KR20140139744A - Liquid composition for stripping a color resist and an organic insulating layer - Google Patents

Liquid composition for stripping a color resist and an organic insulating layer Download PDF

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KR20140139744A
KR20140139744A KR20130060161A KR20130060161A KR20140139744A KR 20140139744 A KR20140139744 A KR 20140139744A KR 20130060161 A KR20130060161 A KR 20130060161A KR 20130060161 A KR20130060161 A KR 20130060161A KR 20140139744 A KR20140139744 A KR 20140139744A
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weight
color resist
potassium
minutes
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KR20130060161A
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KR102010593B1 (en
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방순홍
김우일
윤효중
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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
    • G03F7/423—Stripping or agents therefor using liquids only containing mineral acids or salts thereof, containing mineral oxidizing substances, e.g. peroxy compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/30—Imagewise removal using liquid means
    • G03F7/32—Liquid compositions therefor, e.g. developers
    • G03F7/325—Non-aqueous compositions
    • G03F7/327—Non-aqueous alkaline compositions, e.g. anhydrous quaternary ammonium salts
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
    • H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
    • H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers

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  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Manufacturing & Machinery (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
  • Optical Filters (AREA)

Abstract

The present invention relates to a color resist and an organic insulation film peeling liquid composition, which comprises a quaternary ammonium salt compound, a polar solvent, an alkylamine, an alkoxyalkylamine of the formula (1), an inorganic base or a salt thereof and water .
[Chemical Formula 1]

Figure pat00006

Wherein R 1 is a C 1 to C 6 chained or cyclic alkoxy group, and the alkoxy group is substituted with a C 1 to C 6 chained or cyclic alkyl group or a C 1 to C 3 alkoxy group And R 2 and R 3 are each independently hydrogen or a C 1 to C 6 chain or cyclic alkyl group, and n is an integer of 1 to 4.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a color resist and an organic insulating film,

The present invention relates to a color resist and an organic insulation film peeling liquid composition for reusing a color filter by removing a cured color resist and an organic insulation film of 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. In order to reuse the defective color filter, it is necessary to develop a composition for removing a cured color resist.

In addition, in the present flat panel display device manufacturing process, when an organic insulating film is used for coating a color filter and coating defects of RGB of the color filter occur or coating failure of the organic insulating film occurs, instead of discarding the color filter, There is a need for a stripping liquid composition capable of simultaneously removing an RGB color resist and an organic insulating film for reuse of a color filter because the process yield is improved and the cost is reduced.

Korean Patent Laid-Open No. 10-2009-0019299 discloses a color photoresist stripper composition comprising an inorganic alkali hydroxide or an alkylammonium hydroxide, an alkylene glycol or an alkylene glycol ether, a hydroxylamine, an alkoxyalkylamine and a residual amount of water However, since the use of hydroxylamine causes a problem of deterioration in long-term use due to volatilization during a high-temperature process, there is a problem that the effect of simultaneously removing the color resist and the organic insulating film at high speed can not be exhibited.

Korea Patent Publication No. 10-2009-0019299

In order to solve the problems of the prior art, the present invention provides a color resist and an organic insulating film peeling liquid composition which simultaneously removes a cured color resist and an organic insulating film of a color filter at a high speed to enable reuse of a color filter .

In order to attain the above object, the present invention provides a process for producing an alkoxyalkyl (meth) acrylate compound, which comprises, based on the total weight of the composition, 1-10% by weight of a quaternary ammonium salt compound, 40-80% by weight of a polar solvent, The present invention provides a color resist and an organic insulating film peeling liquid composition, which comprises 1-10% by weight of amine, 0.001-1% by weight of an inorganic base or salt thereof and 1-40% by weight of water.

[Chemical Formula 1]

Figure pat00001

Wherein R 1 is a C 1 to C 6 chained or cyclic alkoxy group, and the alkoxy group is a C 1 to C 6 chained or cyclic alkyl group or a C 1 to C 3 alkoxy group And R 2 and R 3 are each independently hydrogen or a C 1 -C 6 chain or cyclic alkyl group, and n is an integer of 1 to 4.

The stripping liquid composition of the present invention is used for removing cured RGB and transparent organic insulating films of LCD color filters and dissolving resin to minimize clogging of filters in the equipment and effectively removing color filters and organic insulating films to reuse glass or lower vapor- the productivity of rework can be improved.

FIG. 1 is a graph showing the results of evaluation of volatilization of the composition of Example 3 and Comparative Example 6 of the present invention with an open cup at 70.degree.
2 is a graph showing the results of evaluating the removability of a color resist substrate while volatilizing the composition of Example 3 and Comparative Example 6 in an open cup at 70 ° C.

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

The present invention relates to a composition comprising 1-10% by weight of a quaternary ammonium salt compound, 40-80% by weight of a polar solvent, 1-20% by weight of an alkylamine, 1-10% by weight of an alkoxyalkylamine of the formula [1] A color resist and an organic insulation film peeling liquid composition characterized by containing 0.001 to 1 wt% of an inorganic base or a salt thereof and 1 to 40 wt% of water.

[Chemical Formula 1]

Figure pat00002

Wherein R 1 is a C 1 to C 6 chained or cyclic alkoxy group, and the alkoxy group is a C 1 to C 6 chained or cyclic alkyl group or a C 1 to C 3 alkoxy group And R 2 and R 3 are each independently hydrogen or a C 1 -C 6 chain or cyclic alkyl group, and n is an integer of 1 to 4.

The organic insulating layer is used as an insulating layer for preventing connection between metal electrodes stacked on glass as well as being laminated on a color filter to protect the color filter. The organic insulating film is made of an acrylic polymer resin, a polyimide resin, a polyether sulfone resin, or the like. The composition of the present invention can remove the organic insulating film as well as the cured color resist for reuse of the color filter.

The hydroxide ion introduced by the quaternary ammonium salt compound penetrates into the color polymer resist and promotes the dissolution of the polymer resist.

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 is not limited thereto.

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 it is contained in an amount of less than 1% by weight, penetration into the color resist polymer of the hydroxide ion is reduced, and if it exceeds 10% by weight, the content of water is increased to decrease the solubility in the polymer resin.

The polar solvent penetrates the swollen polymer resist and dissolves the resist.

The polar solvent is preferably at least one member selected from the group consisting of dimethylsulfoxide, diethylsulfoxide, dipropylsulfoxide, sulfolane, n-methylpyrrolidone, pyrrolidone and n-ethylpyrrolidone , But is not limited thereto.

The polar solvent is preferably contained in an amount of 40 to 80% by weight based on the total weight of the composition. If it is contained in an amount of less than 40% by weight, the solubility of the polymer resin is lowered, and if it exceeds 80% by weight, the activity of the ammonium salt compound is inhibited and the removability is lowered.

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

Wherein said alkylamine is selected from the group consisting of primary amines including methylamine, ethylamine, isopropylamine, and monoisopropylamine; Secondary amines including diethylamine, diisopropylamine and dibutylamine; Tertiary amines including trimethylamine, triethylamine, triisopropylamine and tributylamine; Diamines including ethylenediamine, propylenediamine, 1,3-propanediamine and 1,2-propylenediamine; And polyamines including diethylenetriamine, dioctylenetriamine, triethylenetetramine, and tetraethylenepentamine, but the present invention is not limited thereto.

The alkylamine is preferably contained in an amount of 1 to 20% by weight based on the total weight of the composition. If it is contained in an amount of less than 1% by weight, it is difficult to dissolve the dye component of the color resist. If it exceeds 20% by weight, there is no increase in the effect due to the increase of the amount, The solubility of the compound

The alkoxyalkylamine is a compound represented by the following formula (1).

[Chemical Formula 1]

Figure pat00003

Wherein R 1 is a C 1 to C 6 chained or cyclic alkoxy group, and the alkoxy group is a C 1 to C 6 chained or cyclic alkyl group or a C 1 to C 3 alkoxy group And R 2 and R 3 are each independently hydrogen or a C 1 -C 6 chain or cyclic alkyl group, and n is an integer of 1 to 4.

The alkoxyalkylamine may be selected from the group consisting of methoxyethylamine, methoxypropylamine, ethoxypropylamine, propoxyethylamine, isopropoxypropylamine, methoxyethoxypropylamine, oxolan-2-ylmethanamine, Yl-methyl) butan-1-amine and methyloxolan-2-yl-methanamine, but the present invention is not limited thereto.

The alkoxyalkylamine compound of Formula 1 is preferably contained in an amount of 1 to 10% by weight based on the total weight of the composition. If it is contained in an amount of less than 1% by weight, the force to break the bond due to penetration into the cured resin is lowered, and if it exceeds 10% by weight, the solubility of the polymer resist is lowered due to the relative reduction of the quaternary alkylammonium compound and the polar solvent.

The inorganic base or its salt compound improves the peeling force with respect to the organic insulating film and includes a metal salt of lithium, sodium or potassium. Specific examples thereof include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, It is preferably at least one selected from the group consisting of potassium, sodium nitrate, potassium nitrate, sodium sulfate, potassium sulfate, sodium silicate, potassium silicate, sodium acetate, and potassium acetate.

The inorganic base or salt compound thereof is preferably contained in an amount of 0.001 to 1.0% by weight based on the total weight of the composition. If the content is less than 0.001% by weight, the peeling force against the organic insulating film is lowered. If the content exceeds 1% by weight, the effect of increasing the content is insignificant and not economical.

The water may be included in an amount of 1 to 40% by weight based on the total weight of the composition. When water is added, the activation of the alkaline compound is improved to increase the removal rate of the resist. In the rinsing step, the organic contaminants remaining on the substrate and the resist stripping solution can be quickly and completely removed.

In the above, it is preferable to use deionized water having a resistivity value of 18 M? / Cm or more as water for semiconductor processing.

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

(1) Preparation of release liquid composition

The components shown in the following Table 1 were mixed according to the determined composition ratios to prepare the release liquid compositions of Examples 1 to 13 and Comparative Examples 1 to 6.

(2) Evaluation of removability of color resist

A color filter substrate on which Red, Green, and Blue (hereinafter referred to as RGB) were respectively applied was used for the removal evaluation of the color resist. The color resist was applied, pre-baked at 90 캜 for 120 seconds, exposed, and then developed. Thereafter, the substrate having the pattern formed in the oven was hard baked in an oven at 220 캜.

To confirm the removability of the color resist, the resist was immersed in a solution at 70 캜 for 3 minutes, 5 minutes, and 10 minutes, and the presence or absence of the resist was confirmed by an optical microscope.

◎: 100% resist removal

○: Resist 80% or more removed

?: Less than 80% resist removal

X: No resist removal

(3) Evaluation of removability of organic insulating film

In order to confirm the removability of the organic insulating film, an organic insulating film was coated on the glass substrate, and the substrate was immersed in a solution of 70 ° C for 5 minutes and 10 minutes using a hard baked substrate, and the organic insulating film remained by optical microscope. The results are shown in Table 2 below.

◎: 100% removal of organic insulating film

○: Removal of organic insulating film more than 80%

DELTA: Less than 80% removal of organic insulating film

X: No organic insulating film removed

Figure pat00004

A1: Isopropylamine

A2: Diethylamine

A3: Ethylenediamine

A4: Propylene diamine

A5: Diethylene triamine

B1: Methoxypropylamine

B2: Propoxyethylamine

B3: Oxolan-2-yl-methanamine

B4: Ethoxypropylamine

HA: Hydroxylamine

MDG: diethylene glycol monomethyl ether

RGB substrate Organic insulating film substrate Rework time 3 minutes 5 minutes 10 minutes Removal time 5 minutes 10 minutes Removal time Example 1 ○ ◎ ◎ 5 minutes ○ ◎ 9 minutes Example 2 ○ ◎ ◎ 5 minutes ○ ◎ 8 minutes Example 3 ○ ◎ ◎ 3 min 30s ○ ◎ 7 min 40s Example 4 ○ ◎ ◎ 4 minutes ○ ◎ 7 minutes 20s Example 5 ○ ◎ ◎ 5 minutes ○ ◎ 9 minutes Example 6 ○ ◎ ◎ 5 minutes ○ ◎ 8 minutes Example 7 ○ ◎ ◎ 5 minutes ○ ◎ 7 minutes Example 8 ○ ◎ ◎ 3 minutes 10s ○ ◎ 8 minutes Example 9 ○ ◎ ◎ 5 minutes ○ ◎ 7 minutes Example 10 ○ ◎ ◎ 5 minutes ○ ◎ 7 minutes Example 11 ○ ◎ ◎ 5 minutes ○ ◎ 7 minutes 20s Example 12 ○ ◎ ◎ 5 minutes ○ ◎ 8 minutes Example 13 ○ ◎ ◎ 5 minutes ○ ◎ 9 minutes Comparative Example 1 X X △ 15 minutes X △ 30 minutes Comparative Example 2 X X △ 18 minutes △ △ 20 minutes Comparative Example 3 X X X 14 minutes X X 18 minutes Comparative Example 4 X X △ 12 minutes △   ○ 18 minutes Comparative Example 5 X △ ○ 12 minutes X △ 20 minutes Comparative Example 6 X ○ ◎ 9 minutes X ○ 14 minutes

As shown in Table 2, in the peeling liquid compositions of Examples 1 to 13 of the present invention, 80% or more of the color filter resist was removed within 3 minutes, 100% of the resist was removed within 5 minutes, I could see. In addition, it was found that the organic-based insulating film resist was also removed by 100% within 10 minutes, showing excellent removal effect of not only RGB but also organic insulating film in a short time.

On the other hand, the compositions of Comparative Examples 1 to 5 required long time to remove the organic insulating film as well as RGB, and it was found that the removal effect thereof was also insufficient.

According to the results of Examples and Comparative Examples, when the alkylamine and the alkoxyalkylamine are contained simultaneously, the removal effect of the RGB substrate and the organic insulating film is better than when the alkylamine or the alkoxyalkylamine is used alone. It was found that the wet penetration of the resist was facilitated by the mutual synergistic effect of the alkylamine having a good RGB removing effect and the alkoxyalkylamine having a good organic-insulating-film removing effect, thereby improving the resist removal rate.

When the hydroxylamine and the alkoxyalkylamine were simultaneously contained in the composition as in Comparative Example 6, it was difficult to remove the RGB or organic insulating film in a short time, and the consumption of the chemical solution was increased due to excessive volatilization at the time of using at a high temperature. , And it is difficult to use for a long period of time.

Fig. 1 shows the result of evaluating the composition of Example 3 and Comparative Example 6 of the present invention at 70 캜 in an open cup. In the case of Comparative Example 6, the amount of the chemical solution required to remove RGB and the organic insulating film was increased due to the volatilization of the chemical liquid twice or more even though the temperature was the same. FIG. 2 also shows the results of evaluating the removability of the color resist substrate while volatilizing the composition of Example 3 and Comparative Example 6 at an open cup at 70 ° C. As the volatilization rate increases, the degradation of performance over time is also observed.

As described above, the color resist of the present invention and the organic insulation film peeling liquid composition of the present invention can sufficiently remove the color resist of the color filter as well as sufficiently remove the organic insulation film and improve the productivity of the color filter reuse .

Claims (6)

1 to 10% by weight of a quaternary ammonium salt compound, 40 to 80% by weight of a polar solvent, 1 to 20% by weight of an alkylamine, 1 to 10% by weight of an alkoxyalkylamine of the formula 0.001-1% by weight of a salt compound and 1-40% by weight of water.
[Chemical Formula 1]
Figure pat00005

Wherein R 1 is a C 1 to C 6 chained or cyclic alkoxy group, and the alkoxy group is a C 1 to C 6 chained or cyclic alkyl group or a C 1 to C 3 alkoxy group And R 2 and R 3 are each independently hydrogen or a C 1 -C 6 chain or cyclic alkyl group, and n is an integer of 1 to 4. The quaternary ammonium salt compound of claim 1 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) Wherein the color resist is at least one selected from the group consisting of a polyimide resin and a polyimide resin. The process of claim 1, wherein the polar solvent is selected from the group consisting of dimethylsulfoxide, diethylsulfoxide, dipropylsulfoxide, sulfolane, n-methylpyrrolidone, pyrrolidone, and n-ethylpyrrolidone. Wherein the color resist and the organic insulation film peel liquid composition are at least two or more species. The method of claim 1, wherein the alkylamine is selected from the group consisting of primary amines including methylamine, ethylamine, isopropylamine, and monoisopropylamine; Secondary amines including diethylamine, diisopropylamine and dibutylamine; Tertiary amines including trimethylamine, triethylamine, triisopropylamine and tributylamine; Diamines including ethylenediamine, propylenediamine, 1,3-propanediamine and 1,2-propylenediamine; And polyamines including diethylene triamine, diethylene triamine, diethylene triamine, triethylene tetramine, and tetraethylene pentaamine. [2] The method of claim 1, wherein the alkoxyalkylamine represented by Formula 1 is selected from the group consisting of methoxyethylamine, methoxypropylamine, ethoxypropylamine, propoxyethylamine, isopropoxypropylamine, methoxyethoxypropylamine, 1-amine and methyloxolan-2-yl-methanamine, characterized in that the color resist is at least one selected from the group consisting of (meth) And an organic insulating film peeling liquid composition. The method of claim 1, wherein the inorganic base or salt compound is selected from the group consisting of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium nitrate, potassium nitrate, sodium sulfate, potassium sulfate, sodium silicate, potassium silicate, And potassium acetate. The color resist and the organic insulation film peeling liquid composition according to claim 1,
KR1020130060161A 2013-05-28 2013-05-28 Liquid composition for stripping a color resist and an organic insulating layer KR102010593B1 (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20030037177A (en) * 2001-11-02 2003-05-12 주식회사 아담스테크놀로지 Stripping aqueous solution for Photoresist
KR20060010366A (en) * 2004-07-28 2006-02-02 주식회사 삼양이엠에스 Aqueous resist stripper formulation
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 (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20030037177A (en) * 2001-11-02 2003-05-12 주식회사 아담스테크놀로지 Stripping aqueous solution for Photoresist
KR20060010366A (en) * 2004-07-28 2006-02-02 주식회사 삼양이엠에스 Aqueous resist stripper formulation
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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