyimide coating.
  • the polar solvents used in the present invention are solvents having a superior affinity to the organic coating, preferably an aprotic aqueous organic solvent, including, but not limited to, glycol compounds, N-methyl pyrrolidone (NMP), N,N,-dimethyl acetamide
  • DMAC N,N-dimethyl formamide
  • DMSO dimethyl sulfoxide
  • glycol compounds suitable for use in the present invention as the polar solvents are preferably carbitol and the derivatives thereof, including, but not limited to, diethylene glycol monobutyl ether (BDG), diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, diethylene glycol acetate monobutyl ether, and mixtures thereof.
  • BDG diethylene glycol monobutyl ether
  • diethylene glycol monoethyl ether diethylene glycol dimethyl ether
  • diethylene glycol diethyl ether diethylene glycol dibutyl ether
  • diethylene glycol acetate monobutyl ether diethylene glycol acetate monobutyl ether
  • the content of the polar solvents used in the present invention is about 5 wt% to about 90 wt%, preferably about 20 wt% to about 85 wt%, based on the total weight of the composition.
  • the alkaline compounds used in the present invention are preferably selected from the group consisting of amino alcohol compounds, quarternary amine compounds, and mixtures thereof.
  • amino alcohol compounds suitable for use in the present invention as the alkaline compounds are preferably selected from the group consisting of monoethanolamine
  • MEA Methyl ethanolamine
  • N-N-dimethyl ethanolamine N-ethyl ethanolamine
  • N-ethyl ethanolamine N- methyl-N-ethyl ethanolamine
  • N,N-diethyl ethanolamine N-diethyl ethanolamine
  • the quarternary amine compounds suitable for use in the present invention as the alkaline compounds are preferably selected from the group consisting of trimethylanilinium hydroxide, benzyltrimethylammonium hydroxide, choline hydroxide, tetramethylammonium hydroxide (TMAH), tetrapropylammonium hydroxide, and mixtures thereof.
  • TMAH tetramethylammonium hydroxide
  • the content of the alkaline compounds used in the present invention is about 0.01 wt% to about 50 wt%, preferably about 0.1 wt% to about 50 wt%, based on the total weight of the composition.
  • the metal corrosion inhibitors used in the present invention are preferably selected from the group consisting of benzotriazole derivatives, sugar alcohol derivatives, and organic phenol compounds, and mixtures thereof.
  • the sugar alcohol derivatives suitable for use in the present invention as the metal corrosion inhibitors are preferably selected from the group consisting of maltitol, polydextrose, xylitol, lactitol, mannitol, maltitol syrups, isomaltitol, sorbitol, and mixtures thereof.
  • organic phenol compounds suitable for use in the present invention as the metal corrosion inhibitors are preferably catechol.
  • the amount of the metal corrosion inhibitors used in the present invention is about
  • composition for stripping an organic coating of the present invention may optionally comprise additional components well known by persons having ordinary skill in the art, for example, a surfactant for lowering the surface tension or for preventing the organic coating from adhere to the substrate.
  • the composition of the present invention can effectively remove the organic coating from the glass substrate.
  • the composition of the preset invention comprises the metal corrosion inhibitor, which can prevent damage to the surface of the metal substrate, and thus the metal substrate from which the organic coating is removed can be recycled and reused.
  • the present invention further provides a method for stripping an organic coating, comprising contacting a metal substrate comprising the organic coating with the composition for stripping an organic coating to remove the organic coating from the substrate without
  • the preferred stripping temperature ranges from about 40 0 C to
  • FIGs. 1 to 3 are scanning electron microscope photos.
  • FIG. 1 shows an etched polyimide on the substrate.
  • FIG. 2 shows the polyimide cleaned by a conventional composition, in which the etched polyimide was not completely removed.
  • FIG. 3 shows the polyimide cleaned by a composition of Embodiment 1 of the present invention, in which a favorable polyimide removal effect is clearly shown.
  • compositions for stripping polyimide comprising a metal corrosion inhibitor (such as sugar alcohol derivatives or organic phenol compounds) and without a metal corrosion inhibitor were prepared.
  • a metal corrosion inhibitor such as sugar alcohol derivatives or organic phenol compounds
  • a metal substrate having an etched polyimide was immersed in the composition for stripping polyimide for about 5 minutes to about 30 minutes at a temperature ranging from about 4°C to about 90 0 C.
  • composition without the metal corrosion inhibitor the composition comprising the metal

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Public Health (AREA)
  • Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Atmospheric Sciences (AREA)
  • Paints Or Removers (AREA)
  • Environmental & Geological Engineering (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
PCT/EP2008/050080 2007-01-05 2008-01-07 Composition and method for stripping organic coatings WO2008081045A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2009543488A JP2010514875A (ja) 2007-01-05 2008-01-07 有機被覆の除去のための組成物及び方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TW096100419 2007-01-05
TW96100419A TWI338026B (en) 2007-01-05 2007-01-05 Composition and method for stripping organic coatings

Publications (1)

Publication Number Publication Date
WO2008081045A1 true WO2008081045A1 (en) 2008-07-10

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Country Status (4)

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JP (1) JP2010514875A (ja)
KR (1) KR20090122181A (ja)
TW (1) TWI338026B (ja)
WO (1) WO2008081045A1 (ja)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101957565A (zh) * 2010-08-28 2011-01-26 汕头超声印制板(二厂)有限公司 一种有机退膜剂
CN103468052A (zh) * 2013-09-27 2013-12-25 国家电网公司 一种电瓷绝缘子表面失效涂料的剥离剂
CN112230520A (zh) * 2020-11-24 2021-01-15 合肥普庆新材料科技有限公司 一种水性pi膜剥离液及其pi膜玻璃方法
CN112255899A (zh) * 2020-11-24 2021-01-22 合肥普庆新材料科技有限公司 一种水性pi膜剥离液及其制备方法

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017197589A (ja) * 2014-09-04 2017-11-02 横浜油脂工業株式会社 紫外線硬化型塗料用剥離剤
WO2019143202A1 (ko) * 2018-01-19 2019-07-25 주식회사 엠티아이 다이싱 공정용 보호코팅제 박리용 박리제
TWI751568B (zh) 2020-05-29 2022-01-01 新應材股份有限公司 蝕刻劑組成物、增黏劑、鹼溶液、移除聚醯亞胺的方法以及蝕刻製程
CN113736466B (zh) * 2020-05-29 2023-05-12 新应材股份有限公司 蚀刻剂组合物、增粘剂、移除聚酰亚胺的方法以及蚀刻工艺

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US20010001784A1 (en) * 1998-06-16 2001-05-24 Marilyn R. Leduc Method for removal of cured photosensitive polyimide
US20010034313A1 (en) * 1997-05-05 2001-10-25 Arch Specialty Chemicals, Inc. Non-corrosive stripping and cleaning composition
US20040067860A1 (en) * 1990-11-05 2004-04-08 Lee Wai Mun Cleaning compositions and methods of use thereof

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Publication number Priority date Publication date Assignee Title
US4276186A (en) * 1979-06-26 1981-06-30 International Business Machines Corporation Cleaning composition and use thereof
US20040067860A1 (en) * 1990-11-05 2004-04-08 Lee Wai Mun Cleaning compositions and methods of use thereof
US5496491A (en) * 1991-01-25 1996-03-05 Ashland Oil Company Organic stripping composition
US5753601A (en) * 1991-01-25 1998-05-19 Ashland Inc Organic stripping composition
US20010034313A1 (en) * 1997-05-05 2001-10-25 Arch Specialty Chemicals, Inc. Non-corrosive stripping and cleaning composition
US20010001784A1 (en) * 1998-06-16 2001-05-24 Marilyn R. Leduc Method for removal of cured photosensitive polyimide

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101957565A (zh) * 2010-08-28 2011-01-26 汕头超声印制板(二厂)有限公司 一种有机退膜剂
CN103468052A (zh) * 2013-09-27 2013-12-25 国家电网公司 一种电瓷绝缘子表面失效涂料的剥离剂
CN112230520A (zh) * 2020-11-24 2021-01-15 合肥普庆新材料科技有限公司 一种水性pi膜剥离液及其pi膜玻璃方法
CN112255899A (zh) * 2020-11-24 2021-01-22 合肥普庆新材料科技有限公司 一种水性pi膜剥离液及其制备方法

Also Published As

Publication number Publication date
JP2010514875A (ja) 2010-05-06
TW200829667A (en) 2008-07-16
TWI338026B (en) 2011-03-01
KR20090122181A (ko) 2009-11-26

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