KR20140082418A - color resist stripper composition - Google Patents

color resist stripper composition Download PDF

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KR20140082418A
KR20140082418A KR1020120152360A KR20120152360A KR20140082418A KR 20140082418 A KR20140082418 A KR 20140082418A KR 1020120152360 A KR1020120152360 A KR 1020120152360A KR 20120152360 A KR20120152360 A KR 20120152360A KR 20140082418 A KR20140082418 A KR 20140082418A
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South Korea
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group
weight
salt compound
carbon atoms
color resist
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KR1020120152360A
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Korean (ko)
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KR102040064B1 (en
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윤효중
김우일
방순홍
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동우 화인켐 주식회사
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/02—Inorganic compounds
    • C11D7/04—Water-soluble compounds
    • C11D7/10—Salts
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen
    • C11D7/3209—Amines or imines with one to four nitrogen atoms; Quaternized amines
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/34—Organic compounds containing sulfur

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Inorganic Chemistry (AREA)
  • Optical Filters (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)

Abstract

A color resist stripper composition containing no alkylene glycol ether, comprising a quaternary ammonium salt compound, dimethyl sulfoxide, an alkylhydroxylamine represented by the following formula (1), an alkylamine, an alkali salt compound, To a resist stripping liquid composition. The color resist stripping composition of the present invention can sufficiently remove the color resist of the color filter and minimize the change of the removal force over time.

Description

[0001] The present invention relates to a color resist stripper composition,

The present invention relates to a color resist stripper composition, and more particularly, to a color resist stripper composition for removing a cured color resist of a color filter to reuse a color filter.

A color filter can be embedded in a color imaging device of an image sensor, such as a complementary metal oxide semiconductor (CMOS) or a charge coupled device (CCD), and can be used to actually obtain a color image (PDP), a liquid crystal display (LCD), a field emission display (FEL), and a light emitting display (LED), and the application range thereof is rapidly expanding. Particularly, in recent years, the use of LCDs has been further expanded, and accordingly, color filters have been recognized as one of the most important components in reproducing color tones of LCDs.

The color filter substrate includes a black matrix that blocks red (R), green (G), and blue (B) patterns and leakage light between the pixels and improves contrast, and a common electrode .

The color filter is manufactured by applying a black matrix material selected according to the application to a glass substrate, forming a black mask pattern, and then forming an RGB color resist pattern by a photolithography process.

In such a color filter manufacturing process, a defective color filter may inevitably occur, and a composition for removing a cured color resist for reuse of such a defective color filter has been developed.

For example, JP 1995-028254 A discloses a composition comprising sugar alcohols, DMSO, alcohol amines, quaternary ammonium salt compounds and water for the removal of cured resist resulting from dry etching of wiring materials by halogen gas. The composition can remove the resist using a quaternary ammonium salt compound, dimethylsulfoxide, alcohol amine, and water, but has a disadvantage in that it can not exhibit sufficient removal power for a thermosetting color resist.

In addition, Korean Patent No. 10-2005-0006980 discloses a release liquid composition for reuse of color filters containing inorganic alkali hydroxide or alkyl ammonium hydroxide, dimethyl sulfoxide, alkylene glycol ether, and water. The composition can remove the color resist pattern by using alkylammonium hydroxide, dimethylsulfoxide, and water. However, since the low boiling point of the hydroxylamine includes the hydroxylamine, the life of the solution is not prolonged have.

Therefore, there is a need for a color resist stripping liquid composition which can sufficiently remove a cured color resist and maintain a long-time removing power for reuse of a color filter.

JP 1995-028254 A KR 2005-0006980 A

In order to solve the problems of the prior art, it is an object of the present invention to provide a color resist stripping liquid composition which can sufficiently remove a cured color resist for reuse of a color filter, and can maintain a long-time removing power.

In order to achieve the above object,

The present invention provides a color photoresist stripping liquid composition containing no alkylene glycol ether, which comprises 1 to 10% by weight of a quaternary ammonium salt compound, 30 to 80% by weight of dimethyl sulfoxide, an alkyl The present invention relates to a color resist stripping liquid composition comprising 1 to 20% by weight of a hydroxylamine, 1 to 20% by weight of an alkylamine, 0.001 to 1% by weight of an alkali salt compound and 1 to 40% by weight of water.

Figure pat00001

In this formula,

R 1 and R 2 are each independently an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms, a carboxyl group, an alkoxy group having 1 to 10 carbon atoms which is substituted or unsubstituted with a hydroxy group An alkyl group having 1 to 10 carbon atoms, a phenyl group, or a benzyl group.

The color resist stripper composition of the present invention is used to remove the cured RGB color resist pattern of the LCD color filter to remove the color resist in such a manner that the color resist is dissolved without lifting off the substrate from the substrate, The resist can be sufficiently removed, the clogging of the filter in the equipment can be minimized, the long-time removing power can be maintained, and the productivity of the color filter reuse can be improved.

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

The present invention provides a color photoresist stripping liquid composition containing no alkylene glycol ether, which comprises 1 to 10% by weight of a quaternary ammonium salt compound, 30 to 80% by weight of dimethyl sulfoxide, an alkyl Characterized in that it comprises 1 to 20% by weight of a hydroxylamine, 1 to 20% by weight of an alkylamine, 0.001 to 1% by weight of an alkali salt compound and 1 to 40% by weight of water.

 [Chemical Formula 1]

Figure pat00002

In this formula,

R 1 and R 2 are each independently an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms, a carboxyl group, an alkoxy group having 1 to 10 carbon atoms which is substituted or unsubstituted with a hydroxy group An alkyl group having 1 to 10 carbon atoms, a phenyl group, or a benzyl group.

The quaternary ammonium salt compound penetrates into the color polymer resist to promote the dissolution of the polymer resist.

The quaternary ammonium salt compound is preferably contained in an amount of 1 to 10% by weight based on the total weight of the composition. If the quaternary ammonium salt compound is less than 1% by weight, the penetration ability of the quaternary ammonium salt compound into the color resist polymer of the hydroxide ion is decreased. The content is increased and the solubility to the polymer resist decreases.

Wherein the quaternary ammonium salt compound is selected from the group consisting of tetramethylammonium hydroxide (TMAH), tetraethylammonium hydroxide (TEAH), tetrapropylammonium hydroxide (TPAH), and tetrabutylammonium hydroxide (TBAH) But it is not necessarily limited thereto.

The dimethylsulfoxide penetrates the swollen polymer resist and dissolves the resist.

The dimethylsulfoxide is preferably contained in an amount of 30 to 80% by weight based on the total weight of the composition. When the amount is less than 30% by weight, the solubility of the resist decreases. When the amount exceeds 80% by weight, The penetration into the resist is reduced.

The alkylhydroxylamine penetrates into the crosslinked structure of the color resist to increase the swelling power of the polymer to increase the peeling force from the substrate

The alkylhydroxylamine represented by Formula 1 may be at least one selected from the group consisting of dimethylhydroxylamine, diethylhydroxylamine, dibutylhydroxylamine, and dipropylhydroxylamine. However, It does not.

The amount of the alkylhydroxylamine is preferably 1 to 20% by weight based on the total weight of the composition. When the amount is less than 1% by weight, the solubility of the color resist decreases. When the amount exceeds 20% by weight, There is no increase, so it is not economical and the number of processing can be reduced

The alkylamine serves to dissolve the dye component of the color resist.

Examples of the alkylamine include, but are not limited to, primary amines such as methylamine, ethylamine, isopropylamine, and monoisopropylamine; Secondary amines such as diethylamine, diisopropylamine and dibutylamine; Tertiary amines such as trimethylamine, triethylamine, triisopropylamine and tributylamine; Diamines such as ethylenediamine, propylenediamine, 1,3-propanediamine, and 1,2-propylenediamine; And triamine such as diethylenetriamine, dioctylenetriamine, and the like.

The alkylamine is preferably contained in an amount of 1 to 20% by weight based on the total weight of the composition. When the amount of the alkylamine is less than 1% by weight, the dye component of the color resist is difficult to dissolve. It is not economical because there is no increase and the solubility of the polymer resist is lowered due to the relative decrease in the content of the quaternary ammonium compound and dimethyl sulfoxide.

When the amount of the alkaline salt compound is more than 1 wt%, it is difficult to improve the peeling performance of the color resist due to secondary contamination .

The alkali salt compound is not particularly limited but is preferably at least one selected from the group consisting of potassium acetate, potassium nitrate, potassium sulfate, potassium silicate, monopotassium phosphate, dipotassium phosphate, and tripotassium phosphate.

Hereinafter, the present invention will be described in more detail by way of examples. However, the scope of the present invention is not limited to the following examples.

Example

Color resist Peeling liquid  Preparation of composition

The components shown in the following Table 1 were mixed according to the determined composition ratios to prepare color resist stripping compositions of Examples 1 to 9 and Comparative Examples 1 to 4.

Color resist Peel force  evaluation

A color filter substrate on which Red, Green, and Blue (hereinafter referred to as RGB) were respectively applied was used for color resist peeling force evaluation. The color resist was prepared by prebaking at 90 ° C for 120 seconds after coating, exposure and development, and then hardbaking the substrate having the pattern formed thereon at 220 ° C in an oven. The prepared color resist substrate was immersed in the color resist stripping solutions of Examples 1 to 9 and Comparative Examples 1 to 4, which had been subjected to 1 day, 10 days, and 2 weeks after the production, respectively at 70 DEG C for 5 minutes, And the results are shown in Table 2 below.


Quaternary ammonium hydroxide DMSO Alkylhydroxylamine Alkylamine Alkaline salt compound Hydroxylamine water Kinds weight% weight% Kinds weight% Kinds weight% Kinds weight% weight% Example 1 TMAH 2 50 Dimethylhydroxylamine 10 Ethylenediamine 10 Potassium acetate 0.1 - Balance Example 2 TMAH 4 50 Dimethylhydroxylamine 15 Diethylamine 5 Potassium nitrate 0.1 - Balance Example 3 TMAH 6 50 Diethylhydroxylamine 10 Ethylenediamine 10 Potassium sulfate 0.1 - Balance Example 4 TEAH 3 40 Diethylhydroxylamine 15 Diethylenetriamine 10 Dipotassium phosphate 0.05 - Balance Example 5 TEAH 3 60 Dimethylhydroxylamine 5 Diisopropylamine 15 Potassium acetate 0.1 - Balance Example 6 TEAH 6 40 Dibutylhydroxylamine 15 Triethylamine 15 Potassium nitrate 0.05 - Balance Example 7 TMAH 2 70 Diethylhydroxylamine 5 Ethylenediamine 15 Potassium sulfate 0.5 - Balance Example 8 TMAH 2 60 Dibutylhydroxylamine 10 Diethylamine 5 Dipotassium phosphate 0.05 - Balance Example 9 TMAH 2 70 Dimethylhydroxylamine 10 Ethylenediamine 5 Potassium acetate 0.2 - Balance Comparative Example 1 - - 80 Dimethylhydroxylamine 5 Diethylenetriamine 5 Potassium nitrate 0.1 0.5 Balance Comparative Example 2 TMAH 2 60 - - Diisopropylamine 15 - - 15 Balance Comparative Example 3 TEAH 5 35 - - Triethylamine 30 - - 5 Balance Comparative Example 4 TEAH 15 20 - - - - Potassium acetate One 19 Balance

TMAH: tetramethylammonium hydroxide

TEAH: tetraethylammonium hydroxide

DMSO: dimethylsulfoxide

Remaining of resist 1 day 10 days 2 weeks Example 1 ○ ○ ○ Example 2 ○ ○ ○ Example 3 ○ ○ ○ Example 4 ○ ○ ○ Example 5 ○ ○ ○ Example 6 ○ ○ ○ Example 7 ○ ○ ○ Example 8 ○ ○ ○ Example 9 ○ ○ ○ Comparative Example 1 X X X Comparative Example 2 ○ X X Comparative Example 3 X X X Comparative Example 4 X X X

As shown in Table 2, the color resist stripper compositions of Examples 1 to 9 showed almost no time-dependent change in resist removal force even after the elapse of time after the preparation, while Comparative Examples 1 to 4 containing hydroxylamine The color resist stripping solution composition of the present invention shows a marked decrease in resist removal force with time. This is because the boiling point of the hydroxylamine is low and the lifetime of the peeling liquid is not long.

Accordingly, the color resist stripper composition of the present invention can sufficiently remove the color resist of the color filter and minimize the change of the removal power over time, so that the productivity of color filter reuse can be improved.

Claims (5)

A color photoresist stripping liquid composition containing no alkylene glycol ether, which comprises 1 to 10% by weight of a quaternary ammonium salt compound, 30 to 80% by weight of dimethyl sulfoxide, an alkylhydroxylamine represented by the following formula 1 to 20% by weight of an alkylamine, 1 to 20% by weight of an alkylamine, 0.001 to 1% by weight of an alkali salt compound and 1 to 40% by weight of water.
[Chemical Formula 1]
Figure pat00003

In this formula,
R 1 and R 2 are each independently an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms, a carboxyl group, an alkoxy group having 1 to 10 carbon atoms which is substituted or unsubstituted with a hydroxy group An alkyl group having 1 to 10 carbon atoms, a phenyl group, or a benzyl group. [2] The method of claim 1, wherein the alkylhydroxylamine represented by Formula 1 is at least one selected from the group consisting of dimethylhydroxylamine, diethylhydroxylamine, dibutylhydroxylamine, and dipropylhydroxylamine. By weight. The quaternary ammonium salt compound according to claim 1, wherein the quaternary ammonium salt compound is tetramethylammonium hydroxide (TMAH), tetraethylammonium hydroxide (TEAH), tetrapropylammonium hydroxide (TPAH) and tetrabutylammonium hydroxide (TBAH) Wherein the color resist stripping liquid composition is at least one selected from the group consisting of polyvinyl alcohol and polyvinyl alcohol. The method of claim 1, wherein the alkylamine is selected from the group consisting of methylamine, ethylamine, isopropylamine, monoisopropylamine, diethylamine, diisopropylamine, dibutylamine, trimethylamine, triethylamine, triisopropyramine, Characterized in that it is at least one selected from the group consisting of tributylamine, ethylenediamine, propylenediamine, 1,3-propanediamine, 1,2-propylenediamine, diethylenetriamine and dioctylenetriamine, Composition. The method according to claim 1, wherein the alkali salt compound is at least one selected from the group consisting of potassium acetate, potassium nitrate, potassium sulfate, potassium silicate, monopotassium phosphate, diphosphate phosphate and triphosphate phosphate. / RTI >
KR1020120152360A 2012-12-24 2012-12-24 color resist stripper composition KR102040064B1 (en)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0728254A (en) 1993-07-08 1995-01-31 Kanto Chem Co Inc Resist release solution
KR20030037177A (en) * 2001-11-02 2003-05-12 주식회사 아담스테크놀로지 Stripping aqueous solution for Photoresist
KR20040064234A (en) * 2003-01-09 2004-07-16 미츠비시 가스 가가쿠 가부시키가이샤 Photoresist stripping agent
KR20050006980A (en) 2003-07-10 2005-01-17 주식회사 동진쎄미켐 Stripping composition for removing color resist of tft-lcd manufacturing process
KR20070075277A (en) * 2006-01-11 2007-07-18 주식회사 동진쎄미켐 A color resist remover composition for tft-lcd preparation
KR20090019299A (en) * 2007-08-20 2009-02-25 주식회사 동진쎄미켐 A color resist remover composition for tft-lcd preparation
KR20090032640A (en) * 2007-09-28 2009-04-01 삼성전자주식회사 Composition for stripping and stripping method

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0728254A (en) 1993-07-08 1995-01-31 Kanto Chem Co Inc Resist release solution
KR20030037177A (en) * 2001-11-02 2003-05-12 주식회사 아담스테크놀로지 Stripping aqueous solution for Photoresist
KR20040064234A (en) * 2003-01-09 2004-07-16 미츠비시 가스 가가쿠 가부시키가이샤 Photoresist stripping agent
KR20050006980A (en) 2003-07-10 2005-01-17 주식회사 동진쎄미켐 Stripping composition for removing color resist of tft-lcd manufacturing process
KR20070075277A (en) * 2006-01-11 2007-07-18 주식회사 동진쎄미켐 A color resist remover composition for tft-lcd preparation
KR20090019299A (en) * 2007-08-20 2009-02-25 주식회사 동진쎄미켐 A color resist remover composition for tft-lcd preparation
KR20090032640A (en) * 2007-09-28 2009-04-01 삼성전자주식회사 Composition for stripping and stripping method

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